The Intentional Investor #7: Rusty Guinn

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In this episode, Matt Zeigler talks with Epsilon Theory co-founder Rusty Guinn. Rusty shares his life journey, from growing up in rural Texas to working on Wall Street and eventually co-founding Second Foundation Partners. He discusses his experiences in finance, including roles in investment banking, private equity, and asset management. Rusty reflects on the lessons learned throughout his career, emphasizing the importance of humility, earnestness, and agency. He also talks about his decision to move to a farm in Connecticut, where he now balances his work in finance with homeschooling his children and running an apple orchard. Throughout the conversation, Rusty provides insights into the investment industry, personal growth, and the search for meaningful work and life balance.

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  1. sharing these notes here (and even if you know @rguinn, I am sure you’re going to get at least one new story from this one):

    Rusty Guinn Is An Intentional Investor

    In an alternate universe, Rusty Guinn becomes a Christian rock star. Or a video game music composer. Or, any scenario where he misses finance completely so that he could never become a… home schooling parent / GPT-enabled apple farmer / professional asset allocator / multi-instrumentalist / all the other things he is today.

    I’ve been thinking about this Eels quote a lot again lately, “Life is funny, but not haha funny / peculiar, I guess.”

    I’ve been thinking about the attentional awareness required to see the essence of a thing (the “soul” of a thing, borrowing from Daniel Crosby).

    I’ve been thinking about how choices, pursuits (borrowing from Justin Castelli), and phases of life stack.

    Rusty Guinn’s Intentional Investor could have been 6 hours and we still wouldn’t have covered half of it.

    Talking to Rusty is funny and sometimes, but not always, haha funny. It’s often peculiar. It’s full of blind guesses and lots of follow-up questions.

    He took me back to his grandparents and their ambitions - for not just their kids, but their grandkids’ lives.

    How their Texan, local heavy industry driven career paths were hopefully intended to get a future generation closer to pursuing the arts.

    How the ethic of following what you’re interested in, in at least a semi-practical way, with enough smarts to not quit when it gets hard - got imprinted on his parents, and eventually onto him.

    How it showed up in his music. In picking where to go to college and later live. Lots of later’s and where’s to live by the way. Lots of instruments too. Lots of how it all follows today into how Rusty and his wife are raising their kids with an eye on their futures.

    Yes, the stories about money and career are in here, but the big thread is relationships.

    Rusty explains all of his relationships in terms of agency. Listen for it. Agency is an almost romantic calling to him. The freedom to choose. The notion each person’s callings are unique to them, and every life possesses this voice if you’re wiling to listen for it.

    When agency goes wrong, it’s alienating. An identity can push you out. It can make you feel alone or disconnected.

    But when agency goes well, it’s artistry. It binds you to the others. To your others. It connects you. It creates, with intention, the gifts (and investments) that keep on giving.

    We never do it alone. Despite how it may feel at times. So how can we co-invest in a collective future, together, with agency intact?

    Listen to The Intentional Investor: Rusty Guinn, on the Epsilon Theory YouTube channel.

  2. Hi Matt:
    Just finished listening to the podcast you made with Rusty Guinn. It’s very interesting to hear the stories that define the lives of the people that you are interviewing in this series. I’ve read Rusty’s writings, spoken with him at the ET Connect events, and have a great deal of respect for his contributions to Epsilon Theory. But I really don’t know him very well. After listening to the podcast, I now feel that I actually know who he is as a person. Your engaging conversation with Rusty has made that happen. So often we only know people through their resumes, but when the veil is lifted through simple conversation, we discover that people are just people who share many similar life defining experiences. The simple things, that often seem mundane, define who we really are.

  3. A lot there, and interesting to see how it all unfolds.
    Absolutely loved the part near the end where they buy an older farmhouse in (the deep south of) New England and Rusty notices an old cider press and puts it to appropriate use. Hard cider and brisket is a great combo.
    For the mindfulness “living in the present” column I would add one thing though - when walking through the woods/fields and you spy an old apple tree with fruit, don’t look at the apple and relegate it to “inedible cider-apple”. No. Pluck one, rub the dirt off the side with the least worm infestation and take a bite. It won’t hurt you and might even reveal a surprising secret that will bring you back.

  4. Thank you @davibw1 - these two sentences alone mean more than to me than you can know.

    And, on top of that, the margins around the resume stuff, it’s where the humanizing happens. With anybody, with everybody. “Go forth and pull the damn thread, why not” is my emergent motto, I’m quickly realizing…

  5. There’s a repurposing of the old artifacts bit inside of all this, that you are also nailing in the mindfulness add @RobMann, that I’m still thinking of too. The intentionality in finding that presence - of putting our spirit into our experiences - it matters.

    Off to dust off some old apples.

Continue the discussion at the Epsilon Theory Forum


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