John Moakley has spent decades building, running, and investing in data-driven companies—long before “data science” had a name. In this conversation, John joins Mike and Corey to pull back the curtain on what private equity really looks for, how companies often miss the value sitting right in front of them, and why the current hype around AI mirrors the early days of data monetization.
From turning a magazine subscription list into a revenue stream, to helping scale a $70M data business, to earning the nickname Dr. No inside a private equity firm, John shares lessons from both the operating and investing sides of the table.
This episode is about more than data. It’s about pattern recognition, strategic pivots, and the often-overlooked cultural cost of change. And yes, we finally go remote for the first time because when the guest is this good, we don’t let geography get in the way.
What does a board member really look for in a CEO? What signals competence, and what quietly erodes confidence?
In this episode, Mike and Corey sit down with returning guest Ira Weiss—educator, investor, and longtime board member—to decode the often-misunderstood relationship between boards and founding teams. Drawing from over 60 investments and hundreds of founder interactions, Ira shares how he evaluates early-stage CEOs, the underrated power of persistence and curiosity, and the true markers of success (spoiler: it’s not always the outcome).
They dive into:
Whether you're raising your first round or leading a growth-stage company, this episode is a practical guide to working with your board, not just reporting to them.
Anar Isman didn’t start Ageless RX to build a business—he started it to challenge one of humanity’s most accepted limitations: aging. What began as personal curiosity turned into a mission-driven company now generating over $70 million in annual revenue.
In this conversation, Anar joins Mike and Corey to unpack how he built Ageless RX from a late-night side project into a fast-growing, telemedicine-powered platform at the center of the longevity movement. He shares how COVID unlocked the company’s early traction, how off-label science meets mainstream demand, and why he still interviews every hire to protect the culture.
We also get into customer listening, red tape, and what it takes to scale a direct-to-consumer health company in one of the most regulated and misunderstood categories in the market.
From a farm town in Ohio to penthouse events with billionaires in Chicago—Andrew Gunderman’s journey is anything but ordinary. By his early twenties, he had already founded and sold a startup, built founder communities from scratch, and begun curating some of the city’s most exclusive circles of entrepreneurs, investors, and influencers.
In this conversation, Andrew joins Mike Shannon and Corey Ferengul to unpack the strategy behind building Renowned Chicago, why exclusivity works when it’s paired with openness, and how relationships—not just capital—can accelerate a founder’s trajectory. He shares how aggressive outreach, mentorship, and an obsession with learning shaped his path, and why he believes networks can be one of the most valuable assets an entrepreneur can build.
We also dive into the evolving world of creators and influencers, the hidden leverage in connecting siloed communities, and how AI is already beginning to reshape how networks form.
If you’ve ever wondered how to break into circles that feel closed off—or how to turn relationships into real opportunities—Andrew’s story offers a playbook worth studying.
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:
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.
This week on Momentum Mode, we’re joined by Amanda Lannert, longtime CEO of Jellyvision, for a conversation that goes deep into the mechanics of building a strong, sustainable company culture. Amanda breaks down how Jellyvision’s values—like trust, responsiveness, and the deceptively powerful mantra “be helpful”—translate into everyday decisions, from hiring and onboarding to managing through layoffs. With clarity and candor, she shares the thinking behind the systems and rituals that have made Jellyvision consistently recognized as a great place to work.
We also explore the evolution of leadership in fast-growing companies, what post-COVID culture building looks like, and why authenticity at the top sets the tone for risk-taking and creativity across the org. Whether you’re scaling a team, rethinking your leadership style, or navigating tough transitions, Amanda offers a masterclass in leading with humanity, humor, and purpose.
What does it really take to lead a company through high-stakes growth, acquisitions, and transformation? Dan Dal Degan—known to many as Triple D—returns for a deep dive into what most leadership playbooks leave out.
Drawing on decades of experience scaling enterprise software companies, including an early role at Salesforce, Dan shares what it means to build strategy that’s not just understood by the C-suite but felt across the company. We get into why trust is the bedrock of strategy, how culture shapes execution, and what it looks like to lead with clarity during times of pressure and change.
From redefining what “adoption” actually means to gamifying financial fluency across teams, this conversation is a masterclass in operational leadership that drives alignment—without losing the human element.
What actually happens after a founder steps aside and a new CEO steps in? Kelsey Behringer, CEO of Packback, joins us to unpack the emotional and operational realities of leading a company through a major transition—from a VC-backed startup to a growth-stage business under new ownership.
Kelsey opens up about what surprised her most in the CEO seat, including the often-unspoken loneliness of leadership, and how she’s built systems of support, communication, and culture from the inside out. We get into how her background in teaching shaped her approach to change management, why financial transparency builds trust, and how she balances performance with humanity in a mission-driven company.
Venture capitalist and Booth professor Ira Weiss joins Momentum Mode to break down what great board members actually do, how investor dynamics shift across funding stages, and why early-stage founders should rethink how they engage with their boards. A candid conversation on strategy, signals, and the real work of scaling.
Amanda Lannert became CEO of Jellyvision by surprise—literally. In this episode, the longtime leader of Jellyvision shares how she grew into the role, navigated scale without losing soul, and learned to balance rapid change with operational stability. It’s a candid look at leadership, authenticity, and building with intention, even on the fly.
If you’ve ever questioned whether you’re ready for the next big role—or if you’re already in it and figuring it out as you go—this one’s for you.
We’re back—with a new name! Opening the C-Suite is now Momentum Mode. Same podcast, same candid conversations—now with an even sharper focus on building and sustaining momentum in leadership and business.
In this episode, Dan Dal Degan (Triple D) joins us to unpack the realities of leadership, mentorship, and company-building. A seasoned SaaS executive, investor, and board member, Dan has played a pivotal role in scaling companies like Salesforce and leading major acquisitions—including a $250M sale to DocuSign.
Whether you’re leading a company, building a career, or investing in the next generation of leaders, this episode is packed with real-world lessons on how to build and sustain momentum in leadership.
