Sam Gerstenzang
@gerstenzang
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The world's slowest incubator: @boultonwatt . Build products, teams, companies. Previously @stripe @a16z and more.
Brooklyn
Joined March 2007
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All of us living in small NYC apartments already knew it cost nothing to live in a mansion in the middle of nowhere.
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I love the idea that you could have a kid with Sergey Brin, and be like "oh, the autism was from the vaccines"
truly unhinged story.
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Insanely cool. BVP opens up their original investment memos for Shopify, Twilio, Linkedin, Pinterest and more:
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~News~ Excited to share that I’ve joined the
@Stripe
team, working on Stripe Checkout, and helping build out a team in NYC + remote 1/11
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Once you have good taste, so much of making something good is just high tolerance for grinding it out when it's still not. yet. good.
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This is my last week at Stripe. It was the best job I've ever had. Thank you to our customers and to my one-of-a-kind teammates. What an incredible company, product, culture, team. I learned so much.
I'm starting a new company – more on that soon.
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So much VC-founder discourse doesn't pass the sniff test. Like searching for "mission driven" founders.
Do you think Larry Ellison cared that much about databases? Travis about transportation? Drew about file storage?
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"When an adult reads a great book, they say 'that was a great book' and put it down.
When a child reads a great book, they say 'that was a great book' and start from the beginning again."
-Roald Dahl
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I might be the only one but I hate the PM interview question: "what product you do like and why"
I'd rather hear about a product you don't like and why it's working anyway. And would your changes move the needle. And then why it's likely those changes haven't been made already
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Slack is the worst product I use that others consider well-designed. What's yours?
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Incredible video where Travis tells the story of his first 2 startups:
* Investors withheld funding to get better terms & then sued him
* Co-founder mutiny, leaving behind IRS debt & poaching employees
* Years of by-the-teeth funding – down to 0 employees
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I've extended ~30 job offers, and still get nervous before each one. Don't feel the same about pitching investors or many other opps to be told no to my face :)
Maybe because nothing seems as rewarding and vulnerable as asking someone to spend many of their waking hours with you
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Operating well – what I learned at Stripe
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@zebulgar
You and I aren’t persecuted by MAGA today - like we would have been with the swatiska. But to deny that others rightly feel this way - and to acknowledge at the same time it is hope for others - that is wrong. How many people terrified for their lives is too many?
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Maybe start a company yourself (at least once) before saying stupid stuff like this?
Something sad about entrepreneurs who lose their risk tolerance as they get older.
Like seeing a talented artist give up their dreams for a desk job.
I’m at the age where this is happening more often in my friend group.
Same thoughts go through my head sometimes too.
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I agree with a lot of Basecamp's philosophy but with two notable exceptions:
1) Venture capital can be a useful tool.
2) To make anything great, you have to work on the weekends.
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We extended address auto-complete globally on Stripe Checkout and saw conversion increase .8% on desktop and 1% on mobile (!)
Just one of many ships that saves you time and makes you money:
And we pay your Google Maps API bill ;)
cc
@patrickc
Stripe Checkout now loads *65% faster* and now supports Stripe Climate, dynamic tax rates, and usage-based subscriptions.
And that's just the January release!
By using Checkout, teams of Stripe engineers + designers improve your payment flow every day.
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Uh, now's probably a good time to share that I'm hiring a senior/lead PM to lead mobile payments at Stripe.
Remote/NYC/SEA/SF. Required: high agency & strategy, fun to work with, experience working with API products.
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Surprisingly great feature, now live in Stripe Checkout: if a user misspells their email domain on Checkout, we make a smart suggestion to fix. becomes .
Try it live here:
Great first ship
@reddyourmind
!
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Starting second company five years later... and everything is just easier? I know more good people, make quicker decisions, know where to focus.
The hard things are still hard, but the medium things are easy. Plus every tool is now 2 to 10x better.
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Excited to finally share our funding round – "Alphabet’s Sidewalk Labs backs Umbrella, a community marketplace for boomers"
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Is there a name for the technical, non-coding skillset? Can push Zapier, Airtable, etc but aren’t deploying code.
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Craigslist's design from 1999 to 2012, presented without commentary.
http://t.co/3XQP8qaeH2
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Are you a startup who wants to integrate Stripe?
If so, we'd love to watch you do it, so we can make it better for everyone:
If you're chosen:
* $175 gift card
* I'll spend 30 minutes helping you in any way I can (product, fundraising, etc)
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Best founders unreasonably driven, but rarely because that project is their life's work: it's because they're on to something big and they have something to prove.
Almost doesn't matter what it's about, as long as it's attached to a big opportunity.
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One stat I don't see used often enough as a benchmark for VCs: number of founders who repeatedly worked with the same investors as leads.
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I feel like the Thiel Fellowship has been more successful than anyone has discussed. Would love to see a feature/review of what the fellows have gone on to do so far...
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Another good one: AWS. I get an email weekly saying they'll suspend my account for an unpaid $0.40
I once spent 30 minutes trying to figure out to how to pay and now just don't bother. *Please* suspend my account.
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The most VC-like move would be for Marc & Ben to now donate to Harris now that the momentum has shifted, without telling Trump. Got to back the winners.
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As I've gotten older, it's been amazing to realize exactly how much of people's behavior is driven by fear. Most decisions by most people, often barely below the surface.
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Guide for reaching out:
1. Share context on who you are
2. Share context on what I can do to help
3. Consider asking directly in email instead of asking to meet.
It seems kind of... rude.. to have to say this. But you'd be surprised how often someone misses 1 or 2.
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This is bonkers. I wonder how much revenue they just turned off.
Today we're making GitHub free for teams of unlimited size, for private and public work. 🎉
Every developer on earth should have access to GitHub, and price shouldn't be a barrier.
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Vision Pro:
@benedictevans
with the clearest, most nuanced take on what the future might hold, as always.
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In 1932, the founder of Panasonic said his company’s 250 year goal was “the elimination of poverty around the world” - that the role of the manufacturer in society was to not just enrich its owners, but to lift its society in to wealth.
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Amazing how four well-sourced articles come out about how Jony Ive has been less involved at Apple for years, immediately after he resigns.
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Startup 'studios' suggest an industrialization to the creation process which I'm not sure holds.
The right model might be more like an artist colony. Some shared resources, sure, but also a bit of madness.
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Three types of VCs:
* Those who are late and apologize sincerely
* Those who are late and apologize insincerely
* Those who are late and don't apologize
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I bet Carta has the best data on speed and severity of startup layoffs.
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"If You’re Offered a Seat on a Rocket Ship, You Don’t Ask What Seat. You Just Get On.” -> standard but terrible advice.
Real advice: don't let your ego get in the way. Fastest way off a rocketship is with bad boss + terrible (for you) role.
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I wished some email newsletters went straight to my Instapaper and then I realized I had just re-invented RSS.
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I think there's something to the fact that both Honey and Plaid didn't have structural advantages, just good execution. One was "just a Chrome extension", the other "just some scrapers". And yet compounded with some good wrappers, worth a lot.
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While Joi Ito and the Media Lab deserve what’s coming re: Epstein, it’s bizarre how we completely let go the (much larger) donations from Saudi Arabia, and SA’s SoftWashed funding of tech generally.
A far more systematic opression, but “further away” and without specificity.
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First time back in SF, after 1.5 years. I’ve missed it. I love NYC and I love LA but the Bay Area has such a special energy and set of people.
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~4 years later, seems pretty clear that Uber has no network effect.
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Within a big company, it's your network within the company that allows you to get stuff done. In startups, it's your network outside of the company.
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Few things as humbling as revisiting old writing you once thought was good.
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I've owned and read some interesting corporate histories: Home Depot, Mcdonalds, Walmart, Sears (1989), Disney, MSFT (multiple), RIM – what others should I read? cc
@kevinakwok
@benthompson
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Moving back to Brooklyn today (from LA, not Miami, my goodness). See y’all soon.
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Best example of network effects is LinkedIn, whose product continues to be an unbelievable mess and yet still extremely difficult to unseat.
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We started using Rippling for one of our companies (and had very high hopes) and have been pretty disappointed. Whenever I want to add a $10/month module, I have to spend 30 minutes with a sales person. On the other hand, support issues take days to resolve. Some simple stuff
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@danprimack
Feels worth mentioning how he dumped LPs and staff for last external fund. Hard to overcome that.
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We're building an inclusive, diverse, humble, talented team on Stripe Checkout, and we're looking for full stack engineers and a product designer, based in NYC, SF, or remote.
Why join Checkout?
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If you're not looking forward to work tomorrow, we just opened an EM role for an experienced candidate that is a huge opportunity for the right person
Brand new
@stripe
product, *huge* impact, backend/frontend. Pro/con, we'll work together. Shoot me an email sgerstenzang@
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One of the companies I most admire: IAC
* Long tenure of employees and proven training ground of incredible leaders (Dara + many others)
* Diverse portfolio of built and acquired brands
* Mix tremendous product + business acumen with intellectual honesty
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@eriktorenberg
I’m not sure if that’s actually what Kara is saying. Elon can be a jerk who has contributed incredible things to society. That’s not complicated. Both things can be true, and doing good things for society doesn’t make him not a jerk.
You can still prefer that Elon not being a
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I get emails from VCs daily asking to meet. When I say we're not fundraising (exceptions are friends and known thoughtful people), they say they like to meet ahead of fundraise.
But that's what *every* investor says. And it's not a company-oriented view. We'll meet when it
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Some personal news: I’ve transitioned into an advisory role at
@askumbrella
! I couldn’t believe more in the opportunity, the company, and what
@leullman
and co are doing. I’ll still be around as Umbrella’s most ardent supporter. More on what’s next for me soon.
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So proud of the team: in <12 months since serving our first customer, we raised a Series A in the toughest climate in years.
Why? Because we've built a great, fast growing business that's changing lives and enabling entrepreneurs in a massive, fast growing market.
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Things I thought would a bigger deal in adulthood: ordering of the planets, quick sand, writing in cursive, not having a calculator.
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Wow. Pagerduty filed for IPO. My friends at
@A16Z
own >18%, and especially impressive for
@mcgd
who led the seed and owns >5%.
Congrats all –
@askumbrella
just became customers this week.
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Dubai had 60k people & no electricity in 1960. Incredible. From Daniel Brook's excellent "A history of Future Cities"
http://t.co/bNJDIv1ipY
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I've been learning a lot about 'product marketing' these last few weeks. Here are the three best articles I've found, all (maybe no surprise) from
@firstround
:
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Holy cow. This is a big deal: no more brokers’ fee in New York.
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I'm looking forward to when the Minecraft children start creating things for the rest of us
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One of the most astonishing things to me is that there isn’t a VC firm focused on consumer insights, in a deep, people-driven way.
Most consumer VCs follow growth, which should work eventually. But look at the intersection of US demographics and senior GPs - whole lot missing.
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Enjoying watching Jason Fried’s favorite basketball player, Michael Jordan, argue for work-life balance in The Last Dance.
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Just registered a new domain :) Favorite this tweet if you want to get early access when we launch in 3 weeks.
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Neat Chrome extension that will show local library availability while browsing Amazon:
http://t.co/nJvkVgtygG
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In a few years, it's going to be interesting to "re-integrate" folks who spent formative part of their careers in crypto. Some transferable skills...but a whole bunch of pattern recognition in the wrong areas.
And yes, many of my smart friends work in crypto (~30%?)
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I love the entrepreneurial creative energy and investment in others of David Chang.
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Thrilled to share Boulton & Watt's second company: Meadow Memorials, a contemporary, transparent, and hospitality-driven take on the traditional funeral home.
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👋 My team is hiring an engineering manager for Stripe Checkout.
We're 8 engineers today and will be growing rapidly – this is a key entrepreneurial opportunity to be a part of building out the NYC office and at the center of a pivotal product for
@Stripe
.
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A fun thing to see would be a site that randomly rotated through venture funds’ mission statements and had you guess which venture fund it was for.
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Reading Charles Schwab's memoir, and a few things stood out:
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It’s my birthday! Reading this am, zen meditation for next 3 hours, lunch and Knives Out with family, working, and dinner with my girlfriend. Pretty perfect day.
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Moxie just passed $1m annual net revenue 7 months after launch. A lot more to do - but good incremental milestone.
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I'm surprised there isn't a better IRC-like app to chat online with non-company people.
Slack clearly isn't meant for inter-company, and there's so much you could do.
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@zebulgar
Right - my point is a symbol like the swastika can represent both pride *and* terror. And so too for the MAGA. There isn’t in a different of type, only degree.
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A small detail I hate: when you authorize a free download from the Apple App Store, there’s a brief moment it displays “processing payment”.
So lazy.
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If my math is right, the founders of Smile Direct Club will own ~64% post-IPO. Astonishing for a consumer company.
(It helps when your dad is serial entrepreneur who finances and then runs the company.)
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Debunking the Myth of the Job-Stealing Immigrant
http://t.co/naBif8U9nh
http://t.co/2Zae73wIfC
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If I request the meeting, I’m traveling to you.
If you’re paying me, I’m traveling to you.
Otherwise, you’re traveling to me.
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Favorite film genre: beautiful, good music, melancholy, simple plot.
Lost In Translation, Diving Bell and the Butterfly, Boyhood, A Single Man, Her.
Any recs?
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For well-paid, high pressure careers I think this going to become increasingly common. Seeing a lot of this in tech right now. “She Took a Two-Year Break in Her Career. Now She’s CEO.”
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One of the things I’m having to remember speaking to people outside of Stripe is how much context they’re missing on how ambitious we are.
Stripe does a good job communicating externally, as far as these things go. But inside it’s so much (and realistically) bigger.
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The worst named transit stop ever is probably the one named “Newark Penn Station” that is between “Newark Airport” and New York’s “Penn Station”.
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There's a narrative component here as well, that speaks to both anchoring in global trends and recruiting. It's easier to "expand the internet GDP" than "deal with archaic credit card bullshit on behalf of Salesforce".
If there isn't a larger story, it's probably a smaller opp.
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Venture capitalists who want to meet new companies should stop asking "how can I help" and instead ask "who can I introduce you to?"
VCs who introduce us to great candidates immediately jump to the top of our list.
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95% of the time someone is slow to reply to an email of mine, it’s because they’re busy.
But 5% of the time it’s because they hate me. And that’s what I spend all my time worrying about.
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Mercury is such a great product. We operate 3 companies off of it, and it just keeps getting better. Have now had experience multiple times where I discovered a feature exactly where it should be that just made my life easier in an unexpected way. Thanks
@immad
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