Jason Tartick On How The Bachelor Upgraded His Career & Love Life - Exclusive Interview

True "The Bachelor" fans have followed Jason Tartick's journey since day one. The dating show alum began popping up on television screens in 2018 on Becca Kufrin's season of "The Bachelorette." Since then, he has found himself in a loving relationship with fiancée and former Bachelorette Kaitlyn Bristowe, all while finding career success and financial freedom. In an exclusive interview with The List, Tartick detailed his personal endeavors and summer plans, and he revealed where he'd be if he hadn't accepted that Bachelor rose.

In addition to the television personality's social media stardom, the "Trading Secrets" podcast host utilizes his previous corporate banking experience to encourage transparency between money and careers. Tartick also gave The List some nifty career and financial advice and explained how his newest entrepreneurial partnership came to light — the Cubicle Caddie. It turns out that you can actually mix business with pleasure, and the best-selling author combines his diligent spirit with his love for the golf course. We also got to hear about his partnership with Wyndham Resorts and how you can earn the Cubicle Caddie with their rewards program.

I want to start with talking about your newest project, the Cubicle Caddie. I'm curious as to why you teamed up with Wyndham Rewards to launch this new amenity. How'd it come about?

First and foremost, what's cool is that I'm here right now at the Grandover Resort. This resort is also going to be the host hotel for the 84th year of the Wyndham Championship, and it's the final stop in the PGA tour, which is super exciting by itself. But I partnered up with Wyndham Rewards because I am a Wyndham Reward member. It's always cool when I could partner up with a company and a loyalty program that I believe in, that I'm aligned with, and that I've been using before they even reached out. That's a beautiful thing.

The other thing is with my lifestyle [and] Kaitlyn's lifestyle — we work, we're on the go, work hard, play hard, all the things. When I heard about this Cubicle Caddie, I was like, "This is the coolest thing I've ever seen." I'm in a golf cart right now. It's crazy. I can change the background so you think I'm somewhere I'm not, but really, I'm on the 18th hole, which is pretty cool.

With the Wyndham Rewards Program, if you're at one of the five resorts [where] they have the Cubicle Caddie, you can get this for free when you book a tee time, which is awesome. It's got wifi in here. I have my laptop on a stand that's in the golf cart. This is probably my favorite part — they have this button that makes these crazy noises. If I wanted to go putt, I could hit the button. It's like a dog barking — like, "Sorry, Robin's barking. Got to go." Isn't it incredible?

You also mentioned you have a lot of projects going on — this partnership, the podcast, your best-selling book, the consulting company, and the list goes on and on. How do you keep the entrepreneurial spirit alive?

It's all about doing what you love. To keep the entrepreneurial spirit alive, you have to be energized and electric about what you're doing, the impact you're making, and what it provides [you]. The things that I love about the entrepreneurial side of my passion projects are [that] they provide me the income that gives me flexibility and freedom. I can use something that I do to make an impact, and it's something that I'm aligned with. When you hit all three of those, you're in a position to be fired up. I was making a joke earlier — when I worked for the bank, I would have to set my alarm every day, and I would hit snooze five times. I don't even remember the last time that I had to set an alarm. That's a result of being aligned with something that I'm excited about doing.

Kaitlyn also has several endeavors, from a hair accessory brand to a wine brand to television appearances — all that jazz. Do you ever find yourselves having a hard time balancing it all?

There's a ton that comes into play when it relates to personal and professional balance. Sometimes it comes at ease, and other times, it's challenging. [It's] communication — we're both not the best planners, but trying to plan is definitely extremely helpful. Even [with] this partnership, it's about aligning the things that you can do for work but also have fun with.

This week, I'm going to hit four birds with one stone. I'm going to be at Grandover Resort. I'm going to get my membership points. My parents live in Charlotte, so my dad's going to come up. We're going to play golf tomorrow. My mom's birthday is June 16. The ability that I get to see Mom, see Dad, and also do work ...

Kaitlyn right now is in LA. She's got a podcast with Iman Shumpert and a few other people. Iman won "Dancing with the Stars" the year after her. She'll get to do a lot of her work stuff, but I know she's seeing a ton of friends too. Then we're back in town together next weekend in Nashville. We're actually doing CMA Fest together with Charity [Lawson], the Bachelorette. They're doing a big premiere out there with Charity that we'll be part of next weekend. It's a balancing act, but it's fun. That's a lifestyle we love.

For the CMA Fest, is that the OG "Bachelor" crew that's coming together? Do you know who's going to be at that?

CMA Fest ... This is through ABC to promote the premiere of "The Bachelorette," and Charity will be there. Kaitlyn's going to do this portion where she's interviewing Charity. Katie Biggar and Zach [Shallcross] will be there, and Noah [Erb] and Abigail [Heringer] will be there as well. Kaitlyn and I are doing something Sunday.

I'm still buddies with Tyler Cameron — I shot him a text. We were talking yesterday: "When are we getting together?" He asked me, "Are you doing CMA Fest with those folks?" I said, "Yes, I'm doing CMA Fest," so we'll be heading back there.

You quit corporate America after appearing on "The Bachelor" and restarted your career. I'm curious to know if you think you would still be working at that corporate bank if you decided not to do the show.

The quick answer is no. I had a plan in place. I moved from Rochester to Seattle. I talk about it in the book — I talk about exactly how much I was offered to go out there. Part of that was to build the safety net to give me my next step. I actually wanted to ... I grew up, I got to watch Rob Gronkowski early and often, and I got to see some of the people on his team. I thought it was pretty cool what the agents were doing. That was one thing I was thinking about trying to pursue, becoming a sports agent. Well, I get this opportunity to go on the show, I go back to work for a year, and then all of a sudden, social media agents are calling me to do work. I'm like, "Well, this is cool."

A few years ago, I learned I could really help people. I created an agency that I had an investor in and helped fund and get up and running, and we helped creators and comedians and actors and musicians and athletes on the agent side. I got to pursue that.

What's cool about the podcast is I get to talk to all these people about breaking this taboo about where they make money and how. While having them on the show, we get to do a lot of educational stuff. I get to have a lot of finance gurus and or partners come in to talk about how and what they do to separate themselves, then bring that to my following, which was all derived from "The Bachelor." [It's] everything from talking money, travel tips and tricks to asking Gronk how much he made on his last partnership. It's been fun.

You've talked a lot about your experiences on "The Bachelor," and you told The List once before that some part of you always feel a little bit indebted to the franchise in terms of your career success. I don't want to credit it all to that, your career success and relationship with Kaitlyn, but ... do you still feel that way?

Yes. Oh my God, absolutely. I'm on a golf course right now. I joke around — the three luckiest things that I ever got in my life: getting on "The Bachelor," meeting Kaitlyn because of the show, and getting a hole-in-one. Those are the three things I find the luckiest. I'll always be indebted to that franchise. Without that platform, the majority of my life and my world doesn't exist personally, professionally, and financially. [I'll] always be extremely thankful. Now, we can still be critical at times — we can give some feedback, but I still will always be a supporter of the franchise.

If you could give advice to someone considering taking the leap on a dating-focused reality show, what would it be and why? Whether they're looking to take the leap or they're afraid to go on a reality show because of what other people think.

The biggest piece of advice I'd give someone if they're thinking about going on a show is: Think about 50, 60, 70 — hopefully 100 years from now — when you're on your deathbed and you remember marquee, exciting times in your life. It may or may not be this next year of work, but doing something like this might be. We get such a finite amount of time in this world to experience things and enjoy things. You [have] to take a shot — especially if they excite you.

Once opportunities come in the past, they're gone, and living with regrets is a tough way to live. If you're going on a show and you commit to it ... Like everything, commit to it. The analogy I say is, "You're going on a roller coaster; you're strapped in. There's no reason to try to panic to get out of that ride, because you are strapped in and you are going for that ride. Enjoy the twists, turns, ups, downs, lefts, and rights. Scream and have fun as opposed to trying to battle and control the ride because there's no controlling the ride."

That's well-spoken. Great advice. Because you're in that OG "Bachelor" group, have you ever had any wild fan interactions — either during or after the show — that stand out in your mind?

That's an interesting question. The whole idea of having fan interactions is still numbing to me in the fact that how does that exist? What does it mean? Even to this day, the whole concept is pretty crazy. But one of the most special things was going back to my hometown, going back to Buffalo. My family lives in Charlotte, so my parents are able to drive here to Greensboro at the Grandover Resort because they live in Charlotte. They're two hours away; they didn't live in Buffalo. My brother lives in New York City with his husband, so they had to rent a house to call it my house so that my hometown could be in Buffalo and bring the show back for that. Every now and then, I go back to Buffalo, and people [are] like, "You're the Buffalo kid from the show. You brought them to the show at this restaurant and this experience." I always found that to be pretty exciting.

That's so funny. You're getting together with the OG "Bachelor" crew next week. Do you have any other things in the works for the summer that you're willing to talk about?

We [have the] CMA Fest next week. Kaitlyn's birthday is June 19, so they're planning for that. We're talking about going up to Canada. Because before [the] pandemic, we'd always go up and spend some time in British Columbia. More to come on that — in the meantime, [I'm] using the Wyndham Rewards membership to get all these points for all this travel, which is going to be pretty crazy. Now that I'm here, and I know that this is the host hotel for the PGA Championship, I might have to put this into my summer plans and get back up here.

I have some rapid-fire finance questions for you, a for-or-against thing, if you're ready.

Cool. Let's do it.

First, cash stuffing has been a big trend as of late. It's stashing paper money in envelopes that's supposed to help ease financial anxieties. Do you have any thoughts on that?

If it does ease your financial anxiety, I'm for it. If you tell me the technical concept of stuffing cash in an envelope, I'm against it. The reason I'm against it is because at the rate at which inflation is moving right now, you're losing money on that cash. That cash is losing value by the second. However, the value that it's losing is not as big as money mismanagement. If you are not properly managing your money, then that's a trick that has definitely been proven to work.

There's now a strong emphasis on getting rich quick with side hustles. I've seen that all over my TikTok page. What are your thoughts on that?

[With] side hustles in general, what you're doing is you're exchanging your time for money. Whenever you're exchanging your time for money, depending on what it is, there's only going to be so much of a limited upside with the wealth that you can earn from that. Some of the biggest wealth that's created is investing in appreciating assets — that's a deeper discussion.

But the high-level thing is when you hear, "Get rich quick," that immediately puts red flags up because the whole concept of getting rich quick goes against every type of economics and financial theory out there. It's the exact opposite. Do your due diligence and don't get caught in a lot of get-rich schemes, because there are a lot out there. If it sounds too good to be true, especially when it comes to money and returns, it is too good to be true.

The 30-Day Financial Cleanse recently went viral. I don't know if you've seen that yet. Do you feel like it's worth the hype?

The 30-Day Financial Cleanse, essentially, is just starting to practice good financial behaviors. Imagine you want to get back in the gym — you got to start with small wins, having that healthy lunch, or getting one workout a week. That's the idea behind it. If you can change your money habits because of something like that, then give it a go. The idea is money mindfulness matters, and it also matters what you're spending.

Think about what we're talking about here today. You have to look as a consumer where you can go to get the best return on where your dollars are being spent. For example, if you're spending a lot of money on hotels and transportation and hospitality, go with programs that are the most generous. Go with programs that are the most efficient, that'll give you the best points return on your dollar, that'll give you free stays. It's so important as a consumer that you look where dollars are going, you limit where they're going, and when you are spending them, you're using the right programs and means of paying for them.

My last one for you is investing in big companies individually, like Tesla, Amazon, Whole Foods, et cetera. Are you for or against that?

Unless you're really doing due diligence on the company, because so much shifts so quickly in today's world, you'd be better off looking at an index fund. As opposed to one specific company in one industry, why not own the entirety of the industry? It'll mitigate your risk; it'll reduce volatility. In today's world, unless you're glued to analysis and due diligence — which, quite frankly, most people are not — your concentration in one company becomes riskier. But if you're in a company like some of the ones that you mentioned, they're pretty large. The larger they are, the greater volume they have, the less risk associated. But I would recommend an index fund over one specific technology company, especially in 2023.

You learn more about the Cubicle Caddie on the Wyndham Rewards website. You can also head to Jason Tartick's Instagram account to keep up with his latest projects.

This interview has been edited for clarity.