Midlife Comfort, The Grateful Dead, & Long Term Investing
I had the privilege of seeing Dead & Company in Las Vegas over the weekend with my wife and friends. As a soon to be 45 year old white guy, that can’t dance, I’m all in on jam bands. I’ve come to accept my place in the music universe: parking lot filled with Subaru’s, flannel layered over tie dye, and meandering 15 minute songs that have never sniffed a top 40 radio station. Only recently did I even discover the joys of going to see Phish at the Hollywood Bowl, or noodling to the Tedeschi Trucks Band at SDSU’s amphitheater. Heck, I just bought a 1970 Scout 800 that doesn’t run. From the outside, you could call it a mid life crisis, but from the inside I see it as mid life comfort.
I have grown comfortable, not complacent, with my values and appreciating things that really matter in life: relationships, setting a good example for my kids, creating wins / wins in business and sticking to these values even when it means less for me. I’m a newbie in the jam band scene, but there is something great about seeing live music that connects everyone in the audience. Similar to going to a football or basketball game, without the competition. You’re watching highly skilled players doing their thing, who are reacting the mood, their bandmates, and making it all look seamless. The crowd is all in on the shared experience, enjoying the moment.
So how does my mid life comfort phase and The Grateful Dead relate to my job? They are a perfect example of how real relationships and talent come together to create a sustainable business. I realize the irony of Dead & Company playing the Sphere for months with outrageous ticket prices, but in my opinion, Bob Weir has earned the right to cash in some chips and bring the Dead experience into the modern era. Their focus on fans, community, and in my opinion, great music, has resulted in a financial windfall, not selling out.
The Long Term Business of The Grateful Dead
The Grateful Dead weren’t a band, they were a rebellion with guitars. Born from the primal chaos of 1960s San Francisco, they were the musical embodiment of a society spiraling into revolution. War abroad, protests at home, and an entire generation reeling from the hangover of postwar optimism, the Dead offered a new kind of show: one with no rules, no walls, no clocks, and definitely no corporate sponsors.
They weren’t chasing chart-toppers or Grammys; they were building a tribe. Their concerts weren’t performances; they were communal experiments in sound and space. Songs lasted 20 minutes, floating like sonic LSD trips through a sea of tie-dye and dust. The only metric that mattered was the vibe. Somehow, despite their refusal to play the game, the Dead won. They outsold expectations, outlasted critics, and outlived most of their contemporaries.
The Deadheads, didn’t just listen, they followed. Literally. Town to town, in VW vans, bootlegging shows (which the band encouraged), and living the message: freedom over conformity, community over commercialism, meaning over money. The money was a result, not a goal.
What made them last?
· Authenticity: The Dead never sold out because they never bought in.
· Fan obsession: They treated fans like family, not consumers.
· Cultural timing: They weren’t a brand, they were a movement.
With Dead & Company the original sound still echoes, but the spirit feels... digitized, a bit sanitized. A polished version of a once messy revolution. However, for me, and all the other newcomers, it’s a bridge to the past, an opportunity to distantly feel connected to a movement that swept the country before I was born.
Investing Influence
Pulling this back into investing, there is plenty of focus on one hit wonders and manufactured idols, but chasing these quick hits only leads to volatility and portfolio blow ups. I’m looking for investments that have some real talent, developed a mutual relationship with customers & suppliers, and will be around in 10 years still jamming away. Will the band members change over time, definitely, but if the core is strong, and the value proposition clear, the music never stops.
Long-term investing isn’t about chasing the next big thing, it’s about truckin’ through the ups and downs, keeping your eyes of the world on the horizon. The market will test patience, shake confidence, and whisper dire wolf warnings in the night. However, if you keep on dancing through the daylight and stay committed to your strategy, the ripple effect compounds. You don’t need a miracle every day, you need discipline, perspective, and the humility to know that the wheel is turning and you can’t slow down. Play the long game. Let others chase the hype while you focus on building something that touches the soul.