An Opinionated Spreedly Bibliography, Part One of ???

“You will be the same person in five years as you are today except for the people you meet and the books you read.” — Charlie Tremendous Jones

While it’s a gross simplification, there’s a lot of truth in that Charlie Tremendous Jones quote: relationships and reading will define and encompass most of our personal growth over our lifetimes, and the same holds true for the formation and growth of an organization. Someday I’d like to tell the people-side of the story of how Spreedly came about, but in this (hopefully) ongoing series of posts I’m going to focus on the other half of the equation: the books – and more generally the writings – that inspired me to found Spreedly originally, and have influenced me as I’ve been a part of it since.

The caveat is that this bibliography is opinionated. While the Spreedly co-founders and the others who have joined us along the way may have read some of these books, they definitely haven’t read all of them. And, if they have read them, they might completely disagree with my analysis. Maybe they’ll post their own opinionated bibliographies someday – I know I’d love to read them!

I’m chunking this bibliography into general areas of influence. The first set of writings are all about how I came to want to start a business in the first place…

Catching the Entrepreneurial Bug

I grew up in a pretty average, American, middle-class household in the 80’s and 90’s. My dad was an architect, and my mother was an RN. In my mom’s case, “RN” stood for “Retired Nurse,” since upon getting pregnant with me she decided to shelve her syringe for a few decades to pour herself into myself and the two sisters that followed three and nine years later. We never went hungry, and we often had a surplus, but there were lean times too. One period in my early teens stands out   when for over a year, Dad kept the lights on by throwing newspapers in the wee hours of the morning and Mom kept the larder stocked by being incredibly frugal.

I remember my parents taking a few stabs at entrepreneurship as I grew up. One in particular stands out: a short-lived attempt to sell water filters that looked too good to be true and was; I got inoculated for life to high-buy-in multi-level marketing schemes as a result. But while personal financial literacy was clearly demonstrated and taught – balance your checkbook, stay out of debt, save for the future, etc. – I never got much exposure to what I would now recognize as “real world entrepreneurship.”

And yet here I am, a couple of decades later, a real world entrepreneur starting and running two successful businesses. The first was a software consultancy, followed by Spreedly. Forget learning entrepreneurial skills, what was it that made me want to actually be an entrepreneur in the first place? From a “things I read” perspective, I highlight two authors in particular: Robert Kiyosaki, and Paul Graham.

The Cashflow Quadrant by Robert Kiyosaki

Look, here’s the deal: I’m going to level with you that I read and was influenced by Robert Kiyosaki of Rich Dad, Poor Dad fame, and you’re going to promise not to laugh. Because from where I sit a few decades later, if the typical business “novel” is over the top, Kiyosaki is plain outrageous with his smarmy self-help and supposedly autobiographical sketches that are surely 99% made-up. But as we retread my path to founding Spreedly, I’d be remiss to pretend Kiyosaki didn’t influence me.

But while many might cite the famous book, Rich Dad, Poor Dad, as their biggest influence, Kiyosaki’s simpler, less well-known follow-on book, The Cashflow Quadrant, had the biggest impact on me personally. I’d already read Rich Dad when I picked up Cashflow Quadrant, but I remember the key idea of the latter much more clearly and still think back to the basic premise of Cashflow Quadrant on a regular basis.

What is that premise you ask? It’s so simple you can draw it on a whiteboard in sixty seconds or less:

an opinionated bibliography

The basic idea is that you can earn your money from one or more of four different quadrants: Employment, Self-employment, Business ownership, and/or Investing. What resonated with me, especially as someone who wasn’t raised in an entrepreneurial household, was the difference between being self-employed and being a business owner. The best way to sum up that difference is as follows: if you go on vacation for a month and you’re self-employed, forward progress (and income) stops while you’re gone. If you’re truly a business owner with a well-managed business system, when you go on vacation for a month and come back the business has gotten better while you’ve been away (and continued to generate income).

Should you read The Cashflow Quadrant? Well, it’s a quick read, and it’s still the best breakdown of the four different places you can earn income that I’ve read anywhere. But be be prepared to roll your eyes a good bit as Robert Kiyosaki absolutely loves himself some hyperbole.

How to Make Wealth by Paul Graham

There are hundreds, if not thousands, of financial self-help books that encourage you to “build business systems,” “stop trading time for money,” just like Cashflow Quadrant did for me. But as a person who loved to write software, the next step for me was starting to read Paul Graham’s essays. Graham, or “pg” as he’s often referred to, co-founded and wrote much of the code for one of the first e-commerce platforms – Viaweb – later acquired by Yahoo and renamed Yahoo Stores. He moved on from there to do angel investing, and eventually started Y Combinator, the iconic startup incubator.

As I prepped for this blog post, I looked back through pg’s archives trying to figure out approximately where I started reading and which essays were most influential. I settled on How to Make Wealth as being fairly representative, but that’s kind of unfair since they really affected me as a body, not individually per se. The basic idea I picked up was thus: my ability to write software, and the rapidly falling costs of building and delivering software systems, could be leveraged to build a business system with much less up-front capital and in a much shorter period of time than was previously possible.

Needless to say this was a very exciting prospect. It set me on the hunt for business ideas worth pursuing and people worth pursuing them with. How to Make Wealth was published in 2004, and Spreedly was started in 2007. There is no doubt that the former influenced the nature and timing of the latter.

At this point maybe you’re thinking, “So if I just read the things that Nathaniel did, I’ll have the same outcomes he did!” Or maybe you’re thinking, “This is all fine for you Nathaniel, but how is it going to help me?” If I could circle back around to the idea I began with: it is our reading and our relationships that shape us. I hope that if it does nothing else, this series will convince you to invest time in reading good books that expand your horizons and challenge your pre-conceived notions. I’ve heard people say, “I’m just not a reader,” and it makes me cringe inside since it’s basically the same as saying, “I’m just not into growing as a person.” So go forth, pick up an insightful, hokey business novel or a book that will challenge you to communicate better or a book about the theory behind an interesting topic and never stop learning and growing as a person.