Does MBA spell entrepreneur? Part 3

Here’s our interview, slightly edited.

How has your MBA degree proven valuable in your entrepreneurial pursuits? 

Jack: For me, it’s not the degree per se that proves valuable, but rather every single person you went to school with, every potential alumni you could interact with, not to mention all future students as well.  My background was not sports, it was not venture and I was not from the Bay area.  (I did corporate bankruptcy/turnaround based out of NYC). I always felt that the value of the MBA was 10% in the classroom and 90% outside of it.  The connections and the knowledge locked in the heads of those around you are pretty powerful and should be tapped.  The Haas network was hugely valuable as I transitioned geography, career and industry.  Grad school tuition is a pre-pay on these intangibles. 

Why did you become an entrepreneur?

Jack: I come from a very entrepreneurial family that has started up a number of small businesses, so the idea was always kicking around in my head.  It was probably a bit naive, but in a lot of ways it seemed like more of a natural evolution than some huge risky leap.  One of the roadblocks that stood in my way was determining what business to start.  Perhaps the biggest epiphany was to realize that I wanted to work in a field that I really enjoyed.  I didn’t want work to feel like “work” ever again. At the time, working for enjoyment trumped all other priorities…size of venture, size of exit, etc.  I knew I had a passion for sports and simply wanted to figure out a way to live off of it.  Everything else snowballed from there.

Yardbarker’s model evolved from user-generated content site to ad network. Talk about the evolution and what you learned along the way.

Jack: The initial concept for Yardbarker was user-generated content for Fantasy Sports. This was back in 2005, and the alpha site was launched in 2006. We learned that when you give people a platform to write about things, they take a lot of liberty to write about anything and everything.  This meant more often than not, writing about everything but fantasy sports.  Many people submitted gossip articles about scandals, such as A-Rod going out with Madonna, rather than sports scores and analysis.  Turns out guys really enjoy rumors and gossip and they needed an outlet.  We also learned that many were intimidated to write for the public eye. We decided to lower the barrier to content contribution, and opened the platform to a Digg-like contribution model. The content contribution skyrocketed, specifically amongst an active group of existing talented contributors, sports bloggers, who were looking to promote their content.  However, this pivot also created new challenges.  We were an ad-supported business and we were often directing traffic off-site.  In parallel we recognized there were two major pain points in the industry.  Bloggers were having a tough time monetizing their blogs and advertisers were having a tough time reaching a rapidly growing, valuable audience on the long tail of sports content.  We recognized that there was a valuable role that Yardbarker could play by uniting our promotion of great content and with the creation of a strong platform for brand advertising.  This was the seeds of our migration to a vertical ad network in 2007.  It was a win-win-win situation for advertisers, bloggers and Yardbarker.

What’s the most difficult thing you have to had to deal with as an entrepreneur?

Jack:  It is extremely difficult, if not impossible, to shut off.  The day does not end when you leave the office, it does not end when you are separated from all your electronics and it doesn’t even end when you go to sleep.  I find myself constantly thinking about the business, sometimes even dreaming about it.  I keep a notepad on my nightstand because I often wake up in the middle of the night with an idea for work.  That passion fuels progress but it can be draining as well.  The business becomes a part of who you are, so when things are going poor, they weigh exceptionally heavy on you and on the flip side, when things go well, the high is greater than you can imagine and is intensely more satisfying than anything I felt while working for someone else.  That high is addictive and is probably a major catalyst in creating serial entrepreneurs.

Give us one piece of advice rooted in your experience.

Jack:  “You are wrong…but that’s ok” is the single best piece of entrepreneurial advice I ever received.  This is not just advice, it’s a philosophy.  If you go into your venture believing that your initial business idea/plan is right, you will miss all the warning signs of why you are wrong, fail to adapt, and inevitably fail to succeed because you are too busy trying to prove the world that you are right.  Instead, if you go into the process with the idea that you are already wrong, you will seek to find out why, adapt, iterate, and move on.  You are much more likely to find a solution to customer pain points by listening to them instead of trying to convince them of your initial concept.  Our business model has changed a number of times from the beginning and we are better for it.  This philosophy also helps preserve capital because if you think your initial concept is wrong, you are encouraged to experiment small until you isolate the real success variables and then can invest heavier.  If you go all in initially, you won’t have enough capital left over to pursue a winning path once you realize your initial assumptions are off.

See the last two interviews:

Part 1: Hotwire and Tripit co-founder Gregg Brockway
Part 2: Trulia co-founder Sami Inkinen