Matt Wielbut: Startup Story, Funding & Lessons (2026)

Your Startup Is Staring at a $100 Billion Problem

Homeowners insurance is a massive, sleepy industry. It’s also incredibly inefficient. For every dollar a homeowner pays in premiums, an estimated 40 cents doesn't go to covering losses. It's eaten by administrative bloat, legacy systems, and manual processes. This leakage amounts to a $100 billion annual tax on homeowners.

This is the problem Ty Harris and Matt Wielbut attacked when they founded Openly. They didn't just want to build a slightly better insurance agency; they wanted to rebuild the core infrastructure of insurance itself. The result? A company that raised nearly $200 million by creating a product so fast and efficient that it went viral among the very insurance agents who were supposed to be disrupted.

Their story isn’t just about insurance. It’s a playbook for founders in any industry on how to find a powerful insight, build a world-class team, and raise the capital you need to win. Here are the key lessons.

Lesson 1: Find a Problem You Have Lived

The most durable startup ideas come from "earned secrets"—insights gained from years of firsthand experience. The Openly founders had this in spades, but from opposite sides of the table.

The Insider: Ty Harris spent 13 years at Liberty Mutual, rising to Chief Product and Underwriting Officer. He lived the pain of an incumbent trying to operate with clunky, outdated systems. He knew exactly where the costs were buried and why agents were frustrated. · The Outsider: Matt Wielbut was a technologist and repeat founder. He had already built and sold an insurance company (Elements Insurance) and experienced the friction from a consumer and entrepreneurial perspective. He saw how broken the customer experience was.

This combination is potent. They weren’t guessing at a problem; they had felt its consequences for years. Their shared diagnosis of the industry’s ills—that dealing with traditional insurance companies was a painful experience for everyone involved—was the foundation for Openly.

The Common Mistake to Avoid

Too many founders start with a cool technology (a "solution") and go hunting for a problem to solve. This is backward. Investors fund founders who are obsessed with a problem, not a solution. Your unique insight into a massive, underserved pain point is your most valuable asset. If you can’t articulate the problem better than anyone else, you haven’t earned the right to solve it.

Lesson 2: Define Cofounder Roles Religiously

While the source article mentions the importance of this, it’s worth digging into the tactical application. Ambiguity in cofounder roles is a leading cause of early-stage startup death. At Openly, you had a natural split:

Ty Harris: The insurance and industry expert. He understood the product, underwriting, and the agent-based distribution model. He could be the "internal CEO" focused on the core business logic. · Matt Wielbut: The technology and engineering visionary. He understood how to build a scalable tech platform from the ground up and had experience as a startup operator. He could be the "external CEO" or CTO, focused on the build and the fundraising narrative.

This division of labor allows for focus and speed. When every decision doesn’t require a two-person consensus, you move faster. It also signals to investors that you have a mature, professional relationship and have explicitly defined ownership.

How to Do This in Your Startup

Don't leave this to chance. Have the hard conversation early. Grab a whiteboard and create two columns with your names. Start listing every key function in the business and assign a "Directly Responsible Individual" (DRI).

Fundraising & Vision · Product & Engineering · Sales & Marketing · Hiring & Culture · Finance & Operations

If you find yourselves fighting over who owns what, that’s a red flag you must address immediately. The goal isn’t to build silos, but to create clear accountability.

Lesson 3: The Acquisition "Grind" Is Real

Matt’s previous startup, Elements Insurance, was acquired. He warns founders that the process is nothing like the celebratory headlines in TechCrunch. Selling your company is often a grueling, soul-crushing marathon.

An acquisition isn't a party; it's an audit. At scale. For months.

Once you sign a term sheet, the real work begins. Due diligence is an exhaustive process where the buyer's lawyers, accountants, and engineers pick your company apart. Be prepared for:

Financial Diligence: Scrutiny of every line item in your P&L, balance sheet, and cap table. · Legal Diligence: Review of every contract—customer agreements, employee offer letters, vendor NDAs, IP assignments. Any ambiguity can kill a deal. · Technical Diligence: A deep dive into your codebase, architecture, and security practices. · Team Diligence: Interviews with key employees to assess talent and cultural fit.

The process is designed to find reasons to lower the price or walk away. It’s a period of extreme uncertainty that can demoralize your team. The lesson: build your company with clean books and clear documentation from day one, as if you’re going to be acquired tomorrow.

Lesson 4: Master Your Fundraising Narrative

Raising $200 million requires more than a good idea; it requires world-class storytelling. Openly mastered the ability to distill a complex business into a simple, compelling narrative that VCs could grasp and get excited about.

The Problem: The insurance industry is saddled with 40% administrative costs, creating a $100B opportunity. · The Solution: A tech-first platform that uses data and automation to eliminate this waste and provide a superior experience. · The "How": Openly built its entire tech stack from the ground up, allowing it to cut quote times from days to seconds. · Why Now: Independent agents are desperate for better technology to compete. · Traction: Our product went viral with agents, proving the demand. · The Team: We have the perfect blend of insider knowledge (Ty) and technical expertise (Matt) to win this market.

This isn't just a set of slides. It's the core story you tell everyone—investors, hires, partners, and customers. It must be clear, concise, and repeatable.

How to Apply This This Week

Pressure-Test Your "Earned Secret": Write down the one core insight you have about your market that others don't. Is it strong enough to build a company on? · Hold a Cofounder Roles Meeting: Book two hours with your cofounder(s). Whiteboard every key business function and assign a single, clear owner. Document the result. · Practice Your 30-Second Pitch: Can you articulate the Problem, Solution, and Why You'll Win in the time it takes to ride an elevator? Practice it on five people who know nothing about your business. · Start a "Due Diligence" Folder: Create a folder in your company drive and start saving key documents: incorporation papers, key contracts, your cap table. Getting organized now will save you months of pain later.