A lot to unpack in your post, but some things worth mentioning:
A. Savings rate is everything. How much can you save and get compounding?
If you're high earning early in your career and can keep your costs of living down, you come out way ahead. This is much easier said than done. Also a big deal in college savings—being able to put away $5k / year in a tax advantageous account for your kid(s) makes a huge difference if you can do it when they're infants. If you're not a high earner until they're in high school, it's a different scenario.
2. Have seen a lot of friends (particularly engineers) go freelance and build up consulting work while in a city like NY or SF—and then once they have stable income they move to a cheaper location.
Kingston, NY in the Hudson Valley is a really interesting example of this. A small but steadily growing community of technical talent that works remote, but knows each other—making 90%+ of what they'd made in a major city and only two short hours to NYC by train or bus to meet clients, etc. And very nice housing stock in the $200-300k range. I would expect to see even more of this as we move into an age of autonomous vehicles, etc.
3. Cities. It's not clear that the party line of cities for the past decade is true. The 2008 crash did a number on younger people's ability to buy homes and finance them. They opted to stay in cities and rent instead. That trend seems to be reversing quite quickly.
There are some funds out there that will help employees exercise their stock options (for a %). 137 Ventures is one of them. Generally, these types of funds will only be interested in the stock of truly breakout companies.
I think the biggest qualification factor of a cash flow positive business mitigates quite a bit of risk (as long as there's some minimum bar of >= $50k / year).
The part that's tough is: what's the use of raising additional capital?
Is it to go full time on the product? Is it for marketing?
Positive cash flow is a great indicator although with early-stage companies that haven't achieved meaningful scale or been in the game very long it still seems a tricky sell. That said I like the idea and hope the model proves success for people.
Sidenote: is $50k/year a generally accepted figure or were you just demonstrating the point?
Thank your friend for writing a wonderful biography about a beautiful soul. That book really opened up the world for me by introducing me to a lot of the history and ideas. I'd dropped out of school many years ago and never learned Calculus. After that book, I was inspired to take evening classes and finally learn calculus. As it turned out, I needed to take a few refresher classes before I got to calculus, but I did and I finished up to calc 3. I've been meaning to go back and do some linear algebra and differential equations... Hopefully, I will go back soon.
Tell your friend he's doing the SF's work. Then again, maybe he's doing the devil's work if the SF is bent on keeping all the good theorems to himself.
I've thought about executing something similar with friends. I think there's a market for it—but the question is how big you think it can be?
ie: Birch Box works (sort of), because they're not paying for their merch samples. Would be great to try and make that happen for yourself.
Also, I think there are a lot of complications involved in shipping hard liquor across state lines. The alternative is to only be sending mixers and not liquor, which doesn't seem like as big of an idea.
If someone shows up in early days before a company has product market fit and is one of the people that truly shapes the business, call them whatever you want.
It’s hard to encourage and nurture positivity on the web. Tumblr’s done it by not explicitly building comments into the product—so if you’re going to say something critical, it shows up in your personal space. It's conflicting to build a growing community vs. a good one. One of the only ways to do it is to have some sort of asymmetric follow relationship that allows all users to create their own smaller communities.
Clay Shirky: “The downside of going for size and scale above all else is that the dense, interconnected pattern that drives group conversation and collaboration isn’t supportable at any large scale. Less is different — small groups of people can engage in kinds of interaction that large groups can’t.”
David Foster Wallace: “TV is not vulgar and prurient and dumb because the people who compose the audience are vulgar and dumb. Television is the way it is simply because people tend to be extremely similar in their vulgar and prurient and dumb interests and wildly different in their refined and aesthetic and noble interests.”
David Foster Wallace: “We should keep in mind that vulgar has many dictionary definitions and that only a couple of these have to do with lewdness or bad taste. At root, vulgar just means popular on a mass scale. It is the semantic opposite of pretentious or snobby. It is humility with a comb-over. It is Nielsen ratings and Barnum’s axiom and the real bottom line. It is big, big business.”
A. Savings rate is everything. How much can you save and get compounding?
If you're high earning early in your career and can keep your costs of living down, you come out way ahead. This is much easier said than done. Also a big deal in college savings—being able to put away $5k / year in a tax advantageous account for your kid(s) makes a huge difference if you can do it when they're infants. If you're not a high earner until they're in high school, it's a different scenario.
2. Have seen a lot of friends (particularly engineers) go freelance and build up consulting work while in a city like NY or SF—and then once they have stable income they move to a cheaper location.
Kingston, NY in the Hudson Valley is a really interesting example of this. A small but steadily growing community of technical talent that works remote, but knows each other—making 90%+ of what they'd made in a major city and only two short hours to NYC by train or bus to meet clients, etc. And very nice housing stock in the $200-300k range. I would expect to see even more of this as we move into an age of autonomous vehicles, etc.
3. Cities. It's not clear that the party line of cities for the past decade is true. The 2008 crash did a number on younger people's ability to buy homes and finance them. They opted to stay in cities and rent instead. That trend seems to be reversing quite quickly.
https://www.bloomberg.com/view/articles/2018-04-18/growing-m...
https://www.bloomberg.com/view/articles/2018-04-03/millennia...