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In this episode, Drew sits down with Igor Gorlatov, founder of Advisory5, to talk about building in regulated industries in the age of AI. Igor explains why FDA clearance is only the open gate, how the payer and provider fight shapes every product, and why the founders who win find a wedge instead of trying to rebuild the system. Drew shares the moment an executive coach told him his bias toward action had become a weakness, and they dig into why reflection feels good but action is where things change. They close with Drew’s VHS, DVD, and streaming view of AI maturity, an Iron Man metaphor, and why most companies skip the unglamorous foundation work.
Takeaways
Chapters
00:00 Cold open: reflection versus action
01:21 Intro to the show and Igor
02:01 Igor’s story: go to market to health innovation
03:42 Why building in healthcare is still slow in the age of AI
04:48 The fog: payers, providers, and who profits
06:58 Trust and relationships when you are an industry outsider
10:56 Aligned incentives and the Garner Health example
12:48 Helping early stage founders in Charlotte
14:56 Should you offer equity to strategic advisors?
17:37 How Advisory Five builds trust through a team of advisors
19:49 How executives can use advisors
23:18 Reflection versus action
24:46 Drew’s coach and the bias toward action
29:52 Finding your wedge: three health tech case studies
33:20 The same problems show up in every industry
35:51 Incremental efficiency versus big bets
38:46 VHS, DVD, and streaming: AI maturity
42:03 Software on demand and the plumbing nobody sees
45:18 Iron Man and agent harnesses
47:22 Why the people stuff is the real barrier
49:29 The unsexy foundation work
50:35 Practical advice and what to stop doing
54:02 Closing thoughts
54:53 Where to find Igor
Connect with Igor & Advisory Five
LinkedIn: https://www.linkedin.com/in/gorlatov/
Website: https://www.advisory5.com/
Connect with Drew & StealthX
LinkedIn: https://www.linkedin.com/in/drewhburdick/
Website: https://stealthx.co/
In this episode, Drew sits down with Harold Hughes, founder and CEO of Divi and an angel investor, to talk about how to build a company in the age of AI. Harold shares why starting is easier than ever but staying in the market is harder, why a prototype beats a pitch deck, and a simple trick for getting honest feedback from friends: tell them you are thinking of investing. Drew tells the story of how posting about Charlotte Startup House in public, and going to a lunch he did not want to attend, led to finding the house. They also get into why content and education build trust, why design and taste matter when anyone can build with AI, and why information should work like a library, not a vault.
Takeaways
1. AI makes it easy to start a company, but harder to stay in the market, because a competitor can start tomorrow.
2. If you want investor money, show up with a working prototype. A pitch deck alone no longer works.
3. Execution is no longer the bottleneck. Finding a real customer pain point is.
4. The most common reason startups fail is no market demand, so talk to more humans than you think you need to.
5. To get honest feedback, tell friends you are thinking of investing in the idea instead of telling them you are building it.
6. Treat your company like a content studio. Education and entertainment build trust.
7. Your social capital is your biggest currency, so show up online as a round character with your work and your personal interests.
8. Everything you want is on the other side of discomfort, and the cringe of posting and talking to people is a barrier to entry for your competitors.
9. Products built with AI often look like it, so design and taste are what make people remember you.
10. Treat information like a library, not a vault. They can copy the recipe, but they cannot copy the chef.
Chapters
00:00 Cold open: "Easy to get into market, hard to stay in"
00:29 Intro to the show and guest
01:55 Harold's story: corporate, Bandwagon, and Divi
05:15 What Divi does for angel investors
06:22 Building a company in the age of AI
09:24 Pitch decks, bootstrapping, and building alone
11:11 Talk to real humans, and the "invest in it" trick
15:01 Why likes do not equal sales
17:38 Getting customers in a noisy market
20:51 Luck surface area and zagging
23:27 Everything you want is on the other side of discomfort
26:31 How Charlotte Startup House got built in public
31:40 Building with AI without it looking like AI
37:14 Non technical founders and vibe coding
39:38 Information as a library, not a vault
43:00 Where to find Harold
Connect with Harold & Divi
Website: https://divi.fund
LinkedIn: https://www.linkedin.com/in/haroldphughes/
Instagram: https://www.instagram.com/haroldph/
Connect with Drew & StealthX
LinkedIn: https://www.linkedin.com/in/drewhburdick/
Website: https://stealthx.co/
In this episode, Drew sits down with Sal Perez, founder of Totem Wealth Management in Charlotte, to talk about what AI means for client experience. Sal grew up in Orlando, played soccer at Winthrop, started his career at Vanguard, and opened his own firm in 2023. They get into why AI note takers make advisors more present, why clients still want a person to hold accountable, and what a handwritten note from a Tupperware CEO and a Ritz Carlton guest notes system teach about paying attention. They also cover hiring for what can't be taught, how AI helps a team personalize at scale, and why Drew tells clients to work in four to six week bets.
Takeaways
Chapters
00:00 Cold open: the handwritten note
00:36 Intro to the show and guest
01:10 Sal's background: soccer, Winthrop, Vanguard, starting Totem
03:04 Drew's 2022 story: live AI coaching for wealth advisors
04:53 Getting clients comfortable with AI and whether it replaces advisors
08:30 People buy from people, and note takers for doctors and advisors
10:23 AI as a filter and why people hire white glove service
12:01 Accountability: who do you yell at?
14:11 Listening instead of solving
15:34 Moments that matter and big life events
17:30 Testing Gemini with a loss scenario and Sal's mom the hairstylist
19:45 Curation and investing in relationships
22:24 The Tupperware CEO and the handwritten note
25:42 Jelly Bellies and the Ritz Carlton Mystique system
28:40 Who is doing AI well and hiring for the intangibles
30:56 The core four
33:07 Using AI to personalize at scale
34:36 Staying present with an AI note taker
35:59 The Iron Man suit
37:26 High agency: build the raft
38:56 Why Copilot alone is not a strategy and what AI does to software companies
40:58 Four to six week bets and the betting table
43:30 Good Strategy, Bad Strategy: Blockbuster and Kodak
44:49 Generation or mindset?
47:18 Final takeaways and where to find Sal
Connect with Sal
LinkedIn
Instagram
totemwealthmanagement.com
Connect with Drew
LinkedIn
stealthx.co
In this episode, Drew sits down with Brian Lafontaine, a working actor of over 30 years turned executive coach, to explore what actually differentiates a person or a brand once AI can produce a flawless email, pitch, or blog post in seconds. The conversation covers why two recent job candidates tried interviewing using an AI avatar, why vulnerability builds more trust than polish, and how founders can use acting techniques like eye contact and presence to connect authentically with customers and teams. Brian shares insights from coaching executives, authors, and entrepreneurs, plus a look inside Speakeasy, the storytelling event he runs monthly in Charlotte.Takeaways1. Presence cannot be faked or replicated by AI, it only happens in the room in real time.2. The imperfections and quirks people try to hide are often what make them the most relatable.3. Trust is earned through connection, not through polish.4. The cost of real connection is risk, and that risk is what makes it worth something.5. Attention gets all the credit, but presence is what actually builds trust.6. The things that do not scale, like one on one conversations, will become the most valuable thing a business offers.7. Story connecting means linking someone's personal origin story to their professional identity.8. Building in public brings customers into the journey and builds buy in before the product is even finished.9. Naming your own nervousness out loud actually makes people trust you more, not less.10. AI has no stakes. Humans have everything to gain and lose, and that is what makes the human experience worth having.Chapters00:00 Cold open: "AI has no stakes"01:04 Intro to the show and guest01:58 Brian's background as a working actor02:37 Origin story: from stand up comedy to his first stage role03:52 Movies and shows: Ozark, Stranger Things, Dawson's Creek04:51 Drew's Banshee audition story06:00 Topic kickoff: authenticity in the age of AI06:06 The AI avatar job interview story08:04 Why presence cannot be faked10:38 Drew's own story: the T shirt brand he used to hide12:38 Trust is earned through connection14:05 The sea of sameness15:51 The price of connection is risk18:31 Attention vs presence19:38 Why the things that do not scale matter more24:00 Listening to understand vs listening to respond25:10 Who benefits most from this work29:14 The Mount Rushmore strategy and personal brand31:25 Building in public33:07 Why people like to see the struggle35:15 Brian coins "story connecting"36:13 What Speakeasy actually is39:35 The eye contact exercise45:44 Practical tips for showing up53:56 Be where your feet are57:12 Naming the elephant in the room1:01:11 Wrap up and tying back to the show1:01:58 Where to find Brian and SpeakeasyConnect with Brianhttps://www.linkedin.com/in/brian-lafontaine/https://brianlafontaine.comConnect with Drewhttps://www.linkedin.com/in/drewhburdick/https://stealthx.co/
In this episode, Drew sits down with Tory Thompson, Head of School at Elysium School of Innovation — a hybrid micro school in Huntersville, NC. Students are in the classroom two days a week, learning remotely two days, and out in the world on "field experience" Fridays, at a 10-to-1 ratio. Tory's path to running a school started with her own son: one of the brightest kids she knew, quietly failing fourth grade in a traditional classroom. When the hybrid program that turned him around got shut down, she built her own.
Tory and Drew get into what education actually looks like in the age of AI — not as a threat to be managed, but as the first real chance to teach every kid at their own level.
The conversation explores:
If you're a parent trying to prepare your kids for a world that's changing faster than the curriculum, or an educator trying to figure out where AI actually fits, this one is worth your time.
Chapters
00:00 – Intro: what a hybrid micro school actually is
02:05 – Tory's path: teacher, tutoring company, four kids
04:20 – COVID, homeschooling, and a bright kid struggling
09:06 – From failing fourth grade to the top 9% in the state
11:22 – The program gets cancelled, so she builds her own school
15:52 – 4,000 missing middle school seats and the hybrid model
18:17 – Every new tool starts as a threat: AI as the great equalizer
20:38 – Foundations first: hallucinations and verifying the source
22:57 – What guardrails actually look like
25:09 – "He hacked the game I made him"
29:48 – Protecting childhood and giving family time back
32:02 – Progress over perfection: 1.5x growth in three months
34:24 – Teaching financial literacy: lemonade stands and mutual funds
39:01 – "The valedictorian is often just the best cheater"
43:43 – AI won't replace teachers, it will outdate the ones who ignore it
46:00 – Scaling micro schools, community, and being known
50:36 – The "Age of Innovation": the stuff we wish we'd been taught
55:14 – 700 reports in an hour: amplify, don't offload
Connect w/ Tory & Elysium School of Innovation:
https://www.linkedin.com/in/tory-thompson/
https://elysiumschools.org
Instagram: @elysiumschools
Connect w/ Drew & StealthX:
https://www.linkedin.com/in/drewhburdick/
https://stealthx.co
In this episode, Drew sits down with Ellie Holbert, Founder and Principal of Impact Advisory Services, to explore why psychological safety has become the most critical leadership skill in the age of AI. The discussion covers the neuroscience behind fear and performance, why 47% of employees can't explain their own job responsibilities, and how leaders can create high-performing teams even when uncertainty is at an all-time high. Ellie shares insights from advising executives at organizations of all sizes, including a case study where an underperforming team unlocked $4.5 million in value through foundational team architecture work.
Takeaways
Chapters
00:00 Introduction to Ellie Holbert and Impact Advisory Services
02:55 Ellie's Journey: From Management Consulting to Entrepreneurship
04:14 Why Psychological Safety Matters More Than Ever
06:22 Above the Line vs Below the Line Thinking
08:07 High Agency Teams and Creating Safe Environments
10:10 The Hidden Cost of Repeated Mistakes
16:11 Pixar's Brain Trust: A Model for Psychological Safety
19:29 Practical Advice for Mid-Size Companies
24:18 After-Action Reviews and The Culture Code
29:10 Top 3 Things Every Executive Should Do
34:13 Using AI as a Coaching and Regulation Tool
40:48 The Future of Work: Why Human Skills Matter More
45:12 Case Study: From 2.4 to 4.8 Team Effectiveness
47:30 Where to Find Ellie and the Team Effectiveness Assessment
Connect with Ellie & Impact Advisory Services
https://www.linkedin.com/in/ellieholbert
Take the free Team Effectiveness Assessment
Connect with Drew & StealthX
https://www.linkedin.com/in/drewhburdick
https://stealthx.co/
In this episode, Drew sits down with Brett House, founder and CEO of High Signals, and Rio, leader of advertising and ad tech at Cradera (OmniCom), to explore how AI is fundamentally reshaping go-to-market strategy, customer experience, and the future of software. The discussion covers GTM compression, synthetic data for buyer simulation, the agentic commerce debate, and what happens when AI agents start making buying decisions on our behalf. Drew shares how he built a custom CRM with Claude Code and cancelled HubSpot, and the three unpack why "English is the next coding language." Brett and Rio also host Signal & Noise, a podcast covering ad tech and martech trends.Takeaways1. GTM cycles are compressing from months to days thanks to AI-powereddecisioning.2. Synthetic data and simulated focus groups can now test at scale faster than traditional methods.3. Best product doesn't always win. Best marketing and founder-market fit wins.4. Agentic commerce is coming, but the timeline is debated. Brett is skeptical, Rio is bullish.5. AI agents will eventually make buying decisions based on ROI per token usage.6. You can build a functional CRM with Claude Code and cancel your SaaSsubscriptions.7. The concept of a "power user" is dying. AI-native software won't need 50 knobs and controls.8. English is the next coding language. You don't need to write Python to build tools.9. Leaders should delegate everything possible to AI first, then focus on decisions only they can make.10. Think of go-to-market as an operating system, not just messaging. Alignproduct, marketing, sales, and customer success around one playbook.Chapters00:00 Teaser: I Cancelled HubSpot00:01 Introduction to Brett House and Rio01:22 Rio's Origin Story: Journalism to Ad Tech05:04 Brett's Origin Story: Comp Lit Major to Founder10:23 Trends in GTM, Ad Tech, and Martech12:38 GTM Compression: From Months to Days17:27 Synthetic Data is Actually Good Now19:19 Best Product Doesn't Win, Best Marketing Wins24:06 Agentic Commerce: Will AI Agents Buy for Us?26:16 Brett Pushes Back on Agentic Commerce29:21 Rio Disagrees: We'll Get Comfortable Over Time30:18 I Cancelled HubSpot After Building a CRM with Claude Code35:35 The Death of the Power User40:33 My COO Agent Built a Dashboard Without Being Asked42:53 English is the Next Coding Language43:38 Brett's Advice: GTM as an Operating System45:36 Rio's Advice: Delegate to AI First49:11 Where to Find Brett and RioConnect with Brett & High Signals / bretthouse https://www.highsignals.comConnect with Rio / riolongacre Signal & Noise Podcasthttps://open.spotify.com/show/signaln...https://podcasts.apple.com/us/podcast...Tweet Referenced in This Episodehttps://x.com/flynnjamm/status/202346...Connect with Drew & StealthX / drewhburdick https://stealthx.co/
In this episode, Drew sits down with Webb Bostic, President and CEO of MessageBridge, to explore the evolving landscape of business text messaging and what happens when AI becomes the gatekeeper to your customers. The discussion covers the SMS ecosystem from carriers to platforms, the difference between good and bad text experiences, the upcoming RCS protocol shift, and a thought-provoking look at a future where AI agents screen messages before humans ever see them. Webb shares insights from building messaging platforms for B2B companies and advocacy organizations, and offers practical advice for businesses looking to leverage text as a strategic channel.Takeaways1. Text messaging remains the most direct channel to reach customers in the US market.2. 98% of Americans own a phone and over 90% read texts within minutes.3. The US is unique—SMS dominates here while WhatsApp and WeChat lead globally.4. There's a right way and wrong way to use text messaging for customer engagement.5. Trust must be established before jumping into sales or marketing sequences.6. RCS (Rich Communication Services) is rolling out and will make SMS feel like iMessage.7. AI agents will soon act as intermediaries, screening texts before humans see them.8. AI is actually more predictable than humans—this creates new opportunities.9. Businesses need to learn from their messaging data to stay ahead of these shifts.10. Text messaging should be treated as a strategic channel, not an afterthought.Chapters00:00 Introduction to Webb Bostic and MessageBridge02:49 Webb's Journey: From Bandwidth to Building Messaging Platforms05:10 Why Text Messaging is Underrated in Business06:43 The US Market: Why SMS Still Dominates08:07 The Threat: Don't Let Text Become the Next Email10:00 Good vs Bad Text Experiences: The Doctor's Office and Daniel14:15 Building Trust Through Text: Permission-Based Outreach17:10 The SMS Tech Stack Explained: Carriers, Platforms, and Tools24:00 AI Agents as Intermediaries: The Future of Messaging32:41 When Siri Screens Your Texts Before You See Them37:00 The Flip Side: AI is More Predictable Than Humans41:27 How Businesses Should Prepare for AI Gatekeepers44:30 Practical Advice: Getting Started with Text Messaging48:00 Where to Find Webb and MessageBridgeConnect with Webb & MessageBridgehttps://www.linkedin.com/in/webb-bostic-a761b113/https://www.messagebridge.com/Connect with Drew & StealthXhttps://www.linkedin.com/in/drewhburdick/
https://stealthx.co/
In this episode, Drew sits down with Michael Trivette, Co-Founder of College Transitions, to explore the evolving landscape of higher education in the age of AI, focusing on the role of College Transitions in guiding students through the college admissions process. The discussion highlights the importance of liberal arts education, the impact of AI on job markets and college admissions, and the significance of building relationships and brand equity in education. The speakers share insights on tools and resources available for students and offer advice on navigating the college experience successfully.
Takeaways
Chapters
00:00 Introduction to College Transitions and AI in Education
02:42 Michael's Journey: From Broadcasting to Higher Education
05:30 The Impact of AI on Higher Education
08:21 The Role of Liberal Arts in a Changing Job Market
11:01 Adapting to AI: Universities' Response
13:49 Embracing AI in College Admissions
15:33 Navigating the Changing Landscape of Education
18:22 Adapting to AI in Education
21:04 Building Brand Equity in a Competitive Market
26:48 The Importance of Long-Term Thinking
30:22 Highlighting Successful Innovations in Education
32:03 The Evolution of College Application Platforms
36:45 Navigating the College Admissions Landscape
43:13 The Role of AI in College Admissions
46:37 Embracing the College Experience
Connect with Mike & College Transitions
Connect with Drew & StealthX
https://stealthx.co/
In this episode, Drew sits down with Rob Horton, Senior Vice President of Brand and Digital at the YMCA of Greater Charlotte, to explore the future of customer experience, modern marketing, and how AI is reshaping personalization.
Rob’s background spans iconic CPG brands (Nestlé, Coca-Cola), a decade in architectural coatings, agency leadership, and economic development—before stepping into a mission-driven marketing role at one of Charlotte’s most community-rooted organizations. That breadth gives him a uniquely sharp understanding of what today’s consumers actually expect: clarity, relevance, guidance, and meaningful human connection.
Drew and Rob unpack the Y’s modernization efforts—Salesforce, Marketing Cloud, first-party data, and personalized onboarding and discuss the broader shifts happening across marketing as AI accelerates. They dive into why “guide, don’t inform” is becoming a foundational principle, how brands should blend analog and digital moments, and what leaders should focus on to stay competitive.
What you’ll learn in this episode
Chapters
[00:00] – Rob’s Origin Story & Career Arc
[03:40] – B2B vs. B2C & the Thread Across All Marketing
[05:45] – The Future of Experience: Guide, Don’t Inform
[08:00] – Personalization 2.0: From Segments to Individual Journeys
[12:25] – Modern CRM: Salesforce, Marketing Cloud & Retention Intelligence
[18:25] – Best-in-Class Personalization Examples
[20:30] – The Analog/Digital Intersection
[27:20] – Human Touch vs. AI Automation
[29:35] – Practical Advice for Mid-Market Leaders
[37:55] – Final Lessons & Where to Connect with RobConnect w/ Drew & StealthX
Connect w/ Rob Horton
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