If you bet a startup will fail, you’ll be right most of the time, but not because you’re insightful. (The Critic)
If you bet only on huge ideas, you’ll be wrong most of the time, but because in high tech the financial successes are orders of magnitude larger than failures, this is still a profitable bet. (The Professional Investor)
If you bet only on small, conservative ideas, and stay focussed, you’re most likely to actually succeed, with normal-sized outcomes. This is the best bet for sustainable personal fulfillment and freedom, which after all is the core promise of entrepreneurship. (The Bootstrapper)
In one lifetime you have only a few at-bats at startup-hood, because successful, sustainable companies take 7-10 years to build (yes, even today), and big, change-the-world startups are just as emotionally devastating and just as difficult to solve the product/market/profit equation as little, insignificant ones, so the only endeavors worth your time are big audacious startups. (The VC-backed Founder)
Since all startups are hard and unlikely to survive, you should make only large bets on huge ideas. Risks are high, thus potential returns must be proportionately high to be worth your precious time.
Or no, since all startups are hard and unlikely to survive, you should make conservative choices and retain total control to minimize the risks you absolutely have to take.
Or no, since personal fulfillment is the only true measure of success, you should avoid the world of valuations and evaluations and just build something you enjoy.
Or no, since personal happiness is achieved by doing something that other people will envy or respect, you should use external valuations as the yardstick and money as the way to keep score.
Richard Branson proves that a life of luxury and fun is the goal. Warren Buffet proves that money won’t make you happy but purpose and people do.
Peter Thiel and Elon Musk prove that smarts and persistence trumps luck and timing. Yet every VC will tell you they’d rather be lucky than good.
When are you going to stop, take a breath, think quietly, shut out the cacophony of expectations and press releases and chest-thumping and “disruption” and biased storytelling, and decide what’s right for you?
And then, harder still, when will you truthfully be comfortable and confident in your choice?
Because those who can, are truly rich.