• Terrydale Capital is a commercial real estate financing firm based in Dallas (with ties in Kansas City) that helps borrowers source debt capital across a broad array of property types (multifamily, retail, industrial, self-storage, land, etc.).

• They also provide advisory and structuring services, helping clients with due diligence, capital planning, and navigating non-standard deals.

  
  

• Terrydale Live is their digital platform aimed at bringing more transparency and speed into the CRE financing process. It offers live market quotes, lender matching, and a deal room to manage deal flow from quoting through closing.

• 
  

  Terrydale Capital: https://www.terrydalecapital.com

  
  

• Terrydale Live: https://www.terrydalelive.com

From its founding in the wake of 9/11 by Peter Thiel, Alex Karp, and their team, to its early CIA-backed growth with Gotham, and expansion into the commercial world with Foundry. We trace its pivotal role in intelligence operations, government contracts, and crisis responses, alongside its push into AI with AIP. The episode also explores Palantir’s ethical controversies, privacy debates, and the lessons it offers on mission-driven entrepreneurship, operating at the intersection of technology and policy, and the challenges of wielding powerful data analytics on a global stage.

Are you happy with your CRM? If not, we have an AI-infused one that is really good and talks you.

Try ⁠My Lindy⁠

Add custom AI to your business.

Try ⁠Strawberry Antler

This episode tells the full story of Lemonade, the insurtech startup that set out to disrupt a century-old industry. Founded in 2015 by Daniel Schreiber and Shai Wininger—outsiders to insurance—they built an AI-first, mission-driven company offering renters, homeowners, car, pet, and life insurance.

We explore their early funding, rapid launch, and standout innovations like AI-powered claims in seconds and the Giveback Program that donates unclaimed premiums to charities. The story covers their meteoric growth, IPO in 2020, expansion into Europe, and acquisition of Metromile to enter auto insurance.

We also dive into their behavioral economics approach, their brand’s ethical positioning, and the challenge of scaling toward profitability while fending off both traditional giants and new startups.

It’s a case study in how outsiders can reshape an industry—if they move fast, leverage technology, and align incentives with customers.

Are you happy with your CRM? If not, you'll love My Lindy.

Try ⁠My Lindy⁠

Add custom AI to your business.

Try ⁠Strawberry Antler