My Favorite Mistake — 184: CEO Bryan Clayton Thought Outsourcing Technology Development Would Be Better Than Building It

CEO of GreenPal

Episode page with video, transcript, and more

My guest for Episode #184 of the My Favorite Mistake podcast is Bryan Clayton. He is the Co-Founder and CEO of GreenPal, an online marketplace that connects homeowners with local lawn care professionals. GreenPal has been called the “Uber for lawn care” by Entrepreneur magazine and has over 300,000 active users completing thousands of transactions per day.

Before starting GreenPal, 10 years ago, Bryan Clayton founded Peachtree Inc., one of the largest landscaping companies in the state of Tennessee, growing it to over 150 people and $10 million a year in annual revenue before it was acquired in 2013. Bryan‘s interest and expertise are related to entrepreneurism, small business growth, marketing, and bootstrapping businesses from zero revenue to profitability and exit.

In this episode, Bryan tells his favorite mistake story about outsourcing the development of an app, thinking all he had to do was the marketing. What went wrong and how did he discover the mistake? What did he learn and what did he learn about mistakes, leadership, and culture in an organization more broadly?

We also talk about questions and topics including:

  • Where did you get the idea to outsource?
  • When did you first start discovering that it was a mistake?
  • Using “Lean Startup” principles?
  • What was your Minimum Viable Product?
  • What’s your mindset on mistakes that happen in the company now?
  • From a culture standpoint, what did you learn from the first company that you applied to the second?
  • “You get the company culture that you deserve as a leader”
  • “I made every mistake you could make” – felt victimized
  • “Took me a long time to self reflect about the mistakes I made.”
  • Do you ask for feedback from employees about the culture?
  • Mistakes people make when hiring a lawn care company?

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