Angel Investing Isn't Passive—It’s Personal

What does it mean to be an owner? For me, it has often meant stepping into the fire of uncertainty—staking capital on something that doesn’t exist yet. As physicians, we're used to precision and predictability. But as entrepreneur-investors, we must learn to breathe a different kind of air—one filled with risk, vision, and sometimes, painful disappointment.

Today I want to talk to you about angel investing—from both sides of the deal:

1. When you're the angel investing in someone else's dream

2. And when you're the entrepreneur seeking angels to back your own

I've been both. And I’ve got the scars—and the insights—to prove it.

Case Study 1: The Silent Angel in Solomon Development Group

It started quietly. A trusted contact pitched me an opportunity: an $80,000 silent angel investment in a low-income housing project. I wasn’t managing it. I wasn’t even advising it. I was just the “money guy.” A way to help a community and grow some wealth.

What followed was a classic early-stage investor nightmare.

The managing partner turned out to be unscrupulous. Corners were cut. Decisions were made that endangered the long-term success of the project. And because I was just a silent investor, I had no operational control—until things imploded.

In a scramble to salvage the deal, I had to inject an additional $170,000, becoming the project manager by necessity, not design. What began as passive became very active. I spent two decades holding that property, ultimately selling it—long after the shine wore off.

I didn’t lose everything. But it wasn’t the return I envisioned. And more importantly, I learned the single most important rule of angel investing:

💡 If you’re not willing to lose every dollar you invest, you shouldn’t be an angel.

Case Study 2: Investing in Family — The Emotional Trap

Later, I joined forces with my brother-in-law to support a promising security barrier company, US Stronghold. The idea was compelling, the need was real, and we had early traction. I invested heavily and stepped in with operational support.

Then tragedy struck. My brother-in-law suffered a traumatic brain injury at work. Suddenly, the operational leadership collapsed. The company couldn’t recover. I was left to settle over $100,000 in business debt, effectively absorbing the loss myself.

This was more than a financial blow—it was emotional. Investing in family is fraught with risk, not just of money, but of relationship strain and personal grief. The loss blurred personal boundaries and reminded me that angel investing isn’t just a numbers game—it’s a trust game. And that trust is fragile.

Case Study 3: Receiving Angel Capital for ChatRx

Today, I stand on the other side of the table.

As the founder of ChatRx, I’ve invited angel investors into my own vision—a radically accessible, AI-powered telemedicine service for common infections. In doing so, I’ve relinquished equity. I’ve shared ownership. I’ve faced hard conversations about valuation, risk, and investor return expectations.

And I’ve had to wrestle with this question:

🔁 How do you invite capital in without compromising your mission?

The answer? You only take angel money from people who believe in more than profit. People who resonate with your vision. People who trust you. And you build in protection: clear operating agreements, clean cap tables, and staged funding rounds.

Lessons from the White Coat Investor

In one of my favorite breakdowns of this topic, White Coat Investor’s post on angel investing lays it out bluntly:

• Angel investing is a negative expected value game

• You are very likely to lose most or all of your money

• Diversification matters

• Only use money you can afford to lose

• Invest for fun, mission, or mentorship, not for guaranteed financial return

As doctors, our wealth often flows from stable clinical income. But our entrepreneurial spirit sometimes leads us to make riskier bets. The key is awareness. You must know why you're investing, what you're risking, and what kind of return you're really expecting.

From Passive Angel to Active Steward

So how do you think like an owner in the world of angel investing?

You don’t just write a check and pray. You do your due diligence. You ask the hard questions. You expect failure—and plan for survival. You prepare for the long haul.

And if you’re on the other side—seeking angel capital—you do the same. You protect your dream. You communicate with clarity. You don’t sell out your values for a check.

Angel investing is not glamorous. It’s gritty. But when done right, it can create deep alignment, long-term growth, and shared transformation.

Throwback Wisdom: A Past Lesson in Business Identity

In my prior post, "Stop the Insanity: Working Just One Job for One Employer is Holding You Back", I reflected on how your identity must shift from worker to owner—if you’re ever going to fully control your future. That same identity shift is required when moving from “doctor-investor” to “angel-owner.”

🌀 Read More on The Independent Doctor Blog

→ Stop the Insanity

Free Resources to Build Your Ownership Mindset

If you’re exploring the world of physician entrepreneurship, you don’t have to do it alone. Whether you’re raising capital, managing investor relationships, or evaluating startup opportunities, you need a strategy.

Here are a few free tools and resources that can help:

📘 Why Every Doctor Should Form a Micro-Corporation Understand how a professional entity can help you retain control and reduce risk.

📗 Mindset Shift Mapping Worksheet Clarify your transition from physician to entrepreneur to investor.

📘 Doctor, You Are A Business A full course experience to rewire how you think about your professional identity.

Identity Shift Step

“Still thinking like an employee? It’s time to own your time, your work, and your income.”

👉 Start Your Transition with PEA Explorer Membership → OR

📥 Download Your Free E-Book: Doctor Incorporated →

Final Thought

Being an angel is not about wings—it’s about wisdom. Whether you’re backing someone else’s dream or raising support for your own, ownership begins with self-awareness.

Ask yourself today:

“Am I building something I truly believe in? And am I ready to take full responsibility for its outcome?”

That’s what it means to think like an owner.

— Dr. Tod Stillson Founder, PEA-SimpliMD