Joe Meares has 130 rental units. If he were starting over, he’d slow down.

That got my attention.

Joe is a New York City real estate investor and former Wall Street analyst who bought his first rental in Indiana for $50,000 in 2018. We get into that first deal, the team that made long-distance investing possible, and how buying more properties can turn into a whole new job.

I also asked him about the part that tends to get skipped: what his finances actually looked like when he left banking. We talk about savings, uneven rental income, and why a growing portfolio doesn’t automatically mean you’re ready to replace a paycheck.

Joe was generous with the numbers, the lessons, and what he’d change. If you’re curious about real estate, this is a useful look at the work behind the property count.

What you’ll take away:

• Why Joe would prioritize cash flow per rental over the number of units he owns.
• The four local team members (aka "Core Four") he relies on to invest from another state.
• Why he separates long-term property wealth from the income needed to cover life today.
• Where he tells beginners to start: their own finances, upcoming expenses, and goals.

🔗 Links mentioned:

• Joe’s LinkedIn

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She got a grocery retailer to say yes before she had retail packaging ready. Then she and her family figured it out. Brittney Cook is the co-founder and CEO of Something Sweet, a frozen cookie dough company that had grown to more than 600 stores when we recorded this conversation. It started with her mom’s brown butter chocolate chip recipe, hand-scooped dough, and deliveries out of coolers in their cars.

But the reason they started is what stayed with me. Brittney, her mom, and her sisters launched Something Sweet on the first anniversary of her dad’s passing, using his favorite cookie to honor him and build something together.

What you’ll take away:

• How persistent outreach landed their first meeting with Nugget Markets, and why hundreds of in-store demos mattered after the yes
• How a food product actually gets onto grocery shelves, including the different jobs of buyers and distributors
• Why Brittney saw an opportunity in the frozen dessert aisle when I saw a crowded cookie market
• What building a company with your family looks like when protecting the relationship matters as much as growing the business

🔗 Links mentioned:

• Brittney’s LinkedIn
• ⁠Something Sweet Website⁠
• ⁠Something Sweet Instagram⁠
• ⁠Something Sweet TikTok⁠

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Here's the part that messes with me: one touchdown video, with a sponsor's logo sitting quietly in the corner of the frame, got turned into a sixty five thousand dollar line item. For one post. Mason Platt has run social media for the San Antonio Spurs, New York Mets, Oakland A's, and Dallas Cowboys (twenty million followers across their platforms), and now leads it for Cal's athletics department.

What you'll take away:

• The actual math a sports team uses to tell a sponsor like Pepsi a single touchdown post is worth sixty five thousand dollars, and why the logo in the corner matters more than the play itself
• Why the exact same clip has to get rebuilt five different ways for X, Instagram, TikTok, Facebook, and LinkedIn, down to the order you post it in
• The Best Buy parking lot moment that made a broke college kid buy a camera he couldn't afford, and how it accidentally built his entire career

🔗 Links mentioned:

• Mason’s LinkedIn

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• Website

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