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    Reflecting on My Failure to Build a Billion-Dollar Company

    (medium.com)
    2101 points jamesjyu | 14 comments | 07 Feb 19 15:28 UTC | HN request time: 0s | source | bottom
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    sixQuarks ◴[07 Feb 19 15:53 UTC] No.19105943[source]▶
    Ouch, number 2 employee at Pinterest - a $10 billion company that’s about to go public this year.

    He probably would have been worth an easy 100-200 million.

    replies(8): >>19105991 #>>19106042 #>>19106359 #>>19106363 #>>19106427 #>>19106443 #>>19106742 #>>19109545 #
    1. sahillavingia ◴[07 Feb 19 15:59 UTC] No.19105991[source]▶
    I prefer not to do the math.
    replies(12): >>19106089 #>>19106127 #>>19106166 #>>19106205 #>>19106260 #>>19106473 #>>19106504 #>>19106646 #>>19107150 #>>19108409 #>>19109985 #>>19113528 #
    2. nemild ◴[07 Feb 19 16:09 UTC] No.19106089[source]▶
    Based on your article, you sound pretty bad ass by having gone through the journey. I'm doubtful you'd have that by staying. It's a pretty remarkable path, and I respect you for that!
    3. spuderman123 ◴[07 Feb 19 16:14 UTC] No.19106127[source]▶
    Many years ago, you once mentioned that anyone who wants to build a startup should read Hacker News. I'm still here because of you. You've made an impact!
    4. PakG1 ◴[07 Feb 19 16:20 UTC] No.19106166[source]▶
    I can't begin to imagine what that must feel like, but I gotta say, your kind of company (i.e. non-VC-funded, don't care about the unicorn status, just serve the customers well) is the kind I'd like to do one day. The vision and values just align with me so much more than hypergrowth and whatever it takes to get there. Many hats off to you for making all the decisions you did to keep your customers first. It may not be worth much, but you have my respect forever.
    5. droobles ◴[07 Feb 19 16:25 UTC] No.19106205[source]▶
    Your story speaks to my soul. I've never been too attracted to the VC-funded startup life (although I wouldn't pass it up if it was the correct move to grow my business), but reading about your commitment to your users through thick and thin gives me so much more respect for you, and that is a quality I hope to emulate someday.
    6. sixQuarks ◴[07 Feb 19 16:34 UTC] No.19106260[source]▶
    Haha, sorry didn’t mean to rub it in brother.

    But you’re still in an incredibly fortunate situation, and it’s all about the journey anyway.

    7. dawhizkid ◴[07 Feb 19 16:59 UTC] No.19106473[source]▶
    If there a year at least vested one year of equity...?
    8. kickopotomus ◴[07 Feb 19 17:02 UTC] No.19106504[source]▶
    Hindsight is 20/20. A million different factors outside of your control could have led to different outcomes for both Pinterest and Gumroad. Thank you for sharing your story!
    9. ishjoh ◴[07 Feb 19 17:21 UTC] No.19106646[source]▶
    for what it's worth I think you've created more value at Gumroad then you would have at Pintrest :)
    10. crispyporkbites ◴[07 Feb 19 18:24 UTC] No.19107150[source]▶
    It's crazy that you care about the money, being in your mid-20s with a company pulling in 60k USD net/month puts you squarely in the pretty much unlimited money category of the world.
    replies(1): >>19108148 #
    11. jimbokun ◴[07 Feb 19 20:16 UTC] No.19108148[source]▶
    "It's crazy that you care about the money..."

    Did you read the article?

    12. oh_sigh ◴[07 Feb 19 20:44 UTC] No.19108409[source]▶
    Look on the bright side - maybe Pinterest would have failed if you stayed there.
    13. aeriklawson ◴[08 Feb 19 00:08 UTC] No.19109985[source]▶
    But would you trade the amount of time spent at Pinterest before IPO with the experience you gained at Gumroad? Tough call, given the professional and personal growth you gained from it.
    14. Tepix ◴[08 Feb 19 12:25 UTC] No.19113528[source]▶
    What's the big advantage of having 200m vs 15m or so?

    It's fuck-you money either way.