The Breakout CEO

Every scaling e-commerce business eventually collides with the same silent problem: customers who don't get what they ordered, when they were promised it. Jevon Le Roux, CEO and co-founder of Keeyu, lived that problem firsthand before building a company to solve it — and along the way, a well-known investor told him it couldn't be done.

In this episode, Jevon breaks down why customer service has been built backwards for twenty years — reactive instead of preventive — and what it actually took to pivot his company's entire product, burn through almost all of its cash, and keep raising with five thousand dollars left in the bank.

Jevon Le Roux isn't a typical software CEO. Before co-founding Keeyu, he built and exited a business, became a professional surfer, and later earned an executive MBA at HEC Paris — all without finishing high school. That unconventional path shaped how he approaches problems: get to the root cause, then build the plan.

At Keeyu, Jevon and his co-founders are tackling the "where is my order" (WISMO) problem that quietly costs e-commerce businesses billions in lost revenue every year. His firsthand experience running e-commerce operations — including a crisis where a thousand customers ordered products that didn't exist in the warehouse — convinced him the industry's approach to customer service was solving the wrong problem. This episode traces the pressure, doubt, and near-failure behind that conviction, and the decision to keep building when it would have been easier to stop.

Key Takeaways

• Believing a problem is real matters more than believing your first solution is right. Jevon's team built a "vitamin" before they built a "painkiller" — and had to rebuild multiple times before the product matched the pain.
• Skepticism from experienced voices isn't a signal to stop — it can be the reason to keep going. When a well-known e-commerce investor called the WISMO problem impossible to fix, that became the founding team's reason to fix it.
• Reactive customer service can't prevent the problems it's built to handle. A help desk, like a hospital ER, can only triage after something's already gone wrong — the real opportunity is preventing the failure upstream.
• Running low on money tests belief in the problem, not just the business. Keeyu's founders kept raising — and kept building — with roughly five thousand dollars left in the bank.
• Creating a new category means selling the story before the market has a name for it. Convincing buyers, users, and economic decision-makers all requires a different pitch for each.

00:00 The $213B e-commerce problem

00:14 Meet Jevon Le Roux of KEEYU

03:02 Why late orders silently lose customers

05:34 Solving an “impossible” problem

08:36 The customer crisis that sparked KEEYU

12:35 From internal tool to startup

15:47 Early product lessons and pivots

18:11 Turning detection into automation

23:15 Reinventing customer support

31:23 Building through failure and near-zero cash

36:07 Fundraising, traction, and resilience

45:07 Advice for founders and CEOs

Jevon Le Roux is the founder of Keeyu, an Ecommerce Operations company. You can find Jevon at https://keeyu.com

What happens when someone reaches the top of the financial world—only to realize success isn't enough?

In this episode of The Breakout CEO Podcast, Jeff Holman sits down with Scot Cohen, CEO of WRAP, to explore the deeply personal journey that led him from a successful career in finance to building a company focused on reducing harm in public safety.

Scot shares why he walked away from Wall Street, the leadership lessons he learned after losing sight of his purpose, and how listening to customers—not assumptions—reshaped WRAP's strategy. He explains why training, culture, and evidence matter more than technology alone, and why the best CEOs are willing to challenge their own beliefs when the data tells a different story.

Whether you're leading a high-growth company or navigating your own inflection point, this conversation is a masterclass in purpose-driven leadership and making difficult decisions that create lasting impact.

In This Episode

• Why financial success didn't bring fulfillment
• The decision to leave Wall Street and build WRAP
• The leadership challenges of scaling a mission-driven company
• How customer feedback transformed WRAP's strategy
• Why training and culture outperform technology alone
• Leading with purpose instead of ego
• Building trust in one of the world's most scrutinized industries
• What CEOs can learn about making better decisions under pressure

About Scot Cohen

Scot Cohen is the CEO of WRAP, a public safety technology company focused on equipping law enforcement and first responders with tools and training designed to reduce injury and save lives. After a successful career in finance, Scot shifted his focus to building mission-driven technology that emphasizes better outcomes through innovation, training, and leadership.

Connect with Scot Cohen

LinkedIn: https://www.linkedin.com/in/scot-cohen-643181375/

Company: https://wrap.com

What separates companies that become market leaders from those that remain just another product?

In this episode of The Breakout CEO Podcast, Jeff Holman sits down with Romney Williams, entrepreneur, inventor, and CEO of DRYOUT, to explore the leadership decisions behind building a category-defining business.

Drawing from decades of experience launching companies, protecting intellectual property, and partnering with global brands, Romney shares why breakthrough growth isn't driven by better marketing—it's built on trust, credibility, and solving the right customer problem.

From discovering an unexpected business model through customer conversations to building competitive moats beyond patents, Romney offers a candid look at the realities of scaling a company while making high-stakes decisions with imperfect information.

Whether you're leading a startup or scaling an established business, this episode is packed with practical lessons on innovation, resilience, and long-term value creation.

• Why trust often becomes a company's greatest competitive advantage
• How listening to customers uncovered an entirely new business model
• The difference between protecting innovation and building a lasting brand
• How successful CEOs make decisions despite uncertainty
• Why intellectual property alone isn't enough to sustain growth
• Lessons from building partnerships instead of simply selling products
• How lifelong learning improves executive decision-making
• Why founders should embrace uncertainty instead of waiting for perfect clarity

00:00 Finding Joy in the Building Journey

01:17 Romney’s Career Thread Across Four Companies

03:16 From Digital Cameras to Industry Disruption

07:15 Why Founders Need Trusted Leadership Partners

12:43 Celebrating Milestones While Scaling a Business

14:15 Finding DryOut and Partnering With Its Founder

16:21 How Intellectual Property Creates an Unfair Advantage

19:08 The Accidental Invention Behind DryOut

22:09 Building the Gore-Tex of Moisture Removal

29:10 Evolving From Consumer Brand to Ingredient Brand

36:45 The Board Meeting That Changed DryOut’s Direction

59:16 Scaling Through Brand Partners and Military Applications

Romney Williams is the CEO of DRYOUT, an innovation company focused on moisture removal technologies. Throughout his entrepreneurial career, he has founded and scaled multiple businesses, developed extensive intellectual property, and built strategic partnerships with leading brands. His work centers on transforming breakthrough innovations into scalable commercial platforms by combining product development, trust, and long-term strategic thinking.

Connect with Romney

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

What if your biggest growth opportunity wasn't your product—but your customers?

In this episode of The Breakout CEO Podcast, Jeff Holman sits down with Julie Tylman, Co-Founder and Co-CEO of Group Together, to discuss how relentless customer listening shaped every major decision in her company's journey.

Julie shares how a simple idea to simplify group gifts evolved into an international business, why their biggest product breakthroughs came from customer feedback—not founder assumptions—and how one bold decision during COVID accelerated growth and opened the door to the U.S. market.

She also reflects on the leadership lessons she's learned along the way, including why staying close to customers has made her a better CEO.

Whether you're building a startup or leading a scaling company, this conversation is a masterclass in customer obsession, product evolution, and making better founder decisions.

00:00 Introduction

03:15 The idea behind Group Together

09:40 Building the first MVP

17:20 Learning from customer behavior

26:15 Early hiring mistakes

33:40 The COVID pivot

41:20 Product-market fit and explosive growth

49:10 Expanding into the United States

57:45 Customer service and leadership

01:04:30 Final CEO lessons

Connect with Julie Tylman

Website: https://grouptogether.com

LinkedIn: https://www.linkedin.com/in/julie-tylman-8a160977/

Artificial intelligence is transforming nearly every industry—but according to Sheldon Wolf, AI isn't here to replace real estate professionals. It's here to empower the ones who embrace it.

Drawing on more than 35 years of experience in real estate investing, development, brokerage, and PropTech, Sheldon explains why the future belongs to leaders who understand customer behavior, not just technology. He shares how every major shift—from fax machines to AI—has rewarded those willing to adapt while leaving others behind.

The conversation explores why most companies solve today's problems instead of tomorrow's, how customer acquisition drives every successful business, and why controlling the customer journey has become the greatest competitive advantage in real estate.

Whether you're building a brokerage, scaling a SaaS company, or leading through technological change, this episode offers practical lessons on innovation, customer-centric thinking, and long-term strategic execution.

Key Takeaways

• AI is a competitive advantage for professionals who know how to use it.
• Businesses should focus on customer behavior before building new technology.
• Companies that solve future problems outperform companies solving today's problems.
• Revenue follows customer acquisition—not the other way around.
• Great CEOs continually adapt while keeping the customer at the center of every decision.

About the Guest

Sheldon Wolf is the Founder and CEO of Intellitary AI, a PropTech company using artificial intelligence to modernize customer acquisition and the real estate buying journey.

With more than three decades of experience spanning brokerage, investing, development, and technology, Sheldon has built and scaled multiple businesses while advising organizations through periods of rapid growth and transformation. His current focus is helping brokerages leverage AI to improve customer experiences while preserving the value of real estate professionals.

Connect with Sheldon Wolf

Website: http://www.intellitary.com

LinkedIn: https://www.linkedin.com/in/sheldon-wolf-95011520

What does it take to leave a successful corporate career and build a healthcare startup from scratch?

In this episode of The Breakout CEO Podcast, Seth Merritt shares how a side project became Welby Health, a fast-growing healthcare technology company transforming chronic care management.

Seth explains why moving quickly—not perfectly—became his competitive advantage, how customer conversations shaped every major product decision, and why founders should stop waiting for the "perfect" business plan before taking action.

Along the way, he discusses fundraising, validating ideas, moving up-market, building an enterprise business, and the realities of leading a company through uncertainty.

Whether you're a founder, CEO, or executive leading innovation inside a larger organization, this episode offers practical lessons on building faster, learning sooner, and making better decisions.

Key Takeaways

• Why speed is a competitive advantage in healthcare.
• The importance of talking to customers before building products.
• How Welby Health evolved from a side project into a venture-backed company.
• Why founders should launch imperfect products and iterate quickly.
• Lessons learned from moving from SMB customers to enterprise healthcare systems.
• The mindset required to scale a startup while remaining customer-focused.
• Why profitable growth matters more than growth at all costs.

00:00 Why Speed Beats Perfection in Healthcare

01:17 Delivering Faster Impact for Healthcare Customers

08:06 Why Seth Schedules Weekly Tinker Time

10:47 How WellBe Health Supports Chronic Care

15:30 Validating Ideas Through Real Customer Conversations

20:25 Turning an MBA Project Into a Business

22:34 From First Customer to Full-Time Founder

26:25 Scaling WellBe Health to 75 Employees

28:09 Moving Upmarket to Enterprise Healthcare Customers

33:15 Competing Against Best-in-Class Healthcare Companies

40:12 AI, Profitability, and WellBe Health’s Future

42:59 Start Before Everything Feels Perfect

Resources Mentioned

• Welby Health https://welbyhealth.com/
• The $100 Startup by Chris Guillebeau

As companies scale, the first signs of trouble rarely appear on a dashboard. They show up in stretched teams, founder bottlenecks, and hiring decisions that lag behind growth.

In this episode of The Breakout CEO Podcast, David Khim, Co-Founder of Omniscient Digital, explains why CEOs need to pay attention to qualitative signals before traditional metrics catch up. Drawing from his own experience scaling a bootstrapped agency through rapid growth and AI-driven industry disruption, David shares how a change in hiring philosophy—and in his own leadership—helped unlock the company's next stage of growth.

Episode Description

Rapid growth can hide organizational strain until it's too late. David Khim discusses how his team reached a point where they had to turn away new business because they had optimized for efficiency instead of capacity. That realization changed how Omniscient Digital hires, plans, and leads.

The conversation also explores why experienced leaders increasingly rely on qualitative observations alongside KPIs, how AI is reshaping service businesses, and why founder growth ultimately determines company growth. Rather than treating ambiguity as something to avoid, David argues that CEOs should learn to recognize it as an opportunity to build stronger organizations before cracks begin to show.

Key Takeaways

• Watch for qualitative signals—team capacity, stress, and leadership bandwidth—before the metrics reveal a problem.
• Hiring ahead of demand can prevent growth from stalling when opportunities arrive.
• Founder development often becomes the limiting factor in organizational growth.
• AI changes how work gets done, but judgment remains a CEO's competitive advantage.
• Building capacity requires intentional decisions before they're financially comfortable.

Before the main episode, David joined us for an informal icebreaker conversation about how he recharges outside of work, why he schedules solo CEO retreats, and the routines that help him process difficult decisions.

Watch the Icebreaker on The Breakout CEO LinkedIn page:

https://www.linkedin.com/company/the-breakout-ceo/

00:00 AI Is Changing Business Faster Than Ever

00:40 Meet David Khim of Omniscient Digital

05:18 From Chemistry to Organic Growth

11:42 Scaling from Startup to Growth Company

13:17 The Hiring Mistake That Limited Growth

18:27 Avoiding the Founder-Made Trap

20:34 Why Strong Co-Founder Relationships Matter

24:01 Why Every CEO Needs Outside Support

29:15 Helping Clients Navigate AI Disruption

32:13 Building AI Systems That Create Leverage

34:54 Charging for Outcomes, Not Output

39:58 Grace and Space for Better Leadership

Guest

David Khim

Co-Founder, Omniscient Digital

Website: https://www.omniscientdigital.com

LinkedIn:

https://www.linkedin.com/in/davidlykhim

Host

Jeff Holman

Host, The Breakout CEO Podcast

What separates CEOs who build enduring companies from those who simply manage growth?

For Vikas Sehgal, the answer wasn't a better strategy or a more aggressive sales process. It was a fundamental shift in how he viewed leadership. After helping build Nagarro from a living room startup into a global technology company, Vikas discovered that sustainable growth comes from shared values, empowering great people, and solving customer problems before trying to sell solutions.

In this episode of The Breakout CEO Podcast, Vikas reflects on the leadership lessons forged through the 2008 financial crisis, why his team chose shared sacrifice over layoffs, how that decision reshaped their culture, and how those same principles now guide hyperDart as it reimagines the future of search through AI and creator-first economics.

• Why shared values matter more than organizational hierarchy when scaling a company.
• How choosing pay reductions over layoffs strengthened culture during the 2008 financial crisis.
• Why the best sales organizations begin by solving customer problems—not chasing opportunities.
• The leadership transition from controlling outcomes to enabling great teams.
• Why entrepreneurship can only be learned by building, not by waiting for perfect conditions.

00:00 From Living Room Startup to Billion-Dollar Company

02:10 Why Shared Values Beat Vision Every Time

10:35 Great Ideas Come From Every Corner of the Company

16:50 The 2008 Crisis That Changed Nagarro Forever

25:58 Stop Selling and Start Solving Customer Problems

34:46 Why Taking Time Off Made Him a Better Founder

44:41 Why Search Is Broken and hyperDart Can Fix It

55:57 Building an AI-First Search Platform

01:03:37 Why Knowledge Creators Are the Real Customers

01:08:10 The Right Time to Start Never Comes

01:10:15 Building Confidence One Challenge at a Time

01:12:04 Final Advice for Every Aspiring Entrepreneur

Guest

Vikas Sehgal

Founder & CEO, hyperDart

Former CEO & Co-founder, Nagarro

LinkedIn

https://www.linkedin.com/in/vsehgal/

Website

https://hyperdart.com/

Host

Jeff Holman

The Breakout CEO Podcast

LinkedIn

https://www.linkedin.com/company/the-breakout-ceo/

Most service companies lead with what they do. The ones that grow the fastest lead with the problems they solve.

In this episode of The Breakout CEO Podcast, Mike LaVista, Founder & CEO of Caxy Interactive, explains how one shift in positioning transformed his consulting business from transactional projects into strategic partnerships, dramatically increasing deal size and changing the conversations he was having with CEOs. Along the way, he shares why niching down creates premium businesses and how AI should be viewed as an amplifier of strategic thinking—not a replacement for it.

For years, Mike LaVista described his business the same way most service companies do: by listing the services it offered. It wasn't until he reframed the conversation around customer problems that everything changed.

That single realization reshaped Caxy's growth, leading to larger engagements, stronger executive relationships, and a much clearer market position. Mike walks through the decision behind that shift, why specialization creates opportunity rather than limitation, and how asking better questions builds trust long before a proposal is ever written.

The conversation also explores the practical role AI is playing inside modern businesses. Rather than focusing on automation alone, Mike argues that AI is most valuable when it helps leaders think better, explore more possibilities, and strengthen the capabilities that already make their organizations successful.

00:00 – Musician Turned Tech Entrepreneur

02:55 – Luck Landed Their First Client

06:29 – Performance Skills Built Better Leaders

12:31 – Developers Need Leaders Who Understand

17:54 – AI Should Empower Human Talent

21:46 – CEOs Need AI Thinking Partners

24:29 – Small Teams Can Compete Bigger

27:44 – Focus Before Building New Businesses

33:59 – Sell Problems, Not Your Services

40:05 – Better Questions Command Premium Prices

44:11 – Niching Down Creates Massive Growth

47:12 – Fear Stops Great Companies Growing

Stop describing your services and start leading with the business problems you solve.

Specialization creates credibility, stronger referrals, and premium pricing.

The best sales conversations begin with better questions, not better presentations.

AI is most powerful when it strengthens strategic thinking instead of simply automating existing work.

Great positioning makes it easier for customers to understand exactly why they should choose you.

Mike LaVista

Founder & CEO, Caxy Interactive

Website: https://caxy.com

LinkedIn: https://linkedin.com/in/mikelavista

Host

Jeff Holman

The Breakout CEO Podcast

Every CEO knows people matter. Fewer recognize that hiring is one of the highest-leverage strategic decisions they make.

In this episode of The Breakout CEO Podcast, Fletcher Wimbush shares why building a better company starts with building a better hiring system. From hiring for integrity over raw talent to eliminating "talented terrors" and staying relentlessly focused, Fletcher explains how better hiring decisions shape culture, execution, and long-term growth.

Fletcher Wimbush is the Founder and CEO of Discovered, a talent acquisition platform that helps organizations make smarter hiring decisions. His perspective comes from decades of leading teams, interviewing thousands of candidates, building recruiting systems, and growing multiple businesses through disciplined leadership.

In this conversation, Fletcher explains why hiring isn't simply an HR function—it's one of the most important strategic responsibilities of a CEO. He shares lessons from taking over his father's business, separating two competing business models to unlock growth, building a SaaS platform, and acquiring complementary technology to create an end-to-end hiring solution.

Whether you're making your next executive hire or scaling from 20 employees to 500, this episode demonstrates how better hiring decisions create better companies.

Key Takeaways

• Hire for integrity and attitude before experience or technical skill.
• Great hiring systems reduce turnover, improve culture, and compound business performance.
• Focus is often the biggest growth strategy—doing fewer things exceptionally well creates leverage.
• "Talented terrors" usually cost far more than they contribute.
• Strong reference checking remains one of the most underused tools in executive hiring.

00:00 Why Every Business Is Really in the People Business

01:25 Leadership Lessons That Started at Sixteen

05:30 Growing Up with an Executive Coach as a Father

09:45 Taking Over the Family Business After Tragedy

12:40 Why Integrity and Attitude Beat Talent Alone

17:45 Learning to Hire Through 10,000 Candidate Interviews

22:30 The High Cost of Keeping "Talented Terrors"

26:30 The Hiring Question That Reveals Everything

31:50 Splitting One Business into Two—and Doubling Revenue

36:00 Building a Hiring Platform and Acquiring Integrity First

47:40 How Better Hiring Creates Better Business Results

56:35 The Power of Focus for Every Scaling CEO

Guest Information

Fletcher Wimbush

Founder & CEO, Discovered.ai

LinkedIn:

https://www.linkedin.com/in/fletcherwimbush

Company:

https://www.discovered.ai