Reflecting on My Failure to Build a Billion-Dollar Company

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.

I prefer not to do the math.

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!

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!

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.

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.

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.

Pinterest is a malignant tumor on the face of the Web that exists to trick people who are trying to search for images. Being rich off that would be worse that toiling in obscurity.

Reminds me of Noah Kagan. Employee #30, I think, at Facebook. That should be what - $200M+?

People actually do use Pinterest to collect images, I think, but I agree with you on the other points

You are vastly overestimating what even an early employee (esp a jr one) gets at a unicorn. Not that it wouldn't be substantial today, but nothing close to 1-2% of the entire value of the company.

crunchbase says pinterest has had 15 funding rounds. certainly they weren't all complete rounds and it would've been nice equity but nowhere near the nominal 1-2% early employees get.

If there a year at least vested one year of equity...?

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!

> You are vastly overestimating what even an early employee (esp a jr one) gets at a unicorn. Not that it wouldn't be substantial today, but nothing close to 1-2% of the entire value of the company.

Mmm...based on the valuation even 0.1% would equate to $10 million...not bad ;-)

for what it's worth I think you've created more value at Gumroad then you would have at Pintrest :)

Uh - can you elaborate? I often search for images and sometimes from pinterest - but I don't find pinterest interfering with my searches when not using it.

If he stayed he might have ended up in an executive position, getting additional stock grants down the line.

Probably a fraction of that. Dilution etc.

My guess is he’ll make more from Gumroad over the long run.

you'd probably get around .1% as an early jr person. assuming a 4 year vest period, that .1% will have been diluted to maybe .05%, so assuming a $10b valuation it comes out to $5m. Still not bad, but a far cry from $200m.

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.

fair enough

The poster is likely referring to how Pinterest links now dominate Google image search results. Clicking on the Pinterest link takes you to the Pinterest website, and not the actual image source. Pinterest will often block you from viewing the page unless you sign in or create an account.

"It's crazy that you care about the money..."

Did you read the article?

Look on the bright side - maybe Pinterest would have failed if you stayed there.

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.

Paraphrasing (probably Nietzsche):

"There are only 3 kinds of people: the poor that wants to be rich, the rich that wants to continue being rich and the idealist, that using his ideals wants to be rich."

What's the big advantage of having 200m vs 15m or so?

It's fuck-you money either way.

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