AI can organize information faster than any team you’ve ever built. It can surface patterns, speed up workflows, and remove friction from execution. But it still can’t make judgment calls when the data is incomplete, the market is shifting, and real money is on the line.

In this episode of The Breakout CEO, Jeff Holman talks with entrepreneur and financial advisor Luigi “Lou” Rosabianca about where AI actually fits in a scaling business and where CEOs still have to step in and decide.

Lou has built and advised small and mid-sized businesses through multiple disruptions, from 9/11 to financial crises to the pandemic. His perspective is shaped by operating when capital tightens, banks pull back, and clean answers don’t exist. That experience informs how he thinks about AI, cash flow, and resilience today.

The conversation centers on a simple reality that many CEOs are living right now. Tools are more powerful than ever, but businesses still fail when leaders confuse automation with judgment. AI can help organize the ingredients, but CEOs still decide what gets cooked, what gets scrapped, and when it’s time to pivot.

This episode is for CEOs and founders who are navigating uncertainty, experimenting with AI, and trying to scale without losing control of the fundamentals. It’s a grounded conversation about decision-making, resilience, and why leadership judgment still compounds when everything else levels out.

Listen to the full episode of The Breakout CEO for a candid, operator-level discussion on scaling through chaos without outsourcing your judgment.

Check out Lou's work at https://www.shieldadvisorygroup.com/ and https://creditbanc.io/.

Say hello to Luigi!

LinkedIn: https://www.linkedin.com/in/luigi-rosabianca/

Enclosed is also a copy of his book (free audio version), Buying The American Dream - A Strategic Playbook for Acquiring Small Businesses. https://drive.google.com/file/d/1iCSh0yb8PrwKFo0AZnpjV4Z84YZj2Elx/view

If you want a paper copy, it’s also available on Amazon. http://bit.ly/3ZwSHnz.

Most leadership advice breaks down the moment real pressure shows up.

In this episode of The Breakout CEO, Cydni Tetro, 3-time CEO, board member, and former CIO of Swire Coca-Cola, draws from her experience as a 3-time CEO, enterprise executive, and board member to talk through those moments honestly. Not as lessons learned in hindsight, but as decisions made while the outcome was still unclear.

Cydni explains why people-centered leadership becomes harder as companies scale, not easier, and why many CEOs underestimate the operational cost of misalignment until it’s already doing damage. She also breaks down how “blue sky thinking” actually works inside real companies: not as vision work, but as a way to surface options teams stop seeing once constraints harden.

The discussion also addresses a reality many CEOs quietly face; isolation at the top, decision-making without certainty, and the internal weight of responsibility when outcomes rest on a few calls made under imperfect conditions.

If you’re building, scaling, or resetting a company and carrying the weight that comes with it, this one’s for you.

Check out Cydni's work at https://www.swirecocacola.com/.

Say hello to Cydni!

LinkedIn: https://www.linkedin.com/in/cydnitetro/

Facebook: https://www.facebook.com/cydtetro/

Instagram: https://www.instagram.com/cydtetro/

What does it take to build a company when the mission matters more than momentum?

In this episode of The Breakout CEO, Jeff Holman sits down with Thomas Bishop, founder of Paleblue, for a grounded conversation on conviction, persistence, and building products that genuinely change behavior. Tom shares how a near-death experience reshaped his career decisions and why meaningful missions became the filter for every company he chose to build.

The discussion traces Tom’s path through product development, global manufacturing, and consumer electronics, leading to the creation of Paleblue batteries and its focus on eliminating single-use battery waste. Along the way, Tom breaks down the real challenges of hardware entrepreneurship, from supply chain complexity to fundraising during market shocks, and why progress often comes from simply staying in the fight longer than others.

This episode offers practical insight for CEOs and founders navigating long build cycles, uncertain markets, and decisions that test personal conviction.

If you are building something you believe in and need a reminder of why staying in the course matters, this conversation delivers clarity without gloss.

Check out Tom's work at https://paleblueearth.com/.

Say hello to Tom!

LinkedIn: https://www.linkedin.com/in/thomas-bishop-bb67267/

Instagram: https://www.instagram.com/pale_blue_earth/

https://www.linkedin.com/company/pale-blue-earth/

Think you'd be a great guest on the show?

Apply https://go.intellectualstrategies.com/

Every CEO reaches a threshold where hustle and revenue aren’t enough.

In this episode of The Breakout CEO, host Jeff Holman cuts into the hard operating truths that separate early growth from a sustainable scale. We explore what happens when pricing, financial clarity, team leadership, and systems become the deciding factors—not just harder work or bigger marketing.

This conversation goes deep on the decisions that turn growth into lasting value: tightening margin discipline, aligning incentives, understanding true profitability, and building leadership capacity that can carry the business forward.

If you’re leading a scaling company and feel the tension between growth targets and operational reality, this episode speaks directly to the strategic shifts' CEOs have to make to break through to the next level.

Check out Dan's work at https://winktoolbox.com/ & https://bdexperts.com/.

Say hello to Dan!

Facebook: https://www.facebook.com/blackdiamondexperts

Instagram: https://www.instagram.com/bdexperts/

LinkedIn: https://www.linkedin.com/in/daniel-james-b2716022/

https://www.linkedin.com/company/blackdiamondexperts/

https://www.linkedin.com/company/wink-reports/

Think you'd be a great guest on the show?

Apply https://go.intellectualstrategies.com/

What does it really take to sell a SaaS business successfully?

In this episode of The Breakout CEO, Jeff Holman sits down with Andrew Gazdecki, founder of Acquire.com (formerly MicroAcquire) to unpack what founders need to know about buying, scaling, and exiting online businesses.

Andrew has helped thousands of founders sell SaaS companies, ecommerce brands, mobile apps, and digital businesses. In this conversation, he shares real stories from the trenches including a $2M SaaS exit by an 83-year-old founder and a $12M cross-border acquisition involving a Japanese buyer and big-bank financing.

This is not a theory. It’s what actually happens when founders decide to exit.

If you’re a SaaS founder, tech CEO, or entrepreneur thinking about growth, acquisition, or exit, this episode will challenge how you think about ownership and opportunity.

Listen through to the end for Andrew’s advice on persistence, patience, and why the hard parts of entrepreneurship are not a surprise. They’re the price of admission.

🎧 Subscribe to The Breakout CEO for weekly conversations with founders who’ve been through the hard parts and came out stronger.

Check out Andrew's work at https://acquire.com/.

Say hello to Andrew!

Facebook: https://www.facebook.com/acquiredotcom

Instagram: https://www.instagram.com/acquiredotcom/

LinkedIn: https://www.linkedin.com/in/agazdecki/

https://www.linkedin.com/company/acquiredotcom/

Think you'd be a great guest on the show?

Apply https://go.intellectualstrategies.com/

What does it really take to break through as a CEO when the pressure is highest, and the path forward isn’t clear?

In this episode of The Breakout CEO Podcast, I sit down with Nikky Kho @NikkyKho , an entrepreneur, AI pioneer, and lifelong learner for a wide-ranging conversation on the breakout moments that shape leaders at the highest levels.

Nikky’s journey is anything but conventional. Over a 25-year career, he built a company from zero to over $100 million in revenue, endured massive setbacks including crushing debt and public controversy, and reinvented himself at multiple stages most recently at the intersection of AI, entrepreneurship, and personal growth.

He also shares deeply personal stories from trekking to Everest Base Camp to rebuild businesses after major losses and the leadership principles that carried him through those moments.

This episode is for CEOs, founders, and operators who know that growth isn’t just about strategy; it’s about who you become when things get hard.

🎧 If you’ve ever questioned whether the struggle is worth it, this conversation will meet you right where you are.

Check out Nikky's work at https://nikkykho.com/.

Check out this bonus gift from Nikky to our listeners: https://realaidynamics.com/thankyouYPO/

Say hello to Nikky!

Facebook: https://www.facebook.com/NickKhoOfficial/

Instagram: https://www.instagram.com/nikkykho/

LinkedIn: https://www.linkedin.com/in/nicholaskho/

Twitter: https://x.com/nickkhoofficial

Think you'd be a great guest on the show?

Apply https://go.intellectualstrategies.com/

What does it really take to move from founder control to strategic optionality?

In this episode of The Breakout CEO podcast, Jeff Holman sits down with Heather Griffith Barber, founder of Queen of Wraps, to unpack the real decisions behind building a company that buyers take seriously.

Heather shares her 18-year journey growing a business from a scrappy family operation into a multi-company platform that ultimately attracted an unsolicited private equity offer. Along the way, she breaks down the choices most founders never think about early enough; location strategy, loss of leaders, customer lifetime value, and the leadership shift required when a business starts to outgrow its founder.

This conversation goes beyond tactics. It’s also about how women founders and CEOs build institutional credibility, create leverage, and design businesses that don’t depend on them to survive.

You’ll hear:

1. Why “location” became a growth accelerator not a vanity move
2. How treating the core product as a loss leader unlocked long-term customer value
3. What happens when a founder steps back and the business gets stronger
4. How Heather navigated personal inflection points while maintaining long-term strategic focus
5. Why strategic optionality, not growth at all costs, ultimately led to a successful exit

This episode is especially relevant for:

1. Woman founders scaling beyond the early hustle
2. CEOs thinking about governance, leverage, and exit readiness
3. Entrepreneurs building lifestyle businesses that still want real optionality
4. Operators curious about what private equity actually looks for in founder-led companies

Heather now focuses on helping more women founders gain confidence, knowledge, and long-term financial independence through entrepreneurship and exits, so success like this becomes normal, not novel.

Listen in to hear what it really takes to build a business that works with or without you.

Check out Heather's work at https://www.heathergriffithbarber.com/ and https://www.buy-scale-sell.com/.

Say hello to Heather!

LinkedIn: https://www.linkedin.com/in/heathergriffithbarber/

Instagram: https://www.instagram.com/buy_scale_sell/

Think you'd be a great guest on the show? Apply https://go.intellectualstrategies.com/

Scaling a business does not usually break because of strategy.

It breaks because the CEO is carrying too much.

In this episode of The Breakout CEO podcast, host Jeff Holman sits down with Corinne Morahan, founder and CEO of Grid + Glam, to talk about burnout, boundaries, and the leadership shift that changed how she built her business.

Corinne shares her journey from Wall Street to entrepreneurship, why she burned out more than once, and how getting her home organized unexpectedly reshaped the way she led. What started as a local home organization business grew into a luxury concierge move service and a multi-million dollar company serving high performing clients. They also dig into one of the most pivotal moments in Corinne’s growth as a CEO. Hiring a full-time operator, stepping out of the day to day, and learning to take calculated risks instead of trying to do everything herself.

In this episode, you will hear about:

1. Burnout and why it keeps showing up for founders
2. Organization as a leadership skill, not a personality trait
3. Building and pricing a high-end service business
4. The risk and relief of stepping out of daily operations
5. Why calculated risks matter more than bold ones

If you are a CEO, founder, or business owner feeling stretched thin, this episode will help you rethink where your time, energy, and attention are actually going.

Check out Corinne's work at https://www.gridandglam.com/

Say hello to Corinne!

Facebook: https://www.facebook.com/gridandglam

Instagram: https://www.instagram.com/gridandglam/

LinkedIn: https://www.linkedin.com/company/gridandglam/

Pinterest: https://www.pinterest.com/corinneam/

LinkedIn: https://www.linkedin.com/in/corinnemorahan/