It'll Take Longer Than You Think - Part I

Here’s the big idea, up-front: When building a business, it’ll take longer than you think to land on your feet - and that’s by design.

Look, I’m not one of these shiny, well-pedigreed, Stanford CS degree turned Y Combinator founders (not that there’s anything wrong with that; most of them are wicked smart). I’m a firefighter who was walking down the street one day and accidentally stepped in a big pile of...software (lol).

At least that’s how it felt at the time. It was an accidental journey with no well-defined end point that was driven by my own impatience and dissatisfaction with doing anything at an “average” level.

That being said, looking back on it, it’s a super interesting journey. Incredibly circuitous, filled with failure after failure and bad decision after bad decision, but within that were a few amazingly good ones that were responsible for our eventual success. 

So, what’s the point of this article? There are two, actually. The first one is to reinforce the fact that this stuff is crazy hard, and takes a long time. For anyone out there working their asses off trying to make their first dollar with their business, I see you - and you’re who this is for. 

The second point is to try and extract the couple of good decisions that actually moved the needle for us, which I’ll do throughout the story. My perspective may not align with everyone else’s, and may not be true for every business. That's cool, in fact, because I think that people who write only for universal truths are typically watering down their work. 

In other words, this is my own unique perspective - your mileage may vary. Cool? I hope so, cause it’s my article and that’s what I’m doing 😂

Let’s begin.

The Origin Story

March 2013 - Year 1

I think that my eventual success in business is tied to the type of person that I am. I’m the guy who gets intensely focused on one or two things at a time, but it’s always “all in” or “all out” - there’s never much of an in between.

This was very evident in my passion for the fire department, which was my “first career”. I was by many accounts an overachiever; I wanted to do all the things, take all the classes, and be the fastest and best 100% of the time. Of course there was always someone faster or better than me, but that’s the beauty of it all.

Based on how “into the job” I was, I never had a plan to leave after 9 years. I never had a plan to leave, basically ever. They were probably going to have to force me to retire as a 65 year old broken man who couldn’t pick up a ladder anymore.

Yet somehow, despite that love for the job...here we are.

A great part of the fire department culture is the brotherhood of it all - when someone asks for help, you help them. So when my best friend Jake asked me for help marketing his new CrossFit gym that he opened, of course I said yes.

It was fun to have something that challenged me in a different way. The project got me back into web design, which I hadn’t done since high school, and helped me retrain a certain type of intellectual muscle that had been at rest for about a decade or so.

But it was just that - a side hustle, a way to help a buddy, nothing too serious. Build a couple websites on my days off, maybe a little extra cash to do something fun, no big deal.

My Perspective: I think that first-time entrepreneurs like me tend to make bets that are too big, and make them too early. We were able to keep this super casual at first because we were still working our day jobs. Don’t get me wrong, we eventually dove in and went full time, but it would have been a spectacular failure to do it this early.

Don’t quit your job because you want to be an entrepreneur - do it because you already are one and your job is getting in the way of your business.

Messing Around With Ideas

May 2014 - Year 2

I’m now running a very mediocre “web design for gyms” company called RunYourGym on my days off from the firehouse. 

Jake and I have breakfast to chat about some ideas for his gym’s website, and it’s one of our classic conversations: one idea turns to two turns to ten, and before we finish breakfast we have a ridiculously complicated business plan of how we’re gonna do basically everything for the gym industry. You think I’m kidding...I mean EVERYthing.

After flailing around on this massive stack of ideas for a few months, we settled on creating marketing automation for gyms. We still had no plans to leave the fire department or even to become a software company - we just wanted to build automations that we knew worked for Jake, and sell them to gyms around the world.

But we still really had no idea what that would look like or how we would do it. We spent most of this year just trying different things, building programs in his gym, and casually refining what we thought we wanted to work on.

My Perspective: Everyone tells people to stay super narrow, niche down, do one thing well, etc. And honestly, that’s great advice, and not listening to it will burn us a bit later in this story...

That being said, I also think that people misapply this advice frequently. A narrow focus is the goal, not the starting point. If we didn’t give ourselves permission to think of a crazy, unrealistic, and borderline-stupid business plan up front, we never would have uncovered the opportunity of building turnkey marketing automation for a niche market.

Give yourself some freedom to explore in the early days - then, ruthlessly trim away the stuff that doesn't work or doesn’t excite you before you make a bigger bet.

Idea Validation (Talking To Humans)

December 2015 - Year 3

After we spent about another year or so figuring out exactly what this business was going to be, we decided to start having some conversations. I won’t try to convince you that it was some fancy idea-validation framework or the first chess move in a long-term strategic partner acquisition channel...it wasn’t that well thought out. But we did know a friend who had a big following in the fitness space and a podcast, so Jake jumped on there to talk about what we were doing.

One thing that we DID believe in is providing value in every interaction - Gary Vaynerchuck talks about this a lot, as do a lot of great marketers. We were building our very first automation product - it was built entirely on other people’s software, and was basically cobbled together - but the idea was solid.

So Jake goes on the podcast, and I remember it was the very first time that I had “The Feeling” - you know, the one where you realize that people might just want what you’re building. It was quickly followed by “The Lowkey Panic” - when I realized that I had no idea exactly how I was going to deliver it all.

I was at work the day that the podcast went live, and I remember I was putting my uniform on at the firehouse at about 6:45am, listening to the episode, and smiling. A few hours later I was sitting at the kitchen table (which is basically the epicenter of any good firehouse) with my laptop open in between calls trying to keep tabs on things. My captain Jason walks up to me and says, “What are you doing over there Zuckerburg? You rich yet?”

I was laughing on the outside because not only had about a thousand people downloaded our free content, but we’d sold about 50 of these “standalone automations” - which were a total afterthought. I was planning on maybe selling 5-10...and now had the problem of figuring out how to actually deliver what I said I would.

To answer Jason’s question, I wasn’t rich - in fact, I basically had less money than I did when we started because I’d spend 2x what we earned figuring out how to ship the product (whoops). 

But as far as the actual idea? Solid so far. People gave us money in exchange for the value that our “thing” created in the world. Sweet. Let’s GO!

My Perspective: Don’t underestimate the network effect of industry experts in a tight niche. Justin Welsh pushes this really hard in his LinkedIn course, for instance - you could talk about “marketing”, or you could talk about “marketing via LinkedIn for Canadian B2B SaaS companies who sell via 1:1 demos and have at least $20K in MRR” - which one of those cohorts is it easier to resonate with? 

And if there WAS an expert in the space with a non-competitive offer, how amazing would it be to speak to their audience and have it feel like your content was built JUST for them? Staying tight is what helped this content land so well.

My other takeaway is that it’s ok to talk about stuff before you have it all figured out. I’m a chronic “overthinker” - left to my own devices, I would play the whole chess game before I move the first pawn. But that’s a killer in business.

In this particular case, we had an idea, a vision, and a giveaway that would be valuable by itself - even if our business failed, people would get value from consuming the content we gave away. And that was enough for us to put ourselves out there, which paid massive dividends down the road. 

Give yourself permission to not have all the answers. Just figure out the next right move and go do it.

Wrapping Up - Part 1

So far, we’ve traveled over three years via these short stories, and have still made precisely zero dollars in profit. But I did learn an incredible amount during this time period, and had a lot of fun working on my “side job”.

My viewpoint on this is simple. Some people might look at this and say, “you worked your ass off for three years and didn’t make any money.” And they would be right. But that doesn't mean it’s a waste of time - it’s only a waste if it doesn’t make you smarter.

Building something special, especially for the very first time, will always take longer than you think. Embrace the process and the destination will show up. And if that means that you work your day job for the first three years while you try new things, so be it - just have some fun and take some notes along the way and it’ll be time well spent.

In part two, I’ll follow the same short story + perspective format, and will cover our decision to become a software company, the inflection point of quitting my day job, and the criticality of seeking mentors, coaches, and people who are smarter than you in order to fast track your learning and success.