• 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.

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  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.

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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.

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This episode tells the full story of Brandless, the direct-to-consumer startup founded in 2016 with the mission of offering high-quality household and grocery essentials at “honest prices” by eliminating the so-called “brand tax.” With a sleek, minimalist identity and a bold “everything for $3” model, Brandless raised over $200 million, gained early buzz, and expanded rapidly.

However, the flat pricing strategy strained margins, fulfillment costs soared, and customer acquisition proved expensive. A pivot to variable pricing in 2019 eroded customer trust, leading to a sharp drop in loyalty. By February 2020, Brandless shut down amid financial and operational pressures.

Just months later, former leadership revived the brand in a leaner form—fewer SKUs, a membership model, wholesale partnerships, and tighter cost control. Today, Brandless continues on a smaller scale, embodying the lessons learned about sustainable growth, unit economics, and maintaining brand authenticity.

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This episode tells the full rise-and-fall story of DeadHappy, the UK insurtech that set out to make life insurance bold, simple, and even fun. Founded in 2017 by Phil Zeidler and Andy Knott—both shaped by personal experiences with mortality—DeadHappy disrupted the market with its “Deathwish” concept, a short four-question application, and cheeky branding.

The company grew quickly, reaching 25,000 active policies and £2.5 million in revenue by 2023, earning praise for its speed, affordability, and irreverent tone. But its boundary-pushing marketing—including a controversial ad featuring serial killer Harold Shipman—sparked regulatory backlash. In 2024, its sole underwriting partner withdrew support, forcing the company into administration.

While the DeadHappy brand died, its tech platform lived on—acquired by Octopus Legacy to power new life and estate-planning products. The story offers a cautionary lesson: innovation can shake up even the oldest industries, but in regulated markets, brand trust is as vital as product design.

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MSCHF is a Brooklyn-based art collective and product studio founded in 2016 by Gabriel Whaley, Lukas Bentel, Kevin Wiesner, and Stephen Tetreault. They specialize in “structured chaos”—launching unpredictable, provocative “drops” every few weeks that blur the line between art, commerce, and internet culture.

Their work spans viral products like Jesus Shoes (Nike sneakers with holy water), Satan Shoes (Nike Air Max 97s with a drop of human blood, made with Lil Nas X), Big Red Boots, Birkinstocks, and digital stunts like the endurance game Finger on the App. Each project is designed as a narrative-first cultural moment rather than a traditional product.

MSCHF operates without a consistent logo or brand identity, aiming to surprise their audience every time. They’ve raised about $24 million from investors including 1686 Partners, GFR Fund, and RSE Ventures, and have grown to around 25 employees.

Their philosophy: design for the “spicy present,” create things so strange people can’t help but share them, and treat controversy as a feature—not a bug. MSCHF now expands into gallery exhibitions and publishing, cementing their role as both an art world disruptor and a marketing innovator.

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Every great company starts with an itch. For Acquired, it was two operators—Ben and David—who kept having the same conversations with friends: “Wait, how did Instagram sell for a billion?” “Why did Berkshire buy a railroad?” The early episodes were short, conversational, and, let’s be honest, recorded on gear you would not use to land a rocket. But they had the thing that matters: curiosity paired with respect for the craft of business.

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HawkSoft, a privately-owned insurance agency management system founded by Paul Hawkins in 1995. From its roots in a small apartment to becoming a cloud-native platform trusted by agencies across the U.S..

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