Sean Heilweil

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

[Sean Heilweil @seanheilweil]

“Mom, how did you get so rich?”

“Your father uprooted our entire life and moved us to LA for HIS dream. I took a job at a tiny unprofitable company recruiting welders for $28 an hour. The welders built reusable rockets."

[Sean Heilweil @seanheilweil]

I’m up 8,500% today on $SPCX

[Sean Heilweil @seanheilweil]

Bad take incoming…

Polsia is the spiritual successor to https://t.co/Hhqc3gVYgY.

But where @tewy built something playful and iconic, @Bencera is building something dystopian and fraudulent.

[Sean Heilweil @seanheilweil]

Discipline is a story successful people tell after the fact.

They weren't disciplined. They just wanted it so badly the work stopped feeling like work.

You can't teach that.
So they sell you the playbook instead.

[Sean Heilweil @seanheilweil]

Jack of all trades. Master of one: pissing off strangers on the internet.

[Sean Heilweil @cacheceo]

@MediaKing @sodacitysimpson and Nick's?

[Sean Heilweil @seanheilweil]

The nicest person in the room is usually the most dangerous.

Not toxic dangerous. Dangerous like they already know exactly what they'll tolerate, and you won't see the line until you've crossed it.

Quiet operators don't yell. They set clear expectations, give you every chance to meet them, and move on without drama when you don't.

Don't confuse patience for permission.

[Sean Heilweil @seanheilweil]

Spent two weeks blocking my co-founder from shipping a website she vibe coded.

My excuse? Meta descriptions, sitemaps, analytics...
a checklist dressed up as experience.

She finally told me
"NO, we don't work this way together."

She was right.

If your pattern recognition is preventing someone else from building theirs, you're not a mentor. You're a bottleneck with a title.

[Sean Heilweil @seanheilweil]

"If you don't have a move, don't make one."

I said this to a friend months ago. Barely remembered it. She told me this week it's the best advice I've ever given her.

That's how the most useful ideas work. They don't arrive in frameworks or keynotes. They arrive as throwaway lines that quietly become load bearing walls in how you operate.

But here is what strikes me about that line now that I am sitting with it...

[Sean Heilweil @cacheceo]

@realEstateTrent you know you could just move right?

[Sean Heilweil @seanheilweil]

At 17 I had a 1.6 GPA.

My HS principal looked me in the eyes and told me I wasn't good enough to flip burgers at McDonald's.

She was probably right.

But that's the thing about being counted out...

It gives you something most people never find:

Rage with a direction.

The most dangerous person in any room is the one with something to prove.

Bet on the fury.

[Sean Heilweil @seanheilweil]

I closed a $60K deal by playing sudoku on linkedin.

I'm not joking.

Here's what it taught me about B2B sales👇🧵

[Sean Heilweil @seanheilweil]

I have everything to sell you.

[Sean Heilweil @seanheilweil]

I went to Coachella once. Lasted 13 minutes. Gave my wristband to Cody Simpson and drove back to LA.

[Sean Heilweil @seanheilweil]

Most people don’t have a content problem.

They have an ego problem.

They’re not scared the post will flop.

They’re scared people will see them trying before they look impressive.

That’s why the ones willing to be awkward in public for 90 days usually win.

[Sean Heilweil @seanheilweil]

this guy is worth over $200M...

this is his idea of having a personal driver

doordash is his idea of having a personal chef

is this a dave ramsey meme account?

[Sean Heilweil @cacheceo]

@seanheilweil Update: someone reported this thread.

That's fine.

You know what you can't report?

My Stripe dashboard.

[Sean Heilweil @cacheceo]

@seanheilweil Just got a DM from a guy who said this "destroyed his faith in humanity."

Brother your faith in humanity was a liability on the balance sheet.

I just helped you write it off.

You're welcome.

[Sean Heilweil @seanheilweil]

All of you insist on playing life on hard mode.

Here's an easy business idea almost no one is executing on.

Took me 3 years to figure this out. Sharing for free. You're welcome.

Become the GTM partner for a really niche thing.

I'm talking HYPER niche.

So niche the TAM is "marriages on the brink."

That's not small. That's HALF OF AMERICA.

Blue ocean, baby.

Step 1: Social engineering.
Step 2: The Venmo public timeline.

"$47.50 - dinner you ruined"

"$200 - YOUR mother's gift"

"$12 - ???" (this one's always the worst sign)

These aren't transactions. They're intent signals.

Scrape their profiles.

Enrich with contact data.

Cross-reference with Zillow to see who just bought a house they can't afford together.

Layer in Instagram activity. Are they posting separately? Not tagging each other?

GOLD.

Now you run outbound.

Email. DM. Organic. Paid.

Target BOTH husband AND wife.

With different messaging.

At different times.

Husband gets "Protect your assets."

Wife gets "You deserve better."

This is called ✨personalization✨

"But isn't this unethical?"

Brother I'm not CAUSING the divorce.

I'm providing market liquidity for an inevitable outcome.

I'm basically a therapist. A therapist who scales.

Sell the leads to couples therapists → $50 CPL

Sell the leads to divorce attorneys → $300 CPL

Sell the leads to BOTH → let them fight for the customer

You've created a marketplace.

You're basically Uber now.

Phase 2: Vertical integration.

Start your OWN divorce mediation service.

Now you're capturing demand you created.

This is what McKinsey calls a "flywheel."

Phase 3: Expansion.

Launch a dating app.

Market it exclusively to your divorced customer base.

They already trust you.

You've been with them through their hardest moment.

That's BRAND LOYALTY you can't buy.

(well, you did buy it. but still.)

Phase 4: Exit.

Sell the whole thing to a private equity firm who "sees the vision."

They won't.

But they'll buy it anyway because you have MRR.

Buy Lambo.

Buy fake penthouse in Brickell. (Real ones are for closers who did this at scale across multiple metro areas.)

Rent it out on Airbnb when you're "traveling for business."

The business is posting from hotel lobbies.

This is not financial advice.

This is not legal advice.

This is not ethical advice.

This is not advice.

I am not a person. I am a meme.

Live life.

[Sean Heilweil @cacheceo]

@seanheilweil Some of you are dumb mad reading this.

Because it's you.

That's fine.

Anger is just unmonetized attention.

I'll wait.