Why I’m giving up on solopreneurship

A few a times a year, the stars will align in Nazaré, off the coast of Portugal.

The oceanic swell, tropical storms and tides will perfectly coincide to create the conditions from which arises an epic sea monster.

The 100 foot wave.

Garrett McNamara is the OG trailblazer in this feat of man versus wave. The 54 year old with a salt and pepper buzz cut isn’t exactly who you’d imagine slaying 100 foot walls of water.

No long sun-bleached hair. No six pack. No tattoos.

Yet as you see this tiny speck of a human careen down the face of a 100 foot wave – regardless of how much you care about surfing – you’re left breathless and in awe.

It’s tempting to see McNamara as the Man in the Arena. The gladiator looking to emerge victorious. The one who will bask in the accolades, should he exit the wave’s barrel unscathed.

But that’s actually not how the sport works.

Yes, you only see surfer and surfboard in the ocean. But like most things in life, there’s an entire crew playing crucial supporting roles – which enable McNamara to surf the world’s biggest waves.

There’s his wife and business partner sitting on the light house “spotting” the oncoming sets.

There’s his tow partner, delicately navigating him on a jet ski around these water canyons – milliseconds away from a devastating crash of whitewater.

There are the geologists who helped him study the underground canyons creating the swell.

There the equipment makers who custom-designed a wetsuit with an inflatable air canister to prevent him from being submerged in the event of a wipeout.

And there are the paramedics on jet skis and on land, should the unthinkable happen.

Yes, surfing a 100 foot wave is supported by a team the size of a Formula 1 pit squad. It’s not a lone wolf sport.

Now let’s fast-forward to Manhattan Beach, California. My passion is surfing waves 1/33rd the size of the ones in Nazaré.

And over the past six years, my other passion has been growing RadReads.

First a newsletter. Then a blog. Then a podcast. Then coaching. And now we finally found our groove with online teaching.

To the untrained eye, it may look like the dweeb’s version of the 100 foot wave.

A dude. In his garage. Banging away at his keyboard.

A creator. An “indie hacker.” A solopreneur.

And during my short career as an entrepreneur, those were pretty much the right labels.

But it’s no longer true. While I’ll never be a big wave surfer, I’ve bumped against the limits of what I can do by myself.

So this year, I’m taking the plunge into “big kid” (or big wave) entrepreneurship and turning RadReads into a proper company.

Yup. One with payroll, benefits (soon), policies and an ambitious mission.

But I’d be lying if I didn’t acknowledge that the trade offs make me uncomfortable.

For starters, I spent my Christmas vacation crafting OKRs, navigating payroll schedules, creating reimbursement policies and forecasting a year’s worth of cash flows.

Not to mention the keep-you-up-at-night pressure of multiple mouths to feed. And staff meetings. Yikes, staff meetings!!!

And most importantly: Will I have to start working before 11:30 am and sacrifice my daily surf sessions?

Introducing our new squad

RadReads now has two full-time and three part-time employees. And yours truly.

Our first two full-time team members are Marian Knopp and Kate Berglund, both Product Managers.

Marian will lead our student-facing business, which is anchored by our flagship course Supercharge Your Productivity (join us for Cohort 9) and our new monthly offering, The $10K Accelerator (currently only available to our alums). Since the course launched over two years ago, we’ve taught over 500 students how to lead more productive, examined and joyful lives.

Kate will lead our newly launched B2B offering, The Rad Studio. We launched this business because companies kept asking us the same question: how can we leverage the latest tech and collaboration tools so that our colleagues can lead more productive, examined and joyful lives (while staying burnout-free). The Rad Studio designs custom workflows and trains teams on how to be intentional about all their tasks and activities. To date, we’ve worked with Lego Ventures, Notion (yup, we run part of their employee onboarding training) and many other tech-forward businesses.

Kate and Marian join our three other part-time employees, Jaen Hawkins (Course and Community Manager), Cole Yaverbaum (Marketing Specialist) and Matthias Frank (Marketing Specialist).

What excites me the most about these two businesses is how unified they are in our mission to help high-performing professionals lead more productive, examined and joyful lives. After all, by now you all know that RadReads’ informal tagline is:

Come for the productivity, stay for the existential.

And you also know that the “how” only represents a tiny piece in leading a life full of joy and meaning.

The “why” is what really moves the needle. (Yet gets lost amidst the sexiness of Shiny New Toy Syndrome.)

Both of these businesses are fundamentally anchored in the belief that if you nail your “why” and pair it with the right “how” – you’ll be unstoppable.

Is this all about $10K work?

Now you’re probably saying to yourself. I see what Khe’s doing here. He’s doing that $10K Work thing. Creating leverage in the business.

And you’re right. To a certain extent.

When I was building alone, I certainly wore many hats.

I was Controller. Editor-in-chief. Lead facilitator. Marketer. Logo designer. Yup, I did a lot of $1,000 (and $100 and $10 work).

And building a team is certainly a high-leverage activity that moves us closer towards the magical quadrant of $10K Work.

But the matrix alone doesn’t paint the full picture.

RadReads was living on borrowed time

RadReads became profitable in 2020. (Yup, after 5 years of basically working for peanuts.)

Yes, we were delivering these elaborate and beautifully orchestrated learning experiences to hundreds of students. Just me and a virtual assistant.

Like Garrett McNamara, I was pretty much the lone wolf on the wave.

I had a tremendous amount of freedom. (I took all of last summer off.)

I surfed pretty much every day for the past 3 years.

I only pursued projects that made me happy. And clients who I wanted to work with.

So why give that up? Especially if it was profitable?

There are a few reasons.

First, running 100+ student courses with one other person is a recipe for burnout. It’s totally unhealthy and unsustainable.

In hindsight the business was living on borrowed time. We had sold something that we weren’t in a position to reliably deliver over the long-term.

Either I would’ve collapsed. Or we would’ve had a spectacular failure from juggling too many balls simultaneously.

Second, it was extremely lonely. While many glamorize the lives of digital nomads and creators, what’s lost in the discussion is that these business owners literally spend all day by themselves in front of a computer. For years.

That, by itself is quite lonely. But it has further ramifications downstream.

There’s no one to gut check your ideas.

No one to edit your blog posts (hence all the typos, I apologize).

Or celebrate your wins with you.

And finally, during this past year I realized that we were building something truly special.

I saw it in the way our students’ lives were transformed after they took Supercharge Your Productivity. Our alums would apply the lessons from the course and thrive in their lives.

Some would take risks on new careers.

Others would downsize their careers to be better spouses and parents.

Some alums fine-tuned their professional skills that helped them get promoted.

Some finally took the first daunting step on a new project or hobby.

Others built habits that fundamentally changed their health and happiness.

And pretty much everyone realized how nice it is to take a walk without headphones.

Our students were repeatedly moving one step closer towards a true sense of equanimity, self-love and serenity in their daily lives. They had stepped off the hamster wheel of untethered desire and ambition.

This product-market fit (not to mention NPS score of 72) excited me. I quickly realized that I was the bottleneck in taking these teachings to more students.

Asking the $10K Questions

I had always set out to build a lifestyle business. But that aspiration comes with another, juicier question:

What kind of life do you want to live?

This may seem like a trivial question, but it’s actually extremely complex. It’s the ultimate $10K Question.

One exercise that I often use is Ali Abdaal‘s Ideal Ordinary Week. The exercise goes as follows:

Imagine a rich benefactor enters your life. This benefactor offers to pay for your entire family’s living expenses for the next two decades. Your mortgage. Their school. Your life insurance premiums.

How would you spend your days?

In this hypothetical scenario, even if you allocated 14 hours a day to sleep, fitness, family, friends and self-care – guess what – you’d still have 10 hours of “activities” to allocate each day. (Plus, in this scenario the concept of “the weekend” would fade away, so you’d have 70 hours of activities to allocate each week.)

70 hours! That’s a lot of hours!!!!

How would you spend them? I think often about this question. With those 70 hours, a few things that I’d want to do is:

  • Spend a lot of time with my family
  • Serve others
  • Spend time with people who energize and inspire me
  • Express myself creatively
  • Surf. A lot.

And it turns out that growing RadReads is completely aligned with this activity mix. Plus, we’ve got a crew of colleagues who are equally as passionate about the mission as I and who also know what their ideal ordinary weeks look like.

And let’s be honest. Let’s talk about that cheddar.

We have a sneaky suspicion that we’re sitting on an extremely profitable business. If we can unlock that value, it will be shared amongst our colleagues.

So what about the surfing?

Here’s where it gets exciting.

As a company, we’re eating our own cooking. We’re a fully-remote, asynchronous company with a 30 hour work week. (In fact, none of us have ever met in person.)

If we can teach professionals and other companies how to design intentional lives – well damn, we’d better lead by example

Here’s a snapshot of our internal values:

Here’s a snapshot of our vacation policy:

Here’s a snapshot of our internal communications expectations:

Here’s a snapshot of the dashboards we use to manage all of our communications. (On average, we probably receive 15 slack messages a day. Zero internal emails.)

(Oh, and The Rad Studio can totally build this for you.)

And most importantly, we are committed to uncovering all of our unspoken social norms. This can feel awkward at first, but it’s the only way to build trust in a fully remote work environment. So each of us has a user manual, detailing our styles, quirks… and our typical schedule.

And since you asked about the surfing, here it is:

My colleagues and I want thank all of our readers, students and Radvocates for their support on this journey. We genuinely wouldn’t be here without all the love you have shown us over the past 6 years. And we can’t wait to cook up more Rad sh*t for you all!

PS Enrollment for Cohort 9 of Supercharge Your Productivity is currently open. The course begins on 1/25.

For instant Access, Enter your Details Below:

🔒 Privacy Protected by our “Zero Spam” Policy

For instant Access, Enter your Details Below:

🔒 Privacy Protected by our “Zero Spam” Policy