Adam S.

My life thesis: execution > strategy. Compounding FTW. I'm an optimistic skeptic. Curiosity is the most important quality in life.

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. Subscribe to Entrepreneurial Excellence to learn.

General Partner

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.

My team and I at Chore have worked on this for months, and now we're excited to announce that Chore is launching a product we're very proud of; our AI Document Classification System. But first, let me tell you a little story.
 
Years ago, every Sunday I used to sit with QuickBooks receipts while my wife watched Netflix. Then she'd say "Really? This is what you're going to spend your Sunday night doing?". I'd think, "Fair point."
 
When we first started Chore, we were drowning in the same problem, spending 15+ hours weekly just sorting documents for our clients. Tax forms, contracts, invoices, HR paperwork, and more.
 
So we built something to fix it.
 
It's an AI document classifier that's trained on 20,000+ real documents from actual operations. We set confidence thresholds where anything below 90% certainty gets a human review, and created a super cool interface where team members see flagged documents instantly.
 
Our document processing dropped from 15 hours to 2 hours weekly, with zero critical errors in 6 months.
 
We spent months building this, but now the payoff is permanent.
 
Now when I upload 50 random documents, I watch AI sort them in seconds with confidence scores. The human review queue shows flagged items, and our time savings dashboard shows hours reclaimed.
 
The truth is, you raised $5 million to build your product, not to become a filing clerk. Every hour saved on document sorting is an hour invested in your growth.
 
So let me know if you'd like to try it out. Send me a DM to take a look.

CEO @Chore | Founders shouldn’t do their own HR, finance, and compliance. That’s what Chore is for.

When I started my first company, I made a hire at employee #7 that I regret to this day. We'd just closed our seed round, and we felt like we were supposed to start "building the team for real."
 
So I hired a full-time office manager / HR person.
 
Pretty nice person, and good at their job, but at 7 employees, there wasn't enough work to fill their week. They ended up doing a little bit of everything and not enough of anything. Meanwhile, I still didn't have enough engineers on the team.
 
That one hire cost us roughly $85K fully loaded and probably 3 months of product velocity.
 
I think about this every time a founder asks me who to hire after they raise. Here's the framework I wish someone had given me:
 
At 5–10 employees, only hire people who build your product or generate your revenue.
That's it. Engineers, a founding salesperson and marketer, and maybe a product designer if your product is consumer-facing.
Everything else, like HR, payroll, finance, compliance, equity management? Outsource it. And this isn't because it doesn't matter as much as the other functions. It's because it matters too much to do badly with a generalist hire who's also ordering office supplies.
 
At 10–25, hire your first ops or people lead.
Your outsourced layer should be doing amazing by now. The mistake I see here is founders hiring a Head of People at employee 12 and that person immediately drowning in benefits admin, state registrations, and 409A valuations. You don't need them yet. You need another engineer or another AE.
 
At 25–50, start hiring where institutional knowledge genuinely matters.
This is the danger zone. You feel like a "real company" now. The board might even ask why you don't have a Head of Finance or a People lead yet.
The answer is because your outsourced partners are still handling it better and cheaper than a single hire could. One ops person at this stage can't cover finance, HR, compliance, and equity management well. So you'd need two or three. That's $300K+ spent every year that doesn't even directly contribute to your bottom line.
 
After 50 employees, maybe you can start hiring where institutional knowledge genuinely matters.
This is when the complexity justifies dedicated headcount. Not before. The founders who scale their companies successfully know this difference early.
 
The ones who over-hire into back-office functions before they're ready spend 18 months unwinding it. I've seen it over and over, a startup with 15 people and 3 of them are in ops roles that could've been handled by one good outsourced partner.
 
The rule I follow now: if the role doesn't build the product or bring in revenue, the default answer is outsource until you hit 50. Then hire.

I got a text from a founder a couple of weeks ago at 11:47pm.
"Quick question: do you know what expense category to use for..."

I knew exactly where this was going. Another founder deep in QuickBooks, reconciling March expenses in May, thinking they're "being scrappy."

And here's what I tell founders in this situation:

Founders who are personally in charge of their company's bookkeeping functions think they're saving money. They're not.

The math I walked them through:
- 15 hours/month on bookkeeping
- Founder time worth ~$250/hour in enterprise value creation
- 15 × $500 × 12 months = $45,000/year

They were burning $45K of runway to feel "in control." I asked them one question: "What did your competitor ship while you were categorizing Uber receipts?"

The silence said everything.

Today he messaged me: "Just hired fractional help for ops and it's the best $3,000/month I've ever spent. I used those 15 hours for 3 customer calls and finally shipped that feature."

Sometimes the best advice is about doing less of the wrong things.

What's the one operational task you wish you didn't have to do?

I was going through our legal bills from one of my earlier startups and nearly fell out of my chair. We paid $4,000 to update three employee stock grants after promotions.

The lawyer sent me a nice PDF invoice, breaking it down. Each grant update was between $1,000 and $1,500. For clicking buttons in Carta and changing some numbers.

So I started asking other founders what they pay for cap table stuff. The numbers are insane. One founder paid $750 for their lawyer to export a cap table PDF for an investor. Another paid $2,000 to adjust a vesting schedule. These are literally five-minute tasks if you know where to click.

The thing that gets me is that most lawyers don't even do this work themselves. They have paralegals handle it, but they still bill you at lawyer rates. Sometimes they bill at paralegal rates, which sounds better until you realize that's still $350 an hour for data entry.

I think lawyers know that founders are scared of messing up equity stuff, so they position all cap table work as this complex legal work that requires their expertise. But honestly, once your equity plan is set up, maintaining it is mostly just keeping track of numbers and dates.

The whole thing reminds me of when accountants used to charge thousands to do tax returns before TurboTax came along. Except somehow we're still living in the pre-TurboTax era for cap tables.

What's the most ridiculous legal bill you've gotten for routine work?

Yesterday we launched our AI document classification product. Within a few hours, my inbox filled up with lots of people telling me this one thing 👇🏻
 
“This is what AI is actually supposed to be used for.”
 
What they meant is, we used AI to do something practical. Automatically organizing the messy, unstructured documents that quietly slow companies down.
 
It's the kind of work nobody brags about, but everyone feels.
 
The best AI use cases make you say, “This saves me hours.” AI should integrate into your workflow and make your life meaningfully easier.
 
And day one feedback tells me we’re building in the right direction.

Jack Dorsey just laid off over 4,000 people from Blocks. Every founder should read Jack’s memo. Here's what I think about it:
 
What stood out to me in Jack’s note was the framing. He’s saying the way companies operate is changing, and changing fast, because intelligence (read: AI) tools are fundamentally altering what it means to build and run a company.
 
That’s the real headline here.
 
For years, we’ve talked about AI as a productivity enhancer. Now we’re seeing leaders treat it as an operating model shift. We're seeing smaller teams with AI embedded into workflows, and more and more founders are admitting that the same output can come from fewer people if systems are stronger.
 
There are two uncomfortable truths here:
1️⃣ Technology always compresses labor somewhere.
2️⃣ As Jack said, leaders will eventually have to choose between gradual drift or decisive restructuring.
 
Jack chose decisive.
 
You can debate whether it was the right call. You can question timing, scale, or execution. But I do respect one thing: clarity. A single hard reset is brutal for everyone, but at least it’s honest about the direction.
 
The bigger question for founders watching this isn’t whether Blocks was right or wrong.
It’s: if intelligence tools genuinely enable smaller teams to operate at a higher level, how should you be structuring your company today? Are you building a headcount-heavy company optimized for the past? Or are you redesigning how work gets done based on how things are shifting?
 
This also doesn’t mean “replace people with AI ASAP” That framing is way too simplistic. It means you should redesign your workflows so humans do judgment, creativity, and strategy, and machines handle repetition, pattern recognition, and scale.
 
Let me also be clear on this: transitions like this are painful. The people leaving built real value. Severance and healthcare extensions may help a little, but it still feels like shit. But my note to founders is that how you treat people on the way out is part of leadership too.
 
Moments like this are a signal that the definition of “efficient” is changing. If you want your company to win, you have to rethink how your team is structured from the ground up. And you'll have to do it without losing their humanity in the process.
 
What do you think about Jack's memo?

A software engineer I know lives in Birmingham in the UK. Her company decided everyone had to come into the London office. Monday to Friday.
She can't afford to move, and the commute isn't realistic. She even offered to come in 3 days a week instead, but they said no.
 
There is no version of the world where that decision helped the company.
 
She writes code. The code she writes at home is the same code she writes in an office. Except at home, she starts work at 9. In the office, she arrives at 9, after two hours commuting, and spends the first 30 minutes recovering.
 
Now, to be fair, there's a real argument for being in person when you're early stage. When you're 4 people still trying to find PMF, being in the same room every day can genuinely speed things up and create a better culture. I'll admit that it helps.
 
But this company isn't 4 people figuring things out. They have a product, lots of customers and a software engineer who's been doing the job well from home for years.
 
This is what office mandates actually cost you:
— Your office sits empty more than 50% of the time, even when "everyone" is in.
— You're paying fixed overhead on a depreciating asset while your competitors pay nothing.
— Every hour spent commuting is an hour your team isn't working, isn't rested, and isn't at their best.
— And you've just limited your talent pool to whoever happens to live within driving distance, instead of hiring for the best.
 
And beyond the math, to me, it signals something about how you manage people. If you need to physically see your people to know they're working, you haven't defined outcomes clearly enough. I'd say that's a leadership problem.
 
We're moving into a world where autonomous systems operate 24/7 with zero overhead. The humans competing alongside them need the same operating model, trusted to deliver outcomes, and not managed by proximity.
 
If your team can't be trusted to work remotely, you have a hiring problem. Or maybe an incentives problem. Or even an outcomes problem.
 
And none of those get solved by a commute.
 
I've seen lots of companies enforcing office mandates recently, and I'm curious. What exactly are you trying to achieve by making everyone come in? If you're a founder who disagrees with me, what has changed between when you were remote and now when you see everyone IRL?

Our friends at Stable surveyed 250+ companies and there's one surprising blind spot they all share.
It's sitting in the corner of your office operations looking completely harmless, and it's quietly costing your team more than you'd think. In time, in compliance risk, and in the kind of low-level reactive work that pulls people away from things that actually matter.
 
It's mail. Not email, it's physical mail.
 
Stable's data reveals exactly what's happening inside these workflows. How much time is being lost, where the bottlenecks are, and what changes when you actually modernize it.
 
Next Monday, March 24th, I'm joining Stable's Andrea Paul Salerno to unpack what 250+ businesses revealed about the real operational cost of mail, and what it looks like when you fix it.
 
If you're an operator, founder, Chief of Staff, or finance/compliance lead who's ever thought "we really need to sort out how we handle mail", this one's for you.
 
📅 March 24th | 1pm ET / 10am PT
🔗 Link to register in the comments

A $2M ARR company with 8 employees just raised a Series A at a better valuation than a $2.4M ARR company with 22. They're in the same space with a similar growth rate. So what was the difference?
 
ARR per employee.
 
The first company was generating $250K per person. The second was generating $109K. To a Series A investor pattern-matching across hundreds of decks, those are two completely different businesses regardless of what the top-line number says. One is a lean, efficient revenue machine. And the other is a company that's going to need a lot more capital to get to the next milestone.
 
Most founders don't track this metric until they're already in a term sheet conversation and it's too late to do anything about it.
 
I have a hot take. This is quietly behind a lot of the layoffs you're seeing right now. Founders overhired during a window when headcount felt like a proxy for momentum, then looked up one day and realized their ARR per employee was way too low. Then layoffs happened as a course correction. I'm not saying it's right, but sometimes layoffs don't happen because the business is struggling, but because someone finally ran the numbers and understood they didn't make sense.
 
And the lever that moves this metric the most is where you're putting that headcount. A full-time hire comes with a 6-month ramp before they're fully productive, with benefits, severance exposure, and a cost that hits your ratio immediately before you see any output. A contractor or vendor relationship is a 30-day out, no overhead, and faster time-to-value for scoped work. Back-office functions especially finance, HR, compliance, equity management, none of these need to live on your payroll at the early stage.
 
If you're raising in the next 6 months, divide your ARR by your current headcount right now. What number are you looking at?

Something weird happened last month. I had a call with a founder who's doing about $2 million in revenue, growing fast, and has a great team. But during our conversation, he casually mentioned he still does the company's bookkeeping himself every Sunday.

I asked him why. He said it only takes an hour, and he likes staying close to the numbers. I did some quick math in my head. That's 52 hours a year he's spending on QuickBooks instead of talking to customers or working on product. At his growth rate, each of those hours could be worth tens of thousands in company value.

I told him I couldn't invest in his startup.

This probably sounds harsh, but I've learned that founders who won't let go of basic operations tasks are usually the same ones who become the bottleneck for everything else. They're the ones approving every expense and touching every decision. Their companies hit a ceiling, and they can't figure out why.

I remember working with three different founders who all had this problem. One would literally do payroll during board meetings because "it had to be done right then." Another missed important customer calls because she was dealing with state filing deadlines. The third spent his entire fundraising prep week managing expense reports and then wondered why his pitch was underprepared.

All of them were smart people. All of their companies struggled to scale. The pattern is pretty clear once you see it enough times.

The weird part is that these founders usually know they should delegate. They just can't do it. They tell themselves they're being responsible by staying involved in everything, but really, they're slowly suffocating their own company.

So be honest. What task are you doing for your startup that you know you need to delegate?

New flex: tiny team, insane output. Headcount is last decade’s vanity metric. Why Jack's 40%+ headcount cut at Block is what every team should be doing.
 
Jack Dorsey just cut ~4,000 people at Block (close to half). This is the way.
 
Smaller teams + intelligence tools + ruthless focus beat bloated org charts.

The metric you should obsess over isn’t headcount. It’s ARR per employee (or gross profit per employee).

Every full-time hire you add early comes with hidden costs:
- coordination debt
- slower decisions
- more management
- permanent fixed burn

Hence, STOP HIRING. A bigger team is not a flex. It's a sign you're undisciplined. It's a sign you're still thinking like it's the 2010s [when the only way to scale was with more people].
 
I probably beat a dead drum but the idea of a Seed or Series A founder doing their own back-office operations is as insane as you trying to build your own power plant to keep the lights on or building your own servers instead of delegating to AWS. Both are critical and if you mess them up, your business is screwed, yet...you outsource the work. 
 
Why would you NOT want experts - who also don't require recruiting, management, equity or severance - running your operations? 

It's insane to think you should spend any time on back-office overhead. You are being penny-wise and pound foolish.

Some of Chore's clients are just two founders who outsource everything non-product and GTM to us. Other of our clients are over 100 FTEs and are gutting their back-office teams as they realize they don't need non-specialized headcount.

Block just became way more lean. Are you doing the same?

2026 mantra: tiny team, massive output, zero busywork.
 
[Note: this is my second post on this topic because, well, the fact that founder's dont get this kills me. Wake up!]

Every week I notice a handful of startups that are making moves most people aren't paying attention to yet. I'm going to start writing them down and sharing them here.
 
It's pretty much my list of founders and operators doing interesting things that I think deserve more visibility in this feed.
 
Here's week one:
1. Sandbar — AI smart ring that transcribes voice notes and enables conversational interaction on your wrist. The wearable AI race is heating up fast, and Sandbar is one of the few betting on a clear, specific use case rather than trying to do everything.

2. Mind Robotics — It's a Rivian spin-out building industrial robots for dexterous factory tasks. They just raised a $500M Series A. When your training data comes from a real manufacturing plant, you have a moat most robotics startups can't buy.

3. Standard Kernel Co. — They're building AI systems that generate GPU software & just raised $20M in seed funding. The problem they're solving is very real. Every new model architecture can require months of specialized engineering to optimize performance-critical code blocks, and kernel engineers are scarce. So they're using AI to automate that process entirely.

4. Jazz — A data loss prevention startup that emerged from stealth with $61M just raised. It's enterprise data protection built for the AI era, and I think this category is going to matter a lot.

5. XBuild — The first AI platform purpose-built for construction. It generates detailed job estimates, supplier pricing, and reports in a fraction of the time. Industries that have been underserved by software are finally getting the products they need to be more efficient.

6. PactFi — A platform for managing complex private credit transactions and deal closing. They just raised a $25M Series A. Back-office for private credit is a real problem and they're going after it.

7. Gangkhar — An AI-native embedded insurance infrastructure for carriers and distributors. Just raised a $4.25M seed round.

8. Risotto — An AI-native autonomous help desk founded by operators from Dropbox, HelloSign, and Gusto, raising $10M seed and backed by Y Combinator. It sits between ticketing tools like Jira and the internal systems that actually resolve requests, rather than bolting AI on top of legacy infrastructure. Risotto autosolves 60% of monthly support tickets for Gusto, saving 1000s of hours/month.

9. Sequence — An accounts receivable automation using AI agents to handle contract intake, collections, and revenue journals. The reviews are strong and the use case is super obvious.

10. Factors.ai — B2B demand-gen and account intelligence platform. It helps teams identify intent and prioritize the right accounts. If you're a founder trying to make your sales motion smarter, it's worth a look.
 
That's all folks. If you're building something worth watching (or know a founder who is), drop it in the comments. I had a lot of fun curating this list so I'll be doing this every week.

Your new hire's first week tells them everything about your company. And most founders are accidentally telling them: "We have no idea what we're doing."
 
You spend weeks getting the recruiting right. The sourcing, the interviews, the offer negotiations. All the energy goes into getting someone to say yes. Then they start, and everything behind the scenes is messed up.
 
Payroll isn't set up yet, the state registration you need to even hire them legally never happened, the equity grant is stuck because the 409A expired, or some other stuff. They're asking where to submit their banking info and nobody give them a good answer.
 
Their first impression of the company they just bet their career on? That nobody has their act together.
 
I talk to founders all the time who are scrambling to figure this stuff out the week someone accepts. Here's what I've noticed about the ones who hire well:
 
They treat all of this as pre-hiring infrastructure. Not something to figure out during onboarding.
Before they ever extend an offer, they already have:
→ Payroll configured and actually tested (not just signed up for)
→ State registration complete if hiring in a new state (this takes weeks, not days)
→ Equity grant templates ready in Carta or Pulley so they can issue the grant week one
→ Onboarding docs ready to send automatically instead of built from scratch each time
→ Benefits enrollment figured out so new hires don't miss their 30-day window
 
The major difference is timing. If you think of these as onboarding tasks, you start working on them when someone accepts. And by then, you're already behind.
 
If you think of them as infrastructure, you set them up once and they work for every hire. The offer goes out, the new hire gets a great experience, and you're not spending their first week apologizing for the mess.
 
Most founders have never set up payroll or HR processes before. Why would they? It's not their thing.
 
But that's exactly why it gets pushed to "we'll figure it out when we need to." By then it's too late.

Everyone has been panicking about the SaaSpocalypse. SaaS stocks are getting crushed and AI is killing the per-seat model. Here's what I think ➡️ the panic is real but most people are drawing the wrong conclusion from it.
 
The narrative is "AI will let companies build their own software, so why pay Salesforce?" Which sounds scary until you think about it for more than five minutes.
 
Yes, you think you can now vibe-code a basic CRM in a weekend. But here is what that overlooks: shipping a v1 is not the hard part. The hard part is maintaining it, iterating on it, and keeping pace with what a dedicated company with hundreds of engineers is shipping every month. You are not replacing Salesforce. You are becoming Salesforce's competitor. And that is not a good use of a founder's time.
 
At Chore, we use Pipedrive. Could we build our own version? Probably. Would we save money on seats? Yes. But if I value my team's time honestly, it would take days or weeks hours to build, then an hour every month to maintain, and I would always be chasing what Pipedrive just shipped. The math is negative ROI before I have written a single line of code.
 
You need to stay obsessively focused on what you are uniquely good at and pay other people to do everything else really well. That principle has not changed. AI just made the build vs. buy question louder.
 
The SaaSpocalypse is real for companies that were already coasting on weak product and legacy pricing though. This doesn't apply to them, but for everyone building something genuinely valuable, this is noise. Don't pay attention to it.

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 VC backed companies (one big exit and two learning experiences), all while presenting 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

Big news! I'm so excited to welcome Derek Haswell to the team as a Partner and Founder Coach! 

I met Derek early in my coaching journey, and have wanted to conspire together in some way for years. He's amazing. And now I'm eager to see what we get up to together at IO. 

In 2013, Derek accidentally co-founded a meditation company. He helped build an award-winning product, scaled to 8-figure ARR, and worked with some of the best meditation teachers in the world, including the Dalai Lama.

Today, Derek blends outer work (strategy, goals, accountability) with inner work (self-awareness, resilience, what's actually driving the stuckness).

In his own words:

“I've lived that trade-off as a founder and it sucked... for everyone. Then I discovered they could be part of the same path, and it changed everything. Now I help founders make the same shift.”

I’ve known Derek for years, as a coach, a builder, and a wonderful human being, and I’m so excited to co-create Inside-Out with him, and support our founders in scaling consciously.

Check out Derek's full story in the comments. It's worth the read.

Exited founder turned CEO-coach | Helped early/mid stage startup founders raise over $500m, and create equity value over $12bn (and counting...)

I have big news. But first, a story. 

I talk with founders every day who are in the middle of real inflection points.

Co-founder splits. Post-exit identity crises. Scaling without burning out. The weight of figuring out who they are as a leader.

But I only coach 15 people at a time, which means I can't work with most of the founders I speak with.

That's always bothered me, so we're doing something about it.

Introducing: Inside-Out Virtual Workshops.

Small (around 8 people). Led by me and the Inside-Out team using the same frameworks and modalities we use with our 1-1 clients, finally accessible to a broader group of founders.

The first workshop is Getting Unstuck. It's for the founder or exec who knows how to do hard things, but keeps hitting the same wall in one specific area.

Most approaches to this work outside-in: Better habits, tighter systems, more accountability. And if that's worked for you, great. But if you've tried all that and you're still stuck, the problem probably isn't discipline.

This workshop works from the inside-out, using IFS (Internal Family Systems), an evidence-based framework that has become one of the most powerful tools in serious executive coaching.

Give me 90 minutes. You'll leave with a new way of seeing the stuckness and a concrete experiment to take into your life.

WHEN: March 23rd. Noon to 1:30pm ET.
COST: Free

Space is very limited. Click the link in the comments if you'd like to apply.

A client told me: “The single most important thing for my company right now is the fundraise.”

Then he paused. “And it’s the thing I avoid every morning.”

I see founders in inner conflicts like this every day. This type of dynamic can take years to unwind, and kill companies and relationships along the way. 

After nearly a decade of coaching founders, I've found one reliable method for resolving inner conflicts like these: 

Internal Family Systems, or IFS. 

IFS is a leading toolset at the bleeding edge of exec coaching, and is built on the only scientifically proven method to change emotional learnings, Memory Reconsolidation.

It's a core tool in our practice at Inside-Out, and we're teaching founders how to use it themselves live on March 23. 

When we looked inside at this particular issue, we found two competing parts.

One part wanted the company to grow. The other part said, “If this fails, you’ll look like an idiot in front of your investors.” So we work on the problematic part. Once you do that, the system stops conflicting.

This doesn't take weeks of months. The best coaches help clients get unstuck in an hour or less. 

Want to learn how it works? Apply for our first intimate workshop on March 23. Application in comments.

"The moment you doubt whether you can fly, you cease forever to be able to do it."
–J.M. Barrie, Peter Pan

I've played basketball my entire life, and here’s what I’ve noticed. If I step on the court
believing I'm the best player there, I hoop. If I'm uncertain, I play poorly.
Leadership works the same way. If you believe you'll win, you'll win. If you believe you'll lose, you'l lose.
Confidence is king.

But real confidence isn't peacocking. It's not pretending you have all the answers. It's not even earned through success. You can build a great company and still be one bad outcome away from doubting yourself.

Real confidence comes from alignment between who you are inside and how you show up in the world.
The ball’s in your court.

For most of my career, creativity came from pressure. From big problems I had to solve. From outcomes I needed to hit. 

But there's a different kind of creativity that lives underneath all of that. It comes from joy. From play. From love. I call this place presence. And it's where the most interesting work happens.

I see this all the time working with post-exit founders. During the scale-up, every identity shift serves the company. But after the exit? When that crutch is gone and you're staring at a blank page, wondering what's next?

That's when the real work begins.

Because now you're not choosing who to be based on what needs to get built. 
It's terrifying. And it's also the most creative place I've ever been.

There’s a hidden force behind many “productivity problems.”

It’s not laziness. It’s not discipline. It’s not even time management.
It’s fear.

When pressure, uncertainty, or self-doubt creep in, the brain doesn’t lean into bold work.

It looks for safety. Suddenly emails feel urgent. Slack feels necessary. Small,
controllable tasks replace the ambiguous, high-stakes ones that move things forward.
From the outside, it looks like busyness.
From the inside, it’s avoidance, rooted in fear.
And the insane part? It feels rational.

Understanding how fear quietly reshapes attention, decision-making, and execution is
one of the biggest unlocks for founders and high performers.

Because you’re not always fighting a workload problem.

Sometimes you’re fighting a fear problem.

The most defining part of leadership isn’t certainty. It’s the unknown.
Especially now, when AI and systems increasingly handle the predictable, repeatable, “figured-out” work, what remains for founders and CEOs is ambiguity.

Leadership becomes a cycle:
Enter the unfamiliar.
Navigate the discomfort.
Create clarity.
Hand it off.
Repeat.

The lesson is simple, and I’m trying to follow it myself.
Stop treating discomfort as a warning sign.
It’s usually evidence you’re exactly where you need to be.
Learn to recognize it.

Normalize it.
Build the internal capacity to move forward anyway.

Most people have picked a side on AI.
Either it's the greatest tool ever built, or it's an existential threat we're sleepwalking into.

The binary is comfortable. But the leaders I work with who are navigating this most
effectively have learned to hold something harder: Both.

The fear is real. It lives in the gut. It wakes you up at 3am thinking about the world your kids will inherit. The excitement is equally real. As it should be.

The mistake isn't feeling one or the other. The mistake is collapsing into one becausethe other is too uncomfortable to carry. 

The most important things in life are paradoxical. They resist resolution. And AI may be the defining paradox of our time.

As F. Scott Fitzgerald said, "The test of a first-rate intelligence is the ability to hold two opposing ideas in mind at the same time and still retain the ability to function."

Angry seagulls are going to make you a better leader. Stick with me and I’ll
explain.

You"re in a board meeting. An investor cuts you off. "I don't think you know what you're doing. Your strategy is completely wrong."
Do you fight back or shut down?
When this happened to me once, I made two mistakes.

First, I said "okay" while quietly resenting the investor. That didn't work.
Then I pushed back and defended myself. Also a mistake. It took me years to find the third option. Get curious.

Not the kind of curious where you ask questions to trap them. The kind where you stay grounded in yourself while opening up to what you might be missing.

You're going to run into "angry seagull" investors. It's not if, it's when.
You can fight back. You might win the moment, but you won't grow.

You can blindly agree. You'll lead your company somewhere you don't believe in. Or you can ask questions. Really listen. Stay confident while staying open.

How you react when you're uncomfortable dictates the trajectory of your company and
career.

So…

What angry seagulls are in your life right now?
The investor who keeps pushing back?
The co-founder who questions every decision?

The board member who never seems satisfied?

What would it look like to stop resisting them—or blindly accepting them—and start
getting curious about what they're here to teach you?

https://lnkd.in/gHUzHVcZ

The most comforting and terrifying thing I’ve learned in business is the same truth. Here's the story.

My real education happened inside a startup accelerator. 12 intense weeks, surrounded
by founders, mentors, and Thursday night “fireside chats.”

One moment stuck.
A wildly successful executive paused when asked for his single biggest lesson for entrepreneurs. “Nobody knows what the hell they’re doing,” he said.

“The difference between successful companies and unsuccessful companies is that, with the successful ones, you can’t tell.”
That perspective has followed me through every stage of my career.

Do they teach that in school? I wouldn’t know.

https://lnkd.in/g_P32hAy

One late night, I got a call from a board member.

It was around 11pm my time, which means it was probably 3am his time.

What he said stuck with me forever.

Most leaders don’t have a strategy problem.
They have a validation problem.

The most dangerous addiction in business isn’t money or power.
It’s being liked.

Applause feels like progress.
Agreement feels like safety.

Slowly, decisions stop being about what’s right and start being about what won’t upset anyone.

That’s not leadership.
That’s people-pleasing with a title.

Control is the most expensive illusion in your company.

My Zen teacher used to tell me, “Sit down, hold everything still, and watch what moves.”
What moves is everything you don't control. Your thoughts arrive uninvited. Your
emotions surface without permission. The narrative you've built about agency begins to
quietly unravel.

AI is doing something similar at civilizational scale. It moves too fast, builds too
suddenly, disrupts too completely to let you maintain the fiction. But I've come to believe that confrontation is a gift.

The founders who thrive aren't the ones who reassert control in the face of uncertainty.

They're the ones who find a different relationship to power, one that doesn't require control as its foundation.

That's not passivity. It’s a more sophisticated form of strength.

"You have power over your mind, not outside events. Realize this, and you will find strength." — Marcus Aurelius

This video has been making its way around the Internet. You should stop and watch before you keep reading.

Most people think reading 900 words per minute is impossible. Until they do it.
What changed?

Not their brain. Not their intelligence.
Their belief about what was possible.

We’ve seen this before.

Same with running the four-minute mile.
And having smart machines.

Entrepreneurs do this constantly.

We build invisible ceilings and convince ourselves they’re real.
Then a crisis hits. Or something else forces your hand.
And you discover the ceiling was never real.

When people read 900 words per minute for the first time, there’s genuine shock. Like they discovered some supernatural ability.
But they always had it. They just never gave themselves permission to use it.

Most limitations are just untested assumptions.

Question the ceilings. Test the assumptions.
You’ll probably discover you’ve had the ability all along.

An interesting question to sit with:
What limitation are you currently living with that is, in fact, just a belief?

Scaling a company means giving away the work you used to take pride in.

Watch and listen to why that moment is harder than most founders expect.

I once heard a story that stayed with me.

A little girl walks through a garden for the first time. It was overwhelmingly beautiful, and
she runs inside to tell her mother.

Her mother smiles. “Those are pretty flowers, aren’t they?”
The next day, the girl returns to the garden… and sees “pretty flowers.”

The label stripped the magic. It flattens wonder into familiarity.

I catch myself doing this in business.
A group of complex, brilliant, unpredictable humans becomes “the sales team.”
Or “engineering.”

And without realizing it, I narrow how I see them.

Abstraction isn’t wrong. It’s essential.
But every so often, a moment of awe — in nature, in conversation, in work — reminds
me:

Reality is always richer than the words we use to contain it.

I’m doing my best to remember that.

https://lnkd.in/gxyzemuH

Have had the pleasure and privilege of getting to know Ryan, and +1 to all this

Founder/CEO at HealthBar | Healthcare Delivery & Payor Model Innovator/Entrepreneur/RN

If you don't know Ryan Cummins, you absolutely need to make it a priority!


Having Ryan close our 'Health'care 2026 conference with a keynote address is going to be engaging and empowering

The work he's doing is absolutely incredible 

His curiosity to learn is unmatched

And his focus on future generations is inspiring.....


Don't miss an opportunity to hear from, and meet Ryan at 'Health'care 2026!

healthcare2026.com

#health #healthcare #business #ceo #entrepreneurship #events

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