#150: Jeffrey Stern on Entrepreneurship, Product Management, Investing, Passion & Ambition, the Race to the Bottom of Attention, Founding Insights, Flanuering and lots more (Wisdom, Wealth, and Wellness Podcast)

Lay of The Land

Every 50th episode on Lay of The Land thus far, I’ve tried to honor the request I occasionally get, that from time to time, listeners would like to hear more of my own thoughts and flip the proverbial script from host to guest.

...On the 50th episode, I explored my own professional journey, the concept of startup ecosystems, and what it takes to get the entrepreneurial flywheel going

…On the 100th episode, I reflected on what universal lessons I think we can take with us from Lay of The Land: what are the patterns and commonalities across all of the stories we’ve heard from people trying to build great things — from what inspires and motivates founders to pursue entrepreneurship in the first place, to where founding ideas actually come from, to the meaning and importance of culture.

Which brings us to episode 150. Personally, I’m much more a fan of listening than I am of speaking; to reference the greatest Cleveland entrepreneur of all time, who unfortunately we won’t get the opportunity to ever have on the podcast as he passed away in 1937, but fortunately, there is quite a lot written and documented about John D. Rockefeller — he often recited a poem that reads:

A wise old owl lived in an oak
the more he saw the less he spoke
the less he spoke, the more he heard
why aren’t we all like that wise old bird?

For me, this poem resonates deeply. Lay of The Land has become my Oak Tree in that regard as it allows me to hear, to listen, and to learn! With that said, for the 150th episode of Lay of The Land, I’ll continue the tradition of taking a deliberate pause, deviating from the wisdom of the owl, and share some of my own thinking.

Fortunately, my friend Jonathan Satovsky runs his own podcast called Wisdom, Wealth, and Wellness and hosted me as a guest there where I got to share some of this thinking… and really in great company as he’s featured many far wiser than myself on his podcast like:

• Dan Ariely, one of the pioneers of behavioral economics,
• Greg Harden, an executive and performance coach to folks like Tom Brady and Michael Phelps,
• Joel Greenblatt, a renowned value investor and author of one of the books actually that got me into investing many years ago

… and many others! In our episode, which I’m resharing on Lay of The Land today, I get to unpack a whole variety of unfettered reflections on entrepreneurship, product management, investing, passion and ambition, the race to the bottom of attention, founding insights, flanuering and a lot more! I really enjoyed being the guest on the podcast for once… So with that, I hope you all enjoy this conversation as much as I did — and if you do, I encourage you check out other episodes from Jonathan’s podcast as well !

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Past guests include Justin Bibb (Mayor of Cleveland), Pat Conway (Great Lakes Brewing), Steve Potash (OverDrive), Umberto P. Fedeli (The Fedeli Group), Lila Mills (Signal Cleveland), Stewart Kohl (The Riverside Company), Mitch Kroll (Findaway — Acquired by Spotify), and many more.

Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/

Follow Jeffrey Stern on X @sternJefe — https://twitter.com/sternjefe

Follow Lay of The Land on X @podlayoftheland

https://www.jeffreys.page/