Unglamorous Starts

Ugly, uncomfortable, embarrassing -- yet absolutely crucial

I have always struggled with starting new things. That might sound like an odd confessional for an entrepreneur to make, but it’s true. This is because I struggle badly with perfectionism, which politely but firmly informs me that everything I attempt has to be amazing and get great results right away, or it isn’t worth doing.¹ As a result, I have missed out on a lot of potential joy because I was too busy crafting a fantasy about who I was instead.

That’s a real shame. And I see a lot of the entrepreneurs I work with struggle similarly. Maybe it was the deluge of near-free money that flowed as a result of the longest bull market run in U.S. history, but I’ll be damned if a lot of founders don’t act like the steps to entrepreneurial success are:

1. Come up with a random idea.

   1. Bonus points if you can mix a few elements from the zeitgeist.

2. Tell two college friends and one investor.

   1. Mandatory: over drinks. Preferably: somewhere obnoxious (e.g. club on Vegas Strip)

3. Receive investor check.

   1. Hire engineers and buy white board. Let your college buddies manage both.

4. IPO 🤑

This seems to be especially true for hardware engineers.² It’s wild to see their reactions when after a few months of getting firm no’s from customers and VC’s alike they are ready to hang up their hats. Failed company, they decide.

Sure, if they say so. But I don’t think it has to be. The truth is that starting new things is just uncomfortable. There’s no way around it. No matter if it is a company, a hobby, or some other habit. Even Batman had to go through it³ and honestly, if Batman had to go through it, then so do you. It’s going to be work, and the work will be difficult.

And I think that difficulty may be by design.

Even Batman screws up. Pobody’s nerfect.

Beginner’s Luck

In Paulo Coelho’s The Alchemist he talks about the power of beginner’s luck. The Universe wants us to begin, so it lures us in with some early success. It whets our appetite, or primes the pump, so to speak. In the world of hard tech, this early momentum could be anything from sharing an off-the-cuff idea with an interested investor at a mixer, to meeting the perfect future cofounder over coffee, to having a customer call out of the blue begging you to build them a product. I’ve experienced all of these. They’re great. It feels amazing. But then after that, things stop coming so easily.

All of a sudden, the investor doesn’t return your emails or phone calls. The perfect cofounder oversold their resume or turned out to be a megalomaniac-in-waiting. The customer calls back and says they’ve decided to build the product in-house. I have experienced all of these moments, too. They’re less great, honestly.

I have experienced this often enough to have a hunch that something⁴, somehow, is testing our resolve in these moments. It asks, “Was that inspiration just a flash in the pan? Or can you find a reason to continue?”

Now, that doesn’t mean you must continue blindly (or even at all)! It’s simply a great opportunity to practice a little discernment and decide if, as my good friend likes to say, the juice is worth the squeeze.

If you decide the juice is worth the squeeze, here are some tips for making the most from it:

Start Close In

David Whyte has a great poem that I think of anytime I am trying something new. It’s called “Start Close In” and I’ve shared a few lines below:

Start close in,
don’t take the second step
or the third,
start with the first
thing
close in,
the step
you don’t want to take.

Too often we start with the second or third step — the cool ones, the fun ones. We want to do logos and swag. We want to make fancy renderings, get offices, hire people, and generally head off to the races. Also, too often, we don’t yet know what the race really is.

It’s important to start with the first step. As David says, the one you don’t want to take. Do a strategy analysis. Call customers to understand their problems. Attend a conference or two to make sure you understand the industry. Work on mission and conceptual designs for ideas you have, instead of another pitch deck.⁵

It might not be the most fun thing, but it is the most vital to progress.

Get Curious About Difficulties

I’ve written a lot about my ugly early attempts at business and in the aerospace industry, so I thought that this time I’d share about my ugly early attempts at mindfulness instead. I spent a long time in my 20’s being reactive, impatient at work, and juggling racing thoughts. Over the last half decade or so, I have worked to understand those tendencies a bit and work in a calmer way.

Last fall, I signed up for a weekend meditation retreat. I thought I was ready. I had a clean diet, good exercise, a strong journaling habit, and slept like a rock in the weeks leading up to it. I ended up starting at the wall & ceiling of a cottage in the woods for six straight hours each day over a weekend. The entire first day my mind raced with judgements: This is such a fucking waste of time. I was so stupid to come here. Everyone is bugging the shit out of me. I am bugging the shit out of myself. I’m not going to get anything out of this.

How’s that for an unglamorous start?

I came apart almost immediately! But I sat with that voice so long, I got curious about it. The damn thing just wouldn’t shut up! I finally thought to ask that voice, “Who are you and what do you want?” and guess what — it went silent immediately! It didn’t want to be examined. Now that was an interesting development.

The next day I learned to be curious about that voice, and I realized how often I let it lead in my life. I worked with that idea at home over the months afterward and, just this last weekend, returned for another retreat ready to go deeper. I was able to uncover many interesting things and learned that voice wasn’t an enemy, it was actually trying to protect me.

I feel like I am starting to get somewhere with the work, which is nice. But it required getting curious about the difficulties. Instead of pushing them away, sometimes we need to hold them close. Examine them and try to see what they’re made of. This can be everything from why you cannot find a cofounder, to why the product doesn’t get traction, to why thinking about work makes you tired all the time. Don’t reject it. Look at it. Remember that we make the work, but the work also makes us.⁶

It took me a long time, both in the sense of that meditation weekend and in the sense of my entire life, and it might not have happened if I hadn’t spent two days literally staring at a wall, seemingly getting nowhere.

Don’t Be So Self Conscious

When my 7-year-old pulls a book off the bookshelf that’s too advanced for her, I don’t tell her to put it down. When my 2-year-old mispronounces a word, I don’t roll my eyes at him. They don’t mind messing up, or potentially looking silly. Crucially, we make a home where they are encouraged to experiment and push their limits.

I’m not sure she’s going to get through that Emerson anthology yet, but that’s up to her. And this was before we organized the shelves, so take it easy on me regarding layout & aesthetics :-)

How can you create the same environment for yourself (and your team)? Try asking “dumb” questions. See if you can write out your entire idea without skipping any steps or leaving any fuzzy white space. If a potential client, collaborator, or competitor says something you don’t understand, ask them about it (especially if you feel like you should already know it). Some of the best engineers and managers I’ve ever worked with did this all the time. And the majority of the time one of two funny things would happen:

1. A few other people would admit they had the same question.

2. The person who brought it up admits they don’t know either!

Sometimes, it was both.

Toolkits to Fight Distress

I am working on some toolkits to help get hardware entrepreneurs through the Valley of Death, that place between inspiration striking and securing that first customer or critical investor.

If you’d like to learn more, leave a comment or drop me a line! I have teamed up with some old friends who have developed everything from rockets, to nuclear reactors, to medical devices (and about a million other things in-between). We’re cooking up some cool stuff and I’d love to share it with you when it’s ready!

1. This Substack was born partially from my desire to break that feeling, knowing that I’d struggle onward for quite some time.

2. It’s especially especially true for space tech entrepreneurs, but that’s a whole ‘nother story. They always need a billion dollars to build some objet mystérieux with no real market and no real team. Nine times out of ten it’s just some weird ego trip that could be solved with deep therapy.

3. I used to love the scenes from early missions in Batman Begins when he bumbled around in a ski mask. Of course, now that Batman has been reinvented so many times, the shine has worn off a bit.

4. Hemmed and hawed over whether I should make “something” a proper noun.

5. These will be part of the toolkits I put together. Lmk if you want to see early versions!

6. This is the subject of a near-future post about the way in which we make ourselves.