Adam S.

Chore

Chore exists to kill admin so founders can build their dreams. We are your fractional, expert, Chief of Staff to run your business operations. 

We are the end of admin. Hire Chore and join the future. 🚀

Founder & CEO

Entrepreneurial Excellence Podcast

The Entrepreneurial Excellence podcast is hosted by Adam Spector, 4x founder and investor in 150+ startups. Each weekly episode features some of the world's top founders and investors. Topics include:
- Top skills of the best entrepreneurs
- Biggest entrepreneurial mistakes
- Investing & Venture Capital
- Hiring, firing and team building

Podcast Host

The Autopilot Fund

The Autopilot Fund focuses on early-stage companies that serve and accelerate how companies operate. 

More about us: https://autopilot.fund/

Operations span various “departments”: could be in engineering, operations, sales, finance, product, customer success… the questions we ask ourselves are:

1. Is this a founding team so capable that others should be afraid to go against them?
2. Do they understand the problem better than anyone, and have special “founder-market” fit?
3. Will they rest until they have dragged the world kicking & screaming into their vision of the future?
4. Is the product “infrastructure” in a manner of speaking: structured data, deeply embedded, sticky?
5. Does the advent of AI exponentially increase or decrease their defensibility?

Our portfolio includes special companies such AngelList, Pulley, Puzzle, Levels, Disco, Parallel Bio, Trilobio, GC AI, Cytronic, Copilot, Levels, among many others. 

Smart founders focus. Bad founders distract themselves with all the small, non-product, non-customer work that can easily take up hours but not move your startup forward.

We are sector agnostic and focus mostly on early stage. Our thesis is simple: the best founders come from anywhere, with any background, working in any industry. Focus, joy, dogged determination, and deep knowledge about your product and how you're changing the world is what leads to success.

If you're interested in learning more, drop me a note on LinkedIn.

We believe in the broad-based investing approach to startups. To achieve the best returns, data supports investing in a wide array of startups and rarely following-on. We follow the data even if it's unsexy. Across our fund, we have invested in over 100 startups.

General Partner

Angel Investor

Angel Investor in ~100 startups. 14 unicorns, 8 of which I invested at seed. 

Some of my favorites: Datalogue (exit), August Smart Lock (exit), Diamond Foundry, Checkr, OrderAhead (exit), Classkick, Jet.com (exit), Ginkgo Bioworks (public), uBiome (failure), BetterUp, Human Interest, Relativity Space, PayJoy, Ambient.ai, Zoox (exit), Arka, Kush Marketplace, Shyp (failure), AcreTrader, Cleary, Begin, Long Term Stock Exchange (LTSE), Evenup, Attentive, Metaphor Data, Certn, Boom Supersonic, Otis, Jobox.ai, Mootral, Chia Network, Evernow, Contra, On Deck, Equi, Placer.ai, Vinovest, VoiceOps, Synex, Soot, Inversion Space, Blockfi (failure), Superplastic, Rarify, Airmeet, AtoB, Writer, All Blue Labs, Droneseed, Favor, Stashfin, Copilot Money, Sidebar, Function Health, Comprehensive, BetterBrain, HealthArc, Angelist, Tiny Health, Best Practicer (acquired), Release, Anduril, Puzzle, Ramp, Supliful, Parallel Bio, Wispr, OneImaging.

My preferred focus is on SaaS Enterprise businesses although fantastic, focused founders solving problems aligned with personal theses are always worth meeting. I invest largely at the earliest stages. I prefer to invest directly but also participate in syndicates. 

I'm still trying to comprehend how some of my failures have gone from the top of the heap to bankruptcy (I have thoughts). #startupinvesting #learning

Hustle Fund

Hustle Fund Scout

Community of Angel Investors learning from and teaching each other how to invest in and give back to the dynamic startup community we all love (and that is a constant source of inspiration). Added bonus thanks to the fantastic investment opportunities.

Angel Squad Member - OG Squad 1

Headline.vc

Venture Scout

Correlation Ventures

Network Advisor and Venture Scout for Correlation Ventures

Venture Scout & Network Advisor

PEF Community

World's largest (I believe) community of Post-Exit, building, learning, educating and ideating founders.

Member

On Deck

Fellow - On Deck Scale

Founder Institute

Mentor to early stage companies globally. Helping more founders make their dream and idea a reality!

Mentor

My life thesis: execution > strategy. Compounding FTW. I'm an optimistic skeptic. 

I enjoy pattern matching and read widely. The opportunity to learn every day is a gift. Time is precious. The ability to improve what and where I focus and delegate the rest is ideal. 

I [of course] love my family and friends. I believe I am a logical, thoughtful adult and therefore accept my choices. I am content and therefore I have won.

Founder and CEO @Chore. We are a founder's back-office (HR, finance, compliance, equity) operations team. Back-office operations are an undifferentiated tax on success. Focusing on your superpower enables success. Chore handles the rest (i.e. we specialize in ops so you never have to) so you can achieve your dreams. 

Host of the Entrepreneurial Excellence podcast. I dive deep with multi time founders about their key decisions, actions, hires, drivers and more that they use to achieve "excellence." 

General Partner at the Autopilot Fund. We invest in early stage startups. We love obsessed founders who have a history of breaking through walls. I have invested in over 200 startups across multiple funds. 14 are unicorns (8 from seed).

In previous lives, I founded 3 other companies, been a product leader on a big co API team, Chief Revenue Officer (CRO), Chief Operating Officer (COO), and do-it-all janitor. 

I enjoy building great teams, processes, and stories that unify a company around a shared mission. Helping others build successful businesses brings me joy. More successful startups = a better, more dynamic world.

People describe me as energetic, positive, creative, detailed and optimistic. I enjoy rational, logical, data driven debate built on mutual trust and respect. I'm not an engineer but people view me as "technical" and have built companies with the brightest PhDs and brilliant engineers. The best compliment I received was "you ask great questions."

Honesty, trust, fun, a sense of urgency and mission are what I look for in colleagues and places I work. Passion about my product, my company and my team is what drives me. I work hard and enjoy being surrounded by people who do the same. 

"Leave the world (and your business) better than when you arrived..."
"The greatest risk is not taking one!"

Always curious and learning. Follow my top reads: https://raindrop.io/Jammfam/adam-spectors-top-reads-37295659

The Autopilot Fund focuses on early-stage companies that serve and accelerate how companies operate. 

More about us: https://autopilot.fund/

Operations span various “departments”: could be in engineering, operations, sales, finance, product, customer success… the questions we ask ourselves are:

1. Is this a founding team so capable that others should be afraid to go against them?
2. Do they understand the problem better than anyone, and have special “founder-market” fit?
3. Will they rest until they have dragged the world kicking & screaming into their vision of the future?
4. Is the product “infrastructure” in a manner of speaking: structured data, deeply embedded, sticky?
5. Does the advent of AI exponentially increase or decrease their defensibility?

Our portfolio includes some pretty special companies like AngelList, Pulley, Puzzle, Levels, Disco, among others. 

Smart founders focus. Bad founders distract themselves with all the small, non-product, non-customer work that can easily take up hours but not move your startup forward.

We are sector agnostic and focus mostly on early stage. Our thesis is simple: the best founders come from anywhere, with any background, working in any industry. Focus, joy, dogged determination, and deep knowledge about your product and how you're changing the world is what leads to success.

If you're interested in learning more, drop me a note on LinkedIn.

I'm very excited to announce that we’re launching something new at Chore 🚀
We're introducing the Chore Ops Dashboard. Your all-in-one headquarters or HR, finance, compliance and admin.
 
After years of watching founders waste hours inside spreadsheets, Slack threads, and payroll tools, I’ve realized the same thing again and again.
 
Practically every startup I’ve ever spoken to has struggled with internal visibility.
 
Product has Jira. Sales has CRMs. Marketing has dashboards.
 
But ops? Ops is everywhere.
 
Founders spend 10+ hours a week bouncing between tools, checking statuses, asking for updates, and fixing what shouldn’t have broken in the first place. That’s 10 hours not spent on product, fundraising, or hiring.
 
So, we decided to build something different. Something that brings clarity to the part of your business you’ve been forced to ignore.
 
This launch means a lot to me personally.
Because I’ve lived it and I know it. That sinking feeling when I realize I’m running a company I can’t fully see.
 
Ops shouldn’t feel like that. It should feel calm, measured, and predictable.
And with this new Operations HQ from Chore, you'll finally get there.
 
Check it out here: https://lnkd.in/gF73Pane

CEO @Chore | Host @Entrepreneurial Excellence Podcast | GP @The Autopilot Fund | 4x founder & 200+ angel investor

The day I stopped calling it "back office" was, like, genuinely the day everything changed for me.

So I was talking to this founder, right, and he'd just closed a $5M round. Super smart guy, technical background, building in fintech, and we're having this great conversation about his product roadmap and growth plans. Then he says something that just, I don't know, it stuck with me.

He mentioned needing to hire someone to handle all the back office stuff now.

Back office. Like it's some dusty corner of the business you shove into a basement and forget about.

And that's when it hit me, you know, the language we use actually shapes how we think about things. And how we think about things determines what we build and how we prioritize our time. When you call it "back office," you're already losing. You're basically saying it's secondary. Less important. Something to minimize and grudgingly deal with when you absolutely have to.

But like, what if we're thinking about this completely wrong?

See, the best founders I know, and I've worked with hundreds at this point through Chore and as an angel investor, they don't think of operations as overhead. They think of it as leverage. 

So think about it this way. Your product is what you sell, obviously. Your team is who builds it. But your operations is what makes everything else actually possible.

Great operations isn't visible until it breaks. Then people often notice, right? The payroll that doesn't go through. The compliance deadline you miss and get fined for. The fundraise that gets derailed because your cap table is a complete mess and diligence takes forever.

But when it works? It's invisible infrastructure. The foundation that lets you move fast without everything falling apart behind you.

Your operations should be so good they're invisible. So reliable they're boring, honestly. So systematic that you rarely have to think about them because they just work. That's not back office. That's the invisible infrastructure that lets you actually build the future instead of constantly putting out fires.

You don’t need a Chief of Staff.
You need to stop saying yes to every task that lands in your inbox. Let me explain 👌🏻

A few years ago, I invested in a startup with a product that was just starting to click. Revenue was growing steadily and customers were sticky. Things were looking up, but the founder was drowning in ops.

I like to stay pretty close to my portfolio companies for times like this. Anyway, he messaged me one day and said: “I think I need a COO.”

After 30 minutes of talking, it was clear that he didn’t need a COO. What he needed was to say no more often. He needed tighter systems, not another senior hire.

I’ve seen this story dozens of times as a founder, investor, and now as CEO of Chore.
So when is the right time to bring in fractional help? Here’s what I’ve learned:

✅ When you should bring in fractional help:
You’re bleeding time, and it’s starting to hold back growth.
You’re ready to let go. You’re not secretly planning to micro-manage this person.

That’s when fractional help really unlocks you.
 
❌ When you shouldn’t:
You’re still figuring out your business model.
You’re not ready to delegate. You plan to micromanage this person.
You have no idea what to do with the time you'll get back.

If you're in this stage, the answer isn’t delegation, it’s discipline.

The best time to bring in help is when you're clear on what you don’t want to be doing anymore, and brave enough to hand it over.

That’s when the right fractional ops manager will give you hours back, and the leverage you need to show up better for your business.

If you’ve ever wished operations made sense at a glance, this is for you.

When you finally see everything in one view, something changes:
Your decisions get sharper ⚡️
Your team moves faster 💨

And operations stop being so chaotic.

That's the clarity that Chore gives you.

So I was helping a founder friend last week, and he couldn't find his AWS contract. Took him about ten minutes of digging through Gmail, Slack, Google Drive. Finally found it in a random email thread from three months ago.
I got me thinking about something we see all the time at Chore.
 
You know how you probably search for files every single day, right? Maybe it's that vendor agreement, or last month's P&L, or that contractor's W-9 form. Each search feels quick. Just a minute or two.
But here's what I realized when I actually did the math (and literally, the math is pretty simple):
 
If you spend just five minutes a day looking for documents across all your tools (and you definitely spend more than 5 minutes), that's about 25 minutes per week. Over a full year, that becomes 1,300 minutes. Which is more than 20 hours.
 
Now, I've been working with startups for about five years, and here's how I think about founder time: your opportunity cost is probably around $1,000 per hour when you factor in what you could be building, the deals you could be closing, or the fundraising calls you could've taken.
 
So those 20 hours become $20,000 in lost value. Every year. Just from hunting for files.
 
And look, this isn't because you're disorganized or anything like that. The problem is that your operational world is scattered everywhere. Your HR documents live in Gusto or Rippling. Financial records are stuck in QuickBooks. Contracts might be in DocuSign or HelloSign or just floating in email. Cap table and equity stuff is in Carta or Pulley. Compliance documentation could be literally anywhere.
 
Every one of these tools promises to be your "single source of truth." But you and I both know none of them actually talk to each other in any meaningful way.
 
We've built something at Chore to finally solve this. Our operations dashboard.
 
Not another tool to add to your stack, by the way. We connect to what you already have. QuickBooks, Gusto, Carta, whatever you're using. Pull it all into one view where you can see your cash balance, upcoming compliance deadlines, key documents, equity status, everything.
 
The thesis is simple. You as a founder should have all the key information at your fingertips without having to log into multiple places to get a good idea of how the business is running operationally.
 
The file search tax is real, and it's way more expensive than most founders realize.
 
What's your experience with this? I'm genuinely curious if other founders have noticed this pattern or if we're just seeing it because we're deep in the operations world every day.

⚠️ Operators & founders! This Thursday, we’re doing it again.
Chore's Operators Happy Hour is exactly where you need to be this Thursday.
 
Every month, we pull together the people who actually run companies. The ones fixing broken systems, scaling messy processes, and keeping the entire business glued together.
 
This week, we’re back in SF for another one. And if you’ve never been, here’s what to expect:
🍸 Zero fluff. Real conversations.
💬 Founders and operators swapping playbooks.
⚙️ Sharp, practical discussions about what’s working in AI, ops, hiring, and systems.
🤝 People you’ll want to follow up with the very next day!
 
Every edition so far has filled up, and I know this one will too. Plus I'm pretty excited to share something new with everyone at this edition.
 
📍 San Francisco
🗓 Thursday, November 20
🕔 6:30pm PT
🎟 Register → ﻿https://luma.com/it962c24
 
Let me know in the comments if you'll show up!

Open article: Operators Happy Hour by Chore: Foundersgiving – Setting Up for 2026 with AI Power · Luma by luma.com

Operators Happy Hour by Chore: Foundersgiving – Setting Up for 2026 with AI Power · Luma

What you can’t see, you can’t improve.
What you can’t measure, you can’t scale.
And for most founders, ops is still invisible.
 
But for ops? Chore is about to change that.

Thanksgiving is a great day to zoom out and reflect. As founders, we spend so much time in execution mode that we forget to acknowledge the people and moments that make the journey worth it.

So today, I’m grateful for:
- A family that supports the long hours and the big dreams.
- A team at Chore that turns my ambitious ideas into reality.
- The founders who trust with the deepest parts of their operations.
- My Entrepreneurial Excellence Podcast guests who openly share lessons and wisdom for other founders to learn from.
- The huge pumpkin pie I'm going to have at Thanksgiving dinner soon.
- And the many tiny moments that have made this year truly my best yet. 

Happy Thanksgiving, everyone 🦃

When your product breaks, you know it immediately. Customers complain. Alerts go off. Revenue drops.
But when operations break? There are no alarms. Just slow leaks.
 
A late payroll here. A missed compliance renewal there. A forgotten 1099, a misclassified contractor, an invoice that never got paid.
 
It doesn’t even feel like an emergency, until it suddenly is.
 
Here’s the problem:
Product is tracked ✅
Engineering is tracked ✅
We use Linear, Jira, Notion, dashboards, metrics.
 
But ops?
Still managed through Slack messages, Google Sheets, and “someone’s got it covered.”
 
And that’s why it breaks.
 
Ops needs systems. Visibility. A way to measure progress and spot what’s falling behind. Just like every other part of the business.
 
Until if you figure that out as a startup, your ops will continue to break. At Chore, we're about to launch something to fix that.
 
Keep an eye out for an update 👀

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

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.

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.

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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.

When I first hired a coach while running VNN, it felt like something I had to hide.
Like I was admitting I couldn’t do the job on my own. But once I opened up, it became the most transformational leadership decision of my life:

That was nearly 10 years ago. Coaching was something founders whispered about. Today, it’s far more normalized. VC funds and boards now see a great coach as a force multiplier - helping high-potential founders level up faster than almost any other investment.

Still, many people I talk to don’t really understand it.

What is coaching?
How does it actually work?

Let’s start with how a trained coach helps founders see reality more clearly and make better decisions when the stakes are highest.

1. Leaders can’t see what’s right in front of them.

We like to think the way we see the world is the world. But our perception is filtered through countless lenses - experience, fear, ambition, identity.

Your brain’s reticular activating system decides what you notice and what you ignore - like when you buy a Volkswagen and suddenly see them everywhere. You’re not seeing more cars. You’re just tuned to notice them.

Leaders do the same with reality. We see what confirms our existing models and miss the rest.

Skeptics, look at the image below.

Because our brains are so conditioned to see faces as convex entities, our brain automatically transforms the concave mask into a convex face. This is how our brain distorts reality to fit into our mental model of what reality “should” look like.

2. At the top, honesty gets complicated.

As Jackie Vullinghs from AirTree VC explains, “As your company grows, there are fewer and fewer people you can be 100% honest with.”

You can’t tell your board you’re unsure how to scale.
You can’t ask your co-founder if they’re still the right person to lead.
You can’t tell your team their dysfunction is wearing you down.

Exactly when you most need clarity, you’re on your own.

That’s why they say it’s lonely at the top. 

But accepting leadership myopia as inevitable is a mistake fewer founders make today. This is where executive coaching changes everything:

A trained coach is an objective, confidential partner dedicated exclusively to your growth - not your board, not your company, you.

Through that relationship, you begin to see your own operating system: how you make decisions, what drives you, which blind spots trip you up, and how fear or ego distort your view. That clarity helps you see reality more accurately, make better decisions, and unlock growth that once felt unreachable.

The best founders aren’t doing it alone. They’re building clarity through partnership - seeing reality more fully and leading from a deeper level of awareness.

Yes, it’s lonely at the top. But it doesn’t have to be.

At Inside-Out Leadership, we’re former founders who scaled and exited companies, then did the deep work on our own operating systems.

If your next level requires your next level of clarity, DM me.

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?

For 15 years, I tried to wrench reality to conform to my latest 5-year projection. Then I took on the biggest challenge of my life - Michael Singer's Surrender Experiment. Here's why I haven't gone back:

Singer's approach: "Do whatever is put in front of you with all your heart and soul without regard for personal results. Do the work as though it were given to you by the universe itself - because it was."

We're taught to take charge of our lives from an early age, so giving up agency in favor of a cosmic dance with life seems backward. But it's been one of the most magical experiments I've ever run.

Here's an example:

I spent two months building a leadership peer group called Sangha for entrepreneurs who had reached success and were looking for what comes after. Had 5 commitments, two shy of my target of 7.

Then I didn't touch it for a month. 

When you're close to launching a creative work, the whole thing often seems stupid and pointless. Julia Cameron calls these "creative u-turns." The fear of presenting your soul to the world's judgement. 

Well, I'm not going to fall for that, so I committed to brute-forcing it across the finish line. Created an outreach blitz. Worked out the steps Monday, committed to sending emails Tuesday.

Friday came. Still hadn't sent them.

The venom with which my inner critic spoke: What a slacker. A lazy has-been so scared he can't even launch a project he'd spent months on. All my mental machinery told me to just do it.

But for the first time in my career, I didn't. 

Armed with meditation practice, a financial runway from exiting my company, and fueled by curiosity, I let it go. The 60 days of work, the entrepreneurs committed, the identity wrapped up in it. I let it all go. It felt like giving up, but like it might still work out.

Six days later, On Deck emailed asking me to help them launch On Deck Scale, their first peer-leadership program for scale-up entrepreneurs. 

"I think I built that already," I said.

So with three other coaches, ended up bringing a few hundred top entrepreneurs through this adventure. By letting go of what I thought I wanted, I was handed an opportunity I couldn't have dreamed of.

And it kept happening:

• When I couldn't afford this NLP certification, I was randomly offered another course for free.
• A chance encounter in Jackson, Wyoming, led to my Mindful Magazine series.
• I let go of pushing for IO to become something big, and powerful people reached out to join.

Einstein said there are two ways of relating to life: as if nothing is a miracle, or as if everything is. After years as an intellectually-superior atheist, I'm finally seeing the world's spiritual axis.

I'm not at Singer's level yet. There are still times I panic and wrench the steering wheel. But my grip is loosening as I learn my fear patterns more intimately.

Now I'm living to learn instead of living to win - and I wouldn't trade life's daily magic for all the five-year projections in the world.

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.

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.

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.

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.

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.

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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