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...