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

📬 Follow Curiosity Class:

• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
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• ⁠⁠Website⁠⁠

Have a guest suggestion? ⁠⁠⁠⁠⁠⁠⁠⁠hello@curiosityclass.co

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

📬 Follow Curiosity Class:

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• ⁠⁠Website⁠⁠

Interested in sponsoring? ⁠⁠⁠⁠⁠⁠⁠⁠hello@curiosityclass.co

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

📬 Follow Curiosity Class:

• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
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• Website

Interested in sponsoring? ⁠⁠⁠⁠⁠⁠hello@curiosityclass.co

She was closing $25 million deals at Spotify by her mid-twenties. And she'll tell you she was at her worst every time she focused on the money.

Gabi Rosen went from the youngest client partner at Spotify to building her own thing, then closed 34 clients in 18 months and joined the founders of the company she now helps run.

What you'll take away:

• The 5 questions she asked friends to test a business idea before building anything (including the one that reveals if they'll actually pay)
• The anchor move that made a $200-a-month price feel like a gift
• Why she thinks about a story about a rock and a locked door every single day

🔗 Links mentioned:

• Website: heyeocworks.com
• Gabi's email: gabi@eocworks.com

📬 Follow Curiosity Class:

• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
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Interested in sponsoring? ⁠⁠⁠⁠⁠curiosityclasspod@gmail.com⁠⁠⁠⁠

Every time someone presses play, they hand you an hour of their life they can never get back. Josh Stabinsky thinks about that math for a living, and it changed how he builds.

Josh Stabinsky is a data scientist at Spotify who works on podcast and creator growth, and the host of the Unit Economics podcast, which he has grown to 60 episodes in a year without missing a single week.

What you'll take away:

• Why asking someone to press play is a bigger favor than it sounds
• The two-episodes-a-week experiment that burned him out, and what he does now
• Why an introvert who felt sick posting on LinkedIn does it anyway
• The one question he asks every guest that keeps his lineup full

🔗 Links mentioned:

• Website: uepod.com
• Instagram: ue.pod
• LinkedIn: Josh Stabinsky
• Substack: uepod.substack.com

📬 Follow Curiosity Class:

• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
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Interested in sponsoring? ⁠⁠⁠⁠hello@curiosityclass.co

Chris Roberts spent 30 years writing software. He says the class that actually trained him for it was not computer science. It was 10th grade geometry, and he did not figure out why until decades later.

Chris holds degrees in both math and music education, taught math from the classroom to the college level, spent three decades in software development, and wrote "Math Education in the Age of AI." He now builds free math-fluency tools for students through his nonprofit.

What you'll take away:

• The 10th grade class Chris says trained him for every software project of his career (it was not coding)
• What "math fluency" actually is, and the exact wall it saved his 120 remedial algebra students from hitting
• The 1970s California classroom that let a 2nd grader take 5th grade math, and why almost no school does it now
• Why he wants a multiplication bee to be bigger than a spelling bee, and how one teacher can run one alone
• What stays valuable when AI can compute any answer instantly

🔗 Links mentioned:

• Chris’ book: Math Education in the Age of AI
• Chris’ website: https://classicmathgames.com/
• Multiplication Game: https://whattimeswhat.com/
• Chris’ LinkedIn: Chris Roberts

📬 Follow Curiosity Class:

• ⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠
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Interested in sponsoring? ⁠⁠⁠curiosityclasspod@gmail.com⁠⁠

David thinks that within ten years there will be billion-dollar companies run by one or two people. Not a team of 500. Two. David Currant has founded four companies, been through Y Combinator (same batch as DoorDash), sold two, buried one, and is now building MX Pilot, an AI "marketing brain" for small businesses.

What you'll take away:

• Why David tells his own kids to skip the normal job entirely, and what he teaches them instead
• The 15 percent number at Y Combinator that quietly turns a startup into a unicorn in two years
• How to test a business idea for 1,000 dollars instead of 20 million, even for a product nobody knows they want yet

🔗Links mentioned:

• MX Pilot: https://mxpilot.ai
• Mustard (David's prior company): https://www.mustard.love
• Reach David: David@mxpilot.ai (reach out for free marketing spend for qualifying CPG / e-commerce brands, or if you’re a tech founder looking for guidance)

• David’s LinkedIn

📬 Follow Curiosity Class:

• ⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠
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Interested in sponsoring? ⁠⁠curiosityclasspod@gmail.com⁠

I give myself an unlimited budget for books. I also track basically every dollar my wife and I spend. Those two things sound like a contradiction, but they're actually the whole point.

This is how we decide what to spend on without an ounce of guilt, and what to cut without feeling deprived. Turns out "budgeting" done right feels less like punishment and more like permission.

I'm no financial advisor, just someone who loves this stuff enough to do a whole solo episode on it. This is exactly what works for us.

What you'll take away:

• The "spend ruthlessly, cut ruthlessly" rule that flips budgeting from restriction into permission
• Why you literally cannot fix your spending until you can see all of it in one place
• The forgotten subscription hiding in your statements right now (mine was $20 a month)

Chapters:

00:00 Cold open

00:30 The paycheck-to-paycheck stat that includes high earners

02:00 Monarch: putting every account in one dashboard

04:30 Spend ruthlessly on what you value (and my book budget)

06:30 Housing, childcare, and the expenses you can't change

07:30 The counterintuitive grocery move

08:00 Using AI to audit your spending

09:00 What's your biggest line item? (drop a comment)

🔗 Links mentioned:

• Monarch Money
• I Will Teach You to Be Rich by Ramit Sethi

📬 Follow Curiosity Class:

• ⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠
• ⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠
• ⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠
• ⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠

Interested in sponsoring? ⁠curiosityclasspod@gmail.com⁠