A Founder’s Failure to Build a Billion-Dollar Company

Founder's Journal

Morning Brew

Careers, Business, Entrepreneurship

4.8 • 1.1K Ratings

🗓️ 22 January 2024

⏱️ 45 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

Episode 97: On this episode, I talk with Sahil Lavingia about his 2019 essay titled “Reflecting on My Failure to Build a Billion-Dollar Company.” Sahil is the founder & CEO of Gumroad, an e-commerce platform for creators. Gumroad does nearly $20m per year, is highly profitable, and has no full-time employees. In the essay, Sahil talks about leaving Pinterest as its second employee in 2011, to build his life’s work…a company called Gumroad that would be worth billions of dollars, IPO one day an employ hundreds of people. But that’s not what happened. In 2015, Sahil laid off 75% of Gumroad’s staff to keep the company alive. Of course firing some of his best friends was heart-wrenching. But possibly just as difficult for Sahil was the death of his dream to build a venture-backed unicorn. The heart of this article & much of what you’ll hear Sahil talk about during our conversation is the emotional journey post-layoffs & the decision to build a profitable “boring” lifestyle business. Reflecting on My Failure to Build a Billion-Dollar Company: https://sahillavingia.com/reflecting Send us an email and let us know what you think of the idea! [email protected] #FoundersJournal #Startups #Entrepreneur Listen to Founder’s Journal here: https://link.chtbl.com/OV4W93_W Watch Founder’s Journal here: https://www.youtube.com/@FoundersJournal/ Subscribe to Morning Brew! Sign up for free today: https://bit.ly/morningbrewyt Follow The Brew! Instagram - https://www.instagram.com/morningbrew/ Twitter - https://twitter.com/MorningBrew Tik Tok - https://www.tiktok.com/@morningbrew Follow Alex! Alex Lieberman (@businessbarista) Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

Click on a timestamp to play from that location

0:00.0	What's up everyone? Welcome back to another episode of Founders Journal. I'm Alex Lieberman,
0:04.6	co-founder and executive chairman of Morning Brew. Before we hop into the episode,
0:08.8	I want to give you a peek behind the curtain for a second. Since day one of this podcast, my goal has been to document
0:15.2	the entrepreneurial journey in order to increase your odds of success
0:19.1	while building your business.
0:20.5	That goal has not changed, and as I've said countless times I look to you my
0:25.7	listener for feedback and ideas to help inform the content of the show moving
0:30.6	forward. Well in recent weeks there's been a very consistent theme in the
0:35.2	emails that have been shared with me. Whether it was a note about my episode
0:39.2	breaking down the Lex Friedman conversation with Jeff Bezos or my most recent episode summarizing and analyzing
0:45.6	two great startup essays about spending your money wisely while running your business,
0:50.4	this idea of curation and analysis continues to be surfaced by you all.
0:56.0	You all feel like there's a ton of business content on the internet,
0:59.0	tons of podcasts, tons of people to follow on social media tons of books tons of newsletters tons of blog
1:05.3	posts but you don't have the time to search every corner of the internet to find
1:10.7	the best most important content for entrepreneurs,
1:14.0	which is what I'm now making my job.
1:16.0	For the next little while, I'm going to act as your startup Sherpa
1:20.0	curating the best content for entrepreneurs in the world,
1:23.2	summarizing it so you don't have to read it yourself,
1:25.8	and analyzing it so you have actionable takeaways
1:29.1	to apply to your business.
	...

Please login to see the full transcript.

Previous episode | Next episode

Disclaimer: The podcast and artwork embedded on this page are from Morning Brew, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of Morning Brew and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.