Dropbox

24 statements across 11 episodes · 5 bullish · 0 bearish · 11 people on the record · first statement Mar 12, 2014 by Jessica Livingston · said 105 times in 34 episodes since 2013 · across every show →

Mentions by year

brought up most by Sam Altman (21), Pejman Nozad (9), Tikhon Bernstam (8), Eric Migicovsky (8), Drew Houston (7), Shola Akinlade (4), Paul Graham (4), Craig Cannon (4)

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2024 3 mentions in 2 episodes 2 per episode
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2022 5 mentions in 2 episodes 3 per episode
2019 11 mentions in 4 episodes 3 per episode
2018 33 mentions in 15 episodes 2 per episode
2017 40 mentions in 4 episodes 10 per episode
2016 2 mentions in 1 episode
2014 1 mention in 1 episode
2013 1 mention in 1 episode

every mention, scene by scene, with the transcript →

Everything said about Dropbox, oldest first

Mar 12, 2014 bullish
Assertion Supported
Livingston: YC funded 632 startups valued at over $20B by 2014
“So fast forward to today, and Y Combinator has funded 632 startups that now have a combined valuation of over twenty billion dollars, including Dropbox, Airbnb, Weebly, and Stripe.”
Jessica Livingston Mar 12, 2014 ▶ 9:41 Jessica Livingston at Female Founders Conference 2014 · Y Combinator
Feb 23, 2017
Assertion Not checkable as stated
Arash Ferdowsi dropped out of MIT the day after meeting Drew Houston
“Where Arash just said, hey, let's meet up, and we hung out in the Student Center for a couple hours, and he dropped out of school the next day.”
Drew Houston Feb 23, 2017 ▶ 3:54 Drew Houston : How to Build the Future · Y Combinator
Feb 23, 2017
Insight
Founders need thick skin for critics but thin skin for users
“I think where it gets a little harder is you have to simultaneously have thick skin and be able to tune things like that out. But you also have kind of thin skin, and if your customers are unhappy or your team's unhappy, you have to respond to that.”
Drew Houston Feb 23, 2017 ▶ 7:28 Drew Houston : How to Build the Future · Y Combinator
Feb 23, 2017
Insight
Houston: True focus means killing beloved products and viable ideas
“Everybody loves the idea of focus, but what focus actually means is like shooting stuff you love and turning down things you know you can make work.”
Drew Houston Feb 23, 2017 ▶ 25:31 Drew Houston : How to Build the Future · Y Combinator
Feb 23, 2017
Assertion Not checkable as stated
Drew Houston built a working Dropbox prototype in six to eight weeks
“Probably about, I'd say a couple months. It was six weeks, six to eight weeks. You know, when it's early you can make massive product, progress like that.”
Drew Houston Feb 23, 2017 ▶ 9:36 Drew Houston : How to Build the Future · Y Combinator
Feb 23, 2017
Disclosure
Drew Houston: Dropbox idea was sparked by forgetting a thumb drive
“The sort of origin story of the company was when I was riding the Chinatown bus from Boston, New York, and forgot my thumb drive. Couldn't get anything done on the trip.”
Drew Houston Feb 23, 2017 ▶ 0:21 Drew Houston : How to Build the Future · Y Combinator
Feb 23, 2017 positive
Assertion Not checkable as stated
Houston: Viral Loops Drove Half of Early Dropbox Sign-ups
“Coming up with things like, ah, the referral program, and which had this two-side incentive where if I give you, if I tell you about Dropbox, you get free space, I get free space. That drove, like, 30% of our sign-ups for a while. Shared folders inherently vir…”
Drew Houston Feb 23, 2017 ▶ 28:27 Drew Houston : How to Build the Future · Y Combinator
Feb 23, 2017
Assertion Not publicly verifiable
Early Dropbox demo stayed atop Hacker News for two days
“It stayed at the top of Hacker News for two days.”
Drew Houston Feb 23, 2017 ▶ 5:43 Drew Houston : How to Build the Future · Y Combinator
Feb 23, 2017
Insight
Houston: A CEO's role changes constantly and early strengths become hindrances
“Your job as CEO changes every six months, every year, every couple years. Just nobody tells you that. And in fact, some of the things that made you good at the prior stage are becoming a hindrance for the next stage.”
Drew Houston Feb 23, 2017 ▶ 12:04 Drew Houston : How to Build the Future · Y Combinator
Feb 23, 2017
Assertion Not checkable as stated
Dropbox still runs some of Drew Houston's original code in production
“Some. I think they've done some analysis. That's, there's still stuff in there.”
Drew Houston Feb 23, 2017 ▶ 12:37 Drew Houston : How to Build the Future · Y Combinator
Feb 23, 2017 neutral
Assertion Not checkable as stated
Houston: Dropbox Scaled to 7M Users With Under 50 Employees
“The team, I'm thinking about, you know, seven to seven million, we're probably fewer than, under 50 people.”
Drew Houston Feb 23, 2017 ▶ 26:13 Drew Houston : How to Build the Future · Y Combinator
Jul 1, 2017 neutral
Insight
Benet: Filecoin is an enterprise cloud storage replacement, not consumer Dropbox
“Filecoin is not to be seen as a Dropbox replacement, although there will be Dropbox-like things that build on top of Filecoin. I think you should think about Filecoin as replacing cloud storage. So it's something that Dropbox would use.”
Juan Benet Jul 1, 2017 ▶ 1:54:02 IPFS, CoinList, and the Filecoin ICO with Juan Benet and Dalton Caldwell · Y Combinator
Sep 8, 2017 positive
Opinion
Bernstam: Solo founders can succeed despite Silicon Valley conventions against them
“I actually like solo founders. I know that's an unconventional thing in the Valley, but Drew was initially a solo founder with Dropbox. And a lot of other great companies were as well, or had one founder who really drove the project through.”
Tikhon Bernstam Sep 8, 2017 ▶ 33:10 The Challenges a Repeat Founder Faces - Tikhon Bernstam · Y Combinator
Sep 8, 2017
Assertion Not checkable as stated
Bernstam: Major investors passed on Dropbox at a $2 million valuation
“A lot of famous investors, I won't name, passed on Dropbox at a two million dollar valuation, saying, the space is too crowded.”
Tikhon Bernstam Sep 8, 2017 ▶ 38:22 The Challenges a Repeat Founder Faces - Tikhon Bernstam · Y Combinator
Sep 8, 2017 neutral
Assertion Contradicted
Bernstam: Modern seed rounds exceed Dropbox and Airbnb's Series A rounds
“The seed rounds today, Are bigger than, like, the Series A that Dropbox and Airbnb did with Sequoia, which I think was roughly a mil each.”
Tikhon Bernstam Sep 8, 2017 ▶ 6:16 The Challenges a Repeat Founder Faces - Tikhon Bernstam · Y Combinator
Sep 8, 2017
Insight
Bernstam: Investors don't need to rush into deals on Demo Day
“Like say Dropbox and Airbnb, they took like over a year to go from Demo Day to their Series A. So you don't have to actually rush into things at Demo Day. There's a lot of room in the post seed world where you can kind of invest like maybe at a slightly higher…”
Tikhon Bernstam Sep 8, 2017 ▶ 35:25 The Challenges a Repeat Founder Faces - Tikhon Bernstam · Y Combinator
Sep 5, 2018 neutral
Insight
Rusenko: The best startups create new markets, rendering market research useless
“The best companies will create a market. So if you look at sort of what Weebly's done, if you look at what Airbnb's done, if you look at what Dropbox has done, all, all companies have created their own market. I say this because by definition here, market rese…”
David Rusenko Sep 5, 2018 ▶ 12:22 David Rusenko - How To Find Product Market Fit · Y Combinator
Sep 5, 2018
Disclosure
Rusenko: Weebly raised $650K Series A at $2M pre-money in 2007
“We raised 650 K on a two million dollar pre-money valuation. So 2.65 post. That was considered above average, slightly above average. We were all very jealous of Dropbox, who had raised a five million dollar post money valuation”
David Rusenko Sep 5, 2018 ▶ 7:28 David Rusenko - How To Find Product Market Fit · Y Combinator
Sep 6, 2018
Insight
Reinhardt: True product-market fit is unmistakable and creates uncontrollable growth
“Frankly, I think the really big product market fit moments for every company are pretty unmistakable. Like, the Dropbox founders have called it stepping on a landmine. I just, I really don't think you can mistake it. It really happens in a way that you lose co…”
Peter Reinhardt Sep 6, 2018 ▶ 18:39 Peter Reinhardt on Finding Product Market Fit at Segment · Y Combinator
Oct 10, 2018 positive
Assertion Supported
Ralston: Dropbox raised its first round at a $2M-$3M valuation
“Dropbox raised their first round at like a two or three million dollar valuation. And it worked out okay for Drew and team, right? They won IPO this year.”
Geoff Ralston Oct 10, 2018 ▶ 30:35 Fundraising Fundamentals By Geoff Ralston · Y Combinator
Jun 8, 2022 positive
Assertion Supported
Caldwell: YC's best startups often launch during economic downturns
“Some of the best companies we've ever funded happened when either there was a full downturn or at least a blip.”
Dalton Caldwell Jun 8, 2022 ▶ 3:38 Y Combinator Is Back In Person · Y Combinator
Nov 17, 2022 neutral
Assertion Supported
Dropbox had approximately 20 cloud storage competitors when it initially launched
“So when Dropbox launched, there were already about 20 cloud-based file storage companies. Dropbox was like the 20th company in its space to launch.”
Jared Friedman Nov 17, 2022 ▶ 18:29 How to Get and Evaluate Startup Ideas | Startup School · Y Combinator
Sep 27, 2024
Assertion Supported
Taggar: Dropbox founder Drew Houston was initially rejected by YC for applying solo
“Drew applied to YC as a single founder, and he was actually initially rejected and told to go get a co-founder.”
Harj Taggar Sep 27, 2024 ▶ 4:16 How To Find A Co-Founder | Startup School · Y Combinator
May 13, 2026 neutral
Assertion Not checkable as stated
A Boston VC faxed Dropbox a term sheet with a blank valuation.
“They sent Drew, the founder, a term sheet. They faxed it to him. Anybody even remember what a fax machine is? They faxed him a term sheet with a blank valuation.”
Paul Graham May 13, 2026 ▶ 8:19 Paul Graham, Founder of Y Combinator, Live from Stockholm · Y Combinator
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