Laura Diane Hamilton

Technical Product Manager at Groupon


3 Chicago Bootstrappers Share Their Lessons Learned

Last Wednesday the Chicago Hacker News meetup group met at Basecamp headquarters.

Three Chicago bootstrappers (and solo founders) shared their experiences founding and scaling companies without outside capital.

Mari Luangrath, Founder of Foiled Cupcakes

  1. You aren't an expert at everything. Find experts to do the stuff you can't or won't.
  2. Block out time to be productive. If it takes you 20 minutes to ramp up and 20 minutes to close up, you're not going to get anything useful done in an hour. Mari needs at least four 4-hour blocks a week to be productive.

Ryan Evans, Founder of Rand Media

  1. Failing is OK. If your venture fails, it doesn't mean you're a failure. Conversely, if your venture starts succeeding, you're probably alright, but keep your cool.
  2. Your second customer might be a more important indicator than your first. There's probably one crazy person who will buy anything, but two means you're probably on to something.

Evan Miller, Founder of Wizard

  1. You're going to make mistakes the first time. It's nice to have a warm-up business.
  2. The 2-step formula for a successful software company:
    1. Find shitty $2000 software that people are already buying.
    2. Make it better.
    You don't need to guess what people want or ask them what they want (they don't know anyways). Find what people are already paying a ton of money for.

All 3 founders agree...

  1. Find a peer group. Having a sounding board is important. Ryan, Mari, and Evan all talked about their peer groups and people they bounce ideas off of.

Thanks to organizer Eric Liu for taking notes and summarizing the key takeaways. is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to