Entrepreneur, mentor, A100 pioneer and voracious reader, Carey Houston has been there, done that — and her work is far from done

Tell me how your entrepreneurial path began.

That’s a great question. I actually started in the tech industry in Toronto and worked in three startups there. Then I decided it would be much more lucrative and fun to start a business back in Calgary, so I moved back here with my husband, and started a marketing consulting company. I ran that for about six years before I got the itch to go back in the startup world, so then have worked in three startups here and have done a lot of advisory as well.

Are you from Calgary originally?

I’m originally from Edmonton. That’s why it’s awesome to be part of the A100 and to have rebuilt my network back up — folks like Bruce Alton, who I went to university with and rediscovered through the A100. 

When you came back to Alberta, did you have a sense already of what other companies were doing here in the tech space, or was it something that you discovered once you came back?

You know, when I worked in Toronto, two of the three companies I was with were in fintech. The thing that was very interesting to me was the depth of the network in Toronto. Within a 10-block radius in Markham, for example, there were 10 or 15 other companies that had the same challenges that we could network with, and just lots of community activity. 

When I came back to Calgary, I was just heads down running my own business for a while and it wasn’t until I was between startups at one point that I realized that I didn’t have a network here anymore. But it wasn’t long after that that I reconnected with Rod Charko, who at the time was the CEO of Alberta Enterprise Corporation (AEC), and we had done our MBA together. I ran into him at a coffee shop downtown and he said, “What do you do?” and I said, “Well, I’m actually available.” He told me I needed to come work with him. So that was the beginning of getting plugged back into the network in Alberta.

I was quite unaware of the overall activity across the community, just heads down working in the business. So I don’t know that, at the time, I really had a good understanding of what was happening in the broader community. But I did some advisory work at Evoco with Alice Reimer and Brian Reimer. That kind of led to jumping in more formally into a full time role with them. 

And what year did you join the A100?

Well, that’s a funny question, because when I was at AEC, my job was VP of Industry Development, which was kind of an ill-defined role that was really about, how do we make sure that investors in which AEC was investing as an LP in their funds — how did we ensure they were aware of all the great companies that were starting and growing in Alberta. And on top of that, how did we maximize the likelihood that they would make investments here. 

“We started to hear from investors who were not local was that there was no management talent in Alberta. They were hesitant to make an investment. We thought, well, that’s not true.”

One of the things we started to hear from investors who were not local was that there was no management talent in Alberta. They were hesitant to make an investment. We thought, well, that’s completely not true. It’s just not as organized as it is in other locations. And then we started to hear some rumblings around what the C100 was doing in the Valley and realized we needed an Alberta version of the C100 so that investors could have confidence that there’s a lot of experienced talent to support early stage entrepreneurs, and also that entrepreneurs who were going through a tough spot could ring the doorbell of some folks who had walked in those shoes before and get some help. 

So I was actually the first Executive Director of the A100. We weren’t really sure what the reception would be, you know, because there were a lot of folks out in the community just doing their thing — building their businesses and working hard to succeed. And so we thought, you know, if we could get together a dinner — let’s try to get a table of eight people that would be interested and let’s test the waters. 

We went and had a coffee with Pat Lor and brainstormed who should be at that dinner table. We thought, well, nobody’s going to want to come because everybody’s so busy. So why don’t we invite about 30 people, and then maybe one in four would come and we have a table of eight. We ended up inviting just under 40 and 32 came. Oh my goodness. 

We ended up renting a room at Hotel Arts and pivoted from a little dinner party discussion into an action session where we pulled from the folks in the community to get their sense of what they felt was missing to help the Alberta community and Alberta entrepreneurs. At that first event we had 34 people, and there were people who I hadn’t seen in years and who weren’t really actively participating in any kind of community-driven stuff. We came away from that meeting with a pretty good sense of what we could do. 

So we had a follow up meeting and about 25 people attended and we asked them to write a cheque that night if they wanted to help out. I don’t remember what the exact number was but I think we walked away with about 10 cheques for $1,000. Wow. And that was the beginning of the A100.

Now here we are, more than 80 members and we have you and Rod to thank for it!

It was really all Rod. It’s very interesting how forward-thinking his thoughts were at the time. So many of the things that he believed needed to happen did happen the way he anticipated, and the community has become so much richer and more connected as a result.

So you’ve seen the evolution of the A100. Now, 10 years later, how do you see the A100 impacting Alberta’s entrepreneurs? 

It’s a tough and complex question. There’s a tremendous depth of talent in the A100. I think a lot of the A100 members are as individuals, as private citizens doing a lot of amazing, great work on behalf of our industry, and in particular, working directly to support entrepreneurs. 

“We have a chance to really influence how the tech industry is perceived and the support and recognition that we get as an economic driver in Alberta and in Canada.”

The landscape has changed here in the last year where we have a government that is very familiar with — and has history with — more traditional industries in Alberta. And I think now it comes back to do we as an organization and do we as private citizens and individual members.

I believe that the A100 is the right organization to take a leadership role in that kind of transformation about how this industry is viewed. If not us, then who? And if not now, then when? I do feel like this is an opportunity that’s going to be short lived and we have a chance to really influence how the tech industry is perceived and the support and recognition that we get as an economic driver in Alberta and in Canada. And if we choose not to influence, that’s okay. But then we are going to get the economic circumstances and support for our industry that we deserve.

You’ve seen and done a lot of different things in the startup space and in your own consulting work. So let’s talk about success. What have you learned from your experience?

As an entrepreneur, we have worked with more than 150 startups over the last three years from across Alberta. I would say there’s some interesting patterns that have arisen from that experience. One of them is that we continue to see a lot of entrepreneurs really struggle because they’re starting with the technology. They’re not starting with a deep understanding of a customer’s problem that they’re really passionate about solving. But you know, if founders and entrepreneurs are really interested in being successful — and not all are — but if they’re really interested in being successful, I think they have to be focused not on developing technology, and not on commercializing technology. They have to be focused on building a business.

Is that something that you can speak to personally as an entrepreneur and any successes that you’ve had?

Yeah, definitely. You know, I’ve had some dogs for sure. But I’m a pretty motivated and competitive person, and I really like to win. So it burns when something isn’t successful and I find in that an incredible opportunity for learning. It’s not that I don’t make mistakes, but I don’t very often make the same big ones twice. 

“It’s not that we want to celebrate failure, but we do want to acknowledge it and recognize that it is a normal part of the journey, and encourage entrepreneurs to not let a failure go to waste.”

There’s been lots of discussion around not so much normalizing failure, but making failure a very normal part of succeeding. It’s not that we want to celebrate failure, but we do want to acknowledge it and recognize that it is a normal part of the journey, and encourage entrepreneurs to not let a failure go to waste.

So how do we encourage entrepreneurs to look really critically at their products, at their business, at their team, and make sure that they’re focused most on what the business needs to be successful. And if they’re learning that lesson through making a big failure, that’s awesome. 

Have you had these learnings through your own trial and error or have you turned to other resources — people, books, etc?

Somewhere north of 250 entrepreneurs go through our courses. And the thing that I’m consistently surprised about is how many of them are showing up because they may have some struggles in their business, but they feel too vulnerable to admit it, and so they’re not getting the help that they need. 

I think a lot of entrepreneurs are pretty confident people, but you need to be able to ask for help. I have my little “shadow cabinet” that I rely on heavily. There’s probably 10 people who, over the course of my career, I consistently go back to and get great advice. They give me the real goods — they’ll tell me when my ideas are dumb. And they tell me when I’m being difficult, and they tell me when it’s time to give up, and they tell me when it’s time to hit the gas. I find that everybody needs their own little personal advisory board. 

When I think back to my very first job in tech, I was a product manager and I didn’t know anything. I’d never been a product manager before. I was not a software developer. I didn’t understand the technology very well. But I was so focused on wanting to be successful in this role that I knew I needed to wrap some really great people around me. And I just continued that throughout my career.

“This is a team sport. The idea that, even as a founder, that we have to do this alone is really flawed thinking.”

I’m always surprised when entrepreneurs feel that they have to do it alone. You know, this is a team sport. The idea that, even as a founder, that we have to do this alone is really flawed thinking. If you’re a founder you have your Board and your investors, and then later you have a team and customers, and you have partners and different investors down the line. The idea that we have to do this alone is so flawed. I think that’s really at the heart of what the A100 has been trying to achieve is, how do we allow entrepreneurs to grow and succeed and not feel like they’re alone. To get support and guidance, a fresh perspective, or just to get some moral support because, you know, it can be tough. 

Are there any particular books you’d highly recommend? 

I regularly have a stack that’s about three feet high. One of the books that’s actually back on my desk — which I’m going to re-read — is called “The Hard Thing About Hard Things”, by Ben Horowitz. He was the co-founder of Andreessen Horowitz and was a very successful Silicon Valley entrepreneur. There’s a lot of books that are written about functional things, you know, startup finance or what have you. But this is really about the stuff nobody talks to you about, like what do you have to do when you have to fire your co-founder? What do you do when the culture of your company has become toxic? What do you do if you want to steal an employee from your friend’s company? How do you decide where your boundaries are? There’s some great little tidbits about leadership and how you can be both an ethical and impactful leader during times that are not so rosy. I think we glamourize the life of entrepreneurs a fair bit and so this is an interesting perspective. 

“What do you have to do when you have to fire your co-founder? What do you do if you want to steal an employee from your friend’s company?”

And then I’ve always got a book going on sales. One that was really interesting to me that I read a while ago was “Predictable Revenue”. It was about rethinking your customer and revenue acquisition as systems building, rather than this desperate scramble to make your numbers, and how do you think of sales as building an engine of growth rather than just closing a deal? You know, I’ve had my own company where I wasn’t eating if I wasn’t selling. But the idea of really systematizing growth has been the curiosity itch that I’ve been scratching the last few years.

The other book that’s been transformative is “Radical Candor”. The idea of being very direct and very open — while not using that as an invitation to be unkind — is a real art form. I think many entrepreneurs get a lot of cheerleading advice that doesn’t do them a service. So how can you help people grow, and how can you ask for that feedback for yourself in a way that helps you to really learn, or share how you see a situation without being unkind. I think you can be very direct and still have empathy for what that entrepreneur’s going through.