Comfortably uncomfortable

The first step I take when starting a new project is securing the domain. If I had known about Snagged back in 2020, I probably wouldn’t have settled for the dyslexic version of beehive.

Snagged is a boutique agency that helps clients acquire premium domain names and digital assets.

Rob Schutz was the former Co-founder and Chief Growth Officer at Ro and now spends his days helping founders and publicly traded companies alike secure some of the most exclusive domain names on the internet. The process is dead simple:

Not to name drop, but Snagged is the preferred partner for Silicon Valley legends like Garry Tan (CEO of Y Combinator), Alexis Ohanian (Co-founder of Reddit), and John Zimmer (Co-founder of Lyft).

Whether you’re trying to buy your dream domain or sell one from your library — Snagged is the only partner with verified big domain energy.

There’s a premium on people who actually take action.

That’s already enough motivational fluff for one email, but it’s true. I owe almost all of my success to jumping into the deep end and just going for it.

After graduating from college in 2016, I was back living in my parents basement after a failed startup attempt left me with no internship experience and just a few dollars in my bank account. I used to have a screenshot of my checking account at $0.55 but somewhere along the way I seem to have lost that relic.

One Saturday I was driving home from Washington D.C. and caught up with my buddy Austin Rief on the phone. He opted to pursue building Morning Brew instead of working in investment banking (hindsight: good choice) and told me that they needed some help building some features on the website.

He offered $3,000 (5,000x the amount in my bank account) and without hesitation I told him I’d be able to do it. I was a self-taught software developer, with no professional experience whatsoever, fresh off a failed startup.

The truth is — I had absolutely no idea how to build what he wanted. It didn’t matter; I needed the money and was convinced I would be able to figure it out.

It’s actually wild to think back on, but I almost gave up on that project several times. I was routinely up past 3am trying to configure these bootleg Wordpress files in PHP and doing way more harm than good. I swear I had the text written out a handful of times to let him know I wouldn’t be able to finish.

But I never sent the text, and ultimately did figure it out. (Side note: this would have been a whole lot easier if ChatGPT existed back then).

After completing that project he turned around and asked, “we actually have an entire backlog of things to build… want to keep helping us?” I continued to exaggerate my competence and build feature after feature that summer until it ultimately landed me a full-time job as their second employee.

Fast forward to 2020 and Morning Brew is one of the most successful media upstarts in recent years, home to over 4M daily readers, and is acquired by Business Insider for $75M.

Fortune favors those who take action.

After leaving Morning Brew that fall, I pitched the idea of beehiiv to two of the most talented engineers I had worked with: Ben and Jake. We all agreed that it had real potential, but would require a ridiculous amount of work to get it off the ground.

It was just an idea; and ideas are most vulnerable in their early days. I’ve come to learn that the default action in life is typically inaction.

Everyone is busy. Everyone has responsibilities. Everyone has legitimately good reasons as to why today isn’t the day that they’re going to do something different.

You really have to brute force your way into making something happen… or nothing will. There is far too much friction and “life” constantly pushing you back towards the status quo.

Ben, Jake, and I all had demanding full-time jobs. I was about to move across the country from New York to Los Angeles. Ben and Jake were making moves of their own to Denver and South Carolina. We all had our own trips and vacations planned, and other commitments with work, friends, and family.

I’m going to go ahead and coin this stage the “sprint period” — it’s where the majority of my life’s endeavors have gone and failed. The sprint period is where you need to unabashedly go out of your way to fully sprint at something to make it happen… or it won’t.

Sure, you want to build it… but you have a friend’s wedding this weekend, and then the next week you’re traveling for work. You're back the following week, but your co-founder is on a huge project for work and likely won’t have the time to commit until next month.

Sound familiar?

If you choose to work with others I actually believe that it’s harder to get through the “sprint period.” More people means more commitments and the complexities of life compound. In my experience, it often leaves you working in isolation on a group project (which is demotivating), or waiting around for others to become available (which delays progress and momentum).

…and before you know it.. it just sort of… fizzles.

Fortunately Ben, Jake, and I sprinted at this almost immediately. We set up a weekly meeting and created a roadmap in Notion with timelines to hold us accountable.

For the next 10 months we balanced this side project with our full-time jobs, travel, and other life commitments. At one point Ben and Jake were on an extended vacation in Costa Rica that I absolutely ruined by pushing them to build a handful of new features rather than enjoy time with their families.

I still owe them both a vacation for that.

In the prelaunch days of a company, everything is so fragile. I genuinely don’t know if we’d be here today without some of those relentless sprints.

But we eventually did push through to the other side. We had a working prototype by the summer and raised a $2.6M seed round that July.

Despite the sprinkle of revisionist history, that project almost died a handful of times along the way. The forces of everyday life push even the highest conviction ideas back from progressing.

Even this very newsletter was something that I had pushed off for years. The timing never felt right and I could never carve out the required hours of my week to actually make it happen.

No matter what, it was going to be inconvenient and uncomfortable. But I had enough conviction that it was something worth doing, and I eventually took the first steps to bring it to life. Over Thanksgiving break in 2023 I had a little extra time to build the foundation and announce it.

I have too much of an ego to announce something publicly and turn back on it; so the only way out was up 🚀.

Fast forward to today and…

I’m even heading to Costa Rica next week to host the 3rd Big Desk Energy Founder Mastermind. I’ve been able to build my network and connect with some remarkably impressive founders, all because of this newsletter.

It’s easy to acknowledge that taking action is important… but taking action requires being comfortable with discomfort.

Telling my friend I could build something I was totally unqualified for was uncomfortable.

Sacrificing nights, weekends, and vacations to build a side project with no guarantee of anything was uncomfortable.

Writing a 1,500 word essay each weekend while running an 85 person high-growth startup is uncomfortable.

Maybe I’m just a sick fuck who’s addicted to stress and discomfort, but if it weren’t for that you wouldn’t be reading this right now.

If you enjoyed this post or know someone who may find it useful, please share it with them and encourage them to subscribe: mail.bigdeskenergy.com/p/comfortably-uncomfortable

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