39. I'm Back. Let's Talk About NYC...

42. How to Blow Through $100mm in 10 Years

The world moves too fast for anything to feel grounded anymore, which is why I can jump from culture headlines to Odell Beckham Jr. explaining how “easy” it is to burn through a hundred million dollars without hardly a breath.  The gap between how people actually live and how public figures talk about money is hilarious and kind of the whole point of this episode. I’m digging into perspective, delusion, and also the math nobody wants to look at. Got questions or think I missed a spot? Drop us an email at soup@soupofwallstreet.com and get in on the conversation!

41. The Pink’s Boys Join the Show

You know how everyone online screams about their frameworks and “five-step blueprints” for starting a business? Yeah…  Pink’s Window Services  blew up by doing the opposite. I sit down with Brandon Downer and Carter Smith to talk about Pink’s rise to Insta fame, how to clean windows, and the weird stuff people overthink.I love conversations like this because they remind me how close most people are to changing their entire life. They founded Pink’s Window Services, turned it into a franchise, and somehow convinced the internet that they cracked a code when really they were just having a good time and doing the work. Don’t forget to tell us your favorite soup in the comments…

40. Why Housing Is About to Get Worse (Again)

The world looks normal until it absolutely doesn’t. One minute you’re creeping through downtown traffic like a civilized adult, the next a grown man on a rental scooter is screaming at you in Chelsea boots before punching your window like he’s auditioning for a fight scene. That’s 2025. Everyone’s playing different games. This week I’m talking about all the weird incentives shaping the world right now. Why a 50-year mortgage is a disaster disguised as a gift, how celebrity tequila probably sucks, why comparing yourself to strangers online might be the dumbest hobby we’ve invented, and why some people need the simple brutality of sports just to feel something predictable. Got questions or think I missed a spot? Drop us an email at soup@soupofwallstreet.com and get in on the conversation!

39. I'm Back. Let's Talk About NYC...

A business quarter away and the world went feral without me. New York just hired a 34-year-old foreclosure counselor to run the most financially influential city on the planet, and everyone’s acting weird about it. The craziest part is how the internet tricked all of us into thinking we should have opinions about everything, all the time. Elections aren’t thoughtful committee decisions anymore. They’re individual panic attacks aggregated into policy. And yet… stocks keep going up, we’ve got fresh water, and life is still somehow pretty good. Welcome back to the chaos. Got questions or think I missed a spot? Drop us an email at soup@soupofwallstreet.com and get in on the conversation!

38. Starting a Business is a Terrible Idea

You really think you're gonna win by making the best underwear? The best shampoo? The best anything? Cute. The truth is, most of the time, the world doesn’t want the best. It just wants something. A thing that exists. A hotel that’s not the worst. A gym that’s $10 a month. A pair of Skechers.  This one’s for every founder who’s stalling their launch because they think their product isn’t perfect yet.  Got questions or think I missed a spot? Drop us an email at soup@soupofwallstreet.com [soup@soupofwallstreet.com] and get in on the conversation!