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Hey Reader,

In 2018, I stood in front of the City of Phoenix Department of Transportation and told a room full of government employees they needed to fail more.

Lol. I know.

When I tell you the room went quiet...all of their faces said: This is startup thinking. This doesn't apply to us.

And that's exactly why I was there: to teach these well-established leaders how to think like entrepreneurs.

The 20% Nobody Talks About

That hesitation isn't unique to government, by the way.

It lives inside every established organization: corporate, nonprofit, family business, doesn't matter. The bigger the institution, the more failure gets treated as damage instead of data, and while reputation management is important, I'd hardly argue that avoid embarrassment is a growth strategy.

Steven Bartlett (Diary of a CEO creator) says,

But I find the real constraint isn't competence. It's actually (unsurprisingly) fear.

So here's how you fix it:

1. Map Where You Can Afford to Fail

Every organization has shock absorbers: cash reserves, brand equity, loyal customers, a strong core product. The question isn’t “Can we afford to fail?”

It’s “Where can we afford to fail?”

Find those places. That's where you take intelligent risk.

2. Make More (and Smaller) Bets

I argue for this all the time: high-impact, low-effort experiments are your highest-leverage move––and most leaders overlook them. They try to take big swings.

Sigh.

Instead, how about we aim to make reversible bets: the downside is capped and the upside is unlimited.

3. Build a Tight Feedback Loop

After every experiment, ask three questions:

• What worked?
• What didn’t?
• What changes next time?

That’s it. Don't make your team do a presentation on what didn't work, Ramon. And no blame disguised as analysis, either.

Keep it sharp, honest, and fast.

4. Make Attempts a Regular Thing

When experimentation is rare, every attempt feels existential. Careers feel like they're at stake––a fear that is (understandably) paralyzing.

But when experimentation is routine, it stops being dramatic and becomes operational. It becomes the way we do things.

If you publicly reward thoughtful attempts (even the disappointing ones), you make trying normal.

That's a very good thing.

Just know, the organizations winning right now aren't the ones with the best strategy. They're the ones who ran the most experiments last quarter. And Bartlett's 20% isn't a magic number, it's a mindset: normalize attempts.

Start there.

Proud Partner of Squarespace​ ​ Simply the best for starting up, prototyping an idea, or building a platform. Try it for free

BEHIND THE BUSINESS

One Recording. Lots of Runway.

Last year at a conference in Boise, I booked time in one of Kit's beautiful studios (free for their users btw!) and recorded one long-form video.

Welp, I finally chopped it up.

One long-form recording gives you content for months which you can parse, measure, and reuse across every platform that matters. Those clips live on sales pages, social assets, and anywhere else your audience needs to meet you.

And for the record, this isn't a volume game. It doesn't matter if 20,000 people see your video.

It's an alignment game. Did it reach who you wanted it to reach?

High leverage. One recording. Lots of runway.

Mine are slowly rolling out on YouTube and across my website. Take a peek.

COFFEE THOUGHT Working with people you love is such a life hack.

DAILY QUOTE "Failure is feedback, feedback is knowledge, and knowledge is power." –– Steven Bartlett (and Francis Bacon)

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Big love,

tanya moushi ("moo-shee") Sign up at moushi.co​

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