Failure Diaries: Jeremy Spira
Jeremy shares his experience working at an early-stage startup, and how his passion and optimism became a double-edged sword.
Tell me a little bit about yourself…
I’m a recent Waterloo graduate. I was part of a co-op program and studied Peace and Conflict studies, Speech Communication, and Business. In the past, I’ve worked for Canadian Tire, a dessert catering company, and Student Car Share. I now work as a Marketing Coordinator at Enterprise CarShare.
What are your values or principles — the things that motivate or influence you?
Passion. I find that I need to always be — at least at some level — passionate about the product I’m working on, or the people I’m working with. I also strive for excellence because I think everything I do or represent is an extension of my brand. Another value I’m always aware of is determination — just setting goals and getting shit done.
What is greatest piece of advice you’ve ever received?
Most problems can be dealt with tomorrow; step back, and don’t let them ruin your day. That’s really helped me in many situations because I find that it’s so easy to get wrapped up in things you shouldn’t. Sometimes, all it needs is just taking a step back, sleeping on it, and looking at it from a different perspective. Being able to do that can be hugely valuable and can really change your understanding of the problem. And then you can solve it.
“For me, this forced me into this mindset where I was always trying to be perfect. Even when I wasn’t living up to the expectations, at least I wasn’t failing.”
How has your background and/or upbringing influenced the way you experience failure?
My family was always supportive of me doing what I wanted to do, but I wasn’t really given the ability or the opportunity to fail. Failure was something that happened, but we didn’t really analyze the failure to learn from it. We’d always just brush past it. For me, this forced me into this mindset where I was always trying to be perfect. Even when I wasn’t living up to the expectations, at least I wasn’t failing. So I would sum it up as — do whatever you want, but don’t fail.
How has fear of failure affected you in the past? Can you share a story about that?
There was a day at Student Car Share when we had a media launch in Peterborough and another event in Guelph later that day. The first event went over and I didn’t want to miss the second one. It was really important and I wanted to make sure that we were firing on all cylinders. So when I left Peterborough, I flipped and started driving really fast. In the moment, it seemed like the right decision until I got a call from my manager. Apparently, I had driven past the CEO of the company; he had tried to catch me but couldn’t. On top of that, I was in a branded vehicle.
It was one of those moments where trying to please everyone ended up with me almost getting fired. Not only that, but I could have gotten a ticket or even gotten into an accident.
That incident really taught me that we’re responsible for our actions — even when we’re backed into a corner where we don’t “have a choice”. The reality is that we’ve made decisions to get to that point. In my case, there was pressure on me but I chose to make those decisions. It was a big learning moment for me because I’d wanted to be a superstar employee. But if you don’t know when to say no, it can all slip away from you very easily.
What’s the fuck up story you’d like to share with us today?
My fuck up is related to my experience at Student Car Share. I started there as a co-op student, and ended up working for them for 2 years. We launched in August 2013 and by September, we were in 16 markets in Ontario. So we were moving extremely fast, but we unfortunately didn’t have the right systems in place to support that growth. First, we hired 50 brand ambassadors at various universities not knowing what it meant to hire and manage 50 people. So we ended up firing them all leaving us with no one on the university campuses. Since I was a co-op, I then had to drive everywhere — from Ottawa all the way to Windsor. I drove 25,000 km in my first 4 months, I was paid minimum wage, and I worked 80 hours a week even if I was getting paid for 40. Everything was always frantic; decisions were made quickly and many resulting mistakes were siphoned onto me to fix.
The fuck up for me was staying there for two years and dealing with that abuse. We were making a lot of mistakes as a company, but I convinced myself that that was just how startups were and that it would eventually get better. I allowed myself to struggle without even thinking to say no. I didn’t realize where to draw the line. The worst thing is that in the process, I also fucked up my relationships. I chose to leverage my personal connections to help the company grow, but the company would just pull out and screw them over. So essentially, I allowed my personal connections and my personal being to be negatively affected by a job.
Can you walk me through the emotional and psychological effects of your experience?
It definitely kept me up at night. I kept wondering why I let them take advantage of me for so long. It also made me very wary when I was looking for a job after university. As much as a job is important, I wanted to make sure that I was treated well. That became my priority whereas before, getting experience was what drove me. So, in a way, instead of being as open to things, I became scared.
Another thing I noticed is that I started viewing certain things as negative, because I’d previously experienced them in a negative environment. I didn’t recognize that they weren’t actually negative; they were just negative in that particular workplace.
What was your experience leaving the company like?
What’s interesting is that at some point, they apparently fired me but didn’t tell me — which was really weird. I was working part-time for them, and then everything just slowly kind of fizzled out. They didn’t outright fire me, but at some point we just didn’t work together anymore.
That’s a really messed up way to end a relationship. How did you react to that?
It was very shocking. I felt betrayed because I worked my ass off for this company for two years and they clearly didn’t value me as an employee. Eventually, they ran out of business and disappeared overnight. So in a way, I guess I was happy that I didn’t go down with them and was able to save face a little. But it definitely tainted my brand in Waterloo given that they screwed over so many people.
Were you able to salvage those relationships?
I was able to salvage a lot of them. But it takes time. I’m still trying to salvage one of them a few years down the lane. Trust is very easy to lose, and it’s really hard to gain back when you’ve lost it.
What helped you get to the point of acceptance? Where you fully embraced the failure?
I had really great colleagues and we had a support group of sorts. We’d go out for coffees and chat, which was really cathartic. It was comforting realizing that I wasn’t alone and that other people felt like I did. Plus we were able to reflect on things and realize that it wasn’t all our fault. Obviously, we made mistakes. I made mistakes and the choices I made while there jeopardized some of my relationships. But I also felt responsible for letting down all the students I signed up since the company shut down. So it was important for us to separate our own failures from the company’s failure. You don’t wanna accept responsibility for something that’s not your fault.
From what I can tell, some of your experience resulted from the fact that you were just starting out in your career. What advice would you give people in that situation?
Remember your value. I totally understand the need to be humble and appreciative of the opportunity. But you also need to remember your value and communicate when you feel like you need to. And it’s tough — there’s not always the opportunity to easily address problems. But more often than not, there’s going to be a willing participant you can find to help. So be humble, but also be in tune with the fact that you are worth something.
“You have to make sure that you find a way to communicate the things you need to. If you don’t talk about it, it doesn’t get better.”
There’s this stereotype around how men are meant to deal with difficulties. For example, having to go through such high pressure situations without complaining or expressing their feelings. Did you experience this?
Oh yeah, I definitely experienced that. I’ve worked for companies that had mostly male employees — which I think is always a problem. If you don’t have enough diversity of opinion, you’re really going to miss out on understanding and ultimately thriving. At Student Car Share, I think the expectation was for everyone to shut up and just deal with it. Why would you talk about your feelings? Everybody had to work hard and if you didn’t want to do it, someone else would.
It was hard because when you’re starting out career-wise, you’re afraid of losing that job. But in such situations, you have to try to figure out who your ally is — who the person you can communicate with is. Who’s the person you can openly share your feelings with so you don’t explode? And maybe it’s not at work. Maybe it’s your best friend you tell. But you have to make sure that you find a way to communicate the things you need to. If you don’t talk about it, it doesn’t get better.
What did you learn having reflected on this failure?
I think my experience made me more attuned to looking at the warning signs and addressing them faster. I’d also previously struggled with communicating — I was a co-op and I didn’t want to rock the boat. So I let things fester and they became bigger issues. Now, I’m more attuned with my capabilities and when I have an issue I’m able to speak up. I talk to my boss, we work through the issue, and we figure out a way to make sure it doesn’t happen again.
How did your experience influence your perception of failure? How do you approach it now?
I fess up to it much quicker. I embrace failure more honestly and more quickly instead of waiting to see what happens. I think it’s still partly affected by the environment or community I’m in; but I now realize that failure doesn’t get better with time. Failure always comes with some repercussions, so the earlier you address it, the better. Think of it like an earthquake: failure can be a small earthquake where you only feel a rumble, or it could be a big earthquake with an aftershock that causes more damage than the earthquake itself. You don’t want to experience that aftershock.
