Hey Fearless Friend!

Today on Stay Fearless or Die Trying:

1. If you’re from the Connecticut group, welcomeee!!! By staying subscribed to my weekly newsletter, I’m able to continue to give back to so many of you in Connecticut, host these events, and grow this fearless community!

2. I have been using Grammarly for years now and want you to sound much better perfectly professional. Get 20% off Grammarly Pro here!

3. I need a favor! I’ve been working so hard to grow the Chief Swag Officer Instagram and would love for you to follow us here!

4. The Connecticut Hat Collection has launched: made and produced in Connecticut! Shop the small business here!

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What’s the deal with starting a business?

Thank god I went up to Scott Galloway at that party I wasn’t invited to!

I spoke at the University of Texas a few weeks ago and someone asked me how I maintain my authenticity in my career and online.

Before I started Chief Swag Officer I tracked the market of customized products for 12+ months. We’ve penetrated that market because I knew what the other brands were doing wrong: they were selling. And they weren’t selling in a sexy way.

Last month I went up to 10+ different people who are the biggest game players in media over 2 parties. I was able to do it and not be afraid of the rejection (or getting kicked out) because the minute I walked into that party I knew why I was there and who I needed to meet.

The competition is always me. How good, strong and/or fearless do I need to be to make this happen? I don’t care about what these other creators are doing because I’m not competing against them.

Every month, I fly between Connecticut and London to take girls out to dinner who follow me on TikTok.

Why would I not want to hang out with the people who pay my bills?

They may not pay me directly but their engagement does.

This is where content creators fail: and why thousands start every day and don’t do it the next day.

They’re selling: not leading.

I spend $150+ a month sending people gift cards or items who follow me online.

I posted a video of a gift card I left at the front desk of a hotel in Manchester, Connecticut for a free dinner and told someone to get it. 50 people showed up.

I posted a video of a Jersey Mike’s review (3 videos over 3 days) & people knew I was eating gluten-free bread.

People are smart. They honestly may know me more than I know me.

Being authentic is authentic to me because I’m not selling you: I’m leading you on this journey with me. The highs, the lows, the Etsy situations of the world, the minutes I think about giving up and getting a “real job”.

When corporate clients buy from Chief Swag Officer (90% of our customers are larger corporate clients) I know they want fast customer service, no errors, and connection.

How do I know this? Because I’m one of them. I’m the first person at a dinner table to say my food is cold and send it back. Hate me or love me, it’s just me.

I know what the girls who follow me want because I am one of them.

When I started my blog when I was 12-years-old, I wanted to escape my tiny town and do something with my life. I created that person for the next generation because I didn’t have it.

When you think about what you want to do, or the possibility of being rejected, someone is already out there sending that email, getting into that party, or taking out a credit card to make their company come to life - they may have the same idea you’ve been sitting on.

Business is a game: it comes down to how much you want success.

Everything you do must have a mission behind it or you’ll fail.

Just tell me the answer.

Well entrepreneurship isn’t nearly as fun if I’m telling you the answers, is it!?

I’m going to tell you what you can do BEFORE you establish an LLC. People jump right to all of the logistics of starting and building a business before they even realize how much needs to occur prior, predominantly proof of concept.

✅ What you can do without an LLC:

You can start a business as a sole proprietorship (if it's just you) or a partnership (if there are multiple people). This means you just start operating — selling, freelancing, consulting, etc. You might still need:

• A business license (depending on your location/type of work)

• A DBA ("Doing Business As") if you're not using your legal name

• To report your business income on your personal tax return

✅ Why people get an LLC:

• Liability protection — your personal assets (house, car, savings) are protected if your business gets sued or goes into debt

• More credibility — some clients/partners may prefer working with an official business entity

• Easier to scale — good for opening a business bank account, hiring people, etc.

🧠 TL;DR:

You can start without one, but forming an LLC adds protection and professionalism. If you're doing something low-risk and just testing the waters (like freelance writing or tutoring), starting as a sole prop is totally fine. If you're launching something bigger or with more risk (like a product business, hiring employees, or signing contracts), an LLC is worth looking into early.

Want help figuring out what's best for your specific business idea?

I have room to take on 2-3 more coaching clients this quarter. What does that entail?

I love working with aspiring or current founders who are struggling with tasks like how to start a podcast, how to find their niche, or how to find product market fit.

Reply to this email to get a one-on-one call with me to go over your ideas.

P.S. if you share this newsletter with someone, you get free stuff!

Stay fearless or die trying,

Alexa