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Create Structure from Chaos 

In this episode, we talk with Keri ​Damen, the ​managing director of entrepreneurship at the University of Toronto. Keri explains how she was in​$120,000 of student loan debt ​and in a job that wasn’t working, and how she learned how to find opportunities in her workplace to help overcome her debt and build a great career.

About Keri Damen:

At University of Toronto Entrepreneurship, Keri is dedicated to supporting the next generation of entrepreneurs and the entrepreneurship ecosystem across U of T’s ten incubators. She launched ONRamp, a co-working and event space for the U of T innovation community.

As the founding Director of Entrepreneurship Programs at MaRS Discovery District, Keri created a comprehensive suite of programs from inception to becoming Canada’s largest entrepreneurship education provider. The flagship program Entrepreneurship 101 won Startup Canada’s Entrepreneurial Effect Award for outstanding achievement in advancing entrepreneurship in Ontario in 2014.

Keri has an International MBA (IMBA) from the Schulich School of Business at York University and is an avid speaker about the new world of work and how everyone from new grads to leaders can use entrepreneurial thinking to survive and thrive in the new economy.

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Show Transcript

[Wilson]: So thank you so much for coming onto this interview, Keri. It’s a pleasure of interviewing Keri, the managing director of University of Toronto’s entrepreneurship program, which actually houses all 10 incubators at the university of Toronto.

I’m going to let Carrie do most of the talking.

Can you tell us a little bit more about what you do as a managing director of the University’s entrepreneurship program?

[Keri]: Thank you very much for inviting me and letting me tell my story. I’m delighted to be here.

I think as managing director of entrepreneurship, it’s not really a clear role in the sense of I know what my day is going to look like every day, right?

But I am building the entrepreneurial community across UofT. So whether that’s engaging new students to think about entrepreneurship, social entrepreneurship, maybe interning for us, supporting the 10 incubators that you mentioned, and making sure that they’re able to provide great programs for their startups to finding funding and other resources for incubators.

So I’m involved across all three campuses, all the faculties. I’m in a really exciting area of the university where we’re seeing a lot of demand from students that want to explore the area of entrepreneurship. It’s a unique area that cuts across every single faculty. And it’s really a way for students to gain skills and empower themselves career-wise. 

[Wilson]: That is crazy.

How does anyone get into a role like this? You’re basically teaching the entrepreneurs to become an entrepreneur and giving them all the resources.

And I know you have this crazy passion and this we talked a little bit earlier before the interview about your path being super nonlinear. And I know a lot of people our listeners are trying to do something that’s very inspiring and very ambitious.

Why don’t you share with us the story that you’ve been through to get to where you are today?

[Keri]: Well, I was an undergraduate in English and Sociology and then I spent many years traveling the world.

I’m very curious about other cultures, but most people would describe me as having no career direction. Although I think I was in denial about that and had a good time and was enjoying myself.

I thought an MBA was gonna solve all my problems was really going to help me find a job and figure it out. And, you know, not end up in this sort of job type scenario that they warn arts graduates about, which I totally disagree with. But that didn’t solve my problems either. I really still didn’t find the right fit for me.

What I find really empowering in my career was meeting entrepreneurs who changed my life. So I’m not an entrepreneur and I’m in an entrepreneurial world and I think that’s because I’m a good counterpoint to somebody who has big ideas. 

I can build things. They taught me how to have big ideas and build them. So having tremendous leaders and mentors has been kind of the way I got through being really uncertain about my career.

So when I talk to new grads nowadays, I say, you know, the metaphor of a career being like a ladder. It’s, really not anymore. I think the better metaphor is it’s like a jungle gym where sometimes you gotta reach across or sideways or backwards and it’s scary and awkward. But it will get you where you’re going. So you have to swing around a little bit and try a few things.

It’s definitely not what it used to be in the past, where it was linear and I think we don’t want it linear because things are changing so fast anyway.

[Wilson]: No, totally. That’s what a great metaphor.

I know you actually worked in and traveled across Canada, Europe, Australia, Japan during your travels to when you slowly found your way and met your first mentor. I know you were trying to figure out how to find your dream kind of career, but it never really existed.

Can you tell me a little bit more about that story?

[Keri]: So I grew up in rural Alberta and I never fit in rural Alberta. And we had foreign exchange students that worked on our farm from all over the world. I remember one of them was from Argentina and was running from a revolution. These situations they were coming from blew my mind to kind of want to explore the world and see what was outside of rural Alberta.

So I think this kind of curiosity for how other people thought about things and did things has continued with me and been very valuable.

I think entrepreneurs have to be quite empathetic and think about how the user will use their product or service or how the marketing will be perceived in a business or an organization to understand how you come off, is so important.

So seeing so many different cultures and learning languages was kind of a good baseline. But I didn’t know what at the time since I was just having fun.

And for me, my pivotal point was: I think I’m a creative and I went to business school and I didn’t fit in. But I think of entrepreneurship as like the art of business. It really is the messiest part of business, where you’re creating something from scratch. You’re operating in a total field of uncertainty and ambiguity. You have to organize and prioritize. It’s very difficult and you have to be very flexible and agile.

So I think where I’ve come to be able to do what I do is, I have enough business skills from my MBA, but I still have that creative side. I’m where I love to solve problems and think through issues and see things from different perspectives. But I didn’t discover that until I met a few strong entrepreneurial leaders. They’re the kind of people that definitely people love or hate. Very strong-willed, but they blew your mind. And I think they really, really pushed me.

Another pivotal point for me is I think I had owed like $120,000 in debt and I had gotten a job from my MBA. I got a job at MARS and it was the first real job I got in about six months. Then for various reasons, the job was going to fail and I had to write a report about why the job was going to fail.

I had to figure out how are I was going to make myself useful?

You know, having all this debt and having all this pressure behind me. The entrepreneur that I worked with at the time, basically when he hired me: given me about a paragraph of what the job would look like. It was absolutely unclear.

So I had tried to build something from that. It just for various reasons didn’t work. In the meantime, in a desperate attempt to keep the job, pay my loan, I started to make myself useful.

I filled in the gaps and took abandoned projects.

Entrepreneurs are very good at that, starting things but not continuing them. So they need to hire us, the right people to kind of execute. So what I did is pick up leftovers and improve on them.

One thing he said that was so powerful for me was he said, “you know, responsibilities not given, it’s taken.”

He encouraged me to take it a leap. So I basically created a department and started sending reports to senior leadership, which was kind of an upstart move. It worked within a few months.

They said this is a fantastic idea. Your new title is director. You’re going to get a team, here’s your budget.

And within a couple of years, I had a team of about 15 all-in and we had won Startup Canada award and had about 30,000 people watching it every year.

So that was my taste of fill in the gap. And the entrepreneurial kind of mindset behind that was, is a really powerful one for kind of anything in your life actually.

It’s seeing problems as opportunities.

Understanding that there will always be problems and if you’re able to figure out which problems to solve and in what order and that those problems, those gaps happen in any organization, to solve the gaps is how people get promoted. They start doing something that needs to be done.

But it’s also for an entrepreneur in the market. They’re trying to fill in a gap in the market, something that may be an unexpressed need from customers or maybe it is a need that they didn’t even know they wanted.

So seeing problems as opportunities, I remind myself about all the time.

As a manager, every day, it’s just a lot of problems and you think about where you come from and what you can actually do and what problems need to be solved

Another thing is just knowing that things that are really uncertain and scary, that’s where the growth happens. At that kind of edge.

So I remember being scared even after I had done all this at Mars, when I got this role at UofT, it was like build from scratch. I’m like, great opportunity. And they said, you have six months to open this space. It was still under construction at that time. We had to do everything. I had to get a brand, I had to put a sign on the wall, I had to do processes, hire a team, and I didn’t have a facilities person. I knew nothing about real estate or facilities.

I remember feeling kind of scared. Like I needed a facilities person.

Well, in the end, you just learn. We opened just in time. You just kind of have to roll with it cause six months is not enough but what can I actually get done? What can wait for later?

And I think that’s the kind of mindset I bring. To my team, I say, you know, give it a shot. You know, we’re not doing brain surgery here. We’ll make a process of, we’ll build something and try something for the first time and then we’re gonna come back to make it better next time.

And I know innovation is about the big ideas nobody’s heard of. But I think that can scare people off of innovation. A lot of innovation is also incremental innovation and just working harder, tweaking things, more listening to customers and just moving forward constantly.

People say I create structure from chaos essentially. Trying to figure out how to do that and once you’ve done it a few times, it gets easier, but it’s not less messy. It stays, it stays messy. So it’s definitely an art of business.

[Wilson]: Wow. You shared so many golden nuggets with us. That’s amazing.

One thing that really hit me is that when you actually entered this new role at university of Toronto, you still said it was still difficult for you and it was still scary. And a lot of people think that every one that is at like a really high level has no worries, no fear, no nothing because they feel they’re overqualified and stuff like that. No, I mean at the end of the day everyone getting into a new role and new project, there’s always a fear of the uncertainties and not knowing what’s, what’s, what’s the job holds for them.

So I think like, thank you so much for sharing this. I mean it’s very something that I personally can really connect to. 

[Keri]: Yeah. Growth is definitely at the edges.

People think, Oh, when you’re little, they think adults know everything and when you get older you realize that you don’t know everything.

As a leader, you have to know enough and you have to make quick decisions on the information you have. And then you have to hire a really good team. But I can’t possibly know and do everything I have to. I have to make sure I have great people, but I also have to have enough confidence to make decisions on sometimes limited time and limited information. So if you can handle being in that place of, of not complete certainty.

And I think this is the big transition from going from school, whether that’s high school or university to the work world, is that there are no answer sheets anymore. 

You have to figure out what are the most important things to do and how much time to spend on assignments and you can’t be perfect. If you have a good leader, you can ask those questions. But sometimes you have to work it out and it’s through trial and error. Just giving yourself the space to go a little bit into the uncomfortable place.

Like, I can see sometimes my team, they get a little nervous and I say, “you know, I’m here. Is it too much work? If you can’t handle it or you have any questions, just come, come talk to me, we’ll make it work. I believe you can do this. I wouldn’t give you something that I didn’t think you could handle.”

You know, they’re all new. They’re newly out of school. And I can see sometimes that they just haven’t been thrown into this uncertainty. When they come out of it, they’re just alive. They’re so pumped about what they can do and what they can achieve because they’ve sort of been awakened.

I call it surfing. Just stay on the surfboard, that is our goal. We don’t know what waves are coming, how big they are or from what side, we just stay on the surfboard. Just focus on that one thing.

[Wilson]: That’s, that’s crazy. Thank you so much for sharing like all these golden nuggets and all these such, and you’re such an inspiration.

If there’s only one thing that you can give as an advice or share some of your experience that is actionable right now, that our listeners who are in that shoe, in that pivotal moment where you were, where you felt lost or where you’re in debt, where you’re trying to figure it out, what does that one advice that you would tell them to do right away that would help them change and pivot this whole thing? 

[Keri]: So I think seeing problems as opportunities is really, really powerful.

If you look at the products around you that get launched and you ask yourself, why was that built? People are always filling in gaps and solving problems.

Another way to look at that on a people level. And this can be used with your family, your partner, your friends, or your manager is to ask, what are their needs and how can I meet them?

So I had somebody come to me yesterday that wanted advice on kind of a stalemate and their career. And I said, have you ever asked your manager, what does he need done that he doesn’t have time to do?  Or what are the gaps in the department? She tells me that they have asked him but he doesn’t have an answer. And I said, well, then you’re going to have to find, find the gap because it’s in the gaps where there’s the growth. People see potential beyond the roles that you’re already doing.

So a place for gaps. This is advice for people who want to jump on some rocket ships. I always say, go to LinkedIn, follow a bunch of companies, see what companies are growing really fast by looking at how many jobs they’re posting. Those are the kind of companies you want to work for if you want your career to go really quickly.

You can start in a startup, but not everybody necessarily can work without pay. Some people need to be paid. So it’s like, get with a fast-growing company because if you’re a can-do kind of person that solves problems and can face these walls of uncertainty and tries to figure it out, you will become invaluable. And your career will accelerate because they’re going to need a person like that.

I have hired a few of them in my career and I will do everything for them to get them to the next level. Like, trying to create another job to keep them, to make sure they’re getting promotions to giving them a team later. I’ll be doing what I can to keep that awesome talent because they are the ones that grow with the organization.

So my advice would be:

  • seeing problems as opportunities or
  • seeing the gaps and filling them in, finding out what the needs are and meeting them.

I think that’s not what we’re taught, right?

Like when you’re taught at school, they used to say, Oh, you know, you are a brand and you go to these interviews and you tell them, I’ve got these skills and I can do this and this is my experience. And it’s very one-sided. It’s kind of like if you went on a date and the person that didn’t ask any questions, they just talked about themselves. They’d be like, you’re kind of boring. Right?

But if there’s an interchange and you’re asking questions and they’re responding, then you feel like a camaraderie. I always say to people at the very end of the interview, ask questions. Like, what does success look like in this role, what are the three things that you’d like to see done in six months?

And when you hear their response, answer back on how you can deliver that based on your skill. So you’re using your skills to respond to what they’re saying, their needs and gaps.

I can guarantee you that people don’t do that kind of final sale at the end of the interview. Sometimes they commit the Cardinal sin of not asking any question at all, which just drives me bonkers because that’s their opportunity to shine and show. Be like, Oh, you answered all my questions. I’m like, you should have 30 questions so that you have at least a couple more that you can answer.

But the real trick is to figure out what are they looking for. Use your interview to ask a few questions, not just to talk about your side, but figure out what are they looking for. What are the three qualities that you are most seeking in a candidate? 

They say, you know, conscientious something, something you then you tell them and give them an example. Here’s an example and that’s a sale skill. So I feel like everybody is always selling whether they realize it or not. Smart salespeople are asking questions, just figure out what your needs are and then trying to come in and tell you how the product or service can meet those goals.

I know they tell people in universities to do your research before interviews, but you’d be so surprised how many people don’t. And that’s the same, I think just in business meetings. Just come more prepared. Spend 10 minutes before a meeting, guaranteed something you read, you’ll be able to use and you’ll just look really competent because a lot of people don’t do that. It’s kinda like the 20% that creates 80% of the results. It’s just knowing where to spend your time.

One last thing, I actually am a perfectionist. You asked me before we started, why don’t you go into entrepreneurship?

And I think entrepreneurs have really helped me become what I call it, a reforming perfectionist. I still have extremely high standards of quality. I do a lot of marketing, so that’s good in some ways, but it can be really paralyzing and when you want things to be in perfect shape but there’s no time for it. I think perfectionism try to control the results of something, they’re trying to reduce their anxiety and control the outcome. I think there is no kind of controlling of the outcome all the time, which is more my kind of surfboard metaphor of just staying on the surfboard no matter what happens. You just have to stay on, you’re focused on where you are right now and what needs to be done. And understand that if you’re really ambitious, you won’t have all the time to do everything to the standard you want. MBA was very good for that where we had too much work and not enough time and they try to beat out perfectionist tendencies in people. 

[Wilson]: Right, right. No, thank you. I think that’s, that’s a lot of things that our listeners can do right away is like seeing the opportunity and like actually seeing that gap. Whether it be for building their own career or building a service or product that is for a customer. It’s really about seeing that gap and listening to what people are looking for. For people that are wanting to build a business, I think this is great advice as well and really just being a little bit more prepared, like just that little bit.

That’s something that really resonated with me. So, so thank you so much for all this advice.

I mean, like for our listeners who do want to get ahold of you, do you have any contact information nor social media handle that you’d like to share? 

[Keri]: Yeah, I’m on Twitter at Keri Damen um, I think probably that’s the best way to reach out to me.

Thank you so much. It was interesting to reflect on my career. I think it we’re sometimes so busy doing and realize that somewhere along the way, all the uncertainties became something that if you keep going and look for opportunities, they are there.

And I hope that that well inspire your listeners too, to think through the opportunities that are around them and to grab hold of some of them to improve their to build a career.