From Architect to $8.6M Business: My Journey Building and Buying Back Best Self


 I recently had the opportunity to appear on the AppSumo podcast to share my entrepreneurial journey. For those building—or dreaming of building—a business, here’s a breakdown of the most important lessons I’ve learned along the way.

Turning $550 into $2M in 9 Months

What started as a $550 investment grew into a $2 million personal development brand in under a year.

The secret? I pre-sold more than $300,000 worth of products before producing a single one. It was a real-world market test that validated demand and minimized risk.

Architecture to Entrepreneurship
I didn’t plan on becoming an entrepreneur.

At the time, I was earning $30,000 a year as an architect, commuting 45 minutes each way. In 2012, I launched a side hustle: a Shopify store selling graphic prints and posters.

I used Tumblr to share my artwork, and eventually, my designs were picked up by media outlets like MTV and Fast Company.

As the side hustle outpaced my day job income, I realized it wasn’t the destination—it was a launchpad for something even greater.

How Best Self Was Born

The Best Self Journal wasn’t born from a grand business plan. It was something I created for myself while working on my architecture thesis.

I launched a Kickstarter to help fund the production—hoping that others might want one too, so I wouldn’t have to pay full cost for a single unit.

It resonated far beyond my expectations, raising $326,000 in just a month.

That moment confirmed I had tapped into something meaningful. Within nine months, we had generated $2.2 million in sales with 90% gross margins.

Product Development Through Customer Innovation

What started as one journal evolved into a full product ecosystem, thanks to customer insights.

We initially tried selling blank notebooks, but quickly realized that users needed more structured guidance.

Instead of traditional prompt journals, which often miss the mark if users don’t connect with the daily prompt, I created Discovery Decks—card-based systems offering flexibility.

Customers can select prompts that align with their current mood or needs, leading to products like Idea Decks, Writing Decks, and Decision Decks.

Using AI to 10x My Efficiency

AI has completely transformed how I run the business.

One major breakthrough has been analyzing thousands of customer reviews using AI to uncover “golden nuggets”—authentic language that converts better in marketing than traditional copy.

By segmenting this language by persona (productivity-seekers, relationship-focused users, etc.), I now generate high-converting testimonials in seconds—something that once took hours.

I use AI to automate repetitive, energy-draining tasks, so I can focus on strategic, high-value work that requires human creativity.

The $8.6M Sale and Buyback Story

In 2022, I sold Best Self for $8.6 million. At the time, the company had 10 full-time employees based in the U.S.

The opportunity came through casual networking in Slack groups.

Fast forward 14 months, and the private equity firm that bought the company missed its financial targets by 11%, couldn’t pay my earnout, and offered to shut it down—or let me buy it back.

After initial hesitation, I decided to repurchase the brand. Why?

  1. AI made it possible to run the business leaner than ever.

  2. I wanted a real-world business to test advanced AI tools.

  3. I knew it would be an incredible story—and learning opportunity.

Building My Lean Operation

This time around, I didn’t rebuild the original team. I started from scratch with a lean approach.

I used Fiverr for one-off projects, hired virtual assistants through Quick Hire VA, and tapped into affordable, skilled talent in Latin America via Sagan Passport.

This approach gave me flexibility and dramatically reduced overhead—without compromising quality or growth potential.

My Essential Productivity Stack

Here are the core tools I rely on daily to keep everything running efficiently:

  • Granola – Auto-generated meeting notes

  • SuperWhisper – Voice-to-text email writing

  • Arc Browser – Smoother, faster browsing

  • Finaloop – Automated accounting and bookkeeping

  • CleanShot – Quick screenshot + visual documentation

  • 1Password – Secure team password management

  • Loom – Easy SOP and explainer video creation

Takeaways for Aspiring Entrepreneurs

  1. Validate Before You Build – Kickstarter was a low-risk way to confirm market demand.

  2. Solve Your Own Problems – Best Self began as something I needed myself.

  3. Leverage AI – Use it to streamline operations and reclaim your creative energy.

  4. Start Lean, Scale Smart – Don’t overbuild. Start with what you need, then grow.

  5. Stack Your Skills – Unique combinations of skills create competitive advantage.

  6. Speak Like Your Customers – Real testimonials from customer reviews outperform traditional marketing copy.

  7. Energy > Time – Focus on work that energizes you. Outsource the rest, even if you can do it.

👉 https://cathrynlavery.com/

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