How'd You Learn That?

I’ve taken a strange path...a college-dropout-turned-fireman-turned-startup-founder...and it leads to some cool conversations with people from all of the different phases of my life. When I get into the details of my back story, people are always curious how a person goes from driving an 80,000 pound ladder truck through a city street to writing feature specs, doing strategic planning, and diagnosing marketing funnels.

I don’t know the answer about how “someone” would do it...but I know how I did it and the reasons why. So, let’s dive in.

Early Education Origins

I don’t remember being great at school. I recall being reasonably intelligent but not particularly motivated, especially amongst my peers, most of whom ended up going to Ivy League schools and achieving a ton of amazing things. I also definitely don’t have a photographic memory, although I sure wish I did.

So, if it’s not some innate love of learning, and I’m not some savant with an incredible memory, what’s my process for being a “regular dude” who can rapidly learn new skills? 

Interestingly, I didn’t really understand what I was doing in the moment, but after reflecting on it, there are really four key elements to learning the way that I learn:

1. The “Big Bag of Whys”
2. The Minimum Effective Dose
3. The Deep End of the Pool
4. The Feedback Loop

“The Big Bag of Whys”

This is a saying that I’ve unabashedly commandeered from my business partner, Dan - he always professes that when the going gets tough, having a mental “big bag of whys” to fall back on is what gets him through.

This maps really well to my wonderfully brief college experience. I was studying business, and obviously have enjoyment for business in general...but there were two problems. The first obvious problem was that I didn’t HAVE a business at that time in my life, so everything was basically theoretical and not practical. The second problem was that I was barely studying business due to all of the general education requirements - English, math, basket weaving, etc...but only two actual business courses in an entire year of education.

I think the education part might be a double edged sword - in other words, I do see theoretical value in studying a wide breadth of subjects. However, even if I finished school, I’m not really confident that the shiny, newly-minted, bachelor’s-degree-toting 21 year old Matt would have had what it took to start a business. It just feels like an expensive path to still be at square one.

Education for me has always been very tactical in nature - I have a strong reason to go learn something, have a specific outcome in mind, and realize that I can’t achieve it without learning a specific new skill. So I go learn it to satisfy the “why” behind it.

That’s the first element - for me to effectively learn something, there’s got to be a clear outcome that I’m chasing - ideally, something that’s clearly measurable - and the skill that I’m learning needs to bridge the gap between where I am today and what I want to achieve.

Takeaway: Know your “why”, and revisit it frequently.

The Minimum Effective Dose

This maps pretty closely to my frustration with general education requirements in college; I do so much better when I can focus and learn ONLY the topics that I need to know in order to bridge the knowledge gap that I’m facing.

When I was in the fire department and decided to learn to code, I went through a bootcamp in order to get it done. However, I felt super hesitant about the idea because I didn’t want to do months and months of surface-deep “placeholder projects” just to (again) still be at square 1.

So, I set up a call with the CEO of the bootcamp and asked him straight up if I could just work on my own software platform as the capstone project for the course. Lucky for me, he was on board and I was off to the races. It was wild - I don’t think I’ve ever worked that hard in an academic or academic-adjacent setting...but I was ruthlessly motivated because I knew why I was there. The exact codebase that I started in that bootcamp was the codebase that I used when starting, growing, and eventually selling my first company.

Takeaway: An outcome-oriented approach drives a pace of learning unmatched by theoretical education.

The Deep End of the Pool

Here’s the thing about outcome-oriented learning - you’ve gotta drive hard towards that outcome, or it’s just “learning for fun”. And not to dismiss that either; many people that I know, love, and respect are natural learners and enjoy learning primarily for the sport of it. It’s a trait that I wish I had, but I don’t - for me, my learning velocity maxes out when I know I can take my skills and immediately apply them in a real-life, high-stakes situation.

My situation in my first company reflected this perfectly - I had built a very rough Minimum Viable Product (MVP) on some third-party software, and had about 50 paying customers. The faster I learned how to code and re-built our software, the sooner I could switch them over and start building the functionality that they needed.

As I was going through the code bootcamp and subsequently building the software with my CTO (who I met in that bootcamp, incidentally), our customer count was effectively our “doomsday clock” - we couldn’t open sales again until we got on the market, and we couldn’t get on the market unless we learned how to code and worked our asses off, and our customers were leaving because our product wasn’t good enough.

If I learned slowly in that situation, my company would have been dead. I feel like that’s pretty solid motivation to not suck, to put in the extra work, to keep reading when you’re tired...and it really helped me push through because I knew that I was playing the game for real.

Takeaway: By immediately applying your new skills to a real life problem, you'll massively increase your speed of learning...because it really matters.

The Feedback Loop

There’s a bit of natural curiosity at play here - how do I know that I learned the right thing? How do I know that I learned it well, or if I’m capable of implementing what I learned? How do I know if I’m an idiot?

Enter the feedback loop. Let’s say for instance that you learn a new strategy for advertising your business. The “why” is straightforward - you want to do better at your job, or grow the revenue of your business. You go and grab the “minimum effective dose” off the shelf - meaning that you figure out a quick and relatively inexpensive way to test your fresh new strategy. Then, you dive in the “deep end of the pool” by putting it in play the following week.

How would you know whether or not it’s working? Simple, right? You’d measure results against the previous week using the old strategy. If you’re a real fancypants, you might run a split test, measure the variant against the control, and so on...but let’s not get bogged down in the details here.

The important thing is that you have a framework to measure whether or not the thing that you learned and implemented is actually effective - and to use that to determine whether or not you need to continue to improve upon it. Does it help you achieve your “why”? Does it help you cross the skill gap that you identified? Did you even choose the right thing to learn?

This type of curiosity feels obvious in my marketing example, but it gets fuzzier when you’re learning more soft, philosophical skills. How do you measure whether or not you’ve improved your skills as a conversationalist from that course you took? How can you know whether or not you’re getting better at remembering names after that active listening book you read?

I find it really helpful to literally write out the way that I’ll gauge my improvement, and in the case of non-business goals, to ensure that I put myself in the situation that will give me the data I need.

In other words, the only way to know if you’re better at remembering someone’s name from a conversation is to go have a few conversations. But it’s a feedback loop just the same, and I find it to be critically important.

Takeaway: Write out the specific “definitions of success” before you start learning a topic or skill. This helps to stay focused on why you started in the first place - and provides a specific rubric to gauge your improvement.

Wrapping Up

When people ask me how I learned something, I usually just cut the corner in the conversation and toss up a casual, one-sentence answer. But I’ve gotta admit, it was really fun to actually examine my process as I wrote this article.

The reality is that there’s no secret sauce - no crazy process where I put a book under my pillow, read it back to front, or anything like that - I’ve just gotta have a good reason why and a way to take immediate action. It might not be right, but it works for me.