They cover:
Why the best founders discover their business instead of forcing it into the world
The design partner model and why Mike wouldn't start a company any other way now
Why product market fit is no longer a stable destination, and what to do about it
The real reason is to raise as little money as possible, as late as possible
How fractional talent has changed early-stage team building (and where it still doesn't work)
The six-eight-week cycle framework Mike uses to protect his time and stay focused
Why the technical moat is dead, and what actually defends a business long term
How one great referral from a credible client beats ten thousand cold emails

If you're a founder, operator, or investor trying to understand what building looks like in this moment, this one is worth your time.

Why major layoffs at Meta, Oracle, and Square may have less to do with AI and more to do with overhiring
The "management by magazine" problem and why it's more dangerous than ever in the AI era
Which processes are the glass balls you absolutely cannot afford to break with premature AI deployment
Why AI adoption has to be bottom-up and what happens when CEOs try to force it top down
The sycophancy problem: why AI affirms you 49% more than a human would, and what that means for decision-making
Token costs: how some companies are spending more on AI than they saved by cutting headcount
Why token usage is a vanity metric and what actually matters when measuring AI ROI
Where the agent orchestration problem is already breaking down inside real companies

No predictions that will age badly. Just two operators who work in AI every day, telling you what they're actually seeing.

In this episode of Momentum Mode, Corey Ferengul and Mike Shannon sit down with Alex, a multi-time founder, former CMO of Deloitte Digital, and now CEO of a 110-person AI transformation firm, to unpack what it actually looks like to deploy AI inside mid-market companies at scale.

They cover:
Why "management by magazine" is the most dangerous AI strategy in the boardroom right now
The real reason companies aren't further along on AI (hint: it's not the technology)
Why Quantum Rise prices on outcomes, not hours, and why that's a fundamental shift for the services industry
The difference between AI training and AI change management, and why it matters
How to spot fake AI expertise on a resume and what real credentials actually look like
Where the Sequoia "services is the new software" thesis holds up, and where it gets complicated
Why Alex believes AI will create more jobs than it destroys

Whether you're a founder, operator, or executive trying to figure out your AI strategy, this one cuts through the noise.

Mike is two and a half years into his second startup (Impruve), and this time he's doing it differently. No $4M raised before product-market fit. No chasing the next round before discovering what the business actually is. In this episode, he breaks down what he learned the hard way the first time and why AI makes the case for restraint even stronger today.

They cover:
→ Why raising too much too early limits your operational creativity
→ The "discovery vs. scaling" mindset shift that changes everything
→ How AI is compressing build costs and what that means for your funding strategy
→ The vendor risk paradox: why more capital raised ≠ more stability
→ What product-market fit actually has to look like before you pull the scale lever
→ The real cost of marrying yourself to a financial goalpost too early

Whether you're pre-seed, mid-raise, or reconsidering your next round, this one is worth your time.

🎙️ Momentum Mode is hosted by Mike and Corey, two operators who've built, invested in, and advised technology companies across the Midwest and beyond.
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In this episode, Mike and Corey break down the most pressing question executives are facing: how do you build a genuine AI strategy when the technology is changing faster than your planning cycle, investors are breathing down your neck, and employees are already using AI tools you don't even know about?

We get into why cutting headcount is the wrong first move, what "shadow AI" in your organization is really telling you, and the unglamorous data work that separates companies who will win with AI from those who won't.
What we cover:
— Why the "cut first, figure it out later" approach is organizationally dangerous
— The MIT vs. Wharton AI adoption research and what the gap tells us
— "Management by Magazine" — and why investor pressure is driving bad AI decisions
— Why your data house has to come before your AI strategy
— Shadow AI: what to do when employees are already using tools you haven't approved
— The career opportunity hiding inside the AI disruption (for employees at every level)
— Why you should never get married to a single AI tool or vendor
— The regulatory fragmentation coming for multinationals and the fiduciary risk already here in financial services
If you're an executive, operator, or anyone trying to lead through the AI moment without just reacting to headlines, this one is for you.
🎙️ Momentum Mode drops new episodes weekly. Subscribe so you don't miss the next one!

From the midnight due diligence call to the data gaps that quietly kill deals, they get into the details founders rarely hear until it's too late.

They cover:

• Why not all revenue is equal and how buyers value it differently
• The churn data you should have been tracking years ago
• How succession planning becomes an M&A issue for services businesses
• What separates a PE buyer from a strategic — and why it changes everything
• The curveballs that catch sellers off guard: legal history, executive turnover, and decelerating growth
• Why clean, organized data can add half a turn to your multiple

If you're a founder thinking about an eventual exit, a services business owner navigating succession, or an operator who wants to understand how buyers really think, this episode is a must-watch.

From how startups actually get on the radar of strategic buyers to why integration should start before a deal is even signed, Ann shares hard-earned lessons from decades inside Silicon Valley deal rooms.

They dig into the realities founders don’t always see:
• Why culture mismatch kills value post-close
• How messy IP and entity structure can derail a transaction
• The real purpose of earn-outs (and why they often end in lawsuits)
• Why Intel rewarded “devil’s advocates” for stopping bad deals

If you’re a founder thinking about being acquired, an operator navigating integration, or an investor trying to understand what really drives M&A outcomes, this episode is a must-watch.

With decades of experience across global transactions, Marty shares a behind-the-scenes look at how acquisitions actually happen — and why leadership alignment, timing, and operational discipline matter far more than financial models alone.

The conversation explores common misconceptions founders have about exits, the hidden risks that emerge during diligence, and how companies can maintain leverage while navigating complex deal processes.

In this episode, you’ll learn:
• The one factor that ultimately determines if a deal closes
• Why time — not price — kills most transactions
• How founders unintentionally weaken their position during diligence
• The difference between strategic buyers and financial buyers
• How to maintain operational momentum during an exit process

If you’re a founder, executive, or investor navigating growth, fundraising, or potential acquisition, this episode offers a practical perspective on how deals really get done.

Subscribe for more conversations on leadership, scaling, and strategic decision-making.

In this episode of Momentum Mode, Corey Ferengul and Mike Shannon sit down with Anthony Knierim to unpack what actually drives durable growth inside scaling organizations.

From operational discipline and accountability to leadership evolution and system design, Anthony shares what separates companies that scale intentionally from those that grow into chaos. The conversation explores:

• Why early success often hides structural weaknesses
• The difference between motion and real progress
• How process protects innovation (instead of slowing it down)
• Why accountability must be cultural, not situational
• The leadership shift required to move from founder-led to system-led growth

If you're a founder, operator, or executive navigating growth, this episode offers a practical lens on building organizations that last — not just ones that move fast.

Subscribe for more conversations on leadership, scaling, and building with intention.

As co-founder and CEO of Holistic, Tom is building tools to help companies actually understand and improve the employee experience. Not with vague platitudes, but with measurable, actionable data. In this episode, we dig into what’s really changed since the early days of Holistic, how the modern employee mindset has evolved, and why transparency isn't just a buzzword. It's a survival strategy.

From his time shaping ecosystems at 1871 to building a company rooted in operational rigor, Tom shares what founders still get wrong about culture, how to build alignment before tension erupts, and why playing your hand face up is now the only winning move.

Here’s what stood out:

Entrepreneurship Isn’t Personal. Until It Is.
Seven years in, Tom admits the emotional intensity hasn’t dulled. Every client loss, every critique, still stings. Why? Because when you believe your product genuinely helps people, rejection feels like something deeper. The real challenge is learning how to care deeply without taking everything personally.

Employee Experience Is No Longer Just Perks
Today’s employees want impact, clarity, and to feel part of a mission that matters. But here’s the catch. That mission has to be real. Holistic’s approach is about building cultures that don't rely on surface-level benefits, but instead align expectations, actions, and outcomes.

AI Might Undermine Loyalty. But It Can Also Rebuild It.
In a world where employee tenures are shrinking and layoffs are data driven, Holistic is using predictive tools to help leaders intervene before people walk out the door. Loyalty, Tom argues, isn’t dead. But the companies that want it back will need to earn it differently.

This episode is a must listen for leaders navigating culture in a hybrid world, and for founders wondering what culture really means when the rubber hits the road.

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.

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:

• How founders can turn board meetings into strategic assets
• When and why boards start thinking about leadership changes
• The real reason investors push for independent board members
• Why transparency—especially from the C-suite—is a signal, not a vulnerability

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.