Ask HN: How did your startup change after an exit?

281 points by after_the_exit ↗ HN
Hi HN

I'm an engineering VP in a (maybe) unicorn looking seriously at an exit and the vibe has ... already changed.

Looking at the current climate, I am probably going to be able to pay off my mortgage and send my partner to grad school, but financial independence or FYM isn't on the cards. I like it here, and am not planning to move on yet.

I've been wondering where the stories about what happens (what goes wrong/right) after an exit, like an IPO.

What should I be looking out for after the exit? Any experiences from senior engineering staff? Or even good blog posts or books?

Thanks

160 comments

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The book "before the exit" seems pretty relevant for your scenario
Depends on the exit, I watched an amazing culture be crushed after an acquisition. So sad
I imagine it widely varies depending on a multitude of factors; how many employees are equitably compensated, whether it’s an acqui-hire or a tech/business value acquisition, if the acquiring company/organization plans to take over any leadership duties, etc etc.

Generally though, most of not all were just thankful to not have to depend on VC. Revenue wasn’t high enough to keep the company afloat, and the value in us was largely in our established brand within the market combined with a rather active user base.

Fortunately, most everyone who was in the company pre-acquisition are still around over a year and a half later.

I don't have experience with an IPO, but I did work for a startup that was acquired by a publicly traded Fortune 500 compnay. Short version is that it wasn't a pleasant transition.

The startup had a niche product in higher ed and had done a really good job cultivating their relationships with customers through top notch customer support and rapid iteration on the engineering side. Typical startup strategies for the most part.

Post-acquisition, the support team was essentially goaded into quitting by management, only to realize that the product was far more sophisticated to support than the other products in their portfolio, so they wound up having to rebuild the support team. This was when we realized upper management was a bunch of morons.

On the engineering side, they shifted our product development focus to making the entire app a bunch of SPAs because reasons. The core engineering leadership left, and the new hires that were brought in weren't as good. Apathy set in, the company started stiffing us out of promised bonuses, and I left.

What I imagine is true for both IPOs and acquisitions is that most publicly traded companies usually care a whole lot more about the bottom line than well-funded startups. Getting rid of the crazy retreats and in-house chef is one thing, but when companies start getting squirrely about compensation, it's a good time to think about what's next.

The last company I was at had an exit and it was great for the company's growth. There were some culture changes but for the better.

@after_the_exit can you give us a hint of this unicorn so we have more context?

Be ready for non stop politics and a survivor like atmosphere. The first thing that happens after a merger is they look for people they can fire to save money.
Those are called "synergies."
It was incredibly odd. They paid a good about for our company, then just scuttled it. Didn’t use the source code, sold the hardware, neglected the remaining employees until we left one by one.

They absorbed a few employees who are still there and are just as confused as none of the tech they spent so much money on ever got used.

Maybe it was somehow a giant tax write off, or just buying out the competition?

Or maybe they did one of the investors a favor. Follow the money.
Maybe it was cheaper to buy the competition than to outspend them in customer acquisition?
They were incompetent. Some VP had it in the pipeline then fell out of favor after the deal went thru. Lots of possibilities.
ScreenHero?

Broadcast.com?

I thought ScreenHero was an acqui-hire and one of the guys was still working at Slack?
I wonder if this is a catch-and-kill. Was your company a growing competitor? I'd imagine, for example, Facebook would rather consume budding competitors (cheap) than renovate their entire business model (expensive).
This same exact thing happened with my startup. I was surprisingly the second engineer to trickle out, which is only surprising since I didn’t expect someone to leave before me. The clash of cultures made it difficult to integrate; different geographies, age brackets, experience, practices, tech stacks, you name it.

Overall, I agree with the theories proposed in response to your post — either incompetence of their leadership or favor to an investor. In our case, it was a bit of both and the latter part was clear beforehand. Their crudely constructed plan was to take our industry data to improve their models, but they were not privy to any of it so effectively all they bought was a bunch of tech they couldn’t manage to integrate since all of our tech leads left in the first two months. That’s what they get for not providing an incentive to stay at all, which again hints at both incompetence and a favor.

> age brackets

Careful: I don't imagine this was your intent, but we need to eradicate ageism from our industry, not promulgate it, even as a throwaway comment.

Haven’t you realized that people don’t like being told what they can and cannot say based on yet another -ism?
Are you asserting GP shouldn't be able to comment on ageism because people don't like being told what they can or can't say about ageism?

Just some lovely irony this morning ;)

It all depends on the acquiring party. Whatever you decide to do, do not put too much stock into promises by management (either of the company being acquired or the one doing the acquiring) about the situation post acquisition. History has shown over and over again that those promises are worth absolutely nothing.
And also understand that it's not because they're scheming bastards, but things change and the wave can't be stopped.
Sometimes they really are scheming bastards.
Or they're innocent bystanders with many percents of preferential shares, who simply don't realize that the commoner employees under them have only a fraction of a percent of regular shares, that will all be made worthless by their actions.
I highly doubt you will find a shareholder with 'many percents of preferential shares' who don't know exactly what they are doing and why.
Also, don't put too much stock in stock if you don't get an immediate & liquid payout. Stock you can't sell is worth exactly 'nil'.
If anyone has any post-exit but not yet liquid stock that they would like to sell me for $0.01, my contact info is in my HN profile.
They may want to sell for $0.01, but they may not be able to and you won't be able to buy. See also: articles of incorporation, minutes & bylaws, shareholder agreements.
Of course. But in many cases they will. And even in cases where there are restrictions....there are often things that can be done. But that's not really the point.

My point is calling something illiquid worth "nil" is often silly. Maybe don't consider it worth its face value. Certainly don't go spending money you don't have yet. But automatically writing everything down to zero is dumb.

> not yet liquid stock that they would like to sell me

That's... isn't that impossible by definition?

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When it comes to company stock liquidity isn't really binary. There are degrees.
You can't transfer the stock, but you can sell a contract promising to sell at a specific price once it's liquid.
Except if the company has a right of first refusal.
And in some cases, eg financial services companies, this can be a major violation.
If I sell it for $0.01 can I write off the difference?
Actually, I’ve heard from friends with extensive careers in finance that the value deduction for illiquidity is 30%. I’m sure this figure varies based on how far from liquidity said asset is likely to be.
That's also assuming you can find someone to buy it.
Rest and vest... rest and vest...

https://www.youtube.com/watch?v=6BaoxI75TRs

I couldn't watch that clip when it first came out. Too close to home.

He got a contract and nothing to do? Perfect, it's free money on the table and he can also take another paid job at the same time! <3
It’s soul destroying, I’ve worked on contracts where it took 3 weeks just to get an account before I could start work. I hated it.
At least they made it clear to him that he had no responsibilities. That's better than it could be.
If you are a vp it is very important to develop a relationship quickly after merging because your position is usually the type that get absorbed.

Usually it's a process where the company tries to push what you have into an existing product. The remaining staff support that product until the switch over happens. Some are forced to stay with option vesting deals. But usually happens over two years.

Imposter Syndrome is a phenomenon I've observed post-exit. With sudden success some people believe they'll be exposed as a "fraud", despite evidence of their competence.

The longer the vesting period, the more they have to lose with each decision. So they simply stop taking risks.

Most people left within 2 years. Founders phoned it in immediately after the acquisition. We were a small, nimble company and were acquired by a HUGE corporation, which ran us to the ground.
If the stock starts tanking after an IPO, and the company is in upheaval, there might be blackout periods where you cannot sell your stock and can only watch as the price plummets.
People spent a lot less time working and a lot more time checking the stock price and estimating their net worth. As the stock headed south, and the press started writing mean articles about us, morale went south.

Lunchtime talk started to focus on money. Some people nursed unrealistic fantasies about an upward turn in the stock. Those of us who were more cynical sold our shares earlier and were happier in the long run. Eventually most of us moved on to other companies. The company is headed down the drain, but many of us are still friends. I bought a condo.

Spooky how similar this sounds to my own experience.

I would add as well that if the acquiring company does not have a solid plan for how to integrate your team/product... you're gonna have a bad time.

100 virtual upvotes as this is my exact experience for 2019 after an acquisition.
I don’t think it makes sense not to sell your stock from a portfolio theory standpoint.
Yeah unless you like unnecessary risk, or have some solid inside knowledge that something amazing is about to happen, you should sell as soon as you can. Ask yourself if you would buy shares at that company if you didn't work there.
> Ask yourself if you would buy shares at that company if you didn't work there.

Worse: if you did work there. You’re already heavily invested in other aspects of your life. Do you really want to put more eggs in that basket? The answer could be yes, but be aware of the risk.

I’m pretty sure that people who say things like, “if I’d have invested $10k in Apple in 2008 I’d be a millionaire” are so far from right that they aren’t even wrong.

Nobody holds on to a winning lottery ticket that long. You cannot exit at the top and trying to do so will drive you crazy.

I think you and your friends were right. I had a coworker that was selling his stock as fast as he could and it finally dawned on me that he was doing the right thing. When you work at a place, you are investing your time an energy into an idea. If you hold stock in that place, you aren’t diversified.

If the stock tanks, layoffs are more likely to happen. And then you are broke and jobless. There are very few companies you can work for where your own stock is the best bet on the stock market, and second best is often pretty darn good. Gamble on a different income stream.

There is no right or wrong, it also comes down to personal preferences. Many seriously rich people probably havent been diversifying that much.

Also, a middle ground is possible. Sell some of the stock for safety, and take risk with the rest.

Seriously rich people, yes.

But comfortably rich? You’re more likely to get there with diversification than concentration.

I dont really see the difference, wealth is wealth. Also what is enough money varies from person to person. In a low income country you can retire nicely on couple of millions, somewhere else you need ten millions to have a nice house and lifestyle.

Whether you want to take bigger or smaller risks is up to the person in question.

"Seriously" rich people got lucky.

You shouldn't bet on getting lucky.

That's focusing on a small % of rich.

Even to keep among the 'rich' list assuming you inherited it all takes enormous talent because money inflates away.

There may be a bigger incidence of luck (I am not sure of this either btw - almost all the contacts you get as a rich person are very much the effect of you being rich) but unless you're well prepared to take full advantage of it, there will be no returns.

What I will concede though: Luck when you're poor might mean securing a week of food. Luck when you're a billionaire probably means the stock market goes on a 15 year bull run.

"Enormous talent?". How about a good investment firm and a high paying job because your status automatically grants you a 6 figure salary. It's extremely easy to be rich and stay rich in the us of a
There is zero talent involved in investing such that you beat inflation. Inflation rate hovers between 1% - 3% per year. Stock market returns hover between 5% - 10% per year for fairly conservative choices like an S&P 500 index fund.

There is nothing luckier than being born rich. Treating it as some sort of skill to remain rich is part of the dysfunction in US society where wealth is equated with virtue & character.

I prefer to being born smart over being born rich.

If you are rich, but not smart -- it is hard to avoid temptation to invest into risky projects. It is hard to identify people who just want to drain away your money.

Right - that is moving the goal posts though: This was talking about being in the top x% of the rich. If you don't keep working at it, you will drop off that list pretty quick. It is pretty much a slippery slope when you don't know how to manage money. And there is probably a very very miniscule portion of the top 1% of rich who live on index funds. When you're that rich - these don't work the way it works for us.

I did acknowledge the luck part in being rich. I do acknowledge it is far better than being poor. But if you want to remain rich and ensure your generations remain rich, that's a ton of work.

PS - seriously rich might mean different things for us though :)

Since you're focusing on "normal" rich people: One of my best friends is smart but was extremely unwise when he was young.

Did a lot of drugs, didn't pay attention in uni, didn't work, didn't build the habits of a successful person. Still, he got one chance after another, and in his late 20s he actually did. From what he told me, realizing how insanely privileged he is was one of the major influences for him to change.

But still, a normal person would have been long out of chances at that point, and would fight serious debt and worklessness without any support.

You maybe cannot afford to be a total wanker forever as a rich person, but you certainly have a lot more leeway in your wankiness.

I definitely agree - luck runs out faster than money when you're poor. Or the chances will be to secure basics rather than your future.
Well I don't like when people tell me what I should do or not. Also when it comes to gambling. And I also see nothing wrong if someone likes to gamble. Better wirh stocks than with something where you are statistically guaranteed to lose money, like lottery.
You are statistically guaranteed to have worse expected value as a retail stock trader than at the blackjack table.
Huh? You’re highly unlikely to go to zero making trades.
The same is true for Blackjack. The house has a 0.5% edge if played properly, so as long as you're not making bets that are most of your capital, it'll take a long time to go bankrupt.

Meanwhile, trading stocks on margin...

Remember: Stocks that don't pay dividends are not an asset, they are a time capsule you hope is bigger by the time you unearth it.
I have no idea what you base this statement on. You are absolutely likely to go to zero by continuously making market trades as a retail investor. Every trade has two sides and the side you're trading against is for the most part significantly better informed than you. That's why Robinhood makes its money by selling their 100% retail order volume.
Tech stocks outperformed market even when market was on a historical bull run. This might not (and probably won't) hold true in the future but it does bias all our current anecdotal samples.

I think the FAANG people I know who supposedly make 500k/yr only got to those numbers by never selling a single share and then reporting total net worth including appreciation divided by time worked. Their base salary isn't actually that crazy. People who sell all their shares for index funds didn't do as well.

I am guessing this isn't what you wanna hear but, They don't do a post hoc calculation.

It is usually the salary + stock award that will vest over 4 years. For most companies with a flat vest, the total will come to 500k/yr for certain levels.

The appreciation is all yours. Future perf bonuses which will be each 6 months or a year are on top of this. Some companies do adjust for what you're making in that year and cut down the perf bonus (In a previous company I once got a promotion without any stock because our stock had tripled in the time...) - but these companies have a serious growth outlook. Once the stock flattens, there will be a major drain and they know this.

Some people supposedly working for Netflix have total comp mostly in cash within $100K of the $500K figure you put out. But of course if other companies total comp isn’t that good in future, Netflix won’t have any reason to give out that much cash salary either if it’s true.
> Tech stocks outperformed market

On average over a long period, but in this case you are invested in one company over a very specific entry date and period of time, with some critical periods blocked from selling.

Facebook peeked around the end of July 2018 at 209$, if you got stocks then you might be in trouble, or already sold out after seeing 124$ during December 2018.

Exactly this. Best to cash out immediately. If you are serious about investing, then build a diversified portfolio. This might include your employer but certainly at a much lower asset allocation rate.
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My friend made a fortune with Ethereum because he bought in early and forgot his password.

When it got up to around 700, he started to get frantic, figured out how to crack his own password, and sold it all.

He's from an Indian family so poor that they didn't own any books growing up, and he made in the low seven figures. But if he had known his password, he probably would have sold it early for like $10k.

I sold 500 eth for 12$ a piece after the drop from 20$ and felt like a genius.

Mind you, I make about 30k after tax. (Not in US)

I remember selling 1 BTC so I could buy an AMD Radeon 290x to mine even more. Still have about .5 BTC left and just can't part with it.
> Nobody holds on to a winning lottery ticket that long. You cannot exit at the top and trying to do so will drive you crazy.

The only people that do hold on to a winning lottery ticket that long are the people for which that $ would not significantly change their lives.

I bought AAPL at ~$20 pre iPhone, AMZN at ~$50. And sold them when I doubled or tripled my money. The only reason the choice to sell those looks stupid is hindsight. I'm still happy I sold, because I'm not independently wealthy. I used that $ for good purposes that impacted my life at the time. I cashed out for an immediate, excellent ROI instead of risking it.

Edit: If I find myself in a position at a startup where I could liquidate shares for a currently fair $ despite the strong potential for growth in value over time, I probably would, in order to de-risk the situation. I'd sell some and keep some.

I think this is true for most middle class people, because as soon as you have say $100-$200k you don't want to keep 'betting' and you'd rather put that into a house deposit or pay off the mortgage.

However if you are already a millionaire you might as well keep holding it.

A reason why the rich can get richer, because by holding you get tax-free reinvestment of the current value. By selling you pay tax and then get to use it for something else. This plus average stock returns beating other investments or paying off the mortgage.

Exception is with crypto and 'true believers' who held and held. Maybe they'll never sell their entire stash.

Is there any way for a founder to turn the acquisition/liquidity event into a half decent moment for employees of the startup?
Yes, but they probably have to want to do it. I have heard that this happens a lot but that’s probably only anecdata.
Would still be good to hear even if it's anecdata if you're able to share?
It's not only talking about money. According to this classical experiment [1] it reduces productivity even while solving problems, because the prospect of a reward occupies some of your brain's problem solving capacity constantly.

[1] Sorry this was the first link that came up in Google: http://thepsychreport.com/books/how-incentives-hinder-innova...

Our founding team left or were made to leave by the acquirer. For one year everyone kind of relaxed because we all made money. After that our management team left had no vision because they were bunch of execs hired recently. They lacked innovation and kept beating around the bush and left in 2 years of the acquisition. At this point most of old timers left the company because of lack of innovation or anything to do. I becomes like a graveyard.
Been through both IPO and acquisition, but not life changing money.

The IPO was a lot of fun. We were still in charge of our own company culture. I wasn't privy to all the financial information, but we were told the company was skirting profitability and it would've been just a small push to get there. People worked harder afterwards to try to get to profitability. You also realize stock price has nothing to do with your day-to-day work - it's not in your control.

The acquisition was... well, a lot of us didn't stay. For one, a lot of people's RSU's had already vested. The acquisition meant a company cultural change. 1/3 of us left initially, some people were waiting for their RSU's to vest. I think in all, 2.5 years after acquisition, only 1/3 of the original staff is still there.

So depending on the exit, really understand what your yourself want out of life and career. It's ok to be selfish in this scenario, as not everything will be in your control, as others are also considering if they want to take large sums of money, even if it's not FYM. For being higher up on the corporate ladder, be honest and truthful to your reports. Don't make promises you can't keep.

Looking through the comments, has anyone has a mundane or positive experience? Or is it always bad? Not anywhere near having this kind of problem, but fascinated
I've been part of two buyouts, have joined recently bought out teams, a recently IPOed team, and part of four teams looking for a buyer.

I'm talking for personal experience from someone mid-career that moves around a lot in the industry.

The best buyout experiences are the slow embraces instead of a big bear hug. A slow embrace allows both sides to grow while they learn how to support each other. A big bear hug will suffocate the purchased company while all energy is spent assimilating instead of helping customers.

When you say slow embrace, do you mean the acquisition happened slowly and with transparency or the acquirer handled it well? This is a problem I’d love to have to deal with tbh
Post-acquisition example: Acquirer has a VP that's pushing the deal. VP makes promises to make the deal seem as attractive as possible (eg: X will improve in Y time). New team is pressured to move quickly. New team uses the honeymoon period to flex all of their political capital. Existing teams get frustrated as their work is de-prioritized/marginalized. Culture clashes happen if new team isn't silo'd from existing teams. And so on...
The more the acquirer leaves you alone, the better it is (usually).
I work for a company that is #2 and chasing hard against our #1 competitor.

That competitor was bought in the last couple of years and we all thought this would be our chance to go #1 as their head office inevitably screwed it up somehow.

That hasn't happened yet. They're still #1, we're still #2, and the gap hasn't closed. The only sign of trouble might be that their product, which was already lagging, hasn't seen a major release in that entire period.

An exit is not always bad. Big companies have vast resources and established sales channels. Acquired companies can offload peripheral corporate functionality to their new parent and focus their efforts on core competencies such as research and development.
One thing to look out for is that until you’re wholely absorbed in, expect your parent company to offer high powered but disgruntled or burnt out managers and individuals from elsewhere in the company positions in your department. They’ll do this in an attempt to retain these folks by offering them an interesting new challenge, but in the vast majority of cases, they’ll spend a few months to a year half-heartedly trying you out and then leaving anyway.
The only exception to this is if your company actually is a different atmosphere from the parent company and the people coming in have some reason they'd fit better there than in the rest of the company. I had good luck collecting dissatisfied high performers from a parent company, but they always went through an interview process, and I always started by having them take two weeks of vacation and only then come back for on-boarding, as though they were new hires I had just successfully poached.
I got brought-out by an organisation who purchased me to fill a hole in their main software product. Their plan was to take my 800 clients, deprecate my software, and force everyone to move to their platform. Problem was a) my clients liked my software, b) their platform was 3x more expensive, c) their platform was a nightmare to configure.

I was tasked to sell their monstrosity and it was hell. To see the faces of my clients as they looked at this 'new' platform was very demoralising for all concerned. We ended up with about 20 clients who stayed and eventually the organisation just got out of the industry segment all together, and they gave me a redundancy package.

This sort of situation is one it the pillars of my thinking that the sale is and always has been about the founders getting rich, and everyone else gets a pittance compared to what is asked of them.

But it sounds like sometimes the founder is fucked too.

They buy your product out from under you. They are never, ever going to be as emotionally invested in it as you were. To you it was a pet, possibly even a child. To them it’s just an asset.

How often has the product really gotten better after a purchase? Investment, sure. Bank loan, all the time. But how often to mergers result in good news for the customers? Maybe, possibly, if the products complement each other. But even Bitbucket was better off before, from a customer standpoint.

That's right. They imposed their will on the customers and they responded.

It's always about the culture. They were just corporate.

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We had a bizarre experience. Our acquisition was motivated by the value of our contracts and came with a number of earn out goals to ensure that management kept these going for a year. All of the money for the acquisition was held in escrow for this time period, with payouts at the end of the year.

Our executive management was very savvy and negotiated that the acquiring company couldn't interfere with our operations for the first year in any way that could threaten our meeting the earn out goals.

The net effect was just weird. In many ways, nothing really changed for a year. In other ways, everything kind of ground to a halt because there was no motivation to do anything and no new management to steer.

I left at the end of the year.

How much you got out of it?
Enough that I don't technically have to work, not so much that I won't keep working.
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I didn't get life changing money but got good money. I like the new position, I've had some amazing opportunities. But it's high stress. The market segment is hot and the buyer is betting on us. It's great in the way a huge messy challenge is great. It's hard problems. For me, I got stock buyout from sale and on hire stock grant that I have to stay for some years to earn out. I plan to stay. Altogether maybe 700K. Maybe more. Not sure. I feel pretty good but it's intense. For our size startup it's hard to imagine how it could be better than this. Nothing is easy.
It is always an interesting time. You didn't say "what kind" of exit, that is important.

In one, people go from owning options in their company which is private to owning options in another company that is also private. In the two companies where I have seen that happen things didn't change a whole lot but the "new way to do things" which is to say the way the acquiring company did things was sufficiently different than the way the acquired company did that there was churn.

In one the "exit" is really sort of an aquihire with no value transferred, rather the employees are all given some form of retention package depending on their perceived necessity to the success of merging in the acquired company. In those, people are typically both happy to still be working and conflicted because they now feel "trapped" as the only way to get value out of their previous investment of time into the startup is by working through their retention.

The rare, but happier version, is the one where stock options become "tradable" at some future date for non-zero amounts of money depending on the current stock price of either the acquiring (and already public) company, or the rarest where the company itself goes public.

A lot here varies by scale. At Sun I watched[1] a number of people become "overnight" multi-millionaires. Some people it didn't change at all, others became insufferable prima donas, and a number basically scaled back their work while they 'rested and vested.' A number of folks left to start their own companies (some as groups like Legato) now that they had enough money to self fund. Some, like John Gilmore, went off to do advocacy because of all the crazy stuff going on in the Crypto wars.

Bottom line is that if its a big uptick in wealth for a number of people they will all respond a bit differently. Life will be different.

For me, I came to recognize that there are many levels of "wealth"

Perhaps the first is when you have enough extra to insure your kids can go to the college of their choice (within reason I suppose). This can empower one to take some riskier bets and reap potentially some bigger rewards.

The next is when you have enough to send your kids to college and you can pay off your mortgage so that your "burn rate" is manageable regardless of your salary. This often empowers people to speak 'truth to power' since they don't really care if their truth makes those in power so uncomfortable they are asked to leave.

The third is when you own your living space outright, your kid's college is taken care of, and you have diversified the surplus into an investment strategy that is kicking off enough returns to cover your nominal burn rate (taxes, insurance, food, gas, car maintenance, home maintenance, etc). I used to talk about as being 'raman rich' much like a startup talks about being 'raman profitable' meaning that you don't have to work but not working means you might not get to take vacations or invest in other interesting endeavors.

So how your life changes will be based on both how you respond and how those around you respond to the way you respond :-).

In the first decade of the 2000's one of those Sun people who had turned into an insufferable prima dona came by looking for a job. They had mistaken (or over estimated) how much of their new wealth was because of what they did and how much of it was just luck. As a result they embarked on a number of risky startup ideas and I suspect never took anyone's advice on solving the hard problems. As a result, a string of failed startups and a trail of people who would listen to their pitch, nod politely and decline to participate. They ended up selling their house, moving to the midwest near their ex-wife's parents so that they could visit with their kids. Not a happy story.

[1] Not me though since I had started on the Monday after they went public.

Love the term “ramen rich”. Sums it up well, happened to me.
How is the experience of being "ramen rich"? Care to expand how it changes your day to day work or relationship with work?
I would identify myself as “ramen rich“. Specifically, my post-tax living expenses (rent, food, gas, entertainment, ...) are ~30X my liquid portfolio, all invested in a bunch of diversified index funds that throw dividends/interest income, as well as increasing their NAV.

It improved my life in the sense that I don’t feel the pressure of having to keep a job I don’t like: I can quit and not work for several months and nothing will happen. Even if I don’t actually quit, just the thought of me being able to do it gives me a lot of comfort. I suffered significantly from this in the past, where I was stuck in non-ideal work situations for financial/immigration reasons.

But it’s far from being truly liberating: I constantly think that a significant drop in the market could jeopardize my position (and I can’t move more than 30% to fixed income investments, since I am young enough that inflation is otherwise going to eat all my capital away), or a crazy medical emergency force me to go bankrupt (and I say this as I have a pretty good health insurance plan covered by my employer).

And, I think it would be nice to have more money for discretionary (e.g. more traveling) or unforeseen expenses.

The source of the 3.5-4% “safe withdrawal rate” theory suggests that that is designed with historical market declines in mind, so you might be better immunized against that than you think.

Side note: You have the ratio inverted and probably should be thinking of the portfolio income as pre-tax.

I am familiar with the Trinity study. Even if that is going to be true going forward (which I am very skeptical, as I think global warming is going to have a major impact on market returns over the next few decades), I am young enough (32) that I really can’t trust these level of frugal expenses to be maintained for the rest of my life.
I was an early employee (<100) in a scale up. Late in my first year I “took one for the team” after some typical startup personnel drama, and was offered equity for keeping the ship steady. Fast forward past an IPO lockup:

Love my job. Team is great. Get on fine with the board, work pretty closely at times with almost all of them.

What I’m surprised at was/is the difficulty of choosing how to invest the lucky windfall capital (I diversified out as soon as I could, heard enough horror stories about not doing it), I think that it’s harder than if I’d been independently wealthy - far less room for error, fewer options and far less support from private bankers and the broader financial industry which helps people with an excess of capital. It’s going fairly well now after some time, but there was a lot more cognitive load than expected.

For me, I am facing a rebalancing of personal goals - they’ve come second to my work, and the health costs of that have been more clear over time.

At work this means I want to achieve more impact in less hours (why didn’t I think of that before?), delegate more effectively (see above), and do things with more strategic impact (which also happen to be more fun).

All of these things were in my power to do before. I’m not even sure it was the “ramen rich” thing that made the difference than having external validation during discussions with bankers and investors during the pre-IPO phase.

It’s also become clear how much the business values my work, as I’ve been navigating these changes (from “not much” all the way to “a lot” ha ha). With a lot of social capital it’s working out.

I guess that some colleagues were big shareholders. Some left fairly early on to fulfil dreams, some hung on until irritations built up enough to force a departure. Two years later, I miss nearly all of them a lot, they were my “seniors” and direct peers, replaced by talented but less battle-hardened individuals who - mostly - only have the successful pre-IPO phase as reference.

Newer, driven, engaged, staff do ask relevant questions about reward for their level of commitment which cannot be answered except in platitudes. There are more smart, enthusiastic 9-5 types who want to be part of a success rather than build a success. These people are my challenge - motivations and communication styles (meetings! goddamn meetings!) have to be different, and leadership tactics that worked need serious adjustments in the years to come.

Our 500 person shop was gobbled up by the same company a few years after you. The reason why we were gobbled up - we went public and share prices tanked in the Enron time period. I think I was in the first 100 or so people, which after converting the stock and waiting a few years, was enough to put the devs and other technical folks in that first or second band. It was interesting transitioning from 500 to 80k people or so. (So many timecards. Crazy it was easier to order a NAS than a single hard drive.)

Having no loans was really empowering. Even with that - it amazed me how much 'normal' living costs. We've not hit that ramen rich stage. Our kid is half way through college... and the costs are ridiculous as we will launch her with no loans as well.