Born Again Bootstrappers w/ Wistia
Back in 2016, I got a strange note with a strange request to meet a founder dealing with a strange, but somewhat familiar, problem.
This founder had raised money for their startup, grown slowly, then quickly, then suddenly found themselves with a nine-figure offer to purchase their business. Investors were excited for them to sell. But they found themselves feeling differently.
This is a dream outcome for most founders. Having only raised $1.5M total, these founders still owned a massive amount of their business and would have themselves a life-changing amount of money once the deal was closed.
But what if they liked the life they were in the middle of building? And what if the only thing they’d want to do once selling the business and collecting their cash was to basically hire all their old colleagues back and start building again?
Those are the questions that brought me to a table in Manhattan that day.
What if, rather than selling the business, they could buy out their investors and continue building the business that they loved?
The founders of Wistia, Brendan and Chris, quickly discovered the answer to that question. After securing a $17M loan, cashing out investors, and refocusing the business, they flipped from negative $500k EBITDA to positive $6M in less than a year. What a difference focus can make!
In this conversation we unpack their journey of building a “lifestyle business”. Some takeaways:
— Chris and Brendan emphasize the importance of patience, focus, and long-term thinking in building a sustainable business. They challenge the notion that raising large amounts of venture capital is necessary for success by finding that being profitable allows for more long-term focus and creative risk-taking. Compounding growth over time can lead to significant results, even if initial growth rates seem modest compared to venture-backed peers.
— After the buyback, there was a shift in company culture towards greater ownership and cost-consciousness among employees. They introduced profit sharing and later reintroduced stock options to align incentives with long-term growth. They stress the importance of building a team you enjoy working with and taking risks on people with growth potential.
— Wistia focuses on solving big problems in large, growing markets rather than chasing short-term trends. They’ve learned to be patient with new product initiatives, looking for early qualitative feedback before expecting significant revenue. The company balances short-term metrics with long-term vision, understanding that meaningful growth often takes time.
Since that fateful lunch in Manhattan I’ve gotten to know Chris and Brendan much better. We even hosted one of my favorite indie events ever with them at their Cambridge HQ — Founder Field Trips (should we bring those back?!?). They’ve grown so much as entrepreneurs and leaders over the intervening years, which I think really comes out in this conversation. They talk often about “profitable confidence” and “patience”, which is often lacking from the mainstream startup vernacular. They embody both and articulate the value of each so well. I’m beyond impressed with what they’ve built and how they’re building it. I think you will be too.
I hope you enjoy listening to this conversation as much as we enjoyed recording it.
— Bryce
