In 2019, I was the VP of Product at Teachable and managed a talented team of product managers and designers. I joined as the first design and front-end hire five years before that, and had seen Teachable evolve from a handful of folks to a team of more than a hundred, and become one of the leaders of the online creator movement.
As someone who went from an individual contributor to a VP in a short amount of time thanks to the trust of Teachable’s CEO, I picked up years’ worth of lessons in a few months (I wrote about those lessons here.)
But after five years at Teachable, I found something amiss.
It started with a simple thought that I had in the back of my mind, but was now in the forefront: I moved from New Zealand to the United States in 2012 with the goal of becoming an entrepreneur — not a VP of Product (as great as that role is!)
The decision to leave was not easy.
For one, Teachable was growing faster than I ever could have anticipated when I joined, and I had spent over a year recruiting a Product team, which was now finally staffed up. (Teachable continues to lead the online course creator movement, with over $400 million in online course sales last year.)
For another, I felt extremely fortunate to be in this role, earning a salary I hadn’t even dreamt of a few years ago.
In 2002, my parents immigrated to New Zealand from India without a job or an income, opting to enroll in a university in their late 30’s. They worked multiple jobs to ensure my brother and I got an education in one of the world’s greatest countries. At Teachable, I was making much more than my parents’ combined salary growing up, and couldn’t fathom to let go of the comforts of a well-paying, well-respected job.
Also, I lived in Brooklyn with a wife and four-year-old and had almost no savings at the time (all of my net worth was in Teachable stock.) We paid close to $1,900/mo for childcare alone. I didn’t want my entrepreneurial dream to affect my family’s lifestyle, or rack up even more debt than we were in at the time.
And finally: though I was extremely passionate about the creator space and knew that I wanted to serve creators with my next startup, I didn’t really know what the specific idea was going to be.
I needed the time to incubate ideas and opportunities without worrying about where my next paycheck was going to come from.
After months of being on the fence, I chose to make the tough decision to leave and bid farewell to my Teachable colleagues, whom I’d shared some of my best life experiences with.
The consulting incubator
We were teenagers, and Sahil was one of the first users of the journaling app I launched, as was I of the early apps he built.
I watched him go from an indie app maker to building the Pinterest app, and then to starting Gumroad. Watching Sahil grow as an entrepreneur and human was always a huge inspiration to me.
Months before I joined Teachable, Sahil reached out to me and asked if I wanted to come work for Gumroad. As much as I wanted to, I had to say no, as I’d already committed to living in New York City after my green card processed (Gumroad was based in SF and in-person only at the time.)
Flash forward to 2019: Sahil and I reconnected over my departure from Teachable. Within a few days of exchanging ideas, he made me an offer I couldn’t refuse: while I was “incubating” my next idea, I could contract 20–30 hours a week for Gumroad and get paid more than a reasonable hourly rate as an engineering and design contractor. If things worked out, Sahil would support me as an investor and help me start my next company.
This felt like a dream gig (in hindsight, it was!), and I could breathe a sigh of relief knowing that my risk as an entrepreneur wouldn’t mean lowering my family’s living standards, or racking up even more debt while I incubated ideas.
As I’ve tweeted before, my nine months at Gumroad taught me everything I know today about how to run a leveraged remote startup. Gumroad is a small remote team that gets a lot done, and serves customers at scale. At Circle, we’ve implemented a lot of the remote async practices I observed at Gumroad.
Solo founder? No thanks!
Having worked for two solo founders in the past, the journey of a solo founder was not one that appealed to me. As great as the control and perception can be, it always felt to me like not having co-founders to share the journey with was a lot less fun and much harder.
It helped that I met both of my co-founders in 2014, and for years had known that I’d knock on their doors when I was ready.
I met one of my co-founders, Rudy Santino, while I was contracting for a design agency in Australia while waiting for my green card to process.
Rudy and I clicked because our tastes instantly aligned on almost everything we discussed — from the products we liked to the podcasts we listened to. It helped that both of us identified first as designers, and saw most things through the lens of systems thinking.
Whenever we talked, simple conversations often turned into jam sessions that lasted for hours, and we’d walk away feeling exhilarated and excited.
A few months after I left Teachable in 2019, we found ourselves vacationing together in Portugal with our families. After bouncing ideas late into the night on the terrace of our Airbnb, we made a commitment to start a company together. Everything felt natural and organic; neither of us had to convince the other.
Andrew Guttormsen, my other co-founder, and I couldn’t be more different in our skillsets — though we’re extremely aligned in our values.
Andy was the VP of Growth and Marketing at Teachable while I was the VP of Product, and he set in place the growth engine behind Teachable, which recently passed $40 million ARR.
If you look at Teachable’s early growth numbers, you can see the impact Andrew had.
Over the years, Andy and I built a deep friendship as first-time Teachable VPs, and supported each other through our highs and lows.
Because our skills don’t overlap much, the opportunity to learn something from each other in every single conversation is always pretty high. In fact, most of what I’ve learned about startup growth and SaaS fundamentals comes directly from my conversations with Andy.
When it turned out that both Rudy and Andy were interested in starting a company with me, I couldn’t imagine better folks to take this leap with.
One of the first things we worked on together was a shared document about our values, and outlined what we wanted our company to be in spirit.
Despite having known each other for years, this was an extremely useful exercise for us to start with before any real work got done. It helped us align our goals and vision right off the bat, as it meant we had to discuss all the hard things first.
We didn’t exactly know what we were working on just yet, but we knew how we were going to work on it.
The modern community platform for creators
With Gumroad as a consulting gig, and Rudy and Andy as my co-founders, we had some of the ingredients of a startup, but were far from being full-time and deep in the idea maze.
Our process was to jam on ideas once a week, and talk to every creator we knew about their workflows, opportunities, and problems. After listening to them, we ran our ideas and mockups by them with the intention of finding similar themes across creators.
It helped that Rudy had built CoursePro, a website builder for course creators, and was working directly with some of the world’s top course creators.
We’re incredibly thankful to some of these folks who spoke to us early on for little in exchange: Michael Schmidt (SmarterGerman), Tiago Forte (Forte Labs), Giovanni Dienstmann (Live and Dare), Peter and Michelle Dalmaris (Tech Explorations), and Billy Bross. All of them are Circle customers today.
Through our conversations and many attempts at coming up with helpful ideas, one opportunity came up repeatedly and excited us more than anything else: community.
Online creators earn a living by monetizing their product, time, and content. If you’ve read a blog, watched a YouTube video, taken an online course, subscribed to a newsletter, or listened to a podcast, you’ve participated in the creator economy.
Dave Ambrose, who became one of our early investors, talks about this trend as “the greatest shift of empowerment and wealth of our generation.” In 2019, Li Jin coined the phrase Passion Economy to encapsulate what they’re all about.
But historically, the dominance of platforms like YouTube and Facebook has meant that creators have not been able to own direct access to their consumers, which makes it hard for them to scale and create sustainable income. Startups like Teachable and Gumroad are changing that by giving creators direct access to their customers, but this movement has just started.
Even worse is the landscape of options available to creators for their communities. This has led creators to co-opt products like Facebook Groups (for mass consumers), Slack (for workplaces), and Discord (for gamers).
It became apparent to us that none of the incumbents were focused on serving creators with a quality product focused on clean engagement. What we saw were co-opted products, stale incumbents, and low customer satisfaction.
We felt we could do much better.
The opportunity in building a community platform focused on creators appealed to us for a bunch of reasons:
- Creators and brands need superfans for their products to thrive. A superfan is a strong advocate and a source of feedback — she wants to engage with the creator, and with others like her. She wants to engage with the wider community.
- Online educators are starting to see learning as a social experience. Learners in tight-knit groups can lead to profound personal growth experiences and have built-in accountability.
- Communities reinforce a creator’s value to new members. The captured social proof makes new members trust a creator’s products and helps onboard them.
- Communities generate ideas and solutions in public. If you’re listening, these can be harvested into future opportunities — new features, product lines, and iterations.
- Communities are built-in distribution for the creator’s projects, which means creators get a long shelf life.
Above all, we loved the idea of empowering creators by helping them build clean, distraction-free, non-toxic communities that prompted loyalty from their members, and open up monetizable opportunities for them like memberships.
After a few conversations with people who shared our excitement, we went heads down and started building our MVP in October 2019.
In November, we spent a week in Venice Beach: heads down and distraction-free.
Unlike most other ideas I’ve worked on, the momentum after a basic prototype wasn’t like anything I’d observed before.
A link to a quick prototype and few messages exchanged with my former boss and one of our first investors, Ankur Nagpal, led to a commitment from him to invest and for us to contemplate our fundraising strategy.
Within hours of deciding to raise, my friend and former colleague Conrad Wadowski committed to a check, as did Sahil.
Brian Tobal, an entrepreneur I was introduced to by one of our early customers (Tiago Forte) introduced us to a handful of angels. And within days, we had checks from a few individual angels — including Ankur Nagpal, Sahil Lavingia, Conrad Wadowski, Dave Ambrose, Matthew Ziskie, Paul Yacoubian, Chris Lu, and others.
Initially, we entered the fundraising process looking to raise a small pre-seed (< $750k), and anticipated raising a much larger seed later in the year. Either way, our goal was to be profitable within 12–24 months.
But when we spoke to and met the team at Notation, who turned out to be extremely aligned with our vision, we were convinced that raising more than we needed at the time made sense.
The argument was simple: if we raised more now, fundraising again is not something we’d have to worry about for a while, and would not be a distraction for a long time. This turned out to be a great decision, and allowed us to focus after closing the round.
Notation ended up leading our $1.5 million seed round in January 2020.
Building a new community platform in 2020 meant we had catching up to do. So we got to work, and listened closely to our ideal customers.
We differentiated Circle with our clean design aesthetic, easy-to-structure spaces, integrations, and embeds.
We shipped features that our ideal customers couldn’t “live without”: in-app notifications, moderation tools, analytics, single sign-on (SSO) integrations, custom domains, member profiles, member directory, CSS customization, weekly digest, Zapier integration, an API, and more.
After our first couple of customers and some help from our earliest backers, we started to see some happy accidents we (truthfully) didn’t expect to see so early.
Ankur made some intros to folks who turned out to be key early customers. Our waitlist grew organically after Sahil retweeted one of my tweets about starting Circle, and we added 1,000+ leads from this initial push.
We recruited three engineers with the help of our friends at Saeloun. We hired a full-time customer support rep. They’ve turned out to be incredible and I’m insanely grateful to work with them.
The initial momentum led to certain customers we ourselves were fans of reaching out — people like Tiago Forte, David Perell, Anne-Laure Le Cunff, Makerpad, Pat Flynn, Tyler Tringas, Jay Clouse, Kevin Fremon, Mackenzie Child, Carrie Melissa Jones, and others.
A handful of folks, like Ben Tossell (Makerpad), Noele Flowers (Teachable), Will Mannon (Forte Labs), and Marian Knopp turned into something more than just customers: they became our product confidantes and earliest advocates, sending us valuable feedback in droves of Loom videos while being passionate supporters externally.
In essence, our earliest believers kickstarted Circle’s own community, and we were dogfooding our product from day one.
When our customers invited their members, some of those members heard about Circle and joined our waitlist. When they tweeted about our product, people noticed. We’ve continued to add 1,000+ organic waitlist leads a month since January, without an ounce of marketing or promotion.
After some back-and-forth, we signed on Teachable as our first enterprise customer (and largest community by far), Pat Flynn and Matt Gartland from Smart Passive Income as customers and advisors, and partners in the memberships space like Makerpad, Memberstack and MemberSpace.
Smart Passive Income launched its paid membership community in July and passed $200,000 ARR in a single month.
Teachable launched teachable:hq, and has shut down its 45,000+ member Facebook group in favor of Circle.
Our initial customers are still with us, and usage has continued to increase. We hope they’ll continue to grow their thriving communities with Circle.
It takes a community
The great man theory applied to entrepreneurship is, in my opinion, a great myth.
In reality, my experience has taught me that an entrepreneur brings just one thing to the table: momentum.
And if that momentum is the right momentum, an ounce of snow can turn into a snowball, and a company is born.
But momentum is nothing without happy accidents and the emergence of a community.
For one, I’m not completely sure I would have had the courage to start something without my co-founders to share the journey with, investors who believed in us, customers who took a chance on us, and acquaintances who made critical introductions.
It takes a community to build something meaningful, and to drive that momentum forward.
And in building the modern community platform, our community is just getting started. Join us!