Winning Big with Chutzpah: Lessons from the Titans of Entrepreneurship

Harley Finkelstein (00:00):
So season one.

David Segal (00:02):
That went better than we thought.

Harley Finkelstein (00:03):
That went way better than we thought.

David Segal (00:04):
Yeah.

Harley Finkelstein (00:04):
I mean, I thought people would like it, but the outpouring of support and gratitude and excitement about Big Shot, I didn't expect it.

David Segal (00:13):
It's amazing. I mean, the biggest takeaway I took from it was how long it took for some of these people to become overnight successes.

Harley Finkelstein (00:21):
That's right.

David Segal (00:21):
How they were able to day in, day out, keep showing up despite all the odds, keep pushing ahead despite everybody telling them it wouldn't work, and how they were able to maintain and build such incredible lives both around family, philanthropy, and business.

Harley Finkelstein (00:38):
Yeah, it's quite amazing. I mean, look, as many of you know, David and I started on this journey as this incredible passion project to archive the stories of some of the greatest entrepreneurs that have ever lived. We wanted to share those stories with all of you, and I don't think we expected that season one or that the show would've received the amount of attention that all of you gave it. So first and foremost, thank you. This weird little project that David and I wanted to put together for our own consumption, right? I mean, it really was like something we wanted for ourselves.

David Segal (01:08):
It's just timeless wisdom from people who you don't normally hear from.

Harley Finkelstein (01:11):
That's right, and we just want to do this for ourselves. But the fact that all of you not only enjoyed it, but you shared it with your friends and your family, and you wrote to us, and you DM'ed us, and you emailed us, and frankly you stopped us in the middle of airports to say, "Oh, my God, I love Big Shot." That means so damn much to us.

David Segal (01:27):
Yeah.

Harley Finkelstein (01:27):
So first and foremost, thank you. We loved season one, we had a great time.

David Segal (01:32):
We're going to do season two, right?

Harley Finkelstein (01:33):
We're thinking about season two. Yeah, we'll do season two. Okay. We will do season two, but we will do season two at a later date. But the one thing that we thought we would do to close out season one and put a beautiful bow on it is that there were a couple themes that emerged in season one. And I think one of the ideas that David and I have had is that what if we actually created these incredible compilations where we focus on one particular topic, one subject, one lesson, and then we actually create a very short video where you can hear from each of the guests about what they think about that particular topic.

David Segal (02:07):
And of course, what better topic to start with than chutzpah, which is so unique to the Jewish entrepreneurial experience. And each one of these guests had such an incredible... I mean, there were common threads with what they said. You look at Charles, Charles talks about how chutzpah is a good thing in some context-

Harley Finkelstein (02:27):
But not in others, yeah, that's right. Personal chutzpah, bad, business chutzpah are very good. That's right.

David Segal (02:30):
That's right. Yeah. Issy with if, the word if and how you can keep going when others don't think you should?

Harley Finkelstein (02:37):
Yeah. What about Jonathan Wener? Jonathan talked about that no is maybe on its way to yes.

David Segal (02:42):
I think that's the title of his book.

Harley Finkelstein (02:44):
And I think he has new book coming. This is not a pitch for his book, although you should probably read his book because he's an amazing guy.

David Segal (02:47):
He also made an incredible amount of money at a very young age doing things that he had no business doing.

Harley Finkelstein (02:53):
I mean, one thing with this, what about Eddie Sonshine? Eddie Sonshine created a different type of real estate model using the REIT model where he bought real estate and didn't have to put up any of his own capital.

David Segal (03:05):
We also had Aldo in there. Aldo drops his biggest supplier.

Harley Finkelstein (03:10):
Doc Marten. Right?

David Segal (03:12):
And he didn't know what would happen. And we're going to learn what happens next.

Harley Finkelstein (03:15):
And actually, in that meeting where he talks about dropping Doc Martens and going at it himself, that's actually the same time where the company of Sketchers was created. The guy took out, no pun intended, a sketch from his pocket and showed Aldo and said, what do you think?

(03:27):
Anyways, there's so many amazing stories. We have to compile them into one episode. Some of the stuff you've seen, some of the stuff you've never seen before. And we're going to create a few shorts where we talk about specific topics and we create sort of this really cool compilation. And we're going to start with the very, very important topic of chutzpah.

David Segal (03:49):
And one more thing, because we can't just end like that.

Harley Finkelstein (03:51):
You're going to pitch-

David Segal (03:52):
I want to pitch season two.

Harley Finkelstein (03:53):
Okay.

David Segal (03:54):
We should pitch season two.

Harley Finkelstein (03:55):
I thought you were going to pitch Firebelly tea.

David Segal (03:56):
Oh yeah. Well, we've forgot the Firebelly.

Harley Finkelstein (03:57):
Also, if you haven't bought Firebelly tea, buy some Firebelly tea.

David Segal (03:59):
You need a Firebelly. We did a whole commercial that was like... But season two is going to be amazing. We're thinking, we're not sure which market. We might go to New York, we might go to Boston. We are not sure yet. But let us know. Tell us in the comments.

Harley Finkelstein (04:12):
Tell us where to go, who we should interview. If you have anyone who you specifically think has to be on season two of Big Shot, we are beginning now to create our list, our cities who we want to interview. So if any of you watching have any great ideas, let us know. Because we thought season one was great, but we really want to scale things up, and make it even better for all of you for season two. Anyways, there's so many amazing stories, but we thought we'd create these incredible, super episodes on one topic across all the guests. Ladies and gentlemen, Big Shot presents Big Shot Shorts.

David Segal (04:47):
Chutzpahs.

Harley Finkelstein (04:48):
Big Shot Shorts. It's not that short. It's 25 minutes.

David Segal (04:48):
It's not that short. Yeah, it's not that.

Harley Finkelstein (05:08):
It's iffy.

Speaker 3 (05:11):
(singing)

Harley Finkelstein (05:12):
Okay, now you're going to hear from Eddie Sonshine, the founder of Rio Can. And he's going to talk about chutzpah in a way that asking for things that you have no right to actually leads to incredible results.

(05:24):
There is a theme, another theme that sort of underlies this entire project around Big Shot, which is chutzpah, and call it whatever you want to call it. In fact, I'd like to hear what you think it is. How do you define chutzpah?

Ed Sonshine (05:38):
In one word, you could say nerve. You got the nerve. They all come, but it's basically, chutzpah is either asking or doing something that you got no right actually believing you should either get or be able to do.

Harley Finkelstein (05:54):
Yeah.

Ed Sonshine (05:55):
That to me is chutzpah. It's like you got a nerve to think you're going to invent a new form of real estate company? Who do you think you are? Well, I'm going to try. So I showed a lot of chutzpah, I guess. So yeah, I guess in, well, you're a Canadian right? And you're going to start buying-

Harley Finkelstein (06:12):
American properties?

David Segal (06:12):
Right.

Ed Sonshine (06:13):
American properties.

Harley Finkelstein (06:13):
In Texas.

David Segal (06:13):
When everyone else has gone to the US and lost their shirt.

Ed Sonshine (06:16):
Right? Yeah. So those are examples of chutzpah. It's, you know, dare. Dare to try something. Dare to go start your own business.

Speaker 3 (06:25):
(singing)

Harley Finkelstein (06:29):
Now, you're going to hear from Charles Bronfman, the famed philanthropist and entrepreneur behind the Montreal Expos, Cadillac, Fairview, Birthright, and of course, his family is the Seagrams family.

Charles Bronfman (06:39):
Chutzpah is sort of daring, but in a not nice way. The Chutzpah is that person to think that he can rule the world. Chutzpah in business is damn good.

Harley Finkelstein (06:51):
Damn good.

Charles Bronfman (06:51):
Because if you don't have some chutzpah, you're not going to get very far. I'm sure that both of you... You weren't the first tea company in the world.

David Segal (07:00):
No.

Charles Bronfman (07:01):
You weren't the first Shopify company in the world.

Harley Finkelstein (07:03):
Certainly was not.

Charles Bronfman (07:04):
But you had the guts and the drive. Chutzpah, in business, I think, is really drive and not giving a damn about all the procedures and things that are in the textbooks.

Speaker 3 (07:17):
(singing)

David Segal (07:22):
Okay. Now you're going to hear from Aldo Bensadoun, the founder of Aldo Shoes, which had over 3000 shoe locations, tell us about how he dropped his biggest supplier and what happened after that.

Aldo Bensadoun (07:36):
I could think of chutzpah, like you said, is when I made the decision to leave my former employer, then leave Chateau, and there was other moments in my career that you had to make big decisions. For example, we used to sell not only Aldo, but we used to sell Doc Marten in our store.

David Segal (08:11):
Which was a big brand in its time.

Aldo Bensadoun (08:13):
It was a... Yeah, and we were doing extremely well. At one point, they told us that we were the second-largest user or account after England.

David Segal (08:26):
Wow.

Harley Finkelstein (08:29):
On the planet.

Aldo Bensadoun (08:29):
On the planet.

Harley Finkelstein (08:29):
Wow.

David Segal (08:29):
Incredible.

Aldo Bensadoun (08:30):
And we had a great relationship with them. And we even, we designed... Our company designed some of the product that Doc Marten is still carrying today.

Harley Finkelstein (08:45):
Wow.

Aldo Bensadoun (08:45):
And we had a very, very close relationship. And they were very, very nice people too. And then they said, well, if Aldo is doing so well in Canada, maybe what we should do is that we should not only sell to him, but we should sell to everybody.

David Segal (09:06):
Of course.

Aldo Bensadoun (09:06):
And at the time, the only people they were selling to Neon and to ourselves, and that's it. And in fact, Neon was going through us to buy the shoes.

David Segal (09:21):
So you were almost like a distributor for-

Aldo Bensadoun (09:23):
So then they said, we are going to open our own, and we said no. And at that point, certain store, we are at store in Chicago, when 90% of our sales came from Doc Marten rather than Aldo.

David Segal (09:41):
Wow. So high stakes.

Aldo Bensadoun (09:42):
So you talk about chutzpah, I remember I was with my wife at a meeting with the Griggs, which owned Doc Marten in Scotland, or in England, I should say. There was also... What's his name now, Robert Greenberg that was also selling in United States. And they had asked us to come and visit them, the Doc Marten. So they announced to us that they were going to open their own distribution in North America, in Canada, and in United States. And we went to bed that night. And then in the morning we told them, we said, listen, we don't want to buy anymore from you.

Harley Finkelstein (10:37):
Wow. So that was one of your biggest products, and because you didn't like what they were proposing, you said-

Aldo Bensadoun (10:42):
Correct. Because our business model was always going from factories to the-

Harley Finkelstein (10:47):
If there was intermediaries you didn't want to do that.

Aldo Bensadoun (10:50):
Yes. Exactly.

David Segal (10:52):
I mean, were you scared? I would've been terrified.

Aldo Bensadoun (10:53):
I was very scared, very, very scared. So then at that point, we decided to stop working with them, and then the following morning they came to us, and they said, "Could you set up for five years a distributorship in Canada on our behalf?"

David Segal (11:20):
Oh my God.

Aldo Bensadoun (11:20):
It would go through us, but it belonged to them. Okay? And we said, okay, that fine. We could at least control where we were going to sell the good, and we were making a commission too, so we accepted it. Same thing in the case of Robert Greenberg in United States. And what he said, he said no too. And what did he do?

David Segal (11:46):
They gave it to you?

Aldo Bensadoun (11:48):
No. He started, he said... Remember at that breakfast? He said, "So Aldo, what are you going to do?" I said, "I'm just going to sell Aldo." And he said... He pulled a few sketches from his pocket, and he said, "What do you think of those sketches?" And I said, "It looks pretty good. I mean like that style or that style." And he said, "Perfect." And that's how he founded Skechers.

David Segal (12:16):
Wow.

Harley Finkelstein (12:18):
Wow. So he founded Skechers because he didn't want to deal with Doc Martens anymore.

David Segal (12:23):
He didn't want to be just another customer.

Aldo Bensadoun (12:23):
Exactly.

David Segal (12:23):
And so he decided he wanted to also be vertically integrated, like you.

Aldo Bensadoun (12:25):
Exactly.

David Segal (12:25):
And that's the beginning of Skechers.

Harley Finkelstein (12:27):
And did you-

Aldo Bensadoun (12:28):
From those little sketches?

David Segal (12:29):
That's unbelievable.

Speaker 3 (12:31):
(singing)

David Segal (12:32):
Okay, now you're going to hear from Jonathan Wener, who's iconic for building Canderel, which was one of the largest real estate development companies in Canada, and he's going to tell an amazing story about how he convinced the mayor of Montreal to do something really important.

Jonathan Wener (12:45):
At 16, I went to see Maxwell Cummings, and they were building a large portfolio in Calgary. And I said, "Listen, I'm 16, I'm going into university next year, and I want a job in management." He said, "Tell you what, go buy yourself a pair of hard-toed construction boots and a helmet, and I'm sending you to Calgary and you'll learn about management."

David Segal (13:10):
Hit the site.

Jonathan Wener (13:12):
And I learned to build from the ground up, bottom of the totem pole, and they put me through the ringer, and I wouldn't quit. End of the summer, I became clerk of the works on the job, and so I moved up quite a peg. I wasn't anymore on the construction site. I was in the office. The next year, they hired me to act as a general contractor for the same building, selling tenant improvement packages to the tenants, and I made a million dollars in the six months in my second year, first year of university,

David Segal (13:48):
You're like 17 years old.

Harley Finkelstein (13:48):
I mean, that takes a certain level of chutzpah to call and say, I'm going to be management now. Was that something, is that chutzpah, is that something that you always sort of had, you always felt the audacity, the confidence to do, to take something?

Jonathan Wener (14:04):
Yeah, I believe not taking no for an answer. So figuring it out, I was probably a bit brash and a little, very naive at the time.

Harley Finkelstein (14:13):
You were 16. I mean, who's not?

David Segal (14:13):
Right. Yeah.

Jonathan Wener (14:17):
I knew that I was going into management at Concordia, which was Sir George at the time. I obviously wanted something that was aligned to that. But if this was a route to get there, and he told me, he said, "You hunker down. Learn. Learn everything." And the amount I learned about construction that summer, and I remember a cement truck driver saying to me, "You must be Jewish." I said, "Why?" He said, "You asked so many questions." And I was asking about the different aggregates and what's the difference between this concrete and that concrete. And I was learning. I learning like a sponge, and I've always been a sponge for learning from people and or experience.

Harley Finkelstein (15:06):
And then you get to Concordia, which you describe as a part of you.

Jonathan Wener (15:11):
So I was very active at Sir George. I was the first student member of the Board of Governors. I was chairman of clubs, chairman of a pledge drive, skiing and all kinds of other activities. I was president of the student union in that last year. I had renovated that student union.

Harley Finkelstein (15:32):
What do you mean you renovated the student union?

Jonathan Wener (15:33):
Okay. So a group of us bought the student union, which is where Villeneuve had his bar.

Harley Finkelstein (15:41):
Yeah, yeah. So, a group of... You were student and you bought the building?

Jonathan Wener (15:46):
Yeah.

Harley Finkelstein (15:46):
How old were you?

Jonathan Wener (15:47):
20.

David Segal (15:48):
This is privately or through the school?

Jonathan Wener (15:51):
Through the school. Through the school. And that year I renovated it, and it's actually in itself quite a story because I kept going for a building permit and I set of plans. And the first time, these are all part of the no is maybe. First set of plans, the building permit department said, you need to make these, this and this and this change. And I said, okay. So I went back, made the changes, came back, made application for the permit, didn't get it.

(16:26):
This happened three times. I finally... I'm only 20, but I'm realizing that I'm being held up, and I'm an institution, and this isn't right. So I go back to the student association floor on the fourth floor at Sir George, and I said, "I'm calling the mayor." "Oh yeah. Who are you? You're going to call-"

(16:45):
"I'm calling the mayor." So I pick up the phone, I call the mayor's office, and the woman says, I'm sorry, the mayor's busy. I said, "Well, I kind of knew that that's what you were going to say, but just let me interject a few words here, and then we'll see where this conversation goes." I said, "My name's Jonathan Wener. I'm president of the student union. I don't know whether you realize it or not, but the mayor's running for reelection in October, and this is the first time that students will have the right to vote at 18 years of age. They are going to be furious when they find out that city hall has been holding up the student union from being able to renovate and be open in September."

Harley Finkelstein (17:25):
Wow. That got her attention.

Jonathan Wener (17:27):
Just a moment, please.

David Segal (17:27):
The mayor's not busy all of a sudden.

Jonathan Wener (17:31):
Mayor gets on the phone, he said, "Tell me the story Mr. Wener." I tell him the story. He said, "You come here at 9:00 tomorrow morning, you'll pick up your permit." And he made the guy hand it to me. He was so red-faced.

David Segal (17:47):
Wow. Chutzpah. Yeah, total chutzpah.

Harley Finkelstein (17:51):
But the chutzpah part of it is the fact that you decided call him to call the mayor directly. Whereas most people would never even think to do that. They'd be like, "Well, I guess it's the way it's done. I guess we have to wait in line."

David Segal (18:00):
Yeah. I mean, you're 20 years old.

Jonathan Wener (18:01):
Yeah, but I also... Because of the ethos that I was given by my grandfather, payoffs were just not in the vocabulary.

Speaker 3 (18:09):
(singing)

Harley Finkelstein (18:12):
Now I got to hear from Issy Sharp, the founder of the Four Seasons, and he's going to talk about what happens when you remove if from your vocabulary.

Issy Sharp (18:21):
It's not a personality as a braggart. I think it's a personality that you have a subliminal belief in yourself that when you believe with what you're doing will work, even though there's skeptics all around you telling you why it won't work, all the reasons that they can give you. But that doesn't stop you from saying, "I know what you're saying is true." Because what they are telling you are facts of the past. And you say, "I know. You're not telling me something I haven't heard before, but I think this will work, it's not going to deter me."

(19:13):
You have an inner feeling, and you don't know where it comes from, but it's part of you, in terms of your ability to have the courage to be able to persevere against all the odds and take and accept the consequences. If you're going to roll the dice with everything you own-

David Segal (19:38):
You may lose.

Harley Finkelstein (19:39):
You may lose. Yeah.

Issy Sharp (19:41):
You may lose. So I think that that comes from your genes that you inherit. It's not what you learn in school or you can read in books. It's your natural personality that gives you the drive and the energy. And I think it's not like being a narcissistic trump, not that at all. You don't have an ego. It's not like you're doing this because, "Hey, look how good I am."

(20:17):
So I think it's personality, and I have to say our Jewish heritage goes back a long way that gives us the belief of can do. If it doesn't work, so be it, but I'm going to give it my all. Sometimes I tell the kids, when they all ask these questions, I say, "Look, in your vocabulary when you're doing things, take the word if out of your vocabulary." Don't say, "If I would've studied, I could have passed in honors. If I would've practiced, I could have run faster." That's bullshit. If is a crutch. You're afraid to say, I gave it my all, I ran as fast as I could. I came last, but you know what? That's good. I know how fast I can run now. So that is what the chutzpah is.

Harley Finkelstein (21:28):
Beautifully said.

Issy Sharp (21:29):
They're able to say, I'm giving it my best, and I'm making no excuses. If it doesn't work, I will say, "Hey, I wasn't good enough." And that's okay.

Speaker 3 (21:44):
(singing)

Harley Finkelstein (21:44):
Where you and I really connect, the common thread of my story and your story and who I am and who you are is, it's chutzpah. And we're meeting all these incredible entrepreneurs towards the end of their right entrepreneurial journeys. Not the end of their journeys, but the end of their core entrepreneurial ventures, and we're not at the end of our journeys. We're kind of still in the midst of it, in fact maybe at the beginning of our journeys.

David Segal (22:12):
We're just getting started. Yeah.

Harley Finkelstein (22:13):
And I'm curious, how has your experience affect your chutzpah?

David Segal (22:19):
I think what people miss about entrepreneurship is how much failure is involved, and I don't... It's one thing to say it. It's another thing to feel it, and to feel it on a daily basis. A day feels like a week, and a week feels like a month, and a month feels like a year. And in the moment, it can sometimes feel like everything is just not moving, and it's just not going to work, and it's not going. And we live for those moments where it's like, oh my God, the stars have aligned. It's working. This is amazing. You get that entrepreneurial high, right? But the reality is that's not most days. Most days are a grind, and it takes-

Harley Finkelstein (23:00):
How many times do you call me on a Monday to talk about something related to Firebelly? And you're like, oh, this is not working and this hasn't happened, and we lost a bunch of inventory, and this pallet came in wet. I mean, that is part of the journey of entrepreneurship. But I think where chutzpah is such an important ingredient to it is, it gives you the audacity to just keep fucking going.

David Segal (23:21):
Well, and the chutzpah is like, you get used to failure and all of a sudden you're not afraid of it, and you're not afraid to... You sort of say, fuck it, I got nothing to lose at a certain point.

Harley Finkelstein (23:34):
We asked all our guests, what does chutzpah mean to them? One of them said, it's sort of like doing something when everybody else would say, "Who do you think you are?"

David Segal (23:42):
Right. The nerve of this guy.

Harley Finkelstein (23:43):
The nerve of this guy, the nerve of this person. And I think that, more important than all the other things, capital and connections and an understanding of the market, ultimately that may be the most important ingredient in all of this. In business, in building, in entrepreneurship. It is doing something that most people would never dare to do. And realizing that those days where you are down, you're a bit depressed, you're anxious, you're feeling exhausted, that you just keep going because you know that no one else dared to do this, but you as an entrepreneur, fucking right you're going to do it.

David Segal (24:24):
I think I've told you this before. I've never said this on air. The biggest fear I have is not being able to get up and do what I love to do and be an entrepreneur. That's my biggest fear.

Harley Finkelstein (24:37):
Yeah. I love that.

David Segal (24:38):
Is this idea that, I mean, and I think about that whenever... I mean chutzpah is, it's to have the nerve to have the, who do you think you are? To be daring in that regard requires you to... It's not that you're not going to be afraid. I think there's a misconception that, oh yes, chutzpah. He's just got so much guts, he's not afraid at all. I mean, there are times where I'm sure you've made phone calls or gone into meetings or had a very important situation that could impact a big outcome for you, where you were nervous, but you did it anyway. You show up, you prep, you get ready, you channel that energy, and you don't let that stand in the way of at least trying.

Harley Finkelstein (25:20):
Also, and then maybe chutzpah is actually slightly different than what we've been describing. Maybe chutzpah is doing the thing that is daring, getting a result that you didn't want and still doing it again, and doing so with a perpetual level of energy that you keep doing the thing that others would say, "Who does that person think he is?" That is not something most people will do, but you do it with enough enthusiasm, and you don't reduce the enthusiasm as time goes on.

David Segal (25:47):
Right. And the greatest feeling as an entrepreneur is realizing, who do you think you are? This is who I am.

Harley Finkelstein (25:53):
I'm an entrepreneur.

David Segal (25:53):
I'm an entrepreneur. This is who I am. That's the point. I'm never going to stop trying. You can knock me down, but I'm getting back up. You better knock me out because it isn't... forget it.

Harley Finkelstein (26:03):
Yeah. You're not going to knock me out. In fact, that's what this show is. This show is a celebration of chutzpah, which fundamentally is a celebration of entrepreneurship.