AI Insurance

Progressive Insurance

Progressive Insurance began in 1937 when Joseph Lewis and Jack Green set out to insure drivers that other companies ignored. From the start, the company built its edge through innovation: drive-in claims centers, safe-driver discounts, and later, online rate comparisons that made pricing transparent. Under Peter Lewis’s leadership, Progressive doubled down on experimentation, technology, and bold marketing, eventually introducing telematics and the well-known “Snapshot” program. Today, Progressive is the third-largest auto insurer in the U.S., consistently profitable, and admired for staying ahead of industry trends. Its story shows how serving overlooked customers, embracing transparency, and fostering a culture of innovation can turn a niche player into a market leader. Independent agents need ways to grow revenue without adding complexity. That’s what SmallGiant [https://www.smallgiantins.com] delivers. It’s not insurance—it’s a membership you can offer your clients that covers towing, rental cars, and glass repairs outside the insurance system. Your clients stay protected, their records stay clean, and you get 100% of the first month’s commission plus ongoing revenue. No quotas, no extra paperwork—just a simple way to add value for clients and income for your agency. Compete with big insurers through digital presence 74% of insurance consumers research policies online. We help independent agencies appear in local searches and provide helpful content to win those leads. https://tomorrowatetoday.com/industries/insurance

SmallGiant | Ep #24

Most drivers don’t realize that the smallest auto insurance claims can have the biggest impact on their premiums. A $200 tow, a rental car after an accident, or even a chipped windshield may seem minor — but when filed through your insurance, these “little” claims often get logged just like major accidents. That can push your premiums up by hundreds of dollars a year for several years, or even trigger non-renewal. SmallGiant was created by independent insurance agents to solve this problem. Instead of running minor claims through your auto policy, SmallGiant is a low-cost membership that covers: Rental reimbursement up to $60/day, Towing & roadside reimbursement up to $120 per incident and Glass/window repair up to $300 on the premier plan. When a member needs a tow, rental, or glass repair, SmallGiant reimburses the expense quickly and directly — keeping the incident off the insurance record. This protects the driver’s claims-free status and helps prevent premium surcharges that typically add $1,000 to $1,500 over three years. For agents, SmallGiant provides a unique advantage: it safeguards clients from small claims rate hikes, improves retention, creates a new commission stream, and even allows agents to quote lower base premiums by removing carrier add-ons. [https://www.smallgiantins.com] Agents receive 100% of the 1st months commissions, where something like AAA pays agents nothing. In short: SmallGiant fills the gaps that cost drivers the most — not in the repair shop, but at renewal time.

Revolutionizing Life Insurance: The Rise and Fall of DeadHappy | Ep #23

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. Are you happy with your CRM? If not, we have an AI-infused one that is really good and talks you. Try ⁠⁠My Lindy⁠⁠ [https://mylindy.com/] Add custom AI to your business. Try ⁠⁠Strawberry Antler⁠ [https://www.strawberryantler.com/] Agents get paid for rental reimbursement/window/towing Try ⁠SmallGiant [https://www.smallgiantins.com]

The story of Lemonade | Ep #22

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, we have an AI-infused one that is really good and talks you. Try ⁠My Lindy⁠ [https://mylindy.com/] Add custom AI to your business. Try ⁠Strawberry Antler [https://www.strawberryantler.com/]

ElevenLabs | Ep #21

ElevenLabs is reinventing how machines speak—making synthetic voices sound human, emotional, and multilingual. Founded in 2022 by two Polish childhood friends frustrated with robotic speech, the company quickly raised over $180 million and built a platform that can clone voices, dub content in 70+ languages, and create real-time conversational agents. For insurance agents, this tech is a game-changer. It powers AI voice agents that can sell, support, follow up, upsell, and market—all with human-like warmth and clarity. Whether it’s a lead follow-up or a multi-language customer support line, ElevenLabs lets insurers scale personal voice outreach without sacrificing trust. The future of voice in business? It’s here—and it sounds a lot more human than you’d think. My Lindy⁠⁠ [https://www.mylindy.com/]: AI-infused smart CRM w/ AI agents that do work for you. ⁠⁠Strawberry Antler⁠⁠ [https://www.strawberryantler.com/]: Custom AI anything. ⁠LemonPhone⁠ [https://www.lemonphone.com]: LemonPhone automates thousands of outbound calls with AI agents that book meetings, generate leads, and retain clients, enabling businesses to scale their sales and customer engagement efforts without hiring additional staff.