A few years out of college, I was sure I had found my golden ticket.
Some college friends had launched a venture capital firm and had what they called the “perfect” investment. Not just any investment—this was the investment, the kind that could change everything. It was the next great thing, a competitor to Netscape, which at the time was huge.
The excitement was contagious. The projections looked incredible. The potential return was staggering. We couldn’t lose.
There was just one problem: I didn’t actually have the money to invest.
But when faced with an opportunity this good, you don’t let minor details like cash flow get in the way, right? So, with all the confidence of a young professional convinced he was about to outsmart the system, I did something bold. I took out a cash advance on my credit card—somewhere in the range of $5,000 to $6,000—and made the investment.
With visions of financial freedom dancing in my head, I imagined all the ways this would change my life. I could pay off my student loans. Upgrade my car. Maybe even start investing more seriously.
All I had to do was wait.
The Waiting Game
At first, things looked promising. The company sent updates. The business seemed to be making progress. My friends and I would check in with each other, buzzing with anticipation.
But then the updates became less frequent. Questions were met with vague responses. Enthusiasm turned into silence.
And then, it was over. The company collapsed. My “sure thing” investment was worth exactly zero dollars.
I was devastated. And I wasn’t alone—several of my friends had invested too, all believing we had found our early-career lottery ticket. Instead, we had front-row seats to a very expensive lesson in reality.
The Three Questions I Didn’t Ask
Looking back, I now see all the warning signs I blissfully ignored. As a seasoned investor today, I know I violated three fundamental principles of investing:
What do you know about the management team? I trusted my friends, but I didn’t actually know anything about the people running the company. Experience, leadership, and a track record matter.
What do you know about the product? Beyond the pitch deck and spreadsheets, I didn’t really understand what made this company better than Netscape. Was there a competitive edge? A clear differentiator? I never stopped to ask.
What do you know about the market? The tech world moves fast. Just because a company wants to be the next big thing doesn’t mean there’s room for it. I had no clue about the actual demand or market conditions.
Instead of doing my homework, I had placed my faith in excitement, hype, and a deep desire for a shortcut to success.
The Truth About Shortcuts
So why do I call this my worst best investment?
Because it taught me a truth that has shaped everything I’ve done since.
Shortcuts rarely work.
That’s not to say they never do. Sometimes, people win the lottery. Sometimes, startups strike gold overnight. But those are the exceptions, not the rule.
The real path to success—whether in investing, business, health, or life—is rarely a straight shot. It takes time, effort, and persistence.
- Great investments don’t turn into massive wins overnight. They compound over years.
- Sustainable weight loss doesn’t happen in 30 days—it’s the result of consistent effort over time.
- Successful businesses don’t explode out of nowhere. Even the ones that seem like overnight successes often have years of struggle behind them.
We live in a world filled with people selling quick wins, promising instant results, and making it look easy. But the truth is, the ones who achieve real, lasting success are those who stick with it, push through the setbacks, and play the long game.
The Best Investment I Ever Made
So yes, my worst investment was a disaster financially. It set me back in the short term. It hurt. It humbled me.
But in the long run, it was one of the best investments I ever made—because it taught me the value of patience, persistence, and doing the work.
Whether you’re investing money, building something new, or trying to make a change in your life, don’t fall for the illusion of the shortcut. Play the long game. Stick with it. Keep going.
That’s where the real returns are.
See you next week,
Brent, your Rivr Guide
