I joined Stripe four years ago to make starting an Internet business easier, mostly by work on Stripe Atlas. This has been a series of adjustments for me: to working as an employee, to experiencing hypergrowth, to being closer to the Silicon Valley culture, and to some of the challenges in balancing career and other commitments during my life stage and the global coronavirus pandemic of 2020.

Perhaps some commentary will help other folks make decisions, so here it is. I’ve previously written about my experience after two years and my thought process in joining Stripe.

What do you do at Stripe?

I’ve had a very fluid job at Stripe for much of my tenure, which has had pluses and minuses. It has allowed me to work on broad challenges throughout the company’s operations, but sometimes means less legibility internally and externally. That has started to matter more as we’ve scaled.

When I was hired, there was a fiction for my business cards but the job rounded to “Do anything required to make Stripe Atlas successful.” I contributed on a part-time basis to things outside of Atlas. For about a year I was formally in the Marketing department while continuing to do a broad portfolio of things, many of which aren’t classically considered marketing.

As of December or so, I’ll be joining a new cross-functional team with designers, publishers, and writers. We will run some of Stripes publishing properties (like Stripe Press and Increment), continue doing not-quite-software-product experiments to make the Internet more hospitable to starting and scaling businesses, and help to maintain and improve the developer experience and candidate perceptions of Stripe.

My job within the group will remain a bit tough to pigeonhole. I’m not and haven’t been a manager at Stripe; I’m a senior IC.

No really, what do you actually do every day?

I work from Tokyo and most colleagues close to me on projects are in San Francisco, Seattle, or remote in North American time zones. This means I get up early frequently and (thankfully decreasingly) sometimes go to bed late.

A typical day for me is an hour of meetings starting at about 7 AM in Japan, an hour helping my kids get to school, another hour to two of meetings, and then focused work time which may include a meeting or two with someone in an APAC time zone in the afternoon. Due to the coronavirus situation, I’m presently working from home; prior to it, on most days I would work from the Tokyo office, commuting in after morning meetings.

I wouldn’t call myself a paragon of work/life balance; I’m a recovering salaryman and used to run businesses which routinely paged me during core user hours when I was sound asleep. The nature of my work makes it hard to give a rigorous estimate of “how much I work.” My job and my main hobby overlap. I’m basically never not thinking about the Internet economy. My sleep schedule has ranged from atypical to disastrous, but that has been true for almost all of my adult life.

My work falls into three buckets which are approximately equal weighted in importance and time spent:

Project work: This is the core work for my assigned team. A typical smallish project would be getting a blog post written; a largish project would be assisting a Stripe product launch. My actual involvement work on the project generally involves planning, execution on particular bits of it (often involving writing directly public-facing artifacts and internal plans), and being a generalist happy to do anything required to ship.

Back when I was working on Stripe Atlas, due to how that team operated I was more directly involved in product work. These days I’m generally brought in early during the ideation and customer discovery phases and late in the launch / go-to-market phase, but don’t frequently contribute directly to design or implementation of the products.

Consultative work: I spend a lot of time on community work (including on HN and Twitter), work directly with individual users, and advocate for some user personas internally.

I have been described as an evangelist, and that makes me feel a little weird, but part of the job is turning personal karma into corporate karma. Stripe makes products which are much more central to our customers’ businesses than most software. We have to demonstrate good taste and probity, and we have to do so prior to winning the customer’s business. I love talking to founders and acting as an entrepreneurial commentator, and would (and did, and do) do it for free, but part of the reason I can do from a work laptop is that, at the margin, it makes it more likely that you will build your next business on Stripe.

In addition to this, every time I convince a Stripe customer to raise their prices or otherwise improve their business, we benefit directly. “I am employed to tell people to Charge More^TM” sounds like a self-deprecating joke, but you could imagine me attaching a spreadsheet to performance reviews. One sheet would be my best guess of how many software founders would listen to my advice, one would calculate the relative distribution of $100k, $1M, $10M, and $100M annual revenues among software companies, and one would include observed uplift after implementation of advice.

My consulting business used to be centered on turning $20 million a year software businesses into $22 million a year software businesses. A quick perusal of our pricing page will suggest why we can afford to give my advice away for free.

Sometimes this involves scalable writing such as the Stripe Atlas guides. Sometimes I work with a single founder to get their B round accomplished.

People sometimes ask whether we’ll retain our startup-focused soul while increasingly serving enterprises. A portion of my job is helping folks communicate that we’re serious, reliable infrastructure for the largest participants in the global economy while also keenly appreciating that the user might be on a small team trying to sell
bingo cards or politically-themed breakfast cereal. This sometimes means intervening if it looks like we’re not living up to our expectations. We care about supporting upstarts because that increases economic opportunity worldwide, which is a worthy mission to have. Also, directly relevant to the business, you never know what people are going to go on to accomplish.

Non-core projects: Every few quarters, I rotate to a new team to spin up some new experiments and see if they’re worth doing long-term. If they are, I try to set an appropriate team up to own them.

Two notable successes:

YC application review, where we solicit applications before founders send them to YC, and help the founders tell their story better (and sometimes provide direct business advice). That started with me solo reviewing every application. We built it into a repeatable process with 100+ Stripes involved every six months.

The Remote Coffee Chat series, where we experimented with radically decreasing the barriers to actually meeting future coworkers by doing Zoom meetings with a panel of six Stripes and anyone who wanted to hear us talk shop. Coworkers are the best possible advertisement (and one core benefit) for working at a company, so just exposing potential candidates to people talking about just actually doing work has led to great opportunities. We have hundreds of remote Stripes and a surprising number are here because they decided to drop by to a coffee.

This is a refinement of a previous process, where I just took requests from anywhere at Stripe to pitch in. That became acutely unsustainable, because…

What has changed over four years?

Stripe has experienced hypergrowth over the nine years where it has been publicly available, and I’ve seen four years of that personally. You’ll forgive me for not putting a number on it.

Read “hypergrowth” as “sustained, geometrically compounding growth in most metrics of interest, persisting for years at a time, at growth rates which one does not see sustained for years in almost any field of human endeavor except at hypergrowth companies.”

From this simple observation about growth rates you can predict many statements about the world, and those statements will sound outlandish. Many of them are true, which might not make them less outlandish.

Here’s one: I started in September 2016. At that point, Stripe Payments had publicly been available for 5 years. Stripe is, qualitatively and quantitatively, about as different counting from my start date to today as it was counting from launch to my start date. The midpoint isn’t an arithmetic mean, it is a geometric mean; huge changes happened over short intervals.

What does that mean concretely? Well, I was employee #650 or so. A common worry of folks joining around the time I joined was whether there was anything left to do. Have we solved all the challenges we’re going to solve? Have we built all the things we’re going to build? Has all the fun work already been done?

This was a serious worry in 2016. It is laughable now. We have almost 3,000 employees and it feels like too few to do all the work. We have solidified a lot of our operations, security posture, resiliency, etc, and it still feels like we have huge opportunities for improvement.

We keep shipping things, including both incremental improvements to the N dimensional capabilities matrix that is Payments (e.g. expanding JCB acceptance) and fully new products like e.g. Corporate Card. One thing coming down the pipe is more exciting to me personally than anything since Stripe Atlas.

This has required a lot of work, including metawork on the organization itself. This has been the defining challenge of hypergrowth for me, and it never stops: if a company is hypothetically growing at 2X per year, then on the day you join half of your coworkers will have less than a year of experience. A year later, half of your coworkers will have less than a year of experience. A year later…

This means that, while working on the project that should land in mid-October and also working on infrastructure to keep the lights on, you are also working on making sure your organization (or sub-org, or team, etc) can quickly spin up people who recently joined and get ready for the next phase of organizational scaling challenges.

When I interviewed at Stripe the Marketing Department came to meet me. Her name was Krithika. We now have about 60 people in Marketing. Every milestone is simultaneously project work, attempting to teach newer members the company voice and tone, letting more experienced team members stretch their wings a bit in their careers, and updating the list of things that are on the cusp of breaking.

And break they do! We got an incredibly long way on having a very small group of Stripes care passionately about e.g. product launches, but “the entire team working on this page could split a pizza” doesn’t scale to e.g. needing to localize it for 40 countries, give regulators in many of those countries a heads-up, get formal approval for quotes from enterprises with A Process For That where previously we could have just texted a startup founder, etc.

And so the way we work changes.

Organizational and career growth corresponding

I used to read essays about how some people don’t “grow with the company” they founded and leave it to start something again, or how some people have a preferred stage of company. These never made intuitive sense until seeing much more range in four years than my career had exposed me to in the 15 prior.

As Stripe has matured around some of these challenges, the type of contribution I do most often has changed. If I were doing exactly what I did on day 100, I’d probably be useful at the margin but underperforming my desired contribution to Stripe and the Internet at large.

When I was on Stripe Atlas, a small, focused team with many high-horsepower generalists who largely didn’t have a huge amount of entrepreneurial experience, part of my job was bringing skills and connections and part was just standing up portions of our offering by sheer force. We wanted helpful advice for founders and didn’t have it; I locked myself in a room for a month and wrote a 30,000 word guide plus the ERB to put it on the Internet. We wanted to inculcate an Atlas community; I installed Discourse, wrote our SSO code for it, sent out invites, and commented on every thread for months.

These days, while I still do have occasionally grindy just-do-all-the-things sprints, a lot of my value to Stripe is understanding Stripe. As an organization gets larger, an increasing portion of its activities turn inward.

There is a line in Hollywood set design: “Make sure your budget gets on screen.” In startups, you want your efforts to be directly customer-visible. A well-operated early stage startup should spend basically no time on things which aren’t either product or talking to customers. Productive work is, by definition, “on screen” to users. You minimize (and regret) nuisances like incorporation, setting up payroll, and the gigantic productivity tarpit that is fundraising.

Stripe is still a relatively small company. The high school I attended was larger; AppAmaGooBookSoft have individual products with more engineers than our company has people total. But even at our scale, a large portion of all effort expended is “off screen.” It is interviewing candidates, writing performance reviews for teammates so that they have a career path, teaching new hires how to be effective, contributing to company planning exercises, running retrospectives on what happened such that the Japan team learned of a product launch when untranslated English appeared on an important page, etc.

When I ran my own company, I looked at BigCo and wondered “What is it they do all day?” I still think there are pretty vast differences in aggregate productivity per employee, and I think that is fairly obvious to anyone who takes software seriously, but I have much more appreciation for how much effort goes into just keeping a complex organization moving.

There exists a theory that much of the work involved in keeping complex organizations running either doesn’t create or actively destroys value. I think this theory is heavily overendorsed. There is value created off screen, too, but if your relationship to companies is as a user, you will not perceive it and therefore underestimate it.

HR departments don’t exist to fill seats on a headcount plan; HR departments exist because as you scale you will inevitably hit predictable challenges and the simplest solution to them, well-trodden by many companies before you and with minimal execution risk relative to alternatives, is to have a HR department. You can’t continue shipping software to users if your intermediate developers leave because they see no career path. You won’t continue talking to users if your sales reps repeatedly do not actually receive the promised amount of money on the right day, or if their local government is dissatisfied about withholdings. These don’t feel like challenges when you have three people in a company but get a bit more acute when you have 3,000.

(In a way, every scaling startup is an experiment in empirical microeconomics research on “What parts of the typical corporate form are necessary and which are pageantry which we only keep around due to anchoring, the sunk cost fallacy, and tradition?” Every time a startup bites the bullet and hires a VP of Sales, a lifecycle email copywriter, a retirements benefits administrator, or a cook, count that as a published result saying “Yep, we found this to be necessary.”)

As Stripe scales, I find the forms of my contributions changing. I sustained 250,000 words written a year for many years while running my software companies. I feel like I still write as much as ever, but increasingly off of the public Internet. They might instead land on e.g. our Japan strategy for 2020, feedback on positioning for a new product launch, helping a colleague think through their career goals 2 years out, etc.

I still do customer-visible work. One project was a customer-facing email series which, according to our A/B test, added probably $THIS_NUMBER_HAS_A_LOT_OF_DIGITS of enterprise value. Scale has its advantages. Those emails weren’t subjectively the best writing of my career; it was a meat-and-potatoes drip campaign. Most of the challenge was getting us organizationally comfortable with the notion of doing it. The important result wasn’t either the words or the observed uplift; it was producing organizational certainty that “Yep, turns out every B2B SaaS company has a lifecycle email campaign for a reason and we definitely should, too.” That’s something that I believed on day one and which many stakeholders agreed with, but there was an art to getting the organization to successfully ship it.

“Stakeholder” always felt like a funny corporate word for me, but it is a useful one. A perennial problem a few years ago was that we were, generally, rubbish at doing stakeholder identification in advance. This meant that projects were frequently organized by informal social networks over Slack and email. That has some scaling challenges. We’re better at it these days, though that is a major work in progress. A recent ship had sixty identified stakeholders on it; that number simultaneously strikes my founder brain as absurdly high and my commentator brain as “Wow, that’s lower than I would have expected for novel financial infrastructure, by more than an order of magnitude.”

The global startup and tech communit(-y/-ies)

I’ve joked for years that I orbit Silicon Valley at a distance of approximately an ocean, largely due to spending a lot of time on HN. I think I may have to deprecate that joke.

Silicon Valley was a place. It has become a metonymy for a community of practice. You can find outposts of Silicon Valley in Tokyo cafes, in WeWorks in Bangalore, and on the coast of Cape Town.

This predates the 2020 coronavirus-induced boom in remote working, but in many ways that is forcing acknowledgment of an existing trend. The argument for continued hyper-concentration of the tech industry in a particular location had observable fact going in its favor, and now observable fact is that many of the nodes central to the network are Zooming in from elsewhere.

The Schelling point was sustainable when the talent went where the money was and the money went where the talent was, but now that everyone knows that a tech company can thrive over Zoom meetings, minutes of commute time from Sand Hill Road should no longer be a dominant driver of access to capital.

This genie feels unlikely to go back in the bottle.

Much of my job is being an accelerant for this change. It involves democratizing access to the folkways of Silicon Valley, both via scalably publishing about them (e.g. writing this guide about pitching a startup) and via less public conversations. I also have spent many cycles working on Stripe’s ongoing expansion, including our acceleration of remote work and helping to make a heavily international organization a cohesive culture.

Working at Stripe has caused an interesting change in my relationship to the Silicon Valley ecosystem. One way is that the domain name sometimes opens doors that the username did not. (That doesn’t feel great to me, to be honest, but is a useful observation about life, particularly to folks who are early in their careers.) I know a lot more venture capitalists, executives, etc than I did a few years ago, and am treated as a more serious professional than I was despite no obvious corresponding change in skill in the intervening time.

It is my perception that I will probably keep these newer advantages in the future; I wish I had understood how this part of the ecosystem worked 15 years ago. (I am aware that I am saying this from the perspective of someone who had a reasonably deep network when I joined; it turns out that there are levels here.)

Working at Stripe affords me a lot more leverage to help software people than I had previously. The most direct way is by improving our products and services, and as time goes to infinity I assume that will be Stripe’s largest impact. At the margins, though, there is some benefit to being able to play a social capital marketmaker. You would benefit from meeting this investor; they have expertise in your core challenge. You should take a meeting with this startup; they’re incredibly on-thesis for you. We should reconsider a decision on this compliance edge case; it negatively affects a single startup.

(I can’t provide much color commentary on that, for the obvious reasons. I will say that part of the work is doing the work, and part of the work is teaching the organization how to do the work. A major purpose of me spending an “economically irrational” amount of time working to improve one startup’s experience is to help maintain the organizational culture such that our newest employee understands that overwhelming support for startups is the default expectation.)

Speaking of marketmaking, I’ll observe that I seem to be drawn to finance as a source of analogies and models of the world more than previously. Partly that is due to having my baseline business model reconfigured from a recurring revenue SaaS company to Stripe’s somewhat more complicated one (see below). Partly it is due to talking to many more investors and financially-oriented professionals than I did previously. I cannot say this enough: pick your peer group wisely because you’re giving them write access to both your conscious thoughts and your entire worldview.

I mentioned two years ago that the Stripe Atlas team was the strongest one I had ever worked on. I continue to like my peer group at Stripe and the folks I interact with outside our Slack. I’ll note that a bittersweet part of this is that a combination of Silicon Valley math and having ambitious friends means that many of my close peers moved on to new adventures over the course of four years. Frequently that is for founding a company; sometimes it is for taking a career upgrade elsewhere. The salaryman part of my brain has despaired about the number of “Here’s my contact information if you ever need it” emails that I have to write, and the entrepreneur part of my brain feels the same temptation constantly.

(We are given a survey every six months to measure employee engagement. One of the questions is “Do you ever think about taking a job elsewhere?” and I always answer it truthfully and then add the freeform note “I apologize because I know this answer will be scored negatively but if I weren’t constantly thinking of starting a company I would be rubbish at this job.” It’s an amusing superposition: I feel like I’ve done the best work of my career to date but that if it ever becomes the best work looking forward something went deeply off the rails.)

Being an employee versus being an entrepreneur

There are many differences in being an employee versus running your own business. Most are covered adequately elsewhere.

This was a surprise to me: I had never deeply considered career goals prior to having a manager who had “Make sure to talk to patio11 about career goals this quarter” on their todos. It was always “Eh, running a company now, will probably run other ones in the future, what is a career anyhow, the priority for the business this week is…” for the last decade.

On having space to reflect on this, and being forced by the Stripe written culture to actually put the words to paper, I firmed up my understandings of what I want out of my career, what I hope to accomplish through the (fairly large) chunk of life that is working, how that relates to my other values, etc.

I’ll spare you the whole writeup, but my career success metric is making a large improvement in the lives of a large number of software people. I encourage anyone who isn’t already planning on a 45 year time scale to try taking a stab at this and reviewing the plan every year; the weeks are long but the years fly by sometimes.

At present I’m at Stripe because I think it is probably the best option available in working against those long-term goals. 15 years down; 30+ to go; still early innings.

I’ll note that working in a growing startup will give you many, many ideas for companies to start. Basically every internal tool at a company capable of putting good engineers on a “boring” problem should be used across the economy at companies that can’t get that caliber of engineer on that sort of problem. Working here has also helped me better calibrate my understanding of how companies in strange countries like the U.S. actually work; I would certainly do some of our Starfighter experience differently having seen how a recruiting team works up close, for example.

What Stripe does differently

I thought when I joined that I had a fairly well-developed mental model of Stripe as a user. Here’s where I’ve refined that model over time:

I have persistently underrated the usefulness of ambition and the amount of it that Stripe has.

I have been a long-time skeptic of Silicon Valley’s “changing the world by $INSERT_HERE” memeplex and preferred running businesses which were small patches to capitalism. I retain a great love for small businesses, and have no deep regrets, but I’ve gained a strong appreciation for having an expansive view of one’s future possible impact and on moving quickly to get there. Considered in hindsight, I think my businesses would have been more successful and I would have been more fulfilled had I hit harder, bigger problems faster rather than tackling ones I was more sure that I could take on.

There exists a class of errors that I think English lacks an adequate name for: one which you know about, believe yourself to have adjusted for, and are still underadjusted for. I thought I had an adequate mental model for how ambitious Stripe was rather early in its life. I believe that tweet to be underadjusted in scoping the ambition. I believe I am likely, here in 2020, still underappreciating its true scope of ambition.

That probably sounds crazy. Again: my worry is not that I am crazy, it is that I am not crazy enough. I think I understand the underlying drivers of the hypergrowth graph sufficiently to understand what the sources of risk to it are. While those sources of risk are a constant, daily struggle, the market opportunity clearly does not have an asymptote close to where we are.

I also have the benefit of looking back at Stripe’s extensive internal library, including the contemporaneous thoughts of many internal and external smart people at various points along the curve, and almost all of them substantially underpredicted both what would be achieved and what concrete instantiations the big ambition would take on over time.

I know this sort of thinking gets widely mocked in online watering holes, including by myself many years ago, and all I can say is “Pick a peer group where ambition in the service of humanity is seen as positive and where actual progress is seen as achievable.” A huge portion of the value creation of Silicon Valley is through directly intervening on the ambition of impressionable people. I suspect one reason it echoes in culture outside of the technology industry is that this ambition effect is repeatable elsewhere. (And I suspect that one reason Silicon Valley draws such criticism is because this ambition effect is demonstrably repeatable elsewhere. Examples left as an exercise to the reader.)

Set one’s operating cadence to ‘run.’

Organizations have a lot of difficulty operating at a cadence which is unlikely their default one, and that cadence tends to get slower over time as the organization’s energy gets taxed to support the organization itself. People also seem to have a set operating cadence, though theirs is more context-dependent; I’ve noticed wild swings in mine over my various jobs, mostly in conforming to local norms.

Relentless execution is something of a cliche, but it is a cliche for a reason. Organizations that need to hire a Head of X to start Xing will necessarily pay a multi-month cost to start Xing; you can get a lot done in months. Many organizations will have a culture which says “Why do X in the interim when we don’t know the best practices and will inevitably throw it away?”; they will lose out on months of progress.

The returns to pushing your cadence to faster are everywhere and they compound continuously, for years. Don’t send the email tomorrow. Don’t default to scheduling the meeting for next week. Don’t delay a worthy sprint until after the next quarterly planning exercise. Design control and decisionmaking structures to bias heavily in favor of preserving operating cadence.

I don’t think Stripe is uniformly fast. I think teams at Stripe are just faster than most companies, blocked a bit less by peer teams, constrained a tiny bit less by internal tools, etc etc. There are particular projects which have been agonizingly long to ship; literally years after I would have hoped them done. But across the portfolio, with now hundreds of teams working, we just get more done than we “should” be able to.

A stupendous portion of that advantage is just consistently choosing to get more done. That sounds vacuous but hasn’t been in my experience. I have seen truly silly improvements occasioned by someone just consistently asking in meetings “Could we do that faster? What is the minimum increment required to ship? Could that be done faster?” It’s the Charge More of management strategy; the upside is so dramatic, the cost so low, and the hit rate so high that you should just invoke it ritualistically.

Most organizations operate at nowhere near the frontier of their capabilities. That is a choice, and strikes me as a valid choice, but you can choose to move closer to the frontier, too.

Stripe has a much better economic model than most software companies.

Without spilling too much secret sauce:

B2C software companies’ success scales with the count of their users. Growth in users is their primary lever in growing the business, which you can further decompose into acquisition, conversion, retention, etc. To a first approximation, no metric except those impacting growth matters. Software people use a lot of B2C software and their intuitions of the software business are overly informed by this fact.

B2B software companies’ success scales with both the count of their users and those users’ success, because their pricing model will generally (unlike most B2C companies) capture a portion of the customer’s upside. They have the same incentives in growth that B2C companies do, but they have an additional lever: making the user more successful directly incrementally helps them. Additionally, they participate in underlying growth of users, similar to an equity holder.

A B2B business selling to healthcare providers in the United States includes an embedded synthetic call option on U.S. healthcare. Finance-to-geek translation: “If you sell to doctors you prefer futures in which more money goes to doctors. Those are much better futures for you than futures with less money going to doctors. However, even should you find yourself in a future with less money going to doctors, you will probably still have doctors to sell to, so it is difficult to imagine that future being much worse than today, given that you have only sold to a tiny percentage of all doctors so far.”

My view on Stripe’s business prior to joining was “Stripe is basically a B2B SaaS company with extremely reliable capture of upside when users succeed.” I believe that substantially underappreciates the actual business. Large portions of Stripe’s business add another loop on top of the B2B SaaS loop, where Stripe is effectively indexing on its ability to grow the count and success of customers who are themselves structurally equivalent to B2B SaaS companies.

Combine this model and what a former colleague dubbed Patio11’s Law (“The software economy is larger than you think, even after taking into account Patio11’s Law”) and you have my biggest surprise since joining Stripe.

I believe that Stripe likely has another trick to play, which plausibly includes a loop on top of this one, where Stripe will perhaps index on the number and success of companies which index on the number and success of their customers, where those customers are structurally equivalent to B2B SaaS companies, who index on the number and success of their customers.

As for the specifics of that, well, we’ll see what the next few years look like.

2020 has been a tough year

I feel like no writeup about the last four years can avoid 2020, which: it has been the toughest year of my life. I have struggled with low-grade depression for most of my life; events this year (*gestures*) exacerbated that into a severe depressive episode. Props to very supportive colleagues (and a company policy which was extremely generous to employees needing extra help in 2020) for assisting me in working through this.

I’ll probably write more about this sometime, but since the short version may be useful: Strongly consider talking to a medical professional; treatments exist and may help you. I’ve had a revolutionary improvement in QOL as a result of medication and daily exercise. There is still a struggle, but it’s my normal struggle and not causing nearly the degree of impact to my life that it was earlier this year.

Strongly consider working at Stripe

I’m broadly happy at Stripe and presently intend to be here for at least a few more years. I think the company is likely going to change about as much in the next four years as the last four, again in a compounding fashion. It is entirely possible that products the world hasn’t seen yet will be bigger than Stripe itself was in 2016, 2018, or 2020.

Want to work on them, or other worthy challenges, as our company starts to exit the awkward teenage years? We’re hiring.

There is still more to build. There are still more entrepreneurs to help. There are still challenges to be solved and fun to be had.

1. IC is short for “individual contributor”, which is corporate America speak for “directly does the work rather than managing the people who do the work.” At the same time, senior ICs are also supposed to exercise a form of leadership. Capacity to do that and also “get my hands dirty” in the same day is part of the job. ↩

2. I will say that growth rates at many software companies which would generally be considered to be past the hypergrowth stage have been historically unprecedented in the last few years. Microsoft—Microsoft!—has added four Microsofts—four Microsofts—since 2015. I think tech has spent far too little brainpower on figuring out how that happened. Our models of the world were shattered and we have largely slept through it. ↩

3. Stripe doesn’t have a CMS yet, though we are getting around to it. Almost every page on stripe.com is an artisanally crafted .erb file. ↩

4. There is a meritocracy in our class system and a class system in our meritocracy, and I feel that this is underexamined because the nuances discomfit both people who understand the nature of merit and those who understand the nature of class systems. ↩

5. There is beauty, purpose, and dignity in running the neighborhood sandwich shop. Contrary to some memeplexes in Silicon Valley, I don’t think that a firm (or founder) which would sacrifice growth rates for other worthy goals is even implicitly doing something wrong. ↩

6. Structurally equivalent? Just like finance people see an office building as a balance sheet and cash flows, I see an office building as a SaaS company plus some glass and concrete⁷. ↩

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12. I take this joke extremely seriously. How many office buildings could we find capital for in Chicago, at rent rolls of $100k a year to $10M a year? That’s about how many SaaS companies should exist. In Chicago. Office buildings aren’t venture fundable, but that doesn’t mean they’re not an investable asset class. I think non-rocketship SaaS is getting there, too. ↩

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