ISSUE #36

Welcome to the Forward Obsessed Founder, my newsletter with insights, awesome tools, and real-world advice to grow your business and career.

GO FORWARD THOUGHT OF THE WEEK ➡️

The #1 Mistake NOT to Make as a Founder

Today’s newsletter is some raw, unvarnished, painful AF truth. It’s my lesson learned, and I’m sharing it with you.

Your first job as founder is don't run out of money.

Your second job is to have a clear and inspiring vision.

Your third job is to set the culture.

And guess what?

I failed at all three.

Last week, I had to lay off a bunch of amazing people from one of my companies.

I wasn't building a pipeline.

I wasn't pushing my people hard enough to generate revenue, nor did I hold them accountable when they didn't.

I could have blamed the market.

I could have blamed AI.

I could have blamed my team.

But the buck stops with me.

So, let's be real here: You gotta spin the flywheel.

Sounds easy, but it’s not. As a massive fan of Jim Collins’ Flywheel Model from his book Good to Great, I am reminded of how he describes it:

Then, a breakthrough! As founders, we’ve all had it—that point where the thing goes on its own. Every turn of the flywheel builds upon your earlier work, compounding your effort into what feels like an unstoppable force.

Welcome to the Doom Loop

But then, we get distracted.

We stop doing the basic thing — figuring out what needs to be done and doing it — and start chasing other shiny objects.

We skip the build-up phase and think we’ll be able to coast on the momentum we once built.

Doesn’t work like that.

I can see where I fell into what Collins calls a “doom loop.”

I let the vision lose the clarity of a mission.

And I expected the operators I had hired and appointed to be visionaries, but they weren't.

When you expect a fish to climb a tree, you fail.

I used to be embarrassed that I didn't start a tech SaaS company.

I had a big chip on my shoulder.

I didn't have an MBA — I was the first person in my family to go to college or start a business.

Maybe this is part of why I lost my way. As luck had it, months ago, when things were in a much different place, I signed up for a two-day business retreat for high-growth founders and CEOs. Turns out the event was this week, and the timing was perfect.

$36 billion dollars.

That was the combined exit value that the people at this retreat had created.

There, I met some of the world's leading founders — people who have built and sold their businesses for hundreds of millions and some of whom have worked with the Zucks and Musks of the world (literally).

Guess what we all had in common?

No, it wasn't our net worth. I was a molehill compared to their mountain of success.

The #1 thing we all shared was we were afraid that people would think we weren't enough.

This is a depressing, debilitating thought. And it got to me: recently, I found myself steeped in sameness, exhaustion, and burnout.

In pursuit of more, I found myself taking my eye off what I loved most. I let other people and the TikTokification of the world get into my head.

I thought I wanted different.

What I really wanted was better.

Better outcomes start with better questions.

The Question Is…

How do you ask for what you want?

I hate making asks.

But I know what I love: I love helping brands become better versions of themselves.

So here's my ask (for you and now, for anyone I meet 😉):

If you can, that would be helpful.

Because I hate asking for help, but not nearly as much as I hate laying off people.

This is perhaps one of the biggest bumps in the road we founders have to weather. And when we do, just remember: lean into your flywheel.

Always here to help 🙌
​
​Pete Sena​

Podcast 🎙️: Bouncing Back from the Brink

You know what the best part of doing a podcast with forward obsessed entrepreneurs is? Hearing not only about their insane successes but also their greatest failures — a great reminder that those crushing moments are part of the deal.

That’s why I loved speaking to Jess Lynch, exited co-founder and CEO of Wishroute, a tech company she built from scratch. Most people would want to hear about her triumphant exit in 2022, but I loved what she said about her lowest point, which happened after countless attempts to gain traction during the pandemic:

Been there, and you probably have, too. It's well worth listening to this interview to find out how she got her flywheel cranking again. (Hint: It’s not just your IQ; it’s your EQ, too.)

Listen: ​Life Begins At The End Of Your Comfort Zone With Jess Lynch​

CREATIVE CAFFEINE ☕️🍵

​Jerry Seinfeld Talking to Tim Ferriss About Black Stallions (and Other Systems, Routines, and Methods for Success)

During a conversation with a new friend at the retreat, I mentioned that meditation saved my life by helping me grasp and hold onto my superpower. (Here’s the story.) My friend replied that it sounded like that meditation was actually what helped me learn how to ride my “Black Stallion.” Then he turned me onto Tim Ferriss’ convo with Jerry Seinfeld, which includes sage advice on how to spot your genius — comedic, engineering, caring, whatever — and harness that "Black Stallion" to ride it to its fullest.

​How to Find Your Leadership Superpower​

As long as you’re thinking about your Black Stallion, maybe you’re not even sure how to find that beast. I assure you, it’s in there… and to discover it, I can’t recommend this exercise by the incredible Angela Parker enough. I’d love to hear what you come up with — hit reply and let me know.

MY OBSESSION OF THE WEEK 🖤

The Power of Disconnection to Reconnect

Some people think going to a business retreat is about the programming or the networking. That’s how we rationalize it, anyway. But looking at it that way is seeing it as just another way we’re caught up in the swirl of life.

But it’s not. A retreat is specifically about disconnecting, even for a day. The change of scenery and focus creates enough space to see the problem differently. Sometimes, the way that we can start to think about the problem differently is by not dwelling on the issue itself but rather on the things that surround it.

Bottom line: As Charles Eames once said, “Eventually everything connects” — but if you don’t prioritize making room to step back and gain a new perspective, you can spend a lifetime passively waiting for breakthrough connections to line up.

If you think you can’t afford to go on a retreat like I did, I’d counter this: you can’t afford not to.

Thanks so much for reading this edition of The Forward Obsessed Founder — you can also check out this issue on the web [Link].
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