SuperFriendly 2021 Wrap-Up

SuperFriendly’s worst year to date and one of my biggest professional failures. Time for a big change.

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Against many criteria, 2021 was SuperFriendly’s worst year to date and one of my biggest professional failures. It was time for a big change.

2021 SuperFriendly in numbers

From a quantitative perspective, a lot of things seemed to be headed in the direction I wanted for the company. I decided a few years ago to try to scale the company up, to see how far the business model could stretch, and the trajectory seemed to be appropriately headed in that direction, especially against some of the goals I laid out around this time in 2020 and 2019.

Time spent

I’m generally happy to see my time spent working decrease year over year, but I also want to think that I’m learning how to have more impact with less time. This year, I felt the opposite. I worked less than I ever have, but I also felt like I had little to no impact. And yes: I was languishing. And yes: despite working less than I ever have, I was burnt out.

Here’s how I spent my time in 2021.


We did 25 projects in 2021, a 32% increase from 2020’s 19 projects, including:

Some of these are the best work to come out of SuperFriendly in a long while.

Revenue & Profit

By the end of August of 2021, we had already made the same revenue we made in all of 2020. 2021 was shaping up to be the highest-grossing revenue year yet.

However, by the end of August of 2021, our profit was at -4% and continuing to trend downward. In other words, we were doing more projects than ever making more money, but also spending too much money in order to do so. Another month and, for the first time ever, we would have been completely out of cash.

Why didn’t I spot that sooner? A number of reasons, really.

  1. I simply wasn’t doing a good job paying attention. I was both busy and burnt out.
  2. Project work is often a feast or famine business. Our pipeline has been consistently full for a few years, but we can’t control when work lands. The right project at the right time turns grim profits into abundant pockets. So there’s always hope that “if this project or that one hits by the end of the month, we’ll be just fine.” Until we’re not.
  3. Refunds. I’ve always wanted SuperFriendly to earn its income. One of the outcomes I want for every one of our projects is for the client to feel or even say, “That was money well spent and I’d gladly spend it again.” In SuperFriendly’s history, we’ve only had 1 project where we felt we didn’t fully deliver what we should have, so we returned $5,000 to a client after completing the project. In 2021, we had 3 projects where we weren’t able to fully deliver, to the sum tune of $106,500 that we refunded to those clients. None of them asked for a refund, but I couldn’t keep that money in good conscience, knowing that we hadn’t delivered on what we promised. As CEO, all of that is my fault for not being able to lead our teams to deliver the kind of work we promise. We never withheld or retracted pay from any of our SuperFriends, so this is money we paid out of our already-thin and dwindling profits.
  4. There continues to be a global pandemic. I imagine that had at least some effect on the undercurrent of how work has been getting done—or not—in the world over the last year. I simultaneously feel like all of this was solely my fault and also that none of it is because of the state of the world. It’s probably somewhere in the middle.

People & Purpose

In short, we didn’t improve really at all on any of our goals in hiring and creating better opportunities for more underrepresented folks in tech, and we didn’t pay our SuperFriends as much either.


As important as that info above is, it’s still just reporting, not really analysis. Or—more crudely put—data puking. What should we do next year as a result of all that data?

It turns out that there’s another metric that’s more important to me, one that I didn’t even realize existed until 2021, despite running SuperFriendly for almost a decade. When I think about what I want SuperFriendly to do, what impact I want it to have in the world, I want it to change people’s lives.

And sure: lots of business owners wants their company to change lives. It’s a trite idea by now, which is partially why I never really gravitated toward that kind of language before. But 2021 made me realize that that’s the specific phrase many of our previous SuperFriends and clients use when talking about their experience working with and for SuperFriendly. I realized it in 2021 because it didn’t happen as much, and I started to notice the lack.

The phrase “working with SuperFriendly was life-changing” often came up in the context of our apprenticeship. It was an intentional format to help people learn more, and, as a result, earn more too. (Expect to see the “learn and earn” language show up in future versions of SuperFriendly.) This was a direct action tied to our mission of “creating better opportunities for those who wouldn’t otherwise have them.”

I stopped the program in 2018 because I wasn’t doing a great job creating those kinds of opportunities for my apprentices between all the other things I was also doing. That was the primary impetus for wanting to scale SuperFriendly up. At the time, I was directing most of SuperFriendly’s projects myself. My hypothesis was that removing myself from client work and business development allowed others—and more of them—to occupy those roles us to create more pairing scenarios for more apprentices, interns, and junior people. And thus began almost 3 years of trying to scale up with more projects, more senior people to pair with, more money to provide more support to more people.

What I learned was that there’s a hefty overlap between those who say SuperFriendly was life-changing for them and those who worked directly with me (vs. indirectly with me or not at all). In 2021, I only count 2 SuperFriends that mentioned to me that their interactions with SuperFriendly were life-changing, and both of them worked directly with me. There have been other versions of the idea for others, like the fact that they learned a lot or that they love their team, but that particular phrase that was so prevalent before is now all but gone.

I can’t help but think that this decrease in changing lives is correlated with my lack of involvement in client work. As a CEO, I have less relevance to an apprentice than I have as a creative director, designer, or engineer. That’s an uncomfortable idea to me, but I’m trying to create space for the idea that this isn’t at all a judgment on others as well as giving myself permission to be better and more interested in an aspect of work that other people aren’t.

Changing someone’s life is difficult. It’s also a completely separate effort to take on. I lament that it’s not part of our industry’s job descriptions for creative directors or tech directors, but that’s the current reality. I didn’t expect for our more senior SuperFriends to figure out how to improve the lives of the other SuperFriends on their teams, but I certainly wanted it. I watched our SuperFriends struggle to balance tension between delivering for clients and supporting their team, and, as much as I encouraged them to prioritize the latter, I didn’t have a clear rubric for how to do that. “Do it how Dan would do it” is not a playbook, and I actively discouraged that line of thinking. But I also didn’t have a good alternative to put in its place.

Scaling is difficult too. I’m learning that it’s not my gift, and I’m not sure I’m interested in doing the work to get good at it.

What I am gifted at is seeing how there’s not tension but synergy between growing people and creating successful work and clients. One begets the others. I often remind our senior folks about the principle of “SuperFriends over clients,” which I’ll admit sounds a bit counterintuitive for a client services agency. It often confounds them, but I see it clearly. I’m slowly growing more comfortable around the idea that I have a vision for that that others don’t, and that’s where I should be putting my focus.

The edges of the SuperFriend Model

The SuperFriend Model—a network-based approach to staffing projects real-time with appropriate expertise—was ironically one of the things that got lost in the scaling (ironic because it’s a model designed specific to respond to the ebb and flow of scale). As much as I’ve actively rejected it over the years, 2021 saw SuperFriendly starting to act like a traditional agency, embracing the flaws of that model—mainly the crushing pressure of continual overhead against irregular and unpredictable pipelines—and not really adopting any of its benefits.

In 2021, I learned more deeply what the SuperFriend Model needs to succeed, some of which we had and some of which we didn’t. It needs a network supply that exceeds the pipeline demand. It needs someone whose job it is to continue to grow the network. It needs a steady supply of work. It needs laser focus on a niche. It needs ways to support and engage the people in the network. It needs a mechanism to train people in what it means to work like a SuperFriend. It needs a large and steady amount of working capital. All of these things and more combine to create life-changing opportunities for a SuperFriend, and, when that happens, it always translates to benefits for our clients. As many of those things become less available—especially capital—the SuperFriend Model becomes more and more difficult to sustain.

Back to the future

What does all of this mean? It means I’m concluding the experiment of scaling SuperFriendly.

A friend and mentor of mine recently shared with me that they often longed for their days of running a small company even though they worked at one of the largest companies in the world. Why? They had more impact at their smaller company, despite the massive scale difference. Their parting words to me in that conversation were, “Scale isn’t all it’s cracked up to be.”

I’m returning to working on client work again, for a number of reasons.

With profits down to almost nothing, frankly, we need the cash. I’ve often shied away from working on projects myself with the logic that we could probably get someone else to do better work for less money. But I often forget that I’m also one of the most profitable SuperFriends because I can play multiple roles on a project from design to strategy to engineering and more. With less people who can do more things, there’s less to manage and more money to put away for a rainy day. I’m returning in part to the original, older version of SuperFriendly, albeit in a new way with the benefit of a decade of hindsight.

The other big reason for me to return to client work is that it’s the best vehicle for me to teach, which I love doing. Pairing someone with me while I’m working has historically been one of SuperFriendly’s most successful ways to accomplish our mission of creating better opportunities for those who wouldn’t otherwise have them.

SuperFriendly in 2022

With a decade of hindsight, it’d be foolish to throw out some of the things that have worked in the past. Alex Hillman recently compared the opportunity to start over to the ability to replay a video game after you’ve beat it but with the new powers and items you earned the first time around.

Here are some advantages and principles SuperFriendly’s had over the years that I’d like to play up in 2022:

A lot of that is continuing what we were already doing, but the big change is going to be relinquishing trying to do it a some large level of scale. I’ll probably share more of this in detail in the future, but I’m aiming for 4 clients or less in 2022, all of which I will personally be heavily involved with. I think less clients and less revenue will lead to deeper impact, larger profits, and better opportunities for SuperFriends. Less quantity, higher quality.

I’m grateful for the ability to run a business where I can change, experiment, and try different ways to accomplish my mission. Amongst all the change over the years, a constant has been that SuperFriendly is my better opportunity that I wouldn’t otherwise have.

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