There’s a funny thing about experience: It doesn’t always make you immune to failure. In fact, some of the most seasoned, intelligent founders I’ve met — including myself — have walked straight into the same fire multiple times, thinking this time would be different.
After buying, building, burning and selling businesses ranging from $1 million to over $20 million in annual recurring revenue, with teams as small as five and as large as 500, I’ve seen these mistakes up close. Not once. Not twice. But over and over. I’ve made them myself. I’ve watched peers make them. And most frustratingly, I’ve watched incredibly smart entrepreneurs make them while fully aware of the warning signs.
Why does it keep happening?
Because we convince ourselves that this time is different. We raised more capital. We’re in a new vertical. The economy has shifted. We’ve got better advisors. But these so-called differences rarely change the fundamentals. These mistakes don’t care about your funding round, your pitch deck or the decade you’re building in. They always find a way to show up … unless you deliberately learn to recognize and avoid them.
Here are the top five mistakes smart entrepreneurs keep making — because intelligence alone isn’t protection.
Related: 5 Common Entrepreneurial Mistakes There Is No Excuse for Repeating
1. Outsmarting simplicity
Smart founders love strategy. We love architecture, systems and layered thinking. But too often, that intelligence leads us to outsmart ourselves by overcomplicating something that should’ve stayed simple.
In one of my earlier ventures, we created an onboarding system so “intelligent” that it required a five-step identity verification, AI scoring and three user roles. It was technically perfect — and completely unusable. Not a single customer made it through the first interaction without needing help. We had engineered a fortress when all the customer needed was a front door.
Simple is not a synonym for lazy. Simple is scalable. Simple gets used. If your product, process or pitch can’t be explained in one sentence, you’re not impressing people — you’re confusing them. Don’t make the mistake of confusing complexity with value. Often, it’s the opposite.
2. Overbuilding before testing
It feels so good to build. It feels like progress. It’s measurable. It’s exciting. But building without real customer validation is like sailing without checking the tide: You might be moving fast, but you’re heading toward a sandbar.
I once spent months and hundreds of thousands of dollars building a tool we were sure the market wanted. We built features on top of features, tied in AI recommendations, created dashboards, reports, you name it. But we hadn’t tested the core value with real users. When we finally launched, the silence was deafening.
We didn’t fail because we couldn’t build. We failed because we didn’t listen.
Your MVP should hurt a little. It should feel unfinished. Because the moment you build past the point of user feedback, you’re building for yourself — not your customer. Build to learn. Then build to scale.
3. Ignoring customer feedback that hurts
Let’s be honest: Some feedback cuts deep. Especially when you’re passionate. When you’ve poured years into a business or a product, hearing that it’s confusing, clunky or not worth the money feels personal.
At one point, while scaling one of my companies, we were receiving consistent complaints about our service response time. We brushed it off. “Growing pains,” we said. “We’re expanding.” But the complaints kept coming, and we kept rationalizing — until the damage was no longer subtle. Clients started leaving. Our reputation took a hit. And fixing the problem cost ten times what it would’ve if we’d acted earlier.
Feedback, especially the kind that makes you wince, is gold. Don’t dodge it. Don’t argue with it. Use it. Because every complaint you ignore becomes someone else’s competitive advantage.
Related: 5 Common Mistakes Leaders Make and How to Fix Them
4. Misjudging your own burn rate
This is one of the deadliest mistakes. And ironically, it’s more common among founders who’ve raised capital or had prior exits. You think you’ve got room. You think you’re being strategic by “investing in growth.” And suddenly, your company’s financial discipline goes out the window.
I’ve run tight operations. I’ve also run operations with fat budgets and too much confidence. The tight ones were stressful, but lean and sharp. The overfunded ones got bloated fast — extra hires, experimental campaigns, unnecessary vendors. All in the name of growth. But here’s the thing: Growth doesn’t matter if you don’t survive long enough to reach it.
Every dollar should work. If you can’t justify it with near-term utility or long-term leverage, you’re probably burning money you’ll wish you had six months from now.
Being a smart entrepreneur doesn’t mean ignoring your burn rate; it means obsessing over it. Because financial waste isn’t just inefficient — it’s existential.
5. Hiring more people to solve the problem
This one is almost a rite of passage. Things start breaking — operations, marketing, delivery — and the instinct is: “We need more people.”
Founders tell themselves that scaling the team will fix it. VCs sometimes push for headcount growth as a signal of momentum. But nine times out of ten, it’s the wrong move.
I’ve scaled teams from five to 200+. I’ve watched entrepreneurs stack up departments like LEGO blocks, trying to fix broken pipelines, unclear roles or systems that never worked in the first place. The result? More meetings, more chaos, more burn. Not more progress.
Throwing people into a broken system just gives you more breakage.
What I’ve learned is that most problems can be solved by a few qualified individuals with clarity and autonomy, not by hiring a battalion. Talent density beats volume every time. If your house is on fire, you don’t fix it by moving in more tenants. You put out the fire.
Related: 10 Stupid Mistakes Smart People Make
Intelligence isn’t insurance
It’s easy to assume that once you’ve built or sold a company, you’ve “earned” your wisdom badge. But the real test isn’t whether you’ve experienced these mistakes before — it’s whether you keep making them.
Experience without reflection is just repetition.
I’ve built companies with world-class teams. I’ve also watched great ideas burn out because I refused to listen to the basics. These five mistakes show up over and over, usually wrapped in new branding, new market conditions or new funding. But they’re the same patterns, and they still kill momentum.
So here’s your call to action: Audit yourself.
Where are you overcomplicating? Where are you building without feedback? Where are you hiring instead of solving? Where are you ignoring warning signs because they’re inconvenient?
The smartest move you can make isn’t being clever — it’s being clear. Because clarity builds endurance. And endurance is what separates the companies that survive from the ones that almost did.
There’s a funny thing about experience: It doesn’t always make you immune to failure. In fact, some of the most seasoned, intelligent founders I’ve met — including myself — have walked straight into the same fire multiple times, thinking this time would be different.
After buying, building, burning and selling businesses ranging from $1 million to over $20 million in annual recurring revenue, with teams as small as five and as large as 500, I’ve seen these mistakes up close. Not once. Not twice. But over and over. I’ve made them myself. I’ve watched peers make them. And most frustratingly, I’ve watched incredibly smart entrepreneurs make them while fully aware of the warning signs.
Why does it keep happening?
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