How to Bootstrap

Jason has built four companies and produced two unicorns: Smart Bear (bootstrapped to millions in profit, sold in 2007; later resold for ~$2B) and WP Engine (bootstrapped for two years, then raised $300M+ to fuel hyper-growth to a unicorn with 1,200 employees). That combination, built one bootstrapped and built one funded, is rare. He knows when each path is right and how to make the switch.

His writing is the most useful "operator's handbook" out there for early-stage founders: pricing, positioning, finding repeatable customer acquisition, and getting to true product/market fit. The one I quote most often is his use of Fermi estimation for decisions that look like they don't have a quantitative component. It brings real rigor to calls most founders make on gut feel alone.

Reach for him when you're stuck on a decision and need a framework for breaking it into knowable parts.

Jason has been profitably bootstrapping 37signals since 1999, building Basecamp, HEY, and ONCE without taking a dollar of venture money. He's the co-author of Rework, It Doesn't Have to Be Crazy at Work, Getting Real, and Remote, some of the most influential books on running a calm, profitable software company.

For founders in the building stage, Jason is one of the longest-running voices for an unglamorous-but-resilient path: charge for your product, keep your team small, build the company you actually want to work at. He's been making this case for 25+ years and has the receipts to prove it. A truth-teller who shares the nitty-gritty and isn't afraid to say what no one else will.

Jasmine is a Registered Nurse who founded Navi Nurses, a private-duty nursing company in Phoenix, in 2021, and has bootstrapped it to a network of 200+ nurses providing in-home care across Arizona. She's a non-tech, services-business founder who has deliberately chosen profitability over outside capital, and she shares her thinking openly on LinkedIn about that choice.

She speaks openly about what it's like to build a business focused on profitability now, and she got there after seriously considering outside capital, so she knows both sides of the conversation. She's pursuing a business that fits her own goals: creating an opportunity for other nurses, serving an underserved population, and letting her live the life she wants. Not the rise-and-grind vision of entrepreneurship that gets pushed everywhere else.

Especially good for female and underrepresented founders who are mission-focused and trying to reconcile that mission with building a real multimillion-dollar business. And she's a great example for anyone starting without a traditional business background. Jasmine built Navi Nurses by leveraging local resources (starting with ASU Venture Devils) and growing from there.

Marie is a long-running entrepreneur, host, and educator. On MarieTV and the Marie Forleo Podcast she's interviewed Oprah Winfrey, Brené Brown, Richard Branson, and hundreds of other leaders, researchers, and entrepreneurs. She also runs B-School, her flagship online course for new entrepreneurs, and writes regularly on her blog. Her body of work is built for non-tech founders, especially those who haven't taken the leap yet.

What makes Marie distinctive on this list is that she takes the human side of building a business as seriously as the mechanics. She talks about heart, soul, courage, and identity alongside marketing, pricing, and customer acquisition, and her interview library brings in voices on vulnerability, creativity, and leadership that you wouldn't encounter in a strict business curriculum.

She fully embraces her personality, including her unique takes and musical tastes, in everything she puts out, which makes her content feel personal and unmistakably hers. Great for those moments when you're feeling stuck and need a push, or if you're a recovering perfectionist like me, when you're procrastinating to make things "better" instead of just doing the thing that needs to be done.