Adam Robinson’s Lessons from When a Bootstrapper Tries to Grow like a Venture Backed Company

The SaaS Revolution Show

In this episode of the SaaS Revolution Show our host Alex Theuma is joined by Adam Robinson, founder & CEO of Retention.com, who shares his lessons from when a bootstrapper tries to grow like a venture backed company. "The word bootstrap mostly describes 'okay, I got it to 3 million, it's making a million and a half bucks. I don't have a lot of employees, I don't have a lot of problems, this is great'. The problem is like, most of those companies are actually just slowly dying. But what creating companies like that can allow you to do is you get it to that; you get somebody else running it, and then you try to tinker around and like, make another one. By the time you're like, 'oh, this is working, I'm actually going to focus on it', It ends up being bigger than the last one." Adam shares: - His 10 year stint working "The Big Short" - Equating entrepreneurship with being able to be present - Hustle meets reality: why five years went by before he paid himself a dollar - Churn dynamic and financial discipline - The most capital efficient way to spread awareness in your buyers - The art of getting unstuck and the entrepreneurial cycle and more!Check out the other ways SaaStock is serving SaaS founders 🇺🇸 SaaStock USA 2025: 13-15 May 2025 | Austin, Texas. Connect, learn and thrive at the leading conference for B2B SaaS Founders, Operators and Investors from Pre-Seed to Series C. (https://ti.to/saastock/saastock-usa-2025) 🇮🇪 SaaStock Europe 2025: 12-14 October 2025 | Dublin, Ireland. "The best SaaS conference for founders, execs & investors in Europe, period." - Christoph Janz, Partner, Point Nine. (https://share.hsforms.com/1FbUpCXpJT8um3MehUUYcAg3upof) 🤝 SaaStock Founder Membership: A private members group of B2B SaaS founders between $100K - $10M ARR who are committed to growth and helping others (https://www.saastock.com/founder-membership/) 🌎 SaaStock Local: Monthly meet-ups in cities all around the world, bringing together SaaS enthusiasts and experts to discuss the most pressing topics in SaaS (https://local.saastock.com/home)