May 30, 2025
I recently appeared on the AppSumo podcast to share my entrepreneurial journey, and I wanted to break down the key lessons for anyone looking to build their own business.
Turning $550 into $2M in 9 Months
I transformed a simple $550 investment into a $2 million self-development company in just 9 months.
What made this achievement remarkable was my approach: I pre-sold over $300,000 worth of products before manufacturing, effectively validating market demand before taking major risks.
Architecture to Entrepreneurship
I didn’t set out to become an entrepreneur.
Starting as an architect making $30,000 annually with a 45-minute commute, I began a side business in 2012 – a Shopify store selling graphic art and posters.
My unconventional marketing strategy involved posting my designs on Tumblr, which eventually caught the attention of major publications like MTV and Fast Company.
The transition happened naturally when my side business began out-arning my day job.
Rather than viewing this as my final destination, I saw it as a “freedom vehicle” to explore what I truly wanted to do next.
Video
Watch the full podcast on YouTube.
Or, watch it below.
How Best Self Was Born
The Best Self journal emerged from my personal need rather than a calculated business decision.
Initially created as part of my architecture thesis project, I launched a Kickstarter campaign, hoping others would help fund the production so I could have one for myself without paying excessive costs.
The Kickstarter’s success was immediate and overwhelming—raising $326,000 in approximately one month.
This validation moment made me realize I had discovered something special.
The business achieved $2.2 million in sales within nine months, with impressive 90% gross margins.
Product Development Through Customer Innovation
Best Self started with a single journal but expanded through customer-driven innovation. When attempting to sell blank notebooks, my team and I recognized the need for guided prompts.
However, we identified a flaw in traditional prompt journals – users might not connect with the daily prompt, leading to skipped pages.
This insight led to my creation of Discovery Decks—card-based systems that offer flexibility.
Users can choose prompts that resonate with them on any given day, resulting in idea decks, writing decks, and decision-making decks.
Using AI to 10x My Efficiency
I’ve become a pioneer in using AI to streamline business operations.
One of my most effective strategies involves analyzing customer reviews for “golden nuggets” – authentic customer language that resonates better in advertising than traditional marketing copy.
By feeding thousands of reviews into AI systems with specific prompts, I can quickly extract compelling testimonials segmented by different audience types (productivity-focused, relationship-focused, etc.).
This process, which previously would have required extensive manual work, now takes seconds.
My philosophy centers on using AI to handle time-consuming, energy-draining tasks that don’t require human creativity, allowing me to focus on high-value activities.
The $8.6M Sale and Buyback Story
In 2022, I sold Best Self for $8.6 million when the company had 10 full-time US-based employees.
The sale wasn’t planned—an opportunity arose through networking conversations in Slack groups.
Fourteen months later, the private equity firm that acquired the company approached me with unexpected news: they had missed their numbers by 11%, couldn’t pay my earnout, and were considering shutting down the business.
They offered me the chance to buy it back.
Initially hesitant, I ultimately decided to repurchase the company for three reasons: AI capabilities now allowed me to handle tasks that previously required full-time employees, I wanted to test AI applications in a real business environment, and I thought it would make a compelling story.
Building My Lean Operation
Rather than rehiring my previous team, I chose to start fresh with a lean approach.
I utilized platforms like Fiverr for specific projects, hired virtual assistants through services like Quick Hire VA, and employed nearshoring through Sagan Passport for Latin American talent.
This strategy allowed me to maintain operational efficiency while significantly reducing overhead costs and avoiding previous organizational patterns that might limit growth.
My Essential Productivity Stack
My current toolkit includes several key tools that keep me operating efficiently:
- Granola for automated meeting notes
- SuperWhisper for AI-powered voice-to-text email composition
- Arc Browser for improved web browsing efficiency
- Finaloop for automated accounting and bookkeeping integration
- CleanShot for quick screenshot and diagram creation
- 1Password for team password management
- Loom for recording and creating standard operating procedures
Takeaways for Aspiring Entrepreneurs
1. Validate Before You Build: My success stemmed from pre-selling products through Kickstarter, proving market demand before significant investment.
2. Solve Your Own Problems: The most successful businesses often start with entrepreneurs addressing their personal pain points – Best Self began because I needed the product myself.
3. Use AI for Operational Efficiency: Leverage AI to handle repetitive, energy-draining tasks while focusing human creativity on high-value activities like strategy and innovation.
4. Start Lean and Scale Smart: Begin with minimally viable operations and add resources only as needed, rather than building large teams from the start.
5. Skill Stacking Creates Unique Value: My combination of design background, business acumen, and AI adoption made me uniquely valuable in the marketplace.
6. Customer Language Beats Marketing Copy: Mining customer reviews for authentic testimonials creates more effective marketing than traditional copywriting.
7. Energy Management Trumps Time Management: Prioritize activities that energize you and use tools to handle tasks that drain your energy, even if you’re capable of doing them.