What if I told you that emotions can make or break your investments? Most people think emotional investing is a fatal mistake—but sometimes, it’s the best decision you can make.
At the end of the day, investing is 80% mindset and 20% strategy. The ones who master their emotions play the long game—and win.
Every seasoned investor has heard it before: stay rational, don’t let emotions cloud your judgment, and never buy high or sell low out of panic.
And yet, I found myself making an emotional investment. And surprisingly?
I wouldn’t change a thing.
A Life-Changing Encounter in Nairobi
During my investment week in Nairobi, Kenya, I met 20 local entrepreneurs, each with their own journey, struggles, and ambitions. (You can read more about my investments in Kenya in this blog series here)
But then came the moment that truly shook me.
John, the owner of a small garbage collection company, stood up to speak. But instead of asking for funding like the others, he said something that stopped me in my tracks:
“I’m not here to ask for money. I’m here to learn. I want to grow, improve my business, and better serve my community.”
His words carried a weight of humility and determination that I rarely see. As he spoke, he shared his excruciatingly difficult journey—one that was still ongoing. His voice trembled at times, his eyes glistened with emotion, but his spirit never wavered.
Then, he told us how he used to push a handcart for over 40 km a day, collecting garbage from households on foot. Slowly, he built a company with a small team, but his challenges were far from over.
I asked him, “Who do you want to become? What is your ultimate goal?”
Without hesitation, he locked eyes with me and said:
“I want to build the biggest garbage collection company in Nairobi and beyond.”
I sat there, speechless.
That night, I couldn’t stop thinking about him. His drive, his relentless hunger to grow, and his sheer willpower kept replaying in my mind. I wanted to mentor him, help him streamline operations, improve pricing, and scale efficiently.
I even considered personally donating $5,000 to help him replace one of his two broken trucks—because I knew that a single upgrade could exponentially change his business.
Yes, I know many entrepreneurs have come from nothing. I, too, have had my fair share of struggles.
But John’s story? It hit differently.
He wasn’t begging for money. He wasn’t looking for handouts. He just wanted someone to guide him, believe in him, and help him take his business to the next level.
More Than Just an Investment
I wasn’t the only one who felt this way.
In the end, our group of investors, together with the investment program organizers, rallied behind John—even though he didn’t meet all our usual investment criteria.
✔️ We collectively sponsored his enrollment in a local mentorship program, where he’ll learn directly from successful business owners in Kenya.
✔️ We pledged $5,000, not as a handout, but as an incentive—he’ll receive it to replace his broken truck once he completes the program.
Moments like this make me wish I could help even more entrepreneurs like John.
Because here’s the truth:
I’ve always had a soft spot for hardworking people with a good heart. I don’t care if they’re the smartest in the room or if they meet every checkbox on a selection form.
If I see fire, determination, and an unbreakable spirit, I’ll always take them under my wing.
And you know what? I don’t think John will ever fail.
It’s hard to beat someone who’s come from nothing—someone who used to walk 40 km a day just to collect garbage and build his dream from scratch.
But even if he does fail, I’m still happy.
Because at the end of the day, sure, returns matter, but sometimes, doing a little good for others—without expecting anything in return—enriches our lives, our souls, and our happiness.
Just imagine hitting the lowest point in your life, when you see no light at the end of the tunnel, and someone reaches out, lifts you up, and asks for nothing in return.
How uplifting and amazing would that feel?
Hold onto that feeling. Embrace that moment. And whenever you can, in any way that feels right for you, try to do the same for others—whether big or small, within your own limits and comfort zone.
For us, the group of investors who believed in John, it was never just about money.
We’re honored to play even a small role in his life, his business, and the people connected to it.
And to me, that’s a win worth celebrating.
Why Emotional Investing Might Not Be So Bad After All
This experience forced me to ask myself an uncomfortable question:
What kind of investor do I want to be?
Because the truth is, my real estate investments don’t bring any real benefit to the community—except for myself.
Yes, I make good returns. I buy, develop, and sell. But investing in people like John—or the two businesses I mentioned in my previous post. That’s what truly changes lives.
👉 It creates jobs.
👉 It creates opportunities.
👉 It creates a ripple effect that transforms entire communities.
And yes, I know it sounds cliché. But moving forward, I hope my investment path continues to evolve—not just toward profitable businesses, but toward impactful entrepreneurs and investors who want to create meaningful change.
Because the best kind of investment is one where everyone wins:
✅ Win for the investor.
✅ Win for the entrepreneur.
✅ Win for the community.
Final Thoughts
So, is emotional investing always a mistake?
Not necessarily.
If you let emotions cloud your judgment, you risk making poor financial decisions. But if you invest with heart and strategy combined, you can create both impact and profit.
Because sometimes, the best investments aren’t in stocks, real estate, or companies.
Sometimes, the best investment you’ll ever make is in people.
