Mark Sinatra joins Sam Rosati and Kaustubh Deo to reflect on his 15-year journey through entrepreneurship, search funds, and leadership. From launching his first search in 2007 to navigating the 2008 financial crisis as a new CEO, Mark shares how perseverance, self-discipline, and purpose carried him through some of the most difficult chapters of his business life. He discusses building resilience during downturns, the evolution of the ETA ecosystem, and how his experiences led him to his current role at Aspen HR, where he helps professionalize HR operations for small and mid-sized companies. They discuss: • How Mark discovered the search fund model and built conviction to pursue it • Navigating the 2008 financial crisis just months after acquiring his first company• Lessons learned from employee turnover, client loss, and leadership under pressure • Why physical and mental health are essential to sustaining long-term success • The transition from owner-operator to investor and executive at Aspen HR Topics: 00:00 - Intro 02:23 - Mark’s career and background 07:24 - Launching a search fund 13:53 - Navigating the Great Financial Crisis 21:17 - Operational challenges and employee turnover 24:44 - Inflection point and recovery 33:03 - Building a strong management team 35:50 - Navigating non-linear business paths 41:04 - Winning competitive deals 43:28 - Insights from investors and turning points 47:24 - Challenges of change management 49:56 - Joining Aspen HR during the pandemic 52:40 - Aspen HR's business model and client focus 01:03:37 - PEO model explained 01:07:54 - Advice for searchers and operators