The Breakout CEO

What do you do as a CEO when the supplier behind most of your inventory disappears overnight? Rupesh Sanghavi, founder of Ergode, faced exactly that when half.com shut down and took 80 to 90 percent of his inventory source with it. In this episode of The Breakout CEO, he walks through how each disruption, from a lost supplier to a ceiling on C2C margins, the COVID acquisition window, and tariff uncertainty, pushed his ecommerce company into its next business model.

Rupesh started by buying a textbook on eBay and pre-selling it on Amazon, then wrote software to automate the buying while still working as an application engineer. He explains why he launched a second business to work directly with brands, how moving to brand ownership pushed margins past double digits, and the acquisition criteria that led him to walk away from deals that looked great on paper while others were reportedly paying 9 to 12 times EBITDA.

He also gets candid about the two decisions he believes held the company’s growth back: closing his mind to outside investors, and the years he let someone else run technology, which he calls the least growth years. For founders weighing growth capital, team building, or how closely to stay involved in technology in the age of AI, this conversation shows what those choices can cost. Rupesh Sanghavi is the founder of Ergode, ergode.com.

00:00 Lessons From Scaling E-Commerce

01:59 From Engineering to Entrepreneurship

05:17 The $1,600 Textbook Sale

08:05 Building a Side Business

12:21 Creating a Brand Ecosystem

16:38 Losing Most Inventory Overnight

18:58 Acquiring Brands During COVID

22:41 Prioritizing Team and Technology

25:09 Becoming a Servant Leader

27:02 Choosing Will Over Skill

34:14 Evaluating Brand Acquisitions

47:51 Lessons That Limited Growth

What should a CEO do when the team and the offices are built for a $2M investment that never arrives? Asaf Darash faced that decision after spending about a year funding Regpack with his own money and loans while an angel investor’s committed $2M kept getting pushed back, until the investor went bankrupt. He had to choose between searching for new investors or bootstrapping, and he chose to cut the team from 12 or 13 people to 3 and spend a year working 14-hour days.

Asaf explains why he believed the technology had to prove itself for 400 organizations, not just 4, before taking outside money. He also describes the revenue signal that told him the company would make it, and how staying founder-owned changed the financial outcome available to him. Along the way he shares how Regpack turned a marketing message that produced no leads into one that brought them in, why a free trial attracted exactly the clients the company didn’t want, and how a serious burnout led him to give his team full authority over their goals and budgets.

00:00 Firing Everyone to Survive

01:19 From Academia to RegPack

06:11 Learning Beyond Technical Expertise

10:02 Mastering Sales and Marketing

15:00 Building Infinite Product Flexibility

21:02 Why Feature Marketing Failed

25:11 Marketing in Four Seconds

30:14 Customers Want Clear Actions

35:00 Free Trials Attract Wrong Customers

40:49 Bootstrapping With Two Teammates

45:43 How AI Changed Technology

50:23 Burnout Forced Leadership Change

Asaf Darash is the founder and CEO of Regpack, onboarding software for education and service-based organizations, at regpack.com.

Most CEOs get hiring wrong in one of two ways: they wait too long to bring someone on, or they panic and fill the seat with the wrong person the moment the pressure hits. Darren Tompkins, founder of Vader-Rey Companies, has spent years watching that pattern play out across the scaling businesses he works with in Houston's oil and gas, engineering, and construction market, and he has a simple diagnostic for when a CEO is overdue to delegate: watch your own personal time, not a revenue number.

In this conversation, Darren breaks down why support functions like legal, IT, and back office operations quietly fall behind while a company chases new revenue, and why that gap is often what actually crushes a scaling business, not the sales slowdown everyone expects. He also explains why he treats recruiting less as a transaction and more as a strategic partnership built around a client's real long-term plan, and why most job descriptions fail to attract the right talent because they were never written for the specific person a CEO actually needs.

00:00 Avoid Hiring Too Late

01:18 Three Companies, One Talent Mission

04:13 The First Executive Decision

08:18 Recruiting as Strategic Partnership

11:22 Set a Date and Leave

20:00 The Virtual Workforce Advantage

24:31 Common CEO Hiring Mistakes

28:13 Why Support Teams Fall Behind

34:05 Where Process Meets Creativity

37:24 Beyond Generic Job Descriptions

41:06 The New Employee Marketplace

42:45 Getting Time and Peace Back

Darren Tompkins is the founder and CEO of Vader-Rey Companies, which provides recruiting, project staffing, and virtual professional support to scaling CEOs and owners.

Most businesses chase new clients while leaving real revenue sitting untouched inside the ones they already have. In this episode, business coach and consultant Stacey Hylen — who mentored under Chet Holmes and later served as VP of Consulting for Tony Robbins' Business Mastery brand — breaks down her Hidden Profits framework: a way to grow revenue through upsells, client reactivation, and deeper account mining, without spending another dollar on marketing.

Stacey also explains why the real constraint most CEOs face isn't a lack of resources, but a lack of resourcefulness — and why that reframe changes what to focus on first.

Stacey Hylen works with seven- and eight-figure B2B founders who are excellent at their core business but haven't built repeatable marketing and sales systems around it. Her Hidden Profits methodology, born out of a moment she witnessed live at a Tony Robbins event during the 2008 recession, centers on a simple but often-overlooked question: what revenue is already available inside your existing clients and products? In this conversation, she walks through how that question has driven results ranging from a 48% sales increase at a family-owned auto parts store to multi-million-dollar account growth built entirely from mining relationships that were already in place.

00:00 Resourcefulness Unlocks Hidden Profits

01:24 Learning From Chet and Tony

04:13 When Successful CEOs Need Coaching

06:12 Coaching Should Remove Work

09:20 Scaling Sales Beyond the Founder

11:13 The Cost of Endless Hustle

15:20 Creating Boundaries for Family

18:20 Finding Hidden Profits

21:32 One Upsell Grows Sales 48%

25:06 The $700,000 Reactivation Mistake

30:40 Mining Your Existing Clients

33:14 Working in Your Genius Zone

Most brand and portfolio decisions inside scaling companies get made from the inside out — shaped by org charts, legal deadlines, and internal politics rather than what customers actually experience. Behavioral-science brand strategist Kevin Perlmutter, founder of Limbic Brand Evolution, argues that the fix isn't a bigger rebrand — it's a standing question leaders ask before any brand or portfolio decision gets finalized: where are the insights?

Drawing on real client situations — from a four-day deadline to name a newly acquired company to untangling a four-brand portfolio boxed in by its own building — Kevin walks through what changes when customer insight, not internal convenience, drives the decision.

Episode Description

Kevin Perlmutter has spent more than three decades in advertising and branding, including 16 years at ad agencies and seven years at one of the world's largest brand consultancies, before founding Limbic Brand Evolution in 2019. His approach is rooted in behavioral science: the idea that customers choose and stay loyal to brands for emotional reasons, not because of features or internal talking points.

In this conversation, Kevin explains the diagnostic pattern he sees repeatedly across CEO engagements — brand and naming decisions made from internal logic instead of customer insight — and the framework he uses to correct course, including how he handles pressure-filled moments like acquisitions and portfolio restructuring.

00:00 Building Brands From Customer Insight

01:14 Behavioral Science Meets Brand Strategy

04:15 Why Internal Messaging Falls Short

07:28 Emotions Drive Customer Decisions

09:33 Why Brand Names Need Strategy

13:19 What a Brand Truly Is

15:46 When CEOs Need Brand Help

18:06 Navigating Brands After Acquisitions

20:14 Simplify the Customer Experience

22:30 Why Customers Choose Easy Paths

25:37 Turning Insights Into Brand Desire

29:12 Always Ask Where Insights Are

Most CEOs already agree AI belongs somewhere in their business — the harder problem is knowing where to start, and getting a team comfortable enough to actually use it. Bryant Oberg, founder of Human Co-Pilot, argues that most AI struggles aren't AI problems at all. They're human governance and adoption problems, and they show up as "shadow AI," stalled initiatives, and teams too overwhelmed to begin.

In this conversation, Bryant explains why AI needs an active human guide rather than passive reliance, why most companies are missing even a basic usage policy, and why the psychological work of getting a team "into the elevator" often matters more than the technology itself.

Bryant Oberg spent 15 years in finance — banking, then the buy side, eventually becoming a partner at a hedge fund — before building his first AI-powered business in six weeks with no technical background. That business was wiped out overnight by a regulatory change, a setback that pushed him to pivot fully into AI advisory work through Human Co-Pilot.

His perspective is built on a recurring pattern he sees across CEOs and their teams: agreement that AI matters, paired with uncertainty about how to actually implement it. He walks through the concept of "shadow AI" — employees using personal AI tools with company data because no policy exists — and offers a framework for closing that gap through governance and hands-on adoption support.

00:00 Humans Must Lead AI

01:02 From Finance to AI Entrepreneurship

02:46 Escaping AI Productivity Pressure

07:14 A Failed Business Sparks Reinvention

12:22 Understanding Nondeterministic AI Responses

14:27 Allow AI to Admit Uncertainty

17:18 Keeping Humans in Control

20:53 Shadow AI Creates Business Risk

23:20 The Elevator Operator Analogy

24:45 Start With Policy and Education

28:01 The Fractional Chief AI Officer

31:36 Too Busy to Implement AI

Many CEOs can tell you what happened: the market shifted, pricing changed, the quarter improved. What gets lost is what actually broke, how they recognized it, and what they were thinking when they made the decision. For episode 100 of The Breakout CEO, host Jeff Holman goes solo to share the Breakout Arc, a four-stage framework he identified after conversations with 62 CEOs across 99 episodes.

The arc moves from Build, the business and the leader’s background, to Break, what disrupted momentum and how you recognized the signal. It continues to Breakout, the reflection, insights, constraints, decision and action behind the scenes. It ends at Breakthrough, the new trajectory for the business and for you as a leader. Jeff explains why each stage matters when you tell your story to your team, investors or peers, including feedback that pushed him to dig deeper into the build stage in his own interviews. He points to two past episodes per stage: 34 and 85 for build, 33 and 79 for break, 48 and 99 for breakout, and 42 and 77 for breakthrough.

He also shares where the show is headed as it grows into a community for scaling CEOs, with an online community, events and the Breakout CEO Awards planned for 2027, details to come. Jeff Holman is the host of The Breakout CEO.

00:00 Episode 100 and the Start of Season Five

00:29 62 CEO Conversations Reveal the Breakout Arc

02:03 Why CEOs Tell Better Stories With a Framework

03:31 Show Recap: CEO Episodes, Advisory Insights, Global Guests

07:18 From Podcast to a Community of Scaling CEOs

08:40 The Breakout CEO Awards and Why CEOs Deserve Recognition

10:16 A Missing Stage Means a Missing Piece of Your Story

11:26 Stage One, Build: Business and Leader Context

13:31 Stage Two, Break: Name It and How You Recognized It

15:36 Stage Three, Breakout: Reflection, Constraints, Decision, Action

19:09 Stage Four, Breakthrough: New Trajectory for Business and Leader

21:33 Eight Past Episodes That Illustrate Each Stage

Episodes Mentioned:

• Ep. 037, Andrew Ackerman (Second Century Ventures): The CEO Decision to Stop Competing and Redefine the Market
• Ep. 058, Jim Tracy (Legacy Enterprises): The Customer Concentration Risk CEOs See Too Late
• Ep. 062, Ricardo Arcia (Teravision Technologies): What Happens When CEOs Delay AI Adoption in Engineering Teams

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When a services company and a product company try to grow under the same roof, one of them eventually has to lose. In this episode, Jared Shepard explains the decision that forced him to spin Hypori out of his 20 year old, bootstrapped services company, Intelligent Waves, and raise venture capital for the first time in his career as a founder. He walks through the moment he realized a secure communications tool built for a narrow military use case was actually a massive BYOD opportunity for banks, healthcare systems, and eventually consumers, and the tradeoffs that came with chasing that bigger market, including giving up control, taking on a board, and learning to sell against competitors with no comparable category.

Jared talks candidly about what it took to reposition Hypori's pitch as it scaled from a few hundred thousand dollars in revenue to roughly 35 million dollars today, including the moment investors told him security was table stakes and the real value was in data sovereignty. He also gets into what it means to lead when every adjacent platform, from phone manufacturers to Microsoft, sees your growth as a threat to their own business model.

For CEOs weighing whether to spin a product out of an existing operation, or trying to reposition a company that has outgrown its original pitch, this conversation offers a clear look at the decision points, cost of delay, and leadership shifts involved. Jared Shepard is the founder and CEO of Hypori, and also leads Intelligent Waves and the veteran-focused nonprofit Warriors Ethos. Learn more at hypori.com.

00:00 Jared Shepard’s Unconventional CEO Journey

01:22 From Homelessness to Military Service

06:49 Building Intelligent Waves in Iraq

11:19 Redefining the Ultimate Sacrifice

15:08 Creating Warriors Ethos

20:19 The Mission Behind Hypori

24:27 Products and Services Cannot Coexist

27:34 Swimming With Silicon Valley Sharks

32:05 Disrupting Secure Mobile Computing

38:25 Why No-Brainers Become Hard

45:13 Hire Diamonds, Not Shiny Rocks

50:12 Learn From Everyone Around You

Most CEOs never admit what they are bad at, and it costs them the exact hires and decisions that could help their business scale. Larry Gould built one of the world's largest language companies, The Big Word, and years earlier built and sold a recruitment business, but neither started with a plan. Both trace back to moments most founders would rather bury: a childhood spent selling comics door to door for ice cream money, a misdiagnosed medical condition that pushed him out of school at fifteen, and a sales job crisis where a suspiciously low expense report nearly got him fired for dishonesty. Instead of losing his job, Larry was reassigned into international sales, where a lack of budget for support staff forced a decision, insisting on translated materials and direct communication with clients in their own language, that eventually became the foundation of his translation business.

In this episode, Larry walks through the operating philosophy he still uses today: knowing exactly what he is not good at, whether that is finance or technology, and building his team and his leadership decisions around people who are clever where he isn't, then letting them go once they stop being the sharpest option as the business grows. He also unpacks the framework behind his obsession with the word irresistible, a discipline he pushes on every client, employee, and investor conversation, and why most CEOs cannot answer a simple question about what makes their own company worth choosing over the competition.

Larry Gould is a serial entrepreneur, founder of The Big Word, and a mentor to founders at Cornell Tech. (Guest website not confirmed in transcript — recommend confirming with Larry's team before publishing.)

Most scaling CEOs assume a revenue problem is a sales and marketing problem, and it costs them the real diagnosis. In this episode, Kati Peterman, founder of the fractional executive firm YourFRX, breaks down why so many operations issues get misread as leadership or marketing failures, and what actually happens when a CEO gets too far removed from their own numbers.

Kati walks through her five five four framework for diagnosing where a growing company is breaking down, from meeting structures to KPI tracking, and shares a case where a founder was blaming their CMO for a revenue shortfall that turned out to be sitting untouched in an unmanaged accounts receivable process worth millions of dollars. The conversation covers when a fractional leader makes more sense than a full-time hire, why CEOs often make the mistake of hiring another version of themselves instead of the operator they actually need, and how staying curious about the numbers, even when things look fine, prevents small gaps from becoming expensive ones.

Kati Peterman is the founder of YourFRX, a fractional executive team helping scaling businesses close operational gaps across leadership, finance, and operations. Learn more at yourfrx.com.