5 Lessons I Learned the Hard Way About Business Success

I’ve been through it all — companies that soared, companies that sank, deals that looked like gold and turned out to be sand and partnerships that either multiplied value or silently killed it. If there’s one brutal truth I’ve learned after decades of building, buying, selling and sometimes burying companies, it’s this:

Relationships — not ideas, capital or even timing — are the ultimate determinant of success.

It’s a lesson that no spreadsheet will teach you and no pitch deck will fully convey. But it’s the one thing every founder, CEO, investor and partner needs to internalize if they want to build something that lasts.

Let me explain through five unfiltered truths I learned the hard way — some through exits, some through bankruptcies.

Related: How to Build and Sustain Deep, Meaningful Business Relationships (and Why It’s the Key to Long-Lasting Success)

1. Bad partnerships are more expensive than bad products

A bad product can be fixed. A misaligned partner? That’s a cancer in the system.

I once co-founded a company with incredible potential — strong unit economics, great early adoption and even some early buzz in the media. But internally, the leadership team was fractured. One partner prioritized short-term revenue. Another obsessed over product perfection. And I, caught between the two, tried to play referee.

Guess what happened?

We burned cash arguing. We stalled decisions. Morale tanked. Ultimately, the company died — not because of the market, but because we couldn’t get out of our own way.

Looking back, I now ask this before every deal: Do I want to be in a foxhole with this person when things go wrong? If the answer isn’t a hell yes, it’s a no.

2. Bankruptcy is a leadership failure, not a market failure

Yes, markets change. Yes, industries shift. But most of the bankruptcies I’ve seen — including my own — weren’t because of the economy. They were because we made poor decisions, delayed hard conversations and ignored red flags.

We had a company that seemed unstoppable — fast-growing, flush with investor interest and scaling quickly. But internally, management was siloed. Sales leadership was misaligned with operations. Decisions were made based on ego instead of data. We ignored tension because things were “good enough.”

Until they weren’t.

When it collapsed, it was easy to point fingers at external market conditions. But the truth? We failed ourselves.

That experience forever changed the way I build. Now, every leadership meeting starts with alignment. If leadership isn’t rowing in the same direction, I don’t care how good the boat is — it’s going nowhere.

Related: Want Strong Business Relationships? Avoid These 3 Mistakes.

3. Buyers don’t buy products — they buy people

When I’ve successfully exited companies, there’s a pattern that shows up every time: We were aligned with the buyer on values, vision and execution style.

One of our best exits came not because we had the best tech, but because the acquiring team said, “We want to work with you guys.” They knew we had strong relationships across departments, high employee retention and a culture of transparency.

Deals get done when there’s trust. Period. It doesn’t matter how great your EBITDA is if the buyer doesn’t believe in your leadership or your people.

If you’re preparing to exit, ask yourself: Would you buy this company if you didn’t know the numbers, but just knew the people running it?

If the answer is no, you’ve got work to do.

4. Decision-making is a muscle — train it or lose it

Poor decision-making doesn’t show up all at once. It’s a slow erosion — a hundred little moments when you defer, delay or delegate decisions you should own.

One business I led started slipping when we over-delegated key choices to mid-management without ensuring those managers were aligned with the company strategy. Over time, execution drifted. Product launches missed the mark. Marketing lost focus. And we didn’t notice until revenue plateaued.

Strong companies don’t just have good leaders — they have good decision-making systems.

Now, in every company I touch, we prioritize decision hygiene. Clear frameworks. Accountability. Retrospectives. You can’t outsource judgment. You have to train it.

Related: 8 Strategies for Building Long-Lasting Business Relationships

5. The exit isn’t the end — it’s the mirror

When you sell a company, the terms of that exit reflect everything you did right — or wrong.

Great exits happen when:

• You have strong internal processes

• Your financials are airtight

• Your leadership team is trusted

• Your reputation precedes you

Bad exits — or worse, failed exits — happen when:

I’ve lived both sides, and I’ll tell you: Nothing haunts an entrepreneur more than realizing they killed a great business by not focusing on the fundamentals early enough.

So, what’s the takeaway? If I could give one piece of advice to any founder building a startup today, it’s this:

Invest in relationships before you invest in features. Build trust before you build scale. Fix your internal operating model before you chase more revenue.

Money follows alignment. Buyers follow leadership. Teams follow purpose. And if you get those right, the next big thing might just follow you.