Case Study – From Bootstrapped to Venture-Backed


About the Episode

Serial entrepreneur Ryan Buckley returns to M&A Talk to discuss lessons learned as he moves from bootstrapping to seeking venture capital backing with his current company, Shovels. Ryan talks about his decision to pursue climate tech as his next project, how the idea of mining and analyzing building permit and inspection data can help people make better decisions about contractors they work with, what went into his decision to pursue VC money, and the importance of focusing on providing the most value.

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In this Episode

1:26 What’s changed with Ryan’s businesses since he last spoke on M&A Talk in March 2022?
7:28 How does contractor permit work across different jurisdictions, such as cities vs. unincorporated sections of counties?
12:23 Is it possible to tie litigation trends and social media into the predictive model of Shovels?
19:11 What are the types of companies that Coelius Capital invests in?
21:04 What were the elements that went into deciding to pursue venture capital money with Coelius Capital for starting Shovels?
31:54 How did the co-founder of Shovels come on board?
34:25 What are the operating principles Shovels is working on as it is starting up?
36:26 Where is the talent pool coming from? Are the engineers coming from local, national, or international talent pools?
41:44 What is the most important lesson Ryan has learned so far as an entrepreneur since his last visit to M&A Talk?

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Acronyms or Terms Used in This Episode

  • ARR – Annual Recurring Revenue
  • B2B – Business-to-Business
  • API – Application Programming Interface
  • ETL – Extract, Transform, Load
  • GC – General Contractor
  • MVP – Minimum Viable Product
  • MRR – Monthly Recurring Revenue
  • ADK – Assessment Deployment Kit

Meet Our Guest

Ryan Buckley

Ryan Buckley

CEO of Shovels

Ryan Buckley is an entrepreneur with over ten years of experience building, running, and selling web technology companies. He currently is CEO of Shovels, a building contractor analytics company. Ryan most recently was CEO of MightySignal, a mobile app data company, which he sold to AirNow in 2021. Prior to leading MightySignal, Ryan was co-founder and CEO of Scripted, a marketplace for content marketers, as well as EmailFinder, and TrackJobChanges. Ryan is the author of The Parallel Entrepreneur and an associate professor at Diablo Valley College, where he teaches entrepreneurship and marketing. He serves on the advisory boards of both the Business and Computer Science departments and is a board member of the DVC Foundation. Ryan holds bachelor’s degrees in economics and environmental sciences from UC Berkeley, a master’s in public policy from the Harvard Kennedy School, and an MBA from the MIT Sloan School of Management.

Location Location: San Francisco Bay Area, California

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