Three simple lessons from 25 years in sales
And how they can inform your investing strategy
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Good morning, this is Thinking Capital. A weekly mission for you to optimize your financial life. Today’s mission: reflection.
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My career in sales began long before full time employment, an internship, or even college. It was some time during grade school when I realized that the candy my mother bought for our building’s Halloween party was sold for only a fraction of the retail cost. Eureka!
Lesson one: Your margin is my opportunity.
— 4th grade me & Jeff Bezos
It only took a few weeks before the dean of the school summoned me to her office. Candy wrappers were spilling out of desks, lockers, and the pockets of students. Besides littering the grounds, students were eating during and in-between classes, and everyone wanted to know who was selling the candy.
I went viral. I had to deal with a slow supply chain, changing consumer demand, and sanctions from an unfriendly governing body. As much as I enjoyed my new found purpose, I quickly realized that these small sales were not worth the risk of getting suspended.
Three syllables defined the mid to late 90s for me: Pokémon. Most of my profits were going into the slot-machine experience of buying packs of cards and hoping for rare holographic cards. No one was even playing the card game, we just wanted the treasure chest effect of seeing what was inside. Eureka!
Lesson two: Scratch your own itch.
While I liked the occasional piece of candy, I was obsessed with Pokémon cards. That passion allowed me to better understand what a potential customer was looking for. It also allowed me to take bigger risks holding inventory, with the worst situation being a dream of having more cards for myself.
The interesting thing was that despite starting with a love of the cards, the more packs I sold, the less I wanted to keep for myself. I noticed that my taste and the taste of my older customers started moving on to other card games, and that first-hand feedback informed what would eventually happen to the rest of the market.
That stuck with me. If you really loved a product, you would know when it was time to move on. It was frustrating to question my own judgement and see something I swooned over go from being super cool to childish and lame, but it helped inform the final lesson:
In Naval’s epic tweet thread, “How to Get Rich (without getting lucky)” he shares many lessons, but the quote above has always stuck with me. Whether it was Pokémon cards, specific clothing brands, or Nextel phone housings, I was early to learn what would eventually be the darling of the public markets… recurring revenue.
The biggest lesson from selling items one by one was how time-consuming it was to actually process the transactions. Buying my first rental property changed that. It allowed me to iterate on the first two lessons and satisfy the third:
Your margin is my opportunity; college dorms were twice as expensive as what I needed to satisfy my mortgage.
Scratch your own itch; I knew there would be other students who wanted the independence of off-campus housing without the inconvenience of being too far from campus.
Play long term games, with long term people; while this can mean so much more, it was an introduction to recurring revenue on a 12 month contract. The sale happened once and it was very easy to tell who would and wouldn’t renew, well before the next sale had to take place.
Yes, I know that’s a little bit of a stretch on what Naval was likely going for, but that’s just another compliment to his brilliance.
So, what can you do with this information?
Hopefully you can learn from my lessons, but it’s far more important to reflect on your own. Specifically, how can lessons from work and play impact the way you invest?
<3
Armand