2021 was an epic year for Earlywork HQ - we launched our community, Gigs by Earlywork, Talent by Earlywork, a rebrand and brought a weekly cheeky tip to your inboxes every week. Check out a snapshot of what we got up to below 👇
We’re more than ready to take on 2022 and we’ve got some big announcements coming soon - stay tuned! 👀
For the first newsletter of the year, we thought we’d throw it back to Earlywork’s largest community event to date - a fireside chat with Sahil Lavingia.
Sahil Lavingia is the founder and CEO of Gumroad, a service that helps creators get paid for their work. His startup has attracted prominent investors like Naval Ravikant, Chris Sacca, and others.
The inspiration for the book started with a now-famous essay (and pinned tweet) about the history of Gumroad - 8 years of ups and downs, and it really hit home for a lot of people. Sahil’s audience started growing from there (as well as his inbox) and he wrote the book to “scale myself and the conversations I was already having with people”. Efficient 👌
Let’s dive into two of the key lessons from his book…
Product Market Fit? More like Community Market Fit
Product-Market Fit has been touted as the holy grail for startup founders and product people. Heck, we even wrote a newsletter on it.
A lot of Silicon Valley A-listers including Marc Andreessen and Sean Ellis have weighed in on the importance of achieving product-market fit and created frameworks for the startup community on how to get there.
Hands up if you’ve surveyed users or have done a survey that sounded like this: “How would you feel if you could no longer use product x? Very disappointed, Not disappointed…”
Sahil argues that building an audience or a community first is more important than striving for product-market fit.
“If you start with a group of people it’ll be much easier to get to product-market fit because you just need to solve the problems of the people in your community”
Market by being you.
Sahil is a big advocate for building in public - just check out his Twitter @shl and essays on his website. We asked him about how people early in their careers or early founders can share authentically in public and his advice was quite simple:
“Confidence is something you get after the fact, not before.”
It’s about finding a personal niche - something that you can talk about because it’s something that you care about or it’s just fun. Building in public is so much easier when it’s something you enjoy.
“People want to learn from people who are only slightly ahead of them. There are always going to be 10x the amount of people who haven’t started compared to those who have started”.
Nothing crazy about being the second employee at Pinterest
Sahil might be well known for Gumroad and his tweets but he started his career as an operator, not a founder. We thought that starting as the second employee at Pinterest would be a pretty important predictor of Sahil’s success. He simply said, “It’s not that crazy, there’s nothing special about it”.
Ok, we had to dig a bit deeper.
“People think that working at Canva is so crazy but it’s not any different to working at another startup. The difference is that Canva built something that people wanted…It’s like painting, a beginner and a master will do the exact same thing. Only that the master is much much better at it”
It comes back to Sahil’s confidence and fearlessness to go against the grain in his career.
“People think it’s impossible to build a billion-dollar business or a 10-billion-dollar business. It’s unlikely because there’s a lot of risk, there’s a lot of serendipity. But in terms of skill and difficulty, there are a lot of things that are harder than that. Arguably, learning English is much harder. It’s a very weird language but we’ve all put in thousands of hours towards it”
“Failing” to build a billion-dollar business
In 2011, Sahil left Pinterest to work on what he thought would be his life’s work - starting Gumroad and turning it into a billion-dollar company.
As he wrote in his now-famous blog post - “Reflecting on My Failure to Build a Billion-Dollar Company” he had a lot of early wins on the board - 52K people checking out a pre-launch on Hacker News, raising $1.1M from all-star angel investors (the likes of Naval Ravikant and Chris Sacca) and only 19 years old.
Things were always heading in the right direction: up. But as Sahil says, being venture-funded is like playing a game of “double or nothing - it’s euphoric when things are going your way and suffocating when they are not”. The growth rates were not enough to raise the next round of funding and eventually the runway started drying up too.
Sahil had to lay off the entire team until Gumroad was just left with himself. Keeping the business alive meant that creators would still get paid, but also without the “weight” of external investors, Sahil was in charge of where Gumroad went.
We asked Sahil about how we had the resilience to go through the layoffs and hold onto the business.
“Honestly at the very start it was just fear of failure, I felt obligated to our creators. Turning off their livelihoods felt wrong. I picked a problem I care about, people that I cared about so if I really started another business it would probably be for the same community. So I figured, why would I start from scratch?”
The most important takeaway in Sahil’s eyes was about how success is all about perspective. No one actually determines success - it’s an arbitrary thing.
“Your failure is probably somebody’s success…reflecting on that post, my failure of building a billion-dollar business is probably already a success in some people’s views”
Leading the way for the future of work
“The meta-narrative of Gumroad about the future of work is almost more compelling than the company itself”
Gumroad is a particularly interesting company in the way it is structured. Get this - no full-time employees, no meetings and the team are is fully remote. This has been the case since 2017 - way before COVID made remote work the new norm. We asked Sahil how he decided to run Gumroad in this way and how he’s made it stick.
“Honestly it started as a selfish decision. I write and paint almost full-time so when I needed to start hiring again I really couldn’t be sitting in meetings all the time…I made a Kanban board where people can just pick from the top and work whenever they wanted. And since that time it stuck.”
In his view, it will still take some time before companies like Gumroad will become the new default, but he sees it as a new “north star” of the company:
“I think it (the new way of working) will happen, but it won’t be the default. We’ve got 2 years of remote work during COVID vs. a century of office working. But I see it as a responsibility to see this experiment out to the end.”
Customer success has dramatically evolved to a proactive and strategic function that's critical to most startups. By all accounts, it's still a relatively non-competitive route into startupland. So, how do you break in?
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