Most companies do not fail because they make one catastrophic decision.
They fail because they keep repeating a decision that once worked.
Sam Jacobs put it better than I could: “I think most people, companies and teams fail not because they do the wrong thing, they fail because they did the right thing for too long.”
That is one of the clearest explanations of scaling failure I have heard.
A tactic works in one phase. It helps the company grow. The team starts to believe that what got them here will keep them here. Then the company changes. The customer changes. The market changes. But the playbook stays the same. That is when growth starts to stall.
Sam has lived that from multiple angles. He helped scale GLG during a period when revenue grew from $30 million to $300 million. He built commercial teams. He founded Pavilion. He also did something rare in this conversation. He talked openly about the mistakes he made while scaling it.
That honesty is what made this conversation so valuable.
Hypergrowth Exposes The Talent Problem Fast
When I asked Sam what tends to break first during a period of rapid growth, he did not point to systems or messaging or product.
He pointed to talent.
He said that the early group at GLG was “truly exceptional.” That matters because in the earliest stages of growth, a company often runs on a small concentration of unusually strong people. They create the tempo. They create the standard. They create the belief that the impossible might actually be possible.
The challenge comes later.
As hiring accelerates, many companies start relaxing the standard in the name of speed. Sam said that one of the first things that breaks is “the framework that you have for attracting and importantly retaining top quality talent.”
That is exactly right.
The danger is subtle. You do not wake up one morning and say, we are lowering the bar. You tell yourself you need to move faster. You tell yourself this person is close enough. You tell yourself the team can coach them up. Sometimes that works. Often it does not.
And once the bar slips, the cost spreads through the organization. Decision quality drops. Trust drops. Managers start compensating instead of building. The CEO ends up spending more time cleaning up than moving forward.
Retention Is A Strategic Issue
Sam also made an important point about retention. He said attracting strong talent is one thing, but they also have to want to stay.
That does not happen because you tell them the company has a great culture.
- It happens because they can see a future for themselves.
- It happens because they believe in the mission.
- It happens because the company feels like it is winning.
Sam said, “Culture is the exhaust of high performance.” That line is worth sitting with.
A lot of leaders act as if culture is something you can manufacture separately from results. I do not believe that. I believe culture strengthens when the company has clarity, standards, momentum, and trust. Culture is what people feel when they can do meaningful work with strong people in a system that works.
That is why retention cannot be treated as a soft metric. It is one of the clearest signals that the business is either building energy or leaking it.
Sometimes The First Fix Is Just More Intensity
When I asked Sam what he does when a revenue team stalls, he made an important distinction.
If overall revenue slows, the real issue might be retention, and retention usually takes time to fix. That is not a quick lever. That is a 12 to 18 month process.
But if you need immediate momentum, the first question is much simpler: are we actually doing the work?
Sam talked about arriving at The Muse and discovering that the SDR team did not even own telephones. Activity was being measured, but “activity” could mean blasting emails through a marketing automation system. That is not the same as real prospect engagement.
So the first move was not some elegant strategic overhaul. It was making sure the team was actually doing the kind of work that creates forward motion.
That lesson applies well beyond sales.
A surprising number of teams look busy without creating momentum. Before you redesign the system, make sure the system is truly on.
Pavilion Grew. Then It Drifted.
The most powerful part of the conversation was Sam’s willingness to describe what happened at Pavilion.
He said, “I’ve made pretty much every mistake at Pavilion that I tell other people not to make.”
That is not self-criticism for effect. That is self-awareness. And in my experience, self-awareness is one of the most important qualities a scaling CEO can have.
Sam described Pavilion in three chapters.
The first chapter was organic and powerful. The business emerged from a real need. It resonated. During COVID, Pavilion was there for people with benchmarking data, severance guidance, support, and community. It felt like one of those rare periods when everything you touch works.
Then came chapter two.
Pavilion raised $25 million. On the surface, that sounded like validation. Underneath, it triggered something else.
Sam said, “For me, I started chasing some ideas about myself that I had let go of in chapter one, that I needed to be a certain status, that I needed to have a certain amount of wealth.”
That is a brutally honest admission. It is also the kind of thing more CEOs should say out loud.
Because once that shift happened internally, the company started making decisions that reflected it externally.
Sam said, “What happened as a result of that? We chased growth and we chased revenue and we made a bunch of decisions that were bad for a membership organization.”
That is the real danger. Strategy drift almost always starts inside the leader before it shows up in the business.
Growth Can Break The Thing You Built
Sam gave one example that says everything.
“In 2022, we turned on self-serve and anybody can join the Pavilion that signed up on the internet. Well, that’s not really the way to build an exclusive membership organization. You can’t just join Skull and Bones at Yale by walking up and knocking on the door.”
Exactly.
The tactic itself was not irrational. It would make sense in a different kind of business. But it was the wrong move for Pavilion because it weakened the very thing that made Pavilion valuable.
This is one of the most common mistakes in scaling.
A company adopts a tactic that is “good for growth” in general while ignoring whether it is good for this business model specifically.
That is how companies slowly break their own differentiation.
When Too Much Flows Back To The CEO
Sam also described what happened inside the organization as Pavilion drifted.
The team was not operating at the scale the company needed. Strategy kept shifting. Decisions came back to him. He said he thought he was delegating, but too much kept returning to his desk.
This is a pattern I see all the time.
Leaders often think they have an execution problem. What they really have is a talent problem and a clarity problem. If the team is not strong enough, and if the strategy is not stable enough, the CEO becomes the forced center of gravity.
That creates an illusion of control while actually making scale impossible.
The Turnaround Started With One Truth
The turning point came when Sam was with a group of CEOs who told him what he most needed to hear.
Fix the talent quality in the organization.
That became the priority.
He hired a president. He rebuilt the executive team. He narrowed the focus. He returned Pavilion to the premise that made it valuable in the first place.
He told me, “We are removing self sign up. We are tightening our admission criteria. We are focusing on a small number of experiences for depth rather than a wide number of experiences for breadth.”
That is what recovery often looks like. Not more complexity. More honesty. More discipline. More return to first principles.
Financial Literacy Is Now A Leadership Requirement
Another important theme from Sam was financial literacy for go-to-market leaders.
He pointed out that many revenue leaders grew up professionally during a long stretch of cheap capital and growth-at-all-costs thinking. In that environment, it was possible to be good at driving revenue without deeply understanding the economics of the business.
That era is over.
Today, go-to-market leaders need to understand the P&L. They need to understand equity. They need to understand compensation design. They need to understand how enterprise value is actually created.
Sam made a subtle but important point here as well. Sometimes leaders were never taught these things because nobody had an incentive to teach them. In some environments, there was a kind of gatekeeping around how much commercial leaders should understand about the deeper financial mechanics of the company.
That is changing now, and it needs to.
AI Will Reward Better Thinking
On AI, Sam’s view was sharp and practical.
He believes the biggest opportunity for go-to-market leaders is not just speed. It is better focus.
- Better data.
- Better signals.
- Better targeting.
- Better understanding of actual customer fit.
He said the number one thing AI can do for go-to-market leaders is “help focus on better customer fits.”
That is exactly where many teams need help.
AI should not just make you louder. It should make you sharper.
Internally, he is pushing Pavilion to ask a simple question again and again: did you use AI for this?
Not because every task needs AI. But because leaders need to challenge old assumptions about how work gets done. Some jobs will change dramatically. Some roles will become more strategic. Some workflows will disappear.
The leaders who benefit most from AI will not be the ones who talk about it the most. They will be the ones who redesign their organizations around what it actually makes possible.
What This Conversation Really Says
Sam’s story is not just about Pavilion.
It is about how scaling can tempt a CEO away from the truth.
- You can start with a clear purpose.
- You can build something that resonates.
- You can create real momentum.
Then growth, money, and status can quietly pull you off course.
The correction usually does not come from a clever tactic. It comes from a deeper question:
What kind of business are we really building, and what kind of leader do I need to be to build it well?
Sam answered that question honestly. That is why chapter three sounds so much stronger than chapter two.
I Coach CEOs
If you are in a phase where your company is growing but something feels off, where the team is stretched, the strategy is drifting, or too many decisions are flowing back to you, that is exactly the kind of work I do with CEOs.
I help CEOs:
- Identify when growth is starting to distort the business model
- Spot the places where talent quality is holding back scale
- Rebuild executive teams that can truly carry the next phase
- Reconnect strategy to what made the company valuable in the first place
- Separate personal identity from the pressure to chase status, scale, or optics
I am Glenn Gow. I coach CEOs. If you want to build the next chapter of your company with more clarity, better talent, and stronger alignment, let’s talk. Listen to the full episode of The Scaling CEO here.
