Rey Flemings – Stipple 2 of 2

"True success is not measured over small intervals." Stipple's digital media platform allows users to label, discover, and monetize the content found within photos.

Matthew: What are some things that you make look easy, that come intuitively for you and what has been difficult and how do you manage that?

Rey: Product. Business development and strategic work, those things are kind of natural skill sets for me. The tougher things, the toughest part of any start up is that true success is not measured over small intervals. You look at Facebook and you say, “What a gigantic company that happened overnight!” It happened overnight right? That’s because it’s seven years old, right? And yet we all talk about it today because it’s a giant company, you’ve got to be bigger but there were many points in it’s history where, “Is Facebook going to be better than MySpace? Will it be the next AOL and shoot up and then go out of business? Nobody knows.” 

The hardest part, I think, for anyone, well, certainly for me, is the daily energy and commitment required really 24 hours a day, 7 days a week to execute a company like this. It’s hard on you individually, it’s hard on your family, it’s hard on your team. We certainly think it’s all worth it but that’s not to say that it is not easy. I certainly have been suffering the entrepreneurial curse, which is the fact that for one reason or another you probably get good sleep less than half of your days because either something has been so positive that you’re too excited to sleep or so negative that you’re too bummed to go to sleep, but either way, you’re not going to get a whole lot of sleep. It would be like kind of perpetually having a 3 month old in the house the entire time. They stay 3 months old for like 3 years or however long it is that you’re the early entrepreneurial stage with your business. So that’s the thing that comes hard. 

I think the things that come easy are really kind of setting up and doing kind of my core work on product and biz dev. But the tough part is doing it every day, no matter what, no excuses and doing it again, and doing it again, and, “Oh, I just worked a 19 hour day,” guess what, there’s 18 more hours of work waiting on your tomorrow, “But tomorrow’s a Saturday,” but it’s your company and if you don’t do it, no one else’s going to do it. Just discovering that really no one but you and your founder in your early stages, nothing happens unless you personally execute that thing and if you want to be great or you want to be successful with your business, it just requires a tremendous level of high output consistently over a long period of time and that’s, I think, the toughest part.

Matthew: What bit of advice or piece of information do you wish you would have know before starting Stipple?

Rey: I wish I knew what the right business model was before I started it. There were things, like I said, a lot of smart people had been working on, “how do you monetize images?” for a long time. We don’t think we’re actually being smarter than any of them. We do think, perhaps we’ve outworked some people because we have totally worked our butts off. Our team has been, for the longest time, one-fifth the size of our closest competitors. And I believe we’ve built a better product with better revenues and better customers than any of the people in our space. And it has purely been primarily attributable to the fact that these guys really, like I said, just work their asses off and do their best. So, if anyone could have told me what the right path was upfront, I don’t think anybody knew, but that would have been a great thing to have.

Matthew: What mentor has played a significant impact in your development?

Rey: I had a number of great, great mentors here. I’m really fortunate to have [Agosto Amaguiz], formerly of Intel Capital and an angel investor here in the valley. As a board member, Agosto has been a godsend and has just spent a lot of time really helping me personally and helping the company. Rick Marini, another one of the great adviser, an entrepreneur’s entrepreneur. There’s nothing I’ve ever asked of Rick that he’s been, that he’s not given and given effusively. He’s an adviser to Stipple and investor in Stipple. And we actually share space here in the office. Mike Maples, definitely comes as advertised. 

When you take money from an investor, you rarely have a chance to fully get to know someone before you take an investor. Mike and Ann have been really good to us. And I think that’s part of the process, as an entrepreneur, I had a young man come in the office today who essentially makes a competing product but the most important thing that we can do for each other is to be supportive. You never want to be “that guy,” you know what I mean? Where, “Oh, you’re too important, or you’re too cool to be helpful to another entrepreneur trying to start a business.” 

So, I very much appreciate the people who have been good to me and good to us as a company and I think it’s important that everybody in the community remember to give back and remember to keep an open door and to stay humble when people come in to see you. 

Matthew: What advice would you like to share with the audience about launching a start up? If you have to distil it, what are the key elements?

Rey: There’s a great article that I read about standardized testing not being a good measure of long-term success. That guys that perform really good on the SAT and people who perform moderately on the SAT that the people who perform super well on the SAT are no more likely, ultimately, to make any more money or to be more successful in life. Ditto for the L-SAT, ditto even for the NFL-combine, right? That the guy that runs the 40 the fastest is no more likely to ultimately be a better running backer in a league if he ran it in a 4.2 and the other guy ran it in a 4.6 or a 4.8, that he’s actually no more likely to run more yard ultimately or score more touchdowns. 

The thesis behind it is that short term measurements of ability fail to be an effective gauge because success in life is measured over large blocks of time. So if there were any “start up advice” or “start up secrets” that I’d share, I’d say the very first thing is if you’re going to start a business, be willing and be committed to diligent, high output over long periods of time. The counterpoint to that is also be willing to take a break. Force yourself to look out for yourself and your own health and try to stay healthy. 

Pick a disruptive market. I think there is, arguably, too much echo chamber work picking up dollars today because running a start up becomes kind of fashionable and everyone wants to do it and I would encourage anyone who wants to do it, to try, I only encourage people to continue to invent, to continue to be intellectually curious at the point that they’re forming a start up. I also advise anyone starting a start up to not think of themselves in the beginning as starting a, “I have this product.” 

I really believe that we’re experimenting, trying to find what an investor would call product-market fit and we’re in the process, continual process of testing things, until we’ve built a black box that’s efficient, that we can take to scale. At that point, you’re really a company, right? You’re scaling it up, but when you’re starting one of these businesses, you’re really in the business of experimentation and the better you are at executing something you want to experiment with, communicating it to viable customers, taking their feedback, iterating it, the whole start up customer development process that we all hear so much about. The better you are at that, the better and more successful you’re going to be as a start up. 

So, being diligent, thinking big, and then realizing that it is a very iterative process to get these things going and find the right position. Ask for help. I have found the community here to be very willing to take a meeting to talk to people and be very, very giving of their time. That would probably be my list of things that would be important. 

Matthew: Ray, before we close, we would love for you to share with the audience, your vision for Stipple and how you hope it will change the world.

Rey: At the end of the day, we would consider it a win if web users, in the most general case, believe that they can simply touch a photo on their phone, iPad, or mouse over one on the web and that they expect to see accurate, meaningful information that’s relevant to what they’re looking for. If users think of tactile search, by tactile I mean mousing over or touching photo, in the same way that they think of a Google search, I expect to get real information, I expect to learn something, I expect to be able to buy when I touch this photo, then we’ve won, we’ve done our job. If users believe that the behavior of exploring a photo is fun and if they find value in the results that see, then you’ve really built a great company. 

As a vision, imagine all the photos on the web that matter being interconnected, being aware of who’s looking at them, being able to provide you with accurate information on the things that you’re looking for, not spamming you. And really delivering information you want to see, when you want to see it and staying the hell out of your when they’re not. That web objects carry searchable and shoppable information that’s accurate and always there and always available as a system. That’s really the vision for where we want to take the company.

Matthew: Ray, it’s been a pleasure having you as a guest on FounderLY, we’re routing for your continued success at Stipple. For those in our audience who would like to learn more and join their community, you can visit their website at This is Matthew Wise with FounderLY, thanks so much, Ray.

Rey: Thank you


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