Ep #252: Selling Authentically on Social Media with Kristen Boss

The Design You Podcast Tobi Fairley | Selling Authentically on Social Media with Kristen Boss

If you sell a product or service in the online space, this episode is for you. I’m joined this week by my friend and marketing genius Kristen Boss, a super-savvy marketer who has a blast taking the ick out of marketing, helping her clients show up and build a following so they can sell without hustling and burning out. Whatever business you’re in, this episode is full of nuggets you can implement.

Kristen Boss is a coach, keynote speaker, podcaster, and author known for her fresh approach to marketing and sales in the social selling and network marketing industry. She believes in teaching people to work with diligence and focus, while leaving hustle culture in the past.

Tune in this week to discover how to start using social media to present your fully authentic self. Kristen Boss is discussing her own journey of finding her voice, the constant evolution of sharing your authenticity, and why showing up in your uniqueness is what’s going to help you build an audience you can sell to.

What You'll Learn From This Episode

  • How Kirsten helps her clients take the ick out of marketing.
  • What stops entrepreneurs from showing up authentically on social media.
  • Why people with MLM businesses may be selling someone else’s product, but they still need to build a personal brand.
  • What you communicate to your audience when you’re brave enough to be yourself on social media.
  • How to integrate the aspects of yourself that will allow you to shine through social media.
  • Why pivoting in your marketing is a constant evolution, not something that only happens once.
  • A vulnerable story from Kristen about deciding to elevate her brand in a way that didn’t feel authentic.
  • How Kirsten decided to take her own path on social media.

Featured On The Show

Full Episode Transcript

You are listening to The Design You Podcast with Tobi Fairley, episode number 252.

Welcome to The Design You Podcast. A show where interior designers and creatives learn to say no to busy and say yes to more health, wealth and joy, here’s your host, Tobi Fairley.
Hey, hey friends, happy middle of January if you’re listening to this when it first comes out, or happy day whenever you’re listening. I hope you are having a wonderful year so far. It’s really good for me. January’s my favorite month or one of them maybe because my birthday is coming up in just a few days. So who doesn’t love their birthday month even when it means we’re getting older? So I love every year better than the last and this one is no different.

And I kind of feel that way about podcasts sometimes. So this episode is going to be a really good one. When I recorded it a few weeks ago with my friend Kristen Boss, she was just in rare form that day and just being so transparent and so open. And that’s what I love about the guests we have on The Design You Podcast because that’s what really helps us, as the listeners to hear the truth, to hear real stories from powerful women and today’s episode is no different.

So Kristen Boss, that’s her real name, she is a boss. She is badass but she is also the host of one of the top marketing podcasts and is known for her fresh approach to marketing and sales in the social selling and network marketing industry. That’s right. She works in an industry that gets a bad rap but she is so honest and such a great guide to the people selling in this way. So she believes in teaching people to work with focus and commitment and diligence and really leaving hustle behind. And you all know I’m a big fan of anybody who’s anti-hustle.

Kristen’s book that came out last fall was all about, I think it was last fall, at least it was last year. It was one of my favorite books of last year and it was all about leaving the hustle behind. It’s really a good one but she brings us so many amazing nougats today in this episode. So she’s a coach. She’s a keynote speaker. She’s an author. She’s a podcaster. She’s all the things and she’s really, really savvy in the reels space, the social media space. She does beautiful things with reels and is very inspiring. If you’ve wanted to show up more on social media she’s definitely a person to follow.

So let me be quiet and let you hear this fabulous authentic transparent conversation with my friend, Kristen Boss.

Tobi: Hey, Kristen, welcome to The Design You Podcast. It’s kind of been a long time coming with our schedules colliding so this is a treat. What’s happening?

Kristen: It’s been a minute, I know, we’re here, we made it happen. The planets aligned. We are having the conversation, I’m so excited to be here.

Tobi: I am so excited, me too. Okay, so I obviously know who you are. We’re friends. But tell everybody who hasn’t encountered you which hopefully they have because you’re quite a force, especially in the online space but tell everybody who you are and what you do.

Kristen: Yeah. So I’m Kristen Boss, that is actually my last name. I lived into that one so I married my husband so I definitely am in, in the online space as I’m trying to find my words here. So I have a marketing podcast, it’s known as Purposeful Social Selling with Kristen Boss. We’re actually going to be rebranding that shortly here. And I teach people who sell a commissionable product or service in the online space how to better market and sell their business in a way that aligns for them and their audience, essentially in a way that feels good.

I dig the ick out of marketing for a lot of people that are growing businesses from home. So that’s what I do. That’s what I’m about, having a blast doing it.

Tobi: I love it. I love it. So everything from literally, I know early on and I know you probably still have a lot of these customers. You’ve definitely worked with people in the MLM space and a lot of anybody that will sell anything like you said, small business, sell it from their home, sell it for their company or work for a different company. Anybody that’s just really learning how to sell and show up. But even though smaller companies and people doing things like MLM work, they’re required to essentially build their own brands.

They may be selling a product for someone else but they have to be able to show up. So it’s not unlike the creatives who are following me that still need to show up and create a following and a presence and sell without feeling icky even if you’re an interior designer or an event planner or any of those things. Same things apply, right?

Kristen: Yeah, it’s universal principles, it’s all the same. You have to show up in a way that connects with your audience and gets them to show interest and purchase from you. So the only difference is how you’re making the money, what you’re actually offering. So it’s the same across the board, universal principles.

Tobi: Could be anything, yeah, could be rooms, it could be leggings, it could be lipstick, it could be anything.

Kristen: It’s all of it, all of it. And I have coached interior designers and photographers and brick and mortar. I’m coaching a mayor right now and that’s fun. I’m actually coaching somebody going through a candidate mayoral race. And I’m like, “Well, coaching politics now, here we go.”

Tobi: It’s so fun. Well, I love politics so that sounds exciting. Well, I love to watch you. I love to follow you. I’m often sending you little DMs and comments but it’s been fun. Just recently you have been having some shifts again which when you’ve built a multimillion-dollar company as you have those shifts do and have to come every few years I’m sure. But it’s also when you’re being authentic I think you just, what I see that’s so beautiful is you truly allow your own personal shifts to show up in the way that you are seen in social media.

So when I asked you today, “What was lighting you up?” And you’re like, “I want to talk about how to really be authentic, not the buzzword, authenticity but actually be authentic in a curated space like on Instagram or TikTok or with a certain audience.” And I so want you to talk about that because I see so many people getting stuck, getting frustrated, trying what the ‘gurus’ say. You and I were even talking about how you even were looking to people that were ahead of the game with you. And you’re like, “Yeah, never mind, I’m not following your path.”

So can you just take us into that conversation? What are you seeing? What’s lighting you up? What are people getting wrong? What’s in the way? Let’s go all the way there.

Kristen: Man, that’s a lot to unpack but I’m excited to unpack it. I like to think of social media as kind of like your dating experience. And how I kind of view authenticity and especially as a business owner your goal on social media is for people to get a sense of who you are, what you’re about and what you offer. So you do want them to relate to you. And a lot of times I think people either think I can’t be fooling me because then they’re not going to take me seriously about my business.

And then, or they’re thinking, okay, I have to present my business in such a way where I can’t bring me to this otherwise I need to make it very business focused. It’s all really polished. And so I see people dancing that line and presenting and this is why it kind of goes back to dating, I kind of go back to my dating days which was a very long time ago. But one of the lessons I had learned in that was for a while I remember engineering myself in such a way where I would change who I was based on who I was dating being like, “You like this, I could be this. You like this, I could be this.”

And really what I was lacking was standing in my own power and understanding that, okay, who are you? I love the movie, Runaway Bride, at the end, she doesn’t even know what she likes. And she goes on this journey to discover herself and be like, “I just realized I didn’t even know what I liked because I was too busy being what they liked.” And I liken that to social media because I think when you get caught up in thinking what you think the audience wants, of putting a version of yourself out there that you think that they want while leaving yourself behind.

And often getting too caught up in okay, well, I see a lot of business owners do this, especially in the early days. And I remember I did this myself, is when I started I looked at really successful coaches. And I looked at their photoshoots and I was like, “I’m going to pose like that and I’m going to get outfits like that and I’m going to do it in a space like that.” Because what I was doing was I was looking at someone successful and I was like, “Okay, I need to just recreate that photoshoot or that brand or that feel.”

But really what I was doing was I was trying on all these hats to see, okay, is this one me? No, don’t like it. And so I think what’s important, is, and this is true for me just with my audience is you’re going to evolve as you grow your business as you first start out, your photoshoots are going to evolve, your brand colors might evolve, how you talk to your audience might evolve. But as you get to know yourself more you’re able to show up a lot more powerfully on social media.

So what I see people getting wrong is, not getting wrong but not letting themselves be, is, be a serious business owner while also letting yourself come through your platform. I remember for me, I think this was last year I had decided to really get into reels, dive in and I was like, “Okay, I’m going to do this reel thing.” And I remember feeling like I can’t be dancing around and pointing at things if people want to take me as a serious business coach. If people want to believe that I can help them make a lot of money. In my mind, it didn’t feel like they could coexist.

And I decided, well, why can’t I? Why can’t I dance around? Why can’t I point at things? Why can’t I be really silly because that is part of me? And so learning to integrate all parts of myself into the business and really trusting, okay, the people that like this fully integrated version of me are my people. And so there’s been evolutions and I’m going through another one right now and we can talk about that more but it’s this idea of are you willing to be brave enough to be yourself on social media?

And for example, I just did a reel two days ago with no makeup. I was wearing an oversized Disney zip-up sweatshirt. And I don’t even think my hair had been brushed. And I just decided to get on and be like, “You know what, I’m tired of the bullshit over here. I’m tired of the people faking over here, smokescreen, smokescreen.” And I just kind of went on a very honest rant with my audience.

And it had some of my highest engagement because they’re like, “Thank you. Thank you for showing up in this way because it helps us see you, that we were late to you. You’re a human and what you’re doing is you’re showing us there’s not much difference between where we are and where you are.” And it kind of closes the gap in their mind of they believe more is possible when they see you just letting your guard down and be like, “This is how it is. I’m going to literally let my hair down with my lashes off and say it like it is.”

Tobi: Yeah, I loved it, I saw it and definitely it was perfect timing to see, right before I knew we were having this conversation. And I agree with you completely and I think one of the things that’s so interesting about the audience I work with is we come from the place of smoking mirrors by nature. You look at a magazine photograph, photoshoot of a room, it does not look like that real space. Everything is perfect. Everything is placed in the right way. Anything is ugly or people really use it, it’s been removed from the photo.

Grandma’s throw is probably not still on the sofa even though you sit under it in your sweats every single night. And so we have learned to create not only the highlight reel that Instagram already has you create. But we come from an industry where everything is about looking like perfection. And even our audience is very tired of that, they’re so over the, yeah, Martha Stewart really did not get, she never went to bed if she got all those chicken eggs by herself and baked all those cakes by herself before 8:00am and squeezed the orange juice.

Nobody believes it yet we don’t know how to show up in the opposite way because kind of like you said with dancing, we’re like, “So am I always just supposed to look like I actually look when I’m at home with holes in my sweatpants?” I can’t figure out what’s the in-between and I’d love to hear you talk about that a little bit more because I think that’s kind of what you were saying. You’re like, “I can be both a dancer and a real serious business person.” But even for the people who are thinking, well, I don’t dance like that at home.”

But they do act silly or relaxed or have connection. And that’s what’s not – they don’t know how to integrate the two. They don’t even know what that means. So can you help us a little bit more understand what that means to do that work of integration? Is it just being willing to be seen? How much of it do we curate? Talk to us a little more about that.

Kristen: So I love the concept of, I’ve heard it from someone saying, “Share scars not scabs.” You don’t want to have it all hanging out there but there is the concept of relatability and someone seeing themselves in you. And so a lot of the time if I’m not on camera filming I’m wearing loungewear, I’m wearing yoga pants, I am super chill. And so sometimes I do reels. Now, I usually have my lashes on, that’s my thing, I like my lashes. So for me, I’m like, “It’s fine.”

And also I think it depends on the context of the conversation I’m having. So if I’m talking about, “Hey, let’s talk about five ways that you can boost your sales this month.” I’m probably going to be a little more polished in that video because I don’t want to detract from what I’m saying with like, “She’s not wearing her lashes today.” It’s like okay, what’s the focus? The focus is the content.

Whereas the other day when my lashes were off and my hair was down and I was saying it like it is, it was a message about vulnerability. So it made sense to show up without my lashes and with my hair down. Because it’s, okay, how I’m presenting was an honesty of the moment, honesty in my looks, honesty in my feelings, honesty of my true self. So I think you just have to ask, “Well, what am I conveying in this message and in this post, am I conveying my silly self?”

Well, I’m probably not going to convey my silly self if I’m trying to show off a layout of a room or something, what is the focus here? And so the idea of integrating yourself is I would just ask you, who are you when if you were on a Zoom call with your client or chatting or hanging out with your friends, what’s your personality like? Are you reserved? Are you quiet? What are you about? Do you tell funny jokes? Are you witty? What are you about? And that’s where I would say, “Let people see that part of you.”

I think a good example of that is the Rambling Redhead. She’s hilarious on Instagram. She has all this personality. She cracks me up. I always know I can go there for a laugh even though I’m not in the interior design space but what people do is they feel a connection to her personality along with her taste in design. And so it’s just a matter of letting people see all of you, not just your skill but the person behind the skill. Because connection does matter in this marketplace because here’s what I’m going to say about this.

Let’s say they’re following, you have your consumer that’s consuming content and they’re following home décor accounts or interior design accounts. And if they’re following two interior design accounts who have a similar look, similar feel, similar vibe, how are they going to decide between the two if they both look the same and the services are the same? I guarantee you, your consumer, they’re going to go to your Instagram stories and they’re going to look for your face. They’re going to look for, how is she talking, how is she showing up?

Because they’re going to relate that to the consumer experience with you. She’s kind of goofy but she’s really grounded, she’s soft, I like this. And they’re going to choose the person that they relate with most. In fact, they’re more likely to choose the person that they relate with more than even if that particular person maybe has a less elevated brand or is even more expensive than the other person because of relatability. So that’s what I mean with integrating and let people see you.

Tobi: Yeah, I love that so much. Okay, so tell us a little bit about this kind of fire that’s lit in you because you’re like, “And I’m going through another shift in myself.” So this is not just something you go through once at the early part of your business or when you finally get comfortable enough to get on reels and then you’re set for life. This is going to keep happening. Things are going to keep coming up. So tell us about what that feels like for you this far in after looking like a complete success in every way. It’s still going to evolve and change, right?

Kristen: Yeah. I literally tell people, entrepreneurship, “You’re just dying a 1,000 deaths just when you thought you were reborn, you’re dying again.” And you’re like, “Alright, here we go.” It’s like I don’t know how many times this phoenix is supposed to go into ashes but here we are yet again and I have been reborn. So it’s really fun talking to your audience because I’m a creative at heart too and I did hair for 15 years so I was in the industry in Hollywood in that way. And I liken your brand at leveling up to a room that you have curated and you’ve loved for a very long time.

And maybe 10 years ago you were really into velvet, you like velvet seats, velvet couch. I’m obsessed with velvet. And then you kind of look around and 10 years later you’ve realized, I’m onto something else. Velvet isn’t feeling like me anymore. I’m really wanting to re-curate the space to better reflect who I am and what interests me today. So your brand is the same way. I’ve done the same with my business. It’s like okay, the Kristen that made a 100K shows up very differently than the Kristen who’s making eight figures or whatever.

And so I was like, “Alright, this is a very vulnerable story and so just to kind of show the audience how do we be vulnerable, I’m going to tell you right now. So I was in the space where I felt like I had all the success in my business and I had this very niched audience that loved me and I love the community I created but I was ready to elevate my brand.” I was like, “Okay, I want to elevate so that I’m perceived as a thought leader, as a big deal. I kind of want to be seen as the next Mel Robbins, I kind of want to have a Jay Shetty vibe, those things.”

And I was like, “Okay, and I want to grow my following. I want to look more robust on this platform, especially to a cold audience.” I really just thought about time to take myself more seriously. And I was looking at these big people and I was like, “Well, what are they doing?” And I love following Alex Hormozi and I’m watching his stuff. And I’m noticing as I’m saying this, I was like, “Mostly men, interesting.” So I’m looking at what they’re doing. And I’m like, “Well, that must be what I do.”

And so I’m like, “Time to go to my account.” I hired this media team, but they’re a ‘big deal’. And they were like, “Yeah, we grew Jay Shetty’s account. We grew Mindvalley’s account. We grow this person.” They were dropping all these big names. They’re like, “We’ve got you, we’re going to take you from, right now, Kristen, you come off. You’re very relatable. You have a lot of value with your audience through your content but we feel that your audience doesn’t perceive you as a thought leader. You’re not seen as being up there.”

And what’s so interesting and I’ll kind of break that down a little bit more but they were like, “Okay, we’re just going to elevate your brand.” So they were taking my video content. And if you’ve seen it, it’s the neon letters, it’s emojis popping up, it’s sound effects like pop and weird swooshy sounds. And I had a follower say, “Thank God you’re done with the zoomy videos.” It zooms in and you zoom out.

Tobi: I saw some of that, yeah.

Kristen: And secretly that was – God, me too. But they were like, “Okay, this is what we’re going to do. This is where we’re going.” And they told me, they’re like, “Hey, give us 90 days.” And I play everything by the long game, I’m like, “That’s fine.” They’re like, “Give it time, your audience, they’re going to have to adjust.” So we’re pushing this content out and there’s this thing in me where I’m like, “I kind of hate it.” It looks good and it looks just like the big names and what they’re doing.

And so quality and editing, producing quality is fantastic. Production value is great. But I’m just sitting there and I just, I’m like, “Ooh, alright, I’m just going to keep trusting them. I’m going to keep trusting them.” And I’m noticing my engagement is kind of dropping, my reel views are dropping. The engagement’s not the same and I’m starting to feel disconnected from my audience. I’m starting to feel, and I love the feeling of community through my platform. And so I’m starting to feel disconnected. I’m seeing all these metrics.

And I’m just sitting with this icky feeling. I’m like, “It’s okay, I do everything long game, I’m going to make sure I have enough data.” This is what I teach my students to do. I’m like, “Don’t just make emotional decisions, make database decisions.” Well, finally I went on this therapy retreat with my therapist and I was just telling you before we started that I feel like I took an emotional enema. I just cleared out so much junk.

Tobi: I need a therapist retreat. Is this a thing?

Kristen: Oh my gosh, it is a thing, I will send you her number. I’m like, “Everybody needs to do this.” Even my COO was like, “I think we need to schedule an intensive before every big launch because how you came back is just insane.” I’m like, “I know.”

Tobi: I want this number.

Kristen: I will give it to you after the show. So I do this thing and I process so much, I come back and literally, it brings everything into such perspective where everything feels so small. But in the sense of right, I know what I’m going to do. And I was like, “You know what in fact, I hate this. We’re not doing this anymore, I’m not giving this another day.” Turns out the day I decided that it was the end of the 90-day agreement with that team. And I was like, “Perfect, great.”

Tobi: We’re done.

Kristen: We’re done. So literally between the feeling of I think I’m going to be done to actually getting on the call with him and saying, “You’re done, I’m not paying you for December. Please release to me all the assets you’ve created. In fact, it’s okay if you don’t. Thank you very much but this is no longer aligned.” Was two hours literally from the feeling to actually executing the task, two hours. I let my whole team know, I told my COO. I was like, “Look for a social media manager. This is a shift we’re making.”

And I literally, I called them a hostile takeover. And literally, I just took my Instagram platform back and be like, “I’m going to do what I know. And here’s what I know that my people love.” And I literally sat down and I think I created over 90 days of content, written content. And it was just flowing, exploded out of me. I was like, “I know what I’m going to say.” And again, because I processed such big emotions in therapy I came back and I’m like, “I don’t care how many unfollows I get. I’m going to unleash myself.”

And my audience was flipping hair for it. My engagement shot up. The sharing, and when the media team was running this it was maybe 5,000 views on a reel when I had been averaging 30/40 before that. And once I took it back, 100,000 views, 50,000 views, sharing everywhere. It just exploded. And my audience was like, “Thank you. Welcome back. Please say you’re done with the zoomy videos. Please say you’re done with that.” I was like, “I know but you know what, guys.” And here’s also what I mean about vulnerability is my audience saw me try something.

Tobi: I love that, I was just going to say the same thing.

Kristen: They saw me try something.

Tobi: And you would not have the clarity you have right now had you not tried it because that other version of you was, I need to be like Mel or like Jay Shetty. And then you saw what that was really like and then you were like, “Wait a minute, I need to be like me.” But sometimes it takes us trying and investing in the thing and putting ourselves out. And I love, as I was listening to you I was like, “This is so fascinating.” Because what you’re not even probably weren’t noticing and I don’t know if you’ve thought of it this exact way, probably.

But what I’m noticing from the outside is by the time the Jay Shetty’s and the Mel Robbins’ have become themselves the way to become them is the old way. Probably what [crosstalk] is the fresh way of becoming the next thought leader. And so it’s so interesting because we don’t know how to get there without a path and we don’t like the uncertainty so we try like you said even from the beginning. We try to copy a path somebody else had but a lot of times by the time they’ve arrived the path isn’t even the same path anymore. It’s a totally new path for you.

So I love, that’s so inspiring to me and I’m sure to the people listening because watching what you’re doing right now would be so inspirational for us to say, “Now is the time to try what she is doing now in our own business, not what she becomes a thought leader. At that point, the rules have probably already changed because things move so fast.” So I love this.
I think absolutely, I hear everything you’re saying and I can see that (a) you already are a thought leader, (b) you’re probably doing exactly the right things to become the next version that’s going to look completely different than what they did, so how fun. But you can’t know that unless you try it, you can’t know.

Kristen: Yeah. And I think there were a couple of things that I want to talk about in firing the media team that someone might need to hear as a business owner is one, my audience saw me try something. And saw me take it back and say, “You know, I’m actually going to be more me.” And I talked about it and people were like, “Man, this is very powerful for me to watch and see.”

The other thing is I realized that when the media team was creating my content what was happening was they were trying to build a relationship between my audience and the content and essentially cutting me out of the relationship. And that’s what I noticed is I noticed, wow, the focus is on the content but we’re losing connection where they feel connected to me and they know me. Because it was so, oh gosh, it was just, I mean they literally and some people know. It’s not like they were coming up with their own words.

They were pulling words out of my books, out of my content. So it wasn’t like they were saying things I wouldn’t say. But it was dry and without heart, and without soul, and without personality and so it just felt empty. And here’s the other thing a business owner needs to hear, is that was after me spending close to, I want to say $60,000 or more with them in a 90-day period. And it’d be very easy for a business owner to think, I’ve given so much money to them, I’ve invested so much, maybe I just need to stick it out a little bit longer.

And I had them coming at me saying, “But we’re the experts. We’ve grown these platforms.” They tried to tell me, “We know better than you.” And it could be very easy for some business owners to think you’re right, you do know better, I’ll just keep paying you. Instead, I’m like, “No, actually I know better.”

Tobi: Right. But what I can see is sometimes you have to spend $60,000 to remind yourself that you know better.

Kristen: Yes, exactly, yeah.

Tobi: Sometimes you do and I’ve done it too. Somebody on my team today was saying, “Can we have a marketing consultant look at this?” And I’m like, “Not right now because I’ve tried five different marketing consultants in the last five years and I haven’t found them to know any more than me. So what we need to do is to lean into what I know.” And so that’s a hard place to get to and that feels very scary and vulnerable but that’s essentially what you’re saying and I’ve done it too, paid thousands and tens of thousands of dollars to remind myself that I do know me.

Now, it doesn’t mean we know everything and it doesn’t mean we don’t need consultants and coaches and other things. But I think it’s such a beautiful lesson to keep coming back to yourself.
One of the things you also told me when we were chatting before we got started is in this process, also it kind of showed you. You’ve done a beautiful job of connecting with your audience but you were trying to go next level of connecting with brands and gurus and influencers and it kind of showed you a different side of yourself and maybe where you were playing small. And maybe where you thought you were but you really weren’t. Can you talk to us about that?

Because there are so many people that listen to me and they’re like, “I’ve gotten to a certain level in my business and I’m happy with that but I’m not in the club of these people I admire.” I’m watching, like you earlier said, “I’m not in the Amy Porterfield club or I’m not in the club of the fancy coaches. Or I don’t have drinks with Amy and Jenna Kutcher on the weekends. I’m not in the club so I must not be as good as them or big as them or important as them.” Can you talk about that? Because I think we do this to ourselves all the time.

I had a coach last year or the year before go, “Tobi, you know there’s not a club, right?” And I was like, “But it seems like a club and they look like a club.”
Kristen: Okay, I don’t want to be coached on this stuff at all. I want to keep my thought but there absolutely is a club. And I’ve collected evidence for that but we’re not getting coached right now. We’re not getting coached right now.

Tobi: And I think what she was trying to say, maybe what she was really trying to say is there is a club but the club’s not the thing that you think the club is or it’s not the value that you think it is.

Kristen: Yeah, I would believe that. I would believe that. But there still is a club and I have evidence for that.

Tobi: Okay, so tell us how we think we’re comparing ourselves to the club and thinking we’re not enough.

Kristen: Yeah. So more honest vulnerability here, just getting a little more naked. Another part of the reason why I wanted to elevate my brand was not necessarily for my audience but to be perceived a certain way around my peers. Because I felt like I was underestimated. I feel like I’m kind of like the dark horse in the entrepreneurial circle where unless I tell you, most people have no idea the revenue my business brings in. And I think I was pitching myself onto some podcasts where my businesses were the same size as theirs.

And I have a bestselling book and all that, but I noticed there was this, a brushoff and at the time I made it mean it’s because my account doesn’t look robust enough. It’s not impressive enough and it doesn’t look like the other big names. So part of why I went and elevated my brand was so that I could be perceived a certain way among the next level of people like my peers, my so-called peers. And so there I was trying to do that and I was still getting brushed off. And funny that you say club, here’s a funny story.

So I was at this networking event, met big names and I was in a picture with several big names. We know a couple of them, you may have mentioned one of them. So I’m brought into this picture with these really big names. They ask me, “Come in the picture, Kristen.” I get this picture and I’m like, “This is amazing, I’m in this big-name photo.” And I’m noticing as I’m even saying this I’m like, “Man, I’m just hearing high school Kristen talking who just so badly wants to be seen and validated by the cool kids.”

But there I was, yes, I’m in this photo, I have this picture. And then one of them, one of them hosts this picture on their social media and I am cropped out. I am cropped out. This is why I’m confident there is a club.

Tobi: That’s great and you’re like, “Of course, because they’re like get rid of the no-name lady on the left and squeeze everybody else in.”

Kristen: That has lit the biggest fire under my ass.

Tobi: That was awesome.

Kristen: I was like, “I might be a no-name to you today but five years from now you’re going to be digging in your phone for that photo and saying that you knew me.” But that was probably my outrage reel.

Tobi: I love it. Yes, I love it though.

Kristen: I’m cropped out.

Tobi: Well, and it’s so funny because it does show we pedestal everybody and we compare ourselves to them at every, no matter what level you are you’re pedestalling the people one or two steps ahead of you and thinking you’re less than them or you need to be where you are. So what did you really learn in that, although it did light you up to go become whoever you want? What are the other lessons there that can help people who might quit because they don’t think they can ever play in the playground with those people, they can’t play on the field with them?

They’re not going to get there because I see so many people struggling with that. They don’t all just get motivated like you do or maybe they don’t quite have the funds yet to be like, “Watch me, I’ll go make this happen.”

Kristen: So I think I had to get to the point, the place where I got was, okay, I just don’t have evidence that there’s somebody just like me out there. And maybe I need to be the person that creates that evidence. And I think I just decided to be okay going my own way and that was what the reel was where I’m like, I am not going to try and be like that person. I’m not going to try and be like that person because honestly, it’s exhausting. It doesn’t feel good. So I’m just going to be Kristen Boss and we’re just going to go and I don’t even care how long it takes and who knows my name anymore.

And what’s funny is the person who cropped me out I’m actually having them on my podcast to promote their book in the spring. I’m like, “Dude.” But I’m like, “It’s okay, I’ll still serve, I’ll still give, I’ll still network.” But I kind of feel like that dude on this is dark humor but you’re about to find out a little bit more about me. Hey, we’re being vulnerable. I’m thinking of Billy Madison where he goes back to school and he tells the guy he bullied and he’s like, “Hey, I’m sorry about that.” And the guy’s like, “No problem, Billy.” And crosses the name off the list.

Tobi: Yeah, but he was going to kill him, he was going to be a target.

Kristen: Yeah, I have my own entrepreneurship list right now and you’re on the list. I’ll still have you on my podcast but you’re on the list.

Tobi: Well, yeah, that’s good. Well, I love that you’re saying you’re going your own path. And what’s coming back to me is, we haven’t even talked about other than you mentioning you have a bestselling book and it came out not that long ago. In fact when it first came out was when we first tried to start getting you on the podcast and we both were just swamped and you were swamped. But I think your book, I mean I think I sent you screenshots of I was underlining every page.

But it is so about this hustle culture and being on the treadmill and trying to live up to everything. And as you were just talking I could see how there is such a risk if you’re not careful of trying to become the next version of you compared to everybody else is just getting back on the next version of the hustle bus too and you don’t even notice it. And then you think you’re just growing, you’re elevating. And I’ve done that to myself where I’m like, “I burned out, I’ll never do this to myself again.” And then I’m pitching myself for all these product lines.

And I got five national product lines in a year and all of a sudden I’m hustling again and didn’t even mean to and didn’t know it and I’m burned out again. So I can see how in such a way this is a blessing to remind you to go your own way and not forget even those things that are in your book. So anything come up around that for you when you’re thinking about that?

Kristen: Yeah. It’s always something I’m working on. I feel like you’re never a recovered hustler, you’re a recovering one. You’re always going to be catching yourself when you’re moving into it and hopefully sooner, you catch it sooner than later over time. My therapist said this to me recently, she’s like, “You need to have your regular booster shots from hustle.” And I was like, “Damn, that’s so good.” I was like, “You’re right, I do.” Because where mine snuck up was actually in a very mundane thing.

It was meeting with our financial planner and she was talking about the financial plans. And then she kind of just said something very subtly and it wasn’t with ill intent. She’s like, “Yeah, but then you’re going to keep growing and you’re probably going to have this revenue the next year and that revenue the next year.” And I noticed recently, again, conversations with my therapist, everybody, therapy, it’s amazing. I’m just going to talk about that.

She was just like, “Hey, when did you notice this scarceness really start to creep up and this anxiety start to hum along in the background?” And when I really traced it back it was when I met with my financial planner and she told me what the financial plans were for the year. And suddenly I felt married to her vision of how quickly we should be moving along. And I forgot that I was in charge. I forgot that I got to set the pace. And so I just noticed that I just ever so quietly slipped into it and okay, but we’ve got to hit this, we’ve got to do this.

All because of this proposal, literally, it was just a financial proposal that has flexibility and I was acting like it was in charge of me, it was the boss and I had to meet it, there was no flexibility. So I just had to remind myself, oh yeah, I’m in charge.

Tobi: Well, and it doesn’t necessarily help that you’re also looking at other peers who are like, “Well, I’ve hit 10 million and I’ve hit 15 million and I’ve hit 40 million and I’ve hit 100 million”, or whatever. And our brains forget that we also don’t have to grow forever. And we don’t have to keep getting bigger and bigger. And some people may decide a $2 million company is big enough. Some people might decide it’s 500,000. Some people might decide it’s 12 million. But the 12 million doesn’t always have to become 20 million or 50 million. It doesn’t have to.

Kristen: No. I mean, hey, some days I fantasize about a 200K business. I’m like, “Man, it was so simple then. I just had one VA and a podcast and it was so easy.” And now I own a company, that’s been a whole another uplevel where my God damn, I’m a CEO. I didn’t wake up saying, “What sounds fun, is being a CEO.” Now I’m like, “Well, damn it, I’m a coach and a CEO.” And most days, 90% of my time I’m CEO-ing and then the other 10% I’m coaching.

Tobi: Yeah. So okay, well, this has been amazing. I think people are going to be so inspired by this in so many ways and it just reminds people that it is okay to try all the things and to try to grow. And it’s also okay to decide to slow it down or stop or change your mind or try something different or go a different path. So as people are thinking about this no matter where they are in that trajectory and that continuum of I want more visibility or I want to go next level. How do we stay in that authentic space the most? How do we stay grounded and in that space do you think?

Kristen: I think you have to go back to what’s driving your decision, who’s driving that decision? Is it me or is it somebody else? Why is this important to me to do now? Just to make sure that a story isn’t driving it, a story that you don’t like or don’t want and just really understanding, okay, does this thing I’m thinking about doing, does it align with who I am? Does this feel like me? And maybe you’re going to try it and be like, “Well, no.” And listen to your gut and be like, “No, that’s not me but I’m going to try something.”

But in the beginning, you have to be willing to try a lot of things and not make yourself wrong because you try something and it doesn’t work out. And especially I think this is huge I think, with entrepreneurs, I think they’re afraid to try new things publicly in front of their audience. And their audience thinks she tried that, must have been a fail. I haven’t had thought at all. I was like, no, no one thought it was a fail. Everyone was like, “Hey, you learned something but thank God you’re back.”

So you have this idea of what’s driving your decision, if I was to go back to my original decision it was the desire to be perceived a certain way. And any time that is driving your decision it’s worth pausing and going deeper and being like, “Okay, but if it wasn’t about being perceived a certain way if it was just about me and where I’m going, does the show still fit?” So if it doesn’t I’m not going to put it on.

Tobi: I love that. So did you release that desire to be perceived that way or do you still want to elevate?

Kristen: Yeah. No, bye.

Tobi: Yeah, you’re done.

Kristen: I’m done. I’m like, “Bye.” I mean my podcast rebrand is going to be super elevated, it looks pretty kickass but it’s not for anybody but me and a reflection of my own evolution and uplevel. But for me, I’m like, “No, I’m done.” I put my video guy back on retainer and we’re building the studio. And I was just like, “Hey.” There are some things that I like about what they’re doing but we’re going to do my spin on it and that’s where we’re going. And I don’t care if I don’t see anybody else doing it, I’m doing it. So I don’t care, bye.

Tobi: Well, and it’s so much more relatable honestly because when I do think about some of the names that either you’ve mentioned or that at some point in my life, I have aspired to be like or whatever. Similarly, I don’t feel I could sit and have the same kind of open relaxed and personable conversation we just had with those people. Maybe if I was in the inner circle of theirs, I don’t know, but I mean what’s so beautiful about you is that it’s not all perfectly curated and it’s not all orchestrated and it’s not the smoking mirrors.

That’s probably the best thing about your brand and so I love that you noticed that that’s the very first thing that they were squeezing out so yeah, so good.

Kristen: Yeah, they’re taking me out of it. I’ll say this too, I think you kind of asked have you just let that go or is there a club? I think I had this fantasized idea of – romanticized idea of what I thought the club was. And I think what I’ve seen is the honest picture of it and think everyone’s…

Tobi: I was just about to ask that.

Kristen: I think it’s more like I actually don’t want to be in that club now.

Tobi: That’s exactly what I was going to ask. I was going to say, once you get a seat at the table or a peek into the club is it even what you thought you wanted? Because I don’t think that it usually ever is, yeah.

Kristen: Honest to God I could not imagine cutting somebody out of a photo. So for me, this person is perceived as a sweetheart. So for me, I’m seeing more here. And it’s hidden behind niceties and I’m busy and we have so much going on. Let your people talk to my people. There were so many layers between them and that. And it’s just like, you know what, I mean I have layers between someone trying to contact me and me just to protect my energy but not to keep people out. And that’s very clearly how it came across.

So for me, I’m just kind of disenchanted by ‘the circle’. And I realized I actually don’t want to be in that circle anymore. And I’m actually kind of glad I’m not.

Tobi: Yeah, I had a very similar experience, I was pedestalling a lot of people right before the 2020 George Floyd murder, all the shit hit the fan and all of a sudden I was right there where I was looking at pedestalling people, wanting to be in this club, thinking how do I get in this group or that group. And then I watched some of what happened and how people struggle. And then I was like whoa, and not to be judgmental, they’re humans and I could have messed things up too. But it just brought them back, they made it really quick for me to see, we’re all humans.

And so much of that is just fabricated, it was a façade of what we want people to think, we’re important or whatever. And we do lose connection. To me, I lose a lot of the meaning and the fulfilment when I try to put myself kind of in the club. And so yeah, I love that you learned that, so good, such good reminders to me, I thank you so much for that. Okay, well, if everybody wants to find you, follow you, see the real you which they will find, they can also go back a few weeks and see the other version of you and be like, “Yeah, I see the difference”, which is fun.

Kristen: Well, just scroll my feed, you’ll see it.

Tobi: Yeah, it’s so fun because I know exactly what you’re talking about here when you describe it. And then also they definitely need to read your book which is no kidding, game-changing, life-changing stuff. Tell them where to find all that, how to follow you, how to work with you, all the things.

Kristen: Yeah. You can find me @thekristenboss on Instagram. My podcast, when is this going to air? That’s the scariest, I’m like, what’s my podcast going to be called?

Tobi: I think it’s early January but we’re recording in December, yeah.

Kristen: Yeah, the podcast will be The Kristen Boss Show on any of your podcast platforms. So you can listen to me there. And my book is called Pivot to Purpose. You can get it on Amazon. And if you have any questions about how to work with me, I have a free money guide if you go to my Instagram bio or It’s just a fun little money mindset journal, some of the exercises that I did to really unlock some of my own money stories.

Tobi: And one of the things we didn’t even get into which they’ll hear more about when they read from me and follow you is that you did go from zero to – I mean I know it’s beyond that now but even just a year ago or so, $5 million in what, three or four years?

Kristen: Less than two years.

Tobi: Okay, two years, zero to 5 million in two years so you exploded your business and so I think that that’s something for, so there is a reason you’re talking about money mindset. You’re not just one of the million gurus who’s like, “And I have a money mindset thing too.” No, literally I went from zero to a multiple million dollar business in two years so awesome, yeah. That’s a whole other, we’ll have you come back and talk about that next time. People are going to be like, “Wait, you didn’t talk about that part.” Okay, so we’ll have you come back. We’ll have you talk about that.
We’re going to be watching all the things you’re doing with your brand. Thank you so much, it was so fun. And thanks for trusting us to be so vulnerable and yourself, that’s the best kind of podcast.

Kristen: Love it. So glad to be here. Thanks for having me.

Okay, I hope we inspired you to know that you can be you exactly the way you want to in your business in your socials in your marketing in all the places without the hustle. This is such an important message. So go out there be yourself, we can’t wait to see it. That’s exactly what we all want, is the real authentic you. And we’ll be over here trying to do the same in our spaces and I’ll see you back next week with another great episode of The Design You Podcast, bye for now.

Thank you so much for listening to The Design You Podcast, and if you are ready to dig deep and do the important work we talk about here on the podcast of transforming your mindset and creating a scalable online business model, there has never been a more important time than right now. So, join me and the incredible creative entrepreneurs in my Design You coaching program today. You can get all the details at

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Hi! I'm Tobi

I help creative women (and a few really progressive dudes) design profit-generating, soul-fulfilling businesses that let them own their schedule, upgrade their life and feel more alive than ever!

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