I’ve built 3 companies, each of them was acquired by a public conglomerate.
In the process, I’ve made every mistake a founder can make. All of them.

I’ve hired wrong, fired wrong, and waited too long to do both. I’ve been the smartest person in the room and the most oblivious one. Usually in the same week, sometimes in the same meeting.

So when I speak with a founder and they say, “I don’t know why I’m having these problems,” I usually know exactly why they’re having those problems. Because I’ve had the same problems. And I know the way out.

Founder coaching, at it’s best, helps you feel heard, feel seen, and feel comforted that you have a resource to help move you and your business forward, fast.

But before you find any old person for your founder coaching, take it from me, as somebody who’s been there, just having a smart person to coach you will probably leave you unfulfilled.

You need a founder who became a coach. Because that’s the only type of person who recognizes what you’re experiencing. You don’t know the roller coaster ride of a founder, until you’ve been in the seat yourself.

In other words, when it comes to founder coaching, people who haven’t been entrepreneurs simply don’t understand the nuance of the entrepreneurial personality.

Let me explain.

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The Founder Journey Has Stages

The first stage of the founder’s personality is what most people picture when they think of an early stage entrepreneur.

You’re scrappy. You’re fast. You’re following every revenue opportunity that blinks in your direction like it’s the last time you’ll have a chance at making money.

You make all the decisions because there’s no one else to make them. Besides, nobody will ever know or be able to articulate the business vision like you do.

Everything is temporary and everything is agile, especially as you’re looking for that scalable product-market fit. Heck, if your product isn’t fitting the market, even what you’re selling might be completely different in 6 months.

Stage 2 is when you begin to find product-market fit and the business starts scaling. It’s exciting. Revenue is growing and you begin hiring. You feel great that you have a team firing on all cylinders. Suddenly you can’t believe that your vision is actually coming to fruition.

And then there’s Stage 3.
The part where you begin to scale up.
This is the stage nobody warns you about.

In fact, Stage 3 doesn’t feel like a different challenge than Stage 2. It feels like the exact same challenge. And that’s the problem.

Because the rules have completely changed, and everybody’s realized it but you.

Whereas the start-up mode of Stage 1 requires agility, continuous change, and saying “yes, we can.” The scale-up mode of Stage 3 requires consistency, process and knowing when to say “no, we can’t.”

The company was built as an extension of you, but for you to be successful in Stage 3, it needs to run more effectively without you at the center of everything.

Stage 1 rewards your deep involvement. Stage 3 punishes it.

That transition is the reason 99% of founders can’t scale.

Not because you aren’t smart.
Not because you aren’t working hard.
Because the exact patterns that got you to Stage 3 are now the ones preventing you from getting through it.

And that, my friend, is why founder coaching is not a nice-to-have, it’s a must-have.
In fact, if you don’t believe me yet, you should read this article in Forbes: “For Founders, Coaching Is Here To Stay.“

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Why the Skills That Built Your Company Will Stop Working at Scale

Here’s the funny thing about the founder personality: it is exactly the right personality type to help you scale your company.

Your personality isn’t a weakness. Until it is.

The personality needed to build a company, is the same one that will tear it down.

Your ability to make fast decisions works really well when you have 7 people at the company. At 35 employees, you become the bottleneck that frustrates the staff.

Chasing down every revenue opportunity worked well when you were searching for product-market fit. At scale, all that chasing will cause lack of focus, lack of accountability and enough poor productivity to keep you up at night.

Your patterns don’t get worse when you are at Stage 3. Your patterns don’t even change.

It’s the environment that changes.

This is what I call the Pattern Environment Loop. The behaviors that built the company are so deeply ingrained that most founders don’t even see them as behaviors. It’s just who they are. And that’s exactly the problem. Because “who you are” is suddenly limiting the company’s growth.

The 0.1% of founders who break through this transition share one thing in common.
It’s not intelligence.
It’s not luck. (OK, maybe it’s a little luck).
It’s the willingness to challenge their own patterns before those patterns challenge their business’s potential.

That’s why founder coaching is critical.

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The 3 Founder Transitions That Break Most People

The reason 99% of founders flail isn’t random. There are 3 specific places where the Pattern-Environment Loop does its worst damage.

Almost every founder I’ve worked with got stuck at one of these – and didn’t know it until we discovered it together.

Transition 1: Doer to Delegator (at roughly 10-30 employees). You’ve been the one doing everything – and you were good at it. Now you have people who should be doing the things instead. But every time you hand something off, it comes back wrong. Or slower. Or missing the thing you would have caught. So you take it back because, well, that’s easier and faster. So the team learns to wait for you to do the work. And suddenly you’ve become the bottleneck you swore you’d never be. This is the difficulty delegating pattern – and it’s the first failure most founders succumb to.

Transition 2: Manager to Leader of Leaders (at roughly 30-70 employees). You’re no longer managing individual contributors, you’re managing people who manage people. The thing is, nobody told you the skills are completely different. Managing direct reports is about execution. Leading leaders is about environment – the culture, decision-making, strategic accountability. If you’re still operating like you did at 20 people, you’re not leading at scale. This is exactly why newly promoted VPs struggle with this transition – and founders aren’t immune to the same issue.

Transition 3: Founder to CEO (70+ employees). At this stage, you’re not building anymore – you’re institutionalizing. You’re creating the systems, culture, and senior leadership team alignment that will outlast your direct involvement. The founder who can’t make this shift is the one who keeps inserting themselves into every important decision, keeps maintaining control, and slowly becomes the limit to what the company can become. Honestly, the irony is brutal: the thing that makes you irreplaceable becomes the one thing that makes you replaceable.

Founder coaching is most valuable at these 3 inflection points – not because you’re failing, but because the unconscious leadership patterns that got you to each transition are exactly the ones that’ll prevent you from getting through it.

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Why Founders Need to Talk to Other Founders

I’ve talked with entrepreneurs who are skeptical of founder coaching. I get it.

They hired executive coaches before.

But their experience has always been some version of the same thing: “Nice person, but they didn’t really understand me.”

Understanding founders only comes from having been a founder. That’s the cold hard truth.

The executive coach needs to understand the anxiety and the roller coaster of emotions. They need to know what it’s like when you can’t let other people make decisions, even though you may lose employees because of it. They need to understand how following a big revenue opportunity can hurt the company more than it helps. And they need to have experienced sitting in front of investors explaining why growth stalled, and knowing, somewhere underneath the explanation, that you were the reason.

Sure, coaches can read about that. But you can’t feel it by reading about it.

When a coach has been through the founder experience themselves, the conversation is completely different. They’re not asking you questions from a framework – they’re recognizing the pattern you keep repeating. They can (hopefully) say, “I know exactly how you feel. I’ve been there before.”

That’s not a small thing. It’s the difference between founder coaching that works, and founder coaching that doesn’t.

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Why the Choice Isn’t Between a Coach and a Mentor — It’s Both

Most founders who’ve tried out executive coaching or mentoring describe the same issue, but from opposite viewpoints.

Pure coaching without founder experience feels like useless therapy. You’re getting better at understanding yourself, but nobody’s helping you use that understanding to scale your company.

Pure mentoring without coaching feels like someone else’s answers to your questions. It’s sometimes useful, but you’re just listening to their judgment instead of developing your own. Regardless of the mentor’s experience, I guarantee it was different than yours.

What founders actually need is someone who moves between both executive coaching and mentoring in the same conversation. Someone who can sit with you in the fogginess of entrepreneurialism and help you get clarity, while, at the same time, they can say, “here’s what I did when I had the same issue, and here’s what I’d do differently now.”

When I work with founders, I don’t fit neatly into either the executive coaching or mentoring box, because that wouldn’t be helpful to you. Coaching and mentoring aren’t mutually exclusive approaches. They’re tools for different moments in the same conversation – sometimes in the same sentence.

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What Founders Actually Work On In Founder Coaching

Most executive coaching descriptions are vague. “Better leadership.” “Improved self-awareness.” “Enhanced executive presence.”

That’s not what founders are hiring for.
These are probably closer to what your problems actually look like.

“My co-founder wants to hire their friend for the VP of Sales role and I think it’s a disaster.“ This is a co-founder dynamics problem that people think is a hiring decision. The founder coaching isn’t about whether to hire the friend. It’s about the conflict resolution patterns underneath – why this keeps coming up, what it’s exposing about your relationship with your co-founder, and whether the two of you have ever actually resolved how decisions like this get made.

“My board is pushing me to bring in a VP of Sales, but I’ve been the lead seller for 3 years and I don’t think anyone can do it like I can.” That’s not a sales problem. That’s an identity problem with the founder. It’s because the part of you that built the company by doing everything yourself is now resisting the thing the company needs next. Founder coaching unravels this pattern and helps you decide whether the resistance is protecting a real competitive advantage or protecting your ego.

“I rewrote my VP of Product’s roadmap again. She’s frustrated. I know I should stop. I can’t stop.” This is the Pattern-Environment Loop in real time. You don’t need someone to tell you that you should delegate – you already know that. You need someone to help you understand why you won’t delegate, and what it would take to actually change the behavior rather than just deciding to white knuckle it again… and failing.

“I’m working 80-hour weeks, my best people are leaving, and I don’t know why nothing I do is making a difference“ This is one of the most common calls I get from founders. And the answer is almost always the same: you are the reason. Not because you’re bad. Because you built a system that routes everything through you, and the system is now too big for one person to run.

Founder coaching is specific work. It’s not always comfortable, but it’s exactly the kind of conversation that only happens when the coach you’re talking with has been in the same seat as you (which is where my story comes into play)

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Founder Coaching: 5 Signs You’re Ready.

If you’ve ever wondered whether founder coaching is right for you, there are 5 signs that can help you quickly make the decision. You don’t need all 5 to occur. If only 2 or 3 of these are true, you’ve got a problem that can use coaching and mentoring.

Your people are quitting. When people keep leaving, that’s a huge red flag. They probably feel like they have no room to grow, no autonomy, and/or they think you’re the bottleneck. Will they say this? Rarely. How will you find out? Founder coaching (it’s the entire reason I’m telling you all this stuff!)

You’re working harder but the company isn’t moving faster. Your clocking in more hours than anybody else at the company, but the growth isn’t matching your effort. In almost every situation like this, the founder is the bottleneck.

Every important decision still runs through you. Even though you have employees who are good at what they do. Even though you’ve said multiple times that you want them to own their work. You still are involved in almost every decision, because that’s what helped build your company. And now, that’s the pattern your environment rewards.

You know you need to delegate more. You’ve been saying it for awhile, but nothing has actually changed. That’s not a problem with difficulty delegating – that’s an identity problem that you need some founder coaching to confront.

The thing that made you successful is now the thing limiting the company. Maybe you can feel it happening, but you can’t quite figure out exactly what it is. You just know something doesn’t feel right. Something is keeping your company from becoming something bigger than you. And the way you try to address it (with more control) is exactly the thing that will make it worse.

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What to Look For When You Want Founder Coaching

Founder coaching should have a higher barrier to entry than other types of leadership coaching. Not because founders are more important (actually…), but because the specific transition you’re navigating requires a specific kind of understanding. Most coaches don’t understand it at all.

So here’s what I want you to do:

Look for someone who has actually built something – someone who has been in the muck and mayhem of entrepreneurialism. You want a coach who has struggled with the need to control, when the company needs them to let go. You want to find a coach who has made the identity shift themselves and can describe what it actually feels like, not what some random book says it feels like.

Also, and this is important, look for someone who pushes back on you. Assuming you’re an entrepreneur, you need that. A good coach doesn’t just validate your story – they help point out the holes and figure out what is working in your favor and what isn’t. If every session ends with you feeling confirmed rather than challenged, you’re not getting what you need from founder coaching.

And, finally, look for someone who can be both a coach and a mentor. Founder coaching is about sharing real experiences to help you figure out how to overcome your biggest obstacles.

Founders who can grow their companies the fastest are the ones who get coaching and mentoring in the same relationship. That combination isn’t common. But when you find it, it’s the right fit.

And this is the part where you probably should read about my story.

If you want to find out what’s actually happening within your leadership blindspots – specifically which patterns are limiting you – the Leadership Diagnostic Workshop is where to start. It’s free. It’s 90 minutes. And most founders who go through it say the same thing: “I knew something was off. I just didn’t know it was that.”

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Executive Coaching vs. Advisory: What Founders Actually Need at Each Stage

Most founders use these words interchangeably. They’re not the same thing, and confusing them leads to getting the wrong kind of help at the wrong time.

An advisor fills a knowledge gap. You need someone who’s been through a Series B raise, navigated an acquisition process, or built a channel sales system in your industry. They tell you what worked for them. You filter it through your situation. It’s useful for specific functional problems where experience and pattern matching are the resource you need.

A coach addresses a pattern gap. You don’t need more information – you need to understand why you keep making the same kind of decision, why the same friction keeps showing up on your team, why the thing you’ve decided to do differently keeps reverting to the old way. That’s not an information problem. No advisor can solve it.

Here’s the clarification I give to founders: if you can describe the problem clearly and you need someone who’s solved it before, that’s an advisor. If the problem is fuzzy, or you’ve tried to address it multiple times and it keeps coming back, that’s a coach.

Most founders at Stage 2 and Stage 3 need both – advisors for the functional gaps (go-to-market, finance, legal), a coach for the operating system gaps (how you make decisions, how you build environment, how you lead people who lead people). The mistake is using an advisor for a coaching problem, or expecting a coach to give you an advisor’s answers – unless, of course, you found a fellow founder who is both an advisor and a coach. Someone like, say, Jeff Matlow.

If you want to go deeper on the coaching vs. mentoring distinction specifically, this article on leadership coaching vs mentoring breaks down exactly how the two differ and when you need each one. And if you’re trying to figure out how to choose an executive coach who’s actually right for a founder at your stage, that’s worth reading before you make any decisions.

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Frequently Asked Questions About Founder Coaching

Q: What’s the difference between founder coaching and regular leadership coaching?
Founder coaching focuses on the transition from Stage 1 to Stage 3 — from agility to consistency and scale. General leadership coaching builds skills. Founder coaching addresses identity: the behaviors that helped you build your company are now the same behaviors that are limiting it. Changing those behaviors requires more than skill-building. It requires a fundamental shift in how you see your own role.

Q: What’s the difference between founder coaching and therapy for founders?
Therapy addresses psychological health and past wounds. Founder coaching addresses how you currently operate – how you make decisions, delegate, and design the environment your team works in. If you’re anxious because your childhood taught you that control equals safety, that’s therapy territory. If you’re anxious because you’re the bottleneck in 47 decisions a week and don’t know how to redesign that, that’s founder coaching territory. Many founders benefit from both. They’re not competing – they’re just solving different things.

Q: Do I need founder coaching or mentoring?
Probably both. Founder coaching without founder experience leaves you with insight and no map. Mentoring gives you someone else’s answers instead of developing your own judgment. The most effective relationships for founders combine both — someone who can do the pattern work with you and draw on real founder experience in the same conversation. In that sense, founder coaching is somewhat of a misnomer. It should probably be called executive coaching and mentoring for founders.

Q: How do I know if I’m ready for this?
If 2 of the 5 signs above are true, trust me, you’re ready. The most common trigger that you can benefit from founder coaching is when you feel that something is off, and you don’t know what. It’s highly possible that the thing that made you successful is now the thing limiting your growth. That’s the Pattern-Environment Loop knocking on your door. Time to answer it.

Q: How long does founder coaching typically last?
Most times I work with founders, it’s usually for 6+ months. We’ll start with understanding your patterns, how they are benefitting you, how they are working against you and how you repeat the same mistakes. After that, we start building new patterns. Finally, we create the systems that allow you to maintain your trajectory, even when things get hard.

Q: What’s the best way to start?
Good question. The Leadership Diagnostic Workshop is a free 90-minute session that will allow you to see the specific patterns shaping how you’re leading right now. No pitch. No commitment required. Just a clear picture of what’s actually going on before you decide on anything.

Q: How much does founder coaching cost?
Founder coaching typically ranges from $3,000 to $10,000 per month depending on engagement structure and coach experience. For most founders, the ROI calculation isn’t the monthly fee – it’s the cost of a bad executive hire ($250k+ in comp plus 12 months of organizational drag), or a scaled decision bottleneck that stalls growth for a year. Most engagements run 6-12 months. And if your coach offers a free diagnostic session first, take it. That’s either proof they’re confident in their work, or the fastest $0 you’ll ever spend finding out they’re not the right fit. If you find a coach that gives a 30-day money back guarantee (like Jeff Matlow does), by all means, explore that.

Q: Should I get founder coaching before or after raising my Series A?
Before is better. The Pattern-Environment Loop that worked to raise the funding – you doing everything, high control, fast unilateral decisions – is the exact pattern that breaks post-A when you’re hiring 30 people in 12 months. Most founders wait until they’re drowning: turnover spikes, board pressure mounts, they’re working 90-hour weeks. Starting coaching during the fundraise or immediately after lets you redesign how you operate before the breakage becomes a crisis. It’s a lot easier to redesign a system that’s under pressure than one that’s already failing.

Q: How do I know if I need a founder coach or an advisor?
If you can describe the problem clearly and need someone who’s solved it before, that’s an advisor. If the problem is fuzzy, or you’ve tried to address it multiple times and it keeps coming back, that’s a coach. Advisors fill knowledge gaps. Coaches address pattern gaps. Most founders at Stage 2 and beyond need both – advisors for functional gaps like go-to-market or finance, a coach for operating system gaps like how you make decisions and lead people who lead people.

Q: What does a typical founder coaching engagement look like?
Most of my founder coaching engagements run 6+ months and follow the High-Performance Protocol: the first phase is diagnosis – mapping your patterns, how they’re serving you, and how they’re working against you. The second phase is design – building new operating systems around delegation, decision rights, and team environment. The third phase is transition and sustain – making sure the changes hold when things get hard, which they will. Between sessions, there’s async support for the real-time situations that can’t wait for the next call. The goal isn’t to make you dependent on the coaching. It’s to make you not need it anymore.

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Related Articles

• Leadership Coaching for Founders: When Startup Skills Break at Scale
• How to Choose The Right Leadership Coach
• Executive Coaching ROI: What Actually Matters (Beyond The Spreadsheet)
• Imposter Syndrome in Leadership: What’s Actually Going On

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Jeff Matlow is a leadership coach, mentor and 3x entrepreneur who helps senior leaders spot the unconscious patterns keeping their teams dependent on them – then redesign the environment so everyone can actually perform. He’s spent 25+ years working with leaders at Disney, Porsche, Nestlé, and hundreds of high-growth companies. Think Ted Lasso meets Brené Brown meets a Navy SEAL. Learn more about working with Jeff or subscribe to The Best Leadership Newsletter Ever.