Episode 14 now available!

Ep 14 - Michael Ceely, High Performance Executive Coach

​Helping Founders Get Out of Their Own Way​

Michael Ceely has been a competitive bike racer, a high school Spanish teacher, and a licensed psychotherapist. Now he coaches founders and executives to stop overthinking and start moving. His clinical background gives him an edge most coaches don't have: he can spot when a high-achieving founder actually needs therapy before they're ready for coaching.

This conversation covers the mental patterns that keep founders stuck, from imposter syndrome (which Michael calls what it is: plain old insecurity) to the self-sabotage that kicks in right when things start working.

We dig into his reframe of anxiety as an action signal, the 80% rule for killing perfectionism, what he learned going through the Level Set program at StartingBlock in Madison, why he thinks Wisconsin founders need to stop playing small, and his goal of scaling his coaching business to $10 million in revenue.

Topics discussed:

• The line between psychotherapy and executive coaching, and why it matters for founders
• Why the coaching industry's lack of regulation is a problem for people seeking help
• Reframing imposter syndrome as normal human insecurity, not a disorder
• Anxiety as an action signal: identify the decision, take the step, move on
• The 80% rule for breaking analysis paralysis and shipping faster
• How self-sabotage shows up subconsciously when founders start succeeding
• Madison's biotech advantage and the "it's just Madison" inferiority complex
• What the Level Set program at StartingBlock unlocked for Michael's business thinking

→ Listen to the Interview​

Key learnings

Imposter syndrome is just insecurity, and there's nothing wrong with you.

Michael doesn't dance around this one. Imposter syndrome sounds like a clinical diagnosis that needs to be untangled over months of work. In reality, it's just insecurity, and every human being feels it when they step into unfamiliar territory. His point: if you're walking into a Series A meeting for the first time and you feel completely confident, something is probably wrong with you. The self-talk of "should I be here?" and "do I belong?" is the most normal thing in the world.

The problem is when founders pathologize it. They think there's something uniquely broken about them. There isn't. Michael's advice is to stop making it about you and flip the focus to your customer. Instead of "how will I do?", ask "how can I help them?" That shift from self-focused to mission-focused is one of the fastest ways to quiet the noise. It's almost counterintuitive: by not focusing on your anxiety, the anxiety goes away.

For Wisconsin founders specifically, this matters because the ecosystem already has a built-in inferiority complex compared to the coasts. Layering personal insecurity on top of geographic insecurity is a recipe for playing small. Recognize the feeling, name it, and redirect your energy toward the people you're trying to serve.

Anxiety is telling you to do something, not telling you something is wrong.

This was one of the most useful reframes in the conversation. Michael treats anxiety not as a disorder but as an action signal. Your brain is flagging that there's a decision to be made or a step to take. Once you take it, the anxiety usually resolves. It could be as simple as sending an email you've been putting off, having a hard conversation with a co-founder, or just making a choice between two options you've been going back and forth on for weeks.

He coaches founders to build the habit of asking themselves one question when they feel anxious: "What's the action I need to take?" That reframe turns anxiety from something you suffer through into something that keeps the ball moving. It's empowering instead of paralyzing.

Now, Michael is careful to note this is a simplification. Generalized anxiety disorder is a clinical issue that needs a different approach. But for the day-to-day founder anxiety of "what if this doesn't work" or "what if I make the wrong call," treating it as an action signal is a game changer.

The 80% rule is how you stop researching and start building.

Is it 80% good enough? Ship it. Michael uses this rule with clients who get trapped in perfectionism, spending weeks researching the ideal scheduling software or obsessing over internal tools that customers will never see. His question cuts through it: if your goal is happy customers and a product that helps people, does it really matter if your internal system is 95% optimized instead of 80%? The ROI on that extra 15% is almost always not worth the momentum you lose.

This one hit close to home. I see this pattern constantly with founders in the ecosystem. They want everything buttoned up before they go to market, before they pitch, before they hire. The 80% rule gives you permission to move. It doesn't mean shipping garbage. It means being honest about what actually moves the needle versus what feels productive but isn't.

Self-sabotage isn't laziness. It's your brain trying to keep you safe.

This was one of the more eye-opening parts of the conversation. Michael explained that when founders self-sabotage, like oversleeping before a big meeting, forgetting to send an important email, or dropping the ball right after landing a major client, it's not because they're careless. It's their subconscious trying to protect them from change. Your brain is wired for survival. It wants food, shelter, and stability. Scaling a startup is the opposite of stability, so your brain hits the brakes in sneaky ways.

The founder who just landed their biggest client ever might suddenly start missing deadlines. Not intentionally. Their nervous system is flooding them with fear of the unknown, and the sabotage is an unconscious attempt to return to safety. Michael's approach is to help founders recognize the pattern without beating themselves up about it. Once you can see it happening, you can override it.

This is especially relevant for first-time founders who came from corporate environments where the stakes felt lower. The transition to "everything depends on me" triggers exactly the kind of survival responses Michael describes.

Wisconsin founders need to stop apologizing for their address.

Michael has lived in California. He's seen what coastal ecosystems look like. And his take is direct: Madison isn't Silicon Valley, but that doesn't mean you should shrink your ambition. He's seen it happen, founders lowering their standards because they think "it's just Madison" and nobody outside Wisconsin will take them seriously.

His counter-example was URL Genius, a deep linking company based in Madison that he discovered while living in California. One of the best in the world at what they do, and they're not in San Francisco. Product quality doesn't care about your zip code. Michael also pointed to Madison's biotech ecosystem as a genuine differentiator, with Epic as the anchor company creating ripple effects similar to what big tech companies did for Silicon Valley.

The practical takeaway: build your travel budget. No matter where you live, you need to be at conferences, meeting people, expanding your network beyond your city. Geography is less of a limitation than the mental ceiling founders put on themselves because of it.

Hire right and trust them, or fire fast. There's no middle ground.

Michael was pretty blunt about this one. If you hired the right person, trust them. Delegate to them. They're putting in blood, sweat, and tears to build your business, and you should be grateful. But if someone isn't working out, stop micromanaging them and let them go. The worst thing you can do is keep correcting someone's errors because you're avoiding the hard conversation.

This connects to the self-sabotage pattern. Founders who avoid firing underperformers are often doing it out of conflict avoidance, not loyalty. And the cost is massive: you lose momentum, your good employees get frustrated, and the culture suffers. The 80% rule applies here too. You don't need the perfect hire. You need someone who's 80% right and fully trusted.

Your peer group needs to push you, not just drink beer with you.

Michael takes the "you are the five people you spend the most time with" idea seriously. His argument: if you want to grow, you need a peer group with high standards who will actually hold you accountable. Not people who will nod along at a barbecue while you describe a business model that clearly isn't working. Real accountability means a friend saying, "Your business model needs to change, dude. It's not going to work."

This is something I think about a lot with Startup Wisconsin. There's no shortage of networking events and happy hours in the ecosystem. What's harder to find is the kind of peer group where people push each other, where the conversations are uncomfortable but productive. Michael's experience in the Level Set program at StartingBlock reinforced this. Being in a room with peers at the same stage who are equally ambitious validated his experience and raised his standards. That's the kind of environment that actually moves the needle.

Upcoming episodes 👀

• Jillian Bichanich (Cubbi / Pocketchange)
• Russ From (Wayfi Wireless)
• Angela Damiani (Midwest Founders Community)
• Joey Friedli (Trashpoint)
• Justin Byers (Axio BioPharma)
• Jon Eckhardt (UW Madison School of Business)

What is the Startup Wisconsin Podcast?

It's a new show where you can learn about Wisconsin's growing tech scene. Hear the stories of startups, founders, investors, and the incredibly generous people making it happen every single day.

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jacob@startupwi.org