253 | How AI Is Changing the Way Companies Scale with Casey Woo
The Business of You with Rachel Gogos
Release Date: 01/13/2026
255 | The Hidden Cost of Growth and How Smart Leaders Fix It with Megan Crabtree
The Business of You with Rachel Gogos
Behind every growth problem is a lack of structure. Many businesses scale fast, only to realize they've outgrown their systems, their teams, and sometimes even themselves. The result? Burnout, chaos, and missed opportunities are hiding in plain sight. In this episode of The Business of You, we explore what it really takes to grow a business with intention — learning from someone who survived the burnout and chaos caused by the hidden traps of growth for growth’s sake. This conversation is about leadership that balances people and performance, and why data without heart (or heart without...
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254 | How Accountability Creates Freedom in Business and Life with Robert Hunt
The Business of You with Rachel Gogos
What if the thing you’re avoiding is the very thing holding you back? Accountability often gets a bad reputation — as pressure, control, or punishment. But what if accountability is actually the key to freedom, clarity, and sustainable success? In this episode, we explore why so many leaders feel stuck even though they “know what to do,” and how ownership — not excuses — is what creates real momentum. Robert Hunt is the founder of REF Dallas, a CEO peer group and leadership platform he’s grown since 2013. Known as “The Accountability Guy,” Robert helps leaders reclaim...
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253 | How AI Is Changing the Way Companies Scale with Casey Woo
The Business of You with Rachel Gogos
What if the most important people in a company are the ones no one talks about? They’re the builders behind the scenes. The operators who organize chaos, fix what’s broken, and quietly turn vision into reality. Scaling isn’t glamorous — but it’s essential. In this episode, we explore what it really takes to grow companies fast and smart, and how AI is accelerating the shift toward adaptable, cross-functional leadership. Casey Woo is a public market investor turned high-growth technology COO and CFO with more than two decades of experience helping companies scale. He’s served as a...
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252 | What Founders Need to Know About Bringing a Product to Market with Kerim Kfuri
The Business of You with Rachel Gogos
If you’ve ever dreamed of launching a physical product—turning an idea into something tangible—you’ve probably noticed how overwhelming the process can feel. Manufacturing, sourcing, quality control, logistics, global suppliers…every step has layers most founders never see until they’re already in trouble. In a world where disruptions happen daily and the global economy shifts without warning, the founders who succeed aren’t just innovative—they’re prepared. Today’s guest, Kerim Kfuri, brings more than two decades of global supply chain expertise spanning technology,...
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251 | What It Really Takes to Succeed on Amazon with Pasha Knish
The Business of You with Rachel Gogos
If you’ve ever looked at Amazon and wondered how some brands scale effortlessly while others disappear into a sea of competitors, you’re not alone. Amazon can feel like an unpredictable giant—full of opportunity, but also packed with complexity. And as more entrepreneurs jump in, the brands that win aren’t the ones chasing trends…they’re the ones building with intention. Today’s guest, Pasha Knish, has lived through every era of Amazon—from the Wild West days of early e-commerce to today’s data-driven, hyper-competitive marketplace. With more than 13 years of hands-on selling...
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250 | The New Rules of Paid Advertising and What's Working Now with John Horn
The Business of You with Rachel Gogos
Have you ever wondered why some brands seem to crack the code with paid ads while others burn through budget with nothing to show for it? If you’ve ever dabbled in Google Ads—or avoided them out of fear of expensive mistakes—this conversation will open your eyes to what’s possible when strategy and execution align. John Horn, CEO of StubGroup, has helped hundreds of companies transform underperforming campaigns into profitable acquisition machines. His team is ranked in the top 1% of Google Partners worldwide for performance and customer care—and their reputation is...
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249 | The Hidden Skills That Make Great Leaders With Vicky Brown
The Business of You with Rachel Gogos
You know that moment when someone sees something in you long before you’re ready to claim it? For many leaders, that moment becomes the spark that changes everything. For Vicky Brown, it was the gentle (yet persistent) nudge that pushed her from devoted “number two” to founder of a thriving HR firm that’s been supporting high-performance companies for more than two decades. Too often, business owners think of HR as paperwork, policies, or “the stuff you deal with when something goes wrong.” But Vicky’s story—and her expertise—reveal a very different truth: HR is leadership....
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248 | The Most Powerful Leadership Skill No One’s Talking About with Keri Ford
The Business of You with Rachel Gogos
When success starts to feel like stress, what if your body could tell you why? For high-achievers, it’s easy to push harder, hustle faster, and ignore the quiet signals of exhaustion. But for Keri Ford, those signals became her greatest teachers. A former Creative Director turned award-winning CEO, Keri discovered that the real key to high performance isn’t found in strategy or mindset — it’s found in the nervous system. Through her groundbreaking Somatic Success® method, Keri has helped elite women — from celebrity clients like Alison Sweeney and Kaley Cuoco to powerhouse founders...
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247 | Turning Your Story into Sales With Dr. Danny Brassell
The Business of You with Rachel Gogos
What if the fastest way to grow your business isn’t marketing harder, but speaking smarter? In this episode, Dr. Danny Brassell shares how to make storytelling and public speaking your most powerful tools for attracting clients, building authority, and confidently closing deals. Known as the “Jim Carrey with a Ph.D.,” Danny has spoken to over 3,500 audiences worldwide and co-founded The WellCrafted Story Workshop™, where he teaches entrepreneurs how to transform their stories into client-generating presentations. The Power Of Clarity And Connection If you’ve ever struggled to...
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246 | Don’t Scale Your Business Without Hearing This Franchise Model with Bennett Maxwell
The Business of You with Rachel Gogos
What happens when business growth outpaces the guardrails that keep it sustainable? This week, I sit down with Bennett Maxwell, serial entrepreneur, investor, and founder of Franchise KI—best known for scaling Dirty Dough Cookies from one store to over 450 franchises sold in just two years. After experiencing both the highs and the chaos of hypergrowth, Bennett now helps entrepreneurs build wealth through franchising the right way: with systems, structure, and staying power. How To Grow Fast Without Burning Out Bennett reveals the critical mistakes founders make when scaling too...
info_outlineWhat if the most important people in a company are the ones no one talks about?
They’re the builders behind the scenes. The operators who organize chaos, fix what’s broken, and quietly turn vision into reality. Scaling isn’t glamorous — but it’s essential.
In this episode, we explore what it really takes to grow companies fast and smart, and how AI is accelerating the shift toward adaptable, cross-functional leadership.
Casey Woo is a public market investor turned high-growth technology COO and CFO with more than two decades of experience helping companies scale. He’s served as a six-time CFO and two-time COO across software, hardware, marketplaces, and eCommerce.
He’s also the founder and CEO of The Operators Guild, a global community of over 1,000 top operators, as well as FOG Ventures and Guild Talent — all built to support the people who actually make companies run.
In this conversation, Casey breaks down what it means to be a “scaler,” how AI is reshaping the value of specialization, and why operators are the backbone of every high-growth company.
From Investor to Operator
Casey shares his journey from Wall Street to Silicon Valley and why leaving a prestigious investing career was both terrifying and freeing.
The money and status were there, but fulfillment wasn’t. That realization pulled him into early-stage tech, where he discovered his true passion: building companies from the inside out.
As an operator, Casey learned that scaling isn’t about titles — it’s about solving problems. Finance, operations, strategy, leadership — whatever the company needs, the role stays the same.
That mindset eventually led to the creation of The Operators Guild, which began as a small breakfast group for overlooked CFOs and COOs and grew organically into a global community.
Why AI Rewards the Elite Generalist
Casey offers a practical take on AI — not as a threat, but as leverage for the right leaders.
As AI replaces narrow, repetitive specialist tasks, the advantage shifts to people who can think horizontally, connect ideas, and move across functions with ease.
Early-stage founders and operators are uniquely positioned to thrive in this environment, using AI as a team of “semi-specialists” to move faster and build smarter.
Rather than abandoning your strengths, Casey encourages leaning into them — and using AI to amplify what you already do best.
This is the rise of the modern business artist.
Enjoy this episode with Casey Woo…
Soundbytes
13:42-13:55
“Scalers are highly creative. They are generally impatient. They love the intellectual stimulation of organizing chaos, solving problems. So they run towards problems.”
19:26 – 19:44
“AI literally is intelligence, right? Artificial intelligence. Right. So it’s starting to be like a human and specifically, the easiest thing for it to start is anything specialized. Because anything specialized is homogenous.”
Quotes
“Scaling is actually very nuanced. It’s not just, ‘Oh, finance needs a CFO.’ No — you don’t need a CFO at Series A.”
“Scalers are highly creative. They are generally impatient.”
“AI is moving the world away from hardcore specialists.”
“I could go to a corporate job, but my soul would die.”
Links mentioned in this episode
From Our Guest
Website: https://operators-guild.com/
FOG Ventures: https://fog.ventures/
Connect with Casey Woo on LinkedIn: https://www.linkedin.com/in/caseywoo
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