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Silicon Valley's best kept secret: Founder liquidity

stefantheard.com

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Re: Silicon Valley's best kept secret: Founder liquidity

#31

Earlier quoted context omitted.

I think he means 83b early exercise: https://www.esofund.com/blog/early-exercise-options-83b-elec... Extremely beneficial when paired with QSBS and liquidity.

Does anyone restrict 83b elections? Is that even allowed?

Ive seen it restricted so yes

Re: Silicon Valley's best kept secret: Founder liquidity

#32

Having only worked for larger companies (RSU stage), I'm curious what the typical breakdown of founder to early employee to investor to later employee equity looks like. I'm sure it differs pretty wildly, but I'd love to know what a 'typical' case for mid-to-late-stage start up looks like.

I can share some details.

Employee 1: ~1%

Employee 10: ~0.1%

Employee 1000: 0.01%

I'm extrapolating from past experiences in SaaS companies where I was employee number X and X has varied fairly widely.

Re: Silicon Valley's best kept secret: Founder liquidity

#33
post #24

How common is this? How many founders that raise series A are liquidating? What are the amounts typically?

It's fairly arbitrary, but there is at least one constraint on how much you can liquidate: You cannot liquidate much more than 10%, because you're taking money from the company and investors would not appreciate that.

Re: Silicon Valley's best kept secret: Founder liquidity

#34

I’d also push for allowing early exercise along with secondary sales restricted only by a short right-of-first-refusal period.

> allowing early exercise along with secondary sales restricted only by a short right-of-first-refusal period Do you mean cashless exercise?

No, although it could also be cashless.

Early exercise is purchasing shares before your options vest, making you a shareholder sooner and solving a bunch of tax issues. The company retains the right (basically the obligation) to repurchase any unvested shares should you leave the company before fully vesting.

Re: Silicon Valley's best kept secret: Founder liquidity

#35
post #6

The best startups have a concept which is summed up thusly: “We all go to the pay window at the same time.” It’s ok for founders to take a little bit of money off of the table if they extend that to their employees as well. Asymmetry is where things get weird. I’ve seen many founders who got deep into the fundraising cycles without ever realizing they could take a cent out. VCs will constantly tell you to let it all…

It’s like trading windows and blackout periods for employee RSUs, but equity selloff on a schedule for the c suite.

Re: Silicon Valley's best kept secret: Founder liquidity

#37
post #14

Making less money isn't really the risky part about founding a startup. The risky part is missing out on years of other life experiences, stressing (or losing) your closest personal relationships, failing and feeling personally responsible for disappointing everyone you convinced to believe in you, and developing an anxiety disorder (or worse) from chronic long-term stress. Author's suggestion that they could have ta…

Having been a key early employee at a failed startup, horseshit.

The employees bear the burden too, if they're working their asses off at an early stage startup they believe in the cause just as much. Viewing founders as somehow magically special is a symptom of the broader misguided hero worship the US has right now.

Re: Silicon Valley's best kept secret: Founder liquidity

#38
post #17

We are talking SV here, and that's very different from my European experience. I've known of founders in Scandinavia who walked out from startups that weren't doing so bad and that could have gone for another round of investment because they were earning as much as a bus driver, had zero savings, and were experiencing burn out after almost a decade of work. Maybe that bit of SV culture that lets founders be on par wi…

Having cofounded both bootstrapped and funded startups, I can say that in each case there was a deadline associated with success: for bootstrapped, we set hard targets in terms of maximum spending and time in order to test our hypothesis. This allowed us to fail fast in our own way and go back to a better paying day job.

For funded startups - at least with a healthy seed round, the investors expected us to burn fast and hard in order to prove our hypothesis or fail trying as quickly as possible, but they also expected us to not pay ourselves very much. As we found product-market fit and raised Series rounds, it was understood that we would pay ourselves competitive salaries.

Being stuck at the seed stage for 10 years is not healthy - neither in Europe, nor in Silicon Valley.

Re: Silicon Valley's best kept secret: Founder liquidity

#39
post #16
post #6

The best startups have a concept which is summed up thusly: “We all go to the pay window at the same time.” It’s ok for founders to take a little bit of money off of the table if they extend that to their employees as well. Asymmetry is where things get weird. I’ve seen many founders who got deep into the fundraising cycles without ever realizing they could take a cent out. VCs will constantly tell you to let it all…

I have seen a lot of companies, a lot of rounds. I have known zero founders who have turned down an option to take money off the table (and zero A raises that offered that to employees). I love the idea of your universe, though.

The very first startup I joined after grad school allowed all employees to cash out significant chunks of their stock in the Series A round.

Also Elon famously put 200 million of his own money into Tesla and SpaceX to keep it afloat, which is the opposite of cashing out early.

Re: Silicon Valley's best kept secret: Founder liquidity

#40
post #4

Love the movement and glad there are founders out there pushing the envelope for their team. (aside: 51 points but only 1 comment? It's a front-page worthy article, but sort of feels like there's some vote gaming happening. I've never seen 50 points w/ 1 comment.)

The usual problem of late on HN is people commenting without upvoting, even if they like the article.

On this post, I started reading, then paused to hurry back and upvote on HN, to do my part to keep it from falling off the front page, before I returned to finish reading.

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