I've Been W-2 Free for 25 Years. Here's What I've Learned.

WE'RE GONNA FIND OUT

Real-world experiments in business, side gigs, and a life beyond the W-2.

Welcome to the first issue of We're Gonna Find Out.

I've been self-employed for roughly 25 years. I've built businesses in plastic resin distribution, consumer reselling, and media communities built around Facebook groups. Different businesses, same lesson: you don't have to know everything before you start.

This newsletter isn't about promising you can quit your job in 90 days. It's about sharing what I've tried, what worked, what didn't, and what I'm testing next.

A side gig doesn't need to replace your salary on day one. Start with a small experiment: one customer, one sale, or one community worth building. The goal is to find out whether people value what you're offering enough to pay for it.

One of my Facebook groups started simply because my family had useful information to share. Years later, community building became part of a media business. You never know what a useful first step might grow into.

Here's a business you can test without inventory or a storefront: build a local networking group for people who genuinely benefit from meeting one another. Think independent business owners, tradespeople, sales professionals, or entrepreneurs in a specific industry.

Illustrative example: 30 members at $25 per month would generate $750 in monthly gross revenue. If expenses were $250, you'd have $500 left before taxes and compensation for your time. Those are sample figures, not a prediction. Real costs, retention, and attendance will determine whether the idea works.

Find initial members through LinkedIn, local business groups, chamber events, and referrals. The biggest challenge is retention: people won't keep paying to attend another sales pitch. You need to help them make meaningful connections.

Your first experiment: Ask 10 people whether they'd attend a networking meetup designed for their industry. Their answers are worth more than weeks spent designing a logo.

In 2012, after our family's first Disney World trip, I started the Disney Food Allergy Group. Our son has serious food allergies, and I wanted to share what we'd learned about eating safely at Disney. Making money wasn't the goal. Helping other families was.

Over time, I learned that a focused, engaged community can be valuable to businesses that serve the same audience. Rather than filling the group with random advertising, I looked for relevant sponsors who could benefit from a long-term relationship.

One sponsor began paying $300 per month. As the community grew and the relationship developed, that increased to $3,350 per month. At that monthly rate, that's $40,200 in annualized gross sponsorship revenue from one sponsor—not net profit and not a typical result for every Facebook group.

I send an invoice each month and receive an e-check. It's recurring income built on years of work, not a one-time viral post.

My approach comes down to four things: build a community around a real need, keep members engaged, choose sponsors that fit, and protect the trust that made the group valuable in the first place. Our communities have also helped us build newsletters and other media channels.

In future issues, I'll get into the specifics of finding sponsors, pricing packages, and what I offer businesses in exchange for their monthly payment.

One of my three businesses is 5 City Liquidation. We buy closeout and liquidation merchandise and resell it, including through Facebook Marketplace. The sourcing is one challenge. The day-to-day work of getting products listed is another.

Every item needs attention: figuring out exactly what it is, researching a sensible selling price, writing a description, organizing photos, and keeping track of what's available. When you're handling a lot of different products, those repetitive tasks add up.

That's why I've started exploring MUSE as a way to handle more of the Marketplace listing workflow. My goal is to move from doing every listing task manually to a more repeatable process where I can provide product details and photos, have AI help research and prepare the listing, and review the result before it goes live.

I'm not going to pretend the entire process is perfected or that every part of Facebook Marketplace can be automated without limitations. Platform rules, listing accuracy, buyer messages, and actual inventory availability still matter.

But this is exactly the kind of experiment I want to document here. If I can reduce the time it takes to turn liquidation inventory into quality listings, that could make a meaningful difference in the economics of the business.

I'll share what MUSE actually handles, where I still need to step in, and whether the time savings justify the effort. No hype—just the results as I learn them.

You work hard to get people to reach out. CallBack Engine helps home-service businesses get more from those inquiries through managed follow-up on missed calls and web leads. Give good-fit customers a clear next step while your team stays focused on the work.

Each issue, I want to ask a practical question: What would it cost to try this? How would I find the first customer? And how would I know whether to keep going?

Hit reply and tell me: What's one repetitive task in your work or side gig that you'd love to stop doing manually?

— Larry