Reid Hoffman of LinkedIn, Brian Chesky of Airbnb, and How to Scale to 100M+ Users (#326)

“In order to scale, you have to do things that don’t scale.” — Reid Hoffman

This episode is a showcase from Masters of Scale, one of the few podcasts I recommend repeatedly to entrepreneurs. It’s a conversation between LinkedIn co-founder Reid Hoffman (@reidhoffman) and Airbnb co-founder Brian Chesky (@bchesky), and it focuses on how you can scale your company by, paradoxically, doing things that don’t scale.

This is, in some ways, part two of my conversation with Airbnb’s co-founder Joe Gebbia (which you can check out here). I also highly recommend subscribing to Masters of Scale, which just began its third season and features interviews with founders of Spotify, Instagram, TaskRabbit, Shake Shack, and Glossier, among many others.

And if you’re looking for a companion piece to read with this episode, I can recommend none better than 1,000 True Fans by Kevin Kelly (@kevin2kelly).

Please enjoy this short conversation between Reid Hoffman and Brian Chesky, with a few cameo appearances in the mix.

You can find the transcript of this episode here. Transcripts of all episodes can be found here.

#326: Reid Hoffman of LinkedIn, Brian Chesky of Airbnb, and How to Scale to 100M+ Users

Want to hear another podcast with an entrepreneur who understands the meaning of “traction?” — Listen to my conversation with Bryan Johnson, the rags-to-riches philosopher who founded Braintree, which was bought by eBay in 2013 for $800 million in cash. (Stream below or right-click here to download):

#81: The Rags to Riches Philosopher: Bryan Johnson's Path to $800 Million

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QUESTION(S) OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.

Scroll below for links and show notes…


  • Connect with Reid Hoffman:

Masters of Scale | LinkedIn | Greylock Partners | Twitter

  • Connect with Brian Chesky:

Medium | Facebook | Instagram | Twitter


  • The 2008 PR campaign that turned things around when Brian and Joe of Airbnb were in dire need of a lifeline. [06:43]
  • Brian gets his hands dirty (and burnt) for the team. [08:35]
  • “In order to scale, you have to do things that don’t scale.” Reid introduces the program. [09:18]
  • Y Combinator’s Paul Graham reminds Brian of an important lesson he’d forgotten between design school and Silicon Valley: to design with empathy. [11:14]
  • How the Airbnb founders immediately put this lesson into practice. [12:59]
  • How these early personal visits with hosts gave Airbnb its roadmap. [14:29]
  • Passionate feedback from early users is one sign you’re doing something right. But you need to separate the wheat from the chaff to turn that feedback into growth. [15:12]
  • A thought exercise for increasing the distance word of mouth travels when people talk about your business: how many stars would this experience be worth? [17:18]
  • What are the two stages of a start-up’s product, and which one should be scaled first? [20:15]
  • How Brian decided on what to scale first. [21:16]
  • Input from Airbnb’s Ellie Thiele about how they began to automate for scale and build features that users really wanted. [21:39]
  • How Stripe’s Patrick Collison and Kayak’s Paul English personally weighed customer feedback in the early days. [23:19]
  • Thoughtful founders may look back on these early days with mixed feelings, but they’ll often consider them their career’s most creative phase. [24:41]
  • Nancy Lublin founded Dress for Success out of her New York City Apartment as a clothing drive to help women interview confidently for jobs. [25:11]
  • Two opposing mindsets required for the transition from the handcrafted phase to the massive scale phase — think of the difference between writing and editing. [26:01]
  • The non-glamorous work that goes into making the adjustment from one phase to the next. [27:42]
  • The importance of maintaining the handcrafted mindset no matter how big your company gets. [28:50]
  • Looking to reinvent an industry? Get orthogonal. Airbnb peered outside of hospitality and found inspiration from cinema. [30:00]
  • What are the essential ingredients for a perfect trip? Here’s a master class in finding the answer by handcrafting. [30:51]
  • Using this handcrafted experience to create a blueprint for operating on a global scale. [32:49]
  • Brian’s surprising message for early-stage entrepreneurs worried about traction. [34:36]
  • Reid’s closing good news for early-stage entrepreneurs. [35:21]


The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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10 Replies to “Reid Hoffman of LinkedIn, Brian Chesky of Airbnb, and How to Scale to 100M+ Users (#326)”

  1. How funny – I literally just listened to the Masters of Scale episode 17 with Sam Altman, ‘Why Customer Love is all you need’ and that one is a terrific companion to this and the KK article. I’ve had blinders on lately wabi’ing the heck out of some sabi, working intensely with individuals to test and ensure the RIGHT products and services to dazzle and delight…one. by. one. It’s grueling and it’s awesome. Love that when I come up for air, this theme is coming across loud and clear. 🙂 Thanks for the reassurance, when otherwise many folks argue to push social media marketing and scaling ASAP. (And Love the hot glue cereal box story!! Yes, be willing to do things that don’t scale)

  2. My favorite takeaway from Masters of Scale wasn’t covered in this outtake by Reid, which was Reid speaking to Sara Blakely about how she kept asking herself “Will this idea get me on Oprah?” Since hearing that, I’ve been asking myself, “Will this idea get me on TTTT?” I just answered yes to that question. I am applying the lessons from this most recent episode, including asking listeners “What feature would make you share this product with all of your friends?” and handcrafting an amazing product for a small group of people, and then looking how to scale that. Tim, thank you for your inspiration, vulnerability, and strength.

  3. Re: 5BF Bozeman

    Bozeman and the surrounding Gallitan Valley has become the fastest growing community in the US and for good reason, but with that growth it has lost much of its character, history and identity that often happens with time, development and homogenization of any suburbia.

    I hope that if you are gonna make the effort to come out you would make a road trip of it and truly experience Western Montana and the other communities that haven’t been so bastardized. Not just our other larger towns like Missoula but you would be doing yourself a disservice by not spending a day or two in Butte; a scrappy mining town with incredible history, sense of place and architecture. A city where in days past and even recent history more people per capita have “made it” than any other place.

    We look forward to your visit.

  4. Tim,

    Thank you for all your work. I have found regardless of the topic, book, blog or podcast you present, I always gain a useful takeaway that can be applied immediately.

    It is a great investment in my time.

    I appreciate what you do.

    Thank you,

    Libby Antognoli

  5. Hi tim, thank you for teaching me to be a better student and ask better questions. a few of your tools that have been game changes for me are morning gratitude practise, cold exposure and intermittent fasting. Funny how principles can apply to such diverse circumstances, from the business world to me – a first year nursing student in New Zealand. xx

  6. Hey Tim,

    I’ve heard & read most of your content and really like almost all of it. I understand that your selection of and focus on elite performers is good and thorough. But I can’t ignore the skewdness in your subjects toward those that were primed for success or just fortunate to be in the right place at the right time (I use the term ‘providenced’) for such cases.

    Since your focus has been so close to the most elite and to an extent you’ve joined an elite group [maybe you’re losing touch], have you considered there may be subjects that are near-elite status but are crippled by circumstance or have become disenprovidenced? [lots of made up vocab here] Like many others I was born into the country club of white male privilege. The powers you’re granted really have nothing to do with race and class, but the network you inherit. I also know billionaires and extraoardinary people; you might have even seen me at a party.

    I just wonder if you know anyone that has been able to truly bridge the divide (extreme poverty to wealth) in the current era or if you can appreciate the orders magnitude how much difficult it is to do today. You’ve interviewed old people who say they didn’t have much when they were young, but do you have a recent version of that? Are you mentoring any founders from Chiraq?

    I was lucky when I was a young teen to go to this really cool camp for a lot of the summer. There were all normal campy things like sports/games/lake/etc.. but then there were exceptionally cool activities like capoeira and circus disciplines. I took to trapeze.. it became really easy learning aerial stunts knowing I had a net to fall on safely.

    How successful do you think your founders and older subjects would be today – if when they try a new trick they will either succeed or die (and importantly know that before even trying)?

  7. Good afternoon

    I’m currently reading ‘the four hour work week’ and came across this paragraph on page 89.

    ‘i only read the sections of the book that were relevant to immediate next steps, which took less than two hours.’ I feel this is the section for me that triggered action and I decided to email you and ask you personally… I want to do what you do and influence people whilst making a good living. I’m currently finishing up university in England, originally from America and trying to start my own business with football out here. I’m trying to improve the sport at all levels as it is not very popular out here and decided to make a business to do just that.

    Tell me how it was for you when you decided to go all in and some hurdles you overcame to become successful. I know your book will tell me that, however I need to make immediate action as my visa is limited and I have to make moves now.

    Hope to hear from you soon,


  8. I hate it when you introduce me to new podcasts. Its already hard to find time to listen to my current ones.

  9. Hey Tim! I know you aren’t doing any personal work with people right now… do you have any suggestions of other investors and/or who may have more time to connect?