AMA
Official ask-me-anything conversations with notable guests
Sahil Lavingia

I'm Sahil, founder of Gumroad and author of The Minimalist Entrepreneur. AMA.

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Started as a weekend project in 2011, Gumroad has grown–with its fair share of ups and downs–to helping 94,000+ creators earn over $500,000,000. In February 2019, I published a Medium essay, “Reflecting on My Failure to Build a Billion-Dollar Company,” that struck a chord with thousands of aspiring entrepreneurs who’d much rather build a sustainable business like Gumroad than chase a binary billion-dollar-or-bust outcome. I wrote The Minimalist Entrepreneur to help anyone start, build and scale their own sustainable business. AMA!
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Yusuke Nishijima
Pee York
What did you throw away recently?
Sahil Lavingia
Fweb3
@yusuke2424 I throw away all of my figure drawings.
Mehul Agarwal
How to build long term thinking?
Sahil Lavingia
Fweb3
@mehul_agarwal Get profitable.
Tarek Besbes
I'm currently writing my book about how to build ethical startups. In the past, I chased the idea of building a big startup, getting funded, and making lots of money until my first investor came in and ruined every piece of me then I have to disappear to recover and rebuild myself and as aimed to self-fund everything I do otherwise let it fade. Lost trust and that's probably a hard thing to recover, probably the only thing that would unite me with other people is ethics. I just launched my product today and it seems like it is going to be another failure so I have already given in to that. Say, a person like me who lost his entire network, and has to start from zero again and have no reach. How would you go about launching your products with no audience?
Sahil Lavingia
Fweb3
@tarek_besbes I would "start with community." (And if you've already determined failure on day one, you need to revisit your commitments.)
Tarek Besbes
@shl as building a community takes a lot of time and that's what I'm currently doing. Failure to me happens from day to day based on the tasks that I need to complete, I wouldn't refer to it at a large scale or a complete absolute, for example, it goes like "Okay, ProductHunt Launch Failed, what's next". As for my commitments, I have spent a significant amount of time so walking away is not an option regardless of what might happen, that's related to my internal beliefs.
Oliver Kraftman
Hey Sahil, do you think the billion-dollar-or-bust pressure comes from the businesses that people choose to work on that makes them need huge scale to succeed? Or rather a belief in the founders that that's what all successful startups looks like?
Sahil Lavingia
Fweb3
@oliver_kraftman It's because the failure rate is high, and so the winners have to pay for the losers (if you're an investor).
Oliver Kraftman
@shl thanks! So pressure from investors transfers to founders? Your article suggested you put the pressure on yourself at the start of Gumroad
Imran Khan
Where Money
Hi Sahil, what's the next thing you are looking forward to innovating on? Also, what's something you think can be innovated but don't have the time to?
Sahil Lavingia
Fweb3
@strongsoda The future of work. Doors.
Raj Bohra
Hey Sahil, how has working on your own personal brand on Twitter helped with Gumroad and other ventures?
Sahil Lavingia
Fweb3
@rajbohra No idea, not something I measure. (Is it measurable?)
Sharath Kuruganty
Hey Sahil! Thanks for doing the AMA with the Product Hunt community! You recently took a new identity as an author. What's the most difficult thing you encountered when writing The Minimalist Entrepreneur?
Sahil Lavingia
Fweb3
@5harath Believing that the world needed another business book; believing I was the right person to write one; believing that I could write a super-dense book, without fluff.
Clint Watson
Are you still oil painting?
Sahil Lavingia
Fweb3
@clintavo Not so much! I've focused on just figure drawing with charcoal (instagram.com/shlpaints) as that's a little easier to spin up when I have time. (Cheaper and less clean up too.)
Nate
Hi Sahil - do you think the rolling funds can outperform Sequoia? Asking seriously, because it would take somebody of your status and network within the industry to do so.
Sahil Lavingia
Fweb3
Nilton
Hi Sahil, Big up on the new book! I'm super excited to get to read it when it drops. I'm a fan of how you built a sustainable community behind Gumroad both how you crowdsourced funds & your flexible talent model. 1. I am wondering if you have any insights to share on how it is to manage so many shareholders? Aligning expectations with a few board members is hard enough. 2. With such a flexible model how does the Gumroad team manage the lag that sometimes happens when people onboard on new tasks?
Sahil Lavingia
Fweb3
@leza_app 1. Super easy to manage. Honestly less hassle to manage 7,000 individual investors than 10 institutional ones. 2. We're profitable; in no rush.
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