investing @BananaCap_ podcasting @ThePeelPod (sign-up for emails below)
Ann Arbor, MI DM’s open
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We got people saying you need $1B+ to do Seed investing
Meanwhile @credistick explains how your risk can actually go up if you raise too much money
Half of venture says capital is a moat.
The other half says huge rounds make your startup more risky.
@credistick on what you really sign up for when a mega-fund writes a big check:
"Their value prop, part of it at least, is that they will be less price sensitive when they invest. So they will give you much more money on much more friendly terms potentially.
The downside of that is the growth that you kind of obligated to deliver as a part of getting that huge check is way higher. The stakes of failure are higher. The risk you're taking on as a company by accepting that much money is much greater.
What should happen through a startup's life is as they develop, the risk slowly goes down. You end up raising these huge rounds and your risk shoots back up to the top again, and then you need to work it down again.
For some companies in some categories, it's the right move.
But for many it's probably not."
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Really interesting guest data on the biggest venture-related podcasts
This is telling me @ThePeelPod probably leans more Founders and VC's, less experts/media than the others
This was a fun one. Had the team look at who our favorite venture pods are having on.
20 shows, over 4,500 guest appearances.
I think it’s really cool how Jack consistently gives other investors his platform and lets us hear how they think. Harry and Patrick, too.
Great at what they do. Generous with the spotlight. 🫡🔥
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I don’t care if it’s the mother of all bubbles, $2T of AI CapEx was worth it just for this
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Ken Griffin says AI is "almost certainly" in a bubble.
Back in 2024, @loganbartlett of @Redpoint told me how VCs actually play bubbles:
"From a pure incentive standpoint, your job would be to lean into it. Raise as much as you can, deploy as much as you can.
If you're right, you get to say, 'I told you so.' If you're wrong, you justify it as the mania of the markets. You hope enough people did it that it's forgivable.
That's what happened with the internet in '99, 2000, 2001. That's what happened with crypto. And it feels like that's what's happening with AI in some ways as well.
If everyone is saying something is true, and it's getting covered on CNBC on a daily basis, it's generally something I want to stay away from.
But bubbles lay infrastructure for enabling technologies. The internet was a bubble, and no one would argue it wasn't ultimately correct. It just wasn't a great investment at the time.
If you were in Google, eBay, PayPal, Amazon, you did very well. If you were in Lycos or Ask Jeeves or Friendster, you got totally wiped out.
Just because you're right on the tech doesn't mean you're right on the opportunity."
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We got people saying you need $1B+ to do Seed investing
Meanwhile @credistick explains how your risk can actually go up if you raise too much money
Half of venture says capital is a moat.
The other half says huge rounds make your startup more risky.
@credistick on what you really sign up for when a mega-fund writes a big check:
"Their value prop, part of it at least, is that they will be less price sensitive when they invest. So they will give you much more money on much more friendly terms potentially.
The downside of that is the growth that you kind of obligated to deliver as a part of getting that huge check is way higher. The stakes of failure are higher. The risk you're taking on as a company by accepting that much money is much greater.
What should happen through a startup's life is as they develop, the risk slowly goes down. You end up raising these huge rounds and your risk shoots back up to the top again, and then you need to work it down again.
For some companies in some categories, it's the right move.
But for many it's probably not."
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Last year we talked through the data in a dozen academic papers on VC + startups if you want to nerd out on the full thing thespl.it/p/untold-startup-l…
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What's the best example of a team with the highest empowerment culture today?
Stripe’s 1st employee @darraghbuckley on how it held its high agency culture longer than Facebook, Google, or Microsoft:
"I enjoy working in high-empowerment cultures, and with people who do too. High empowerment means the ability to wander and make the change you need to build the product.
There are prerequisites. You have to hire well. And you have to trust the people you hire. And trust that they trust you to go effect that change.
It also means you can't silo too strictly. You let a compliance person wander into engineering, and an engineering person into compliance. More than allow it, you expect it.
Stripe was very good at this for many years. Stripe maintained it to a higher headcount than Facebook did. Facebook maintained it higher than Google. Google higher than Microsoft.
I'd hope at Increase we can maintain it to an even larger headcount."
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I am open to receiving $10,000 or even $10,000,000 if anyone is interested
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New @ThePeelPod talking data centers in space dropping soon
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Turner Novak 🍌🧢 retweeted
.@IncreaseDev moves $500B+ per year with a 33 person team.
CEO @darraghbuckley on how they do it:
"It's fascinating how much you can scale when you're building on top of the Federal Reserve, when you don't have those traditional abstractions.
A lot of the operational work in financial services is adjusting for the abstractions. Figuring out how to get around them, or what happens when things leak through.
An example from Stripe: ACH return allocation. You send a transfer, it can't reach the account, it gets bumped back, and now you need to know which transfer bounced.
Sounds trivial. But the identifier you're supposed to use, the trace ID, is 15 characters, and you don't even get all of them, so they repeat. They're not actually unique to you.
So you build heuristics to map it back. Then things fall out of the queue, so you build a team to handle those. You're writing software to make up for the lack of capability in the original software.
That's reasonable, to a point. At that point, the right thing to do is go back and fix the fundamental problem. Hence why we built Increase."
New @ThePeelPod with @darraghbuckley
From employee #1 at Stripe, to starting @IncreaseDev and moving $500B per year with 33 people.
And they just bought a bank.
He talk how to acquire a bank when they can't tell you they're for sale, why putting an API on a bank is like "strapping a jet engine to a go-kart", why The Fed actually has great technology, the overnight build that turned on Stripe’s first dollar of revenue, why Patrick and John Collison sprinted everywhere, and why you want your banker to be bored.
Watch here + links below
0:00 Stripe's 1st employee bought a bank
1:38 Fixing the stone in his shoe building Stripe
7:59 Banking looks like 2010 payments
11:11 Merging two layers into one, just like Stripe
14:52 Why he finally bought the bank
16:26 How do you actually buy a bank?
20:20 The first bank that got away
22:04 Why banks can’t chase new fads
25:26 Compliance as code, from day one
29:46 Talking straight to the Federal Reserve
32:19 The Fed migration that nobody noticed
33:50 The missing last mile of banking
35:44 Getting customers to switch
38:23 The challenger sales model
40:33 What customers use Increase for
41:48 How Ramp's bill pay works
42:37 $500B a year with 33 people
45:31 Hiring for a high-empowerment culture
47:08 Growing up with the Collisons
50:27 150 test cases in one night
54:23 What really made early Stripe work
57:07 Why Patrick and John sprinted everywhere
1:00:00 “You're not in payments, you're in fraud”
1:02:31 Where AI hits a wall on fraud
1:05:08 Giving payment cards to AI agents
1:09:27 Use boring technology widely
1:11:37 You want your banker to be bored
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I invested in @artie_labs three years ago and they've been consistently early and right.
Really fun learn from them as execute and build out the essential plumbing for every AI product that makes real-time decisions.
Every single customer told Jacqueline Cheong (@JacquelineSYC19) they didn’t want the feature. She built it anyway. Six months later, 40% of them had turned it on.
She’s the co-founder and CEO of @artie_labs, which moves data between databases in real time: the unglamorous plumbing that lets AI agents reason over what’s happening now, not what happened yesterday.
We got into:
•Building the feature customers said they didn’t want
•Founding a company with your spouse (and why she’s loud about it)
•Why her whole team sees the revenue and burn numbers
•Why she stopped watching the metric and started watching the inputs
•Why real-time data is the layer AI agents actually need
𝐓𝐈𝐌𝐄𝐒𝐓𝐀𝐌𝐏𝐒
(00:00) Transamerica, and Why This Spot
(02:00) What Artie Actually Does
(05:00) Why Real-Time Data Is Hard
(08:00) The AI Agent Angle
(12:00) The History Table Everyone Said No To
(18:00) Founding a Company With Your Husband
(24:00) Radical Transparency With the Team
(30:00) The “Working With Me” Doc
(34:00) Focus on Inputs, Not the Score
(38:00) The Wedding Cake Metaphor
This is a @Composio “Agents at Work” podcast, where I chat with founders building the next leap of AI.
Follow for more :)
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Turner Novak 🍌🧢 retweeted
Stripe’s 1st employee @darraghbuckley on the wave of community banks that chased fintech and blew up:
"Around 2010, a bunch of community banks chased fintech partnerships. They saw it as a growth mechanism, and a lot of them didn't have the capability or capacity to do it safely and soundly.
Choose your directions carefully. See where you have a differential advantage based on what you're already good at.
Purposefully wander. But don't chase the next fad."
New @ThePeelPod with @darraghbuckley
From employee #1 at Stripe, to starting @IncreaseDev and moving $500B per year with 33 people.
And they just bought a bank.
He talk how to acquire a bank when they can't tell you they're for sale, why putting an API on a bank is like "strapping a jet engine to a go-kart", why The Fed actually has great technology, the overnight build that turned on Stripe’s first dollar of revenue, why Patrick and John Collison sprinted everywhere, and why you want your banker to be bored.
Watch here + links below
0:00 Stripe's 1st employee bought a bank
1:38 Fixing the stone in his shoe building Stripe
7:59 Banking looks like 2010 payments
11:11 Merging two layers into one, just like Stripe
14:52 Why he finally bought the bank
16:26 How do you actually buy a bank?
20:20 The first bank that got away
22:04 Why banks can’t chase new fads
25:26 Compliance as code, from day one
29:46 Talking straight to the Federal Reserve
32:19 The Fed migration that nobody noticed
33:50 The missing last mile of banking
35:44 Getting customers to switch
38:23 The challenger sales model
40:33 What customers use Increase for
41:48 How Ramp's bill pay works
42:37 $500B a year with 33 people
45:31 Hiring for a high-empowerment culture
47:08 Growing up with the Collisons
50:27 150 test cases in one night
54:23 What really made early Stripe work
57:07 Why Patrick and John sprinted everywhere
1:00:00 “You're not in payments, you're in fraud”
1:02:31 Where AI hits a wall on fraud
1:05:08 Giving payment cards to AI agents
1:09:27 Use boring technology widely
1:11:37 You want your banker to be bored
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Turner Novak 🍌🧢 retweeted
Stripe’s 1st employee @darraghbuckley on their overnight sprint that turned on the first dollar of revenue:
"One of the most meaningful things I learned early was how much a small, empowered team can get done.
We got on a call with a partner to work through our first product. The person in charge of certification said the next date was six weeks out.
In startup world, six weeks might as well be ten years.
So someone asked, is there anything sooner? And they said, “well, there's tomorrow at 10am. But you won't be ready.”
There was a pause as everyone looked around the table. We said, “sign us up”.
We hung up with 18 hours to do 150 test cases. One of us started at the top, one at the bottom.
We worked through the night. What do you do after test case 36? Test case 37.
Around 8am, to talk to the certification service, we needed an old plain telephone connection. So I ran to Fry's Electronics in South Bay right as it opened.
By 11:30 we'd passed the test. They said they'd never seen anyone certify this fast. We turned on our first live transactions.
That's the enjoyment of startups. Not doing it alone, but sharing that stress and struggle with a group dedicated to helping each other learn and grow."
New @ThePeelPod with @darraghbuckley
From employee #1 at Stripe, to starting @IncreaseDev and moving $500B per year with 33 people.
And they just bought a bank.
He talk how to acquire a bank when they can't tell you they're for sale, why putting an API on a bank is like "strapping a jet engine to a go-kart", why The Fed actually has great technology, the overnight build that turned on Stripe’s first dollar of revenue, why Patrick and John Collison sprinted everywhere, and why you want your banker to be bored.
Watch here + links below
0:00 Stripe's 1st employee bought a bank
1:38 Fixing the stone in his shoe building Stripe
7:59 Banking looks like 2010 payments
11:11 Merging two layers into one, just like Stripe
14:52 Why he finally bought the bank
16:26 How do you actually buy a bank?
20:20 The first bank that got away
22:04 Why banks can’t chase new fads
25:26 Compliance as code, from day one
29:46 Talking straight to the Federal Reserve
32:19 The Fed migration that nobody noticed
33:50 The missing last mile of banking
35:44 Getting customers to switch
38:23 The challenger sales model
40:33 What customers use Increase for
41:48 How Ramp's bill pay works
42:37 $500B a year with 33 people
45:31 Hiring for a high-empowerment culture
47:08 Growing up with the Collisons
50:27 150 test cases in one night
54:23 What really made early Stripe work
57:07 Why Patrick and John sprinted everywhere
1:00:00 “You're not in payments, you're in fraud”
1:02:31 Where AI hits a wall on fraud
1:05:08 Giving payment cards to AI agents
1:09:27 Use boring technology widely
1:11:37 You want your banker to be bored
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Turner Novak 🍌🧢 retweeted
Stripe’s first employee Darragh Buckley reveals Patrick and John Collison literally sprinted while unloading Ikea furniture, and says their sense of urgency was embedded in Stripe’s culture
“As is the tradition of all startups who first get their office, you arrive into the office and the place is empty. Great, what are we going to do? Ikea trip. Jump in the car to Ikea, get six of the cheapest desks and cheapest chairs you can get, put them back in the car and drive back to the office.
“You’re unloading the car: pick up a box, put it down, you walk back to the car. That’s not what John and Patrick do. They pick up the box, walk into the office, put it down and sprint.
“Me as observer, I’m like: ‘Did we park illegally? Did I miss something? Why are you running?’ They just always have this sense of urgency. There’s always: ‘We can just do it faster. Why would we not just do it faster?’
“If you’re in an environment where someone else is running, are you going to be the one person who’s not running? Of course not. You’re going to run too. Not in an obnoxious way, not in an ‘I’ll race you, and if you’re slower than me I’ll rub it in your face’ way. It very much is: ‘This is all of us here together doing this. Get there faster.’
“The cultural prevalence of the importance of urgency—John and Patrick are fantastic at creating it. It’s not an obnoxious, ‘Why haven’t you done it yet?’ It’s just: ‘Why wouldn’t we do it now?’ Given in a very friendly, pleasant—but, boy, you’re going to want to keep moving—way.”
New @ThePeelPod with @darraghbuckley
From employee #1 at Stripe, to starting @IncreaseDev and moving $500B per year with 33 people.
And they just bought a bank.
He talk how to acquire a bank when they can't tell you they're for sale, why putting an API on a bank is like "strapping a jet engine to a go-kart", why The Fed actually has great technology, the overnight build that turned on Stripe’s first dollar of revenue, why Patrick and John Collison sprinted everywhere, and why you want your banker to be bored.
Watch here + links below
0:00 Stripe's 1st employee bought a bank
1:38 Fixing the stone in his shoe building Stripe
7:59 Banking looks like 2010 payments
11:11 Merging two layers into one, just like Stripe
14:52 Why he finally bought the bank
16:26 How do you actually buy a bank?
20:20 The first bank that got away
22:04 Why banks can’t chase new fads
25:26 Compliance as code, from day one
29:46 Talking straight to the Federal Reserve
32:19 The Fed migration that nobody noticed
33:50 The missing last mile of banking
35:44 Getting customers to switch
38:23 The challenger sales model
40:33 What customers use Increase for
41:48 How Ramp's bill pay works
42:37 $500B a year with 33 people
45:31 Hiring for a high-empowerment culture
47:08 Growing up with the Collisons
50:27 150 test cases in one night
54:23 What really made early Stripe work
57:07 Why Patrick and John sprinted everywhere
1:00:00 “You're not in payments, you're in fraud”
1:02:31 Where AI hits a wall on fraud
1:05:08 Giving payment cards to AI agents
1:09:27 Use boring technology widely
1:11:37 You want your banker to be bored
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Turner Novak 🍌🧢 retweeted
Stripe’s 1st employee @darraghbuckley and @IncreaseDev founder gives his AI agents their own bank account and payment card.
How it works:
"I have agents wandering the world doing things for me, and I want them to be able to economically interact. I want them to be able to pay.
Right now I'm traveling to San Francisco, so I need to send flowers home, thanking my wife for being with the kids. I can just set the agent on that task.
The flower shop already has a checkout. The agent needs to enter 16 digits on the site. It doesn't need crypto
So I give my agents payment cards. They have their own bank account. And if they need more, they ask me. “I went through the $100 you gave me, can I have more?”
The point is I'm not sitting in the synchronous approval loop for every transaction. It picked the thing. If I had to go enter the card details, it would time out and we'd spend forever trying to sync schedules.
It's like giving an employee a charge card. Here's what you can spend, here are the rules. The control plane is simple: it can only spend what's in its account, and it asks for more when it runs out."
New @ThePeelPod with @darraghbuckley
From employee #1 at Stripe, to starting @IncreaseDev and moving $500B per year with 33 people.
And they just bought a bank.
He talk how to acquire a bank when they can't tell you they're for sale, why putting an API on a bank is like "strapping a jet engine to a go-kart", why The Fed actually has great technology, the overnight build that turned on Stripe’s first dollar of revenue, why Patrick and John Collison sprinted everywhere, and why you want your banker to be bored.
Watch here + links below
0:00 Stripe's 1st employee bought a bank
1:38 Fixing the stone in his shoe building Stripe
7:59 Banking looks like 2010 payments
11:11 Merging two layers into one, just like Stripe
14:52 Why he finally bought the bank
16:26 How do you actually buy a bank?
20:20 The first bank that got away
22:04 Why banks can’t chase new fads
25:26 Compliance as code, from day one
29:46 Talking straight to the Federal Reserve
32:19 The Fed migration that nobody noticed
33:50 The missing last mile of banking
35:44 Getting customers to switch
38:23 The challenger sales model
40:33 What customers use Increase for
41:48 How Ramp's bill pay works
42:37 $500B a year with 33 people
45:31 Hiring for a high-empowerment culture
47:08 Growing up with the Collisons
50:27 150 test cases in one night
54:23 What really made early Stripe work
57:07 Why Patrick and John sprinted everywhere
1:00:00 “You're not in payments, you're in fraud”
1:02:31 Where AI hits a wall on fraud
1:05:08 Giving payment cards to AI agents
1:09:27 Use boring technology widely
1:11:37 You want your banker to be bored
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Turner Novak 🍌🧢 retweeted
.@IncreaseDev founder @darraghbuckley on why putting an API on a bank is like strapping a jet engine to a go-kart:
"You can strap a jet engine to a go-kart. You'll promptly find a wall.
The money movement has to be right. But how it interacts with compliance is just as important.
And it's very useful if that's not a post-hoc tag-on. You want to embed the compliance regimes as code early. Which means engineers who are comfortable reading the source docs for the regimes, and compliance people who are comfortable in the engineering.
Take the travel rule. Certain data has to travel with a wire above a $3,000 threshold. Build that into the wire system from the start, instead of discovering it in your first audit and bolting it on.
There's this sigh of relief during an examination, when you pull the data and it's all correct. You should make that sigh of relief asymptote to zero. The way you get there is by running the examination on yourself, more and more often.
When we built engineering products, we built a test battery so a new version wouldn't deploy unless the tests passed. Do the same with compliance, and you help yourself a lot."
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Turner Novak 🍌🧢 retweeted
Why the best founders are like Moses (@bznotes):
"The people who are very good at painting a picture are sometimes not very good at execution.
They paint a great picture, but they haven't shipped anything in 10 years, just one hype story after another.
Moses was followed in the desert for 40 years until they reached the Promised Land.
You'd think at year 39 somebody would have said, 'This dude has no idea what he's doing.' But people kept following him.
Entrepreneurs are like that. People have to be able to follow them. But they also have to know where they're going.
I don't think we'd be singing the story of Moses if he hadn't reached the Promised Land."
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This puts patrickcollison.com/fast in a whole new light
Stripe’s 1st employee @darraghbuckley on how John and Patrick Collison would sprint to get things done faster:
"As is the tradition of every startup getting its first office, you arrive and the place is empty. So, IKEA trip.
Six of the cheapest desks and chairs, into the car, back to the office.
You're unloading. Pick up a box, put it down, walk back to the car.
But that's not what John and Patrick do. They pick up the box, walk it in, put it down.
And then they sprint back for the next box.
And you're standing there as the observer thinking, did we park illegally? Did I miss something? Why are you running?
They just always had this sense of urgency. And if everyone else is running, are you going to be the one person who isn't? So you run too.
Not in an obnoxious, I'll-race-you way. Just in a, why wouldn't we do it fast way?
They really built cultural prevalence around the importance of urgency."
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"Use boring technology widely"
The lesson Stripe’s 1st employee @darraghbuckley learned from the co-founder of Anthropic:
"Tom Brown, one of the Anthropic founders, previously at OpenAI, has this impactful technical view from early on: use boring technology widely.
Don't over-optimize for the perfect tool for each job. Benefit from a broad tool that can do many things.
What he's pointing at is the price of complexity. When you use the perfect tool in each place, now you have many tools, and understanding all of them is hard.
So be careful about the complexity cost of what you're doing. I reach for that one almost daily.
It's okay to do something in the wholly uneventful way. It doesn't need to look bright or clever. It just needs to be maintainable."
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Nicolas Neubert
TIL the US financial system almost had a Y2K moment in 2025.
Stripe’s 1st employee @darraghbuckley on how the Federal Reserve re-wired everything overnight last year and nobody noticed:
"About a year and a half ago, the Federal Reserve updated the messaging spec for wires. Fedwire moved to an international standard called ISO 20022.
Nobody knows about this outside a small group. But it required coordination across every financial institution in the country.
It was basically a hard cutover, one Sunday night. If anyone described a technology transition like that to you, you'd put your head in your hands.
Please don't do that, it'll go horribly.
It's kind of like Y2K. And the Fed pulled it off, through months of planning, testing, and good operations.
Success was defined as you didn't know it happened. You didn't read on the front page that wires across the nation stopped.
So the underlying US payment networks are actually great. We have real-time payments.
What's missing is the last mile."
New @ThePeelPod with @darraghbuckley
From employee #1 at Stripe, to starting @IncreaseDev and moving $500B per year with 33 people.
And they just bought a bank.
He talk how to acquire a bank when they can't tell you they're for sale, why putting an API on a bank is like "strapping a jet engine to a go-kart", why The Fed actually has great technology, the overnight build that turned on Stripe’s first dollar of revenue, why Patrick and John Collison sprinted everywhere, and why you want your banker to be bored.
Watch here + links below
0:00 Stripe's 1st employee bought a bank
1:38 Fixing the stone in his shoe building Stripe
7:59 Banking looks like 2010 payments
11:11 Merging two layers into one, just like Stripe
14:52 Why he finally bought the bank
16:26 How do you actually buy a bank?
20:20 The first bank that got away
22:04 Why banks can’t chase new fads
25:26 Compliance as code, from day one
29:46 Talking straight to the Federal Reserve
32:19 The Fed migration that nobody noticed
33:50 The missing last mile of banking
35:44 Getting customers to switch
38:23 The challenger sales model
40:33 What customers use Increase for
41:48 How Ramp's bill pay works
42:37 $500B a year with 33 people
45:31 Hiring for a high-empowerment culture
47:08 Growing up with the Collisons
50:27 150 test cases in one night
54:23 What really made early Stripe work
57:07 Why Patrick and John sprinted everywhere
1:00:00 “You're not in payments, you're in fraud”
1:02:31 Where AI hits a wall on fraud
1:05:08 Giving payment cards to AI agents
1:09:27 Use boring technology widely
1:11:37 You want your banker to be bored
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