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Matt Fleissig didn't find his life's work in a boardroom. He found it at a community barbecue in the Catskills — talking about snow plowing. That casual conversation with Steve Braverman, the man whose family invented the powder-free latex glove and sold it to Kimberly Clark for $1.4 billion, turned into a Monday morning meeting in Fort Lee, New Jersey. Which turned into a founding partnership. Which turned into Pathstone — a firm with nearly 1,000 employees overseeing over $200 billion in assets for ultra-high-net-worth families. Oh, and the other guy named Matt almost didn't hire him because of the name conflict. In this episode, Matt breaks down: The barbecue moment that changed his entire trajectory — and why he almost didn't get the job What Steve Braverman taught him about culture, mentorship, and treating people like partners from day one Going from 19 families to 2,500 — and what it actually takes to scale without losing who you are Why "terminal velocity" is the greatest insult you can tell a founder — and what they did about it The moment he realized out-hustling everyone wasn't enough anymore Why ultra-high-net-worth families need more than an investment manager — and how Pathstone built around that The uncomfortable feeling in your stomach when you pick up the phone — and why that's the size of your business growing What it means to never say no for a living If you believe the best opportunities in life show up when you least expect them — this one's for you.

Raj Singh spent almost a year and thousands of dollars on coaching, therapy, breathwork, and meditation. It was transformative. It was also completely inaccessible to most people on the planet. Then he sat down at a poker table in Venice next to Mark Manson — author of The Subtle Art of Not Giving a F*ck — and everything clicked. Both of them had been circling the same idea: what if the world's best personal advice didn't have to cost a fortune? What if AI could deliver the kind of deeply personalized guidance that only the top 1% can currently afford — and bring it to everyone else? That conversation became Purpose — an AI-powered personal growth companion built to be the mentor, coach, and thought partner that most people never get access to. In this episode, Raj breaks down: The year-long sabbatical that changed how he sees personal growth — and what he learned about himself that surprised him most Why the best advice in the world doesn't scale — and how AI changes that equation for the first time Starting his first AI company in 2014 — a decade before it was cool Why every adaptation eventually becomes maladaptive — and what to do about it The social media trap: how platforms hijacked the comparative mind and the mental health cost we're all bearing Why he's wildly optimistic about AI — and what he thinks it will finally get right The 300 notifications a day problem — and how AI might actually give us our attention back If you believe the best version of yourself is just one right conversation away — this one's for you.

It was just before Christmas 2008. Eddy Arriola had spent the entire year building a community bank from scratch — the team, the investors, the strategy, everything. Then the phone rang. Florida regulators told him their priority wasn't opening new banks. It was shutting down the ones already failing. He wasn't their problem to solve. Eddy was devastated. And then his brother said four words that changed everything: you just keep going. That perseverance — forged first on wrestling mats, then in the depths of the financial crisis — carried Eddy all the way to founding Apollo Bank, building it for over a decade, and eventually selling it on his own terms. In this episode, Eddy breaks down: What it actually felt like to start a bank during the worst financial crisis in modern history Why he always knew the exit before he even opened the doors How wrestling taught him that the most skilled person rarely wins — the most persistent one does The silver linings he could only see in retrospect — and what that taught him about trust Why relational leadership is the only framework that actually scales What happened to his identity after the sale — and how he found his way back The pool moment: why presence is the real luxury most successful people never allow themselves The bronze medal analogy that reframes everything about what it means to make it If you've ever gotten a phone call that felt like the end — and had to find a reason to keep going anyway — this one's for you.

Rich Thompson learned everything he needed to know about business behind the counter of a frozen yogurt shop in Northern California. His parents ran it. All five kids worked it. And from the time he was four years old, Rich watched his parents show up every single day — opening, closing, fixing orders, building relationships with every customer who walked through the door. That foundation followed him through a career in finance, into founding his own investment fund Caprice, and eventually into leading Dreamliner — a staffing and workforce solutions company with 600 employees — where he still shows up every day, in the trenches, the same way his parents did. In this episode, Rich breaks down: What a frozen yogurt shop in NorCal taught him about customer experience and community Why he's always bet on the jockey, not the horse — and what that means for how he invests The decision to leave corporate finance and build something on his own terms How athletics shaped his competitive edge and work ethic long before business did Why the owner in the trenches always outperforms the owner in the ivory tower The balance framework he uses to make decisions when hundreds of families are depending on you Why his next chapter is about helping founders who have the idea but don't know who to call What watching someone grow from individual contributor to leader does for him If you believe the best businesses are built on relationships, not spreadsheets — this one's for you.

In 2005, Benny Czarny had a simple mission: build a cybersecurity language that helped products talk to each other. Twenty years later, that mission has evolved into something far bigger — protecting the world's critical infrastructure. But the real turning point? A discovery buried inside a product test. While running compatibility checks on hundreds of antivirus tools, Benny found something alarming: antiviruses are only about 45% accurate when scanning a file. A coin flip. And most of the major cybersecurity incidents happening in enterprises? Caused by file flow. That insight changed everything. In this episode, Benny breaks down: Why he started with an OEM model — and why every founder building for the long term should consider it The accidental discovery that revealed a massive gap in the cybersecurity industry What it actually means to pivot from OEM to enterprise — and how it changed his job overnight Why critical infrastructure protection is so much bigger than OT security How he's built a company that promotes from within — interns becoming GMs, junior marketers running global teams The five year plan he updates every single year — and why they're beating it 290,000 certified students and counting at OPSWAT Academy Why making at least one mistake a day means you're not on vacation If you're building something for the long game — this one's a masterclass

Mitch Slater wanted to be in broadcasting. He worked for Larry King. He worked for Howard Stern. He produced game shows in Los Angeles. And then his dad's manager looked at him across a desk and said: you've got communication skills, you can handle rejection — we'll teach you the rest. That was 35 years ago. Today Mitch is one of the most respected financial advisors at UBS — and the lessons he learned watching Larry King every night still drive how he builds relationships with every client. In this episode, Mitch breaks down: How a career in broadcasting accidentally became a career in wealth management What Larry King taught him about listening — and why he never learned anything with his mouth open The return on relationship framework that has defined his entire career Why managing expectations is the most underrated skill in financial services How he built his niche — and why going deeper always beats going broader What he thinks AI will and won't do for the financial advisory business Why after open heart surgery last year, he's more convinced than ever that human to human will always matter 300 Springsteen shows and counting — and what that passion has to do with how he shows up at work If you believe relationships are the real currency in any business — this one's for you.

Harold Jurado packed everything he owned into a small Subaru Crosstrek, left his family in Chicago, and drove west with almost no money and no plan. He didn't know where he'd land. He ended up in San Francisco — and a job at Google running their noodle cafe, Threads, changed everything. Serving 2,000 people a day, watching lines stretch out the door rain or shine, Harold saw something most chefs never see: consistent, year-round demand. Not seasonal. Not trendy. Just people who always wanted a great bowl of noodles. That data point became a restaurant. That restaurant became Ramen Well. And now Harold is building his second company — Umami Hadi, a frozen ramen and chili oil brand built to go national. In this episode, Harold breaks down: Why leaving Chicago with almost nothing was the most important decision of his life What cooking at Google taught him about demand, scale, and proof of concept Why he chose ramen over sushi, steakhouse, or fine dining — and what that says about who he wants to serve The gastropub philosophy: taking everyday food and elevating it without losing accessibility What it's like running two companies at once — two rents, two payrolls, two babies The short term goal (one grocery store) and the long term vision (national, nine figures, exit) Why he thinks going out to restaurants more is one of the best things you can do for society If you've ever packed up your life and driven toward something you couldn't quite name yet — this one's for you.

Andy Hilger never planned on a corporate career. English and philosophy major. Master's in creative writing. Spent his 20s working in a group home and an environmental company — pretty sure the corporate world wasn't for him. Then he took a job at Allegiance Group just to pay the rent. And one chaotic meeting changed everything. A flip chart marker rolled in front of his chair. He reached down to pick it up. His boss pulled his chair away. And suddenly the behind-the-scenes note taker was standing in front of four angry people being told to "land the plane." What happened next set the trajectory for a 25-year career that took him from note taker to President of Allegis Group — one of the largest staffing companies in the world. In this episode, Andy breaks down: The one moment that pulled him out of the background and into the arena Why the best leaders breathe in stress and breathe out calm How a startup with "fire, fire, fire, ready, aim" energy became a billion dollar company The agility vs. ability framework — and why your degree's half life is about 2.5 years Why careers are still being run on waterfall when the world has gone agile What lifelong learners have that makes them nearly AI-proof How he's spending his next chapter: teaching at Duke, writing, and helping people retain their agency in a world that keeps changing If you've ever felt like a square peg in a round hole — and wondered if that might actually be your superpower — this one's for you.

At 11 years old, Dusty Holcomb's parents pulled him out of school. No classroom. No curriculum. Just a library card and a world of books waiting to be devoured. What felt like an oddity at the time turned out to be the greatest gift of his life. Dusty spent his formative years reading biographies of Eisenhower, Rommel, and Lincoln — not because anyone told him to, but because he was fascinated by one idea: ordinary people doing extraordinary things. That curiosity planted a seed that grew into 28 years of leading organizations, 15 of them as President or CEO — and now a second career coaching the next generation of leaders through the most disruptive moment in business history. In this episode, Dusty breaks down: Why being homeschooled at 11 became the greatest inflection point of his life What military history taught him about leadership before he ever ran a team The first principle of leadership that most managers never figure out: it's not about you Why clarity and alignment are the two most underrated tools in any leader's arsenal How great leaders architect machines — and let go of who gets the credit The 86% problem: why most organizations are paralyzed by AI and what to do about it The three pillars every leader needs to evaluate AI decisions: return on capital, return on time, return on new opportunity Why "designed by a human" needs to become the only acceptable standard If you believe leadership is a craft worth mastering for life — this one's for you.

Aaron Vaccaro was a senior in college, striking out on every internship, staring into the abyss. One spring afternoon, after an investment club presentation, he spotted a board member in the lunchroom and did something most people wouldn't — he asked if they could grab lunch. That board member knew a guy in Seattle. Didn't really know what he did. Just had a feeling they'd connect. That feeling turned into a phone call. That phone call turned into a summer internship. That internship turned into 12 years working alongside Eric Anderson — investor, visionary, and the man Aaron credits for everything he knows about business and life. In this episode, Aaron unpacks what it actually looks like to find the right mentor, earn their trust, and grow alongside them for over a decade — from scaling TopGolf to building Singularity University. We get into: The one lunchroom moment that changed everything What to look for in a mentor — and what they're looking for in you Why capability plus values alignment is the formula for any great partnership The art of unbundling complex problems — and why most people conflate everything Visionary leaders vs. execution leaders — and figuring out which one you are What succession planning looks like when your mentor is your north star Why deep tech, energy, biology, and robotics are where Aaron is placing his bets next The unexpected lesson of becoming a first-time dad If you've ever wondered what it takes to find the right person to learn from — and how to make the most of it — this one's for you.

Marc Shaw never planned to be in the title business. He wanted to prosecute insider trading at the SEC. Never got the callback. Instead, at the 2002 NFC Championship Game — a loss, by the way — he struck up a conversation with the guy sitting in front of him. That stranger was in the title space. And he offered Mark some closings on the side while he finished law school. That one conversation turned into a career. And that career turned into Worldwide Title — one of the fastest growing title companies in the country, built on a simple belief: technology doesn't replace trust. It just relocates it. In this episode, Marc breaks down: How a stranger at an Eagles game changed the entire trajectory of his life What he saw in the title industry that nobody else was paying attention to Why his first employees are still with him today — and what that says about culture The human expertise layer that no amount of AI can replace Why title insurance is fundamentally a promise, not a transaction The Atari to PlayStation 10 analogy for where AI is headed — and what it means for his industry Why judgment, relationships, and trust are about to become the most valuable skills in business If you've ever stumbled into something that turned out to be exactly where you were supposed to be — this one's for you.

Naren was a lawyer at three different venture-funded tech companies when the dot com bubble burst and took all three of them with it. So he did what any reasonable attorney would do next. He started a children's book company. It started with a bedtime story for his three-year-old daughter, a Virginia Tech mascot named the Hokie Bird, and some truly terrible illustrations. That one book sold 5,000 copies in six months — and unlocked a niche nobody had touched: children's books at the intersection of licensed sports content and university pride. 350 universities later, he had a publishing company. Then in 2018, he pivoted again — into thought leadership publishing through Amplify, helping executives, entrepreneurs, and experts turn their ideas into books that open doors nothing else can. In this episode, Naren breaks down: Why he went from law to publishing — and why it made more sense than it sounds How one proof of concept became a deal with 350+ universities and Major League Baseball The 2018 pivot to thought leadership books and why it changed everything Why a book is the ultimate long-form content flex — and what LinkedIn posts will never be able to do The AI writing question every author is wrestling with right now — and where the line actually is Why your email list is still your single most valuable asset at launch The bureau strategy that gets speakers more bookings from a single book tour If you've ever thought about writing a book — or wondered if it's still worth it — this one's your answer.

Stephanie spent 20 years helping her dad grow his natural ingredient business. She fell in love with the work, the industry, and the meaning behind it all. Then they sold it — and she was left staring at a blank page. What do you do when the thing that gave your work its soul is gone? You build something new. From scratch. On your own terms. And if you're lucky, you get to do it with the person you love most. In this episode, Stephanie and Tyler share the story behind Dabble & Dollop — a kids' personal care brand built on values, not venture capital — and what it actually looks like to build a business together as husband and wife. We get into: Why selling the family business was the catalyst Steph needed to bet on herself How Tyler went from investment banking to Mint Mobile to co-founder — and why the timing finally felt right What working with her dad taught Steph about autonomy, risk, and what meaningful work actually feels like The real consumer insight that changed their entire product strategy Why parents of newborns will spend anything — and what happens at age three The cash flow reality of self-funded consumer products (spoiler: it's brutal) Why the entrepreneurship unicorn story is a lie — and what seven years of fighting actually looks like How Steph stays positive when the road gets hard If you've ever wondered what it takes to build something real — with no outside money, no safety net, and everything on the line — this one's for you.

Derek Coburn has made a lot of decisions in his life. Good ones. Bad ones. But ask him which one changed everything — and the answer comes without hesitation. Marrying Melanie. Not a business deal. Not a career pivot. Not a bold financial bet. The person he chose to build his life with. And 17 years, two kids, and a thriving wealth management practice later — he's more convinced than ever that who you marry is the most important decision you'll ever make. In this episode, Derek gets refreshingly honest about what it actually takes to build a great marriage, a great career, and a great life — at the same time. We get into: Why "happy wife, happy life" is some of the worst advice ever given Starting therapy while engaged — and never stopping The privilege nobody talks about: waking up next to someone you love The Tale of Two Tonys — and why you probably only need to save 1% to retire well The $50,000 moment every parent is taking for granted right now Why he restructured his entire day around being available when his kids want him What it means to be in the "regret minimization business" Why he's not selling anything — and why that makes everything he says more worth hearing If you've ever wondered what it looks like to actually design a life you don't want to escape from — this one's for you.

In February 2020, Willie Litvack had his biggest month ever. Squadup — the self-service ticketing platform he'd spent six years building brick by brick — had just crossed $400K in monthly revenue. The business was profitable. The momentum was real. Then the phone rang. Within nine days, revenue went from $400K to zero. Willie had to furlough 17 people on a call with a lawyer billing $700 an hour — a lawyer he couldn't afford. And he had to figure out how to keep the lights on with almost nothing in the bank. What he did next is a masterclass in leading through chaos. In this episode, Willie shares: How he built Squadup from zero to $5M ARR without VC money — and why that made COVID hit harder The emotional reality of letting 17 people go in a single day and what it took to carry that Why the CEO's job is to be a shield — and what happens when the shield breaks How they used the downtime to rebuild the product and came out stronger on the other side The eventual exit and what it actually felt like Why he started Press On Ventures — and what "press on" means to him personally The three I's framework he uses to evaluate every founder: Integrity, Intensity, Intelligence The role his wife Madeline played in making all of it possible If you've ever had to hold it together when everything was falling apart — this one's for you.