On Loneliness & Lumberjacks with Andy Ellwood

Actionable insight about how we have all the time we need, how holding complexity is key, and the importance of asking the right questions.

Referenced in this Episode:

Andy Ellwood is Co-Founder of Basket (where he seeks to revolutionize the way we buy groceries) and coaches aspiring start-up founders and executives.

Playlist Contribution: “All I Do Is Win” by DJ Khaled


Episode Transcript:

Liz Wiltsie:  So today we’re going to welcome a good friend of mine, Andy Elwood. And I asked him to be here with us because he is a multiple founder. And he’s been leading both within organizations that he worked in, also as CEOs and founders in various different organizations.

And he’s been a part of successful acquisitions by Google, by Facebook. And now he is running Basket, which is revolutionizing the way that we get groceries across the United States. And also, Exosphere, which is an in-residence education program in Spain that focuses on learning through experience.

So, I am super excited for Andy to be here and answer all of our questions. So, we’re going to get to it. Hi, Andy. 

Andy Ellwood:  Hi, Liz. Thanks for having me. 

LW: Of course. So, what do you think is the biggest challenge for leaders?

AE: Loneliness. I think that the conversations that I would love to have with other people, the conversations that I want to have with friends, most of my friends, a lot of my friends are not in similar positions to where I am.

They work for themselves but a lot of, there’s just a different type of conversation that you have when you got 14 kids collectively that if you don’t keep the company going, their parents don’t have health insurance. It’s a, you know, a different type of conversation you have when they’re out on the edge of things, and you really want to be able to share it with somebody.

And people will listen, but they don’t have really much to say besides, “Wow, that sounds hard”. And so, finding other folks that are going through similar things, or similar challenges at the same time as you, I think is a really important thing for anybody who’s in leadership position to do.

But even then, you know, the challenges are going to be yours and yours alone and figuring out how you handle and deal with that loneliness being out on the edge, fighting the wind, when other people are finding other easier ways, seemingly easier ways, not wrong, which is easier ways to live their life is, it’s a challenge.

And it’s a lonely battle but it’s one that I find to be pretty consistent across people that are in a traditional leadership. 

LW: Yeah. So, what do you think is like a tip that you have, it could be about loneliness, it could also be about something else, but the number one tip you have sort of as a leader yourself for someone else?

AE:  Get right with yourself, even if it means taking time away from the team, from who you’re leading. Steal time, make time, cancel meetings and things with your team if you’re not really where you need to be with yourself about why you’re doing what you’re doing, why you’re rolling into the situations that you are.

There’s nothing worse than seeing a leader come unhinge because they weren’t taking care of themselves. And that one little thing that catches them off guard causes them to undo a lot of goodwill, because they weren’t in a spot where they were being honest with themselves, about how hard the leadership was really wearing on them, and what was really wearing on them.

And they walk in thinking that they’re going to be Superman and be able to, you know, be Atlas with the world on their shoulders. And one little thing hits in the wrong way and without knowing that they lose it and not just lose it for themselves will probably lose it for in front of the others and it changes the whole dynamic of the conversation because, you know, sometimes that means that you’ve got to go back and repair some relationships.

That means you’ve got to take, you know, you’re going to have people that are maybe tap dancing around you for a little bit and not to be dishonest with folks, but it is really okay to just take a moment. Take 10, walk around the block after a hard meeting, step out, and you know, call a loved one. Call your girlfriend, call your boyfriend, and just say, “Hey, I just need to take 10 big breaths, would you mind listen while I do”. I mean, sometimes that’s what it needs. And I think that it’s the responsibility of the leader to know themselves well enough to know when they need to tap out for a second so they can jump back in full speed. 

LW: Yeah. There’re so many thoughts I have about that which is like, there’s these two tensions between, one, like the leaders supposed to always be on, right? The idea of you’re not like, “No, you don’t get to take a break”.

And then there’s also the side of me that says, like, wouldn’t it be nice if we sort of embraced a kind of imperfection in it? But also, I think about it regularly and so many leaders are sort of the charismatic heart of their organization.

And it doesn’t necessarily mean the CEO, right? Like you’ve been in an organization where you weren’t in senior leadership. Where like, you can feel kind of the energy of folks, right? And so, there’s always that thing that says, but yeah, you got to step back and recognize your own thing and go like, “Whoa.”

AE: Well, I think it really, it sets an example for your team that, hey, we’re all showing up and we’re showing up right. We’re showing up with our best and if that means we’ve got to take a moment to slow down for half a second, you know,

I always tell the story of The Legendary Lumberjack of the Woods, and being a lumber sexual man myself, I like stories about lumberjacks. And there was the legendary lumberjack that everybody knew he was the best.

And for years and years and years, he was the best, hands down, nobody even question it. But as the years wore on, a young upstart lumberjack jumps up and says, “You know what, I think I’m the best now”.

And challenges the legend to a chop off and say, “For five hours we’re both going to chop trees, whoever cut down the most trees in those five hours is the king of the wood.” They go about it and true to form the young lumberjack like just outpaces boulder lumberjack. Just chops literally nonstop straight for five hours and nobody’s ever seen anybody chop as much as quickly.

And the young lumberjack gets even more confidence when he sees the older lumberjack like sitting down, and like sitting next to a tree for like 10 to 15 minutes a couple different times throughout the chop. In the end, they tally up the total and the old lumberjack beat him by a decent number of trees.

And the young lumberjack cannot believe it and is irate and says, “How’s that possible, like I chopped non-stop, and you kept taking breaks”. He said, “I wasn’t taking a break, I was sharpening my axe”. And I always, like, I tell that story to my team. I’ve told it to a bunch of conferences. I’ve been like, slow down to sharpen the axe.

Like, if you’re swinging a dull blade against, I mean, it’s like beating your head against the wall. There’s nothing worse. So slow down and sharpen the axe and come back, you’re going to be able to do less work with more efficiency. And that’s an example that I think everybody should set for their team. 

LW: Yeah, absolutely. So, kind of in that vein, what’s been the most impactful, sometimes concept, book, talk, something that you, that’s really stuck with you outside of your lumberjack story? 

AE: Yeah. I think that the, I mean, the buck stops here is kind of just the always that, when it’s all said and done, anything that my team is doing, by them being on my team, I am effectively signing up for it.

And making sure that I sit with folks for as long as it takes to where they can be, and they can understand how I would handle situations to where I don’t have to be there to handle every situation.

And I think, you know, I think a lot about that, that I start every single hiring conversation, like, when somebody joins my team, I tell them that we don’t earn trust around here you have it. If you are here, everyone knows that you’ve been signed off on by me and my co-founder, and you don’t have to earn our trust.

You have it on day one, full trust on day one, but you can’t lose it. And so, we’re starting you off with 100% full tank. And we want to give you every way possible to maintain that. To keep it. And you’re not starting from zero trying to earn your way up to 100. Like, you’re here, if you made it through our hiring process, you’ve got full speed.

And here’s the principles and the values. So that’s the first thing we go through, we go through the 10 principles and values of our company. The things we stand for and the things that, like, we operate against. There’s a, if you do these things, if you buy into these things, then we’re going to have a problem.

But the goal is, you know, with as many moving parts as are happening, I’m on the road, you know, a lot. So, I’m not in the office with my team all the time. I’m checking in virtually and communicating through all the different ways, but not there face to face. Because I want them to be able to not even have to, they don’t have to ask, “Well, what would Andy do?” They know, right? And I try to be that consistent so that they can operate and with the same level of consistency and confidence.

LW: Yeah. So, what should I have asked you that I didn’t?

AE: Good question. When talking about leadership, I think it’s so immensely personal. And I think that, you know, I’m really fascinated just by all the different ways that it manifests itself. Just because every single person is going to have a different style because every single person is unique and individual.

There’s a million books out there, there’s a million programs and conferences and things along those lines. But I really think that the thing that I admire the most of the leaders that I look up to, and then the leaders that I see that are the most effective, is they have figured out what their style of leadership is, and they just own it.

And they attract people who want that style of leadership. And they’re also quick to say to people who don’t want that type of style of leadership, “I’m not changing, so, either we figure this out and you figure out how these blends into you being a part of this team, or we need to probably just part ways.”

And, you know, I did like a handful of times last year where just, they were saying, “I need you to be a different person”. And I was like, “Then I think you need to find a different job.” And just being able to understand that like, some people are just not going to jive. Some people are not going to work well with the other. And it’s okay. It’s not wrong. But the sooner you can figure that out, I think the better.

And if you have been a consistent and in integrity leader, it’s okay to say, “Hey, this just isn’t really a thing.” I mean, and we do that a million times a day with like, people that we meet on the street, we’re like, there’s no way that that person and I are going to be friends. And that’s okay, right? And I think that that’s the other piece that a lot of like, for myself, you know, I care what people think, I really do.

And I always have, and I always will. But figuring out that caring what other people think is a way to sharpen, you know, to sharpen my axe. To get myself smarter and understanding and being more responsive, and a lot of times more empathetic and sympathetic to, you know, the situations are. Looking for, “Oh, that’s why they reacted that way in that situation.” I feel that’s helpful just, but it starts with knowing who I am. And then being able to, you know, and hopefully that being a constant, and then looking at how my constant interacts with in consistencies.

LW: Mic dropped.

AE: Bam.

LW: That’s our interview. Thank you, Andy. 

AE: Absolutely.

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