Ironclad Brand Strategy [logo] Ironclad Brand Strategy

North Star Leaders Podcast

Kristen Hamilton

Season 1 Episode 10 12 Dec 2023

Transcript

Kristen Hamilton:

Oftentimes, people who start companies fall in love with their product instead of falling in love with the problem. When I hear that, "We're doing this and here's what it's going to do for people", and so forth, that's great. But back up and start with the problem. What problem do you really care about? And let's spend some time there and make sure that you deeply understand what that problem is. Because if you're early, this is just the first way you're trying to solve it. It will change. By nature, by definition, it will change. It will evolve. That's a living, breathing thing, your solution to the problem. The problem may evolve, but it should be a big problem that you care deeply about.

Lindsay Pedersen:

The world needs what only your business can bring, and as a leader, it's your job to deliver. But where do you focus? Where do you direct your time, your team, your budget, and your emotional energy? We are learning this together on the North Star Leaders Podcast. I'll be talking to purpose-driven leaders about the choices they make to create audacious economic value while also realizing their distinctive purpose. I'm Lindsay Pedersen, brand strategist, author of Forging An Ironclad Brand, and host of the North Star Leaders Podcast. Let's get to it. Today, I am so delighted to be joined by my guest, Kristen Hamilton. Kristen is a multi-time tech founder and CEO as well as a board director. She was co-founder and CEO of Koru until Koru was acquired in 2019, which is how I know Kristen. And she is currently a general manager with Enjoy The Work, which teaches great founders to become great CEOs. Kristen, welcome to the show.

Kristen Hamilton:

I always love spending time with you, Lindsay. You know this. So I'm so happy to be here.

Lindsay Pedersen:

I love spending time with you too. This is such a treat for me. Okay, so to kick us off, what I want to ask you is what is your favorite thing about what you get to do?

Kristen Hamilton:

Well, there are many favorite things about what I get to do. The reason I'm doing the work I do with founders is because I love starting companies. I love the company starting process myself, the invention of it, the creativity of it. And now I get to do that by supporting other people through real deep connection with them personally. So I know that's two things, but it's really about the impact that that drives. I get to have this impact on the world by supporting founders on their journeys. And to me, that level of connection is a real privilege that I get to spend time with people who are doing such hard things and helping them achieve their objectives and their goals and their dreams. It just really feeds my soul and it brings me so much energy. And I'm super grateful. I feel privileged to be able to do this work. And it feels like a calling, which is wild to say, but it really does feel like I found my purpose at this phase of my life.

Lindsay Pedersen:

I feel it. I know you. We've known each other for a long time, so to me it's not at all surprising that it feels like a calling for you to be a support system and an advisor to people who are in the trenches. Because you've been in the trenches and you yourself have a lot of skill, but also a lot of empathy. So it makes so much sense to me that that brings you joy. And listeners can't see you right now, but I can see you and you're very lit up talking about it. Now that you're not in the trenches, you're supporting people in the trenches, you have this distance from it. What have you been surprised by, now that you're on the other side? The contrast between CEO advisor and CEO. What has been really surprising to you now having seen both?

Kristen Hamilton:

One of the surprises or acknowledgements is that I know some things. Like yes, someone put in a chat on a workshop I was giving online like, "You've seen some (beep) with the (beep) emoji." I bring that up because when I was a founder, I was on constant steep learning curves. I had to get really good at a lot of things very quickly. Like you're raising money, you've never done it before. You need to be an expert. Go. You're selling enterprise customers with a brand new product. You've never done it before. You need to be great at it. Go. Because I was constantly climbing those steep learning curves, I really was in a state of mind that I'm constant learning, which is great, but also that, "Gosh, I'm not an expert at anything." I'm constantly having to make it up as I go, hack it together. And there's some feeling of terror in that.

And I think what's been fun in this role now as an advisor is both holding the idea that I'm a lifelong learner and I will constantly be learning. I learn from the founders I work with. And on the other side, I do feel in a place where I can be really helpful to them because I know some things. It turns out that after 25 plus years of building and running companies and helping my friends when they're in the muck and them helping me, and going through eight rounds of funding and therefore, hundreds of pitches and going through the agony of defeat and the joy of some victories here and there, that I've learned some things and I can really help other people. So I guess maybe I tell people that and they say, "But of course." But when you're living inside that state of constant learning, it's easy to the fact that I've accumulated some knowledge and I can be really helpful. That's been good for me. I think it's been really good, to say I have genuine confidence around some of these things now, which feels great.

Lindsay Pedersen:

Absolutely. I get this sense of the pain and agony of those steep learning curves and the days that are hard days. It's almost like now you get to amortize that pain across so much more. It's so much more worth it. You get so much more bang for your buck from those lessons because you get to impart them to other people who you have a lot of heart for.

Kristen Hamilton:

So true. And I tell stories a lot now. They'll come to me. When I'm talking with a company, particularly a CEO, and they're talking about a story and what's going on for them right now, I come from a place of listening and deep empathy. And then I'll say, "Well, here's something that happened for me and here's what I did and here's what I learned." And it feels really good to share, especially the hard things. Because people look at your resume and your background and say, "Oh, you've had exits, an IPO, and things like that," and they think it was easy or there was all up into the right, which of course it never is. And those lessons, the painful lessons where I was really learning the hard things, those are the things that are most useful frankly. And I think it really gives people a sense of comfort because it is such a lonely job.

Lindsay Pedersen:

Yes.

Kristen Hamilton:

It's such a lonely job and it's so brutal and you can't really be directly open with your investors and your board and your employees for all the reasons that I really appreciate. When I have a connection with a founder and they're willing to be really vulnerable with me, then we can do the real work. It's such a privilege to be in that place, to be able to receive people's openness and vulnerabilities. And then we can teach them and people are open to learning and being real.

Lindsay Pedersen:

Yeah. You mentioned stories. It makes me think of the idea of a North Star for a company or for an organization or for a team, and you've led a number of companies. And I know you had a North Star at Koru. Have you always, whether it's a brand strategy or a mission statement or a purpose statement or vision and values, has that always been a tool that you've used as a lead1? Or is that something that you developed while at ... Was Koru the first time that you really leveraged that?

Kristen Hamilton:

That's a really interesting question. I say that the first company that I co-founded was an eCommerce business, and we took advantage of a wave I think. We weren't so much saying, "Here's a real problem in the world. Let's solve it." It was a little bit like, "Wow, people are buying things online. Let's sell them things." And that can work when you're in the midst of a major revolution, which was like eCommerce was just getting started. However, the most effective way to start companies and to build lasting durable companies is to deeply sink into a problem and pain that you're desperately put on this earth to solve that you care so much about. And so that, plus I think for me personally had experience in the middle of my career, which is around education and international development, ever since then, I was really impact oriented and wanted to make a positive change.

I always had that in me, but with my businesses, really they became impact oriented. So the North Star around Koru was really around there is this terribly wrong thing in the world, which is people who are graduating from college can't get jobs that are essentially well paying. They were unemployed or underemployed. And so that was just this huge problem and the employers not being able to find talent that had the skills. It was really around that, and our North Star came out of that. It really came out of how can we create opportunity for people who are capable of doing things? There's a mismatch. And so that North Star really inspired our team and it inspired our customers. It inspired our enterprise customers like Citibank, saying, "Yes, actually we are doing this thing called insanity over and over again and hiring people based on the wrong signals, which we know in our intuition are not right."

We proved it with data. Because really, the grit over grades revolution was one of the ways we instantiated that mission in simple terms. Like hire people for grit instead of grades, and actually you'll have better performance. And for people who didn't have the opportunity to go to school in a way that was supported so they could get grades but had three jobs during school for instance, for them, it was very inspiring to be recognized. To say, "Yeah, I have that thing. I have that thing called grit, or I have that thing called curiosity." Anyway, that was really a big part of how we built the company and how we led the team.

Lindsay Pedersen:

Yeah, I love this idea of all of the stakeholders across, whether it's investors or employees or managers or leaders or customers, that it makes them feel seen when there is this problem solution, this really satisfying matching of, "We, this company, deserve to exist because we're able to solve this problem and that's our rally and cry." And that in turn makes the customer feel seen and heard because they recognize themselves in that problem, because you've taken the time and the energy to get really sharp about what that problem is. And you care about it. You can't fake that. It's so deeply human to have that sense of, "This is my problem," or, "We're a company who is around in order to solve this problem." It is visceral for the customer and it feels like a gift. They see me.

Kristen Hamilton:

Yeah. A way in which that [inaudible 00:12:08] with framework to pull that into strategy from mission was a lot around the help you gave us around, where's the deep unmet need of the customer? Really understanding that and then constantly doing discovery, never ending discovery, customer discovery. Where's the unmet need? And then where are we strong to be able to meet that unmet need? And then where is there space in the market where our competitors are not strong? So that helped us go from this aspiration to, what's a strategy that will help us achieve that? And that was huge. The discipline around the positioning that we did I think made it even more inspiring to customers because they're like, "Yes, that is my pain. You are speaking my language." And that was another really important factor for us to take. Here's the market need. Turn it into a strategy based on those principles.

Lindsay Pedersen:

I'm fascinated right now with the relationship between that very lofty mission, vision, values, people call it different things. Sometimes it's really amorphous, but it's very big. It's always a big thing. And the brand strategy, which done well, enables that mission. Its purpose is to enable that mission, but it does exist at a more grounded level. It's like the strategy. It's like, "Well, how are we going to make that mission come true?" But I am interested in the interaction because different things speak to different people. Some people really like to think of their purpose and their mission at a very lofty level. And that's wonderful. There's also more like maybe an even lower level would be product strategy. Like what are we going to really nail at the product level?

I'm really interested in connecting the dots between those and also just letting people know that there is a way to connect the dots between those two things, that it doesn't have to be all amorphous or pie in the sky, and it also doesn't have to be all hard, factual product attributes. So I love hearing the way that you think about that. We started Koru because we were desperately trying to solve this problem for the world. And then it came down to, "Okay, what's Koru right to play in this space?" Like what's the specific way Koru shows up for that? What is the best moment in the journey to define that? Is there a better time? Is it always a good time to be defining the North Star? Is it better to do it early or is it better to do it later once you have more market traction?

Kristen Hamilton:

I say in this talk that I gave recently that it's important in a company that's going to be venture funded to have an audacious game-changing vision and a very solid business model underneath it, and both of those things. So how are you going to change the world? How's the world different after you do your thing? And then how are you going to execute on that? Sometimes, people dive in with like, "Oh, we're going to have all this data and people are going to be able to use this data to completely transform how they do their business. They're going to have dashboards and so forth." That's all well and fine, but usually it starts with solving a pain in a really pragmatic, practical way. The interplay between those two things is really important all the time. It's really easy to make the simple complex, but it's hard to make the complex simple.

So you're talking about that. It's great you have this audacious vision and so forth. But practically what are you going to do? There's two ways I'd answer the question specifically. You need to be constantly seeking the truth around product market fit by always listening to customers for surprises and doing customer discovery in every sales meeting. Because product market fit is hard to achieve and also can be elusive because the market shifts. It'd be great from day one if you had this North Star metric like the North Star around what it is that we're trying to achieve in the world, and you had the clarity around, "This is exactly how we're going to offer our product or service." However, you're constantly developing that. You're constantly learning how the pain is lived by your customer and how you can best solve that, and you're constantly adapting. So sometimes, people think you do customer discovery at the beginning and then you're done. You figured out that process, then you figured out what to do and you're finished. But you're constantly having to iterate on that. So the time to do that is always.

Lindsay Pedersen:

I love that. It reminds me of just the idea of a friendship or a relationship where you don't just listen when you're meeting. You're always listening, you're always in communication, whether literally or figuratively. You don't stop listening to them once you've said, "Oh, yeah, now we're friends." That would be weird.

Kristen Hamilton:

Yeah, it's empathy, right? And customer empathy is core. Being a curious person is a superpower of founders, and then having empathy in there for what must that be like for you. And it's challenging because I was talking to a founder this week who said, "I know I need to do some more work with the economic buyer. I've been really focused on the user. But I'm afraid to do it because I'm afraid to ask the questions because of what I might hear." And that's normal. It's normal because it's daunting. Like, "We built this thing. What if I hear something that makes me realize that it's not what they want?" Well, the sooner you hear that, the better. She was really honest. I appreciated that, that she could be so forthright about that and say that out loud. But I think people, that's going on for them inside and they don't say it. So you've got to ask the questions and listen to the hard things and not ask questions to confirm your bias, but rather really look for what's going on for a user or a buyer emotionally and viscerally and try to understand it.

Lindsay Pedersen:

It struck me when you just said, "And that's normal." I just got this sense of what a vulnerable act it is to be a founder, to be a leader. Because you're creating this thing that you care about and then you're putting it out there asking people whether your baby's ugly. And you're expected to be glad if they say yes. It's such an act of courage. If it's going to be successful, it seems like that's like a necessary ingredient, and it's not for the faint of heart. Not everybody should do this or not everybody is going to enjoy that in the long run.

I feel like what is helpful for leaders that I talk to is coming back to first principles, coming back to, "Well, why are we doing this? What's our why?" You might say, "What's the thing that inspired this to begin with?" And that creates some of that courage, some of that willingness to be vulnerable. But I also wonder if you experience resistance from the CEOs that you advise to put that stake in the ground. Like, "This is what we're going to stand for. This is our North Star." Or do people embrace that as a tool that's going to help them? What do you find among the founders that you advise when it comes to this?

Kristen Hamilton:

Founders tend not to resist big ideas and the willingness to be bold. I had noticed a few things. Oftentimes, people who start companies fall in love with their product instead of falling in love with the problem. When I hear that, we're doing this and here's what it's going to do for people and so forth, that's great. But back up and start with the problem. What problem do you really care about? And let's spend some time there and make sure that you deeply understand what that problem is. Because if you're early, this is just the first way you're trying to solve it. It will change. By nature, by definition, it will change. It will evolve. That's a living, breathing thing, your solution to the problem. The problem may evolve, but it should be a big problem that you care deeply about. That connects to the why of business.

That's really important in terms of when you're going to talk to an investor who has to squint and see this could be a billion-dollar company one day, you really want to be able to talk about a big problem that is painful to people who have a lot of money to spend on. The other why I think that's so important to founders is their personal why. What is it inside of you that's going to keep you motivated around the very hard job you've just chosen of starting a company? It's a lonely and very challenging experience, and it's not glamorous like some people think. And so what's your own personal why? That's something that I've gotten really clear on the importance of doing that, and also getting clear on why around the work that I'm doing now. So I talked about it in fact that I'm joyful about it. And I spent the last year before deciding what to do next. Really focus on that. What is my why? What matters? What are my priorities? And it evolves throughout our lives. But getting really clear on that is super important.

Lindsay Pedersen:

So it's the first principles, the starting point, the source of inspiration and motivation for the person intersecting with what's the why, what's the reason for being for the company? Because if you're the founder and you're the CEO, you're the one who's probably going to be making the most sacrifices and trade-offs in service of that thing. They don't need to be the same why. But there needs to be a connection or it benefits from having a connection. So that on those hard days or those hard years, that inspiration can come to bear because this is a human being. If you're a leader, you're a human being and you're going to have bad days and you're going to have times when you're bored or when you're uninspired. That's going to harm the company if you haven't defined what's going to be the source for that fuel.

Kristen Hamilton:

And this is really the principle of know thyself. Reiterate, self-awareness is key here, because some people know that about themselves. And there are really cool ways of finding this out. There are some pretty amazing assessments you can do to help you with the self-awareness. The biggest thing you can do is ask for feedback from people who know you and experience you. If you're struggling with, "I'm not really completely clear on what my life themes are, the things I must have, my non-negotiables that are so critical to me, my values, what are they?" But opening up your window of self-awareness can be done by two things. One, asking for feedback and secondly, disclosing things about yourself that others people don't know. Making yourself be known better. That actually helps you know yourself better as well.

And so I really started to geek out on this a lot in the last few years around deepening my self-awareness. And I've done some assessments and I have a group I work with other founders that we meet on a regular basis, and we use some tools. But that helped me get to a place where I realize what are the three most important things for me right now? Which are connection with people, impact, being able to have impact on the world, and three, freedom of movement, which I ignored, denied myself in the past. But it's a really important thing for me. I don't like sitting in one place physically in an office and having a calendar where all day long someone else has control over when I do. And so mixing in the ability to literally get up and move, but also be other places or do the things I need to do to keep myself healthy, which involved mountain biking and skiing for instance, and integrating that into my life and my work.

Whereas in the past, I thought, "Oh, if I want to achieve things, I just have to work hard and suffer." Actually be better if I'm not suffering and I can have them be more productive and I can actually have bigger impact. Anyway, those became my pillars, but that came through a lot of self-awareness. And then I used that filter when I looked at new opportunities for myself and turned down some things that really spoke to my ego, but going to make me happy.

Lindsay Pedersen:

I was going to ask you that because the idea, and especially when you bring it down to pillars like you just did, I love pillars, they become decision-making filters. When you can externalize by making it a word or a pillar or a picture or whatever speaks to you, then it can keep you honest. You can actually use it as you're confronting decisions big and small. Sometimes, it's actually a little decision that becomes really powerful if you can use it according to your pillars to whatever are the correct filters in this case. Do you have examples from being a CEO when you actually said no or said yes to something that you wouldn't have if you hadn't defined and articulated your North Star?

Kristen Hamilton:

Definitely. We had more than the North Star though. We had that and then we had what we call the working theories, which is we would create a point of view based on our strategy and our North Star, and based on what we know about the market. And those, we would document, to say, "These are our working theories about what's true." Customers will not buy if they are under these conditions, for example. Or this is the primary need that we are solving for because of market analysis. And we'd call them working theories because they were true. We would not revisit them on a regular basis unless we got new information. So we would be really formal about changing that working theory. And this was my co-founder, Josh and I, who did this. He labeled them, so I'll give him credit, working theories.

And I really like this idea because you can only have so many moving pieces at once, and there are already enough moving pieces. So you have to get some sort of stability to say, "Okay, well, we know these things to be true as of now." And we do a lot of work to make sure that that is right and true. And then until such time as we have new information that changes what we knew, then we might revisit. "Oh, we're changing that working theory to something new." And that really helped because when making decisions, if there are too many moving pieces, it's very hard to get to a choice where you feel confident and also to get everyone aligned around it, to even disagree and commit. Because people will say, "I don't believe that, the basis of this decision."

This really came into play when I got hired at Guild Education to do a particular job, which was involved really changing the business, and I noticed that everyone was thinking about it differently. So we started to put in place, it took a little while. "Okay, what do we know to be true?", and documenting these working theories. And then it helped us to actually choose not to do that thing which I was hired to do.

Lindsay Pedersen:

Wow.

Kristen Hamilton:

Yeah, it was great. And so I applied that in that situation, and especially coming in as a new person to do this job where people had a lot of strong opinions about things, but it was a little bit inconsistent what people were believing in why. And so that has been an incredibly helpful process to use during decision-making,

Lindsay Pedersen:

I feel like the real value with any decision-making tool is in allowing you to say no. Because it's easy ... There're so many bright shiny objects and there's so many good ideas and there are even so many great ideas. But to have something that filters out all but the absolutely excellent things and everything else gets a no, that's the crucible. That is what really creates a useful North Star or set of mechanisms to guide you as a leader. Because it's easy to have a principle that makes you say yes to things when there's lots of good ideas. What's really helpful is something that allows you to say no to things, that aren't going to get you closer to whatever is the promise that you're on this earth to fulfill. I love that.

Well, starting to wrap up, if you're game, I have some rapid fire questions that I'd throw at you, five of them, and it's just one word answers for each. Are you ready for me?

Kristen Hamilton:

Yeah, I love it. Let's do it.

Lindsay Pedersen:

Okay. What's your favorite kind of candy?

Kristen Hamilton:

Chocolate, dark chocolate.

Lindsay Pedersen:

Any specific brand of dark chocolate?

Kristen Hamilton:

There is one particular brand at the Trader Joe's. I'm forgetting the name of it, but we did a taste test over COVID of every single chocolate bar at Trader Joe's and we landed on this one. It has a little green bean on it. I don't remember the name.

Lindsay Pedersen:

Oh my gosh. That sounds like a good chocolate.

Kristen Hamilton:

Scientifically, my kids and I, we did a whole taste test ladder.

Lindsay Pedersen:

That's my kind of quarantine activity. Okay. Next rapid fire question, would you rather have invisibility or flight?

Kristen Hamilton:

Flight, for sure. I like an adrenaline junkie, so that'd be great, to fly.

Lindsay Pedersen:

What is your favorite sport to participate in?

Kristen Hamilton:

Used to be skiing, and now I can tell you that mountain biking is probably even so. Skiing and mountain biking.

Lindsay Pedersen:

Okay.

Kristen Hamilton:

It's going downhill fast. It's just sometimes there's snow and sometimes there's dirt and rocks.

Lindsay Pedersen:

Okay. We can call that one. Okay, what was your last splurge purchase?

Kristen Hamilton:

Trip to Nepal with my daughter. I mostly spend money on experiences easily, and I don't spend money on things that much because I don't really care for things. Also, I got a new mountain bike, so maybe that one, splurge purchase. But it's because my last mountain bike was stolen, so I got a new one, which was exciting. But it was a must do, so it didn't feel like a splurge. It was just a replacement.

Lindsay Pedersen:

Love it. Okay, and last rapid fire question. What is the most recent song that you've had stuck in your head?

Kristen Hamilton:

The theme to Ted Lasso.

Lindsay Pedersen:

Oh my God, yes.

Kristen Hamilton:

Morning. I couldn't believe it was in my head because I finally finished the last season and I was so sad that it was over. But that song, that is that theme keeps coming in my head, driving me crazy.

Lindsay Pedersen:

Oh, it's so feel good.

Kristen Hamilton:

Warms my heart. That was such an amazing show and such a beautiful thing to have a show that's about leadership lessons coming from a place of positivity.

Lindsay Pedersen:

Yeah.

Kristen Hamilton:

The world really needed that and still needs it.

Lindsay Pedersen:

I know. It's a show about kindness. I loved it. Well, Kristen, this has been such a joy. Thank you so much for joining me for this conversation and for sharing about yourself and your experiences. Thank you. For folks who are listening and they want to learn more about you, follow you on social media, where should they go?

Kristen Hamilton:

LinkedIn, for sure. Kristen Hamilton, and check out enjoythework.com as well. That'll teach you a little bit about how my partners and I support founders and the work that we do. There's a bunch of good blog content there as well that I think is really high quality.

Lindsay Pedersen:

Awesome, and we'll include that in the show notes as well. Enjoy The Work. Perfect. Thank you so much for joining me. Have a wonderful rest of your day.

Kristen Hamilton:

You too. Thanks, Lindsay.

Lindsay Pedersen:

Thanks for listening to this episode of North Star Leaders. Make sure you don't miss an episode by subscribing on your favorite podcast app. For show notes, transcripts and newsletter signup, visit ironcladbrandstrategy.com. Please join us again for another episode of North Star Leaders.

Lindsay speaking

About Lindsay

Lindsay Pedersen is a bestselling author and brand strategist with a scientific, growth-oriented approach to brand building. She has advised companies from burgeoning startups to national corporations, including Zulily, Starbucks, T-Mobile, Coinstar, and IMDb.

Her background as a P&L owner at Clorox fostered in Lindsay a deep appreciation for the executive’s charge: increasing the company’s value. There, she led mature, billion-dollar businesses and newly-launched categories, from Clorox Bleach to Armor All to Brita. In each case, she was solely responsible for increasing the business’s value.

Thanks to this executive perspective, Lindsay demands that brands be hard-working, disciplined and rigorous in growing a business. Her brand strategies are tested in the crucible of her proprietary Ironclad Method. Lindsay arms leaders with an empowering understanding of brand, and an ironclad brand strategy to guide choices as they grow.