Entrepreneurs are Everywhere – Show No. 16: Wayne Sutton and Dave Kashen

Silicon Valley’s pay-it-forward culture means that others will help when you’re starting up. Yet this same network of connected people affects who gets funded, how startup teams form, and who gets hired

And a company culture and values need to be design and engineered just like the product

These topics were the focus of interviews with the latest guests on Entrepreneurs are Everywhere, my radio show on SiriusXM Channel 111 (airing weekly Thursdays at 1 pm Pacific, 4 pm Eastern.)  The show follows the journeys of founders sharing their experiences of what it takes to build a startup – from restaurants to rocket scientists, to online gifts to online groceries and more. The program examines the DNA of entrepreneurs: what makes them tick, how they came up with their ideas; and explores the habits that make them successful, and the highs, lows that pushed them forward.

Wayne Sutton.jpg

Wayne Sutton

Joining me this week at the Stanford University studio were:

Dave Kashen

Dave Kashen

Listen to the full interviews by downloading them from SoundCloud here and here. (And download any of the past shows here.)

Clips from their interviews are below:



Wayne Sutton is a partner and co-founder of BUILDUP VC, a Bay Area non-profit that connects, mentors, and educates underrepresented technology entrepreneurs. He is also the co-founder of Tech Inclusion, dedicated to exploring innovative solutions to  diversity and inclusion in tech.

Looking to create their accelerator/incubator, Wayne and seven other founders rented a Silicon Valley house together one summer.

The experience proved to be a wealth of learning opportunities, but one lesson in particular stood out:

… I learned (from) that experience that if you show that you’re willing to put in the work and the effort, there are mentors and people out there willing to volunteer to help you, but you have to take a risk. You have to put yourself out there.

…By creating the BUILDUP VC incubator and accelerator … we’re got into the business of providing education and access. We learned that people were willing to provide us resources, provide mentorships, and open their doors. …It proved to us and our companies that … if you are willing to take the risk of coming to Silicon Valley and work on your startup, people want to help.

If you can’t hear the clip, click here.

Dave Kashen is co-founder & CEO of Worklife, a Y Combinator-funded startup whose mission to have everyone love their job. Their first product aims to make meetings more productive. Prior to Worklife, Dave was a CEO coach, leadership trainer and culture consultant to some of Silicon Valley’s fastest-growing technology companies. Previously, he was co-founder of Wellsphere, an online health and wellness company that grew to over 6 million monthly visitors.

He faced several challenges with Wellsphere early on:

We were a little bit too early in a couple different dimensions so I learned the importance of timing…  

In ’05, social networking was not quite as prevalent as is it today. The idea of a social network inside of an organization wasn’t a thing yet so that was a little bit scary and even the linkage between healthy behaviors and saving healthcare costs and becoming more productive and being less absent and all of that, a lot of that research has emerged over the last 10 years. 

(Just as important as the product) we did not pay a lot of attention and we’re not particularly intentional about how we were building the company (and its culture.)  

We had this mission. We were both non-technical co-founders so that had its own challenges. We were probably a little bit arrogant in our thinking of what we could create and how we could lead developers to create these ideas that we have.

We were also arrogant in the sense of we have this idea of how the thing should work and we built it … This was a little bit before Lean Startup was very popular, so we just built this thing that we thought would work and lo and behold, it didn’t work. …The features didn’t match what ultimately the customers would buy or wanted.

If you can’t hear the clip, click here.

Wayne set his sights on entrepreneurship when he was a teen, working in the tobacco fields of North Carolina:

I remember working in the tobacco field one morning. It was about 10 am, and it was hot, maybe one of the hottest summers that season. It was maybe 100 degrees. … around me, I saw people my father’s age, I saw some family members as well, and people that could have been even my grandfather’s age working in the field with me.

I understood that this was their opportunity to make money, and in their generation there wasn’t many other opportunities besides farming for them to make money.

I looked at myself, and was like, “When I get older, I’m not going to be working in a tobacco field.” I wanted my own company. …I wanted to be in charge of my own destiny, and that started my drive.

If you can’t hear the clip, click here.

He first startup idea had potential, but he gave up on it too quickly:

It was going to ESPN before ESPN. … North Carolina is big basketball country, a big basketball world like ACC, Duke, UNC. I met these two athletes … one had a little bit of stint in the NBA, the other one had just graduated college and played overseas a little bit. I was like, “… It’s going to be big. People are going to go online and vote for their favorite athlete and all, post pictures.” This was around 2001.

… They were like, “Oh, this sounds good and everything, but I’m not sure if this thing is going to work out.” … I bought the domain and started doing events… launched a website, and was doing polls (but his co-founders gave up on it, and so Wayne did as well).

… The lesson there is that if I believed in the vision of what things could be. … You have to realize that you may be too early, the market may not be ready, but also … there’s benefit in sticking it out. I look at that lesson (and think) heaven knows what could’ve happened if I would have stuck it out.

If you can’t hear the clip, click here.

Wayne also spoke about working to increase the number of minorities in tech:

It’s not an easy problem to solve. It is not just one thing, -… it’s not just about (a lack of) people in the pipeline, its not just as a problem in terms of biases. Not just a problem in terms of access to technology. (It’s all of these.)

We don’t think about that in 2016, everybody doesn’t have a smartphone. Everybody doesn’t have hi-speed Internet. Everybody doesn’t have or is even aware of success stories such as Steve Blank or the process of launching a startup.  

Even though we have all this information online, not everybody is aware or have access to this, and (on top of this there) is lack of role models … especially for underrepresented entrepreneurs. And it’s a culture issue.  

…Look at the history of America and what has been the role models or the examples of a way out for a lot of underrepresented entrepreneurs minorities? It has been sports and entertainment, not tech.

I feel like now we’re beginning to see people focus a little bit more on tech, but it’s not just one thing. It’s all those pieces. …

…(Silicon Valley) is a network-based system — about who you know … who gets funded, how teams are forms, who gets hired in certain companies, how promotions (are determined) — that is all relationship-based.

Steve:  You think there is implicit rather than explicit bias?

Wayne: Yes.

Steve: That’s an interesting … It’s truly an ‘old boy’ network.

Wayne: Yes. 

Steve: Even though the old boys are not very old. 

Wayne: No.

If you can’t hear the clip, click here.

Right out of college, Dave chased a dream of being rich, becoming an investment banker. It turned out to be the wrong path for him.

Long Island, (where Dave grew up, is) a fairly materialistic place and I was reasonably intelligent, so everyone said to me you’re going to be a millionaire. I thought that was what I was supposed to become, and so that kind of got drilled in my head. … The point was to make lots of money and that’s what led to happiness, and that was kind of the mindset for a while.

…my dad was a doctor, my mom was a teacher. … They were divorced when I was 5, so the distinction between my dad’s lifestyle and my mom’s was very apparent to me. I think that was part of the fuel, but there was no entrepreneurs, no real business people in the family, no finance people, I didn’t know what investment banking was, but there was this really, I think, deeply embedded mindset of like you’re supposed to become wealthy and do high-status things, and that’s how you become happy.  

If you can’t hear the clip, click here. 

Wellsphere found success, but not in the way Dave had anticipated.

…We pivoted the company toward what the market wanted, and what our users and customer wanted, but away from my initial vision and passion.

It worked in the sense of we built value. We were able to grow really quickly from a very small to 6 million monthly visitors. We found a core distribution model that worked in terms of long-tail search. … but by the time we did, it was no longer aligned with my passion, and the vision of the impact I wanted to have.  

In some way, part of the decision to sell the company at that time was because I lost that alignment. I think we could have built more value, had we continued.

Steve: That’s another great lesson. If you’ve founded something, but find you’re no longer passionate about what you’re doing, it becomes just a job.

If you can’t hear the clip, click here.

The experience led him to create Worklife and, he said, helped him become a better manager:

I’m way more conscious about hiring for values and listening for alignment (with the company’s values). … As I moved from (a founder of my own company) into the world of coaching, and training, I’ve worked with clients on discovering their own (personal) values and their company values, then devising systems and processes used to make sure that 1) that they’re hiring for values; 2) they’re actually living them day to day.

As a coach over the last five years (I learned) that the way to motivate somebody is to have the situation occur to them as if it’s in their best interest. …. When I talk about values, in part it’s trying to understand, what does this person value and do those things overlap with the experience would be like working here. …

If you can’t hear the clip, click here.

Listen to my full interviews with Wayne and Dave by downloading them from SoundCloud here and here. (And download any of the past shows here.)

Next on Entrepreneurs are Everywhere: Tiffani Bell, co-founder of the Detroit Water Project; and Clay Hebert, founder of Crowdfunding Hacks.

Tune in Thursday at 1 pm PT, 4 pm ET on Sirius XM Channel 111.


Want to be a guest on the show?  Entrepreneurship stretches from Main Street to Silicon Valley, from startups to big company’s. Send an email to terri@kandsranch.com describing your entrepreneurial journey,

One Response

  1. Great to meet you in tel aviv!!!

    I am the guy who shook your hand and told you I was a fan

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