If you want startup stock, I'd think "Charge biggest/most sophisticated companies a LOT of money, reinvest a portion into angel rounds." This does mean that you'll have stock from companies you didn't work for.
Note that angel investing is, for most angel investors, a fun way to lose money. (I have three small angel investments.)
An angel who invests $50k into a startup at a $5 million valuation gets a MUCH better deal than an employee who is offered 1% of the company, by the way. Ask me why if this isn't immediately obvious to you.
Have you successfully got stock as part of your consulting compensation and if so, why do you think you succeeded even though it's a really tough sell?
For the $50k angel investment, I'm guessing that you mean because its preferred stock with no vesting?
I wrote up the reasons for angel stock being better than employee stock on Twitter and, as I am on a phone right now, cannot conveniently paste it. Can someone please link that conversation here?
The numbers I'm going through right now show that, even if I can make a lot of income consulting, if I just join the right startup I could earn stock options worth effectively more than I'd ever be able to make consulting (assuming I don't get stock consulting).
if you are able to earn $150k / year from consulting in a relatively small fraction of your time (incl. the overhead of networking, etc), that frees you up to use the remainder of your time on other activities, perhaps profitable or something else you value.
some ideas: start your own startup, start your own small business, focus your energy on building a diversified investment portfolio, buy and renovate a house to sell, plan and run a series of workshops, start your own hobby farm, spend more time with people whose company you enjoy.
Generally, unless you have a team, if you're finding that you can multiply your hourly rate by 2000 and get within shouting distance of your annual gross, that means you're not charging enough.
There are a lot of good things that come from jacking your rates up, beyond just being able to make the same amount of money while doing far less work.
A pretty common strategy is to dial your rate to a point where you're consistently between 70-80% utilized, and to raise your rates some % for all new clients annually.
At a consultancy with a team of people, a utilization rate over 85% might be considered overheated, risking burning people out.
(Though if you're running a body shop you don't care about overheating).
If it was just me and a partner consulting, I'd use rates to dial utilization back to 50%.
There is a sense in which stock compensation to a contractor is equivalent to raising cash from an investor and exchanging that cash with a contractor for services. During the first dot-com bubble, equipment vendors famously did that with startups; it allowed those vendors to book totally unrealistic sales which juiced their numbers even though they'd never see a return on the stock. It was, in effect, channel stuffing.
Today, though, a company that is willing to, in effect, raise an ad-hoc random funding round in order to get a contractor programming job done is a company whose stock is not going to be worth anything.
There are a lot of people who will trade you stock for things. I'm certainly not saying nobody will offer you stock!
When did this equity compensation deal start? The most important feature of employee options vesting is the cliff; your deal was something like "if I'm still consulting for you 12 months from the start of our first statement of work, I get 1/4 of the promised options"?
How does tax treatment of those options work? Most of the reason that employees are put into a crunch period after they leave where they have to spend real money on shares is that US tax law requires employee options to expire within some number of days after the employee relationship terminates. But you're not an employee at all; how can you have employee stock options?
And what startup has liquid stock? I'd love to work there.
A willingness to pay in equity for consulting would to me be a red flag that the startup I was talking to was poorly managed.
Further I too would never consider stock instead of pay for any consulting activity. That's a loser move.
You may ask for an actual stock but it still won't be a fully vested grant but some conditional trickery promise.
I'd rather take maximum cash squeeze and re-invested [part of] it into some more dependable.
With that said, you may be able to negotiate to reduce your hourly rate in exchange for earning a equity position. You could also work out a convertible debt type arrangement. But again, I would walk cautiously here. Having $100 today can be worth a lot more than the gamble on possibly having $1000 five years from today. Just because a company is offering employees stock does not mean that the stock will be worth anything or that the employees will be rewarded on an exit.
I am working on a startup that is currently bootstrap and am very open to getting work done for shares vs salaries.