Episode 33: Following Your Startup’s North Star w/Sahil Lavingia

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In this episode, Gumroad founder Sahil Lavingia opens up about VC, recent layoffs, the bright future of the company, and how having a startup “north star” has helped him to find his way as a founder.

Bootstrapped Product Talking Points

  • What a “north star” is and why it’s important
  • Why VC is just a tool, not a pair of shackles
  • The role of automation in a small company
  • Important lessons from being an early employee at a startup
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 Show Notes:

Sahil on Twitter
Gumroad
Gumroad on Twitter
Small Product Lab – Gumroad’s contest for product creators
Show HN: my weekend project, Gumroad – Gumroad launch in 2011

Sahil lavingia has had an interesting ride. Getting into the game as a teen doing self-taught freelance logo design, Sahil moved on to ad banners, web design, app design and eventually app development to meet market demand as brochure sites became less and less desireable.

The connections he made led him to landing a job at Pinterest in 2011 (which was not “the” Pinterest we know today). Being an early employee at a funded startup taught Sahil a number of valuable skills, including:

  • Learning to adapt to goals
  • Taking charge of one’s personal destiny
  • Managing up/down/sideways
  • Learning to develop & articulate a vision
  • How to not be idle

During that formative time at Pinterest, Sahil came to understand the concept of a startup “north star” – core values that vet every decision a founder makes. Sahils own north star led him to launch a startup of his own, Gumroad. After coding up a proof of concept consisting of a hew hundred lines of code/html/css, the next indicated step was to turn it into a business that scales well.

Being plugged into the Valley startup ecosystem, Sahil discovered that there was a system & process for turning ideas into money. After securing $1mm in seed funding, Sahil proceeded to behave like a bootstrapped startup, building out Gumroad on his own for an extended period of time and letting most of the money sit in the bank. The decision to take funding was guided by Sahil’s startup north star to help creators be able to earn a living from selling their creations.

“My default answer is, yes, I totally can.”

In recent years, that same startup north star led Gumroad away from further VC and back to being a bootstrapped business. Sahil talks frankly with me about his experience with VC – which he says has been very positive – and what recent layoffs mean for the company.

We also talk about how his startup north star led the development of a high degree of automation at Gumroad, why the Gumroad team continues to roll out new features, and why the company never needed more than a few employees to handle the day-to-day operations of the startup. Sahil further tells us how his startup north star will guide him through the decisions facing Gumroad as they continue to operate as a bootstrapped company for the foreseeable future.

“People like saying you’re either bootstrapped or VC-funded, and I don’t think it’s that binary…it’s a spectrum.”

We also talk frankly about what VCs expect from their portfolio businesses, and why this works out acceptably well for Sahil and Gumroad, according to his startup north star.

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