No, *I’ll* tell you the answer!


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.


15 responses to “No, *I’ll* tell you the answer!”

  1. Thanks Jason. This was a thought provoking piece, especially for me right now as I mull over my options. And, although I know this wasn’t your intent, it’s perhaps the most succinct description of the various forms of entrepreneurship that I’ve read.

  2. I’ve been slowly realizing the exact sentiment of your post over the past few months and it’s made me feel free. The question everyone should be asking is as you pose it…what’s right for you?

  3. As usual, you are the voice of reason in a cacophony of trendy advice. One footnote perhaps to this thoughtful piece: once we have understood the italicization “what’s right *for you*”, we need to move on to “what’s *right* for you.” And when it comes to creative endeavors like startups (or arts, music, literature, for that matter), the “right” in “right for you” is a tricky concept. In your blog post, you give examples of how vastly different it can be for different people. What I’d like to add here is that sometimes, the right thing for you is not even your choice. It can be what you’re driven by, what you feel you’re destined to do. And that can be more of a burden than anything else. Rudolf Diesel is perhaps an example.

    “Do what you must do, do it well.” ~Bob Dylan

    • I love your notion that what’s right for you isn’t your choice. In one sense, it seems like the ultimate thing that defines you, and thus isn’t it ironic that it’s not something you get to chose? :-)

  4. Beautifully put Jason. I think one of the hardest things on the entrepreneurial path is to not be distracted by the cacophony of information coming at us from all sorts of devices via the Internet.

    I think the key is to be able to go within yourself and really understand what’s right for you.

    And unfortunately, I don’t think this understanding comes in one hour or one week.

    It requires observing yourself over a long period of time and ‘watching’ how you react to various situations and why. It requires developing insights into our thought patterns and our natural tendencies when we come up against various situations that life throws at us.

    I’ve found that a mindfulness practice (self-awareness as often as you can remember to practice it) helps. After 3 years of practising mindfulness I decided to quit a career in finance that spanned 15 years and 3 continents. I started a blog.

    Unfortunately I haven’t got to the part where I’m confident in my choice. Hope that happens soon. :-)

  5. This is so ridiculously refreshing; something I think a lot of us think about and are aware of, but nice to see it all spelled out. I’ve experimented with a couple of side projects over the past 18 months, whilst working at a company I love, (, and one of my biggest and most unexpected challenges was figuring out how to communicate each thing I was working on with family/friends/colleagues, etc. Do I want to sound all in? Or should I casually mention them as pet projects to set low expectations? What if people think I’m spread to thin, or not a good product guy because of how many things are going on?

    In the end, I had to ask myself why I wanted to work on side projects. I was in it to learn and to stimulate myself with things different from the day job. Once I figured that out, nothing else mattered, as I knew what success meant for me. Made a huge difference. (Article I wrote on this a while back here:

    Great post, thanks for the reminder.

  6. Thoughtful and insightful as per usual. The difficulty though for me and I think for other people is that the only way to be “comfortable and confident in your choice” is often to make the wrong choice.

    There’s such a large amount of emotional and intangible aspects associated with any of those choices that you don’t really get it until you do it and mess it up.

    I recently re-read the 4HWW 5 years later and the entire time I was re-reading it, all I kept saying was “Yes! I made all the same mistakes!” Even when I was intellectually warned about them all on the front-end, I still fell into all the same traps.

    In my experience, the precursor to being “comfortable and confident in your choice” is actually making all the wrong choices and doing all the wrong things for all the wrong reasons.

    • A million plus 1s to this comment. I’ve been stumbling around like an idiot for the last few years making all manner of mistakes but it’s the lessons from those mistakes that inform my contentedness now.

  7. Crazy insightful man. It’s more important than anything to have your own genuine sense of drive and ambition. After all, that’s the only thing that sticks around when the going gets tough. Great thoughts.

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