This as-told-to essay is based on a conversation with Jason Tartick, a former corporate banker turned reality star, podcaster, author, investor, and entrepreneur who appeared on season 14 of "The Bachelorette" in 2018. It's been edited for length and clarity.
I was working as a senior corporate banker right before I applied to be on "The Bachelorette."
As the vice president at KeyBank, I was working with companies that earned revenues of $100 million and greater, and I was doing all the lending to them.
Throughout my career in corporate banking, I executed over $150 million in lending transactions. My base salary as a senior corporate banker was $165,000. I'd also gotten a $110,000 signing bonus. Back then, the bonus opportunity was up to two or two-and-a-half times your base salary, based on your performance and execution of your work.
What I liked about the corporate lifestyle was the consistency, the safety, and the benefits that come with working in a large institution, like 401(k) options, healthcare, all those things.
What I disliked was the bureaucracy, and that what dictates your success there is so subjective. You could control so much, but the uncontrollables of how you were promoted and what you were paid and if you were paid on your bonus were just way too large.
I couldn't stand the lack of creative ability, the frustration of guardrails, of having to do things because they say so. There's a lack of freedom to build and grow at your own rate.
When I told my boss I needed to take time off to go on "The Bachelorette," he thought I was joking.
He's like, "You can't be real." I'm like, "No, I'm serious." He's like, "No, come on." He's like, "You messing with me? Is this an April Fool's joke?" I'm like, "No, this is real. I'm going." He's like, "I don't know how to handle this. I don't even know what to say to you. I'll call you back." He started talking internally, and he was like, "OK, well, I have your memo. You've definitely put me in a tough spot, but I'll move it up the chain."
That exact memo I sent to my boss about taking time off is reprinted in my first book, "The Restart Roadmap."
It breaks down the likelihood of when I would come back to work, which was based on me studying other seasons of "The Bachelor" and then talking with producers. I learned that the cast usually starts with 30 people, but also, after one night, they usually eliminate one-third, so there's a 33.3% chance I'm actually back after 24 hours. I did this whole table. Most of the contestants before the final four are all gone after a month. So there's a huge percentage chance that I would be back within a month, and I had five weeks of vacation to use anyway.
That memo went all the way to the regional president, the community bank president, all the way to the president of the entire bank, and he signed off on it. When he signed off on it, I heard that the head of HR stormed into his office and was like, "Do you know what you just gave approval for?" He's like, "Not really." The final decision was essentially, "You can go, but recognize that there are consequences for how things turn out."
So I went, I burned through my vacation, and the rest of the time I was there where I didn't have any vacation banked away, I was not paid.
When I was on "The Bachelorette," I did try to talk about finances.
I started with careers — it's usually what I'll do when I have these conversations. Let's talk about jobs first, and then jobs can naturally integrate into finances.
From what I remember, she wasn't very interested in talking about that. And then additionally, I don't think the producers really suggested those as topics of conversation while we were filming. Which makes sense — you're putting on a TV show and you want good ratings and you want a good, entertaining show. You're not going to be talking about your career track to corporate America. It's just a little vanilla, it's boring.
The only place that people have this opportunity to talk about it is in the Fantasy Suite when they're with each other for the overnight stay, and no cameras are on. That's my understanding of where those conversations about how finances could affect your relationship would happen if they could.
I came back from filming in March 2018 and was back at work by April.
Based on how I felt the show went, I thought I was in a pretty good space. But the show wasn't even premiering until late May, and then interest didn't really pick up until June. So there were two or three months there where there was really no news — other than my coworkers wondering if I won.
It was absolutely nuts. I'll never forget going into work after that episode where I kissed the Bachelorette and she said, "Jason's a great kisser."
The next day I go in, and the assistant of the regional vice president was like, "Oh, Jason, I heard you're a good kisser." At that point I was like, "OK, life has changed in a weird way."
I kept working there for a year after filming until my boss sent me an ominous text saying to call him one day when I'd taken off work in April 2019.
The whole story of how it ended is in the first chapter of my new book, "Talk Money to Me," but basically, I was placed into a predicament in which I had to choose between eliminating any form of media (podcasts, social media, etc) and keeping my career at the bank or restarting my career outside the bank.
I made the decision that I was going to leave in Q2 of 2019.
Since then, I've diversified my income stream. I have a talent management company called Rewire Talent Management. This year, we'll have revenue in the $4 to $8 million range. I take as little of a salary as I can from the company so we can keep the cash in it to reinvest.
I also have an investment company that I own with some individuals that I owned before "The Bachelorette" where we do real-estate projects and different seed-stage and early investments. The first company I ever invested in was called Evoke, a muesli cereal company — I went to college with the founder.
Then I have a company that is focused on my Trading Secrets podcast brand and a monthly business membership. Annually, that does around $400,000 in revenue, or about half a million dollars in revenue, with Trading Secrets and all access.
Then there's my personal brand, which includes all speaking engagements, all my brand endorsements, and influencing deals. This year, that'll be in probably the $1 to $2 million range.
"Influencer" has such a negative connotation, but it's a massive, massive industry. When I started doing it in 2018, people looked at me like I had four heads. Now that it's 2024 and this will be the largest year that I've ever had in influencing income, people are more like, "Teach me how to do it."
I also have some stuff in private equity and some alternative investments and other stuff that's out there that's just deploying capital into building wealth. I learned about the importance of investing from my grandfather. He was so keen on making money on your money, the idea of just continuing to build passive income and build and build and build.
Today, I'd estimate my net worth is about $4 to $5 million.
We just came off a massive book launch for "Talk Money to Me," where we went to eight cities. Once this press tour wraps, I'm pivoting a lot of my branding to the whole love and money topic, and I have a few speaking engagements lined up for that — that is one area I want to continue to really push and build.
My podcast, "Trading Secrets," has become a top business podcast. In addition to our first episode, we've just started adding a second weekly episode called "More Than Money." Depending on what goes on with the market and podcasting, we're in talks about building a podcast network.
I have aspirations to do so many weird and different things in my career, and financial freedom will allow that. So, I'm still trying to work to gain more of that financial freedom, in order to take shots in all different directions.
Jason Tartick's new book "Talk Money to Me" is in stores now.