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?
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.”
Biggest question: how does Fabrice's analysis play out for someone that isn't extremely wealthy?
Yes, if you have $20 M dollars and are talking about simply allocating assets he is probably correct. However, what about for the avg working person who's buying a house with money that isn't his (a mortgage) so that by the time he retires, he isn't burdened with paying for a place to live.
Also, as an aside: I think most people don't have the personal fiscal discipline to take the money they would save by not paying a mortgage and invest it--they spend it. A mortgage is like a forced savings account for many.
Standard is a 4 year vesting period. So, for example, if a cofounder had 100,000 shares, they would vest 25k shares each year--possibly with a one year cliff.
If you've already put considerable work into a company prior to any financing event, etc, it's common to keep 50% of your equity upfront and vest into the remaining 50% over a four year period.
Continuous periodic vesting is important. It's usually set at a quarterly or less time interval for the reasons mentioned by markstansbury.
Don't you think it's something like the following: think of a country's economy as a technology stack. You need to have the base levels of the stack in place before you can make more abstract things.
In places like Africa and India, there's a lot of access via mobile phones. But there's also a lot of missing pieces: transporation goods and services, smartphones, etc.
It seems to me like there's a lot of opportunity for media startups in both places, but that actual monetization is difficult because there isn't much in the way of ecommerce (due to logistical issues) and there isn't much in the way of advertising (because there's a lack of a base level of businesses to support it).
As for going global from a place like Africa: totally possible. But most startups follow a plan of succeeding at something small first.
I also think that Africa is going to leapfrog certain stages of technology / development and not others. For example, mobile banking in Africa is more widespread than it is in the US. My guess is that the first huge ecommerce company in Africa will be some weird hybrid of mobile, local, and banking infrastructure that people already trust.
There is a gentleman named Solomon Hykes (@solomonstre) who was working on something Heroku-like for wsgi apps. Last I heard, they were trying to remove a lot of dependencies from their stack. Doing a quick search, it looks like they've made some progress: http://bitbucket.org/dotcloud
I say this as a former developer who created some of the first video chat rooms ever (CUworld in 2000). Talking to random people online eventually devolves into porn. You can't help it. Chatroulette got around that stigma by eliminating all approach anxiety to a conversation (Parker's words)--sort of like the exact opposite effect of perusing profiles of people on a dating site and messaging someone very attractive (who probably gets inundated with requests).
I think the notion of turning chatroulette into a performance platform is very interesting. Some of the Ben Folds chatroulette performances were pretty fascinating and managed to get at the one-to-many-ness necessary to drive large amounts of traffic on a consumer site (you don't need that to make an interesting product--but Skype seems to have nailed 1 to 1 video pretty well). Being able to have different bands 'battle' on chatroulette or have comics or musicians present new material could be great.
For political reasons, it's usually best to pay yourselves the same amount. Reasons for different amounts: children, loans, trust funds, etc. When you're medium successful, that may change if one of you is still CEO. For now, don't sweat it.
I interpret pg's comment to mean that any dollars that you aren't spending growing your business are doing harm to the value of your equity. Realistically, I think this means that if you achieve some degree of product market fit, it's a bad idea to pay yourselves more than you really 'need' as those dollars could be more valuable to the 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...