Doug Bernstein

Mediocre VC Lawyer. 1988 Blue Team Color War General.

[Dan Primack @danprimack]

Introducing a $250 bill, regardless of whose face is on it, is a screaming reminder of high inflation.

[Josh Kopelman @joshk]

Beginnings Matter.

Who you are is a reflection of how you were raised. I am a reflection of how my parents raised me. And all of the founders I’ve been privileged to work with are a reflection of how they were molded by their parents.

On Mother’s Day, @firstround thought we’d give some of our founders the opportunity to acknowledge the impact their mom had on them.

@martabralic’s mom came to the US from Serbia without knowing anyone, learned English and programming languages to pick up new jobs to support the family. She gave Marta the confidence that she, too, could do hard things, like building @pomelocare.

@kareemamin's mom modeled grace under pressure (even when Kareem once crashed her car). That’s probably why Kareem has an insane ability to remain calm under pressure, which he uses every day at @clay.

@celinehalioua's mom pursued her PhD and instilled a love of research in Celine, which inspired her to start @loyalfordogs.

Happy Mother's Day!

[Liz Wessel @lizwessel]

Beginnings Matter. 

Behind so many founders are the moms who first shaped them. Happy Mother’s Day.

[Doug Bernstein @DougBernstein]

I don’t like the new #NoahKahan album. Do I owe my therapist a bonus?

[Doug Bernstein @DougBernstein]

This!

[StripMallGuy @realEstateTrent]

Explain this:

Today, instead of bringing a carryon suitcase onto the flight, I chose to bring a small backpack.

This should save space in the overhead bins, benefiting everyone, right?

Wrong.

Instead of encouraging more people to do this, Delta is doing the opposite.

They're penalizing us by requiring that our backpacks be kept on the floor in front of us, rather than allowing us to stow them in the overhead bins.

So, even though we're freeing up overhead space for everyone, we're not allowed to use it ourselves.

Make it make sense.

[Doug Bernstein @DougBernstein]

@MSolomon22 He admitted he faked it….

[Doug Bernstein @DougBernstein]

@MSolomon22 Pretending you got hit by a pitch when you didn’t isn’t cheating?

[Adam Bernstein @Bernie_044]

Was just shown The Epstein Files

[Josh Kopelman @joshk]

We just opened up applications for the Fall 2025 cohort of PMF Method, and here’s my pitch to early founders thinking about applying:

You get to spend 4 intense days with a wildly talented group of builders as you figure out if your startup idea is worth the next decade of your life while @tjack shares everything we’ve learned from 20+ years of investing in pre-PMF companies, all for free. Yes, it's free. We take 0% equity. This makes it more of an IQ test than a decision. I hope you pass the test ;-)

That’s it. Deadline is Aug 15. Can’t wait to read applications!

[Adam Bernstein @Bernie_044]

I'm gonna throw out a wildcard name for the Knicks job: Timothée Chalamet.

I doubt he'd take it, seems like he wants to keep acting, but if he wants to coach, his experience as Lisan al Gaib shows a demonstrated ability to take a long suffering group to the promised land.

[Doug Bernstein @DougBernstein]

@realEstateTrent Cheaper than getting divorced.

[Adam Bernstein @Bernie_044]

The pope went to Villanova and is from Chicago?

[Adam Bernstein @Bernie_044]

@chipotlhey “And if your generation starts blindly referring to any technological advancement as evil… good luck Charlie”

[Ramon van Meer @ramonvanmeer]

Everyone says they’d pay more for “Made in the USA.”

I tested it.

We make a $129 filtered showerhead manufactured in China. With tariffs surging to 170%, we explored reshoring. We found a U.S. supplier. Our costs nearly tripled.

I ran a clean A/B test:
👇

[Doug Bernstein @DougBernstein]

@zachweinberg You made my wife laugh; no small feat.

[Doug Bernstein @DougBernstein]

@AdamLox @StevenACohen2 Take. My. Money.

[Brett Berson @brettberson]

The best filmmakers are lifelong students of their craft. They immerse themselves in film history, analyzing the work of legendary directors and cinematographers to understand what makes a scene and film unforgettable. They break down shot composition, lighting techniques, and storytelling structures, learning not just what works, but why it works. However, they don’t use this knowledge to replicate what others have done—instead, they draw inspiration from it to forge their own distinctive style.

We believe the same holds true for building important companies. There’s no guaranteed formula or paint-by-numbers approach, but studying the greats—those who have built consequential companies before—increases the odds of creating something truly special.

That’s what The @firstround Review is all about. It’s a corner of the internet dedicated to long-form stories, written by builders for builders—open-sourcing how great startups are built, brick by brick.

If you’re passionate about startups and storytelling, we’re hiring a writer to join The Review team in SF.

Check out the job posting in the comments.

[Todd Jackson @tjack]

Big full circle moment today.

If you told me back when I was at Dropbox 10 years ago that I'd be leading my then-colleagues @jgreze’s & Tony Vincent’s $18M seed round, I would have been floored that my future self became an investor (not a VP Product or a founder again) — and I definitely would have been shocked by how big seed rounds had gotten. But I wouldn’t have been surprised that I'd jump at the chance to back Jean-Denis and Tony.

Even back then, it was clear they were destined for big things. JDG went on to become Plaid's CTO, while Tony sold his next company to Google and became a big part of their AI initiatives (on the main stage for the I/O keynote last year).

Today, they're launching @TownTaxCo — something special they've been quietly building to help SMBs tackle taxes.

Small businesses are getting crushed here. They don’t have in-house teams working year-round to minimize what they owe, so they have to go it alone or rely on overwhelmed CPAs who drop balls, cause last minute scrambles, or even straight up ghost them mid-season.

Automation has been hard to get right previously. It’s the kind of messy market most startups avoid. With a dusty industry and a hard to distribute product, it takes a team like this to get it right.

JDG is amazing technically, but he’s an atypical CTO who’s also really strong commercially — he joined us for First Round’s PMF Method last cohort, and it was cool to see how advanced his thinking already was around distribution and partnerships.

And Tony is an incredibly strong product founder with a design background and a great sense of craft — he just makes killer products.

They’ve been super thoughtful about how to rebuild tax technology from the ground up with AI. With Town, your (human) tax advisor works year-round on strategy while their AI handles all the tedious compliance work and remembers every detail about your business, year after year.

Only a few months in, they’ve already got impressive traction to show. There are 100+ businesses on board (from e-commerce shops and dental practices to startups) and they’re partnering with bookkeeping and fintech platforms to embed tax support right where owners already do their day-to-day work.

Very honored that they chose to work with @firstround, and very excited for Jean-Denis, Tony, and the whole Town team — this is just the beginning of something special.