Michael Frankel is co-founder and managing partner of Trajectory Capital and president & CFO of Trajectory Alpha, a special purpose acquisition company (SPAC). He has held c-level executive roles (corporate development, strategy/innovation, CFO, COO) at large and small growth companies. Michael has extensive experience sourcing, leading, and negotiating over 110 strategic transactions, as well as integration planning, management, product development, strategic planning, and portfolio management. Michael has served on public and private boards of technology and information services companies. He has written three books and many articles on various aspects of growth and strategic transactions and is a frequent speaker on growth and disruptive innovation. Michael holds a BA, MA, MBA, and JD from the University of Chicago.
Jeff Wald is a serial entrepreneur, board member, best-selling author, keynote speaker, and investor. He founded WorkMarket, an enterprise software platform that enables companies to manage freelancers, which he sold to ADP in 2018. Jeff is co-founder and chairman of several technology startups, including Bento Engine (a toolkit for financial advisers), Sonero (an AI tool that provides summaries and action items from meetings), and Spinback, a social sharing platform (eventually purchased by salesforce.com). Jeff is the author of The Birthday Rules and The End of Jobs: The Rise of On-Demand Workers and Agile Corporations. Jeff frequently speaks on startups and labor issues at conferences and in the media. Jeff holds an MBA from Harvard University and an MS and BS from Cornell University.
- What are some insights Jeff has learned from Michael? [5:27]
- M&A for an acquirer vs. M&A for a seller [7:05]
- What is a big lesson for entrepreneurs that Michael has learned from Jeff? [9:10]
- The process and the cautionary tale behind selling Jeff’s business to ADP Ventures [11:09]
- What is the most important highlight post-acquisition from ADP Ventures? [13:33]
- How did the employees react when they learned of the acquisition? [14:00]
- The importance of a leader’s message to employees during the transition [17:32]
- What has Jeff learned from his acquirer (ADP)? [18:21]
- Differentiation between managing a large-scale organization vs. an early-stage company [19:40]
- Why does Michael prefer a company with lower EBITDA but with more infrastructure over a company with higher EBITDA but with no infrastructure? [21:23]
- One of Michael’s significant failures early on in his career regarding integration [23:13]
- How do you remain excited about a vision for disrupting an industry and still be commercially focused? [26:45]