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

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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/

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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/

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• Spotify: https://open.spotify.com/show/3cFpLXfYvcUsxvsT9MwyAD?si=f5a14e779777487d
• Apple Podcasts: https://podcasts.apple.com/ca/podcast/liftoff-with-keith-newman/id1560219589
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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

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• Apple Podcasts: https://podcasts.apple.com/ca/podcast/liftoff-with-keith-newman/id1560219589
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