How to spend money as a bootstrapped SaaS company with Bridget Harris, youcanbook.me

Bridget Harris, CEO and co-founder of youcanbook.me, had initially assumed she would be raising money for the online scheduling tool she was building with her co-founder. Bridget and Keith Harris spoke to many investors, looked at many term sheets and soon began grasping a peculiar fact - running a company with VC funding doesn’t make things easier, if anything, it may make them more difficult.

The latest guest on the SaaS Revolution Show, Bridget has been bootstrapping youcanbook.me for the past six years. While the bootstrapped route is not for the faint-hearted, it allowed them to grow as fast as they wanted, even if that required expert knowledge of the difference between cash flow and actual income

The company now employs 13 people and recently reached $2 million in ARR and is well on track to get to $3 million by the end of the year.

Listen on to learn:

• How you learn to determine which expense makes sense and which doesn’t


• What made Bridget well suited for the bootstrapped path


• How to know when to take a risk and when not to


• How to make the finances work in a bootstrapped company and still grow


• What is a defining characteristic of a great entrepreneur

P.S.

We are bringing SaaStock on Tour. First up is London on March 21st. Spend the day in the company of 300 SaaS founders, their executive teams and local VCs and see Des Traynor Co-founder and CSO of Intercom, Ryan Singer, Head of Strategy at Basecamp, Peter Holten Mulhmann CEO of Trustpilot, Philippe Botteri Partner at Accel and Laurence Bret Stern, CRO at Pipedrive to name a few. https://www.saastock.com/ontour/city/london

Check out the other ways SaaStock is helping SaaS founders move their business forward: 

🇮🇪 SaaStock Europe: 14-15 October 2025 | Dublin, Ireland
Book tickets: https://saastock-europe.com/tickets/

🇺🇸 SaaStock USA 2025: April 2026 | Austin, Texas
Book tickets: https://saastock-usa.com/

🤝 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)