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From the outside, entrepreneurship often looks like a highlight reel: rapid growth, media coverage, successful exits. I’ve lived that story — building and running multiple companies, serving as CEO of SetSchedule and exiting businesses in real estate and tech before moving into venture investment. But the truth is, my real education didn’t come from the wins. It came from the mistakes.
Now, as a venture investor focused on identifying what makes companies sustainable and founders resilient, I often reflect on the choices I would never make again. These aren’t just my battle scars — they’re the very things that made me a better entrepreneur. And in my experience, there are three big mistakes that many entrepreneurs, including myself, have made. If you’re building something now, let these serve as guideposts.
Related: 5 Lessons You Learn From Your Business Mistakes
1. Believing everyone can be a partner
In the early days of entrepreneurship, there’s a rush to build momentum — and in that rush, it’s easy to mistake proximity for alignment. I made the mistake of elevating early team members into partners without truly understanding if we shared the same values or long-term vision. Sometimes I felt a sense of obligation. Sometimes it was about giving someone a bigger stake to keep them around. But what I’ve learned is that true partnership is about more than titles or equity — it’s about shared sacrifice and belief in the mission.
When partnerships are built on convenience, compensation or charisma alone, they usually crack under pressure. Some of the most public business breakdowns stem from this same misjudgment. Facebook’s early falling-out between Mark Zuckerberg and Eduardo Saverin is a prime example. Saverin was there at the start, but their priorities diverged quickly — and that divergence led to a legal and personal battle that defined the early company culture.
Steve Jobs and John Sculley’s infamous fallout at Apple is another cautionary tale. Jobs brought Sculley in from Pepsi, thinking they could complement each other. However, their values and leadership styles clashed. Jobs was eventually forced out of the very company he founded.
I’ve been there. I’ve handed out trust before it was earned. I’ve mistaken transactional loyalty for long-term commitment. And I’ve paid the price in time, money and emotional bandwidth.
Lesson: Not everyone who starts the race with you is meant to finish it by your side. Partnerships require aligned values, not just aligned goals.
Related: I Made These 3 Big Mistakes When Starting a Business — Here’s What I Learned From Them
2. Chasing growth at all costs
If you’ve ever pitched a VC, you’ve probably said some version of: “We’re growing fast.” For a while, I believed that speed was the only thing that mattered. I expanded teams, opened new verticals and pushed marketing spend to the limits — all in the name of growth. But fast growth without a strong foundation is like building a skyscraper on sand.
I once doubled the size of a team before understanding what our most efficient systems were. The result? Burnout, bloated overhead and a product that wasn’t improving fast enough to justify the scale.
There are plenty of case studies here. Fast, a one-click checkout startup, raised $120 million before shutting down in 2022 — despite growing headcount and marketing spend aggressively. The product couldn’t keep up with the hype. Or consider WeWork, which became the poster child for “growth at all costs.” At its peak, it was valued at $47 billion. By 2023, it was struggling for survival, largely because it expanded faster than its core business model could support.
In both cases — and in mine — growth wasn’t the enemy. But chasing it without discipline, without product-market fit and without unit economics is a fast way to scale failure.
Lesson: Sustainable growth is a byproduct of a strong product, efficient operations and clarity of mission — not just ambition.
3. Becoming unconditionally obsessed with the business
Entrepreneurs are told to be obsessed. Live it. Breathe it. Sacrifice everything for it. And yes, you have to care deeply. But here’s the trap: When your identity is too tightly tied to your company, you lose sight of its natural life cycle — and your own.
I’ve seen brilliant founders miss exit opportunities because they believed they were building something eternal. I’ve done it, too — clung too tightly, too long. But here’s what I’ve come to understand: Businesses have a shelf life, and smart founders learn when to enter, when to scale and when to exit.
Jeff Bezos, one of the greatest builders of our time, famously said: “Amazon is not too big to fail… In fact, I predict one day Amazon will fail.” He pointed out that companies have lifespans, and the goal is to prolong it as much as possible while accepting that no company lasts forever.
Think about the S&P 500 twenty years ago. Many of the current giants — Tesla, Meta, even Google — either didn’t exist or weren’t relevant yet. In 2004, Facebook was just launching from a Harvard dorm room. The average lifespan of an S&P 500 company has dropped from 33 years in 1964 to just 18 years today, according to Innosight’s Corporate Longevity Report.
That data doesn’t lie. Companies fade. Markets shift. Technology outpaces even the most dominant firms. Your job as a founder isn’t to defy that — it’s to stay aware of it.
Too many entrepreneurs wrap their personal worth into the success of their company, and it clouds their judgment. They ignore red flags. They pass on acquisition offers. They burn out. But being obsessed with your business doesn’t mean you should be blind to its evolution — or to your own.
Lesson: Be passionate, but not delusional. Every business has a cycle. Know when to build, when to pivot and when to walk away.
Related: The Path to Success Is Filled With Mistakes. Do These Four Things to Tap Into Their Growth Potential.
I’ve built companies. I’ve exited some, pivoted others and shut a few down. Today, as an investor, I spend more time evaluating the founder than the product. Because what I’ve learned — through success, but mostly through failure — is that mindset, judgment and self-awareness matter more than the perfect pitch.
Would I undo these mistakes? Not a chance. They taught me things no MBA could. They hurt. They cost time and money. But they also gave me clarity.
So if you’re building something today, ask yourself: Am I partnering with the right people? Am I chasing growth or building a great product? Am I obsessed … or aware?
The answers might just be the difference between a lesson and a legacy.
