Humanizing Your Brand with Kirby Winfield

I think the first order of business was just thinking, well, how am I going to conduct myself? Or how are we going to like prosecute our go to market?

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 Peterson, brand strategist, author of Forging an Ironclad Brand and host of the North Star Leaders Podcast. Let's get to it. Today I am thrilled to be joined by Kirby Winfield. Kirby has been CEO of multiple venture backed companies including Ad, Expose and Dwellable, which is how I know Kirby. Kirby is now a venture capitalist himself, currently the founding general partner at Ascend. Kirby, welcome to the show.

It's so good to see you. Thank you for having me. I'm stoked to catch up. It's been too long.

Me too. Okay, so to start us off, Kirby, we. What is your favorite thing about what you do?

Oh, it's gotta be talking to founders every single day. You know, it's either founders that I've never met, who I may or may not invest in, but from whom I'm always learning. I just think my job is to basically learn like eight cool new things every day.

Ooh, I like that.

Which is crazy. So, you know, if I get nothing else out of it now I know something that I never would have known. And then. And founders, existing founders in the portfolio of. There are dozens and dozens now who I get to check in with who've become, you know, good friends in a lot of cases and, and who are out there actively in the arena, as they say.

Yeah.

Pursuing their dreams and pursuing success. And we've got a little, little skin in the game with each of those people. And so every conversation is like, it's funny. I haven't really thought about it this way, but it's sort of like, I don't know if you probably experienced the joys of being a sports parent.

Totally. Yeah.

Or a theater parent, or a music parent, or a ballet parent. And whatever it is, you've got a little investment in those people out there who are doing the thing. And not to infantilize founders because they're all more mature than I am for what they're doing, but there is a little bit of that sort of. Okay. I'VE got dog in the fight and you want to check in and see how the fight's going. That's pretty exciting. So those are my favorite conversations always with founders.

I love it. There's such an act of vulnerability to being a founder. And like, they are in the arena, they are doing something really challenging with their heart right out there. And it feels like such an honor to be in conversation with them because they're doing something really brave.

Yeah. I mean, having tried to do it myself a couple of times, it gives me an extra level of empathy for what folks are going through, which I think hopefully is helpful and unique. Us as an investor.

Yeah. You've been there. You know what it's like when there's like blood all over the floor around you in the arena. And you know that feeling.

Mostly my blood.

Sure. Right. I have heard you talk about AI and in a way that I have found very refreshing and very grounding. So you've said, and I'm going to quote this because only Kirby could put it this way. You said AI is just a technology applied to problems that people have to solve. Nobody cares about your AI. They care about the problem that you're solving and are you doing it 10x better? Same as it ever was. So talk to me about the importance, importance of keeping your eye on the problem instead of the product, or in this case, on the AI.

It's funny because this is always a challenge for founders and always has been. And the challenge is this. Usually if we're investing, certainly always very talented builders. They're very talented makers of things. What do makers of things want to do? They want to make the thing. And they take a lot of pride in the artistry with which they are building the software, building the product. But the first principles thinking for startups needs to be, what is the problem? It's a problem driven process. And then you make and you build and you form a solution to the problem. And it seems simple, but people that start the journey with a solution already in mind are going to struggle. And to me, the concept of AI as a thing to do versus AI as a tool to use, that's where I think it gets tricky. And frankly, it's kind of frustrating to see a lot of really talented people sort of saying, well, this is the thing that I did at this company with AI and so I know how to do it and I think other people will want me to do it, so I'm going to do it versus, like, well, there's this massive problem that I see in the industry that I'm in, that wasn't even solvable, you know, two years ago because of the lack of, you know, affordability or availability of generative AI. And so now we can solve that. And here's why I'm the right person to do it. So that's kind of what, I guess what I mean when I say it's.

Just a tool, it's sort of a trick of the mind, right? Because, of course, like, as human beings, the thing that we're closest to, especially if it's something that we've created, we have so much pride in that thing, the thing that we're making with our bare hands, we care about it so much. So it's such a trick of the mind to be like, actually, it's not about that thing that you're so proud of. That thing that you're so proud of is merely a means to a solution. And the customer doesn't care about the thing that you're proud of. They care about the thing that is their reward because of your thing. You're right. It doesn't seem like it would be worlds away from each other, but in the marketplace, it is.

Yeah. And I think you probably know this as a branding expert and a marketing guru, like, the worst thing you can do is walk in and talk about your technology to a buyer. Two startups ago, I remember this, we'd come in, we'd say, we've got this big data solution, and they're like, what, okay, what does it do? And what is the benefit to my business? And benefits over features. But it's very hard when you are so deeply involved in the product, to kind of pull yourself out of it and realize what someone else needs to understand is how it changes their life, not where the pixels are.

Right. I think the phrase is the curse of knowledge, that sometimes when you're really close to something, the closer you are to it, the harder it is to relate to the you that isn't close to it. So it's like, you know, you could take this with any subject in life and something that you have a lot of knowledge. The more knowledge you have about it, the more difficult it is to make it as simple as somebody who's never heard of it needs it to be. It's a funny paradox and a talent when people can do that.

I struggle with it mightily, but again, that's why it's best left to founders these days.

Well, it's human. We all do it. We all do it. And I just love that you put A bright light on it so that you can be aware of it. There's nothing to be embarrassed about. If you should be proud of your product, it's not about the eschewing the amazingness of it. It's about not having the spotlight on that because those features and that product are enabling something really important. It's just keep the spotlight on that thing rather than on the reason behind that thing.

That's right. It's like when I'm. I have to remember this when I'm raising money from LPs and investors in the fund, they maybe don't care so much about really how many fancy startups we invest in. They probably care a lot about how much money we're going to make them. And I think you can be. You can get caught up as a manager in our business in, you know, building your brand and making sure that you're out there and getting the most deal flow and having the best reputation and being authentic and doing the things that we try to do because really, at the end of the day, our customer is the founder and that is what is going to make everyone successful. However, you go speak with people who are limited partners, potentially limited partners in the fund who are going to give me money to deploy into these startups. They are less interested in our marketing machine, except for in as much as it feeds into something that's going to create outsized returns for them. And so whether you're a founder, whether you're in sales, whether you're at a nonprofit, or whether you're a GP of a venture fund, I think that's always the challenge is going into these conversations and understanding how are they looking at you when you walk in? Are you steak? Are you dessert? Are you.

And knowing. And just because they're human beings again, all of us do this. They care about what's in it for them, just like I care about what's in it for me. All of us have an orientation around that. And just having a respect and sort of an acknowledgement that it might be different from your orientation can be really powerful. And it's. You're right. It's the same whether you're marketing your fund or a piece of AI or a bottle of bleach. In my case, nobody ever wants to hear about the contents of bleach. But I could talk for a really long time about the 6% sodium hypochlorite mixed with water and the bonds. I could if you wanted me to, but nobody ever has wanted me to, so it's enough. Just to say it's going to whiten your whites and it's going to disinfect your clothes.

I think you need both though, right? When you were running these brands, like how did you build the story and then support it without sort of getting into the weeds?

So a couple of things that in consumer packaged goods, first of all, our products are kind of boring. You know, if you just look at the thing that's inside the bottle, it's 6% sodium hypochlorite, 94%. It's not as jazzy as the latest AI. So it's easy to be really humble about how your product is really nothing to your customer. They care about the thing they get as a result of your product. It's easier in some ways. And then the other thing is these are very mature categories. People don't need to know about the features of bleach because they already understand what it does. Right. So it's not as tempting to educate them in a lot of ways. I do think that that makes it sometimes easier to think about benefits instead of features. But the other thing is that in a category like consumer packaged goods, we have, and maybe this is part of being a mature category that we have the funny situation where all of our competitors are really, really good at brand. Why? Because you have to be. Why? Because it's your only source of differentiation. So you can't talk about your features. In a category where people are too smart to talk about their features, you would get pummeled if you talked about your features. And that's why such world class branding happens in consumer packaged goods because that's their source of differentiation. So they have to be. Otherwise they wouldn't survive as a business. So in some ways it's fun to talk about the stylized example of a consumer packaged goods and take it to technology or like a whiz bang. It is kind of a neat because yeah, you would never want to hear about the bonds between the sodium and the chloride and the bleach. Just like nobody ever wants to talk about the AI. They want to talk about their company is going to save all this money because of it. Or they're going to talk about how they were able to look really good in front of their boss or all of these things that are very human. I love it.

I actually wanted to ask you another question.

I'm the one who does the asking here. Mr.

I got one more.

Okay.

Because we're talking about venture capital and we're talking about brand. You know, you've worked on some venture Capital brands and professional curiosity for me, maybe. But how did you apply sort of consumer grade brand strategy to something that is in a lot of cases, you know, more of a business to business value proposition? Although for me, frankly, I'm raising money from individuals and so it's a lot of actually maybe it's just really high end consumer marketing.

Yeah, well, I think that this is it. Here's the secret. If you're selling to human beings, it doesn't matter whether it's B2B, B2C, B2B2C, marketplace, venture capital, it doesn't matter what category it is, because at the end of the day, human beings have human drives. So it's a false dichotomy. So, so how do I build a brand strategy for a venture capital firm? The exact same way I build a brand strategy for anything that serves humans. What's the unmet need or in your language, the problem that needs to be solved? What's it like to be the person who's experiencing that problem, like on a brainstem level, what happens with them? What are the feelings that come up? What are the rational and emotional things that come up? All of that is rich raw material for building your brand strategy. And it doesn't matter whether it's marketing to a soccer mom who's buying soccer balls or whether it's the head of procurement for a utility who's buying gas. Those are still human beings. I think the secret is in recognizing that it's a false dichotomy. You're marketing to humans.

Yeah, that's really helpful. I'm taking notes.

Good. Okay, here's another thing. When I was interviewing you for my book a number of years ago, you were talking about the usefulness of building your brand strategy really deliberately. So you said by not deliberately positioning your brand, you're making your job harder and you're making it less likely that you'll be successful. So it's about that being intentional, that being deliberate, forward leaning, proactive. So talk to me about the usefulness of being more proactive in defining what you're going to stand for. Call it a brand or a mission or values or whatever, your North Star. What is the usefulness of doing that in a really proactive way?

The first thing that comes to mind is just you make time your friend by doing that. And let's say for example, that you're launching a venture capital fund and you want investors and you want founders to have a sense for what that fund is about, what you're about. You might be about all sorts of things. You might be a former founder and you might be a hard charger and you might be a type A personality, but you need to identify something to stand for. You can't stand for everything. And so, and I'm talking about myself, so I'll go out of the third person and just say, like, I decided to be about being me and just being authentic, Which I don't love the term authentic because it's inauthentic to talk about being authentic. But I guess authentically, I wanted founders especially to trust me and to be able to build relationships from day one with them that would allow me to help them and work with them in a way that felt right and felt like I was on the journey with them, supporting them. And so it was kind of a natural thing to expose to the world. But because I kind of made the decision like, I'm going to be me, I'm going to be me. This fun is going to be about myself and how I do things, how I conduct myself. I was then able to use my daily activities in the community and certainly on social media and in the world at large, sort of reach and frequency for the brand that I was trying to build for the fund. And so now, five years in, because people could be Valley Venture Capital funds, could be investors who invested in our fund, who've literally found me on Twitter, could be founders who have found me on Twitter. What I hear over and over is, hey, you know, I just, I really like how you do things like, you're so authentic. Because I decide I'm not going to edit myself from sharing the random rap album that I'm listening to on my morning run every morning. And I'm not going to edit myself from retweeting every Special Olympics tweet I ever see. I'm just going to do what I want to do, which is people always say, be yourself. What they mean is, be yourself. As long as that's going to help. And I think in my case, fortunately, I think it's really helped because what people, especially founders, want from an investor, they want to know that person. They want to understand what they're getting themselves into when they take a check. And a lot of times it's very hard to understand that. And what, are you going to meet with someone for an hour on Zoom and then, you know, get into a eight year relationship with them. But that's what people do. And podcasts are a great medium to get to know people, but also very controlled. So I think back to the question, the Advantage of choosing something to really stand for early is then you can make it compound.

Oh, that's beautiful. Yeah, it's the compounding effect of the same stake in the ground, minute by minute, year after year, accumulating, not diverging. And one day I'm like this and another day I'm like that. So that would forego the compound effect, but it would also breed distrust. Right, Right. You build trust with consistency. So you can't be consistent unless you decide what you're going to be consistent about.

I mean, and it's funny because once in a blue moon, I get so pissed off about something that I'll tweet about it. And I very mindful of almost always, I keep it positive. Nobody needs to hear anyone complain. Like, I hate, like, powerful people who complain about customer service at American Airlines. Who cares? Like, go cry at a beer. Like, it just bothers me. So I try not to be that guy. And I try to stay apolitical in terms of. I weigh in on specific things I care about, but I don't think anyone needs to hear my opinion on the presidential election. So I consistently don't do that. And when I have, I go, ah, shit. Because not only is it kind of just distasteful to me, it's also off brand. So that's the challenge when you say, okay, well, I'm the brand, the brand is me. You know, you must have this brand. Ironclad is you got to ride for the brand. And so sometimes that means keeping a lid on it.

You're right. Like, there's a. There's sort of like these intersecting circles. I picture a Venn diagram between, like, company branding and personal branding. A phrase that I don't like, by the way. But when there's overlap. In your case, there's overlap. In my case, there's overlap, too, where the brand of the firm is very highly overlapped with the person who runs the firm. And to be deliberate in advance about what you're going to do and not do. And I don't talk about my kids, for example. I don't even know if I could explain why, but I just don't. And I just don't go. And if I ever did, I would probably feel a little bit weird about it for the same reason as you. So having those guard, it gives you the compound effect of being consistent over time with the same thing, but it also saves you time and emotional energy in the minute when you don't have to adjudicate. Am I going to talk about politics? Yes. Or no. No. The answer is no. I already decided that.

Right. We have brand guidelines.

We have brand guidelines that say, no talk of presidential politics, and then it's just not a thing. And then this is like the power of focus with anything. You have energy for other things because you're not spending time trying to figure out whether you're going to talk about presidential pulse. All that time and energy can go into something that is on brand and that does feel good and energy begetting for you.

Yeah, I actually do try to apply it at home as well, actually, as it turns out. Like, I just really try to focus on things I can control and not bring more. More input into my life than I need. You know, from external. I mean, you know, when you're on Twitter all day, sporadically, all day, it doesn't help.

Yeah. I think I hear you saying too, that in a way, it's a special privilege to be like you and me, where you're actually defining your business and your personal boundaries. There's high overlap there. Because then you can say, this is me when I'm at my best, which is actually almost the definition of what a brand is for a company. Right. This is us at our best.

Right.

And so if you say, well, this is me at my best and I'm going to apply it in a professional and a personal setting, then you're just giving yourself the clarity of this is what I'm optimizing for. This is what I have already decided is important to me so I don't have to think about it. It's guardrails.

Yeah, yeah, yeah. That's a really helpful conception.

When do you think is the best time for a company to define what you're going to stand for? Is it early stage startup? Is it when you are past the Series A? What do you think?

That's really hard. I mean, I think we've talked about this in the past. Brand's going to happen. You can control it or you can not control it.

Right. Brand or position or be positioned. Yeah.

And so there's something to carving out a space early on. Maybe it's more ephemeral. It's almost values. It's almost more like, what do we stand for? Yeah, I mean, we're having this discussion internally right now. Like, what do we stand for? I think it's authenticity. What's the thing that we deliver to founders? I think it's trust, actually. I think that's actually the thing we deliver. I think that's the thing. And authenticity is the brand value. That supports that. Right. But I don't think I knew that five years ago. But I think the first order of business was just thinking, well, how am I going to conduct myself? Or how are we going to like prosecute our go to market and what do we care about when, when we do that? And I think I did ask myself those questions. Most founders just innately know. Yes, but they don't always codify it. We made a decision, I mean, I keep talking about me because it's just the most recent experience, but we made a decision about our, our logo before I even raised money. And the decision was to have a more consumer influenced design ethos from a palette perspective, from a font perspective. We particularly didn't want to be another sort of banking, you know.

Yeah, I can picture it.

That works if you've been at it for 30 years. But when you're fresh and new, you got to be fresh and new. Right. I'm not trying to fool anyone. And. And also leans into my. I think maybe it's my personality a little bit. And yeah, with the solo GP fund, it's kind of. It isn't like we just spent time on. It is about me in a big way. So. So I think we made decisions like what does the brand look like? And that was informed by like, well, what's our personality? And we always wanted to conduct ourselves in a way that's like, that is sort of authentic. And you know, very early on got really good tight feedback loops from founders on like, hey, I like how this works. Like, I like that you have a toolkit on your website that you know is completely a mishmash that you clearly just did yourself on Squarespace. But that resonates like, and it makes you approachable and it's sort of like know what direction you're going in.

Yeah, it doesn't have to be high fidelity. In fact, it probably benefits from being low fidelity initially, as long as it should feel true in that moment. But don't go crazy with granularity.

And yeah, I've made that mistake before. I think you can overcook it and then you can lose credibility. You can sort of set yourself up for disillusionment because if you do the hard work and then like, what's the yield? It's sort of like shooting a Super bowl ad and then not having any money left to buy the ad space.

That would suck.

Right. But it's like you do all this work and you think about, about it so hard and then it's just one hand clapping right? Because you aren't at scale yet. And so to your point, like the fidelity and when you bring that to bear really does matter. And I do think that's post series.

A. Yeah, market fit is there.

Yeah. You know, like why people are buying from you and who they are. You don't even really know your audience until the series A.

Well, if you're a heat seeking missile, that would be a really poor time to carve something in stone. So once you have product market fit and you also know yourself better, you've had some time with this and you know the things that are fueling, then by codifying it with some more rigor, you allow for that compound effect to really fly.

I mean, the thing is, it doesn't matter till it matters. So having it right, right before your inflection point is when you want it.

Sometimes you pick the direction early and the stars align and you don't have to change the direction. And it sort of reinforces your point that there are certain inflection points that are more useful than others for this. So that's like, if you're going to get to the point where you're about to start spending meaningful money on marketing, then higher fidelity is better. But before that, it's more debatable. Like how granular to be. Okay, are you ready for some rapid fire questions? One word answers? Ready, Set. Your favorite kind of candy? Reese's Peanut butter cups or pieces.

That's two words.

Oh, touche.

I will say Reese's pieces.

Okay, your favorite form of exercise?

Running.

Are you an introvert or an extrovert?

I'm an extrovert who needs a lot of recovery time.

I feel that. Are you a dog person or a cat person?

Cat person all the way.

No way. I didn't know this about you. Yeah, Kirby's a cat person. But you have a dog.

Oh, no, never. That's the only rule I have with my family that I said that I've held since day one is we will never have a dog. If you want me here, there will be no dog.

So you're not only a cat person, you're a dog hater.

You can have a dog, but I don't want to have your dog with me. So I'm okay with dogs in the abstract. Like, they're. They're great.

They're neat as far away from you. The more far away from you they are, the less you care.

I like seeing them run and jump and swim and all that stuff. It's really cool. Appreciate that people appreciate them. But I am a cat person. I don't like massages. Okay. I don't like being touched. I'm a little bit fussy and cats are my kind of people. Oh, my God.

Okay, I love this. I learned this about you. What is your guilty pleasure these days?

Words with friends. Yeah.

Okay. Awesome. This has been so great, Kirby. Thank you for taking the time. What should I direct my audience to if they want to learn more about Ascend or about you?

If you're on Twitter, it's Irby Winfield. Otherwise, go to Ascend vc.

Awesome. Perfect. Thank you for joining me today.

Thanks for having me. This is a blast.

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