Inspired with Alexa von Tobel

From the Microsoft boardroom to Harvard to Ukraine’s economic recovery, Penny Pritzker has held one of the rarest vantage points in business and public life. She sits on Microsoft’s board at a defining moment for AI, helps lead Harvard, served as U.S. Secretary of Commerce, and was the U.S. Special Representative for Ukraine’s Economic Recovery. She’s also the co-founder of Inspired Capital alongside Alexa von Tobel. Alexa and Penny’s relationship started more than a decade ago, when Penny built the Presidential Ambassadors for Global Entrepreneurship program from scratch as Commerce Secretary and invited Alexa to serve. A shared belief in founders turned into a friendship, and eventually into Inspired Capital. In this episode, the two sit down together and Penny shares what it was like growing up as her family built Hyatt, the letter to her grandfather that got her into business, and the framework she leans on when the stakes are highest. They also talk about what makes Inspired different, from the hustle and the network to the intensity and care the team brings to every founder, and why, with the firm’s $450M Fund IV, they’re only getting started. 🔗 Penny Pritzker • LinkedIn: https://www.linkedin.com/in/penny-pritzker/ 🎙️ Inspired Capital • Website: https://www.inspiredcapital.com/  • LinkedIn: https://www.linkedin.com/company/inspired-capital-partners/ • X: https://x.com/InspiredCap • Instagram: https://www.instagram.com/inspiredcapital/ • Substack: https://alexavontobel.substack.com/ Chapters: 0:00 Intro 0:49 Welcome to Inspired 1:19 Growing Up in the Hyatt Family 5:00 Taking Hyatt International 5:44 Losing Her Father at 13 9:14 The Letter to Her Grandfather 12:45 From Harvard and Stanford to Building Businesses 14:03 Starting a Senior Living Company at 27 16:48 Early Mistakes and Learning to Fire Someone 17:45 Why Building Businesses Is Noble 20:11 Seven Companies and Becoming Secretary of Commerce 22:16 Promoting Entrepreneurship Around the World 25:25 American Ambition and Risk-Taking 29:16 “Oh My God, I Work Here”: Life at the White House 31:51 Listening to American Businesses 33:11 Diplomacy, Privacy Shield and the CHIPS Act 36:17 A Fist Bump from President Obama 37:17 Helping Rebuild Ukraine 41:01 How to Make Hard Decisions 43:48 Life Is a Team Sport 45:33 Inside Inspired’s Culture 48:34 Closing Fund Four and Portfolio Results 51:49 Inside the Microsoft Boardroom on AI 55:07 AI and the Future of Work 57:40 Inspired’s Big Bets 58:48 Closing Thoughts

James Cadwallader thinks the most important reader on the internet isn’t human anymore.  When he asked ChatGPT for a better showerhead, it visited 65 websites. He expects that number to hit 6,500 within five years, and most brands have no idea what those agents are saying about them. Profound is his bet on that shift, and it’s already inside a third of the Fortune 100. In this episode he explains why AI slop is a skill issue, why he thinks billboards and dinners are about to matter more than ever, and why he believes humans are quietly becoming the API between reality and AI. 🔗 James Cadwallader • Website: https://www.tryprofound.com/ • X: https://x.com/thejamescad • LinkedIn: https://www.linkedin.com/in/jamescadwallader   🎙️ Inspired Capital • Website: https://www.inspiredcapital.com/  • LinkedIn: https://www.linkedin.com/company/inspired-capital-partners/ • X: https://x.com/InspiredCap • Instagram: https://www.instagram.com/inspiredcapital/ • Substack: https://alexavontobel.substack.com/ Chapters: 0:00 Intro 1:10 What Profound does 2:56 Lessons from his first company, Kyra Media 6:46 AEO and GEO explained 10:19 Why ChatGPT ran 65 searches for one showerhead 12:19 How one model update can swing a brand's AI visibility 14:27 Why marketers will need 100x more content 15:55 How Profound keeps pace with the AI labs 18:28 Building a paranoid culture 20:47 How Profound won a third of the Fortune 100 23:20 Dead internet theory: the internet in 5 years 25:30 Humans as APIs between reality and AI 27:25 Why every brand will own its own evals 29:08 Marketing a product in 2030 30:20 How to avoid AI slop 32:56 The barbell: agentic marketing vs. human marketing 34:26 What excites him most: Profound Labs 35:42 Building the next Salesforce 37:30 Social media as a "biozone" for human data 40:56 Contrarian take: the AI labs won't eat every industry 41:49 How he stays sane

Boris Sofman, co-founder and CEO of Bedrock Robotics and former leader of autonomous trucking at Waymo, has built consumer and industrial robots. He discusses retrofitting construction machines into fully autonomous excavators. He explores how autonomy can ease the construction labor shortage, reshape cities and logistics, and what it takes to make heavy machinery reliable outside test environments.

Windmill co-founders Max Shaw and Brian Distelburger are building the AI-powered people platform for how companies develop and manage their talent. Founded alongside Mark Tanner, Windmill replaces the broken, once-a-year performance review with something faster, smarter, and that employees actually love. Since launching in November 2025, they've reached more than 100 customers including Kalshi, The Farmer's Dog, and Rho, and Inspired is so proud to have led their recent seed round. As AI makes every employee more powerful, the companies that win will be the ones that put the best talent in exactly the right role. What You'll Learn: Why the current state of performance management is broken How AI will change the relationship between managers and their teams What the future of work looks like as companies grow more complex Why skills assessment is about to become one of the most important things a company can do Why Max and Brian are optimistic that AI will benefit people at work Chapters: 00:00 Introduction  02:33 Meet Max and Brian  03:44 What Is Windmill 05:38 The State of Performance Reviews  09:20 Where Windmill Is Headed  13:20 AI Coaching for Every Employee  16:15 Why They Chose This Problem  18:33 The Biggest Change Management Moment of Our Lives  24:15 Early Traction and What's Working  27:30 Where the World of Work Is Going  34:55 The IKEA Example  36:16 Skills Assessment and Workforce Redeployment  41:18 Why New York  43:35 Quickfire Follow Max, Brian, and Windmill: • Website: https://gowindmill.com/ • LinkedIn: https://www.linkedin.com/company/gowindmill/ • X: https://x.com/trywindmill • Max's LinkedIn: https://www.linkedin.com/in/max-shaw-82287025/ • Brian's LinkedIn: https://www.linkedin.com/in/briandistelburger/ Follow Inspired:‍ • Website: https://www.inspiredcapital.com/ • LinkedIn: https://www.linkedin.com/company/inspired-capital-partners • X: https://x.com/InspiredCap • Instagram: https://www.instagram.com/inspiredcapital/ • Substack: https://alexavontobel.substack.com/

Runway founder and CEO Cristóbal Valenzuela grew up in Chile before moving to New York to study at NYU's ITP program, where the seeds of Runway were planted. Since co-founding the company in 2018, he has built it into one of the leading generative video AI companies in the world, having raised more than $500M in funding and pioneered some of the first widely used text to video and video to video models. Runway is now pushing toward what Cristóbal calls world models, systems that can understand and simulate reality in ways that are reshaping film, advertising, gaming, and beyond. The next era of human creativity is just getting started. What You'll Learn: Why world models represent a fundamental shift in how we create and consume content How the democratization of storytelling will change culture as we know it What real time video generation means for the future of entertainment and gaming How AI is poised to transform the advertising industry from the ground up Why optimism, not fear, is the right response to AI and the future of work Chapters: 00:00 Introduction01:30 Growing Up in Chile04:20 What Is Runway06:38 Real World Use Cases10:25 The Technology Behind the Breakthrough12:00 Underestimating the Speed of Progress14:55 If Content Is Free Does It Lose Value20:10 How Runway Makes Money24:05 The Real-Time Generation Revolution29:15 Gaming and Interactive Experiences33:00 The Future of Advertising35:45 The Consequences of Infinite Content37:20 Why Billions of Stories Are Waiting41:00 Will AI Kill Jobs44:00 Quickfire Follow Cristóbal and Runway: Instagram: https://www.instagram.com/runwayapp LinkedIn: https://www.linkedin.com/company/runwayml/  X: https://x.com/runwayml Youtube: https://www.youtube.com/runwayml Cristóbal's LinkedIn: https://www.linkedin.com/in/cvalenzuelab/ Cristóbal's X: https://x.com/c_valenzuelab Follow Inspired:‍ Website: https://www.inspiredcapital.com/  LinkedIn: https://www.linkedin.com/company/inspired-capital-partners  X: https://x.com/InspiredCap  Instagram: https://www.instagram.com/inspiredcapital/ Substack: https://alexavontobel.substack.com/

Chainguard founder and CEO Dan Lorenc is building the security layer the entire software industry should run on. After nearly a decade at Google working on open source infrastructure, Dan co-founded Chainguard in 2021 to solve a problem hiding in plain sight. 90 to 95 percent of the code powering the world's software is open source, free, and largely unsecured. Now leading a $3.5B+ company with more than 600 customers, Dan shares his unfiltered take on where software security, AI, and the future of engineering are all headed. What You'll Learn: How Chainguard is securing the open source software the world runs on Why the AI coding boom is making software security harder, not easier What the future of software engineering actually looks like Why CISOs can't afford to say no to AI, even when it scares them Whether we've already hit AGI in the software space How to think about your own digital security right now Chapters: 00:00 Introduction01:30 Growing Up a Builder04:22 The Origin of Chainguard08:20 How Chainguard Works and Who It's For13:20 How Chainguard Cleans and Secures the Code15:20 How Dan Decides Where to Expand17:15 The Future of Software and Software Engineers25:30 Where Chainguard Goes From Here26:48 Are We Already at AGI?28:30 The Security Crisis No One Talks About31:27 Why CISOs Can't Afford to Say No33:25 Biggest Trade-Offs and What's Next for Chainguard38:00 What Disappears in an AI World39:22 What Shocked Dan Most and What Scares Him42:30 When Security Becomes Part of Engineering44:39 QuickfireFollow Dan and Chainguard: Website: https://www.chainguard.dev/ LinkedIn: https://www.linkedin.com/company/chainguard-dev/  Youtube: https://www.youtube.com/@chainguard  X: https://x.com/chainguard_dev  Dan’s LinkedIn: https://www.linkedin.com/in/danlorenc/  Dan’s X: https://x.com/lorenc_dan  Follow Inspired: Website: https://www.inspiredcapital.com/  LinkedIn: https://www.linkedin.com/company/inspired-capital-partners  X: https://x.com/InspiredCap  Instagram: https://www.instagram.com/inspiredcapital/ Substack: https://alexavontobel.substack.com/

Michael Brown, Co-founder and CEO of TeamShares, builds a programmatic acquirer that buys retiring-owner small businesses and turns them into employee-owned companies. He explains how the model scales, what nearly 100 acquisitions revealed about small businesses, why going public is only the beginning, and how a 200-year mindset shapes long-term strategy.

What happens when humanity faces the sixth mass extinction event in Earth's history? Serial entrepreneur Ben Lamm believes we need a backup plan. With a track record of building and exiting companies across AI, gaming, and conversational intelligence, Ben took on his most audacious venture in 2021: co-founding Colossal Biosciences with Harvard geneticist Dr. George Church to bring extinct species back to life. The company has already successfully de-extincted the dire wolf and aims to return woolly mammoths to the Arctic by 2028. In this episode, Ben shares how his self-described "unemployable" streak became his entrepreneurial superpower, why asking naive questions helps him tackle impossible challenges across industries, and how Colossal's breakthrough technologies represent humanity's essential insurance policy for planetary survival. Follow Inspired: ⁠Website⁠ ⁠LinkedIn⁠ ⁠X⁠ ⁠Instagram⁠ ⁠Substack

Watershed CEO Taylor Francis is building the infrastructure for companies to decarbonize at scale. After building Stripe's climate program, he saw how technology could move the needle faster than policy alone and set out on his journey as a founder. With a 500 million ton CO2 reduction goal by 2030 and customers like FedEx, Walmart, Airbnb, and Spotify, Taylor is proving that climate action can be both urgent and profitable. What You'll Learn: Taylor's journey from An Inconvenient Truth to founding Watershed What he learned at Stripe about scaling impact and building mission-driven companies How supply chain collaboration is the real lever for decarbonization (and why it matters more than you think) What the next decade of climate actually looks like and why the world is winning faster than predicted The frameworks and principles that attract the best people to solve the hardest problems Chapters: 1:57 Growing Up and An Inconvenient Truth 5:35 From Princeton to Policy 7:40 What Stripe Taught Him About Scale 9:54 The Origin of Watershed's 500 Megaton Mission 13:09 Breaking Down Scope One, Two, and Three Emissions 16:00 How Watershed Works With Fortune 500 Companies 18:50 The Story Behind the Name Watershed 21:00 Why Network Effects Matter in Decarbonization 23:15 What the Best Investors Taught Him 28:15 The Truth About Climate Today 33:10 Where the World Is Actually Headed 36:20 Product Footprints and AI Done Right 39:42 Why Domain-Specific AI Beats Generic Models 41:00 Quick Fire Follow Watershed and Taylor: Watershed Website Watershed LinkedIn Taylor Francis LinkedIn Follow Inspired: Website LinkedIn X Instagram Substack

Julia Berolzheimer and Thomas Berolzheimer have spent 15 years turning a fashion blog into one of the most powerful e-commerce brands in the creator economy. What started with a camera and an idea in 2011 has grown into a multi-platform empire spanning a blog, Instagram, Substack, ShopMy, Amazon, and their newest venture, Coreli. What You'll Learn: How Julia and Thomas built one of the most trusted brands in the creator economy Why curation beats creation when it comes to driving real commerce How they think about managing content, platforms, and technology as a team Where AI fits in and where it doesn't for creators who've built on authenticity What the next decade of the creator economy actually looks like Chapters: 01:52 Intro 02:35 The Beginning of Julia and Thomas's Journey 04:45 Milestones and Evolution of Gal Meets Glam 06:41 Curation and How Julia Starts Every Morning 11:30 Managing Content Across Different Platforms 15:34 ShopMy 20:25 Tools and Technology 25:20 How Julia and Thomas Work Together 29:00 The Future of the Creator Economy 31:05 Using AI for Influencer Content 35:45 Quickfire Round Follow Julia and Thomas Berolzheimer: Julia Berolzheimer Blog Julia's Instagram Thomas' Instagram Substack Coreli Follow Inspired:‍ Website  LinkedIn X Instagram Substack