Jeff Dennis, Entrepreneur in Residence, Fasken Law | Curiosity and the desire for lifetime learning | 36:12


DA: Hi, I’m David Abrams, and I want to welcome you to this edition of the Tenant Experience Network podcast. I want to welcome today’s guest, Jeff Dennis, entrepreneur in residence at Fasken, trusted advisor to the CEOs of fast growth companies, and author of “Lessons from the Edge”, a book which is a collection of stories by 50 entrepreneurs sharing their biggest mistakes in business and the lessons they have learned. In this episode, we’ll learn about Jeff’s journey to his current position at Fasken, where he combines his learning from being an entrepreneur, with his expertise as a business advisor and lawyer. We will tap into his thinking around curiosity, his desire for lifetime learning, and the ability to reinvent himself as his keys to success, and get a glimpse into what is top of mind for Jeff, as he continues to navigate through new challenges and emerging opportunities. We’re excited to be sharing this podcast with you, so make sure to subscribe so you never miss an episode of the Tenant Experience Network. And now I’d like to welcome Jeff to the show. Hey, Jeff, I’m really glad you could be with us today. How are you?

JD: I’m great, thanks. Thanks for having me on. I’m really looking forward to this.

DA: Alright, so let’s start with your journey to your current position as entrepreneur in residence at Fasken. Certainly, an interesting description right out of the gate. I would love to hear how you got started and what led you to this particular role.

JD: Yeah, I’m definitely the oddball at a place like Fasken. When I started there eight years ago, I think I was the only entrepreneur in residence in a law firm anywhere. It’s now become a bit of a thing. But my background, I’m a lawyer by education, practiced briefly a long time ago, started a business in the late 80s. I was in finance, we raised money from essentially high net worth people for various types of projects and investment opportunities. And after exiting that business after many years, like 25 years, I started working with early stage entrepreneurs, helping them share the things that I had learned and helping them launch businesses, scale businesses, finance businesses, and ultimately, I joined Fasken as their entrepreneur in residence. I wasn’t really looking for a job. I hadn’t had a job since 1989 and this was 2012, but I was looking for a place to hang out and I did networking and talking to people about, you know, “Give me an office, we’ll do this, you’ll do that.” ‘Cause I’ve always been very self-sufficient. Anyhow, I bumped into a buddy of mine at Fasken, and they were struggling with “how does big law do business with emerging tech companies”. Very expensive offices and fancy lawyers, and it was intimidating. And so I joined them as the entrepreneur in residence to help them figure that out. So my role is two-fold. I’m part intrapreneur, building a small business, they’re offering legal services to early stage companies on a completely different business model. And I’m part business advisor, sharing my network, sharing my experience, sharing my expertise, I guess. And then I guess, to a small extent I’m part lawyer, although I’m surrounded by lots of really smart lawyers who do a lot of the heavy lifting. So for me it’s just really been the perfect role. Eight years later, we now have over 40 lawyers across Canada, full-time dedicated to the space, I think we’re the leading firm in it. So it’s been a great pretty good run, and I’ve really enjoyed my time there.

DA: Amazing, well, as you know, you and I first connected, I heard you speak at the DMZ through their Sandbox program. And I was suitably impressed at the time, you and I connected immediately. As you said, you’re always willing to meet with founders, you met with me I think the next day, and within a couple of days I was welcomed into the Fasken startup program, and it’s been a great ride. So I’m really excited to have the opportunity today to delve deeper, and get to know you even better.

JD: Thank you.

DA: So why do you think you were uniquely suited to this opportunity? Are there any unique skill that have helped you to be successful?

JD: Well, I’ve had a lot of experience. I guess my strengths I would say are being very curious. Always interested in every business, trying to learn new things, lifetime Learning. So I’m just very curious and it’s something that drives me. Almost every day a new company comes through the door. It’s all new technology, solving problems with new solutions. And I’m just like a kid in a candy store, maybe I have ADD I don’t know, but that’s really something that drives me, is the curiosity and the desire to understand. And the other thing that seems to motivate me is a desire to help people, to try and solve problems, and to try and figure out the solution as people present them. I’ve thought a lot about what it takes to succeed in business, in life. That’s a big question. But I think that there are some life skills that people develop that help you, I guess reinvent oneself over and over again during one’s career. And that’s really what I’ve done. So it’s a big conversation ’cause I’ve actually been thinking about a book, or an online course, or something along that topic, as a sequel to my earlier book, “Lessons from the Edge”.

DA: So you talked about really wanting to be helpful to others. And I was probably going to talk about this a little bit later on, but I know that during this difficult time for so many people you extended an offer out to other founders, to encourage them to connect with you. And I wonder if you could just share a little bit of what that process was like and anything you may have learned from that.

JD: Sure, when the COVID situation arose back in March, like everyone else I was dazed and confused, and was sitting at home trying to figure out, you know, “Now what do I do? I’m the outside guy.” I’m out speaking, writing, doing, and trying to figure out how does one be relevant in that environment. And then it occurred to me, well, everyone else was dazed and confused. And I know from my own experience as an entrepreneur and working with so many, that it can be lonely at the top, that at times of crisis entrepreneurs don’t have a lot of people sometimes to talk to and go to. There’s well meaning people surrounding them, but if they haven’t walked a mile in their shoes they don’t really understand. You can go talk to your lawyer who can give you great advice, but they’ve never had to make payroll like this. You can talk to your accountant, same thing, your spouse, your employees, like some stuff you just can’t discuss with them. So who do you go to? So, a lot of people have their EO or YPO, form groups and tech and all these other things. But I knew that there was a lot of people out there twisting in the wind, who would just like someone to talk to. Not that I had any answers or thought that I would have any answers, but it was almost like business therapy. You know, “Tell me your story, how can I help?” And if it’s just listening, that’s help enough. But if I can share my network, or my experience, or whatever then so be it. And I think I helped a few people, certainly, just by giving them someone to talk to. But I learned a lot. Like for me it was just an incredible learning experience. Because in the midst of this terrible situation, I really had my finger on the pulse of the startup community. I spoke to over 60 founders in about three weeks, half hour sessions, Zoom like this, and just trying to figure out if there was something I could do to help them, or just talk it through or whatever. And what I realized that there was kind of a spectrum. There were the casualties and you know who they are, retail, restaurants, hotels, I mean just obvious stuff. And then there were a bunch of lottery winners, people who, vaccines, PPE, ventilators, E-learning, E-commerce, anything with an E in it was was a winner. And then everybody else was kind of in the middle. And my feeling about it at the time, and I think I’ve been borne out is that people had to pivot. If you stay standing still you could end up being a casualty. But if you found a way to become relevant and pivot in this environment and understand that this trend and the effects of the COVID will be certainly longer lasting than 60, 90, 120 days, then you had to make changes and that those people who came to the problem that way, were going to be winners and lottery winners too, hopefully. So that was really what I learned and I was grateful for it. So like anything else, when you give and you help, there’s always a benefit coming back the other way. It’s not necessarily linear, one-to-one, there’s a bit of a karmic element of it, where just things come back eventually. And I live by that.

DA: Alright, well, big shout out to you for making that overture and taking that time, and helping to invest in our community. And I know for me and for my team at HILO, certainly, you can’t you can’t invent opportunity coming out of COVID, it’s either there or it isn’t, but you have to at least be aware enough to see it, and as we’ve looked at our platform and how it can be more effective in helping our clients repopulate workplaces and invite people back to the workplace community and feel safe and secure, we know that for example, our platform has a role to play in that. So I think it’s where companies can find that unique opportunity. Not that any of us would have wanted COVID just for the sake of finding that opportunity, but I think when it’s there it certainly will help us move forward. When I think about your path, lawyer, entrepreneur, and now founder, and then entrepreneur in residence within that legal environment. Again, it’s certainly a unique path. If there were people that wanted to follow that path, any suggestions, any advice for them as they explore how those avenues can all intersect? 

JD: When I finished school, we were taught and socialized to think that you get this great job with some kind of corporation or government or institution, and 30 years later you’re going to get a gold watch and retire, and that was success. And it didn’t turn out that way for my peers. Some but not as many as thought it, and it’s not turning out that way for millennials. I mean nobody graduates school these days with that expectation. So it seems to me that the most important thing people can be is self-sufficient, and that’s the life skill, if you can figure out how you can always eat then the rest is easy. So that’s really been my approach is really trying to figure out how to be self-sufficient. Not rely on other people. If things end at Fasken and after eight years, because of a COVID, or retirement, or whatever, it doesn’t come as a surprise to me, that’s just part of life’s journey. So I come to it with that outlook, I guess number one. For me about 15 years ago as I was going through all these various reinventions and career shifts, or whatever you want to call it, pivots. I thought it was time to be intentional about it. So somebody had introduced me to a great book called, “Unique Ability”, by a woman by the name of Catherine Nomura. And that book had a big impact, I actually bought two copies, gave one to a coach. And he and I, over the period of about 120 days, we worked on me in the context of this book. And the idea is that we all have this unique ability. It’s your superpower, it’s your passion, whatever you call it. But the problem is that you become competent in various things that aren’t necessarily your unique ability. You go to law school, and you learn how to be a lawyer, and you can draft leases and contracts, and negotiate, and go to court even. But maybe that’s not your unique ability. Or you can go to business school and you can learn how to do accounting, and marketing and strategy. And so the more educated you are, the more intelligent you are, the more experienced you get, it becomes harder to figure it out, I think, at least it was for me. And what this book allowed me to do was figure out what my unique ability is. And it’s driven me ever since, every action and every career choice or decision has really been guided by that principle. And so that was helpful for me. And like I said earlier, I think lifetime learning and this curiosity ’cause I may be overconfident, or delusional, or something, but I really think that if you give me a set of problems I can find a solution. And if not me, I can bring in a team that can find a solution. So I have a level of confidence, I guess maybe it’s from age and experience, maybe it’s just delusion as some people think. But I don’t know. I don’t know if that answers the question. It’s a difficult question to answer. 

DA: No, really interesting. And we’ll talk more about influences in your life, but clearly this book was one of them. You just spoke about problems, and now you address those. So what’s the biggest challenge you’re currently experiencing? And how do you think you’ll overcome it?

JD: Well, I think this whole COVID business has really accelerated a lot of change that was in the pipeline. I mean, we live in this age of digital transformation. And it’s a revolution. It’s whatever the fourth, the fifth, the sixth Industrial Revolution. And I don’t think most people have figured that out completely. If you look at politics in the United States, for example, there’s 30 or 40% of the population are trying to turn the clock back, to make America great again as opposed to try and figure out what a great America looks like in the 21st century. And I think there’s a lot of people who haven’t come to grips with it. I think the biggest challenge of our generation is understanding how to deal with this exponential change. And humans adapt over millennia. And we’re now adapting exponentially quicker and quicker and required to do so. And that’s the challenge, I think.

DA: Very interesting. So if I gave you an extra $100,000, for you, your team, your business right now, what would you do with it? How would you spend it and why?

JD: I’ve always been a small budget guy.

DA: Well, I didn’t say I didn’t say 100 million, I kept it low.

JD: No, I know. But even at Fasken I was a bootstrap operation in terms of building this program. It was a bit of an experiment at the beginning, and so hiring me in the first place, and my salary was budget enough. And so I had a small marketing budget, but really, it was grass roots. And it was hand-to-hand combat, that speaking and getting out and volunteering. You saw me at the DMZ. That’s ’cause that was my budget, it was my time. And so I’m used to getting by on little budget. So I’ll start with that. But having said that, if I were to throw money at something today, I think it’s education. I think it’s training. I think it’s up skilling. If I was a leader in a business that’s where I’d focus, to create a culture where people are adaptable and agile, and to help them grow with your business. I think is key these days. And a lot of people are afraid to spend money on education and in business because they think that goes up and down the elevator, out the door, or could go out the door if you lose them. But I think that education creates stickiness because people really appreciate it, and it creates a culture. So I think that’s what I would do. 

DA: I love the notion of skill building. We’ve done that with our own team members and over the many years of being an entrepreneur myself, I’ve always tried to invest in those around me. There’s always that short term payback. And depending upon their length of tenure there’s the potential for long term payback, but when you also hear that the experience that you’ve helped them acquire, and or the knowledge you’ve helped them acquire, maybe two three years later has also helped them to leverage that and evolve their career, not always with you, but other opportunities. I think there’s still some gratification in knowing that you’ve helped them along their journey as well. So I think there’s payback all along the way.

JD: I agree.

DA: You about, my next question was all around resources, mentors, colleagues, or books that have helped you on your journey, you talked about a book that was hugely influential, just wondering, any other sources of influence in your world that have helped you to be successful?

JD: Yeah, I was lucky. I was a YPO brat. I don’t know if you’re familiar with the Young President’s Organization, but my dad was a member of YPO when I was a kid, so I was exposed to that organization and cultures at a young age. And when I got involved in business, I became a founding member of the EO, the Entrepreneurs Organization chapter here in Toronto, and became very, like I drank the Kool-Aid and got very involved, I was a leader here and globally, and my book, “Lessons from the Edge” came from that. And I was a sponge for all their content over many years, I must have attended 10 or 11 conference, they call them universities, and rightfully so. So that was really my business school and the speakers, and my forum group of founders, and the network that I built globally. It was huge just because of that organization. So I would say that was a big, big part of it. A lot of opportunities came to me from a lot of learning. I’ve read a ton about business, “Good to Great”, “The Rockefeller Habits”, “E-myth”, I’m forever recommending books to clients, so for me it’s been lifetime learning, and trying to understand and be curious. And there’s been a lot of mentors along the way who have helped me. So, people that I admire, people who gave me some advice along the way. So, yeah, I’ve been lucky that way I think.

DA: Well, I think building that network of whether be it content, or colleagues, or mentors, is so hugely important. And I know for me, during the last few years, as I’ve gone down this new path as a founder, I would not have been nearly achieved what I have today without creating that network. And for me that’s come much later in life, running a traditional business for the first part of my career, that mentality was not always as present. And I think we live today, particularly in this startup tech ecosystem with just so much support and resource, and a community that’s very willing to share and counsel.

JD: I agree, and you got to take advantage. And like I said earlier, things are changing so fast. So if you don’t lift your head out of your bunker, periodically, to figure out what’s going on in the world, it’s going to pass you by, so doing those kinds of things, being in the community, being part of a peer network, all that stuff is just critical.

DA: Yeah, I think it’s amazing to see all the different organizations that given the outcome of COVID have created these virtual learning opportunities. And now I have found, ’cause I’ve been a sponge for all of that, I found myself having to just really evaluate, and pick and choose more to certainly because there are just so many options. You could literally spend your whole day consuming content and information, and learning opportunities. So you really have to sort of pick and choose as we go forward. So just curious in your role, doing an entrepreneurial role in a traditional law firm, can you share any details about anything new that you’re working on, that you think our listeners might find interesting? 

JD: Yeah, thanks for asking. It’s actually a bit of a left turn. I started a side gig during COVID. I had some time stuck home, too much, watched everything on Netflix. So I started thinking about some of the learnings that I’ve had over the years, I think I mentioned earlier that I’ve reinvented myself many times in my own career. And I thought that I might write a sequel to my book about that, what does it take to be agile and adaptable? What does it take to reinvent oneself? As I said, a minute ago with all this exponential change, with the need to be self sufficient, I thought that there’s really something interesting around trying to figure out how to do that. And what is it that I’ve done and what is it that other people have done? So I’ve decided to build content around that subject to help other people. I’m thinking about launching a podcast where people can share their inspiring stories of reinvention. I’m thinking about a book, I’m thinking about an online course. And maybe some coaching program around that. I’m early stage on it and doing a lot of research and trying to decide, I’d written the book many times in my head, outlines and didn’t pull the trigger, ’cause self-publishing is a whole new ballgame. And you got to spend money to write books, and I find books these days are marketing devices for some other business. So, but I have all this content, and I want to figure out a way to share that. So I’m pretty excited about it, ’cause I think it is, there’s a real need for this, the people have to learn how to be, as I said, agile and adaptable and to be able to reinvent and pivot as I have. 

DA: That’s really interesting. And the need for reinvention can be triggered through so many different situations, some you self-select and some might be imposed. And I for one, I did not plan necessarily to start a tech startup, at a certain point in my career, I certainly was excited about the opportunity of maybe exploring new opportunities, and this path presented itself, but I love the idea of being more intentional in that reinvention. Your career could span 25, 30, 35, 40 years, its a long time. And to think about being in a position to take different directions and recognize unique opportunities, I think is a really exciting avenue to pursue. So I think there’s a real opportunity. 

JD: Thanks, thank you. Yeah, it’s funny, I’ve interviewed a bunch of people in the last month or so just to see, I guess, auditions for a podcast to see what people’s experiences are like. And I put out a call for people to share their stories and I’ve spoken to a couple dozen people. And they fall into two main categories. They’re either hit a wall or a glass ceiling, and something bad happens, pandemics, and they have to make a change and may be not be well equipped to do so, but it kind of forced upon them. And then there’s a crew that are very intentional, who are in the rat race, got the golden handcuffs, they’re called the cliches, but then look at themselves in the mirror and say, “Is this what I want to be doing for the next 20 years? Is this me, is this the greatest use of my time and energy and talents?” And they go through this kind of self assessment and evaluation and end up on a very different path. And I don’t know, I think in terms of the content that I’m creating, it could be applicable to either, although I do tend to think that there’s more self-sufficiency through entrepreneurship as opposed to just pivoting and getting another job. But that’s, each their own.

DA: You have a bias on the entrepreneurial side, but I don’t disagree. So, this is one of my favorite questions. If you could have one superpower, what would it be and why?

JD: Well, I have a superpower. My superpower is I’m just curious. And I’m always trying to figure stuff out, and it’s just I’m hard wired to do that. So I’ll stick with that. I really feel like it’s my unique ability to do this and to be an advisor to people, through channeling that curiosity. 

DA: Alright, well, that is a segue to the next question, which is all about curiosity. Now, I know you’re curious about pursuing this path of helping people to reinvent themselves. But aside from that, what are you curious about right now? And is anything that has you thinking differently in light of the current circumstances? And yes, that’s probably specific to COVID. But maybe in terms of how you engage with founders or the services you provide to founders, or just in the world, specifically around the tech ecosystem, what’s got you thinking now? 

JD: Well, I don’t know, I’m worried about, I’m just worried about recovery. I’m not that, I’m curious about what’s going to happen, ’cause I think we’re in a bit of a period where there’s a cushion because of the government programs and so forth. And I think that when that falls away, there’s going to be some real, more casualties that have been able to hang on, and I’m worried about United States, I just think that it’s a bit rudderless right now. And they’re focused on the wrong things and don’t really understand what’s important. There’s too much infighting, not really trying to find a vision for the future, and what what role, and they’ve abdicated so much responsibility on the global stage that, the entire global economy is reeling from that and then the pandemic. So I’m curious about how that’s going to play out ’cause I think it’s going to, Americans get a cold and we get the flu. And so I’m thinking a lot about that and I try not to get depressed about it. But it is a bit depressing, I’m really shocked by what’s going on south of the border, frankly.

DA: Well, you’re not the only one thinking about it. In our earlier podcast interview with John Love, the CEO of KingSett Capital. He also spoke about the role of the US globally, and as they have removed themselves and pulled themselves out of so many different organization, the concern about who fills that void.

JD: I agree with John. I heard that interview, it was a very interesting comment. And yeah, it’s really scary ’cause we need that kind of leadership. And on the other hand I think there’s great opportunities, ’cause somebody will fill the void. And so there’s opportunities, for example, because of the immigration situation in the US, for Canada to attract great people. We’re 35 million in a landmass that’s the biggest or second biggest in the world. So we got lots of room. So come on board, I mean, people that they don’t like we’ll take them, because I think there’s some great people coming from all over the world, engineers and all sorts of skills that can really help advance our economy.

DA: I think you’re right. I think we need to clearly as entrepreneurs, maybe we need to look at how we can, it’s not just about bringing more people to the same cities within Canada. I think it truly is about expanding the outlets, the number of places that we can really build that kind of infrastructure and those kinds of resources and give people purpose. And I think that’s the advantage that the US does have in terms of so many places that people can go and build great businesses, and build great careers, and have families, and I think that is one of our limitations on this side of the border.

JD: Yeah, I mean, I think, listen, if you look at entrepreneurs, they’re always immigrants. They don’t fit into the normal institutional lifestyle. So immigrants have to figure it out and they solve problems, and most of the great success stories are all immigrant success stories. So you want great immigrants. I just don’t get it but anywho.

DA: I agree. Is there anything you wish you had known when you first started out? We always learn a lot along the way, but anything that would have been helpful to have known then.

JD: It’s a lot of stuff. I wrote a book, there’s 50 stories, 50 lessons in my book of mistakes that entrepreneurs make. I don’t know, I guess, I was a bit of more of a risk taker as a younger man, and if I could have done it differently, I would have maybe taken less risk. Or maybe taking more chips off the table. As a young man you tend to roll the dice a lot and I did. So maybe that was a lesson learned, save more for a rainy day ’cause they do come for sure. Look what’s going on now.

DA: Yeah, we’ve seen that.

JD: So that’s a good lesson is, a lot of entrepreneurs don’t pay themselves first, they’re growing the business, and they’re begging, borrowing, stealing, to try and make payroll, and get going, and feed the burn rate. And they tend to pay themselves last. And so it’s ironic because it’s supposed to be the other way around, more risk means more return. But maybe there’ll be return down the road, but you’re taking a lot of risk. And so you should take care of yourself a little bit. And that was a lesson I learned later.

DA: Yeah, that when I wish, I certainly took a lot of counsel in my early days as I began to start my startup, but I didn’t quite realize how you prioritize yourself last. So that’s been a bit of a learning process. Now, I’m not sure it would have changed anything. But that is life as a founder and the ecosystem in general, it continues to support that line of thinking.

JD: Yeah, you just got to be smart about it. And yeah, remember why you’re doing it. People are in business to provide for the economic well being of their family. That’s the point. You’re not building, yes, we’re solving problems. Yes, our egos get involved, but at the end of the day you got to provide for your family, that’s the bottom line, it’s the bottom line. 

DA: Well, I agree. I want to thank you, Jeff, for taking the time for being with us today. I continue to value our friendship as well as your professional role that you provide through Fasken for our firm, and we’re glad to have you by our side, and I look forward to continuing to collaborate, and investing in this amazing tech ecosystem, and seeing what comes from it all.

JD: Oh, it’s been great. My pleasure, I really enjoyed this. Thanks for having me on. We’ll see you soon.

DA: You bet, have a great day, bye now.

JD: Bye bye.

DA: I want to thank Jeff Dennis for joining us on today’s podcast, and for sharing his journey. From early beginnings as an entrepreneur to now leading the team at Fasken, with over 40 lawyers across Canada, dedicated to the startup space, a great learning for all of our listeners, and an opportunity to gain insight into what it takes to be an effective leader. Please be sure to tune in again for future discussions with leading professionals and industry experts who all have something to say about experience in the built world and the impact that technology is having on the largest asset class in the world, commercial real estate. If you or someone you know would like to be a guest on a future episode, please reach out to me directly at And until our next episode, I wish you all continued success in building community where you work or live, thank you.

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In this episode, Lisa sheds light on key market drivers influencing real estate decisions, such as the rise of amenities and spec suites. She describes the future of work as “accommodating employees with great space.” The impact that unique community spaces have on potential tenants as they are touring prospective spaces is something else she sees in the market.

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