The Accidental Entrepreneur Who Thinks Like a Family Office

My mission has always been simple: to pull back the curtain on how the wealthiest families actually build and protect their money. Is it a family office, entrepreneurship, investments, or a mix?

The ultra-wealthy don’t win because they’re smarter or luckier. They’re winning because they’re using a different playbook — one based on private markets, smart leverage, and asymmetric risk.

In particular, I want to share that playbook with people who want to stop thinking like employees, stop looking for the next big thing, and start thinking like long-term wealth builders.

Chris Van Dusen exemplifies the mastery of this transition best. As an entrepreneur who navigated the high-stakes journey from founder to sophisticated allocator, Chris isn’t just a theorist; he’s a proven serial entrepreneur. In addition to building and exiting multiple powerhouse brands, Chris cofounded one of the largest CBD companies in the world before becoming a Senior Equity Partner at Solyco Capital.

In addition to overseeing a sprawling ecosystem of over 38 portfolio companies, he specializes in helping founders make the necessary transition from high-performance operators to disciplined, strategic investors. As someone who has bled for his own companies and now protects others’ capital, Chris is a rare individual. Bringing real scars, successful exits, and the perspective of someone who has actually put skin in the game, he brings priceless value to the table.

An Entrepreneur by Necessity, Not Design

Chris describes himself as an accidental entrepreneur. But I would even go so far as to call him a forged entrepreneur.

Having graduated from William & Mary and started his career in sales, Chris moved from Virginia to California in late 2009, only to be laid off 75 days later during corporate restructuring. New state. Increased living costs. No job. No safety net.

The moment didn’t inspire a motivational poster. It forced action.

After dating for four months, Chris and his now-wife started a marketing company to stay afloat. What followed over the next decade wasn’t a straight line. Rather, it was a portfolio of experiments. There were both wins and painful losses. And there were even a few outcomes that most entrepreneurs dream of.

During this time, however, the following highlights were notable:

• Co-founding the second-biggest CBD brand in the world, which was sold in 2021.
• Launching and exiting a liquor distillery.
• Exiting a beauty care brand.
• Building multiple business solutions focused on high-intent media buying and conversion optimization.

Yes, those are the companies you put on your wall. Chris admits, however, that there were far more gravestones than trophies during the journey.

Today, he invests with the same humility that informed his investing in the past.

Why Chris Thinks Like a Family Office

In 2022, Chris joined Solyco Capital as a senior equity partner. What attracted him wasn’t just deal flow, but philosophy as well.

Among the markets in which Solyco operates are:

• Venture capital
• Private equity
• Private credit
• Real estate

In other words, true alternative investing — similar to what a large family office does because their focus isn’t headlines, but durability.

Chris spends most of his time “power brokering ecosystems” — connecting portfolio companies, aligning operators, and engineering situations where one plus one equals three. That’s not passive investing. That’s involved capital.

This is exactly why a family office would trust managers like him.

The Lesson Most Entrepreneurs Learn Too Late: Timing Matters

Chris’s journey revolves largely around exits. For example, he pulled the trigger on multiple sales right at the peak of valuations in 2021. It wasn’t because he timed the market perfectly, but because he understood a hard truth: “Your emotional valuation of a business is almost always higher than the market’s.”

Entrepreneurs love their companies as if they were their children. In the eyes of investors, they are assets.

To illustrate this, Chris referenced an old saying that applies painfully to founders: “Pigs get fat. Hogs get slaughtered.”

When it comes to selling, clarity is more important than greed or fear. When it comes to growth, though, sometimes squeezing out one more turn isn’t the best decision. In other words, it’s realizing that someone else is better suited to continue the story.

Only that mindset separates operators from allocators.

Reckless Optimism vs. Rational Capital

The entrepreneur-investor divide is perfectly captured by a phrase Chris’s firm uses internally: Reckless optimism.

Entrepreneurs need it. Investors can’t afford it.

As builders, we’re confident that we will find a way. We will hire the right people. We’ll eventually figure it out. When left unchecked, that mindset creates companies, but it can also destroy capital.

When Chris invests, he starts with the opposite mindset: This is a bad deal, unless it is proven otherwise.

That inversion is essential. This is why so many great entrepreneurs have trouble becoming investors. It’s a different set of skills. There are different filters. Emotionally, the posture is different.

One thing Chris excels at is bridging that gap by focusing on the human across the table.

Bet on the Jockey — Always

I’ve been saying this for years, and it was refreshing to hear Chris articulate the same principle so clearly: You’re not betting on the horse. You’re betting on the jockey.

There are times when decks can be perfect. Often, markets appear massive. Seductive TAMs can be hard to resist.

However, if the founder lacks:

• Grit
• Resilience
• Alignment with co-founders
• The scars of having done it before

The deal is fragile.

As Chris points out, entrepreneurship is like getting a black belt in Brazilian Jiu-Jitsu — you can only get there by staying the course when it’s easy to quit.

That’s what he’s looking for. It’s not hype or polish. It’s all about proven endurance.

How the Wealthy Actually Allocate Capital

For Lifestyle Investors, the most important takeaway is how closely Chris’s worldview matches the data I share.

The wealthiest families in the world:

• Hold 15–25% in public equities.
• Allocate 50–60% to alternatives.
• Use public markets primarily as collateral, not as growth engines.

In other words, true wealth is built on private equity, real estate, private credit, and selective venture exposure.

This was beautifully explained by Chris:

• Venture: Minority stakes, long-term MOIC focus, and higher risk.
• Private equity: Cash flow, distributions, and Internal Rate of Return.
• Private credit: A predictable yield with downside protection.
• Real estate: The ultimate wealth-building tool.

This isn’t a theory. This is how a family office can compound across generations, as Chris has demonstrated.

Smart Capital Beats Capital Every Time

What truly differentiates Chris and firms like Solyco? Their commitment to smart capital.

It’s not just about money. But operators, advisors, networks, pattern recognition, and real help when things get messy.

In fact, one of the things Chris said stuck with me: “I wish I had this when I was building my companies.”

That’s what makes a great investor. Shortening someone else’s learning curve by using your experience.

Why Chris Van Dusen Stands Out

Chris isn’t flashy. He’s not chasing vanity deals. He’s not selling dreams.

However, he’s doing something far more powerful:

• Aligning incentives
• Respect for risk
• Understanding the cycles
• Thinking in decades, not quarters

Because Chris plays the long game, sophisticated capital listens to him in a world obsessed with speed and scale.

This is the mindset anyone who wants to build sustainable wealth, rather than just fast money, should study. And this is the kind of person you want on your side of the table.

Key Takeaways

• Access beats intelligence every time. The wealthiest families aren’t smarter — they just have access to a better playbook. In the end, leverage, private markets, and disciplined allocations matter more than IQ or hustle.
• Most real wealth is built outside the stock market. Private equity, real estate, and private credit are the main alternatives in which a family office invests their capital, with the public markets serving mainly as a source of liquidity and leverage.
• Entrepreneurship and investing require opposite mindsets. Building a business requires reckless optimism. Investing begins with skepticism. Being able to switch hats and not confuse them is a rare skill.
• Timing matters more than perfection. A great exit often comes from realizing when the market is giving you a gift — not from squeezing the last drop out of a business. When ego gets in the way, otherwise life-changing results can be destroyed.
• Always bet on the jockey, not the horse. Even a mediocre idea can be salvaged by a resilient, experienced founder. But when a founder is weak or misaligned, it can ruin an otherwise great company. Results are driven by people, not decks.
• Smart capital is more valuable than capital alone. The stakes are high when it comes to money. Private markets are particularly reliant on experience, pattern recognition, and the right network to compound value.
• Think like a steward, not a speculator. To build long-term wealth, you must balance wealth creation and wealth preservation-allocating risk intentionally, not emotionally. It’s that mindset which professionals like Chris Van Dusen bring to every deal.

Featured Image Credit: Kampus Production; Pexels: Thank you!