Chantelle 00:02

I kind of learned to be comfortable in my own skin and recognize that my team knows I'm human. They want me to be human, and the more transparent I can be about my own growth, the more comfortable they feel talking about theirs.

Leah 00:19

Hi, thanks for being here. And welcome to Season Two of The Founder Mindset, brought to you by ATB. I'm Leah Sarich, your host, and I'm super excited to talk to more Founders about the human experience of being an entrepreneur. In this podcast, we're digging into what it really feels like to build a company from nothing. I was a broadcaster for over 20 years. So, I've interviewed thousands of people, but entrepreneurs, not that many. And yet they have the best stories. They're solving big problems and they're creating incredible impact. But it is hard work. So, why would they do this? Let's find out.

Leah 01:04

Joining me in studio today is Chantelle Little, Founder and CEO of Tiller, a web design and brand agency in the B2B SaaS space, serving clients across North America. Chantelle, thank you so much for being here today.

Chantelle 01:17

Thanks for having me. I appreciate it.

Leah 01:19

Wonderful. Let's go back to the beginning, as we do in all of these conversations, so how did you first come to being an entrepreneur?

Chantelle 01:27

Well, I was in university, and I was trying to find a summer job, and I got a summer job at a health benefit company, and it was a small team, about eight people, and they didn't have anyone in the marketing side of the business, so they hired a summer student me to essentially come in and help them market a couple of their HR products to HR managers, and I, of course, knew nothing. So, they were very kind to have faith in me. And I spent the summer basically trying to figure out how to create explainer videos and landing pages and all of those kind of one-off marketing pieces to try and help them market that product. And I just fell madly in love with marketing. And I mean, 30 days in, I was like, I want to do this for lots of different companies. And so went to my bosses and said, hey, I'll finish my contract here with you. But I also wanted to start my own thing on the side and try and actually do marketing for other companies. And that's kind of how it began.

Leah 02:24

Wow. So, talk to me a little bit about this idea of just falling madly in love. Like, What did that feel like? How did you know that this was what you wanted to do?

Chantelle 02:32

It's a good question because I think that now that I've been doing it so long, I'm even more in love with it. But in the moment, I thought I wanted to be an engineer. I thought I wanted to be in finance for a while. There I was like, oh, I should be a futures trader. I should be a lawyer. Like, I was kind of all over the place, but the storytelling part of marketing really got me and the idea that companies have solutions that can really help make people's lives better, but it requires very clear messaging and really highlighting the values in order for that to translate and cause people to buy a solution that actually will better their lives. So, there was sort of this, this storytelling piece that I just really fell in love with. And I liked the variety too. Like trying to understand the story for a whole bunch of different companies versus just one. Which is what's appealing about the agency space for me.

Leah 02:32

Right. Well, I mean, I get it with the storytelling, right? Because, yeah, obviously, I love storytelling too. But what I'm really curious about is, you are, what, 19 when you're putting this together. Like, how did you how did you go? Okay, I'm 19, but I still got to figure out how to make a business out of this.

Chantelle 03:36

I don't know. I've had so much fun in the summer job, and I was like, well, I could make some extra money if I did this on the side. And so, at the very beginning, I think I saw it as a way of funding getting through the rest of school because I was in the middle of my business degree, and I was thinking, Okay, well, I can make a little bit of extra money. It will help me pay the bills for schooling, and then I'll revisit when it comes time to graduate. But then after I've been doing it for a short time, I was having a hard time imagining not doing it. So, as I neared graduation, some people were saying you should go get a real job. But I was like, but I'm really committed to this now. I really like this now, and I wanted to scale it, so I don't know it just kind of happened. Yeah, naivete is bliss, right? Because I didn't know how hard it would be, and I had very little responsibility to being 19. Like–

Leah 04:27

Were you still living at home?

Chantelle 04:28

At home, yeah, my parent's loft is the first office. Yeah, for sure.

Leah 04:33

See, that's so great. You know, I hear that a lot in this podcast. There's some naivete involved, like a lot of people, like, well, I thought this would just be a really good idea, and I would just give it a go, but I didn't realize how hard it was going to be.

Chantelle 04:44

Yes, I definitely did not.

Leah 04:45

No kidding, amazing. But you know, what still strikes me is this idea that you even knew what scaling this opportunity meant. Do you know what you mean? Like, I didn't know what that meant before I started working in this sector. Like, what is scaling? Why do they keep saying scaling? I don't know what that means. And here you are, and you were just like, this young person going, I just want to do more of this. And so you just knew that that's what was motivating you to grow this thing.

Chantelle 05:09

Yeah. In the early days, the projects I were doing were really small, and so sometimes it was difficult to calculate the impact of them, but I could see the impact that it was having in little ways for the entrepreneurs or the businesses that I was helping, and I found a lot of fulfillment in that, and I just got excited about the idea of scaling that further. I hired a couple of summer students to help me. I had to pick one of the guys up from the bus at the Rec Center and drive him to my parents' house, and we worked there during the day, and I’d drive him back. And it was sort of an odd situation, but we had a little pancake breakfast, like in my parent's loft with a couple of the summer students. And my sister was there, working there for a bit. I recruited my mom to volunteer for a little bit. We tried all this stuff, and I think once I started building a team, I also got even more excited because I really liked the team-building side of it quite a bit more than I expected.

Leah 06:02

Okay, see. But again, here's me going, Okay, but how did you even know I need some summer students, and how am I gonna keep these guys happy? And how did you even know how to be like a boss, like person? You know, at 19?

Chantelle 06:14

I'm still wondering if I know how to do that. I don't know. I have always loved learning. So, I think that while I was faced with so many things I didn't know how to do, there's something thrilling about trying things and sometimes failing isn't super fun, but sometimes it is because you're like, I learned this really big thing, and now I can take that learning and apply it. Now I like failing and learning even more, but it's like the immature me at that time with zero experience. I still liked the challenge of having to figure something out that I didn't know how to do. So, of course, I asked my professors, because I'm in university, right? I asked my professors, for example, my first-year end. Didn't know how to do it. So, I went to my financial accounting professor, and I was like, hey, is there any chance I can get 30 minutes of your time? Can you help me do my year-end? And he was so gracious. He's like, Absolutely. So, I sat in his office, and he helped me. So, I think I just reached out to people within my school community. And my dad was always a wonderful mentor to me, and like other people kind of contributed to that. And then, of course, there's Google and reading books and just figuring out what, sifting what works for you and doesn't right, and just trying and failing a lot. Yeah, yeah, a lot.

Leah 07:24

Classic entrepreneurial journey, right? Classic, classic. Okay, so let's get to Tiller. So, this is the work you're doing. I'm assuming this all led to the formation of Tiller. So, tell me a little bit about Tiller.

Chantelle 07:36

So, Tiller is a digital marketing agency for B2B SaaS Founders and Marketers and we essentially help different companies at different stages in their life cycle with solving various challenges. And some of them are branding-related challenges. Some of them are web and conversion related or customer acquisition challenges. Some are even product challenges. We have built our service offering around that audience and those different challenges, and they differ depending on whether someone's brand new as a Founder or they're scaling up.

Leah 08:07

So cool. That's amazing. Yeah. And how many employees do you have at this point?

Chantelle 08:10

We have 30 now, and then some contractors on our team and hoping to scale it further. So, I'm excited about that.

Leah 08:19

Look at you go, amazing. This is so great. And you were telling me that 60% of your client base is currently in the US.

Chantelle 08:25

Yeah, that's correct. So we, in about 2018, decided to expand into the US, and we did a whole bunch of campaigns, and we've grown it through word-of-mouth referrals. And so it was kind of exciting at first. It was a bit of a spray-and-pray methodology, and we were kind of doing a little bit too much and too broad, but we found some specific areas, geographically speaking, in the US where we could focus more of our energy. So, yeah, 60% of our business is there today.

Leah 08:53

Wow, yeah, that's incredible, yeah. And now you were telling me that you're really curious about, you know, doing some work in your own backyard here in Calgary.

Chantelle 09:00

Yes, yeah, absolutely, yeah. When I started Tiller, we were the agency for all, like we served any kind of business, and then we had a moment where we decided to pivot and focus on the B2B SaaS space. And during that time frame, the tech ecosystem has changed so much in Alberta. I mean, it's been here for a long time, but it's accelerating so rapidly and not only is there a greater presence of B2B, B2C, SaaS companies in Alberta, but there's also a lot more ecosystem partners, and there's a lot of VC activity and things like that happening. So, we're actually quite excited about leaning more into our own backyard and working locally and being part of shifting Alberta's tech ecosystem.

Leah 09:40

I like hearing that. That's very exciting, very exciting. I want to dig into a little bit about what it was like for you building this company that is now Tiller. You would have been a very young boss and a young entrepreneur, raising money, asking people for money and clients, and tell me a little bit about what that experience was like.

Chantelle 10:00

Yeah, well, in the very early days, it was incredibly challenging because I was so young and I had no experience. And then I made the mistake of hiring very young people with no experience, right? So, it didn't help. I was quite intimidated by hiring people that were older and more experienced than I was, because I kept thinking, why in the world would they want to come work for, like, a 20-year-old or a 19-year-old or a 22-year-old, right? Like, why in the world would they want to–

Leah 10:30

Which I think is a real concern.

Chantelle 10:34

Yeah, very valid, especially when you see some of the things that we were trying to do, right? I think it was really tricky because I think I spent quite a bit of time trying to overcompensate for my age, and I think that it took quite a bit of time for me to just lean into my authentic self and just be comfortable in my own skin and just be sort of the passionate, energetic, like entrepreneur that I am. And I wish that I would have just leaned into that sooner. Because I think it really stunted our ability to grow in the early days, but it was challenging.

Leah 11:06

Sure, but you were young, and you were learning, right? Tell me a little bit more about this overcompensation that you, that you're talking about, because I think there's a lot of young entrepreneurs that could really learn from that.

Chantelle 11:16

One of the most obvious things was I like, would dress to the nines, like every day. Like, I would wear high heels every day to the office. We were up until COVID, we were in the office, like, five days a week and I would just, like, really try to overcompensate, and I would try to almost talk differently as well, and just use bigger words. And it almost got to the point of, like, almost speaking too intellectual and not clear. Like, there's things where you're just trying so hard. And I think people can snuff that out. They can, like, feel that you're doing that. And so I think those are just like, little ways that I was finding myself doing that. And I think I was also kind of sensitive too. I was probably a little bit too sensitive. I'd read too much into things, be it with a client or in conversations and just think that, oh, they don't believe in me, and it would kind of create a narrative in my head that I don't know. I had a lot of limiting beliefs that started to come up for me, and I sort of–

Leah 12:12

You were taking it personal.

Chantelle 12:14

I was taking it personally, yes. I had to work through that.

Leah 12:18

I was going to say. So, how did you move through that?

Chantelle 12:21

I think some of it came through experience, and starting to get some wins, and realizing that maybe I knew a little, just a touch more than I thought, you know, that maybe the experiences that I was having were building to something bigger, and I could start to connect the dots between those experiences, and I could start to leverage those experiences to build confidence with potential customers. So, I think that was part of it. But actually, the journey went on a long time, and it was actually, I think, 2018 that I hired an executive coach, and I worked with her, and she really, actually helped me identify that I had quite a few limiting beliefs and kind of helped me see how those limiting beliefs were connecting to Tiller's growth.

Leah 13:02

Oh, interesting.

Chantelle 13:03

Like, I put them on myself. But inadvertently, had put them on my company. And so it was actually kind of crazy. She had me write down, I'm right-handed, but she had me write down all my limiting beliefs with my left hand one night, and I started, like, bawling. I was like, I can't believe I think this about myself. But the idea was, like, I had to slow down when I was using my left hand right, because I couldn't write fast right. And as I did that, it kind of revealed how silly some of the statements were. Like, just things like, I'm not a visionary, or I can't lead a team of more than 20 people, or all these types of things I could never inspire people. Like, just things that are, I think there were 60-plus of them. It was actually pretty transformative for me because I realized how silly they were, and then I realized that it was holding Tiller back, which pained me more because I'm sitting there looking at my team who all wants to scale this thing with me, and I'm thinking like, I'm holding them back. That cut deep. But it also inspired a change in my mindset, for sure.

Leah 14:00

But I mean, there's a couple of ways you can go once you have that realization, right? Yeah, like, I mean, some people could, you know, turtle in the corner and fetal right? I mean, others can be like, Oh, I now have the awareness. I can approach this as an opportunity, right, and not as a failure, as an opportunity for growth and change, yes, which is exactly what you did, yeah. How did you know that was the right thing to do? And how did you sort of have the, I don't know if it's courage or or even confidence to go, you know what? That's okay. I now see it. I got it. I know what I'm doing, and I'm gonna just change.

Chantelle 14:32

Yeah, I think one thing that I realized is that I needed to talk very openly about it at Tiller with my team. And I think that was an interesting shift for me, because I came up with this, like no ceilings kind of concept, and I went back to our culture. So, we created a culture deck, and we created a whole bunch of like principles that go beyond our values, but they really describe how we will approach challenge and how we will approach success, and all these types of things. And I think just the process of going through and documenting that and then actually trying to embed that into the DNA of the whole company. It was cool because it became an accountability mechanism for me because now I need to live that, like and breathe that. I want to inspire the rest of the team to do the same, or if I want to attract talent that is inspired by that growth mindset. So, I felt like it raised the bar for me from an accountability perspective while also helping to slowly shift the way we speak because we try to change the language of the organization quite a bit to shift more towards that growth piece. So, it was through that process that I kind of learned to be comfortable in my own skin and recognize that my team knows I'm human. They want me to be human, and the more transparent I can be about my own growth, the more comfortable they feel talking about theirs.

Leah 15:49

Oh, that's exciting, yeah. And then, of course, leading to the growth of everyone and the organization together. Oh, that's amazing. Culture is very important to you. I know we talked about this in the pre interview. It is extremely important to you, is that, because it's an extension of this work that you're just talking about, but tell me a little bit about how you think about culture?

Chantelle 16:05

I think it is an extension of that. I think early on in my entrepreneurial career, I think you think, Oh, I'll set the culture, and then it's like a one-and-done textbook, like, I learned a little bit about culture and university, in business school, but like, you don't really know what that looks like in a real living organism, a company until you start to play with it. And so I think in the past, I would make one-off investments in culture, not one-and-done, but like, one-off investments periodically. But I didn't know how to, like, really make it live and breathe. And I eventually realized, yes, it's my job to set the tone, and it's our leadership team's job to set the tone. But I started thinking about how every person I hire is either going to really grow the culture and, like, kind of make it better, or they're going to actually take away from it. So, yeah, it changed the way that I thought about even hiring. And so, as we started to scale the company based on culture being very, very important, I think that the company culture just started to blossom in a new way, because we had a whole bunch of people that were contributing to it. Everybody is contributing to it. And so I think that that was a game changer because now it's still my job to set the tone, and now I invest more intentionally and more consistently. But everybody's doing it. So, that's kind of the most rewarding piece because you see what they're doing, and you're like, Well, I didn't even ask them to do that, yeah.

Leah 17:33

Look at that. They're doing it all on their own. Yeah, yeah. Also takes a bit of the burden off you too, right?

Chantelle 17:38

Absolutely, yeah, because everyone's elevating it together.  

Leah 17:43

Oh, that's really neat. Talk to me a little bit more, too, about just being this young boss and even talking to clients, for example, and convincing them that, yeah, you're the company to go with, even though we are young and we are, you know, growing. That would have been tricky, I would imagine.

Chantelle 18:01

Yeah, yes, it is. It is hard, and it got trickier the more that we scaled. Because, at first, I'm asking someone to part with $2,000, right? Like just $2,000, and sometimes that was hard, and then the ask gets bigger, as as our company, we had higher price points and things. And now you're like, well, now I need you to part with 100,000 or 200,000 in different cases, or 300,000 whatever it is, and I would say that, I think that without knowing it, the way that we won was on attention to detail.

Leah 18:29

No, kidding.

Chantelle 18:30

It sounds so simple.

Leah 18:31

No, but how did that change you?

Chantelle 18:32

I have a high attention to detail. If my team were sitting here, they would laugh and be like, Oh yeah, she does. And I think that that can be a pro and a con superpower, and it can be also something I have to work on because I'm a perfectionist. So, you know, sometimes you can slow things down because you're in the pursuit of every detail. But I'd say that when we were competing against other agencies that were bigger or had more years of experience, the detail and the thoroughness and the like, we listened to the customer, and they could tell when we gave them the pitch or the proposal, it started to help us win. So, the most common feedback we would get in, like, every pitch was like, Oh, this is way more thorough than that agency or that agency, or that agency or, like, we got kind of like a templated thing from them, but like, I can tell that you're already kind of trying to solve our business problems. So, I think that that helped because then age was a little bit less relevant. It was more like this seems more interesting to me. So, it helped.

Leah 19:29

For sure, it did. And this is the team that's going to get the job in a unique and special way for us. It's interesting.

Chantelle 19:33

So, that was part of it I think.

Leah 19:35

I love it. I love it.

Chantelle 19:37

We had to work hard for that business, so I think we put lots energy in.

Leah 19:41

Good for you guys. That's amazing. We've talked a lot about, you know, being an Entrepreneur is like for you. But I'm also really curious, particularly in this podcast, we talk a lot about how being an Entrepreneur and a Founder of a company affects your personal life. I mean, how does it affect your personal life? What does it mean to you?

Chantelle 19:57

I was thinking about that because there's so many facets to it. And I think that the thing that I thought would be interesting to talk about is was more like health, like, just the health side of it, because there's so many facets to it. I mean, being an entrepreneur like, it's difficult to ever turn it off. There's constant pressure. And depending on what's going on in the business, the pressures can be, like, really, really high. But there's always pressure. Even when things are going really well, there's pressure. Pressure of success, right? As just as much as there's pressure of failure. And so I think because I started the company so young, and I had a lot of energy, like, I could really, like, pull the all-nighters, like, three, four days a week, like, honestly, like, it was bad. And I think I just sacrificed so much of my health. I was reflecting on this, and I think I didn't want to sacrifice my friendships or my family. I wanted Tiller to grow. So, the thing that I sacrificed was my health. Because I'd be like, Yeah, let's hang out that Friday night. That sounds so fun, but at 11 pm, when I got home on a Friday night. Of course, I'm like, Well, I promise that person to have a proposal to them tonight. So, now I'm doing it till like two in the morning, you know, to get it done. I think I often justified it by saying, well, it's just a particularly busy time. You know, I had to learn that I was running a marathon, not a sprint. Like I had to learn that. I slowly started to hear stories of Founders and Entrepreneurs who, like, at a relatively young age, were burnt out or ended up with these health issues. So, I just really took a moment to pause. This was not even that long ago, like three, four years ago, and I was just like, I have to change my lifestyle, like I have to change the narrative in my head, that I have to look after myself first so that I can be a good entrepreneur, not like, I'll figure that out later, right? Because later is just like an elusive, we don't have time. We like, there's never time. There's never time. So, if I can't figure out how to change my lifestyle and get those disciplines in when I'm busy, I'll never figure it out because I'm getting busier every year.

Leah 21:57

Of course, so, it’s now or never.

Chantelle 21:59

Yeah, so I just decided to change, like, I'm kind of a funny person, because when I'm like, in on something, I'm in. So, I was like, January, you know, the whole, like, New Year's resolution, I was sitting on this chair in my house, and I was like, I keep thinking, like, I'm not fit, I'm not gonna figure out the sleep thing, like I'm not gonna be like, you know, like, whatever, like I'm not gonna be healthy like I'm never gonna understand all that. And I've just told myself that. But instead, what if I just said, like, what are you capable of? Like, what if you just tried and what if you just explored what you really could do and could become? So, that started a pretty big transformation for me, personally and physically and all that, mentally and all that.

Leah 22:37

So, what did that look like for you?

Chantelle 22:40

Well, I started working out five days a week. And prior to that, I hadn't worked out, like, I'd work out, like, once every few months, right? Like, it was like, I mean, I would, like, go on walks and stuff, but I'm talking like, actual working out. So, I was like, you know, Googling, like, what should I do? And then I was like, okay, I did a few days of cardio and, like, hit training, and then I saw I should be lifting weights, so then I started doing that, and then I did, like, a whole audit of my diet. And was like, I need to get I love science, so why don't I just get into the science of nutrition? So, I got into the whole, like, eating high protein, high fibre diets. And, like, I actually found a passion in actually learning about all these nutrient stuff, like it what didn't feel like a burden eventually. First, I was like, Oh, my God, overwhelming, it’s so much. But I kind of got into it. And so I changed my whole diet. And then I really decided, like, I need to start, like, really trying to get seven hours of sleep a night. Like, it sounds so basic, but I wasn't doing it, right? I could get wide awake easily on four because it didn't affect me much. Doing that three nights in a row like that would be bad. So, I just started changing my whole schedule. I started scheduling in my workouts and like things like that. So, none of it's rocket science, but for me, the combination, oh and like, drinking more water and stuff like that. So, it was the combination of all of those things that really gave me, like, a new level of energy that I'd never experienced before. So, I became the fittest, and I lost a ton of weight, like, and just, like, it was crazy. So, now it's cool because I can't imagine living like that now, right? Like, I know it's a lifestyle change because now I'm like, Oh man–

Leah 24:17

I could never go back.

Chantelle 24:19

Yeah, like, if I have a really big week at work, like, you can tell by, like, what I buy at the grocery store and how I schedule my workouts and when I'm like, Okay, well, I need to go to bed at this time so that I do get seven hours of sleep and I can just feel it all day, like the energy. So, it's not rocket science, but for me, it was, like, a really big change.

Leah 24:37

And it was super intentional, like I'm hearing you say I need to schedule. Like, everyone's gonna see this calendar, and here's where I'm doing this, and here's what I'm doing that. Like, you had to be super intentional about it. Good for you.

Chantelle 24:49

So, I became kind of, like, I run jokes that I'm like, passionate about protein now, because I talk about it for, like, our snack day at work, I was, like, bought a did a protein bar. Or like, choose their protein bars. So, I kind of, I just love it. It's fun to find a passion in it. Because prior to this, it felt like something that I had to do, and now it's not like, I like doing it every day. No, like, this morning I woke up, I was like, who I don't know I want to work out right now, but I was like, I'm going to, right?

Leah 25:18

Because I know how I'm going to feel after.

Chantelle 25:20

So, I just am grateful that I figured that out because otherwise, I'm not sure how much longer I could have gone. Because the demands are so intense, that it's just like, I don't know now I feel like I better look after myself. So, that's just my example.

Leah 25:38

That's a great example. Thank you for sharing that.

Leah 25:43

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Leah 26:07

So, every time someone sits in this chair, I ask them about a pivotal moment in the formation of their company. And everybody's got a few of these stories, trust me, but if you can think of one, when it was like, really the Do or Die moment for you. And you really were like, Okay, this is huge. Tell me about that moment for you.

Chantelle 26:25

Okay, so I knew you're gonna ask me that, so I narrowed it down to three. I didn't really want to tell us one because everyone talks about COVID, and then it starts to feel cliche, but that was kind of the most Do-or-die moment for me.

Leah 26:36

Please share it.

Chantelle 26:38

So, I'm just gonna talk through that one.

Leah 26:39

I love it.

Chantelle 26:41

So, the summer of 2019, just before COVID hit Calgary, I was, like, at my parent's cabin, and I was sitting there, and I was thinking about Tiller, and I was just feeling like, Man, this is like, I feel like I'm on a hamster wheel. This is really tough and really intense. And I think what I realized in reflecting on it’s because, like, I didn't really have anything differentiating me in the market. There's tons of agencies, there's tons of freelancers, there's tons of people that could help with brand or web. But I also knew that something that we were doing was special. I just hadn't named it or figured it out yet. And so, as a result, when you're not differentiated, it's hard to charge higher prices. It's harder to have a predictable and repeatable pipeline. There's a lot of sort of ripple effect issues that happen when you're not differentiated. So, I read this book called Niche Down. Have you ever heard that one before?

Leah 27:31

I feel like that's come up.

Chantelle 27:33

Yeah, like Christopher Lochhead, and I can't remember that I should have got the other author's name. Niche down. And basically, he kind of talked through the the power of niching down. And it was interesting because I was sitting there thinking, like, we kind of are the agency for all. We serve everybody, but we had started working in the tech space in 2015, and so we had lots of tech customers. We just hadn't actually positioned ourselves as an agency for tech, and he talks in the book about how you either position yourself or you get positioned by the market. And I thought, Oh, that's interesting. And then he kind of uses real examples of companies that decided to niche down, and it was the very thing that helped them scale. And it feels counterintuitive because you're like, I'm gonna narrow my audience, right? I might even be narrowing my offering, and yet that's gonna help me scale. It feels just kind of like a risk, but in the same breath, everything we were doing wasn't working, and I was reminded of that old saying, like, the cobbler's children don't have shoes. So, I'm sitting there being like, we actually do this for other companies. Like, we know how to position companies. We know how to help them with their value prop and their messaging. We know how to help them at a brand level, and yet, like we're spending all of our time doing that for all of our clients at the expense of figuring it out for ourselves, right? So, I decided that summer that we were going to position ourselves as the B2B, like the agency for B2B SaaS, which felt like a risk because of the time, I have a lot of customers that aren't in that space, and we were struggling at the time when we were figuring out how to do it, but we started to plant the seeds. We revisited our personas, we looked at our value prop. I came back from holidays, and I got, like, everybody in the boardroom, and we drew up the whole like new brand story. And we started to figure out how are we different than other agencies. And we just started to do what we do for other companies, for ourselves? We kind of made Tiller a client of the agency, and I think that was a really pivotal moment. But then fast forward so COVID hits, yes, and it's like, I'm standing in our nearly newly built office like it was like 90% complete. We had put, like, a lot into this, and we were building a space that we could grow the team to, like, 45 people, was our idea over the next couple years, once we moved in, and so I'm standing in the office and then find out that, like, COVID hit here, and I'm like, kind of stressed out, because I'm like, we just put all this energy into this office, and we're supposed to be moving in, like, in a month, and now everything's shut down. And naturally, like so many other people were faced with, you're trying to pivot to remote work. We'd never done that before. Tons of agencies do it, but we had never done it. Then the next week, we lose our biggest client, and I'm like, Oh my goodness. Like, it was a really tough client to lose at that exact point in time because I just hired someone to service that account, because it was so big, and all these things were happening, I'm like, we're supposed to be moving to this office like now we don't even need an office like this kind of what I'm thinking, the remote thing, losing our first client. But it also was an interesting moment because I started realizing that the work that we had done, like the summer before and leading up to this point, created a unique opportunity for us. And I could have never seen that coming, but because we had pivoted to focus on B2B SaaS, a lot of the companies that we were serving, they were losing some of their channels for marketing. So, we have a lot of clients, heavily dependent on events as an example, right? So, all of a sudden, it evaporates. That's gone. And they're like, what are we going to do? So, all this is happening at the same time I'm sitting there, all this is happening, and I'm like, my top thing was, I don't want to have to let anyone go. Because, of course, I'm hearing friends and family members and all these people saying, like, yeah, my company laid me off, and that was facing so many people. The entrepreneur me is like, I just do not want to have to let a single person go. So, with our new positioning in place, mixed with the desire to not have anyone be let go, I kind of just went into crazy sales mode like crazy. I just went crazy. I was working around the clock trying to sell as much as I possibly could, to refill the revenue we lost from the big customer leaving, and then also to see if we could continue to scale and almost take advantage of what was happening in the market at that time, and it ended up really paying off for us. But there were so many moments, because that actually is what really led to quite a bit of our growth. But there were so many moments and so many weeks in that period of time where I was just like, every day, I was like, am I going to have to let someone go? Because it was slow, it takes time, right? And I think it was just like a very stressful moment, but I'm also really grateful that we had done some of that work for ourselves because I look back now not knowing if we would have survived it, if we hadn't done that, right? So, it was, yeah, it was a stressful time, but I think it also really made us better, and it reminded me deeply that Tiller always has to be a priority in terms of, we can't be the cobblers kids situation ever again. Because it’s a super high-risk way to build a business, is like to de-prioritize your own brand. So, we needed to live the walk and or walk the talk and really do it. So, it was a big moment for us, for sure.

Leah 34:42

No kidding, yeah. So, reflecting on that now, I mean, what are some of the big takeaways from that period of time for you, maybe personally and for the organization?

Chantelle 32:52

Yeah, there's a few components to it. Because I think personally it was a moment where I realized how much my team drives me and like my clients and people drive me. I don't want to let anyone down, and I'm sure many entrepreneurs and founders can relate to that, but there's like a deep part of me that just really wanted to perform for the sake of my team because I think that was just a big thing that I realized in that moment. It showed me how important it was to build culture. It was like another time like we were talking about a few moments ago, about the importance of investing in culture and finding creative ways to do it, because suddenly the mechanisms that I had used to build culture were not there. So, it was like, how can we still invest in our culture in creative ways without the ability to be face-to-face? And so we did, we did some silly things. We launched a new website in that time frame. And I remember Brandon, our COO and I, we drove around with like, a big sign on the back of my car, and then, like, dropped off cookies at everybody's houses and stuff like that. And it was like, we just launched our website. We almost scraped some paint off the vehicle. It's probably not a good idea because we use, like, some fish wire to do it. So, not a good idea, but I think you just realized you got to, like, put in the effort and try to figure out ways to do it. So, that was kind of one thing that I learned. But I think really the biggest thing was that you have to really think ahead when you're building a company. You have to, like, find ways to future-proof your business. There's no magic bullet for that, and there's no actual future-proofing of your business. Like, fully, yeah. Like, like, you know, you can only do. There's no certainty. There's only so much you can do. But I think that we all do have levers. Like, I had levers in my hands, things that I could pull and adjust that would position Tiller to be more future-proof. So, even the way that we were managing our money at the time completely changed. There were a lot of things where it was like, you know, I didn't really, for 10 years, have an emergency fund as an example. And I was like, that example, that situation, reminded me of why you have one, right? And, like, we always should have one, not just when there's COVID, right? So, I think you learn a lot of things about, like, there's an unexpected situation that happened to all of us, and there were certain things that we had put in motion that helped us weather the storm and eventually thrive through it. But there were other things where I was like, Oh man, like we were fortunate that we didn't, you know, get wiped out because we didn't have that in place before. So, we've changed a lot of things in terms of, like, money management and practices, how we do revenue forecasting, how we do strategic planning, like there's a lot of things that we've changed, to try and I mean, hopefully, we never have another COVID. I'm just thinking like there's lots of other things that can happen. So, it's kind of just realizing you have to be really intentional about building that future, or you're really at a very high-risk place all the time.

Leah 35:44

You know what I'm just reflecting on here that it sounds to me like you learned so much going through that experience, but you mentioned that right off the top of our conversation how much you loved to learn. That's really what got you started in the first place. Is that one of the core values for you personally and Tiller?

Chantelle 36:00

Yeah, I think so. Like, I like to sometimes talk about learning from anything and everything, like, but you have to sift, right? So, you have to learn both muscles, like, you have to, like, consume. So, I think of myself as a little bit of a sponge because I could be watching a movie on a Saturday night and learn something and apply it to my business on Monday, and I'm and people will laugh about it, but I was just telling some people at work a couple of weeks ago that I watched a show that gave me inspiration for Tiller. But it's like, why not, right?

Leah 36:00

Why not take it from anywhere?

Chantelle 36:27

I think you can learn from anything and everything, but I think that it requires, like, you can't have an ego, to be really good at learning. So, I think as a culture, we've put a lot of emphasis on, like, no ego. We're all gonna learn from each other, and we're gonna sift even things that we can learn from other companies and other markets. We’ll sift what's relevant to us, but I think learning is a competitive advantage for sure.

Leah 36:47

Absolutely. Yeah. It is for us too. We lean to that a lot. Let's talk a little bit more about what you really love about being a Founder. You talked a little bit about this learning, but tell me what lights you up when you're a Founder.

Chantelle 36:59

Oh, I think, like most Founders, I really love the thrill of building something from nothing. And then once your business is established, and then you're scaling it, you're constantly building and reinventing off of the foundation that you have established. And there's just something really exciting about that, right? Because some of the things you try are just gonna fail. But it's kind of like, you don't have to sit there living with regret, right? So, it's just like, it's really exciting to have that flexibility to actually try and create something unique and different. So, I really love that piece of it. I really love building a culture. I know I've touched on that in the building of a team that's really fun. And I really love helping people realize their potential. I think that's like, the leadership side of me that's really deep. Like, I really love that. So, it's been probably, like, the most rewarding part is when I'm like, we hire someone on our team, and we see what they're capable of, and we often see a lot more in them than they see in themselves, and then over time, through opportunity and exposure and learning, they have the opportunity to grow themselves. And those are the moments that, like, make my eyes tear up. You know, it's just like, it's really exciting. Some people have just, like, transformed, and it's really cool to be, to be a part of that, for sure. And in the same way, for our clients, they have so much potential, and oftentimes they just need a little bit of help overcoming some of those hurdles. We come alongside them. We help them overcome those hurdles, and some of those have had a huge impact on the trajectory of that company, and that's really fulfilling. So, I think there's just, I love helping people realize their potential.

Leah 38:37

I love that. We talked a little bit about how you sort of protect your own personal tank and stay filled up. But is there something you talked about the exercise? Is there other things that you're really mindful of to ensure that you're able to keep being this Founder that you want to be?

Chantelle 38:50

I think that there are a lot of different components to it. Yeah, for sure, I think that I'm mindful of, like, trying to be someone who's very reflective on, like, I really tried to be very reflective about what's going on and take moments to really pause and look at what I'm learning.

Leah 39:09

Do you actually schedule that in because I've often thought I'd love to do that more, but I almost find I have to put like time in my calendar to do so?

Chantelle 39:15

Yeah, I should schedule it in. I'm currently doing like, a calendar optimizing thing. And I was like, I'm trying to put in blocks for some, like, deeper focused work, So, I think that's a good idea. Actually. It's more like something, yeah, exactly. Yeah, every day, yeah, yeah. Like, I would say sometimes on Saturday mornings, I just like to, like, have a cup of coffee and, like, sit there, and sometimes I read, and sometimes I'm catching up on emails or something, but it's like a no-pressure situation. And sometimes those are good moments where I like, really like to reflect, because I think sometimes when you are moving so quickly, you don't even realize what you're doing. I didn't know I had that habit, or I didn't know that I've done the same thing 50 times, and it failed every time. You know it's like easy to miss what's going on. So, I think that's a really key piece. Is like trying to reflect. I also try, as best I can, to ask people for feedback in different ways. So, you know, like, is there something that I could do that would help you more in this area? Because then I do think sometimes there's hesitation to give your Founder feedback. I think that can be a challenge. So, I think creating space where people can offer feedback does help you, as a founder, figure out how you can grow because we all have our blind spots. And I think that's really powerful because it's the people that are, like, literally right beside you, right? And it's like, what could I do to better support you? Or can I remove roadblocks for you? They're small things, but I would say that I learn a lot through my team, and I'm really appreciative of that because it helps me to level up. So, for sure, that's another area I would say.

Leah 40:47

That makes me think of the conversation we had in the pre-interview about intergenerational teams. It must be really interesting to have people of all different generations giving you that feedback, for example, or reflecting on the business and its growth and trajectory.

Chantelle 41:03

Yeah, absolutely, yeah. I know I said that I was really intimidated by hiring people that are older and more experienced than me, but I've learned to become less intimidated by that, thankfully. Yes. So, yeah, our age range is like 24 to 63 now, and it's it's really exciting because I'm the youngest person on our leadership team, and I am very fortunate. My leadership team is absolutely fantastic. They're so supportive and so willing to share what they've learned and to be supportive. And there's been moments like I went to one person on our leadership team and I said, I don't even know, how do I do strategic planning? Yeah, and she's been in leadership teams and other organizations larger than mine, and so why not ask her, right? Like, what do you think and like? So, I feel like through hiring people, I've gained a community, but also, I've gained people that can offer their expertise and their insights that have really been helpful to Tiller. And so I think the mix of different generations and different ideas and different experiences is really powerful, especially when everyone's pulling in the same direction. Because then it's not about who's better, whose ideas better. It's really about the sharing and finding the right path. And again, that's why we're all big about no ego in our culture. So, yeah, intergenerational teams are powerful.

Leah 42:22

Yeah, that's cool. You've talked a little bit about impact already in this conversation, but I want to be intentional about this question because at Thin Air Labs, we're very intentional about creating meaningful human impact, and I know that's really important to you, so let's just talk a little bit about what impact means to you and at Tiller.

Chantelle 42:37

Sure. So, at Tiller, as a company and as an agency, I have huge empathy for Founders. Like I have a huge amount of empathy. So, I get really excited like we work with all these Founders and these marketers, and I just have so much empathy for the challenge that there is in founding and scaling a company. And so I think, like the idea of building an agency Tiller that actually helps those B2B SaaS Founders overcome some of those challenges on the path to realizing their goals is really just fulfilling work. So, I think that our hope is to be part of really helping to accelerate the tech ecosystem but also our individual client success and that looks different for each client, right? We have some clients that are trying to get to first revenue. We have some that are trying to get from Series A to Series B raise. We have some that are growing through M&A activity, and that's what's going on for them. And so they have specific goals, revenue goals. There's different goals that each and every one of them have. We really want to help them achieve that and be able to demonstrate measurable impact. So, that's like a very client centric piece to it. And then I think, as an agency, we also have been involved in various nonprofit and community-related initiatives. The one most near and dear to my heart is Lemonade Day. It's a program based out of Houston, and it's active in 90 communities, 1.5 million kids have been part of this program before, but I came across a few years ago because I was Googling, like, different community initiatives that we could be part of that would just really align with Tiller and some of my personal passions. And so I came across Lemonade Day, started in Houston, and it's basically a program that you can bring to your community, and it's the concept is that a whole bunch of kids on the same day every year will host lemonade stands all over the city. But leading up to that, they get access to a curriculum that helps them build a little business plan. And it's so cute, so amazing. So, it helps them with setting goals. And when it comes to money related goals. They're asked to set, spend, share and save goals. So, it also promotes kids giving back to the community at a young age, which I love. And it teaches financial literacy. It teaches branding. So, we ran the program in 2023 for the first time. We brought the program here. We ran it. It was a great success. It was great. We learned a lot because it was the first time, yeah, and there's, of course, challenges with bringing the program here. We had over 160 kids participate, which was awesome. This year, we were able to apply all of our learnings and do things a little bit differently. And we had over 360 kids participate this time around.

Leah 45:14

360 kids?

Chantelle 45:16

Yeah, it was a crazy day. That was July 20th, and we had all of our like taste testers running around the city, buying lemonade from kids. And then we basically host a Young Entrepreneur of the Year Award Competition and a best branding competition. And so then, after the program, the kids submit their business results. They submit revenue, profit, they talk about what they learned through the experience. What would they do differently next time? How do they want to give back to the community? And they share all this. And then we essentially go through a judging process and find our winners. And then this year we did like a live sort of stream award ceremony for all of the kids, and it's just the best. For me, my dad introduced me to like, entrepreneurship when I was eight. My sister and I were selling soda on the golf course in Louisiana when we lived there. And so I didn't know it at the time, but it ended up helping expose me to something that I didn't really know I was going to fall in love with later in life. And so I think just the idea of introducing the next generation of kids to entrepreneurship is just really exciting to me. So, we hope to keep growing the program over the coming years.

Leah 46:26

I love it. Lemonade day. Yeah, go for it. Wonderful. As we start to wrap up this conversation, I ask everybody the same two questions, and so we'll do that with you. You're the Founder of Tiller. You're writing the story for Tiller. How do you hope the story for Tiller goes?

Chantelle 46:40

That's a great question. I have many iterations. We actually just had a leadership huddle last week, and we were talking a lot about this. What we're really excited about in the next 5 to 10 years is we really want to expand our service offering and get a little bit closer to the customer acquisition piece of marketing. So, we have a lot of services that are closely connected to that, but we've made the decision to expand our capabilities and our services to get a little bit closer to the acquisition piece, so that's driving the qualified traffic and helping convert the buyers on the website or through landing pages, and we think that that's going to better help solve some of our client's problems. So, we're excited about that. But I think thinking big picture that's just one step towards the big picture. We're trying to build a world-class level agency that serves B2B SaaS, and our focus right now is North America, and we really want to work hard to own that space and to raise the bar for agencies in that space and to sort of help imagine the agency of the future. So, that's really what we're after. We really want to scale this thing and really set the bar high for what those agencies look like. So.

Leah 47:46

That sounds very exciting.

Chantelle 47:48

Yeah, very excited about that.

Leah 47:50

Okay, and then as a Founder, you're the Founder of this company, how do you hope your own personal story goes?

Chantelle 47:58

Well, I have lots of, like, personal goals that I would like to achieve. And I think in the Tiller context, I really want to grow to be the CEO that Tiller needs. And I want to start to, like, live in the space of I need to be the CEO that Tiller needs 24 months from now, like, now, right? Like, you always have to be ahead. You kind of have to be ahead of the organization. So, you can create this, like, healthy tension that pulls the company forward. I'm really working on that, like, public speaking is like a simple thing, like, I need to get really good at that, and even networking. I mean, I'm more of a behind the scenes type Founder CEO, but I know that what Tiller needs is for me to have a stronger presence in the community. And so I think there's opportunities for me to actually overcome some of my own fears and get a little bit uncomfortable and practice building those skills that I think will be really helpful to growing Tiller and our presence in this market and others. So, I think that's a really important piece. Long term, I would love to be an angel investor one day. I would love to do some investing. I would love to just get really involved in the tech ecosystem and in a bigger way. So, I've dabbled in some of that a little bit, but that's sort of a future aspiration.

Leah 49:08

Wow, that's so exciting. I'm so excited for you and for you and for Tiller. Chantelle, thank you so much for this conversation.

Chantelle 49:14

Thank you for having me.

Leah 49:24

As the lead investor in Thin Air Labs - Fund One, Sandstone Asset Management believes in building the comments through innovative founders who are creating meaningful, positive impact, both locally and globally. Sandstone is doing just that by backing the next generation of emerging entrepreneurs. Picture this, a founder start-up goes from idea to international impact supported by strategic investors who believed in their vision. That's the power of Sandstone's approach. Sandstone doesn't just manage wealth, they cultivate it, supporting founders at all stages. Visit Wealth Management | Investment Expertise | SANDSTONE Asset Management to learn how sandstone builds legacies that last.

Leah 50:09

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