How to Turn Frustration Into a Million Dollar Software Business (Part 3)

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"I was the opposite of a 'model student'"

"Even if you know nothing about entrepreneurship, you are more qualified now than I was."

"How do I get hired? I had no idea."

"It made me realize how I'd gone from zero to an authority in the niche by being totally obsessed with something."

"That business turned out to be the worst decision I ever made."

"Eventually, it dawned on me that I need to learn about marketing."

"I have a better life now than pretty much anyone I meet – thanks to the hard work I've done over many years."

What's the best business advice you ever received?
What book would you recommend?
What's one attribute or characteristic of a successful entrepreneur?
What's your favorite productivity tool or habit?
What new business idea would love to pursue one day?
What's an interesting or fun fact most people don't know about you?
What's one of your most important passions outside of your work?

This episode is part of our First Customers series.

Links

Thrive Themes: Website
Omer Khan: LinkedIn | X

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Nate Baker is the co-founder and CEO of Qualia, a software platform for title companies that helps coordinate the complex process of buying a home. Today, Qualia generates over $100 million in ARR with a team of 600 and has raised more than $200 million. In 2015, Nate was 21 years old and decided to build software for the real estate industry. He had no experience in that space. He didn't talk to any customers. He just did some research and decided that was the thing he was going to do. Then he started building. Still without talking to anyone. Nate admits this was a mistake. He and his co-founders got key things wrong about how the business would work. They wasted months building things they eventually threw away. It wasn't until they found their first customer that they started making real progress. Their first customer was Barry Feingold, a state senator in Massachusetts who also ran a real estate law firm. Barry believed in the vision, taught them the industry, made introductions, and helped them understand what actually mattered. The relationship was unconventional: Nate and the first 25 employees rotated through living in Barry's basement. New hires would get a call Sunday night: "Your onboarding is in Andover. You're going to live in Barry's basement for two weeks. He's going to teach you title. You have to tutor his kids in math." But then Barry's existing software vendor found out he was working with Qualia and shut off his access overnight. Nate and his team didn't even have the core features built yet. They had to figure it out fast. It became the most productive month in company history. Barry didn't just become a customer—he introduced Qualia to his competitors. Those network-based relationships became the foundation for the first 10 customers. Nate learned that your first customers must come from your network, not cold outreach. In this episode, you'll learn: 1. How to find your first customers through network-based selling instead of cold outreach 2. The multi-year upfront contract strategy that brings cash forward and locks in commitment 3. Why geographic focus beats national expansion in the early days 4. How to embed yourself with customers to truly understand the problem 5. When to hire your first sales leader and how fast to scale

Richard Hollingsworth, Fyxer

Agency to AI SaaS: Scaling from $1M to $18M ARR in 9 Months

Richard Hollingsworth is the Co-founder and CEO of Fyxer, an AI-powered email assistant that predicts and drafts emails for busy professionals. Richard and his brother Archie grew up on a farm, but they knew the slow pace of agricultural life wasn't for them. They saw tech as the opposite environment—fast feedback loops, results within your control. They started by building the UK's largest executive assistant agency, bootstrapping it to $5M in revenue. But from day one, they had a bigger vision: turning the service into software. For years, they tried to build "tech-enabled" solutions, but nothing worked to pull the price down enough for the mass market. Then GPT-3 launched. It was the breakthrough they'd been waiting for. Unlike other AI SaaS startups starting from scratch, Fyxer had a secret weapon: six years of detailed logs from human assistants. They knew exactly how an EA organizes an inbox because they had thousands of hours of data on it. They used this proprietary data to train their AI models, ensuring their product was more accurate than a generic LLM wrapper. The growth was explosive. They started the year with $1M ARR and a team of four. Within 9 months, they hit $18M ARR. They moved to San Francisco, joined an AI residency, and shifted their focus from "Tech Bros" to "Professional Services"—real estate brokers, consultants, recruiters—people who actually drown in email. One of their biggest wins came from a single signup via a Facebook ad. That user turned out to be the CEO of a massive real estate brokerage. Within 7 days, Richard's brother Archie flew to Seattle, met the CEO at his lake house, and closed a $1.2M deal to roll Fyxer out to 5,000 employees.

Stefan Bader, Cello

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