From Challenges to Transformative Experiences: Navigating Business and Immigration w/David Cantor

Welcome to another episode of the Whole Human Podcast. I'm your host, Peter Sorgenfrei. And today I have David Cantor with me. David, welcome on the show.

Thank you for having me, Peter.

So David is an interesting story in many, many ways. And we're going to get into that in a couple of minutes. But first, and before we do that, David, what are, what are a few words about who you are and what you're up to right now?

Yeah, sure. So who am I? I mean, I guess I would consider myself a global citizen. I'm sitting here in Florence, Italy, where it's been my home base for the last 5 years. I uprooted with my family. I have a wife and 2 kids, so I'm also very much a family man. We left New York City respectively in our careers because it was a good time And we'd always been coming to Europe on and off throughout our relationship, 10 plus years. So we're settled here now. And yeah, I mean, I guess the, I say global citizen with a, you know, a definition that's not yet like fully defined, right? Because what does that even mean? So I guess, I mean, I consider myself a worldly person and within even my career path and my personal life, I've always kind of stepped outside of borders.

Understood.

Yeah.

And it started early on, right? I think you went to school in New York and then you had an exchange year or something in China. Is that when your, the global citizen part of your life started?

If I had to say where are the roots, Peter, I think it even goes back further, a couple of years before when I left a full-time job in Chicago and took 3 weeks to go to Costa Rica and Guatemala. My first time with a backpack, first time staying at a youth hostel, first time meeting people on the road. And I remember my American colleagues and friends were like, well, how are you? What are you doing? You're going for 3 weeks. What about your career? You know, and your, my parents and everyone else. That's, that's a long time, David. What are you doing? And I'll never forget, I, I met 2 backpackers at a youth hostel I stayed at my first night in Costa Rica, 2 Israeli guys carrying surfboards. Like long hair, kind of like Cheech and Chong. And I'm like, they're like, oh, Cheech and Chong, we should. Oh, that's a little throwback.

Guys essentially traveling in a VW van, smoking a lot of ganja weed.

Yeah.

Long hair, long beards.

And these guys had just gotten like out of the Israeli Defense Forces, you know? And, and I was like, 3 weeks. I got these whole 3 weeks ahead of me. And when they asked me like, how, you know, how long you going for? And I said it with like, you know, a bit of pride. And, and I'm like, well, how long you guys? going for, like, they're like 6 months. So like they were going from like Mexico to like Patagonia. And, but after that, my world kind of opened up and, you know, I never looked back. I went to China again, kind of backpacking right before law school and traveled all through the country. Low, low budget, shoestring budget, no budget out west into Tibetan regions and have some great stories. And it left a deep impression. Got really interested in the language and the culture and something very foreign. And then as, yeah, you referred to, I mean, I kept going back. I carved out basically a curriculum and made a proposal to the dean and kind of the international affairs office at New York Law School and said, I'd like to go to this university in Beijing, study comparative law, and will you give me credit? And they said yes. So I went back there. I also met my future wife at some point along one of these trips there in Shanghai. And yeah, I mean, so that's, this story is still going.

So, so I want to get a little bit personal here. So you're a student in Beijing, it sounds like, and then you're going to Shanghai to meet friends, see something, and then you just run into your wife on the street or what's the story?

Well, I met my wife actually on one of the first trips that I went and I was backpacking and I was coming back east. A college friend was coming out to meet me and we had just arrived in Shanghai by train, sat down in a cafe. And yeah, there were 2 women next to us who were chatting and they weren't speaking in Chinese either. They both were from Asian descent, but they were speaking in Italian, which was, you know, even more interesting, but they weren't paying any attention to us. It was literally like a cafe. We were sitting elbow to elbow. So like, okay, you know, mind our own business. And then, yeah, this is a true story. Like my wife, well, at the future wife that she was eating and a piece of potato. Like a baked potato came on my plate, literally, and like on my lap. And I, that opened up a whole conversation and said free food, you know? And yeah, got some tips of like what to do in Shanghai and crashed on one of their couches for the next few days, rode their motorino around Shanghai and yeah, plugged into like this whole new world of, uh, and yeah, it's, it's relationships that we still maintain to this day.

I, and, and that's an amazing, amazing story. And it reminds me of the, of that little thing that we all kind of know, but that the magic or the wonder can happen in a baked potato in your lap, right? In the sense that, you know, we, you know, you and I both have young children. Yours are under the age of 10 and mine is now 12. And we try to teach our kids to be curious and they are curious, right? Innately, they're curious as they start their lives. But then as they become teenagers, they become maybe a little bit insecure. Maybe they become a little more comforted.

Mm-hmm.

Maybe in their 20s, they expand their horizon again, and it kind of goes in and out in a way. But encouraging them, like you did, to go sit at a café because that might be where your entire life is changed.

And you have to be open to that, right, Peter, to a certain degree? Like, I mean, you have to be open to that, right? Like, there's a lot of elements in life's equation, and you just addressed, you know, One of them. And, and I think that this is like also an element of, well, you know, curiosity, of course, the openness to, to these chances and uncertainty has always been one of these elements in my life's equation, right?

Mm-hmm.

So how do you face uncertainty? Like most are like, I don't want uncertainty in my life. I want something stable. I want routine. I want something predictable. And I guess it depends also on where you are in your context of life, what age you are, how much risk you can take.

Yeah. And, you know, we're getting deep in— I already have 6 other topics I want to talk to you about. But then, as you're saying, risk, right? Like, what is risk? I was asked about that the other day by a founder. It's like, oh, I think we're taking on too much risk. And I'm like, well, what is it? In his case, it was because he was leveraged with venture debt and other things, right? So there was a financial component to the risk. And I think a lot of people associate risk with some kind of financial implication in the startup land. Of course, there's also risk going bungee jumping or paragliding or something else that is more like a life risk, right? But when we talk about what you did, you were open to go have an experience in a foreign country You know, I've lived in America for 13 years. Back then, also when you traveled, not a lot of Americans would venture out in the world and just be like, I'm going to go here and explore.

Yeah.

It was a little more confined. So what is risk in the context of this stuff? Is it just being open? And then if it is, is it really a risk? Should we reframe that? Should we re-talk about it?

Yeah. And it's like stepping outta your comfort zone to a certain degree. Right?

Right.

And, and to me, and again, it's all contextual, right? To me, it's been transformative in every step of the journey, whether it was, again, like making decision to just hop out of my traditional confines of a full-time job in a city of Chicago and open a new door to a new part of the world. Um, You know, that was stepping out of a comfort zone and it, it planted a seed where, you know, going back to your first question, like, how do you define who you are? I mean, I've defined myself and redefined myself, you know, in my 20s, in my 30s. I'm almost 40 now. Well, I am 40 now. But one of the things, one of the greatest human flaws I believe is that like, we, we almost believe we cannot change ourselves. We cannot evolve. We kind of look at ourselves at a certain point in life and be like, this is who I am. I accept it. But I've learned so much from people along the way. I've learned professionally as well in launching, you know, one of my first startups around 5 years ago. And all of this to me has also been experiential, you know, learnings, learnings that are firsthand learnings that I've had to go through in order to fully comprehend and fully understand. You know, the meaning of that. So, so I'm going a little bit into abstract land here, I know. But there's, there are, there is real-world application to all this. There is.

And as you're saying this, one of the things I like to do on this podcast is, is give people like a couple of nuggets that they can take home and be like, okay, I listened to David and Peter having a conversation. I'm going to change my life in this way now. So if we're going to try this on for size, if you were to give like One piece of advice to somebody who feels stuck, that they cannot change, as you say. What is that one practical step that they can take today to maybe get unstuck?

Speak with someone, right? Like, like organically try and, you know, engage someone in conversation and bit by bit, or read a book to a certain degree, like connect with something that you feel is genuinely gonna move you. And I, so I don't have necessarily have like a direct Answer to that. 'Cause like, what is it you're looking to change? Is it your career? Is it a relationship? Is it like getting a new hobby? Right? One of the hardest things is just taking that one step, right? And then, and then like just opening the door and then you'll see you don't have to plan for all those doors that are gonna open after that. It just, it just happens.

And I think that's, that's also often advice, which is like, just do one thing or just take that first step. And I like the fact that you caveat this by saying, I don't know if it's about your job or if it's about your relationship or if it's about something else. So, you know, it's not like sit down and work on your CV, right?

Right.

That's not appropriate if it's your relationship you're working on. I hope not. So maybe this idea of saying the thing that you're going to do now, let it be something that you don't always do, right? So get out of your comfort zone. So let's say I'm struggling with my job. I'm not happy in my job. Maybe instead of talking to the same people about the fact that you're not happy in your job, talk to different people about it, right? Try and seek out somebody who doesn't necessarily know you super well, who doesn't necessarily have heard the story before, who doesn't know your job that well, and see if a conversation with them will give you new ideas.

New ideas.

We go in the same circles, right? And there's— we talked a little bit about bias previously. If we talk to the same people, we're going to get the same answers. So, or if we spend time in the same countries, you know, we're going to get the same habits.

Yeah. Yeah. No, but I mean, and that's like true for like a Google search, right? You know, you can find answers to some— That you're looking for. Like, it's all an algorithm that's, if you wanna, if you think you already know an answer and you're Google searching for that answer, you'll find it. And that will be like, it'll confirm, you know, confirm a theory that you had. And, you know, that can lead to some type of, I guess, false illusions to a certain degree or a lack of perspective. So yeah, I, I think there's, hopefully there's some nugget to take away, you know, from all this, Peter, which is like, how How do you assess risk? You know, and what type of risks are you willing to take in, you know, in your life? And what are you looking to change? You know, so yeah, hopefully there's some nuggets that people can take away from all of this.

I'm sure there is. Let's— so all this international experience and your own kind of led you to where you are today, obviously physically in Florence in Italy with your wife that you met in Shanghai and your children. But you're also doing, you're in a business right now that also kind of works with, yeah, an international life. Tell people a little bit about what it is that you're doing.

Yeah, sure. So I'm doing several things and, you know, it's all at this intersection of, let's say, an international dimension to it, right? When, after studying law school, even during studying law school, I always knew that I wanted to do something international, international law. But like, what did that mean? How do you, how do you define that? So my journey to where I am today is just an aggregation of certain events and coincidences and also hard work. I got out of law school, I hung up a shingle, did whatever I can do at the time, and immigration fell into my lap specifically with my future wife, right? I had to help her get a green card. I did all the filing myself. And then I started to work with a private law firm and take on some cases and You know, working with people and there was an international dimension to it. And yeah, that's always been kind of my thread professionally. So, you know, fast forward a bit to, you know, around 2019, 2020 in a COVID era, I had experienced enough in about a decade of being in the private immigration practice, working with individuals trying to come to the United States, a variety of individuals from founders to investors to highly skilled workers. families, always focusing on U.S. immigration. And I was doing it remotely. It was kind of a dream. Like I was a remote working immigration lawyer even before COVID And I loved it. I loved dealing with people, but I also started to think a bit broader about the entire sector, the immigration sector. And I recognized that there were certain challenges within the immigration sector. There was a lack of transparency. There was a lack of access to information. There was a lack of access to, you know, immigration advisors globally, and there was a lot in between. So the journey to even move somewhere, to immigrate somewhere on a global scale, to me was very burdensome. And I heard this firsthand. I've experienced this firsthand as well. So yeah, of course, like anybody who lived through COVID, like you start to get ideas. Um, and, you know, Some people decide to, to leave and, and launch a war. But yeah, I decided to dig in and, you know, launch a startup. So, you know, and, and I, I guess that's where, you know, I started to manifest this vision of, of, uh, Relocate and yeah, launch, which, which still exists today and is bubbling today in the global migration space.

Again, another example of somebody having a fairly personal problem and trying to find a way of solving that. You know, immigrating your now wife to to to where you were, and then turning it into a business. Right? Some of the best businesses are are created out of that personal problem that somebody is trying to solve. So what kinds of of you know is it? So if I'm if I'm immigrating, I'm the person listening to this, and I'm in. A highly skilled worker in Sweden and I want to move to the United States. They call you and, and you say, this is, this is how you need to go about it. These are the requirements you need to fulfill. This is how it works. Or is, is that your business? Just to get a little bit more specific.

Yeah. I mean, I actually, I like, I guess there's several different dimensions to what's on my desk, right? In my current capacity, I'm, you know, leading strategic partnerships in the global mobility space for an entity called Build. And this is a startup company, but in many ways they have roots going back around 10 years, working with startups, working with founders, working with highly skilled workers. And I joined them around, you know, well, the beginning of this year to scale what's called the BUILD Fellowship. And it's essentially a very niche immigration solution and pathway for highly skilled workers who have a job offer in the United States or or want to launch their own company in the United States because the U.S. immigration framework itself, if we think about it in terms of just a, where, where we are in the global talent race, how we're retaining foreign national talent, the mechanisms that control migration into the United States, it's complex. It's, it, it in itself, it's one of the most complex immigration frameworks in the world that other countries have actually modeled itself off of. And the BUILD Fellowship, kind of why I was motivated to join the team there, A, because it's, it's, it's a really great team, young team of entrepreneurs and, and doers. And also the mission itself to, to really fuel the innovation economy in the United States by, in your example, working with a highly skilled worker from Switzerland or from India or from China who, believe it or not, Peter, like even those who have job offers in the United States are struggling to get a visa solution. So, you know, it was really refreshing to join a team like that, especially after around 4 or 5 years of, you know, really struggling to get a startup off the ground. You know, the first startup that I had founded, because when I dove into that, I had a big picture idea, right? It was a big vision. I wanted to, you know, ease the burdens of migration globally. And, you know, this was, I guess, in the startup world, you call it boiling the ocean, right? Where if you compare what Build is doing and the work there, why I say it was refreshing in many ways is because it's like in the startup world, again, it's a wedge. It was a very specific solution to a very specific problem. So yeah, there's several things, I guess, always again in the, in the immigration space that are on my desk at any given time.

I love it, David. So you've done you've done you've done relocate. You're now in the Build Fellowship. I think you've done a couple of other things. You mentioned your first startup some time ago, and I know that when we spoke previously, you were besides you were going on a hike, which I which I love when we chatted. We also talked about some of the the common mistakes that you have seen early startups make. So if we kind of take it back to you putting your founder hat on and we're trying to add some value here to the people listening. What are some of the mistakes that you made early on building your business?

Yeah. Yeah. I honestly feel like I could write a novel about this, Peter. And yeah, yeah, of course. I mean, I think one of the Biggest challenges to being a founder and looking back now, I was very passionate about the idea, the idea itself. And what I learned the hard way is that an idea in itself doesn't mean it's a business.

Right.

Differentiating that when you're kind of in the, in the heat of passion is a very difficult thing for any founder to do with an, you know, with the spirit to actually make it work. So there were several, you know, mistakes that I've made along the way, right?

Mm-hmm.

The timing to launch a business like that was, and still is in many ways, fortuitous, actually. You know, I was actually, it couldn't have been a better time to have an idea like that in a post-COVID world. People are looking to work remotely, move from their, you know, move from where they typically were. So what went wrong? Like I've asked myself this question a thousand times, you know, fast forward 4 years later. I, I had a, an amazing team. I, I, I, you know, a really amazing team. At our peak, we had about 6 individuals who were working on the concept of Relocate, uh, really talented individuals. But I was burning cash. I was burning cash that I didn't necessarily, well, have, but much longer and the operational costs could not justify the business itself when there was no revenue, no revenue. So, you know, at that time it did, I didn't really understand what it meant to build a really a lean startup, you know, to me, I was like, but I, people are the most important asset and we can debate this, right? Because many, you know, founders or individuals who have successfully launched a company perhaps will say the people who you involve are some of the most important. And there were, there were great ideas. There was a great rapport amongst the team. We felt a certain energy. We, we all, I guess, believed that it was gonna go somewhere. And I'll never forget one of the first employees that I had, Catherine Funk. She said at the end, like when, you know, everything dissolved, it's like, I was kind of just waiting for you guys to pull this rabbit out of a hat and it never happened. So, yeah.

If I can build on that point, David, for a second, you're, I, I completely agree with you and I've written about this ad nauseam, right? The importance of the people in the business. And so we see that a lot of people with great ideas are good at attracting other people and doing things and getting good teams. So I think if we were to encourage our founders to do one thing, it is teaching them the financials of running a business, right? Making sure that they're aware of what cash flow actually is and what it means and think about it a little bit long term. And the reason I want us to focus there when we talk to our founders is because all the other stuff, the idea, working on solving the problem, working on building the team and stuff, they love that. They'll get good at that. They'll spend a lot of time on that. But this thing called the money and the accounts is what most people don't enjoy doing, and therefore they don't do it, and they end up getting in cash flow problems, right?

Yeah.

So if you're listening to this and you have to decide what to do today, sit down and look at your financials.

A hard look. A hard, honest look. And even get other people's views, right? Because one of the best things you can do as a founder, well, is A, recognize your skill sets, right? And B, of course, recognize the skill sets that others might have. So You know, get other people to look at those numbers for you. Because, you know, if, if that's not there, you know, ultimately at the, at the end of the day, what you, what you'll have is a beautiful idea, a passion that's, you know, of course important, but something that you cannot monetize.

Right.

So yeah, it, it, it's, it will save a lot of suffering to give that a hard look. an honest look in the beginning to understand if it's something that, that can actually succeed.

I've been wondering a while about how do we make these, these tasks, these things that we need to do as founders that nobody wants to touch with a 10-foot pole, how do we make them attractive? Right? How can we make understanding your financials attractive? And I think the— I haven't found the answer. But I think it comes down to asking yourself, what is it that I worry about at night? You know, when I'm a founder, I typically worry about product-market fit. I typically worry about funding, and I typically sometimes worry about finding the right team or having the right team. But the 2 first topics are typically what comes up when I speak to founders. And so I said, one of the ways to get engaged with this, or the reason you should get engaged with it, is you will sleep better at night knowing what your numbers are, even if they're bad. Because you know, right? You can. It's easier to know what the problem is and do something about it than to fantasize about whether I have a problem or not, or not knowing how big it is. So that hard, honest look that you talk about, I think, is super important. David, unfortunately, we have to start rounding off some parting advice. Back to the one thing people should remember from this conversation. You know, imagine you're a you're a founder CEO. Maybe you've been going for a couple of years with your business. and you're listening to this, what should they learn from, from David Cantor at that point?

Don't give up, but know when to pivot and don't stop listening to other people. I just picked up The Promised Land by Barack Obama and was reading that. I've been devouring it recently and I'm finding so many different themes in his life story. And, you know, one that I just read last night that comes to mind when you ask this question is You know, I was, I'm basically reaching my 40s. My marriage is strained. You know, I didn't have much money. I had this idea to run for a congressional office and he lost.

Yeah.

And, and he lost and, and, and, you know, then it follows where he is like, okay, maybe I should just go back to, you know, my original plans. And he was working several jobs at that time, you know? And not necessarily losing hope, but you can see the thought process of reevaluating and reassessing his motivations, right? For, for wanting to run for congressional office in the first place. And you can see him reassessing and kind of gathering back his courage to do it again because there was a seed planted, you know, and you can, this comes across right away. There's a seed of this entrepreneurial spirit. This, this belief that, you know, you can change the world and any founder or anybody who's launching something, they probably have that feeling as well. It's inspiring. So you're, you're, you're going to face defeat. You're going to face failure. You're going to face struggle. You hear it all the time. I heard it all the time when I was launching a startup, but I didn't even believe it to a certain degree. It's like, I'm going to succeed no matter what. Of course. But I've, yeah. So, so if I were to leave some parting advice, Peter, and we were talking about this right before, I don't see value and success as one single accomplishment or not. I see it as a range, like a mountain range. I see you succeeding in certain things and failing in others and succeeding again. Some peaks are higher than others in life, but it's a range and that range can be as long and vast as you want it to be. Right? So don't give up.

Don't give up. I think those, those are great. It's a great book, The Promised Land, whether you're a Democrat or Republican or something in between, if you're not living in the United States. Reading it will certainly teach you a lot of stuff about perseverance and the power of that seed that you talked about, David. So I'd encourage everybody to pick it up. Thank you so much, David, for being on the show.

Thank you, Peter, for having me. It's been great.

And to everybody listening or watching this, we'll put David's information in the show notes. So make sure to go and follow him and check out what he's doing. With Build and his other projects. For me, I'm easy to find, petersorgenfrei.com, or look at me on LinkedIn. And oh, by the way, a tidbit, Barack Obama follows me on Twitter.

So if you want to be like him, you should do the same.

I'd be happy to have you. Thanks so much for listening. If you have any topics or any ideas that you want us to cover on the show, just let me know. We'd be happy to hear from you. Thanks so much and have a great day.