Last weekend, my business partner and I attended the CNBC/Boardroom Gameday Conference in Santa Monica. The reason I wanted to be there is simple—I’m a huge fan of what Rich Kleiman has built with Boardroom.
His brand, magazine, and event series are becoming increasingly relevant, and I wanted to see firsthand how he brings these elements together. I didn’t attend last year, so this year marked my first experience, and as someone who has had Rich as a guest on my podcast (we actually went to summer camp together), it was amazing to witness the evolution of his career. I’ve watched him grow as a businessman, a brand-builder, and a husband and father. Seeing us both now, in our 50s, from where we started as kids, is inspiring.
I noticed a few key things
A couple of things stood out to me. First, no matter how anyone dressed, almost everyone seemed united by one accessory—a pair of Nike Dunks. Some were subtle, some a bit ridiculous. Even CNBC’s Andrew Ross Sorkin was rocking blue and yellow Dunks, which looked like he asked his kids, “Hey, do these make me look cool?” They didn’t…(And, that’s not a shot at Sorkin, I like the guy, the colorway on the dunks, not so much)
The crowd was a mix of young startup founders and well-established midlife males. I found it interesting to watch the dynamic—especially the younger guys hustling to network with the established names, like Jamie Patricof, Drew Sheinman (no relation), and Kevin Durant. The contingent of successful midlife men were definitely the stars of the show, with the younger crowd jockeying for position to get a moment with them.
I couldn’t tell whether David Adelman (CEO of Campus Apartments and co-owner of the NBA’s 76ers and NHL’s NJ Devils) was really on the phone the entire time, or just wanted to appear on the phone so that there was no opening for anyone to approach him during the breaks.
I caught him just long enough to say “Hey, we both have kids at CU, SkoBuffs, and I’d love to interview you for Midlife Male…” I have zero game and need to work on my icebreakers. It’s always fascinating to see how people in positions of power navigate these types of events.
Andrew Ross Sorkin went pretty hard at Casey Wasserman, bringing up recent sexual misconduct allegations. The timing and venue didn’t feel right for such a topic, and it cast a shadow over an otherwise positive panel featuring Grant Hill, Jessica Alba, and the Mayor of Los Angeles. I don’t think he deserved that. On the flip side, when it came to a panel on sports betting—something that really warranted the tough questions and in the right forum, which this was, (more on that in next week’s Viewpoint Column) —he went soft.
The highpoint was Rich’s one to one conversation with Rich Paul. The best, those at the top tend to not say anything overly complicated, or overly articulate even, and I mean that in a too polished, academic kind of way, but rather you can sense their intelligence, that they’re not trying too hard or that they have anything to prove. They have a likability about them, they come across as capable. Some of the things I took from Rich Paul were “Don’t sit in your success…”…He talked about always seeking improvement. To keep moving forward. “What I thought success was, it’s not…” We get caught up in what success looks like, and the truth is, its never what we thought it was. “Focus on care”. Be the guy, company, brand that cares the most. And the mic drop moment “I’m a toddler in this thing…I may be 52, but I’m just a toddler at this business.”…The most acutely midlife male thing I heard all day…
Overall, the event itself felt somewhat distant, with a noticeable separation between the panelists and the audience. It felt like we were being talked at, rather than engaged in a conversation. This design choice made the experience feel less interactive than what I personally enjoy. Typically, I prefer more of a Fireside Chat format that encourages dialogue between the speakers and the audience. But here, it was clear there was a ‘black curtain’—you were either inside the exclusive circles or not.
All that aside, why I really wanted to go is that I’m simply curious by nature, I’m fascinated by business, sports, and what makes middle-aged men tick.
And this was a largely middle aged male group. I wanted to see how they interact, network, and share insights—I wanted to understand the format of the event and how it compares to what we do at Midlife Male. Would we do something like this? How would we make it better?
I always see these types of events as investments in myself and our brand. What’s interesting? What’s not?
There was no doubt that the production value was high, the venue cool, and there was a cachet in being in the room with names like Grant Hill, CC Sabathia, Rich Kleiman, Albert Pujols, David Adelman, Doug Sanders, Mookie Betts, Casey Wasserman, Jessica Alba and Kevin Durant.
But the bigger question is: How does it help you?
Are you seeking entertainment? Education? Networking? Access? Insights? Or are you simply curious, like me, and willing to try something new each quarter? Did I see potential guests and interview opportunities for Midlife Male? Absolutely.
The point is, we all have our reasons for attending events like this, and there’s always something to take away, even if it’s just a better understanding of what works for you.
And I think that’s key to maximizing midlife—putting yourself out there, trying new things, being strategic and tactical about it. Sometimes you hit, sometimes you miss. That’s why our ‘How I See It’ column exists—it’s so important to get different perspectives, so men can make better choices for themselves.
Because, at the end of the day, success really does come down to the actions we take and the choices we make.
Some things y’all always want to know
I stayed at the Proper Hotel. This was not where the event was held. I prefer the Proper for a few reasons; primarily it’s a Marriott property so I can enhance my status, pick up double points using my Bonvoy Amex, and get upgraded. They also have a great hotel gym, pool, sauna and Morozko forge cold plunge. This gives me no reason to not stay on my routine.
I always try to meet friends, or business connections for workouts and breakfast rather than dinners. Josh Taekman, CEO of Eboost, met me for a great yoga class. If you haven’t tried Eboost, it’s a great product and Josh is a super guy.
I also appeared on two podcasts as a guest. EverForward Radio w/Chase Chewning and Drops of Gold w/Jeff Scult.
And got to have a much needed, enjoyable and productive breakfast with my team and my business partner Kirk Moquin.
