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AMA
p/amaOfficial 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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Goutham
Hey Sahil. Loved how you built Gumroad. If you had to start again all over today, what would you be working on?
Sahil Lavingia
@gouthamj In the ten years since I've started Gumroad, I've learned that some of my favorite people in the world are entrepreneurs and business owners. So I would build a product to serve them–especially those who are remote, and async first, and folks not as close to the Silicon Valley "bubble."
Goutham
@shl Awesome. Thanks for the reply Sahil. I too find building for entrepreneurs to be so fulfilling :)
Andy Cook
Hi Sahil - Great to have you here. I've been following the Gumroad story for awhile and appreciate you taking the time to share knowledge. One thing I've admittedly found hard to reconcile while trying to apply learnings from your story is that the path you took to make Gumroad a profitable indie business isn't all that replicable for other founders (e.g. raise $10M and then have your investors give you all the equity back for free) Obviously, every one's path is different while building a successful business, so you can't really copy anyone. But with that in mind, if you were to start Gumroad now without that $10M of initial VC funding to get it off the ground, what would be your strategy today if you were bootstrapping or working off a much smaller seed round?
Sahil Lavingia
@andygcook Super fair question! I only wrote to share my story, not for others to copy. If I didn't have $10M in funding, I would do what I did in 2015 when I ran out of funding, just right at the beginning: leave SF, minimize my personal burn rate, and hire contractors to scale.
Andy Cook
@shl Makes sense and good advice. Especially around minimizing personal burn rate. Tough to do, of course and not possible for everyone, but makes a huge difference.
Sheida Mirjahani
Launching soon!
If you started Gumroad in 2021, how would you acquire the first 1000 creators?
Sahil Lavingia
@sheidmirj Same thing I did in 2011, 10,000 cold emails.
Rajesh Kadam
Hi Sahil, Which recent investment of yours are you most excited about? And do you invest in Crypto?
Sahil Lavingia
@6kadam I do invest in crypto. I'm most excited about my investment of 500-1,000 hours to write The Minimalist Entrepreneur.
Rajesh Kadam
@shl That's an awesome re-frame! thanks.
Chris Davis
@shl @6kadam very smooth and topical
Oliver Sauter
Hey Sahil, your product development processes have been a big inspiration for us, and helped us to build our product in a much saner, paced and focused way. A game-changer for us was the process you outlined in your chat with Josh Pigford about your Tentpole launches:
I am curious if you have anything written down about the way people decide to work on projects, or generally a deeper dive into those processes. Is that laid out in the "minimalist entrpreneur"? So far I understand that everyone is basically freely choosing to work on stuff that is in the pipeline as "specs complete". How do you make sure that things progress well and don't cause clogging because of dependent tasks, if a person taking on a task is only able to work 2 days a week? Also, how are people compensated right now in the upside of the long term project? From what I understand most people work with a very high salary, but no long term upside e.g. in the form of stocks? I am curious to learn more about the reasons for applying this compensation model, and how you align for long-term commitment without sharing of long-term upside? Thanks so much for your continued insights and desire to share the things that help other founders get to a good place too 🙏
Sahil Lavingia
@oliversauter It's more art than science, but I often use 4 heuristics: 1. What's the worst thing about the product, can we improve it? 2. What's the best thing about the product, can we make it even better? 3. What's the first piece of friction a user happens upon? 4. What's the bottleneck that prevents our most successful users from being even more successful? Rinse, repeat. Ultimately you need experience (and some data) to make better decisions.
Sahil Lavingia
@oliversauter We rarely have dependent tasks.
Sahil Lavingia
@oliversauter We give out equity now.
Chikodi Chima
Hey Sahil, will you still be at Founder Summit CDMX on Tuesday?
Sahil Lavingia
@chikodi Yes! Here now :)
Chikodi Chima
@shl awesome. Looking forward to connecting tmw
Marin Petrov
Have you ever thought of retiring at some point?
Sahil Lavingia
@troll_lock I did, in 2019. That's why/when I published my Failure essay.
Martin Tonev
Hey Sahil, I want to ask how you trigger the initial work of mount to get your product at such a high point. I`ve created a free documentation builder for software projects and all the people I have reached like the product but I just can get to enough users. So how did you initially market your service?
Sahil Lavingia
@microdesignn I would "start with community" and only then build a product. If you're having a hard time with your existing product, I'd just build a new one.
jeff slobotski
Congrats on the new book Sahil and looking forward to getting a copy here soon! Keep moving the good forward friend!
Sahil Lavingia
@slobotski Thanks Jeff!
Sunny Modi
Hey Sahil, Does Gumroad has plans to launch a Web3 product for creators? I would love to see what the Gumroad Web3 could do.
Sahil Lavingia
@sunny_modi Not yet. But we're paying attention.
Yusuke Nishijima
What did you throw away recently?
Sahil Lavingia
@yusuke2424 I throw away all of my figure drawings.
Mehul Agarwal
How to build long term thinking?
Sahil Lavingia
@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
@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
@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
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
@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
@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
@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
@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.
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
@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.