How Raution Jaiswal Built InsuredMine to $5M ARR on Just $40,000
The bootstrap playbook from a founder who turned extreme constraint into competitive advantage, building an insurance CRM that now competes with Salesforce.
The math shouldn’t work. You can’t build a serious SaaS business on $40,000. You definitely can’t scale to $5 million in annual recurring revenue, hire nearly 100 employees, and win business from 17 of America’s top 50 insurance agencies. Yet Raution Jaiswal did exactly that with InsuredMine.
While the broader InsurTech sector collapsed in 2024, with funding hitting a seven-year low of $4.25 billion, Raution was quietly building the exact company venture capitalists now desperately seek: profitable, capital-efficient, and growing without their money.
His journey from a 90-square-foot room in Kolkata to running a thriving software company from India reveals a contrarian playbook for building in legacy industries. The secret? Turn every disadvantage into strategic discipline.
Check out the video of the conversation here or read on for insights.
Building the Wrong Thing Right
Raution’s entry into insurance wasn’t calculated. He started with a consumer app, a digital wallet where people could consolidate their insurance policies after he missed a payment deadline while traveling. He built it, then took it to insurance agencies for feedback.
The response was brutal.
Within the first five minutes, they busted my mouth and said, no, this is not the biggest problem that we face today. I have a much bigger problem that I’m willing to pay for.
That rejection became the pivot point. Raution discovered a fundamental truth about business models: the people receiving value and the people willing to pay aren’t always the same.
Customers want this, where they can consolidate all their policy. Agents are the one who would pay for it. So who is paying and who is getting the value, there is a disconnect.
He scrapped the consumer product and started listening to what agencies actually needed. What emerged wasn’t a predetermined vision but an organic response to their pain points. The shift from product-based to customer-based thinking was exactly what the insurance industry needed but hadn’t yet embraced.
They said, add two eyes. We added two eyes. They said, add two ears. We added two ears. Add two legs, two more legs, add a tail. And then when they’re looking at it, this looks like a dog. So that’s when we say, okay, let’s call it a CRM. We were not building a CRM. We were just solving their business problem.
The key insight: agencies needed better tools to manage relationships, not just policies. Their existing Agency Management Systems (AMS) were excellent as systems of record but terrible at sales, marketing, and customer communication.
The Trojan Horse
Raution faced formidable competition. The U.S. independent insurance agency market runs on legacy systems built by billion-dollar, private equity-backed companies like Applied Systems and Vertafore. These platforms are deeply entrenched, handling everything from policy records to accounting.
Rather than attempt a costly “rip and replace” strategy, InsuredMine positioned itself as a friendly add-on. The pitch was simple: keep your existing AMS, but use InsuredMine for sales, marketing, and customer engagement.
This low-friction approach got them inside. Once there, the superior user experience did the rest. One customer testimonial captures the eventual outcome: “It has become our main hub where all agency communication is initiated. Gone are the days where we would use a management system to store data, a voip system to send text messages. With Insuredmine it is all in one centralized service.”
The legacy AMS becomes relegated to a backend database while InsuredMine evolves into the primary system of engagement. It’s displacement from the inside out.
Today, InsuredMine serves agencies that collectively manage over $8 billion in premiums. The company targets the top 1,500 agencies in America, with an ideal customer profile of 10+ users and average contract values around $13,000 to $14,000 annually.
Discipline as Moat
Raution didn’t quit his day job until he had 50 paying customers. He moonlighted for 18 months, working with a small development team in India while holding down a full-time corporate role. When he finally took the leap, his mother cried. He was the family’s sole breadwinner, and his parents were visiting the U.S. at the time.
It’s like jumping without a parachute. And I told my mom, let me take this shot. I promise you will not regret that. I did my best. Because I don’t control the outcome. I control my efforts.
That extreme capital constraint forced relentless focus. His wife noticed something unusual during those early cold-calling days: “I have not seen a guy who just got rejected and then picks up another call with a smile on his face.”
His response? “Well, do I have a choice? That’s what I have to do.”
The discipline extended to every dollar. At conferences, employees share hotel rooms. Instead of FedEx, they pack materials in suitcases. One early customer would only meet before church on Sunday mornings, from 6am to 8:30am. Raution would go to bed at 4:30am and force himself awake. “If that guy is giving me that time, I’m going to take it.”
The company’s survival mantra during the hardest phase: “We have to survive one more day.”
COVID became an unexpected accelerator. With agencies forced to go digital and Raution working 20-hour days, seven days a week, the company grew rapidly. The timing was perfect, the product was ready, and the market finally had to adapt.
The Architecture Bet
Perhaps most surprising is Raution’s claim that InsuredMine’s primary competitive advantage is its product architecture, a bold statement from a non-technical founder.
Every line of code has been written by us in the last five years. Our competitors are collapsing with old architectures that don’t scale, and they can’t move fast.
His background in project management (he’s a certified PMP and Scrum Master) provided the operational toolkit to build with extreme efficiency. Those aren’t just credentials, they’re frameworks for delivering complex projects on time and within budget, exactly what bootstrapping demands.
The company ships 600 to 700 features or enhancements per year, all driven by customer feedback. But Raution is clear about the key skill: knowing the difference between custom requests and features that can be productized.
We are curious enough to listen to people at the decibels nobody else is listening, and agile enough to be able to react to it and build a first iteration of it.
This philosophy shows up in customer reviews. G2 ratings consistently praise InsuredMine’s responsiveness and support quality, with customers often naming specific team members who went above and beyond.
The AI Evolution
InsuredMine now positions itself as an “AI CRM platform,” evolving through three distinct phases. First came generative AI for writing emails and text messages. Then predictive AI to forecast which deals would close and which policies would renew.
Now comes prescriptive AI, the most ambitious phase. Instead of just predicting a 20% probability of closing a deal, the system recommends specific actions to increase that probability to 70%.
This pivot aligns perfectly with broader market trends. AI-focused InsurTech companies secured $2.01 billion in 2024, nearly half the sector’s total funding. The global AI in insurance market is projected to grow at 33% annually.
But Raution doesn’t believe AI will replace insurance agents.
Insurance is a very niche product. There is a lot of terminology, a lot of nuance. Agent community will embrace AI and leverage it to their strength to deliver superior underwriting capabilities rather than AI being on the side replacing the customer.
The VC Paradox
Today, Raution receives daily emails from venture capitalists. He’s not interested in raising money or selling.
We may be able to capture the market faster, but we will lose the identity of how we operate. It’s not just about profitability and scale. It’s about empathy with the customers, the relationships that we have built, the way we are catering to the market.
He’s seen the horror stories. “Not just the control is gone, it’s also the direction is lost and then the focus is always on the bottom line.”
The irony is rich. By building out of necessity what VCs now seek by design, Raution created a company that no longer needs their capital. He embodies the very traits the market now values: sustainable growth, capital efficiency, profitability, and deep customer relationships.
For founders considering their own path, his advice cuts through the noise:
There is not a single idea that is guaranteed. Not a single idea. Otherwise, you know, there are a lot of good VCs who would have mastered that thought. Nobody knows. So never be so bullish on an idea. Let an idea live its life. Some ideas will live a day, some a month, some five years, and some forever.
Find early customers willing to pay. Don’t just sit on pilots hoping one will convert. Make them your allies, spend time with them, let them teach you the tricks of the trade. Build strong product and strong sales, the two engines that keep you going.
And remember: what would have taken two years to build a decade ago can now be built in two to three months. There’s never been a better time to start, but discipline still matters more than speed.
Raution’s full-circle journey, from studying under street lamps in Kolkata to running a software company that competes with Salesforce, proves that extreme constraint can breed exceptional focus. His Sudama Devi Bhagwandas Jaiswal Foundation now counsels 850 kids in government schools, many of whom come primarily for midday meals. He’s building the next generation of entrepreneurs who understand that limitations aren’t obstacles, they’re the foundation of discipline.
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