In this episode, Laurie Bennett sits down with Rory Capern, COO of Redbrick, to reflect on a decade of building and evolving a thriving business. As Redbrick has grown from a single-brand tech company into a portfolio of digital businesses, Rory has seen firsthand what it takes to scale with purpose and lead through change.

Together, they explore the lessons learned along the way—the leadership qualities that sustain long-term growth, the challenges of navigating uncertainty, and the role of culture in shaping a resilient, innovative company. Whether you’re a business leader, entrepreneur, or someone passionate about growth and transformation, this conversation offers valuable insights on what it takes to build a business that lasts.

Learn more about Within People and the work we do here.

For more information about Redbrick and the work they do, go to rdbrck.com

Hello, listeners.

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Welcome to another episode of

Reimagining Work From Within.

3

I'm Laurie, and I'm

based in Vancouver, bc.

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In this episode, I welcome Rory Capin,

COO of Red Brick, a Canadian company

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that builds and acquires software to

help entrepreneurs unlock greater growth.

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If you've been in a growing tech

company in Canada in the last couple

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of decades, you may well know him.

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If you don't, well, frankly, your loss.

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Rory is a broad-minded, big-hearted leader

who has a storied career in Canadian

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tech, occupying leadership roles at

Microsoft, Google, and Twitter Canada.

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Then as an advisor to VC-backed

startups, and now as COO of Red

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Brick, where I've had the pleasure

to know him as a within client.

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Through all those chapters, Rory's always

been focused on driving growth, which

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made him perfect for this conversation.

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We explore the evolving meaning of

growth, the role of leadership in

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shaping it, and how unique it is

that red brick approaches growth as

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a choice rather than an obligation.

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Let's jump in.

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All right.

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Hello, Rory.

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Rory: Hi, Lori.

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How are you?

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Laurie: How are you doing today?

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Rory: I'm well.

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Glad to be here.

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Thanks for having me.

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Laurie: It's my pleasure.

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Rory.

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We met Almost exactly a year ago.

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in a really remote, wild part

of British Columbia, Canada.

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I was actually, I think

kind of almost sort of.

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Para dropped in there from a float

plane and interrupted you halfway

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through your meal, but what an

amazing spot that was up at Nemo Bay.

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Rory: I was so pleased to

have you join us there.

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I was having what might have been

one of the best trips of my life

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in that short period of time.

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You know, I was a little

jealous of you actually.

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My thought.

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was like, this guy's got one of

the best gigs in the world joining

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in this place, which we get to do

like once every couple of years.

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What a cool experience.

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that for us was an opportunity, I

think, to really, be inspired and

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kind of amazed by how beautiful

this part of the world is.

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And that particular resort is just such

a small scale, such an incredible place

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to be and just kind of live and enjoy.

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And then to be able to crack into

the conversation that we had was.

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Exactly what we were hoping

for, which was transformative.

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we've gone forward from that

conversation a year ago.

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I can't believe it's been that long,

that really did chart a new course for

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how we're thinking about our business.

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so first, thank you, and second, what

a cool gig to be able to come to places

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like that and do this kind of work.

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Laurie: Yeah, it's easy to say you're

welcome for that one, I have to say,

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it's not always, life as a culture

strategist is not always that glamorous.

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And I think maybe you are

upselling it slightly.

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'cause I think one of the first things

we did was drag you out into the rain

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and make you sit around a fireplace and

contemplate what success means to you,

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thought you did tremendously well to be

game to go and sit in the May, drizzle

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on a pier in the middle of nowhere.

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And think about your future.

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Rory: Laurie, the work is hard.

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I distinctly remember a glass

of scotch involved in that

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conversation, which helped immensely.

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Laurie: There you go.

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You see, that's just customer service.

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I don't think I had anything

to do with it, unfortunately.

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But those conversations that we had

and the kind of spark of you and I

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getting to know each other and me

having the real joy of hearing your.

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Stories around growth.

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'cause that was really our context

for that conversation was what's the

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next phase of Red Brick's growth look

like and where do you go from here?

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And how do we have a, maybe a

different kind of conversation

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about what it means to think about

how you want your company to grow.

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the people sitting around us at that

time were your fellow owners shareholders

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in red brick, and this was really

an opportunity to contemplate what.

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What would be most meaningful about

growing from this point on as red brick,

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which is a real privileged conversation

that I get to have with folks.

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I really appreciated your perspective

that you could bring to that

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conversation, given the variety of

different leadership roles that you've

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sat in, with an emphasis on growth

in each of them, from your time in.

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Microsoft and Google and being the MD

of Twitter in Canada, your perspective

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on that was super interesting and I was

just hoping maybe you could start out

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by taking us on a little journey of your

journey to that fireside in Nemo Bay

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and how growth has shown up for you.

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Rory: Totally.

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it's a conversation.

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I don't think I'll ever forget, really,

not just 'cause we're talking about

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it on the podcast, but it was a very,

clear moment for me of appreciating the

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difference of where I was sitting at

that time versus where I had come from.

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The first, 25 years of my career were

spent predominantly for public companies.

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Namely, very fast moving aggressive public

companies looking to do huge things.

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Mostly mission-driven in the pure

tech space, but all at a point of

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maturity where the pressure on growth

as a public company was unmistakable.

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My upbringing through all of these

companies came in sales revenue generation

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and partnerships, very specifically

attuned to the goals set on our behalf.

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In the business the need to achieve

them at incredible expense of time

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and effort and sacrifice and, all

the things necessary to do that.

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The reality of my experience as I got

to Twitter, things got much more senior

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in the context of being on a global

leadership team and seeing how the sausage

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got made at an intergalactic level for

a company like Twitter how these revenue

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plans come together who's responsible for

what and why, and how they do that stuff.

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At Google, my role was much more regional.

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across a whole bunch of different business

units who did it differently, but the

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consistency in that experience was really

one of, here's your number, go hit it.

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And we're hiring you and your

team and giving you these

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resources because you're smart.

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and we'll help you, like, there'll

be some narrative from on high

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that you'll have to work with

within some reasonable boundaries.

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But like, go get it.

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Do it now as fast as you can.

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And if you have problems, tell us early

because we have to hit that number.

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And interestingly enough, as a guy who

pays a lot of attention to finance and

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how the markets work, there's this usually

unknown set of analysts out there that

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set that number for you in a weird way.

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Like you, there's guidance

and all that stuff, but market

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expects you to do, X number is

set at, y, quotas are set at Zed.

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If you want to eat this

quarter, hit your number.

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right.

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Goes through from a revenue perspective.

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And then, so I went from that.

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To advisory business that I started

specifically focused on fast moving

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tech companies that were predominantly

venture backed, not public but with

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this incredible expectation of growth

following an investment of a lot of

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money, the calling card was classically

from a founder saying, we just got a

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very large check from a venture capital

company and we need to stay off the wall.

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Or the venture capital company saying,

we just put a very large check into

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this company and we need you to

keep the founders off the wall and

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help them grow in a way that isn't

gonna create existential issues.

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But by the way, the target for growth

is like, you can't even see it from

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where you're standing right now.

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And you have no time.

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Like you have to do it tomorrow

and you have to hire a team.

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And if you don't find your customers

and figure out what markets you're gonna

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play in don't take a breath because

to hit that goal, you have to grow.

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It's like depending on who you talk to,

triple, double in the first three years

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of a venture business, 300%, 300%, 200%.

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the growth pressure on these companies at

this stage is so intense and it's fun and

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you know, you get a lot of opportunity to

kind of steer the ship, but the question

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of where were those numbers set was

something that happened a long time ago.

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On the back of extraordinary expectations

in a game that a lot of the venture

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capital community is playing to find

breakout winners moderate performance

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across 10 or 15 investments doesn't

cut it incredibly outsized returns

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on one or two of those investments

is necessary to make the formula work

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and a whole bunch of other people

just don't make it in the process.

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There's this extreme growth pressure and

existential threat kind of all the time.

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I love this game.

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I've worked with some incredible founders

to navigate through that and learned a

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ton about what the inner machinations

of these businesses are in the process.

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But there was always this one company that

was just a little bit different in the

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context of how they thought about things.

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And, that was Red Brick

and Tobin and Marco.

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in a fractional business

like I had, working across a

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number of different companies.

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You make choices about where you

allocate your time, and I just

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found myself gravitating further and

further towards this red brick work.

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Part of the reason was

exactly what you described.

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This is a much more carefully controlled,

purpose-driven, thoughtful business

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that's doing exceptionally well,

like it's a very successful business.

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But at that conversation you hosted, the

question that was asked for the first

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time in my life, I've been doing this

for 30 years, was, why should we grow?

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It hit me.

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I think you saw my reaction.

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It was like being hit by a lightning bolt.

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this has never been a question

that I've received before.

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Why grow in the public company case?

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Just grow like, here's the number, hit

it in the venture case grow because you

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have to, to make these numbers work.

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And now this question about,

what direction should we

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grow and how should we grow?

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How much should we grow?

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These are not questions that I was used

to in the tech space, red Brick is one

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of the most tightly run operationally

focused businesses you're gonna find

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out there, and yet had this totally

different mindset around growth.

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And it was a real unlock for

me on the power and potential

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of the company that I had found

myself in around that incredible.

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Fire in this beautiful place, but also

started to tap on a lot of the questions

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that I think we're here to talk about

today, which remove that outside impetus

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on just grow because, or growth at all

costs, and add this layer of intentional

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growth and growth for a purpose.

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And it was a very unique experience

for me to be asked as the guy who's

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generally responsible for driving that

revenue, how much should we grow and why?

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it was like, wow, you mean

we can go wherever we want

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at whatever speed we want?

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that's different.

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And it's been super fun to work

on this purpose with you and

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particularly with Marco and Tobin

who has sort of the key partners in

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the business just think differently.

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Right.

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I think you first saw it with Marco

Marco spends, as much time thinking

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about sustainability and, our B Corp

certification and you know, what we stand

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for in the world than he does about how

profitable we are or how fast we grow.

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He thinks a lot about both by the way.

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Like it's not like he doesn't

think about profitability.

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I was thinking a lot.

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In fact, I think Marco's main focus is on

this interplay between the two of them.

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Like how can we be both?

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this is one of the things you helped us

to nail as a question and continue to

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answer as a really important question.

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And then you have Tobin who's very

focused on the authorship that we

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have in this business around how

we can decide to steer ourselves.

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It's taken a lot of interest in making

this business what we want it to be,

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for the reasons that we want it to be.

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That and, it's very inspiring

and, you know, being at Nemo Bay

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didn't hurt anything either.

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Laurie: I love to hear you say that, Rory.

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And I think for me, it's such an

interesting, almost incremental journey

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in some ways that you've been on from

the public companies where you're

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never asking, why are we growing?

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You just ask, how are you gonna get there?

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I think that the VC-backed companies

where the question of why are you

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growing is, as you say, it's existential.

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So it's not really a que it's rhetorical.

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If you don't grow, you die, which

is a focusing energy, at least

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in an organization, But just

even listening to you tell those

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stories felt exhausted by it.

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how do you as a leader in

those environments where.

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the consequences are so high and the

pressures are high, and you don't

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necessarily get to bolster your energy

With what you've been talking about in

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intentionality and meaning and some of

the things that we've come to think are

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important about growth, what does it

feel like growing in those environments?

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Like what, from your perspective,

do you sort of remember?

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Is it.

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Fond memories of knuckling

down and getting things done?

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Or is it the burnout that we hear

about so much that seems to be an

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almost essential part of running

and growing a fast tech company?

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Tell us, take us into your

world there a little bit.

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Rory: Yeah.

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Well, the answer is yes

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to

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both.

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Lemme start on, the

positive side of it all.

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First of all, I think like most

hard things, you have to love it.

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There's a joy that comes just in the

challenge itself of being able to try

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and stay ahead of or on pace with a

business that has enormous ambition.

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And so to describe it as drudgery

would be a mischaracterization.

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I've really loved the work.

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The stress and pressure of

it is no question there.

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There's a reason why my beard is white

and I've got silver on the side of

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my hair But I think I've been very

fortunate in my own experience to be

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working in really unique environments.

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the feeling of working at Google

was being surrounded by Olympic

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class athletes all the time.

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they're just incredible

people to do it with.

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And so when you're faced with a

challenge like that, growing at

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this incredible pace, quarter

after quarter, after quarter.

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To have great people around you makes

it very inspiring fun and interesting.

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And the challenge is

part of what drives you.

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The other thing I would add

is, for the most enjoyable and

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successful, chapters of my career.

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The mission piece was important

in public companies and venture

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backed businesses as well.

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It's easier to dig deeper When you

ask people to dig that deep and work

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that hard to hit these goals, to

have a mission to strive for that

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you align with makes it way easier.

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You're not swimming against the current.

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In that context, it feels like you

just have to swim faster with the

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current, which is really important.

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And I think that's why mission

driven companies do better than

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non-mission driven companies.

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but being out of control

is part of the game.

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I mean, unless you're one of the four

or five people that sit in the top of

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the ivory tower, you're mostly taking

instructions and, sprinting after it.

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when you have to work that hard

against a mission that is understood

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at a relatively amorphous level, you

know, do no evil is not what we were

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living by at that point at Google.

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But that's pretty amorphous.

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And then like organizing the

world's information and making it

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universally accessible to everyone.

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It's not really that resonant when

your goal is to hit a massive ad

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revenue target for a quarter, right?

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the best in the world.

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And I would put Google as absolutely

the best in the world at this, is

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actually anchoring the individual team's

contribution to that mission in a way that

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makes it inspiring, but no less stressful.

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I mean, damn, you gotta hit your number.

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So there's a lot of pressure that

goes into that, the difference as you

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work in a really big company versus.

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A medium-sized company versus a small

company is the understanding and the

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notion of control and authorship over

what these targets are, so that as you

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have to sprint after them, you have

context for why they are what they are.

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If you look at a company the size

of, of Microsoft or Google at like

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north of a hundred thousand employees,

it's a daunting task to make sure

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that everybody knows how their

work contributes to some top line

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result or mission or, or whatever.

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And, and I think that that

adds stress to the individual.

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They feel out of control.

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They're asked to work really hard.

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They don't always know why.

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You just have to kind of do it,

and that adds a level of stress.

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If I take that same idea to

the venture world also awesome.

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Like so cool, smaller, the best part

about that business for me was the

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quality of the individuals that I got a

chance to get really close to as founders

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So there's, you're a lot closer to

the engine room in the context of

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how we're going to get somewhere and

how we're gonna grow at that pace.

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The pressure that gets added there

is that It seems like sometimes

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you can't see the top of the

mountain from where you're standing.

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there's just so far to go so

fast without having a real

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clear map of how to get there.

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And let's be honest, as a guy who's

paid to write maps a lot of the

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time, there's only so much clarity

you can get over a three year period

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in a business that moves that fast.

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And that is where the stress

and pressure comes from.

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How are we going to do this?

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As a leader in a business like that to

face your team and say, we will do it.

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I have a lot of confidence

in the people that we've been

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able to bring onto this team.

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I don't have all the answers, but

I have a lot of confidence that

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we'll figure it out as we go.

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that notion of putting the plane

together while it's in the air is very

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true in a lot of those situations.

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That's where the stress comes from.

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And on a personal leadership

level, at a team that small.

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These people have mortgages

families and bills to pay.

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the thought of not making it, of not

being able to deliver on the promise

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of the mission of the business and

how that would personally benefit

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everybody involved is enormous and

makes it really hard to sleep at night.

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Also explains why there's white, my

beard and gray in my hair, right?

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So there's a lot that comes from this

external pressure of not being able to

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set the bar and not having the answers

for how to answer those questions

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and needing to inspire confidence

in a world where there's not a lot

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of confidence organically available.

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it's challenging.

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It's fun.

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I don't want to paint the wrong picture.

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nothing hard is easy, but

it's, pressure filled.

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You kind of have to love it to stay in.

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I've been doing this for 30 years.

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I'm either crazy or good at it, I guess.

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. Laurie: Well, you're grinning

as you as you say it.

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Right.

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I can see that there's a fondness

of talking about sort of that

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environment and what's there.

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And I'm curious where does

that come from for you?

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What makes that pressure and that ability

to bring confidence maybe when you're

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not feeling it for yourself all the time?

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For a group of people to be able

to support them in understanding

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what this growth means, what their.

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energy and their own stress is translating

into how do you work with that?

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Rory: it's been done, right?

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Like when I was at Twitter, I had a huge

amount of aspiration for Adam Bain, who

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was the CRO, who had brought the company

to, I think it was a billion in revenue

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faster than any company had ever hit it.

343

And when those benchmarks are out

there, and you know, the people

344

who did it and have some idea

of how to do it, It's inspiring.

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It's been done.

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It's not like it's impossible.

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this is not trying to land on the sun

or something crazy that people have

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talked about but have never done it.

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You know, it's doable.

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You can do it.

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And I guess the other piece of that,

and this is speaks to a very, you know,

352

personal perspective, is if not me,

then who I've got unique experience.

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I'd like to consider myself pretty battle

tested if I can't do this, who else can?

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And if we can find them,

bring 'em in, let them do it.

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that does bring joy.

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I think the other piece to this,

I keep coming back to mission.

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I worked at companies that didn't

have a very strong mission and it

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was kind of soul destroying, right?

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the purpose of this business is to make

somebody that isn't me a whole lot more

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money than we're seeing come in the door.

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and that's hard to grind

against and really inspire

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the people around me because.

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That's a hard story to tell, right?

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the ability at Twitter to have people

aware of what was happening in the moment.

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Give everybody a voice, give this

incredible potential of communication.

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That's a whole other podcast.

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Laurie: I won't ask you about

how you feel about that now.

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Rory: Yeah, exactly.

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super inspiring.

370

Right?

371

the mission itself is often what

you grab onto to find the inner

372

strength, the depth, the ability to

dig deep to make these impossible

373

things happen because it's worth it.

374

Because if we do it, this

great thing will happen.

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Whether it's making sure my

mom can find everything she

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needs on the web at Google or.

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Putting a really important communication

tool in the hands of people who are

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in dangerous positions and don't have

another outlet, these are really important

379

things we did in these technology

companies to provide that functionality.

380

Again, sometimes hard to see when

you're trying to hit, you know,

381

sales quota on an ad revenue target,

but knowing that becomes the fuel

382

for this outcome is where a lot of

strength comes from, at least for me.

383

And it provided me the opportunity

to turn to my teams and say,

384

if we do our part right.

385

This is what the fun part about being

Canadian at a time when it really matters.

386

Inside those businesses, we were able to

position Canada as kind of a lab, right?

387

if we do our job well, we will be able

to let these companies do a better job

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in larger markets because Canada has all

these really unique facets as an economy.

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We can tap into that.

390

And we did and it worked.

391

And we gave Canadian tech people

working for an international company,

392

at least I'll speak for myself

and the team that I had around me.

393

Super inspiring to be able to put

Canada on the map that way and to, have

394

these incredible people perform at this

incredible level on behalf of a country

395

environment that we'd sort of found

this unique and special capability for.

396

So there's inspiration in that,

but there isn't a lot of control.

397

Laurie: what I hear in there, you

mentioned this concept of authorship of

398

who's holding the pen that writes those

missions down and those things that guide

399

you isn't you in those conversations.

400

especially in those stories where you're

starting to kind of connect this back

401

into being a Canadian business and,

the group of people Working with you

402

in service of this inspiring mission.

403

Finding places to pick up your pen and

author parts of that story that help

404

people find what they're passionate

about, and bring that into the work

405

they need to do under sometimes

extremely challenging circumstances.

406

what happens, you know, you step out of

those businesses and into the VC space and

407

then you arrive at red brick and sit by a

fire with me, and I hand you the pen and

408

say, well, now write down, be the author

of this growth story how does that feel to

409

get to now be able to bring choice to that

conversation rather than kind of finding

410

the best way to meet an obligation?

411

Yeah, great question.

412

The first answer I give you

is incredibly inspiring.

413

It's almost like another

level of business, right?

414

It's almost like a, like a

different sport, if you will, right?

415

There is a profound difference between

being told what must be done and.

416

Taking the pen and writing down

what we want to do and why.

417

it's an entirely different

dynamic and I love it.

418

It's, incredibly powerful It's

also in the same breath, daunting.

419

It's intellectually challenging

to have to answer these

420

questions, where prior I didn't.

421

I could face my team and say,

I didn't make the number up.

422

You know, guys upstairs made the

number up and we just gotta hit it.

423

Right now, I make the number up.

424

There's a responsibility

that comes along with that.

425

But even more powerful than that, is

something that we've been working on

426

a lot, as you know, is tying it to

a purpose that isn't the number the

427

number is a byproduct of a purpose.

428

Which is a very different way of thinking

about business from this perspective.

429

And when you tap into the why of a

business, you answer a whole bunch of

430

questions that otherwise as a, fast moving

tech exec, the mission was given to me,

431

the target was given to me, serve the two.

432

And now we get to write down and figure

out the mission and the right pace

433

for the targets to get to the mission.

434

But the mission comes first.

435

the really important insight for me and

anybody from a background of intense

436

business is you get to do that when no

one is telling you what you have to do.

437

to get to that stage, you

have to be profitable.

438

We are in perpetual motion because

we are viable as a business the

439

way that we're currently operating.

440

then you get to make choices

about how you grow from there.

441

that condition.

442

Is critical.

443

One of the reasons why the pressure is

so intense in venture capital is most of

444

the time the company is not profitable.

445

you're burning someone else's

money and they're setting the pace

446

for, where growth has to happen.

447

And in a world where you are

profitable, we could just stay the same.

448

In fact, we could decline

a bit and we'd be okay.

449

no one gets hurt.

450

And then if we want to grow, we have

this great intentionality this is where.

451

I think this sort of purpose discussion

gets so interesting because it does

452

serve as a divining rod for where we're

gonna go with a very solid understanding

453

of what we're trying to accomplish

and how we're trying to accomplish it.

454

We can set far more intentional

goals that feel much better to

455

communicate to the business.

456

I'll speak for myself and say this

unique capability to actually author.

457

The strategy of a company, the

goal of a company, the purpose of

458

a company is incredibly fulfilling.

459

I hope it resonates out

into the entire company.

460

All of the Red Brick employees and

all of our businesses are hopefully

461

feeling this sense of, we're on

our own path here because we care.

462

Well, and they get to be in the

position you are in to some extent.

463

it's interesting to reflect on,

those numbers that you put out.

464

I know you think very.

465

Thoughtfully now as a group around

what that number is and what it

466

means, not just for the speed of

growth of the organization, but

467

for the quality of the experience

of the people who are part of it.

468

I think there's something really

powerful in folding that, in

469

sort of giving that number.

470

Meaning doesn't just translate

into, well, how big will we get?

471

But rather, how's it gonna feel?

472

For the people who are on the

journey with us to get there.

473

And that matters.

474

The people are not an expendable resource

that we must use to get us to the top

475

of that mountain you talked about,

but rather being on the journey with

476

them as part of the joy of doing this.

477

And I think even in your stories so

far of the work in those companies

478

you've mentioned, the people you work

alongside and the quality of them so

479

much, it makes sense that that would be

something you would choose to invest in.

480

Rory: I think in our case.

481

one of these profound moments that

come from an exercise like the one you

482

described and everything we've done since

is when you realize that the output of

483

the business isn't only the profit that

it drives, it's also the experience

484

of the people in the business they're

living great careers enjoying their lives

485

and we're not burning people out they

feel great about what we're doing, and

486

they're doing all this extracurricular.

487

Benefits work and when that becomes

a goal, you behave differently.

488

You're more mindful of what kind of a

culture we wanna create and, and how

489

to go about creating that culture.

490

Not something that is separate

from the core operations of

491

the business, but an essential

ingredient to the business itself.

492

and the judgment that outcome

is something that we look at.

493

Individually and in the context

of, of all the other outcomes

494

things like B Corp certification,

set a higher bar for that right?

495

So what benefit do we have to

create and how do we measure it?

496

How do we make sure that

we're delivering it?

497

That then puts, what used to be,

in the old school business world,

498

the cart before the horse, right?

499

only when you became super profitable

did you think about doing things that

500

were for, charitable causes or whatever.

501

Now?

502

You've set a goal, like you've gotta do

that regardless of what else happens.

503

You've got a objective

that you have to hit.

504

that changes the story.

505

It changes the conversation internally.

506

And, , it's also very inspiring.

507

It helps with this idea that the

mission isn't just this heady objective

508

we're talking about, which might be

an output somewhere down the line.

509

You, tie that to a whole

series of objectives that

510

are not financial in focus.

511

That are also being hit along the way and

the satisfaction that comes from that.

512

And especially in a world where you

can do both and you realize pretty

513

quickly that they fold in on each other.

514

The better you do those things,

the more the flywheel starts to

515

turn, the more inspiring it becomes

and the more effective it becomes.

516

Ironically, from a financial perspective,

which then allows the reinvestment

517

in all these things It's kind of

hard to imagine that we didn't do

518

this in the first place everywhere.

519

Laurie: I guess I'm curious in that sense,

like you're talking my language for sure.

520

I sometimes think that in the VC

space that's a tough sell, right?

521

And there's that sense that we've

touched on before around, authorships

522

all well and good, but when you're

profitable, let's talk about that.

523

But even in Red Brick's case, there's

some intention that's been there In

524

conversation with Tobin and Marco through

this process, there's an understanding

525

of choices that they've made not to go

down that path, which have been quite

526

intentional and that sense of being able

to maintain agency over their destiny

527

and keep that choice at their heart.

528

I know there's been wins and losses

along the journey and moments where.

529

They've been able to indulge

themselves more in being choosy

530

in times where they haven't.

531

But there's something in that that I

think is important because I think there's

532

sometimes an assumption that founders

who wanted to grow their businesses

533

don't get the luxury of that choice.

534

I think that is a choice in and

of itself at the beginning I

535

guess what I was curious about was

now when you look back into the.

536

Businesses that are being backed by

VCs, what might you tell them about this

537

kind of approach that introduces that

sense of agency into their world where

538

they don't feel like they have to be on

this pathway to the top of a mountain

539

they can't see, tripling, doubling.

540

what changes in that conversation,

if anything, for you?

541

Or is that it's, that's a choice.

542

And if people wanna make that

choice, that's the way they, they go.

543

it's interesting.

544

I think, in the last three or four

years, the knowledge that it is a

545

choice at all in the first place

is new especially in tech where

546

there was this like, you're nothing

until the venture capital community

547

wants to invest in your business.

548

And that's a whole other story.

549

But the narrative that says, well

actually we have a number of choices.

550

We could bootstrap this thing

with the money that we can

551

find in our couch cushions.

552

Which usually comes with the cost of time.

553

It's just gonna take

us longer to get there.

554

or we go the venture capital

route, or we try and find bank

555

debt at some period of time that

isn't the same as venture capital.

556

there's a bunch of different path angel

investors, and I think we just went

557

through a period between 2015 to 2022,

where it was either a brilliant branding

558

job from the venture capital community,

or the prevalence of these other options

559

weren't really well known or understood.

560

That's the first thing

that this is a choice.

561

You do have a choice.

562

The other thing I talk about with some

founders is the idea that if you're

563

okay with making X number of dollars

over 10 years and therefore having that

564

much money at the end of 10 years, or

having almost no money for 10 years

565

and then having a big check arrive

at the end of 10 years, do you care?

566

Well, really what?

567

How much of your company are you gonna

dilute yourself from over that window?

568

Killing yourself, not having

that choice and what's that

569

worth versus what's it worth?

570

Just on a more linear path, over

a longer horizon so you can get

571

to the same place, and what do

you want your life to look like?

572

How important is this

authorship discussion?

573

For me, the conversation

started really early in my life.

574

The day before I started business school.

575

My grandfather, who was a fairly

successful retailer in a small

576

town in Ontario, told me that, you

know, one of the things he loved

577

the most about entrepreneurship

and the path that he had taken.

578

Which was not to franchise to a bunch

of different stores, but just do one

579

thing and do it really well for a long

time and create wealth, was that he

580

would know at the end of his career

if he was in a castle or if he was in

581

a ditch, that he got there himself.

582

And that the, that control to

him was extremely important

583

and it's hit really hard.

584

I had two sides of my family.

585

One was climb the corporate

ladder, two was do your own thing.

586

to be in the middle of that

tension was super interesting

587

That claim that one makes at the

end that says, yeah, I did this.

588

This wasn't because somebody told me

what to do, or I followed instructions.

589

Well, it was took a big risk.

590

I had control of those risks.

591

I made my own decisions on the way

through, and I ended up wherever I end up.

592

that's thing one.

593

Thing two, it's important to say, I

think that the story around purpose

594

inside venture capital is possible.

595

It's just that it has to be super

strong from the beginning, right?

596

So one of the examples that I'll

give is actually really close to us.

597

There's a company called Coho here

in Canada, the financial technology

598

company, and they've done extraordinarily

well, both financially and have always

599

stuck really close to their mission

because the founder built this thing,

600

'cause his mom got screwed on bank

fees at a really tough time and they

601

were just trying to find a better

alternative for people that needed a less

602

expensive path to financial products.

603

And Coho was born and it grew.

604

It never left that mission of providing

a better financial experience that

605

was less expensive and provided more

benefits to Canadians and damn if that

606

didn't become the engine, that made

it resonate with the market and, grow.

607

Now they did go the venture capital

route, and I know there were times when,

608

you're put to the test on how you're gonna

grow But I would just say it's possible.

609

It's just that founder's gotta

be a lot more focused on.

610

Those core tenets of the business early

and consistently through the whole thing,

611

and not let go of that choice, not let go.

612

Even though the investor pressure is there

and there's a lot of cooks in the kitchen

613

at a board table and all that stuff.

614

It just meant that the bar was

higher on sticking to his guns in the

615

context of how that business grows.

616

Yeah, I love that.

617

I think to be able to, remind or

reassure folks in that situation that

618

there's choice around the concept

of success so that there's a picture

619

of success that's been engineered.

620

I like what you said there about

well-branded by the VCs or whatever it

621

might be, but there's definitely that

un unbelievable success We've been able

622

to witness over our lifetimes as people

who are, founding businesses in the last

623

20 years I'm going back to what you said

about that gives you real confidence

624

that this kind of thing is possible.

625

But I worry sometimes that it sets an

expectation that unless you achieve

626

this kind of out of the stratosphere

success, then what have you even done?

627

And you dedicate yourself to

this destination of success.

628

That's so.

629

Flimsy in that so few actually are

able to achieve it and kind of put the

630

journey of getting there to one side.

631

I think one of the things that I've been

super inspired by in your story and.

632

in Red Brick's story has been the

dedication to caring about that journey

633

recognizing that that is as important

an aspect of growing as where you

634

actually finish up at the end of it.

635

And to be intentional and to make choices

around that is such a aspect of authorship

636

that I think is really important.

637

Rory: Yeah, totally.

638

Laurie: I remember when we sat

around the fireplace, Rory, what

639

success looked like for you was

about, Hey, how do we get there?

640

Canadian tech scene to believe

in itself and to be the force

641

that it has the potential to be.

642

And we get this interesting moment

right now where our neighbors south

643

of the border from us have an author

who's a little different on that front

644

Rory: Yeah.

645

Laurie: so much of this comes down to

the nature and quality of the author.

646

we're getting this stark lesson right

now of what happens when somebody

647

sits in power for whom success is a

very personal idea for whom control

648

and power and the kind of aspect of

power is so fundamentally important,

649

more important than the role of kind

of service or achieving some other

650

purpose that's external to them.

651

To bridge us over kind of with that,

not necessarily with that context in

652

mind, but just to the importance of

what makes a great author of growth.

653

And we've been, as we go through this,

kind of exploring the qualities that make

654

great leaders of purpose-driven businesses

655

And we've talked to you a bit about this

previously, but I'm curious if you, when

656

you reflect on yourself as an author of

Growth and you think about the qualities

657

that we use there, which at their heart

are anchored in a very human centered

658

understanding of what it means to be a

leader, to possess qualities that anybody

659

gets to possess irrespective of their

lived experience, their education, their.

660

Skin color, their

chromosomes, whatever else.

661

These are sort of ubiquitously human

ideas of creativity and courage and

662

empathy and patience and love that shape.

663

In our research, the kind of

leaders who go on to make choices

664

around growth that tend to.

665

Put businesses on the pathway to

purpose and that kind of thing.

666

So I'm gonna put you under the

spotlight for a moment here.

667

You've had an opportunity to look

at those, and I'm just curious, as

668

you looked at those, which of those

qualities do you think has been sort of

669

your superpower, the thing that you've

used most to author your growth journey

670

Rory: what is the picture of success

in the end that we have today?

671

What does it look like and what it isn't?

672

in my personal view, it isn't me sitting

on a giant hoard of gold coins by myself

673

having, done whatever it took to get

there and not been mindful of the journey.

674

one of the most questions that I got

earlier in my career was in, in the throes

675

of negotiating an employment contract.

676

The question came back, roar, how many

times do you have to renovate the.

677

Why does this money matter this much?

678

Aren't you more enamored by the

mission and the cause and the team

679

and the opportunity than you are

about the incremental X number of

680

dollars that I was negotiating for

681

Why not just give it to me?

682

Who cares?

683

But the point of it that really hit me

hard was again, why would you do this

684

thing that you're about to sign up for?

685

What is the successful outcome?

686

It's not to renovate the

kitchen for the seventh time.

687

in my mind, it's the idea of bringing

great people to a better place than they

688

are either from a career fulfillment

perspective, from the ability to satisfy

689

their own purpose, whatever that is.

690

Somewhere along the way, I started

to sort of repeat this mantra,

691

which is business is about people

before it's about anything else.

692

I really live by that and what it's

meant is, the picture of myself being

693

successful as an individual or any of the

companies that I'm working with involves.

694

A number of us sitting around a fire,

having a conversation about the meaning

695

of life, happily at the end of a long,

satisfying journey that was fruitful

696

across whatever criteria for purpose.

697

We started with the idea

that we don't do this alone.

698

It's not about a personal amount of money

that comes at the end of it, beyond some

699

level of sufficiency and fairness, right?

700

There's a lot of privilege that goes

along with that comment, but once you

701

jump over the, you have a kitchen,

you don't need to renovate it, bar.

702

There becomes a question

of like, to what end?

703

what would all this work and success mean?

704

If not the thing that I really care

about, which is the people around me,

705

the ability to provide a great life,

not just for myself and my family,

706

but for anybody who decides that they

wanna do business with me, either as

707

somebody on my team a client a partner or

anybody that would come across my path.

708

That's what does it for me.

709

The purpose is not to make more money.

710

The purpose is to have a great

experience and provide that great

711

experience for as many people as I can.

712

What I find is, coincidentally,

the more I do that, the more

713

money appears to materialize

outta nowhere and we grow, right?

714

So there's a real virtuous cycle

to how a lot of this stuff works.

715

And you know, in the example that

you described before, if you think

716

about, you know, the, the current path

the current president of the United

717

States is on, he ends up on a pile of

power, probably in a burning inferno.

718

By himself with a bunch of people blaming

him, there's no good outcome there.

719

Right?

720

There's a lot of people that could

have benefited along the way.

721

Like think of the power of the leader

that would have driven these incredible

722

outcomes for hundreds of millions of

people by sharing power and sharing

723

wealth, and having a purpose towards a

political agenda for the most powerful

724

country in the world that would've

created wealth and prosperity for

725

the most possible number of people.

726

Power of that opportunity squandered

in the hands of somebody who wants to

727

sell Teslas on the White House lawn.

728

I think it happens in the path of

the person that's looking for the

729

unicorn outcome, where the fantasy

in their heads, when they're first

730

starting the businesses, that it's

gonna be them alone in a mansion in

731

Florida, it's a very hollow outcome.

732

I think there's a small and

growing number of people who

733

have started to appreciate that.

734

far better to be able to say that

you're in a castle or a ditch

735

because you made a whole series of

decisions that were in line with

736

your own principles and objectives.

737

And my observation of life at the moment

is, a lot more people in the castle at

738

the end got there because they had some

purpose that was beyond having a castle.

739

Laurie: I love that.

740

So, which one was it?

741

Which one served you in that sense

that maybe you would wish you saw a

742

little more of in a friend down south?

743

Rory: Courage,

744

I think is the first one.

745

from a personal perspective, I

find in the world that I've been.

746

Working in, there are these moments where

there's fear that people don't know what

747

to do, and to be okay with that fear and

to do it anyway, make the best decisions

748

you can in the most disciplined possible

way, with the right end goals in mind.

749

To have the courage to do those things, to

have the courage to be wrong, to have the

750

courage to screw up, to have the courage

to be able to walk back and do it again.

751

The courage to learn, the courage

to take on things that otherwise

752

seem crazy, like climbing mountains

when you can't see the top.

753

Those are the things that have grown great

inspiration that I've been able to bring

754

forward in my own career in a way that

might be different than other people.

755

I can see that, and I would encourage,

there's a way to swap out when you talked

756

about confidence earlier how did you bring

confidence and create confidence when

757

you couldn't see the top of the mountain?

758

I wonder if substituting courage for that

is an interesting concept That actually

759

what you're bringing in those moments is.

760

The courage to rally in the face of the

fear you don't know what it was, and

761

you're more aware than anyone of the

consequences of failure in that space, to

762

help other people step into that courage.

763

It's an interesting idea.

764

I, I would tell you, I, I don't

know if good people at the Oxford

765

Dictionary would agree with me, but

the thing that I always felt about

766

confidence is that it can be faked.

767

You could just look confident

and not crack and say things

768

You can't fake courage.

769

I think you're either courageous

or you're not in scenarios where

770

it's needed and there's no veneer.

771

You just have to do the things.

772

confidence is a really important

part of it, but only when rooted in

773

something with a bigger principle.

774

Otherwise it's just, you know, you

could put a mask on and be confident.

775

You can't put a mask on and be courageous

'cause you actually have to do the

776

things you're challenging yourself

with President of the United States

777

of America in 2025, I don't think

what we're seeing is very courageous.

778

I think what we're seeing is a

lot of activity that is personally

779

beneficial or beneficial to a very

small group of people and causing a

780

lot of damage to a lot of other people.

781

And that's not courageous,

that's weak, that's greedy.

782

It's Terrifying in a lot of ways that

it could happen in the first place.

783

When you have, people in leadership

positions that aren't properly motivated,

784

that don't have these qualities, I

think you get these terrible outcomes.

785

And the thing that confuses me the most

right now is why more people can't see it.

786

Right.

787

that this veneer, this confidence, maybe

that's the parallel, the ability to

788

fake it is so convincing in these cases.

789

Hundreds of millions of people are

convinced in the confidence of a conman.

790

And so from that end, I think there's a

lot of real important work that we need to

791

do now in understanding the underpinnings

of authentic leadership and how we

792

reveal those qualities in a way that's

more understandable to more people so

793

that we don't get into these situations,

whether it's people that are voted into

794

office or people that are promoted within

companies With great power comes great

795

responsibility, and when it's wielded,

well, incredible things happen, right?

796

And so I think that's the power of

leadership from that perspective.

797

Laurie: I love that confidence exists

in both places, but in one place when

798

it's paired with courage, you get

something really authentic and brave.

799

When it isn't, it can feel

empty, Still can be convincing.

800

unfortunately.

801

So what about the other side, Rory,

as the last thing I'll ask you today?

802

The quality there that you feel has

been kind of the toughest one for you

803

to bring into your own leadership,

the biggest stretch for you?

804

Rory: Yeah.

805

when we went through this exercise

There's a lot of weakness in here.

806

I can pick out any of these and give

you times when I, could have shown

807

more strength in any one of these

characteristics, but the one that I

808

think resonates the deepest with me, and

certainly any of my managers from Jobs

809

Pass would probably agree is patience, For

all the reasons we described at the top

810

of the discussion, there's not a lot of

room for patients in a business that moves

811

this fast with this kind of expectation.

812

I think the idea that being impatient

drove better results was a real misnomer.

813

That patience with people, patience

with thought, patience with strategy,

814

knowing when to back a bet for a

longer period because the answers

815

don't come easily right away.

816

Patience has not been my long suit

with, with results, with people,

817

with expectations on myself, and

they're all, as I look back through

818

those experiences that weren't.

819

The best through the lens of what

would've happened had I been more patient.

820

Almost all the time the answer

is, would've been better.

821

You made that call too fast.

822

You expected too much too soon.

823

You cut your losses too early.

824

Those types of things is one of the

areas where the little voice in the back

825

of my head is constantly challenging

myself on knowing that this is an

826

area that, I didn't start strong

in and need to continue to develop.

827

Laurie: Yeah, and maybe as a consequence

of the courage that you have, which

828

enables you to jump into things when

other people might take a more tepid

829

look at it, you are good to go.

830

'cause you can hold

that fear and go anyway.

831

So I think it's common to see

those two things together.

832

And I hope that's

833

Rory: I hadn't thought of that.

834

Laurie: Yeah, to be able to ally

that courage with an increasing

835

understanding of patients as you

co-author, red Brick's journey.

836

I love the idea that you can bring

those two things into a healthier

837

relationship with each other.

838

And I, for one, just so, so impressed

and excited, both by kind of how

839

Red Bricks arrived, where it is.

840

And I always find it, you know,

we get to talk to a lot of.

841

Executive teams, boards and leaders

coming together around ideas.

842

I'm not surprised at people who

sit around the table together

843

And I think looking at your team and

the ways you've so thoughtfully come

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into the conversations around what

does growth look like for Red Brick,

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that how holistic you've been, you've

been able to think about that and how

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committed I see each of you being to.

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Pursuing that in the, in the kind

of courageous way you talk about,

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which is through the actions you take

and the decisions you make in the

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face of shortcuts and quicker ways

of getting places those intentional

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choices, make it exciting to watch

how you unleash greater growth.

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Rory: I would say it's incredibly

inspiring and I feel very fortunate

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to co-author this story with Marco

and Tolin and the rest of the team.

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It is that story of why grow the

ability to look at a question like that.

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Really for the first time in my career,

they've been doing it for a long time.

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I consider myself lucky to be able to

enter that equation and add to it and,

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put my own pin on it to some degree,

Really it's the vision that's come from

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years of this extraordinarily impressive

ability to look at the larger field of

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play in business from all these different

lenses, from a purpose perspective,

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where that purpose can be defined across

a couple of different, major influences

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in a way that I just haven't before.

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To be able to author a mission

to be able to define purpose.

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Then to be able to build a business that

achieves those ends, is really what Tobin

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and Marco have created from the jump.

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my ability to join the band when I did

was just great timing in a lot of ways.

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also the foundation they built the

business on that I now get to add to is

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extremely strong and sets the stage for.

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great work in the future, I think you're

helping us do it too, which I, I really

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appreciate the conversations that we've

been having on, again, sort of tapping at

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the heart of why we're doing these things.

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The way that we're doing them has allowed

us to become much more conscious of the

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fact that we're doing them and to create a

language and a playbook that surfaces that

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value in ways that only make us better

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Laurie: thank you for helping us do that.

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That's the work we love.

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And thank you for coming on here and

talking to us and inspiring, the folks

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who are listening with your story and

leaving them with something to think

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about in terms of their own businesses

So Rory, it's been a real pleasure.

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Thanks so much for being here.

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Thanks for having me, Laurie.

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What a great conversation.

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Thank you.

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Thanks for listening everyone.

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We hope you enjoyed learning about

the evolving meaning of growth and

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the role of leaders in shaping it

from Rory's insightful perspective.

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You can find a link in our show notes to

more information about Rory and Red Brick.

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Tune into our podcast every month

for more episodes on what's happening

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in the culture and leadership space.

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What's on the minds of the leaders

committed to change in our community and

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other future of work content you crave.

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