5 Lessons from 50 Years in Business: A Guide for Modern Leaders

When you’ve been in the game as long as I have—watching the rise of the personal computer, the dot-com bubble, the mobile revolution, and now the AI wave—you start to see patterns. The suits change, the buzzwords evolve (remember when everything was about "synergy"?), but the fundamental laws of business physics remain stubbornly consistent.

In my five decades of navigating boardrooms from New York to Singapore, I’ve learned that while technology accelerates the pace of business, it doesn't change the nature of people. Whether you are a startup founder in Silicon Valley or running a family business in the Midwest, these hard-earned lessons are your blueprint for enduring success.

1. Relationships Compound Faster Than Interest

In 1985, I did a favor for a young supplier who was about to go under. It wasn't a massive gesture—just an introduction to a bank manager I trusted. I didn't think much of it at the time.

Twenty years later, that same supplier—now the CEO of a Fortune 500 logistics company—tipped me off to the biggest acquisition deal of my career. That one deal paid for my retirement.

The Lesson: Treat people well, not just because it’s the moral thing to do, but because it is the smartest investment you can make. In an era of transactional networking and LinkedIn connections, deep, genuine relationships are your most valuable asset.

Actionable Advice: Spend 20% of your week helping others without expecting an immediate return. The ROI on reputation is infinite.

2. Cash Flow is Oxygen, Revenue is Vanity

I’ve seen brilliant companies with "unicorn" valuations die overnight because they couldn't make payroll on a Friday. It’s a tale as old as commerce itself. Entrepreneurs often get seduced by top-line growth, ignoring the bleeding wound of negative cash flow.

"Revenue is vanity, profit is sanity, but cash is king."

Profit is a theory found in accounting books. Cash is the fact in your bank account. If you run out of cash, the game is over, no matter how "disruptive" your technology is.

Smart Old Guy Tip: Always keep a "war chest" of 6 months of operating expenses. It gives you the power to say "no" to bad deals and "yes" to opportunities when the market crashes.

3. Hire for Character, Train for Skill

You can teach a smart person how to read a balance sheet, run a Python script, or manage a marketing campaign. You cannot teach integrity, curiosity, or resilience.

I once hired a brilliant Ivy League MBA who looked perfect on paper but crumbled the moment a client shouted at him. Conversely, one of my best VPs started as a receptionist who simply refused to let problems go unsolved.

What to look for:

Grit: Have they overcome real adversity?
Curiosity: Do they ask questions, or do they just wait for instructions?
Integrity: Do they tell the truth even when it's ugly?

4. Failure is Data, Not Defeat

I launched a product in the late 90s that failed so spectacularly it made the trade papers. It was embarrassing. My ego was bruised. But the post-mortem of that failure revealed a gap in the market that led to my second successful exit.

In the modern startup ecosystem, "fail fast" is a cliché, but the nuance is often lost. The goal isn't to fail; the goal is to learn cheaply. Don't waste a good failure by wallowing in self-pity. Extract the data, pivot, and move on.

5. Stay Curious or Become Obsolete

The moment you think you know it all is the moment you start dying. I’m 75, and I spend an hour every morning learning about Generative AI and decentralized finance. Why? Because the world doesn't care about your past experience if it doesn't apply to the present context.

Experience gives you wisdom, but curiosity keeps you relevant. The combination of the two is unstoppable.

The Bottom Line

Business is a marathon, not a sprint. Pace yourself, keep your integrity, and never stop learning. That's how you become a "Smart Old Guy" (or Gal).

If you are looking for guidance to navigate your own marathon, consider connecting with a mentor who has run the race before. Join Smart Old Guys today and tap into a reservoir of timeless wisdom.