Live data from Hacker News

No, You can't retire rich at 30 if you sell your startup

tonywright.com

51–60 of 221 posts

Re: No, You can't retire rich at 30 if you sell your startup

#51
> There are too many mechanics out there to make sure that the folks taking the real risks (investors and founders) make the real money.

If a founder invests little to no money in the startup, what is the founder risking that someone working under her isn't? One could argue that employees are risking more - in hard times they are more likely to be out of a job.

Re: No, You can't retire rich at 30 if you sell your startup

#52

I don't think stock options have "zero" value. For a lot of people working on a salary it's hard to save money, so when a startup sells and an employee gets a sizable chunk of money from the sale, it's huge relative to their cash-flow perspective.

Except a liquidity event rarely happens. When they do, it's often a shell game for the investors to mask losses. The early stage employee's options are from the common pool; the investors get preferred options which are paid out first. Generally it's quite easy for the board to zero out employee options if things aren't going as well as hoped.

Many years ago, at the first company I worked for that IPO'd, I think I was something like employee number 30. Employee number 1 was a good friend of mine, and after the event we and a few others decided "I'll show you mine if you show me yours". Jewel was big at the time, total honesty was all the rage. Now I had made "a bit" of money on my stock options, not an amount to be sniffed at, but far from a life-changing amount. Think on the order of, a car, or a year's tuition, or an amazing vacation. What was shocking tho' is that we'd all made that much. We all had exactly the same options package.

Executives hired well after me, mere months before the IPO, were buying racehorses. Go figure.

Re: No, You can't retire rich at 30 if you sell your startup

#53
post #52

Earlier quoted context omitted.

Except a liquidity event rarely happens. When they do, it's often a shell game for the investors to mask losses. The early stage employee's options are from the common pool; the investors get preferred options which are paid out first. Generally it's quite easy for the board to zero out employee options if things aren't going as well as hoped.

Many years ago, at the first company I worked for that IPO'd, I think I was something like employee number 30. Employee number 1 was a good friend of mine, and after the event we and a few others decided "I'll show you mine if you show me yours". Jewel was big at the time, total honesty was all the rage. Now I had made "a bit" of money on my stock options, not an amount to be sniffed at, but far from a life-changing…

Yeah. I've worked at a company where I was middling employee 250 but had the same number of options as important employee 8 simply because I was bros with the founder. I think hackers think the non-technical side of the business is going to be merit based and "fair" but that's generally not the case in my experience.

Re: No, You can't retire rich at 30 if you sell your startup

#55
post #49

Earlier quoted context omitted.

Yeah, I'm not getting where that number comes from. (And I love the suggestion that it's merely "upper middle class".) Personally, I can live a pretty nice lifestyle on "only" a couple thousand in disposable income a month. I really can't imagine what I would do with $20-25,000 / month to spend. With that in mind, I tried a few numbers in the spreadsheet. Just to be more "realistic" I dropped the payday back down to…

Also, perhaps you are young and naive like me and don't think about the real cost of kids ;)

Or maybe I do have a child and have figured out that you don't actually have to send them to private school, pay for their college (my parents didn't for me), buy them a new car for their 16th birthday, etc.

Re: No, You can't retire rich at 30 if you sell your startup

#56
post #41
post #2

...where retiring rich is defined as spending $300,000 annually. I'd personally move somewhere cheaper once my income no longer depended on my location.

> "Let's assume you want to live in a major metro area, send your kids to private school..." That's his problem. When we moved to this country, my dad had an H1B visa and was making far below what an entry level Google employee is making. Nonetheless we had quite a comfortable life: rented an apartment in a suburb with a good school. Later, my parents (both of them finally rising to market rate) were able to afford a…

Agree, except the single family home.

Because the quality of life in US apartment buildings is appalling. I don't want to hear every step that my upstairs neighbors take. I don't need to know when they go to the restroom in the middle of the night. I don't need my downstairs neighbor ask me not to walk after 10pm.

This is ridiculous. I'll live in a US apartment once the sound insulation issue is resolved (hint to US architects: It was solved by 1930 in the rest of the world).

Re: No, You can't retire rich at 30 if you sell your startup

#57
post #44
post #9

As someone who just witnessed two non-founders of a startup that had a recent IPO become wealthy enough to retire -- B.S. You can do it with stock options (even without an IPO). Tony seems to be making a binary argument: it's not guaranteed, so you may as well give up on the idea. Of course I'm doing it for the money. I'm also doing it for other reasons. Did someone die and tell Tony Wright that the world is only com…

I couldn't agree with you more sabat, it isn't an either or scenario. I'm hoping for my first success to just be a springboard into more money making ventures.

A good point that I'd thought but not expressed! Who says any one startup experience will be your only one? If you like startups and the kind of people they attract, you'll want to spend some time in those kind of environments. It's not wham-bam-thank-you-startup.

Re: No, You can't retire rich at 30 if you sell your startup

#58

I don't think stock options have "zero" value. For a lot of people working on a salary it's hard to save money, so when a startup sells and an employee gets a sizable chunk of money from the sale, it's huge relative to their cash-flow perspective.

I've heard the same argument about making interest-free loans to the US government so you can get a refund later. I don't buy it there, either.

Re: No, You can't retire rich at 30 if you sell your startup

#59
post #48

Earlier quoted context omitted.

Yeah, I'm not getting where that number comes from. (And I love the suggestion that it's merely "upper middle class".) Personally, I can live a pretty nice lifestyle on "only" a couple thousand in disposable income a month. I really can't imagine what I would do with $20-25,000 / month to spend. With that in mind, I tried a few numbers in the spreadsheet. Just to be more "realistic" I dropped the payday back down to…

I seriously don't mean this in an insulting/trollish way but I think you are either lacking imagination or underestimating how quickly you can adapt to a richer lifestyle. Given you are even here and thinking about entrepreneurial rewards I'd guess the latter. On the other hand perhaps I underestimate how... modest you like to live? Whilst I also raised my eyebrows at "upper middle class", I know people in that range…

It was more of a rhetorical device. It's not that I can't imagine how to blow through tens of thousands of dollars a month. It's that that lifestyle just isn't appealing to me.

Re: No, You can't retire rich at 30 if you sell your startup

#60
15% tax on $4M is only if you live in a state with no capital gains tax. In California it would be 15% + 9.3% = 24.3% - this makes a big difference.

State by state rates as of a few years ago: http://www.thereibrain.com/realestate-blog/2007/10/capital-g...

Luckily, my take from the Kongregate sale was enough to be real FYM (though I enjoy running the site enough to want to keep doing it for a long time anyway).

Post reply on HN