Liftoff with Keith: Conversations with Super Founders and Growth Experts sharing useful insights

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
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What separates unforgettable brands from businesses that constantly fight for attention?
In this episode of Liftoff with Keith, branding expert Bill Harper, Founder of Brand Boss HQ and one of the world's Top 20 Branding Experts, shares why branding—not just marketing—is the ultimate competitive advantage.
Bill explains why most companies spend too much time optimizing ads and too little time building a memorable brand. From GEICO and Volvo to startups and SaaS businesses, he reveals how successful companies create differentiation, simplify their message, and become the obvious choice for customers.
We also discuss:
Brand Strategy vs Brand Identity
Why performance marketing alone eventually fails
How AI is changing branding and marketing
The psychology behind memorable brands
How startups can stand out in crowded markets
Real-world branding success stories
Creating a brand customers actually rememberWhether you're a founder, entrepreneur, marketer, or business leader, this conversation is packed with practical branding advice you can implement immediately.
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 Bill Harper:
Website: https://www.brandbosshq.com/
LinkedIn: https://www.linkedin.com/in/brandbosshq/
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#Branding #Marketing #Startup #Entrepreneurship #BusinessGrowth #BrandStrategy #AI #MarketingStrategy #Founder #Podcast

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

In this episode, Keith sits down with an AI infrastructure leader to unpack what is really happening behind the current AI boom.
While most conversations focus on models and hype, this discussion goes deeper into the engineering realities of building reliable AI systems at scale.
The conversation explores why observability, telemetry, debugging, and system architecture are becoming critical as enterprises move from experimentation to production AI.
They also discuss why terms like “agentic AI” are often misunderstood, why many AI projects end up being rebuilt from scratch, and why the future competitive advantage may come from the tooling built around models rather than the models themselves.
Topics covered include:
Why most AI systems fail due to poor observability
The real engineering challenges behind enterprise AI
Why “agentic AI” may be the industry’s most overused term
The shift toward commoditized foundation models
Why telemetry and debugging will define reliable AI systems
The underrated founder skill of ignoring distractions
What the AI stack could look like by 2028
This episode is a practical conversation about the difference between AI demos and real AI infrastructure.
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 Greg Whalen:
Website: https://prove.ai/
LinkedIn: https://www.linkedin.com/in/greg-m-whalen
Discord Server (Multi-Agent Systems Engineering Group) - https://discord.gg/sXpr2Hh
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#AI #ArtificialIntelligence #EnterpriseAI #MachineLearning #SoftwareEngineering #AIInfrastructure #StartupGrowth #Leadership #FounderMindset #TechLeadership