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.