How Influencer Anna Kai Turned Failure Into TikTok Gold

“Honestly, if a man leaves you because he thinks he can do better, honestly, my advice would be to let him go and find better so you are free to be more than just better, but to be the best version of yourself,” says influencer Anna Kai (aka @maybeboth on social) on a Sept. 25 TikTok post, subtly smirking as she expertly works a tinted Origins moisturizer onto her glowing face. “Because hell hath no fury like a woman scorned. And honestly, I’ve never met a woman who didn’t get into the best shape of her life, or hike Machu Picchu, or finally get that promotion, or eat the best freaking pasta in Italy after getting dumped by Chad.”

While the Philadelphia-born content creator’s formula is so simplistic in nature — a comprehensive GRWM format while offering cheeky hot takes on dating, “Chads,” self-worth, and general real-life reflections — it’s brilliant all the same. Equal parts beauty marketing and self-help gold, Kai’s social presence has hit a high this past year, generating a TikTok following of 1.4 million and 1.3 million on Instagram. Not too bad, considering the venture came about from what she describes as career failure.

“I like to say to people, ‘I’m a failure-turned-influencer,’” says Kai on a recent Zoom call with TZR. “I think people kind of write off women after the age of 30. They’re like, ‘Oh, if you haven’t made it by 30, what are you doing?’ And I really had not made it by 30. I was born in 1990, so October 2020 was when I turned 30 and I was unemployed because I just lost my job in real estate. I had just moved to Connecticut because my husband worked here.”

In an effort to find some semblance of an outlet during her “quarter-life crisis,” Kai started a blog (“My millennial ass started a WordPress!”), posting home decor and fashion inspo for some time. But the content wasn’t working, and Kai failed to find an audience amid the already saturated realm of style influencers on blogs and Instagram. So she set her sights on TikTok, meeting with a coach who advised her to try shooting to-camera content. “She said, ‘You should tell a story.’ So I was like, ‘Oh, you know what? I can do my makeup, which I’ve always done, and I can talk about my life as a single 20-something-year-old in New York City,’” recalls Kai, referring to her life before marriage and relocating to Connecticut. “I dated a lot of men, I have a lot of stories, obviously. So I just did that. The first video I did went viral, and it took me literally five seconds to realize, ‘Oh, this is what I’m supposed to be doing.’ And the rest is kind of history.”

History, indeed. That initial video from September 2022 lit a fire for Kai, one that’s continued to gain momentum over the past two years. Since then, millions of fans tune in daily to see Kai work through her hair and makeup routine while offering deadpan reflections on life and love. One follower recently summed it up perfectly: “You are like the fairy godmother friend you meet for coffee who tells you truths you don’t want to admit to yourself … also, what is your lip combo?!”

With her popularity at a high, Kai is seizing the moment, launching her podcast, Brutally Anna, this month with AdLarge as part of its Fwd. Network portfolio. The format, like that on her social channels, is simple: Kai sits down with creators and experts across various industries to speak on the topics she loves most: dating, heartbreak, self-worth, and identity. Some initial guests include reality star Katie Maloney (of Vanderpump Rules fame), actor Serena Kerrigan, and beauty influencer Cyrus Veyssi.

Ahead, Kai discusses her accidental foray into the influencer space, how “failure” worked in her favor, and what she’s learned about herself since going viral.

Let’s go back to the beginning. What was the the premise of your very first GRWM video?

The punchline at the end was to tell women to remember that they are the grand prize. Occasionally, I will repost that video because it truly changed my life. And it’s a little controversial in the sense that, for me, I was telling this story of how I realized that I could not have intimate relations with a man before the boyfriend-girlfriend label was on. And that, for some reason, sometimes stirs up more controversy online than it actually does in-person, as most things do.

But people love to have this mid-tier thing now to feel like [the relationship is] headed in the right direction. So I made that rule for myself, and it made all the difference because I think you [should] just show men that you’re not willing to accept less for the sake of your company. And sometimes that means losing that company, which is fine. I probably didn’t need to be in your company anyways. So that first video was [about not letting] him forget you’re the grand prize.

Talk me through your creative process and how you ideate your discussion topics. Is it challenging to churn these out so frequently?

I do beauty while talking because it feels like the most natural thing to me and that’s how I come up with my ideas. When I’m doing my makeup in the morning, when I’m doing my hair, I sort of have this weird running dialogue in my head where I will just think of something. I’ll think of an idea, and I have this notes list in my phone where I’ll just write it down. A video that I posted last week, it’s not even [about] a recent trend. [But it’s about that TikTok convo that centers on] imagining you see “him” again and you are just better. I was thinking about it while I was doing my makeup one morning, and I thought, “Honestly, the moment I knew I had healed from a relationship in college that I was angry about for a very long time, was the moment I realized I no longer cared.” And I was like, “Oh, imagine you see him again and you just don’t care because your life is so good that you’re flying above the mess.” And so I turned that into a video.

With my videos of me doing my makeup and speaking, I sort of want people to feel like maybe they came up with the idea themselves. Because I think the reason my content resonates with so many people is that they already know what I’m saying but maybe haven’t figured out a way to formulate it into the way that I say it. It’s reminding them that you have an inner compass. And I think women, more so than men, should trust their inner compass and their intuition, because only when I have not trusted my intuition have I been led astray. Every time I’ve given a guy a second chance, it has f*cked me over.

How does your family feel about what you do and the topics you cover?

Being [that they’re] Chinese immigrants, it’s very rare to have a parental unit like the one I have. So I know I’m super lucky. They never pushed me to do better in school. I was a decent student; I wasn’t great. I wasn’t good at math or science. And they knew from a very early age that I liked to sing, dance, and do theater, and they just let my freak flag fly, so to speak. But my parents were always very equal in the sense that my dad was the breadwinner in the house, but my mother took care of a lot of things at home. And you have to remember, these are Chinese immigrants, they came to this country with nothing. They didn’t know how to invest. They didn’t know what to do once they made money. And my mom was like, “You know what? My husband’s working. I’m going to teach myself what the stock market is, what our 401(k) should look like.” So she really handles all of that.

So there’s an inherent level of trust between the two and what they’ve built. My dad has always said to me, “Just because I made the money in our family does not mean I think that your mom is a second-class citizen.” [My dad] was always afraid that I was going to get into a relationship with a man who earned a lot more than me but used that money to control me. He was like, “I do not want you to rely on a man.” So I think they’re super relieved now because obviously, I’m earning a living and everything’s great. They love the content. They’re very progressive and they’re really into it.

What about your husband? How does he feel about the topics you cover?

He loves it. I would’ve never married him if he would’ve had an issue with it. I think I like to say we’re both weird in the same way. We’re New Yorkers. We live in Connecticut right now, but we are both very invested in our careers. He was the first one, like three or four years ago when I started [my influencer journey], that said, “I think you have something to say. You have a lot of opinions, you should put them out there.”

Have you ever posted something that you regretted?

I have only taken down one video in the two years I’ve been doing this. I think I took it down because I believe that the conversation lacked the nuance that it needed to have in order to make it a full conversation. It’s just hard to do that in 60 to 90 seconds. It was about my opinion on prenups, which is a pretty controversial topic. I think right now, the general feeling and sentiment towards them is that they’re amazing, but I personally do not believe in them in most cases unless there’s a serious [financial] discrepancy between the two people getting married.

I believe that there is this emotional quotient to a lot of relationships that you cannot quantify, that at some point, you have to stop calculating and start thinking, “I am marrying this person not because I think there’s a chance I’ll get divorced in the future and he’s going to take everything I’m worth, but because I’m trying to build a life with this person.” I personally would not have married somebody that I felt the need to get a prenup with. Look, there are exceptions to this rule. For me, it’s like, OK, if my husband had a $200 million trust fund and there was generational wealth there, I would understand that because there’s just a lot of sh*t going on there that happened before me.

But unfortunately, [in my relationship] neither one of us had that trust fund, which is fine. We were coming into the relationship on somewhat equal footing and building together. So I took that video down because I think people thought I meant don’t get a prenup and don’t look into it. It was this massive generalization and I was like, “You know what? That’s not really the message I want to be spreading because I think there are probably many situations where they’re useful.”

I can do small things here and there and use certain products to enhance what is already there, because what is already there actually never needed to be fixed.

How has your influencer career changed your relationship with beauty?

If you look at my earliest videos, you’ll notice I look really different than I do now. I wear makeup still, but I am opting for a much more natural look these days. And I think what it’s helped me realize is that I used beauty a lot in my 20s to cover up. And I was going full glam every day. I mean, I felt like I could not leave the house without a full beat on in my 20s. I just felt like I wasn’t complete and I didn't feel good about myself.

The last two years has taught me that I can be beautiful without covering up. I can do small things here and there and use certain products to enhance what is already there, because what is already there actually never needed to be fixed. So I’ve experimented more with different hairstyles. I used to think, “Well, if [your hair] is not voluminous and down, it’s not pretty.” I found the Nexxus Slick Stick and I was like, “Holy sh*t, this thing is amazing. I could just throw my hair back and not have to worry about it for the rest of the day.”

My beauty journey has always evolved and will continue to evolve. But I’m like, “You know what? That’s the sign of a life well-lived, if you’re always looking at the version of you from a year or two years ago and thinking, ‘Ooh, I wouldn’t do that now.’” Because if I’m looking at myself from two years ago thinking I looked better, then I’ve done something wrong.

Talk to me about your podcast. You’ve been a content creator for years. Do you feel like this is a long time coming?

I could have, I think, a year-and-a-half ago, bought a mic and launched just like that. But I have always tried to just be very intentional with the way I do things. I always knew I wanted a podcast, but I also was trying to manage and juggle this new life that I was thrown into with traveling and making these short-form videos. And I just was like, “You know what? I’m going to figure this out. I’ll launch a podcast when the time is right.”

And a year-and-a-half ago, my now-podcast agent reached out to me and she was like, “Hey, I’m at WME. I think your content would be great for a podcast.” And so she and I started working together a year ago, and she has been so instrumental in helping me get it to this point because originally, we were going to self-produce. She was like, “OK, well, I think you should record maybe six to eight episodes before we launch so you have a backlog and you’re not constantly trying to catch up if you’re posting every week because consistency is really important.”

Instead of doing that, I recorded 23 episodes. I wanted six months worth of episodes because then I could pick and choose which people to plug during which week. By the time I was ready to launch independently, she was like, “You have so many episodes recorded that I think maybe we should go back out to these buyers and see if there’s any interest in going with a network for the launch.” So we interviewed with a few networks and now we’re launching with AdLarge, specifically on their Fwd. Network, which is centered around female voices. I’m so happy it happened this way because I never wanted to put something out there that I wasn’t proud of, that I wasn’t happy with just for the sake of putting it out there.

I’m really excited about the guests I’ve interviewed so far, and I already have a couple more guests lined up, recording through the end of the year. It’s been a process, but everything in my life has been a process. I wasn’t the 19-year-old that went viral after a few videos. It took me 32 years to even get into the space where I could think about doing longer-form content. Just because something is taking longer than you want it to doesn’t mean it’s not going to happen. Sometimes it just means it’s meant to happen better later. And I think people need to see that, that just because you haven’t hit it in your 20s or in your 30s or 40s, there’s still a chance.

What are you hoping people take away from the podcast?

I hope people feel empowered. I hope people listen to these episodes and see that the life they want to live is maybe not so far from where they currently are. I know what it feels like to be standing on one side of the riverbank, looking across the water, looking at that life and be like, “How the f*ck do I get there? I’m here and I have no idea how to get to the life I want to live.” And the only difference between me and the people who haven’t crossed that metaphorical river is that I just kept jumping and I would fall and I would fail. Eventually, I made it over. And I think that’s what you’ll learn from a lot of these podcast interviewees, is that everybody started from somewhere. And just because you saw them when they finally got to that place doesn’t mean that it was easy.