Hi all,

Noah Kagan 🌮 is the founder of AppSumo and author of the recent NYT best-seller, Million Dollar Weekend.

Last Friday, I asked him why he ignored all the other juicy problems he could have been solving at the time he committed to building a marketplace for software deals. 

I’m a big fan of Noah, but his answer unsettled me in its plainness:

"That was what I was excited about: software, deals and marketing! Nothing else still is more interesting to me.”

🤔

I suspected I was just one of the many people lacking a passion as easily defined as Noah's, instead trawling a ragged list of passing interests and ephemeral hobbies behind me.

But actually, that's not the issue.

I realised I have a monkey on my back; there's something stopping me from pursuing things that are interesting to me.

The issue for me – and possibly you, too – is that I've emerged from a 'mission-critical' industry. In my case, healthcare.

In the world of healthcare, making life-saving medicine is always the soup du jour, the effect of which is that most other problems look trivial by comparison.

Which is not to say they are trivial.

(We obviously need other stuff besides medicine!)

It's really that I've been taking myself too seriously.

I've developed something of a career hero complex; a 'noble' excuse for not taking risks on anything that isn't about saving lives. Or, in the case of Fawn, starting lives.

What fresh creative poison is this!?

How constant moonshots can kill growth... (and an antidote)

Before I joined a venture-building programme, a mentor playfully asked me if I was ‘broken enough’ to build a start-up.

To be honest, I thought he was just being a contrarian.

Not wanting to discard any wisdom in the question, I answered that I didn’t know, and that I suspected it would be exciting to find out.

(I found out 🫨)

What I learned was that, even though the startup game can look like a playpen for chest-beating Stanford drop-outs, many entrepreneurs are actually just taking the path of least resistance to alleviate an invisible discomfort.

AKA, being a little bit broken.

It turns out, deep enough discomfort (like a space race) will drive you to sleep under your desk and build rockets to visit extra-planetary bodies.

Thus, ‘moonshot’ enters the lexicon, born from Kennedy’s famous speech.

But much like the Moon, there’s a dark side to the moonshot, too.

If we only allow ourselves to go after the Big Stuff, we become resistant to the other 99% of potentially more interesting, fulfilling, and realistic Small Stuff that is often equally constructive, but in different ways.

And vitally, taking 'size' as our primary cue for which problems to attack can lead us to the graveyard of burnout victims who tried to save the world every day.

So here’s an antidote I’m experimenting with this week...

If you’ve found yourself in the grip of the entrepreneurial hero complex, perhaps consider taking some time for an Anti-moonshot: an intentionally smaller project that is first and foremost designed to shake things up.

Five characteristics of a good Anti-moonshot:

1. It's rooted in a problem that you've experienced first-hand
2. It's small enough that it feels uncomfortable
3. It's tractable enough that you stand a chance without a strong starting position
4. It doesn't matter if it doesn't work
5. But it might work

An Anti-moonshot doesn't have to (and probably shouldn't) define your career, and you can always set money & time budgets to stop things getting out of hand.

The aim is to expand the terrain of problems that we feel are ok to attack.

So, never one to suggest something I'm not experimenting with on myself, here's how I've been building my own Anti-moonshot this week...

🤡

🦧 In the wild

As a gym-goer who's started growing his hair out, I want to keep my hair from falling into my eyes while I train, but hairbands and clips make me look like a schoolgirl, wearing a hat indoors makes me look like a serial killer, and there's no such thing as a cool sweatband.

I know. Hang in there.

After a bit more Googling and some trips to local sports shops, it looks like sweatbands have been almost totally neglected by designers.

There really aren't any interesting ones.

[Cue the evil monkey on my back]

'But my experience is in the pharmaceutical industry! However will I explain this to my dear, loving parents!?'

My Anti-moonshot appeared, small and proud like a mouse on horseback emerging over a sun-set horizon.

With a little grit, some generous help from AI, and a newly minted devil-may-care attitude, could I reinvent the humble sweatband?

Here's what happened over the next week

First, I set a time and money limit.

I don't want to spend more than £200 on set-up costs, and I won't work on this for longer than three months without getting 300 sales.

And just because the problem is small, doesn't mean the challenge has to be easy; we simply dial up the intensity with which we attack it.

Keep in mind, I have ZERO experience in this industry, so I'm breaking pretty much all the rules... but that's the point.

Back to my check-list:

✅ Rooted in a problem that I've experienced first-hand

✅ Small enough that it feels uncomfortable

✅ Tractable enough that I stand a chance without a strong starting position

✅ Doesn't matter if it doesn't work

✅ But it might work.

And if it doesn't work, you're welcome to enjoy the cautionary tale at my expense.

Off we go.

I started with Google Trends to validate that other people are having the same problem, with intriguing results.

I took a broad look at options across Amazon, Etsy, and Google Shopping, as well as visiting some local sports shops. I saw a lot of plain, uninteresting, and low-quality bands, which I think explains the declining interest in these things.

Next, I turned to ValidatorAI to vet my idea and set some direction.

(This article isn't sponsored by Validator AI but Aaron, the founder, has generously helped me with ProblemKit.)

ValidatorAI gives you immediate feedback on key risks, as well as variations on your idea to explore. For me:

• Sweatbands are likely a trend rather than an evergreen business, so I should be careful around the longevity of the idea
• Sweatbands are not technically complicated, so I should have a clear strategy for defensibility
• I could consider extending my target market to festival-goers and charity runs
• I could experiment with a subscription model for new designs
• Sustainable manufacturing will likely be important to my audience

Since ValidatorAI didn't totally rip my concept apart, I proceeded to search out some celebrities and models who embody my target niche.

Like it or not, mullets are SO back.

And keeping an eye out over the last week, there are ALWAYS at least five people in my local gym who would fit nicely into the picture collage above.

I also collaged some design inspiration from sports stars and fashion models wearing sweatbands through history.

By this point, I was clearly settling on retro-inspired statement sweatbands carrying an 80’s/90’s aesthetic, targeted at yours truly: a wannabe tech-bro in London.

I moved on to naming, using the exercise to find my brand voice by playing with different fonts, mocking up labels in Canva, and pulling inspiration from old books and posters.

I wanted something eye-catchingly gross, fairly seedy, and catchy (ChatGPT refuses to help with this).

After checking domain availability and other registered companies, I'm delighted (and quite horrified) to introduce you to my latest monstrosity:

👋 Sweat Lickers Limited @ sweatlickers.com

Now, before you write me off, I mocked up 12 images of Bjorn Borg wearing some questionable designs and sent them to some friends who I thought might be interested.

And guess what?

💷 Money started coming in 💷

Not much, but enough to trigger a double-take.

The rest of the week was spent with ChatGPT and Claude open, learning an unholy amount about:

• Textile manufacturing and how to work with manufacturers
• How to design seamless repeating patterns
• How to prompt-engineer photorealistic fashion models and photoshop my designs onto them
• Making sweatband prototypes on a home sewing machine using print-on-demand fabric

(If this is your jam and you'd like me to deep-dive on this process in future, let me know...)

Look, like all hair-brained ideas, this might not go anywhere.

But in the meantime, let's see if this Anti-moonshot breaks me out of my box...

🍭 Weekly problem

As someone fixated on a career goal (and often to the exclusion of all else), I want to take advantage of long bank holiday weekends for relaxing trips into nature, but I always forget to plan ahead and end up staying home, rather than fighting the crowds and last-minute prices.

🛸 Misc.

A lot of you THINK you know about computing.

But do you know where those first computers – the ones with the punch cards – came from?

This 2-minute documentary is basically ASMR for tech nerds.

Wishing you lots of problems,

Alex

Looking for a coach? I'm working with Neil Mackinnon.