Amy Hoy and Alex Hillman on Bootstrapping, Community and Fun

alex-hillman-amy-hoyTech-entrepreneur, Amy Hoy popped onto my radar a few years back when I read an article she’d written where she coined the term “entreporn,” or the relentless focus on venture-backed-massive-exit business as the only thing worthy of your attention.

She eviscerated that myth (with some fantastically colorful language) and along the way offered an alternative. An approach to building a bootstrapped business or career not around the race to scale, exit and do it all over again, but around quality of life, values, relationships and presence. The article provoked a massive and polarized reaction in the tech community.

At the same time, Amy’s friend, Alex Hillman was growing his own legend in Philadelphia as the founder of one of the most vibrant co-working communities in the country, Indy Hall. They’d spend hours rapping about a better approach to entrepreneurship for developers and tech-oriented creators and eventually ended up collaborating to create entrepreneurship training venture, 30×500, where they teach tech-entrepreneurs how to build bootstrapped, sustainable, flourishing businesses.

In this wide-ranging conversation, we go deep into each of Amy’s and Alex’s journeys and explore everything from what it took to build the epic community that is Indy Hall to how Amy took a ton of heat for walking away from a successful venture that wasn’t right for the way she wanted to live her life. Both Amy and Alex are incredibly transparent and literally bursting with nuggets of gold for anyone considering building a bootstrapped “good life” venture or community-driven business.


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