How I Got Chief Swag Officer Into Stores

Hey {{First Name|Fearless Friend}}!

Today on Stay Fearless or Die Trying:

How has the start of your new year been?

I genuinely love when you reply to these emails and tell me what you’re up to — especially when you share about the business you’re building. It inspires me more than you probably realize. There’s something really powerful about hearing from people who are in it, figuring things out in real time.

Because let’s be honest… business can be scary. And running a business can feel extremely lonely.

I can’t tell you how many times I’ve caught myself feeling so alone in this process — even when I’m surrounded by people. It always surprises me. I think it’s that weird in-between feeling of not knowing who really gets it. Who understands the pressure, the risk, the self-doubt, the excitement — all of it.

The past few weeks (honestly, month?) of my life have been a little wild. I moved back to LA — where I lived for years when I had my Radio Disney show — and I’m actually back in the same apartment building I lived in during my Disney days. Full circle moment.

I’m from Connecticut, so the West Coast still feels… slow and slightly strange to me. It’s not nearly as chaotic as people make it out to be. It’s very normal. But coming back to this apartment, this city, this version of my life after being somewhere else for the past few years has definitely been an adjustment.

One thing that keeps me grounded? My mornings. They’re honestly my favorite part of my day.

Here’s what they’ve been looking like lately:

There’s something about having that quiet time before the world starts asking things of you. It makes the chaos feel manageable.

Anyway — I’d really love to hear how your year is starting. What are you building? What feels exciting? What feels hard?

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Bringing Dare to be Fearless (my podcast) back for a special episode about The Love List and how the company has been going!

And I’ve never been so excited. On March 3rd, 2026, Chief Swag Officer launches in one of the largest audio retailers out there. How’d I get their attention?

A cold pitch, of course (listen to how to cold pitch here).

I love a good cold pitch. If you’ve followed me since day 1, much of my story revolves around getting myself in front of the right people. I landed my Radio Disney show via a cold pitch to a Disney executive. It wasn’t just one email either. I followed up relentlessly for months. If you plan to land your dream job or mentor with one LinkedIn message or email, you’re nuts. The power is in the follow-up.

Last year, I listened to a podcast episode with the CEO of Sweetwater, Mike Clem. I really admired his story and vision of the brand and I became dedicated to getting CSO product in their stores. After months of emailing and a few phone calls with the CEO pitching my idea, he ultimately rejected the idea because he said we’re too small for their store. I get it, we are. Sweetwater is a billion-dollar company and we are not.

In my mind, getting attention from Mike was enough for me to continue to reach out to similar companies and try and seal the deal. I started researching who the biggest audio retailers in the space were, from Guitar Center to B&H, and landed on a few retailers that are in the same category.

I sent out a similar cold pitch, and heard back from someone. During our initial call, I was semi-rejected. It wasn’t a strong lead, and the guy I spoke to was on the sales team. He mentioned he’d run Chief Swag Officer by his CEO but it probably wasn’t a fit.

The next day, I got an email from him asking if I was nearby Anaheim, CA to meet the CEO and their team that next day at a large audio conference. I rented a car, picked up all the product I had accessible to me, and sold them harder than I’ve ever sold someone.

More to come…but we’ll be live on their shelves March 3rd, 2026!

Stay fearless or die trying,
-Alexa

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