I Failed Three Times Before Building a $2M ARR Company

Between 2018 and 2022, I started three companies. All three failed. I burned through $200K of savings, maxed out credit cards, and seriously questioned whether entrepreneurship was for me.

In 2023, I tried one more time. Today, ClearPath Analytics is approaching $2M in annual recurring revenue with 40 employees and backing from top-tier VCs.

What changed? Everything and nothing. The market didn't change. My intelligence didn't suddenly increase. What changed was my understanding of what actually matters when building a company.

Failure #1: The Solution Looking for a Problem (2018)

The Idea: A mobile app that used AI to help people organize their photos more intelligently.

What I Thought Would Work: The tech was impressive. I spent 8 months building sophisticated algorithms that could categorize photos by content, faces, locations, and events.

What Actually Happened: We launched to crickets. Turns out, people didn't actually care about organizing their photos. The existing solutions (Google Photos, iCloud) were good enough.

The Lesson: Technology doesn't matter if nobody wants what you're building. I was solving a problem I found intellectually interesting, not one that caused real pain.

Time to Failure: 14 months | Money Lost: $65,000

Failure #2: Moving Too Slow (2019-2020)

The Idea: A B2B SaaS tool helping marketing teams collaborate on content calendars.

What I Thought Would Work: This time, I validated the problem first. I talked to 50 marketing managers who all said they needed this. I was smarter now.

What Actually Happened: I spent 6 months building the perfect product before getting it in front of customers. By the time we launched, three competitors had beaten us to market and captured all the early adopters.

The Lesson: Speed matters more than perfection. I should have launched an MVP in 6 weeks, not 6 months. Every day spent perfecting features was a day competitors were acquiring customers and learning.

Time to Failure: 18 months | Money Lost: $80,000

Failure #3: The Wrong Co-Founder (2021-2022)

The Idea: A platform connecting freelance developers with non-technical founders.

What I Thought Would Work: I partnered with a technical co-founder I barely knew because I thought I needed one. We had complementary skills on paper.

What Actually Happened: Within 4 months, we were arguing about everything: product direction, equity split, work hours, company culture. The tension made it impossible to build anything meaningful.

The Lesson: Co-founder compatibility matters more than complementary skills. You need someone who shares your values, work ethic, and vision. Skills can be hired; aligned values cannot.

Time to Failure: 11 months | Money Lost: $55,000

What Finally Worked: ClearPath Analytics (2023-Present)

After three failures, I was broke and demoralized. But I had learned expensive lessons. When I started ClearPath, I did everything differently.

Change #1: I Chased Pain, Not Ideas

I didn't start with a product idea. I started by talking to potential customers about their biggest frustrations. I spent three months doing customer discovery interviews with financial analysts at mid-market companies.

Change #2: I Launched in 3 Weeks

Instead of building for months, I created a basic prototype in 3 weeks using no-code tools and manual processes behind the scenes. It was ugly. It barely worked. But it solved the core problem.

Change #3: I Stayed Solo (Initially)

I didn't look for a co-founder. I hired contractors for specific tasks but kept full control over direction and decision-making. I only brought on a co-founder after 8 months, once I was clear on exactly what I needed.

Change #4: I Focused on One Thing

My previous startups tried to do too much. ClearPath does one thing exceptionally well: mid-market financial analytics. I turned down feature requests. I ignored adjacent markets.

Change #5: I Sold Before I Built

I pre-sold ClearPath to 5 customers before writing a single line of production code. These early customers paid a discounted annual rate in exchange for heavy input on the product roadmap.

The Results

Eighteen months after launching ClearPath:

• $2M ARR
• 120+ enterprise customers
• 40 employees
• $3M seed round from tier-1 VCs
• 85% gross margins
• Sub-5% monthly churn

The Honest Truth About Failure

People romanticize failure in startups. "Fail fast," they say. "Failure is a learning opportunity." That's partly true, but let's be honest: failure sucks. It's expensive, emotionally draining, and hard on relationships.

But failure is also the best teacher. I learned more from my three failures than I could have learned from any book, course, or mentor.

If I Were Starting Over Today

Month 1: Customer discovery only. Talk to 50+ potential customers. Find real pain.

Month 2: Build ugly MVP. Launch to 10 friendly customers. Get brutally honest feedback.

Month 3: Iterate based on feedback. Pre-sell to 5 paying customers.

Month 4-6: Build real product funded by pre-sales. Stay focused on one core problem.

Three failures didn't make me a better founder. Learning from those failures did.