Headspace

company on 18 shows · 42 statements across 10 episodes · said 289 times in 75 episodes since 2015

20VC 150 How I Built This 68 Top Founders 16 My First Million 11 We Live to Build 9 Capital Allocators 7 Acquired 5 the a16z Podcast 4 the Y Combinator Startup Podcast 3 Lenny's Podcast 3 Founder's Journal 2 the Knowledge Project 2 the Startup Ideas Podcast 2 All-In 2 TBPN 2 the Pitch 1 Latent Space 1 WTF is with Nikhil Kamath 1

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2026 2 mentions in 1 episode
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2018 4 mentions in 3 episodes 1 per episode
2017 6 mentions in 3 episodes 2 per episode
2016 142 mentions in 15 episodes 9 per episode
2015 10 mentions in 4 episodes 3 per episode

every mention on every show, scene by scene, with the transcript →

42 statements about Headspace, every show

Acton Smith: Calm's target market is anyone with a mind
“The market we did feel was absolutely enormous. It wasn't just the people who are meditating. It was, you Pretty much anyone with a mind. So we felt there were going to be multiple winners. Not a winner takes all market, but a winner takes most.”
Michael Acton Smith May 26, 2025 ▶ 52:47 Calm: Alex Tew and Michael Acton Smith
20VC Opinion
Stebbings: Mental wellness apps like Calm and Headspace are not great businesses
“Calm or Headspace of the world, which makes mental wellness, health, they're not great businesses.”
Harry Stebbings Jul 22, 2024 ▶ 1:02:53 Kevin Hartz: "How I Lost Airbnb at Seed Because of an Exploding Term Sheet" | E1180 · 20VC with Harry Stebbings
a16z Opinion
Moore: $60/year subscription apps struggle to scale revenue
“Many of those are amazing companies, but it's hard to generate hundreds of millions of dollars of revenue on, on things like those.”
Olivia Moore Feb 9, 2023 ▶ 27:28 The State of Apps with Olivia Moore
TOP FOUNDERS Disclosure
Brian Smith: Leon's marketplace integrates with Calm, Headspace, and Equinox
“We have a marketplace where we've integrated into head Space and the Calm and Equinox and SoulCycle and InsightTrack and all these other things where we'll tell the company the exact service to buy for that employee based off the data that we're seeing.”
Brian Smith Aug 18, 2022 ▶ 3:56 Genius Combo of SaaS Marketplace hits $2.4m ARR for Sales Burnout Tool
TOP FOUNDERS Assertion Not checkable as stated
Smith: Leon takes roughly a 20% cut on marketplace spend
“So we'll actually buy, purchase, manage the whole entire benefit, which will make a percentage on that on the employer, employer side. All right. But also on the other side, we'll make a percentage from Equinox or Headspace or whatever else. So we're making ro…”
Brian Smith Aug 18, 2022 ▶ 5:11 Genius Combo of SaaS Marketplace hits $2.4m ARR for Sales Burnout Tool
WE LIVE TO BUILD Assertion Not publicly verifiable
TRIPP boosts HRV 35% to 40% more than Headspace, test shows
“They had done a test, an AB test of, 20 minutes on headspace versus 20 minutes on trip. And they showed roughly a 35, 40% Increase in HRV, which is a measurement of how calm you are using trip versus headspace.”
Martin Tobias Apr 6, 2022 ▶ 18:59 35% Calmer in 20 Minutes: Why VR Beat the Top Meditation App
HOW I BUILT THIS Assertion Not checkable as stated
Puddicombe Made Pierson A Co-Founder Because He Couldn't Afford To Pay Him
“Andy actually said to me, would you come and, would you like to work with me? And I thought he was saying, it's my business. Would you like to come and work for me? And I was like, yeah, sure. He said, well, I can't afford to kind of pay you. But would you do …”
Rich Pierson Jan 3, 2022 ▶ 32:52 Headspace: Andy Puddicombe and Rich Pierson (2019)
HOW I BUILT THIS Assertion Not checkable as stated
Pierson's Father Seeded Headspace And Refused Equity Until Their 2015 Series A
“He never ever once asked for any shares in the business, or any return for any of the money that he gave us. And to the point that actually when we finally did do A fundraise in 2015, like our first proper fundraise, that was when we kind of forced him to take…”
Rich Pierson Jan 3, 2022 ▶ 38:11 Headspace: Andy Puddicombe and Rich Pierson (2019)
HOW I BUILT THIS Assertion Supported
A Three-Book Publishing Advance Funded Early Headspace Operations
“Secondly, it started a process where we managed to get a book deal, a three book deal with Hodder and Staunton, and the advance from that, which I think, you know, still, at that time, it was like one of the highest advances paid for a debut non-fiction author…”
Rich Pierson Jan 3, 2022 ▶ 42:08 Headspace: Andy Puddicombe and Rich Pierson (2019)
HOW I BUILT THIS Assertion Supported
Virgin Atlantic Agreed To Distribute Headspace Meditation Content Across All Flights
“The first thing was a woman called Kathy Walters at Virgin agreed to put our content on every single Virgin Atlantic plane, and we pitched her down at Gatwick”
Rich Pierson Jan 3, 2022 ▶ 48:23 Headspace: Andy Puddicombe and Rich Pierson (2019)
HOW I BUILT THIS Assertion Not publicly verifiable
The Guardian Distributed One Million Free Headspace Booklets On Its Front Covers
“And then on the back of that, we then managed to convince the Guardian newspaper in the UK to put a million Booklets on the front, and we didn't pay for it.”
Rich Pierson Jan 3, 2022 ▶ 48:51 Headspace: Andy Puddicombe and Rich Pierson (2019)
HOW I BUILT THIS Assertion Not checkable as stated
Headspace Generated £32,000 In Revenue In Its First Month After Launch
“Like, in that first month that we launched, we took 32,000 pounds in revenue in that first January, and that was, you know, based, we'd never made a single penny in any month leading up to that.”
Rich Pierson Jan 3, 2022 ▶ 49:28 Headspace: Andy Puddicombe and Rich Pierson (2019)
Pierson: The US Possesses A Uniquely Supportive Culture For Ambitious Startups
“I think in the UK, you speak to someone about an idea, and they'll give you a thousand reasons why you can't do it, and I think in America, you say the same idea, and they go, there's a thousand reasons why it'll work, and have you thought about making it bigg…”
Rich Pierson Jan 3, 2022 ▶ 51:23 Headspace: Andy Puddicombe and Rich Pierson (2019)
HOW I BUILT THIS Assertion Not checkable as stated
Headspace Met With Over 60 VC Firms Before Closing Their First Deal
“We probably, to be honest, we probably went overboard, but we met over 60 different investment houses, would be the best way to describe it, until we found someone that we really felt aligned with, and we could get the deal done that would work for us.”
Rich Pierson Jan 3, 2022 ▶ 56:27 Headspace: Andy Puddicombe and Rich Pierson (2019)
Krim: The killer app for Calm and Headspace is sleep, not meditation
“The folks like Calm and Headspace have gone on to build great businesses, and I think the killer application for those businesses is not meditation. I think it's sleep”
Philip Krim Jun 28, 2021 ▶ 53:16 Casper: Philip Krim
HOW I BUILT THIS Assertion Not checkable as stated
Puddicombe: Headspace anxiety and stress content engagement jumped roughly 1,000%
“I think that some of the media stars across anxiety and stress content were up sort of a thousand percent.”
Andy Puddicombe May 30, 2020 ▶ 14:38 How I Built Resilience: Live with Alli Webb and Andy Puddicombe & Rich Pierson
HOW I BUILT THIS Assertion Not checkable as stated
Puddicombe: Headspace B2B inbound inquiries surged over 400% during lockdown
“The inbound from businesses, from organizations was up over 400%.”
Andy Puddicombe May 30, 2020 ▶ 14:44 How I Built Resilience: Live with Alli Webb and Andy Puddicombe & Rich Pierson
HOW I BUILT THIS Assertion Not checkable as stated
Puddicombe's Gig Teaching Russian Oil Execs Sparked Idea to Demystify Meditation
“And then one of the expats had invited me to go in and teach his execs at an oil company in, in Russia. And he said, look, you know, kind of, you can't come in dressed as a Buddhist monk, you know, it's an oil company, we're in Moscow. And that had got me thin…”
Andy Puddicombe Sep 23, 2019 ▶ 18:34 Headspace: Andy Puddicombe and Rich Pierson
HOW I BUILT THIS Assertion Not checkable as stated
Puddicombe Saw 6-10 Daily Clients in London Clinics Before Headspace
“I was working full-time in the clinics, Seeing anything from six to 10 people a day. And I started at weekends. I started, I did a few workshops, but it only really changed to sort of much larger, larger groups after I met my now very good, good friend, Rich w…”
Andy Puddicombe Sep 23, 2019 ▶ 23:26 Headspace: Andy Puddicombe and Rich Pierson
Puddicombe: Headspace would have failed without seed money from Pierson's father
“I mean, honestly, if it hadn't have been for Ian, like we wouldn't have made it.”
Andy Puddicombe Sep 23, 2019 ▶ 36:53 Headspace: Andy Puddicombe and Rich Pierson
HOW I BUILT THIS Assertion Not checkable as stated
Pierson's Father Invested Early in Headspace Without Asking for Equity
“He never ever once asked for any shares in the business or any return for any of the money that he gave us. And to the point that actually when we finally did do a fundraise in 2015, like our first proper fundraise. That was when we kind of forced him to take …”
Rich Pierson Sep 23, 2019 ▶ 38:02 Headspace: Andy Puddicombe and Rich Pierson
Headspace Spent £20K of Its £50K Capital on Physical Collateral
“So we spent, of the 50,000 pounds, we spent 20,000 pounds of it on the kind of physical collateral to give out at the event.”
Rich Pierson Sep 23, 2019 ▶ 40:19 Headspace: Andy Puddicombe and Rich Pierson
HOW I BUILT THIS Assertion Supported
Puddicombe's Hodder & Stoughton Book Advance Funded Early Headspace Operations
“We managed to get a book deal, a three book deal with Hodder and Staunton, and the advance from that, which I think, you know, still, at that time it was like one of the highest advances paid for a debut non-fiction author, really funded the rest of the busine…”
Rich Pierson Sep 23, 2019 ▶ 41:59 Headspace: Andy Puddicombe and Rich Pierson
HOW I BUILT THIS Assertion Not publicly verifiable
Virgin Atlantic Distributed Headspace Content on Every Plane for Free
“First thing is a woman called Kathy Waters at Virgin agreed to put our content on every single Virgin Atlantic plane.”
Rich Pierson Sep 23, 2019 ▶ 48:15 Headspace: Andy Puddicombe and Rich Pierson
HOW I BUILT THIS Assertion Partly supported
The Guardian Distributed One Million Headspace Booklets for Free
“And then, on the back of that, we then managed to convince the Guardian newspaper in the UK to put a million Booklets on the front, and we didn't pay for it.”
Rich Pierson Sep 23, 2019 ▶ 48:42 Headspace: Andy Puddicombe and Rich Pierson
HOW I BUILT THIS Assertion Not checkable as stated
Headspace Generated £32,000 in Revenue in Its Launch Month
“Like in that first month that we launched, we took 32,000 pounds in revenue in that first January. And that was, you know, based, we'd never made a single penny in any month leading up to that.”
Rich Pierson Sep 23, 2019 ▶ 49:21 Headspace: Andy Puddicombe and Rich Pierson
Pierson: US Optimism Makes It Superior to UK for Ambitious Startups
“I think in the UK, you speak to someone about an idea, and they'll give you a thousand reasons why you can't do it, and I think in America, you say the same idea, and they go, there's a thousand reasons why it'll work, and have you thought about making it bigg…”
Rich Pierson Sep 23, 2019 ▶ 50:47 Headspace: Andy Puddicombe and Rich Pierson
HOW I BUILT THIS Assertion Not checkable as stated
Headspace Pitched Over 60 Investment Firms Before Closing Funding Deal
“We probably, to be honest, we probably went overboard, but we met over 60 different investment houses, would be the best way to describe it, Until we found someone that we really felt aligned with, and we could get the deal done that would work for us.”
Rich Pierson Sep 23, 2019 ▶ 55:51 Headspace: Andy Puddicombe and Rich Pierson
Pierson: Headspace Can Scale Content Using Instructors Beyond Andy Puddicombe
“As long as we always stay true to the way that we build products, I think there's a huge room to bring in other voices, other experts that aren't Andy, so.”
Rich Pierson Sep 23, 2019 ▶ 1:02:17 Headspace: Andy Puddicombe and Rich Pierson
20VC Assertion Supported
Headspace reached eight million downloads by August 2016
“As it continues to expand the product, which has been downloaded a whopping eight million times now.”
Harry Stebbings Aug 26, 2016 ▶ 0:28 20VC: Maximising Engagement and Retention on Mobile & Why There Should Always Be Availability To A Free Product with Sean Brecker, CEO @ Headspace
20VC Assertion Partly supported
Headspace raised funding from Jim Breyer, Jeff Weiner, and Jared Leto
“Sean was also instrumental in raising the first institutional round of funding for Headspace from some incredible names like Jim Breyer, LinkedIn's Jeff Weiner, Michael Linton's Sony CEO. Hey, they're so cool. They even have movie stars Jared Leto and one of m…”
Harry Stebbings Aug 26, 2016 ▶ 0:37 20VC: Maximising Engagement and Retention on Mobile & Why There Should Always Be Availability To A Free Product with Sean Brecker, CEO @ Headspace
20VC Assertion Not checkable as stated
Headspace had roughly 15 employees when CEO Sean Brecker joined
“At the time the company was about 15 people and primarily designers and content creators.”
Sean Brecker Aug 26, 2016 ▶ 4:19 20VC: Maximising Engagement and Retention on Mobile & Why There Should Always Be Availability To A Free Product with Sean Brecker, CEO @ Headspace
20VC Assertion Supported
Over 2,000 peer-reviewed studies validate the health benefits of meditation
“There have been today over 2000 studies by researchers, and these are, you know, very serious studies, peer reviewed on the benefits of meditation”
Sean Brecker Aug 26, 2016 ▶ 6:57 20VC: Maximising Engagement and Retention on Mobile & Why There Should Always Be Availability To A Free Product with Sean Brecker, CEO @ Headspace
20VC Insight
Secular positioning is key to mass adoption for meditation apps
“We position this practice in a very modern, you know, secular way. And we do that by design because we believe that you know, that is the key to reaching the masses and sort of lowering the barrier to entry.”
Sean Brecker Aug 26, 2016 ▶ 7:34 20VC: Maximising Engagement and Retention on Mobile & Why There Should Always Be Availability To A Free Product with Sean Brecker, CEO @ Headspace
20VC Assertion Not checkable as stated
Headspace co-founder Andy Puddicombe records all guided meditation packs entirely unscripted
“When he's actually recording the pack, it's all unscripted.”
Sean Brecker Aug 26, 2016 ▶ 10:22 20VC: Maximising Engagement and Retention on Mobile & Why There Should Always Be Availability To A Free Product with Sean Brecker, CEO @ Headspace
20VC Assertion Supported
Apple asked Headspace to offer free SOS meditations on Apple Watch
“When Apple released the Apple watch, they came to us and asked us if we would consider putting our SOS meditations, you know, these short form two minute meditations for when you've, you're having some kind of crisis and just really need to sort of very quickl…”
Sean Brecker Aug 26, 2016 ▶ 13:20 20VC: Maximising Engagement and Retention on Mobile & Why There Should Always Be Availability To A Free Product with Sean Brecker, CEO @ Headspace
20VC Assertion Not checkable as stated
The vast majority of Headspace users are first-time meditators
“The vast majority of our users are new to meditation. They have never meditated before.”
Sean Brecker Aug 26, 2016 ▶ 15:14 20VC: Maximising Engagement and Retention on Mobile & Why There Should Always Be Availability To A Free Product with Sean Brecker, CEO @ Headspace
20VC Assertion Not checkable as stated
Headspace users shift from acute stress relief to daily preventative habits
“We have seen, you know, migration of people from aspirin into vitamin, which is great news for us.”
Sean Brecker Aug 26, 2016 ▶ 16:08 20VC: Maximising Engagement and Retention on Mobile & Why There Should Always Be Availability To A Free Product with Sean Brecker, CEO @ Headspace
20VC Opinion
Headspace competes for user time against social media, not other apps
“We don't really view other meditation apps as competition. At the end of the day, what we are doing is we're trying to compete for people's time. The time is, you know, the most precious resource that we all have, especially in today's busy world. And what we'…”
Sean Brecker Aug 26, 2016 ▶ 17:02 20VC: Maximising Engagement and Retention on Mobile & Why There Should Always Be Availability To A Free Product with Sean Brecker, CEO @ Headspace
20VC Assertion Not checkable as stated
Headspace pitched 63 different investors during its Series A raise
“I think through the whole process, we met something like 63 different investors.”
Sean Brecker Aug 26, 2016 ▶ 19:21 20VC: Maximising Engagement and Retention on Mobile & Why There Should Always Be Availability To A Free Product with Sean Brecker, CEO @ Headspace
20VC Assertion Not checkable as stated
Headspace's strategic investors were active fans of the product before investing
“I think the interesting thing is almost universally across our cap table, our investors are big fans of the product and have had, you know, there's been a sort of profound impact on their lives that, that, that has occurred because of their use of the product.…”
Sean Brecker Aug 26, 2016 ▶ 21:07 20VC: Maximising Engagement and Retention on Mobile & Why There Should Always Be Availability To A Free Product with Sean Brecker, CEO @ Headspace
20VC Assertion Not checkable as stated
Headspace holds optional team meditation sessions twice daily
“Our team meets at 10 a.m. And three p.m. Every day, and it's optional, but you know, a number of folks show up and do the meditation during one of those two sessions.”
Sean Brecker Aug 26, 2016 ▶ 23:06 20VC: Maximising Engagement and Retention on Mobile & Why There Should Always Be Availability To A Free Product with Sean Brecker, CEO @ Headspace

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