Foundation Season 1, Episode 18: Sahil Lavingia of Gumroad

1

Jack Dorsey

In this series premiere of Foundation, Kevin Rose interviews Jack Dorsey, the creator, co-founder and chairman of Twitter and the CEO of Square. The conversation talks of entrepreneurship, decision making, trial and error, and the path Jack took that lead to the creation of Twitter and Square.

2

Jeff Smith of Smule, Inc.

A serial entrepreneur, the co-founder and CEO of Smule, the company behind I am T-Pain.

3

Philip Rosedale of SecondLife

Founder and former CEO of SecondLife. In this episode Philip talks about his latest startup LoveMachine/Coffee & Power.

4

Tony Conrad of About.me

Kevin Rose interviews Tony Conrad, cofounder of About.me and a member of the founding team of True Ventures

5

Brian Wong of Kiip.me

After leaving Digg, the then 19 years old Brian founded kiip to reinvent mobile ads.

6

Jesse Jacobs of Samovar Tea Lounge

Turning away from tech after the dot-com boom, Jesse founded Samovar Tea Lounge.

7

Chris Sacca of Lowercase Capital

In addition to being an early investor in Twitter, Chris is the founder of Lowercase Capital.

8

Philip Rosedale of SecondLife

Philip is the founder of SecondLife. In this episode he gives us an update on his new business, Coffee & Power.

9

Jason Goldberg of Fab.com

Jason Goldberg is the founder and CEO of Fab.com, a deal site for design lovers.

10

Dennis Crowley of Foursquare

Dennis is the co-founder and CEO of Foursquare, the check-in app that evolved from Dodgeball.

11

John Borthwick of Betaworks

Kevin sits down with John Borthwick, Founder & CEO of Betaworks, the "company of companies" behind such properties as Bit.ly, Chartbeat, Tweetdeck and many more. Kevin and John chat about the early days of the internet, the challenges of creating products for mobile platforms, how to pitch investors, what to do and what not to do in the initial stages of starting your company, and much more!

12

Leah Busque of TaskRabbit

Kevin sits down with TaskRabbit founder Leah Busque. Leah stepped away from a dream-job at IBM to start her own business. Kevin and Leah talk about what it's like to start to structure a business around a great idea, how to get started in multiple markets, finding executive talent and more!

13

John Ham of Ustream

Kevin sits down with John Ham, Co-founder and CEO of the popular live-streaming service Ustream. They talk about John's time in the US Army, and how that sparked the inspiration for Ustream. They also delve into the challenges in scaling for live video, how to build a core team of employees, how to go about the difficult process of 'editing' your team, and more!

14

Ryan Carson of Carsonified

This week Kevin Rose sits down with Carsonified founder, Ryan Carson, to chat about the benefits and challenges of creating and organizing tech conferences, how to approach building new web products and more. Ryan also talks about his new company Treehouse, which aims to revolutionize technical education, and the way programming languages are taught with affordable online tutorials.

15

Tim Ferriss: Author of The 4-Hour Body

Kevin sits down with Tim Ferriss, author of the New York Times best-selling books "The 4-Hour Workweek" and "The 4-Hour Body" for a chat about his life growing up, and the challenges of writing a book. Plus, he gives Kevin a few details about his upcoming book, "The 4-Hour Chef".

16

Kevin Systrom of Instagram

Kevin Rose sits down with Kevin Systrom, founder of the popular social photo sharing app, Instagram.

17

Scott Harrison of charity:water

Kevin Rose and Scott Harrison sit down to discuss Harrison's path from childhood to New York nightlife socialite and club promoter to founding the non-profit charity: water. This interview brings out Harrison's fascinating personal story about the transformation from "selling selfishness and decadence" to a dedication to providing the most basic of resources (clean water) to some of the most impoverished people in the world through his own reinvention of how a charity can operate.

18

Sahil Lavingia of Gumroad

Sahil Lavingia is a born entrepreneur having created and coded numerous notable projects and recently raised $7M in funding for his first company all before his 20th birthday. Kevin sits down with the first-time CEO of Gumroad, a company that wants to make selling things online as easy as sharing things online. Lavingia talks about what inspires him to create new apps, having tough conversations with investors, plus why he made the decision to leave the founding team at Pinterest.

19

Om Malik of GigaOM

Kevin Rose and Om Malik sit down and discuss Malik's life growing up in India aspiring to be a successful writer and journalist. The interview traces how Malik made his way to the United States working as a writer, then trail-blazing online journalism starting various publications prior to GigaOM. Malik's passion for covering the tech industry, startups, and venture capital shines in this interview as the driving force that has led him to where he is today.

20

Elon Musk of Tesla & SpaceX

South Africa-born entrepreneur Elon Musk joins Kevin Rose in an interview shot at Tesla Motors' Factory, the groundbreaking electric car company he co-founded. Born and raised in South Africa, Musk explains visiting the United States at an early age, his interest in comics and technology and how it all led to him striking out on his own back to the United States to chase opportunity. Musk continues to explain his experiences co-founding Paypal, Tesla, and SpaceX. Tesla is widely recognized for designing and shipping the first electric cars of the modern era. SpaceX is the first commercial company to launch a rocket delivering a spacecraft to dock with the International Space Station. Finally, Musk provides fresh details about his "Hyperloop" project, a new mode of transportation "kind of like a ground based Concord" that would take passengers from San Francisco to Los Angeles in just 30 minutes.

21

Matt Rogers of Nest Labs

Matt Rogers of Nest Labs shows off the newly refreshed Nest Learning Thermostat and also talks about his early days working at Apple where he worked on some of the early prototypes of the iPhone. Matt Rogers' must-do advice for startups: "Build your first core team right. For each of your core competencies of the company, you want to hire a seed crystal for that area - someone who can be hands-on, but also has the strategy and leadership to grow and build that organization."

22

Tom Conrad, CTO Of Pandora

Kevin Rose sits down with Tom Conrad, CTO of Pandora, to discuss Pandora's success, his days spent as an engineer at Apple, why Thanksgiving is huge for Pandora and more! Pandora CTO Tom Conrad shares his inspiration for reinventing the radio. He reveals how a jailbroken iPhone played a key part in Pandora's success, and explains why Thanksgiving is the biggest day of the year for the service. He also tells the crazy backstory behind Web 1.0 flameout Pets.com, what it was like to be an engineer during the "dark years" at Apple, and how he made a killing in high school selling the Apple IIGS. Tom Conrad's advice for finding your dream job: "The happiest I've ever been, the most gratification I've ever gotten from a job, are always instances where two things are true: I'm working with people that I love, and I'm solving a problem that I'm personally passionate about."

23

Ben Horowitz of Andreessen Horowitz

Kevin Rose sits down with Ben Horowitz, co-founder of Opsware and General Partner at Andreessen Horowitz The latest episode of my Foundation video series comes to you filmed live from the Google Ventures Founder & CEO Summit last week. I had the opportunity to sit down with Ben Horowitz, co-founder of Opsware and now General Partner at Andreessen Horowitz. Enjoy! Ben shares how he got his start as an intern at Silicon Graphics, and went on to found and build Opsware into a billion dollar company. He offers candid advice for entrepreneurs on the importance of establishing a thoughtful communication architecture, how to hire for scale, and the secret to getting the most out of board meetings. He also reveals what he looks for in a pitch: Above all else, he asks "does the founder have the courage to build the company?" Ben's advice for CEOs: "Being nice to everybody all the time or never telling them what's wrong turns out to be a really dangerous thing. It's really important in general to be giving feedback always. Negative feedback, not just about people, but about what's wrong in the company is critically important."

24

Melody McCloskey of StyleSeat

Kevin Rose sits down with the founder of StyleSeat, Melody McCloskey, and discusses her company and when it is the right time to start your own venture. Melody shares how her frustration with finding a stylist inspired her to build the platform. She also talks through the challenges of reaching an audience who isn't in front of a computer all day, and how the web helps them grow their businesses and improve their client relationships. Melody McCloskey's advice on when it's time to start your own thing: I started a company because the excitement about doing it suddenly outweighed the fear. I'd been fearful for two years; I sat on the idea for two years. Then finally it was like no I really want to do this, and I don't care if I fail. StyleSeat.com

25

Tony Hsieh, CEO of Zappos.com

Kevin rose sits down with Zappos CEO Tony Hsieh about entrepreneurship, fostering corporate culture, and his latest project to fuel a thriving tech community in Las Vegas. Tony opens up about starting his first company, LinkExchange, an early take on Web advertising which was acquired by Microsoft for $265 million. He tells why his first startup taught him to pay close attention to company culture, outlines how founders can map company culture to their personal values, and explains why Zappos actually pays people to quit. Tony also discusses his latest efforts to accelerate the tech ecosystem in Las Vegas and his goal to fund at least 100 local tech startups. Tony Hsieh's advice on how to hire the right people to build a great company culture: "From the beginning, company culture was always important. Is this someone I would choose to hang out with or grab a drink with, if we weren't in business? If the answer was no, we wouldn't hire them."

26

Dave Morin of Path

Dave talks about getting his start in student marketing at Apple, and reflects that focus is one of the most important things he learned there. He goes on to describe his time at Facebook, where an intense focus on product utility set the product up for long-term growth. Dave also dives into the moments that inspired Path, and the different ways their team thinks about the social graph.

27

Hosain Rahman of Jawbone

Hosain and Kevin discuss the entrepreneurial environment at Stanford in the 1990's, The Jetsons as design inspiration, and how his meeting with Steve Jobs shaped the future of Jawbone's first product designs.

28

Robyn Sue Fisher of Smitten Ice Cream

Robyn Sue explains how she built a solid alumni network at the Stanford d.school, why she turned down a job with the FBI to become an entrepreneur, and the secrets behind the Kelvin, her one-of-a-kind instant ice cream freezer.

29

Chad Hurley, Co-founder of YouTube

Chad talks about life after YouTube, hints at his latest ambition in the video collaboration space and recalls one very important breakfast meeting at Denny's.

30

Jim Gilliam of NationBuilder

In the newest episode of my Foundation video series, I talk with NationBuilder Founder and CEO Jim Gilliam, a two-time cancer survivor and activist. Jim discusses growing up in Silicon Valley, how he made the jump from filmmaker to tech entrepreneur, and the power of community action to turn ordinary people into leaders.

31

Ev Williams

In today's episode of my Foundation series, serial entrepreneur Evan Williams talks candidly about his experiences building Blogger, Twitter, and his latest project, Medium. Ev recounts the early days of Twitter, shares what he's learned about how to scale fast-growth products, and explains his philosophy about the power of collaboration.

32

Phil Libin of Evernote

For the latest episode of my Foundation series, I interviewed Evernote CEO Phil Libin live from START SF. Phil discusses his views on the "cloud" moniker, Evernote's plans to be a hundred-year-old startup, and how to make encryption sexy.

33

David Copperfield

In this episode of my Foundation video series, I travel to Las Vegas to interview famed illusionist, magician, and entrepreneur David Copperfield. David explains how he combines magic with storytelling, recounts the moment when Francis Ford Coppola taught him to text, and shares his theory that people who are eternally curious are never truly satisfied.

34

Matt Galligan

In this episode of my Foundation video series, I sit down over some craft beers with entrepreneur and Circa founder Matt Galligan. Matt and I discuss the concept of breaking news and Circa's second version of its news app for iOS and Android.

35

Brian Armstrong

In this episode of my Foundation video series, I sit down for a chat with Coinbase founder Brian Armstrong. We chat about Bitcoin, his first Android wallet project, and the insane security he uses to protect your coins.

36

Tony Fadell

Nest founder and CEO Tony Fadell following the announcement of it acquisition by Google

37

David Byttow

I sat down with Secret's co-founder David Byttow for a revealing conversation about his time as an engineer at Google, Medium, and Square, and how he gained the courage to break out on his own as an entrepreneur.

38

Jackson Palmer of Dogecoin

Jackson is the brains behind the fast-growing cryptocurrency known as Dogecoin. We discuss the Dogecoin community's ability to raise money for good (like sending the Jamaican Bobsled team to Sochi), and Jackson's views on what digital currency will look like in five years.

39

Anthony Casalena of Squarespace

CEO Anthony Casalena. Anthony provides a fascinating look at the Squarespace ideation narrative, and the company's short-term and long-term goals.

40

Dennis Crowley

Dennis talks about the new Foursquare as well as splitting off check-ins into his new app called Swarm.

42

Jamie Oliver

In this episode of Foundation, Kevin sits down with well-known celebrity chef and entrepreneur Jamie Oliver. He and Jamie discuss his lifelong passion for cooking and how technology can positively impact our food system.

43

Leo Laporte

In this episode of Foundation, I sit down with a long-time mentor and friend, Leo Laporte. Leo was the star of TechTV and is the founder of TWiT. We discuss his early days as a fry cook at McDonald’s, how the concept of This Week in Tech was born, and the importance of keeping a positive attitude.