What if the biggest threat to your startup isn't competition, funding, or even product-market fit—but your own management team?

In this episode of Liftoff with Keith, I sit down with entrepreneur, investor, and author Hunter Hastings to explore one of the most important—and controversial—ideas in modern entrepreneurship.

Hunter is the co-author of Venture Mode: Escape the Administration Trap by Finding and Unleashing Entrepreneurial Leaders, where he argues that companies rarely fail because they grow too quickly. Instead, they lose the entrepreneurial behaviors that made them successful in the first place.

As organizations scale, speed gives way to bureaucracy, customer obsession is replaced by internal process, and entrepreneurial leaders become administrators.

We dive into what Hunter calls "The Administration Trap"—and how founders can avoid it.

In this episode we discuss:

• Why management—not growth—is often what kills startups
• The earliest warning signs that bureaucracy is taking over
• How founders can add structure without losing entrepreneurial culture
• Why customer value—not internal metrics—should drive every decision
• How to identify and empower entrepreneurial leaders inside your company
• Why traditional MBA thinking often fails founders
• Cash flow, value creation, and building resilient businesses
• How AI is changing the economics of startups and leadership
• The biggest misconceptions founders and investors have about scaling companies
• Hunter's personal lessons from decades as a CEO, investor, executive, and educator

If you're a founder, executive, investor, or anyone leading a growing company, this conversation offers a fresh framework for scaling without sacrificing innovation.

Connect with Keith

If you enjoyed this episode, please subscribe, leave a review, and share it with another founder or operator.

Follow Liftoff with Keith for conversations with the entrepreneurs, investors, and innovators building the future.

Sponsor Info: We are strategic business advisors with decades of leadership experience and a proven track record of driving businesses’ growth. We specialize in creating custom-tailored strategies to introduce your company, drive growth, build leadership teams, and ensure companies implement appropriate compensation programs. Our mission is to utilize our expansive network to benefit your company https://www.compass-strategic-advisors.com/Connect with Hunter:

• Book: Venture Mode: Escape the Administration Trap by Finding and Unleashing Entrepreneurial Leaders https://www.amazon.in/Venture-Mode-Administration-Unleashing-Entrepreneurial-ebook/dp/B0FQWF2FP5
• LinkedIn: https://www.linkedin.com/in/hunterhastings/
• Website: https://venturemode.biz/

Subscribe for more founder insights and hit the bell for notifications!

Follow us on our channels for exclusive startup content and behind-the-scenes insights from interviews like this one.

• Spotify: https://open.spotify.com/show/3cFpLXfYvcUsxvsT9MwyAD?si=f5a14e779777487d
• Apple Podcasts: https://podcasts.apple.com/ca/podcast/liftoff-with-keith-newman/id1560219589
• Substack: https://keithnewman.substack.com/
• Newman Media Studios: https://newmanmediastudios.com/
• LinkedIn: https://www.linkedin.com/company/liftoffwithkeith
• Facebook: https://www.facebook.com/KeithNewman285
• Website: https://liftoffwithkeith.com/

Want to build a high-growth company without falling into the administration trap? Subscribe to Liftoff with Keith and follow for weekly conversations with the founders building what's next.

What if your AI assistant didn't just answer questions—but actually understood how you work and helped get things done?

In this episode of Liftoff with Keith, Keith sits down with Jean-Denis Greze, Co-Founder & CEO of Town, to explore the future of personalized AI assistants and what it takes to build AI that can work across the tools people already use.

The conversation dives into how AI can move beyond the traditional chatbot experience to help manage tasks, workflows, email, calendars, and more—while learning from the context of how each person actually works.

Jean-Denis also shares insights into building an AI product, the challenges of creating a truly useful assistant, and the broader opportunity to make AI more accessible to everyday users and businesses.

If you're interested in AI, AI assistants, startups, productivity, entrepreneurship, and the future of work, this episode is for you.

Sponsor Info: We are strategic business advisors with decades of leadership experience and a proven track record of driving businesses’ growth. We specialize in creating custom-tailored strategies to introduce your company, drive growth, build leadership teams, and ensure companies implement appropriate compensation programs. Our mission is to utilize our expansive network to benefit your company https://www.compass-strategic-advisors.com/

Connect with Jean-Denis:

• Website: https://www.town.com/
• LinkedIn: https://www.linkedin.com/in/jeandenisgreze/

Subscribe for more founder insights and hit the bell for notifications!

Follow us on our channels for exclusive startup content and behind-the-scenes insights from interviews like this one.

• Spotify: https://open.spotify.com/show/3cFpLXfYvcUsxvsT9MwyAD?si=f5a14e779777487d
• Apple Podcasts: https://podcasts.apple.com/ca/podcast/liftoff-with-keith-newman/id1560219589
• Substack: https://keithnewman.substack.com/
• Newman Media Studios: https://newmanmediastudios.com/
• LinkedIn: https://www.linkedin.com/company/liftoffwithkeith
• Facebook: https://www.facebook.com/KeithNewman285- Website: https://liftoffwithkeith.com/

If you enjoyed this episode, don't forget to Like, Subscribe and Share.

What do Iraq, SpaceX, the EV boom, and autonomous freight have in common?

In this episode of Liftoff, Keith sits down with Kevin Damoa , Army combat veteran and founder & CEO of Glīd, to explore the future of logistics and the technology transforming how freight moves between road and rail.

Kevin shares how nearly 25 years of logistics experience, including military logistics, SpaceX, and leadership roles across the EV industry, inspired him to tackle one of the biggest challenges in global supply chains: making rail transportation more accessible.

We discuss how Glīd is building autonomous vehicles designed to streamline the road-to-rail transition, why the company has focused on building more cost-efficiently, and how Kevin's experiences at SpaceX shaped his approach to culture, innovation, and solving seemingly impossible problems.

Kevin also shares lessons on:

• Building hard tech with limited capital
• Why culture can make or break a startup
• The importance of solving customer pain before commercialization
• How to evaluate risk before launching an MVP
• The future of autonomous freight and physical AI
• Why logistics is facing a growing labor and infrastructure challenge
• What SpaceX taught him about belief, ingenuity, and making the impossible possible

From combat logistics to rocket logistics to autonomous freight, this is a conversation about building technology that could fundamentally change how the world moves.

Sponsor Info: We are strategic business advisors with decades of leadership experience and a proven track record of driving businesses’ growth. We specialize in creating custom-tailored strategies to introduce your company, drive growth, build leadership teams, and ensure companies implement appropriate compensation programs. Our mission is to utilize our expansive network to benefit your company https://www.compass-strategic-advisors.com/Connect with Kevin Damoa:

• Website: https://www.glidtech.us/
• LinkedIn: https://www.linkedin.com/in/kevin-a-damoa-9b514770

Subscribe for more founder insights and hit the bell for notifications!

Follow us on our channels for exclusive startup content and behind-the-scenes insights from interviews like this one.

• Spotify: https://open.spotify.com/show/3cFpLXfYvcUsxvsT9MwyAD?si=f5a14e779777487d
• Apple Podcasts: https://podcasts.apple.com/ca/podcast/liftoff-with-keith-newman/id1560219589
• Substack: https://keithnewman.substack.com/
• Newman Media Studios: https://newmanmediastudios.com/
• LinkedIn: https://www.linkedin.com/company/liftoffwithkeith
• Website: https://liftoffwithkeith.com/

If you enjoyed this episode, don't forget to Like, Subscribe and Share.

What if AI could understand the physical world as well as it understands text?

In this episode of The Liftoff, Keith sits down with Paul Powers, CEO & Co-Founder of Physna, to explore why the next wave of AI won't just generate content—it will understand objects, manufacturing, engineering, and supply chains.

Paul explains how Physna's "Physical DNA" technology enables AI to understand 3D objects, helping companies dramatically improve product design, procurement, robotics, digital twins, and manufacturing intelligence. The conversation also covers reshoring manufacturing, AI infrastructure, startup timing, and why physical AI could become one of the biggest technology shifts of the decade.

In this episode:

• What Physical AI actually means
• How Physna teaches computers to understand 3D objects
• Why AI struggles with the physical world today
• Saving manufacturers hundreds of millions of dollars
• Digital twins, robotics & engineering AI
• The future of manufacturing and reshoring
• AI, 3D printing & security challenges
• Startup lessons from building deep-tech companies
• Why timing matters more than most founders realize

If you enjoy conversations about AI, startups, innovation, deep technology, and entrepreneurship, don't forget to Like, Subscribe, and Share.

Sponsor Info: We are strategic business advisors with decades of leadership experience and a proven track record of driving businesses’ growth. We specialize in creating custom-tailored strategies to introduce your company, drive growth, build leadership teams, and ensure companies implement appropriate compensation programs. Our mission is to utilize our expansive network to benefit your company https://www.compass-strategic-advisors.com/

Connect with Trip Hawkins:

• Website: https://www.ea.com/
• LinkedIn: https://www.linkedin.com/in/triphawkins/

Subscribe for more founder insights and hit the bell for notifications!

Follow us on our channels for exclusive startup content and behind-the-scenes insights from interviews like this one.

• Spotify: https://open.spotify.com/show/3cFpLXfYvcUsxvsT9MwyAD?si=f5a14e779777487d
• Apple Podcasts: https://podcasts.apple.com/ca/podcast/liftoff-with-keith-newman/id1560219589
• Substack: https://keithnewman.substack.com/
• Newman Media Studios: https://newmanmediastudios.com/
• LinkedIn: https://www.linkedin.com/company/liftoffwithkeith
• Website: https://liftoffwithkeith.com/

If you enjoyed this episode, don't forget to Like, Subscribe and Share.

#AI #ArtificialIntelligence #PhysicalAI #Physna #PaulPowers #Manufacturing #Engineering #Robotics #DigitalTwins #SupplyChain #Innovation #DeepTech #Startup #Entrepreneurship #TheLiftoff

What does it take to build a company that changes an entire industry?

Note: Due to some video connection challenges the host wasn't on the video feed for the entire program

In this episode of Liftoff with Keith, legendary entrepreneur Trip Hawkins, Founder of Electronic Arts (EA) and creator of one of the world's most influential gaming companies, shares the principles behind building category-defining businesses.

From launching EA and helping create the Madden franchise to investing in the next generation of AI startups, Trip explains why lasting companies don't simply build better products they change customer behavior.

In this conversation, you'll learn:

• How Electronic Arts transformed the gaming industry
• The strategy behind creating billion-dollar companies
• Why changing customer behavior creates lasting value
• What investors really look for in founders
• AI opportunities every business leader should understand
• Why enterprise AI readiness matters more than AI hype
• Lessons from decades of innovation and venture investing

Whether you're an entrepreneur, founder, investor, executive, or technology leader, this episode is packed with timeless insights on innovation, leadership and building businesses that last.

If you enjoyed this conversation, like the video, subscribe, and share it with someone building the future.

Sponsor Info: We are strategic business advisors with decades of leadership experience and a proven track record of driving businesses’ growth. We specialize in creating custom-tailored strategies to introduce your company, drive growth, build leadership teams, and ensure companies implement appropriate compensation programs. Our mission is to utilize our expansive network to benefit your company https://www.compass-strategic-advisors.com/Connect with Trip Hawkins:

• Website: https://www.ea.com/
• LinkedIn: https://www.linkedin.com/in/triphawkins/

Subscribe for more founder insights and hit the bell for notifications!

Follow us on our channels for exclusive startup content and behind-the-scenes insights from interviews like this one.

• Spotify: https://open.spotify.com/show/3cFpLXfYvcUsxvsT9MwyAD?si=f5a14e779777487d
• Apple Podcasts: https://podcasts.apple.com/ca/podcast/liftoff-with-keith-newman/id1560219589
• Substack: https://keithnewman.substack.com/
• Newman Media Studios: https://newmanmediastudios.com/
• LinkedIn: https://www.linkedin.com/company/liftoffwithkeith
• Website: https://liftoffwithkeith.com/

If you enjoyed this episode, don't forget to Like, Subscribe and Share.

The AI boom isn't over but the first wave is.

In this episode of Liftoff with Keith, Keith sits down with Clint Chao, Co-Founder & General Partner at Moment Ventures, to discuss where AI is really headed, why enterprise software is entering a new phase, and what founders should focus on as the hype settles.

They explore venture capital, AI adoption, enterprise transformation, startup execution, and what separates companies that create lasting value from those simply following the latest trend.

Whether you're a founder, investor, operator, or simply curious about the future of AI, this conversation is packed with practical insights.

Key Topics

• Why the first wave of AI is ending
• What comes next for Enterprise AI
• Building companies during technology shifts
• Venture capital perspectives on AI startups
• Enterprise software trends
• What investors are looking for today
• Long-term opportunities in AI

If you enjoy conversations with world-class founders, investors and operators, subscribe to Liftoff with Keith.

Sponsor Info: We are strategic business advisors with decades of leadership experience and a proven track record of driving businesses’ growth. We specialize in creating custom-tailored strategies to introduce your company, drive growth, build leadership teams, and ensure companies implement appropriate compensation programs. Our mission is to utilize our expansive network to benefit your company https://www.compass-strategic-advisors.com/Connect with Clint Chao:

• Website: http://www.momentventures.com/
• LinkedIn: https://www.linkedin.com/in/clintchao

Subscribe for more founder insights and hit the bell for notifications!

Follow us on our channels for exclusive startup content and behind-the-scenes insights from interviews like this one.

• Spotify: https://open.spotify.com/show/3cFpLXfYvcUsxvsT9MwyAD?si=f5a14e779777487d
• Apple Podcasts: https://podcasts.apple.com/ca/podcast/liftoff-with-keith-newman/id1560219589
• Substack: https://keithnewman.substack.com/
• Newman Media Studios: https://newmanmediastudios.com/
• LinkedIn: https://www.linkedin.com/company/liftoffwithkeith

If you enjoyed this episode, don't forget to Like, Subscribe and Share.

Most businesses don't fail because they lack ideas.

They fail because they struggle to execute, communicate their value clearly, and connect with the right customers.

In this episode of Liftoff, Keith Newman sits down with Stephen Cozzolongo, Partner & CMO at Digital Position, to discuss growth marketing, customer acquisition, AI, business scaling, leadership, and the mindset required to build successful companies.

Stephen shares why trying to market to everyone is one of the biggest mistakes businesses make, how AI is transforming marketing workflows, why great marketers aren't being replaced by AI, and how discipline and consistency influence every aspect of business and life.

Whether you're a founder, marketer, entrepreneur, or business leader, this conversation is packed with practical insights on growth, execution, and long-term success.

Topics discussed:

• Why most brands stop growing
• The importance of customer segmentation and ICPs
• How AI is changing marketing and advertising
• The future of content creation
• Paid media, SEO and growth strategies
• Leadership and company culture
• The mindset behind consistent execution
• Why "How you do one thing is how you do everything"

Connect with Stephen Cozzolongo:

• Website: https://www.digitalposition.com/

• LinkedIn: https://www.linkedin.com/in/stephencozzolongo

Sponsor Info: We are strategic business advisors with decades of leadership experience and a proven track record of driving businesses’ growth. We specialize in creating custom-tailored strategies to introduce your company, drive growth, build leadership teams, and ensure companies implement appropriate compensation programs. Our mission is to utilize our expansive network to benefit your company https://www.compass-strategic-advisors.com/

Subscribe for more founder insights and hit the bell for notifications!

Follow us on our channels for exclusive startup content and behind-the-scenes insights from interviews like this one.

• Spotify: https://open.spotify.com/show/3cFpLXfYvcUsxvsT9MwyAD?si=f5a14e779777487d
• Apple Podcasts: https://podcasts.apple.com/ca/podcast/liftoff-with-keith-newman/id1560219589
• Substack: https://keithnewman.substack.com/
• Newman Media Studios: https://newmanmediastudios.com/
• LinkedIn: https://www.linkedin.com/company/liftoffwithkeith

#Marketing #GrowthMarketing #BusinessGrowth #Entrepreneurship #DigitalMarketing #AI #Leadership #SEO #PaidMedia #BusinessPodcast #LiftoffPodcast

Healthcare costs continue to rise, employees have fewer choices than ever, and many employers are stuck navigating a system that feels increasingly unsustainable.

In this episode of Liftoff, Keith Newman sits down with Brandy Thompson, Founder & CEO of BenefitBay, to discuss the future of healthcare benefits, employee choice, leadership, entrepreneurship, and building a fast-growing company in one of the most complex industries in America.

Brandy shares why she believes employees should have greater control over their healthcare decisions, how transparency can improve outcomes, and why the future of benefits may look very different than today's one-size-fits-all model.

The conversation also explores founder lessons, leadership, raising six children while building a career, and what it takes to lead through growth and change.

About Brandy Thompson:

Brandy Thompson is the Founder & CEO of BenefitBay, a Kansas City-based company helping employers modernize healthcare benefits through Individual Coverage Health Reimbursement Arrangements (ICHRAs). BenefitBay recently announced an $18 million Series A funding round to expand its platform and infrastructure supporting personalized employee healthcare benefits.

Connect with Brandy Thompson:

• Website: https://www.benefitbay.com/
• LinkedIn: https://www.linkedin.com/in/brandy-thompson-24389536
• Benefitbay just raised a series A, which will lend itself to really good growth questions: https://www.einpresswire.com/article/914114134/benefitbay-raises-18-million-series-a-led-by-ten-coves-capital-to-scale-its-broker-first-ichra-platform

Sponsor Info: We are strategic business advisors with decades of leadership experience and a proven track record of driving businesses’ growth.

We specialize in creating custom-tailored strategies to introduce your company, drive growth, build leadership teams, and ensure companies implement appropriate compensation programs. Our mission is to utilize our expansive network to benefit your company https://www.compass-strategic-advisors.com/

Subscribe for more founder insights and hit the bell for notifications! Follow us on our channels for exclusive startup content and behind-the-scenes insights from interviews like this one.

• Spotify: https://open.spotify.com/show/3cFpLXfYvcUsxvsT9MwyAD?si=f5a14e779777487d
• Apple Podcasts: https://podcasts.apple.com/ca/podcast/liftoff-with-keith-newman/id1560219589
• Substack: https://keithnewman.substack.com/
• Newman Media Studios: https://newmanmediastudios.com/
• LinkedIn: https://www.linkedin.com/company/liftoffwithkeith

#Healthcare #Leadership #EmployeeBenefits #Entrepreneurship #FounderJourney #CEO #FutureOfWork #HealthInsurance #HealthcareInnovation #BusinessPodcast #LiftoffPodcast #BenefitBay