Journeys to the Summit

How do you build two successful businesses in completely different industries and sell them both before 40?In this episode, Ilya Zlotnik sits down with entrepreneur Jeff Glazer to unpack a journey that spans medical spas, manufacturing, private equity exits, and everything in between. Jeff shares how he:-Bought a failing medical spa during the financial crisis—and made it cash flow positive in 30...

What if you could match the market and improve your after-tax returns? In this episode, Ilya sits down with Bob Holdsworth, Founder of Custom Harvest and a pioneer in ETF-based direct indexing, to break down one of the fastest-growing strategies in wealth management. Bob explains how direct indexing works, why it’s gaining traction, and how investors can use tax-loss harvesting to generate “tax al...

Most business owners focus on revenue, growth, and brand when thinking about enterprise value—but overlook one critical factor: taxes. In this episode of Journeys to the Summit, Dean Pearson, Principal at PBG Financial and head of their State & Local Tax group, breaks down how tax decisions made today can directly impact your business valuation tomorrow. From missed filings to multi-state tax...

What if your health issues weren’t random, but signals your body is sending? In this episode of Journeys to the Summit, Ilya Zlotnik sits down with Irina Frenkel, founder of Retreat, a rapidly growing health and wellness boutique redefining modern medicine. Irina shares her journey from traditional healthcare to a personalized, root-cause approach after being misdiagnosed with diabetes at 21. That...

What does it take to build a $100B business from scratch, without raising a single dollar? In this episode, Byron Udell shares the full story behind building AcuQuote into one of the largest life insurance brokerage firms in the country. And selling it in 2021 at exactly the right moment, just before markets shifted. From starting as a solo operator in 1986 to scaling a company with 250+ employees...

What if true wealth isn’t money—but your health? In this conversation, Ilya Zlotnik sits down with Daniel Chille, founder of TBD Fitness & Holistic Health, to explore the powerful intersection of health, longevity, and wealth. Daniel shares his journey from D1 athlete and professional soccer player to holistic health practitioner, and breaks down how optimizing your body can completely transfo...

Buying or selling a home right now isn’t easy, and that’s exactly why this conversation matters. In this episode of Journeys to the Summit, Scott Ottenheimer, a top real estate team lead at Baird & Warner, breaks down what’s really happening in today’s housing market—and what buyers, sellers, and investors often get wrong. With interest rates soaring and inventory still tight, many buyers feel...

What is Private Placement Life Insurance (PPLI) and why is it gaining traction among high-net-worth investors? In this episode of Journeys to the Summit, Ilya Zlotnik sits down with Jordan Katz, CEO and Founder of JR Katz, to break down one of the most powerful (and often misunderstood) tools in wealth management. Jordan explains how PPLI works as a tax-efficient investment “location”, not just an...

Kyle Therriault didn’t set out to build a massive e-commerce company, but that’s exactly what happened. Starting with overstock auto parts sold on eBay, Kyle and his father, Steve, built Auto Accessories Garage from scratch during a time when most people believed “no one would ever buy auto parts online.”They faced rejection from vendors, banks, and even their own industry. But through persistence...

What if you could invest in top private companies before they go public, and at a significant discount? In this episode, Michael Grayson, Portfolio Manager at First Trust Capital Management, breaks down two of the most powerful (and misunderstood) strategies in private markets: co-investments and secondaries. We explore:-The key difference between fund investing vs. co-investing-How investors can...

Elite trader Lance Breitstein joins Ilya Zlotnik for a raw conversation on what it actually takes to become a top performer in prop trading, and what it costs. Lance shares his journey from obsessing over the Market Wizards books as a college student to grinding through a brutal first year with no profitable months, to ultimately becoming the #1 trader at Trillium, setting records and leading/ment...

In this episode of Journeys to the Summit, Ilya Zlotnik sits down with Craig Lemoine, Director of Financial Planning at the University of Illinois, to talk about the real evolution of wealth management and why the next generation of talent is entering the profession differently than ever before. Craig shares his unconventional path from physics major to financial planning, his early career inside...

In this episode of Journeys to the Summit, host Ilya Zlotnik sits down with healthcare entrepreneur and climbing partner Ian Strug for a candid, high-altitude look at risk, failure, and building again. Ian walks through his path from: -Liberal arts major at Vanderbilt with PhD dreams -Early career at Epic and management consulting -Co-founding Virgo, an AI-enabled GI/endoscopy company -Surviving C...

What does it take to pivot from military service to co-founding a multi-billion-dollar wealth management firm? In this episode of Journeys to the Summit, host Ilya Zlotnik interviews Randy Golden, co-founder of Vivaldi Capital Management. Randy shares his unexpected path from academic probation to the U.S. Army, the lessons he carried into finance, and the bold moves that helped him and his partne...

From kitchens to private equity boardrooms: Partner Sam Bendix of Chicago Pacific Founders (CPF) shares how classical culinary training shaped his discipline, how healthcare private equity shares common demographic and operating fundamentals with healthcare real estate, and practical advice for owners preparing to sell. He and host Ilya Zlotnik dig into value-based care, senior housing, and medica...

What drives someone to leave the familiar and build something from the ground up? In this episode of Journeys to the Summit, host Ilya Zlotnik sits down with Shane Stiles, founder and president of Gate 39 Media, to explore his entrepreneurial roots, shaped by a childhood working in his father’s gas stations. Together, they unpack Shane’s transition from corporate life to entrepreneurship, the foun...

In this episode of Journeys to the Summit, Ilya Zlotnik sits down with business leader Josh Rogers to explore the early struggles, strategic pivots, and leadership lessons that helped shape his success. Whether you're building a startup or leading a team, Josh's story offers insight into what it takes to grow with purpose. 🔗 Subscribe for more: @journeystothesummit  #JourneysToTheSummit #...

What does it take to build a thriving, forward-thinking manufacturing business in America today? In this episode of Journeys to the Summit, host Ilya Zlotnik sits down with Alex Khakham, co-owner of Gil Sewing and High Performance Uniforms, to explore his family’s inspiring immigrant story, their start with six sewing machines, and how they’ve grown into a powerhouse serving retail brands, Fortune...

In this inspiring episode of Journeys to the Summit, host Ilya Zlotnik sits down with Chicago entrepreneur and restaurateur Dimitri Syrkin-Nikolau, the founder of Dimo’s Pizza and upcoming Southport Betty's. From crafting experimental slice combos to creating face shields during COVID, Dimitri's entrepreneurial spirit is as creative as it is resilient. In This Episode: How an 8-year-old wi...

Join me in an exclusive conversation with David Sternberg, CEO and Co-Founder of Vivaldi. From his unexpected leap into trading at the Chicago Board Options Exchange to navigating market crashes with precision and discipline, David shares the pivotal moments that shaped his career. Discover how he reinvented himself after trading, built a firm that redefines wealth management, and empowered the ne...