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Grow Your Network: Bob Seawright Is A Cross-Generational Sports Investment Philosopher
Here's HOW and WHY to connect with Bob Seawright
Matt Zeigler
July 17, 2025
For years, I've been connecting with interesting people and documenting insights that might help my clients and myself. What was once private is now (mostly) public.
People often ask: "How do you know all these people?" and "How do you connect these (re: random) ideas?" The answer is simple: consistent relationship cultivation and thoughtful note taking. My north star is trusting my instincts, my maps are the constellations in these reflections.
This approach to multidisciplinary networking has helped dozens of clients, colleagues, and friends strengthen their networks and unlock new opportunities. Find my Personal Archive on CultishCreative.com, watch me build a better Personal Network on the Cultish Creative YouTube channel, and listen to Just Press Record on Spotify or Apple Podcasts, and follow me on social media (LinkedIn and X) - now distributed by Epsilon Theory.
You can also check out my work as Managing Director at Sunpointe, as a host on top investment YouTube channel Excess Returns, and as Senior Editor at Perscient.
Feel free to steal these ideas directly - that's what they're for! I can't promise you'll learn FROM me, but I guarantee you can learn something WITH me. Let's go. Count it off: 1-2-3-4!
Introducing... Bob Seawright!
Do you know Bob Seawright? He's a brilliant financial writer, sports enthusiast, and cross-generational community builder who writes "The Better Letter" on Substack.
If not, allow me to introduce you. Bob is someone who sees the deep connections between sports, investment philosophy, and human behavior across generations. He's been a Manchester United fan since before the Premier League existed and coaches his grandchildren while watching games with them every weekend. I wanted to connect with him because he embodies something I value deeply: the ability to find profound wisdom in everyday shared experiences, whether that's a soccer match or a family gathering.
Our conversation is LIVE now on the Just Press Record YouTube channel (and this Cultish Creative Playlist). Listen and you'll hear us dive deep into sports as community assets, the psychology of fandom across generations, and why accountability matters more than talent in building lasting success.
THREE: That's The Magic Number of Lessons
In the meantime, I wanted to pull THREE KEY LESSONS from my time with Bob Seawright to share with you (and drop into my Personal Archive).
Read on and you'll find a quote with a lesson and a reflection you can Take to work with you, Bring home with you, and Leave behind with your legacy.
WORK: Accountability Creates Consequences That Drive Performance
"I love promotion and relegation. Why? Accountability. One of the great frustrations with American sports is the idiot owner. Now, to be sure, owners in other countries are idiots, but there are consequences when there's promotion and relegation, there are consequences to being an idiot."
Key Concept: True accountability systems create real consequences for poor performance, which drives better decision-making and effort. When there are no meaningful consequences for failure, mediocrity becomes acceptable and excellence becomes optional. Bob's insight about promotion and relegation in soccer versus American sports franchises reveals how structural accountability can transform entire industries and organizations.
Personal Archive Note-To-Self: I won’t explain promotion and relegation (you either already know or you’re curious enough to look it up), but I will fully agree with Bob on this point - real consequences raise the stakes. Bad franchise owners know next season will be another shot. But bad club owners, who can get dropped from whatever league they’re in if they don’t perform, they have a whole other level of pressure.
Sports are there to entertain us. They’re a lot more like art than than old jocks versus music dorks schtick would suggest. You know what everything entertaining has? Tension. Stakes. Consequences.
Much like in life, death is the meaning maker, and since there’s a million ways to reach that end state, it gets pretty interesting when you start to think about it. Especially at work, in an increasingly lazy world of slop and easy-passes, consequences just feel weightier than normal to me right now, and Bob really made me appreciate it with this point.
Ask not just what success looks like, but what failure really means, and how that can drive all the other layers of forward progress more often.
Work question for you: What accountability structures exist in your work environment, and how might adding real consequences for poor performance change behavior and outcomes?
"There are very few live shared experiences, which was part of what the clip talks about. And sports are one place where they can have it. And, you know, a whole city gets charged up about a team and a sport. I'm a big Padres fan still, and the day we're taping this, the Padres beat the Dodgers in a wild one last night. It was just insane. But of course we watched."
Key Concept: In our fragmented digital world where we rarely consume the same content at the same time, live shared experiences become precious community-building opportunities. Sports, concerts, and other real-time events create collective memories and emotional bonds that can't be replicated through individual consumption. These moments matter because they give us something to rally around together.
Personal Archive Note-To-Self: Two behind the scenes things you should know that go with this quote - 1) Bob lives on the East Coast but was on the West Coast at the time of our recording, and 2) he didn’t realize he’d be in California when we booked our recording so he was up really early after a Padres game that finished really late.
But, Bob showed up, because even if he was a little tired still, he’s the kind of guy who honored his commitment to and this experience of recording together.
While we unpacked the Roger Mitchell clip, we kept hitting these ideas. When we share the emotional range of sports, aka the least important most important thing on earth, we build bonds. He talked about how whatever the thing is about watching sports (or any events, really that are) live, it’s the non life or death meaning-maker in this case.
So if we know it, why wouldn’t we lean into it more? We can share them with our city, we can share them with our family, but we have to take the step to participate in order to share. I can’t help but think about how pro-social and communal experience, without politics, are worth directly investing our time in.
Life Question For You: What live shared experiences are you creating or participating in with your family, friends, or community, and how might you prioritize more of these connection opportunities?
LEGACY: Cross-Generational Wisdom Flows Both Ways
"My grandsons who are enormous football and EPL fans have been incessant in their mockery of me and my team. We have talked about - if you were a multi-billionaire, what does every multi-billionaire do? Well, every multi-billionaire buys a sports team. And in our family we talk about it a lot and we love to watch together."
Key Concept: The best intergenerational relationships involve mutual learning, playful competition, and shared interests that evolve over time. Bob's relationship with his grandchildren shows how wisdom doesn't just flow downward from elder to younger, but creates a dynamic exchange where everyone teaches and learns. The mockery and banter around sports fandom becomes a vehicle for deeper connection and understanding across generations.
Personal Archive Note-To-Self: I love that Bob’s grandkids love mocking his Manchester United fandom. I partially love it because Man U were so good for so long and I like seeing them get some comeuppance. But I mostly like it because intra-family trash talk is one of my love languages.
Kids need these type of status games. They need to be able to pick on people in a logical way that doesn’t upset the normal balance. Sports, watching and playing, allows for it like few other things.
And at a higher level, the put your money where your mouth is multi-billionaire status seeking level, the same is still true. The richest people on earth just want to be able to talk a little smack, you know? So who cares what the valuation multiple is? All of life is a middle school cafeteria. Enjoy the food fights.
Legacy question for you: How are you creating opportunities for mutual learning and playful exchange with different generations in your family or community?
BEFORE YOU GO: Be sure to…
Connect with Bob Seawright on Twitter @RPSeawright and LinkedIn
Subscribe to "The Better Letter" on Substack for his brilliant takes on finance, sports, and human behavior
Take a moment to reflect on all these ideas!
You have a Personal Network and a Personal Archive just waiting for you to build them up stronger. Look at your work, look at your life, and look at your legacy - and then, start small in each category. Today it's one person and one reflection. Tomorrow? Who knows what connections you'll create.
Last thing: Don't forget to click reply/click here and tell me who you're adding to your network and why! Plus, if you already have your own Personal Archive too, let me know, I'm creating a database.