Why do some new businesses succeed and others fail? Dreamit Ventures has been ranked as one of the top 10 business accelerators in the world, and David Bookspan, Founding Partner, shares his insight into the role of the brand in growing early stage companies. If you like our podcast, please subscribe and give us a rating!

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David Bookspan: Most fabulously successful companies are brands first. I think you have to build your company around the brand. It’s never to early to start thinking about it.

Bill Gullan: Greetings, one and all. This is Real-World Branding. I’m Bill Gullan, your host and President of Finch Brands, a premier boutique branding agency. Here we are, January’s in full swing. It is freezing on the East Coast, with possible snow coming this weekend. Back to the balmy days in December, when we recorded the interview that we are going to express to all of you today with David Bookspan, who is a lot of different things. Recovering attorney, he’ll take you through his career journey. Two important things to note were his role as founder and currently board member of Monetate, as well as a founding partner of DreamIt Ventures, which is an accelerator for early stage concepts that has had a profound impact on the entrepreneurial scene in greater Philadelphia and beyond.

Seems like we’ve really been focused on start-ups with the last couple of interviews, and One Big Ideas, etc. but at Finch, our business is obviously broader than that. Thinking about brand and as it relates to business concepts, it’s so interesting when you think about the start-up community, and there’s just so much oxygen around entrepreneurship these days, in higher ed, and certainly well beyond that. We want to make sure that start-ups and idea driven ventures are well represented on the roster of Real-World Branding guests and topics. Enjoy, David Bookspan.

Bill: We are here in the wonderful, chaotic, crazy, innovative, fun, high energy headquarters of DreamIt Ventures, with David Bookspan. Thank you for your time sir.

David: Thank you Bill.

Bill: Our pleasure. What an environment this is. The energy level in this part of Philadelphia, and certainly here in these offices is palpable. Tell us a little bit about, where we’re sitting, and what this all about here at DreamIt.

David: We’re in the heart of the innovation neighborhood in West Philadelphia, at 3401 Market, on the second floor. Right now, the offices are a bit quiet because we’re between sessions. The last session of DreamIt just finished up, and a new one will begin in March. This all came about through the Science Center, Drexel, and DreamIt, coming together to locate an innovation hub and headquarters here. Prior to this, we were located in other offices in the Science Center, for each of our Philadelphia cycles. We also have operations that we run in New York, Austin, Texas, Tel Aviv, and in Baltimore. When we came together with Drexel, we decided to make 3401 our world headquarters.

Bill: Terrific. It’s a great boon to this region, and obviously all the entrepreneurs who come through here. Let’s move backwards a bit, into what has been an amazing journey of a career for you. Could you tell us a little bit about the major twists and turns that have led us up to today.

David: Sure, and you’re kind, thank you. I started out, my professional life, as a lawyer. I was a litigator for 15 years.

Bill: We need more of those.

David: Not according to Shakespeare. I had an idea for a business, that was based upon a need I had in my practice, where there was information, which was obscure but important that I needed in my practice. I looked around, was sure somebody was providing it, but nobody was, and I decided to launch off with my partner, Mark Pankhurst, who was a technology guru. MarketSpan was the fourth company that Mark had founded, and I learned at his side.

Bill: Wow, that’s really cool. I think you have indicated you’re a recovering attorney in your bio. Bachelor undergrad, typical Liberal Arts guy, or was is more directed?

David: Psychology major, but yeah, pretty typical liberal arts guy. I chose a major that doesn’t have a thesis, and I was fine.

Bill: Fair enough. That’s sometimes the way to do it. How did you get from there to law school, was it a fairly obvious thing, or did it hit you one day?

David: Yeah, I decided that I was going to embark on a career as a film producer, so I went to law school.

Bill: Perfect, right?

David: Yeah, exactly. Between college and law school, I took a year and a half off. Part of that journey was to Los Angeles. Met with a very famous, and very charming producer, Arthur Hiller. He was the producer of great romantic comedies, like The In-laws, and Outrageous Fortune, Plaza Suite. A whole bunch of great romantic comedies in the 80’s and 70’s. He was kind enough to meet with me and he said to me when I told him that I thought that I wanted a career producing film, he said, ‘Well, there’s two ways to go about it. One is, I can help you get a job in any of the movie houses right now. You’ll start in the mail room, cause they want you to know where everybody is and who everyone is. You work your way up after about six months, you’ll be a system producer, or associate.’ I forget which one it is. That’s basically running coffee.

‘Then you’ll take the next step up, which is a little bit more hands on. Then the rest of your career is based upon your own talent and achievement. Or you could do what I did.’ He said he went to law school and he flunked out in his first semester. My take away from that, of course, was that the way to become a very successful producer was to flunk out of law school.

Bill: Sure, so you went to law school. You’ve got to go first.

David: Yeah, exactly.

Bill: Contrary to the intent, you made it through.

David: Yeah, I had the misfortune of doing well.

Bill: Yeah, right. Darn it!

David: At that point, fairly typical in the 80’s, from a middle class background, you follow the path of least resistance. If you do well in law school, at least at that time, the market certainly has changed, at that time you do well in law school, and a lot of law firms are throwing lots of money at you. It’s hard to resist.

Bill: From that springboard in law, and a need in your practice, moved you into the entrepreneurship realm. MarketSpan was first. What are some of the stops along the way? Obviously Monetate is one we’re going to spend some time on. Could you tell us kind of the steps up to here?

David: Sure. In terms of the personal journey, I started MarketSpan. We released the product commercially on September 1, 1997, and sold the company in June of 2000. If people remember what happened later in 2000, a lot of people think that I was really, really smart, but the truth was I went kicking and screaming to the closing table. I didn’t want to sell the company.

It turned out real well. After that, I sat on a bunch of boards, including the company that acquired MarketSpan. Did a bunch of consulting, but really spent a lot of time trying to make up for lost time with my kids. I was at every doctor’s appointment, every parent-teacher conference, every sporting event, and just had an absolute blast. Around 2007, I was doing some advising and things along the way, and I had an idea for what turned out to be the germ of Monetate, but no where near what it turned into. Also, Mike Levinson came to me with the idea of DreamIt Ventures.

At that point, my older son was already out of the house, so I went to my younger son, Jesse. What I said to him was, I said, ‘Jess, we know what I’m like when I’m starting a company. I know what I’m like when I have customers. I know what I’m like when I have employees. I can’t say it would be any different this time around, than it was previously. I don’t have to do either of these, or I could do both of them, or I could do one of them. What do you think?’

Jesse said, ‘Dad, after all these years of all Dad, all the time, I think it’s a great idea.’

Bill: That’s funny. At what point did the entrepreneurial bug kind of grab you?

David: My friends would say from the very beginning. One of my early entrepreneurial ventures was when I grew up in Westchester County, New York. We had a lot of snow and we did the winters there. I had a business, shoveling walks, shoveling stairs and walkways of the houses in the neighborhood. My friend and I, we would go up, knock on the doors, and we’d have the shovels and the ice choppers, and the salt and everything. Lugging it up the stairs to somebody’s house, and ask if they wanted their walk cleared.

After we negotiated the deal, our third friend would come along with a snow blower. That was probably among my earliest entrepreneurial ventures.

Bill: Find a better way, manage more. You were the neighborhood kid, do they exist anymore?

David: Those kids still exist, thank God. Those kids are wonderful. I love them.

Bill: Everything would be clean. Leaves would be strewn all over the place [without them].

David: We have people far more creative than that, who come through DreamIt, and who I have had the privilege of working with in all of my businesses.

Bill: Right. Indeed. You mentioned the germ of the idea for Monetate. For those, the uninitiated, Monetate is an incredible personalization platform for leading brands. Tell us about, the vision for it, the operating thesis, if you will, and how Monetate became what it is today.

David: The vision for it has been consistent throughout, which is helping brands create fantastic experiences for their customers, one experience at a time. The way we evolved to that, was that I had an idea for something, which didn’t work out along those lines. David Brussin and I co-founded Monetate, and Lucinda is the one who introduced us. The current CEO of Monetate is the person who introduced David and me. She served as the original, independent board member. She was the third member of the board.

Bill: A referee.

David: Yeah, exactly. After she had introduced us, David and I started kicking around an idea that I had. We killed it off pretty quickly, because it was dependent on large companies. We needed to get access and content from large companies in order to do it. It was all based upon the information that came across in the browser session and what we could do with that information to create a great experience for different brands’ customers. We killed that pretty quickly because we realized that we wouldn’t be able to get it to market in any time frame that was acceptable to David and me by working with the big brands.

David came out of a company that had built technology that David had invented, which was truly brilliant, in terms of stopping spam at its source. Before it ever hit the server of the company. At that time, spam was a huge problem. That company was called TurnTide. Lucinda was the CEO of TurnTide.

Bill: All fits, doesn’t it?

David: Josh Kopelman was the chairman of TurnTide, and David was the founding CTO of TurnTide.

Bill: I like that name. I always liked the name TurnTide.

David: That was a huge success. They spun it out from another company privacy group, and 6 months later, they had sold the company to Symantec.

Bill: Yeah. It works.

David: Yeah. It worked really well. It’s one of the terrific Philadelphia success stories. David’s experience in e-mail, led him to think about the germ of what we had been talking about, in terms of how can we use the information coming across in the browser session to create a great experience for different brands’ customers. He thought it would have great application in retail.

We started testing it with various customers. Testing it in concept, not so much in build. We decided that there was something there, and decided to green light it. David and I started working, basically full time on it in October of 2007. We launched the company formally in January of 2008. We built a prototype. Got our early customers. We’re fortunate in the Philadelphia community to have great support from early customers, like QVC, PetFoodDirect, and Urban Outfitters. Fantastic early customers, RevZilla. That really launched us forward.

At the time, we probably were a little ahead of the market. We had various detours along the way. Until the market started to catch up with us. And it finally has. Even with all of the great success that Monetate has had, the future is unbelievable, in terms of where the market is catching up to the whole personalization concept.

Going from testing and targeting, which is where we tucked in originally, and had our initial success, but the path all along for Monetate has been personalization. Creating that unique individual experience for every visitor, to any brand’s digital platforms.

Bill: It certainly sounds like the right idea, at the right moment. You mentioned early on, that your exit from MarketSpan was fairly well timed. Now, when Monetate began, little did we know, 9, 10 months later, the world would change. For you all, bubbling through that, was all of a sudden demand choked or not? How did it feel?

David: I love starting companies in bad economic times. Seriously, I do. Largely because if you can navigate your way through that, you’re incredibly well positioned when the market strikes. Our biggest challenge then, was to be cash conservative.

We understood and David as CEO, I think made some exceptional decisions, in terms of how to manage us through that. We started slow. We worked really hard on making sure that our customer experience was spectacular. Both in terms of the UI/UX, the user interface, and the user experience for our customers, as well as the impact that it had on our customers’ customers. Then we used the time very effectively to basically nail it.

We kept our burn very low. We worked very closely with the customers we had. Luckily, our customers were able to weather the financial storm of 2008. Then when things started to pick up, we were on the rocket ship.

Bill: That’s terrific. In your own career, and sort of moving us back into the name of the podcast, Real-World Branding, in your own career, as well as all the counseling you do with entrepreneurs, what’s the right level of thinking about the brand, for early stage companies, or for concepts that are sort of still coalescing?

David: I think that most fabulously successful companies are brands first. I think you have to build your company around the brand. It’s never to early to start thinking about it. A brand, it’s fundamental, it’s the promise of an experience.

Apple, one of my favorite companies, is really a lifestyle brand, it’s not a technology company. Obviously, it’s a technology company, but the reason that it is so valuable and the reason that people are such fanatics about Apple products, is because of the experience that they deliver. Something like the Nest thermostat also. Everything from packaging, to the presentation, to the experience itself, it’s all very brand conscious.

I think that, getting to the subject of the podcast, I don’t think it’s ever too early to start thinking about brand and to start building it. I don’t think you can fake it. It has to be an authentic brand that’s built around an authentic experience.

Bill: One of the things you mentioned, PetFoodDirect. We spoke recently with Brock. One of the points he was making is, we’re up here near Drexel University, which is obviously involved in this, and teaching folks to think through and understand some of the functional excellence’s that drive entrepreneurship and company formation. Brock and I were talking about how we do notice that there are some folks who are kind of white space entrepreneurs. One of the challenges I think that we identify, with some folks, not to paint to broadly, but you have to have a ‘why’ to your point.

Sort of the point of departure for the business has to be some sort of identified righteousness, around ‘this could be better,’ or ‘let’s do it this way.’ When you think about the profusion of entrepreneurial education and the systems, and the structures that exist like DreamIt, to help channel and accelerate that in entrepreneurial ventures. What’s the difference between intuition, or the role of intuition and depth of feeling on one hand, and sober market analysis and structural business building on the other? That was a meandering question. Did it make any sense?

David: I think I followed it, or at least I can take it in a direction. I think that fundamentally what drives people to create great companies, is a passion for people. You can be looking at anything that goes on during the course of your day, and think, ‘How can I make this better?’ Not necessarily for yourself, but how can I make this experience better for other people.

I don’t think intuition plays a particularly large role in that. It might provide the spark for a thought, but the fundamental decisions have to be data driven. I like to quip that I’m the market for zero products. That has served me well because I don’t want to hear what people think.

Bill: I love that.

David: I don’t want to hear that. I want to see what people do. The first thing I advise entrepreneurs to do, is to sell it before you build it. Take the idea, whatever the concept is. Take it to your customers. See what the reaction is. You don’t need a product in order to do that. You can do that with wire frames. You can do that with mock-ups. Now a lot of this is in the tech business, which is where most of my business is. The only time you’re not burdened by legacy code, is when you don’t have any code.

If you think you know what the market wants, and you’re building it without having that validated, you are going to have trouble. Even if you’re ultimately very successful, and navigate your way to what the market really wants. You’re going to have a tremendous anchor that’s going to be holding you back because of all the things that you put a lot into before then.

Fundamentally, find something that you think really will make people’s lives better. Understand what that market is, and go talk to that market. Then build quickly, and start the continuous iterative process of launching, learning, and then releasing.

Bill: If you go to someone and say, ‘Wouldn’t it be great if you could, or I could, or we could blank.’ If they say, ‘Yeah’, then the process of delivering against that becomes obviously critical. It’s critical the whole time, but then it becomes sort of linear and yeah, that makes sense.

David: You found something earlier, Bill, which is you don’t want to hear the, ‘Oh, that would be wonderful.’ Cause when you talk to people about an idea that you’re thinking about starting a company around, people are just generally very polite. They’ll say, ‘Oh, that’s wonderful, that’s great, of course I would use it. I don’t know how I’ve lived without it.’

If you can really dig down deep, and figure out a way to make it a real experience for somebody then see what they do. One of the things that we advise DreamIt companies to do is, to see how much you can learn for little or no capital.

Spend intellectual capital before you spend financial capital. Can you buy adwords that will validate the underlying theme? For a couple hundred bucks you can see how that theme resonates with a broader audience. You can actually see how many people click. Things like that, where you’re not dependent on people, or even a survey, or a focus group, where there’s all sorts of other pressures that influence people’s behavior.

Bill: Well as a firm, Finch does a lot of sort of structured and formal custom market research. One of the challenges always, to your point, drawing the distinction between sort of reported and observed data that the costs to a focus group participant of saying, ‘Yeah, I’d buy that and spend eight million dollars’, is zero. You’re not making them write a check, and so you need to build question constructs, or find a different way to observe the way that people are interacting with ideas. It’s fascinating. It makes perfect sense.

Along those lines, we talk about brand, we talk about product development, we talk about the role and the sequence of this. You said earlier, when you were talking about your younger son, the preparation that you gave, that if dad is going to get back to this world, you know how I am. Obviously evoking or expressing something that you’re passionate about and the way you behave when you have one of these concerns that are going. What is the role of passion around this? Product development has to be excellent, you have to be a strong marketer and seller, you have to go through, you have to raise money responsibly, and all these different things, control burn. Talk about the role of passion in business success.

David: Yeah. I think passion is critical to any business success. Passion I think is, what gives you the fortitude to persevere when times are bad. In the good times as well, it’s got to make you feel good. What you’re doing has to be fun. Otherwise, you don’t get through those rough patches. I think that passion, as I said earlier, passion for people, I think is essential. Passion for improving people’s lives is essential, and then passion for the mission is what motivates you to success.

Bill: When you see entrepreneurs who come through DreamIt here, obviously focused on different categories, with different ideas, different products. Are there common denominators of the kind of barriers and hurdles, some of which may be structured in obvious business building processes? Which maybe emotional or psychological, are there any common threads of experience that you see that maybe the types of hurdles that entrepreneurs through this experience and in general, will need to surmount if they’re going to be successful in the way, that perhaps their concept gives them the right to be?

David: Yes. I think that, first of all, I’ve been very fortunate in my career to be able to work with people who are way smarter than I am, and way more capable than I am.

Bill: Don’t believe that David.

David: It’s really true Bill. If you’re the smartest person in the room, you’re in the wrong room.

Bill: Right, or you’re alone.

David: Exactly. The confidence to be able to surround yourself with people who are better at anything that you set yourself to do, than you are in some aspect of the business, is something which I think does mark a successful entrepreneur. Certainly the successful DreamIt entrepreneurs.

Also, the lack of fear of failure. Nobody wants to fail. Failure can be a great motivator, but it can’t control you. I frequently quip that after I sold my first business, I became a whole lot smarter. After I sold MarketSpan, I became a whole lot smarter because I didn’t have the fear of getting fired, or the fear of financial impact. Being able to say that I’m making this decision, not because I’m afraid of getting fired, but because it’s the right decision for the company, is incredibly liberating. That is a common denominator.

All of the DreamIt entrepreneurs, both academically, as well as in their life – we have had Grammy winners, we’ve had Olympians, we’ve had unbelievable successful people – the academic credentials are much better than any that I ever have achieved, or could have achieved. A lot of Ph. D’s. Unbelievable talent, unbelievable education, but in terms of the leadership components of what they do, the really successful founders are the one’s who are not afraid, who have confidence, but are also humble.

Bill: We’ve spoken to many folks on this podcasts over the past, almost a year, not quite, and there seems to be … when we think about life stage, you are refreshingly atypical of some folks. We talk about Nick Bayer, who is across the hall in Saxbys, he did it early, no kid, maybe even single, no spouse. The cost of failure, set it in quotation marks is different.

Then you see folks who parlay success in something, into something else, but you’re somebody who, right in the throat of that career litigating, decided that you wanted to do something else. All of the risks associated with that, all of probably the nights of terror associated with that. Could you speak about perhaps, you had responsibilities along the way, you talked about that? Once you had achieved success with MarketSpan, you were able to go back and make up for lost time with kids, and sort of ride that period. Talk about your own life, as it relates to choices, and fear, and risks, and all of these different things.

David: A lot of people give me way too much credit for, perhaps being brave or courageous, when I don’t think of it that way. My decisions may have been naïve, but I certainly don’t think they were brave or courageous.

In that, I figured that I had a very marketable skill, and I was a relatively good lawyer.

Bill: You could always go back, right?

David: Yeah. I knew the kids would get fed, they’d get educated, and the mortgage would get paid. It might take me a while to dig myself out of debt if things had gone poorly, but this wasn’t courageous. Courage is on the battle field, and for people who overcome much greater obstacles. Perhaps naïve. It wouldn’t have been fun if it had failed, but it was not that much risk.

Bill: It’s what we would call a ‘first world problem.’

David: Yes, exactly.

Bill: That said, you’re humble and thoughtful about this. You talk about path of least resistance, so maybe courage isn’t the right word, but the awakening at a certain point when you’re on that path, when you’re 12 years into a career as a litigator, or progressively successful career that, maybe on some level you knew that wouldn’t satisfy you until the end of days. There was a u-turn for you.

David: Yup.

Bill: Whether brave, courageous, may not be right – you’re not fighting ISIS, but at the same time that’s … Was there a shock to the system? How … I sort of asked it a couple different ways, but do you recall the moment where you’re like I want to do this, I want to zig instead of zag?

David: Yeah. To a certain extent, it was sort of an opportunity that I didn’t feel I had to do. I liked being a lawyer. I really liked my cases. Every case I had, I had to learn a new business. I was working, again, with, the constant in my career has been incredibly smart people. My partners were unbelievably talented and unbelievably smart. That is an incredibly invigorating environment to be in.

I had the support of my ex-wife at the time. I had the support of my kids, in going ahead and starting MarketSpan. It was really just sort of thinking it would be fun.

Also, going back to my partner, Mark Pankhurst. He was one of the greatest guys I’ve ever met. He’s my best friend today. Just the ability to be able to learn with somebody like that, seems like it would be fun.

Bill: It certainly has been. Baseball guy, right? You a baseball guy?

David: I have a bit of a baseball problem.

Bill: Do you? Where are your loyalties, if I may ask?

David: Now I’m going to get in trouble. I grew up as a Red Sox fan, and I still am.

Bill: From Westchester?

David: I lived 10 miles from Yankee Stadium, as a Red Sox fan.

Bill: I was going to say. That’s tough.

David: I could only afford bleacher seats when I would go to the games. Of course I would go to Yankee stadium for the games. Wearing my Red Sox cap in the bleachers of Yankee Stadium, was an early test of character.

Bill: It’s where you learned to box. Right?

David: I learned to run. The most humiliating experience I had was opening day of the 1979 season.

Bill: Bucky f’ing Dent.

David: You got it. I was sitting in the bleachers. The Red Sox were opening against the Yankees, in Yankee Stadium that season. This really beautiful woman about 3 rows ahead of me, turned around at one point and just showed me her t-shirt, which said, ‘And Yaz popped up.’ That was it. For people who don’t remember how that game ended, that play-off game ended with Jim Rice on third base, and Yaz at the plate. Yaz popped up to third, Greg Nettles squeezed the ball in foul territory and that was it.

Bill: That was it. You couldn’t ask her out after that. That’s a shaming.

David: Yeah.

Bill: The Sox are spending a lot of cash here, if they want to. They seem to have this horribly surprising last play situation, write some checks, and then they’re back the next year. I wish the Phil’s were. Optimistic for the men of summer?

David: I wish I could be more optimistic. I think that the Phillies still have a lot more to do.

Bill: Here they do, certainly.

David: I’m impressed with what Dombrowski has done, in terms of the Red Sox’s team. I’m not a big fan of spending that kind of money.

Bill: That’s true. The price is high. It’s not your money but still.

David: It’s 7 years. Even for somebody as great as David Price, who I think is fabulous, to spend that kind of money is … I’ll be singing a different tune, when they’re playing in October but as of right now, looking at it from the business side of it, you need a hell of a return in order to get that.

Bill: Great new first base coach, right?

David: Great new first base coach. Unbelievable.

Bill: Hey, it’s history. I want to get down and wear the uniform.

David: Although I’m a Sox fan, I have season tickets to the Phillies.

Bill: Good seats available.

David: Yeah. Now there’s really good seats available. It’s one of those wonderful things, where our seats have been too good to give them up. Which is why we continue to be, my syndicate continues to be season ticket holders.

Bill: Even while a losing baseball season, that is obviously a losing season, gets pretty boring after July, if there’s young players out there. Just the overall experience, particularly here in Philadelphia, with the stadium and the food. Summer without baseball, no matter how bad the team is, I can’t even imagine.

David: The first game of the season for anybody, whatever your individual first game is, just walking into the ballpark, and seeing the green expanse of the field is to me, a transformative moment every year.

Bill: Yeah. No, same here. Growing up as a Phillies fan with … I was 7 in 1980, which was great, and 10 in ’83, but then there was the meaningful kind of gap. Then in ’93, out of no where … Makes you think, if you walk in and everyone’s 0 and 0, you never know.

As we wrap, and this has been terrific, and thank you so much for your time and insight, and all the things you’ve learned, and how deeply you feel, all of this is palpable. Any other words of wisdom for those who’ve been inspired by your path, maybe that we haven’t hit on. Things that are either important to the curriculum here at DreamIt, or just important to you as a business person.

David: Yeah. I would hark it back to make other people’s lives better. Surround yourself with people who are smarter than you, who are better than you at what you do. It’s like that thing, inverse of that Saturday Night Live skit that use to be on the affirmations. ‘No, I’m good enough.’ ‘I’m smart enough.’

Or another take on that is Will Smith’s commentary about when he was on the Tavis Smiley Show. Which I do use many times when I talk with people about innovation and entrepreneurship.

Bill: Local guy as well.

David: Terrific local guy.

Bill: Doesn’t get back probably too much.

David: Here and there.

Bill: Got a part in the Sixers, right? Small part.

David: Yeah. I understand he owns somethings around Philly as well. He said there’s two things that will happen. He said, ‘You may be smarter than I am, you may be better looking than I am, you may be sexier than I am, but there are two things. If we get on a treadmill, you’re getting off first, or I’m going to die.’

Bill: Perfect. It’s true. Everyone has what one has, but you can control the amount that you work, and how much you care, how hard it is. David Bookspan, very inspirational. Grateful, for obviously all you’re doing for this region, and to nurture the entrepreneurial ecosystem, as well as what you share with our listeners today. Thank you so much.

David: My pleasure, Bill. Thank you.

Bill: Many thanks to David. What a passionate, interesting, obviously smart person, who is a great asset and resource for entrepreneurs in this region and beyond. His thoughts about the role of the brand, and the passion in business building as driving forces, as people figure out things about product and channels and everything else are tremendously valuable. Thanks to David for his time and insight, and for all the work he does to help nurture the entrepreneurial community in this region and well beyond.

Three ways, as always to support us at Real-World Branding. We’d love a review, if we earned it in the app store of your choice, we’d love it if you’d click subscribe, so you don’t miss a one of these. Every two weeks, we do an interview with a brand and business builder. On the intervening weeks, we do what we call, One Big Idea, which is more of a focus topic, shorter form. We really enjoy all the time we spent with various folks, and helping us think through some of the lessons of their careers, as well as, our ability to think through some of the things we’re seeing, as we’re serving clients, and helping them accelerate profitable growth, and activate the full potential of their brands.

The third way to help us is to keep the dialog going here. We would love to hear, and we’ve so enjoyed hearing from listeners, primarily via Twitter @BillGullan or @FinchBrands. Ideas for future guests, future topics, questions to ask those guests, as well as just general feedback. We’re not quite a year into this. Our skin is thick. We’re trying to provide as much value as we can, and we’re having a heck of a good time doing it, so we appreciate feedback of all types. We want this to be as valuable as it can be. Signing off. Huddling down for warmth, with snow on the way. All best from the Cradle of Liberty.

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When used correctly, technology can enrich brand experiences. In this week’s episode, Nicole Staple, Co-Founder of Brideside, shares her insight into the how optimizing the customer journey has helped her company provide a better experience for bridesmaids. If you like our podcast, please subscribe and leave us a rating!

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Nicole Staple: First of all, the millennial woman and the millennial consumer really values brand and she really values that emotional connection to the brand that she’s buying from. So we knew that was going to be very important.

Bill Gullan: Greetings one and all, this is Real-World Branding and I’m Bill Gullan, President of Finch Brands, a premier boutique branding agency. Today, a conversation with Nicole Staple. Nicole is a co-founder of Brideside, which is a fascinating, progressively multi-channel business that at least started by focusing on a better experience for bridesmaids’ dresses. If any of you have sisters, or spouses, or are yourself a woman who has been a bridesmaid, you will relate to the horror stories that one always hears about bridesmaids’ dresses. And so Nicole and her partner Sonali [Lamba] went out to change that.

What they’ve built is a very very, again to use the word, progressive, approach which includes certainly an e-commerce piece and they have that national scale through e-commerce. It does include a physical showroom, has a really innovative try-at-home program that e-tailers are using to kind of blur the lines and close the loop on the customer journey and she’ll tell you about it and do it much more justice than I ever could. Nicole Staple, founder of Brideside.

Bill: We’re joined by Nicole Staple, the founder of Brideside. Nicole, thank you for your time.

Nicole: No, thank you. It’s great to be here.

Bill: Is holiday a big time for you all? I would imagine that a lot of the events that people are purchasing from you for is a summertime type of thing, although not exclusively, but obviously many e-commerce and retailers, holiday is it. Is your business really seasonal like that?

Nicole: You know, it’s not. It shouldn’t be necessarily seasonal as people in our category aren’t buying for the holidays. With that being said, people are buying 4-6 months before their wedding, so it’s funny you should ask that as a first question because we’re doing this interview on December 1st. Actually, November was our biggest month ever in the history of the company. Largely actually driven by Black Friday and Cyber Monday.

Bill: That’s great.

Nicole: So we are coming off a really big month and are just really excited internally here.

Bill: Congrats. We will do a virtual hoisting of the glass or whatever in your honor. Why do we still call it Cyber Monday, by the way? Nobody calls it cyber space. We should probably rename Cyber Monday.

Nicole: I don’t know. It’s so silly. We are a big fan of Mondays. We do #MaidsMonday. So maybe we should just call it Super MaidsMonday or something.

Bill: Awesome. Not to get ahead of ourselves, your journey to where you are, the paths, the twists, the turns, I won’t steal it, but involved in finance and venture capital, going to grad school, could you take us sort of through the career journey up to this point and kind of how you landed here at Brideside?

Nicole: Sure. Absolutely. I went to Wellesley College outside of Boston, it’s an all-women’s college. Early on, I had pretty strong passion for, at the time, economics and business. I come from a family of entrepreneurs, so it was always something that was at the forefront of my mind. Particularly, going to Wellesley where there’s the messaging of women who constantly were taught to really break through glass ceilings and enter into non-traditional industries for women, which even just a few years ago, women in doing technology startups was even more unrepresented than it is now.

I always had that sort of fire in the belly, but I didn’t really know where to apply it. Like every good college graduate in the early 2000s, I went into investment banking and actually was in the healthcare industry. The funny story there and one moment that completely changed my career trajectory was when I was on my final round interviews in college for my investment banking job, I sat next to this man and he started chatting with me. He asked me ‘If you could do anything in the world, what would it be?’ I was like, ‘This is ironic, because I’m going to this interview for this job that I’m pretty sure is going to be terrible.’ It turns out that guy was Jeff Pulver, he was actually a pioneer in voice-over IP, and an incredibly well known investor and start-up guru.

That conversation ended up changing my complete trajectory. He’s still someone I keep in touch with and I knew that when I went into finance that I wouldn’t be there for very long, but I needed to figure out how to get to where I wanted to go. After doing investment banking for two years, I decided that I wasn’t quite ready to start a company because I had no operating experience and I really didn’t know anything about start-ups. Back then, in New York City, there wasn’t really the Silicon Alley that there is there today.

I got a job at a venture capital firm. The venture capital arm of Silicon Valley Bank, actually, SVB Capital and moved out to Palo Alto. That’s really where this entire path was born for me and Silicon Valley was incredibly inspirational. It allowed me to learn about the growth path of early stage tech start-ups. It allowed me to build a really strong network, and from there I went to business school knowing that someday I’d probably be in this position.

Although, at the time, I was much more focused on social enterprises. I helped launch a national non-profit chapter here in Chicago before business school, was pretty involved in the social enterprise space while at Kellogg, but always kept my ear to the ground in technology and Brideside was born out of my time at Kellogg, which is another story as well.

Bill: To that end, someone with a really strong finance background who was an economics person, at least undergrad, Kellogg has such a strong reputation across disciplines, but we hear of it a lot in the marketing and consumer packaged goods realm. I know that you’re concentration was innovation and entrepreneurship. Was there some grand plan at work in terms of why Kellogg made sense for you versus anywhere else? Was it that you liked the campus or other people you met?

Nicole: I did have a boyfriend who lived in Chicago at the time.

Bill: Ah.

Nicole: Although, I don’t like saying that. I had a little bit more of a focus on the Chicago area, but I was actually deciding between Chicago Booth University of Chicago and Kellogg at the time. The reason I chose Kellogg in many ways is one of the reasons that I think Brideside has been so successful. Some of what you mentioned, Kellogg does have a reputation in marketing and CPG, but it’s actually broader than that in that they’re really, really good at teaching students to think about their customer first.

For us, that was the way we were. That was the lens with which we were taught everything that we learned. That’s really, really important. I chose Kellogg. The culture seemed great. I actually liked that it wasn’t known for ‘finance’ because I wanted something different. If I were choosing Kellogg today, it would even be completely different. They’ve completely overhauled their curriculum towards more of an innovation and entrepreneurship focus. I told my husband last night ‘I think I would have saved a year of my life had I gone to Kellogg now and launched a company,’ because it’s amazing. I think every business school is starting to teach much more practical courses around how to start and scale a start-up.

Bill: Yeah, it’s amazing. I think what we can take from your journey, among other things, is that you’re smart. Which brings us to Brideside, and anyone who’s ever either been a bridesmaid or has friends or siblings who have been bridesmaids, spouses, has certainly heard the ballad of the bridesmaid when it comes to dresses and everyone’s got to wear teal, and you never get to wear it again, and you have to pay for it, and you’re an afterthought, and you can’t choose. Tell us about the founding thesis for Brideside and how all this came to you and you knew that this was what you wanted to build.

Nicole: To your point, Brideside was definitely born out of personal experience. Actually, my co-founder Sonali was planning her wedding while applying to business school, and she had 14 bridesmaids in her wedding. She was relatively young when she got married and she experienced the emotional turmoil that goes with coordinating women of different body types, personalities, and all of that. She came in to Kellogg thinking about the wedding industry.

She often tells the story that she showed her wedding planner Google Docs and her wedding planner had never seen such a thing. Her mind was blown, and she was actually one of the most well-known wedding planners in the Orlando area. Sonali was like ‘You know what? There’s something here.’

Bill: Yeah, there’s an opportunity we have to progress how this category works, right?

Nicole: Exactly. When I joined, I really didn’t want anything to do with the wedding industry. I was like, ‘You know, I know a little bit about start-ups from the investing side, so I can maybe help, but I’m not sure I’m really going to be involved.’ Once I started building up the financial model and we started truly working on it together, a lot of things came to light for me which convinced me that this was the right business to jump into.

Bridesmaids, there’s a very clear pain point, right? There are women that live all over the country. They have to coordinate all of these purchases. There’s a very clear pain point there and they spend a lot of money. We felt it emotionally, and we wanted to solve that problem that we are feeling. Bigger than that, bridesmaids really, there’s a Trojan horse for the entire bridal retail industry, which is a 14 billion dollar industry. Bridesmaids’ dresses make up just under 2 billion of that, so its really just part of that bigger story.

For us, at the time, 98% of retail transactions were happening offline in this industry. It was incredibly antiquated. It hadn’t evolved with the way that women like us were shopping, and there were some business components of this industry that made it really interesting to us. The first was that there are incredible network effects among these groups of women.

We had historically heard that customer acquisition costs in the bridal industry is incredibly high. It’s really hard to get a bride’s eyeballs online. It’s a very long purchase cycle, it’s a one time purchase. It’s just really tough. Everyone told us ‘Don’t do it’. We said, ‘Okay, if we can get these women to love us, there are 8 of them that buy at one time. So while we might spend a lot to get the bride, we’re getting 8 purchases out of it, and all those women are either going to get married themselves or be in other weddings.’ Then you start to have this sort of viral coefficient and word of mouth that starts to spread, and actually makes a unit economics of a bridal party quite attractive.

The other part of it is what’s super cool about this industry, for people that know retail, is that bridesmaids’ dresses, in many ways, is still a cut to order industry. We only carry inventory for our home try on program, which makes the working capital of starting the business in this space really interesting, because then you really can focus working capital on customer experience, technology, and marketing, and not so much on the inventory and overhead risk of that side of the business. We still operate that way. We don’t place the final order with the manufacturer until the entire bridal party has ordered, which is pretty cool.

Bill: You obviously have a strong grasp, not surprisingly, of both the emotional side of this and the economic fundamentals that drive the category and in particular, these types of purchases. Back to that sort of softer side, being true to the name of our podcast, could you take us back to when you all were starting out? You had the idea, you gamed it out financially, and the time came to think through the name, the identity, and the brand personality. How was the thinking and how did it evolve on that?

Nicole: We knew that we needed a really fresh approach, from a brand perspective, to this market. Some of what I mentioned to you before, what comes to mind when you think of wedding boutiques, for example? At least what came to our mind was appointment only, expensive, rude salespeople. When you looked, at the time, at what was offered online really was nothing. It was these discount retail sites, websites that looked like they were built in the early 90s. It was a complete mess.

Back to what Kellogg taught us, which was really customer first and brand first, the first thing we did was tons of focus groups and tons of data collection on our customer. What we realized is that, first of all, the millennial woman and the millennial consumer really values brand and she really values that emotional connection to the brand that she is buying from. So we knew that was going to be very important. What we also learned early on was that it was really stress, emotional stress, which was driving the dissatisfaction in this industry. We knew that every part of our experience, from the user experience online, to the way that we communicated to the customer, to the products that we offered, and to the pricing needed to focus on removing that stress and drama from the purchase process. What we say now, and that way that this identity has evolved, is that we’re here to provide peace of mind to wedding parties.

We say internally that we want to be the exhale that every wedding party feels when they walk down the aisle. When you come to Brideside, you want to feel at ease. You want to feel taken care of, you want to enjoy the journey and this moment because it’s an incredibly emotional time. It’s important to the bride, it’s important to her friends, so she shouldn’t have to think about the coordination aspects, and that’s what we want to remove from her plate so that she can really enjoy the emotional experience of getting married.

Bill: The name, as one artifact of that brand development process, is a great example of ‘nailing it’. It rhymes; it has sort of a great acoustic rhythm to the way that it sounds. It speaks to, as you say, being on the bride’s side – if you’re a bridesmaid, being by the bride’s side. It really kind of checks all the boxes, and obviously you’re able to own it and use it in the digital sphere. Was that name sort of a thunderbolt or was it a painful laborious brainstorming process? How did you settle there?

Nicole: It was a little bit painful, I’m not going to lie. Actually, if I’m going to be totally honest with you, the name was originally Bella B. That was our project name, our working name when we were at Kellogg. We were sitting around a kitchen table drinking wine one night, brainstorming all of these names, and Sonali’s husband, from the kitchen, who was cooking dinner – actually, I think he was playing video games. Not even thinking about anything, he screamed over ‘What about Brideside?’

Bill: That’s perfect, that’s the right way to do it. You play some Grand Theft Auto and you figure out the name, that’s super cool. There’s so many stories of coming to great things that way, whether it’s names or other things. That’s really funny. She was married when this happened, were you also? If I may pry.

Nicole: No, no. I was not married. I got married just about a year ago. I met my husband at Kellogg. I had only been through this experience as a bridesmaid before, and she actually only been through it as a bride. She hadn’t yet been a bridesmaid. It was interesting experiences and point of views that were coming together.

Bill: Yeah, perfect, and having 14 bridesmaids, she’s either too popular or doesn’t want to make tough choices, but either way.

Nicole: I’ll leave that to her to comment on.

Bill: Fair enough. You mentioned a few, in the try it home program, obviously Warby Parker and other kind of retail pioneers are driving this and really connecting a bridge between traditional pure e-commerce and all the other things that are important in an experience like this. You have the try at home piece, you do, I believe, have several showrooms in the Chicago area, obviously, you have the e-commerce storefront. Given the channels involved here, the touchpoints in your business model, how do you think about the customer journey as you choreograph what it feels like for her, to deliver all the things that we know are important to the brand?

Nicole: This is an incredibly good question. I’m glad you’re asking it. It was very insightful for you to ask this question because, in fact, the customer journey, in my opinion, is our biggest competitive differentiation, and in many ways is where we’ve positioned in this market by having the best understanding of the customer journey.

Our product really is the way that we manage the customer journey, almost more so than what we sell, it’s how we sell it. We often call it our bookend. The bookend being how you reach your customer and how you sell to the customer, and the book in the middle being what you sell. Which is sometimes to us, it’s less hard than figuring out the customer journey. Around the customer experience and understanding, from start to finish, it’s an incredibly long sale cycle. It required us to have and to manage a bunch of different touchpoints, and what was important to us is that every part of the company aligned around the customer journey we were trying to build. That’s our front-end technology, that’s our internal business processes, that’s even our organizational structure.

The way that we think about it through our sales funnel is a combination of online, offline, and human touch. We have a team of internal style consultants. It is one of the pieces of the business we’re most proud of. Every bridal party that signs up on the site, regardless of where they live, is assigned a style consultant. That style consultant can manage up to 300 or 400 active bridal parties at any given time.

Our communication tools, our internal technology, and funnel management systems allow them to easily understand and have the right data to personalize their messaging, to make sure they’re touching people at the right point during that process. Then the offline piece, our headquarters is in the West Loop of Chicago, and here we have one big showroom with multiple fitting rooms. That experience is incredibly complementary to the online piece, because if the bride lives in Chicago, or maybe she’s here for a weekend to visit her sister, she can come in, meet her style consultant face to face, and then use her online account and her bridesmaids that live in other places can use our home try on program to still go through that same concierge process and have the same style consultant that the bride met that first day in the showroom. Everything is actually very complementary and provides this really smooth experience for the customer.

Bill: Yeah, that’s super smart. Obviously this is a business with the digital piece of this that scales geographically, you mentioned the fact that everyone’s all over the place, all over the country and all over the world. What is the incidence of the actual live showroom participation within the customer base? Is it a big chunk of it?

Nicole: About 20% of our customers touch the showroom.

Bill: That’s a lot. That’s great.

Nicole: Yeah. In the stage where we are now, where we just have really this one offline showroom, that’s about where we want it. We’ll see as we think about geographic expansion. Chicago’s actually the biggest wedding market in the country, and it’s really this hub for the Midwest. They often say if you win the Midwest, you win the rest.

Bill: Right. If it plays in Peoria, right, perfectly. One of the things that may be part, and don’t tell me things that are private or that you don’t want to tell me, just slap my wrist through the phone. That full sort of authentic Brideside experience, by the way the showroom obviously isn’t required to have a great experience but does seem to enhance it, possible geographic expansion around, bricks and mortar isn’t exactly the right term, but I mean, is it an important part of the expansion strategy to think about more showrooms in more places?

Nicole: Absolutely. Yeah. Weddings are actually not as seasonal as you would think. Nationally. They are seasonally by geography. When you think about how to balance out that seasonality throughout the year to build a really big consistent and stable business throughout the year, and not just in certain months of the year, that’s where you think about geo-targeting.

Bill: Makes sense. That is maybe one piece of it, and again, feel free to keep secrets secret, of course. When you think about the growth path from here, some of the major hurdles, the significant opportunities that the size of this category, the foothold that you’re gaining within it, major topics that are on your plate and that of the team? Obviously, there’s continual demand generation and awareness and conversion, all of the normal mechanics of this, but what are the kind of top of the table types of topics that you’re dealing with at this point?

Nicole: This year, recently, the second half of this year, we’ve almost quadrupled the size of our style consultant team, or our sales team. That has been managing that growth and keeping our culture and everything that, moving to a new space, everything that goes with increasing headcount so rapidly has been a big focus as we started to near the end of 2015 and we’re on-track to triple revenue this year over last year.

So it’s been really successful. When we look into 2016, now that we really have this model down, there are a bunch of cool things in the pipes. One that is very public now is the launch of our new exclusive collection with an incredibly hot bridal gown designer out of New York City called Kelly Faetanini. So we launched the Altar Ego Collection, A-L-T-A-R Collection with Kelly. It’s actually a new concept in bridesmaids’ dresses. It’s a series of short dresses and long skirts that can be worn together or separately for lots of different types of looks, so it plays into that idea of mix and match, it plays into re-wearability and it’s something that’s exclusive to Brideside. Not only the actual dresses, but also the concept was really differentiated and really cool and different to the industry.

When we think about how do we stay ahead of the market, I think all the proprietary technology we’re building both on mobile and desktop and in our showroom is important, but also exclusive product and collaborations is incredibly important as well. That’s heading to the New Year, we’re also thinking about new product categories. We recently launched men’s accessories; socks, bow ties, pocket squares to help with color matching and the stylist then has more tools in her toolbox to help up sell that bridal party on different things that help them complete the look. We also just launched flower girl dresses, so we’re thinking about now how can we really leverage that personal concierge experience that we’re providing to sell more items to the bride and help make her life ultimately easier.

Bill: Yeah, and part of that is making sure that when her bridesmaids look as great as they do that the groomsmen are not a bunch of schlubs here-

Nicole: Exactly.

Bill: You got to measure up. We got to get the cuff links done, we got to get everything done.

Nicole: Totally, totally.

Bill: Historically, one of the reasons why this is so interesting, in addition to it being just super smart given anecdotal experience hearing from angry, disaffected bridesmaids over and over, is that, as you say, the traditional bridal channel, where they’re selling the dress to the bride, is antiquated but seemingly the primary way since forever and ever. There are economic reasons for that, but do you think that this ultimately gets to the gown, or are we really focused on the concierge sort of constellation of services around that central gown piece? If you don’t want to answer, feel free not to.

Nicole: It’s a great question, and it’s hard to know. For a bride that’s a bit more casual, we actually sell her some of our more formal dresses now as the gown. The gown is definitely much harder, and there are several real players that have entered that space in the consignment space, which I think is very cool, and are helping brides lower the cost that way. To be honest, it’s probably pretty far out. I think there are other things that make more sense for us, but you never know.

Bill: For the traditional gown experience, obviously the more showrooms you have the greater the potential to deliver, glass of champagne, hopefully not the snooty women working there but the positives of that experience.

Nicole: Absolutely.

Bill: Super interesting concept and the growth that you’re experiencing and obviously the way you all think about this is very progressive, and it’s a breath of fresh air for a category that seems to have desperately needed it.

Nicole: Yeah.

Bill: When you look back at both the art and science of building this company, and all the other things that you’ve achieved, I’m sure that many of our listeners, in addition to furiously Googling or entering Brideside into their mobile browsers, are also saying ‘Wow, this woman is awesome and very inspirational.’ From your career path, for those who have been inspired by it, a couple of words of wisdom or sort of rules that you followed as you’ve built this incredible career?

Nicole: I think one of the biggest learnings for me is that this is really a marathon and not a sprint. We went through a tech incubator. You probably know this, Dreamit Ventures in the Fall of 2012 and I’ve been in your offices before, obviously. At that time, thinking back to those days when you see all the momentum that builds around articles in TechCrunch and massive fundraising rounds, it is incredibly easy to get caught up in that and have the expectation that your business is going to go from 0 to hero in less than 12 months.

My attitude is that’s actually how really strong, long-lasting businesses are built. It takes a lot of testing and a lot of fundamentals to lay the infrastructure for the business you really want to build. The first thing, and I think this is a very Chicago attitude as well, is just really keep your head down. The longer that you are plugging away at your business and tweaking things and fixing things and testing things, and just keep going at it and figuring out the right solution and hanging in there, the better you’re getting at honing your own business model. The more competitive you’re inherently making your own business by becoming an expert at the field that you’re in.

That’s really important for us, is just staying really heads down and just staying focused on the fundamentals. With that, I think it’s important to set the right milestones for your business. What are the right metrics that are going to determine your success? We got some great advice very early on from a well known venture capitalist who said, ‘Strip away everything that money can buy and find the thing in your business that you can do right that doesn’t need a lot of money to do. That’s your secret sauce.’

We focused on that a lot, in a lot of our key performance indicators and a lot of the internal milestones that we set for ourselves are really focused on that. We challenge ourselves to not always just think about top line, for example. Many times, top line is the most important thing, but there are underlying levers in our business that might be more important. How can we set appropriate milestones for ourselves that we know in every given point in time if something is working or if it’s not? For someone that’s just starting a business, it’s important to know if you should keep working on the business or if you should not.

We’re not naïve about that. We’ve always, even times that we’ve had harder months or harder stretches of time where we said, ‘We don’t know if this is working’, we’ve said, ‘is this really not working? Are there things that we can find in the business that are working?’ By sticking with it and figuring out our own model and what makes us special, we’ve now seen a tremendous growth and tremendous success this year, I think, in many ways and I’m really glad that we stuck with it.

Bill: Yeah, that’s great. Do you and Sonali have a clearly defined division of labor? You were co-founders, you were friends, you were obviously business school colleagues that had a great respect for one another and warmth to the friendship, but how easy or how clear are those lines functionally within the company?

Nicole: They’re very clear, and one reason that I decided to jump on board with this company and to launch it with Sonali is because she was so tremendous and because we both had such clear strengths that were complementary and not competitive. Sonali operates, the lines are very split in that she operates essentially as COO and manages everything that services revenue. Everything from customer care to sales operation, she manages our whole technology team. She manages merchandising, all of that piece. I’m really head of growth, so I oversee sales goals in the sales team. I manage all of our marketing and fundraising and business development. That’s really actually how it’s been from the very beginning, so it worked out really well.

Bill: That’s great. You mentioned some of the growth that you’ve experienced on the stylist side as well as obviously throughout the company. When you look at, and again it obviously depends on the function, but when you are bringing new members of the team in, what are some of the characteristics that you’re looking for? What do you think can be taught versus what someone needs to walk in the door with to be a productive member and a happy member of the Brideside team?

Nicole: That’s the name of the game for us. Particularly given that we do have a sales force that’s a different sort of structure from a lot of tech businesses maybe. This is the coolest thing for me, personally. It’s been a challenge for me, and one that I really welcome, and has been super cool to learn about.

First and foremost, what a lot of people say is cultural fit is first. That’s the do you get to keep talking to us type thing. With us, what cultural fit means is incredibly down to earth, a little quirky, tends to be just very sort of flexible person. We need to see that you’re going to be okay with uncertainty. We try to get the best and the smartest talent we have, and often that means recruiting people from really top tier, brand name companies and asking them to take a 50% or more pay cut, right?

A lot of it is telling the right story to them to get them on board, and then making sure that they’re truly okay, that they have the gut for it. From there, particularly when it comes to our style consultant team, there are very different types of personalities that make a great saleswoman. Particularly here where they’re working with customers offline in a more traditional retail styling and online, where it requires them to be incredibly tech-savvy and understand how to analyze data. We’re really looking for unicorn-type people. We walk them through a series of case studies. We do a lot of mock appointments. We’re testing a lot of different right-left brain characteristics just to see do they have that perfect mix?

So far, we’ve had a pretty amazing retention rate. The team, I think, is tighter than ever. We often say one of our values internally for the style consultant team, we want to be a team of cool girls who sell you what they wear and tell you what no one else told them. We look for people that are honest, smart, witty, and can sort of play off that broader brand that we talked about earlier.

Bill: That’s great. We’ve overstayed our welcome in addition to me fiddling with the audio for what seemed like forever before we started, so thank you so much, particularly at this exciting moment, best month ever just completed, the excitement of the holiday season ahead. Really grateful for your insight and your time, I’m sure that coming out of this conversation our listeners will be incredibly excited to see where this career and this company goes, and really grateful for you sharing what you did.

Nicole: My pleasure. Thanks so much.

Bill: Nicole Staple, co-founder of Brideside, a fascinating business concept that just looking at her career and the way that she’s thought about obviously the practical elements of the business model, the financial model, the structure as well as the sort of emotional side of this, the why -the problem that needs to get solved, the thing that needs to be improved or done differently. Brideside is it in that category and it’s going to be a really, really fascinating story to watch unfold. If any of our listeners are in the market, I can guarantee you that you’ll have a great experience with Brideside.

Three ways to help us at Real World Branding, sound like a broken record here, but we’d love it if you’d give us a rating if we deserved it, I’ll mix up the order this week so we stay fresh. 4 or 5 stars if we do deserve it, and our skin is thick, so we certainly want to hear feedback. The best way to do that is on Twitter: @BillGullan or @FinchBrands. Ideas for future guests, ideas for future topics, questions to ask different guests, let’s keep the dialogue going. As noted, we are doing this in a humble way, learning every time. Both on the production side as well as certainly on the hosting side, so we’d love to hear feedback. Things that we’re doing well, things that we could do better to make this ever more valuable. Then, the third way to help us is to make sure you do not miss an episode by subscribing in the App store of your choice. Every other week we have an interview with a business and brand builder. In the off weeks, we have what’s called One Big Idea, where I focus on a particular topic and talk about it for 8, 9, 10 minutes based on our experience here at Finch, and what we’re seeing in the marketplace. That is about it. It’s hideous outside. Winter is coming. However, a great week to all of you, and in that spirit, we’ll sign off from the Cradle of Liberty.

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There are many differences between emerging and defined brands. Scaling a business from a startup venture to a ‘grown-up’ organization not only requires a specific management style, but also special consideration of how the brand will grow with the company. In this episode, Brock Weatherup shares his insights into taking startups to grown-ups, developed over years of both founding and growing existing businesses including Pet360, Fathead, PetsSmart, and many others. If you like our podcast, please subscribe and leave us a rating!

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Brock Weatherup: At the end of the day it’s, ‘What are you? Why are you existing? What is the dynamic? How do you want to operate? What do you want to be foundational?’ Those all then build up what your brand is. If a CEO, or an entrepreneur, or frankly anyone individually doesn’t think about brand all the time, but in the broader sense of brand, then they’ll never get there because it has to be genuine.

Bill Gullan: Greetings one and all. This is Real-World Branding. I’m Bill Gullan, President of Finch Brands, a premiere boutique branding agency. This week, an interview with Brock Weatherup – Brock is an executive, he’s an entrepreneur, he’s an investor, and he’s a mentor. His career, which he’ll tell you about in just a minute, is a set of examples of how passion and hard work drive success – both for existing organizations that are larger, as well as entrepreneurial ventures. Brock says, and he’ll tell you in a minute, that he sees himself as the bridge between startup and grown-up companies. His career path is perfectly exemplary of that.

Most recently, Brock built the Pet360 brand, which originally began with petfooddirect.com and petmd.com, which were e-commerce sites focused on the pet parent community. He built, at the risk of being cliché with the phrase, a lifestyle brand called Pet360, which was recently after six years of growth acquired by PetSmart. Through that acquisition Brock served as Chief Digital Officer and Senior Vice President at PetSmart before rolling off the business. Tremendous experiences early on with FatHead and American Express and beyond. He’ll tell you about it right now – Brock Weatherup on Real-World Branding.

Bill: We’re here with Brock. Thank you, Sir for your time.

Brock: Awesome to be here.

Bill: Incredibly interesting career with organizations that we’ve all heard of, many we haven’t. This combination of big company, entrepreneurial venture, could you take us through this journey? To a degree that you’re comfortable.

Brock: Yeah, sure. I’ll do it in a pretty quick tone, but I’ve kind of been in the space of selling a product or a service to consumers, leveraging technology and the Internet since that existed, since the early 90s. Starting in the early days with American Express, and helping create new business, helping special deals with AOL to send CD’s, for those of you who know what CD’s were, to get preferential access.

Bill: I got a few of those in the mail, and I felt really good about myself back then.

Brock: I sent a lot of them. Amazing experience, kind of my MBA so to speak because I didn’t do that. I left and ended up, in the early to late 90s, joining what was a company called Ticketmaster Online-Citysearch, somewhat self-descriptive, but it’s ticketmaster.com, citysearch.com, and match.com. All the same base model of traditionally offline businesses moving online at the time, I jumped into that.

I had a great run with what became now an organization called InterActive Corp, Barry Diller consisting of things with little names like Expedia and Home Shopping Network, and College Humor.

A couple things here and there – I jumped into the outdoor recreation world, a company called Reserve America. Think of Ticketmaster for the outdoors, hunting and fishing licenses, back country permits, camp ground reservations, that whole –

Bill: Talk about the promise of the internet to aggregate and organize something.

Brock: Exactly. Then I joined an organization called Entertainment Publications in Michigan, which was another IAC company, and stayed there for a little bit. Groupon before Twitter, Facebook, and iPhones. Made a nice business out of it, but then left that and started at a company called Fathead – wall graphics, sports and entertainment passion based business, which I loved.

That was quite a trip. We can talk about that a little bit more. Then I left that, and jumped into the pet world. What was PetFoodDirect, and that was about six or seven years ago, up until selling that to PetSmart about a year and a half ago. That was quite a run.

Bill: Where are you from originally?

Brock: All over the place. I’ll say Connecticut. I lived overseas as a kid, lots of other places.

Bill: Undergrad at Boulder, yeah?

Brock: Boulder, Colorado. You bet.

Bill: Poor thing.

Brock: My professional career, it led me from New York City back to Colorado to Pasadena, California to Toronto, Canada to Detroit, Michigan and now good ole Philadelphia, PA.

Bill: Yeah. The Cradle of Liberty. The ‘City of Champions’.

Brock: You bet.

Bill: Actually not, not so much.

Brock: Not so many champions, but –

Bill: Yeah. We have our moments. One of the things again that jumps out to me, and obviously as you say this was … Even for larger organizations that right now we look at as maybe not being old economy, but being somewhere in between old and new, big organizations, entrepreneurial ventures … What have you seen in terms of the differences? Even if you were with larger organizations it sounds like it was an entrepreneurial type of assignment, but when you think about your level of comfort, the things that fire you up, big company experiences smaller types of things, what are the common denominators that get you wired for something?

Brock: One of the interesting thing that happens is it’s the same issues. It’s the same strategies. It’s the same reasons why things do or don’t work. It’s just, relatively speaking, scale.

Bill: Right.

Brock: That’s where things can fall apart. A lot of times … I’ll never forget I had this discussion with our team at FatHead. We were small, there were ten of us at the time, and we launched this FatHeads Tradables line, and we literally took it from hair-brained idea to actually presenting it to the NFL with actual product, website, webkins-ish type scenario in almost four weeks, which was amazing … Working prototypes, everything else, and we said, ‘Okay. This should be the longest it should ever take us to get something done.’ The reality is [however] as you grow, that almost is harder, and harder, and harder, and harder.

The big difference between the two is how do you maintain decision-making at the point where the decision needs to make, which are not at the top. The strategy and general direction should be organized and communicated in some broad fashion at the top, but the decision-making still happens. That’s what gets to me, the loss. Successful large organizations don’t lose that, and ones that aren’t so successful, they become dictatorships, or in a very different scenario.

Bill: That’s interesting. I would imagine that some of the smaller organizations that struggle lack the upstream structure strategy, and organization that drives the downstream decisions.

Brock: Yeah. I took a spot on where I think my career has found itself, is what I call the stage between startup and grown-up. There are a lot of people who can start things. Frankly, it’s a very trendy thing right now to be an entrepreneur and be a startup guy. People think it’s really easy. It’s really, really, really hard.

Anyone can start something. To get something to any level of scale is where it gets hard, and then there are fabulous people that know how to run things at scale. That may not work. It’s mostly finding where your place is in that spectrum. I think it’s both a self-directed element of what you need to know about yourself, but also where do you fit into that scenario.

Those challenges that are small can translate as you get larger, but they need to work together, and you need to find a way to achieve that, and leverage it, and scale it. That’s where, frankly it gets hard. I like that middle ground, frankly.

Bill: Is that what has attracted you to the investor realm, and the advisor realm –the mentorship that you’re doing with entrepreneurs, the role that you’re playing with folks that maybe trying to make that leap?

Brock: Yeah, after exiting PetSmart, and going through that process I started to think, ‘What do you want to do next?’ It was a very odd career step. A very lucky, and a very unusual, but highbrow issue of what do I do next. I kind of looked at the market, and said, Gosh. I’ve learned all of this. I’ve created all of these things. I’ve had the luck to have amazing teams. Had huge problems, and overcome them; huge problems, and not overcome them. Some wins, a lot of losses, and things along the way.

Could I translate that, and help other people to not make the same mistakes that I made, or our team made, and if I could help people get further quicker, then that might be great. If I could combine that with some investment, then that sounds really interesting. I’ve kind of focused on finding entrepreneurial or startup organizations where I can put both capital as well as time and hopefully try and bring those two things in a more leverageable way.

Bill: It makes sense. One of the interesting things also, again either coincidentally or not that has marked some of the career steps that you’ve walked us through, is there’s often a very enthusiastic consumer base. Certainly, FatHead in the early days and still, sports enthusiasts, man caves, children’s bedrooms, etc. Obviously, the IAC brands are, niches may not be the right word, but they’re vertical plays. What led you to the pet category? What is it like to build a brand [in that vertical]? Pet parents, as we may call them, astonishing in their passion, not surprising as many of us feel it in our own lives. What led you there? Anything you can tell us about what it takes to succeed when you’re being watched and scrutinized in the way that pet parents watch the brands that they trust?

Brock: Yeah. I think for me, I want to wake up really excited about what I do everyday. I’ve been lucky enough to make career choices around subject matters that I love. I’m a huge outdoors person. I love sports and entertainment, and I love pets. The consistency around all of them is they are people who are very excited and very passionate about what it is. At the core, I love figuring out human dynamics. Why do we as individuals make choices to buy, or not buy, or do, or not do? Digitally you can test, try, and figure it out all the time.

Bringing that to the pet category was a natural next step of something really interesting where you had a core consumer base where pets are not a pet, they are part of the family. The way to get excited about people is to help them become better pet parents, help them become more enjoyable in their interaction with their pet, have their pet be a better pet to other people. At the end of the day, I think pets bring incredible joy to lives. My sister, by total circumstance, happens to be a veterinarian. She’s a small animal surgeon in Arizona. I’ve always been around it, but I’ve always had a dog. It’s always been a part of my life, and I think they bring great joy because they bring unconditional love to the world. If you can leverage that, and make a business around it, that’s what I got really excited about.

That passion can take many forms. Most of that in the general middle is a great thing. People are passionate. People are excited about it. Like any, you can have the extremes of that. How those things transpire are often quite fascinating, the crazy cat lady totally exists.

Bill: She does, there’s a lot of her.

Brock: I love her as a customer, and she is amazing, but you get a lot of critical stuff. You find different elements along the line where someone’s like, ‘Why don’t you have x? Why don’t you have y? This should be right. You’re not strong enough about this, or strong about that.’ Which is wonderful because that’s hopefully what you can facilitate, and help people find their piece of that equation.

Bill: As you started out, what became Pet360, there was petfooddirect.com, there was PetMD shortly after. These were e-commerce businesses that had content around pet parenthood, and pet health, and other things wrapped around the transactional core of these sites. By the time Pet360 as a whole was acquired, it had made the transition to full lifestyle brand, if you will, for the pet community. It had added BlogPaws, it had added a variety of different things beyond just the core transactional mechanic. Over the course of that five or six years starting with, ‘We have to drive traffic, and we have to convert it,’ to being a place where that was taking place, but it was surrounded by the rich, deep, and textured series of content sources around pets, can you speak through that transition across the life of Pet360 from selling food and meds online, all the way up to something that was sort of 3D.

Brock: The story started with a pretty broken PetFoodDirect. That was a pure e-commerce play, totally undifferentiated in the market minus the fact that they carried a lot of brands that weren’t as accessible in the marketplace. We needed to figure out whether there was a model there. That’s where we got into subscriptions, starting figuring out what that was, and had the concept of, ‘Boy, if we could add some content to this this would be fabulous.’ We had some great guys down in Florida who had built PetMD, which was a small site at the time, started to bring that content together. I’m like ‘We’re on this content-commerce idea, it’s really going to be great.’ Totally bombed. We couldn’t get the customer from PetFoodDirect to care about content – a tiny bit, but nothing meaningful. We could get none of the people on PetMD to move over and buy.

This should make a whole lot of sense. Obviously, you do a little bit of research, then after that realize it seemed like a really smart idea, but the beauty of digital is you could test that. I was dead wrong. Our team, we were dead wrong because when somebody’s reading an article about hip dysplasia, or the more likely, ‘My dog ate, fill in the blank, and they’re now throwing up on the floor.’ Your idea of going online and learning what you should be worried about or not isn’t going to take you to buying something, that just didn’t work.

We looked at the market, and said, ‘How do we do this?’ We had this nice e-commerce business, and this nice media business. Both were doing really well independently, but the parts were not adding up to anything more. We looked at it, and said, ‘What can we bring together? How could we compete against Amazon? How could we compete against Walmart, Target, PetSmart, and Petco?’ All of those elements, and at the end of the day we needed something unique, and said, ‘Okay. Let’s take these platforms of e-commerce and platforms of media, let’s really bring content and commerce together,’ but that wasn’t really enough. We said, ‘What could we do that might create something unique?’ We said, ‘Look, let’s bring a personalization aspect of it to the equation,’ which was at the time people talked about ‘pet owners’. The fact of the matter is, yes, I am a pet owner, but I’m actually a pet parent to a four year old retriever named Boulder, which is very different than a pet owner of a cat, or even another dog owner that owns a Chihuahua, or a puppy owner, or a senior dog.

All of those are very different pet profiles. When you think about the traditional four-walled store, that store has very little relevance to me except for a small part of it. We took that concept said, ‘Look, let’s really build Pet360.’ That’s when we went out, and raised some capital, and said, ‘Look, let’s bring this together. Let’s bring the convergence of content and commerce.’ Community seemed to make a whole lot of sense. How could I get golden retriever owners all together? How could I get Siamese cat owners all together? That’s where pet ownership gets really exciting, and people get really passionate about it because now I can have a conversation with you in a very different way. That becomes fun. That becomes knowledgeable. I become smarter about it. I enjoy my pet better. I treat my pet better. The health of my pet is better.

All of those things add up to a much more enjoyable experience for everyone. That was the foundation of Pet360. When we went out to build, we built it from scratch leveraging the knowledge and the platforms that we had. That’s what really took off. We really proved in that model that if you really are genuine about addressing people’s needs, and attaching to what their passions are, you could really transform what that might look like.

We had a clean brand, in essence, to work with at Pet360, obviously somewhat descriptive, pet and 360. It was clean. Nobody really knew, or had plus or minus feelings about what was or wasn’t Pet360. PetFoodDirect, super efficient, get in the store, get out. Couldn’t really transform that. PetMD, really great about answering your health and wellness questions, but couldn’t really get outside of that. Could we leverage those? Absolutely for what their benefits were, but they also have restrictions, and you have to know that around that brand.

We had this flat platform or blank slate with Pet360, and said, ‘Let’s really build this to where we are talking to individual pet owners. Creating dynamic elements.’ That’s what got me really excited. Got our investors really excited, and we had an awesome team to really pull it off.

Bill: To the point about team, I would imagine in a category like this, just as you found at FatHead and elsewhere, that often when you either enter or seek to build a company, you attract folks who are enthusiasts for the category. How do you balance when you talk about, between startup and grown-up, this notion of people, we’ll talk about pet parents, I’m sure that it’s really important that folks get it, and feel it deeply. At the same time you need to layer functional skills in terms of what you’re trying to get done within this organization. How did you think about building the team and mentoring folks? Was it easier to get digital marketing people to care about pets, or to get a pet lover to care about and understand SEO and paid search? How does this work? I’m sure it’s case by case, but –

Brock: Yeah. Actually, what makes it really nice about our category is that 60% of households have pets.

Bill: Sure.

Brock: First off, you’re talking about a very large part of the world that are pet enthusiasts, or have had pets. The ‘get it’ factor is pretty high straight out of the gate; versus if you’re into underwater basket weaving, that’s a pretty narrow group. When we got into that scenario is, ‘How do we get people to come in?’ Also, depending on job function, for example, we never hired anyone in our customer service team that didn’t have or own a pet because you just couldn’t have a conversation. You would become disingenuous immediately. You’d be immediately disregarded for your knowledge because you would speak a different language. That’s not okay.

Bill: We care about what was happening to Fuzzy.

Brock: Yeah. We try in customer service to get dog owners to our dog agents and cat owners to our cat agents because there’s a different language. There are cat owners, there are dog owners, there are small dog owners. All of those have different sorts of dynamics. That’s an easier example of what it is, but when you get into core function of, ‘Okay, somebody who really knows how to do CRM, somebody who really knows how to code. How important is it or not?’ We always look for the balance. We always needed that pet element, that pet passion, but they also had to know they’d walk into our office, there were pets walking around. If they walk in, and go, ‘Eh I’m not sure about this.’

Bill: Start sneezing uncontrollably, that’s going to be hard.

Brock: They fairly well self-selected out. It wasn’t that hard, but you also had to match. When you were designing the digital product, or your doing merchandising, you needed people who really knew what they were talking about, but when you move to some more periphery function, you had to have enough surrounding it in terms of why or what, or how it needed to come together.

Again, we were able to … It was actually a way to intertwine differentiated talent in many ways because people who are really passionate about their animals say, ‘I want to do something about that.’ When people are passionate about the subject, even if their core skill isn’t at the level of what somebody else might be, that passion and energy can make up for it a lot of times. If you had two equal candidates, and one was, quote unquote, on paper, skill wise a little less, but was incredibly passionate about the pet category, I’d probably go that way because I want that energy. I want somebody who knows, and they’ll make a little tweak here, they’ll make a little tweak there, and all of a sudden it makes a huge difference because they know what their dealing with.

Bill: Right. I would imagine they connect with vision, mission, values intuitively and that helps.

Brock: You bet.

Bill: To that end, just to take it one level up, you talked about it as an ingredient in your own career path, and certainly as you built teams. What is the role of passion in one’s business life? Not to get too self-helpy here, but you’re thinking about what you want to do next, and I think there’s a lot of folks who look at the entries on your resume, and see them as one passion play after another, but obviously with a strong subtext as you’ve described. When you think about passion, and when you think about skill, what’s the role of passion and belief and depth of feeling about either particular industries or particular topics that then become monetizable as business ideas?

Brock: I’ve been lucky enough in my career, and my career choices, and the people that have been around me – family, friends, my amazing wife – to be able to go after things that I believe in and things that I would define as, ‘I’m interested in. I’m excited about,’ and I’ve tried to trust in the fact that if I’m really excited about it, that I’ll find a way to be successful at it. Successful doesn’t necessarily mean economically, it means, ‘Am I finding joy? Am I finding excitement?’ I’ve been lucky enough to also have some financial success with it, but that was an outcome, not the goal. I think that gets lost a lot of times for people.

It’s easy to say when I had a very privileged upbringing, I had every opportunity given to me, I’ve been lucky enough to be very successful in different manners. I know that’s not true of everyone, but I do think people make choices a lot of times where they don’t work to change their situation. There may be some limits on what they can and can’t do at that moment or at that time, but people should wake up excited about what their diving into. Doesn’t mean I woke up excited everyday. There are days where you’re like, ‘Uh, I’ve got to deal with this,’ or, ‘This isn’t going to be great. I don’t want to go there,’ but you’ve got to love what it is. When you can match people, when they love what the subject is, and they’re competent in the role that you’ve put them in, that is unbelievably powerful.

However you find that out individually, however you create your support network around you. I looked at teams as two different things. There was my personal team, and there was my team at the office. The team at the office, you look for highly diverse groups of people because I know what I think, I don’t need other people to tell me the same thing about what I think. It’s easy to hire people who are like you. That’s the easiest thing because it’s like, ‘Oh, that person, I know them. I can get along with them. I understand where they come from. They have a similar background,’ but that gets you nowhere.

How do you make sure when you look around the table as a leader to go, ‘Who do I have there? Do they all bring different aspects to what I’m trying to do?’ If I’m eternally an optimist, and I always want to think things are always going to be figured out, then I need some balance of some people who are maybe a little realistic at times because sometimes I’m going to be right, sometimes I’m going to be wrong. That’s okay, that’s how you get great decisions.

If you have people who are really good at consumer side, people who are really good at project management, people who are really good at vision, people who are really good at being creative, all of those things need to come together, and that’s a variety of backgrounds, and a variety of how they grew up. A variety of how they think. A variety of different sorts of packages that we all become through our life, and that becomes critically important. That’s how you get a lot of excitement out of it.

In that are people’s passions. How do you leverage on those individuals’ passions? Hopefully the person who loves project management, not my thing personally …

Bill: Nor mine.

Brock: The person who loves it, it’s awesome when you see them get excited about it. I can be excited for a moment about project management when I’m with them. I want those people in the room because you want people to get it. That its a very necessary function, I may not like it, it may not be my ideal, it may feel restrictive to me, it may feel like it’s too cumbersome, but it really is important. When somebody’s passionate about doing that, they’re great at it.

You have that on one side. Then the other side to me is the personal team. That’s parents. That’s friends. That’s spouse. That’s kids. That’s all these things that fit around you. For me, it allowed me to take risks. I’ve been able to go after things. The idea of coming to PetFoodDirect was, relatively speaking, a very risky thing. It moved me from Michigan to Philadelphia. Never lived here, didn’t know anybody. The business was losing a lot of money. It was going to run out of cash. Everything on paper, you’d look at it, and go, ‘That was really dumb,’ but it was like, ‘If this works out, great. If it doesn’t, we’ve tried something interesting.’

I needed a spouse who was excited to say, ‘Yeah. Let’s go do that.’ It may or may not work out. You need a support network to know that if I really fall, somebody will be there to help pick me up, to tell you when things do fail that you’re not a failure, and how do you keep those things.

That becomes then passion and excitement, and whether that’s about life, whether that’s about a career, whether that’s about a subject, whether that’s about a personality, whatever you want it to be, just kind of own it, is what I would always want people to do professionally or personally. I think it just makes such a difference in life, and professional success, personal success, and how you define it.

Bill: Right, no question. Centering in a bit on the Real-World Branding topic here, we talk about the trajectory of companies as they grow, and how challenging it is to get to that point. In your work with entrepreneurs and maturing organizations, what’s the right level of thinking about brand for companies that are at an early stage? I can see, and strange for someone in the branding business to say, I can see people obsessing about it too much, but then there’s other situations where you see an organization that if they could just get the brand right, that would be the next propeller to get them to the next stage. When you think about, again it depends on the category, it depends on the company, but the role of brand in an early and in a growth stage.

Brock: I think one big misnomer about brand is it doesn’t mean the visual representation. I think that’s where most people start. ‘What’s your brand? I want to look at it.’ Yeah, when you look at it, it needs to be representative, but the point is it’s not who you are, it is representative of what you are.

The concept of brand to me when I talk to entrepreneurs is, ‘Who are you as an individual? How is that going to translate into your business? How is your business? What is your business? What do you stand for?’ People might roll that into mission and vision, and those are different ways to publicly describe it, and you need that more when you get larger, but at the end of the day it’s, ‘What are you? Why are you existing? What is the dynamic? How do you want to operate? What do you want to be foundational?’ Those all then build up what your brand is.

If a CEO, or an entrepreneur, or anyone individually doesn’t think about brand all the time, but in the broader sense of brand, then they’ll never get there, because it has to be genuine. It has to be foundational. It has to be a part of what you are. I always tell people to start there. ‘What does it mean to you?’ It can change, and it can evolve because hopefully we’re learning everyday, and getting smarter.

The core elements of it are generally true. If you make big changes, and you need to know when you’re making those big changes of elements, I think then as you start to develop that, and start to grow up in your company, and figure out who and what you are, you then need to translate that brand into visual representation. That can be what does your website look like? What does your business card look like? What does your actual, quote unquote, traditional smaller sense of the word brand look like? How do you pull all of those things together.

For example, we were in the front of a warehouse when I first got to PetFoodDirect. Our brand was a bit scrappy. That’s what we were, we had to work out of that. All of a sudden, ‘Okay. We need to be more than just this scrappy front end of our warehouse where we jump in the back, and pack packages, but that’s our brand at the beginning. We needed to touch and feel the business, but that was kind of core of our brand. Over time, we all talked about how you were touching, and feeling, and being a part of it, yet if you had to pick up the trash in the hallway, you did. If you had to do whatever you needed to do, you got it done. If you had to answer emails for customers because we got overloaded with something or we screwed up, you better be a part of that. Not because you’re the marketing manager do you stay away from having to answer customer issues.

All of those things build up. We moved our office to Plymouth Meeting. We’re in a more traditional office. It’s what we could afford. We always talked about how it was a really cheap place even though it looked expensive, but the importance was, this was cheap. We were being frugal, we were a startup. We were doing it with the limited capital that we had. Then we started to move into a larger organization, so we moved to another building. All of a sudden we designed that. Then it became ours. It was a big step in our company where all of a sudden, our visual workspace ended up being highly representative of who we were. Somebody walked into our office, and were like, ‘I get these people. I get this company. I get what they’re trying to do.’

Those are all representations of your brand. Even though there’s obviously more of the consumer brand, and everything else with that. You use that to acquire and retain amazing people, and how you build team, and how that then translates until you deliver it to your consumer.

Bill: No, it seems like it’s hard for whether it’s startups or folks even a couple of years in make it through the chaos, the fog of war. Not that it ever really ends. There is a belief or a series of beliefs, this could be better or it should be different, that are sort of couched in righteousness. It isn’t just about financial opportunity, there are some cases where folks analyze the marketplace and see white space, fine. Unless you feel that righteousness later, you don’t need, probably when you’re raising series A, the best logo that the world has ever seen, but you certainly need that core belief.

Brock: You need the passion with it. When you add the passion because the passion then is your brand. Especially as an entrepreneur or as a CEO, there are many things, hopefully, that I thought I did well that translated into the culture of our organization. There are also some things about me personally that became the culture of our organization. Whether you want it to or not, that’s what happens. That translates into your brand, and you have to be aware of that, and that’s okay. How do you manage them? Hopefully minimize, you can’t make them go away, but minimize those lesser desirable elements. Hopefully how do you accelerate the ones that are on the plus side of the equation.

Bill: I’m scared to ask my colleagues about that in the case of me and Finch, but this is great. You’ve shared a few as we’ve gone, but when you look back at your career path, I’m sure that many of our listeners are inspired by the places you’ve been, and the things you’ve seen, and the things that you’ve done and built, are there a couple guiding words of wisdom that you’d share for those who are either finding or seeking inspiration from what they’re listening to?

Brock: We talked about it a little bit before which is just love what you do. That’s a very altruistic statement, so I get it, but love it. If you’re in something that you don’t love, do it exceptionally well until you get to that point where you love it. I hated my first job at American Express. I was a junior, like every other person who starts out, a junior analyst working on spreadsheets, supporting a field sales force of 20,000 that are getting American Express card acceptance. Very, very sexy job.

I hated it, but I did it, and I worked really, really hard at it. I was going to be the best damn analyst that the place had ever seen, I worked really hard. You know what? Ten months into that job, I got this phenomenal opportunity at American Express to go to this new division that was being put together. That was all this entrepreneurial element. I didn’t even know it was being planned. Didn’t even know it existed. I knew nothing. I was 22, and lost like every other 22 year old. All of sudden somebody says, ‘look I’ve seen how hard you work, come over and do this.’ All of a sudden I’m like, ‘This is awesome.’

That element of it, and what I would tell people is don’t get lost with that. Know what that is, but you always have to do great. If you don’t like it, fix it, but while you’re in it you still have to be great because things will always come around. Things always find there way back to you in one form or another. It may not be immediately. When I actually left American Express, the woman who’s the head of our division that came in, she’s a wonderful person, Ann Buskay, she asked me why I was leaving. We talked about it, left on very positive terms, it was great.

Fast-forward ten, eleven years later. I’m in Michigan. I’m working for Entertainment Publications. We have a temporary CEO that’s coming in to be announced. It’s Ann Buskay. The odds of that, New York City, Detroit, totally different worlds, completely different industries. No reason they would ever collide ever again, and she was so excited to see me when she walked in. That was amazing. Here I was, the President of the Digital Division, so I’d obviously done some things, and she’d obviously continued to do amazing things as she was, but you have to stay around that.

I didn’t like it when I left American Express, but I left there loving American Express because I worked hard at it, and I think for people it’s always about how do you stay engaged with that. How do you have your personal team around you help you understand what you love, help you understand what you’re good at, question you? Sometimes we might say, ‘Hey I’m really good at that.’ Then somebody says, ‘You know, you might want to rethink how great you are at that,’ but maybe it’s passion, so learn it or get better at it.

If you’re going to the point of starting something, the thing that I would say to anyone in that scenario is you have to love it. I don’t really believe in the folks that kind of look at a white space, and go try and build it. I’ve not been excited about those. Some have gotten lucky in that scenario, but I would say it’s far less successful in there because when you’re building against something it’s super, super hard.

You need to have the passion, the love, the energy, the excitement, whatever that next thing is because you’ve got to break through walls. You’ve got to hit low points, and pick everybody else up. You’ve got to manage the high points. You’ve got to figure out when it’s not working, or when it is or isn’t working. You have to talk with a bunch of other entrepreneurs about different things.

There’s things that you find along the way that most people don’t know, which is you wake up one morning, and you’ll think, ‘Oh my God. Things went so well yesterday. I think this thing is going to be a billion dollars. This is going to be fabulous for our entire team. This is working so well. It’s unbelievable.’ You wake up 24 hours later, and you’re like, ‘Oh my God. We’re going to go bankrupt. I don’t know how this is ever going to work. This is totally falling apart.’ That cycle, but yet you have to walk in everyday with the same passion to try and figure it out, the same excitement. Not get too excited. Not get bummed out. That all comes from you’ve got to love it. You’ve got to be a part of it. It has to be who you are.

Bill: Nothing else sustains you if you don’t in a case like that.

Brock: Correct.

Bill: It’s interesting because you always hear about the person, and some of us have been the person, when you think about subjects in school, you do really well at the things that you’re interested in, and you don’t do well at the things that you’re not, but your point about American Express, I think with all of the great successes that are underlined and bold and italicized that entrepreneurs have had, to your point earlier, it seems easy, and I think the marketplace may be inadvertently sending the message to kids who are just coming out, or figuring out what they want to do that if you’re in a job, and you don’t automatically love it that you’re doing the wrong thing.

To your point, when you reach a point where you’re starting something, and you’re the guy or the gal that is going to have to walk through that door everyday, it has to very much align or be congruent with your values and what motivates you and your energy. When it comes to developing and growing in your career, to find a place where you’re paying some dues, where it doesn’t connect at the deepest levels of your values necessarily, where you’re not bright eyed and bushy tailed every morning, but you do a great job at it just because you uncover or express your own sense of value, and your sense of self and pride and everything else, it does open doors as it did in your case.

Brock: I’ve always been a believer that you learn from every interaction. You just have to be able to see it. That is everything from the person you may respect the most in the world, and you’re starstruck when you see them, and you think, ‘This person’s just going to throw me pearls of wisdom.’ Sometimes that’s disappointing because you’re setting an expectation that’s so high, but you think you’re going to learn so much.

Then all of a sudden you have an unusual or different interaction with someone who’s homeless on the street that actually strikes a cord in you. All of a sudden you have these and everything in between. In that scenario you learn every time as long as you’re willing to see it. That’s a hard thing to do, and it’s a very hard thing to do, but you have to stay open to that, and that’s how you get better. That’s how you get smarter, and you just continue to develop what it is because at the end, diversity of experience gives you perspective on diversity of experience.

Those two things help you solve unusual circumstances. Go and lead where, like a lot of entrepreneurs are, where things don’t exist already. When you go into those voids, it’s now ‘do I know enough about what I know or don’t know? How do I surround myself with people who know what I don’t know, and know a bunch of other things, and that we’re all aligned in the same way so that when we run into the wall, and it really hurts that we’re able to pick ourselves back up, and try to figure out a different way to go over it, around it, through it, whatever way it is.’

You have to learn all along the line, and be very self aware. Be very aware, know that those things exist because those points of where you learn or don’t learn … I always love it when somebody says, ‘Who taught you the most in your life?’ Those are and they should be hard questions.

If it’s super easy sometimes, then you’re not thinking broad enough. Yeah my father is an amazing person, and I love him to death, and he’s taught me an amazing amount. My mom has done the same. Then I had a 12th grade high school teacher who was my Earth Science teacher who had one of the biggest impacts, but it was very short. Tiny in some respects. My first job at American Express, my boss there taught me lots and lots of things. Very influential, not someone I’ve stayed in touch with, but okay. Those things all build. I think just being aware of that, being involved with it is so exciting to life in general, personally. Are what build your character and who you are. Then you can impart that, and help other people with it.

Bill: We are the sum total of our experiences. If you are somebody who doesn’t have the luxury of picking and choosing when you come out of school, or moves to a new place, and needs to get a job, if you fall into something, or the first door that you knock on opens and you go through it. I think back at my own career, the first six months, no one else … I was a liberal arts guys, and I was clueless as any 22-year-old could be in life insurance and mutual funds. They let me come, so I went. You realize quickly that wasn’t what I wanted to do. That was a learning experience that had value in and of itself. Then some of the skills you learn along the way. Very rarely is it as linear as the articles or the movies might suggest that it is.

Brock: Absolutely. Even as the next step. I’ve been figuring out Philadelphia. This is not a city that I know. I’ve gotten to know it over the last six or seven years, but it’s not where I’m from. All of a sudden it’s like people keep telling me, there isn’t a startup scene on the consumer side in Philadelphia. I started raising my hand over the summer. Started to go into the Fall like, ‘You know what? There’s a pretty amazing scene here, and we need to start talking about it.’ All of a sudden if you start looking, again opening your eyes in a different way to it, all of a sudden, all these opportunities, all these people, amazing people doing amazing things in the community, and around Philadelphia. It just takes looking for it, and being aware to see it. All of a sudden starting to help other people talk about it, and then creating a little momentum around it, and then other people get excited about it, and then all of a sudden people are more excited about it. One feeds off another. That’s really exciting to help be a part of, that makes it a whole lot of fun.

Bill: Speaking of which, we have overstayed our welcome, but this has been tremendously insightful. We can’t wait to see what comes next. Both with the work that you’re doing mentoring folks and investing, as well as your own career path. Every single stop has been fascinating and intriguing for an interview like this. I’m sure, as noted as you were in it, some days were better than others, but it continues to grow. Brock we’re so grateful for your time. Thanks.

Our thanks to Brock for his time and insight. In addition to obviously the discussion of his history and his past, and some of the functional expertise that he’s acquired along the way, and expressed through his career, some really insightful perspectives on mindset as one things about first, second, third opportunity, as well as how one steals themselves to go through the roller coaster of being an entrepreneur and building a company.

Three ways to help us on Real-World Branding, and to support what we’re doing here. The first is to subscribe to this podcast through the app store of your choice. Every other week have an interview, such as the one with Brock, with a brand and a business builder. In between we do smaller, shorter, One Big Idea podcasts we call them, ten, 12, 15 minutes on one particular topic that seems to be current, and interesting in our world. We would love to make sure that you do not miss a one, and to make sure that that is the case, subscribing is the best way to do it. In addition we’d love to see a rating if we’ve earned it. On the app store again of your choice; four stars, five stars, six stars if they begin to offer that. Either way we appreciate the feedback. Lastly in that spirit, keeping the dialogue going on Twitter. @BillGullan or @FinchBrands on Twitter with ideas for future guests, ideas for future topics, feedback. Again, skin is thick. We’d love to hear the good, the bad, and the ugly as we seek to always improve, and deliver ever more interesting content to all of you every week on Real-World Branding.

That’s about it here. Hope everyone had a great holiday, and a great couple of weeks ahead as we gear up for the next one. Signing off from the Cradle of Liberty.

The post Startups to Grown-ups: Brock Weatherup, Former Chief Digital Officer of PetSmart appeared first on Finch Brands.

When starting a business, there are many things on which entrepreneurs must focus – everything from developing prototypes to raising capital. However, one aspect every business owner or founders need to address, especially early on, is the brand. In this week’s One Big Idea, Bill explains the role of brand in early stage organizations and how early thinking about brand helps prepare companies for success. If you like our podcast, please subscribe and leave us a rating!

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Bill Gullan: Greetings one and all, this is Real-World Branding. I’m Bill Gullan, President of Finch Brands, a premier boutique branding agency and this is One Big Idea. Today’s topic we’ve entitled Early Stage Branding. A couple of thoughts about this. First of all, we’ve recently recorded over the last couple of weeks a couple of really, really interesting podcast episodes, interviews with a diverse group of brand and business builders, but it seems like recently some of the folks we’ve been and we’ll be featuring are those who really have the entrepreneurial spirit and often have worked with early stage companies – making them bigger, exiting in a favorable positive way, as well as nurturing entrepreneurs and the overall entrepreneurial eco system.

One of the interesting topics that each of these podcasts have gone into is for entrepreneurs and those who are working on early stage business concepts, how do you think about branding. Obviously with large organizations with multiple touch points, with many, many different customers and prospects the notion of brand development and brand management is a fairly well understood discipline. We’ve spoken about it at great length on this podcast.

The question though, ultimately, becomes for those who are in a mode of conserving capital, for those who are at a stage where they may be building their product and those twists and turns of the meetings they’re having or the epiphanies that they have, the studies they’re doing, are helping shape the way products are built and constructed. For those who are at that early juncture, how should they think about branding?

The topic today is: what do you need to get done early, and how you ought to think about it if you’re an entrepreneur who’s working on a venture, or you’re a little way in but haven’t hit your stride, you’re still in the planning mode, how should you think about the brand? What do you need to get done versus what perhaps comes later? First of all, there are different answers to this question but my take is as follows. We’ve outlined on this podcast in terms of first principles what branding really means.

Branding is a much bigger topic than just look and feel, than identity or colors or sales materials. Branding is ultimately about purpose, it’s about promise, and it’s about differentiation. If entrepreneurial ventures start with a core sense of why, with a core belief of the righteousness of a business cause, whether it’s to do something different, to do this better, or ‘why should we as a population have to deal with X, Y, and Z, and my company is going to make this better.’ That sort of endeavor, intellectually and otherwise, is a core element of what branding is. It’s getting to the why, it’s establishing the purpose, it’s organizing the passion in pursuit of a business goal.

So as it relates to first principles, in terms of brand, it is essential to get that done early or to arrive at that entrepreneurial activity and energy with a clear sense of what that is. The first principles of branding are important to get done or have early, finding the why.

More tactically, things that are important to think through and get right or as close to right as possible in the early stages of a venture, let’s think about identity. A good name. Our last One Big Idea was about some ways to think about the naming process. The potential of a strong brand name in terms of conveying energy, of demonstrating and expressing a position in the marketplace, a differentiable position, as well as beginning the process of getting your prospects and your customers to feel something. To balance that emotional and rational piece is important. Entrepreneurs should not miss the opportunity to use the name as part of that positioning arsenal.

It’s important to think through, maybe not to spend months on, not to spend thousands of dollars on, but to think through naming with a seriousness of purpose, as well as the requisite creativity. It’s also important obviously because you don’t want to have to go back and redo this later. It’s important that you do due diligence when it comes to naming in terms of legal availability, in terms of linguistic appropriateness, in terms of a domain name that is conducive to your sales and marketing program. You really ought to do well when it comes to naming pretty early on.

The pitch, the simple distillation of the why into the right kind of boiler plate copy, positioning statement, tagline perhaps, that kind of platform for pitching, for sales and marketing, is something to spend some time on early and to definitely pressure test with those around you with the prospective customers, with those on whom you seek to have influence, certainly your investor partners if applicable, your business partners. Getting the bare bones of the pitch right early is important.

Also we talk a lot about research and obviously we at Finch do a lot of custom and as well as picked out a panel driven market research. It is important to pressure test your message, as noted, but at this early stage our perspective is, it’s perhaps most important to do this by doing it. The best way to start doing something is to start doing something sometimes. There is the opportunity to be paralyzed by study, paralysis by analysis as we call it, and to fail to launch in a way until things are absolutely perfect, which they ultimately never will be.

When it comes to research there are low cost market research tools that entrepreneurs can harness, but in some ways I think bouncing off ideas both for business concepts but also for pitch items, bouncing them off of prospects, bouncing them off of thought leaders, investors, and others is probably all you need in the early stages when you are conserving capital and thinking through what you need to get done early on the branding front.

The overall operating principles in the early stages of business development and bringing the idea, the sense of why, the purpose into an actual business plan and fully articulated multifunction business execution – you want to save dollars, you want to control your burn rate, you want to conserve capital wherever possible. This does not mean depriving yourself of the oxygen required to enable the business to reach the next phase, but it does mean being very, very smart about the investment you make in terms of external partners. One of those investments, sounds strange for me to say is, is you certainly want to conserve capital when it comes to branding and marketing in the early stages.

Secondly, many entrepreneurs have a perfectionistic, if that’s a word, impulse. You really need in the early days to apply that impulse elsewhere. You are not going to get marketing right, at least not 100% right, from day one. You are going to discover. You are going to perfect what you do based upon market fact. While you do want to get ahead of that, in terms of again bouncing ideas, pitch items, and marketing pieces and ideas off of those whose input can help you steer, you definitely want to make sure that you are not caught in an endless loop of analysis and something that deprives you from getting to market and from learning from those early successes, and failures too. Obviously time must be spent when it comes to crafting the right value proposition, the right message, and the right suite of marketing tactics and techniques, but not so much so that you delay the learning and go-to-market process.

There you have it this week, importantly, and I guess the One Big Idea for this week is it’s important to apply the right level of thinking and resources to a couple of key things early on in the entrepreneurial journey, but, it is not essential that you go through the depth of analysis, thinking, and resource allocation that might be required when you are at a later juncture in terms of the business that you are striving and working so hard to build. That’s One Big Idea, Early Stage Branding. Bill Gullan here wishing you all the best as we sign off from the Cradle of Liberty.

The post One Big Idea: Early Stage Branding appeared first on Finch Brands.

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