From Aspiring Billionaire to Indie Hacker with Sahil Lavingia of Gumroad

Episode #100

After leaving his post as employee #2 at Pinterest, a teenage Sahil Lavingia (@shl) raised millions in funding from high-profile Silicon Valley to build a unicorn startup that could change the world — Gumroad. Today he lives in tiny Provo, Utah, spends much of his time learning to write and oil paint, and runs Gumroad as an indie business with the goal of making himself happier. In this episode we talk about what happened in between, and the lessons Sahil learned that can help every indie hacker create better lives for themselves by building more "successful" businesses.

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    Gumroad has become such a feature-rich and robust e-commerce platform for digital product entrepreneurs --- and developers like myself --- that I've been recommending it to my startup clients selling software products online. Congratulations to Sahil for his sustained efforts to improve Gumroad to its current status as a reliable platform for e-commerce startups.

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      Thanks! So much more to come. What features do you think are missing?

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      Very cool product!

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        Thanks Travis. If there's something else you'd like to see along the notes, please let me know. I am always looking for ideas that can add more value!

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      Just wanted to chime in and say that I've never heard of this smashnotes tool but it is a phenomenal product!

      And your notes are very thorough. People would surely pay for podcasts to be easily digestable and searchable like that!

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        Thank you! Appreciate your kind words. Let me know if there are any particular podcasts or topics you'd like to learn more about, and I'll make sure to have more of them. Did you know there was a way to subscribe to both newsletter and a weekly podcast?


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    Yes!!!! I am so excited about this episode. IH podcast has been getting better and better lately. @csallen

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      Ooh, interesting! Which episodes have stood out to you recently? I feel like the podcast has always been strong. My favorite episodes are sprinkled through the past years, and my opinion mostly depends on the guests - I feel like @csallen's interviewing has been strong throughout.

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        No doubt, he does a great job interviewing. The topic and guest is the deciding factor for me and they haven't been interesting to me personally as of late. The last recent podcast that I liked was with Natalie Nagele (wildbit).

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          Yes! Loved the Wildbit interview :) Past favorites are Pieter Levels ( of course ), Saron Yitbarek, and Stephanie Hurlburt.

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    Wow, this is one of my favourite episodes, love it so much! I already loved the product, but was so good to hear Sahil speak openly and give his insights. So much good stuff in this episode!

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    Episode 100! Congrats to Courtland & Channing.
    I’ve been an avid listener since episode 2, keep up the excellent work

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      Nice! Have you listened to all previous podcasts?

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    My Main Takeaways:

    • Quality of life > Business operations: Sahil switched from prioritising his business above his health and personal life, to prioritising his quality of life above business.
    • Different cities have their own underlying philosophies: In San Francisco the underlying philosophy is about money, success, and business. In LA the underlying philosophy is about money, success and entertainment. In Provo, Utah, the underlying philosophy is about family, respect and community. Sahil moved from San Francisco to Provo, Utah. This move reflects his change in underlying philosophy.
    • Build projects and build an audience: Sahil got to be the second person hired at Pinterest because he was spotted by the CEO. Sahil was spotted because he frequently posted and commented on the Hacker News forum and an app he built and shared got to #1 on Hacker News.
    • Sometimes things don’t go to plan… for the better: Sahil initially planned to get a 4-year Software Engineering degree then work at Google, then he’d work at a small company, then he’d start a company when he was 35. But he ended up dropping out of college to work as employee #2 at Pinterest, and then start his own company by 26.
    • Your greatest strength may also be your greatest weakness: Sahil’s boldness, ambition and confidence enabled him to drop out of college and become employee #2 at a soon-to-be billion dollar business, Pinterest. But this same boldness, ambition and confidence made him leave Pinterest to start his own company… only a few months away from making multiple millions at Pinterest, causing him to lose out on those millions.
    • Solve your own problem: Sahil got his idea for Gumroad when he wanted to sell some icons that he made, but realised that there were no light-weight ecommerce solutions.
    • Build and launch fast: Sahil built the initial Gumroad during a weekend, and it got to the top of Hacker News on Monday morning.
    • Leverage your network: The Stripe API made payments very easy for Gumroad, but it was in Beta when Gumroad started. Fortunately, Sahil knew the people at Stripe and managed to get a Beta key.
    • Embrace failure and embrace the stress.
    • Share what you’re working on, put yourself out there: An investor, Craig from Collaborative Fund sent Sahil a contract and $10k after seeing his Gumroad post on Hacker News, since he believed in it. This was huge validation.
    • You don’t need to be the stereotypical nerd to be a successful tech founder.
    • Network and meet people: Over the past 8 years Sahil says that he has probably had coffee meetings with about 7,000 people.
    • Friends take time to build, savor the people you’ve known for a long time.
    • Take advice from people who were at your level in more recent years: Taking advice from someone who is 10 years ahead of you is a bad idea because times change. Rather take advice from someone 2-4 years ahead of you.
    • Start off with one-on-one sales, direct outreach and building relationships.
    • You may have a few whales using your service: Whales are the users that make up the majority of your revenue.
    • You won’t understand what someone has been through unless you’ve been through it yourself.
    • It’s OK to do things for yourself: It’s OK to not be productive every now and then. It’s OK to take breaks. It’s OK to do things for yourself only.
    • It’s not worth it to sacrifice your health for work.
    • Advice for beginners: Just build stuff. Start small. Get ideas from the problems of the people around you. Build and launch quickly.
    • Build momentum: Train your brain to come up with good ideas, by coming up with good ideas.
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      Dude, thank you for this. I will be sharing some of this and the whole thing in the coming days if that's okay with you.

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        No problem, do as you wish. Thanks for the podcast episode!

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    On the "it shouldn't be dangerous" comment, something about it bugs me. Entrepreneurship is a form of economic mobility that's not accessible to everyone. Not everyone can take several months off to build a business, or even run a side project. Maybe they're already working two jobs.

    I just think it's unrealistic and somewhat exclusionary to say "you shouldn't be risking your health to start a company." It seems similar to saying, If you aren't privileged enough to buy your own health insurance, support yourself, or have free nights and weekends, you shouldn't start a company.

    For a lot of people starting a company would require taking personal risks. Maybe it would be more helpful if we told the stories of how people overcame those risks and made it work at the beginning. How did they cover healthcare? How did they save up? How much debt did they take, and what was their fallback strategy? Maybe we can inspire a larger community than well-off, young and unencumbered engineers. Or at least have some honest conversations.

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      Just to be clear, I'm one of those well-off unencumbered engineers. I'm sure nobody needs me to be upset on their behalf. I'm just vocalizing something that feels off.

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        I'd love to hear more of those stories. When I mean it "shouldn't be dangerous" I don't mean that people shouldn't take those risks, but moreso we should work so that it isn't dangerous for everyone to do longterm.

        (Universal healthcare, etc)