Howdy from Durham,

Welcome to the 10 new subscribers from last week.

Today, we’re relating a 2008 waveboard experience with my 2023 experience of starting a company.

When I was 11 years old, my sister and I got waveboards.

Surely, you remember the must-have Christmas gift from 2008. They were 1/2 skateboard and 1/2 something out of an 80’s workout commercial.

My sister Jacquie’s was pink. Mine was blue. We were so obsessed with them that we begged our dad to let us bring them on a family trip down to North Carolina. That way, we could show our aunts and uncle our newly acquired skills.

There was just one issue with us bringing them to NC: I hadn’t yet figured out how to waveboard.

My sister, on the other hand, feared no terrain. Choppy asphalt and the occasional patch of dirt were no match for her.

Jacquie was especially a sight to see in North Carolina because my aunt Sherry’s driveway wasn’t just any driveway. It was a clean, smooth concrete. The wheels glided across the surface with ease.

Even though the concrete was pristine, Sherry’s driveway presented a bit of a challenge. The driveway turned into a dog leg left sidewalk that brought visitors to the front door.

Only a madman (or in this case, madwoman) would take such a treacherous route, such as my sister.

She was unfazed by the cracks in the sidewalk and ripped that waveboard into the deep-end of the hard, 90-degree turn towards the front door.

Me? I was still in the shallow end of the smooth, concrete driveway trying to figure out how the heck you generated momentum on the thing.

Suddenly, there was a breakthrough while I was outside by myself. For just a moment, I saw my reflection in the glass of the front door as I did a sort-of hula hoop motion to keep my board up.

“That can’t be the way to do it,” I thought. It looked whacky. At that time, being only 11 years old, I thought that whacky was surely bad. I pushed what had given me success to the side.

Another day passed, and I still struggled to generate momentum on my waveboard. My sister joined me in the driveway. Out of frustration, I did the whacky hula hoop motion once more.

“You’ve got it!” yelled my sister.

I was confused. No, that couldn’t be the way to do it. It simply looked and felt too weird. “Are you sure?” I asked my sister.

“Yes. Do it again,” she replied.

Suddenly, I was off and running (or waveboarding). From then on, no street between North Carolina and the great state of Pennsylvania was safe. We ripped those waveboards until the wheels fell off.

In 2023, I’m trying a lot of new things for the first time as a first-time founder. I’m learning about legal structures, accounting systems, product strategy, marketing, and more.

There are times that I’m doing the right thing for the startup (but it feels whacky), so I stop doing it.

Startups are more complicated than waveboards, and there isn’t an exact science to generating momentum.

Regardless, I need to rid of what I think the “right form” looks like and talk to someone who has done it before. Even if the more experienced person can’t provide an exact, tactical plan then they can at least help me build the confidence to keep going.

How funny is it that we long to push new boundaries but fear that we might look whacky if we do?

Better yet, how funny is it that we have trouble asking the person with more experience than us for help?

We seek to become exceptional but fear how others will view us if we stand out as an exception.

By definition, these two things are always at odds.

The bottom line: you don’t know what right/wrong looks like when you’re just starting out, so be sure to ask folks with experience for help.

Last thing: if the waveboard stays up, and folks who know how to waveboard say that you’re doing great, then lean into it and rip away.

What I’m paying attention to:

The most heartwarming thing that I read this week. Click to read more from Luke Burgis

Michelle Varghoose reminding us that step 1 is to get on the waveboard. Per my piece above, step 2 is to ask for help once you get started

Photo of the week:

Thanks for reading

Reply if you miss waveboards,

Josh

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