Struggle Bus with Dave Finnegan

board. I'm going to count myself in, then I'm going to give my standard intro, and then we can go from there. But I'm going to count to 5 in my head, then I'm going to intro us and go from there. Welcome to the Struggle Bus VSpot Show, the home of the e-commerce and early news. I am Vinny O Brien, or as my friends love to call me, hey you in the bushes. With me today is Dave Finnegan, or Finn as his friends love to call him. He is the Ross Geller of the e-commerce world. He is an operating partner of Blackfin, a PE firm helping brands create momentum that lasts. He holds many advisory roles, including ones with the NRF, the Retail AI Council, and is a keen member of the Explorers Club based out of New York, but one of 34 chapters around the world. He's also studying anthropology, a master's in anthropology at Harvard right now, going up to 2028. Dave, Fin, welcome to the Struggle Bus.

Thank you, my friend. It's great to be with you. It's good to have Finny and Vinny together.

It's, well, I don't even know if there's a word for it. Like, it's like a palindrome, but it's not quite there. But I want to make you smile today because you do so much for our community. So I'm going to try and open up with something that might make you smile and hear your thoughts. I said in the pre-call conversation that I listened to, I was reading some Bill Bryson last night. And in order for you to know how special you are, not just to our industry but to the world, I'm going to read something to you and then see what you think. So hear me out. If your two parents hadn't bonded just when they did, possibly to the second, possibly to the nanosecond, you wouldn't be here. And if their parents hadn't bonded in a precisely timely manner, you wouldn't be here either. And if their parents hadn't done likewise, and their parents before them, and so on and so forth. So if you go back to the time of Shakespeare and the Mayflower pilgrims, you've no fewer than 16,384 ancestors earnestly making love in such a way that you would miraculously end up here. If you go back 25 generations, there are no fewer than 35 mil— or 33,554,432 men and women whose devoted couplings your existence Depended upon. How does that make you feel?

I'm super grateful. I'm super, super grateful for the whole thing. For me, my dad is a Montana— you know, he grew up in the mountains of western Montana in a mining town, and my mom is Scottish. And so the ancestry that brings those people together, it's a real miracle. Where we end up, um, over time. So, you know, years ago I was in a meeting with some guys that were at Harvard where they were talking about— one of their colleagues had passed away. He was the guy that started Staples. And one of the things that he said in raising a toast to this guy is, none of us made it here by ourselves. We're all the product of others who got us here. And so these guys may be the smartest— some of the smartest people on the planet. They could all be saying, hey, look how cool we are, look at all the accomplishments. What they talked about was the value of who got them there. And, uh, our ancestors are hugely important. So are the people that we surround ourselves with in the industry and our, you know, our friends and our family is huge, hugely important to realize that we don't do this by ourselves.

You always strike me as somebody who is firmly rooted in your ancestry. How much Montanan and how much Scottish do you feel on a day-to-day basis?

Well, I wore a kilt to enter Aberdeen, so I do have a couple of kilts and I think my dad was kind of a quiet cowboy poet type. My mom was more of a driven Scot who was super entrepreneurial. And I had a handful of aunties as well. So I had no chance. I could get away with nothing. I had like multiple aunties that were raising me and a mom Scot on. I had this really, really strong group of women that, that helped raise me, and I think that helped me a lot.

There's common traits in people I speak to on this podcast, and it's more about the human story rather than maybe our brand backgrounds or the, the companies we work for. It's the work we do and the way that we do it. How, how important or how influential was it having such strong female leadership in your life and role models? Do you think it shaped you dramatically or shaped you differently to how other people think about the world?

That's a good question. I look back and think about the companies that I worked for. You know, I may be working with strong women in my life. If I think about how that has shaped who I've worked with, you know, I worked with Maxine Clark, who started Build-A-Bear, founded Build-A-Bear. Extremely, um, competent, very, very smart, very driven. I can see such similarities in what I was raised with, right? And so, you know, one of my best friends on this planet is Vicki Cantrell. Very strong woman, great perspective, is a real mentor for me. So as I look back on my life, I can see how, you know, having that strong woman influence from my aunties building my own confidence and telling me that I was smart and capable to the women that I actually worked with. All throughout my life, there's a number of women that I can point to that really matched up with what I was raised with. In fact, my ChatGPT voice is a British woman, and that might tell you something.

As long as it's not Nigella Lawson. I always remember when you say that, that scene from Modern Family where Phil is dancing around the kitchen, thinks he's on music, and they pull away the headphones and he's listening to Nigella massaging a turkey breast. Is that who you have on yours?

No, no, no, no. She sounds more hip, more Emma Watson.

No, I, I'd settle for that. That's okay in my world. Um, you get, you get asked loads about the intersection, or at least you get to talk about it a lot, I think. People bring you on as a marketer, but you have this great crossover in human condition and where we are. And the question that kind of inverts that a little bit for me is more, are the tools changing the humans or the user? And if so, how do you view that? Because you always get asked about the tools, but how are we as humans responding to this change and this rate of change?

I do think that the tools change a human. I think that's part of what we do. Or at least they have us think about ourselves in a different way. So I could illustrate with a story. Please do. So I was sitting with, um, uh, Rob Garf. We were just hanging out as friends at the Explorers Club, Fireside Explorers Club. And these young guys were in the other room. They had a robot and it was robotic arms that were sitting on a table. And being curious guys, we, we said, hey, what are you guys working on? What are you doing? There was some conference going on upstairs. These guys were clearly part of that conference, but we wanted to learn from them. These young guys started talking to us about what project they were working on. They were working on the first robot that would be in the space station. It was at a more, you know, it had two arms, it had no torso, it just had two arms. And what we started talking about was the idea that they had learned that they had to make their robot friendly. And I found that very curious. I said, what does that mean? And they said, well, if you think about interacting with humans, if I were to get really close to you and talk to you, or I move too fast or I move too slow, yeah, my likability, this kind of unwritten rule of what we are as humans my likability goes down. And so what they had to think through is what makes us most human that I can reflect in this experience so that as humans we can interact with it in a more meaningful and a more helpful way. And so I feel like that play of, of these new tools are actually teaching us a lot about ourselves as we reflect on what makes us human. So I feel like it's a back and forth.

Where, where do we get the time to do it? Because most people that are at a seniority you're at don't enjoy the time to embed the cultural psychology and mindset that you require to be a modern brand marketer. Because we've gone through this phase of, you know, this hedonistic mantra of better, faster, more, quicker all the time, where now we need to slow down a little bit. And we, we've exchanged a few stories, but How do you earn that time for yourself? Or is it available at all?

I think it's a mindset and a commitment to learning constantly. I feel like really, really good marketers, really, really good storytellers are intellectually curious. And they're empathetic. And we often overuse the word empathy, I think, when we talk about creation of products and things like that. Empathy is an investigative process, right? It's asking a question over and over and drilling more and more into it, and it's an ongoing investigation of what the real need is. That's what I think really, really good marketers do. So I'm, as a marketer, I'm a huge, huge proponent of of performance marketing, hugely important. But I think sometimes we throw all of our chips into that one part of the board to the detriment of good telling great stories, which are the things that actually connect to humans in a more meaningful way. That's empathy, that's thinking about the story. And I, so I find that the combination of those two are the, the combination that creates the best result.

The original construct behind this show was that we talk about the beautiful friction of building, and we try to provide— I'm reading verbatim, I just pulled it up so I could read it back to you— but we provide a seat for everyone who knows the job is tough but shows up regardless, proving that shared empathy is the fuel that drives innovation. And you've kind of touched upon that. Then if I fast forward into the world of AI where things have got exponentially quicker and more demanding, and it means that we got to assimilate things even quicker. Being consistent in your point of view is something you maintain better than most people I know, which I'm always astonished at when I hear you speak, because that consistency is part of the ability to not just tell a story but know where it comes from, which I think is a skill in itself. But I sent you over this crazy story about Clinton's folly and the kind of rebirth of New York. And it was a part of my own NRF building experience, trying to understand where New York was 300 years ago, 33,000 people, not really a center of commerce, to today is the center of the earth, depending on who you speak to. But it is this huge, big ball of energy where global trade takes place. The part of the story that I loved was the idea this guy took it on himself to go to the UK Candace White, to try and build canals. And I'll go backwards on the story in a few minutes. And he, he kind of seems like you a little bit to me. He took time to walk the path and learn how canals were built, and then during that journey he learned there was this new cement that could be there to stop water leaking out of the canals and save people millions in maintenance contracts and all these kind of things. Firstly, did you think it was crazy when I sent you this story? And secondly, I'm sure someone like you was probably aware of the Erie Canal and its importance importance to North American trade.

Yeah, you know, I, I did know about the Erie Canal and how important it is because I used to live in southern Vermont and I would drive over to Albany to fly out or take trains. So I would start where the Erie Canal started.

Amazing.

I'd go through Troy all the time. So I, I'm very familiar with Erie Canal and, and how, how critical from a technology perspective that transformed the eastern seaboard of the United States and spurred growth for so many other communities like Chicago and other places where it connected the East Coast. So I was aware of that. I wasn't aware of Canvas White, but now he's one of my heroes. So thank you for— thank you for putting him on my radar. You know, since you shared that story with me, I've I've watched hours of footage about, about this guy and what made him special. What was interesting about him is he, I, you know, the problem of the water in the canal going out, seeping away, would be detrimental and fall apart. So they had to figure out how they were going to, you know, create a cement that would, that would do this. No one knew how to do this. No one in America had done this before. Yeah. So what was interesting about what you shared is— and which I think is really, really, really special about this guy— is that real progress happens when someone takes responsibility for the problem that no one owns yet. So everyone saw it as a problem, but real progress happened when someone owns that problem and goes to do something about it. And that's what he did. And what he did is he went to Europe to, to see how the Europeans were doing it. He didn't have to start from scratch. He wanted to get inspiration from other places and then bring it back. So that was, was so significant in my, my view.

Yeah, it was amazing as well that he did it on his own dollar. He, he was a 21, 22-year-old man at the time. Went to the UK and, and did all of that great work and brought it back. And then he took what was a 100-year project known as Clinton's Folly, the governor's desire to have this, this canal built, and it became an 8-year project and was delivered in record time. And, and it celebrated its 250th anniversary last year— or sorry, its 200th anniversary— which is an incredible feat that in, in this time New York has evolved so much. And now we talk about AI and where, where it's going and there's two other parallels within that, and there's so much more I'd love to get into, but I want to respect your time and get to a few more questions I have for you. But in the book Flash Boys, I don't know if you've read that, by Michael Lewis, where it was about the advent of high-frequency trading after, after Wall Street, or sorry, after the crash of 2008, there was an Irish guy called Ronan Ryan who was the guy who was able to determine getting a cable from point A to point B was going to result in millions, if not billions, in saving cost savings because it was the endpoints between trade centers. It was Chicago and New York Trade Center. And it ended up that when he was bringing the final cable into New York, he had all the big banks bidding like millions for a place having a data center closest to the server coming in, um, because they were going to get signals on trades quicker. Than their competitors. So he solved that. And then there's this other kind of symbiotic relationship we have with America in Ireland, which is the transatlantic cable, which comes into not far from where I live. And I just remember we held a conference here in 2019 and we had this great speaker. He's a musician by trade, but this guy's called Philip King. He came in to talk about the opening of the cable and how important it was for him. He had two daughters. He'd emigrated to the East Coast of America and Now this fiber optic cabling meant it was possible for his daughters to come home with their grand— with his grandkids to do their work in Ireland. He said it's not likely, but it's now possible. And he talked about the power of possibility. So when I get to that power of possibility, when it comes to things like AI and the responsibility of doing the job, where does the responsibility lie for making sure that we do it right, Fin? And what are those guardrails that we should be building to help us evolve as humans and to make the job better that we do? Because you talk a lot about recognition over supervi— over surveillance, I should say.

Yeah, so for me, especially where we are with AI, being early is less about being right than it is about being willing, right? The willingness to do is way more important than the— than being right, because you're going to figure it out. What was really interesting about the building of the canal is that they learned how to build the canal by building the canal. They didn't have anyone that had done this before, right?

Yeah.

And so the fact that they had identified, here's what we want to do, and they had a willingness to do it even though they knew that they run into a whole bunch of— in fact, Jefferson said this was near madness to do this, right? And he was a super, super smart guy. And so they were— because of their willingness to do it and their iterative process of problem solving, that's what innovated this. That's what created this innovation that was really, really meaningful. So for me, it's a lot less doing about trying to figure out how to do it right and more about a willingness to jump in.

Is the parallel today— so if I go back to NRF and why I was even researching it, is that all the companies who are on the basement and in the second floor or the innovation lab, are those people the kind of canvas whites of our day willing to get stuff wrong knowing that the bigger pictures to be solved?

I think there are a number of those, and those, those new innovators, um, you know, on the private equity side, we look at companies to invest in. One of the things that we're finding is every one of the things that we're talking about investing in is years or months old. It's not been around for 5 years, or it's, you know, that time horizon of how long they've been in existence doesn't— isn't there. It's so new, right? So you're not going to talk to someone who ran an AI shop 10 years ago or 5 years ago. Um, and so I think we are seeing a number of those Canvas White type characters in, in that space. I would also observe that that's one level of innovator. The other innovator that's really interesting is embedded in brands that are willing to take risks, right? Because those innovators, those young innovators are looking for people who they can marry up with and say, hey, we're going to work on this together. And so I feel like it's a one-two punch from a retail innovation perspective with great brand leaders in great brands identifying that this is about a willingness and less about being right as well. And so when they both understand that and they both partner together, that's when we're seeing super cool results that are coming out of some of these really, really cool companies that are emerging.

And, and putting your private equity hat on, so when you look at a person and they're in the room and they're pitching to you How much then are you drawing on your anthropology hat, or do you have to separate yourself from that to say, I'm almost investing in the person over what it is they're doing, because I know that the second version of this is going to be so much better?

It is at least half about the person. The idea and the ability, you know, proven market fit hugely important. But the other half of the equation is the person themselves. Are they the type of leader that will attract others? Are they the type of leader who will be willing to jump in to own a problem that no one else owns? Do they draw other people to them? Do they help build a rockstar team? That is huge in success of companies. And so yeah, when we, when we're looking at investments, we're looking at the human part of the equation just as much as we're looking at the idea.

And a kind of a follow-on to that then, how do you factor in that, the two dichotomies for me? One, you experience time over millions of years given your personal interest in anthropology, and then you've got this whole other side where companies only exist for a few months. How do you reconcile those things, or do you even bother trying?

Anthropology is about studying human meaning and understanding human meaning. And that is great context for what we're experiencing today. And it's also great context for tribes that we came from. And so It's not kind of time-bound, like anthropology isn't old stuff, it's understanding what we're experiencing today. Because what's interesting, especially underlying the thesis of the story that you're telling, is the fact that we can learn from our past. We can learn from the innovators of our past, and when we do that and we apply that meaning to our current day, it can help us navigate things in a much more meaningful way, in a much more successful way.

What, what will future generations look back on today and say, what can we learn from this? What meaning are we giving to people right now?

I think there will be something that's similar to Candace White in that there'll be— there are certain guys that got a lot of flack by stepping into the void and owning problems. Lots of people who said that couldn't happen, or lots of let's wait and see how this works. But there are some that, that are moving forward because of their willingness and their agility to learn. Right now, agility to learn and willingness, I think, is the, the thing that's going to win the game. And so I think, you know, if we look back on it, the early days of what this means, we're, we're go— we're moving through a change historically that is at the scope or size of the Industrial Revolution for humans. And if you think about in the Industrial Revolution, we were automating muscle power. Now we're automating intellectual power, brain power. And when we look back on it, we're just at the beginning of that process, right? Um, and it's exponentially changing faster. The difference between those two times One of the main differences is the AI side of this is much more compressed. In other words, it's— we're doing it faster. It took decades for the Industrial Revolution to roll through humanity. This is going to take a much shorter time, and so our ability to learn and adapt rapidly is going to be much more important.

Yeah, it's one of those things I think about in relation to my kids and where it's going to be when, when they reach the stages where they're making decisions on, on their future and what we've left behind them. Um, we're getting to the stage in conversation— I tried to keep this to 25 minutes even though we could talk for days— where I get to my stupid question, which is a complete step change, but I want to respect your time too. Looking back at your career to date, if it was a song right now, what would it be?

A song?

Yeah, that always throws people.

Uh, let's see, a song. Um, you know, one of my favorite songs— I don't know if this really, really, uh illustrates my life, but one of my favorite songs that I've ever had is Temple of the Dog, Hunger Strike, which is— it's essentially about as you become successful, remembering where you're from and the people who got you there. At least that is the story for me. And so Maybe it's a mashup of a bunch of songs, but that one, that one would certainly be in my mix for sure.

I'm gonna be throwing it on the, uh, Struggle Bus playlist and sharing it out. I'm gonna have to listen to it later on with the lads and, and see what they think. Um, Finn, you've been so kind with your time. I, I want to let— I want to try and get to wrap this up, but I think in saying knowing where you're from, you're one of those people who lives that quality really, really well. The kilt as well is a giveaway. Now, just on the kilt, maybe you can answer this with a quick yes or no. Scotsmen usually wear nothing underneath the kilt, and I've asked numerous people to confirm or deny. At NRF, were you full Scot or part Scot?

A Scotsman, gentlemen, never discloses. The mystery lives on, brother. The mystery lives on.

That is the Montanan coming out in you right now. But Dave, thank you so much for spending time with me on the Struggle Bus. It was, as ever, entertaining, educational, and just really, really interesting and good for the soul. So thank you so much. I really do appreciate it, as do everyone listening.

It was always— it's always a pleasure to see you, my brother. It's good to spend some time with you. Thanks for— thank you. See you soon. See you, brother.

Thanks, Dave. Amazing. Uh, thank you so much. The only thing