The interesting discussion is how much you should take off the table if the offer is uncapped.
50% for security, let the remaining 50% run. We can spend countless hours modeling the risk and return delta of various percentages and against non correlated asset classes you might diversify into once liquid, but most of life is luck; you can do everything right and still lose. This makes it easy, imho.
(not investing advice, just a rando, n=1)
Edit: noir_lord indeed! Good eye. https://www.youtube.com/watch?v=1TCX90yALsI
I'd even go so far as to recommend putting that money specifically into things that promote your long-term economic stability, e.g. is it enough to let you buy a home that's going to have monthly expenses below what you're paying in rent? There's plenty of economic uncertainty out there right now, but I feel confident in one thing: Even if the entire economy goes into the crapper rent will not go down. In addition the real estate market is pretty soft right now because of uncertainty, so if you're in a position to purchase that may let you basically lock in your monthly housing costs for a decade or more.
ST:TNG fan? - That was an important lesson for me as a kid.
“It is possible to commit no mistakes and still lose. That is not a weakness; that is life.” - Picard
Obviously you are guessing probabilities to plug in but they can be based on other exits etc. Someone in the know on startup equity could offer this as a consultation service.
The mathematical answer is that if your interest rate is lower than the expected returns of some kind of portfolio you have, than you'll make more money investing.
But I like to bring up what Morgan Housel, author of the book The Psychology of Money, said on paying down his mortgage:
> It just increased our independence, even if it made no sense on paper. So that's another element of debt that I think goes misunderstood. And a lot of that for both of those points is this idea that people don't make financial decisions on a spreadsheet. They don't make them in Excel. They make financial decisions at the dinner table. That's where they're talking about their goals and their own different personalities and their own unique fears and their own unique skills and whatnot. So that's why I kind of push people to say like, it's okay to make financial decisions that don't make any sense on paper if they work for you, if they check the boxes of your psychology and your goals that makes sense for you. And for me, extreme aversion, what looks like an irrational aversion today, and I would say is an irrational aversion to debt, is what works for me and what makes me happy, so that's why I've done it.
Obviously you need to consider both net worth and cash flow when making a decision like that, but don’t underrate the difference that improved cash flow makes!
Owing no one anything is incredibly liberating. It changes how you behave and what you are risking.
Sure, I’d be richer on paper if I had kept the first house and rented it out, buying the second house with debt. But the worry and hassle and was my concern and I’m far happier. Perhaps 20 years from now my position would be different.
Yes, that is the mathematically correct answer.
You maximise expected value not by putting everything into the single highest-EV bet, but by sizing your bets according to https://en.wikipedia.org/wiki/Kelly_criterion
2) Time is far more valuable than money. If you can take life-changing $$$ off the table in exchange for time, do so. The 2nd $1M buys you a tiny proportion of the benefits that the first $1M did.
3) You have a v. high risk concentrated portfolio that is aligned with your income. That's massive risk.
4) Taking it now buys you time & optionality. Leaving some still buys you blue sky. Best of both worlds.
So basically the only time I had the opportunity to theoretically earn $110k, at the peak of my 15 year career after working insanely hard including nights and weekends, was not even feasible in practice and it turned out that I earned more money holding and forging over the following 4 years than I would have gotten for selling.
But damn, when I see some of these corporate 9-to-5'ers sitting on $1 million+ which they got after only 5 years or so and they're not selling because they think they deserve more. It seems insane to me. It's a lot of money, they can sell anytime, probably still keep their job. As they say in crypto, I would dump the shit.
Each time you get money you get to deploy that elsewhere. If you have super risk tolerance, push $25k cheques as seed.
Frank: What you got on you?
Jim Bennett: Nothing.
Frank: What you put away?
Jim Bennett: Nothing.
Frank: You get up two and a half million dollars, any asshole in the world knows what to do: you get a house with a 25 year roof, an indestructible Jap-economy shitbox, you put the rest into the system at three to five percent to pay your taxes and that's your base, get me? That's your fortress of fucking solitude. That puts you, for the rest of your life, at a level of fuck you. Somebody wants you to do something, fuck you. Boss pisses you off, fuck you! Own your house. Have a couple bucks in the bank. Don't drink. That's all I have to say to anybody on any social level. Did your grandfather take risks?
Jim Bennett: Yes.
Frank: I guarantee he did it from a position of fuck you. A wise man's life is based around fuck you. The United States of America is based on fuck you. You're a king? You have an army? Greatest navy in the history of the world? Fuck you! Blow me. We'll fuck it up ourselves."
Seize the moment, friend! What you can do NOW with that 10% slice will never exactly be on your possibilities map again.
Me finding the money to climb Kilimanjaro at 23 is different than me having the money at 40 but worse knees.
Thank you for pointing this out and I hope someone formalizes it more.
Excellent point. You may have just talked me into retiring.
> What you can do NOW with that 10% slice will never exactly be on your possibilities map again.
Maybe not... but "once in a lifetime chances" come around more often than you think. You don't have to take every one right now. (As you get older, options narrow, as you said.)
- https://www.diewithzerobook.com/welcome
Read it earlier this year and it definitely changed some of my thinking along those same lines.
My loose summary of the book:
"Any money left in the bank when you die is essentially wasted - you could have used it to have experiences when you were alive, or given it to family / charity earlier when it would have had more benefit. Figure out what major experiences and memories you want to have in life, plan to do them earlier when you have health and time, and build up memories for later in life."
I didn't find the discussions of how to plan out retirement savings very useful - there's a lot better info on withdrawal approaches in various FIRE-related groups.
But the "be willing to spend now on activities you might not be able to do later / don't hold off on 'living' until you're retired" argument made a _lot_ of sense to me for a variety of reasons, and it was a major factor in researching early retirement a few months later (and deciding to make that a new goal. along with taking more vacations before then).
Physically, I don’t feel a lot different than in my 40s. ( I’m pretty firm in my exercise schedule. ) But looking over almost anyone in their 80s, I’m reminded that the 60s likely kicks off ‘the fourth quarter’, to use sports parlance.
Time to let it all hang out, leave nothing on the table.
I should point out that it's cheaper to travel when young: Back then I stayed in a tent in the desert and in a friend's room near Amsterdam. If I did the same trip today, I'd have my family in tow, and would need more comfortable accommodations.
I should also point out that startup equity is not retirement savings. Selling 10% of your equity, investing most of it, and then doing something that you won't be able to do when you're old is a very wise and mature decision.
After 40 you've already made many of your major life decisions - career, partner, education, kids etc. There's less room for new experiences to alter that trajectory meaningfully.
One thing I've also realized through being lucky enough to enjoy some "semi-retirement" between work is having a healthy balance makes me appreciate both work and "leisure" more. It gets pretty boring to go to the beach every day, it turns out. I was itching to get back to building something by the end.
Do you really believe people who have health issues at an early age are simply stupid?
If you can retire at 40 having lived your 20s/30s to the fullest then game on, but it would be crazy to sacrifice that time when you are so free and full of energy otherwise IMHO.
FWIW I am fortunate enough to have really enjoyed by earlier years and be mostly retired in my early 40s.
Then consider it as an offer to buy into the startup at the same dollar amount.
Would you invest?
Not selling is the same as investing in the startup.
This same logic applies to stocks you are holding.
If you sell your business, it's because the value of the business to you is less than the purchase price. Likewise, the value to the buyer is greater than the purchase price.
Ideally startups are about creating value, and making a return on that value, but more and more they look like they are instead selling hype to a series of investors who are trying not to get stuck with the hot potato.
not getting it.
Selling a part of your business can help spread risk to a new investor reducing your own personal risk.
