Shensi Ding-Lopez, Co-Founder & CEO of Merge, joins Clint Betts for a conversation on AI agents, integrations, startup culture, and the future of enterprise software infrastructure.

Merge helps B2B software companies securely integrate with third-party systems across HR, accounting, ATS, ticketing, file storage, and more through a unified API platform. In this episode, Shensi explains why integrations are becoming one of the biggest bottlenecks in AI adoption — and why secure infrastructure for AI agents may become one of the most important categories in enterprise software.

The conversation also explores startup fundraising, product-market fit, technical leadership, company culture, and what it takes to build deeply technical products at scale.

00:00:00 - Introduction and Background
00:00:22 - Founding Merge
00:00:54 - Launching the Second Product
00:02:05 - AI Agents and Security
00:03:36 - Fundraising Journey
00:04:36 - Early Customer Validation
00:05:10 - Co-Founder's Background
00:06:00 - A Day in the Life of a CEO
00:07:16 - Technical Contributions
00:08:22 - Future of AI
00:09:01 - Economic Environment and Optimism
00:10:01 - Company Culture and Hiring
00:11:56 - Reading Habits and Recommendations
00:13:32 - The Importance of Giving Chances
00:14:51 - Closing Remarks

If you’re interested in AI, APIs, enterprise software, cybersecurity, startups, or the future of agentic workflows, this conversation is packed with insights for founders, operators, and technical leaders alike.

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Jill Schulman, Founder & Principal of Breakthrough Leadership Group and author of The Bravery Effect, joins Clint Betts for a conversation on fear, leadership, resilience, and the science of bravery.

A former United States Marine Corps officer and happiness scientist trained in positive psychology at the University of Pennsylvania, Jill has dedicated her career to helping leaders overcome fear and unlock their highest potential.

In this episode, Jill explains why bravery isn’t about fearlessness — it’s about taking action despite fear — and why that mindset is essential for CEOs, executives, and anyone navigating uncertainty in today’s world.

The conversation also explores Stoicism, leadership under pressure, difficult conversations, AI, and how courage can fundamentally reshape both organizations and personal lives.

00:00:00 - Introduction and Guest Background
00:00:21 - Discovering the Study of Bravery
00:01:03 - The Role of Fear in Happiness and Self-Actualization
00:01:56 - Defining Bravery
00:02:08 - Writing "The Bravery Effect"
00:02:41 - The Book Writing Process
00:04:04 - Collaborating with a Ghostwriter
00:05:05 - Publishing Challenges
00:05:27 - Practical Examples of Brave Leadership
00:06:07 - Leading Through Uncertainty
00:08:14 - Having Difficult Conversations
00:09:46 - Motivation to Join the Marines
00:11:29 - Founding Breakthrough Leadership Group
00:14:57 - A Typical Day in Jill's Life
00:16:35 - Speaking Engagements
00:17:25 - Impact of AI on Work
00:19:23 - Reading Preferences and Recommendations
00:22:05 - The Importance of Giving and Taking Chances
00:22:23 - Acknowledging Key Supporters
00:23:04 - Closing Remarks

If you’re interested in leadership, psychology, resilience, personal growth, or becoming a more courageous leader, this conversation is packed with practical insights and inspiration.

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Leslie Ann Hall, Founder & CEO of ICED Media, joins Clint Betts for a conversation on AI, beauty marketing, digital commerce, and the future of consumer discovery.

ICED Media has become one of the leading digital agencies in the beauty industry, helping brands navigate the rapidly changing worlds of TikTok Shop, social commerce, and now AI-powered discovery. In this episode, Leslie explains why ChatGPT and generative search may completely reshape how consumers discover and purchase beauty products online.

The conversation also dives into thought leadership, company culture, accountability, and what it takes to build a trusted brand in one of the fastest-moving industries in the world.

00:00:00 - Introduction and Guest Welcome
00:00:20 - Leslie Anne Hall's Background and Iced Media Overview
00:01:04 - Specialization in Beauty and Performance Marketing
00:01:57 - AI Integration in Iced Media
00:03:08 - AI's Impact on Consumer Discovery in Beauty
00:04:45 - Search and Discovery Discipline at Iced Media
00:05:51 - A Day in the Life of Leslie Anne Hall
00:07:06 - Building Relationships and Company Culture
00:10:30 - Challenges in the Beauty Industry
00:12:31 - Reading Recommendations
00:15:25 - Proud Projects and Advisory Board
00:18:24 - Advice for Aspiring Thought Leaders
00:22:01 - Acknowledging Those Who Gave a Chance
00:24:11 - Closing Remarks and Gratitude

If you’re interested in AI, digital marketing, e-commerce, leadership, beauty, or the future of consumer behavior, this conversation is packed with insights for founders, operators, and marketers alike.

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Brendan Noud, Co-Founder & CEO of LearnUpon, joins Clint Betts for a conversation on AI, personalized learning, startup culture, and building one of the world’s leading learning management platforms.

What started around a kitchen table in Ireland has grown into a global SaaS company serving more than 25 million learners worldwide. In this episode, Brendan shares how LearnUpon scaled from a bootstrapped startup into an international learning platform helping companies train employees, customers, and partners at scale.

The conversation explores the future of AI in education, company culture, global expansion, and why personalized learning may become one of the most important business challenges of the next decade.

00:00:00 - Introduction and Background
00:00:26 - Founding LearnUpon
00:01:18 - Initial Focus and Evolution
00:02:00 - Funding and Tech Scene in Ireland
00:04:27 - Realizing Success
00:05:42 - Impact of AI on Learning Management
00:07:17 - AI in General Education
00:08:48 - A Day in the Life of a CEO
00:10:18 - Reading Recommendations
00:11:00 - Company Culture
00:12:23 - Becoming a Global Company
00:13:49 - Macroeconomic Environment
00:15:19 - Learning from Failures
00:17:06 - Future Roadmap
00:18:57 - Final Question: Who Gave You a Chance?

If you’re interested in AI, SaaS, education, leadership, or building global technology companies, this episode is packed with practical insights for founders and operators alike.

Jonathan Shank, Founder & CEO of Terrapin Station Entertainment, joins Clint Betts for a conversation on the evolution of the music business, live entertainment, AI, authenticity, and building iconic entertainment experiences.

From hanging flyers at the legendary House of Blues in New Orleans to producing global live tours for brands like Peppa Pig, Disney Junior, and Gabby’s Dollhouse, Jonathan shares the journey that shaped his career in music and entertainment.

The conversation dives into artist development, the rise of streaming and viral discovery, leadership in creative industries, and why authentic creativity still matters in the age of AI.

00:00:00 - Introduction and Guest Background
00:00:34 - Early Career at House of Blues
00:01:17 - First Job Responsibilities
00:01:58 - Learning the Music Business
00:02:33 - Interning with Kim Fowley
00:03:26 - Moving to Los Angeles
00:03:49 - Representing Classic Rock Bands
00:04:10 - Working on Jazz is Dead
00:04:32 - Managing Second-Generation Rock Stars
00:05:25 - Managing Particle and Festival Success
00:06:57 - Transition to Producing Shows
00:07:50 - Founding Terrapin Station Entertainment
00:09:07 - Changes in the Music Industry
00:11:01 - Impact of Technology and AI
00:11:55 - Bob Dylan at House of Blues
00:14:26 - Leadership and Company Growth
00:17:12 - Impact of AI on the Industry
00:19:42 - Typical Day in the Life
00:21:23 - Promoting the Podcast "The Jam"
00:22:33 - Acknowledging Mentors and Supporters
00:23:55 - Closing Remarks

If you’re interested in music, entertainment, creativity, entrepreneurship, or the future of AI in media, this is a conversation you won’t want to miss.

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Carrie Joy Grimes, Founder & CEO of WorkMoney, joins Clint Betts for a conversation on the shrinking middle class, the future of the American Dream, and how collective bargaining power could reshape the economy for everyday people.

WorkMoney has grown to more than 9 million members by helping Americans save money, lower bills, access discounts, and better navigate an increasingly difficult financial system. In this episode, Carrie explains why so many people feel financially stuck — and what can actually be done about it.

The conversation explores AI, economic inequality, remote work, monopolies, and why the next generation faces a dramatically different financial reality than previous generations.

00:00:00 - Introduction and Guest Welcome
00:00:10 - Founding of WorkMoney
00:00:25 - Mission and Vision of WorkMoney
00:01:14 - Economic Inequality and Wealth Transfer
00:02:04 - Challenges for the Next Generation
00:02:41 - WorkMoney's Membership and Scale
00:03:22 - Negotiating for Members' Benefits
00:03:33 - Impact of AI on Jobs and Economy
00:04:11 - Personal Financial Struggles and Housing Market
00:05:03 - Economic Challenges Over the Decades
00:06:18 - Capitalism and Wealth Distribution
00:07:00 - Rand Corporation Study on Income
00:08:37 - WorkMoney's Response to COVID-19
00:09:41 - Empowering Individuals Through Collective Action
00:10:53 - Personal Definitions of a Good Life
00:12:06 - Nonprofit vs. For-Profit Structure
00:13:23 - Growth and Member Engagement
00:14:52 - Remote Work and Organizational Culture
00:16:35 - Advantages of Remote Work
00:16:55 - A Day in the Life of the CEO
00:19:33 - How to Become a WorkMoney Member
00:20:04 - Negotiating on Behalf of Members
00:22:05 - Future Plans for Negotiation Services
00:24:26 - Revenue Model and Philanthropy
00:27:09 - Role of AI in WorkMoney
00:28:28 - Reading Recommendations
00:31:46 - Reflecting on Who Gave a Chance
00:34:25 - Closing Remarks and Gratitude

If you’re interested in leadership, economic mobility, AI, public policy, or the future of work and money, this is a conversation you won’t want to miss.

Seth Sternberg, Co-Founder & CEO of Honor, joins Clint Betts for a powerful conversation on aging, AI, mental health, leadership, and what it means to build technology that is genuinely “world good.”

Honor is transforming how society cares for older adults by helping seniors safely age in their homes through technology-enabled care. In this episode, Seth explains why the aging population crisis is one of the most important challenges of the next decade — and how AI can help solve it.

The conversation also dives into Silicon Valley culture, the responsibility of founders, social media, political division, and why the best companies are built around mission and impact rather than just valuation and wealth.

00:00:00 - Introduction and Honor Technology Overview
00:01:00 - Aging Population and Societal Challenges
00:01:53 - How Honor Technology Helps Older Adults
00:03:01 - Seth's Background and Motivation
00:04:06 - Importance of Meaningful Work
00:05:00 - Silicon Valley's Focus on Valuations Over Impact
00:07:01 - AI's Role in Honor Technology
00:08:30 - AI's Transformational Impact
00:10:07 - Balancing AI's Benefits and Risks
00:10:27 - Typical Day as a CEO
00:13:00 - Maintaining Company Culture
00:15:22 - Reading Habits and Recommendations
00:16:47 - Audio vs. Physical Reading
00:17:24 - CEO's Role in Addressing Societal Issues
00:20:01 - Encouraging Positive World Change
00:21:41 - Mental Health Crisis and Societal Division
00:25:16 - Importance of Constructive Dialogue
00:26:09 - Social Media's Impact on Society
00:28:04 - Legacy and Positive Change
00:29:22 - Final Question: Who Gave You a Chance?
00:31:04 - Closing Remarks

If you’re interested in AI, healthcare, leadership, startups, or the future of technology and society, this is a conversation you won’t want to miss.

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Dax Dasilva, founder and CEO of Lightspeed Commerce, joins Clint Betts for a conversation on building one of Canada’s most successful tech companies from the ground up.

From launching Lightspeed in 2005 to scaling it into a global public company serving 145,000 businesses worldwide, Dax shares lessons on leadership, AI, company culture, profitable growth, and why human connection still matters in the future of work.
00:00:00 - Introduction and Background of Lightspeed Commerce
00:00:54 - Evolution and Expansion of Lightspeed's Services
00:01:26 - Target Market and Customer Base
00:02:07 - Early Success and Key Milestones
00:03:38 - Impact of AI on Business Operations
00:04:45 - Role of the CEO in Modern Times
00:06:03 - Public Statements and Political Opinions
00:07:27 - Going Public: Decision and Reflections
00:08:48 - Benefits of Being a Public Company
00:10:09 - Company Culture and Hybrid Work Model
00:10:25 - Returning as CEO and Office Dynamics
00:12:28 - A Day in the Life of a CEO
00:14:22 - Reading Recommendations
00:15:35 - Writing Books: Process and Inspiration
00:17:44 - Qualities of a Great Leader
00:19:49 - Building a Global Company from Canada
00:20:48 - Economic Outlook and Consumer Sentiment
00:22:49 - Acknowledging Those Who Gave a Chance

If you’re a founder, operator, investor, or aspiring entrepreneur, this episode is packed with insights on building enduring companies in a rapidly changing world.

Jay Kulkarni, Founder & CEO of Theorem, joins Clint Betts for a conversation on AI, video commerce, hybrid work, and building a global technology company without outside funding.

Jay bootstrapped Theorem more than 20 years ago from a spare bedroom in New Jersey and grew it into a global digital marketing technology company serving major media, streaming, and commerce brands around the world.

In this episode, Jay explains why the future of commerce is shifting toward video-driven experiences, how brands are navigating AI and automation, and why authentic human storytelling still matters in an increasingly automated world.

The conversation also explores leadership, company culture, operational discipline, and how hybrid work can succeed when built intentionally.

00:00:00 - Introduction and Jay's Background
00:00:50 - What is Theorem?
00:01:12 - Theorem's Business Model
00:01:55 - Upword: Theorem's Automation Solution
00:02:29 - Video Commerce and Its Importance
00:03:24 - Evolution and Future of Video Commerce
00:04:08 - Benefits of On-Site Video Commerce
00:05:02 - AI in Digital Marketing
00:06:08 - AI and Brand Safety
00:07:03 - AI in Advertising Processes
00:08:16 - Human Touch vs. AI
00:09:38 - Jay's Daily Routine
00:12:00 - Hybrid Work Model
00:14:01 - Building Company Culture
00:17:18 - Internal Use of AI and Automation
00:19:38 - Economic Environment and Future Outlook
00:20:58 - The Importance of Giving Chances
00:21:13 - Personal Story of Opportunity
00:22:56 - Conclusion and Farewell

If you’re a founder, operator, marketer, or leader thinking about AI, media, commerce, and the future of business, this episode is packed with practical insight.

Susan Odle, CEO of StorMagic, joins Clint Betts for a conversation on leadership, remote culture, AI, and the future of edge infrastructure.

StorMagic helps organizations keep critical systems running in remote environments around the world — from retail stores and warehouses to utilities and manufacturing sites. In this episode, Susan explains how the company simplifies virtualization and infrastructure for businesses that can’t afford downtime.

The conversation also dives deep into modern leadership: why empathy matters, how remote-first companies build culture intentionally, and why the best leaders today must balance performance with humanity.

00:00:00 - Introduction and Background
00:00:32 - Joining StoreMagic
00:01:08 - StoreMagic's Edge Solutions
00:02:41 - Democratizing Business
00:03:23 - StoreMagic's Stability and Reliability
00:04:09 - Transition from CGO to CEO
00:06:05 - Daily Routine and Meditation
00:07:43 - Importance of Notepads
00:08:41 - Company Culture and Remote Work
00:10:33 - Management Strategy and Culture
00:12:41 - Reading Recommendations
00:14:19 - Changing Management Paradigms
00:15:03 - AI and Operational Data
00:17:45 - AI Implementation Strategy
00:18:24 - Market and Economic Impact
00:21:00 - Leadership Qualities
00:23:16 - Reflecting on Opportunities Given
00:25:00 - Closing Remarks and Future Topics

If you’re a founder, operator, IT leader, or executive navigating AI, remote work, and modern leadership, this conversation is full of practical insight.