Jason Cohen: About the Author

Twitter: @asmartbear

Thanks for visiting. As a four-time entrepreneur, both bootstrapped and fundraised, with two sales, I’ve been writing about startups for 15 years. I hope you’ll find it useful!

Currently I’m the CTO of WP Engine, which I started in 2010, bootstrapped for two years, then raised small and then large rounds totaling over $300M, fueled hyper-growth to a unicorn with 1,200 employees across eight global offices, serving many billions of web requests daily for 180,000 customers.

Prior, I bootstrapped Smart Bear for seven years, built it to millions in profit, and sold it in 2007. It changed hands again in 2017 for $450m and in 2020 for nearly $2B, and continues to create new products. Before that, co-founder of IT Watchdogs, which was also bootstrapped and profitable, sold in 2004 and is still producing its products under parent company Vertive.

I’m also a mentor at Capital Factory (like TechStars or Y-Combinator in Austin) and an investor in a few companies including StackOverflow, SpareFoot, Cratejoy, Signup.com, SwimTopia, Pingboard, and Osano(And others that didn’t work out, but I’m no less proud to have been a part of the journey.)

Some folks enjoy my talks on bootstrapping and startups over the past decade. These are the favorites:

  • 2017-10, Business of Software, “Healthy, Wealthy, and Wise”  (Video) (Video from SaaStr Feb 2018 version)
  • 2013-04, MicroConf, “Designing the Ideal Bootstrapped Business” (Video)
  • 2012-10, Business of Software, “How data makes you do the wrong thing” (Video)
  • 2011-10-24, Business of Software, “Naked Business: How Honesty Makes Money” (Video) or (YouTube)
  • 2011-02-13, WebStock, “A Geek Sifts Through the Bullshit.” (Video, 50m)
  • 2010-10-03, Business of Software, “When to break the rules and ignore advice.” (Video, 55m)