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 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.
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.
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.
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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Agents get paid for rental reimbursement/window/towing
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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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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: AI-infused smart CRM w/ AI agents that do work for you.
Strawberry Antler: Custom AI anything.
LemonPhone: 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.
AI is a tool that mimics human intelligence by finding patterns in data, helping with everything from spam filters to medical scans, but it doesn't truly understand anything—it just predicts based on training. It's everywhere, often invisible, making life more efficient by handling boring, repetitive tasks, yet it has real limits like bias, lack of common sense, and no genuine creativity. While it may automate parts of many jobs, it also creates new roles and will likely become a standard tool people use, much like electricity did. The real risks are how humans choose to use it, making ethics and careful deployment essential for the future.
My Lindy: AI-infused smart CRM w/ AI agents that do work for you.
Strawberry Antler: Custom AI anything.
LemonPhone: 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.
Success in insurance sales supported by statistics
The insurance industry's success heavily relies on data-driven strategies across digital, phone, and in-person channels. Let's break down the most effective approaches for winning new insurance prospects, supported by concrete statistics and proven methodologies. This podcast episode breaks down success in insurance sales supported by statistics.
AI to help agents:
My Lindy: AI-infused smart CRM w/ AI agents that do work for you.
Strawberry Antler: Custom AI anything.
LemonPhone: 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.
We explore how AI is quietly transforming independent insurance agencies — not just big carriers or Fortune 500 firms. From AI voice agents that handle cold calls 24/7, to quoting systems that deliver estimates in minutes, the tools are here — and they’re already making a measurable impact.
We break down real-world examples:
• How one agency uses AI to follow up with 100 internet leads each night — without lifting a finger
• Why AI-powered CRMs are helping agents focus more on relationships, less on admin
• How voice AI is replacing voicemails with real conversations — and pre-qualifying leads before your producers even clock in
• And how automation tools are cutting quoting time from hours to minutes
Only 6% of independent agencies are using AI today. That’s the bad news. The good news? You can still be early.
Whether you're a one-person shop or a 10-person team, this episode shows you how to start small, automate the right tasks, and stay ahead as the industry changes fast.
My Lindy: AI-infused CRM w/ AI agents
Strawberry Antler: Custom AI call agents
A clear, jargon-free podcast for insurance professionals who want to understand AI. Each episode breaks down key AI terms and concepts, with real-world examples and practical insights. No fluff—just what you need to know to stay informed and ahead.
If you're looking for a smarter CRM...My Lindy, is a truly smarter CRM with custom AI agents built for you. Lindy deploys an army of AI agents across your company to help you run a smarter agency. Lindy turns hours of work into minutes of automation and efficiency. She handles proposals, quoting estimates, emails, and connects to almost any insurance platform, like Hawksoft Agency Zoom, Now Certs and Progressive.
What makes prompt engineering particularly valuable in insurance is its ability to handle complex, industry-specific requirements. When crafting prompts, insurance professionals should consider regulatory compliance, accuracy of technical terms, and the need for clear, unambiguous language. A well-engineered prompt might include specific instructions about incorporating state regulations, industry standards, or company-specific guidelines. This attention to detail ensures that AI-generated content meets the stringent requirements of the insurance industry.
If you're looking for a smarter CRM, My Lindy, is a truly smarter CRM with custom AI agents built for you. Lindy deploys an army of AI agents across your company to help you run a smarter agency. Lindy turns hours of work into minutes of automation and efficiency. She handles proposals, quoting estimates, emails, and connects to almost any insurance platform, like Hawksoft Agency Zoom, Now Certs and more.
Get custom AI agents at strawberryantler.com
The sovereignty of God remains unaffected by technological advancement. Jesus Christ, described in Revelation as the Alpha and Omega, maintains lordship over all creation, including our technological developments. This truth should reassure Christians who might worry about AI's implications for faith and divine authority. The text emphasizes that AI doesn't threaten God's control, surprise Him, or have the power to alter His plans for history.
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Lindy deploys an army of AI agents across your company to help you run a smarter insurance agency. Pre-built agents, add your own agents, or we'll have us build custom AI agents for you. Lindy turns hours of work into minutes of automation and efficiency. See handles ACORD's, quoting estimates, email, AI-infused CRM and connects to almost any insurance platform.
Try it at https://www.mylindy.com
Most of the AI we interact with today is behind someone else’s interface. You use ChatGPT, or Claude, or a customer service bot on a company website—but you don’t control what happens behind the scenes.
When you build your own agent, you control the behavior. You can tune the prompt, define what kind of inputs it handles, and where its responses go.
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Lindy deploys an army of AI agents across your company to help you run a smarter insurance agency. Pre-built agents, add your own agents, or we'll have us build custom AI agents for you. Lindy turns hours of work into minutes of automation and efficiency. See handles ACORD's, quoting estimates, email, AI-infused CRM and connects to almost any insurance platform.
Try it at https://www.mylindy.com
Lindy is your AI-powered business assistant—more than just a chatbot. Insurance agencies can now do more with less.
It actively handles work across your emails, calendars, documents, CRM, and tasks. Think of it as an always-on team member who never forgets a detail, understands your business systems inside and out, and gets things done without being asked twice.
Try Insurance Lindy!
Lindy deploys an army of AI agents across your company to help you run a smarter insurance agency. Pre-built agents, add your own agents, or we'll have us build custom AI agents for you. Lindy turns hours of work into minutes of automation and efficiency. See handles ACORD's, quoting estimates, email, AI-infused CRM and connects to almost any insurance platform.
Try it at https://www.mylindy.com
The fundamental challenge in insurance technology has been fragmentation - different systems, databases, and AI models speaking different languages. This fragmentation creates inefficiencies, increases costs, and slows down innovation. MCP addresses this by establishing a universal communication standard, essentially creating a common language that all components can understand and use. Just as USB-C eliminated the frustration of carrying multiple chargers for different devices, MCP eliminates the need for multiple integration protocols across insurance systems.
This podcast explains how insurance is being transformed by Anthropic's MCP.
Strawberry Antler (https://www.strawberryantler.com)
Insurance magic. Custom AI-native agents that help insurance agents do whatever needs to be done. Debra, Lindy, ACORD Me Not and more.
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Lindy deploys an army of AI agents across your company to help you run a smarter insurance agency. Pre-built agents, add your own agents, or we'll have us build custom AI agents for you. Lindy turns hours of work into minutes of automation and efficiency. See handles ACORD's, quoting estimates, email, AI-infused CRM and connects to almost any insurance platform.
Try it at https://www.mylindy.com
Interview from IA Forward podcast with Strawberry Antler
Implementation Strategies
One of the most valuable segments of the podcast addresses how agencies can implement AI solutions without disrupting their existing workflows. The team shares a phased approach that allows agencies to see immediate benefits while building toward more comprehensive AI integration. Explore our flexible pricing options designed for agencies of all sizes.
The conversation concludes with insights into the future of independent insurance agencies in an increasingly AI-driven landscape. Rather than replacing agents, Chad and Justin explain how AI will enhance the human elements that make independent agencies valuable—personalized service, trusted advice, and community connections. Request a demo to see these solutions in action.
IA Forward is a leading resource for independent insurance agents looking to grow their businesses and adapt to changing market conditions. Their podcast features conversations with industry leaders, technology experts, and successful agency owners who share practical strategies for agency success.
Agentic AI is a type of artificial intelligence that can make decisions and take actions on its own—for example, an insurance assistant that notices a policy is about to expire, emails the customer to renew, and updates the CRM without being told.
Agentic AI represents a significant evolution in artificial intelligence technology, functioning more like an autonomous employee than a simple tool. Unlike basic AI that responds to commands, agentic AI can make decisions, take initiative, and learn from experience while interfacing with various business systems. It accomplishes this through key capabilities including memory of past actions, forward planning, integration with existing software systems, and continuous learning.
Try Insurance Lindy!
Lindy deploys an army of AI agents across your company to help you run a smarter insurance agency. Pre-built agents, add your own agents, or we'll have us build custom AI agents for you. Lindy turns hours of work into minutes of automation and efficiency. See handles ACORD's, quoting estimates, email, AI-infused CRM and connects to almost any insurance platform.
Try it at https://www.mylindy.com
Listen to Debra, a commercial insurance rater help an agent get a commercial insurance quote online and over the phone.
Learn more: Strawberry Antler
U.S. commercial insurance shops are stuck in a tech time warp: creaky legacy management systems, siloed carrier portals, and duplication-heavy workflows burn staff hours and jack up E&O and cyber risk. Because AMS and CRM rarely play nice together, producers limp along on spreadsheets, automation is basically MIA, and any whiff of innovation stalls under a mix of “if-it-ain’t-broke” mind-sets and option overload. Toss in ransomware villains circling those unpatched servers and you’ve got an industry aching for a digital exorcism.
The fix is equal parts tech and culture: modern, cloud-first platforms that integrate quoting, policy, CRM, and client self-service; open APIs that nuke double entry; built-in automation for certificates, renewals, and comms; plus rock-solid security and user-friendly change management. That shopping list lines up almost item-for-item with what Strawberry Antler delivers with Debra—making it a straight-up antidote to the flip-phone-in-a-5G-world problem agents face today.
Yes, AI agents are becoming increasingly popular across various industries. They're moving beyond simple chatbots to perform complex, multi-step tasks that improve efficiency and customer service. In insurance and other sectors, businesses are using them to automate processes like quoting, customer follow-ups, and data handling.
Major tech companies like ServiceNow and Salesforce are developing advanced AI agents, and reports from LangChain and Liberty Mutual show growing interest in their use. However, challenges remain, especially around accuracy and oversight, since AI agents can make compounding errors in complex workflows.
Overall, the momentum is clear, AI agents are gaining traction and are set to play a central role in the future of work.
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Podcast Summary: Picking the Right AI for Insurance—There’s No One-Model-Fits-All
In this episode, we unpack a truth many overlook: there’s no single “best” AI model for insurance—just the best one for the task at hand.
OpenAI (ChatGPT) helps agents craft personalized emails and summarize complex policies with top-notch natural language skills.
Google Gemini thrives in data-heavy workflows, helping agents analyze policies and automate tasks within Google Workspace.
Anthropic Claude is your go-to for safe, compliant, and consistent communication—especially with sensitive client info.
DeepSeek gives you total control with its open-source flexibility, making it perfect for agencies building in-house AI tools.
We also dive into how to structure your AI strategy—starting with understanding your agency’s pain points, matching the right tool to each task, and integrating AI without disrupting your existing workflows.
The bottom line? Use the right AI, at the right time, for the right reason—and you won’t just keep up with the future, you’ll help shape it.
👉 Want to learn more or talk about how your agency can use AI? Visit us at strawberryantler.com
Try Insurance Lindy!
Lindy deploys an army of AI agents across your company to help you run a smarter insurance agency. Pre-built agents, add your own agents, or we'll have us build custom AI agents for you. Lindy turns hours of work into minutes of automation and efficiency. See handles ACORD's, quoting estimates, email, AI-infused CRM and connects to almost any insurance platform.
Try it at https://www.mylindy.com