How To Financally Plan Before Marriage | Jason Tartick & Kaitlyn Bristowe

50m read

·Nov 7, 2024

It's a crazy thought process to leave 10 years of NBA grinding all over the country in corporate America to go on reality TV, but it was that thought process that actually changed my life.

Somebody in your family, either side, comes to you and says, "Look, let me give you ten thousand dollars. Here's your answer: I'm going to give you 10,000, it's a gift, but it only has one condition. You never, ever, ever ask me for money again."

Everyone, Jason, I'm going to start with you. You had a very successful Wall Street career, and from what I can tell, you basically quit to go to reality television. Are you basically out of your mind? What is the story there?

I mean, that is like the most fair question out there, and I think that's a question that most people that abide by the system would ask: why would you ever leave this great job to go on reality TV?

It's the same system that kind of had me checking the boxes for promotion after promotion, and I was just miserable inside. But on the surface, everything was good. It was actually probably breaking that whole thought process that the system created that changed my life personally, for sure. Definitely professionally and financially.

So I think back at it, and what I'm doing now with the platform of trying to get people to restart and rewire the way they think about their career development and personal finances, and what I've been able to do in just three years with now this platform on Restart, Reset Instagram—we're making a million impressions a week, and we're making an impact on the way people change their careers, think about their careers, and personal finances.

So, it's a crazy thought process to leave 10 years of NBA grinding all over the country in corporate America to go on reality TV, but it was that thought process that actually changed my life. And I think in the last three years, Kevin, with what we're trying to do, I've made a bigger impact than I could have in probably five careers of being a banker.

Okay, but the basic theory there, what you're telling everybody and me is that you're able to monetize social media—that's basically what you're saying, right?

Correct. I mean, yeah, precisely. You're able to monetize social media, and I think you've got to take risks when opportunities come to fruition. I could be a banker any day I want to.

I could go be a banker—snap my fingers today. Do you have the chance to like take a shot at going on a reality TV show every day? Absolutely not.

So for me, I was kind of unhappy with the career and I'm like, "Let's take a shot. Let's see what happens." But there's a lot of risk there. First of all, you take a shot, you could have sucked, and that would be the end, right? That's risk number one.

Not number two; you may have never got traction. Lots of people go on reality television, never get any traction on social, but neither of those things happened to you. You somehow found the path.

Just, you know, before I go to Kaitlyn, I want to talk to her about this too. But, yeah, what number—everybody's interested. Everybody wants to have a social media base. Everybody wants to do what you did. Tell me the number. Just follow us. Let's pick any platform—let's just go Instagram—at what point did you say, "This is working"?

That's a good question, and the difficulty in answering that question is that based on your engagement on Instagram, the ability to monetize could be drastically different. You could have an Instagram account with 50,000 followers and monetize much more successfully than an account with 2 million followers.

So there's not this architectural blueprint with Instagram. For me, I think when I did cross like the 500,000 mark, that was when I would say deal size and deal quantity was inflowing at a pace that at that time I was trying to keep up with, as opposed to trying to find more opportunities.

Alright, Kaitlyn, over to you. Same thing—you've got a reality television background, right? And you basically meet this guy, and all of a sudden, you're two kind of social media stars. Are you driving off each other? Is it like a jet? One of you finds the other and you're getting the hydrofoil? How does it work?

Well, I think we both help each other in the best ways possible. I'm definitely not a numbers person, and I'm starting to learn the business behind social media and how it can be a business. I'm more of a creative thinker, and social media has just worked for me because I am like what you see is what you get.

I say inappropriate things; I've just always been myself on my platform. Jason has helped me on the business side, and I've kind of helped him be more of himself on social media because I see the power in authenticity and what that attracts people. It keeps your engagement up and everything with brand deals, love to see it.

So, I think we've helped each other in that way and kind of have been able to compartmentalize like that's a business, but we can also use it for fun and engage people in our own relationship and grow a business while doing that.

And Kaitlyn won't say it, but I'm going to say Kaitlyn was a social media powerhouse well before her and I started getting together.

She had been crushing everything she was doing within that space well before, so that was much, much before I came along. Would you agree?

Well, I mean, I went on TV before you.

Yeah, but I mean, Kaitlyn, when you started television, and you just, you know, I remember when social media in reality television was frowned upon because the networks wanted to control the message. Then all of a sudden, they started to realize that you could push eyeballs with social media—that was about six years ago.

And now it’s all about social media. You went through that transition, I assume, right?

Yeah, I was actually—so it was six years ago when I went on The Bachelor, and that was really when Instagram was taking off, and you did not know the power behind what could possibly happen or that you could create a business or that you could start things like that on social media. It was just the unknown at that point.

So, for me, I was really going on the show for an experience. I didn't have the background that he had. I didn't actually have education besides my high school graduation. And so, I was like, "There's really no loss here for me, and I would love to have a platform and a name and try and get into hosting or doing something like that."

So, I was able to watch social media really grow, and I was able to have a really good team on my side because I went from, you know, working in a restaurant thinking like a hundred dollars in tips was a lot of money to Flat Tummy Tea telling me, "Tell everyone you poop out this tea and you're gonna make 10 grand."

And I was like, "What?" And so, I was so excited, and my team was like, "Absolutely not. If you want the longevity of some sort of social media career, you are going to turn down a lot of money to build a really important platform, and that's the only way you're going to do it is if you turn down all this money."

So, I've seen social media go through a lot, as I'm sure you have too.

Okay, so let's explore that for a minute because that's fascinating. So many people would like to have the lifestyles you both do and sort of monetize social media, but you just cued on something that really turned out to be important—one of the factors that I think a lot of people didn't understand about social media just 36 months ago is that this aspect of honesty, particularly when you're promoting a product.

People smell it a mile away. So if you're being offered 10 grand to poop out a tea and you don't poop tea, you know you can't take that 10 grand—is what you're saying, right?

Yes, exactly. And coming into that world, that was a lot of money to say no to. I mean, it's still a lot of money to say no to. But, yeah, that's exactly right.

And once you realize that and see the power behind engaging your audience and having them trust you, that's what's going to make them loyal, and that's what keeps them around.

And that's how you keep—you know, that’s why a lot of people come off reality TV and crash and burn after, because they're just trying to make money in that moment.

Alright, let's talk a little bit about Kaitlyn's wine business. Now, I'm also in the wine business, so I really know how hard that is. I've been in at it for about 10 years and only started making money four years ago.

My model's a little different than yours—you're selling through big box retail; you're in Walmart, right?

Yep. Let's talk about that model. You're basically licensing your name, but I'm going to make the assumption—I'm making assumptions. I don't know the model, but I'm going to make an assumption because I know the business so well.

The best strategy for you is to partner up with a winemaker who has logistics to ship to somebody as big as Walmart, and then you brand it? Is that what happened here?

Yeah, exactly.

Okay, and have you told it? I mean, how much work do you have to do to go and get people to pull a bottle off the shelf? Do you have to actually show up for tastings?

I mean, I would if it wasn't quarantined. I wanted to do that so bad and go in there. Actually, no one's doing tastings right now because of that. I mean, maybe they're starting to again, but yeah, it was—I have a really incredible team. I have two business partners that really have helped me navigate this whole journey because, again, I am the brand, right? Like everyone knows Kaitlyn Bristowe loves to drink wine.

I've always wanted to create my own wine label that I have a very loyal audience, and my podcast revolves around drinking wine. It's called Off the Vine, and it just was such a natural thing for me to get into. I worked in the restaurant business for over 10 years, and I learned from sommeliers, and I was taught by them. I had to train servers with wine pairings and knowledge about wine, so I was always really passionate about it.

And I think everyone, again, they could see through the—they knew this was something that was like a dream come true for me to do. So it is a lot of work and effort, but I'm so grateful for my team because they're the ones that are doing—you know, well, I mean I'm on every call, and you know, but they're the ones that really do the business side of things.

And I'm just able to, you know, be the brand and push it through that way because social media, again, I'm reaching so many people in different cities and different states. You don't need billboards anymore, and you don't need—obviously, I could just go on my social media and say, "You know, go check out this Walmart," and like I'm going to go to a couple today—maybe I'll run into you—and people go out and buy it.

And I really believe in the wine too because it's all we drink; it's really good. And I think, again, people just know I'm super honest and they believe in it.

Interesting story to the social media aspect: she actually didn't immediately go to big box, right? So she started going direct to consumer through social media, built the brand, they were selling at a pace they couldn't keep up with. They then went through distribution and they blew records out in British Columbia, Alberta, and Ontario once they actually got into stores.

And so Kaitlyn put all the money up front. Within the first year, she was profitable, got her investment back through distribution.

And when some of these big retailers were seeing these numbers and these endorsements from these distributors and things that were happening, they were like, "Alright, we got to give this a shot." So the model from D to C to being in Walmart effectively happened in less than a year and a half.

And it all goes back to that conversation—the power of authenticity, brand building, and being able to also use social media to promote to so many people, right? So Kaitlyn's like Bethenny Frankel, except nicer.

Yes, that's exactly right. I am Canadian; I am much nicer.

I know Bethenny very well, so I say that with a little humor and humbleness. But, so Jason, back to you. You know about investing and understanding investing, and you know, now that I understand you guys are contemplating marriage here, we're going to get into that in a minute. How do you handle that now? What do you think has changed in terms of your Wall Street attitude versus how you take care of your own money and Kaitlyn's?

What do you do?

I mean that’s such a good question. One of the difficulties I would say is when you're W-2, when you're working for a big corporation, there's so much security, right? You know what check’s coming in, when it's coming in, you know your bonuses, although those are subjective, and that's a whole different conversation.

I think one of the big challenges for Kaitlyn and I is making sure that we're on the same page with our finances, and that we are—while we're in this period of being able to monetize at an accelerated rate—the big question everyone has to ask themselves is like how long is this sustainable?

So one of the big things Kaitlyn and I do is we are wide open with our finances, and while right now income is at a point that we probably never expected, we're trying to scale back our expenses so drastically so that we can plan for a longer period of time from a financial perspective.

And I think, you know, one thing that's interesting that I'm going to ask you a question actually is we open our finances, but now we're starting to like look at a home and we're starting to plan for our wedding and things like that.

Do you have, as the Shark, the investor, with all your experience, what type of advice would you have for us as we're trying to plan for both the long term and the short term in a world where you kind of grew up in entrepreneurship, building a business, selling it, and the ups, the downs, the highs, the lows—like what insight do you have?

So let me give you some advice that comes from experience, but also what I learned from my mother, who was very pragmatic when she was single and growing up. She was taking 20 percent of her paycheck, and she worked in a family business that made children's winter clothing and worked for her grandfather. They used to pay the girls in cash each week, and she took 20 percent of it when she was 19 years old.

I didn't know this till after she died, but she was packing it away in her own name in basically telco bonds and the S&P 500 stocks. That portfolio was there for 52 years. She was married twice; she kept it secret from everybody. When she died, the executor called my older brother and said, "You got to come down here. Your mother died a really wealthy woman."

And I went, "What?" I always wanted to know how she paid for cars and university—paid my own college and took care of her own family. It never occurred to me that she was investing this way.

So she basically only spent the interest and dividends, but over that period, this thing grew to a huge amount of money, and she was all about just taking a portion of what you make and setting it aside.

Not saving it—saving doesn't make you money. You make 0.3 percent investing it. I learned from her, and now I apply it to sort of marriage, and I look at it this way: when I got married, we had nothing—zero dollars and nothing at all.

So we started the journey together; we were pretty open just like you guys. But there's two things I would say that I have learned: a woman should never give up her own financial identity. She should keep an account in her name, credit cards in her own name, as the guy should. You need your own personal identity in terms of the markets because they don't consider couples a financial identity; they consider individuals.

You don't want to harbor bad karma, but fifty percent of marriages in America and any Canada and Mexico end in divorce within seven years, and it has nothing to do with infidelity.

This is what's so incredible: it’s never infidelity. Most marriages can actually survive infidelity, but what they can't survive is financial pressure.

So it sounds to me like you guys are doing the number one thing: planning together because the marriages that break up, it’s usually one thing—one of the two never did any financial due diligence on each other, and maybe that other party was a spendaholic or a gambling addict or had bankruptcy in their family or had some secret financial issue that they didn't disclose and it just completely corrupts the marriage.

It's planning and saving, and it's really boring, but it's so important because the third member of a marriage is money. I wrote a book on it; I call it "Men, Women, and Money."

It really looks at all of this stuff and realizes that great marriages that last a lifetime have a lot of financial stability; if that's your plan, you guys are going to make it.

I got a follow-up question because I think we live in a world right now where incomes are just all over the place, and they're changing drastically within partnerships.

So there was, you know, a point several years ago I was making more than Kaitlyn, and there's a point today Kaitlyn's making more than me, and who knows in 10 years if that changes or five years.

So what are your thoughts on just the whole idea of budgeting and spending based on what your individual entity—like my entity is making, right? So if Kaitlyn today is making more than me, how do you think budgeting should be?

Should it just be correlated to your only income? Should the couple look at it as a whole? Like, what's your thoughts on that?

Here's how it has to work; this is the only way to do it, okay? Otherwise, you're going to run into problems. Your income—and you're right, you're absolutely right—incomes are all over the map.

There's capital gains, there's income, there's royalties, there's your check from YouTube if you're running a channel, all these things are different: speaking gigs, advisory businesses, all that stuff.

So what I would do is buy a home together in both your names, after you're married. It is an absolute mess to buy property if you're not married, because there's just no way to resolve it.

So you rent until you marry, and then you buy a property in both names. But you keep your own accounts, and you both keep—you both have accounts, you both have credit ratings, you both have your own investments in your own name, and then you have this third account.

And you both contribute to it to basically pay for the house, the mortgage, all the things you buy for the home, everything you share together, all the money you spend on vacations together—you contribute equally.

You know, because you're basically baking—you're both in a business together, but you still have your own gig. So if Kaitlyn makes more dough one year because her wine's exploding to the upside, good for her—that's in her name.

And then if you have something else going on, maybe you make an investment; it's a huge capital gain—that's in your name.

Yeah, now you're still married, and I would highly recommend a prenup that says we go in together; we know we've got to have a number, you know what you're worth, and then you grow together.

And where it matters is when you have children, because if you never have kids and you divorce, it's much easier to separate the assets. You sell the house; you've got your own dough and your own accounts, and you fight a little bit about should there be a true-up amount, but it's not a big deal.

But if you’ve got kids, all bets are off. All these prenups are worthless once you have children because you can fight like hell for their support, and they should get it. I mean, you brought that person into the world; it's your responsibility.

Where people screw up is one of them gives up their financial identity—usually the woman—very stupid idea, very hard to get back.

I mean does that not sound like common sense?

I'm like, why didn't I ever think about the third account? It is complete common sense; you're right. That third account makes so much sense.

And even we could do, like, you could do fun activities, right? Like you go out for a nice dinner and stuff. You can just like use the third account or something.

One thing you both have, that credit card—you both have that card, right? "Honey, we're doing this off our combined account."

"Honey, I'm doing this on my own account because I want to buy a watch, and you don't need one."

I have that fight with my wife every week. She says, "We don't need another watch; you're an idiot." I said, "It’s for me! This watch is for me! I'm putting it in often when I die along with the other thousand watches. It's just one of those... I love it."

Now, one thing we—I have a podcast called "Trade Secrets," and we talk—get uncomfortable, or we get comfortable talking about uncomfortable things as they relate to money. And breaking the taboo of talking about money, I think prenups is like the definition of that, right? Like people hear prenup and they're like, "I don't want to talk about it."

But I think getting comfortable with those conversations saves so many more headaches moving forward. So would you say, obviously, you just gave Kaitlyn a suggestion in our situation, but in general, do you think every couple should have a prenup to some level, or do you think there are certain thresholds, or what's your overall take on prenups?

100 percent get a prenup for one reason: it forces you to do financial due diligence on each other. It forces you to ask the tough questions; it forces you to expose any weakness that could eventually kill the marriage off.

I mean, you really got to—when you do due diligence on each other, it's really something you're doing out of love. That's why I look at it. You're saying, "I'm making a lifetime commitment to you, and I want to know everything—the good, the bad, and the ugly, the crazy aunts you have, the nutbar uncle—all that stuff. I want to meet them all; I want to know what I'm getting into."

And I'm going into this 100 percent because if you don't do that—and that’s kind of what happens—a prenup is sort of a commitment to marriage. You're forming a union.

Eventually, look, it's fantastic—you’re in love; that's so euphoric. Everybody should have that. But 20 years from now, the reason you stay together is you built something together. You had friends; you have a home; you’ve got kids, whatever it is.

And that is a family you built, and you did that which is really a business at the end of the day. The reason the family stays together is financial soundness.

I wrote a book on it; I call it "Men, Women, and Money," and it really looks at all of this stuff and realizes that great marriages that last a lifetime have a lot of financial stability.

If that's your plan, you guys are going to make it.

I got a question—follow-up question because I think we live in a world right now where incomes are just all over the place and they're changing drastically within partnerships.

So there was, you know, a point several years ago I was making more than Kaitlyn, and there's a point today Kaitlyn's making more than me, and who knows in 10 years if that changes or five years.

Should it just be correlated to your only income? Should the couple look at it as a whole? Like, what's your thoughts on that?

No, here's how it has to work—this is the only way to do it.

Otherwise, you're going to run into problems. Your income—and you're right, you're absolutely right—incomes are all over the map.

There's capital gains, there's income, there's royalties, there's your check from YouTube if you're running a channel—all these things are different—speaking gigs, advisory businesses, all that stuff.

So what I would do is buy a home together in both your names, after you're married. It is an absolute mess to buy property if you're not married, because there's just no way to resolve it.

And then if you have something else going on, maybe you make an investment; it's a huge capital gain—that's in your name.

Yeah, now you're still married, and I would highly recommend a prenup that says we go in together; we know we've got to have a number, you know what you're worth, and then you grow together.

But if you’ve got kids, all bets are off. All these prenups are worthless once you have children because you can fight like hell for their support and they should get it.

I mean, you brought that person into the world; it's your responsibility.

And so, the way I look at it is everything is 50/50 in terms of all the costs together, but you keep your own accounts, your own investments if you wish. And that way, if something goes wrong later, it’s very easy to separate where people screw up is one of them gives up their financial identity—usually the woman—very stupid idea, very hard to get back.