Inspired with Alexa von Tobel

Inspired Capital

Inspired with Alexa von Tobel dives headfirst into conversations with the most ambitious people on the planet. Host Alexa von Tobel, Founder and Managing Partner of Inspired Capital, gets under the hood of guests’ ambitions, from pivotal childhood moments to the critical advice that shaped their life paths. What does it take to be a true visionary, one who stares down monumental challenges with grit and resilience? Learn directly from those builders and problem-solvers whose determination is shaping a brighter, more inspired future.

  1. Max Shaw and Brian Distelburger on Reinventing People Management with Windmill

    May 20

    Max Shaw and Brian Distelburger on Reinventing People Management with Windmill

    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/

    53 min
  2. Cristóbal Valenzuela on How Runway's World Models Are Changing Storytelling

    May 6

    Cristóbal Valenzuela on How Runway's World Models Are Changing Storytelling

    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/

    52 min
  3. Dan Lorenc on Building Chainguard into a $3.5B Open Source Security Company

    Apr 22

    Dan Lorenc on Building Chainguard into a $3.5B Open Source Security Company

    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/

    51 min
  4. Teamshares CEO Michael Brown on Why Going Public Is Just the First Inning

    Apr 10

    Teamshares CEO Michael Brown on Why Going Public Is Just the First Inning

    Teamshares CEO Michael Brown is on a mission to address one of the biggest problems in the American economy. Millions of small businesses are owned by Boomers and Gen X approaching retirement, and most will never find a buyer. Teamshares buys these businesses from retiring owners. With more than 90 companies acquired across 30 states, over 500 million in revenue, and a Nasdaq listing on the horizon, Michael is proving that the small business economy deserves a better solution. What You'll Learn: How Teamshares actually works and why the model gets stronger as it scales What nearly 100 acquisitions have taught Michael about small businesses that most people don't see Why going public changes everything for Teamshares and why Michael says it's still the first inning How he built through COVID and the 2022-2023 rate shock without losing conviction The long-term mindset behind building a company with a 200-year plan Chapters: 01:30 Michael's Childhood 04:04 What Is Teamshares 07:44 Why Going Public Is Just the Beginning 15:30 Lessons from 90 Acquisitions 18:50 The Future of Teamshares 28:19 The 200-Year Mindset 32:25 Building Culture at Scale 36:00 Leading Through Market Shocks 37:55 Quickfire  Follow Teamshares: Website: https://www.teamshares.com/ LinkedIn: https://www.linkedin.com/company/teamshares/ X: https://x.com/Teamshares 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/ Important Disclosures and Disclaimers This podcast episode features a discussion with Michael Brown, Co-Founder and CEO of Teamshares, Inc. (“Teamshares”), and Alexa von Tobel, Founder and Managing Partner of Inspired Capital. Ms. von Tobel and Inspired Capital are existing investors in Teamshares and may have a direct financial interest in the outcome of the proposed business combination described below. Proposed Business Combination. Teamshares has entered into a definitive agreement for a business combination with Live Oak Crest Acquisition Corp. (“Live Oak”), a special purpose acquisition company. In connection with the proposed transaction, a registration statement on Form S-4 (the “Registration Statement”) has been filed with the U.S. Securities and Exchange Commission (the “SEC”). This podcast does not constitute an offer to sell or the solicitation of an offer to buy any securities. For important information about the proposed transaction, including where to find the Registration Statement and other legal disclaimers, please refer to the press release available at https://www.businesswire.com/news/home/20260403515446/en/Teamshares-and-Live-Oak-V-File-S-4. Clarifications. References to Operating EBITDA throughout refer to Pro Forma Operating EBITDA, which includes pre-acquisition results of acquired businesses as if they had been owned for the full year. References to “Corporate EBITDA” throughout the episode refers to 2025 Pro Forma Adjusted EBITDA. Investors should review the full set of assumptions and risk factors accompanying these metrics in the Registration Statement, including a full reconciliation of any non-GAAP measures.

    49 min
  5. Taylor Francis on How Watershed Is Solving the Climate Crisis

    Mar 11

    Taylor Francis on How Watershed Is Solving the Climate Crisis

    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

    47 min
  6. Solace Founder Jeremy Gurewitz Raises $130M to Transform Healthcare Advocacy

    Feb 11

    Solace Founder Jeremy Gurewitz Raises $130M to Transform Healthcare Advocacy

    Solace founder and CEO Jeremy Gurewitz is building a marketplace that connects patients with healthcare advocates—covered by insurance. After losing his mother to pancreatic cancer and witnessing firsthand how difficult it was to navigate the US healthcare system, Jeremy founded Solace to help every American manage the overwhelming complexity of healthcare, from finding the right doctors to dealing with insurance. Now, after raising $130 million in a Series C led by IVP, Solace is expanding into commercial insurance and scaling nationally. With a patient NPS of 90 and data showing improved outcomes and lower costs, Jeremy shares how he is building for a future where healthcare advocacy becomes as standard as having a primary care physician. What You'll Learn: Jeremy's personal journey from losing his mother to building Solace How healthcare advocacy works and why patients achieve a 90+ NPS Why the US healthcare system is so broken and how advocates fix it Where Jeremy sees healthcare heading in the next decade Chapters:02:00 Growing Up with a Doctor Mother06:45 From Quantitative Finance to Healthcare09:00 What Solace Does for Patients11:38 Why Inspired Invested in Solace12:45 Real Stories of Solace Saving Lives17:35 Why the US Healthcare System Is So Broken20:35 Building a Marketplace of Healthcare Advocates22:45 Measuring What Matters: Outcomes and Costs28:50 Announcing Solace's $130M Series C30:31 Building Culture at Scale33:00 Where Solace Is Headed36:30 When AI Helps and When Humans Are Essential40:20 Jeremy's Predictions for Healthcare in 2035 Follow Solace and Jeremy:‍ • Solace Website • Solace LinkedIn • Jeremy Gurewitz LinkedIn Follow Inspired:‍ • Website • LinkedIn • X • Instagram • Substack

    52 min

About

Inspired with Alexa von Tobel dives headfirst into conversations with the most ambitious people on the planet. Host Alexa von Tobel, Founder and Managing Partner of Inspired Capital, gets under the hood of guests’ ambitions, from pivotal childhood moments to the critical advice that shaped their life paths. What does it take to be a true visionary, one who stares down monumental challenges with grit and resilience? Learn directly from those builders and problem-solvers whose determination is shaping a brighter, more inspired future.