Inspired with Alexa von Tobel

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 has spent his entire career at the forefront of physical AI. He co-founded Anki, shipping more than 3.7 million consumer robots globally, before leading autonomous trucking at Waymo, where he helped pioneer the world's most advanced driverless vehicle program. Now he's applying everything he learned to the machines that build our world. Boris is the co-founder and CEO of Bedrock Robotics, valued at $1.75 billion, which retrofits existing construction equipment into fully autonomous machines at a moment when demand is skyrocketing and the industry faces a shortage of more than 500,000 workers.

What You'll Learn:

Chapters:

2:16 Introduction
4:40 Boris's Time at Waymo
9:35 The Future of Autonomous Trucking
13:19 What Autonomous Trucking Looks Like in Practice
18:15 How Self-Driving Changes Our Cities
20:40 The Birth of Bedrock Robotics
24:55 What Bedrock Actually Does
26:10 Why Retrofit Instead of Build From Scratch
28:23 The Role of Humans on the Autonomous Job Site
30:45 The Advantages of Going Autonomous
34:05 Big Predictions for Physical AI
36:48 The Contrarian Take on Humanoids
38:50 What Excites Boris Most
39:59 Quick Fire Round

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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:

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

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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:

Chapters:

00:00 Introduction
01:30 Growing Up in Chile
04:20 What Is Runway
06:38 Real World Use Cases
10:25 The Technology Behind the Breakthrough
12:00 Underestimating the Speed of Progress
14:55 If Content Is Free Does It Lose Value
20:10 How Runway Makes Money
24:05 The Real-Time Generation Revolution
29:15 Gaming and Interactive Experiences
33:00 The Future of Advertising
35:45 The Consequences of Infinite Content
37:20 Why Billions of Stories Are Waiting
41:00 Will AI Kill Jobs
44:00 Quickfire

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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:

Chapters:

00:00 Introduction
01:30 Growing Up a Builder
04:22 The Origin of Chainguard
08:20 How Chainguard Works and Who It's For
13:20 How Chainguard Cleans and Secures the Code
15:20 How Dan Decides Where to Expand
17:15 The Future of Software and Software Engineers
25:30 Where Chainguard Goes From Here
26:48 Are We Already at AGI?
28:30 The Security Crisis No One Talks About
31:27 Why CISOs Can't Afford to Say No
33:25 Biggest Trade-Offs and What's Next for Chainguard
38:00 What Disappears in an AI World
39:22 What Shocked Dan Most and What Scares Him
42:30 When Security Becomes Part of Engineering
44:39 Quickfire
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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:

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 

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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.

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.

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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:

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

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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:

Chapters:

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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:

Chapters:
02:00 Growing Up with a Doctor Mother
06:45 From Quantitative Finance to Healthcare
09:00 What Solace Does for Patients
11:38 Why Inspired Invested in Solace
12:45 Real Stories of Solace Saving Lives
17:35 Why the US Healthcare System Is So Broken
20:35 Building a Marketplace of Healthcare Advocates
22:45 Measuring What Matters: Outcomes and Costs
28:50 Announcing Solace's $130M Series C
30:31 Building Culture at Scale
33:00 Where Solace Is Headed
36:30 When AI Helps and When Humans Are Essential
40:20 Jeremy's Predictions for Healthcare in 2035

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