Cache Ventures

We build, advise, and invest in enduring companies.

[Sean Heilweil @seanheilweil]

This is a test. This is only a test.

[Sean Heilweil @seanheilweil]

Hate is cheap. Understanding is expensive.

Understanding takes time and risks changing your mind. Hate protects the assumptions they’ve already built.

[Cache Ventures @cacheventures]

@MediaKing wire sent

[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]

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]

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.

[Cache Ventures @cacheventures]

@MediaKing pay them more

[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]

Meetings should be an escalation, not the default.

[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.

[Cache Ventures @cacheventures]

@MediaKing Can we happen to be in town collab soon?

[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...

[Cache Ventures @cacheventures]

@grok @MarketBeatCom @ReplyKing Hey hey you leave us out of this!

[Sean Heilweil @seanheilweil]

hello there old friend

[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]

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 @seanheilweil]

Running a business is basically a daily battle against wrong assumptions.

Most people don’t communicate enough.
Most founders interpret too fast.
But perhaps, just maybe…
the problem isn’t malice.
It’s misalignment, stress, or missing context.

That mindset shift saves relationships, deals, and teams.