Lessons in Diversified Investments, Risk Management, and Trust
A Painful but Powerful Teacher
It was a crisp fall morning when I opened an email that changed everything.
Not because of the numbers, though they were bad, but because of what they revealed: a deal I had personally invested in, championed by someone I knew through a mutual connection, had gone completely off the rails.
And it wasn’t just one deal.
I wish it were.
There were a couple of investments I had made around that same time, all in the name of diversification. On the surface, that’s exactly what I was doing, spreading risk across different projects, which is a core principle of smart investing.
But here’s what I learned the hard way: diversification only works when it’s done right.
In both cases, the sponsor wasn’t a general partner, so they had no control. I was a passive investor putting trust (too much of it, it turns out) in people who didn’t deserve it. One delay here. A “small glitch” there. And then, the truth unraveled. Mismanagement. Misrepresentation. Even, in one case, outright deceit.
I lost money. More than I’d like to admit.
The initial emotions were gutting: anger, frustration, and that sinking feeling of betrayal. But after the fog cleared, what emerged was something more lasting – clarity.
These losses forced me to take a long, honest look at what “safety” in investing really means. They reshaped how I evaluate deals, who I partner with, and how I approach not only my capital, but yours.
And they became a cornerstone of how we do things at Apta Investment Group.
Because if you’re a physician or surgeon working long hours and trusting someone else to help build your financial freedom, you need to know those people are operating with the highest standards of integrity, transparency, and diligence.
I’ll walk you through the hard-earned lessons from those losses, why they matter, and how we use them to help you grow wealth.
The Loss That Changed Everything
One of the most formative losses came from a deal outside my usual network. It was packaged beautifully, a glossy pitch deck, slick presentation, and what seemed like an easy win.
And that’s exactly what made it dangerous.
Caught up in the momentum, I skipped steps I normally wouldn’t. I didn’t vet the operators like I should have. I trusted the surface instead of digging deeper.
That deal didn’t just underperform, it failed completely. The collapse was swift and costly.
I lost multiple six figures.
But it wasn’t just the money. It was what that money represented: years of discipline, missed weekends, long shifts at work, and precious time away from my family. It was capital earned through sacrifice, and I had let it slip away through complacency.
That loss cracked something open. It forced a brutal audit of my own process and a recommitment to never letting that happen again.
From that failure came the strengthened systems and standards we now use to evaluate every deal we bring to our investors at Apta. Because it’s not just about generating returns. It’s about safeguarding the time, energy, and dreams behind every dollar you invest.
3 Key Lessons from Losing My Own Money
Lesson 1: Relationships don’t replace due diligence.
Just because someone is a “good person” doesn’t mean they’re a good operator. Character matters, but so does competence. I learned that the hard way.
At Apta, we go beyond surface-level trust. Before we consider any deal, we dig into the numbers, stress test assumptions, and review track records with a fine-tooth comb. We ask tough questions and verify every answer, because integrity without capability is a recipe for failure.
And one crucial point to consider is whether the sponsor is actually a general partner in the deal. If they don’t have control or decision-making authority, even your trust in them can’t safeguard your investment.
Lesson 2: Shiny doesn't equal safe.
If it sounds too good to be true, it probably is.
The deals that promise sky-high returns with minimal risk? They’re usually built on shaky ground. At Apta, we don’t chase hype or fall for flash. We pursue conservative, resilient growth rooted in fundamentals. We consider deals that are sustainable, not sensational.
I’d rather underpromise and overdeliver than sell a dream that turns into a nightmare.
We ask the critical questions: How much leverage is involved? Is the team overexposed with debt maturing in just a couple of years? If the debt matures in less than five years, that opens the door to risk, especially in a volatile interest rate environment. Without enough runway, even a solid business plan can fall short.
Lesson 3: Risk isn’t always obvious.
Some risks don’t show up in the headline numbers or executive summary. They’re buried in assumptions, hidden in the fine print, or masked by optimistic projections.
That’s why I now approach underwriting like a pessimist, assuming the worst, and capital deployment like a steward, protecting every dollar as if it came from my own family.
Because often, it does.
Why Investor Capital Is Sacred at Apta
Those losses forever changed how I think about money, especially other people’s money.
At Apta Investment Group, we treat every investor’s capital with even greater care than we give to our own.
Because here’s the truth. If I had performed the same level of due diligence on my personal investments back then that we insist on for every deal at Apta, I would have never put money into those deals where I ultimately lost.
Experience taught us the hard way that protecting capital isn’t just about trusting a good story or a familiar face, it’s about a relentless, disciplined process.
Today, we’ve built rigorous systems and taken deliberate steps to reduce risk. Not because risk can be eliminated, it can’t, but because we know firsthand the cost of getting it wrong.
That’s why we work exclusively with seasoned, proven operators. We scrutinize every deal structure, every projection, and every assumption embedded in the business plan.
We avoid the traps I once fell into: short-term debt that limits flexibility, over-leverage that squeezes margin for error, and glossy narratives that mask fragile fundamentals.
Because this is more than just investing.
This is stewardship.
And the lessons from my own losses have made us far more thoughtful, diligent, and disciplined about protecting what matters most: your freedom, your time, and your legacy.
How We Avoid the Mistakes I Made
The lessons from my losses are now woven into every part of how we operate at Apta Investment Group. We’ve turned those hard-earned experiences into a disciplined framework designed to minimize risk and maximize clarity for our investors.
Here’s how we approach each investment with care and intentionality:
We’re General Partners With Real Control
We don’t just sit on the sidelines. At Apta, we are always general partners, either solely or as co-general partners with trusted operators. This gives us direct control and decision-making authority in every deal.
That’s critical. It means we’re not just hoping things go well, we’re actively shaping the outcome. We’re involved in the strategy, execution, and oversight from start to finish.
When we say we’re hands-on, we mean it
Rigorous, Multi-Layered Underwriting
Every opportunity must pass through a multi-step underwriting process. We don’t rely on one analysis or one model, we stack perspectives like a Swiss cheese model to systematically reduce risk. We dig into market dynamics, expense projections, income trends, and exit strategies. We assume the worst, test for resilience, and only move forward if a deal holds up under pressure.
We analyze not only the upside but the downside, and ask, “Can this project still succeed if the economy doesn’t?”
Only Partnering With Seasoned Operators
When we do co-GP, we only work with teams who’ve been through multiple market cycles and have the scars to prove it.
These are operators who don’t just chase deals; they manage risk. They treat investor capital with reverence. We vet their processes, their communication style, and how they’ve handled challenges in the past. If there’s a red flag, we walk away.
Stress-Testing Every Scenario
Optimism can be a liability in investing. That’s why we pressure-test every deal with pessimistic assumptions.
What happens if rents soften? What if we can’t refinance on schedule? What if interest rates spike or rehab delays stretch months longer than planned?
If the deal can’t survive those scenarios, it doesn’t make the cut.
Full Investor Alignment
We don’t offer deals we wouldn’t invest in ourselves – period.
In fact, we do invest in every deal we bring to our investors. Our capital is in the same pool as yours, under the same terms. That’s not just a philosophy, it’s a non-negotiable.
Because alignment isn’t just about skin in the game. It’s about trust, accountability, and honoring the effort behind every dollar you invest.
Your Capital Deserves More Than Hope
Many physicians are told to “just diversify” or funnel their hard-earned income into Wall Street and hope for the best.
But hope isn’t a strategy.
At Apta, we believe your capital deserves more. More transparency, more intentionality, and more resilience. When done right, real estate provides more than just returns. It offers control and long-term wealth building. But only when it’s built on a foundation of discipline, experience, and stewardship.
That’s our approach at Apta. And I’m proud to share two things that speak to our process:
- We have never lost investor capital.
- And in over 20 years of investing in real estate, I’ve never had to issue a capital call.
That doesn’t mean there’s no risk. It means we are intentional about how we manage it, choosing projects and partnerships with care, building with margin for error, and operating with a deep respect for the trust you place in us.
Final Thoughts from the Heart
Losing money in my investing journey was painful, but it was also a gift. It made me a sharper investor and a more responsible steward of capital.
If you’ve ever lost money in an investment, I see you. I’ve been there. It’s not just about the financial loss, it’s the frustration, the doubt, and the feeling of being let down.
But there is a better way forward. A way built on transparency, discipline, and shared commitment.
If you’re ready to invest differently, with clarity, care, and a team who treats your capital like their own, I invite you to explore what we’re building at Apta Investment Group.
Join Our Investor Network to take your first step toward financial independence.
*Apta Investment Group does not provide financial, legal, or tax advice. We recommend consulting with a qualified financial advisor before making any investment decisions.
