Episode 02 | Part One: Bridging the Generational Gap

Gregory Shepard, an entrepreneur who's built and sold 12 businesses, a recipient of 4 private equity awards, TEDx speaker, and Forbes author. This is The Boss Podcast with Gregory Shepard.

Thanks for joining me on another episode of The Boss Podcast. Us Gen Xers and Boomers are still going strong as entrepreneurs, but the next generation is coming in hot, making their mark. And now the generational shift continues as Generation Z enters the So this week I wanted to talk to a millennial CEO who is handling a staff made up of Generation Z folks during a crisis. His name is Ben Crudo, the CEO of Diff. Hey Ben, how are you?

Hey, thanks for having me.

Yeah, you've got a fantastic story and I really want to start from the beginning. How did you know you wanted to be your own boss and start your own company as an entrepreneur? I mean, did it just hit you?

No, I got hit with a pink slip actually. So that was—

That happens to some people, right? You're like, if you're your own boss, at least you can only fire yourself, right?

Well, it's a good motivator. I mean, I had kind of grown up around entrepreneurs my whole life. My dad had a clothing business, you know, ran a chain of stores in Canada. And so I guess I wasn't ever, you know, shy to kind of do something on my own, but it wasn't my first instinct. I would say that it was more out of necessity. You know, working through the retail biz with my dad, I learned a ton about the importance of computers through that process and being really insecure about what I didn't know, but having tons of ideas. I was very forward-thinking and I always knew that I was working harder than my computers were. And that didn't make any sense to me. So through the experiences of hiring consultants, getting all my wacky ideas out, uh, that kind of got me turned on, I suppose, to that path. And I had quit the retail biz so that I could go back to school to become a software engineer because I was sick and tired of relying on other people's opinions to let me know what's possible and what's not. I kind of wanted to get to the truth myself. So—

I get that, man. I totally get that.

It was the long road.

Yeah, I'm picking up what you're throwing down. I hear you clucking, big chicken. So let me ask you this. So we all know about Silicon Valley. In past episodes, I've talked about San Diego becoming this thrive. You know, everybody's always talking about Silicon Valley and so, you know, people are, this is the little Silicon Valley for that. And you're in Montreal. Montreal is, you know, like the Vegas of Canada, right? So tell me about how you became an entrepreneur there and how it is You know, starting a business in that city and what it's like because there's a very specific reason why I wanted you on the show. It has to do with the generation that you deal with. And so, let's talk about Montreal and how that connects to the type of employees and the type of staff that you go out there and get.

Yeah, absolutely. I mean, Montreal is a very metropolitan town but we have a ton of universities here actually, both French-speaking which is the dominant language and English and I think the French is probably why we're a little bit less connected to North America than maybe Toronto per se might be. But we've got tons of talent here. I mean, these people are first world. They've all got iPhones. We're North American in every way. It's just the language barrier, I think, really makes our talent pool inaccessible. You can probably tell from my English accent that it's my native tongue though. But I've been able to sort of connect, I think, with a local population that certainly amongst the English guys at the English universities, which are quite prominent here, and further more within engineering, I think it has this extra layer of English associated with it that is a little less common in other disciplines. So I think it's like pooling all together, right? Where like the young people are interested in computing, English is the language of the internet, and, you know, our business is internet-focused. So it makes a good sort of connection between that.

I started a company in Santa Cruz, California, and Santa Cruz, California is like stuck in the '60s, right? It's like hippie-ville. I mean, it's like Super hippieville USA. It's right on the beach. Everybody wears flip-flops and t-shirts and shorts even at work. You get the feeling. There's a university there. And I intentionally went over what we call the hill, which is like this little mountain, to set up the office there because everybody— it's right next to Silicon Valley and everybody wanted to live in Santa Cruz but work in the valley. And the traffic took like 3 hours to get over that mountain and get into the valley. So I was like, well, if I set up there, Yeah. I can get all these people that want to live here and not drive the hill, and it saved me a lot of money, right? Because of the, you know, the cost of living in Silicon Valley is just crazy. Is there some connection that you had like that that you were thinking about? I mean, what— or did this just land, or how did you come about it?

Yeah, I think I kind of got lucky. I mean, you know, I grew up here, but, uh, I'm not sure I was necessarily in touch with all of the great reasons why starting a tech company here would work out well. And It turns out there's quite a lot actually of backing that is supporting, I think, a really strong engineering trade here. So, you know, the government's got their headspace right. They're handing out grants to help companies get off the ground and reduce the cost of engineering labor, certainly funneling money towards people that are embarking on ambitious R&D projects as well, which again helps mitigate risk. And of course, you know, there, I think there's about 4 or 5 substantial universities in Montreal itself that, that's feeding a tremendous talent pool. So I think the conditions are actually right. And another thing that helps, certainly as it relates to a lot of the French-speaking people that may have English as their second language, they're like, Yeah. Really intimidated to go down to Santa Cruz, work down in the Valley, and get a job in the middle of America. It's quite foreign to them.

But yeah, I feel like I would imagine it would be rough, you know.

Yeah, it's tough. They got no connections there, they got no family, and the language is keeping them on the outside. So we're like a stepping stone toward that, you know. We're, we're trying to bring that Valley spirit and that way of running a company and that level of thinking into our local economy.

Man, that's so cool. It's like, it's like a little island almost, right?

Yes, it is.

It's like a little island.

And I feel like the English people here, we're the ambassadors to North America. We're the ones that like have better visibility and it's our job to bring it in and keep this place vibrant and fresh and relevant.

Oh, that's so cool. Yeah, I felt like when I was in Santa Cruz, I felt similar. I was like, man, it's just all hippies down here and surfers and skaters and stuff like that. And there was no like real business being done. And I was like, if I could set something up down here, and actually it turned out to be really cool. Like I had bikes in the lobby and people are going to the beach at lunch. And it was the same kind of thing as these kids that grew up going to the university. And I don't know, for some reason, some of these smaller towns like Toronto, people get stuck. But you know what the other thing is that I noticed too, is that when you're an investor, like I look at deals and constantly invest in companies. And when you're looking at businesses, some of These underserved markets, like I've noticed Toronto is, you know, for Canada, it's like a big, you know, you're finding deals that are priced really high, right? They're expensive to invest in. Valuations are high. Montreal though, you have better opportunities for investors because the valuations are lower. And I think that what you said leads to that, which then just presents more opportunity, right? If you start a business there, right?

But you need a little extra know-how to get into the market and the willingness to recruit people that you're maybe not used to culturally. Yeah.

Well, let's talk about that a little bit. So, I've heard about you when I read an article in Business Insider that was titled, I'm the Millennial CEO of Mostly a Gen Z Team. Your company, Diff, in Montreal, can you tell me a little bit about this company?

Yeah. So, tagging along the tail from before about coming up through the retail biz, I gained the appreciation for software there. Going back to school to get my engineering degree left me kind of wondering what my next move might be. I thought that I'd going to have to earn my stripes, work in a large company and take a real traditional path. And I really wanted to do that. And I tried to do that, but unfortunately it didn't work out well for me. I felt as though there was a serious lack of meaning in the work. I would spend too long working on a bug, get a pat on the back. I didn't know I didn't really contribute anything. that day, but still the same pat on the back came whether I achieved something or not. So I felt like a cog and like I couldn't really, I just didn't have any visceral connection to the work. So I was moonlighting on the side because I've been ambitious and I wanted to increase my compensation. And a friend came over, asked me if I could help him with an e-com site for a local company here. Last guy, he said, paid him $15,000. He ran away with the money, never got a website. At that time, I was working $20 an hour. I was like, $15 grand, I'm all over that. I'll work the whole time. I promise you.

How old were you at that point?

28 years old.

Okay, okay, go ahead.

Through that project where I hadn't actually put the pieces together yet that I know a ton about the retail business and probably could fit in really nicely in the world of e-com. So first project I did for him, I just like, felt the clay being molded in my hands and I was like, this feels good. Like, I know that I'm doing a good job here and I got great results.

You found your place.

I found my place. It's so silly that it wasn't more obvious to me, but I kept doing that and I parlayed that success and that's how DIF started. So one job at a time building up and of course, we decided to focus on a particular tech platform called Shopify, which Back then was a 40-person company that nobody heard about. Today, they're— what are they at on the stock markets?

Monster.

$50+ billion valuation. So I became like the poster boy actually for their partner ecosystem, literally the one-man band, the guy that took his laptop from school, started cranking out code, and now we've got over 100 employees and we're one of the largest global partners that they rely on to Serve their enterprise merchants.

Well, let me say congratulations from an entrepreneur to an entrepreneur. Like, well done, man. I know it is a bitch. It is really hard. I've done it 12 times and I was part of the eBay divestiture in Magento and all those 14 companies. So I know the space really well. And I have a similar story where it's just like, I mean, you are just clawing your way through.

Right.

I mean, it is— people don't understand how hard it is to be an entrepreneur.

Absolutely. And a consultant to bet. I mean, uh, people judge us based on our output, and when we send them a bill, they scrutinize every minute of time that, that we're charging them for. So you got to be really sharp to be able to make an impact and actually get paid.

Yeah. I mean, I want to— so I want to dig into something. So this— we have a series right now that has to do with this whole COVID nightmare.

Mm-hmm.

And it is just taking people out. Businesses are getting just destroyed. And so this article that you wrote really got me interested. I was like, this is— guys, this guy's perfect, right? Not only are you dealing with a group of people that haven't been through anything like this before that you have to lead them through, but at the same time you're dealing with a crisis that nobody has ever dealt with. Now I know that retail sales are actually— online retail sales are actually up. Yeah, right. Like, I know that, you know, I talked to a bunch of companies, they're like, yeah, we're 80% up or 50% up, stuff like that, because people are at home bored.

Conversion rates are through the roof.

Conversion rates are incredible, right? But that still doesn't help with the entire situation that has to do with just the impact of this, right? I mean, you have to take a workforce, put them in their work from home, your meetings change. Like, I mean, this is a fundamental shift, you know, especially for people that are also being shocked because they're young and they're at home alone. You know, a lot of them aren't married yet, right? So I just, I'm anxious to hear from you. How did you handle it? And what were the steps that you took like immediately, like day one, you're like, holy shit, shit's coming off the rails. What did you do?

I think the first step was being really proactive about shutting our office down. We didn't wait for For the government to tell us that all businesses need to shutter, we recognized right away that we needed to send a message to our people that your welfare comes first and we're not gonna ask you as a company to make sacrifices that don't need to be made at any point in time. So right away, just, you know, signaling to the team, we see this coming and we're putting a plan together to help you out on that.

One of the things I tell people is that to do good business with somebody, you need like, trust, and respect. And so by doing that, you showed them integrity straight away, right? So the first indicator of this before the rest of the stuff hit, right? The first indicator is, look, I care about you. And to Gen Z, that is more important than money, right?

Yes, it is.

Okay. The second thing you did was what?

I mean, right away we're like putting our— I think our business, you know, we were lucky that we could transition to work from home like decently. Like we're used to logging all of our time a lot and doing things. So getting people's homes set up right, was the next most important thing. We knew we already had the tools that we needed. We're all hip. We got Slack, we got, you know, all our FaceTime, whatever, whatever we need there to keep in touch. But we wanted to see what we can do to help make people's lives a little more comfortable at home. So we kind of ransacked the office to grab any supplies and arrange for delivery trucks to get things over to people.

So you walked in the office, how did you socialize this? Because now you're getting into more tactical stuff. So, how did you— did you just walk into the room and say, hey everybody, what? I mean, what?

Yeah. So, we were actually— I was actually out of town coming back from Miami and I sent an email to my head of HR. I'm like, you need to clear the office and get everybody out of here. So, at the end of the day on the Wednesday, which was, you know, at the very beginning of March, We just advised everybody, like, don't come back tomorrow. You leave today, take your stuff with you, and we'll be in touch about a plan of how we're gonna deal with this. But for now, take what you need to be self-sufficient and don't worry about coming back. So, okay. It wasn't super organized at first.

No, I mean, what, what, what, I mean, how could it be, right? It's just like, you know, it's like getting hit, T-boned on a Tuesday afternoon by a semi, you know, it's like, what, you know, What can you do?

Very active.

Yeah, right? So, what were the fundamental moves you made? You told everybody go home, you ransacked the office, got everything, delivered everything to the head. What did you do now? How did you get things organized? And this is really important because there are people listening that need this sort of guidance.

Well, it was, you know, the next thing I think that needed to be addressed was the morale of the team. Obviously, with hearing that businesses are closing immediately, everybody was really, really scared. You know, what's gonna happen to us and our clients? So, we made it our business to create a town hall every week to week and a half so that we could update people on what's happening. And we were extra transparent about the state of our portfolio. So, I didn't walk in there and just dish out platitudes and say, hey guys, everything's going to be fine. Don't worry about it. We'll be cool. I was really, really open about the clients that we have, which are having problems, and the steps that we're taking. to mitigate these issues and diversify the portfolio and ensure everybody will be able to stay employed. So, not blowing sunshine up their asses is a pretty good move.

Yeah.

Right. Yeah. These are smart guys.

So, you're being— you just been honest with them and say, look, this is what's going on. These are the clients that are in trouble. Did you find that that helped or did you find that like with this generation and this pandemic, did you find that that helped them deal with it or did you find them sort of I have to say, that's like, it's, uh, I'm not exactly sure because people who are in their first jobs who are lacking business experience don't really know what to make of it.

But I just knew that I wasn't going to take the position where they should wonder what the worst-case scenario might be in order to curb their imaginations. I painted it for them directly and gave them concrete steps that we're taking to mitigate that pain and that damage.

So did you feel like— do you feel like you're one of the guys, so to speak, in your business, and that enabled you to socialize this in a way that they could digest the information without scaring the living shit out of them?

I mean, I generally try to be approachable, and I'm pretty close to the generation that I employ. I am normally, I would say, humbling myself and trying to operate at their level so that we can maintain this, you know, good relationship.

That's awesome. This wraps up part 1 of my interview with Ben Crudo, the CEO of an e-commerce company called Diff. Coming up in part 2, Ben tells us what Diff actually does.

On the surface, it looks like we make websites, but I'd venture to say we go deeper And we help build businesses.

Thanks for checking out the BOSS Podcast with Gregory Shepard. Get more on Greg's Business Operating Support System, BOSS, at GregoryShepard.com. This has been a production of Forbes Books Radio.