Episode 06: Annie Stancliffe

Annie Stancliffe is the Founder and CEO of High Five, a reimagined nail salon on a mission to improve the lives not only of customers, but also employees. Inspired by “the now-infamous New York Times expose detailing the mistreatment of nail salon employees… Annie is committed to providing ethical treatment and fair pay for our nail techs and a modern, delightful service for our customers.” In this episode, she talks to us about preserving a spirit of creativity in the midst of routine operations, the decision to bootstrap her business, and how many delightful ideas are sparked by everyday observations of and interactions with her customers.

Finding Ikigai with Annie Stancliffe from High Five

Episode 6: Show Notes [Transcript Below]

Many, many businesses suffered during the restrictions brought about by the COVID-19 pandemic; those who rely on face-to-face interactions probably more so than most. But in today’s episode, we’re joined by an entrepreneur who didn’t let the lockdown dull her spirits or her motivation. Annie Stancliffe creatively pivoted the focus of her nail salon business, High Five, during the lockdown, and she stayed true to her goal of creating a space and a brand that “feels like home” when things opened up again. Annie’s pattern-recognition and people skills, along with her fresh perspective on the beauty industry, have allowed her to break down some of the pervasive, harmful norms which exist. In today’s episode you’ll hear some examples of how Annie and her team have solved operational challenges, how they respond to the desires of their customers, why Annie chose not to raise venture capital, and how she lives out the concept of Ikigai. We always thought Annie was going to solve some of the world’s big problems, and after speaking with her today we know we were right!

Key Points From This Episode:

•   How the pandemic altered their plans, and how they made the most of the lockdown.

•   The importance of being motivated about the direction you are taking your business.

•   What excites Annie about her job.

•   Why Annie decided not to raise any funding for High Five, and how this impacts the company’s growth.

•   Pressure that people feel to raise venture funding.

•   Annie’s experience of working in a venture backed start-up.

•   What Annie learned about herself while doing her MBA.

•   How Annie sees her future unfolding.

•   The problem with tipping.

•   Why Annie sees her lack of background in the beauty industry as an advantage.

•   Learnings that Annie has had along her journey of running High Five.

•   How Annie utilized the High Five space when nail salons were not allowed to operate, and how this benefited her business in the long term.

•   Creativity prompts that Annie uses in her team meetings.

•   The transferable nature of the skills that Annie utilizes in her business.

•   An example of how High Five responds solves operational challenges in an on-brand way.

•   How High Five promotes conversation in the salon and online.

•   A trait that is common amongst women, and one of Annie’s key goals which relates to this.

•   Advice from Annie for dealing with the stresses of being a founder and CEO.

•   High Five’s approach to service and product options, and how they have evolved over time.

Tweetables:

“Our business involves being hand to hand and face to face with another human being, and that’s something that was impossible or very difficult with the pandemic so we had to get really creative.” — Annie Stancliffe [0:03:18]

“Just because it’s a viable direction, if it doesn’t fit with what motivates you personally, it’s probably not something you’re going to be able to direct energy to for a long time.” — Annie Stancliffe [0:04:48]

“We are growing more slowly, but at the same time, I have complete ownership over how and in what directions we grow.” — Annie Stancliffe [0:06:44]

“What’s motivating to me are those kinds of smaller moments of connecting with my team and with our community.” — Annie Stancliffe [0:08:47]

Links Mentioned in Today’s Episode:

Annie Stancliffe Email Address

High Five

High Five on Instagram

Launchpad

EPISODE 6 [TRANSCRIPT] 

[00:00:03] MH: I’d love to hear an update. Where’s High Five now? Your website is beautiful. It’s really pretty.

[00:00:16] AS: Thank you. We like to joke, the photos on website, you might remember actually, Jeremy, we did that photoshoot in May of 20 –

[00:00:24] MH: Oh, really?

[00:00:26] AS: During LaunchPad. It is the long – like the most evergreen photoshoot. I can’t believe it. 

[00:00:30] MH: It’s amazing.

[00:00:31] AS: [Inaudible 00:00:31]. We’ve been able to use it forever, so thank you. That’s very appreciated. Since then, I mean, we’ve been on a real journey. Just to kind of rewind, when I launched full-time after graduation, we were totally mobile salons. We were exclusively doing events, corporate events, campuses, private events, et cetera. We opened our first brick and mortar location at a really apt time in January of 2020, so we were actually only open for a couple of months at our first shop before we closed down on March 13th.

[00:00:01] MH: Oh my God!

[00:00:03] AS: Yeah. At that time, we were sort of gearing up to have a really big year. We wanted to be profitable in 2020. We were going to do sort of a hybrid model, keeping our pop ups going, with the brick and mortar. Obviously, things dissolved, life got in the way, but it actually prompted us to be really creative. I can speak more to what we did over the course of 2020, but lots of interesting new initiatives and connections. One of the things we did during our downtime is actually lay the groundwork to open our second location. Yeah, it’s something we’ve been sort of quietly working on, but we are gearing up to open up in Marin on April 16th, so less than a month. We’ll have two locations, which we did not anticipate if you would have asked me a year ago, but it was really exiting. We’ve been able to stay productive and keep growing. Now, we can now hire capacity, 50% as of today.

[00:00:55] MH: I love it. Well, I’m going to book, I mean, I’m going to try to book for my friends.

[00:02:00] AS: Yes, please. That would be great. We just opened up the books for April. We tend to release each month about a week in advance. April is live for the SF location and then Marin will be going live next week. So very –

[00:02:15] MH: Awesome.

[00:02:17] JU: Without regard to you, I mean, feel free to share on what the developments were, but walk us through, because you had an enormous disruption to your plan. I’s love to hear – what Mar and are really interested in is, how are resilience and fantastic female founders going about the business of building a new venture? I think turbulence is an incredible opportunity to explore creative practice, resolve, ability to pivot, et cetera. Walk us through for you, I mean, everybody was affected obviously in this last year, but certainly your business was, so I’d love to hear just how you thought about the various upending and waves after waves of changes and surprises.

[00:03:05] AS: Yes. Yeah, we’ve had to, it was a real exercise in resilience and optimism as it has been for everybody around the world, which was like kind of the one thing that you come back to is like it’s affected everyone, so you can’t have a pity party. But yeah, our business involves being hand to hand and face to face with another human being, and that’s something that was impossible or very difficult with the pandemic. We had to get really creative. I think something that I thought about a lot is, one, what can we do in the constraints of the pandemic? Within those constraints, what was interesting to me as a founder and what stayed true to our business?

I often think, as an entrepreneur, we’re a very small team, like my energy and ability to keep up, keep getting up every morning and doing this is like a very, very important resource to High Five alive and staying for our key team members. I had to make sure that whatever we directed our energy toward during this time of pivot and experimentation was something I was excited enough about and like that I can see is sustainably working on for a long time.

In the context of nails, we explored a few different directions there. We did some virtual manicure events, with mixed success. We did some other things that I’ll talk about in a moment that felt more true to us. A lot of folks were like, “Well, you should have launched a polish line. You should have folks paint their nails at home.” There are businesses that do that. There are great businesses that do pop-on nails. I mean, [inaudible 00:04:34] I haven’t been in touch with them, but it makes total sense. Awesome for them. That’s something they’re really excited about.

I don’t see myself building a cosmetics business, and that was something I had to be really, like, take a hard look at. It’s like, just because it’s a viable direction, if it doesn’t fit with what motivates you personally, it’s probably not something you’re going to be able to direct energy to for a long time. I kind of had to look at it through a few filters, all the available paths and then the paths that I was excited about. Unfortunately, or fortunately, the things that excite me about High Five are also things that make it hard as a business. I’m really excited about building an in-person environment and experience, kind of – we think about High Five as this drumbeat in people’s lives. We see people every two weeks for years on end and see them get new jobs, and get married, and have kids, have hard things happen and it’s really cool to be a part of that. That’s what exciting to me. We just so happen to paint nails almost.

[00:05:32] JU: Can I ask one question there, Annie? To me, it’s really important and it gets to – I see in LaunchPad Office Hours for example, folks bring in like a matrix, like where they’re trying – they’ve got nine ideas and they’re trying to decide which one and they’ve got their various criteria, and I would say, your perspective is unique. Tell us more about this notion that just because it’s viable doesn’t mean I should, or can, or want to do it. What are the other considerations that you’re layering onto that decision, like really practically for yourself and how did you come to those personal convictions?

[00:06:11] AS: Yeah. It’s a great question and I think it’s very – especially at the GSB and like as a business school student, you’re so trained to think about how big can this get, how fast can this grow? For some, like that might be the goal. I think there were times, especially in the early days. I was amped up. My ambitions for the scope and for the growth rate of High Five were different maybe then than they are now. I made a very deliberate decision for example not to raise any funding, not just specifically raise any venture funding as well. We’re totally bootstrapped, which means that we, by definition, are growing more slowly, but at the same time, I have complete ownership over how and in what directions we grow. That’s become really important to me.

That might be very different, like someone that’s looking at something with a matrix and analyzing decision making might be based on, like I have a bunch of classmates doing search funds. Their criteria is, “What’s the best opportunity, the biggest and best with the most financial gain that I’m positioned to perform well at?” For me, they’re sort of like, I’m just motivated by like, I want to make a living at a certain level. Above that, like I also just want to be engaged with my work and create a team environment and workplace that I’m proud of that is a meaningful part of people’s lives and on the customer side, create a space and a brand that feels like home. Where they walk in the door, it feels like belonging. Like, that’s enough for me. That’s more than enough. That’s so exciting. That’s like what I can get up and do every day. I so happen to be building that in this particular domain right now. I hope the next step, I might explore that in some other ways.

Also, as I look back, think that I have a different title now, I’m working in a different domain, like I said. But I think I sort of always had that same perspective in my job and what I bring to the table, I have always kind of be the same. Like I used to run a sales team at a tech company in New York, in the art world. I think the way that I showed up to work every day and the value that I provided with my team was probably not that different, even though the content that I’m spending my time doing now is a little bit different and I sort of honed my skills. Hopefully, my MBA was worth it. I spent a lot of time and money.

But it’s not different in nature, it’s just sort of moved and accelerated in the same direction. Yeah, it’s basically a long-winded way of saying like, what’s meaningful to you and why? I think like, there was the shiny object and it’s okay to shoot for something big and to shoot for something big and to shoot for financial aim, but that just hasn’t been, you know, it’s really, really hard and this is a marathon. What’s motivating to me are those kinds of smaller moments of connecting with my team and with our community.

[00:08:58] MH: [Inaudible 00:08:58] kind of advice maybe you can give me, because I do believe that there’s so much peer pressure on students to build something big and a lot of them, I feel really bad they – clearly, a lot of them do not have venture scale businesses, but they’re forced to – their peer pressure is so high. It’s so hard that you go off on that route and then it’s a tragic situation because you can’t raise those friends and family money or whatever small seed money, but you get to a Series A and it’s impossible. You haven’t built the strength of your business on being bootstrapped, “I know how to spend money and et cetera.” I have this all the time and I don’t know how to convince people and tell them, it is okay to not raise venture money. [Inaudible 00:09:48]. 

[00:09:50] AS: Right. Totally. I mean, that’s really –

[00:09:54] MH: What would you tell somebody if you were me?

[00:09:56] AS: In Silicon Valley, it’s hard. We’re kind of like in this hyper concentrated place where it’s – everyone wants to build a technology company and raise venture. That’s sort of like, in media too, all the headlines are about how much money did you raise? It’s like, “Are there sound economics?” A lot of these consumer brands that have raised a bunch of venture money, the bubble has burst on some of them where it’s like, “Wow! The numbers never worked.” The founder was charming and had a very clear vision, and was super great at fundraising, and like it’s kind of this popularity contest. It depends on the business, but a lot of times, it doesn’t pan out.

Yeah. I think this isn’t my sort to tell, but I have a couple of friends who are in that position, who got on the venture treadmill and I think one thing you could bring up is like, “How do you want to spend your time?” If you want to spend your time managing your board and fundraising, I mean, that’s a very pessimistic way of looking at it, but ultimately, if you’re always thinking about the next round and you are adding more folks with ownership and stakes, you’re probably not building, you’re probably not an individual contributor as much on projects. Maybe that’s okay for some people. Some people are awesome at that. But like, I spent my time, like, I consider myself very much like a creative person and I want to spend my time – I designed all of our spaces like by the inch. You come into our Marin store like, with cape on the floor, and pencil and paper. Like I wouldn’t get to do that.

That’s really exciting. You can decide the pieces of the business that you play at. You can design your role a little bit more. You have more ownership there, because there’s lots, sort of like politics in fund raising to juggle. Then of course, yeah. Then there’s the real truth that a lot of these businesses might not have the right fundamental economics for venture anyway. But maybe you can approach it with, “Hey! How do you want to spend your day?”

[00:11:52] MH: [Inaudible 00:11:52]. I’m just going to send them to you.

[00:11:56] AS: I mean, we’ll –

[00:11:56] MH: [Inaudible 00:11:57] role models. There’s multiple GSB role models that are venture ones, but there are fewer that are like, “I’ve built my business. I’ve bootstrapped it for whatever many years, and it grew, and I have a great life and whatever.” I don’t think we have those role models.

[00:12:15] AS: It’s a couple of years ago now, but there was a conference that I attended that was on this subject, that was long-term organic growth versus raising venture or other kind of faster trajectories. It was really helpful. One of the companies I remember, is it Balsa? They make Christmas trees. They make amazing Christmas trees [inaudible 00:12:35] and they’re just like super successful. Their economics are like really strong. It’s just like a great place to work. They’ve kind of grown incrementally over decades. I was like –

[00:12:47] MH: [Inaudible 00:12:46] just see if I can find the conference.

[00:12:49] AS: It was really eye opening and helpful. Because yeah, you kind of feel you’re like not ambitious enough, like you definitely question, especially when you’re in the hot bed. I don’t think it’s a question of ambition or how good the business is. There’s just different types and different ways that you might want to spend your time. There’s not a value judgement, there’s not one that’s better.

[00:13:09] MH: No. I completely agree with you and you see it all the time. I’m a witness of like hiding the fact your business is not working with venture dollars.

[00:13:18] AS: Yeah.

[00:13:21] MH: People do it with the promise that you’ll eventually get better, but you may never get there, you know.

[00:13:26] AS: Really, yeah. I think it’s sort of like difficult because often, like I’ve worked for venture backed startups and like, the founders are super charismatic and just excellent sales people. They spend their time closing these fund-raising rounds and then recruiting, which are basically the sales functions and they are too good. Then the operations under the hood, the wheels aren’t really on the bus. That’s partly what prompted me to come to business school. I was kind of early at a startup team that fit the bill there, I was like, “I don’t want like – whoa! You’re making all these promises and I’m the one trying to fulfill them. I don’t know if this is going to work.” That company is doing well though, but it’s a software play and that’s one of the categories that tends to work.

[00:14:13] JU: This seems formative to your development as an entrepreneur. I’d love to dig into, how did that realization dawn upon you? Were you aware of it as it was happening? You talked about founders who are charismatic and who are good at sales. How did the processing take place and how did it shape your ambition? Was it something that was kind, like a seed was planted and how did you realize that that was something that was going to influence the way you thought about building your own, or whether you wanted to build your own?

[00:14:46] AS: Yeah. I think being in the environment at the GSB is, yeah, it’s kind of this frenzy, it’s Silicon Valley, everyone wants to raise money and you kind of get stirred up by it. I think one of the things that’s been helpful for me as far as trying to look objectively at what my ambitions are for High Five and as an entrepreneur, and how I want to approach growth and fund raising according to that, is that I always felt kind of different coming into business school. I joked with a couple of friends that like, each class has like two, like whacky creative people and we’re like, “Oh! It’s these two or three in this class,” and we all kind of know who one another are and we’re the ones that LP the quantitative classes and use the tutoring time and like are humbled.

That was useful because I’m like, “Wow!” I really feel like I think about things very differently from a lot of my classmates.” And it was – everyone had brains of all different types. It’s not like it was one herd and then my brain. But I heard the word operator for the first time in business school. I didn’t know what it meant the first like ten times I heard it. Then I was like, “Oh! Wait!” It’s because like most people are investors, consultants or God forbid, operators that are out there in the world doing things or managing business. I was like, “Wow! There’s a word for that. Okay. Got it.” So I like learned all this jargon. I’m like, “Well, I guess I’m an operator.”

It’s not like I had to like keep up, I didn’t have a traditional career path, I like wasn’t on some track. I didn’t think I was going to get my MBA. It’s not like I was tearing away from a predestined like, “Well, I must take this [inaudible 00:16:27].” I’m like, “Well, I’m already on the fringe, so it’s fine.” I do think it’s easy to get caught up when you’re in school, but even more so when I graduated and kind of got into the day to day of it, you know, it’s also really hard and I think there’s part of it that’s like, it’s nice to know that you maintain more ownership and decision making. Whereas, I had actually a friend who is sort of – she’s like, I don’t know, we’re like in parallel paths. She’s running a business, it’s called Naza. If you guys are familiar with Naza Beauty. It’s here in SF. It is kind of like a driver concept for textured hair, really, really cool.

She took money from a VC that had offered us a seed round back – I wasn’t actively raising, but they had wanted to invest. She took that path, that’s where we diverged, and that’s always what she wanted to do, but it’s been interesting to stay in touch with her, because we’ve just like – she’s making decisions, maybe with a lot of other folks right now and I think ultimately, it’s the right thing for her. She's committed to doing this business for 20 plus years. She really is connected to it. I like that I have a little bit more flexibility. I have other ideas that I want to pursue. I don’t know if this is – if I want to work on this specific domain for 10 or 20 years. I might have other chapters. I like that flexibility as well.

[00:17:47] JU: This is surprising. What I love about these conversations is, we have no script, we have no agenda, we don’t know where they’re going to go. To me, I thought I was going to ask you about this in a different way, but now that you say that, I’m going to ask you about it this way. You have always struck me, from the very first time you came to LaunchPad, as a purpose-driven founder who was really – I’m not saying – you’ve said something that makes me disbelieve that by the way, but I’ve always felt, “Annie is going to solve this problem.” You read the New York Times article about nail salon workers. I have always been willing to bet on you because of that sense of – you can say anything, it probably wouldn’t change that opinion, but tell me how you think about that north star, social purpose and how that kind of jump starts things.

But then also, on the other hand, I’m hearing this kind of willingness to maybe change directions, do something different. How do you balance that inspiration, that purpose, with the willingness to evolve?

[00:18:51] AS: Yeah. It’s a great question and I have more conviction than ever about, kind of, the problem and the opportunity. I think, I’m not going to say this word right, is it ikigai? I’m sure you’re familiar with that Venn diagram. It’s all these overlapping circles that are meant to sort of like channel you towards your life’s purpose. It’s like what you’re good at, what the world needs, what you love. It’s the overlap of those things that that’s where you should occupy and that’s where you should do and that’s where you’ll be disproportionately impactful. I think what I – again, I’m super convinced about both the opportunity and the importance of solving this space. I’m maybe less convinced over time that I am the person in the middle of that Venn diagram to solve this problem at scale.

In addition to that, just like very frankly, I know so much more about the problem now. And man, it is even harder than I thought it would be. Then you throw a hundred-year pandemic in there. Yeah, I don’t want to just be a cop-out of like, “Well, it’s too hard and I’m giving up on deflecting.” But I think it’s a combination of those two things, and I think the ways that I viewed this kind of industry consolidating into a brand that scalably supports people, it’s just so huge. Like we are talking today. We just had our content discussion for the month, and tipping is like a hot button issue that we’ve incorporated into how we think about our business from the beginning.

Tipping is essentially a legacy of slavery in other institutions that allow people to be paid or frankly not paid enough and unfairly, hundreds of years old, that reaches into many different industries. Nails are not the only industry where tips are mostly what’s relied upon for earning money. We flip that on its head and we pay people a sustainable hourly rate and a tip is just sort of icing on the cake. We didn’t want to have a tip involved at all, but it’s so deeply entrenched in our culture that people want to tip and that people want to make tips that I’m just like, “Danny Meyer hasn’t been able to solve that. I just don’t know if I’m going to be able to solve that. I just don’t know if I want to. I don’t know if that’s my ikigai.” That’s one example of a hundred different components of this kind of very hairy industry that I’m like, “There could be someone better suited for the long haul.”

I would like to play my role and contribute, but I think the things that excite me about High Five day to day, again, are more, this could apply to any industry; creating a workplace that people are proud of, that supports them, that supports their career growth, that they’re excited to come in every day. Same thing on the customer side, I think I’ll apply that lens to a few different ideas over my time. For me, that’s like, that’s my ikigai. I think that’s the word. I feel like it could be.

[00:21:41] JU: If it’s not, you said it enough times, that it will now be the one.

[00:21:45] AS: [Inaudible 00:21:45] but now it’s in the lexicon, yeah. You can blame me on that yeah. 

[00:21:50] MH: Think about what you said, what was – this is a question I often ask founders, what have you learned since you left LaunchPad? What are the biggest learnings, biggest surprises?

[00:22:02] AS: Yeah. Well, so many things about the industry specifically. I mean, I basically had no business, I have no background in beauty, in running an hourly team, in development and education in a regulated industry. Like none of it. I think that has been a real advantage in a lot of ways, because we don’t do anything at High Five because it should be that way, or because we’ve always been that way in the industry. Like I have no preconceptions about how things are done because I don’t know how they’re done and we’re just figuring it out. That’s been great because it’s allowed us to solve everything very upstream. We really focus on like addressing the need or the customer pain rather than just doing things a certain way.

That has been valuable. I think, again, it’s sort of like, a lot of it is what you learn by yourself. Especially, I don’t have a co-founder so I’ve been – I don’t actually know many other folks who are solo founders or don’t have a business partner and I think that’s been hard too, because that means I talk to myself mainly, so I’m in my head a lot. That dialogue is happening up here. A lot of that learning has been around how to manage myself, and what motivates me and kind of like a study in psychology. That’s been one big thing.

Then, I’ve also applied that out to like, it all ultimately boils down to people and what motivates them. We’re having trouble hiring right now. It’s always hard, but just the dynamics right now of the market and great unemployment support being available and various other factors. It’s pretty hard to be hiring at the moment, so we’re using some of those psychology lessons to figure out what might motivate people.

[00:23:46] MH: I almost think like psychology should be a requirement for all people with entrepreneurial interest.

[00:23:52] AS: Totally. Oh my gosh! I completely agree. I took AP Psychology in high school and that’s about as far as –

[00:24:02] MH: One of my biggest regrets is not taking more of those classes at Stanford, because I’m sure they have great people. It’s all psychology at the end of the day. [Inaudible 00:24:11] customers. Anyways.

[00:24:13] AS: Oh my gosh! Completely. Yes, it all boils down to people and how they work. Yeah. I don’t know if I have all the right jargon or names for it, but yeah, it’s been a masters in psychology for sure.

[00:24:26] JU: Tell us about maybe one recent problem that you felt you all solved in an elegant way or in an unexpected – you talked about breaking with the norms of the industry. What I’d love to hear is like, what’s the lineage of that solution? Where did it come – maybe tell us about the solution, but then tell us what was the process by which you arrived at it?

[00:24:51] AS: Yeah. I mean, I think there’s a bunch of examples, but the one I’d love to use specifically related to the pandemic is, we were closed for over six months last year. Back to that decision at the beginning of like, “What can we do legally and viably? What are options that are available to us? Then of those paths, what’s interesting to me that feels aligned with my values and the brand’s values?” There were fewer paths there, but one of the things that we looked at is we – a silver lining is, I actually lived – until I moved, I lived above High Five, upstairs, like a shopkeep so when we’re closed, I could use the salon space as an office.

I’d see all these people walking by, and everyone, I’m like, “That could be a customer. How can we reach them?” We also had this empty space that was beautiful that people weren’t like able to use, then at the same time, seeing all these other small businesses really struggling. Kind of instead of like, “Well, we’re a nail salon, we should be doing nails.” We kind of thought like, “Okay. Well, these small businesses need a way to connect with customers. We need a way to connect with our existing customers and our community. Like how can we kind of zoom out and use those resources and those needs rather than necessarily staying within our domain?” We did this awesome series over the summer, the summer pop up series where retail was allowed. That was one of the things too. It’s like, “Well, okay. Also, what’s allowed?”

Then at that time, retail was allowed, but doing nails wasn’t. We transformed our whole space basically into like a mini West Coast Craft, and we did it every weekend for about six weeks in the summer, and got a rotation of new women and black-owned businesses from the Bay Area, let them set up shop. We connected with, I think 75% of folks that came through the door at those events were all new customers. I need to look at the numbers, but some huge percentage of those have now creeped over to being customers in the shop for getting their nails done.

Then on top of that, there was all this cross promotion with all these wonderful brands. Now, I’m full on in this recruiting push to find front desk folks for both of our shops, and like some of my best leads are coming from these contacts from small businesses. We never would have done that had the pandemic not forced us to get creative in that direction. We also never would have done that had we been operating under the assumption of like, “We are only a nail salon. What do nail salons do?” I’m really proud of the team for sort of like zooming out a little bit and using our space and our resources creatively.

[00:27:23] JU: That’s amazing, first of all. I saw your emails that were coming through about the weekend pop ups and I was sad that I live so far away. SF feels like a long way away. How did that idea emerge? You said you were watching people walk by, “What could we do?” Walk us through what is the team doing where that – it’s like what’s the sausage maker that ends up with that idea? How did it go?

[00:27:48] AS: Yeah. Well, first of all, we try to – that’s sort of something that – we try to have the team always be in that sort of mindset of like openness and creativity, and sort of like – I studied art history in undergrad and it’s like my biggest pet peeve when people are like, “Well, I’m sure that degree was very useful.” I’m like, “Yes, it was. I stand by it.” For me, art history is basically pattern recognition. It’s the ability to look at two things visually and understand what’s the same and what’s different, different artist careers, how things tie into society at the time. It’s a great toolset I use every day. We try to foster that for example at the beginning of every meeting, just sort of like remove any like, “Oh! This is only this type of meeting. I can only bring these types of ideas.” It’s like, “No. If what you ate for breakfast three days ago is relevant to our sales strategy, let’s hear it.” Often, we’ll start out with like a creativity prompt at the beginning of a meeting, or a week and –

[00:28:46] JU: Such as what? What’s an example of a creativity prompt?

[00:28:49] AS: One of the ones we did recently, and we’ll have different people lead it. But like, our designer came up with this one, she’s like, “Okay. Everybody go choose a color, think of a color.” All right. People are thinking. “Take 90 seconds, walk around your space and find at least five things that are that color.” First of all, you’re getting up, you’re walking around. It’s very easy and you’re giving people these constraints one problem at a time. “All right, bring them back, sit them on the desk.” Then she had us create a composition and kind of gave us an excellent, kind of how to approach that. It’s very easy. You’re not drawing, so people aren’t scared. It’s very quick. We only had I think 30 seconds to do it. Then we snapped a photo and I’ll share them to Slack. Like immediately, there’s just all this like – then we’re also connecting because it’s like, “What is that object?” and it’s just very cool.

Then suddenly, like whatever that colorful object is, like you bet that came into play when we’re thinking of ideas later on. We try to like freeze the gears a little bit at the start of –

[00:29:50] JU: Beautiful. That’s great. Sorry. I kind of interrupted you on what’s an example. You were saying you’re in the habit of getting your team to think creatively. Go back to how the weekend pop up unfolded?

[00:30:07] AS: Right. I think we were sort of like – we try to be in a good, ready position creatively by doing things like that, to always be open to those sorts of ideas. Then from there, I think we also, by not making the assumption of like, “This must be explicitly related to doing nails.” What if we thought about it as a more values-based approach? We want to be a place where people feel like they belong. We want to be a place where people connect with their community. What are some ways that we could foster that? We actually even leveraged the pan handle, which is less than a block away. We also did outdoor workout classes. It’s like, we did have mani-kits available and some things that aligned with our online, like virtual manicure class programming, but it was much more zoomed out and about community, so that opened up the floodgates around what could make sense.

Then I think it’s back to that point of like, my sense that the value that I bring and the way that I think about things is sort of industry agnostic, despite what title I have or what role I’m playing. I love to have parties. I love to host people. Whether we’re hosting people and doing nails, or hosting people in a retail setting, for me, the way that I think about that and make that happen isn’t actually that different. It felt pretty natural.

We can apply the same skills for example, like managing our vendors that we recruited, and all the operations to get them set up, prepare them for the event, make sure they all showed up in time, wore their masks, et cetera, wasn’t so different from the skillset that we had gained through working with all of our appropriate partners for doing our onsite events so we could sort of like transfer those, and we’re sort of just like, actually it’s somewhere like, “Oh! We know how to do this. We have this muscle.”

Yeah, it felt fairly natural and we just got into such a rhythm. Actually, we did kind of an encore. We did a holiday edition in early December as well. It certainly won’t be the end of it and yeah, it’s now part of our blueprint.

[00:32:06] JU: I was going to ask almost on the, “Where are they now?” kind of vein. Will we see something like that in the future? How do you think about that in terms of institutional memory, organizational capability? Now that you say, maybe High Five is going to be a steward and provide editorial, kind of curatorial value to a community, how do you think about those experiments now driving a new identity, reinforcing identity and how do you think about that?

[00:32:38] AS: Yeah. I mean, I think, we don’t limit how we think about our relationship with our customer to the 30 minutes that they spend with us. We kind of want to think through, “All right. What’s the rationale for booking a service? What do they do right before this and what are they going to do after? How can we fit into that most effectively, and memorably and create a positive experience?”

One example, this is kind of – this is a silly one, but it came up today, is that often, we have a lot of data that, first thing in the morning, appointments on weekends tend to be slightly – run a little bit behind and they often bring coffee and a pastry. Which, you can’t take your mask off when you’re getting your service done, and you’re often late, and [inaudible 00:33:22] wet nails and a croissant, it doesn’t work. We’re like, we understand that that’s what they might want to do on a weekend. Now, we’re going to pursue a partnership with some of our nearby coffee shops and do a 50% off coffee after your manicure, so that you’re not late, you’re preempted. We understand that that’s part of your day and sort of like solve that for you. But also, you’re on time for your appointment and we can start the next one on time. Everybody kind of wins.

[00:33:48] JU: That’s amazing. What a great example. That’s so cool.

[00:33:55] AS: That’s one that came up today. You’ll see on Instagram sometimes in the next few weeks, we’re going to run some content that’s, “Manis and muffins don’t mix,” so [inaudible 00:34:02].

[00:34:05] JU: You’re solving an operational challenge, but doing it in a way that’s actually more on brand, creating stronger relationships with partners. 

[00:34:16] AS: Yeah. It’s a fun one. Yeah.

[00:34:19] JU: That’s great.

[00:34:21] MH: I want to come work at your company. That’s how I’m feeling right now.

[00:34:26] AS: Great! Because we’re hiring.

[00:34:28] MH: I have a question for you. Are you kind of more intentional about – are you intentional I would say, having such a creative environment, taking your customer’s voice, how do you bring your customers into your decision-making journey?

[00:34:46] AS: Oh my gosh! Well, that’s another thing that’s live today. Every week, we have a really fun – we always have fun playlist in the shop and we have a TV going, and we have vote on Instagram every week around what people want to –

[00:34:59] MH: I love that.

[00:34:59] AS: That’s on Wednesdays. Then another thing that we love, it’s called Small Talk, it’s another series we do. One of the things that I’ve been passionate about from the beginning with nails in particular is fostering conversation between the customer and your nail technician, as well as between other customers, between nail technicians. Often in the nail salon, it’s kind of quiet or there’s a language barrier, and there’s potentially some class hierarchies or other things going on. We want to break that down and create conversations that you could draw a diagram and then be lines in all directions, different languages spoken, et cetera.

Small Talk is just these kind of like mini conversation starters that we prompt and we share them on Instagram and folks who weigh in with polls and can add their answer. But we also have them posted in the shop and there’s a question of the day. That also ties in with what we roll up at the end of –

[00:35:46] M: Right.

[00:35:47] AS: It’s kind of this online-offline way of prompting connection. Where if you were in the shop that week, you’re like, “Oh! That was the question on my day when I came in,” and then you’re kind of [inaudible 00:35:57] engaging online and then vice versa. If you’re not there that week, you’re like, “Oh! It sounds fun what they are chatting about in the shop. I’m going to book for next week or what have you. We have some fun things like that that we work in.

[00:36:09] MH: Like part of your day to day.

[00:36:13] AS: Yeah.

[00:36:14] MH: I know part of the reason we’re doing this, maybe Jeremy told you but he is a lucky man because he has four daughters.

[00:36:24] AS: Oh my gosh!

[00:36:25] JU: I’m lucky indeed.

[00:36:27] AS: So busy.

[00:36:28] MH: Part of it is like, how do these role models for female entrepreneurs, so we’re trying to get as at a better – we’re trying to learn, Jeremy and I are like, okay, “What does it mean to be a female CEO, and start a company?” And we’ve talked with women that are also sisters, moms, spouses, everything. It’s been really interesting. I’m wondering from your point of view, how do you think being an amazing woman, this artistic background helped you or not helped you or, shift you, shift may be a better word? I know you’re not the traditional person that we – I may see as typical that is like, “Let’s go raise venture money,” but you’re building this business at its hard operations, people that you have to run, retail. You don’t have people showing up to work.

[00:37:24] AS: Yeah, it’s hard for sure. I think that my mom is certainly like this and I’m probably this way as well, and I think this tends to run along the lines of many women have this characteristic. It’s just like taking on everything, holding the space for everyone, by default assuming, “I will do the things.” We’re moving right now and I just assume that it will be me that schedules the electrician, and schedules the washer, dryer delivery. It probably shouldn’t be, and that’s like – yeah. It’s kind of this like, I’m also a perfectionist. I’m also really fast and type A and I’m just like, “Well, one is my default assumption that I should do everything. And two, I think I can probably do it better so I guess for everyone, I’ll just do it.”

That’s like a slippery slope because it’s a snowball, because then suddenly, then I have all the context about the thing that I did that one time so if it comes up again, it will also be me that’s managing the repair. I use that example because I think that exact thing can happen in the work environment. That’s something I’ve tried to be really conscious of, it’s like, that’s one of my key goals for this year actually, sort of like teaching to fish instead of immediately stepping in. Because it’s also sort of like, so much more creativity and richness will come from it. I have hired an incredible team around me that I’m so proud of, I don’t need to be stepping into their circles. The ideas that will come out of that and the capabilities that will come out of someone else taking lead on something will be super productive, and unanticipated and exciting, and that’s going to open up space in my circle. I’m very Venn diagram heavy, I’m realizing. [Inaudible 00:39:04]

[00:39:06] JU: I heard it’s called ikigai. I think that’s the word.

[00:39:09] AS: It’s the hot word. It’s the buzz word. But yeah, I think like both in the home sphere and at work, I constantly have to challenge like, “Oh! Well, let me take care of that.” It’s like, “Well, maybe not. Maybe someone else either is better suited or should be contributing and like carving that up.”

[00:39:27] MH: Somebody once told me that you have the permission to say no to too. I think you’re right that women – I have the same problem at home and at work. My work husband and my real husband. It’s the same dynamic. I’m like, “Wait a minute. Wait!” But it’s your own fault in a way and you have to work on it.

[00:39:51] AS: I think along with that, there’s also this like – everything has to be done. All the laundry has to put be put away by the end, all this stuff. It’s like, nothing is ever – it’s a [inaudible 00:40:01]. It is not like a finite, “Oh! I closed the box on it today. It’s like, “No, no, no.”

[00:40:06] MH: Yes, correct.

[00:40:07] AS: It’s just happening and we’re just like blowing down the river. You have to have a moment where it’s like, you need to go to sleep. You need to like reach enough peace at a certain point where you’re like, there are so many loose ends and fires, and like we kind of have to make peace with that. I don’t have kids, but like the way my parents talk about the first kid or the second kid is kind of a little bit how I feel about like starting a business. At first, I really just cared about every little thing so much, and you still have to but it’s just literally not feasible to finish everything on all the timelines that you want. You just have to sort of accept that like it’s just sort of forever. It’s almost like Tetris or Candy Crush, like things are…

It’s like, “Okay. I haven’t crashed but it’s also [inaudible 00:40:55]. It’s just maintaining some sort of chaotic equilibrium.” That’s okay.

[00:41:01] MH: Another question for you, because you’re a female founder, but you’re also a solo founder. I think people don’t realize that being a CEO is actually very lonely. If you’re a solo founder and a CEO, it’s double lonely. How do you regain your strength because things go wrong 49% of the time?

[00:41:28] AS: Yeah. Well, I found a lot of support in other founders, whether solo founders or not. One of the things that’s been like a great relief as – this sounds pessimistic but I think it’s actually positive, no one cares as much as you. No one in the world cares, even probably 1% as much as you. This business is your baby, so like, when a stressful thing happens and this goes back to like first kid and second kid thing, it’s like, things will come up. You’ll send a subject line with a typo and that, early in your business, might feel like a really big deal and think this is not a big deal. Probably, no one even noticed it, so you need to just immediately let that go.

Then there are big things that do matter, but then like, especially related to people, you need to respect people and all of that, but a lot of the stuff that you think matters, sort of doesn’t, or you just can’t let it weigh on you because it’s not productive. That’s been a really helpful exercise for sure. Then also, this has been very hard in work-from-home times. I feel like it’s very trendy to be like an introvert these days. I'm not an introvert. I’m an extrovert, always have been, always will be. Loving around people, so it’s been particularly hard. But I deliberately sought out a space, unfortunately they closed during the pandemic, called the Assembly, which is a women's coworking space and like a wellness space in the city and like that was so important to me to be around other people. I know that I get energy from people, so that’s key.

Just sort of like that know thyself, what have you learned? I’ve learned a lot about myself and I’m like, what are my levers? I think of the business as a machine where I want to understand all the different levers, and inputs, and outputs.

[00:43:15] MH: Allow yourself.

[00:43:16] AS: What do you know? I feel hopeless and like scattered. Well, I haven’t eaten today and it’s 4:00 PM. You need to feed the machine, literally, and that’s important. Because if your machine stops, everything stops.

[00:43:29] MH: I joke with people that a group like Founder Anonymous should exist.

[00:43:34] AS: Yeah.

[00:43:35] JU: That’s great.

[00:43:36] AS: Oh gosh! Totally.

[00:43:39] JU: A question that has emerged and we’ve been asking folks, Annie, just inadvertently, and now I’m really curious about all the answers is, how do you know when you have an idea problem versus an execution problem? Like there are some things like the task to be done is, “Implement a solution.” There are other times the task to be done is, “Imagine new possibilities.” I have observed in myself, many times, the realization of “Oh! I need ideas,” is actually the important – it’s like the meta ‘aha.’ Are there ways that you become aware of the need for new ideas, become aware of the need to diverge and how to tap into a different way of thinking?

[00:44:25] AS: Yeah, definitely. One of the ways that we think about this specific problem is related to our services. One of our core values from the beginning, and based on a lot of these interviews, is simple [inaudible 00:44:39] and we have two menu items. We have a manicure and a pedicure. It’s really easy. It’s really simple. We have a very curated selection of colors, right? That’s been really important too, for people that have this decision fatigue of like 100 of polish bottles, when in fact we found that most people actually, at least for our target customer, choose the same color or the same two or three colors every time forever.

I wear red on my nails, always, always will. It’s like your favorite pair of blue jeans. If it ain’t broke. That’s a specific point of view. We’re not everything to all people, but for what we offer, that’s what resonated. I think one of the areas where that started to be –– as we grow and as we have more customers, where that sort of be challenged a little bit is like, “Okay. But can I have a slightly longer massage on this pedicure?” or “Man, this time of year, I really like to swap to this type of color.” What we’re trying to sort of do is be faithful to what our core customer resonates with, while still accommodating some of these changes. It’s like, “All right. Instead of adding a separate pedicure that’s a longer, more extensive service, is there a way that we can still – like what our customer loves is to make only one decision at a time so, question one is like, “What type of service? Manicure or pedicure? Okay, pedicure. Color or not?” Then, “Do you want to stick around for long?”

Instead of asking those all at once and having all those different options. I love to think about it. Do you guys have the Philz app? Do you like Philz coffee? So like, I’m obsessed with their app and I’m like, “Yes. [Inaudible 00:46:10] and it’s medium and it’s this, and it’s that.” Like that is exactly how you should be able to – one day, we’ll have our own app to book a mani.

[00:46:17] JU: I agree. It's beautiful. I don’t know why more people don’t do it that way.

[00:46:20] AS: I love it. So it’s like, they don’t present that whole matrix of the 50 different permutations. They present it as very streamlined, so we’re in the process of working towards some version of that for ourselves. It’s still, it’s like – yes, there’s a few more sort of permutations that we want to introduce and have in our operation and be able to offer. But we don’t want to change this core thing, which is sort of like simplicity and reducing decision fatigue. We solve that elegantly. That sort of like – I don’t know if that directly answers your question, but it’s sort of like, the idea is there and we haven’t – we’re finding ways to execute it appropriately, while staying true to what’s special about us.

[00:47:01] JU: What is the sensory mechanism that allowed you to know that you need it? Is it complaints? Is it a staff that is aware of customer friction? What is the sensory mechanism that allowed you to go, “You know what, simple pleasures is the thing, but we got to redefine how we’re implementing that”? You know what I mean?

[00:47:20] AS: Yes. No, it’s direct customer feedback. It’s often in the vein – we’re very lucky we got a lot of positive customer feedback. It’s in the vein of like, “Yes and,” or like, “What about this circumstance?” Another example is, we have – instead of just having the same colors always, we have a core collection [inaudible 00:47:38], forever favorites, always on the menu. We cover the key basis. You know they will always be in stock. We also track polish colors so folks always know that we can either make personalized recommendations or have your favorites ready based on your profile. Then we just did a very simple thing where we added, just like a restaurant might do, we have seasonal specials that are introduced every month, that can sort of scratch that itch where it’s like, we want to be careful because you don’t want to be skewed and like completely expand and be like, well, this person, they need to still be your target customer. We really try to be rigorous about like, we just might not be the right fit for this type of person. But this is the kind of way for us to be like, “All right. This still fits within our target audience and how we can sort of like have our cake and eat it too without changing our ethos?

There are couple kind of operational tweaks like that that have really unlocked our ability to keep everybody happy and satisfy a slightly different customer demand, but remain true to what makes us unique. Yeah. Through feedback, though, is always where it comes from.

[00:48:43] MH: I like simple, by the way.

[00:48:46] AS: [Inaudible 00:48:47]

[00:48:48] MH: Like if you want to be successful, you need a simple offering.

[00:48:51] AS: Yeah.

[00:48:53] JU: Annie, we’re super grateful for your time. Last thing is, or just your sign off is, where can people find you. If they want to know more about High Five, where do they go on the gram, on the web, whatever the new hot platform is. Where do they go?

[00:49:07] AS: Please come say hi. Our website is wehighfive.com, all spelled out. Our Instagram is @highfivenicenails. Come say hello. Our San Francisco shop is located at 1893 Hayes Street. That’s the intersection of Hayes and Ashbury. Our new Marin location opening on the 16th of April is at Marin Country Mart. If you all have been up there, we’re right next to Sarah Shepard Gallery. There’s a Soul Cycle. There’s a Hog Island Oysters. There are all kinds of fun stuff out there.

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