Don't get me wrong, I really like DMC, but it strikes me as somewhat contradictory for a piece like this to be written by anyone but a person who consistently/repeatedly spreads risks a lot of what they have on bigger ventures. Once you have an exceptional network and reputation, there are few positions, besides maybe being a lawyer, that come with less risk in Silicon Valley than that of an investor.
Risk-wise, setting up and running your own fund is somewhere between starting a new business with an unproven business model and opting for a career path. IMHO it's not the risk profile described in this post.
But I've since learnt that a certain breed of entrepreneur-investors continue to disrupt (innovate) in other ways and in other arenas. One example is 500Startup's overseas initiatives like the one in India.
At the end of the day, fear is fear, we all have it, you either keep going or you let it stop you.
Maybe not. Maybe soft landings are possible, just don't put everything you got in just one shot.
Do you mean a 'life-style business', or trying a few smaller ideas simultaneously?
(Genuinely interested, not sniping or anything).
Most of fund managers shouldn't be called investors, they make bets in companies like some people do in horse racing. Which is ok, but they sell this image where the only path to succeed is by getting huge like instagram or crashing like a thousand other startups. They are distorting reality for profit. Making bets is part of speculative investment, doing this to startups is cruel - specially when you have direct influence in the whole 'community'.
How it works:
Let's say you have: a set of ideas I, which pretty much englobes all ideas that have a some chance of succeeding right now, some ideas slightly overlap others, but that's ok. Now, you take N startups which are willing to take one idea and blindly go full throttle, to fly or die. Your job as a VC is pretty much igniting them and (that's the cruel part) making sure they do never 'pivot' to something smaller with a more long-term approach/returns. You worth more dead tomorrow than evaluated at 'only' 2 million in 24 months.
My point is: for every airbnb there are hundreds of very successful companies that have million of users and also impact the world and didn't play russian roulette.
Almost forgot (explaining soft landing):
The idea is pretty simple, find some market that are willing to pay (read: if you ask the money before the product, they would pay and then you ASK) build the product without spending your savings. Get more similar users. If the first 50 users you got are the only ones that want the product (very unlikely) maybe it's time to shut down the product and take the losses which will not be huge. You might even keep your old job when doing that. Most of ideas I got from Amy Hoy and DHH/Jason (book 'Rework').
Landings per se are constructs of the market, not the entrepreneur. IMO obviously.