How to Think Like a Founder with Amy Smilovic

What if the biggest risk is letting other people define success for you?

In this episode, Meghan Stevenson sits down with Amy Smilovic, founder of Tibi and author of Almost Reckless, to talk about building a life and business that feels true to you. Amy shares how chasing outside markers like money, status, and industry approval can leave you deeply unhappy, even when things look successful on paper. Instead, she explains why contentment comes from three things: agency, shared mindset, and doing work that lets you be creatively at your best.

This conversation is a strong reminder that success is personal. Amy breaks down why your best decisions come from knowing your own principles, not blindly following someone else’s playbook. She also talks about the value of being present in every stage of life, because even small jobs and ordinary experiences can become the “dots” that shape your future. For listeners building a business, writing a book, or trying to carve their own path, this episode offers a thoughtful framework for defining success on your own terms and having the courage to pursue it.

This week’s guest is Amy Smilovic. Amy is an author, founder, and creative director. Born in the American Midwest, raised in the South, she moved to New York City and Hong Kong after college. In 1997, she founded the designer clothing brand Tibi, where she is the Creative Director. Tibi has grown to be America’s longest standing independently owned women’s designer brand, something Amy is intensely proud of. 

Amy said, “I built this business with an incredible team that looks like a veritable UN Assembly. I have no doubt this fact has played a role in our success — not the optics of it, but that the composition of our team has always forced us to be very clear in our communications and work through the discourse that arises with varied points of view. And if I’m honest, the team’s shared mindset — exhibited every day in their work ethic and their willingness to take risks — is, in my opinion, the result of a through line that runs through our respective experiences.”

Find Amy at amysmilovic.com.

Find Amy on social 
instagram.com/amysmilovic 
instagram.com/tibi 

Episode Highlights:
(0:00) Intro
(1:23) Meet Amy Smilovic and her new book
(2:35) Why she decided to write it
(4:00) Who Almost Reckless is for
(6:31) What contentment really means
(8:25) Defining success for yourself
(10:50) Why following others can mislead you
(13:03) The three principles behind real contentment
(18:25) Collecting the dots of your life
(24:21) Turning personal story into practical lessons
(29:20) Building your “reckless resume”
(41:32) Why thoughtful people connect with this message
(45:47) You are your own algorithm
(48:38) Outro

Have a great idea for a book but don't know where to start? MeghanStevenson.com/quiz


Traditional publishing expert Meghan Stevenson blasts open the gates of the “Big 5”—Penguin Random House, Simon & Schuster, HarperCollins, Hachette, and Macmillan—to share what every entrepreneur and expert needs to know about landing a book deal. 

In episodes released every Monday, Meghan shares wisdom and stories from 20+ years in publishing as well as interviews with authors, literary agents, and editors. She also answers questions from listeners like you. 

Whether you are an experienced entrepreneur with an empire, or are just starting out—this podcast will help you understand what you need to do in order to turn your dream of being a bestselling author into real life. 

Transcript

Why Traditional Publishing Still Matters

Speaker 1 0:00

Some of the subjects that we talk about, I think that there is an inclination, whether it's in entertainment, whether it's in publishing or whatever, to really just serve something up that is so pithy and catchy and just run with that.

Meghan 0:22

Welcome to the Kind of a Big Book Deal podcast where entrepreneurs come to learn about traditional publishing. I'm your host, Meghan Stevenson. After working as an editor for two of the biggest traditional publishers, I started my own business helping entrepreneurs to become authors. To date, my clients have earned over $7 million from publishers including Penguin Random House, Simon Schuster, Harper Collins, and Hay House, just to name a few. In these podcast episodes, I will blast open the well-kept gates to traditional publishing. I'm going to explain what every entrepreneur needs to know about landing a book deal without losing your mind. I'm going to share stories, answer your questions, interview the successful authors I've had the pleasure to work with, and probably say platform more than a tech bro. So if you dream of landing on a bestseller list but have no idea how, this is the podcast for you. And I am so, so glad you're here. Y'all, we have a great episode for you today. Something fresh, something new. So Amy Smilovic is the founder and creative director of Tibi, a designer clothing brand for women. Amy launched this brand and company without any formal fashion training way back in 1997, and has grown Tibi to be the longest standing independently owned designer brand. If I could snap my fingers, which is physically impossible for me, I would be doing that right now. Amy is also the author of two books: Creative Pragmatist, a guide to style that she published herself, and Almost Reckless, this amazing book, which was published by Portfolio slash Penguin earlier this year. So also joining me on the pod is Friend of the Pod, Blair Thornburg. Y'all know her as my fellow collaborator

Meet Amy Smilovic Of Tibi

Meghan 2:10

on the team, and she is here because she worked with Amy on the book. Welcome both of you, Blair and Amy. Thank you. Thank you. Okay, so I've got to admit that for the most part, I was just cheering on the sidelines of this project. I only did the contract and the money like a true boss. And so I am going to kind of let Blair lead the situation. But I have a primary question for you, Amy, that I want to kick off with, which is why did you first decide to write a book when you decided to write Creative Pragmatist?

Speaker 1 2:44

Um, you know, Penguin reached out to me, and we had two super fans there, and their chief general counsel and the publisher Bria. And they reached out to me asking if I had ever taken this concept of this mindset about personal style and applied it to everything else in life. And because these two women found that they were applying it in their office in the way that they did things, they were applying it to how they uh conducted their relationships with others, and they wanted more. They wanted more from this idea of what it means to be a creative pragmatist and living that every day. And so we started ideating, you know, really about four years ago, and uh and landed where we landed today. And each, you know, each place where we thought we had gotten to the destination of what it was going to be kept getting iterated as we together kept coming up with different ways to make it better, stronger, um, more relevant to more people. And um, and I'm really super proud of what what we ended up with.

Meghan 4:00

Yeah, agreed. So tell us about Almost Reckless. What is this book? What kind of book is it? Who do you think it's for? And what was the impetus for you to start writing outside of Bria telling you that she loved you?

Speaker 1 4:15

Um I think that it it really hits a broad spectrum of demographics, um, in terms of age, in terms of where you are in life, in terms of where you're living your life. But it hits hardest with people who have this shared mindset of wanting to do big things, wanting to end up somewhere great, but wanting to find that confidence to be able to do it with the certainty that the outcome will happen. And, you know, years ago, I had put out a question onto Instagram and I asked my followers, you know, what risk would you take if you were assured that it would all work out? And people wrote back right away and they said, well, is it really a risk if we know that it will all work out? What does all work out mean? And so I wrote back and I said, Great

From Style Concept To Life Framework

Speaker 1 5:20

question. What does it mean to you to have it all work out? And so people wrote to me and they said, three million. They gave it a number. And a surprisingly unbelievably high percentage gave it the number of three million. That was a really common answer. And I thought, first of all, you know, currency is a hard thing to give. Like it gets devalued very easily, right? And um, and it gets devalued also in how much you use it up, right? Like three million to my neighbor who makes a billion is nothing. So it's a constantly changing target. And no one said to have it all work out means that I will feel happy and I'll be content. And so when I put that up there and I said, really, truly, guys, doesn't to have it all work out mean to be happy. They wrote back and they were like, Well, yes, but happiness means something different to everyone. And they're right, it does. Happiness means something different to everyone. And so to me, to have things all work out means to feel content. And I feel content when I have um power over my own life, you know, when I have control. And control means that, you know, when I'm faced with problems that they are mine to solve, when I have wins that they are mine to celebrate. Same with my team, our problems are our own, our wins to celebrate. I am content when I am around others who share a similar mindset, who really appreciate discourse, who are very hard workers, who are very open-minded. And I am content when I am doing things that I love. When everything I'm doing is something creatively that I believe in. When I believe in it, I can defend it, I can make it better, I can uh be very open-minded about receiving feedback on it because I'm very in the flow. So, agency, shared mindset, and being able to be my creative best, those three things make me content. And so once you put that into focus, what risks are you willing to take to make sure that you live a content life? That is much easier to start to work towards than three million. What is no one ever, you know, like how are you feeling today? Three million. It's not a thing, right? Like it's not the thing. So um, really, I wanted people to really focus in on what it is that they're working towards, what has to be in place in order to achieve that. And then how do you get there? And um, and that's what the book does. It really helps you build that framework, and you are really doing it in a way that you realize when contentment, and only you can define what contentment means, it means that all your measurements for what is successful or not have to come from you. They're not going to come from an industry, they're not going to come from your parents, they're not going to come from your society's expectations. They've got to come from you. And when you start to be your own driver, when you start to be able to be your own measure of success, then you realize that the steps that you are taking to get there to anyone else, they really just might seem almost reckless. But but when you know better, when you know that it will all work out because you've got that much control over the situation, it's very empowering to do very big things. But again, it's big defined by you. Because to be honest, the big things that we do in my industry, they'll be like 70 million, like trump change. You know, like if I if I value my worth based on the different people that I would circulate at around a cocktail party at like the CFDA, I would go up and down. I'd go stand by a young designer and feel like I'm the biggest shit in the world. And I could go stand by the head of the row and maybe just want to like go hide under a couch. Like you are at the whims of so many other people's opinions if you do not have your stable this goal in mind for yourself. You're ricocheting all over. Multiply that now, compound it with not even a cocktail room, but just the feedback that you'll get on Instagram. You can feel different every

Trading Money Targets For Contentment

Speaker 1 10:10

five seconds depending on who's sliding into your comments.

Meghan 10:14

Amen. Yeah, and that's definitely something that I want everyone listening to this podcast to hear because it's entrepreneurs, experts, creators who want a book deal. And there's no better slew of unwarranted, unsolicited, inapplicable opinions than among authors, in my opinion. So I'll all bust out there, y'all. You got to be careful on who you're taking advice from and who you're like paying attention to in a lot of ways.

Speaker 1 10:42

Well, especially as a writer, as an entrepreneur, as even a student starting out in life, I think that um for a lot of us, the dream is to carve our own path, do something unique. And if you are insisting on doing something unique, yet mentoring and talking to everyone within the industry to get their playbook, you by definition are following someone else's playbook. Yeah. You know, so you information is good to kind of help, like, okay, what gross margin? You know, what if I am negotiating a contract, when am I being taken to the cleaners or not? Right?

Meghan 11:27

Right.

Speaker 1 11:27

That is good information. But you know, when you get convince yourself that someone is gonna give you this like 10-step exact method to follow, you will land up exactly where that other person is. And you better make damn sure that you want to be everything about how that other person is. If you were gonna follow that tightly behind them, log step. And most people don't want to follow someone else to that degree.

Speaker 11:57

It's why. Well, Amy, this is so interesting because it makes me think of the very beginning of working together when you know you had done a lot of thinking with Bria and just on your own, because like one thing I learned is that you write all the time. Like, I think you really think by writing, which was great. So you had tons of material to work with, but like the shape of the book was still something that was like in flux. And that's, I mean, that is what we do a lot of the time. So here we come. And I know that there were some things you felt very strongly that like this was not just, it was not like a founder's memoir where like you're on the cover, you know, like posing and like talking about your own experience. And it also wasn't just like how to make it in the fashion business, because as you say, you really you carved your own path, and I don't think you were really interested in writing that book. So talk a little about like how you found that measuring stick and how we worked together on shaping what the book was, uh, because you had such a clear sense of what it wasn't gonna be and and what you weren't gonna follow.

Speaker 1 12:57

I think that um, you know, in the book I lay out that the measuring stick really came about when we really uh during 2020, when it was a uh a time in the company where we were on sitting on sales over 70 million. We were very on track to do 150 million according to our like beautiful five-year plan. And we were deeply, deeply unhappy. You know, I really um I wanted to like find a way to toss out the bathwater without the baby being in it, and that was impossible to do. But after 2020, uh there wasn't there was an opening. You could actually pull the drain and kind of walk away with something and move on. And this was a time where my husband and I had to really come to a reckoning and say, do we want to go on with this business? Do we want to make it work? What would make us want to stay? And when we realized that we would want to stay, if we could feel content, that content was our definition of happy. It's not everyone's definition of happy, but it was mine. That if we could feel content, that we would want to put in everything that would be required to um to get there and maintain that. Once we created those principles, that when they were in place, they would put us on the right path. And that when they weren't in place, we knew from history that every time they weren't in place, that it added it led to discontent, right? Um, so that those three principles became the measuring stick. And we use them all the time. And the thing is, is when you drill to first principles, first principles always have to be in place all at once, always together. So it became the thing that every single decision that we made going forward, uh, we had to have creativity, agency, and mindset, all three at once. If we just had creativity, but no agency, what does that mean? Like you, you, it's not a thing. And agency without a shared mindset can never truly happen. So those three things had to be in place all the time. And I think it's the definition of what it means to live a principled life. I always thought of that as like having morals, right? But I I view living a principled life, a first principled life, as one that keeps you, you know, feeling moored. You're grounded,

The Three Principles Measuring Stick

Speaker 1 15:40

and you are really in a place to make decisions. And I think that it's for a lot of people too, when you've got your principle so intact, it things come easy because you know instinctively when things now are right or they're wrong. Yeah. And I think oh, go ahead. Well, I think it's about um, you know, a lot of us when we're younger, you do things based on your gut. You don't realize that it's necessarily based on your gut because at the time it just seems that you're doing things like creatively, like it feels good, and it makes sense pragmatically, you know, because also because you're you were so you were so constrained, anyways. You really got to deal pragmatically, you know, because you don't usually have the finances or the resources to be able to act outside of pragmatism. But once you gain knowledge, once you get a seat at the table, once you get more money to play with, you can start to do things that are not pragmatic and that don't make sense for you necessarily creatively. And when you start to take those steps, you you get further and further outside of acting and responding in a way that is from the gut. And so I found that once we found those first principles, we all of a sudden got our gut back. We were moving in a way that just felt very natural. It wasn't overly studied or constipated or anything.

Speaker 17:18

Yeah. Yeah, it was it was free-flowing in that sense. Yeah, that makes that makes a ton of sense in the context of the book because I do think what what we did a lot was that iterating in terms of finding the structure and figuring out how to get the reader through everything you had to share. Because um, it was it was like, okay, this is the right thing, but it doesn't feel like it's coming across correctly. So then we would sort of circle back. And I know it's it's interesting you talked about being younger, because one of the first decisions I remember making with you about the book structure was to do it as a sort of linear timeline of your life. It's not, it's not a memoir, but it does you start with your childhood and move forward because, as you say, there's good examples and like teachable moments throughout. But I'm curious because you know, you are such a deep thinker who loves to think about this and also run a business. What was it like for you to write more kind of biographical material to do the more memoiry writing? There's there's just so many good details that you have this recall of. I was really impressed. So I'm curious what that experience was like from the writing perspective.

Speaker 1 18:22

It made me wonder why I didn't journal more growing up, first of all, because I was very, I loved this notion that um that all along in life you're connect, you're collecting these moments, what we refer to as like these dots, that like a Surat painting, when you're up close to these dots, you can't make heads or tails of anything that you're looking at. But when you step back and you see how they've all come together, it usually creates a very clear picture, right? And um, and so the thing is, is for all of us, those dots don't, they cannot create the picture until much later in life, right? Um, that's just a fact because dots come with time and they come with change and they come with different relationships and experiences. And so for me, what I loved being able to validate now at the ripe old age now of 58, is that those dots are making a picture. You do not know it at the time, but knowing the certainty that they are going to make a picture for you is very rewarding. And so I think when we talk about like what does it mean to all work out, just the knowledge that these dots are going to create something. It may not be something always beautiful or whatever, but it's going to create a picture is very settling to me because it lets you kind of just jump on that wave and ride it. But one of the things that's been a very important piece for um people who've read the book is to realize that if they are not present in their life at all times, they will not be collecting their dots. And so if you are taking the waitressing job, the babysitting job, you know, if you're doing these things in life so begrudgingly that you have just put an iPhone in your front hand and you're just gonna scroll through these moments while, you know, until you have to go bring the food out to someone's table, until you have to actually bag the grocery. If you refuse to be present, you will not collect your dots. And, you know, in each one going back with you, uh Blair, and going through the newspaper route, the waitressing jobs, the bagging the groceries, I realized how I was building this resume where I was learning how to interact with people. I was learning how people deal with a bad situation, how they handle when things are late or when they're early. And, you know, you were you were building a resume, whether you knew it or not. And those are all things that I have used equally, if not more, in my life than anything that I learned in a business class in school.

Speaker 21:31

Yeah, I I completely agree. And I think like the mu the word that comes to mind is like you have this reconter or reconteuse kind of tendency to tell these stories that prove out your point. And so I'm actually curious because I don't really remember what order this happened in. I'm thinking of all like the dots. I'm thinking of like the character specifically. Like I will never forget the woman with the Barney purple suit or like Benny and Ivan at the factory, or all these people that you bring up throughout your. Know building the business. But did the concept of bringing dots together as gathering your life story come as you were doing that writing? Or did you have that going in and it sort of was amplified as you actually put together the story?

Speaker 1 22:15

No, it came about as I was writing. And I

Collecting Dots By Being Present

Speaker 1 22:20

think that one thing that I always I mean, I thought I was good at, but I've definitely been told that I'm good at is coming up with like the very apt analogy that captures a moment visually for people. And you know, growing up around art and Surat, like I it's always just so I just thought that was the perfect analogy to use for how things come together. And but it you gotta get a lot of dots before you get your Syrah painting, you know?

Speaker 22:52

It's true, yeah. And I think to your point about like, yeah, not just staring at your phone, you have to observe a little bit. It's a very, it's a very novelist, I think, tendency on your part. Yeah, but you do also, I mean, like we said, this is not just a memoir and it's not just a business book, it's sort of the prescriptive memoir.

Meghan 23:08

So um Which I personally hate and don't believe exists. And I wanted to talk about this because I think it's it's interesting. Because you, when I got into this book, because again, I was relatively hands-off during the editorial process because Blair is a great collaborator, so I don't need to be micromanaging, which I'm sure you understand as a leader as well, right? When people do good work, you just kind of like back off and be like, I'm here if you need me, see ya. But like that's kind of how it was. And so when I got into it, I was like, oh shit, did we work on a prescriptive memoir? And then I was like, wait, we kind of did, but it worked. And the reason it worked is because a lot of people that come to me without as big of an audience or as much experience as you, Amy, think that they can just share their story and that somehow that will magically then transcend like to-dos and tasks and like personal growth and the work that happens in transformation, and so that people can magically learn from you and lead from example, which I I think people can get takeaways, but like it's very hard to do that. So your book uses your personal narrative, like Blair has been saying, as the narrative arc, right? Like this is how we work the way through the book. But there are actually sections of how-to's, and I've got them dog eared because I wanted to go back to them and do them. So I'll show them visually here. So, like for those of you watching on YouTube, um, and for those of you listening, it's just a grayed-out box text that clearly visually separates the narrative from sort of the how-to's. So there's still like, you know, exercises and how-to's for the readers. So it's not just like do what Amy did and you'll be successful. Yeah. So, like, how did you and Blair, and both of you, all of you can answer this question of like, how did you shape that, or where did those like to-dos come from?

Speaker 25:02

Well, I I do remember, Amy, that when we had talked about the need to have that section broken out, your your first crack at it was like, I'm gonna just call it do this. And I thought, perfect. Like, yeah, why why like gussy it up? And I just thought that sort of directness was so perfect. But yeah, I think in in my memory, a lot of it came from your creating those really good metaphors and anecdotes to start. Um, but we did work through kind of getting them to a point where it felt doable, right? Like, if that makes sense, like something concrete that that was really removed from your specifics and that anyone could try.

Speaker 1 25:40

Yeah. And I because I think um, because I personally, I mean, there's a lot of times like I want to read a memoir of someone who I'm I'm learning something historical, you know, and maybe there's a takeaway, like, wow, that person we were just talking earlier about uh Maggie Thatcher and and um Steve Jobs, you know, people who you're just you know, you have like a key takeaway, but there's no like step by step by step, right? There's no like real, I'm gonna put this into action learning on this. And um, and I think what I I love being able to learn and put things into action. I really do. And I and I know that the people who I engage with love that as well. And, you know, one of the things that I was very cognizant of of writing this book was that I do live in the gray. I don't have these extremes of the black or the white, you know, and um because we're writing a memoir about a company that, like I said, by many industry standards, it's like really, this is this is what you got. You know, I don't really have the extremes that are so sensationalized when people write biographies, right? And I don't have the really sad stories either, you know. I my parents are alive and well and they can't stop kissing and they love each other. Like, what do I say about that? You know, like exactly sad you. Um, so it's more like I but I do know that a lot of us are quite average in this way if you view yourself through these extremes, right? A lot of us are average. There's a reason why average is called average, like it's it's a big group of us in that area. And um, but we want to do big things, and so I think taking these examples and then universalizing them so that people can take action on them was really important to me. And I did grow up, you know, on the newspaper staff, and I loved studying journalism, and I love that way of talking where you know you um say what you're gonna say, you explain what you said, that you then you explain what you just, you know, you reiterate what you just said. Um I think that newspaper format is I've I've just always loved how it's definitely more words than something pithy. And it's not so many words that you can't really comprehend it and do something with it. So I think the book kind of struck that right tone.

Meghan 28:27

Also, spoiler alert, that is what we tell our authors to do when they write their books. I'm like, you remember term papers? Do you remember basic comp in high school? Yeah, same rules apply. It's just longer, right? Like it's not people make it overly complex, and it actually does not need to be overly complex. It's it's very funny.

Speaker 1 28:45

Exactly.

Speaker 28:46

Your sales background probably plays into that too, just because you know, like talking about all the work you did when you were at American Express and like sort of putting together those decks and you know, selling people on stuff literally is the same principle, right? I mean, you're you're

Making Memoir Actionable With Exercises

Speaker 29:00

trying to make an idea very clear, but not so abstract that they don't understand the point.

Speaker 1 29:05

So it's absolutely but even when you talk about the sales background, like it was funny when I was on the Tamron Hall show, one of the things that Tamron had like zoomed in on was this whole idea of kind of building a reckless resume that really does like take those dots and puts them into resume form. So sure, sales background right at American Express, but you know, when I was selling the kid my like drawing of my Apple in third grade, I was a salesperson. When I was selling those shitty crocheted scarves, when I was, you know, doing all of those things as a you know eight-year-old entrepreneur, I was a salesperson. And so, you know, I love this notion of a reckless resume for people because you can build it out so much further than literally the classes that you've taken or the job responsibilities at a real job. You know, you can say very succinctly, I'm a great salesperson. I, you know, I bring tasks through from beginning to end. And then you've got good examples of it, but they just don't live in those traditional corridors that people normally expect to see on a resume. I want to try and think of a way for people to build these reckless resumes.

Meghan 30:27

No, I completely echo that, and we've done content on that of like, what is the ironically, you are not the first of our clients to work at American Express. Nor are you one of our clients that work at Oglyby either, which is like unshocking, right? Like it's very funny to see, like, and y'all are uh the other client I'm referencing is in her 30s, the other one's in her 50s, and so it's just very funny to think about that in terms of those weird through lines. But I always say, like, of course, I was good at sales. I grew up as the daughter of an insurance salesman who's take us on calls, and then on top of that, I was a cocktail waitress, and that was my most favorite job, and it was my most fun job. And it taught me the most about managing people, yeah, right, and their emotions, because in that situation, you're dealing with people who either want to avoid their emotions or are really in their feelings.

Speaker 1 31:17

Well, it's like, you know, it's like for all the unbelievable strengths of Tracy, my head of design. Her core core strength, though, is the whole time she was at Parsons, she was putting herself through school by being a waitress at this place called the coffee shop in Union Square. And the coffee shop, like that place was just like banging all the time. You can talk about Tracy and her amazing creativity skills, but everyone in the office knows that where Tracy is just so invaluable is she is the ultimate multitasker. She has got so many things in the air and she is just working them and prioritizing and doing a phenomenal job at that. That skill set was fully acquired at the coffee shop. It was not acquired at Parsons, it was not acquired in her high schooling. You know, this was honed at the coffee shop. But I, you know, I hear, you know, from a lot of Gen Zers, especially, you know, when they talk to me, they are really seeing a waitressing job as something that they are closing their eyes and they're getting through it until they get their real job and they're not collecting their dots.

Meghan 32:31

I know a lot of millennials that operated that way too when we were younger. I mean, I'm in my mid-40s, and like now I'm starting to see my Surat painting of being like, oh yeah, I studied speech. No wonder Instagram reels are easy for me. I learned speech. Like, hello. And so, yeah, so it's just one of those things that's really interesting. I I would encourage all the listeners to think about their debts and like how I think a lot of times we get focused, especially us high-achieving women, get focused on the next and the next and the next, and we forget to think about what we're doing now and what's going right.

Speaker 33:06

Yeah. Well, and it's moving the goalpost, right? Yeah, about your wish that you had kept a journal. And I think that's such a similar impulse. It's like, yeah, it would be nice to really like see where I am in this moment and like collect that in a journal or you know, just mentally even. Yeah. Um, but it's hard to do. And I've never kept a journal as a writer. It's like it's hard, but I imagine it would make that writing process easier.

Meghan 33:31

I am a journaler and I throw out my journals.

Speaker 33:34

Oh.

Meghan 33:35

I only, yeah, I only keep because I realized they were like in my 30s, I realized they were just pain because I'd only write when I was unhappy. So I was like, why am I keeping this around? And then I would just keep a couple that were like, oh, this is emblematic of this time in my life. I'm gonna keep this. So there's only cool. Otherwise, they get recycled.

Speaker 33:59

Amy, I wanted to talk a little bit too about our revision process because we did something that I have rarely done actually as a collaborator and writer, but you had uh requested, asked about, and I said, let's go for it, which is we worked in person together for a day. It was like a kind of a marathon day. We really just like went through the book chapter by chapter. I think we had like some sort of sticky note, serial killer board. It was it was intense, but I thought it was really cool. I'm curious like what that was like for you, sort of going in. You had drafted the complete manuscript, and then we kind of you know dissected it and came out with a plan. But um, how did it, how did it feel doing that sort of live for 10 hours or whatever it was?

Speaker 1 34:39

Well, uh first of all, I thought it felt great because of you know, I was very comfortable with it because that's how I would approach anything in our business as well. But I also thought

Building A Reckless Resume From Real Life

Speaker 1 34:50

it was great because when I approach it in my business, I'm usually doing it with people who have a um much more organizational mindset than I do, and so I find it to be a very necessary step to happen in order for me to stay on track. So knowing that I was working with someone who had that skill set to augment mine was very relieving for me, and so um, you know, I'm I've always been a person who sometimes what I say can just be all over the place, and I see things in my head when I'm talking, but I that's why I tend to not look at people sometimes when I'm talking because I'm like mapping it out, but it's hard for me to like get that out of my mouth and get it organized. Yeah. So I think working with you and taking that and then bucketing it out was so helpful to see like how one was leading into the next and leading into the next. Um I mean, I remember once we got that outline really done and gotten the chunks of meat into each one of those buckets. We were like off and running.

Speaker 36:10

Yeah, it it took shape after that. And I think that that's what was so cool for me is that it really did almost sort of feel like a black box. Like I know we've worked hard and we talked about a lot of things, but it really was like beginning was this sort of shaggy draft, and the ending was, you know, things to be revised and stuff, but it had like a shape. So it was very cool. And I I appreciated, you know, usually we work, you know, maybe an hour or so on Zoom once a week, but to have that like continuity of discussion over a full day was really cool. And I think probably got a couple weeks worth of work done essentially by jamming it together. Totally. So speaking, speaking of process, because you had been working on and writing the creative pragmatist at around the same time when we were working on Almost Reckless, and it's a very they're very different books. They have the same, I think, core idea. They both sort of have these like almost contrasty titles, right? Like Almost Reckless, Creative Pragmatist. It's very aimy. But I'm curious from the you know book perspective, what it was like for you as an author to to work on both and how they were different. Because, you know, creative pragmatist is uh it's much more visual and it's you know uh the writing is just different by nature because it's I would say a little more instructive. But um, you tell me.

Speaker 1 37:30

Um I mean that was that was definitely challenging for me because I had to really try and um bifurcate my time, not in terms of um because the the written part to me was easy and contiguous. I where you know where almost where creative pragmatism addresses understanding who you are and how to bring those visuals together, almost reckless is like the the last third. It's really like getting in that mindset to understand who you are, live it every day, and um and do big things with it. And so the written part was easy for me. What messed with my head a lot was I very much saw and I had not recognized it until that till the situation occurred. But if I had a day where I started out doing all my illustrations, which I was doing for the creative pragmatist, my brain could not switch into writing. It was you know, it was I was using one part of my brain, and that part then would dominate the day. And so it was, you know, it was like if I started out just drawing all day, I would almost be speaking as if I'd had a stroke, like I couldn't get words out. Like you would you would actually maybe want to call a doctor if you were talking to me because you're like, Amy, it's a cup. The word is cup that's in your hand. So I had a really hard time speaking by the end of the day if I had spent the whole day drawing. So I had to really make sure that if I was gonna spend the day drawing, I was gonna let it be there. If I was gonna be writing, I was gonna let it be there. But I had a hard time going from one to the other. That's yeah.

Speaker 39:32

I don't I don't know that we've ever had an author who also was illustrating another book at the same time.

Meghan 39:37

Yeah, never.

Speaker 39:38

Yeah, just it does remind me.

Meghan 39:40

I don't know if this happens to you, Blair, but I I call it like final written exam mode, where if I've been writing heads down for a long time, I feel like I just did a written exam in college. Where you're just like so focused, and like you're like, I gotta get it right, I have one shot. Uh that's not true professionally, right? But like I walk away in this like fugue state, and it takes me like a good 10 minutes, usually of being outside to like come back.

Speaker 1 40:05

Yeah. Well, my sister's a clinical psychologist, and when I

The Marathon Revision Day That Worked

Speaker 1 40:10

told her about this, she was saying that it in psychology, it's absolutely a true thing. And she said to like what she would do with even with their school where she was a psychologist, that even doing things like this was crazy. As I Googled it to make sure she wasn't lying to me and just making a joke. But she said, doing windmills, the act of like doing windmills, yeah, literally shakes up your brain. That's wild. I know it's like you have to Google it because I swear it's true. Um, but it shakes up your brain, and that is one thing. She said, if you really are, if you've got to be doing both in one day, try doing windmills. Like the whole action of going back and forth literally like gets your brain reoriented.

Meghan 40:56

Super cool. I'm gonna do that from now on.

Speaker 40:59

Yeah. Yeah. I, you know, it's interesting that you bring that up, Amy, because one thing I didn't put this in my questions, but I do want to ask you is that your sort of fan base and the people who gather uh for your talks and your lives and everything come from such a broad professional background, which I think is so cool. You know, clinical psychologists, TV executives, doctors, lawyers, everyone. What do you think draws them to you and to Tibby and to the almost reckless ethos? Because that's really what the book is about, I think. Um, but it's also singular.

Speaker 1 41:31

Some of the subjects that we talk about, I think that there is an inclination, whether it's in entertainment, whether it's in publishing or whatever, to really just serve something up that is so pithy and catchy and just run with that. And it and yes, in terms of the numbers, it will attract, you know, millions. You know, there are you know that the books that have the three-letter names, you know, like that are just like one very shallow concept on the book cover, you know, like it's a thing, right? And but we've got a group that we always say, like they know that you cannot have better abs in seven minutes. There's no such thing as seven-minute abs. And they're okay with that, but they also don't want you to start like talking to them about this three-year exercise regimen either. Like, there's somewhere in the balance of in-between. It keeps coming back to this balance notion. So, our people they want information, they want you to have done the research and then they want you to lay things out so then that they can draw their own conclusions and have a conversation about it. They really, really, really appreciate that. So, I would say on one end, like the person who wants to overanalyze it to the nth degree, they're not our people. If you are satisfied with the pithy, like, you know, I mean, listen, sometimes the pithiness, like it's a mantra that you live with. Don't sweat the small stuff, right? Like we can all quote it, right? But it's a quote, like it did it, it doesn't need to be like a 400-page book, right? So somewhere between the pithiness and the gigantic encyclopedia tomb is where our people reside. And so I think it's no surprise that we attract a lot of people who are intellectual but not overly intellectual. Um, they're thinking, but they don't like go around in circles. Um and it's so it's a lot of these executives or entrepreneurial mindset people or people who ask why and they mean it. They're not like why, like they're like, why? You know, there's a tone in why, and yeah, those are our people.

Meghan 44:00

I love that.

Speaker 1 44:01

And they and they show up in young people too. I mean, one thing that's been so much fun out of this that Blair, you know, this wasn't even at all on the radar when we started was we've taken a lot of the notions from the book and we turned it into these games. And so we've turned it into a deck of playing

You Are Your Own Algorithm

Speaker 1 44:20

cards that take people for through the first third, the second third, and the third third. And um, so we've even got a whole separate podcast called uh the Gray Area Podcast, where we've got three Gen Zers in our office who are playing the almost reckless game and equating it to them. And it's this whole thinking game. And we've got a whole nother one that is like, you know, building a mentor as if it were like a Lego man and not, you know, having expectations that one industry or one person could represent at all, but really thinking about what those components look like. So these accompanying almost reckless games are really fun to take these notions that we uh wrote about and take them much further. I love that.

Meghan 45:08

That's very cool. And it actually segues really nicely into our last question we ask all our guests. So, based on the numbers we have for our own audience, most of the people that are listening to this podcast absolutely need to grow their author platforms. They need to grow their audience, they need to test their frameworks and their concepts out with real people. They need to, you know, really hone in on their frameworks. You know, they they need to be almost reckless in building their author platform and just trust that their book will come out someday. So, given all of that, given that context, what would be your advice to those people based on your own journey?

Speaker 1 45:46

I think that the best advice that I could give anyone right now, today, is you are your own algorithm, you are your own AI. And the minute that you give that off to someone else, the minute you take it in from someone else, you are altering your DNA, and that is all you have. When we are in a place of with all the AI threats that we have, with the overwhelming amount of information coming at us that is maybe some of it can be used for good. It's often used to make you feel destabilized. Um, when you realize you are your own algorithm, you are your own AI, you will do things that that are going to be different. You're going to be on a different path than others. And in a world of sameness, that is as good as it gets. And that's a great thing. It is good. It's a good place.

Meghan 46:56

Yeah. I love that so much. Uh I just love that because I do think there is like other things going on that maybe in five years, ten years, twenty years, we'll look back on this time in America, spring 2026 when we're recording this, like and think, oh shit, that was what was happening for real. Like, I do not to be a conspiracy theorist, but I'm kind of being a conspiracy theorist.

Speaker 1 47:21

But but I think that for an entrepreneur as a business person, when everyone's looking one way, you look the other. And everyone is on algorithm, everyone is a combination of AI output right now. Not everyone, but a lot. Look the other way. It is where you will find your differentiation, it's where you'll find your individuality, which is great as a business and it's great as a human.

Meghan 47:50

Agreed. Amy, thank you so much for joining the podcast. So we're gonna include a link to that podcast you mentioned because I would love to share that with our audience. I think it'd be really helpful. I'm gonna listen to it. And then, of course, a link to Buy Almost Reckless, her new book, as well as her first book, Creative Pragmatist, if you're looking for some fashion and style inspo. Um, it's a great book to have.

Speaker 1 48:15

So thank you so much. Thank you. Yeah, so the the gray area podcast and the almost reckless podcast can be found on Spotify and on our own site as well.

Meghan 48:26

All the different ways and places, all the spaces and places, as I like to say. Well, thank you all for this great interview. Thank you, Blair, thank you, Amy, and to all of you listening. Cheers to your success. We'll see you next week. Thanks for tuning in to the Kind of a Big Book Deal podcast. If you enjoyed this episode, I would love it if you subscribe and also leave a review. Not only is this good for my ego and annoying for my enemies, but it also helps more entrepreneurs like ourselves find this podcast. Also, I'm pretty sure it's good karma. See you next time.