Cole Striler

founding engineer

[JD Ross @justindross]

In 2014, I took on real estate brokers w/ my company Opendoor

In 2023, I took on the $500B insurance broker industry

Now we protect $50B in revenue across 1000+ clients

Don't be deceived by insurance brokers. I’ll personally show how we can help: [email protected]

[Cole Striler @colestriler]

My brother recently graduated from Air Force SERE school and told me about a concept they teach there called “quitting by action.”

He said many people who fail aren’t incapable. They quit internally, but stick around until they get kicked out because it’s easier to say “I didn’t make it” than to admit “I quit.”

This applies to work, relationships, and almost everything else.

Either be all in or be out. But don’t quit by action.

[Cole Striler @colestriler]

So great is man’s hunger for truth that he will gladly devour a lie, provided it has the taste of certainty.

[Cole Striler @colestriler]

Spec review is the new PR review.

[JD Ross @justindross]

Not exaggerating: WithCoverage's growth team's calendar is booked back-to-back until mid July... but old school AEs won't succeed here.

I'm hiring if you are:
- IQ + EQ
- Curious + Kind: every client is a puzzle to solve
- HUSTLE

Great comp + equity. DM me

[JD Ross @justindross]

WithCoverage Engineering is < 10 people

Huge opportunities to own scope across Growth, Platform, and Product. NYC, in person. Doubled team since Jan, Cashflow Positive in April

You:
- Experienced with a history of excellent work, OR
- Young, smart & ambitious
- DM/Reply!

[Cole Striler @colestriler]

ChatGPT can write code, pass the bar exam, and explain quantum physics but it still can't convert a .heic to .jpeg

[Cole Striler @colestriler]

Modern anxiety often comes from running tribal hardware in a planetary-scale software environment.

[Cole Striler @colestriler]

@derekkohn @justindross @CuriousClub Been great working with you!

[Cole Striler @colestriler]

@goodquestionai The biggest bottleneck is now code review

[Cole Striler @colestriler]

@TheVixhal I thought that until I read JIRA

[Cole Striler @colestriler]

Two years ago, I got introduced to JD.

I knew nothing about insurance. Turns out it's a $300B+ market that still runs on emails and PDFs. Brokers are incentivized to sell expensive policies. Customers end up overcharged and underinsured at the same time.

The pitch: use AI to give every business the kind of risk management that only Fortune 2000 companies could afford. I wanted in.

We've spent the last two years building tools that let us operate differently than any other brokerage. AI that audits policies line by line. Systems that catch what brokers miss. Software that replaces the endless manual work this industry runs on.

This is how we save customers up to 30% while actually improving their coverage.

Today we announced our $42M Series B led by Sequoia and Khosla.

Really proud of what we've built. Hiring engineers if you want to come break stuff with us.

[Bill Perkins (Guy) @bp22]

@big_duca Not useless a gun is much more useful in a navy's seals hands then some random shooter. You're the navy seal

[Cole Striler @colestriler]

Context is king.

[Cole Striler @colestriler]

We're hosting a dinner in NYC tomorrow for engineers & founders. 15 spots. Come meet interesting people and share ideas. DM me.

[Cole Striler @colestriler]

Your website / app should be a generator of information that tells you what to build next.

[Cole Striler @colestriler]

Complexity implies lack of understanding.

[Cole Striler @colestriler]

NextJS + tRPC is incredible. Farewell Supabase.

[Cole Striler @colestriler]

@_nicolealonso It's surprisingly decent coffee

[Cole Striler @colestriler]

@_mattwelter @0xHendrix If you are constantly in a state of anxiety, you are almost certainly ignoring some truth that you don't want to hear the answer to.

I think @0xHendrix's comment is worth considering.