Succession Part 1: Seeing the World Through the Next Generation's Eyes

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John Maddison
January 27, 2022
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A few weeks ago, the HBO drama “Succession” was honored with five nominations and three wins at the 2022 Golden Globe Awards. The show centers on the conflict between octogenarian Logan Roy and his children Conor, Kendall, Roman, and Shiv, as they wrestle for control of his media empire. Though watching the Roy children vie for position, money, and power creates drama that is fun to watch, we know from our experience advising wealth creators for over thirty-five years that familial conflict, especially in the context of running a family business, is everything but entertaining for the participants.

In their book “First Generation Wealth,” my partners Robert Balentine and Adrian Cronje,1 address some of the same themes present in the show: running a family business, navigating relationships between family members, and having courageous conversations. They identify three principles for addressing these themes in your own life: don’t mistake wealth for legacy, distinguish between your business and the business of your family, and see the world through the next generation’s eyes.

Over the next few weeks, we will break down a situation from an episode of “Succession,” identify the corresponding principle from First Generation Wealth, and provide advice to avoid the pitfall yourself from our experience advising wealth creators over the years.

Introduction to Succession

Logan, once a poor immigrant from Scotland, built Waystar Royco over decades. Though we are not told exactly what the company looked like when he founded it, over the course of the series we learn it encompasses theme parks; a prominent fictional news station on par with Fox News or MSNBC; and a cruise line. We also know that Logan Roy and his children enjoy incredible affluence. In season one, they travel to an afternoon softball game in a fleet of private helicopters.

On the way back from the softball game, Logan Roy suffers a stroke. He had not created a succession plan, so while Logan is convalescing in the hospital, Waystar leadership looks to his children, Conor, Shiv, Roman, and Kendall, for direction as to who should take control of the company in his absence. This tension, of who will inherit Waystar and if that person can fill Logan’s shoes, is the conflict driving the series.

Seeing the World Through the Next Generation's Eyes

Each person is shaped by the world around them, which creates different attitudes towards life – and wealth. Though families do shape some of these preferences, there is no guarantee that children will share their parents’ beliefs and values. In First Generation Wealth, Robert and Adrian counsel wealth creators not to assume they know how their children feel about their family’s wealth and business. They encourage parents to:

“Spend time together with the intent of stepping into [your children’s] realities. Observe how they move through the world, ask questions, and listen intently without judging. By taking the time to understand what makes your next generation tick, you foster trust, reveal new veins of conversation, and make money and many other critical topics far easier to discuss.”

Logan Roy does not take the time to relate to his children empathetically – to disastrous consequences. When we’re introduced to Kendall, he is the only Roy child who works at Waystar, and he is the presumed heir-apparent for CEO when his father retires. On the surface, this seems like an implicit indication of Logan’s trust in Kendall. In reality, Logan communicates distrust by coldly dismissing Kendall’s ideas and actions.

During Logan’s convalescence following his stroke, Kendall learns that Waystar owes $3 billion to a creditor, who is demanding payment. Waystar is unable to pay $3 billion outright to the creditor, so to save the company from ruin, Kendall makes a deal with a private equity investor to cover the debt. Kendall, who is acting CEO while Logan is ill, is proud of himself for keeping the company from taking the financial hit. He hopes that this will show Logan that he is capable of holding the CEO role one day. However, Logan shows anger and contempt when Kendall tells him about the deal. Though he does not explain his anger, Logan is so dismissive that it appears he would not have approved of any action undertaken by his son. Kendall leaves the meeting feeling deflated and hurt.

Unfortunately, this is not an isolated incident. Repeated treatment like this erodes the relationship between Kendall and Logan. Over the course of the season, Kendall becomes resentful of his father’s treatment and plots how to usurp his father as Waystar CEO.

Avoiding this Pitfall

Logan is a successful CEO, and he presumably has decades of experience collaborating with internal and external stakeholders. Unfortunately, the openness this requires does not extend to his relationship with Kendall.

In First Generation Wealth, Adrian and Robert write:

“Most entrepreneurs are skilled at putting themselves in the shoes of others – say, their customers, their competition, or an employee. They know how to play mental chess, anticipate the reactions of others, and analyze problems from different points of view. But they sure can struggle with perspective when the matters are closer to home.”

In the scene described above, Logan does not empathize with the stress that Kendall is under. Kendall is grappling with the incapacitation of his father, someone he admires and loves, by a serious medical event. In addition, without much training, Kendall is striving to save his family’s company from defaulting on a loan, which would mean financial ruin.

With a decades-long age gap and different life experiences, it is not surprising that Kendall made a different decision than Logan might have. Logan’s inability to recognize this and show empathy to his son shuts down the opportunity to learn and grow from the situation. Had Logan tried to listen generously to Kendall’s decision, instead of judging him immediately, there would have been an opportunity to discuss Kendall’s point of view and perhaps the possibility of a teaching moment for Kendall. In addition, a few months down the road, Kendall might not have felt compelled to usurp his father as CEO.


Wealth creators are bright, driven, and creative. They move through life at 100 miles per hour, and with all that they juggle daily, it can be challenging to slow down and see the world through their children’s eyes. Taking the time to stop, challenge assumptions, suspend judgment, and listen empathetically is crucial to building strong relationships with the next generation. Investing in these relationships provides a foundation for acceptance and fruitful discussion that will benefit all discussions in the future – including those around wealth and legacy.

This is evident in “Succession,” where we see how the absence of an empathetic relationship adds extra stress to an already difficult situation for the Roy family. Had Logan stopped, thought about where Kendall was coming from, and evaluated Kendall’s decisions in that context, he could have provided feedback that would have allowed Kendall to understand where he fell short and empowered him to make a better choice in the future. Not only would it have made this specific situation better, but it would have given Kendall the confidence to continue working as acting CEO and set him up for success in the future at Waystar.

“Succession” details situations that may be familiar to wealth creators, though perhaps not quite on the same scale. We’ve spent more than thirty-five years advising entrepreneurs like Logan Roy on navigating questions surrounding wealth and legacy. If you’d like more information, we hope you will consider visiting, where you can learn more about the steps you can take to ensure enduring wealth and a long-lasting legacy.

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