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One investment. Every day.
For 366 days. In public.
What started as an experiment turned into the proof of concept for everything else I'm building. This is the full story, the data, and the invitation to run your own version of it.
Why I Did It
I was financially ruined in 2008. Fraud and system failure. Most people would have stopped at who to blame.
I kept asking why.
Why did the system fail the way it did? Why is it so hard to invest locally? What does a stock market investment actually fund? How do you build an economy that serves the people living in it?
Each answer opened the next question. That trail led me through a decade of following threads from social enterprise, impact investing, CDFIs, B Corps, the circular economy and Regulation Crowdfunding. I got a securities license to understand the system from the inside.
By 2024 I had a direction worth proving.
So I did what curious people do.
I ran an experiment. 366 consecutive days of investing in the public capital market that most financial advisors had never heard of. To learn what I didn't know yet.
The experiment didn't answer the question. It deepened it.
That's still happening.
The Rules
One investment per day. No exceptions, no skipped days, no make-ups.
Regulation Crowdfunding, Regulation A+ and any other productive crowd-sourced financing vehicle accessible to a retail investor. Not just equity offerings either. Revenue shares, loans, community bonds, anything that demonstrated the breadth of this new market.
Documented in public. Every investment got a social media post. Every month got a portfolio review. Every platform got an honest evaluation, including the ones I would not recommend.
Always the investment minimum. Some days that was $100. Some days it was $10.
366 consecutive days. From February 29th, 2024 to February 28th, 2025. The leap year was intentional. The Leap Year Portfolio was born.
The Numbers
These are publicly reported as of the most recent portfolio review:
total positions held
deals evaluated to make the daily selections
platforms vetted across the duration
annualized cash flow return on the mature portfolio
days missed
Cash flow return defined as interest plus dividends plus realized returns plus return of principal, against deployed capital. Investing carries the risk of financial loss. Past performance does not guarantee future results.
What I Actually Learned
A few months in, I realized I was not as good an investor as I thought I was.
I knew the theory. I had been writing about Reg CF for years. But putting real money down every day, against real founders, with real consequences, is a different practice. You learn what your blind spots are when they cost you something.
Here is what I learned.
Most deal structures are wrong for the business they're funding. Founders reach for SAFEs because they're free and familiar. But a SAFE is an equity instrument designed for a venture-scale exit. Most community businesses will never have that exit. The instrument doesn't fit the business. That insight became the CARE Note, a debt instrument designed specifically for community-scale enterprises.
You can't build a productive economy on a feudal base layer. The monetary architecture underneath our economy was designed for a different era with different assumptions about who capital serves. Productive instruments sitting on top of extractive infrastructure will always be fighting upstream. That insight became the inspiration for the white paper.
Circular investment vehicles are nearly impossible to track. There is no reporting standard for revenue-share notes and community debt instruments. That's why institutional capital can't enter at scale. That insight became the data standard now adopted by the CfPA and presented to the SEC.
Nobody in this market has the right map yet. Reg CF is brand new. Platforms modeled themselves after Y Combinator. Founders built pitch decks for demo days. Investors came in reading VC blogs. Everyone borrowed frameworks from other ecosystems. The territory is different. The maps don't exist yet. Building them is the work.
Researching a founder is like hiring a new employee. The financial model matters. The cap table matters. But what you're really evaluating is the person. Their judgment. Their transparency. Their willingness to engage with hard questions. You already know how to do this if you've hired people before. Trust that instinct.
Every lesson became a tool when curiosity fueled me to push past the surface problems. The experiment ended and the building began.
The Story in Quarterly Chapters
This section will expand into a serialized blog over the coming months. Brief outlines below.
Q1: The Cold Start
February to April 2024
Setting the rules. The first ten investments. The early platforms. The first time I caught myself rationalizing a bad deal because the calendar said it was investment day.
Q2: The Reframe
May to July 2024
The moment I realized my evaluation framework was incomplete. The first time a founder pushed back on my public comment and I had to defend it. The first big losses.
Q3: The Pattern
August to October 2024
The structural insight that became the white paper. The data standard hypothesis. The first time an institutional investor asked me how I was tracking the portfolio.
Q4: The Compound
November 2024 to February 2025
Returns starting to flow. Recursive reinvestment. The closing arc.
The experiment is over.
The work continues from a different posture now.
I'm no longer investing every single day, but the cadence taught me what daily looks like. I know what the asset class can do because I lived inside it for a year. Everything I write, everything I advise, and every instrument I design now comes from that lived ground.
You don't have to do what I did. But you do have to do something.
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