Uncertainty isn’t just a buzzword -- it’s basically the operating environment for every leader in 2025. From economic volatility to the unknowns of AI’s impact, executives are navigating conditions where the variables outside their control keep multiplying. In this episode, Mike and Corey break down how to lead through the fog—identifying what’s controllable, building flexible plans for the uncontrollable, and creating the right communication cadence with boards, teams, and customers. They share real-world stories of pandemic playbooks, financial “break points,” and unpopular calls that paid off. The takeaway: leading in uncertainty isn’t about having all the answers; it’s about knowing when to decide, what levers you can pull, and how to keep trust intact when the stakes are high.

Arnav Dalmia didn’t set out to build a fitness brand for older adults—but listening to customers led him there. In this conversation, Arnav joins us to unpack the unlikely evolution of Cubii, the company he co-founded that sold for north of $100 million after a decade-long grind that began with Kickstarter and a desk pedal idea.

They dig into why early investors passed, what everyone got wrong about the market, and how a hard-earned product-market fit with seniors turned Cubii into a category-defining brand. Arnav shares the inflection points that changed the company’s course: from bootstrapping out of necessity, to embedding customer feedback into the culture, to resisting the temptation to scale too soon.

If you’ve ever wondered when to pivot, how to listen better, or what lean actually looks like in practice—this one’s a blueprint.

In this episode, Corey and Mike dive deep into one of the defining trends shaping AI’s next chapter: verticalization. They explore why general-purpose AI isn’t enough—and how the most compelling solutions are now being purpose-built for specific industries, starting with Mike’s own experience building an AI operating system for independent financial advisors.

The conversation traces the journey from general tools to tailored workflows, covering:

• How to choose the right vertical by listening for signal, not just scale
• Why true differentiation lies in domain depth, not just technical features
• And how trust, service, and context are shaping the future of human-in-the-loop AI

From relationship managers to compliance nuance, they unpack why vertical-focused AI is creating a new class of companies—ones that feel more like high-leverage service partners than classic SaaS. Whether you’re building, buying, or just trying to keep up, this is the blueprint for what’s next.

In this episode, Mike and Corey sit down with Divey Gulati, co-founder of ShipBob, to explore a challenge few founders navigate successfully: staying in the seat as your company scales from basement hustle to global operation. They unpack what it takes to evolve from a single-product startup to a multi-product logistics platform, and why ShipBob’s culture—rooted in transparency, customer obsession, and founder access—has become its real competitive edge.

From rethinking product strategy around customer behavior to transforming internal processes for a 1,200-person team, the conversation offers a rare inside look at how to scale without losing your core. It’s not just a story about growth—it’s about endurance, reinvention, and building systems that can carry the weight of ambition. Whether you're early in your journey or leading at scale, this episode is a blueprint for staying sharp while moving fast.

In this episode, Mike and Corey dive into one of the most urgent divides forming in the business world: AI-native startups vs. legacy companies scrambling to retrofit their operations. They explore what it really means to build with AI at the core—not just as a tool, but as a fundamental shift in how problems are defined and solved.

From legal bottlenecks to misaligned incentives, the conversation unpacks the cultural, operational, and strategic barriers that slow-moving companies face. And they don’t just talk theory—they lay out a practical framework for how businesses should be thinking about AI across three critical areas: customer experience, product development, and internal operations.

It’s not about hype. It’s about speed, clarity, and the new battleground for differentiation. Whether you're leading a startup or navigating change inside a large org, this is a sharp look at what’s coming—and who gets left behind.

Guest Howard Tullman shares hard-won lessons from decades in tech—on grit, leadership, and why most startups are built on shaky ground. From AI’s limits to the collapse of workplace culture, this is a candid take on what founders, CEOs, and Gen Z need to hear right now.

What really changes when you build your second company? In this episode, Corey and Mike discuss the mindset shift that happens when you’ve done it before—from forcing a business plan onto the world to discovering what’s actually needed. They dive into why iteration beats vision, how to turn low-fidelity ideas into learning engines, and the underestimated power of staying lean. Whether you're scaling your first startup or rethinking your next move, this conversation unpacks how second-time founders think, move, and build differently.

What happens when a private equity executive and a PhD scientist team up to fix the way we consume news? In this episode, Mike Shannon and Corey Ferengul sit down with Tim Huelskamp, co-founder and CEO of 1440, the fast-growing media startup with over 4.5 million subscribers and some of the most enviable unit economics in digital publishing. Tim breaks down the strategic bets, early missteps, and flywheel mechanics behind building a high-trust, curiosity-driven brand from scratch. From his days turning around industrial companies in Alabama to building a fully remote team with zero employee churn, Tim shares what it really takes to scale something enduring—and why treating your team like royalty might be the smartest business move of all.

Karl Hughes has done what many founders aim for but few actually achieve: he built a company that didn’t need him. In this episode, Karl shares how he scaled a technical content agency to seven figures, took a full month off, and began acquiring other small service businesses through micro M&A.

We dive into:
 – How to design for founder independence
 – Why reps beat perfection when building teams
 – The overlooked opportunity in acquiring niche agencies
 – How to grow sustainably without outside funding

If you're a founder thinking long-term, this episode is a blueprint for building companies that last.

AI isn't just another tool—it’s a complete shift in how companies are being built, scaled, and operated. In this episode, Mike and Corey sit down with Eric Mills, founder of Density and Y Combinator alum, to explore what it really means to build an AI-native company. From early-stage experimentation to shipping with agents and orchestrated workflows, Eric brings a practical lens to the hype and a systems-level view on what’s actually working.

They dig into how AI is collapsing cost structures, changing the rules of offshoring, and reshaping org design—from engineering teams to mid-level management. The conversation also touches on knowledge graphs, the rise of “vibe coding,” and why the winners in this next wave won’t just be faster—they’ll be fundamentally different. Whether you’re building, investing, or leading through change, this is a crash course in what the future of software looks like.