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Apply HN: Pinboard – Make Y Combinator Great Again
409 points by idlewords on Apr 6, 2016 | hide | past | web | favorite | 59 comments
A tremendous, huge opportunity to fund the Bay Area's slowest-growing unicorn.

This is a funny thread, but if any of you are amused and hopeful about the idea of Pinboard becoming a YC company, and you don't already have a Pinboard account, go get one!

I was a bookmarking skeptic before I signed up for Pinboard. In fact, I think I got my Pinboard account as repayment for a favor Erin and I did for Maciej. But now, I have no idea what I would do without it. Pinboard has more or less become a search engine for my life.

Part of what makes Pinboard great is knowing it isn't going to break; it's going to keep doing what it says on the label, pretty much the way it does, and I'm never going to have to switch to some crazy iOS app or download an Electron shell or really even click or scroll on anything.

If you're not already using something like Pinboard, I think you should consider starting, right away, and probably the thing like Pinboard you should use is Pinboard.

> Part of what makes Pinboard great is knowing it isn't going to break

If you're not following him on Twitter, you really should be.

I've yet to determine if I can cancel my HBO subscription that I keep around for the show Silicon Valley and just read that account.

> But now, I have no idea what I would do without it.

I use it every day. It's hard to believe that in 2016 neither Chrome nor Safari has support for bookmark tags... my favorite feature of Pinboard.

I know you're ribbing us, but paying for a Pinboard account is like buying shares in Berkshire Hathaway. It's for true believers. I think there's always opportunity in concentrations of users like that.

Of all the partners at YC, I ran the startup that was the most different from everyone else. And my approach might be more aligned with your values. If you were seriously interested, I'd be delighted to work with you.

That's a very kind and flattering analogy. Thank you!

I feel like after seven years, I have a pretty good sense of what bookmarking/archiving needs people have, but am at the limits of what I can personally build. If the votes swing my way, I'd be happy to have a good-faith conversation with you.

How is buying shares in Berkshire Hathaway for "true believers"?

A lot of the buyers believe Warren will keep doing well. Holder since '96. Though you can buy to flip if you want.

"Do Things That Don't Scale"


Since a hosted bookmarking service obviously scales well, that can't be the heart of the Pinboard value prop. What does Pinboard do that no one does, that seems totally nonscalable?

How about @Pinboard? He's just one man, hand-crafting tweets about the SF tech industry in his spare time... it can't possible scale to every city and industry, can it? (Can it?) And bonus: the Twitter handle is producing $0 revenue!

The answer is clear: $100 million of investment. $50 million for a machine learning system that will ingest the @Pinboard snarky tweet corpus, and output tweets adapted to other industries and localities. And $50 million for a custom ad bidding system that injects subtle product placements into the tweets at the ###### possible CPC.

###### - If you are an investor, please read this as "highest". If you are a customer, please read this as "lowest."

EDIT - My numbers are all wrong. It should $20 million for the AI, $20 million for the ad system, $55 million for marketing and signing bonuses, and $5 million for the cafeteria.

Eliezer Yudkowsky made me swear on the Necronomicon never to feed the Pinboard tweet corpus into any self-modifying learning algorithm.

But that won't stop the rest of us

Necronomicon oaths work even if you don't swear them.

    $5 million for the cafeteria
Sounds right. It costs a lot to import enough Argentinian beef to feed your engineers two steaks a day.


This excellent essay is just further evidence I'm right: the future of Pinboard is writing.

Maybe the best thing Ycombinator could do for Pinboard is sell the bookmarking service and send Maciej around the world with a laptop and a publishing contract.

"Pinboard's Guide to Argentina"

"Pinboard's Guide to Antarctica"

"Pinboard's Guide to Silicon Valley (volumes I-X)"

'idlewords once demonized the last 2 industries I worked in, in a single presentation and it was one of my proudest moments.

I feel like with proper funding he could hit all 5 and possibly call me out for my high school indiscretions as well. I for one can think of very few things that deserve funding more than that.

What steps would you take to make sure Pinboard is taken to the next level?

Where would the money go? Would you consider investing, assuming you get the funding, at least $1m into a $plashy landing page?

Finally, what is your strategy (and God help you if you do not have it) towards convincing potential investors to give you $80m and not think about the revenue?

For Pinboard, the next level is 'get an office and a sysadmin'.

Spending $1M on a landing page sounds like a fun challege. If that pledge makes people invest, I'm happy to make it.

I realize that having revenue makes many investors uneasy. If that remained a stumbling block, I would consider moving to some kind of free plan.

Now tell us how this would affect your plans for the next round of Co-Prosperity Cloud awardees.

$41? $43? Sky's really the limit here.

"Co-Prosperity Cloud 2: the Trickle-Down"

It's a delicate question. There's an irresistible temptation to spend lavishly once you pass the $40 psychological milestone. I don't want to make the same mistake YCombinator made.

I have been using Pinboard for five years, I have 3500 bookmarks in it. Along with GitHub, it is probably the SaaS that has improved my life the most.

Don't get me wrong, I'm sure Pinboard is great for what it does, and it obviously has a fan base, but in a world where Evernote and Pocket exist and are massive, there is not a lot of room for a service like Pinboard to become huge. If I were an investor I'd be wondering "how does this become a massive internet consumer service" and I just don't see the answer to that question.

I back up everything I save to Pocket into Pinboard (via IFTTT) because I know it's not going to randomly dick about with my experience like Pocket sometimes does and also that it's much less likely to flame out/sell out/"continue our journey with [CORP]" and shaft me.

(In fact, I have a whole bunch of IFTTT rules to save "faves" into Pinboard from Flickr, Instagram, Twitter, etc.)


Wait until Evernote and Pocket flame out and pick up the leavings? (It worked with Delicious...)

Evernote is doing a pretty good job of it right now.

It's not a glamorous business model, but with so many online services aiming for the stars, one can make a decent living gathering up the wreckage.

I am going to be very sad if Maciej does anything that keeps him from writing prose as much as he wants to.

I promise not to be seduced into a dead-end poetry career. But seriously, thank you very kindly.

How will you handle people that say "you mean pinterest?"

(btw, love pinboard!)

Short term: raising awareness, clever ad campaign

Long term: acquired by Pinterest

ITYM "acquire Pinterest"

> Long term: acquired by Pinterest

I will find you.


This is huge people! This is the one way to make YC great again.

gets YC money

immediately acquires delicio.us

I almost got them on the last sale!

Delicious costs $9K/month to run on AWS, so funding would definitely help there.

As far as I can tell, the site is now being run by some regretful SEO dude in Canada, and I don't think it would take a large suitcase of money to get it away from him.

Surely you mean del.icio.us ?

I honestly don't care about any startup (especially a dying one) enough to remember where the periods are supposed to go if there is more than one.

Is this "still" a startup? It must have been around for decades.

Both del.icio.us and delicio.us forward to http://www.delicious.com/ now

When I talked to them about buying the site, the Science Inc. people were very clear that they intend to keep the delicious.com domain for some (presumably awful) new project.

The current redirect is temporary.

I have been dumping my links into an email address for years - reading with thunderbird. a long while ago, i was turned off by not being able to try it for a few weeks (i'm slow to take something like this and integrate it into my life)

alright pinboard, ill give you a shot.

Don't miss the reading list feature in Pinboard :)

Though I use Instapaper myself, I'd consider using it more in Pinboard if there were support for a parse webpages into plain text service.

no point messing about with delicious, pinboard should take over yahoo.

Wow, didn't expect to see this here. I'd love to see Pinboard go through YC.

I will go through YC like a bowling ball through a python

You are very hard to understand. You have many times criticized HN and YC for many different things (the most memorable examples being objecting to how HN uses the word "startup", and to PG hellbanning you), and yet here you are, cleverly using "Apply HN" to raise awareness about Pinboard in the community you dislike while having no intention of being part of YC.

I am hoping to attract a certain protest vote of the silent majority who enjoy this community, but are uneasy about the values of its founders and more broadly, Silicon Valley.

As far as HN proper, I don't dislike this community at all, particularly since dang took the reins. It's an interesting place and I've tried to contribute in good faith for many years now, besides just making fun of it.

Let's say you attain this goal and the protest votes are in, signalling to YC that a (no longer) silent majority feel this way. Now they get the message that the community is "uneasy about the values of its founders and more broadly, Silicon Valley". What's next? I imagine reading posts by the community here does not play a huge role in day-to-day operations at the company, they still have day jobs and financial pressures to deal with whether we like them or not. Is there a plan or end game or is this pure trolling (or maybe I put it more kindly and call it 'performance art' or something like that)?

I'm pretty sure Silicon Valley are quite well aware that privacy is an issue and a growing number of users are uncomfortable with the surveillance-as-a-service business model, but it pays the bills so why would they change? How can you create this demand so that the pro-privacy business model works?

I'm curious to see what you can make of the opportunity, if one even exists here.

I understand your point, but established Silicon Valley investors are not the audience I'm trying to reach, or persuade.

I would call what I do 'impure trolling', since I run an actual business, and have given an earnest series of talks calling for regulations on mass surveillance.

Following in this earnest vein, I live a life of independence and fun, and would like to encourage young technical people to live that life too, rather than wasting their youth in pursuit of a one-in-ten-thousand shot at plutocracy.

As a 20-something startup engineer, I'd love to hear you write a blog post with more on that last bit.

I gave a talk called "Barely Succeed - it's easier!" where I tried to make the case. There's a video version here [https://www.youtube.com/watch?v=5Vt8zqhHe_c], unfortunately I haven't transcribed it yet.

Every court needs its clown and I've been grateful to Maciej for being that clown for years. He's been the only one -- the only one -- that has consistently managed to make me feel less crazy and make Silicon Valley look a little bit more crazy.

The startup scene hasn't been content with "paying the bills". They've been chasing demand even when that demand doesn't bring actual money along with it. It's completely nuts, and maybe it should change a little.

I mean, you sort of imply that the pro-privacy business model doesn't work, but Pinboard is more profitable than Twitter. Does that mean profitability is no longer the measure of whether a business model "works"?

> the _only_ one

The folks at Basecamp (formerly 37signals) have been pretty consistent too at criticizing the Silicon Valley rhetoric, and their company is undeniably profitable. They write at https://signalvnoise.com and I also recommend their books.

I get so much use out of pinboard (and laughing at your tweet snark) that I would gladly pay $5/month instead of the one-time fee of whatever I paid when I signed up.

It Just Works, and that's all it does, and that's all I need it to do.

A big python or a little python?

edit It may also be useful to know the size and weight of the bowling ball.

I* am curious about your growth.

Did signup conversion change when you switched from one-time fee to recurring?

Do you have any current weird channels for user acquisition? I mean, besides those last few del.icio.us users...

*as a Pinboard customer

P.S. For anyone who hasn't seen, Pinboard's Twitter account is pretty amusing startup satire.


I think conversion changed, but I don't know. I don't do a very good job at tracking it.

My weird channels for acquisition are a variety of publicity stunts and Twitter drama. Something like IFTTT recently threatening to turn off their Pinboard channel is manna from heaven for me.

That was a heart-stopping day given how many Pinboard rules I have.

i have a different take on this . I think buffer and pocket have done great work in this year. Obviously pinboard as well. I am not sure if I am the only one but I think the problem is bookmarking. On HCI terms, bookmarking is not intuitive to how human brains work. Instead we just go through events and the nature of events makes us AUTOMAGICALLY index them in our brain and when we wish to retrieve them our brain just uses that index.

On those lines I think it should be more like log everything that I hit on all my devices and make the search organized. Something similar using apriori algorithm was my school project and I used it a lot until now when I have slowly moved to pocket.

My 2 cents - "In short better to have a smart search and indexing instead of bookmarking "

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