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Pack Your Own Chute – The Personal Decision to Join a Startup


So, you’ve got a cushy job building software at a big company. But you want something more challenging. Maybe you’ve got an idea for your own company, or maybe you’re getting recruited to join an existing early-stage start-up. It sounds exciting! But you’ve got college loans, or a mortgage, a spouse, two kids, or whatever. So it still just seems a bit risky, expensive, and scary.

What kind of lifestyle should you expect? What happens to your career prospects if you fail? How do you figure out what your worst case scenario is, and avoid it? Or maybe you just have no idea how to answer the basic question, “Is this something I can even consider?”

There are plenty of resources for discussing business models, fundraising, Lean Startup, MVPs, and the like. We’ll discuss none of that here. We want to discuss the very personal decision to found or join a start-up, and tactics for how you can arrange your personal life to enable your adventure while managing the risk.

This decision process is different for everyone, and the way to implement the decision varies widely. Not everyone can or should work for a start-up. Our goal is to demystify the whole thing, even if we can’t make it less scary.

This is an open, no BS discussion. We’ve assembled a panel of techies to represent various angles on this question. And we want everyone else in the room to be asking questions and sharing their own experiences.

  • Todd Gardner, who recently co-founded track.js, still has his day job, and is dealing with these questions right now
  • Matt Hardy, Co-Founder of KidBlog which has reached traction, gotten funded, and seeing success
  • Liz Tupper, who Co-Founded SieEnt (as a single mom!) and not only survived its ultimate demise, but thrived
  • Paul DeBettignies, start-up friendly tech recruiter who sees these decisions play out every day
  • (moderator) Neal Tovsen, left a big-enterprise job five years ago to start a company, failed, and is starting again with Apruve

Who knows? Maybe a few people will leave the room with a little more confidence that they should give it a try.


Minnebar 9 (2014-04-12)


Neal Tovsen, Paul DeBettignies, Liz Tupper, Matt Hardy, Todd H Gardner