In this episode, we sit down with René Lacerte, founder and CEO of BILL, the financial automation platform serving hundreds of thousands of businesses. What started as a bold idea to fix broken, manual financial workflows has grown into a company generating around $1.5B in annual revenue with a market cap of roughly $5B. René shares what it really means to carry CEO responsibility at scale. He talks about why even top leaders need CEO coaches, how culture becomes your true competitive edge, and how to balance patience with urgency. As he puts it, “The best ideas always seem obvious in hindsight.”0:00 Intro2:27 The Problem That Sparked BILL6:30 What Made You Actually Take the Leap?9:53 How BILL Survived — and Won — in a Tough Market13:32 The Hardest Leadership Lessons17:05 Scaling Strategy: Playing the Long Game23:42 Why Culture Decides the Outcome27:24 Speed vs. Impatience: A Founder’s Dilemma36:01 How Will BILL Be Remembered?Essential viewing for founders, executives, and operators navigating growth. // LINKS //Instagram / jeromedwightx Youtube / @jeromedwightx TikTok / jerome.dwight Spotify https://open.spotify.com/show/47yRU8V...#Renélacerte #Bill #fintech #FutureOfWork #leadership #leadershiptraining #ChallengerMindset #AI #TechLeadership #ScalingUp #BusinessGrowth #OperatorMindset #TeamExecution #JeromeDwight #challengerx #motivation

How do you scale a tech company from $3.6B to nearly $10B and lead 35+ acquisitions without breaking the organization?In this episode of ChallengerX, Jerome Dwight sits down with Stephanie Buckner, former COO of Altair Engineering and now Co-Founder of Escape Investment Management, to unpack the real operational, leadership, and M&A lessons behind hyper-growth in deep tech.0:00 Intro2:26 What drew you to the world of tech?4:40 Navigating your early career6:07 Returning to Altair and the path back8:58 The major transformational milestones at Altair15:26 The North Star priorities that guided your leadership18:17 What you looked for when building your leadership team20:30 Managing the exit to Siemens23:08 What led you to become an investor28:37 Your strongest convictions when evaluating investments30:44 The KPIs companies should focus on34:00 Lessons for the next generation of leadersEssential viewing for founders, executives, and operators navigating growth. // LINKS //Instagram / jeromedwightx Youtube / @jeromedwightx TikTok / jerome.dwight #Stephaniebuckner #Altair #engineering #FutureOfWork #leadership #leadershiptraining #ChallengerMindset #AI #TechLeadership #ScalingUp #BusinessGrowth #OperatorMindset #TeamExecution #JeromeDwight #challengerx #motivation

In this episode, Anne Raimondi, COO of Asana and a seasoned operator across companies like eBay, SurveyMonkey, Zendesk, and Guru — breaks down what it really takes to lead teams and build products in a world being reshaped by technology.

Anne didn’t begin her career in tech. She found her way into the industry by solving real operational problems inside a retail company, and that experience shaped how she thinks about technology today: as a tool that should make people more effective, not overwhelmed.

From scaling eBay during its explosive growth, to defining product-led culture at SurveyMonkey, to transforming customer experience at Zendesk, Anne shares the lessons she’s carried across decades of building, leading, and operating inside some of the most influential companies of the last twenty years.

Now as COO of Asana, she’s helping redefine how teams work in an era where AI, automation, and collaboration tools are changing expectations faster than ever.

In this conversation, Anne breaks down:

- The mindset shift leaders need as work becomes increasingly tech-enabled

- Why companies must remove friction — not add complexity

- How to build teams that stay innovative as organizations scale

- Why your product is your brand (especially as customer expectations accelerate)

// LINKS //

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

Youtube https://www.youtube.com/@jeromedwightx

TikTok https://www.tiktok.com/@jerome.dwight

Spotify https://open.spotify.com/show/47yRU8VeRXZjvwwbS2CWgn?si=TFWYhoKYRziQbTjaXjuOjw&nd=1&dlsi=1ae5fe7561434a39

#AnneRaimondi #Asana #FutureOfWork #Leadership #ChallengerMindset #AI #TechLeadership #ScalingUp #BusinessGrowth #OperatorMindset #TeamExecution #JeromeDwight #ChallengerX

In this episode, Alex Dogliotti, Chief Operating & Human Resources Officer (COO) of Mindvalley, shares how the company is redefining education and leadership in the age of AI. He explains why the future belongs to leaders who can bridge technology and people, and how he guides one of the world’s leading edtech companies, impacting 20 million learners across 135 countries

With a community spanning millions, Mindvalley’s mission has always been clear: to unlock human potential through transformational education. But as AI reshapes industries, Alex explains how Mindvalley is evolving—blending technology, emotional intelligence, and purpose-driven systems to build the future of learning.

Alex discusses what he calls “The Future Human”—where mindset, technology, and health converge to help people live longer, smarter, and more fulfilled lives. He dives into how AI is disrupting traditional education, why emotional learning still matters, and how leaders can integrate AI without losing the human element that drives connection and culture.

For founders and executives, this episode is a roadmap for future-proofing your organization—where innovation isn’t just about adopting new tools, but reimagining how humans and AI can grow together

We cover:

- How Mindvalley evolved from an education company to a transformation platform

- Why AI will reshape learning, leadership, and HR as we know it

- How to train AI as if it were part of your team—not a replacement for it

- How to balance technological progress with human connection

// LINKS //

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

YouTube https://www.youtube.com/@jeromedwightx

TikTok https://www.tiktok.com/@jerome.dwight

Spotify https://open.spotify.com/show/47yRU8VeRXZjvwwbS2CWgn?si=TFWYhoKYRziQbTjaXjuOjw&nd=1&dlsi=1ae5fe7561434a39

#AlexDogliotti #Mindvalley #AILeadership #FutureOfLearning #Transformation #DigitalLeadership #ChallengerX #Innovation #FutureHuman #BusinessStrategy #AIMindset #OrganizationalDesign #FounderMindset #LeadershipEvolution #HumanPotential

James Keyes has led two of the most recognizable brands in the world, 7-Eleven and Blockbuster, steering both through some of the most defining moments in modern business.

At 7-Eleven, Keyes transformed a company buried in $4 billion of debt into a global brand. Through data-driven innovation and a relentless belief that “change equals opportunity,” he led the company’s IPO and 37 straight quarters of growth, turning a convenience store into a technology-driven retail empire.

Then came Blockbuster. Keyes took the reins during one of the most misunderstood business battles of our time: Blockbuster vs. Netflix.

In this conversation, James reveals the untold story — from a near partnership with Google and YouTube that could have rewritten history to the devastating impact of the 2008 financial crisis. He reveals what it takes to lead when every decision counts, making billion-dollar calls under pressure, and staying composed when the world is betting against you.

Today, James is using those lessons to empower the next generation. Through his foundation, Education is Freedom, he’s reimagining how we teach curiosity, creativity, and cultural literacy.

His story is more than a corporate saga. It’s a masterclass in resilience, reinvention, and leading with truth in the face of perception.

We cover:

- The real story behind Blockbuster vs. Netflix

- How 7-Eleven became a $30B global brand through data and adaptability

- The near Google–YouTube deal that could have changed entertainment history

- Leadership lessons from the edge: crisis, confidence, and clarity

- Why the future of education depends on meta-skills like creativity and curiosity

// LINKS //

Instagram https://www.instagram.com/jeromedwightx/?next=%2F

YouTube https://www.youtube.com/@jeromedwightx

TikTok https://www.tiktok.com/@jerome.dwight

Spotify https://open.spotify.com/show/47yRU8VeRXZjvwwbS2CWgn?si=TFWYhoKYRziQbTjaXjuOjw&nd=1&dlsi=1ae5fe7561434a39

#JamesKeyes #ChallengerX #ChallengerMindset #Leadership #BusinessResilience #Blockbuster #Netflix #7Eleven #Entrepreneurship #Innovation #Education #AI #JeromeDwight

Paul English is a tech entrepreneur, computer programmer, and philanthropist, Paul is best known as the Co-Founder and former CTO of Kayak, the travel search engine that redefined how millions book trips and later sold for $2 billion.Raised in a working-class Boston family, Paul learned early that limitations could be fuel for creativity. When his mother brought home a computer, he taught himself to code.After several early ventures, Paul co-founded Kayak with Steve Hafner, determined to simplify online travel. Despite early challenges and setbacks, their relentless focus on product quality and user experience turned Kayak into a billion-dollar success. The company went public in 2012 with a $1.2B IPO, and was later acquired by Priceline for $2B.Yet for Paul, the true reward wasn’t wealth — it was seeing his team win and using that success to fuel something bigger.Today, he channels his energy into philanthropy and innovation — building schools in Haiti, leading homelessness initiatives, supporting mental health programs, and launching an AI institute to empower the next generation. His mission now is to use technology and empathy together to create lasting human impact.Paul believes AI will shape the next great revolution, and that leaders must guide it with creativity, ethics, and heart.His journey proves that success isn’t about exits or valuations — it’s about how you use what you’ve built to serve others.We cover:- How Paul turned early struggles into lifelong motivation- The lessons behind building and scaling Kayak to a $2B IPO- Why leadership starts with honesty, vulnerability, and team trust- How philanthropy fuels long-term purpose and fulfillment- The evolving role of AI in business, education, and human potential// LINKS //Instagram: https://www.instagram.com/jeromedwightxYouTube: https://www.youtube.com/@jeromedwightxTikTok: https://www.tiktok.com/@jerome.dwightSpotify: https://open.spotify.com/show/47yRU8VeRXZjvwwbS2CWgn?si=TFWYhoKYRziQbTjaXjuOjw#PaulEnglish #Kayak #ChallengerX #ChallengerMindset #Entrepreneurship #Leadership #StartupJourney #AI #Innovation #Philanthropy #Resilience #JeromeDwight

Julia Hartz didn’t plan to be an Entrepreneur, but she built one of the most influential platforms in the world of live experiences. As Co-Founder and CEO of Eventbrite, Julia turned a simple idea into a global business that, in 2024, powered 4.7 million events across 180 countries, connected 89 million monthly users, and sold 83 million paid tickets.Eventbrite sits at the intersection of digital culture and real-world connection. Helping creators and communities bring online connection into real-world belonging.Starting her career in television, Julia learned the power of storytelling — a skill she later used to build culture, inspire teams, and connect millions around the globe. Alongside her husband and co-founder, Kevin Hartz, and their technical co-founder, Renaud Visage, Julia bootstrapped Eventbrite from scratch. Building a platform that empowered anyone to turn an idea into an event, making it faster and easier than ever before.Then came 2020. The world went quiet — concerts, festivals, and conferences disappeared overnight. Eventbrite’s business stopped instantly, and Julia was suddenly faced with a challenge that tested everything she’d built. Through data-driven decisions, empathy, and an unwavering focus on her mission, she led Eventbrite back to growth.Today, Eventbrite is tracking—and powering—the cultural shifts redefining how people connect, play, and recharge. Julia continues to lead the future of human experiences — where AI enhances creativity, and Gen Z’s demand for authentic experiences is driving the next wave of live engagement.For leaders navigating change, Julia’s journey is proof that clarity, adaptability, and belief in people - can turn disruption into opportunity.We cover:- How to rebuild and refocus when your business model breaks- Why clarity and empathy are critical to resilient leadership- Lessons on scaling culture, systems, and global reach- The evolving role of AI and human creativity in business growth- How to stay grounded while leading through uncertainty// LINKS //Instagram https://www.instagram.com/jeromedwightxYouTube https://www.youtube.com/@jeromedwightxTikTok https://www.tiktok.com/@jerome.dwightSpotify https://open.spotify.com/show/47yRU8VeRXZjvwwbS2CWgn?si=TFWYhoKYRziQbTjaXjuOjw&nd=1&dlsi=1ae5fe7561434a39#JuliaHartz #Eventbrite #ChallengerX #ChallengerMindset #Entrepreneurship #Leadership #Resilience #Innovation #FutureOfWork #JeromeDwight

Carl Gambino is the Founder and Principal of The Gambino Group, a leading luxury real estate firm with over $2B in lifetime sales across New York, Los Angeles, Miami, and the Hamptons. He represents world-renowned talent and investors, while also mentoring the next generation of real estate leaders.

Born in New York City and raised in New Jersey, Carl grew up fascinated by architecture and real estate. His journey wasn’t linear — he faced challenges early on, but used them as fuel to reset, refocus, and rebuild.

From walking dogs in Los Angeles to closing his first $6M real estate deal, Carl turned small opportunities into career defining moments. By combining relentless work ethic with an obsessive drive to learn the market, he quickly built credibility and earned the trust of clients at the highest level.

Carl’s story is more than a career highlight reel — it’s a lesson in resilience, belief, and the power of relationships. His journey shows that success doesn’t come from shortcuts, but from the willingness to bet on yourself, keep learning, and never stop moving forward.

We dive into Carl’s story of hard work, key turning points, and the mindset that keeps him growing. Proof that belief and resilience drive lasting success.

We cover:

- The role of mindset, discipline, and daily habits in building success

- Why relationships and discretion matter most in high-stakes business

- How knowledge and preparation create confidence before experience

- Lessons for entrepreneurs on pushing through setbacks and seizing opportunity

// LINKS //

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

YouTube https://www.youtube.com/@jeromedwightx

TikTok https://www.tiktok.com/@jerome.dwight

Spotify https://open.spotify.com/show/47yRU8VeRXZjvwwbS2CWgn?si=TFWYhoKYRziQbTjaXjuOjw&nd=1&dlsi=1ae5fe7561434a39

#CarlGambino #GambinoGroup #ChallengerX #ChallengerMindset #LuxuryRealEstate #Hollywood #Entrepreneurship #CEOInsights #Resilience #Startup #Founder #Mindset #Leadership #BusinessGrowth #RealEstate

In this episode, we sit down with Songe LaRon, the visionary co-founder and CEO of Squire, the world’s leading barbershop management and fintech platform. What began as a frustrating experience trying to book haircuts during his time as a corporate lawyer turned into a multi-national SaaS business now powering over 20,000+ barbers across the US, UK, Canada, and Australia.

After graduating from Yale and launching his career in M&A law, Songe left behind the security of the corporate world to solve a problem nobody else was looking at. Alongside his co-founder, he built Squire from the ground up—bootstrapping early growth, running their own barbershop to understand the customer, and eventually raising $165 million in venture capital.

Today, Squire is not just a booking tool—it’s a fully integrated operating system and fintech engine helping barbershops run more efficiently, grow faster, and stay financially empowered.

But behind the product is a deeper story—one about bold pivots, overcoming rejection, and why customer obsession is still the most powerful growth strategy in business.

We cover:

- How solving his own pain led to a billion-dollar opportunity

- The leap from Yale Law to barbershop entrepreneurship

- The brutal Series A journey: 59 rejections and 1 life-changing “yes”

- Why every founder needs to live inside their customer’s world

If you’re building a vertical SaaS company—or chasing an opportunity in an overlooked market—Songe’s story is a playbook in grit, intuition, and scale.

// LINKS //

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

YouTube https://www.youtube.com/@jeromedwightx

TikTok https://www.tiktok.com/@jerome.dwight

Spotify https://open.spotify.com/show/47yRU8VeRXZjvwwbS2CWgn?si=TFWYhoKYRziQbTjaXjuOjw&nd=1&dlsi=1ae5fe7561434a39

#challengerx #jeromedwight #songelaron #squire #fintech #startuplife #founderstory #barbershoptech #verticalsaas #entrepreneurship #customerobsession #startuplessons #scalingtech #ycombinator #growthmindset #blackfounders #ceomindset #leadership #buildinpublic #startupgrind

In this episode, we sit down with Allie Egan, founder & CEO of Veracity, a wellness brand transforming how we approach metabolic health, hormones, and beauty. With $14M in funding and a projected $20-30M in revenue by 2025, Allie is reshaping the health space with a personalized, science-backed approach.

What I admire most is how Allie turned her own health struggles into a mission-driven brand. From her journey into functional medicine to empowering others to take control of their health, she’s changing the game.

Before launching Veracity, Allie was the CEO of Cynthia Rowley, doubling revenue in just two years. She also worked at Estée Lauder, leading top brands like Tom Ford and La Mer.

We dive into how Allie scaled Veracity from scratch, her journey from fashion CEO to wellness founder, and her 3 tactical tips for early-stage CEOs.

// LINKS //

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

Youtube https://www.youtube.com/@jeromedwightx

TikTok https://www.tiktok.com/@jerome.dwight

Spotify https://open.spotify.com/show/47yRU8VeRXZjvwwbS2CWgn?si=TFWYhoKYRziQbTjaXjuOjw&nd=1&dlsi=1ae5fe7561434a39

#Entrepreneurship #Wellness #Health #Founder #Growth #Business #Leadership #Veracity #Startup #ChallengerX #Veracity #AllieEgan #JeromeDwight