Inside Out Leadership

CEO coaching, for founders, by founders. We help early/mid-stage startup founders scale into executive leaders & build low-drama companies, through CEO-coaching that blends psychological growth and operational excellence.

Founder, Executive Coach

Endeavor

Endeavor is a global non-profit that for 19 years has helped entrepreneurs and their companies in 25 countries reach global scale and relevance.

Endeavor Entrepreneur

GVSU Center for Entrepreneurship & Innovation

Board Member

On Deck

Helping founders step fully into their lives and scale their masterpieces.

Coach for Scale-Up Founders (via On Deck Scale)

The largest and fastest growing high school sports communication platform in America.  As the exclusive web/mobile platform for over 11million passionate fans across 40+ states (20% of the total US market), VNN is rapidly aggregating the fragmented, multi-billion dollar high school sports market onto an intelligent platform, and transforming high school sports.

Co-Founder + CEO

Helping entrepreneurs in West Michigan connect to the resources they need, while cultivating strategic positioning within the Michigan startup community.

Entrepreneur in Residence

West Michigan All Star

The largest high school sports publication in Michigan.  A tight knit group of sports junkies who made it their business to ensure that high school athletes in West Michigan got the positive coverage and recognition they deserve.

Founder

Exited founder turned CEO-coach | Helping founders discover who they are as leaders and build high-performance, low-drama companies

Over 15 years I founded and served as CEO to three companies. The last of those, VNN, became the largest and fastest growing high school sports marketing platform in the US. I raised $20M from leading VCs, built a world class team of over 100 professionals, and scaled that company to nearly 20% of the US market.

All while doing everything I could to present only the most polished, hyper-competent version of myself and my company, at all times.

And then in 2020 I left it all behind.

When I signed the papers, officially removing myself as CEO of the company I’d started a decade prior, it felt like I’d been punched in the gut.

Without my persona as the “CEO of VNN,” I realized that I had no idea who I was anymore, or what to do with my life.

It was the opportunity of a lifetime.

I spent the next 2 years searching, meditating, hanging out with monks, diving into psychedelics, and trying on new identities that never felt right.

I was stuck.

And then, I finally opened up.

I started being honest about my struggles, despite the voice in my head telling me to play a role. I let go of my compulsion to be “Ryan the CEO,” or “Ryan the entrepreneur,” or even “Ryan the guy who’s raised a ton of money and scaled a media company.”

I was just, Ryan.

And the most surprising things happened.

1. The more I opened up, the more everyone else did around me. My network grew and developed into one of deep relationships spanning life and business.

2. The more I let go, the more the universe seemed to place exactly what I needed on my doorstep. Things began to happen organically, in ways much better than I could have planned.

3. The quieter my mind got, the more I was able to access an innate wellspring of creativity and inspiration that, frankly, made work feel easy and joyful.

Me, the guy who’d worked so hard his whole life to be perfect, when I learned to let go and be me, great, meaningful work flowed out of me.

And from that foundation, I started Inside-Out Leadership, a boutique executive coaching firm that helps founders transform their companies into their masterpieces and step fully into their lives.

Today, in my work as a coach I see the tendency to present that veneer of polished competence in nearly every founder I meet. And while I recognize the need for presentation in some cases (fundraising, recruiting), I also see how that need to look good actually gets in the way of our learning and growth.

If you're tired of doing your own impression of the "perfect leader," you're not alone.

Shoot me a DM. There's another way. And it's fucking incredible.

Ryan H. Vaughn

When I co-founded VNN in 2010, I didn’t know what I was doing. My degree was in creative writing, not business. But I learned fast how to play the part - to be whoever the room needed me to be.

Raising $20 million from top VCs? I could project unshakable confidence.
Scaling from two people to nearly a hundred? I could figure it out.
Even when I had seven days of runway with fifty families depending on me, I kept that mask perfectly polished.

For years, I mistook this performance for leadership. I thought my job was to absorb the fear so my team didn’t have to. When we were down to weeks of cash, I’d make decisions through the lens of survival, while my team wondered why I wasn’t thinking bigger.
They didn’t know we were on the edge of collapse.
And I was too afraid of being vulnerable to tell them.

The startup bias toward action became my nervous system. Move fast. Check boxes. Solve the next crisis. Never stop.
But the armor that once kept me alive was now suffocating me.

Then in 2020, I signed the papers and walked away from the company I’d built for a decade. The moment the title disappeared, so did the identity that had kept me upright. It was as if I’d been holding my breath for ten years - and now, all at once, I was empty.

Without the performance, I didn’t know who I was.
I’d spent a decade building something that looked successful on the outside, but I’d never stopped long enough to meet the person underneath it.

So I went searching.
I stayed at a monastery.
I studied meditation under Zen masters.
I sat in silence until the noise of ambition started to dissolve.

Meditation taught me something simple: when you learn to sit with urges without acting on them, you discover a space between stimulus and response.
In that space, I began to see how much of my leadership had been driven by fear disguised as responsibility.

When I finally dropped the armor, something unexpected happened.
Real conversations began.
When I shared the truth of what I was struggling with, everyone around me began to do the same.
It turned out we were all exhausted from pretending to be unbreakable.

I started a small meditation group for ten founders. Within six weeks, it grew to five groups - just people calling, saying they needed this space.
They were tired of performing too.

And then, because the Universe is weirdly awesome, that somehow evolved into Inside-Out Leadership - a place for founders to do the inner work while they’re still building.

Because you don’t have to wait for the exit or the breakdown to become whole.

If you’re tired of performing the perfect CEO and ready to lead from clarity instead of fear, let's talk.

Sometimes the most courageous thing a founder can do is to take off the armor and see who’s been waiting underneath it all along.

Exited founder turned CEO-coach | Helping early/mid-stage startup founders scale into executive leaders & build low-drama companies

Years ago, I gave a talk on risk that included jail time and went semi-viral. In my experience, risk is profoundly misunderstood. And this talk is every bit as relevant today...

I got to that jail cell by chasing the great American novelist dream the way Hemingway and Hunter S. Thompson did, which is to say I drank like a fish and experimented with everything I could get my hands on. It led exactly where you'd expect.

Sitting there, I couldn't see past the next hour. The novelist dream was dead. My relationships were damaged. The path forward looked like court dates and probation, not companies and meaningful work.

I'd like to take the opportunity now to say that I'd advise you all to avoid jail at all costs. But that cell did teach me something pretty profound about risk:

Most of what stops us isn't the actual risk. It's our imagination of what the risk could be.

Risk = the actual possibility something bad happens.
Fear = your automatic emotional story about it.

When you've hit actual rock bottom - not the fear of failure, but genuine loss of freedom, you gain perspective on this distinction. And it changes how you evaluate every decision after.

The framework for separating these: 

First, name your catastrophic fear story. 
Then name the actual risk, stripped of drama. 
Most founders realize their fear is playing a 10 when the risk is a 3.

This distinction powered everything that came next for me.

I hid the concept for my second company, VNN, for months, terrified someone would steal it. Then Matt Anderson approached me at Ford Field and pitched the exact same idea I'd been sitting on. Turns out if you have a good idea, a hundred other people probably already have it.

I started VNN with Matt in 2011. During our first funding round in 2012, I had to separate the real risk (they might say no) from my fear (I'm a fraud). I can tell you now, the risk was not equal to the fear. 

I also remember being terrified when our two largest competitors announced an alliance. We had 20 schools, they had 500+. I remember walking around telling a friend it was over, and he agreed.

My fear said: We're finished, I'm exposed as a fraud, it's all over.

The actual risk: Competitive dynamics might shift.

Separating those two kept me building, and we ended up being 10x their size.

I learned this through a painstaking process of trial and error, and now I see a ton of other founders trapped in the same pattern. Every overwhelmed CEO convinced they're about to be exposed, every founder paralyzed by decisions, confusing actual risk with fear stories.

I gave this talk nearly a decade ago, running an entirely different company, and yet parts of it have become the foundation of how Inside-Out Leadership helps founders move from fear-based decisions to clarity-based action.

If you're making decisions based on fear rather than actual risk, DM me. I've sat exactly where you are, scared the next choice will be the wrong one. There's a better way.

My parents got divorced when I was 15, and 15 years later, it almost killed my business...

I was blindsided when my dad told me, driving home from school, that he was moving out. At the time, I played it off like it didn't faze me - no big deal. But I can see now just how thoroughly that event shaped my view on life. On relationships. On business. On people leaving me.

Fast forward 15 years. I was running a venture-backed company. We'd scaled from 15 to 75 people in 9 months post Series A, hitting all our numbers.

But I'll never forget the specific brown of the boardroom chair in which I was sitting when an investor told me the presentation I'd spent weeks on was garbage. He instructed me angrily to take an entirely different angle.

The CEO's job is to push back, and I knew this. But I didn't, because fear took over.

I remember the wave of shame hitting me. A bodily rush that turned me from a competent CEO to a defensive little boy, scared his father would leave if he didn't do what was asked. That fear whiplashed me into a 180-degree turn in how we were going to market.

None of this happened consciously. I simply found myself executing a new plan because the investor was so convinced.

I changed the pitch to what he wanted. And naturally, because I didn't believe in it, the investors I pitched didn't believe it either. Our raise failed. We closed a bridge round with our tails between our legs, and it took years to recover.

We can call this poor leadership, but ultimately it's just a symptom of unexamined fear.

"Until you make the unconscious conscious, it will direct your life, and you will call it fate." - C.G. Jung

The issue is that we treat this internal fear as a personal flaw to be hidden, rather than a quantifiable business risk to be controlled.

Think of how many times you've seen:

• Burnout
• Being uncoachable
• Flat investor pitches
• Flinching in a negotiation
• Defensiveness or blaming
• Underhiring key direct reports

These are all fear-based. Mostly unexamined. We can see it in others easily, but struggle to see it in ourselves. For founders, ignoring this can mean the difference between success and failure.

So what do we do?

In short, we look at the fear directly and talk about it openly. In this way, we can learn the texture of our fears and manage them consciously.

For those brave enough to do the work, the best bet is to do this with a trained professional, which is one reason why so many venture funds are funding mental health programs for their founders. 

As in my case, we’re often too close to see how our decisions are being made, so it’s helpful to have an outside perspective to help us see what’s going on. 

Doing this, helping founders navigate their fears consciously to enable authentic leadership, is one reason why I coach.

We need to treat fear as a business risk to be managed, not a weakness to be shunned.

If you're ready to look at what's really driving your decisions, send me a DM.

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I’ve invited one of our awesome clients to tell his story about working with Inside-Out. Stories like these are usually highly confidential, but this client has agreed to share theirs. Here goes:

I reached out to Ryan on Twitter in 2021 after launching my business the year before. From the outside, everything looked good - new company, new role, clear opportunity. But inside, I was drowning.

I'd been to therapy and worked with coaches before. It had always helped, but I'd plateaued. I had this gnawing sense that if I didn't overcome my personal challenges, I could experience very scary consequences.

The first year Ryan and I worked together, we focused 80% on my personal life and 20% on work. Because, as I came to learn, there's no separation. It's all just me issues. Early on, Ryan would ask where a feeling was located in my body, and I'd go completely blank. I felt embarrassed, deficient.

So he'd guide me: "Do you feel it in your throat? Your chest? Your stomach?"

Eventually, I could say, "I guess... in my throat," and that felt okay.

I was learning the language of my own feelings. I remember thinking, "It's like he's speaking a language I don't speak. I feel really illiterate."

Ryan helped me see my disconnection wasn't a problem. It was reasonable. It had served me. That release of shame let us go deeper.

2022 became the year I learned that awareness alone is progress. I got curious about my patterns without trying to immediately change them.
In 2023, we landed on a theme of where to go next: messy and connected.

I'd spent my life creating safety through control. Being the "good" son, husband, CEO. But control is an illusion. Real safety comes from being messy and connected. From showing up as who you actually are.

At work, I started speaking from uncertainty. "I'm feeling fearful about this decision" instead of always having the right answer. My team didn't pull back - they leaned in. They wanted more of the real me, not less.

My business grew from 1 company with 75 employee-owners to 4 businesses with 250+ employee-owners. Enterprise value up 200%. But more importantly, my stress dropped from unsustainable to manageable.

Here's what captures it best.

I always felt I needed to be perfect. Now I understand I was put on earth to be me. The best version isn't perfect. He's the messiest, most connected version. How much more fulfilling could life be if just being me is the point?

---

Nearly every founder I work with wears some version of the perfect CEO armor. Achieving externally while struggling internally.

If you recognize yourself in this journey, if you're achieving but not thriving, send me a DM.

I work with founders at this inflection point. The work isn't easy. But it might be the most important work you do.

For years running a startup, I only used 2 notes: On and off. On meant running full tilt toward the next objective, and off meant recharging so I could do it again. 
But I became so optimized for productivity, my creativity died...

While I checked boxes efficiently, my company's innovation slowly died. What had once been a font of creative output, slowly, by degrees, became an optimized machine driving ever more efficiently to where the puck used to be.

It's remarkable how quickly nimble startups turn into slow legacy companies when they stop nurturing the creative recklessness they started with.

I've since learned there's a spectrum, with productivity on one side and creativity on the other, and I'd been stuck at the productivity extreme for so long that I'd forgotten about everything else.

So the question became: is it possible to optimize for creativity?

I used to think creativity was chaotic. Something spontaneous, unmanageable - useful for artists, not CEOs. But I’ve learned it can be cultivated deliberately, like a muscle you’ve simply stopped using.

Creativity begins where control ends.

It can't emerge from pressure or optimization - it emerges from permission.
From leaving a little space in your schedule unclaimed.
From walking without plugging in to a podcast.
From noticing what your mind does when it isn’t told what to do.

The irony is, the less I tried to be creative, the more creative I became.
I’d gone from “on/off” to something much richer - fluid, alive, responsive.

As leaders, we model the behavior we most value. If we only reward output, our teams will learn to suppress imagination. But if we make space for curiosity, they’ll follow us there too.

You can’t build a masterpiece from binary inputs.
You need the full range.

If you're wondering how to rediscover play after optimizing it away, try the Imaginary Lives exercise, modified from Julia Cameron's The Artist's Way.

If you had 5 other lives to lead, what would you do in each?

I'd be an astronaut, author, professional basketball player, hippie, physicist. You might be a cowhand, psychic, scuba diver, belly dancer, painter, rock drummer.

Write down whatever occurs without overthinking it, then select one and do it this week. If you put down country singer, can you pick up a guitar? If you dream of being a cowhand, what about horseback riding?

The secret is realizing you only have one life, and you won't get another chance unless you take steps now.

Not only does this work wonders for juicing your creative capacity, it is a great launchpad to a more nuanced, complex, and complete way of life.

---

Proud to coach with Inside-Out Leadership, CEO coaching by exited founders who've been there.

I've never been big on business books. Most say their point in 3 chapters, then repeat themselves for 200 pages. But these 5 books changed everything for me - in my business and my life:

1. Reboot by Jerry Colonna

Written by a former VC turned executive coach, this was the first time I felt someone really understood what I was going through as an early-stage CEO.

Colonna's questions helped me see how my need to appear competent was actually making me a less effective leader. After reading it, I stopped presenting only the polished version of myself in meetings and started being honest about my struggles with my leadership team.

Perfect for: Founders struggling with the weight of the role.

2. The Second Mountain by David Brooks

This book transformed a monthly book club I set up over a decade ago.

So many of us spent years chasing success, only to realize upon getting there that it was an incomplete goal. Brooks helped me shift my focus from optimizing my company's appearance to investors to building it around what truly mattered to me.

Perfect for: Accomplished leaders questioning their "why."

3. The Meaning Revolution by Fred Kofman

The former head of culture at LinkedIn taught me that people yearn to dedicate their lives to work that outlives them and connects to values beyond themselves.

His framework helped me reframe our team's work from hitting metrics to building something that mattered. We went from tracking outputs to talking about impact.

Perfect for: Second-stage companies hitting a ceiling.

4. The Artist's Way by Julia Cameron

Most founders look back at their early days as a time of tremendous innovation. Then the constant demands of running a company beat the creativity out of them.

Cameron wrote The Artist’s Way to help people rediscover their creative spark. For a leader, this can be the key to unlocking previously inaccessible levels of growth, as founders are simply artists working at scale.

Perfect for: Leaders looking to regain their edge.

5. The Advantage by Patrick Lencioni

The most useful "how to run a business" book I've read.

Lencioni's blueprint for company operations was foundational to how we rebuilt our corporate culture at VNN, aligning a 100-person team with only a few key structures.

Perfect for: Entrepreneurs leading companies >20 people

Reboot helped me see my patterns. The Second Mountain helped me question my goals. The Meaning Revolution helped me rebuild culture around purpose. The Artist's Way reignited my creativity. The Advantage gave us the structure to scale it all.

These books provided the frameworks. But turning frameworks into lived transformation is where the real work begins.

That journey from founder to conscious leader is exactly what we help navigate at Inside-Out Leadership.

And to save me some time, help me out. What other business books are worth reading all the way through?

In 2015, when Volkswagen’s emissions scandal broke open, the world focused on the software - the quiet lines of code that made 11 million cars look cleaner than they really were. But what struck me was the culture required to create it...

To build something that deceptive, you first need a room where truth has become dangerous.

A room where engineers are aware that the math doesn't quite add up, but also know that saying so might cost them their careers.
A room where fear, often slow, invisible, and cumulative in nature, has more influence than integrity.

Every founder builds some version of that room.

I certainly did.

Early in my first company, there were days when I moved through the office like a storm. I didn’t yell or threaten. I just radiated tension - the kind that makes people speak in careful, buffered sentences. I thought this was me being “focused.” My team thought otherwise: Don’t bring him anything he won’t want to hear today.

It happens gradually. A roadmap that’s slipping. A sales forecast that needs optimism to survive. A technical debt warning softened because last time you talked about it, your jaw clenched and your tone tightened.

No one lies. They just start performing.

This is how cultures drift - not through dramatic moments, but through tiny shifts in reality. The truth becomes something people handle with gloves.

Volkswagen’s investigation blamed “individual misconduct and weak processes.”
But the deeper, human truth is far simpler:

When leaders react poorly to hard truths, teams learn to stop sharing them.

And it almost always starts inside the leader.

For me, it started with fear:
Fear of slowing down. Fear of appearing uncertain. Fear of confronting the parts of myself I’d spent years outrunning.

When I couldn’t hold difficult truths internally, I couldn’t hold them externally.
So people shielded me. Humans are prone to protecting each other from discomfort, especially when power is involved.

It took burning out, emotionally and physically, to realize the actual cost of this. Once your team learns to protect you from reality, you very quickly lose the ability to lead it.

Unfortunately, like all complex things, the antidote isn’t as simple as transparency training or an open-door policy.

It’s inner work.

The slow, sometimes painful excavation of the fears, patterns, and old identities that make certain truths feel threatening.

When a leader builds internal safety - the ability to hear hard things without collapsing, defending, or retaliating - a strange thing happens:

People start telling the truth again. They bring you problems earlier. They stop curating the world on your behalf.

And the company breathes.

Volkswagen is an extreme example, but the pattern is universal. A culture of honesty starts with a leader who can sit with uncomfortable truths without flinching.

If you’re scaling fast and want to make sure fear isn’t quietly writing your culture’s code, DM me.

A 2020 study found that 88% of languages face such severe AI neglect that they are at risk of extinction. We're building a biased foundation for how humanity will access knowledge - and it's causing a global "knowledge collapse..."

A recent analysis found that nearly half of all ChatGPT queries since launch were attempts to understand the world or solve a practical problem. We’ve already crossed a threshold. We've outsourced knowing to these systems without questioning what they actually know, or more importantly, what they're systematically forgetting.

Knowledge doesn’t enter these models evenly. It flows in through particular, narrow channels, shaped by power, literacy, colonization, economics, and the long shadow of which cultures were digitized early and which were ignored. They privilege certain epistemologies, typically Western and institutional, while marginalizing everything else. Oral traditions, embodied practices, and ways of knowing that never got written down are simply omitted.

Look at the evidence. Common Crawl, one of the largest AI training datasets, contains 300 billion webpages. 45% of its data is in English, a language spoken by only 19% of humans. Hindi speakers make up 7.5% of the global population but account for only 0.2% of the data.

When I sit with those numbers, I see a slow collapse of the tributaries feeding the river of human wisdom. A deliberate, almost willful intellectual atrophy.

The computing world classifies 97% of languages as "low-resource." But that framing reveals the problem. These are languages with millions of speakers and rich traditions that simply aren't represented in digital spaces that AI systems can access.

To make matters worse, these systems are now training themselves. AI models are ingesting AI-generated content at a pace no human can audit. Each cycle sifts the world through the same sieve, tightening the mesh. Dominant ideas become more dominant. Niche knowledge, local wisdom, and context-specific understanding gradually disappear from what the systems can retrieve. 

Researchers are calling this "knowledge collapse."

What's at stake isn't representation in some abstract sense. It's whether future generations will have any connection to ways of understanding the world that evolved over millennia.

I believe Small Language Models (SLMs) are the solution to this systemic problem. We must be intentional about building models that preserve localized wisdom rather than flatten everything toward statistical dominance. 

The main challenge - and the profound arbitrage opportunity - is that the knowledge being marginalized often sits within communities that are not able to digitize it and train their own models.

One perfect example of this opportunity I see is a Wisdom Tradition SLM.

Question for the builders and thinkers: 

Are there any projects or tools you've seen focused on creating an open-source, non-commercial SLM trained specifically on the world's wisdom traditions?

Moneyball came back to Netflix recently, so Laura and I watched it for the umpteenth time. Billy Beane’s quest to change baseball teaches us a surprising lesson about disruption in any industry...

In every field, the status quo resists outsiders. Disruptors must push against inertia, often alone, with a hunch, limited data, and a willingness to risk more than others. Beane spends the movie confronting the possibility that he’s wrong, and the failure and ridicule that would follow.

Even inside his own organization, people push back. They tell him all the reasons he’s wrong, all the reasons he should give up and build a team “the way it’s always been done.”

But as the disruptor, Beane’s job is to keep going. Disruptive ideas aren’t recognized as such until after the fact. Until then, the leader’s task is to persist through doubt.

Once he’s “convinced” his staff to sign players based on on-base percentage instead of conventional value, the pressure ramps up. For the first dozen games, his approach seems to fail - providing early data that “proves” the old way is best.

At the early stages, success is often indistinguishable from failure when measured by traditional metrics.

He keeps going.

“A good process produces good results.” - Nick Saban

With every reason to quit, Beane continues because his team’s actions align with success, even if results don’t yet show it. He sees that consistent actions matter more than short-term outcomes. It’s one of the deepest truths in entrepreneurship.

He doubles down on his belief that optimizing for on-base percentage will win in the long run. He sees his players getting on base and trusts his system to translate that into wins.

And it does.

The same story unfolded in the NBA with Daryl Morey and the Houston Rockets. “Moreyball” valued threes, layups, and dunks above all else. Early on, focusing on shooting threes, and not necessarily making them, looked absurd. But when the Rockets started winning, every team copied them.

As The Athletic put it, “Results, often, are the least important thing. The process of what happens does matter.”

Beane’s A’s looked like a misguided experiment until they rattled off 20 straight wins. Now, every team in baseball follows their playbook.

Moneyball shows what real disruption looks like. We imagine it as a bold founder rewriting an industry overnight. In truth, it’s an entrepreneur pushing an unproven idea uphill while everyone says he’s wrong and every metric says he’s failing.

When the world finally catches up, the disruptor feels vindicated. But after so many sleepless nights, doubts, and near-collapse, the first thing he actually feels isn’t pride.

It’s relief.

Keep going, friends. Second-guessing yourself is part of the process.

“How will your company become a unicorn?” The question seems innocent enough. But there’s a trap inside, just like there’s a trap in any question that asks a founder to predict the future with certainty... 

No matter how much you know about your business, how compelling the opportunity, or how confident you feel, you cannot predict the future.

Describing a spectacular outcome and a straight path to get there can seem like the norm when we pitch our companies. But predicting the future with certainty, besides being inaccurate, may also cause you to hold onto a bad strategy for too long and sink your company. This is backed by science.

A famous study once showed that rats preferred receiving shocks to the brain in the present to the possibility of receiving bad outcomes at some later time in the future. They feared the uncertainty of the future more than the pain itself.

We're not so different. Humans also hate uncertainty - so much so that we are immensely attracted to folks who seem certain. Given that, it’s no wonder startup founders project certainty in order to attract others. Certainty gets coffee, because certainty is a closer. 

But as effective as certainty is at closing deals, it’s equally effective at closing minds. 

The minute we fixate on a singular solution, not only do we stop looking for alternatives, but our minds (specifically the Reticular Activating System) filter out any evidence to the contrary. For example, when you buy a new car, and you suddenly start seeing that car everywhere. It's not that there are more of them; your mind just notices what it chooses to notice.

So when someone asks you how your company will become a unicorn, and you tell them precisely how you’ll get there, you’re locking your nervous system - and your company - into a single path.

If everything goes according to plan, you're fine. But the moment something off-script happens, your previous prediction may become your blindfold.

The best leaders, on the other hand, are confident but never rigid. 

They are confident, even when they’re uncertain, because their confidence is rooted not in their plan coming to fruition, but in their ability to navigate the uncertainty. Some leaders hide the areas in which they are unsure. But the most effective leaders own their uncertainties, knowing that uncertainty is unavoidable, and are confident in their ability to pivot and figure shit out.

Next time you spot the trap, “How will your company become a unicorn?”, I invite you to smile and confidently own your uncertainty:

“I don’t know. The current data suggests it might happen this way. But if not, we have a plan for that, too.”

Why would someone follow a leader who answers like that?

Because they see that you have the same doubts that they have, but you are confident in your ability to navigate the unknown, and you’re betting your life on it anyway.

Proud to coach with Inside-Out Leadership, CEO coaching by exited founders who've been there.

I chased achievements for 20 years and felt empty the moment I got each one.
Only the next goal mattered, until that became meaningless too.
Here's the pattern that kept me trapped (and how to break it):

Everything humans do is either to steer toward feelings they interpret as positive or to avoid those they interpret as negative. There isn’t much more to it than that.

I’ve gone to incredible lengths to curate the feelings I’m exposed to. Ended relationships rather than face my failings. Blamed others rather than confront what I’ve done wrong. Most often, I imprison myself in tunnel vision, diminishing everything that isn’t the Goal to avoid my deepest fear: 

The fear that I’m not good enough.

That fear leads to knee-jerk decisions that seem right in the moment but that I regret later. I’ve sent so many emails that gave me a dopamine hit of productivity, but did more harm than good.

I learned early in life that I wasn’t good enough, and decided I’d do anything to prove otherwise. My life became one long chain of achievements, each seeming like the most important thing until I attained it, at which point it became irrelevant. I was still not enough. Only the next achievement would prove otherwise.

It wasn’t until I stopped achieving - forced through failure to slow down - that I could see the operating system I was living through. It was painful as hell, but it forced me to confront my inadequacy head-on. Through that pain, I finally saw the pattern and realized I had a choice.

Instead of achieving to outrun inadequacy, I could stop. Face it.

Sitting in that inadequacy was exquisite torture, yet freeing. I didn’t have to reflexively jump into action. I could simply be and, as Trungpa Rinpoche says, “lean into the sharp points.” Feel what I’d been running from and let it pass.

By sticking with the feeling, I developed familiarity with it.

For me, fear feels like:
• Wired eyes, like I haven’t slept
• A tight chest, like after smoking too much
• A pounding heart when I see success in others
• A spinning mind, comparing my achievements to others

I can now recognize it when it comes, and resist the reflex to act. I know it always passes, even when it feels like it won’t.

I’m familiar with my primal fear. Not friendly with it, but acquainted enough to recognize it. The fear I once jumped through hoops of fire to avoid is just bodily sensation mixed with an urge to achieve.

For years, that feeling drove my actions - fueling both success and destruction.

Now, when it arises, there’s a choice. Most of the time, I sit with it and appreciate how its intensity reminds me I’m alive.

Then I look at the situation with clarity and do the next right thing.

That shift from reactive to conscious changed everything.

I created Inside-Out Leadership to guide founders through this transformation because I know how powerful it is - and how difficult it is to do alone.

If you recognize this pattern, let's talk.

It seems self-evident that the harder and longer you work, the more you get done. It's also not true. NASA's long-term study showed that taking a 26-minute nap in the middle of each shift increases job performance by 34%:

To restate: take a 26-minute power nap and you'll get 1/3 more done.

Before you dismiss this as "interesting but I gotta get back to work," recognize that most major breakthroughs come from leaning into something that's both counterintuitive and true.

I speak with stressed CEOs regularly, and when I talk about self-care I usually hear the same thing: 

"I'm too busy. I know it's important, but right now I'm just strapped. Maybe tomorrow."

If I share this NASA data, most get excited about it. Many even think about how their teams could power-nap. But almost none would take a nap themselves later that day.

If I told them that Harvard Business Review found:

Healthy eating leads to better moods and higher energy, exercise increases blood flow and boosts learning and memory, and good sleep improves focus, creativity, and empathy... they'd probably still think that's compelling for someone else, but they themselves have too much to do.

I get it. I've been there. And now I spend 5-7am every morning on a rigorous self-care routine, simply because it makes me more effective.

Here's the thing: trying to outwork your problems is precisely how most leaders react to the idea of taking care of themselves first. 

And that's the popular choice.

Which means there's a competitive advantage when you lean into the counterintuitive benefits of self-care.

Eat healthy, exercise, sleep well, and take naps. Go win your market.

If you're ready to address the deeper patterns driving your burnout and your inability to stop, shoot me a DM. I'd love to help.

Ben Horowitz says most successful companies will experience 5 "WFIO" (we're f*****'d, it's over) moments. It’s an entrepreneur’s resilience in those moments, not strategy or tactics, that separates the successful companies from the rest:

I use the word resilience intentionally, deliberately drawing a distinction between it and its close cousin: persistence.

Most founders hear "resilience" and think of a stone-cold badass shrugging off every challenge. A scarred warrior gritting through the pain, lifting up his spear once more.

That's persistence. 

Persistence is force.
It’s the inner voice that says, “Keep moving, no matter what.”
It gets you out of bed when everything hurts.
It carries you through the sprint, the crisis, the all-nighter.

But persistence runs on pressure. And while it works in the moment, it comes with a huge cost.

It demands control, suppresses emotion, and burns a fuel that will eventually, without fail, run out.

As decades of psychological science will attest, every time you push down your emotions to get shit done, you incur what I call emotional debt.

Like companies incur technical debt, leaders incur emotional debt when they repress fear, worry, or anger to keep moving. A little can be useful when managed consciously and paid back quickly. But perpetual emotional debt clouds your judgment.

Think of a time when you’ve seen a leader bite an employee’s head off for asking a question. Or think of the dreaded burnout. I know this one personally. I thought I could will myself past the unpleasant stuff with no repercussions. Then it all came due at once and I had to take a sabbatical. 

It can be a good decision to max out your emotional credit cards by persisting in the heat of a crisis. Just remember that debt compounds, and if you don’t pay your bills, don’t be surprised when the creditor comes calling to break your kneecaps.

Resilience is different.

Resilience is supple. It bends.

It's the way skyscrapers flex in the wind, moving with every gust before returning to center. It's water adjusting to every obstacle but never stopping its flow.

Resilience is intentionally feeling the emotions without changing them, all the way through to completion, and then moving forward with a clear head.

As counterintuitive as it sounds, leaning into your negative emotions - consciously feeling the texture of your fear rather than trying to fix it - produces profound results.

By processing emotions in real-time with curiosity rather than resistance, you allow them to move through you and be completed. You pay the emotional cost in cash, not credit.

Next time you get bad news, try this:

Before opening Slack or calling your team, take 90 seconds. Close your eyes. Notice where the emotion lives in your body. Chest tight? Stomach dropped? Just observe it without trying to make it go away.

That's resilience.

How about you? Are you habitually practicing persistence or resilience?

I ask one question in every CEO group I run: Tell me about the time when you felt most alive. 90% of the answers are the same (and not what you'd expect):

One CEO, fresh off selling his company: "Halfway up a mountain in Patagonia, alone between everything. Looking back at how far I'd come. Looking forward at where I was going. That moment."

Another: "Almost dying in a truck in Asia during a freezing rainstorm. I'd never felt more alive."

A third: "After 100-hour weeks, standing at our kickoff watching it unfold. Everything went wrong the day before. But we did it. I felt like I could do anything."

These moments have something in common. They all happen in liminal space. 

The transition space between who we were and who we're becoming. When we step off our path and see it clearly. In these spaces, stripped of our everyday answers, we're awake to the fundamental question of ourselves.

We feel infinite. Alive.

Yet we spend most of our lives avoiding these moments.

We optimize away uncertainty. We convince ourselves we know exactly where we're going - Series A by Q3, Series B by next year, exit in 5 years. We shine our pitch decks and LinkedIn profiles until every rough edge is gone. We tell ourselves once we hit the next milestone, close that round, get to profitability - then we'll have time to figure out who we are and what we want.

But when faced with the fundamental question of our lives, we race for the next answer. The next salve of certainty, in a milestone, a compliment, or a white picket fence. The very moments that could wake us up - uncertainty, transition, not-knowing - we treat like problems to solve as quickly as possible.

The power of liminal space, and the importance of intentionally creating it in your life, is actually the oldest topic in the book, and as close to perennial human wisdom as it gets.

Richard Rohr: 

"If at least one-seventh of life is not consciousness, presence, and naked human being, the other six days will be caught up as human doings that have little depth, meaning, or final effect. 

If at least one-seventh of life is somehow Sabbath and sabbatical, the rest will take care of itself. 

Without daily, weekly, and yearly choices for liminal space, our whole lives eventually become liminoid and we end up just doing time.”

Read this post ten times and you'll find no answers. No four steps. It's uncomfortable publishing this way. But I'm not writing for comfort. I'm writing to feel alive.

Life will create opportunities for liminal space whether we like it or not. The question is whether we'll rush toward the next answer, or allow ourselves to be changed by the question. 

This is some of the work we do with founders through Inside-Out Leadership. Creating the liminal spaces where you see yourself clearly, stepping off the path long enough to know if it's the right one, and accessing the aliveness that's always been available.

What a fun job I have :)

I worked with a founder recently who was about to begin raising his Series B. His company was doing well, its unit economics outstanding, and its growth rate solid. But he was still worried he was going to f**k it up...

He had tried and failed to raise the year before. He’d told investors the story, generated interest, gotten partner meetings with top-tier funds, moved through diligence quickly. But then every firm passed.

Failed fundraises are traumatic.

It’s not for nothing that people refer to a founder’s company as “their baby” - founders pour every ounce of their lifeblood into their company for years in an effort to help it grow up. Then, when other smart people tell you your baby isn’t worth their time, it tends to leave a mark.

As a good CEO, he went back to the drawing board, broke down the story he’d been telling investors and himself, and identified critical issues that needed fixing. He and his team spent twelve months ruthlessly addressing them.

And yet, preparing for the growth round, he hesitated.

What if it turned out the same as last time?

His failed fundraise had given him valuable data, which he used to improve the business. But the driver of that change was also traumatic.

The reptile part of our brains deals with trauma in a way so highly adapted to survival that it hurts. His nervous system was “helpfully” reminding him how dangerous fundraising was. It recognized a threatening situation it had survived and sent the same red alert.

Our brains are wonderful tools, but trauma can sabotage high performers and prevent them from regaining confidence. And to get a fundraise across the finish line, confidence is everything.

So he needed to process the trauma.

One way to deactivate a traumatic response is to look analytically at the present with your more evolved brain, clarifying what’s different now so the fear center calms down. For him, that meant examining the previous raise closely.

Looking at it through a process lens, we noticed something important: all investors passed post-diligence. That meant he’d actually done a great job getting them excited - otherwise they never would have completed diligence. They passed because they uncovered flaws in the business - the same flaws he’d gone on to fix.

Which meant this: 

If he was the guy who convinced smart people to invest time into a fundamentally broken business, he was certainly the guy who could get them to invest time in the rocketship he was running now. And if they invested time now, he was confident they’d invest capital.

This simple reframe turned a confidence-sapping failure into a proof point of his fundraising mettle.

And this time, the odds were in his favor.

Nothing had changed. But by looking more closely, everything had. He left our conversation jacked up (a term I don’t use lightly) and ready to pitch. 

I felt like Wendy Rhoades in Billions.

I’ve always liked Paul Graham’s essay about how to do what you love. He describes a two-step process for achieving the career you've always wanted. However, research from Johns Hopkins suggests that he got this all wrong...

Graham's first step: working hard, with ridiculously incomplete information, to determine what you actually love to do.

Second step: incrementally steering toward that outcome via a specific process of either A) gaining influence to enable you to do more of what you like and delegate what you don’t, or B) moonlighting in what you love to do until you can make money at it.

This process is very similar to how I got started in entrepreneurship. 

I first decided I wanted to watch sports and call it “work,” then figured out how to make that happen. That also happens to be how Inside-Out Leadership started: I identified a passion for helping entrepreneurs build life-giving companies without self-immolating, and from that I’ve constructed a business to make that happen. The hard part, and Graham talks about this, has always been figuring out what you want.

So we’ll call this paradigm “How to do what you love.” 

It turns out, it may not be the best way.

Research from John’s Hopkins University indicates that it actually works the opposite of this. They showed in a clinical setting that humans random choices lead to preferences, not the other way around. We decide something, and then create reasons why we like that decision. From this, it follows that choices lead to preferences lead to habits lead to identity, to us becoming the person we somehow decide we were born to be.

In other words, from a granular, neuroscientific, process perspective, human beings don’t choose what we like - we like what we choose.

The implications of this on doing what we love are profound. The process of painstakingly finding what we like to do and then creating a life in which we get to do that is a tried-and-true one. But it’s hard, as Graham illustrates:

"Whichever route you take, expect a struggle. Finding work you love is very difficult. Most people fail. Even if you succeed, it's rare to be free to work on what you want till your thirties or forties. But if you have the destination in sight, you'll be more likely to arrive at it."

However, based on the science about how we actually develop what we love, there may be a better option, significantly less arduous and more in keeping with the mechanics of what it is to be human.

Instead of searching for what we want, we can simply search for why we love what we do. The “how to love what you do” paradigm, if you will.

As Seth Godin said: If we commit to loving what we do, we’re more likely to find engagement and satisfaction. And if what we do changes, we can choose to love that too.

---

Where in your life are you still waiting to “feel passion” before making a choice?
And what might happen if you flipped the sequence?
DM me or let me know in the comments.

I see over and over how traditional goal-setting methods can actually demotivate founders. Here's a quick, 7-step process for setting goals that actually produce momentum:

Here’s a typical case:

You set a long-term goal - say 1M users. You break it into milestones, like 500 users in 30 days. You build an action plan: SEO, paid ads, landing pages. You work nights and weekends, sacrifice everything - and miss.

Maybe your software went down, or Facebook changed its rules, or your target was just too ambitious. Either way, you worked hard and still missed. Now you’re not just fighting market challenges, you’re questioning whether you even have what it takes.

This is the trap: tying your self-worth to outcomes. Society tells us this is how it works. But it doesn’t have to.

Starting a company is hard enough without setting yourself up to feel like a failure when things outside your control go wrong.

The most effective founders attach their sense of accomplishment to completing actions, not to producing results. That way, they can generate momentum - the lifeblood of any startup - through their own efforts, regardless of outcome.

Here’s what that looks like:

You set your goal, break it down, and execute your plan. You finish your landing page, your SEO, your ad campaign. You celebrate completion because that’s the win. Then something breaks. You miss the goal - but you’re still winning. You iterate, adjust, and keep going.

You can imagine which approach produces better results.

The best founders I know follow this 7-step process:

1. Set your goal
2. Break it into milestones
3. Build an action plan for the first milestone
4. Complete the plan (this is where you either succeed or fail)
5. Analyze, dispassionately, whether actions taken produced expected results
6. Accounting for that analysis, iterate action plan to reach revised milestone
7. Repeat

Your job as a founder isn’t to control outcomes - it’s to complete the actions you commit to.

So by all means, set goals. Big hairy audacious ones. But remember: you control your actions, not the results. Be ruthless about doing what you said you’d do, and leave the rest to the universe.

Proud to coach with Inside-Out Leadership , CEO coaching by exited founders who've been there.

Active:
• PM career coach (January 2025 - present)
• Fractional PM at Series A fintech startup (Sep 2024 - present)
• Maven course instructor (July 2024 - present): Teaching "PM Interview Bootcamp with AI Copilot: Product Sense & Analytical Thinking", a top-rated Product course on Maven (selected by Lenny Rachitsky for Lenny's List).

Concluded:
• User research project to interview 20+ customers for seed-stage AI startup (Dec 2024 - March 2025)
• Product Advisor to pre-seed women's health startup (June - August 2024)
• Interim Head of Product & Design at stealth seed-stage AI company (March - July 2024)
• Fractional PM at seed stage fintech startup (March - April 2024)

Portfolio Career

Supra

Supra is an invite-only network focused on connecting, supporting, and growing high-caliber Product leaders. I co-host the Supra Insider podcast with Marc Baselga, the founder of Supra. Check out the podcast here: https://suprainsider.substack.com/

Member & Podcast Host

Continuum

Continuum is a premium executive talent marketplace matching venture-backed companies w/ vetted execs for consulting, advising, interim, and full-time opportunities.

Continuum raised its seed round from Uncork (Jeff Clavier) and secured a Series A from Pelion Venture Partners. I joined shortly after the Series A as the first full-time product hire.

Head of Product & Design

Attentive

Led high-visibility product initiatives to expand TAM and deliver more value for customers. 

Managed team of 2 Senior PMs solving problems around SMS and Email deliverability.
---
Attentive is the most comprehensive text message marketing solution, driving 18.5% of total online revenue for businesses by creating thoughtful SMS experiences. Over 5k leading businesses like CB2, Pura Vida, Urban Outfitters, Rebecca Minkoff, Steve Madden, and more rely on Attentive and see strong performance, like 30%+ click-through rates and 25x+ ROI. 

Attentive is backed by Sequoia, Coatue, Bain Capital, IVP, and other leading venture firms.

Lead Product Manager

Facebook

Led a team focused on helping millions of small business advertisers succeed through personalized guidance. Drove $300MM+ in incremental annualized revenue for FB (statsig).

Product Manager

Abstract

I joined Abstract as the first product manager. As the Collaboration team PM, I defined our product roadmap for collaborative workflows in the product, including features for design review, presentation and delivery/handoff.

At the time I joined Abstract, it was a Series B company with 60 employees.

Abstract is an enterprise SaaS collaboration tool for mature design teams. The company counts Disney, Hulu, Microsoft and many other Fortune 500 companies in their customer list.

Breathe

Breathe was a simple iPhone app that allowed users to set reminders to take deep breaths throughout the day. I built Breathe as a side project while at Life360 and launched our app a full year before Apple launched their own Breathe app for the Apple Watch.

Before sunsetting, Breathe earned 65k downloads and 4.9/5.0 stars w/ hundreds of reviews.

Creator

Canvas

As lead PM for the Canvas shopping and checkout experience, I worked with a cross-functional team of engineers and designers to build an entirely new customer-facing experience from scratch. We then iterated over the following two years to optimize conversion (primarily focused on driving new reservations). 

Canvas was launched as a subsidiary of Ford post-acquisition of Breeze and was later acquired by Fair.com in the summer of 2019. 

For the full year prior to Breeze's acquisition by Ford, I was the first and only product manager, leading a team of four engineers and one designer to build Carmada, our flagship fleet management product. When I joined Breeze, it was a Series A company with 50 employees.

Life360

While at Life360, I supported our product managers and built processes for communication between our customer support center in Las Vegas and the QA + Product teams in SF. I also designed from the ground-up an improved tool for our customer support agents to resolve issues. 

I joined Life360 when it was a Series B startup with 30 employees. 

www.life360.com 
IPO in Australia in 2019 (ASX: 360) followed by IPO in the US in 2024 (NASDAQ: LIF)

Project Manager

​Shwrüm

When I was a young and dumb 22 year old, I founded a company with the vision of building “Resy for clothing stores”. Learned a ton and discovered a passion for customer research and product development (despite being bad at both).

Co-Founder & CEO

I've been a founder, joined three different startups as their first PM, and held senior PM roles at Meta and Attentive. After leading product & design at Continuum, a marketplace for fractional executives, I now partner with early stage founders as an advisor and coach PMs to help them land their dream roles.

My experience spans many different models: B2B SaaS (Abstract), martech (Attentive), ads (Facebook), consumer (Life360, Breathe, Canvas), automotive fintech (Breeze -> Canvas), marketplace (Continuum).

I've also worked across the entire spectrum of funding cycles: founder, Series A (Breeze, Continuum), Series B (Life360, Abstract), Series C (Life360, Abstract), Series E (Attentive), and post-IPO (Facebook).

Ben Erez

This week has been full of bangers w/ Gamma, SuperMe, and Reforge flooding my feed. Why I'm excited for each of these: 

Monday: Gamma's Series B is a massive validation for a product I love (Marc Baselga and I literally couldn't run Insider Loops without it). The product is straight-up magic and we're happy paying customers. Diana Kimball Berlin on the product team @ Gamma is a friend of the Supra Insider podcast so we're extra happy to see the company crushing. Also, Lenny Rachitsky annual subscribers get the Pro tier for free which is more than enough to make dope things 🔥

Tuesday: SuperMe's public launch with the announced seed round brings wider attention to a product that aims to solve a problem many creators (myself included) experience intensely: scaling access to an ungodly amount of published content in a central conversational UI. I'm onboarded and users can sign up and chat with my SuperMe today. The professional network is intriguing too but I suspect that'll be a longer play. I'm bullish on anything Casey Winters (co-founder & CEO of SuperMe) touches so it'll be fun to see how this part shakes out.

Wednesday: Reforge's launch of their new product, Reforge Build, feels like a fresh take on the AI-powered prototyping category because you're never starting from scratch. Marc & I recently had Brian Balfour (founder & CEO of Reforge) on the Supra Insider podcast and did a deep dive on the company's expansion from courses to software products and I can't wait to publish the conversation next week because it's a behind the scenes look at world-class strategy.

I always talk about this being a golden era for builders but let's be honest: as a user of great products this feels like Christmas every week. 

What a time!

I help PMs ace product sense & analytical interviews | Ex-Meta | 3x first PM | Advisor

My course has generated over $100k in earnings but I almost didn't launch it at all. The push came from Maven's instructor whisperer:

When I first talked to Claire Chen at Maven about teaching a course, I was torn between two potential topics: (1) user research or (2) interview prep.

Claire has worked with hundreds of operators launching courses on the platform and has seen the full spectrum. She's seen the breakout successes and the ones that never get off the ground. 

Claire's pattern recognition is world-class because her entire job is to identify instructors who are likely to succeed on the platform and help them identify the right starting point.

When I mentioned interview prep to Claire, she was skeptical: “That’s a tough topic. It’s incredibly time-sensitive. You have to catch people at the exact right moment when they’re actively interviewing.”

But then she added something every great advisor and coach does: “You know your market best. If you think there's something here, I think you should go for it.”

This is one of the most counterintuitive things Claire and the Maven team broadly have learned from watching thousands of courses run. 

No matter how much data Maven has about student behavior and interest, the instructor is always closer to their market.

And in this case, I was way closer to my market than Claire and the Maven team.

I was talking to candidates every day. I had been doing paid mocks and coaching for 2-3 years. I could feel the gap in the market in a way that wasn’t obvious to those on the outside.

So instead of telling me “yes” or “no,” Claire pushed me to validate it myself.

Here’s how I tested demand:

1) I polled the Supra community about interest in attending a live talk about product sense & analytical thinking interview advice
2) I ran the session with 30+ people and the response was strong
3) I hosted a lightning lesson on Maven that brought in 700+ signups
4) I filled my first cohort with 10 students and iterated from there

Fast forward to today: I've run 10 cohorts over the last 1.5 years and earned over $100k on Maven. While it's not $1mm, it's been a meaningful contribution to my income in this solopreneur chapter.

I also would have never built my Copilot if the course didn't force me to wrestle with an insane amount of questions from students. The Copilot was born from an effort to answer student questions at scale and has also become a real portion of my income.

And none of the above would’ve happened if Claire hadn’t pushed me to launch.

If you’re considering launching a course, our latest episode of the Supra Insider podcast with Claire is packed with advice, lessons, and what she’s seen work for new instructors.

It’s exactly the kind of conversation I wish I had heard before I started.

🎙️ Episode links:

Spotify: http://bit.ly/3Kn2g4E
Apple: https://bit.ly/4prGA69
YouTube: https://lnkd.in/eER6HxTy
Substack: https://lnkd.in/e3h9wss2

I help PMs ace interviews at Meta, OpenAI, Stripe, DoorDash + | Ex-Meta | 3x first PM | Advisor

I just discovered a new twist on Product Sense interviews that caught a candidate (and me) off guard.

One of my students recently interviewed at a growing tech company. The recruiter said to "download [prototyping tool] ahead of time because they'll be expected to prototype live."

The interview was titled "Product Sense." My student expected the usual flow: motivation, segmentation, problem selection, solution design. 

Instead, the interviewer shared some revenue data and asked them to start by modeling retention recurring revenue, then to diagnose an issue in the data worth solving.

So my student built a model live, on Zoom, while screen-sharing. No code, no design prompts. Just rows of data and a blank spreadsheet.

Then, with ten minutes left, the interviewer said: "Now open [prototyping tool]. Here's a PDF of our current flow. Prototype how you'd fix conversion."

My student uploaded the PDF, mocked up a page with a major improvement, and talked through the UX. 

Needless to say, it was all messy.

This "Product Sense" interview felt more like a hybrid business case + live prototyping test.

What's interesting to me as a coach is that the same PS interview fundamentals were still being evaluated, just in a different way:
✅ Demonstrating business literacy
✅ Narrowing in on a specific audience
✅ Diagnosing root causes preventing growth
✅ Exploring creative solutions to a problem

My advice for candidates prepping for "Product Sense" interviews: don't assume every company follows the same script. Get clarity about the tools you'll use, what's being evaluated, and how time will be spent.

The more you understand the expectations, the better you'll perform.

But you'll never have perfect information.

So... expect the unexpected.

And do your best.

All year long I bombard the Maven team with (hopefully) constructive feedback about what could be better so in the spirit of Thanksgiving, I want to recognize 10 aspects of Maven I'm grateful for as an instructor:

This is not in any order but here we go:

1) Their “send test email” flow is instantaneous and super helpful because I can test different subjects to see which land in the Promotions tab and which land in Primary.

2) Duplicating a cohort is super easy and the dates all update automagically based on the new cohort start date in Settings.

3) Promo code generation for individual students on an ad-hoc basis works perfectly.

4) Lightning lessons have been a major unlock that allowed me to grow my list to ~12k emails.

5) Being able to get human feedback on landing pages from Rachel Kennedy, Claire Chen , Chelsea Wilson, Rishin Banker, Runqiu (Rachel) Cai, etc boosts my confidence with changes.

6) The Canva templates for LLs and social images save a ton of time with marketing assets.

7) The constant flow of marketing opportunities are a helpful mechanism that forces me to make decisions faster than I would without the deadlines - the Fast Track promo going right now has driven a wave of enrollments for me!

8) Attribution is notoriously challenging but I can see the Maven team making an honest best effort to provide real attribution for revenue, spot-checking samples of enrollments and back-tracing individual journeys to develop a qualitative sense of the accuracy of attribution.

9) I'm genuinely rooting for other instructors (even if their courses are slightly competitive with mine) because it feels like we're growing the pie together. Rising tides raise all ships, etc - Maven's team actively reminds instructors of this dynamic and encourages collaboration b/w what could be seen as competing instructors.

10) The instructor town halls offer an insanely transparent look into the team's thought process, priorities, etc. I'm never wondering what's top of mind for Gagan Biyani and the company.

Maven has been an incredible partner in this phase of my career as I've completed 10 live cohorts helping 200+ students prepare for their PM interviews. 

Their team has been an excellent sounding board along the way as I've iterated on the structure, packaging, messaging, and pricing of the course over the last 1.5 years.
 
Last but not least, I attribute a lot of my course growth in 2025 to Maven's collaboration with Lenny Rachitsky. Being featured on Lenny's List as a "top leadership and career course" has allowed me to get discovered by students who wouldn't find me otherwise.

Thank you for everything you've done to help me grow, Maven team! It means a lot 🙏

One year, Sachin Rekhi decided to ride his bike while listening to Billboard’s "Top 100 Albums of All Time". Every single album.

Start to finish. No skips. From Michael Jackson to Taylor Swift.

He didn't do it because he was bored. He did it because he treats "Taste" as a discipline, not a gift.

On this week’s episode of Supra Insider, Sachin (ex-LinkedIn, ex-Microsoft) gave us the simplest, most useful definition of Taste I’ve ever heard:

"Taste is simply the ability to recognize high-quality work when you see it."

And taste has never been more important, especially for PMs.

It’s not just about pretty pixels. It is the ability to look at a Strategy Doc, a growth metric, or a user flow and instantly discern if it is winning work, or low quality slop.

But you can't recognize quality if you haven't studied what quality looks like.

Drawing from Rick Rubin, Sachin argues that Taste is a muscle built through two specific, repeatable habits.

𝟭. 𝗖𝗼𝗻𝘀𝘂𝗺𝗲 𝘁𝗵𝗲 𝗖𝗮𝗻𝗼𝗻 (𝗧𝗵𝗲 𝗛𝗼𝗺𝗲𝘄𝗼𝗿𝗸) 
This is why Sachin listened to those 100 albums. He was building his baseline for recognition.

For Product Managers, Sachin suggests building your own "Canon." His personal list includes:

♟️The Strategy Canon: Every shareholder letter Jeff Bezos has ever written.

🎨 The Design Canon: The history of Apple Design Award winners (studying why they won).

🧠 The Thinking Canon: The collected essays of operators like Scott Belsky and Paul Graham.

𝟮. 𝗜𝗻𝗰𝗿𝗲𝗮𝘀𝗲 𝗦𝗲𝗻𝘀𝗶𝘁𝗶𝘃𝗶𝘁𝘆 (𝗧𝗵𝗲 𝗗𝗮𝗶𝗹𝘆 𝗥𝗲𝗽𝘀) 
Most of us sleepwalk through the products we use. To build taste, you have to turn on the "active critique." We actually did this live on the episode.

I was frustrated that I couldn't control individual guest volumes on our recording platform, Riverside. 

But instead of just complaining, we paused to deconstruct the trade-off the PM likely made: centralized consistency (Admin control) vs. localized chaos (Guest control).

That mental pause (switching from "annoyed user" to "curious builder") is the exact kind of activity that builds taste.

If you feel like your product sense is stagnating, stop waiting for inspiration.

Go do your homework and get some reps.

P.S. What's one resource in your personal "Product Canon" that you think every PM should read/consume because it's so good?

Episode links:
Spotify: https://lnkd.in/dbvrvTEY
Apple: https://lnkd.in/dgGGa4Dy
YouTube: https://lnkd.in/div45WXq
Substack: https://lnkd.in/dq_Jp2Xu

We almost didn't launch Insider Loops because of my cold feet. Here's what changed my mind:

By August, Marc Baselga and I had been working on Insider Loops for over a month. We'd done interviews, synthesized insights, and had early drafts of our first two guides: Figma and Uber. The momentum was building.

But while I was in France for August, I started questioning my excitement about the project. The research was interesting, but turning it into a real product suddenly felt heavy and overwhelming. I had just wound down my fractional product work and needed to plan the future of my course, Copilot, coaching, and advising. 

I asked myself whether we can really deliver on the promise of Insider Loops in a low time commitment while also hitting our high quality bar? And more importantly, can we do it while keeping our relationship strong and healthy?

Since I'm always honest with Marc, I told him exactly that. I wasn't sure I wanted to launch.

His response was simple and characteristically mature: "Let's talk when you're back from France."

When we caught up a few weeks later, we had a conversation that changed the trajectory of the project.

We realized we were each wrestling with completely different types of hesitations:
↳ Mine was about whether this could be big enough to keep me excited long-term and justify saying no to other opportunities
↳ Marc's was about how to build something we both genuinely care about without burning out or damaging our friendship due to imbalance

That talk became our turning point. We ironed out what we wanted Insider Loops to be, what would make it worth our time and energy, set some specific milestones, and divided up the work in a way that felt sustainable.

After that conversation, Insider Loops clicked into place.

Fast forward a couple months... Marc and I invited our bestie Joshua Herzig-Marx to join us on the podcast and do something that terrified us: run a live coaching session for us as business partners. Today we published that coaching session and titled it fittingly: "The scariest episode we've ever recorded." 

The episode dives into the full "Marc and Ben story" and how we're steering together right now through our two collaborations: the Supra Insider podcast and Insider Loops. It was part retrospective on the Insider Loops launch, and part raw honest look at what it actually feels like to build something meaningful with someone I genuinely care about.

If you've ever been curious about navigating co-founder tensions with expert coaching, I think you'll love this episode. 

P.S. Big thanks to JHM for making space for us. We appreciate you 🙏

Episode links:
Spotify: https://lnkd.in/eaPGF64r
Apple: https://lnkd.in/ePDtqZU4
YouTube: https://lnkd.in/efSSRFn5
Substack: https://lnkd.in/e7CA7NBe

If you’re a founder with capital and real distribution leverage, take a note from Brian Balfour about your M&A strategy for 0->1 bets.

The most interesting acquisitions might not be the ones with hockey-stick dashboards.

They might be the tiny teams with incredible product instincts, some traction, and obvious GTM friction.

Brian Balfour recently joined us on the Supra Insider podcast to go into Reforge's multi-product strategy, and it completely reframed how I think about mixing 0 to 1 bets with M&A.

Reforge built 5 AI products in 9 months. With only 25 people!

That headline is impressive but the details are the best part.

They didn’t buy teams because they had crazy ARR growth.

They bought teams because their product had outpaced their distribution.

Here’s how Brian described the ideal target:
✅ fewer than 10 people (ideally closer to 5)
✅ founders who know how to build, prototype, and ship quickly
✅ a working product with real users, not just a proof of concept
✅ clear technical depth in the team
✅ signs of traction, but also signs of GTM struggle
✅ zero founder burnout
✅ a product that Reforge could plug directly into its distribution engine

One example he gave was a team of six builders who had created a powerful workflow tool. The product was genuinely good. Validated users, clear pain relief, strong feedback loops. But their distribution channels were inconsistent, and the founders were spending most of their time trying to unblock GTM.

Reforge didn’t see that as a red flag. They saw it as an opportunity.

Brian’s point was simple: if your company already has distribution, you shouldn’t buy distribution. You should buy teams whose product is better than the size of the audience they reached.

When you give those founders a bigger distribution platform, you can unlock value almost immediately.

And if the founders are energized, not exhausted, you get a fully formed 0 to 1 tiger team ready to rock.

This is how Reforge spun up four new product lines shipping in under a year. They paired startup DNA with Reforge’s audience, brand, and GTM channels.

The value that was bottled up inside those teams finally had room to cook.

I left the convo with Brian inspired by the elegance of this strategy.

It’s not M&A for the sake of M&A.

And it’s not “innovation theater”.

It’s a practical way to combine three things that rarely sit together:
	1.	0 to 1 speed
	2.	distribution leverage
	3.	founders who want to keep building

This approach won’t fit every company, but if you have capital and a strong audience and/or GTM engine, it might be a more interesting path than chasing the hot startups everyone else is bidding on.

Sometimes the most undervalued teams are the ones whose product deserves a much bigger stage than the one they’re standing on. Especially if you have that stage.

Episode links in comments 👇

If you approach Stripe interviews the same way you tackle a typical PM loop, you’re going to bomb it.

Marc & I recently debriefed with someone who purchased our Insider Loops guide for Stripe and landed the offer. 

He told us he thought he had "a solid plan" before buying the guide, but once he saw how intense the expectations are for the process, he realized his prep wasn't close to Stripe's bar.

A few weeks later, I saw this note in my inbox:

"I have cleared the loop at Stripe and am going through team matching now. The recruiter said all interviewers were strongly inclined. In Product Sense specifically, she said my performance was outstanding. Thanks for the Insider Loops guide, it was very helpful. Since you stressed that the interviews were very rigorous, I doubled down on my prep by taking time off from work."

I love stories like this because they highlight something a lot of candidates don't want to admit:

𝗦𝘁𝗿𝗶𝗽𝗲'𝘀 𝗯𝗮𝗿 𝗶𝘀 𝗻𝗼𝘁 𝘀𝗼𝗺𝗲𝘁𝗵𝗶𝗻𝗴 𝘆𝗼𝘂 𝗰𝗮𝘀𝘂𝗮𝗹𝗹𝘆 𝘄𝗶𝗻𝗴. 𝗬𝗼𝘂 𝗵𝗮𝘃𝗲 𝘁𝗼 𝘁𝗿𝗮𝗶𝗻 𝗳𝗼𝗿 𝗶𝘁.

This candidate didn't get lucky. He understood the level of difficulty he was about to face, he respected it, and adjusted his plans to maximize chances of success:

↳ He took a full week off work because he realized this wasn't something he could squeeze into evenings and weekends.

↳ He followed our advice on leveraging the Stripe recruiter to extract more signal about what they really expected to see from him in each interview.

↳ He followed our systems design study plan because it helped him realize he had blind spots he didn't even know existed.

^ This is why he cleared the loop. 

The work ethic and rigor required to ace Stripe's interviews are not just interview skills. They're what it takes to thrive as a Stripe PM.

If you're aiming at Stripe in 2026, you're competing with world-class people who really want it and have zero hesitation about putting in the legwork.

You're also up against people who aren't leaving anything to chance.

They're going in equipped with insider knowledge, which I'm happy to provide.

Remove the guesswork. Get Insider Loops.

Shameless promo: my self-paced Maven course is now available at a 25% discount until Monday November 24th as part of the Maven Fast Track series (bringing the price down from $1,500 to $1,125).

The course includes 30+ hours of recordings, 1:1 access to me, and my popular AI Practice Copilot ($500 value), making this sale an awesome deal.

If you've been on the fence about enrolling, now is a great time to lock in lifetime access to the course materials. Even if you're not planning to actually go through the course until the future (e.g. Q1 2026), this is the best price you'll get for the next 12 months.

As a reminder, I've shifted to a self-paced course structure which means it will fit your busy schedules and be just as useful 2-3 months in the future as it is today.

To find the course, go to Maven and search for my name (don't want to upset the LI algogods with a link here).

Interview timelines don't map cleanly to live cohorts. So I overhauled my bootcamp to make it fit into busy student schedules.

After I announced that the 10th run of my course would be the final live version, my inbox filled up with messages from PMs:

“I have a Meta screen in two weeks. Can you help me?”
“I’m interviewing at Stripe before the holidays. Can you help me?”
“I can’t join live sessions, but I'm cramming for OpenAI. Can you help me?”

Interview timelines never map cleanly to a cohort schedule and candidates shouldn’t have to line up their prep with my calendar in an already challenging job market.

The right thing to do is help PMs prepare for interviews on their own timeline.

So I decided to restructure my Maven course from 100% live sessions on my schedule to 100% self-paced on the student's schedule.

Interview preparation just can't be tied to someone else's schedule.

In this market, if Meta, OpenAI or Stripe call, you need to be ready on *their* schedule.

My newly redesigned syllabus offers students lifetime access to:
↳ 30+ hours of session recordings available on-demand but with an opinionated timeline
↳ My AI Practice Copilot ($500 value)
↳ Direct 1:1 access to me for questions

The new package is perfect for PM candidates preparing for Meta-style interviews who need flexible, structured preparation that fits their interview timelines and busy lives.

Enrollment is now open and for the next week, you can get 25% off with Maven's annual Fast Track promotion. Code and link in comments 👇

Yesterday we hosted our first-ever live recording of the Supra Insider podcast.

150+ people showed up.
50 stayed for the full 90 minutes.
It was a blast (and won't be our last).

Marc and I sat down with Jacob Bank (founder of Relay.app, formerly Director of PM at Google) to break down how senior PMs are getting real leverage by “hiring” AI agents.

Here’s the quick version of what we covered:

🎯 PMs are sitting on some of the best agent use cases because so much of our work is structured and repeatable.

📝 The right starting question isn’t “What can AI do?” It’s “What would I hand off to a great junior person?” Then get precise about the what, when, and how.

🧩 The biggest early win comes from giving agents a small number of clear responsibilities instead of a giant catch-all job description.

🔄 Agents improve the same way teammates do. Tighten instructions, refine workflows, and iterate based on output.

If you missed it and want to watch the full session:
https://maven.com/p/7b8354

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