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Startup Stock Options – Why a Good Deal Has Gone Bad

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Re: Startup Stock Options – Why a Good Deal Has Gone Bad

#31

Post by throwaway5752 »

seibelj wrote: post #3

Valid reasons to work for a startup: - You are a cofounder. - You have little experience and you are using this to break into the industry, and get experience on many different technologies ("wear many hats"). - They are working on a very specific problem or using a specific technology that you strongly desire to work on and it's difficult to do it anywhere else. - You want to work a certain way (remote, on the beach…

"Making a lot of money in salary."

I think a bit of perspective is in order. When the bar for comparison is technical principles at FAANG, yes.

If you want to own a house, have paid-for cars, put your kid through school, put away savings, and otherwise be completely comfortable then you can do just fine. That is "wealthy" for a lot of people in this country.

I know someone that delivered food to restaurants. He woke up at 4am, and periodically did double shifts. His work life balance was worse than almost any developer I know. And he had to carry stuff. [That was a bad work/life balance].

Seriously, count you blessing if you're in software now. I have been doing this 20 years and this is the best it's been since before the .com bubble ended.

Re: Startup Stock Options – Why a Good Deal Has Gone Bad

#32

Post by luckystartup »

l2c1928 wrote: post #2

It's bad for most people, but when it's good it's really good. I was lucky to join a now unicorn as one of the first few dozen employees a few years ago. I forward exercised with a few thousand out of pocket (section 83b) an equity grant now worth around $1.5m. Because I forward exercised my options at a low valuation I didn't have to worry about paying taxes if I exercised at a later time when the company's valuatio…

I have a very similar story: Was on the first 10 employees at a now unicorn, forward exercised with a few thousand dollars, and my shares are also now worth around $1.5m. But unfortunately the company blocked all attempts at selling any shares on secondary markets.

Something you might not be aware of: If you joined the company before they had $50M in assets, your stock would also qualify as QSBS [1], which means you don't have to pay any tax on gains of up to $10 million.

[1] https://www.andersentax.com/services/for-private-clients/bus...

Re: Startup Stock Options – Why a Good Deal Has Gone Bad

#33

Post by toomuchtodo »

ohaideredevs wrote: post #11
seibelj wrote: post #3

Valid reasons to work for a startup: - You are a cofounder. - You have little experience and you are using this to break into the industry, and get experience on many different technologies ("wear many hats"). - They are working on a very specific problem or using a specific technology that you strongly desire to work on and it's difficult to do it anywhere else. - You want to work a certain way (remote, on the beach…

Not exactly a unique experience, but my .05 - I started of at a startup with a "lol just do it" attitude to whatever the problem was. Worked 12 hours a day a lot, was stressed out all the time, didn't have a life, got calls at odd hours to deploy...but, if I didn't have that experience, I wouldn't have grown nearly as fast. Got to see all aspects of the products and the consequences of the decisions we made early on.…

> Worked 12 hours a day a lot, was stressed out all the time, didn't have a life, got calls at odd hours to deploy...but, if I didn't have that experience, I wouldn't have grown nearly as fast.

Congrats on using the opportunity to grow in an abusive role. It should not be normalized is the point.

Re: Startup Stock Options – Why a Good Deal Has Gone Bad

#34

Post by l2c1928 »

mlthoughts2018 wrote: post #22
l2c1928 wrote: post #2

It's bad for most people, but when it's good it's really good. I was lucky to join a now unicorn as one of the first few dozen employees a few years ago. I forward exercised with a few thousand out of pocket (section 83b) an equity grant now worth around $1.5m. Because I forward exercised my options at a low valuation I didn't have to worry about paying taxes if I exercised at a later time when the company's valuatio…

Your story still leaves a lot of room for skepticism. For one, 1.5MM is not actually a very good deal for an engineer in your situation, and likely the company gave you very unfavorable terms. Electing 83b is a fairly irrelevant detail in your story as it only affects taxes, not the outcome of the company. Your shares are likely going to get hugely diluted exactly because of growth investing like in the article. Inve…

There's a myth that you can't realize gains if a company doesn't IPO...I've already sold some shares in a tender offer. There is an active secondary market for shares if I chose to sell more.

Not sure what your point is about $3MM over 10 years. Why would you divide it over anything other than the number of years you actually worked at the company?

You've assumed I was a senior engineering hire. I was in a junior non-technical role a year out of college.

Re: Startup Stock Options – Why a Good Deal Has Gone Bad

#35

Post by bloomer »

throwaway5752 wrote: post #31
seibelj wrote: post #3

Valid reasons to work for a startup: - You are a cofounder. - You have little experience and you are using this to break into the industry, and get experience on many different technologies ("wear many hats"). - They are working on a very specific problem or using a specific technology that you strongly desire to work on and it's difficult to do it anywhere else. - You want to work a certain way (remote, on the beach…

"Making a lot of money in salary." I think a bit of perspective is in order. When the bar for comparison is technical principles at FAANG, yes. If you want to own a house, have paid-for cars, put your kid through school, put away savings, and otherwise be completely comfortable then you can do just fine. That is "wealthy" for a lot of people in this country. I know someone that delivered food to restaurants. He woke…

The comparison isn't between working at a software startup and delivering food. It is between working at a software startup and a different software job. The other software job is almost always better for the reasons listed above.

Re: Startup Stock Options – Why a Good Deal Has Gone Bad

#36

Post by marcinzm »

andrew311 wrote: post #25
save_ferris wrote: post #10

Why don't startups offer actual equity grants instead of options? It seemed strange to me when I was starting out in my career that I needed to take a lower salary and options to exercise upon my exit, which wound up costing me thousands of dollars from that lower salary. Two years later, one founder forced out his two other cofounders, started a new company in the exact same space, and poached his best employees, es…

Share grants would be seen as income by the IRS and most states and taxed at their Fair Market Value. Options on the other hand usually qualify as Incentive Stock Options that aren’t taxed at grant time and “when exercised, it isn't necessary to pay ordinary income tax. Instead, the options are taxed at a capital gains rate.” [1] Options are better up front because there is no outlay for the employee. They are a hass…

>Instead, the options are taxed at a capital gains rate

As I understand it, they ARE taxed as income for all intents and purposes at exercise time (based on the value difference at exercise). They are not regular income but they are part of Alternative Minimum Tax income. You pay taxes on the greater of the two. The difference between exercise price and sales price is then taxed as capital gains assuming you held the stock for a year (or two?).

The one trick to this is that if you exercise very early then the tax is on basically nothing (literally nothing if your option price and current value are identical). However, you still need to buy the options so it's not free but just tax free.

Re: Startup Stock Options – Why a Good Deal Has Gone Bad

#37

Post by dleslie »

rooam-dev wrote: post #27
dleslie wrote: post #13

Earlier quoted context omitted.

> You want to work a certain way (remote, on the beach, whatever) and they are willing to go this route. This is me. I quit my well paid job and took a massive pay hit so that I could work from home and so be able to spend more time with my daughters. Absolutely worth it.

At a start-up? How do you manage live/work balance? Are there any on-call duties? Thanks in advance.

It's a startup, yes.

I work eight hours a day on average, and being that we have staff on most continents we don't really have a need to be on call. That said, I've had a handful of 3am emergencies over the course of the last few years.

I work in my garage; so I have no commute, and I no longer lose over two hours a day to commuting. That's meant I contribute far less to open source, which I did while on transit. However, I don't miss commuting at all and am thankful for the time recovered.

Balance is blissful. While my wife was on maternity leave for twelve months our girls were at home as well, and so my breaks consisted of spending time with my family. Now I walk them to daycare before work and listen to the rain on my roof while I work.

Re: Startup Stock Options – Why a Good Deal Has Gone Bad

#38

Post by dxbydt »

throwaway5752 wrote: post #31
seibelj wrote: post #3

Valid reasons to work for a startup: - You are a cofounder. - You have little experience and you are using this to break into the industry, and get experience on many different technologies ("wear many hats"). - They are working on a very specific problem or using a specific technology that you strongly desire to work on and it's difficult to do it anywhere else. - You want to work a certain way (remote, on the beach…

"Making a lot of money in salary." I think a bit of perspective is in order. When the bar for comparison is technical principles at FAANG, yes. If you want to own a house, have paid-for cars, put your kid through school, put away savings, and otherwise be completely comfortable then you can do just fine. That is "wealthy" for a lot of people in this country. I know someone that delivered food to restaurants. He woke…

> “If you want to own a house, have paid-for cars, put your kid through school, put away savings, and otherwise be completely comfortable then you can do just fine.”

lol wut ? if you work in a typical SF startup, you can do precisely none of these things. Like, literally zero.

Re: Startup Stock Options – Why a Good Deal Has Gone Bad

#39

Post by deanmoriarty »

rooam-dev wrote: post #27
dleslie wrote: post #13

Earlier quoted context omitted.

> You want to work a certain way (remote, on the beach, whatever) and they are willing to go this route. This is me. I quit my well paid job and took a massive pay hit so that I could work from home and so be able to spend more time with my daughters. Absolutely worth it.

At a start-up? How do you manage live/work balance? Are there any on-call duties? Thanks in advance.

In my very personal experience, many times startups are not full of the brightest engineers, especially if they are based in a major tech hub such as the Bay Area: most talented engineers these days, if location is not an issue, first try a shot at FAANG or similarly big companies where they can experience problems at massive scale and very high compensation.

Hence, many folks who end up accepting to work at a startup are less talented engineers (you're left with the "scraps" of the market), so if you're a high performing individual you might find that you really don't need to put that many hours in to be effective, as compared to your peers (and that's deeply depressing as well, and one of the reasons why I left startups for FAANG, other than compensation; talent is SO SO SO much better).

I speak for direct experience, I rode a startup train for a long time at a company that grew a lot, and rarely put in more than 40 hours a week into the job, while others were routinely putting 60+. And I kept being praised by the management and technical leadership.

The problem (lack of local talent due to big company competition) became severe enough that we had to bootstrap multiple remote teams in easily overlooked areas because the new local hires (San Francisco) were literally trashing the product due to poor development/testing.

Re: Startup Stock Options – Why a Good Deal Has Gone Bad

#40

Post by nrmitchi »

thesausageking wrote: post #21

He glosses over an important point: it's now typical for founders to take money off the table as part of financing rounds, sometimes as early as the A round. Founders will request it as part of a funding round and, there's so much competition to invest in the top startups, that VCs go along with it. Decades ago, this wasn't the case. Founders waited for the IPO like employees. If you're an engineer sitting on $5m of…

It was mentioned about half-way through the article.

> And finally, in many high valued startups where there are hungry investors, the founders get to sell parts of their vested shares at each round of funding. (At times this opportunity is offered to all employees in a “secondary” offering.) A “secondary” usually (though not always) happens when the startup has achieved significant revenue or traction and is seen as a “leader” in their market space, on the way to an IPO or a major sale.

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