The beauty and terror of being an entrepreneur is found in the unknown — and the frequency of staring down that dark corridor of uncertainty. Beautiful, beautiful, terror… I often find myself in meetings that, upon reflection I’m asking myself “how did this happen”. Everything, including success is always different in hindsight. What seem to be small decisions to go left or right in the proverbial “fork in the road” can have long lasting impacts within your business.
“How’d you get into this racket?”
It’s the strategic decision making process and journey that inspired me to create this series that I’m calling “How’d you get into this racket?” Partly to reflect on our journey and document it, but also in the hopes that someone else going along the entrepreneurship journey can find some value in these reflections.
As the title says, this entry is just an intro into what I’m envisioning with this series. I feel like entrepreneurial advice is a hot topic that gets a lot of attention and eyes but I also feel a lot of the advice out there is excessively aspirational, or borderline motiv-ainment (see what I did there)?
I would like to get as practical as possible.
My goal is to create a space where people can ask questions that may lead into dedicated additions of this series to certain topics or just share opinions directly or personally.
The act of starting, running, sustaining, and growing a business is definitely the most difficult experience I’ve ever been exposed to. The numbers and stats are consistently stacked against anyone venturing out on their own and failure rates are high — businesses, ideas, processes, direction, aspirations, all of it. If it’s not the core structures you have to worry about it’s soft stuff like culture, or burnout. It’s all challenging.
Now, a brief explanation of this title which is one of those “how did we get here” moments.
Early in my journey we got our first big break, a huge milestone for Tennis which was then transitioning from our previous brand ALSO Collective. Our early history — which I think I’ll start with in this series — was probably not your average “start story”. Ours should have probably pushed us closer to a high percentage chance of failure.
It involved the following constraints:
- Starting with absolutely 0 capital
- Starting two businesses by year 2 — Why!?
- A major break up of the founding team — Not terribly shocking...
- A rental building in a great part of town where the landlords were aggressively kicking out tenants
- And a squirrel that lived in our storage closet and would scare the shit out of us every now and then — It might still be living there.
Starting with absolutely 0 capitalStarting two businesses by year 2 — Why!?A major break up of the founding team — Not terribly shocking…A rental building in a great part of town where the landlords were aggressively kicking out tenantsAnd a squirrel that lived in our storage closet and would scare the shit out of us every now and then — It might still be living there.Somehow we made it through those early formative years (zero claim that we have figured it all out at this point).
At some point during all the chaos, we landed our first big break. The “biggest” project we had ever landed (at the time) and on top of that we competed and won against a larger agency *boom*. As I write this all these thoughts pop into my head about process, project size, profitability, how to run a process efficiently, and how much time we spent on-site; but at the time, all we were thinking was F$@$ Yea!!
During this project we had an opportunity to interview one of Canada’s most successful entrepreneurs which was one of those moments where you’re in a room with your business partner sitting at a 15 person boardroom table interviewing one person thinking “how did this happen?”
Our naivety showed before we even arrived in the lobby, when we couldn’t figure out how to open the entrance doors — which felt “stuck” because it was a pressurized door. The door was pressurized because this particular office was on the top, top, top secret floor and needed it’s own dedicated hvac.
Once finally in the lobby, we were again taken aback by the breathtaking view, all while laughing about how a few blocks away our landlords were shutting off the heat “accidentally”. Photos of my business partner Symon in both scenarios below.
In hindsight it’s moments like this that I love. Those realizations and milestones that you’re pushing towards and all of a sudden “just happen”.
Towards the end of our meeting Mr. X asked me “so how’d you get into this racket”. Think about the last time someone asked you “how did you get into this racket?”. Never? Yeah, me neither before or after that moment. It’s something I think about, to me it shows a certain level of “let’s get real here for a minute, what are you actually doing?”
We told him our story, a more PG story to which he responded “Good Luck with that” which genuinely felt like it was coming from someone who has been through the grind and understood the journey. That was it and we were out the door still laughing to this day about that comment.
I’m always hugely inspired by other entrepreneurs at all levels because I totally respect how difficult the journey can be at all levels. This series will most likely align with people in their first 0–7 years and will probably follow that thought process. At the same time we have been lucky enough to generate an incredible mentor network that have been really invested in steering us in the right direction and I can’t describe how thankful and how much we have learned from a group of people who we are inspired by and have reached levels of their careers that are aspirational. Through this there are thoughts, processes, and concepts that we are also growing into and thinking about for the future that might be interesting to discuss with people in their 10+ yrs of experience.
This is the first part, and it’s less specific about our journey, and more about kicking this off with, “Let’s get real here for a minute, what are you actually doing?” in regards to being an entrepreneur.
I’m still mulling over the exact title, but the working title for the next piece is What is the plan? Exploring the decisions and blindspots at the very early stages after you decide that you want to start or pursue X as a career for yourself.
My business is in the creative + tech world, we build digital products for organizations with a $0 seed round of investment (meaning cashflow is king). We didn’t start here but we knew we wanted to move towards this direction from day 1. I want to explore some general ideas and questions that would have been a great exercise before I started this journey.
- How do you start? (don’t do it the way I did)
- Is it worth it? (A lot of personal complexity there)
- What is the idea and potential success rate?
- Partners, partners, partners (the good, the bad, and ugly)
- Why so fast? (Investment pros and cons? Do you need it?)
That’s it for now. Any initial ideas, comments, questions, topic ideas let me know.