Daily Hive’s “Something or Nothing” series features both up-and-coming and established entrepreneurs from around the country and asks them why they do what they do, their biggest failures, success strategies, and more. Know someone who should be featured? Let us know.
Jerrid Grimm has always been a great storyteller.
When he graduated from university in Alberta, he started working at an advertising agency. After some time in the industry, he realized that companies had interesting stories to tell when they were given the chance.
But industry standards weren’t quite aligned with Grimm’s values — passive ads and banner ads were king, which meant that, while companies were getting their branding and name out there, their stories weren’t.
And when Grimm tried to coordinate longer-form paid content pieces (AKA branded content) it was next to impossible to get them published. There simply wasn’t technology available to process and track their results that.
So Grimm and his business partner, Tiam Korki, decided to do something about it. They started Pressboard.
Pressboard’s technology makes it easy for brands to get their stories published in top publications worldwide. Companies can tell their stories and publications can make money — it’s a win-win.
Grimm took the time to speak with us about his journey as an entrepreneur, what some of his biggest challenges have been so far, why you need to get good at falling, and what he does to stay sane.
- Birthplace: Beaumont, Alberta
- Place you consider home: Vancouver, BC
- Age: 39
- What you wanted to be when you were a kid: Angela Bower from Who’s the Boss?
- Favourite class in school: Math or science
- Previous job: I worked at an advertising company called Newad
- How do you commute: Bus or bike
- What you always have with you: AirPods (yes, I’m aware they’re douchey) and Chuck Taylors
- Favourite vacation spot: Maui, Hawaii
- What time you normally wake up at: 6 am
- What time you normally sleep at: 10:30 pm
- Normal breakfast: A granola bar, a banana, and an apple
- Reading/listening to right now: “Reply All,” a Gimlet podcast
- How many employees you have today: Around 20
What’s your elevator pitch?
At Pressboard, we think companies are super interesting. More interesting than banner ads. So if you’ve got a company and an interesting story to tell or products that are useful, you should be able to tell them in more interesting ways than a banner ad. So we make it easy for companies to get their stories on major publications, whether it’s Daily Hive or the Wall Street Journal, and any other outlet.
How did all of this begin?
I’ve always been in marketing and advertising, and we were starting to do a lot of banner ads. I didn’t really like it — I mean, it does the job, but it just wasn’t interesting to me.
Then I started seeing more branded content and starting seeing how brands could share a story that people were interested in. I thought it was cool and started suggesting it to my clients. One of my clients was all over it. They were like, yeah, this is great, but when I started to try and run these branded campaigns, it was impossible to find out what media publisher to work with and how much it was going to cost and how to get it published.
There was no tech to support this process. So, me and my now business partner, Tiam, decided to change that.
What was it like quitting a stable job and income and starting your own company?
I have a theory about stress. I think as humans, we get “max stressed” and that’s it. We can’t go any more stressed out than that.
So having a second kid, I was already messed up. Tie along whatever you want from there, you don’t even feel it.
I was also lucky to have Tiam, who is the perfect business partner. I had known him for a few years. I needed someone to be the technology side of the business and he needed someone to be the business side of it. So we were a match made in heaven for that and we trusted each other. So we were in it together, and our significant others were on board as well.
It actually didn’t feel like a risk when we did it. It felt like the right thing to do. But I think the things you don’t realize when you’re working at a company is the stuff that now you have to do. Like accounting – you forget that someone has to send an invoice to your customer and make sure they’ve paid it and then go to the bank in time to deposit a cheque and pay an employee you’ve hired and do the HR and… you do everything, all pieces of it.
If you thought you were busy before, you just didn’t realize how many things you had to fit into a day now. But there are so many great things that come with it, like the ability to control your own destiny, hire the people you want to work with, work with the customers you want to work with and the partners you want to work with. It pays off, all the extra work is worth it.
Have you raised any money to date?
Yep. We’ve raised just over $2 million, all from local Vancouver investors, Angels, and a little bit of Venture Capital.
How has Vancouver played a role in the development of the company?
To be honest, being in Vancouver in our industry is a massive disadvantage from a proximity and customer base side. A lot of the advertisers and their agencies and major media publishers are based in New York, which is 5,000 kilometres away, a three-hour time change, and a big flight. While our competitors can walk down the street to go to a meeting or an event.
It makes you think in much different ways. But the good thing about that is, it forces you to be really creative because you’re at such a disadvantage that you try out new business muscles.
People also just love it here, so you have happy employees, which is a massive advantage. People can’t get enough of the oceans here, the mountains here — so you hire people and they’re enjoying their life, and as long as you can build a business that works here, the hiring and the culture is second to none.
There’s nothing better than being a Canadian right now either. When I first started the company, I’d go to New York and I wouldn’t really say that I was Canadian. I felt like they wanted to work with other US companies. Now I lean into it. People love what Canada is about right now.
How did you overcome the distance?
First thing we did was built the company to be entirely remote, so I could be sitting on a plane in the air and as long as there was WiFi I could do everything I was able to do from my office. We setup a couple of satellite offices, like really small shared spaces, that could grow with us in Toronto and New York, putting us closer to our customer.
We also created a team of interested, like-minded individuals that shared our values of ambition and creativity. So we’ve got people that work from a beach or a campsite or an office or a plane – you can work from anywhere. I think people really like that and it’s created a really interesting culture. It also means we can open up in any market. We can be in the UK and open up a “UK office.”
There’s a lot of opportunity and we see the world as our office.
What’s one of the biggest challenges your team has faced?
The flip side of being a Canadian company is that Canadian companies are quite often at a disadvantage from raising money and having access to partners, compared to someone in the Valley, especially in the tech space. We’ve had to extrapolate to create a profitable company off the bat because we couldn’t go out and raise $10 million on a keynote slide.
So we’ve had to build a real business from the start, that was profitable, and that gave us a lot of longevity. We haven’t been hunting for cash, we took money from people that we wanted to when we needed it.
What do you wish you knew before you started?
They say having a startup is a marathon, not a sprint. And I heard that when I started and was like, cool, that sounds fine for you guys but we’re going to sprint and everything’s going to be in the first year, this is going to blow up.
Then what you learn, what I wish I would’ve known, is just how committed and persistent you need to be every day, just moving the company ahead inch by inch.
You’re going to need the right people around you to be able to support that, whether it’s investors or team members or business partners, like I have with Tiam, because you go through good times and bad times – and you need people willing to go through all that with you.
I also wish I would’ve known to offload the tasks you’re not good at. When you start a company, you do everything. So I wish I would’ve started offloading some of that to partners or team members earlier on because that probably would’ve made it so that I didn’t have to work a ton of nights and weekends doing stuff like bookkeeping, which isn’t my skill set and probably doesn’t add that much value to the company if I’m the one doing it.
As an entrepreneur, what’s the biggest pain that you yourself have had to overcome?
A lot of people would say work-life balance, but for me, my biggest challenge is brain space. Trying to turn your brain off from the business is incredibly difficult because you’re so passionate, you’re so in love with it — but it’ll literally keep you up at night. So trying to find ways to be able to switch your brain off for a little while I think is healthy, but it’s something I haven’t mastered at this point.
How do you prevent burnout?
If you love the thing you’re doing and can’t get enough of it, and you can focus your tasks on that, I think you’re less likely to burn out.
And then, you need to give your brain some space to rest. You have to have some other interests, set aside time each day to be do something that isn’t work-related.
I like being outside. So if I can just do anything outside — either go for a hike with my family, ride my bike, or go skiing in the winter — as soon as I’m outside, nothing else exists except what I’m doing. I can be really present in it.
What are you learning right now?
I’m learning a lot about business models right now. One thing about a startup is you hear a lot about pivots. We’ve pivoted our business model several times and I find it fascinating.
It’s fascinating you can change the underlying economics of a business without changing the product, and the company can look entirely different. So I’m reading a lot about business models, and we’re trying a lot of different business models.
What is the biggest failure you’ve experienced?
Not anticipating the effects of change.
Internally, we’d make these changes but not realize how those changes would affect someone’s job or compensation, or career aspirations. Not anticipating that far enough down the road, I think has been a big failure and realization on my part.
I think you have to understand yourself, that you don’t know everything, so you’re going to make mistakes. I used to waterski, and my dad always said if you’re not falling, you’re not learning. And he told me that when I wasn’t falling.
Is there a quote or line that’s changed the way that you approach business?
It’s actually one that I mentioned earlier, from my dad. I get a lot of inspiration from him.
He was the one who taught me to think about failure in different ways. He’d always say, “falling is good because it means you’re trying, so you should keep falling and keep trying.”
I really like that idea more than “fail first.” I hate the fail first as a startup term. I think it’s a VC term, and I think what it’s usually used to mean is “here’s some money, use this money, and get big or die trying because we can’t be giving you money to try stuff forever. So either make it happen or don’t make it happen, it’s all or none.” Whereas with my dad, he’s saying fall once, get up, learn, fall a little bit again, but keep trying.
Besides sales, how do you measure success?
From the business side, we focus on profitability. It’s a trailing signal, so it says you’re doing a bunch of other things — you have the right people, you have the right customers, you have the right business model, but it’s a really clear signal that says you have a business that deserves to exist in our capitalist society.
Then, from the company culture side, we think if someone’s getting exponentially better while they’re at Pressboard, then we’re doing well. If someone comes in as a coordinator and leaves and can get a job as a director of sales in two years, then we’ve exponentially created more value for that person. We help make this happen by offering a lot of training and providing tons of opportunity for growth.
What is your exit strategy?
Tiam and I have said from the beginning that we were going to build a business that could be acquired. We always said we would sell the company when someone valued it more than we valued it ourselves. That’s the signal that we take to say that this is the right time because someone else can do more.
What’s the likely exit strategy? Probably a larger company that covers a lot of different marketing pieces, like an Adobe or something like that. Something that covers a lot of different aspects of marketing but doesn’t cover content marketing that well and they need to plug that hole in their system.
What’s the most surprising part of your job that most people wouldn’t think is part of your day to day?
I would think they’d be surprised how little of it is glamorous. We picture CEOs in these big board meetings and raising money and pontificating from some sort of tower above everyone.
In reality, I’m up early because the eastern time is three hours ahead. I start at their time, and I send out cold emails to a customer that I really want to land. I’m in the trenches — I don’t defer everything off to everyone else and just sit there and do thought experiments or anything like that.
I think the idea of like Chief Operating or Executive Officer sounds like you’re running this faceless corporation. But in reality, you’re just aggressively trying to move the company forward and make sure that you have the right resources on site.
Do you have any mentors?
Yes, I do — from a business perspective, my dad is one of my biggest business mentors. He’s had a business for 35 years and he built it from the ground up and it’s gone through several booms and busts fusing Alberta. My mum was always a great mentor to me too. She passed away, but she had the soft skills of entrepreneurship. She always had a vision for things. She did yoga in the ’80s before it was cool.
Then I have mentors through our investors, who can be great mentors since they have a vested interest in the same thing that you do, which is a successful company, but they come from different backgrounds and they have different domains.
How do you want people to remember you personally?
I think you can be in business and you can be a capitalist without being an asshole. I’ve never subscribed to the idea that nice guys and nice girls finish last. I’ve never thought that was true. In the long run, being a good person is good karma for your life.
So I’d like people to think that I was ambitious but that it didn’t make me an asshole. And that I was a good person to be with. I’m talking as if I’m dead, yeah. I think that my legacy would be to try and change that idea, that nice guys finish last.
Interview edited for clarity
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