I didn't get as much exposure to the rest of the company as parent comment, but I'll say I saw a weird air of complacency and assumed success.

I first ignored my instincts that something was wrong, but as I saw more of how the company operated, I became convinced that the single largest problem the company had was the culture. On the surface, I agree with the parent comment, things were definitely positive, but rather than toxic, I think it was more of a naive one, like most of these people had never worked at a startup before, and didn't understand that it's always easy to snatch defeat from the jaws of victory, and that if they didn't understand what they were doing and how it affected the company then probably nobody else did either. It felt like everyone was very smart, but somewhat foolish (myself included).

That being said, I enjoyed my time there, and definitely learned a lot, especially organizationally. The people are solid and I think Affirm is going to get a pretty sweet deal.

But if you are an early employee with equity, you are not just an engineer. You are, figuratively, a shareholder. One of the reasons they give you stock options as opposed to actual shares is that shareholders have a ton of rights against companies, and can e.g. sue for investor fraud, vote the board out, get quarterly reports with financial & performance statements therein backed by federal law and the threat of investor fraud lawsuits. You, on the other hand, are given the financial exposure to the company's performance without any of the attached rights. And they will happily lie to you in order to keep you happy & get you to project enough positivity to hide flaws & keep outside investment flowing until it all collapses.

So as an employee, you should be trying to claw back some of what being a shareholder would get you, given you are so heavily exposed. I've worked at companies where there is a monthly meeting, nearly everyone present, where the entire company's business position, prospects and challenges are discussed openly. The employees (largely) didn't even have equity. Any cracks (like an imminent complete collapse in the next three days) would show very early on, but there were none, because the employees were empowered to do something about any challenges.

So, yes, there are warning signs, and your response isn't a binary choice between staying and leaving. I would like people to come away with a better model of this than "if they are hiring exclusively from big tech, that's a red flag, get out of there". You can demand more transparency if you know what transparency looks like. If you are content to sit at your desk and happily churn out React components, satisfied with management sending enough emojis at you via slack, then you can't protect yourself at all.

You want to be at the company where the CFO gets up at the monthly all hands and goes over the numbers in gory detail and doesn't hold anything back. You do not want to be at the cargo cult company where they get up and cheerlead and never talk about numbers. It took me a shockingly long time to figure this out.

In the end the stock gains have all been in the periods where I didn't work at startups but instead worked at public companies. Go figure.

"Toxic positivity" and ISOs/rights:

ISOs nominally give you "ownership" in the company, an extra incentive to make sure it succeeds. But you lose them within some time period after you leave (say, are fired), and there's no way to sell them during that time unless the company has gone public. So this thing that's supposed to make you an "owner" just makes you a hostage. It does not motivate you to take risks on behalf of the company, and it does not motivate you to speak the truth.

If they couldn't take it from you, then you'd speak the truth.

Double-trigger RSUs are AFAIK just a way to avoid paying taxes on illiquid assets. The reason to shift from options to RSUs at all is (I think) that once the company's FMV gets high enough, the strike price and taxes due for the options will be so high that employees won't be able to afford paying them if they leave the company.

I thought it was common knowledge that fb started the double trigger thing to avoid this limit, and I heard something similar when a startup I was in converted options to RSUs.

HR would tell us we were extraordinary, we would have world-class catering for lunch every day, and yet we had no customers, no contracts, and no money except the investors'.

It was a sobering realisation on the damage that can happen when you are submerged in toxic positivity. You forget that companies still need to earn actual money, that it's not a party every day.

I'd like to point out that this is not the case for every Silicon Valley start-up: the three start-ups I worked at (CollabNet, Aeluros, Ardatech) were incredibly frugal with money (exception: salaries were competitive).

At one of the companies, the CEO and I took a trip to Safeway to buy soft drinks for customers. When we got back, I walked around the office telling everyone the soft drinks were _not_ for them, only for customers.

At another company, I had to make a compelling presentation to the CTO to buy a $1.5k printer. "The Linux workstations need a PostScript printer!" We bought the printer, but he didn't like parting with the money.

Being frugal doesn't guarantee success: my CollabNet stock was washed out in later rounds, Aeluros had a fair-to-middling exit to Broadcom, and Ardatech had a good exit to Google. But it's good to keep an eye on the money.

The lesson should be buy whatever the hell people want, just stop buying people until you need them. They're the expensive bit.

3 great devs can do about the same work as like 30 average ones. People massively underestimate communication overhead. As soon as you lose the 'startup feel', you lose the speed, and it's gone for good. The transition is probably inevitable, but there's a threshold of revenue you have to reach before you make it. If you don't reach it, you're cactus.

150 devs and 50 sales people to generate $600k yearly revenue is laughable.

Absolutely. We were frugal, but not to the point of self-sabotage. Our biggest expense was payroll, followed by the Cadence/Synopsys EDA software licenses.

So, for example, no catered lunches or breakfasts, but if there was a customer or investor dinner, it would be expensed.

We had good health insurance, but we didn't have gym memberships or (gasp!) an onsite gym.

The workstations were powerful, but we shaved costs by buying "gamer rigs" instead of the more expensive "engineer workstations". We bought prosumer equipment (Netgear) instead of enterprise equipment (Cisco).

If someone needed, say, a Wacom tablet to accommodate a wrist injury, we made that happen.

We had a well-stocked lab, but some of the electrostatic benches we got at a good price secondhand.

Our office was near the train station to accommodate the engineers who commuted from the city, but it wasn't expensive space (all glass & chrome); it was a "B" office. We shared a bathroom with the other tenants. It was a little run-down, but it was clean.

We didn't have offices or cubes, just desks, and the CEO & President sat next to each other in the big room we all shared.

If only they could be bought that easy right when you'd need them. At least in a corporation, the HR will tell you "50 engineers? That's going to take X monts, judging from the hiring rate we had so far."

Fast pitched itself as taking the prudent path compared with e.g. Bolt. The latter went for big clients first. Fast started with small businesses.

There were clearly other issues. But the closing era of cheap capital favoured the bold, and Bolt’s seizure of the fertile low grounds cut off Fast from its growth. Despite Fast taking the orthodox path.

Fast did great job hyping the company on Twitter, likely the founder also was a good storyteller. The old adage is that you raise with a story, team or traction. Sometimes the story actually pans out, like with YC Airbnb is often an example of company that struggled for a long time in the beginning and no-one could really predict how big they could become.

Who? (Also, given an open market, as was the case when the Amazon patent expired in 2017, the company fundraises to scale will beat its more timid competitor. This is basic strategy.)

If you were in a different industry…great execution in the wrong industry is as good as a Ferrari in a swamp.

> all that matters is knowing people

Sounds like you’ve been through some shit. I’m sorry for that.

The point I was making, summarily, is that Bolt ate Fast’s lunch. It went straight for the big customers. Fast wanted to grow towards them incrementally. In this story, if anyone had a fundraising connections advantage, it was Fast—they were Stripe backed. Bolt outmanoeuvred them (and was lucky).

This is unorthodox strategy. Fast played it conservatively. Bolt swung for the fences. Curiously, Bolt landed the home run.

Fast made what was manifestly the wrong decision, both in hindsight and in foresight (I'm happy to post my WhatsApp screencaps from a year and a half ago when I was exploring starting a co in that space). It's not possible to build a hands-off 'platform' like Stripe in that space - integrations are complex, and so integrating a large number of small clients predictably bogged them down till they ran out of money.

(That's not the only reason, I'm sure. It was also a shitty implementation of one-click checkout: most saliently, it wasn't one click. Anyone who actually tried Fast at the time - and I & my prospective cofounder shared the few tiny client websites either of us found like they were rare gems - could see that it was a terrible implementation, in a space where UX is literally the entire game. Many actually did, e.g. this guy from back then: https://chrisfrantz.com/checking-in-on-fast/)

maybe Bolt knew a couple of things Fast did not.

We failed to raise money exactly because we had a bunch of small clients and not enough revenue. It was a prudent decision for the potential investors - but the main failure on our side was not to network enough with our current investors in order to get another friendly round of investment.

We had a competitor that was doing exactly the same thing (with worse metrics) that raised several millions a few months later, so it wasn't too far fetched.

VCs invest in a lot of baseless crap - sometimes the crap turns into gold and sometimes in order to be the chosen crap you need to know the right people.

I detailed a case where a recent deploy I had done had resulted in elevated error rates for some of our clients and how I had solved it with a quick follow up push to prod. The interviewer asked why it wasn't caught in staging and I mentioned that it could have been but as a small company we have to make velocity vs bug tradeoffs and in general it feels like we are currently at a sweet spot. The interviewer was unwilling to explore that space at all, or the concept that different companies might want to land in different places.

Later I was given feedback that I did exceptionally well in the technical interviews but the company didn't want any cowboys on their team. All of that is probably just a long way of confirming the other anecdotes in this thread that from the outside fast seemed somewhere between delivery hostile and overly cautious.

But to be deemed as a cowboy - utterly hilarious, given where they ended up. Pretty cowboy with the investor money instead I reckon?

Fun fact: The 2011 article Cowboys and Pit Crews (https://www.newyorker.com/news/news-desk/cowboys-and-pit-cre...) points out that modern cowboys actually spend a lot of time on communication and checklists.

That’s a gross generalization, but gives you the flavor. I couldn’t do what they do (huge budget, low incrementalism) and would hate the environment. But they can’t do what I do, and when hired to do so, typically fail. Not because they are dumb, or lazy, or foolish, or anything negative — typically they are none of those things. Just haven’t experienced the startup environment.

There's a big difference between the product strategy side (v0 of N different chat products) and the tech side which is that all those products are made of many of the same components arranged differently.

i'd say that if you plan on scaling, you need a bit of both. a lot of tricky scale/process/architecture questions have effectively been "solved" in big orgs, it's useful to have people who can bring this experience

to take a completely random examples: setting up a performance improvement plan, performing incident post-mortems, organising oncall rotas, branching strategies when you have a mix of small customers on standard product and big accounts with customisations etc

Quite likely to happen of the founders / existing hiring managers have no idea themselves how big corp solved these problems.

Meanwhile, good startup engineers are used to learning new technologies quick, can work across the full stack, can own all aspects of their app/feature, work without much direction, never mind a formal spec, and generally are used to solve problems over shipping code.

Often, the key drawback with startup engineers who are available after working at one or two startups, is that they pick bad companies and do not really understand the business end of the equation. However they are still excellent problem solvers.

This is from my experience as a hiring manager who has worked at multiple startups and now works for a large public tech company.

There aren't many good startup engineers with experience at successful startups who are floating around, especially from when the company in question was actually a startup.

edit: i re-read, my comment "failed startup engineer" may have read differently to what i intended. I meant they worked at a failed startup, not that they were a failure. It's largely unfair, but people do seem to think people who worked at a successful company are better than those who worked at a failed company.

For example, a pattern I noticed among the pool of BigTech engineers recruiters would pitch to me was the following. The engineer would join a startup with an immediate promotion in title, and then 18 months after the fact, they would jump back to BigTech to a higher level than the one they had when they left. When you asked what they delivered at the startup, it was clear that they didn't do much or often couldn't correlate the impact of their features to the ROI of the business. Nevertheless, the title upgrade in their resume helped them game the recruiter search and the BigTech ladder.

https://www.teamblind.com/ is full of recommendation for similar strategies that BigTech engineers use to climb the ladder.

Also, the good startup engineers aren't floating around, but you can still poach them. You'll have to give them a big signing bonus to cover the purchase of their options, but it isn't a risk to me when they are sure bets; a recommendation from my network for example.

There seems to be a significant number of tech industry employees still floating around that are convinced that instant financial independence is available for all.

This is a stupid view of motivation and competence.

First, it implies people are only motivated by money. At the first startup I worked at, one of the senior engineers had been through 4 successful exits and was in the business to build things.

Second, competence of the engineering org and individual engineers is orthogonal to successful exits. An engineer can successfully ship many iterations of a product that are just a bad market fit and the company will fail. I’d still take that engineer any day over the typical FAANG cog who’s big project was a 2 year tax billing database migration.

It's a fund raising and public marketing trick.

It means your leadership can't think of a way to make the business work other than to get bigger checks from the same size customer base. "If only all our customers could pay us an extra zero!"

Moving upmarket doesn't work that way. They are totally different companies with purchase requirements and habits that will generate tons of work orthogonal to your core product. Spend a few quarters on compliance accreditations so you can tick boxes, multi-month sales conversations where you aren't even sure if you're just there to pressure the real Belle of their ball, etc.

If you can't do it small, you can't do it.

I've been on companies that did the opposite from going small to big. They started big, very big, with Fortune 50 costumers. That meant they hired a small but very specialized sales team with the right connections very early on.

Because the burn rate was very small (due to needing just a few engineers and employees and a small infrastructure) and the sales cycle took months, we could easily develop a strong product with the requested features, and then it turned out when we moved down to medium and small businesses most of the features were already in place all we needed to focus was on scaling the architecture.

Plus, big costumers pay very good and are loyal as long as you don't cause them headaches.

The only downside of this approach is if we hired the wrong sales people, the company would never take off.

The companies I know that succeeded with that strategy either have great starting relationships with insiders in their first sales, and had contracts signed before committing to a big staff, or got into said companies when they were small: If one of your customers turns into a rocket ship and you are tied to their revenue stream, their growth is your enterprise-sized company.

Enterprise sales might not even be all that profitable when it's all said and done: How many other companies are going to try to bid on their business? With their large size, how good is their leverage to squeeze down the profits of the winning bid.

You might have a relatively unique product, the right connections, and end up being Palantir, but it's a very narrow road with steep cliffs everywhere.

You would have companies where you have existing relationships, they love what you offer, and really want to work with you, but the deal just gets delayed by some other priority or reality of their business. The solution they already have is good enough (even if it’s barely good enough), and sticking with it is not actively putting them out of business for the time being.

It’s just reality… just like VC investing, selling into 100 small companies and growing along with some of them is waaaaay more likely to pay off than landing one whale

I'm currently at a seed-stage startup with a few Fortune 500 companies as users. We're lucky to have a great sales team that can bring that business in. If we're solving a problem for them, they're willing to use us regardless of our size, though they do care about some small particular issues around size.

- It saves all the details needed for 1-click, not only your card (which is just PayPal). So: shipping address, name, possibly even 'pre-done' age or fraud checks, etc.

- It 'maps to' the business's API far better than a browser's autofill can do, which only has some random HTML tags and a helluva lot of guessing. (In other words, users won't have to keep filling in the, like, 4 out of 9 inputs that it didn't understand.) Your advantage is that the merchant itself does the integration work themselves - though ideally your API/SDK will make that as easy as possible.

(Essentially, it's just: "user has a third-party cookie for your site, comparable to SSO, and you charge their saved details and call the merchant's API on the backend [or, for small businesses, a Shopify integration or whatever fresh hell the Fast engineers must've gone through]".)

It's an enormous potential market, though that's also true of the shipping industry and it doesn't guarantee big margins. I'm interested to see what comes of it all. I expect something boring like "Yeah, eventually [company X] got big enough, that's why Apple released the Apple Pay Checkout Fields API for JS".

As a footnote: Amazon has actually offered this as a service for ages, which I know because of the precisely one website I used which happened to offer it. If it weren't for the terrible antediluvian UX and the lack of any evident marketing, it probably wouldn't have been such an open goal for these startups. Here, this is what Fast was trying to sell a shittier version of, without a user base: https://pay.amazon.com/what-is-amazon-pay

The reason this is possible for us is because our tech isn’t mission critical for them.

I doubt the CEOs/CXOs of any of these companies even know we exist.

We’ve just been fortunate that a lot of ops teams in these companies need our thing.

So - that has really changed my paradigm of enterprise sales.

Sometimes, if you’re SAP, you need to get whole of company buy-in. But if you’re SurveyMonkey, you don’t

It definitely is hard to have conversations about what isn't going well, even though it doesn't have to be negative or gloomy. Often the disconnect in results is chalked up to external factors outside of your control, which is sort of depressing because if that is true then you can't do anything about it.

It's like when someone encounters a bug in the stuff they wrote and look every which way they can to blame it on the library, framework, compiler, etc.. - I'd rather have the bug be in code I wrote because then I can fix it easily. You can show someone simple data that shows a strategy isn't working, and then they'll spend a week torturing the data to come up with a contrived counter-explanation.

Ultimately, it is tough because part of doing a startup is remaining positive even in situations where it isn't warranted and there are times where the strategy may not be working out in the short term but needs more time to play out. Being unwilling to ever even entertain the idea that what you're doing isn't working seems like it might be problematic though.

As for theranos and wework - i don't mean those kinds of things. I mean standard non-fraud startups. The always positive culture is there, and at least for folks who take some pride in being rational, it is quite demoralizing.

Fraud is not black and white. "Toxic positivity" can enable shenanigans or conceal problems in an otherwise non-fraudulent startup.

here we go, this is late 90s all over again

The reason late 90's start-ups invested the way they did is because they had no meaningful way to track the effectiveness of their ads, much less the payback. A Super Bowl ad for Pets.com seems fine if you can (more or less) guess that it adds a bunch of customers.

Since then, start-ups have built a bunch of tools to track customer acquisition costs and paybacks in a pretty sophisticated way, and some of the obviously crazier ads dies (or at least become more one-off).

But now we are in a fintech/crypto era and nobody really knows how to calculate paybacks once again, because the business model is so new vs. a traditional ads or commerce business (will this new crypto.com user do $1k of transaction volume every year for the next ten? sure why not?)

As a result of all this, we see crazy 'spaghetti on the wall' style advertising again, usually focused in the crypto/fintech space (See: this year's Super Bowl). I wonder when the music stops.

Remember beanie babies? We call them NFTs today.

Remember HYIP and e-gold? We call them cryptocurrencies now.

The point is that crowd behavior, especially markets driven by envy & greed, lead to the same outcome. every. single. time.

this is why guys like Warren Buffett and Charlie Munger keep making money.

Who cares? Champagne on the Concord, and let's order a bunch of Starfire servers from Sun Microsystems!

I wonder if any doomed startups will order a rack from Oxide Computer. I hope Oxide's primary customer base is established companies that actually need serious efficiency at scale.

At least publicly, Fast never addressed this, and insisted on requiring the user to log into Fast to make a payment even when it was a worse option.

Browsers like Safari are explicitly designed to prevent people from remaining logged into third party sites like Fast. All this was just brushed under the rug and instead it was just a bunch bluster on how Fast was a revolution.

At least Bolt allows payment via ApplePay, and seems more about doing whatever it takes to maximize each seller’s conversion, rather than having an ulterior motive to push its own brand everywhere.

The two of us ditched it when we realised how inhospitable the economics were, but even then we knew Fast's shitty play was bound to fail, and I heard the news from my prospective cofounder sending me a text ("we called it!") when it happened...

“I could not be happier or more proud of my teams and what they have accomplished.”

If the company wasn’t successful, then that’s partially on engineering. As employees, we win as a team and lose as a team.

It seems like they were way overbuilt and should have gone much slower from a hiring perspective.

Perhaps these are just words that folks say to put best light on things as they leave, but it strikes me as disingenuous and lacks that ownership mentality that engineering leadership should display.

You could put that as subtext for pretty much every story you read. ;-)