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Bootstrapping a 2-Sided Market to a 7-Figure Exit

March 25, 2022 |  

About this episode


Anna Maste built Boondockers Welcome, a kind of Airbnb for RVers, to $100,000 in Annual Recurring Revenue (ARR) when she received an offer of 3.9 times ARR. Maste was about to accept the offer when some soul searching led Maste to believe she could do much better. That kicked off a two-year journey of building the value of her business.

Maste more than quadrupled their revenue and ultimately accepted an offer in the “mid-seven figures”. This episode is a masterclass in bootstrapping a two-sided market. You’ll discover how to:

  • Increase your revenue with one simple decision.
  • Overcome the fear of making your first hire.
  • Leverage Facebook Groups to generate new sales.
  • Know when an acquirer has the means to buy your business.
  • Bootstrap the growth of a two-sided market.
  • Accelerate word of mouth advertising for your business.
  • Avoid one of the biggest causes of strife in a family business.
  • Increase your prices without causing churn.
  • Replace yourself inside your business.
  • Find your next great employee.
  • Negotiate for your number with confidence.


Check out the written by John Warrillow on Reasons a strategic acquirer may buy your business.

Show Notes & Links

Chris Voss

Curious about what your company might be worth? Start with a Built to Sell Valuation.

Check out our full M&A Glossary

Past episodes mentioned

Rand Fishkin
Rob Walling
Tyler Tringas


About Our Guest

Anna Maste

Anna Maste and her mother Marianne Edwards co-founded Boondockers Welcome, a platform for RVers to connect and share camping on each other’s property, in 2012. With Anna’s background as a computer engineer and Marianne’s experience and audience writing travel guides for budget-conscious RVers, they were able to create a community that provides unique camping opportunities for RVers while creating connections that last a lifetime.

They grew the platform to over 2,800 hosts and 12,000 annual guest members before selling in 2021 to Harvest Hosts, another company in the alternative RV camping space.


Connect with Anna:

Watch the interview

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