North Star Leaders Podcast

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're learning this together on the North Star Leaders Podcast. In this podcast, I talk to purpose-driven leaders about the choices that 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 so happy to be joined by Todd Dunlap.

Todd is CEO and board chair of OfferUp, the marketplace to buy and sell locally. Todd, welcome to the show.

Todd Dunlap

It's great to be here. Thanks for having me.

Lindsay Pedersen

So glad to have you. To start us off, Todd, what is the most energizing part of your job that those of us on the outside might not know?

Todd Dunlap

I'd say I'd start with the people that I get the opportunity to work with. A group of super passionate people that care about our purpose and care about why we're doing what we do. And I find, I guess, in my career and where I'm at in my career that the problems that I've faced throughout my career seem pretty similar.

I'm working at Microsoft on Xbox or I'm working at Booking.com on hotels or working at OfferUp on our e-commerce marketplace. The business problems tend to be pretty similar, but the people I get to solve them with are not. And I've just really found an amazing group of talented people that are passionate about what we're trying to accomplish.

And that's what I love.

Lindsay Pedersen

That's so interesting that from a travel marketplace, a gaming company, a marketplace for buying and selling locally, that the problems start to look similar or the business conundrums look similar. Why is that? Like, how could it be that they start to look similar pattern-wise after a number of different industries and companies and seasons of your career?

Todd Dunlap

Yeah, I think it's a good question. And that's a fair question since I answered it that way. I mean, let's just talk about there's a common language across all business, and that's typically a P&L.

And so there's how much money are you making and how profitable is it? And how many users do you have? And do you have more users or less users?

Or, you know, so those types of kind of common questions I think are common regardless. If you have a business, you're typically trying to offer value. The more value you offer, the more people use it, the more people that use it, hopefully means the more money you make, the more money you make, the more investment you can make, and the more you grow.

I mean, that's just got to be some commonalities on kind of business. And so I think those are common. And I think those tend to be universal.

Of course, a e-commerce marketplace has unique challenges to a gaming company or a hotel platform. And those things tend to be specific to the business that I'm in. And so it's not all common, but a big bunch of it is.

What are we trying to do today? What are we trying to solve today? What's the hard work that we're trying to get done today?

It tends to be kind of common.

Lindsay Pedersen

Yeah, I suppose after all, you're still selling to human beings who have scarce time and attention to spend on you. And you're still trying to win over the hearts and minds of human beings, whether it's B2B, B2C, whether it's e-commerce, whether it's gaming, whether it's travel, it all does sort of start to come to what drives a person.

Todd Dunlap

Yeah, I agree.

Lindsay Pedersen

With OfferUp, what's the nature of the pain that you're solving and what makes OfferUp so good at solving that particular pain?

Todd Dunlap

Yeah, we took a unique approach when we started. And the uniqueness of our approach is, I wouldn't say the uniqueness of today, the uniqueness of our approach was we were the first to really go after this, how do you get rid of stuff locally? Back in the day when we started, there was eBay and there was Craigslist, but OfferUp came to the scene with a mobile optimized solution.

So, you know, believe it or not, cell phone wasn't part of that equation when we started. And so that was unique and that was differentiated. And I think that helped us certainly in the early days to grow to where we're at today.

Now I'd say we do two things or three things that are super unique and differentiated and offer value beyond just kind of our core beginning. One being, we are really trying to unlock local value. There's so much value locked up locally and that value continues to grow every single day.

And one of the things I like to joke about is every time you push that buy now button on Amazon, that just creates another opportunity for us because you probably have to get rid of something.

Lindsay Pedersen

Well, yeah, wow.

Todd Dunlap

Then some things are, oh no, I just bought something new. Those boxes continue to pile up on your front door. And now you have stuff that you need to get rid of.

And so that stuff that you need to get rid of, we really pride ourselves in providing an easy way to do that. We've differentiated in spending time and energy against doing that in a really safe and trustworthy way. There's some real value in communities connecting, but there's also some risk in communities connecting.

And so what are some things that we can do that are unique and differentiated to make sure that we're creating a trust, a safe and trustworthy experience for users. And so lots of things we do there to unlock that local value, but do it in a way that's safe and you can do it in a way that you can feel confident and comfortable doing that. The other couple of things that we're really focused on lately, and one of these things is not so new, it's new-ish, I'd say six months old is, you know, beyond just the value in goods, there's also real value in local services, people that are wanting to offer you a local service.

And there's some really great people and companies that do this, but have a hard time figuring out how to find people to provide their service to. And so how do we create that market, bring that expertise we have in the marketplace to the services space, and that's working so far so good. And then this final thing that I just highlight, because I'm going on too long for your short question, is in the local kind of e-commerce space, people have questions like, hey, if I want to buy a used saxophone, where do I even go to find out what I should look for?

I've never bought a saxophone. How do I engage a community of people that actually know how to do this really well and get some insight? And so we're really creating this kind of social commerce experience too, so you can have conversations with people in the community about the stuff you're looking to do in the community that helps yield more value for you in the community.

And so it starts with really differentiating on local, really differentiating on services that we provide locally, and doing it in a really trustworthy, safe manner.

Lindsay Pedersen

And the word community keeps coming up, and I can see why, because there's such deep need for it today, maybe more than ever, and your local e-commerce is inherently community building in some senses. What's a community story that really lit you up or that you love to talk about?

Todd Dunlap

I have many, but I'll give you an example of my favorite personal story on Off Rep and how it just shows the power of community and the power of the value that we're looking to unlock in the community. So it starts off a little snobby, and I apologize for the snobbiness, but if you live in the Pacific Northwest, which we do, it's not uncommon to have a house on the water, and we have a house on the water, and it's not uncommon to have a boat that you put on a boat lift on the house on the water, and so we have a boat that we put on our boat lift, and it's not uncommon to put a cover over the boat that's on the boat lift on the water.

And so we had this boat lift and this cover on the boat lift, and the cover is, it's a canvas cover, and those things wear out every few years, and so you need to replace them. I took off this cover and bought a new cover. And so I had this cover, this big canvas cover, and it's not like it's tatters and should be thrown away.

It's actually a, it just, it gets to the point where you, the wind and stuff, you just need to do this. I don't bore you with the details on that, but I'm like, you know what? In the past, I might've figured out a way to recycle this or throw it away.

But I'm like, you know, I bet there's someone who could use this. And so my bet and my hunch was right because I put it on offer up and I got this pretty quick response. This gentleman said he'd love to come get it.

I said, great. So he comes over, comes in a pickup truck. I could hear he had a kid in the back seat and the kid was kind of screaming and that's normal.

And yet I could tell there was something not quite perfect there. And so he rolled down the window and the kid was obviously, he was on the spectrum and he was autistic. Yeah, which is great.

I have a nephew who's autistic and it's great. And so anyway, the dad was like, I can't tell you how meaningful this is to me. I'm like a free used boat cover canvas is so meaningful to you.

Like again, I discounted all the value. I'm like, it's done. I'm getting rid of it, obviously.

I'm replacing it. He said, yeah, he goes, my son, we have a little swing set out in the backyard and he loves to swing and swinging soothes him. And so when he gets into a situation where he can't soothe himself, he goes to the swing and we're just entering into rainy season.

And I've been trying to figure out how can I cover the swing set? And I've looked at tarps and I've looked at, he goes, I've looked all over, tents, things. I just can't find anything.

He goes, this is the exact dimensions that I needed. And it is. It's long.

It's exact dimensions that I needed and it will fit perfectly for him and it will enable him to swing through the rainy season and the feel of a Northwestern rainy season is basically eight months. The story doesn't start there and the emotional impact doesn't stop there. The emotional impact came next.

And that's when he told me, he said, unfortunately, my son, I lost my wife. My son's mom passed away from cancer six months ago. And so the swinging has become a real way for him to help kind of manage this and for me too.

And so this is a story just illustrates the power of community, of connection, of just stuff that I discounted that now is like a difference maker for a family that obviously was in need of something that I had totally discounted. So that's hopefully illustrates community connection and how stuff passing around can really make a difference in the lives of people.

Lindsay Pedersen

Oh my gosh, Todd. I mean, to think that you could have taken that and thrown it in the dumpster.

Todd Dunlap

The past, that might've just been a dumpster run or might've just been a recycling thing and it's like, hmm, maybe someone can use this and ta-da, they can.

Lindsay Pedersen

You made not just the day, but probably the season for a little boy and his single dad.

Todd Dunlap

Isn't that something? Yeah. It's just, it really is amazing.

And, you know, again, that was one example. There's so many.

Lindsay Pedersen

I mean, I can only imagine. And it's because of the nature of local services and local items, a lot of it is very mundane. It's a piece of canvas.

It's a chair. It's a toddler bed. It's not a concept.

It's like something that we can all relate to and it starts a conversation and it starts a human connection.

Todd Dunlap

Yeah. No, that's a- Oh my gosh.

Lindsay Pedersen

I love, I'm so glad I asked you that. That's incredible.

Todd Dunlap

On the human connection bit, I get invited every year, Lindsay, to a wedding of people that have met an off rep.

Lindsay Pedersen

Oh my God.

Todd Dunlap

Last year I got invited, you know, this year I got invited that, hey, Todd, we want you to come to our wedding because we met an off rep and so we thought you should be there.

Lindsay Pedersen

Wow.

Todd Dunlap

Right? It's the power of community. It's the power of connection.

Lindsay Pedersen

Yeah. Yeah. Starting a conversation.

You mentioned earlier the people at OfferUp are so meaningful to you and bring you so much energy. What do you attribute that to? Like what's the magic sauce that leads to a group of people working together so beautifully?

Todd Dunlap

That's great. I think that it's funny because it's a bit of a dichotomy. And what I mean by that is there's an element of commonality, of people just having passion for the why, passion for why we're doing what we're doing.

The story I just spoke to, I mean, there's just the passion of, we're not just creating a platform to get rid of you stuff. We're creating a platform to unlock value in local communities, building community. Certainly there's an element that ties to the environment, et cetera, but we're really looking to build stronger community.

And so there's a commonality of people share that passion. And so that's one element. The dichotomy, the flip side is, I also think what creates such a great dynamic team is the diversity, is that the people on my team are so different.

They all share a same purpose, but they all are so different in who they are and backgrounds and thoughts. And so creating a space by which the diversity can come out and we can all have different points of view and that we can work out problems with different perspectives and experiences with common purpose of solving problems in local communities, that coming together is pretty special and that's pretty cool. That's I think why I love jumping out of bed in the morning and spending time with my team.

Lindsay Pedersen

It sounds like it's almost equal and opposite, like there's this uniformity of congruence with the purpose and then that allows for the opposite of uniformity of other things like lots of variety of life experiences, diversity in different realms because they're driving toward the same purpose.

Todd Dunlap

Yeah, exactly. I've found in my, I guess, careers that harmony is interesting, but I'd rather have respectful challenge. I'd rather have a team of people that respectfully challenge each other to think bigger, to solve broader, to consider different.

And if you find that magic where that can be done in a way that's just part of our DNA and who we are, then that's kind of how it is.

Lindsay Pedersen

I love that. What's something that you're OK with OfferUp not being good at?

Todd Dunlap

You know, something that I've kind of said for a little while is my answer is perfection. But something that I've said for a little while is a right decision, one point. A wrong decision, learn from, one point.

Indecision, zero points. And so I'm OK with us trying things and breaking things. And sometimes that means breaking things for the customer experience.

And certainly it's not something that we love doing and love going and doing intentionally, but it's OK. It's moving fast. It's being disruptive.

It's all with the intention of providing more value. But I'm OK. I'm OK with getting it right.

I'm OK with getting it wrong and learning from it quickly. I have a lot of tolerance for that because that's innovation and that's kind of what you need to do. If you're solving a problem that's been solved a million times before, it's pretty easy.

There's a playbook. You're pushing against things that haven't been solved before. It requires courage.

And so I'd rather have courage and try and fail and learn than always be perfect.

Lindsay Pedersen

How do you provide that psychological safety? Like, what does it look like when a mistake like that happens that gets learned from? What is said or conveyed or modeled to that person or team or your whole organization, maybe even?

Todd Dunlap

Yeah, I just came out of a meeting before talking with you about kind of business, you know, what went on last week and there's something that broke and the team's looking at it. Two things. One, you know, I'm not going to say that because this is kind of cross-trite, but we celebrate it.

I don't like what, you know, pound fist on tables and all that. I'm like, oh, great. We got a good learning here.

Let's learn about it. And so the second thing is that the team just kind of is naturally wired now to rally around. OK, this thing broke.

We want to learn from it. And not only do we want to learn from it, we want to share the learning. And so that rolls in the next week.

And so we just kind of have this natural cadence of one, people are comfortable. Hey, this broke. Two, I've got it.

I'm figuring it out with the team. And three, I'm going to come back and share learning so others can learn from it. So it's just kind of an embraced common practice of how we work at OfferUp.

Lindsay Pedersen

And I love you use the word cadence like there's a rhythm to sharing a structure already there and we're going to use it to share so that others can learn from this. We're not going to call like a special meeting necessarily. Maybe that's sometimes useful too.

But there's like a mechanism for sharing that kind of like remove some of the ego from there. And it's like, this is something we're all going to gain from.

Todd Dunlap

Yeah, right. It's just this is just how we work. It's like something's now.

Lindsay Pedersen

What's something that you've learned about yourself as a person, as you've been a leader of OfferUp or could be as you've been a leader in other companies as well? What have you learned about yourself?

Todd Dunlap

A couple of things and I have to go back to my parents a bit. You know, we all go through that age learning of, you know, my parents don't know anything to my parents, maybe knew something to, oh my gosh, now I reflect back on what I was told by my parents. And my dad once told me, you know, never to ask someone to do something you won’t do yourself.

And I think that's a really important thing. And I may not have the skills to do everything that people do on my team, obviously, in the job I'm in, I certainly have skills that I developed, you know, growing up in business, but, you know, ask me to do what maybe one of our lawyers needs to do or even one of our accountants, and I'll probably certainly not do it as well as they would. But if I'm going to ask for something, it has to be valuable and meaningful enough for me to need it or want it or need to use it.

And so, you know, making sure that I'm willing to do the work. That's just kind of one thing when I think about, and that's what my true love for OfferUp. The second one, my mom, there's this thing called the golden rule, treat people like you want to be treated.

And she said, actually, it's kind of more the platinum rule. You kind of want to treat people how they want to be treated. That's key, because what that requires is that you understand who that person is that you're working with, what makes them tick, what motivates them.

What motivates me may not motivate you. I need to get to know you. So I understand you.

So I understand what motivates you. And then I can treat you in a way that you want to be treated, you know, so that's kind of key. And that transcends kind of all leadership roles that I've been in.

But it's certainly true what I'd offer up for sure is that, you know, one, understanding the work to be done, understanding what work I'm asking to be done, making sure I'm being respectful of folks I'm asking it, and understanding people and understanding what it is that makes them tick, understanding what motivates them. And boy, there's lots of different things that people get motivated to do by different reasons. And understanding those reasons, super important.

Lindsay Pedersen

I love how with the golden rule, if you think about it, you actually don't need to have any empathy because you're just, what would I want? With the platinum rule, you have to have empathy. You actually like they're drastically different in a lot of ways.

Something I love about the way you just described that is that it happens internally. And it also happens with customers because if you're only building for yourself, then you're really going to limit how much it's going to resonate with an audience who's different from you. So if you bring that same value externally as you're bringing internally, that too is a growth driver in a way, like empathy can be a growth driver.

Todd Dunlap

It takes time, it takes curiosity, and it takes intention, intentional about it. And yeah, I agree.

Lindsay Pedersen

Yeah, you have to care. This is my last question before we get to our rapid fire. What's a principle that you hold dear that others might really disagree with?

Other leaders might disagree with something contrarian, maybe.

Todd Dunlap

This is going to come across as simplistic, but I have had disagreement with this principle before and because it can come across as compromising, and it's not a compromise at all. It's intended to be exactly what it's worded as, and that's people first. And so I do believe that successful businesses certainly require successful ideas and successful execution.

And, you know, all the things. But I tell you what, my experience has been that when you get a good group of people together, you treat them right and respectfully, you support them and their development and growth, you're after a big, bold problem that matters, a lot gets done. So people first.

And I've come from environments that we have some in our community that would say, no, it's shareholders first, or it's profit first, or it's, and all that stuff matters. But I think that's core core stuff. I think that comes when you have a great group of people that are motivated to do great work.

Lindsay Pedersen

Right. It's like sort of confusing inputs and outputs. Like there's going to be a happy byproducts of people first.

And strangely enough, if you aim toward those byproducts, you actually might not get them.

Todd Dunlap

Exactly.

Lindsay Pedersen

Yeah. This has been so revelatory. I've learned so much from you.

I've got a few rapid fire questions. These are just fun. One word answers.

Are you ready? Okay.

Todd Dunlap

Here we go. I gotta get ready.

Lindsay Pedersen

All right. What book, movie, or TV show changed your life?

Todd Dunlap

Ooh, Dawes.

Lindsay Pedersen

Me too, but not always in good ways.

Todd Dunlap

I swim less.

Lindsay Pedersen

Yeah. Yeah. Even in pools.

Okay. Awesome. What is a place that you've always wanted to travel to?

Todd Dunlap

Southeast Asia.

Lindsay Pedersen

Just anywhere or like any, like.

Todd Dunlap

I want to go into kind of what I call gritty Southeast Asia. So not like Singapore and, you know, it's like I want to go to, you know, Vietnam.

Lindsay Pedersen

Yeah.

Todd Dunlap

Oh yeah. And I want to really experience kind of the authenticity of that area of the planet. That's on my list.

Lindsay Pedersen

That's next.

Todd Dunlap

Okay. I have some other things in Europe too, but that is like where I want to go.

Lindsay Pedersen

Awesome. What is your favorite way to work out?

Todd Dunlap

I like to run, but then I also have been really getting into kind of my body weight rather than weights, but like the pushups and the sit-ups and the crunches and the lunges and the things that just using my. And the reason that that's been so revolutionary for me is my travel because I travel a lot. I can still always get my workout in.

There's no reason that I can't do the workout because I bring myself with me.

Lindsay Pedersen

Yeah. It's like low maintenance, low drama.

Todd Dunlap

Yeah, I run or I'll do, you know, the walking, like distance walking or, you know, those things are always good too. And that's every day. It has to be every day.

Lindsay Pedersen

Seven days a week?

Todd Dunlap

Seven days a week. Seven days a week.

Lindsay Pedersen

Seven days a week running and body weight or like you'd. All of it too.

Todd Dunlap

All of it. Okay.

Lindsay Pedersen

You're making sure movement is part of your day every day.

Todd Dunlap

Part of my lifestyle, part of who I am, part of, yeah, exactly.

Lindsay Pedersen

I love that. What is the best app on your smartphone?

Todd Dunlap

Boy, the best app on my smartphone.

Lindsay Pedersen

And you can't say OfferUp.

Todd Dunlap

Oh, let's do that. You know, I, geez, I'm kind of a social media junk. Well, maybe it's Jghin and you won't know what that is, but that's my golf handicap score app.

Okay. My golf handicap score app to date at all times. So I know when I'm golfing with someone, whether or not I should bet or not.

Lindsay Pedersen

Oh, that sounds like has a lot of functional utility.

Todd Dunlap

J- G-H-I-N, your golf index.

Lindsay Pedersen

Oh, got it.

Todd Dunlap

And that's a silly one, but I didn't want to say any social media apps.

Lindsay Pedersen

Thank you. I appreciate, I much prefer Jghin. Awesome.

Okay. Last but not least, what was your last splurge purchase?

Todd Dunlap

Golf clubs. I mean, ironically just happened to be golf clubs.

Lindsay Pedersen

Okay. Okay. I see.

I see you. Oh, gosh, Todd, thank you so much. This has been such a nice conversation.

Where can we send folks if they want to learn more about you about OfferUp?

Todd Dunlap

Well, we have an app that you can always download. If you want to know more about me, you can certainly look at LinkedIn. If you want to find out more about OfferUp, we also have a site too.

You're welcome to come take a look at offerup.com.

Lindsay Pedersen

Awesome. Thank you so much. 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. If you know of a North Star Leader whose insights would be valuable for this community, please message me on ironcladbrandstrategy.com. Also on that website are show notes, transcripts, and a way to sign up for our monthly newsletter.

I hope you join us again for another episode of North Star Leaders.