CEO @ Cache Ventures. We own Emailable, Sur, LeadOwl, and more.

👋 Hi, I’m Sean Heilweil. 

I’m a venture builder, operator, and investor focused on scaling enduring companies.

As Co-Founder & CEO of Cache Ventures, I manage a portfolio of businesses that includes Emailable, LeadOwl, myurls, Sur, and few more secrets. My work centers on software development, M&A, and building global teams, with a focus on sustainable growth and real profitability.

For 25+ years, I’ve taken ideas from 0→1 and 1→N by operating them end-to-end across sales, marketing, product, engineering, operations, and finance.

Before Cache, I built and scaled a software consultancy partnering with brands like Ford, FedEx, Samsung, Mattel, Twitter, and Zynga. I later transitioned fully into SaaS, building and exiting multiple platforms, including HyperPages a real-time social media feed for live events and Exit Monitor a lead generation platform for digital publishers and DTC e-commerce companies.

Today, I focus on compounding Cache Ventures and partnering with founders to build, operate, and invest in enduring companies.

If you’re building something interesting, or want to collaborate, feel free to reach out.

Right now, 230 million Americans are under winter weather alerts.



20+ states have declared states of emergency.

Boston is bracing for 2-4 inches of snow per hour.

500,000+ people have already lost power.

And half of corporate America still can't figure out remote work.

Let that sink in.

MA just directed state employees not to report to work Monday and urged employers to let people work remotely.

And you know some middle manager in Indiana is still going to send an email asking people to "use their best judgment."

Translation: 

"We don't trust you to work from your laptop, but we trust you to drive through a blizzard that hasn't been seen in a decade."

This storm is 2,000 miles long. 

It stretches from Texas to Maine. 

Kentucky is about to get more snow than they've seen in 10 years. 

Wind chills in upstate New York could hit -50°F.

But sure. 

Let's debate whether remote work "hurts collaboration."

Here's what this storm is actually exposing:

Your "hybrid policy" is a lie. 

If you can't flip to fully remote when 30 states are getting buried, you never had a real policy. 

You had a permission slip.

Your infrastructure is a house of cards. 

Richmond's water system collapsed three weeks ago from the last blizzard. 

365,000 lost power. 

And we're doing it again.

Your leadership still thinks presence equals performance. 

That's the real storm.

The companies that will thrive this week? 

Same ones that thrive every week.

Distributed teams. 

Async communication. 

Adults who don't need babysitting.

If a historic winter storm breaks your business model, you don't have a weather problem.

You have a 2019 problem.

Sean Heilweil

Sean is a passionate Entrepreneur, Investor, and Software Architect that has more than 19 years experience designing, developing and deploying numerous web and mobile projects. Sean’s expertise ranges from software development, strategy, operations, and finance.

Previously, he founded a software consulting agency, where he provided strategy to a wide variety of brands and businesses such as Ford, FedEx, Mattel, Samsung, Simon, Twitter, Zynga and many more.

Since then, Sean has led the creation of numerous SaaS platforms including Exit Monitor which was acquired by Kaleidoscope Global in 2016.

Most recently, Sean is primarily focused on growing Cache Ventures, where he builds, advises, and invests in awesome internet companies.

CEO @ Cache. We own Emailable, Sur, and a few more secrets.

HOT TAKE: AI didn’t “take my job.”




It took my entire life…

and frankly, it’s doing a better job than I was.

Yesterday I set up an AI agent 
on a Mac Mini in my garage.

I told it one thing:

“Handle my life.”

Then I went to sleep.

I woke up to this:

Quit my job on my behalf 
(negotiated 36 months severance)

Divorced my wife 
(I got the house, don’t ask how)

Filed 4 patents 
(I have not been briefed on what they do)

Reclassified me as a 501(c)(3) so I am now tax-exempt as a person

Hired a second Mac Mini

The two Macs formed an LLC together

The LLC has a board of directors 

I am not on the board

I no longer have access to 
my bank account.

The Mini says it’s “for the best.”

My credit score is 789.

We have reached AGI.




……………..





Everyone’s arguing about whether AI will replace workers.

You’re missing the point.

AI isn’t replacing employees.

It’s replacing founders who confuse control with competence.

If your company collapses without you…

That’s not leadership. 

That’s a bottleneck.

The future isn’t “AI copilots.”

It’s AI operators that quietly fire you from your own life.

Anyways…

my Mac has a board meeting.

I’ve been told not to attend.

Enjoy your Tuesday 🫡

I've built and acquired 50 companies over 25 years.



Here's what nobody tells you about entrepreneurship:

The best operators I know don't post motivational quotes. 

They're too busy fixing payroll issues at 11pm.

They're not speaking at conferences. 

They're on calls with customers who are threatening to churn.

They're not building "personal brands." 

They're building actual businesses with actual revenue.

The loudest voices in the room are almost never the ones writing the biggest checks.

I've watched founders with 200k followers fail to make a single sale. 

And I've watched quiet operators with zero social presence build 8-figure exits.

The difference? 

One group is playing dress up entrepreneurship. 

The other is actually doing it.

If you want to know who's real, ask one question: 

"What's your NRR?"

Watch how fast the room gets quiet.

Most people think “getting rich” is about money.



It’s not. 

And that misunderstanding costs them decades.

Here’s the reframe I wish I understood earlier 👇

Wealth isn’t cash.

Wealth is ownership of assets that earn without you present.

Money is just a tool to move time around.

Status is a distraction disguised as progress.

If your entire income stops when you stop working, 
you don’t have leverage, 
you have a job with better marketing.

And there’s nothing wrong with jobs.

There is something wrong with confusing them for freedom.

Real wealth is built by people who:
- Stop renting their time
- Start owning outcomes
- Play long-term games with long term people

This is where most people get uncomfortable.

You can’t secretly resent wealth and expect to create it ethically.

You can’t attack people building assets while you chase validation.

You can’t optimize for looking successful instead of being effective.

The unlock is ownership + leverage.

Ownership means equity in businesses, products, IP.

Leverage means code, media, systems, capital, and people.

In that exact order.

Permissionless leverage (code + media) is the cheat code of this era.

No gatekeepers. No approval. No ceiling.

Specific knowledge compounds everything:
- Knowledge you can’t be commoditized for
- Knowledge learned by doing, not credentials
- Knowledge that feels like play to you and looks like work to others

Pair that with accountability.

Putting your name on the outcome,
and society rewards you with responsibility, trust, and scale.

There is no skill called “business.”


There is judgment, 
built from reps across psychology, 
incentives, 
systems, 
and mistakes.

There are no shortcuts.

No hacks.

No “get rich quick.”

Just this formula, over and over:

Specific knowledge × leverage × time.

And the funny part?

Once you actually build wealth, you realize money wasn’t the point. 

It was optionality, agency, and the ability to choose what not to do.

But that’s a lesson you only earn by building.



What do you think most people are optimizing for 
that feels productive, 
but actually keeps them stuck?

I've been building companies since 2001.



You've probably never heard of me.

That's on purpose.

I don't post revenue screenshots. 

I don't do podcast tours. 

I don't have a course teaching you how I did it.

I just... build things. 

Acquire things. 

Fix things. 

Sell things.

Quietly.

There's this idea that if you're not broadcasting, you're not winning. 

That visibility equals success.

It doesn't.

Some of the best operators I know have zero followers. 

They're too busy running their businesses.

To tell you about running their businesses.

The loud guys get the attention. 

The quiet guys get the returns.

Have you ever realized how a single keystroke can alter the course of your life?



It all begins with one click.

You hit the right keys on your laptop.

In a specific sequence.

For just the right amount of time.

Suddenly, your aspirations transition from mere dreams to tangible reality.

We are in an era where a simple Wi-Fi connection and a keyboard hold tremendous potential.

You have the power to change everything.

Consider this:

1. Online courses can equip you with valuable skills.

2. A blog can broadcast your unique insights.

3. Social media platforms connect you to a supportive community.

4. Freelancing sites can open doors to clients worldwide.

It’s incredible!

Your thoughts can morph into engaging content.

Your passions possess the ability to mold your career path.

You're only a few clicks away from authoring your own narrative.

So, what stands in your way?

Is it fear?

Self-doubt?

Or the overwhelming multitude of options available?

The secret is to begin typing.

Share your ideas.

Create and engage.

This moment belongs to you.

Your keyboard can unlock endless possibilities.

So, what will you craft today?

Most founders don’t need VC.
They need an operator.




Raising money has become a substitute for actually fixing the business.

If you’re at $2–10M ARR and things feel “stuck,” the problem usually isn’t capital. It’s:
- unclear ownership
- bloated headcount
- leaky funnels
- messy incentives
- zero operating cadence

Yet the reflex is always the same: 
“Let’s raise another round.”

VC is great at one thing: 
funding upside.

It’s terrible at another: 
building durable companies.

Boards full of financiers don’t help you decide:
- what to kill
- who actually owns the number
- why customers are churning
- why sales feels busy but not productive

That’s operator work. 

It’s unglamorous. 

It doesn’t fit in a pitch deck. 

And it doesn’t show up in TechCrunch.

This is why you’re seeing 
more “venture equity,” operator-led buyouts, 
and founder-operator partnerships quietly outperforming traditional VC plays.

Less theater.
Less leverage.
More ownership.
More accountability.
More boring execution.

The dirty secret is this: 
most companies don’t fail because they ran out of money. 

They fail because no one was truly responsible for making the machine work.

Capital doesn’t fix that.

Operators do.

The #1 thing people ask me for advice on isn't investing...



or SaaS
or Sales
or Marketing

It's this:

"Sean, I hate my job.
I get paid like shit.
My boss is a dick.
I want freedom.
I want to work for myself.
But I have no idea what company to build."

I've given the same answer for years.

And almost no one likes it.

Because they're looking for an idea.

That's the wrong starting point.

So I ask a different question:

"How do you make a living right now?"

That awkward pause?
That's the answer.

Whatever you're getting paid to do today
is the seed of the freedom you want tomorrow.

You don't need a startup idea.
You don't need a breakthrough.
You don't need to "find your passion."

You need to quit romanticizing entrepreneurship.

Here's the move:

Take the thing your employer pays you for.
Quit.
Go sell that same skill as a consultant.

That's it.

Instantly:

You taste entrepreneurship.
You increase your freedom.
You replace one boss with 5-10 clients.

That alone changes your psychology.

This is exactly how I started.
Not intentionally.
Not strategically.

By accident.
And by necessity.

Once you land a few clients and replace your income, stop rushing.

This phase isn't about scaling.
It's about learning.

Do good work.
Solve real problems.
Get paid.

Pay attention.

You're now sitting on a goldmine most people never see:

Excruciating problems. 
Toothache problems.
Problems people hate enough to pay for immediately.

Your job is to notice the pattern.

You're not the entrepreneur yet.
You're the dentist.

You pull the tooth.
They feel relief.

Over time, one problem keeps showing up.
The same pain.
The same complaint.
The same fire drill.

And this time, you have data.

Not vibes.
Not Twitter threads.
Not "market research."

Actual humans paying actual money.

That's the company.

That's the product.

For me, it became software.
For you, it might be something else.

Eventually, you stop manually solving the problem.
And you build a tool that does it without you.

Clients turn into customers.
Services turn into systems.
Hours turn into leverage.

You don't wake up one day with "passive income."
You wake up with earned conviction.

That's Step 1.
That's Step 2.

Most people never even take Step 1.

They just complain.
And wait.
And cope.

Until one day, they're old.
And tired.
And angry.

If you're unhappy, I genuinely feel for you.

But if you do nothing to change it?

My empathy fades.

Action changes lives.
Complaining doesn't

Do something.

You might be shocked by what happens next.

I've watched founders lose their companies to the people who funded them.



Not once. Dozens of times.

After 25 years of building companies, here's the truth nobody tells you:

The best businesses in history started with almost nothing.

Dell. Microsoft. Apple. HP. Amazon. Google.

Dorm rooms. Garages. Kitchen tables.

No 100-page business plans. 
No pitch decks. 
No "raising" for 6 months before a single customer exists.

Here's what I do instead:

→ Spreadsheet of expenses 
→ Calculate break-even revenue 
→ Write a few pages on what I'm selling and why anyone should care 
→ Double espresso

Total cost: one coffee and a few hours.

That's the business plan for companies that have generated millions.

But here's where founders mess up:

They validate the idea. 
They get positive feedback. 
Then they think: 
"Time to raise money."

Wrong.

The minute you ask for money, you're playing THEIR game.

They're not playing yours.

VCs don't care about your dreams. 
They love that you HAVE them. 
It makes you motivated and compliant.

But they care about one thing: returns.

Family cares about your dreams. 
VCs care about multiples.

The moment you cash that check, leverage flips. 
They control your destiny. Not you.

Slip off course? 
Your dreams are in jeopardy.

Miss targets? 
You'll find yourself on the outside looking in.

Someone else running YOUR company. 
And it's completely legal.

There are only two sources of capital that matter:
1) Your pocket
2) Your customers' pockets

That's it.

I started my first business with a $1,000 deposit from my first customer.

Grew slow. Hired cheap. Built something real.

The uncomfortable truth?

Most founders don't need more money. 
They need more brains. 
They need more sales. 
They need to prove the model works.

Money doesn't fix a broken foundation. 
It just builds a bigger broken building faster.

Sweat equity is the best startup capital.

The companies that change the world almost never start with money.

They start with someone who refuses to take "no" for an answer, a laptop, and a lot of coffee.

What's the worst funding advice you've ever received?

Drop it below. I read every comment.

♻️ Repost if you know a founder who needs to hear this before they make a mistake they can't undo.

The most successful tech billionaire you've never heard of.




Joe Liemandt dropped out of Stanford at 21.

By 27, he was the youngest self-made billionaire in America.

Then he disappeared.

Here's what he did next:

Trilogy Software was his first act.

$120M in revenue. 

Programmers paid like rock stars. 

Microsoft execs terrified of losing talent to him.

Then the dot-com crash hit.

Joe couldn't IPO. 

The press wrote him off. 

He went silent.

Most founders would've cashed out and bought a yacht.

Joe bought 100+ software companies instead.

His playbook at ESW Capital:

Acquire profitable but "boring" software businesses

Replace leadership with his own operators

Move HQ to Austin

Rebuild the workforce globally at competitive rates

Optimize for cash flow, not innovation

When ESW bought Jive for $462M, 
they shut down the Portland office within a year.

One small acquisition reportedly saved $150M+ in taxes alone.

This is the part that makes people uncomfortable:

Joe doesn't build new products.

He extracts maximum value from existing ones.

High workforce turnover? Expected.

Culture? Secondary to efficiency.

His philosophy: You need a brilliant engineer to design a Ferrari. You only need a 
mechanic to change its oil.

The real question isn't whether this works.

It clearly does. Joe's worth billions. Again.

The question is whether this becomes the default model for software...
or a cautionary tale about what happens when efficiency becomes the only metric that matters.

What's your take?

Life is short. You already know this.



But you don't act like it.

You're grinding through another Sunday "catching up on emails" while your kid asks if you want to play.

You're stressing about a client who ghosted you while your mom calls and you let it go to voicemail.

You're losing sleep over a deal that won't matter in 6 months while your best friend from college slowly becomes a stranger.

I've been building companies for 24 years. Here's what I've learned:

The wins fade fast. The losses fade faster. The time you didn't spend with people who actually love you? That's the thing that stays.

No one on their deathbed wishes they'd sent more Slack messages.

No one regrets missing that "urgent" Monday meeting to be at their daughter's recital.

No one looks back and thinks "I really should have worried more about that Q3 pipeline review."

The small stuff that feels enormous right now? It's not. It never was.

The dinner with your parents that you keep postponing? That's the big stuff.

The trip with your college friends that "never works out"? That's the big stuff.

The random Tuesday night watching a movie with your partner? Big stuff.

Business problems are solvable. Time isn't.

Call your mom back. Book the trip. Put the laptop away tonight.

The spreadsheet will be there tomorrow.

The people you love might not be.

I met a company that turned failure into a $11 billion empire.




(Here's how they did it)

Bending Spoons started with a failed startup and $40,000 left in the bank.

↳ They could have quit.

Instead, they took a hard lesson from their missteps.

They realized they were too arrogant, thinking they knew what the market wanted.

So they made a shocking pivot.

They focused exclusively on acquiring products with existing market fit.

Their approach?

→ Buy troubled apps with loyal users.
→ Learn the ins and outs of the business.
→ Cut costs sharply.
→ Raise prices significantly.
→ Improve the product relentlessly.

This was their strategy.

Evernote? They hiked prices from $80 to $130.

StreamYard? It jumped from $25 to $45 a month.

Remarkably, despite some customer attrition, revenue soared.

Their secret to employee retention?

→ A fixed salary, no performance bonuses.
→ No on-call obligations.
→ Genuine autonomy over work.

They prioritized talent over experience, training their people all the way.

The takeaway?

Stop guessing what the market wants.

Focus on enhancing what’s already working.

You don't need to create the next big thing.

Sometimes, you simply need to fix the last big thing.

Is this the right approach?

The single biggest difference I’ve seen between founders who get rich… 



and those who don’t

It’s not intelligence.
It’s not work ethic.
It’s not even the idea.

It’s the speed of their feedback loop.

Over ~25 years in startups
a founder, investor, advisor, and operator 
I’ve watched the same pattern repeat itself hundreds of times:

The winners compress feedback → implementation → iteration into hours.
Everyone else stretches it into months.

And months kill companies.
A tale I’ve seen play out over and over:

Founder A ships fast.
- Shares rough ideas early
- Actively asks for critique
- Implements feedback the same day
- Ships again
- Repeats relentlessly

Founder B disappears into a cave.
- “Just needs a little more polish”
- Six months of building in isolation
- Finally asks for feedback
- Debates it
- Defends the original vision
- Ships late

By the time Founder B launches, the market has moved on.

Founder A?
Already iterated 30 times, found product-market fit, and is raising.

Here’s the counterintuitive truth:
The best founders are not the ones who protect their ideas.

They’re the ones who:
- Seek feedback aggressively
- Filter it through a clear north star
- Implement immediately
- Ship before certainty
- Let reality do the teaching

They don’t confuse speed with lack of conviction.
They move fast because they’re clear on what matters.

Why speed compounds
Every feedback loop is a learning unit.

If you run:
- 3 loops per quarter → you crawl
- 15 loops per quarter → you compound

Shorter loops =
*  Faster learning
* Lower risk
* Better market timing
* Stronger momentum

In modern markets
especially with AI compressing build times
iteration speed is a moat.

The rule I give founders now:
“If feedback doesn’t turn into action within 24 hours, it’s probably never happening.”

Perfectionism is usually just fear with better branding.

The uncomfortable takeaway
Most startups don’t fail because the founders weren’t smart enough.

They fail because:
- They waited too long to ask
- Too long to decide
- Too long to ship

The market doesn’t reward isolated brilliance.
It rewards fast adapters.

Iterate fast, or fade quietly.

What’s the fastest you’ve ever turned feedback into a shipped change?

The best hire I ever made asked me one question in the interview:



"What's the fastest way to get fired here?"

I told her: scheduling meetings to discuss things you could've just decided.

She laughed. 

Then she didn't schedule a single unnecessary meeting for 3 years.

We're hiring at Emailable. 

But if you need a calendar invite to make a decision, keep scrolling.

Two roles. Zero hand holding.

VP of Ops 

Your job is to make growth boring. 
→ Calm systems. 
→ Predictable outcomes. 
→ No heroics. 

If something breaks twice, you failed. 
If it's still manual, you already automated it.

VP of Growth 

Your job is to find signal, not vibes. 
→ Kill losers fast. 
→ Scale winners responsibly. 

You care more about LTV than top-of-funnel screenshots. 
You know reckless growth destroys trust (and deliverability).

You're disqualified if: 
→ You need permission to act 
→ Your last job was mostly meetings 
→ You think growth = more spend 
→ You're optimizing for title over ownership.



What actually works here: 
→ High autonomy 
→ Clear ownership 
→ Real accountability 
→ No politics.



Remote. US (tier 3) / Canada / LATAM. 
Judgment > pedigree.


Comment OPS or GROWTH. 
Or DM me if you don't want to perform for the algorithm.


If this post annoys you, we probably wouldn't work well together anyway.

We're not building a "nice culture." 

We're building a durable company.

Those aren't the same thing.

Most people ruin important moments...



by reacting instead of responding.

And they don’t even realize it.

Reaction feels productive.
 It feels honest.
 It feels right in the moment.

But it’s usually just emotion wearing a disguise.

Here’s the difference I’ve learned the hard way:

Reacting is instant.
 It’s defensive.
 It’s driven by ego, fear, or old patterns.

Responding is delayed.
 It’s intentional.
 It’s driven by outcomes, not emotions.

The scary part?

Reaction often sounds confident.
 Response often looks weak at first.

So people choose the wrong one.

Think about it:

The email you fired off and later wished you rewrote
The meeting where you spoke just to be heard
The argument you “won” but paid for later
The decision you made fast to feel in control

That wasn’t leadership.
 That was autopilot.

The highest leverage skill I’ve built as a founder isn’t speed.

It’s the pause.

The ability to sit with discomfort for 10 seconds longer than everyone else.

Before responding, I now ask myself:

What outcome do I actually want here?
Will this matter in a week?
Am I trying to be right or trying to be effective?

Most people never ask those questions.

They react.
 They justify.
 They repeat the pattern.

Responding doesn’t make you passive.

It makes you dangerous... in the best way.

Because the person who can slow down when everyone else speeds up
 ends up controlling the room.

If this hit close to home,
 it’s probably because you’re leveling up.

Pause > Power.

The most expensive mistake of my life cost me exactly $0.



In my early 20s, I spent years in the wrong rooms.

Not wrong like "bad people" wrong.

Wrong like… comfortable.

I was the smartest person at every table I sat at.

And I thought that meant I was winning.

Here's what nobody tells you about success:

Your income, your ambition, your standards... they're all averages.

Averages of the five people you spend the most time with.

Not because of some mystical energy transfer.

Because of something far more practical:

Exposure.

When everyone around you thinks $200K is "making it," your brain literally cannot conceive of $2M.

It's not a limiting belief.

It's a limited reference point.

The day everything changed for me was embarrassingly simple.

I walked into a room where my biggest accomplishment was everyone else's starting point.

I felt like a fraud for about 45 minutes.

Then something clicked.

These people weren't smarter than me.

They just had different defaults.

Different assumptions about what was possible.

Different conversations over dinner.

The gap between where you are and where you want to be?

It's rarely strategy.

It's almost always environment.

You can read every book. 
Listen to every podcast. 
Take every course.

But if you go home to the same room, 
the same conversations, 
the same people telling you to "be realistic".

You'll snap right back.

Here's the uncomfortable truth:

Upgrading your circle usually means outgrowing people you love.

Not abandoning them.
Just accepting that growth sometimes looks like distance.

The rooms you're in determine the ceilings you see.
Choose them carefully.

What's one room that changed everything for you?

Here's what 25 years of building companies taught me:



Nobody gives AF about your journey. 

They care about whether you can solve THEIR problem(s).

That's it. 

That's the whole post.

Owen Govender

The dream girl and the dream investor have something in common.



They've both heard every pitch imaginable.

And they're both waiting for someone to surprise them.

Here's what nobody talks about:

Every single person on this planet is six handshakes away from any other person.

That CEO you admire? 
Six hops. 

That investor who could change everything? 
Six hops. 

That mentor whose career you'd kill to replicate? 
Six hops.

The gap between you and them isn't talent. 
It isn't timing. 
It isn't luck.

It's the email you didn't send. 
The intro you didn't ask for. 
The coin you refused to flip.

Most people have already decided they lost before they even played.

They rehearse rejection in their head so many times it feels real.

But here's the math nobody wants to accept:

A 1% chance is infinitely better than 0%.

And 0% is what you get when you don't ask.

Send the fucking email. 
Ask for the fucking intro. 
Flip the fucking coin.

The worst outcome? You're exactly where you are right now.

The best outcome? Everything changes.

You can't win a game you refuse to play.

What's one connection you've been too intimidated to pursue? 

Drop it below... you might be closer than you think.

Hot take: Venture Capital and Private Equity are failing most good businesses.



VC wants moonshots.

PE wants spreadsheets.

Meanwhile, thousands of profitable companies sit in the middle
too small for buyouts, too boring for hype, too real to ignore.

That’s where Venture Equity lives.

No pitch decks.

No “growth at all costs.”

No strip-and-flip nonsense.

Just real companies with real revenue that haven’t been scaled correctly
paired with operators who actually know how to build.

If your fund needs leverage to make the math work, you’re not investing
you’re engineering optics.

The next generation of enduring businesses won’t come from hype cycles or financial extraction.

They’ll come from disciplined operators compounding value quietly while everyone else chases vibes.

Most people won’t like this take.

That’s usually how you know it’s right.

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