Ep.65 The PAST, PRESENT and FUTURE of a FAMILY BUSINESS with JIM O’SHAUGHNESSY

When you have the chance to spend an hour with Jim O'Shaughnessy, you grab it with both hands. Most of us feel like we know him personally based on his thoughtful opinions and Twitter acumen (@JPOSHAUGHNESSY). But Jim is obviously more than just memes and GIFS. Jim is the Principal, Chairman and Co-Chief Investment Officer, Portfolio Manager of O’Shaughnessy Asset Management ("OSAM"). He is a four-time author including the seminal investing book “What Works on Wall Street” and hosts the INFINITE LOOPS PODCAST with Jamie Catherwood. https://www.amazon.com/dp/B005NASI8S/ref=dp-kindle-redirect?_encoding=UTF8&btkr=1 I knew about a decent amount about his career and what his company does. However, Jim is a Renaissance Man and a perpetual student who's mind can't get enough. I wanted to get behind his thinking as he made the move from a once mighty investment bank to starting (and building) his own firm. How does someone with ferocious curiosity make joint decisions with family, with colleagues. How did he use his own attributes and processes that helped him build a successful business to help him build a successful family with his wife and kids? Finally, how does someone like Jim think about the inclusion of the family in his business? Who is going to run the business as he has gets older? Finally, how did he get to the ultimate decision of handing the reigns of the firm to his son, Patrick? I hope you enjoy this episode. This is the story family businesses should hear. While the road is littered with family businesses left in tatters due to dysfunction, Jim talks about some of things that worked for him and his family. I include our outline below, but beware. We veer away from the script early and often. Amazingly, by the time we are done we cover many of the questions I had. Ownership and Operational Succession What does OSAM do?Background on your expertise- Take us throughDevelopment of the CompanyWhat is the company focusing on now?CANVASPositive SumInvest Like The Best / Infinite LoopsCapital Camp Managing Transition You’re 60 now!  What has been your thought process about where the company is?  And where it’s going to be?It seems like you embrace younger people – What does this do for you? Energy, new ideas?How have youAt what point did you start to think about the company with you not at the helm?How have you dealt with your other kids on the participation of the business?Did they self-select in or out? Skills?How do you reconcile what you think vs what they want to do?How is your wife’s input on your decision-making?When did Patrick start looking ready to take on the roles that he’s taking?How have you handled it when someone disappoints another?How do big decisions get made at the company?What does a conflict look like?  Who holds the tie-breaker vote?Do you have a board?  Formal or informal? One of your most endearing traits is your open-mindedness.  How do you get to say no?Managing portfolios vs Managing the BusinessWhat are you good at?What are you bad at?Twinges of mortality- what do you want your legacy to be when you look back on life?What are the values that you want your kids and grandkids to have?What have been the challenges there?  How do you get your kids to communicate about the issues related to the business and their roles in it?How have you involved spouses in family decisions?Whom do you go to help you think through the role of the business in the family?Friends, colleagues, professional advisors?How do you think about the ownership of the company going forward?What do you see as the biggest challenge in managing the transition of the company and your role in it going forward? Fun Questions: What haven’t you achieved yet that you would like to?What does an average Tuesday look like for you?Three people (excluding family) alive or dead that you would invite to dinner. I also went ahead and got a loose transcription for those who want...