Building to Last Forever: What VCs Can Learn from the Rise of Holdcos

Last month, I found myself in an unfamiliar room. 

Surrounded by 50 investors, I was one of two venture capitalists at Sieva Kozinsky and Xavier Helgesen’s Enduring Ventures Summit—an annual gathering hosted by a holding company that "buys exceptional companies in difficult situations and builds them to last forever." The rest of the room? Operators acquiring everything from hotels to media companies to HVAC businesses, entrepreneurs rescuing "VC fallen angels" that couldn't meet astronomical growth expectations, and investors building diversified portfolios across industries most VCs won't touch.

I'll be honest: I stuck out. While everyone else talked about cash flows, EBITDA multiples, and sustainable profitability, I was the one asking about growth rates and exit strategies. 

But as the day unfolded, something interesting happened. Despite operating in completely contrasting investment models, I started to realize the people in that room weren't so different from the VCs I know. They were just as intelligent, well-connected, deeply philosophical, and obsessed with the art of business building. They were also chasing deals, navigating co-founder conflicts, and juggling a bunch of competing stakeholders. 

As I spent more time with these holdco owners, I found it fascinating to learn how they think about returns, risk, and time. And I realized there were a lot of fundamental assumptions about VC that we all needed to question.

🪤 The Binary Trap

Venture capital has trained us to think in extremes. One company in our portfolio will return the entire fund; the other 24 will die. We celebrate the unicorns and write off everything else as “learnings.” Each fund starts from zero, chasing that one legendary outcome that will define our careers for the next decade.

This binary thinking permeates everything we do. We specialize in single sectors—"we're the fintech fund" or "we only do healthcare"—betting that our narrow expertise will help us spot the next breakthrough. We take board seats and provide advice, but ultimately remain hands-off, trusting founders to execute while we wait for lightning to strike.

The holding company world operates on entirely different principles. 

Instead of swinging for one grand slam, they consistently hit singles and doubles. Unlike private equity firms with 3-5 year exit mandates, their business model allows them to hold companies over the long term, operating them sustainably and profitably. Cash flow from one acquisition funds the next. Returns compound rather than reset. Risk gets spread across industries—from tech startups to pool companies to real estate.

This community-first approach created powerful organic growth. Their waitlist exploded through genuine word-of-mouth, and their Series A announcement generated millions of impressions because their audience felt personally invested in the company's success.

📈 The Compounding Question

Warren Buffett didn't become the world's most successful investor by finding the next Google. He did it through compounding—letting returns build on returns, year after year, across a diversified portfolio of businesses that generate predictable cash flows. Yet somehow, venture capital has convinced itself that compounding doesn’t apply to our world.

But what if it does?

Some of the most thoughtful investors I know aren’t just chasing the next big win—they’re building systems that scale themselves. They’re launching media arms (newsletters, podcasts, social channels, you name it!) to grow their firm’s reach exponentially. They’re backing operators from prior portfolio companies, creating a flywheel where one success seeds two or three more. Some are even building internal tools to streamline their ability to support founders, creating operational leverage that compounds over time.

It’s a quiet strategy—but it compounds where it counts. In an age where capital is a commodity and there are more VCs than ever before, the funds that build with longevity in mind and optimize for sustainability are the ones playing the long game.

The same is true in startups. It’s no coincidence that elephant companies—startups that build movements, not just products—share this ethos. These companies generate their own compounding effects through organic growth, community-driven acquisition, and interconnected ecosystems that deepen over time.

This is the intuition holding company investors and founders have already embraced. They don’t just buy businesses—they buy into systems. A hotel acquisition teaches them about real estate, which informs their next hospitality play, which creates synergies with their property management software investment. Each deal builds context and leverage for the next.

🧱 Breaking Down the Walls

The most striking difference between the VC and holdco worlds isn't strategy—it's mindset. 

Venture capitalists have become incredibly specialized, creating artificial boundaries around what we will and won't consider. 

Meanwhile, Enduring Ventures actively seeks out "industry agnostic" opportunities with revenues between $20M-$750M—exactly the kind of "boring" businesses most VCs overlook. Their portfolio spans everything from Dolphin Pools to Scribe Media to broadband infrastructure. They're not looking for the next unicorn; they're looking for sustainable businesses with "easy to understand product offerings" and "recession-proof business models."

There's wisdom in this approach that extends beyond portfolio construction. The best opportunities often exist at the intersection of industries, not within their siloed centers. The most innovative healthcare companies are combining software, hardware, and services. The most successful fintech startups are embedding financial services into entirely different workflows.

By maintaining artificial boundaries, VCs might be missing the most interesting investment opportunities of the next decade.

💡 A New Kind of Venture Fund

I'm not suggesting we abandon everything that makes venture capital work. The high-risk, high-reward model has created enormous value and funded transformational companies that wouldn't exist otherwise. But I am suggesting we can evolve.

What would a more elephant-inspired approach to venture capital look like? I’m imagining a world where instead of starting each fund from zero, we build lasting institutions that compound knowledge, relationships, and returns across vintages. Instead of betting everything on narrow sectors, we invest across the intersections where the most creative companies are emerging. These ideas won’t be a fit for every VC, but I’m imagining a world where more people try things like: 

• Creating a recruiting directory for ex-portfolio talent and operate as a lightweight, in-house talent agency

• Starting a special situations holdco for that "forgotten middle"—the startups that are still alive and profitable, just no longer rocketship-shaped

• Launching a rolling dividends program using minority stakes in cash-flowing startups, giving LPs liquidity along the way (and capital to reinvest)

• Building a marketplace where portfolio companies can hire each other, share contractors, and pool SaaS costs 

• Using DPI from prior funds to buy out LP interests and convert the firm into a fully privately-owned holdco

What if we measured success not just by the one unicorn exit, but by the thriving ecosystem of companies, founders, and operators we help compound over time?

The holding company world has figured out how to build patient, compounding capital that creates value across time horizons and asset classes. As venture capital becomes increasingly stratified—with mega-funds capturing most of the capital and returns—perhaps it's time we learned from their playbook.

After all, the goal isn't to beat holding companies at their own game. It's to build better venture funds by understanding that the best returns often come not from one perfect bet, but from many good ones that build on each other over time.

Elephants don’t rush—and neither does real value. Compounding rewards those who move with patience and purpose.

At Park Rangers Capital, we believe the next generation of great companies will be elephants, not unicorns. If you're building a business that turns customers into community members, we'd love to meet you so email us at [email protected].