"Fake it till you make it" has always made me feel weird.

I coach founders on fundraising, and so much of what I teach sounds like performance. How to send the right signals to investors. How to manipulate investor psychology so they feel compelled to chase you. How to look like an awesome deal.

It can feel superficial. Like you're cosplaying as a great founder instead of being one.

But I've been thinking about this differently lately. You know the old saying, "If it walks like a duck and quacks like a duck, it's a duck"? Turns out there's a reason the duck walks and quacks that way. It's not just for show.

I suck at surfing, I'm okay at singing, and I'm a pretty decent golfer. And across all three, I've learned the same lesson: the style you're mimicking was driven by substance in the first place. When you act like a duck, you become a duck.

Let me explain.

I grew up skateboarding and snowboarding. I'm pretty good at both. So when I started surfing as an adult, I figured it would translate.

It hasn't.

When I see photos of myself surfing, I look absolutely ridiculous. I'm hunched over, legs awkward, face twisted like I'm about to drive off a cliff. On a tiny wave. I look 1000% like a kook.

I look like I suck because I suck.

This past week I had the chance to go to Ubatuba, Brazil to surf and got coached by Dani, a pretty amazing instructor. Early on she coached me much like I coach founders.

She told me I looked uncomfortable out there.

So we started focusing on looking cooler. More comfortable. More relaxed. More like the pros.

"Relax! Stand up straight!" She kept shrugging her shoulders, trying to get me to let my arms dangle with good posture instead of death-gripping the board like it owed me money.

It felt kinda superficial to focus on how I looked. Felt fake to mimic surfers who were light years ahead of me. But I was all into it, especially if it would produce pics that looked less goofy.

Then a funny thing happened.

I focused on looking a certain way, and weirdly it led to me feeling more stable. It allowed me to turn on waves better. And shockingly, I started crossstepping (longboarders know).

I was shocked that it worked. Then so happy. Then a lot of things connected in my head.

Ohhhhhhh. I can see why I can do this now. It's not just posture to look cool.

The pros don't stand that way to look effortless. They stand that way because it works.

Last year I started investing in some things just for enjoyment, including voice lessons with my instructor Jodie. No real reason. Just wanted to sing with a coach for the first time since being in a children's choir 30+ years ago.

We've been working through "The King of Wishful Thinking" by Go West and "Daisies" by Justin Bieber. Songs with notes at the end of my range.

At one point, Jodie starts getting me to do things you normally see pop stars do. Sing with a pained smile (corners of mouth upturned). Do a little dramatic dip in your knees before you hit that high note.

It felt silly. Like theater kid energy cranked to 11.

Until those moves helped me open up my vocal chords and relax my throat to actually hit the notes.

Turns out the reason Kpop Demon Hunters will dramatically dip before ripping that high A isn't because they're being extra. It's because it actually has a functional impact on performance.

They don't do it to look cool.

They do it to perform.

You just think it looks cool.

I started taking golf lessons right after I watched Tiger Woods win his last US Amateur. Played on my high school team and got pretty decent at it.

My golf coaches would tell me to pose for a camera at the end of a swing. Some even encouraged the Tiger Woods club twirl.

Was it so that I could look like Tiger while playing? Kinda!

But it turns out, in order to finish your swing so that you can pose for a great photo, a ton of functional things have to happen. You have to have great balance. Swing with tempo. Finish with good rotation.

The twirl is just icing on the cake. ;)

The pose wasn't about style. It was a forcing function for all the mechanics that make a good swing actually work.

I learned this lesson with golf years ago. But somehow I needed surfing and singing to beat it into my head all over again.

When you look like a great golfer at the end of your swing, you probably just executed a great swing. The duck walked and quacked, so it is a duck.

This whole realization made me think differently about the advice I give founders.

The encouragement to be brief in your emails to VCs. To have a financial model outlined for your business no matter what stage you're at. To be able to succinctly describe your business on the fly. To tell compelling stories about the market you're going after. To sound passionate about the industry you're in.

This is so you sound a certain way. You sound like a great founder.

But what you're doing to sound like a great founder is actually doing things that are driven by function in amazing founders when they do it naturally.

The brevity in emails? It's not a trick. It's because investors are secondary to the actual work, and great founders have other important things to do.

The financial model? Great businesses are run by the numbers, so seeing you have a model means you're likely trying to run your business by the numbers.

Succinctly describing the business? It's not rehearsed polish. It's because they have zero doubts about why the company exists, so they don't waste words.

They're great at telling stories because they have to inspire and convince the best talent to join them and customers to trust them.

They sound passionate because there's nothing else they'd want to be spending their time doing.

When I coach a founder to "act" that way, it can feel performative. But the performance has a purpose beyond looking good.

If you walk like a great founder and talk like a great founder, you're probably doing the things that make you a great founder.

I worked with a founder recently whose background at Twitch and Instagram put her in rarified air. She had an incredible understanding of tastemakers, trends, and the technical underpinnings of going viral.

But when it came time to pitch, she downplayed all of it.

I kept pushing her: You have to believe you're the best. You have to own that expertise.

It felt awkward for her. It felt like it wasn't real.

But here's the thing. She was objectively one of the best people in the world to be working on this problem. The "performance" I was asking for wasn't fake. It was just uncomfortable because she wasn't used to saying it out loud.

Once she started acting like the expert she actually was, everything clicked. Her pitches got sharper. Investors leaned in. And more importantly, she started making decisions faster because she trusted her own judgment.

The performance became the reality. Or maybe it always was the reality, and she just needed permission to show it.

If something in fundraising (or life) feels performative to you, don't write it off as fake.

Instead, take that piece of advice and try to break it down. Figure out what you need to do to fully embrace it as a natural action.

Ask yourself: Why do the best people do this? What function does it serve beyond appearances?

When you find the answer, you'll probably discover you're a better founder for it.

Sometimes the idea of faking it until you make it has made me feel weird. But now I look to understand WHY the things that feel superficial to me have function. And then it becomes a shortcut to learning new skills and improving my approach to things.

Stand up straight on the surfboard not because it looks cool, but because it gives you balance.

Smile through the high note not because it's dramatic, but because it opens your throat.

Pose at the end of your golf swing not to look like Tiger, but because it forces good balance, tempo, and rotation.

Be brief in emails not because it's a power move, but because you have more important work to do.

Act like a duck. Become a duck.

Be chased,
Jason

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