I plan to invest in 50 startups, and you’re invited for the ride. How, and why, you ask? Read on…

My Investing Journey

The journey of a thousand miles starts with a single step.

I began my investing career at age 14, when I lost the majority of my childhood savings in an investment devastated by the Great Recession. Five years later, I cashed out the leftovers of that stock and reinvested it all into a Vanguard account. Two after that, I closed that and reinvested it all in a Betterment account. This now holds my personal investment account, Roth IRA, and rollover’ed 401k from previous employers. Betterment remains my go-to no-brainer recommendation for casual investors.

Joining the Startup Community

Professionally, my career began exposing me to more of the business world. In particular, I was now steeped in the world of early-stage, high-growth startup companies. Slowly, I (clumsily) began to develop skills: taking products to market, bootstrapping a student dormitory, and learning from entrepreneurs at the top of their game. While Vanguard funds still deserve the lion’s share of most portfolios, my personal appetite for risk began to increase as my startup career progressed.

My First Angel Investment

Before I left Miami and moved to New York City last year, I invested in a company called WhereBy.Us on pure instinct. (See my retrospective deal memo here.) Months later, WhereBy.Us received investment from Jason Calacanis, a prolific entrepreneur and early investor in Uber, Thumbtack, and Dyn.com. Intrigued, I read his book, Angel, and walked away inspired. With equity crowdfunding platforms, angel syndicates, and now overall lower investing thresholds, I realized I could start my “angel investing” education for much less “tuition.”

The Plan

Calacanis recommends investing $250k in 50 startups over 3-5 years in Silicon Valley to have a chance at a “unicorn” or a company worth $1 Billion. Using SeedInvest’s Auto-Invest feature, investment minimums drop to $200 per startup, and investors can pass on any deal. At $200 per startup, for 50 startups, investing in 50 startups drops to a relative bargain of $10,000. Calacanis likens this to “…Dagobah, a place where you can learn from other angel masters without losing a limb or your head.”

My Hopes

I’ve already made four investments, and look forward to sharing those deal memos soon. What I like about Calacanis’ ideology is that, early on, the money is less crucial than learning to be a better investor. This means writing deal memos and reviewing them to discover biases in my own thinking as time goes on. In addition, angel investors are evaluated by their combined contribution of money, time, network, and expertise. This is where I hope the upside will be given my career.

Wherever this adventure leads, I’m thankful for your readership along the way.


致富光荣 Zhìfù guāngróng
致富光荣 Zhìfù guāngróng, “To get rich is glorious”

Further notes:

  1. https://dsdoes.com/why-i-joined-jasons-angel-syndicate-13db61876044
  2. https://medium.com/@TheFullRatchet/how-to-angel-invest-like-the-best-featuring-jason-calacanis-ba35ea799227
  3. https://www.linkedin.com/pulse/starting-today-civilians-can-angel-investors-should-jason-calacanis/