How Investing in Culture Will Help You Win the Next Decade

Opinions expressed by Entrepreneur contributors are their own.

Key Takeaways

- Treat culture (media, music, storytelling, events) as infrastructure, not just a line item. Investing in cultural resonance builds trust and lowers future brand awareness costs.

- Instead of chasing short-term “home run” campaigns, focus on “perennial sellers” — consistent cultural assets and experiences that compound brand relevance over time.

- Cultural investments should be evaluated with data, due diligence and risk management, mixing safer bets and bold creative bets — similar to balancing investments in a financial portfolio.

Music and media have been a lifelong passion of mine. Movies, records, the way a great story can shift how people see the world. That’s always been the thing that gets me out of bed. For years, that passion and my work in financial services existed in parallel. Then, during a major rebranding at Siebert Financial, the two collided.

We’d been in business for nearly 60 years at that point. Loyal client base, institutional credibility and the kind of discipline you’d expect from a publicly traded firm. But we also recognized that our industry has a tendency to stay still. People keep doing things the same way because it makes them money, and they don’t always see the paradigm shifting underneath them.

Particularly post-Covid, when audiences started engaging with content and culture at a completely different pace, we saw a huge opportunity. Moving our headquarters to Miami sharpened our focus: There were entire segments of people (across cities and generations) that we could reach with the right cultural and media investment.

So we made a decision: We stopped treating culture as a line item and started treating it as infrastructure.

Cultural match is everything

Gebbia Media exists because of a single conviction: People resonate with services and companies only if a genuine cultural match exists.

We don’t see the content we create, the media we invest in, the music we back as mere promotion. All of it is a long-term investment in cultural resonance with our customers and a means to engage a new generation of investors.

The financial case was clean: Entertainment is becoming a diversified asset class. But the strategic case ran deeper. Outsourcing everything connected to your public perception is giving up control of your own story to external entities. And too many big firms, public ones especially, have done exactly that.

We wanted the opposite. We internalized the storytelling and the creative approach, and we use outsourcing only to produce the vision. That distinction is everything.

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Perennial sellers over home runs

Ryan Holiday wrote about perennial sellers; that key concept has changed how I think about media investment. The distinction between a one-time home run and something that delivers consistently over years maps perfectly onto how we approach cultural assets. You can get lucky with one viral moment. But without a body of work, without a brand story that withstands the test of time, you’re back to zero the day after the spike fades. What we want is a truckload of doubles that keep delivering, alongside whatever home runs may come.

Marketing stunts have a place. But here’s the uncomfortable truth most won’t say out loud: You are only as relevant as your advertising spend if you haven’t invested in the long term. If you haven’t built a brand that can withstand the test of time, you’re renting every client interaction.

Where this gets real

Gen Z developed a genuine yearning to meet in person, not just scroll another feed. We saw that and moved on it. Through the music labels we’ve acquired, we started producing a series of intimate, acoustic concerts — artists playing six or seven unplugged songs in a room with our clients, athletes and influencers. We make it a very intimate evening.

We call them “Off the Record.” The most recent was January 27th at the notorious Whisky a Go Go in Los Angeles, a landmark venue and, for us, a chance to put our artists in front of a live audience that actually cares about the music. While a financial services firm sponsoring a rock show might seem like a distraction to an outsider, it’s a calculated investment in building trust through physical connection. After Chicago and Nashville, we’re expanding to New York next. We’re building something designed to compound.

Head of food and beverages

None of this sits easily with everyone in finance. The pushback from traditional voices always starts the same way: “We all consume media. How complicated can it be?”

My answer: Consuming content does not make you an expert in creating it. The two are fundamentally different disciplines,