October 2025
We’re hit the end-of-summer jackpot when it comes to art and music. New shows have hit the streaming platforms; big new albums have hit the airwaves. And with all the new content come the think pieces about what this new art says about our lives, and what lessons we can take away from it all. Lately, however, I find myself coming back to one question: Are we missing the biggest and most obvious takeaways?
The whole point of Succession…
Lately, I’ve been watching House of Guinness on Netflix, a dramatized account of what happened when Sir Benjamin Guinness died in 1868, leaving the famed Guinness brewery to his children. In reality, two of Guinness’s sons—Arthur and Edward—inherited the brewery with his other son and daughter receiving inheritances that weren’t connected to the business.
he show sets up a more convoluted series of events set against the backdrop of Ireland’s quest for independence. What sticks out to me, however, isn’t the intrigue or the scandal, it’s something far more tangible: Sir Benjamin Guinness didn’t discuss his will or plan for the business with his children prior to his death.
It all reminds me of another great drama about succession planning.
In HBO’s drama—which seems to draw inspiration from a few real-life media empires, most notably the Murdochs, but also the Redstones and the Hearsts. The irony, or perhaps the point, of the show is that by creating a competition amongst his heirs to find the best possible successor, patriarch Logan Roy essentially dissolves the empire he fought so hard to preserve.
And yet, for all the think pieces I’ve read exploring the takeaways from the show, very few talk about the two most basic:
- You need a comprehensive estate plan.
- You need to communicate, ideally via regular family meetings.
Sure, we can talk about greed, leadership, and the balance between business and family. But—and this would make for much less entertaining television—it doesn’t have to be that deep. Sometimes it’s as simple as putting things in writing and having a conversation.
In fact, I’ve written quite a bit about family meetings and even put together some high-level guides to help you get started (no media or beer empire required).
I protect the family
So far, we’ve talked about art that imitates life. But what if we add another layer to the mix? In her latest album, Life of a Showgirl, Taylor Swift channels Succession in her song Father Figure.
Fans presume this is a song about the record label that ultimately sold off her masters until she flipped the script on them, proving she was bigger than a label. Despite the very real inspiration for the song, Swift says she was also inspired by none other than Logan Roy.
“I kept thinking about that scene in Succession where Logan looks at his kids and says, ‘I love you, but you are not serious people,'” Swift told Jimmy Fallon.
In other words: Family meetings may provide you with creative inspiration and help you avoid the drama of a conflicted inheritance.
On a more serious note, though, we once again see a very important business lesson buried in the art. Swift could teach a master class on how to treat creativity and art as a business, protecting your intellectual property, and more.
And yet, so much of the analysis written about her songs focuses on relationships, friendships, feuds, and whether or not she truly understands Shakespeare. So I want to once again fight the trend and focus on (less obvious) business takeaway—this time, in the song Eldest Daughter.
In it, Swift essentially describes an aversion to risk that comes from being the eldest daughter in a family:
You know the last time I laughed this hard was
On the trampoline in somebody’s backyard
I must’ve been about 8 or 9
That was the night I fell off and broke my arm
Pretty soon I learned cautious discretion
It’s a question I asked my business partner, older sister, and Trailhead’s resident eldest daughter, Courtney Ranstrom, about on this month’s podcast. And as she points out, there is a real financial component to this equation.
Data shows women are more risk averse than men when it comes to investing. Studies also show that older siblings tend to take on less risk than younger children. All of this can play out in our career choices, financial plans, and more. It’s a major reason working with a financial advisor—one who works to understand your relationship with money as you build a financial plan—can make such a difference.
Just to take this full circle, we also discuss the dynamics of running and participating in family businesses (and how that impacts our ability to advise families in similar situations).
