Financial Freedom That Doesn’t Cost You Family Time

In financial services, most people follow a predictable path: climb the ladder, gather assets under management, protect the brand, and never disrupt the status quo.

Chad Willardson did the opposite.

Despite the corner office, corporate prestige, and other external markers of “success” that Chad had at Merrill Lynch, he left after nearly a decade. It wasn’t because he failed. Instead, he saw a better way to create wealth, design lives, and serve people who think like entrepreneurs.

The exit isn’t the only thing that makes Chad’s story compelling. It’s what he built after — and the principles that guided every decision he made.

From Time on Wall Street to Entrepreneurial Freedom

Having been inspired by a cousin who managed mutual funds and analyzed companies and markets, Chad started his wealth management career straight after college. As a result of that early exposure, he developed a genuine love for long-term investing, research, and thinking.

He was given a powerful platform by Merrill Lynch. However, after the acquisition by Bank of America and the growth of bureaucracy that followed, the environment changed. There was a narrowing of creativity. Flexibility has disappeared. The decision-making process slowed down.

It became suffocating for someone wired like an entrepreneur.

So Chad did what many dream of but few actually accomplish. He walked away.

At the time, Chad had three kids (soon to be five), no corporate safety net, and plenty of skeptics in his inner circle.

While it was both risky and uncomfortable, it was exactly the right move.

A Financial Advisor Who Thinks Like an Entrepreneur

Entrepreneurs connect with Chad because he doesn’t see himself as a traditional financial advisor.

In most cases, advisors recommend what they’re paid to recommend. Many don’t invest in the same strategies they recommend to their clients. And very few truly understand how entrepreneurs think about risk, opportunity, and growth.

Chad, however, does because he is one.

The approach he takes is open-minded and allocation-driven. Despite his belief in public markets, he does not see them as the only solution. In addition to real estate, private equity, and venture capital, he even incorporates a measure of crypto into his clients’ lifestyles, values, and goals.

That alignment matters. It’s especially noteworthy when you consider that the world’s wealthiest families routinely allocate 50–60% of their wealth to alternative investments rather than stocks and bonds alone.

Why He Walked Away from 75% of His Clients

As President and Founder of Pacific Capital, a family office services firm helping high-net-worth entrepreneurs achieve both lifestyle and financial freedom, Chad made a bold, counterintuitive move: he intentionally shrunk his client base even as Pacific Capital continued to grow.

Rather than sell the entire firm, he sold roughly 75% of its clients — specifically those below $25 million to a partner firm. As a result, he was able to focus exclusively on ultra-high-net-worth entrepreneurs who wanted family office-level advice.

The result? Deeper relationships. Better alignment. More impact.

Additionally, it allowed Chad to focus on what matters most to him — his family, his businesses, and his community.

Building Wealth Without Selling Assets

Chad’s core philosophy mirrors that of the ultra-rich: buy, borrow, never sell.

As opposed to liquidating appreciated assets and paying taxes, Chad uses leverage strategically to fund real estate and private investments. As a result, capital compounds while being deployed elsewhere. In other words, this is where the cash generated by one asset is reinvested into other investments. With this approach, you can receive returns from multiple sources simultaneously. 

In today’s higher-interest-rate environment, this approach remains sensible when used strategically and aligned with cash flow and long-term objectives.

In the end, it’s not about financial engineering. It’s about optionality.

Why He Still Works—Even Though He Doesn’t Have To

After his partial exit, Chad could have walked away entirely. That didn’t happen.

Why? Because he loves what he does.

Besides Pacific Capital, Chad owns and operates sports complexes, runs youth travel teams, leads an elevated entrepreneur mastermind, and serves as an elected city treasurer — managing over $650 million in taxpayer funds.

He also assisted in improving his Southern California city’s credit rating, refinancing debt, and growing the portfolio from $230 million to $650 million as a volunteer. This saved taxpayers an estimated $170 million in interest.

This is exactly what purpose-driven wealth looks like.

Leverage Isn’t Just Financial—It’s Time

Chad’s most powerful insight has nothing to do with money.

Time is the real asset.

By building systems and surrounding himself with the right people, he aggressively buys back his time — including multiple executive assistants with clearly defined responsibilities. With his “right-brain / left-brain assistant” framework, he separates creative, relational tasks from operational, financial ones.

As a result of clarity, momentum is created. And momentum creates freedom.

The Fully Invested Life

Chad’s mission in life is simple: success at work should never mean failure at home.

He opposes hustle culture. It’s not because ambition is bad. But because misplaced sacrifice is dangerous.

Instead, Chad lives what he calls a fully invested life: family first, health second, fulfillment alongside business growth — not after it.

Everything he does, from his calendar to his financial decisions, is influenced by that philosophy. Priority is given to family commitments. The gaps are filled by business.

Balance isn’t the result. It’s alignment.

Key Takeaways

• Corporate success doesn’t equal personal freedom. There are still times when prestige and stability aren’t aligned with who you really are.
• Entrepreneurs need advisors who think like owners. Credentials are not as important as alignment.
• The ultra-wealthy diversify beyond public markets. Concentration is riskier than alternatives.
• You don’t build wealth by selling great assets. Compounding and flexibility are preserved by strategic leverage.
• Exits aren’t about stopping — they’re about choosing. Optionality, not inactivity, is the goal.
• Time leverage beats financial leverage. Money alone does not create freedom as fast as systems and people do.
• Winning in business should never cost you your family or health. The ultimate return on investment is a fully invested life.

Featured Image Credit: Joey Kyber; Pexels: Thank you!