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

Former Journalist, Startup Exec and GTM advisor Keith N
  • 4.6 (40)
  • Entrepreneurship
  • Updated Biweekly

Former journalist turned Silicon Valley dealmaker and entrepreneur Keith Newman talks with Founders, Innovators and Influencers who share their stories of success, pain and impact with a bit of humor and nostalgia mixed in. Hear from Maverick Mark Cuban, SuperAngel Ron Conway, Ann Winblad, Mitch Kapor, Steve Blank and Founders of GameStop, Ancestry, JotForm, Fry's, Intuit, and many more. Find 80+ Episodes https://podcasts.apple.com/us/podcast/the-look-back-a-free-flowing-interview/id1560219589

  1. 2d ago

    How Healthcare Benefits Are Broken—and What Comes Next | Brandy Thompson, CEO of BenefitBay

    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

    21 min

  2. Jun 9

    Greg Whalen (CTO, Prove AI): Why Most AI Projects Fail Before Production

    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 observabilityThe real engineering challenges behind enterprise AIWhy “agentic AI” may be the industry’s most overused termThe shift toward commoditized foundation modelsWhy telemetry and debugging will define reliable AI systemsThe underrated founder skill of ignoring distractionsWhat the AI stack could look like by 2028This 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-whalenDiscord Server (Multi-Agent Systems Engineering Group) - https://discord.gg/sXpr2Hh 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 For sponsorship inquiries, please contact: sponsorships@wherewithstudio.com #AI #ArtificialIntelligence #EnterpriseAI #MachineLearning #SoftwareEngineering #AIInfrastructure #StartupGrowth #Leadership #FounderMindset #TechLeadership

    43 min

  3. Jun 2

    Becoming the VMware of AI Infrastructure: Lukas on Building the Operating System for GPU Clouds

    AI infrastructure is breaking the old data center model. In this episode of Liftoff with Keith, I sit down with Lukas Gentele, CEO & Co-Founder of vCluster Labs, to unpack what it really takes to operate GPU infrastructure at scale in 2026. As AI workloads explode and neoclouds race to meet demand, Lukas and his team are building the operational backbone for modern AI clouds — from managed Kubernetes and tenant isolation to automated node provisioning and GPU lifecycle management. We discuss: Why traditional data center assumptions are collapsing under AI pressureWhat’s fundamentally changed since the VMware eraHow an early partnership with CoreWeave shaped vCluster’s trajectoryAnd the one mistake AI cloud operators are making right now that could hurt them over the next 18 monthsIf you care about AI infrastructure, GPU economics, hyperscaler strategy, or building category-defining platforms — this conversation is essential. 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 Lukas Gentele: Website: https://www.vcluster.com/ LinkedIn: https://www.linkedin.com/in/gentele/ 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 For sponsorship inquiries, please contact: sponsorships@wherewithstudio.comFrom the Host: A special shout-out to our Great Host of the Ignite Studios: https://www.ignitegtm.com/ and Producers of AI Infra5 @Plug and Play World, HQ in Sunnyvale, CA Liftoff is sponsored by a strategic consulting firm and the M&A specialists at Compass Strategic Advisors - https://www.compass-strategic-advisors.com/ and The GTM Firm - https://www.thegtmfirm.com/

    10 min

  4. May 26

    The $7 Trillion AI Infrastructure Boom with Dean Nelson

    Welcome back to Liftoff with Keith, the show where we sit down with the founders, operators, and industry leaders building the future in real time. Today’s guest is one of the most respected voices in digital infrastructure — Dean Nelson. Dean has spent nearly four decades at the center of the internet economy, helping build more than $10 billion in digital infrastructure across four continents for companies like Sun Microsystems, eBay, PayPal, and Uber. He’s also the founder of Infrastructure Masons, a global community uniting the builders of the digital age, now celebrating its 10-year anniversary. In this episode, we unpack the explosive growth happening across AI infrastructure and data centers — including staggering projections that the industry could spend $500 billion this year alone, scale toward $3 trillion by 2028, and potentially hit $7 trillion by 2030. The conversation explores: Why the industry could spend $7 trillion by 2030The explosive rise of AI infrastructureThe shift toward inference and edge computingCommunity and environmental pressures facing data center growthThe labor and construction challenges slowing deploymentWhy Texas has become ground zero for AI infrastructure expansionAnd how power availability may become the defining constraint of the AI eraIf compute scaled like this but power didn’t… are we effectively bottlenecking the AI era on energy infrastructure? This is a fascinating conversation about the future of AI, data centers, infrastructure, and the physical systems powering the next generation of innovation. Let’s lift off. Connect with Dean Nelson: Website: https://imasons.org/ LinkedIn: https://www.linkedin.com/in/deannelson/ Publication: https://imasons.org/publications/ 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 From the Host: A Special Shout out to our Great Host of the Ignite Studios: https://www.ignitegtm.com/ and Producers of AI Infra5 @ Plug and Play World HQ in Sunnyvale, CA Liftoff is Sponsored by - Strategic Consulting firm and the M&A specialists at Compass Strategic Advisors - https://www.compass-strategic-advisors.com/ and The GTM Firm - https://www.thegtmfirm.com/ #AIinfrastructureexpansion #Digitalinfrastructuretrends #Datacentergrowth #Powerandenergyconstraints #Waterstewardship #Skilledlaborshortages #Communitypushback #Digitalsovereignty #dgecomputingandAIinference #PrivateAImodels #Largescaleinfrastructureconstruction

    12 min

  5. May 21

    Anthony Vinci on AI, Decision Intelligence and the Future of Risk

    In this episode, Keith speaks with Anthony Vinci, CEO of VICO, about how AI is changing decision-making for founders, investors, governments, and financial institutions. Anthony’s background spans intelligence, national security, investing, and artificial intelligence. Before founding VICO, he worked at Cerberus Capital Management, Bridgewater Associates, and served as the first Chief Technology Officer at the National Geospatial-Intelligence Agency. The conversation explores how AI is moving beyond chatbots and becoming a real decision-making layer for businesses. Anthony explains why the future is not about replacing human judgment, but improving it through better frameworks, probability forecasting, and scenario planning. They discuss: Why AI alone is not enough without human judgmentHow VICO combines LLMs with mathematical forecastingThe difference between information and decision intelligenceWhy founders need better frameworks for uncertaintyHow AI is reshaping risk assessment and strategic planningThe future of building companies in the AI eraThis episode is a thoughtful look at what happens when AI moves from generating answers to helping people make better decisions. Connect with Anthony Vinci: Website: https://vico.io/ LinkedIn: https://www.linkedin.com/in/anthony-vinci/Book: https://www.anthonyvinci.com/ 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 For sponsorship inquiries, please contact: sponsorships@wherewithstudio.com #ArtificialIntelligence #AI #DecisionMaking #Leadership #Entrepreneurship #RiskManagement #FounderMindset #MachineLearning #StartupGrowth #FutureOfWork

    34 min

  6. May 12

    Most founders know how to start. Few know how to finish | Steven Pivnik

    Steven Pivnik scaled his company to 200+ employees across 12 countries before executing a strategic acquisition to a $4B competitor. Along the way, he completed 17 IRONMAN triathlons and climbed at extreme altitude — including Everest. In this episode of Liftoff with Keith, we break down: The difference between growth and disciplined growthWhy founders should design their exit years in advanceHow endurance training builds better leadershipAvoiding burnout while scaling under pressureWhat it really means to “finish strong”This is a conversation about commitment, structure, and the mindset required to endure when quitting would be easier. If you’re building, scaling, or thinking about your long-term exit — this episode is for you. Connect with Steven Pivnik: Website: https://stevenpivnik.com/LinkedIn: https://www.linkedin.com/in/stevenpivnik/ Instagram: https://www.instagram.com/stevenpivnik/ 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 For sponsorship inquiries, please contact: sponsorships@wherewithstudio.com #Entrepreneurship #Ironman #FounderMindset #Leadership #Endurance #StartupGrowth #BusinessLeadership #MentalToughness #PersonalGrowth

    24 min

  7. May 5

    From Wine Night to Patent: Michael Fors and the Story Behind Liquid Jazz

    In this episode, Keith sat down with Michael Fors, inventor and owner of the Liquid Jazz Experience, to explore how a simple ritual turned into a patented product. What started as a weekly wine night with friends evolved into something much bigger. Over time, Michael began to notice a small but consistent problem. Great wine often needed time to open up, but real moments do not wait. That observation led to an idea. And that idea eventually became Liquid Jazz, a decanter designed to bring wine to life in minutes. In this conversation, Michael shares: How a 26-year tradition became the foundation for a productThe moment of insight that came from watching ocean wavesWhat it really takes to turn an idea into a patentThe challenges of bringing a product to marketWhy not every idea should become a businessThis is a story about paying attention, solving real problems, and knowing when to take something seriously.Connect with Michael Fors: Website: https://liquidjazzexperience.com/pages/about Instagram: https://www.instagram.com/liquidjazzexperience/ 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 For sponsorship inquiries, please contact: sponsorships@wherewithstudio.com#StartupStory #ProductInnovation #FounderJourney #Entrepreneurship #DesignThinking #ConsumerProduct #Innovation #BusinessStory

    33 min

  8. Apr 28

    AI Visibility, Founder Branding and the Minimum Viable Visibility System with Gal

    In this episode, we sit down with Gal, Founder of Borenstein Group, to unpack what it really takes to be visible in an AI driven world. Most founders still think visibility is about content or marketing channels. Gal takes a different view. He explains why visibility today is about building a system that AI can understand, trust and reference. We talk about what he calls a “minimum viable visibility system” and why most companies get it wrong. Instead of trying to do everything, the focus should be on a few clear signals that help AI connect your brand to a specific problem. The conversation covers: Why most founders are invisible in AI searchThe shift from traditional SEO to AI driven discoveryWhat a minimum viable visibility system looks like in practiceHow founders can become the face of their categoryWhy clarity matters more than volume in contentIf you are building a company and want to stay relevant as AI becomes the first place people go for answers, this episode will give you a simple way to think about visibility. Connect with Gal Borenstein: Website: https://www.borensteingroup.com/LinkedIn: https://www.linkedin.com/in/galborensteinexecutiveprofile/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/liftoffwithkeithTikTok: https://www.tiktok.com/@keithnewman74 For sponsorship inquiries, please contact: sponsorships@wherewithstudio.com#AIVisibility #FounderBranding #AEO #GEO #B2BMarketing #PersonalBranding #ContentStrategy #StartupGrowth #DigitalStrategy #AI

    28 min
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4.6
out of 5
40 Ratings

About

Former journalist turned Silicon Valley dealmaker and entrepreneur Keith Newman talks with Founders, Innovators and Influencers who share their stories of success, pain and impact with a bit of humor and nostalgia mixed in. Hear from Maverick Mark Cuban, SuperAngel Ron Conway, Ann Winblad, Mitch Kapor, Steve Blank and Founders of GameStop, Ancestry, JotForm, Fry's, Intuit, and many more. Find 80+ Episodes https://podcasts.apple.com/us/podcast/the-look-back-a-free-flowing-interview/id1560219589

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