📻 — Ben Tossell and Sahil Lavingia Talk Gumroad, Unscalable Community, and Going Open Source?!

This is your Community, Daily.

Reading Time: ~ 5 min.

Good morning yenizens!

A few amazing links to get you started:

  1. Cloudflare analytics… feels like a big deal.

  2. Fantastic insights on network theory. Thanks Brendan!

  3. What is this magic?! Linear?!

  4. Tweetstorm builder@linuz90 @frankdilo @meseali blowing minds!

  5. Speaking of Ben... podcast with Brandon on investing in #nocode.

  6. Survey. Now. ٩( ๑╹ ꇴ╹)۶

Finally, I have a "dormant" account with > 10k followers on Twitter! Help me figure out what to do with it and win yourself a YENIVERSE hoodie!

To infinity & community,

— john

Yesterday I got lucky and was able to hang out with Ben Tossell of Makerpad and Sahil Lavingia of Gumroad as they held open office hours!

Here are my notes from their time together… I think you’ll particularly like these topics that the three covered:

  1. Is Gumroad going Open Source?!

  2. The future of creator economy and SHL’s one-minute crash course on building an launching and building an income via the internet.

  3. Real community isn’t scalable…

Let’s jump in!

Let’s talk the Launch of Memberships!

Sahil and Ben open up and start talking about the next big feature release from Gumroad, which was subscriptions and memberships.

Sahil shares that he had this on the roadmap from as long-ago as Q1 of 2019! But, the original concept was launched back in 2013, around the same time that Patreon launched their basic function.

Creators are processing ~$1.5M per month at the current time! Integrations is going to be the next big area of work for the Gumroad Team.

Sahil shares his product development strategy in one simple note: We build features based on what our community is asking for!

This is the best way to do product development as you walk toward product-market fit! You can always review their public roadmap here.

The SaaS-ification of the Creator Economy

Using tools like Gumroad, Stripe, Substack and others will give a major rise to the creator class as well as the “community gigster” and on-demand community leader.

Sahil and Ben both see the community and creator industry headed into an “open API” type of economy where folks are able to pick and choose the tools they need to build what they need — there doesn’t have to be a lot of overhead or waste.

Sahil shares a bit more of his strategy — focus on value, less pricing for competitive marketing (although they are less costly than systems like Patreon).

Making Your Business More Defensible

Sahil and Ben take an honest approach to the pandemic, sharing empathetically that it did suck (YES) but that it was also an opportunity to really asses where they were as a business and how to become more “anti-fragile” for their survival.

The idea of having “all eggs in one basket” is no longer the the default behavior for creators — most creators are using many different systems to cover their financial needs and Gumroad is just one of the many competitive offerings. It’s nice to hear a founder who isn’t trying to “lock-in” their users and instead has a much more open approach to building a business.

Gumroad Going Open Source?!

Sahil shares that he wants to move towards a WordPress-centric model of having the .com and the .org — one as a paid, premium, hosted solution and one that folks can download for free (open source) and run it on their own hardare and services.

This is an incredible move and I think it’s also a strong way to build a business and there is obvious proof that this model can work, in dramatic ways. Sahil doesn’t have a timeline for this project, but, from his words: “It’ll be multi-staged over years.

I can’t wait!

It’s Hard to Teach People How to Make a Living on the Internet

The most sobering part of the convo is where they began talking about Gumroad University, building an educational system around Gumroad!

But, Sahil speaks a lot of truth:

Creating a living online is not as easy as people think.


They are looking to do a more cohort-based model for education because it’s more about “discipline” and “scheduling” than passion and just “getting shit done” — so true.

“Community Isn’t Scalable”

Developing a system of inspiration, accountability, that helps folks toe the line between community-at-scale (i.e. a “network”).

The transition between this is part of what Sahil and their team are thinking about regarding education. One thing that Sahil believes deeply is that a community is a place where the “new person can be heard” — a wonderful and thoughtful (super-tactical too) way of thinking through our own implementations of community development.

It’s kind of a like a framework in a word.

Focusing on Motivation for Community

A creator’s journey is a multi-year journey and oftentimes you have to “repeat” lessons over and over and over again.

🙌🏻 — Yup, we all know what that’s like.

Building a community with systems (of education) that can be “rolling” and that can focus on developing resilience, formidability, and perseverance is just as important as the outcomes themselves.

The first time you build a project (and community) it usually doesn’t work — so, having the ability for folks to consistently repeat lessons and, over-time, get to a place where you can do this sustainably, is the real and actual process, not a one-hit wonder.

Getting people who have done it to help the newbies is how it’s done.

Are we Supersaturated in the Creator Space?

According to Sahil and Ben, it’s entirely okay to see repeat communities and similar offerings as “everyone has their own unique voice” — content that Sahil would never pay for, other folks can’t get enough of!

The TL;DR: is that everyone needs acceleration and we need more folks who know how to do this and are willing to teach these to others!

So, no.

I love this because this is directly in-line with our mission as yenizensDemocratize Community Building! 2021 is going to be the year of communities! I have a personal goal of helping 1,000 communities turn profitable!

Sahil’s bottom-line: If you want to make money on the internet, get started today. Start shipping. Learn and then practice. Repeat. Network with other folks that know how to do it.

Ben to Sahil: You Have No Meetings… What?

The Gumroad team is famous for all being “part-time” employees and Sahil is actually writing a post on how they get “work done” in Gumroad — he shared a draft of it with me via DM:

In Sahil’s description, they’ve built a “conveyor belt” and system for product development and they only hire folks who can operate in this way. Also, a “cheat code” that most folks forget is that Sahil, himself, can do both design and develoment — not everyone has a “SHL” on their team. 🤣

They don’t have meetings because their system allows this type of behavior. Even if it’s not “perfect” it is working.

Finally, Let’s Talk VC for a Moment…

Sahil doesn’t want to get “canceled” but he is calling it! He’s excited about his plans for venture capital and he thinks there’s a large “whitespace” available for creators and builders, especially with #lowcode and/or #nocode tools on the rise (a’la Makerpad Community).

According to Sahil, venture capital can be the “last resort” for some people, perhaps 1% of creators. But, there’s just so many more ways to build businesses these days, especially indie projects and indie hackers.

Sahil’s fund is currently investing ~$9M / year into early-stage startups.

A One Minute Crash Course on Building, Selling, Monetizing

Sahil breaks it down into a few parts:

  1. Get really good at something and apply that specific skill to an industry that needs that skill — do your homework!

  2. It’s a multi-year journey — don’t quit too early!

  3. Start by giving value away for free — especially good if you already have a full-time job! You don’t need to be too risky.

  4. Be open with you audience — be honest, open, candid about where you want to go and your community can support you.

Remember, everyone wants to make money so this isn’t a unique motivation! Consequently, you don’t need to be afraid of your dreams.

I think that’s a good place to end — have a great day folks!

Appreciate the Q&A via Makerpad! Thanks again to Ben and Sahil for spending their time sharing their wisdom with others! Let’s Democratize Community Building™️!