After 15 years as a founder and CEO of venture-backed companies, I took a detour and taught at the University of Colorado Business School. A group of second-year students asked me a deceptively simple question: What do you wish someone had told you when you graduated business school? I made a list of 20 things. It was part confession, part scar tissue, part operating manual.

I now work at RevelOne, where I spend my time with venture-funded and PE-backed companies on go-to-market and talent strategy. The more investors, founders, and executives I meet, the more I realize the same mistakes I made show up again and again. So here are five of those lessons, the ones that feel most relevant to what I see every day.

1. Hire the right people for the right stage

This sounds obvious until you watch how often smart people get it wrong.

The classic Series A mistake is what I think of as logo goggles. A company finally has real product-market fit, some real revenue, and the founders are ready to make their first serious GTM hire. Instead of hiring the right builder, they hire the person with the shiniest résumé. They bring in a “name” CMO from a famous brand, someone who has inherited large teams, operated with large budgets, and has not personally been in the weeds in ten years. It feels like a milestone. It often becomes a tax. The role usually requires a quantitatively sharp, hungry, mid-career operator who can write copy on Tuesday, build the dashboard on Wednesday, fix funnel leakage on Thursday, and still recruit on Friday.

There is data behind why this matters. Startup Genome’s long-running research found that premature scaling is one of the central killers of young companies, and that startups that avoid scaling too early materially improve their odds of success. In parallel, CB Insights’ analysis of startup failures shows that the biggest reasons companies die are not glamorous at all: poor product-market fit, bad timing, and weak economics. In other words, companies often fail because they behave like later-stage businesses before they have earned the right to. Overhiring is one version of that sin.

The inverse mistake happens in private equity. I routinely see PE-backed companies doing $180 million-plus in revenue and $60 million-plus in EBITDA insist they want an “up-and-comer” CMO because they don’t want to pay market. Sometimes the rationale is almost flawed: if the CMO makes more than the CFO, it will create internal drama. That is penny-wise and value-destructive. At that size, marketing is no longer a collection of campaigns. It is an investment system. You need a leader who can allocate spend rationally, build a team, understand experimentation, and tie CAC, retention, pricing, gross margin, working capital, cash flow, and investor expectations into one coherent operating model.

That is not indulgence. It is value creation. McKinsey has shown that sustainable growth outperformers generate materially better shareholder returns than peers, and more recent McKinsey work notes that roughly half of transformation value now comes from growth initiatives, up from less than 40 percent just two years earlier. If growth is that central to enterprise value, then underinvesting in the person running one of the principal growth engines is not discipline. It is self-harm.

Stage fit beats résumé theater. Every time.

2. Humility is not softness. It is operating leverage.

One of the most useful career rules I know is this: do not try to be the smartest person in the room. Early in your career, that mindset keeps you learning. Later in your career, it keeps you from calcifying.

Founders and executives often confuse confidence with omniscience. That is a terrible trade. The leaders who compound fastest are usually the ones who are willing to admit what they do not know, hire people who are better than they are in key domains, and let those people be great. One of the reasons we succeeded at Craftsy was that we built a team with real depth. We had people who were simply better than I was at technology (Todd Tobin and Bret Hanna), product (Josh Scott), marketing (Danielle Wilke/Kami Kennedy/Amber Minson), operations (Max Miller), production (Emily Lawrence), and finance (Karyn Miller). That is not a threat to leadership. That is leadership.

The research increasingly points in the same direction. Studies on humble leadership have found that it improves psychological safety, knowledge sharing, employee voice, and creativity. A 2022 meta-analysis found broadly positive links between humble leadership and outcomes such as engagement, learning, and performance. More recent work highlighted by Harvard Business Review argues that humble leaders do more than make people feel good. They increase trust and teamwork and can actually inspire more leadership behavior in others.

This matters because business school quietly over-rewards polish. Real operating environments reward intellectual honesty. “I don’t know” is often the beginning of good judgment, not evidence against it. The trap is thinking that seniority requires pretending to have every answer. It does not. Seniority requires asking better questions, spotting weak assumptions faster, and making fewer ego-driven decisions.

Humility also changes how disagreement works. You should get comfortable disagreeing with people, including your boss, your board, and your own team. But you do not get to disagree lazily. You earn the right to push back when you have done the work, looked at the data, stress-tested the alternatives, and can articulate a better path. The best teams I have seen are not polite. They are rigorous. They argue hard, but with evidence. They are willing to be wrong in public. They care more about getting to the truth than winning the moment.

That only happens when the leader models it first.

3. Be honest, face facts, and make failure useful

One of the most expensive habits in business is euphemism. Revenue softness becomes a “temporary headwind.” Churn becomes “customer evolution.” A broken hiring process becomes “some turbulence in talent.” The language gets softer as the problem gets sharper.

What I wish I had learned earlier is that facts do not become less true because you postpone naming them. Usually the opposite happens. They become larger, more political, and more expensive.

That is why I have come to believe in a simple sequence: face reality early, allow intelligent failure, and then execute with rigor. Those are not contradictory ideas. They are the whole game. You want a culture where people can surface problems quickly, say what is not working, and kill bad ideas before they become expensive traditions. But once the direction is set, execution has to be exacting.

Google’s Project Aristotle famously found that psychological safety was the most important factor distinguishing effective teams. Teams perform better when people feel safe taking interpersonal risks, asking questions, raising concerns, and admitting mistakes. Amy Edmondson’s foundational work on psychological safety reached a similar conclusion years earlier: better teams often report more errors not because they are worse, but because they are more honest and therefore better able to learn. That is a profound distinction. Silent teams do not make fewer mistakes. They bury more of them.

There is also a practical planning lesson here. McKinsey has written about premortems as a way to force teams to imagine why a project failed before it launches. That sounds simple, but it is powerful because it punctures optimism bias and status dynamics. The team that asks, “How could this blow up?” before spending the money is usually better off than the team that performs a glossy retrospective after the damage is done.

Too many leaders think being “positive” means shielding people from unpleasant truths. It does not. The most constructive cultures I know are often the most unsentimental. They face facts quickly. They do not romanticize failure, but they extract the lesson. Then they move.

Sidebar: This “facing facts” problem becomes more pernicious when you have multiple venture investors who, even in the face of facts that say otherwise, have disparate strong opinions, or financial goals. Ultimately, coming prepared to a board meeting (or post board meeting) and saying “I hear you, I get why you want us to pursue that strategy, and here is why I don’t think it’s the most prudent path right now for these specific reasons” as fast as possible, rather than prolonging the debate over multiple quarters saves valuable time and effort.

4. Keep learning, because technology (example: AI) is already changing the baseline

I overheard a wise person telling someone recently, “AI is not going to take your job, but someone who knows how to use AI will.” That line stuck because it is directionally right, and the data is now catching up to the intuition.

In his widely circulated 2026 essay, “Something Big Is Happening,” Matt Shumer argues that artificial intelligence has reached a tipping point where it is no longer just a productivity aid but a true collaborator capable of meaningful knowledge work, and that the only way to grasp its rapidly evolving capabilities is through consistent, hands-on use; as he bluntly puts it, “if you’re not using AI every day, you don’t really understand what’s happening,” emphasizing that daily engagement is now essential for building the intuition and competitive advantage required in a world where AI is becoming a foundational layer of how work gets done.

Shumer continues, “Here’s a simple commitment that will put you ahead of almost everyone: spend one hour a day experimenting with AI. Not passively reading about it. Using it. Every day, try to get it to do something new… something you haven’t tried before, something you’re not sure it can handle. Try a new tool. Give it a harder problem. One hour a day, every day. If you do this for the next six months, you will understand what’s coming better than 99% of the people around you. That’s not an exaggeration. Almost nobody is doing this right now. The bar is on the floor.”

Across organizations, AI has moved from curiosity to workflow. McKinsey’s 2025 global survey found that 78 percent of respondents say their organizations use AI in at least one business function, and 71 percent say their organizations regularly use generative AI in at least one function. Marketing and sales are among the most common places where it is being used. This is no longer fringe behavior by the nerdiest team in the building. It is becoming table stakes.

Every function should be experimenting right now. Marketing should be using AI for research, content iteration, segmentation hypotheses, testing frameworks, and creative variation. Sales should be using it for call prep, account research, objection mining, and sequence improvement. Finance should be using it for faster analysis, variance explanations, and scenario framing. Recruiting teams should be using it to sharpen scorecards, sourcing outreach, and calibration materials. None of this replaces judgment. It multiplies the reach of people who have it.

It also changes the buy-versus-build equation. Many organizations still reflexively pay agencies and consultants to produce work that internal teams can now do faster and cheaper with the right AI stack and the discipline to learn it. That does not mean outside help disappears. It means the bar for paying for it should go way up.

The real risk is not that AI makes people obsolete. The real risk is that complacency becomes visible. In the same way Excel once separated operators from pretenders, AI fluency is becoming a practical marker of seriousness.

5. Hire carefully, manage effectively, fire fast

This is the least comfortable lesson and one of the most important.

Bad hiring decisions do not just cost money. They consume time, distort culture, slow execution, and drain the attention of your best people. SHRM has noted that replacing an employee can cost from 50 percent to 200 percent of annual salary depending on level, and that while average cost-per-hire may look manageable on paper, the all-in cost of hiring often runs much higher. SHRM also cites estimates that a manager can spend roughly a quarter of their time coaching a bad hire. That is an astonishing tax on an organization.

The uncomfortable part is that many failed hires do not fail for the reasons executives like to imagine. Leadership IQ’s research on new hires found that a large share fail within 18 months, and that most failures are driven more by attitude and coachability issues than by pure technical incompetence. In other words, companies often interview for pedigree and then get surprised by behavior.

But “hire carefully” is only half the sentence. The middle matters just as much: manage effectively. Gallup has repeatedly found that managers account for about 70 percent of the variance in team engagement. That is not a soft metric. Engagement affects retention, discretionary effort, quality, and productivity. Gallup also reports that employee disengagement imposes an enormous economic cost. If you hire well and then manage poorly, you still lose.

And then there is the final clause: fire fast. This does not mean callousness. It means clarity. When someone is in the wrong role, everyone usually knows before anyone says it aloud. The individual feels it. The peers feel it. The manager feels it. The team starts compensating. Workarounds appear. Standards drift. Resentment builds. Delaying action in the name of kindness is usually unkind to the person, the team, and the business.

The best leaders I know are demanding, but not cruel. They hire with rigor, set expectations clearly, coach specifically, and act decisively when the fit is wrong. That is not harsh. It is respectful.

Business school teaches frameworks. Experience teaches asymmetry. A few decisions matter far more than most. Who you hire, when you hire them, whether you are humble enough to keep learning, whether your team can face reality, and whether you adapt faster than the market changes, those decisions compound.

I wish I had known all of this when I graduated. Then again, part of the problem is that some lessons are only obvious after they are expensive.

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About RevelOne

RevelOne is a specialized go-to-market search & advisory partner that drives Growth through People. Growth strategy and talent strategy are completely intertwined, yet often handled by different people. We staff projects with expertise across both to support our clients in sharpening their growth plans and ensuring they have the right full-time and part-time talent to achieve their specific goals.  

Over the past 10 years, we’ve successfully placed 1,700 people at over 750 clients, including both tech companies and traditional companies looking for modern GTM leaders. Over 50 of these clients are now unicorns.

Our GTM retained search practice focuses on Marketing, Sales, Client Success, and Partnerships/BD permanent hires for all levels, from executives to directors, managers, and team buildouts. We can also source temporary hires – pre-vetted GTM experts – for strategy and execution on interim, part-time, or project-based engagements.

Contact: Have a GTM question, a new hire, or a problem you’d like to solve? Reach out to RevelOne today to discuss: jlevisay@revel-one.com