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?

The best CEOs I know have shorter to-do lists than you.

A perk of my work is getting an intimate look into the habits and systems of leaders across the world.

And something I've noticed about the best CEOs isn't what they do. It's what they decide NOT to do.

Most people let their to-do list become infinite. They pack in as much as possible, check off what they can, and roll everything else forward. The list never ends. And they wear it like a badge of honor.

But here's what they're avoiding: The confrontation of choice.

Saying "I'm not going to do this thing" feels permanent and final. Like you're actively choosing failure in that area.

And that's uncomfortable.

So instead, people keep everything on the list. They tell themselves, "I'll get to it eventually" and avoid the psychological weight of consciously letting something die.

The best CEOs do the opposite.

They stack rank their tasks by importance, look at their calendar, and slot only what will fit. Then they consciously move everything else to next week's list, or kill it entirely.

The result? They finish their work most days. And they get exceptionally good at one of the most important skills in leadership, which is saying no to important things.

Because here's the truth…

Your workload never decreases as you grow. You just get better at leading. And having less time forces you to delegate, empower your people, and build your organization instead of just working harder.

Your to-do list is a daily training ground for this.

Every day, you're forced to confront what dies so something more important can live.

That confrontation is the work.

Not the hustle of doing more, not the performance of appearing busy.

The discipline of doing what counts. And ruthlessly eliminating what doesn't.

https://lnkd.in/gbCGxgNW

Open article: Inside Out Leadership — CEO's Personal Management System: Prioritize Deep Work & Self-Care by leadinsideout.io

Inside Out Leadership — CEO's Personal Management System: Prioritize Deep Work & Self-Care

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

🤖 My Maven course and AI practice copilot for Product Sense and Analytical Thinking interviews (www.benerez.com/copilot)  🔁 Insider Loops: Helping PMs ace their OpenAI, Stripe, Uber, Figma and DoorDash interviews (www.insiderloops.com) I've been a founder, joined three different startups as their first PM, and held senior PM roles at Meta and Attentive. After leading product &amp; design at Continuum, a marketplace for fractional executives, I now partner with early stage founders as an advisor and help PMs land their dream roles.    My experience spans business models and stages:    - Life360 (Series B+C consumer mobile)   - Breathe (consumer mobile in mindfulness / mental health)   - Breeze/Canvas (Series A + acquisition automotive consumer, fleet management)   - Abstract (Series B+C B2B SaaS for design teams)   - Facebook (post-IPO SMB advertiser guidance)   - Attentive (Series E marketing tech)   - Continuum (Series A fractional executive talent marketplace)   - Lettuce (Seed + Series A fintech for solopreneurs)

Ben Erez

This week Meta overhauled its PM interview loop and it's not just candidates who need to prepare.

Three months ago, I posted about Meta quietly testing a "Product Sense with AI" interview as a 4th round in its final loop — mostly a pilot for L6+ candidates going for AI/ML-heavy roles.

This week, it became official. And the scope is much bigger than I initially reported. Here's what I know.

The new final loop for external candidates interviewing for roles in Meta's Central Products org (the largest PM org by headcount) now consists of four interviews:

1. Product Sense with Vibe Coding
↳ Define motivations, target audiences, and key problems, then translate your thinking into prompts and build a working prototype using AI

2. Analytical Thinking & Logical Reasoning
↳ Two parts: a product scenario with analytical questions, plus quantitative reasoning based on two research articles Meta provides in advance

3. Product Architecture
↳ Open-ended system design problem, closer to Stripe's interview than a traditional PM interview. Technical acumen, trade-offs, and engineering collaboration.

4. Leadership & Drive — unchanged.

The former final loop structure (Product Sense + Analytical Thinking + L&D) is gone for PMs interviewing into the Central Products org.

But here's the part that caught my attention even more.

Current Central Products PMs — including senior ones — are being asked to go through the three new interviews above as well (no L&D for the internal loop). They'll need to be interview ready as soon as March!

While there are no officially stated consequences for not passing the internal loop, murmurings within Meta are that failure will likely result in a significant PSC ding. One source was more direct — you won't lose your job immediately, but you may get labeled "legacy PM" vs. "AI PM" (the former label being a step toward the door).

Even VPs are going through this. Everyone is scrambling.

A few open questions I'll be tracking:

❓ What happens to the screening round? The new guide only covers the full loop.

❓ Who are the interviewers, and how are they being calibrated? The logistical lift for March is enormous.

❓ Does this roll out beyond Central Products? One source in a different Meta org expects it will.

❓ What support, if any, are internal PMs being given to prepare?

This isn't just a process change. It's Meta making a bold statement about what a great PM looks like in 2026 and beyond, using both hiring and internal evaluation to enforce it.

I've been studying PM interviews for years and will keep reporting as I learn more.

[Quick update: I have confirmation that *for now* this change is specific to the Central Products org that covers areas like integrity, safety, and trust. The generalist PM interview process is unaffected at this point]

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

Your company's AI training is probably a waste of time. Here's why.

We just published our conversation with Gagan Biyani (CEO of Maven), who spent three months last year exploring whether Maven could sell into enterprise L&D budgets. What he found was eye-opening.

Companies know they need AI education. But the investment is far lower than you'd expect. And when they do invest, it often fails.

Gagan identified five structural reasons why:

1. L&D has a credibility crisis. 
Over the last 15-20 years, the entire discipline of learning and development has developed a reputation problem. AI could be the moment L&D reinvents itself. But right now, L&D teams aren't being asked to lead the charge, and they aren't respected enough within orgs to drive the solution.

2. Companies default to generalized AI training. 
The fallback is company-wide "learn ChatGPT" sessions. Gagan's take: this is like doing "internet training" in 2005. Every PM on the same team will use a different mix of AI tools depending on their product, their team, and their specific challenges. One-size-fits-all doesn't work.

3. AI adoption requires system-level change first. 
Before individuals can be productive with AI, the company often needs infrastructure changes. At Maven, their head of design realized the entire design system needed to be rebuilt to be more legible to AI. That took 4-6 months — and required senior judgment to even diagnose.

4. Companies are listening to the wrong people. 
The internal AI champions tend to be tinkerers who get excited by demos, quick to move on, and bad at translating their experience to the broader org. The people you want driving adoption are the pragmatic middle adopters who use AI because it's useful, not because it's fun.

5. L&D specialists know how to teach but not what to teach. 
L&D professionals are experts in the craft of education. But AI requires you to learn the thing first before you can teach it. That's not where L&D teams have traditionally operated, and it creates a gap that's hard to close quickly.

Gagan's conclusion is that the ideal setup is a C-level sponsor who takes personal ownership: running meetings, leading trainings, etc with a chief of staff amplifying the work. If you delegate it entirely to a mid-level employee, you'll stall.

This mapped to what Marc and I see in the Supra community. The companies making real progress on AI adoption almost always have a founder or senior leader who's personally pushing the transformation.

If you're thinking about driving AI adoption at your company, I think you'll love this episode.

Episode links:

Spotify: https://lnkd.in/dJqNBYvE
Apple: https://lnkd.in/d6X5kyZ3
YouTube: https://lnkd.in/dmZZDgSs
Substack: https://lnkd.in/dq__wyRb

My favorite piece of advice this year so far: ignore almost every new AI thing for 6 months.

We published our conversation this week with Gagan Biyani (CEO of Maven), who said something in the podcast that felt simultaneously grounded and spicy:

"My advice is only learn things that are six months old."

It sounds counterintuitive because we're swimming in a feed that makes every 48 hours feel like a decade of change. 

New models, new agents, new frameworks, and people posting their Mac Mini lobster setups like status symbols. Nobody wants to fall behind.

But Gagan's point is that if you're using AI for your actual work, there's basically zero benefit to being in the top 1% of adoption. 

Instead, his take is that being in the top 10% will make you more effective. 

The top 1% is reserved for tinkerers and content creators. They scout what's new, test what breaks, and post what's exciting. And that's genuinely valuable because tinkerers made things better for all of us. 

Focused operators, however, should be mindful of what Gagan calls the "market digestion period." This is the phase where the market eats a new tool, digests it, and on the other end we'll see whether it still matters.

This maps to something he sees playing out inside companies too. Most orgs pick their biggest AI tinkerer and say: "You. Lead our AI transformation." 

It sounds logical. But tinkerers adopt tools because they're exciting. They get more fired up by demos than daily workflows. And by nature, they tinker and move on.

The people who actually drive real org change are what Gagan calls the 10-to-30 percenters. These are folks not on the bleeding edge but far from behind. They adopt AI because it's useful, not because it's novel. They're the bridge between the scouts and everyone else.

He shared a perfect example from Maven. 

Maven's head of design, Yuan W., isn't in Maven's top 1% of AI adopters. She's in that 10-to-30% range. And that's exactly why she was the right person to lead.

Yuan knew enough about AI to assess that the design system itself needed to be rebuilt as a foundational step for AI to help the team build faster (e.g. enabling anyone to vibe code a solution to a customer problem). 

This rebuild took months of work and required deep craft judgment (and of course - commitment from Gagan as the CEO). A tinkerer would have moved on to the next shiny thing long before finishing it.

The tinkerers scout the territory. The 10-to-30 percenters build the roads everyone else can drive on.

My takeaway from the convo is that it's okay not to jump on every new tool/trend.

I'm trying to be zen, telling myself new tools are like clouds passing by. More clouds will come. I don't have to chase every cloud.

🎙️ Full episode: 

Spotify: https://lnkd.in/dJqNBYvE
Apple: https://lnkd.in/d6X5kyZ3
YouTube: https://lnkd.in/dmZZDgSs
Substack: https://lnkd.in/dq__wyRb

A talent leader recently pinged me they're hiring a product recruiter. I asked around for referrals and was truly surprised what I heard back.

Multiple versions of: "Tell them good luck. it's impossible right now".

And that's from recruiting leaders I trust! 

My reaction: "wait wait wait... what?"

I’ve been operating under the assumption that there are tons of strong recruiters available because so many companies slashed their recruiting teams.

So when someone asked me if I knew a great product recruiter, my instinct was, “there must be a ton of them - one sec...”.

And apparently - nope! There's a surprisingly intense squeeze for top recruiters. They're almost impossible to hire. Had no idea.

So I asked, "why is this happening?"

Not because companies aren’t hiring.
Not because the recruiter role isn’t important.

It's because the top end of that market is extremely constrained.

So I asked "why is that the case?"

Two factors I heard back:

1) The last cycle of tech didn’t actually produce that many truly great recruiters.
2) The ones who are great tend to have extreme agency. They’re either in the best job already, or they’ve gone independent and built their own platform.

Basically, the best recruiting talent is either operating at the top 1% of companies or working for themselves. 

Hmm.

We keep saying it’s a buyer’s market for talent. And overall, that might be true.

But when you zoom in on specific high-leverage IC roles, the market may still be structurally tight.

The truly strong ones don’t float around for long. They choose environments. Or they create them.

Which forces a tougher question for hiring managers: if you can’t hire the top 1%… are you building a system that can grow someone into that tier?

And is recruiting unique constrained?

Or is the top 5% of IC talent simply concentrated than we want to admit across the board?

I’m more excited about work than ever, while simultaneously having less hours to work than ever. 

My life this year so far is basically down to family, work, health/gym, and sleep. 

I’m doing a lot and it feels full.

Yet, I perpetually feel behind.

I don’t know exactly what I’m behind on, but I’m sure there’s something.

Here are a few that my various inboxes are baiting me about:
- If I’m not automating my whole life with AI, I’m a laggard.
- If I’m not buying a Mac Mini to configure OpenClaw, I’m a dinosaur.
- If I’m still doing anything the old way, I’m a boomer.
- If I’m not spending hundreds of dollars per month on tokens, I’m under-leveraged.
- etc etc etc

Every minute not spent tinkering with AI is making me fall behind… right?

Keep reading in the full post 👇

Open article: OpenAI guide, fractional work advice, PM recruiter squeeze, endless FOMO by benerez.substack.com

OpenAI guide, fractional work advice, PM recruiter squeeze, endless FOMO

Don't be a Pikachu. 

I was recently talking to some product leaders I trust about a trend where tenured engineers at established tech companies seem to be dragging their feet when it comes to AI adoption. 

There's a heavy skepticism about the impact of AI, potentially fueled by fear.

You can probably map every engineer to some point on the spectrum between these two extremes: 
1. Engineers eagerly excited to evolve their job using AI
2. AI skeptics/laggards who refuse to embrace AI to evolve

The latter group is losing relevance in the workplace and this is happening at an accelerating rate.

It made me think of one of my favorite Pokémon, Pikachu. 

Pikachu refuses to evolve into his new form, Raichu, because he's stubbornly determined to compete with the best Pokémon at the highest levels of evolution without, himself, needing to evolve. 

I think people dragging their feet with AI adoption are being a Pikachu. 

While that's admirable in a fictional cute and cuddly cartoon character, I don't think that there is going to be a large demand for very cute and cuddly engineers who refuse to adopt AI because they think they don't need it.

To future-proof your career, embrace AI. Don’t reject the opportunity to evolve. 

Don't be a Pikachu.

OpenAI is raising at a $850B valuation and our Insider Loops guide breaking down their PM interview process is now live 🚀

Since launching Insider Loops last September, the most common ask Marc & I have received for new guide is OpenAI. 

So we got to work over the last couple months and had a bunch of off-the-record convos with insiders, as well as a handful of PMs who recently went through the OpenAI loop. The result is our first guide for a major AI lab's PM interview process.

We're launching the OpenAI guide at a lower introductory price because we had fewer insiders and debriefs to draw from compared with our more mature guides.

That said, we're still highly confident in the guide's accuracy and usefulness today: it captures the core filters, stage-by-stage expectations, and preparation strategy that matter most for OpenAI.

As we add more proprietary interview intelligence in the coming weeks, we'll continue enriching the guide and increase the price accordingly.

Since buyers get lifetime access to guide updates, this is a great chance to lock in the early bird price. Get the OpenAI guide at www.insiderloops.com

P.S. more guides are in the works and our existing guides are getting better every week based on real-time insights from PMs

Everyone's talking about forward-deployed engineers but what about forward-deployed product leaders?

"The most important product work we did this year had zero user-facing impact for 4 months." 
- Chase Schwalbach (SVP of Product & Technology at Millie)

On our latest episode of Supra Insider, Chase shared how he spent his first ~4 months:
• Consolidating fragmented data into a single warehouse
• Making everything HIPAA-compliant
• Untangling vendor contracts just to get data access
• Rebuilding infra so experimentation was even possible

No new features.
No shiny launches.
No UI refresh.
Nothing customers could see.

Chase realized he wouldn't be able to build serious AI-powered product on top of messy infrastructure. Without unified data, guardrails, and eval discipline, “AI features” are just demos.

So he bit the bullet and took on major infra work, embracing the role of a "forward-deployed product leader":
↳ He went deep himself instead of delegating prematurely
↳ Shielded the broader team from early-stage chaos
↳ Prototyped in public (in Slack) to build shared intuition
↳ Only pulled the team in once the foundation was real

Speed wasn’t about shipping fast. It about removing structural friction so the next 12 months could move 10x faster.

Many product orgs are trying to layer AI on top of legacy systems right now but very few product teams are pausing new feature work, going dark, and rebuilding the foundation for an AI-native product development process.

If you're a product leader who's been wanting to get your hands dirty with IC PM work but aren't sure how, this episode is for you.

Episode links:
Spotify: https://lnkd.in/edN6u2pC
Apple: https://lnkd.in/ezqbDN3V
YouTube: https://lnkd.in/eMcnSGdv
Substack: https://lnkd.in/eV-G4MUM

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