Monthly Update 6/17

June 2017

Drew Thomas
The Bootstrapped Investor
4 min readJul 3, 2017

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Welcome to the first monthly update on my investment journey. This is the first in a series of monthly letters about my ideas and progress in a “side career” that I’d like to turn into my real career.

Over the past month or so, I’ve established three main goals for my investing career.

  1. Start (in a real way, not just for fun).
  2. Invest 10% of the previous year’s income in 10 different vehicles (every year).
  3. Document the journey in a Medium publication and try to incorporate audio or video at some point.

Start

I’ve been investing in the stock market with “play money” for four or five years. I started by creating a savings account and auto-transferring $100 into it each month. Then, when I saw public market opportunities, I took advantage… sometimes a single share at a time. To date, I’ve almost tripled my stock market portfolio investment.

I’ve also predicted a few large scale trends and placed non-monetary bets on them. For example, I bet on responsive web design early as a way to push our agency ahead of competition (it worked for a couple years).

I’ve always thought that I had the knack to be a professional investor, but I’ll start “for real” one day “when I have money.” Vaguely, I was trying to build and exit a company so that I could use that money to start. Instead, I’ve decided to get serious today. Starting now.

Invest 10% in 10 companies (or other vehicles)

This rule allows me to justify spending for investments in general before I consider a specific investment. This is important, especially working as an entrepreneur without reliable income. Knowing that money is set aside to invest (and that there’s a plan) frees me from making investment decisions based on finances. Ironically, making financial decisions based on current finances is usually a bad thing. (I’ll elaborate on that in the Lessons section of this publication.)

I started this halfway through the year, at a weird time (I recently left a company I’d co-founded to freelance/explore). Therefore, I’m starting with an even $50K top line for this first year. 10% of that is $5,000 and divided over 10 investments, that’s $500 per investment. That should increase next year by default (I’ll make more than $50K this year), but in the future, as investments start to return, the 10% investment amount should grow exponentially (if I do well).

Document the journey

The journey from beginner investor to who-knows-what could be compelling. I know documenting is important to grow an audience, and having an audience is power. If I’d started documenting my tech journey from day one, I’d have a much larger audience to launch this idea to…

Documenting and building a name will help my investment career and my current career in a number of ways, but most practically, it will bring me deal flow in the future and give me a platform to promote my investments themselves.

Ok, that’s the intro. In the future, these emails will be more of an update on what I’m thinking and who I’m looking at (that’s the plan for now anyway). I’ll do a quick one to start, but in the coming months, I’ll be more detailed.

So far, I have 4 out of 10 investments made for 2017 and 2 in consideration.

  • On June 19th, I invested in Lendsnap through SeedInvest, a crowd-funding platform that accommodates non-accredited investing.
  • On June 21st, I bought some Bitcoin through Coinbase. It’s a little late for the current run, but long term, I still think it’s a good idea. Plus, it’s a good experiment. I’m learning so much about cryptocurrency now.
  • On June 26th, I decided to invest my time and whatever money is necessary to create an app with a friend. The opportunity is good. I’m not actually counting my time as the investment, but I’ll be putting a certain amount of money into the idea in order to give it a shot.
  • Before coming up with this investment plan, I’d already bought some public Snap on March 2nd. I decided to count this in my 10 investments for 2017.
  • The two investments I’m considering are Made on Main, another SeedInvest company, and Dance it Yourself, a company my wife and I started and paused a few years ago. In order to consider it an official investment, I’ll hire some development help to get the app to where it needs to be, but I haven’t committed to an actual plan yet.

I’ll write an article about each of my investments, who they are, and why I decided to invest, so I won’t go through that all of that in this first update letter.

More next month! Thanks for reading, and stay tuned!

Drew

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