In this episode, Pete Flint converses with Marco Zappacosta and Kristen O'Brien on the growth and evolution of Craigslist and Thumbtack. They discuss the importance of liquidity and network effects in marketplaces, the misapplication of Uber's model, and the future of human capital in marketplaces. They also delve into leadership, fundraising, competition, and the future of online-offline interaction. Marco Zappacosta (Co-founder & CEO of Thumbtack) talks with Pete Flint (NFX & founder of Trulia) about what it takes to build a billion-dollar marketplace and the lessons he's uncovered along the journey. They discuss how they solved the chicken & egg problem, what he would have done differently as an early-stage marketplace, fundraising lessons, and how short-term metrics can actually hinder long-term retention. Read more essays from NFX - www.nfx.com (0:00) Introduction to the episode and guests (5:13) Observations from the growth of Craigslist and the value of liquidity in marketplaces (10:26) Reflections on Craigslist's network effects and the suitability of the service professionals category for disruption (15:11) Evolution of Thumbtack's business model and transition from a lead generation marketplace to a transactional one (22:43) The need for constant evolution to meet consumer expectations and the misapplication of Uber's business model to other industries (29:05) Managing transitions during major changes and setting expectations (33:58) The future of marketplaces: human capital and its potential & the importance of vulnerability as a leader (40:15) Lessons learned from fundraising and mapping out goals for future rounds (43:15) Discussing competition in the market and the importance of brand (51:22) Future of online to offline interaction in marketplaces and prioritizing customer problems (54:20) Wrapping up the discussion

Marco Zappacosta, Co-founder and CEO of Thumbtack, talks about his unusual path to entrepreneurship, growing Thumbtack through multiple market cycles, and his mindset around leadership. They also discuss the initial market reaction and pitching investors, building a company during a recession, exploring the use of apps for service booking in small towns and big cities, and the challenges of creating a positive company culture in startup companies.

Thumbtack CEO Marco Zappacosta discusses starting a company during the great recession, fundraising tips, and optimizing the consumer experience. They also talk about the impact of the gig economy on overall employment, struggles with finding trade workers, and the debate on worker classifications.