Even post-B, the odds aren't good. They're better than pre-A obviously but it could still be 4-5 years and there are a ton of ways to f* it all up before then.

I just wrote about this last week - https://medium.com/@CaseySoftware/tech-ipos-an-inside-out-vi... - after personally experiencing IPOs of both Twilio (joined post-B) and Okta (joined post-F).

Edit: Replaced the link to my site with the Medium post.

> my [startup] equity was worth about 50% of my salary each year.

The equity of many AmaGooFaceSoft employees is also worth at least 50% of their yearly salary.

Yes but that's if I were to sell it after ~1 year at a company you've likely never heard of. If I wait 3 more and there's a large exit it could easily be worth millions.

Do you have a convenient way to sell your startup equity after ~1 year? (i.e. before there's an exit)

There is a developed secondary market for venture-backed companies' stock. (Source: I do this.)

I thought private stock transactions were subject to board approval, or is that just Canada?

It depends on the company. Some companies are quite liberal with transfers. If you have a bona fide offer, they'll amend the cap table. For others, my having a relationship with the founder or Board is critical. A good starting point for American companies is is their Certificate of Incorporation. If you exercised options, the Restricted Stock Purchase Agreement should also contain terms, e.g. the company's transfer policy or right of first refusal.

I have never heard of a Canadian company looking to raise capital structuring itself under Canadian law. Commonly, you'd have a Canadian law subsidiary wholly owned by a Delaware corporation.

Disclaimer: I am not a lawyer. Hire a lawyer before selling private stock. Do not take investment or legal advice from my Internet comments; they are neither.

There's an EU startup that's trying to create a blockchain based market for shares of pre IPO startups: https://markets.funderbeam.com/market

Depends on the terms. In most startups board can only match the offer.

Lol.. good luck.

Not convenient, but definitely possible. Equidate is a fairly open market for that kind of thing.

That is an exit of sorts.

But there's also a much higher risk that your options will be dilluted to nothing.

> if your company isn't one of the top companies of the decade

GGP covered that option quite nicely. Those are companies that are clearly at the top companies of the decade, maybe even longer.

> Joining a series B startup and waiting a couple years is the easiest, risk adjusted way to make a bunch of money.

Sorry, what?

I'm glad I'm not the only one who did a double-take at that statement. The key qualifier is "risk adjusted", but that's not really meaningful from the employee's standpoint: You can only bet on one company at a time.

Imagine what kind of stock investments you'd make if you were only allowed to invest in one stock at a time.

Let's say 10% of start-ups succeed to the point where employee 100 makes "a bunch of money", which I think is very generous. You would need to join 10 of these start-ups throughout your career (and of course remain at each for the 3-5 years it takes to learn if the lottery ticket pays off) to have an expectation of one case where you end up that bunch of money.

So yea. Risk adjusted. While the EV might look good, the variance makes it a losing game.

I'm not sure what you mean by 'expectation of one case' here, but just to clarify: rolling a ten-sided dice, 10 times, gives a 65% chance of rolling at least one 10. So you still have a 35% chance of zero 'wins'.

I can't comment on the rest of your model, but its worth keeping in mind how the binomials shake out.

Ack, you're absolutely right. Don't know where I was going with the hypothetical example but my math was totally wrong.

Actually, your statement was entirely correct. "Let's say 10% of start-ups succeed ... You would need to join 10 of these start-ups ... to have an expectation of one case [of success]."

It is a true statement that the expected number of successes after 10 tries would be 1. It is also a true statement that your chance of zero successes after 10 tries is 34.8%. (The balance comes from the outcomes that include multiple successes.) It may be that the latter is the more relevant and interesting statement to make, but your math was totally right.

;-)

What about staying for 1-2 years per company? Then, you can diversify twice as much as if you stay 3-4 years per.

Where "a bunch" = 2-3m

Yes. However, you are basically making the argument that your options are worth ~50% salary. The problem with that argument (at least in the valley) is that you are making the calculation off the initial starting salary. Salary/RSU growth at companies like Google, FB, etc is surprisingly rapid in the first ~24 months, to the point where I would argue that if you haven't doubled it in that timeframe you need to work on your extrovert/self promotion skills

I only stayed 1 yr

This is just an anecdotal account of your single experience, it isn't making a strong case for your general point.

> but by series B a lot has been mitigated

Or, the fact that a series B is needed is indicative that there was more risk than anticipated. Series B is not always good news (in general it is though, but there is still plenty of risk at that stage). So always verify what the reason for a funding round was and make sure that it was an 'up' round rather than a 'down' round.

> It's really not hard to find a company with great product market fit, say series B, get a bunch of equity, a decent salary, and wait a couple years for your equity to be valuable.

Still so many phony companies out there even at Series B.

> I actually think, risk adjusted, that's the easiest way to make a bunch of money.

It's really not. Risk-adjusted go work at Google for 10 years and you'll probably make more.

If this is easy for you, you should quit engineering and run a growth equity fund.

> If this is easy

If what is easy? Making a few million in a few years is never easy, but I don't know of a better way to do that on a risk-adjusted than joining startups after product/market fit.

And for what it's worth I don't build very much anymore, unfortunately

> and wait a couple years for your equity to be valuable

Product-market fit does not imply appreciation. Growth is priced in. Unless you think you know more than the market (the VCs), you shouldn't expect a return.

Product market fit and further growth are generally pretty correlated, though

Yes, but growth and appreciation are (theoretically) not. Growth is priced in. You're saying product-market fit -> growth -> appreciation. The first part of that is true. The second isn't. Assuming market efficiency, the VCs know just as well as I do that the company is going to grow, so they'll pay a higher rate, which means my options will be priced higher (or I'll get fewer RSUs, accordingly). Growth does not imply appreciation.

Assuming market efficiency at series B is quite a leap, IMO. That said, let's roll with that assumption; you need to find a company that continues to grow, or in some other way derisks itself.

This is like saying "To make money in the stock market, you have to find stocks that will go up." It's tautological.