44 min

How a One-Time VC Darling Learned to Love His ‘Measly Lifestyle Business’ Unemployable: Advice for Freelancers and Entrepreneurs

    • Careers

What is it like going from the heights of running a company that is growing fast and attracting gobs of VC money ... to being on your own and running a "measly lifestyle business"? Not too many people can answer that question based on experience. Sahil Lavingia of Gumroad is one of them.

Sahil recently published an article titled Reflecting on My Failure to Build a Billion-Dollar Company, and this week on Unemployable we extract some important lessons from this article, as well as a couple others that were recently featured in the Unemployable newsletter.

It’s time for another article roundup episode with Brian, Jerod, and Kat.

This week’s rundown:

• Was the Game of Thrones ending really that bad? And how does Brian feel about the Game of Thrones showrunners helming the next wave of Star Wars movies? (Does he even care?) [00:35]
• We reflect on the recent episode with Brian Cassel about productizing by addressing the #1 potential pitfall of trying to productize your business. [5:08]
• We reflect on the recent Stephanie Sammons episode by discussing how do you take the idea of “truly knowing what you want” from a general, nebulous idea to something specific and maybe even measurable. [9:13]
• Discussion of article “Reflecting on My Failure to Build a Billion-Dollar Company” by Sahil Lavingia for Medium. [14:20]
• Discussion of article “Mark Cuban’s Advice for Recent Graduates: Your Soft Skills Are More Important Than Coding” by Cameron Albert-Deitch for Inc. [25:44]
• Discussion of article “The Value of Community: How and Why to Create (and Join) One” by Allie Decker for Authentik. [30:03]
• Finally, Brian closes by teasing the next interview episodes of Unemployable. [40:56]

To access the show notes, transcript, and links mentioned in this episode, view the episode page at: http://unemployable.com/podcast/discussion-episode-133

What is it like going from the heights of running a company that is growing fast and attracting gobs of VC money ... to being on your own and running a "measly lifestyle business"? Not too many people can answer that question based on experience. Sahil Lavingia of Gumroad is one of them.

Sahil recently published an article titled Reflecting on My Failure to Build a Billion-Dollar Company, and this week on Unemployable we extract some important lessons from this article, as well as a couple others that were recently featured in the Unemployable newsletter.

It’s time for another article roundup episode with Brian, Jerod, and Kat.

This week’s rundown:

• Was the Game of Thrones ending really that bad? And how does Brian feel about the Game of Thrones showrunners helming the next wave of Star Wars movies? (Does he even care?) [00:35]
• We reflect on the recent episode with Brian Cassel about productizing by addressing the #1 potential pitfall of trying to productize your business. [5:08]
• We reflect on the recent Stephanie Sammons episode by discussing how do you take the idea of “truly knowing what you want” from a general, nebulous idea to something specific and maybe even measurable. [9:13]
• Discussion of article “Reflecting on My Failure to Build a Billion-Dollar Company” by Sahil Lavingia for Medium. [14:20]
• Discussion of article “Mark Cuban’s Advice for Recent Graduates: Your Soft Skills Are More Important Than Coding” by Cameron Albert-Deitch for Inc. [25:44]
• Discussion of article “The Value of Community: How and Why to Create (and Join) One” by Allie Decker for Authentik. [30:03]
• Finally, Brian closes by teasing the next interview episodes of Unemployable. [40:56]

To access the show notes, transcript, and links mentioned in this episode, view the episode page at: http://unemployable.com/podcast/discussion-episode-133

44 min