ISSUE #43

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 ➡️

Sam Parr’s 8 Secrets to Hustling Your Way to $100 Million 💰

GO FORWARD THOUGHT OF THE WEEK ➡️

The best part about hosting a podcast about Forward Obsessed entrepreneurs is that you get to ask them probing questions about their experience going from idea to exit — the pain and the pivots, the wins and the WTF moments.

I recently got to sit down with one of my favorite founders, Sam Parr. He founded The Hustle, the popular media/newsletter company, and sold it to HubSpot for north of $20 million. He's also the co-host of the My First Million Podcast and co-founder of Hampton, a private, invite-only network for founders, entrepreneurs, and CEOs I'm proud to be a part of.

In today's newsletter, I’m giving you eight solid takeaways, but I strongly recommend you listen to the whole episode. The guy’s a master class in the grit, resilience, vision, and, yeah, hustle it takes to kill it and make not just your first million but your first $100M.

1. Branding is everything.

It blew my mind that Sam, as smart and successful as he is, had to learn this lesson the hard way:

Not just a pain in the ass — for most, a torpedo that sinks your business if you don’t get it right out the gates.

2. Hire divergent thinkers, lean into obsession.

Sam said this bluntly, but it's spot on:

He does this by being divergent in his approach to hiring: he scans the bottom of the resume for hobbies. He asks the questions others don't. He wants people who are passionate and unique. His team at The Hustle was encouraged to let their freak flags fly.

Want examples? Check out Trung Phan’s newsletter and Steph Smith, who Sam discovered by reading a blog post she wrote, "How to Be Great? Just Be Good, Repeatedly.” (Holds up — great content.)

3. Don’t undervalue your product.

I love learning from others’ mistakes, which for Sam was the brilliant spin-off newsletter Trends. He only charged $300 annually, figuring the product was for his existing audience of entrepreneurs at The Hustle. Later, he realized he could’ve charged companies $30,000 annually, which was “a massive mistake.”

Meanwhile, Trends quickly became a $5 million ARR business, so it wasn’t the worst screw-up.

4. Shoot your shot: cold calls & emails open doors.

Sam’s superpower is being immune to rejection. He didn’t come that way; he taught himself to be a relentless cold caller by opening up a phone book, calling random numbers, and convincing the person on the other end of the line to recommend a movie for him to watch that night.

That little trick empowered him to cold call Airbnb not long after it launched with unsolicited advice, which landed him a job offer. (He got fired before his first day — listen to the episode to learn why — no spoilers here 😏.) But to this day, Sam makes cold calls and sends cold emails, continuously honing his pitch and simultaneously keeping his skin thick.

5. Be relentless when hiring a CEO.

If you’re lucky, you’ll need to hire a CEO at some point. Sam’s approach is genius.

Then, ask yourself if that’s a weakness you can live with. If not, and you still go forward, that decision will haunt you.

6. Focus on building one great product before expanding.

I believe focus is so critical that I created a framework for it.

Sam agrees that shiny object syndrome is the biggest growth killer for startup founders. Here’s how he avoids that trap, even as it seems like he’s everywhere all the time:

7. Envision everything.

Scaling isn’t something you do once you’re successful; it’s a guiding light in your brain that takes you there. Here’s Sam’s thinking on that note:

8. Surround yourself with the best to be your best.

This is an unsolicited plug for Hampton — I’ve gotten more insight into how successful entrepreneurs think and act in the last few months as part of this organization than I’ve learned in more than two decades in business. This has always been Sam’s MO, too:

There’s so much more gold in the interview with Sam (watch the full episode here), but that gives you a taste. I’m curious about your top takeaways or what I missed from mine, so hit reply and let me know.

Always here to help 🙌
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​Pete Sena​

CREATIVE CAFFEINE ☕️🍵

​ConvertKit is Becoming Kit​

Rebranding in public is a bold move, but after 11 years in business, it’s also a smart move. ConvertKit is inviting its community to join in its “design in public” approach, which reflects its core values:

(Notice this announcement is a lead page for newsletter sign-ups — very meta!)

​Sam’s List​

Speaking of building in public, it’s fun to watch how serial entrepreneurs launch new projects — Sam discussed this one in our conversation. (Plus, entrepreneurs like us can always use a kick-ass CPA.)

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MY OBSESSION OF THE WEEK 🖤:

The Blue Angels Documentary

From the time I was a kid, I remember going to air shows. My grandfather fought in the Korean War, and I learned so much from him — I wanted to have that same grit and determination he had.

But why is it the obsession this week? Dedication. Striving for perfection. This new documentary is like watching legit Top Gun without the fiction. And it got me thinking of the sacrifices we make to pursue our dreams.

The origin of the Blue Angels is pretty awesome — it's a testament to the power of thought leadership and branding. The program was designed so the American people didn't forget about the Navy's planes. If you've ever seen a Blue Angels show, you'll never forget about America’s planes.

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Bottom line: The Blue Angels exhibition team, created in 1946, is ultimately the story of staying the course, keeping going, and standing the test of time — flying above the fray and weathering the storms of incredible risks, hardships, and losses.

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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