#259: Sarah Gibson Tuttle, Founder and CEO of Olive & June – Work on yourself

2 Oct 2025 · 55 min · 27 chapters

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In short

Sarah Gibson Tuttle’s journey from finance equity trading to founding Olive & June, and how she leads with self-awareness, customer service, and community. She explains the brand’s at-home nail “salon quality” mission, why she didn’t chase “disruption” language, and how she builds a culture that learns through imperfection.

Guest backgrounds

Sarah Gibson Tuttle is Founder and CEO of Olive & June (nail salon chain turned product brand). She previously worked about 10 years as an equity sales trader at JPMorgan Chase and Morgan Stanley. She studied philosophy (major) and theater (minor). She also references therapy and a childhood where her father restricted nail painting.

Key claims

Nails are a coping mechanism that boosts confidence; high standards and pressure training shaped her leadership. She left finance when she stopped feeling excited to work. Olive & June succeeds by democratizing salon results at affordable prices (e.g., Manny system; polish around $8 after feedback), plus education (“Olive University”). Social content is for inspiring/educating, not direct ROI.

Notable examples

Halloween nail designs (bats, upside-down cats, blood drip); she went live on Instagram 57 days during COVID teaching at-home nails; she credits “good fortune” plus preparation for 16x growth around COVID.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

From Childhood Restrictions to Entrepreneurial Success

0:45 to 2:10

Sarah shares her childhood experiences with nails and how they shaped her identity.

“And I would paint my nails when he was away on business trips.”

The Nail Industry's Seasonal Trends

2:10 to 3:32

Discussion on how nail polish trends change with the seasons, especially around Halloween.

“You know, I want to get into how you're, how you're leading Olive and June.”

Lessons from the Finance World

3:32 to 6:00

Sarah reflects on her decade in finance and what she learned about pressure and customer service.

“So nails has always been this through line for me of when I felt insecure, when I felt like I wasn't sure, you know, what to wear or how to act.”

Challenges in High-Pressure Environments

6:00 to 8:10

Sarah recounts a challenging client interaction and the lessons learned about balancing interests.

“You are, it's very similar to what I do today, but it's just in a different realm where you're making sure their trades are correct.”

Realizing It's Time for a Change

8:10 to 12:00

Sarah discusses her feelings of disengagement in finance and the impetus to pursue her passion for nails.

“So like, you know, you're in this high pressure job.”

The Decision to Disrupt the Nail Industry

12:00 to 14:00

Sarah explains her motivation to enter the nail business and how she envisioned disrupting the market.

“slow evolution, but also a number of external factors that were pushing me to realize that that maybe New York and finance and frankly, my relationship, all of it was kind of not working for me.”

Understanding Decision-Making

14:00 to 14:30

Learn about the importance of taking time to make thoughtful decisions.

“They take, they take time to marinate a bit.”

Olive and June: A New Approach to Nails

14:30 to 16:40

Discover how Olive and June revolutionized nail care from salon to home.

“And so for anyone who's never heard of it, Olive and June started as a nail salon chain.”

The Story Behind Olive University

16:40 to 18:00

Explore the origins and significance of Olive University in the brand's mission.

“But we've also been able to take education and content and really put it on top of the product so that you're not lost in the category anymore.”

Feedback from Truth Tellers

18:00 to 19:25

Learn about the value of honest feedback in leadership and decision-making.

“Because Apple is computers and et cetera, et cetera.”
Show all 27 chapters

Navigating Advice and Decision Making

19:25 to 21:40

Understand how to filter valuable advice for better decision-making.

“tells you this is not the way they go and you know, how do you process it to either stay on course or make a necessary pivot?”

Challenges of Scaling a Business

21:40 to 24:04

Hear about the difficulties of scaling a business and the importance of community input.

“At the very end of the episode, he and I are going to debrief some of the concepts that he talks about with Sarah Gibson Tuttle.”

The Role of Luck and Preparation

24:04 to 25:55

Find out how preparation and luck contributed to Olive and June's rapid growth.

“let things sit with me because often I come to the place where everybody else is.”

Customer Connection During COVID

25:55 to 28:00

Learn how Olive and June supported customers during the pandemic through innovative engagement.

“I always think you have to time it right.”

Building Community Through Social Media

28:00 to 29:26

Learn how Sarah Gibson Tuttle leverages social media for community engagement rather than direct sales.

“And you're going to have done it yourself for a dollar.”

The Role of AI in Business Operations

29:26 to 30:44

Discover how AI tools assist Olive & June in structuring creative processes without replacing human creativity.

“Or I saw that nail art or, oh, they made me laugh or, oh, I saw someone talking about how great those press-ons are.”

Creating a Culture of Experimentation

30:44 to 33:52

Understand how fostering a culture that embraces mistakes can lead to innovation and team growth.

“And I'm, I'm deeply sympathetic to that.”

The Importance of Self-Awareness and Growth

33:52 to 36:18

Explore how self-awareness and feedback contribute to personal and professional development.

“And ultimately, that's sometimes the biggest hurdle or roadblock for you if you're defensive or you don't, don't hear them because then they don't want to do it ever again.”

Lightning Round: Fun Insights About Sarah

36:18 to 39:28

Enjoy a quick-fire session revealing personal preferences and fun facts about Sarah Gibson Tuttle.

“You're not born as one person and you can never change.”

Leading with Structure and Joy at Home

39:28 to 42:00

Learn how Sarah balances discipline and fun in her parenting approach to foster growth and happiness.

“So you talked about your young daughter.”

The Journey of a Passionate Leader

42:00 to 43:14

Discover Sarah's commitment to her role and her vision for Olive & June.

“I am still day in, day out, 24 seven founder CEO and not leaving the business because I love my job.”

The Importance of Hard Work

43:14 to 44:30

Learn why hard work is essential for achieving success in leadership.

“David, I loved this episode with Sarah Gibson Tuttle.”

Navigating Leadership Challenges

44:30 to 46:39

Explore strategies for working with less self-aware leaders.

“So quite apropos for this debrief conversation that we're going to have.”

The Value of Self-Awareness

46:39 to 48:20

Understand how self-awareness can guide career transitions.

“But, you know, I think if you're a really good member of the team, you know, you try to help everybody get better around you.”

Making Purposeful Career Moves

48:20 to 50:14

Get tips on transitioning careers without burning bridges.

“For people listening who might be in a similar spot of thinking about transitioning in their career.”

Boosting Confidence Through Self-Care

50:14 to 53:20

Explore how personal grooming can impact self-esteem and performance.

“And if you can't go grow where you're at, go somewhere where you can.”

The Impact of Feeling Good

53:20 to 54:16

Discover the connection between self-esteem and business success.

“You know, if you talk to anybody in the fashion industry or the clothing industry, you know, what do they tell you to buy?”
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Transcript

Automatic transcript. May contain errors.

0:00So at some point I turned around and I said, as much as I love my clients, do I really love this life? Is this really what I was destined to do? I wasn't thinking about disruption. I was thinking, what am I going to do with the rest of my life? I love this. It's like a therapy session.

0:20So here you are, you're running this wildly successful brand. Olive and June that's pulling in close to$100 million in revenue a year. But as I understand it, you weren't allowed to even paint your nails as a kid. You know, what do your parents think of all this now? I'm sure it's wild because my dad did not let me paint my nails as a kid. You're right. And I used to have a box of nail polish under my beds, you know, secretly hidden. And I would paint my nails when he was away on business trips. And red was especially his least favorite color. so that was my go-to and continues to be my go-to so you know I think it's been a wild journey they now talk about nails as if you know this was this was something they've always loved about me but we all know the truth and I keep telling that I keep telling the truth as much as people will listen I guess that's why they say success has many fathers or many mothers or however you want to think about it, you know?

1:23Exactly. Exactly. As we're doing this podcast, you know, Halloween's coming up. What's the most popular nail polish color for the for the October season? You know, what's so funny is that the seasons change probably about a month or two before the clothes change, like the nail seasons change. And so we start seeing darker colors pop up in August and no one's ready to wear those clothes because it's too hot out still, but people are ready for those nails. So you'll see, we have a ton. Halloween's a huge nail season. So we have a ton of designs that are out across our retailers, everything from bats to literally cats hanging upside down to blood drip.

2:04I mean, Halloween is very, very big in nails. Yeah. I love it. You know, I want to get into how you're, how you're leading Olive and June. We'll do that in a few moments, but you know, I want to stay, stay on your childhood a little bit longer here. Can you tell me another story from your upbringing that shaped the kind of leader you are today? I love this. It's like a therapy session early on this Tuesday. Oh, yeah. I'm known for being a great shrink. Fantastic. You know, my childhood was pretty idyllic from what I knew of it. You know, I look back and my dad's pretty tough and he can be a very explosive person personality wise.

2:49So I look back and I, I have, I'm raising my daughter in a bit of a different style, but I was really, I had the best older brother and I was a really pretty happy kid. I always felt a little bit, you know, I don't know if it was insecure, but for sure kind of scared of things. And I don't know where that really that comes from. Cause my parents taught me every single day or every week of my childhood that I could do anything I put my mind to, but I always felt a little bit kind of not put together and nails has always been my go-to when my nails were done, when they were painted, I felt like I could take on the world.

3:27And so it was everything from sneaking Manny's, you know, my parent, when my dad was away and completely avoiding his rules to when I got to my first job in finance, my weekly manicure was the only thing that made we feel like I know what I'm doing in this job because I was a philosophy major, a theater minor, and I had no idea what I was doing at J.P. Morgan when I started there. So nails has always been this through line for me of when I felt insecure, when I felt like I wasn't sure, you know, what to wear or how to act. If my nails were done, I felt really like a full person and I could do anything.

4:08That's amazing. So your passion for nails goes way, way back and is just kind of rooted in your DNA? I don't even think I knew that it was, if that makes sense. It was something that was a kind of a coping mechanism for me that I, and I just also thought like, it's just nails. That's what I think I thought when I was growing up. I wasn't a big makeup person or hair. I mean, it was always nails for me, but when I look back, it's so obvious what a thread it was for me in order to feel like my best self. And it's what I love about this business because I get to give that to everyone everywhere at an affordable price.

4:44And I feel so proud of that. And, you know, you really didn't get into the nail business right away. As you mentioned, you started out in finance and you, as I understand it, you spent 10 years as an equity trader starting at JPMorgan Chase and then later at Morgan Stanley. Tell us that story. How'd you get into that aspect of the business world? It's kind of boring. My dad was in finance. So finance felt like, you know, the next logical step. All of his friends are in finance and my mom, it was in medicine. So her whole world was medicine. And so it was one of the other, I think in my mind and medicine was, and I mean, even though I brought up blood dripping nails, blood and medicine are not for me.

5:29So on nails, yes, but not as my job. It was kind of boring. It was like, well, he, he was doing this. I did a summer internship on the floor of the Stock Exchange and I loved it. I think my personality was really well suited for something that's fast paced, that's demanding, that you have to make people happy. All those things I thrive in. And so I started interviewing in college my senior year for jobs in finance. And I got a job as an equity sales trader at JP Morgan. And really what that job is, is servicing clients. It's really making people happy. You are, it's very similar to what I do today, but it's just in a different realm where you're making sure their trades are correct.

6:10You're making sure they have all the research. You're just, it's just client service in a different way. And so I did that. And I think in some ways I was on autopilot because this is what my dad had done. It felt really comfortable. Um, I was doing really well at it. I was getting promoted. And so at some point I turned around and I said, as much as I love my clients, do I really love this life? Is this really what I was destined to do? I don't know. I got to see mine and intro to econ twice. It feels like I probably wasn't. I really thought to myself, what do I want to be doing with my life?

6:41And that's where I started to really think about and soul search what was going to be next. So like you're in this high pressure environment though. I mean, the finance world, equity trading, that's a lot of pressure that you're feeling every day. You know, what do you think that that really taught you that you carried into this next world that you moved into? High standards for sure. which of course my family had already taught me that. So that was a lesson I already knew, but then I knew it acutely. But everyone I was working for or with had incredibly high standards and was performing at an incredibly high level.

7:17And so, and also time, right? Where if you're trading a stock, if one of my hedge fund clients was sending me an order to buy or sell shares of a stock, it's milliseconds, it's seconds that you have to get that done potentially, or you have to watch it super carefully over a period of time. And so you're really thoughtful of what time means and what, you know, now fast to market makes total sense to me. But I understand acting under pressure and under a time constraint. And so I think overarchingly, all of it was customer service, but it was also customer service at such a high level that, and with such high stakes that you learn, you learn what pressure looks like.

8:02And you learn to either love it or hate it. I particularly like pressure. I think I perform very well under pressure, better than when there's lack of pressure, frankly, which I see in my daughter. And I'm like, oh, goodness gracious. So like, you know, you're in this high pressure job. Was there ever a moment or was there ever a time where, you know, you thought, oh, my God, I've screwed up so bad. Can you tell us that story and how you got or how you survived it? I mean, so many. There was one time with one of my hedge fund clients where I talked, not talked back to them, but I pushed back. I thought they were being really aggressive about what they thought their execution should be.

8:42And we got into it. And I remember I had to talk to my boss later because they went to my boss and said, I didn't like how that went down. You know, it's an interesting thing because you're balancing the external client, but you're also balancing your internal team, right? And how much importance does your client get versus your team? And I think about that a lot today. I mean, I defended myself, obviously. And I think there was better ways I was a bit reactive, which I get from my dad, speaking of our therapy session. But, you know, I think when I think a lot about, I was highly protective of my team and of their execution and of what they had done with the trade.

9:22And so I really had to learn the balance of internal versus external. And today we still think about that, right, where it's our manufacturer versus our head of ops or, you know, there's always people on both sides of a conversation or a disagreement or, you know, hopefully not a blow up. But, you know, anything below that is normal. And so really being thoughtful of both parties and how do you bridge the gap when you're kind of far apart on both sides of that disagreement. So you go from like getting C minuses and econ to getting into this world and actually being quite successful at it. So when was this moment that you had where you said, hey, you know, it's time for me to walk away and step into something new?

10:11I think the entire journey every year or two, I thought to myself, what, what am I going to do with the rest of my life? I, I never really thought of it as a long-term career, I think, but it was, it was, it was a decade long. And, you know, I can, again, I did pretty well at it. I was not the best person on that trading desk by far, but I, you know, again, you, you get promoted enough and you do well enough that you're doing okay, um, in a cutthroat world, but probably right around like the seventh or eighth year in, I thought, I love making people happy, but this doesn't feel like, I don't, I'm not excited to read the Wall Street Journal.

10:51I'm not excited to come to work. I'm waking up thinking, can I sleep in today? Can I say I'm sick? And it just, when I'm the, when I'm a bad version of myself, when I'm someone who doesn't want to do what's in front of me, I know I'm in the wrong place. And that could be in a friendship. It could be in a relationship. It could be at work. I'm very aware that when I start to disengage, something is amiss. And it doesn't mean you just give up, right? I mean, that was seven or eight years in and I was there for a decade. But I knew I had to start figuring out what my next step was going to be. I just had no idea.

11:25I was completely lost. By the way, I just was getting married for the first time. I was kind of going through that journey. And then I was not happy in my job. And then I was not happy in my marriage. And then it was like, oh, goodness. like there's a tidal wave coming at me. But I did take two or three years to say to myself, okay, I need to change the course of my life and do something that really fulfills me and makes me feel just excited to be at work every day. Because I'd given it again, close to a decade, and I wasn't really happy. So I think it was a slow, to answer your question, I think it was a slow evolution, but also a number of external factors that were pushing me to realize that that maybe New York and finance and frankly, my relationship, all of it was kind of not working for me.

12:15And so, you know, you had this early on passion for the nail business. And, you know, so tell me how you thought about, you know, going into that industry and, you know, everybody talks about the importance of disrupting categories. You know, how did you think about disrupting that category. It's so funny because disrupting wasn't even part of the luck, like the lexicon at that point. You know, I wasn't thinking, I wasn't thinking about democratization. I wasn't thinking about disruption. I was thinking, what am I going to do with the rest of my life? And I was interviewing for jobs in LA and I was sitting in a dry bar, which is a hair blowout bar for those who don't know it.

12:57And it was in its heyday. So it was when everybody loved dry bar. And I sat in that chair. And I thought, this is the best experience I've ever had in a space. Like I just love there's cookies and there's this and there's that. And so, and then I went to get my nails done for the same interview because I was in LA interviewing. This is where the driver was. This is where they started. And the nail salon appointment experience was so starkly different than what the, what the driver experience had been. And I thought, why don't they have this for nails? And that I think sat in my head for a period of time.

13:29Cause I was so focused on getting into entertainment and changing my life. And I love TV. And so this was going to be the new, the new, my new life was going to be entertainment. And then at some point I was on vacation and my mind got to take a breath. And I remember sitting on a, you know, on a, uh, you know, a pool chair by the pool and thinking, wait a second, I'm going to do this. Like this is, I've always loved nails, you know, it all started to click. And so I think that, you know, I don't, these ideas for me don't happen immediately. They take, they take time to marinate a bit. And that's something about my personality that I'm, that I'm now acutely aware of that I take a minute.

14:09I got to reshape things a few times. I have to really be thoughtful of what's, what's going on and not rush to a decision. Um, and so it's a little indecisive Libra in me, but I, it also leads the best decisions. And so I had that light bulb moment, but after I had been marinating on it for a bit. For anyone who hasn't heard of Olive and June, tell us about the product you offer and what makes it so special. Absolutely. And so for anyone who's never heard of it, Olive and June started as a nail salon chain. And so that's where the dry bar of it all came in. It started as a nail salon in 2013. And then we subsequently launched a product line.

14:48But Olive and June is your best friend for all things nails. The idea is that nails is this category in beauty, but also in personal care that feels a bit like a mystery to the consumer. And we want to debunk everything for you. We, I love being people's best friends. So it works out quite well for my personality, but I love nails. And I know that, you know, their stat is something like 96 or 98 % of women feel better when their nails are done. So I wanted to give that to everyone. And so it started as a nail salon chain that we then launched products off of. And the reason we launched products was not so we could have like the best blue in our polish line.

15:27It was really so that you could be able to get a salon quality manicure or pedicure at home. So you were able to, at an affordable price point, really get what people were getting in salons, but paying 80, 90, a hundred dollars for. And it's been incredible to see the growth because what we launched as like our original Manny system kit, which is everything you need to get a salon manicure at home has now expanded to products across the subcategories, whether that be press-ons, obviously classic polish and multiple lines, gel, et cetera. And so what we've been able to do is really, to bring back the word from before, democratize that in-salon experience for everyone, everywhere.

16:09And it's been incredibly rewarding to be everyone's best friend for all things nails, because not only have we had a ton of innovation in the space and changed the category, because before all of in June, DIY was basically not part of nails. It was a forgotten piece for the consumer. And now we've led the at-home Nip Mani revolution, nail revolution. But in addition, we've been able to innovate, obviously, every product. Every product is better. It works. It lasts longer, et cetera. But we've also been able to take education and content and really put it on top of the product so that you're not lost in the category anymore.

16:48Not only do you have the best products that last longer than the competition, but you also have this education. And we do it in a ton of different ways, whether sometimes it's long form, sometimes it's really snackable content, but in a way where if your best friend was talking to you about how to do this, that's the voice that you're receiving it in. And you actually call it a university, right? We do. Olive University. You know, Olive is my great grandmother and June is my grandmother. So it was named after these incredible women in my family who've inspired me. And we say, all of you a lot because obviously it's, it's the slang for I love you.

17:23Oh, that's good. And so then all of university is, is a key part of, of our lives at all of in June. I love the background on the name, but that name is strange. I mean, you know, it's not something you would naturally come up with it. You know, I said, where in the hell did that name come from? You know, but it now, now I get it. It's so funny because people, people have always said, well, you didn't put anything nail in it and you didn't put anything salon in it. And it's not, it's not obvious, right? Like some of the other brands out there. And I said to everyone, I got pushed back constantly.

17:56And I said, if, and they're like, they're not going to know what it is. I said, if they don't know what it is, then I haven't done my job right. Because Apple is computers and et cetera, et cetera. So if you can't figure it out, then I have not done my job correctly. Yeah. Well, I love it. I love the story about it. You know, you know, it's, it's important for, for, for leaders to have truth tellers around them. You know, people, people tell it to them the way they at least think it is. And as I understand it, your, your husband didn't think Olive and June was a very good idea. How'd you resolve that one?

18:26He's one of my best friends. He's also my ex-husband now. So no, but that's not why don't worry everyone. David did not just stumble upon the reason why. Um, but he's, he is one of my best friends and he, to this day tells everyone, which I love, he's like, I didn't think it was a great idea. makes me laugh. And it's why we're such good friends still and why most of my friends, I would say, if not all are no people. I don't want to be surrounded by yes people to your point. I don't want to be with people that just yes me, or just tell me what I want to hear, because I think life's perspective and, and creating something really special for people is about collective thought.

19:07And, and again, to that point of marinating ideas and letting them letting people ruminate over them and going back and forth. And I like people that make me a better version of myself. So my ex-husband included. And so I, I, I like that. I seek that in my relationships in my life. So when you get feedback like that, that from a no person or somebody tells you this is not the way they go and you know, how do you process it to either stay on course or make a necessary pivot? What's, what's your decision-making process? My decision-making process. I filter everything, obviously, through my own, you know, the information I have in my gut and in my instinct.

19:47But I would say that I will really weigh what people say if they are valued people in my life, right? Obviously, people say things to you all the time, and not everyone is a valued point of view. And you have to be able to discern between a valued point of view and just a point of view. But for those that are valued point of views in my life, I really sit with what they've said and I try to adjust if I think that there, if there's, there's merit to it. Often there is, again, I surround myself with some pretty impressive, smart, curious people that, and I ask them their opinions on purpose. One of our advisors of Brian Sugar, who I talk about a lot, who's the founder of PopSugar.

20:30And he has a, he has a fund now called, I believe, Sugar. He, I remember, said to me, don't go into retail. You're going into retail too fast. And the price of your polish is too high at$12 or$14. I ignored him on retail because I thought he was wrong. And I agreed with him on the price of the polish. And we lowered it to$8. And he was spot on correct. And so I tried to, what I did is I went to the market and I I looked at where things were selling and who was I trying to compete with and all of these things. And I what I realized is that all the major names, all the household names, they're all at retail, but they're all at lower price points.

21:10So I was able to take the feedback and then do my own research. And often I take the advice. I mean, I again, I try to really be it's all of in June is not the Sarah Gibson Tuttle company. It's all of in June for a reason. I'm creating it for the community. So to take feedback, whether it be from a great advisor or a community or anyone in between is so critical to our success. Hey, everyone, it's Kula. Stay tuned to the very end of the episode because David and I have a brand new format that we're introducing in this week's episode of How Leaders Lead. At the very end of the episode, he and I are going to debrief some of the concepts that he talks about with Sarah Gibson Tuttle.

21:49So stay tuned because we're just going to get right into it after his interview with Sarah Raps. Watch to the very end. You started this business like any solopreneur. You're doing everything by yourself. What's been the hardest thing for you to give up? Because you've had to scale this business now to where it's a$100 million brand. What's been the hardest thing for you to give up? You talked about how you surrounded yourself with great people. Everything. Everything. Everything is hard to give up. No. Some things are easy to give up. I love giving up operations. So that's totally fine. I'm happy to give up, you know, die lines and projects like that on inserts.

22:31But no, I think the hardest thing is that there's creative that goes out that I don't always agree with. Like, I don't always like it or I don't personally think it's the right creative. But the thing is, is that you're building this for a community of people. You're not building it for yourself. And I always say to our team, we're here to serve the customer. This is not, community is not just a word at all of InJune. It's the heart and soul of our business. And so we have to create lots of different things for lots of different people. So everyone feels seen and loved by the brand. And so there's oftentimes where a creative direction is something that our team is really passionate about.

23:11I don't, I don't see it. It doesn't, but then I'm like, I'm just an N of one, but that's very hard for me, but but it has resulted in some of the most engaged with creative. And so I have to remember that and take a step back. And we hire amazing people to do their jobs, let them do it in the best way possible and see what the results are. But as a creative person, and I worked in the marketing world myself, when you see something that goes out that it doesn't meet what is your standards, doesn't that just eat at you? And how do you put it in the parking lot? A lot of work. I mean, I work on myself.

23:51I try not to react as much. I mean, again, I kind of alluded to it. My dad's a pretty explosive person. So there's a lot of reaction and reactive tendencies that I have. But I work really hard not to have an immediate reaction and let things sit with me because often I come to the place where everybody else is. Sometimes it's a a day or two later or six months later, but I get there. And so I have forced myself to kind of retrain myself to allow for that in our working environment. And frankly, I love it. It's benefited the business so much. And so I think when you see the results, right, where when you take a step back and you say, okay, I don't love this.

24:39Let's see how it goes. But then the results are explosive. By the way, even if they're not explosive, they could be explosive to the downside, but that's okay too, because you've learned something. Once you get the learnings, but especially when they're positive, you realize like, oh, I don't, well, first of all, I don't know everything, which you kind of already know, but it's a good humbling moment. But also I am not, you know, I'm an N of one. I am our core customer, right? I am the core customer of all in June. I do my own nails. I'm obsessed with nails. I, you know, I stress and I think about my color for the next manicure and next pedicure, but I'm still an N of one.

25:17And so, and this community to your point at, you know, close to a hundred million dollars in revenue last year, think of how many bottles of nail polish at$8,$9 that is. So if that's the case, then I, there's so many people in our community that we are here to serve. Yeah, and you've had explosive growth and it really took off in 2020 where I think you grew your business 16 times and launching your at-home kit just before salon shut down, before COVID. How much of that success do you credit to preparation versus just good fortune? I always think good fortune is important. I always think you have to time it right.

25:57Things have to go your way. you have to have luck in some capacity, but you have to be prepared for that luck, obviously. We launched that Manny system a year before COVID hit. And so luckily we had the right product, but to grow 16 times in a year from, you know, 2 million to 32 million in product sales was insane. And so, and then to continue to grow after that, you do need the wind at your back. And so I'm grateful for that. But I think the reality is if we hadn't had the right products, if they hadn't been true innovation, if we hadn't gone live every day for, I think it was something like, I don't even know, 40, 50 days, like in a row, because people were just sitting there with their boxes and they didn't know what they were doing.

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26:43And then continuing to have long and short form content and really supporting people, it would have been a flash in the pan. And that's why we've been able to scale to close to 100 last year, be the only, you know, beauty company that got fully acquired last year, which was really a proud moment for us because we not only were prepared, but then we had incredible execution and support for our community. And we've always put the community first. We've never made it about us. It's always about their experience, their journey. You know, and during COVID, and I think you alluded to this, you went live on Instagram 57 days in a row to teach people at home.

27:22I mean, that's impressive. And what did that season teach you about staying connected to your customers? I have always, because of my background, been a customer service person. So it was just, it reiterated to me what people need in life, which is a pep talk. They need to feel like they can do anything. And we are here as a brand with incredible products, but also we are here with that pep talk. We are here to say, you can do this. It's not that hard. You just need to know a few things and you need the right products. And then you're going to get this$40,$80, whatever it is, manicure at home.

28:00And you're going to have done it yourself for a dollar. Right? So it's just that people need the support and the pep talk in order to get the confidence to try something. And so it really reiterated that for me. It solidified it for me. It didn't teach me anything new, but it was, it was a nice reinforcement for what my vision was for the business and how to grow it. And now you have this massive following on social media, but, you know, sales obviously drive your business. How do you think about converting all the followers and this, you know, the community you have on social media into customers?

28:41I actually don't think about social as an ROI, as ROI. I don't think about it as how do we convert? I think about it as how do you inspire? How do you educate? How do you make people happy? Because I believe I'm like a field of dreams person. For those who have seen that movie, if you build it, they will come. It's like my favorite thing to think about. But I believe that the more we inspire, delight, educate, you know, make you happy, you will try our products. So to me, social is not a conversion metric or funnel. It is about just being a joy and a light in people's lives so that when they're next at Target, Walmart, Walgreens, et cetera, that they say, oh, that brand is that brand so cute.

29:32Or I saw that nail art or, oh, they made me laugh or, oh, I saw someone talking about how great those press-ons are. And so they grab it and they try it. I love it. You know, how do you, how's, how's AI impacting your business, Sarah? What's funny is that we kind of love AI at Olive and June. We use it really to help structure our thinking, whereas sometimes you want to do a plan for a strategy and you can just put what your thought is in AI and they can actually just give you the template for what you have to fill out, which is so helpful because sometimes you're just stuck on how to even structure something.

30:11So it's not affecting, I would say, our core business. I don't see, I mean, they're not making nail polish instead of us, but I do find it to be a helpful tool in some of the operations or structural pieces of our business. Sometimes you're stuck on a creative idea and you just ask like, what, what brand should we collaborate with? Doesn't mean we're going to reach out to those brands, but it gives you something fresh to think about because my team is incredibly talented, but we get tired. And so it's a nice to have, not a have to have for us, but I truly understand what it's doing to the creative field.

30:44And I'm, I'm deeply sympathetic to that. So I think it's a balance for everyone and how they bring it into their business. I've heard you say that perfection is boring. How do you create a culture where people feel safe to experiment and to fail? It's a bit of trial and error, right? Where I have to then own my mistakes pretty publicly, or I have to own my missteps, but also create a bit of a casual environment so that I mean, on a call today, I can't remember what I said, but I said something and I said, sorry, if that came off wrong. And my head of creative started laughing and said, yeah, it came off so wrong.

31:27I'm so mad at you. And the whole team laughed. And the idea is that you're just yourself. You're earnest. You own what you do, but also that we're in an environment where people are really loving and kind to one another. And so you just model it really. But it is a bit of trial and error because I think perfection is boring. And I think there's a lot of beauty in the imperfection, but also I have a team of rock stars. So they all want to be perfect. They all want everything to go right the first time. So you have to just continue to have those conversations. And also when things don't work, you learn so much.

32:07and I think that people forget that. It's not just when things work that you learn. It's also when things don't work. And so then I will constantly reinforce, this is great. We learned our consumer doesn't like that color. Okay, we're never making a color like that again or we're not making it impress-ons or whatever. And so, but again, you don't know until you have the data one way or the other that things are working or not working. And so I think it's a constant reinforcement. You know, one of the things I've noticed just in this conversation, Sarah, is you seem to have a very high self-awareness.

32:44And, you know, do you have a process that you use to really, you know, assess where you are at now in your career and in your business and then what you need to do to sharpen your own acts? I think I was raised with a healthy amount of feedback. So, and I have an older brother who loves to tell me, he's talk about a no person. So I get a lot of feedback. And then again, like, like we said, I surround myself with people that are not yes people. But I enjoy growing. So I would say that I read a ton, I research a ton, but I also go to regular therapy. I really try to be aware of what I've done. And also I welcome, I tell my friends, like you can tell me anything.

33:33If I've done something that has hit you wrong, tell me. I think that the only way that you become the best version of yourself is if you, it's not just one thing or one process. It's if everyone in your life plus is giving you the feedback, plus you're open to it and you're showing that you're open to it. I also think that one thing that sometimes people don't realize is when someone's giving you feedback or they're frustrated with you, personal, professional, anything, if you show that you will accept it, they feel more comfortable in the future to give you more. And ultimately, that's sometimes the biggest hurdle or roadblock for you if you're defensive or you don't, don't hear them because then they don't want to do it ever again.

34:24Well, I don't want to, I don't want to work in an organization where people feel like they can't tell me when, when I've done something right or something wrong. And I don't want to be in relationships, friendships, romantic, otherwise, even with my daughter where she can't tell me how she feels. So I try to be as open as I can. And then I find sometimes a little too much, right? Like it's like, okay, I get the feedback. All right. I'm just kidding. But it's, but I think it's really healthy. And so it's not necessarily a process, more so a lifestyle that I try to embody. Yeah. And one of the things that you mentioned, you said you do therapy and, you know, it takes a lot of courage, A, to do therapy.

35:03And then B, you know, do I think, admit that you do therapy? Where does that come from? I think it's great to do therapy. I think, you know, it's funny. I had someone in my life once say that everyone who goes to therapy thinks they're better than everyone else. And I was like, no, they don't. They in fact think they need more work than everyone else, which is why they're in therapy. As idyllic as my childhood was in my own brain, when I look back, I have a pretty complicated relationship with my father. I had some insecurities that I think I alluded to earlier. I think I inherently knew that I had things to work on and things I wanted to work through.

35:43I've also been married twice and so, and divorced twice. And so there's been a lot of life lessons for me along the way. And I've wanted to make sure that I am always the best version of myself so that I can live the best life. Right. I mean, I'm, I want, I only get one shot. I want to, I want to live it to the best of my ability, but also, um, my daughter is 10. How do I model for her what real growth and evolution looks like? You don't have to be stuck in time and be this one person. It's important for her to know that growing and evolving is frankly a gift that we get in life. We get that gift to grow and evolve.

36:25You're not born as one person and you can never change. And so use that gift. Look at it as a gift. Look at it as great fortune to use your words. I love that. You know, there's been so much there and I want to have some fun with you with my lightning round of questions. So are you ready for this? Here we go. Here we go. Here we go. The three words that best describe you? Loyal, loving, enthusiastic. If you could be one person for a day besides yourself, who would it be? I really, really want to come back as my great grandmother, Olive, because I named Olive and June after them because I was obsessed.

37:01I know this is lightning round, but I'm just going to say one more thing. I was obsessed with my grandmother June my whole life. And then I realized, well, I was told recently by my godmother that actually it's Olive who I embody. And so now I really want to come back and live life as her because she had one beer and one cigarette every day and she was life of the party. And so I just, I want to live that life for a day. I love it. Your biggest pet peeve. I really don't like when people say, I tried my best. I just don't, I don't, of course you did. We don't need to say it. Who would play you in a movie?

37:34My friends would say either Scarlett Johansson or Emily Blunt, which I'm fine with both. They're both icons. I would be too. Well, maybe not me, but if I were you, I'd like that. And I agree. I've heard you're a huge Taylor Swift fan. What's your favorite Taylor era and why? Reputation. You know, I also took the Harry Potter quiz. I'm a Slytherin, which I don't present as a Slytherin, for those who know. If you know, you know. But I am a Slytherin. And Taylor's reputation era is so badass. But I think Showgirl is going to be my new fave. So we'll see. We'll see when that comes out. What's the one thing you do just for you?

38:13Every night that I'm not out, you know. But if I'm home, I get into my bed after I put my daughter down. I get into my bed, and I just TikTok. and I just scroll TikTok. Sometimes I read, but mostly I TikTok. And it's just, I get to be in this comfy bed in my comfy pajamas having just showered and I'm just relaxed. And that is the best thing that I do for myself. Besides your family, what's your most prized possession? My great-grandmother Olive had an engagement ring. Like it was her engagement ring. And I received it from my godmother when my grandmother passed. And so I turned it into a necklace.

38:48I'm actually, I just took it off last night. because I had physical therapy, but I wear it almost every day. And so it's her engagement ring on a necklace. And it's, I love it so much. If I turn on the radio in your car, what would I hear? Already mentioned Taylor Swift, but if I had to give another answer, Eminem is my favorite, so. TikTok and Eminem, no wonder you're on trend. No wonder you're kicking butt, you know. What's something about you that few people would know? That I ever chill. I think I give a very enthusiastic, high energy. I think I act that way, but I do relax a lot. I am calmer than I appear.

39:26Great. Well, we're out of the light. You're on a great job. So you talked about your young daughter. How do you lead at home, Sarah? I really try to be, first of all, I'm a person who believes in structure, boundaries, and making sure that my daughter knows what success looks like. So I can be, I wouldn't say strict, but I can be pretty strict on certain things. And then on other things I'm completely unstrict about. So, and I'm really fun. So, you know, you have to have the right manners. You have to speak to people and look them in the eye. You have to be a person who reads and is curious in the world and works really hard.

40:09And so all of those things matter. And then what I also try to do is make her life as fun as possible and as filled with as much joy as possible. We're seasoned pass holders at Disneyland. We go often, you know, we really, I, I try to make sure she has a huge social life and I do a lot, you know, I volunteer at the school. Like I really try to make her life be, to understand that structure is really important and it's healthy and it's, it helps you be the best version of yourself while also having as much fun as possible. I am lucky because I work from home. So I'm able to structure, we have a remote company, so I'm able to structure my life a bit so that I can prioritize her.

40:53And my parents weren't able to do that. And so I really try to take advantage of that while also instilling the values that my brother and I grew up with that I really deeply appreciate. You know, you talked about, you know, life and the part of the joy of life is evolving and continuing to grow and making the most of that. Can you share with us what your dream come true story would be? In life or Olive and June or? Both. You know, how you look at it. What's your dream come true? Olive and June is part of it? Well, I will say, and I think this is part of who I am. I have a ton of gratitude. And so I already feel like I'm living my dream life.

41:35I don't, I'm so grateful for all the success of Olive and June. and I'm so thankful for it and for my daughter. And I think, you know, I'm obsessed with her. So I feel very happy and I do feel like I'm living a dream life. But for Olive and June to be the number one nail brand in the world is the reason why after selling a business and, you know, all of the success that comes with that, I am still day in, day out, 24 seven founder CEO and not leaving the business because I love my job. And because there's so much left, we have so much left. Like, I don't want to leave it on the field, right? I want to play the game.

42:15And so I get really excited to build all of Injun into the number one nail brand in the world. So that's probably the one dream that I haven't gotten. Well, you're on your way. And you know what they say about business? I always say the best thing about business is the unfinished business. And that's what seems to have you excited is that pursuit of that number one goal. Last question here. What's one piece of advice you'd give to anyone who wants to be a better leader? You can't escape hard work. Hard work and putting in the time and putting in the effort, putting in the research, nothing can be done without true hard work.

42:54No matter what it looks like or appears or someone tells you, it is always about grinding to get to the best answer. That's great advice. And I want to thank you, Sarah, for taking the time to be on this show and to share your insights and congratulate you on the phenomenal success that you've had. And I love it that we haven't seen anything yet. We haven't. And I'm honored to be here. Truly, I love your podcast. So I'm very honored to be a guest.

43:29David, I loved this episode with Sarah Gibson Tuttle. She is so amazing. So amazing. In fact, that I just sent her a DM on Instagram and told her how incredible I thought this interview was. And she actually just responded. So I'm curious, David, what's your reaction to your conversation with Sarah? I mean, you'd never met her before. What'd you think? No, I think Sarah's incredible. And I particularly loved her last answer, which is, you know, don't underestimate the power of just hard work. You know, I think so many people just want things so fast, so quickly. And, you know, they think they can get there for the, you know, 30 to 40 hour work week working virtually, but they don't realize just how you, if you really want to move up and, you know, achieve everything you can possibly achieve, you got to put the hard yards in, you got to put the work in.

44:18And I love that. She's obviously done that. She had vision for something different and she's pursued it and she, she's, she's not stop it. She's got goals. And I love that. I do too. And if you'll notice my nails are painted with olive and June nail polish. So quite apropos for this debrief conversation that we're going to have. I love some of the themes that Sarah touched on and that you two kind of discussed in the episode. So I want to just dive into what some of those themes were so that we can give people listening to the episode, something really tangible that they can take away to apply to their own leadership, to their own life and to their own career journey.

44:55You know, David, David, it was really obvious to me after listening to this interview that Sarah is the type of founder and leader who really knows herself. She knows how she tends to make decisions, and therefore she knows how to manage herself well so that she can show up for her team. And David, it's great when you work for a leader with high self-awareness, but there are a lot of leaders listening to this podcast who don't work with leaders with high self-awareness. In fact, they work for people that lack self-awareness. And I'm curious your perspective on what to do in that scenario when the person that you're working with or for lacks self-awareness.

45:31Well, I think, first of all, you need to do your job really well so you have credibility. You know, once you have credibility, then you may have the opportunity to actually opine on what your boss could be doing better. But I think once you really do start putting some points on the board and you become very valuable to the company, valuable to that leader, you're inevitably going to have some opportunity to be able to coach the person that you work with. And my belief has always been, as a team member, your job is to make your boss better. Your job is to make your boss better, your company better.

46:08And so when you have those opportunities to do it, you should take them. And I think the best way to earn the credibility to help your boss become better is to do your job extremely well and become so valuable that that person really needs you. And so when you have something to say, they're going to listen to you unless they're tone deaf. And sometimes that's a situation that does exist where just people, leaders are in jobs maybe they shouldn't be in. They're probably not going to get to a higher job because they are tone deaf. They don't have high enough self-awareness. But, you know, I think if you're a really good member of the team, you know, you try to help everybody get better around you.

46:47I love that. I love that. And that that theme of just really knowing yourself comes up a lot in the episode. And I love when Sarah talks about that moment that she realized that she was in the wrong role. She worked in finance for 10 years until one day she kind of finally admitted to herself that she didn't like her life or the way that it was shaping up. and she didn't like the work that she was doing. And she had the self-awareness and willingness to admit that and make that pivot. And so obviously she pivoted and now she's running this$100 million nail brand. You know, Bakul, I think one of the things that's interesting about that, and I write about it in my book called Taking People With You, and we teach it in all of our leadership programs, is you need to know yourself to grow yourself.

47:36The only way you can ever grow is to really know who you are and know what your capabilities are. And no, frankly, in the case of what she's talked about, if you happen to be one of these leaders who has low self-awareness, you learn that you've got low self-awareness and you need to move it up the ladder. But, you know, I think she understood the importance of doing what you love. And she was very good at what she did. You know, she was doing well. but she didn't have that positive buzz you got to have when you go to work. She wasn't like, as Warren Buffett says, tap dancing to work. She's going through the motions and she knew that life could be more than that.

48:19And I love how she pursued her passion. For people listening who might be in a similar spot of thinking about transitioning in their career. How do you do that well so that you don't burn bridges or create tension with the company or industry that you're leaving? It's very important to try to grow where you're at first. Look where you're at and say, hey, these are the things I want to do. Can I do it at this company? And then go to whoever you work with and try to pursue that opportunity if it's there. If it's not there, I always feel like you need to be doing your job well enough to where you can actually have a communication with your, with your, the person that you work for.

49:02And you kind of let them know what your frustrations are, where you, what you want to do with your life. And they hear that and you make sure that they do hear that. And they either try to help you do it at your company or when it's time for you to move on, you know, it's not a real big surprise, you know, because you've been honest with them about, you know, how you're feeling about the company and what you really want to do in your life. So, you know, I say you never really surprise people. And then when you leave, make sure you're leaving and going to a place that's going to help you pursue your passions and it's going to help you grow yourself, you know, so know yourself so that you know how to grow yourself and know where to go.

49:40So you move with purpose. Don't move, you know, just to move. You know, very few people change their lives by just crossing the street and doing a job somewhere else with just maybe a little bit more money. You know, that's really shouldn't be the reason why you move. You should move when you know that you can make a quantum leap in your learning and in your growth. And I always feel like the biggest thing you can do is when you're not growing, try to figure out how you can grow where you're at. And if you can't go grow where you're at, go somewhere where you can. I love it. That's a great dovetail into this final kind of theme and concept that I want to debrief with you, David.

50:24Sarah shares in the interview that something like 96 % of women feel better about themselves when their nails are done. And honestly, I agree. So before this episode, I literally painted my nails so that I talk with my hands so that when you see my hands, I'll look put together because my nails are done. And I feel a little bit more elevated and chic because I painted my nails. And I think that what she's really getting at is the little things that you can do on a personal level that boost your self-esteem and confidence and help you show up in a way that's more positive so that you can contribute in a more meaningful way to the people around you.

51:02So David, I want to know, is that something that leaders need to be thinking about? Is it important? And what are some of the things you do to boost your self-esteem? Well, first of all, I love the fact that she understands that. she understands the power of nails. She understands that you feel better because you've got those white nails with that white sweater and your white earphones, you know, and that's why she has so many different colors. That's why she has seasonal nails. That's why Halloween's a big period for her because she knows people like to lift themselves up and lift other people up and create almost conversations around their nails.

51:41And I see that happening all the time with women that I happen to have the opportunity to hang around. You know, they like looking nice. They like being on trend. And I think that's really powerful. So, you know, what do I do to lift myself up? I mean, I don't know. I guess probably the most important thing I do is try to stay in shape. I think it's just when I work out every day, I really enjoy that. And it picks me up. And I like having my whoop watch because I like to see my progress. I like to understand what my performance is. And so because I'm regular and disciplined on this front, I'm constantly making progress.

52:24It's reflected in my whoop. And so that lifts me up. And I'll tell you, the other thing that I have a great appreciation for is being dressed properly. You know, I like to I like to wear things that are stylish, look good and and do the best I can with what little I have. I love that. It feels almost silly for me to say, but there's it actually makes a real impact in the way that I show up and the attention that I have to to share with the people that I work with and with the actual work that I'm doing. When I look good by painting my nails or for you wearing something nice and on trend, you feel good.

53:12And when you feel good, you're more fun to be around. Everyone has a better time. And ultimately, the product that you produce is just going to be better. You know, if you talk to anybody in the fashion industry or the clothing industry, you know, what do they tell you to buy? They tell you to buy stuff that you feel confident in. Totally. And so I think that that's something that, you know, people should constantly be working on is their confidence level. You know, you should be working on something that makes you feel good, makes you project, makes you, you know, have this sense of confidence that can inspire, assuming you have confidence.

53:49I always say confidence goes along, you know, with, you know, with confidence. You can't have the confidence without the confidence. competence. But if you have that, then I think you should be looking for ways to lift yourself up. Hey, Olive and June started out as an in-person nail salon, and now Sarah Gibson Tuttle is growing it to over$100 million. And that is a whole heck of a lot of$8 bottles of nail polish. So don't ever underestimate what feeling good about yourself can do for a business. And how about the Olive and June story? She names it out for her grandmother and great-grandmother.

54:26And, you know, I thought it was sort of a clunky brand name, but it seems to be working. A hundred million dollars isn't bad. Absolutely. David, thanks so much for the debrief. I really enjoyed. I always enjoy talking to you, especially when I'm so obsessed with the person that you interviewed. Well, we try to have people that on the show that everybody's obsessed with, but I'm really glad you love Sarah. Well, that does it for today's episode of How Leaders Lead. Be sure to tune in next Thursday for David's conversation with Nick Green. He's the co-founder and CEO of Thrive Market, and you are going to love this episode.

From the publisher

As a kid, she had to hide her favorite red nail polish from her parents. Today, she’s the founder and CEO of Olive & June, a $100 million nail polish brand.

But in between, Sarah Gibson Tuttle had to navigate a career she wasn’t really passionate about … and find the courage to chase a big idea. 

In this episode, she shares:

The untold stories behind the brand’s rise

How she turned frustration into innovation

Why her ability to work on herself has helped her build a more collaborative, company

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Whichever you choose, you can be sure you’ll get the trusted leadership advice you need to advance your career, develop your team, and grow your business.

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