Transcript

Chris LoSacco Also I just picture Freddy, the Mailchimp monkey, like—

Gina Trapani You know, winking

CL Swinging from tree to tree—

GT Swinging from tree to tree. Winking at ya—

[Intro music fades in, plays for 10 seconds, ramps up.]

CL Hello, Gina!

GT Hey Chris!

CL How are you doing?

GT Just went through a giant Trello board of things to do, you know. Growing busy business, you know?

CL That’s right.

GT How are you doin?

CL I’m doing great. It is a pleasure to be growing and investing in this company we call Postlight. There’s a lot ahead.

GT It really is.

CL I wanted to talk to you today because you were on that website twitter.com recently.

GT [Laughs.] Yeah, I sure was.

CL You posted an interesting sort of call to the community. What did you say?

GT I did. I posted a tweet that was, you know, right off the top of your head as one does. And I said, tell me some good metaphors for building and running a company that aren’t sports or war. Posted this tweet just off the top of my head. Didn’t really think about it afterwards. And then my mentions blew up [laughs] because I didn’t realize that that off-the-top-of-my-head thought was like essentially catnip for every leader, executive, founder, and VC in my Twitter followers list.

CL Yeah. To weigh in with their preferred metaphor.

GT Exactly.

CL There are some real gems in there, and there are some questionable responses that we can talk through. [Both laugh.] I mean, there’s a lot. It’s very interesting how it resonated with people. And again, prompted these very interesting…some made complete sense. Some were like, oh, I’ve never thought of it that way—

GT Yes.

CL When thinking about how to draw a parallel to what running a company is like.

GT It was funny because later that day I was reading something somebody posted in the Postlight Slack, an interview with the new Peloton CEO, Barry McCarthy, who by the way, based on that interview alone, he sounds very competent and very good. I was super impressed with him. But it’s literally like the last paragraph in the interview. And he says this is Barry McCarthy talking about Peloton and, and trying to turn around Peloton, right. Which just had to do around the layoffs and et cetera. Barry says, we’re a sports team and we’re trying to win the Super Bowl. And so we’re gonna put the best players in the field we can. And if you go down the field, we throw you the ball, you drop it a bunch, we’re gonna cut you. Because everybody else who’s trying hard to win the game, deserves to have the best players on the field. And if you’re a good player, you’re gonna love being on this team. I was like, okay. [Laughs.]

CL Yeah.

GT He only wants A players. I’ve said this—this phrase has come out of my mouth—A players like to play with A players. You know, if, if you’re building a company culture, which we are, of subject-matter experts and high performers, there’s very little that’s a drag to a high performer like working with an underperformer, right? So it’s important to do that. But it struck me because I was like, this is as sporty of a sports metaphor ever. I mean, Peloton is a fitness product, so I’ll, I’ll give Barry a pass there.

CL There’s some connection. Yeah.

[2:59]

GT There’s some connection.

CL Two things come to mind. The first one is absolutely what you said before, which is that we’ve echoed the same sentiment to each other. As we talk about how we grow the team here at Postlight, the promise we make to our clients is that we’re gonna bring expertise and top-tier execution to every single project that we do and in order to do that you’ve gotta have a group of A players. So it makes some sense that you want people who are going to have high expectations, both of themselves and those around them. And so if you’ve got low performers on the team, then it doesn’t feel good, you know, in our world, the teams that are executing on project work. And it just makes people question the values of the company and the culture of the company if you’ve got people who are not doing great. Something else that comes to mind though, to take this sports metaphor, I know we’re trying to get away from sports, but just for a minute…

GT There’s usefulness here.

[3:53]

CL There’s usefulness here. Another thing a sports franchise has to do is grow talent from within, right?

GT Yes.

CL It’s very important that teams think not just about who are the players that I’m putting on the field right now, but also who are the people that I’m investing in, who are the younger players, the prospects in the baseball world, it’s the farm teams in the football world. It’s who’s who am I looking at to draft in college? Because you’ve gotta be thinking about, you know, the next generation that you are also thinking about if you want to have continued excellence. And again, an interesting parallel for where Postlight is right now, because that’s something we think a lot about too, is how are we getting in people who can execute day one, right? The week we hire them, they hit the ground running and they’re ready to go. But also how do we get associate level people who have a ton of raw potential, a ton of raw skill, but need to learn a little bit through experience and also through mentorship from those senior folks that are around them. And so doing things like investing in a mentorship program can actually be very, very valuable when you, you think about where you’re gonna be, not in the far future, but like 3, 6, 9 months down the road.

[5:07]

GT Definitely. It’s true. Because it’s about teamwork. It’s about defeating competitors. I mean, you and I pitch new business and we’re competing with other agencies who are also pitching that business. And it’s literally about winning, right? We have to be better than our competitors. And I have a competitive streak and I really like the idea of winning business, winning market share, putting out a higher quality product, or higher quality services than our competitors. So I have to say, and I like sports. I played sports. I don’t think sports works for everybody. And you hear it a lot in the business world. It’s a little cliche.

CL It’s overused, yeah.

GT It’s overused for a reason. It’s a very close parallel to what we’re doing.

CL I would say one area where it breaks down is that sports are very straightforward, right? It’s a very simple thing. You can have a lot of strategies that go after it, but the I gotta put this ball in this basket or I gotta hit a ball hard to get people around the bases. Like it’s very straightforward what you’ve gotta do. And I think our playing field in the agency software world, trying to figure out how you, you know, grow and capture more market share is not a straightforward problem. And you have to think, I think a little bit wider when it comes to how you approach things that require a little bit more flexibility in the metaphor.

GT But it is an existential thing, right? For small companies.

CL How so?

GT For small companies that are trying to get their business off the ground, particularly small companies that are taking venture capital, like you have a certain amount of time and a certain amount of capital in order to do a thing. And if you don’t do the thing, if you don’t get product market fit, if you don’t open up those revenue streams, your company dies. You fail.

CL Right.

GT Like it is actually existential. And I think this is, you know, it’s funny. Like I definitely have a survivalist—you know, my entire career has been in small companies. So I’ve always felt very acutely this existential threat. I founded a company and ran a company which failed, which died essentially. Like we just didn’t make it a couple years after the 9/11 attacks. I worked at a startup and watched half the staff get laid off, like on the floor, watching my coworkers walking out of the office with the box in their hands. And I tell you, this was great for me as a business leader because you have to feel that existential threat, you have to feel that, in order to make the really hard decisions, in order to feel that urgency about getting stuff done quickly about not putting up with bureaucracy or not flagging risks. It’s an important thing to have that kind of survivor’s mindset.

CL Nothing is assured.

GT Nothing is assured

CL You can’t rely on anything, any sense of stability. I think when you’re starting a business or even in the early years of a business, knowing that so much is up in the air and you have to constantly be protecting your flank and thinking about where are your weaknesses and also where are your strengths and how do you play to your strengths and minimize your weaknesses. I do think though, there being an endless stream of challengers. Like I get the spirit behind it but it’s actually not that true. In a lot of the markets that we play in anyway, there’s a lot of room for many companies to succeed. And there’s a lot of things that we don’t wanna be. And a lot of things that our competitors aren’t going after in the same way that we are. So I don’t know that I buy that it’s like, you’re constantly under threat by somebody else or the next 5 or 10 companies that are going after the same thing you are. I think it is more about making sure that your own value proposition is really clear and viable and that you’re constantly going after that, because that is, I think, where the real threat comes from is that—

GT Yeah.

CL You don’t have enough customers basically.

GT Right.

CL Especially early in the business.

[8:46]

GT Like I think about market forces. I mean, I remember when the pandemic hit and the partners at Postlight, we all sat in a room and looked at one another for a minute and went like, are we gonna make this?

CL I remember that.

GT I feel like risks are constantly sort of coming toward the business. Is there demand for our services? Iis the culture going to change? Are we going to go into a huge recession? Is there a new trend that we should be following but that we aren’t? Are we growing? I really think about growth as a hedge against risk actually, like are we growing enough? Are we creating more and more options so that when one path doesn’t become possible anymore, we have others that we can go down. It’s funny, you’re right. There’s room for success. There’s room for everyone to succeed. But there’s also some part of me that’s like, but is there? [Laughs.] Like we have to do more! It’s a battle between those two mindsets, I think.

[9:37]

CL Yeah. I think room for everyone to succeed is probably not the right statement either. I think there is room for a lot of success where you’re not under—it’s not always like you have to be looking over your shoulder expecting that there’s going to be another company that’s ready to eat your lunch. But I agree with the tweak you made: it’s an endless stream of risk, which may be a competitive company, but it may be something else. It may be like you were saying that trend that you’re not capitalizing on, or you can’t hire. Maybe you’re losing hires to your competitors. That’s interesting. That’s a different way that a competitive threat can materialize. And so I think constantly thinking about risk and how you are hedging against that risk, mitigating that risk. I mean, this is something we talk about every day,

GT Every day. Like I’m feeling anxious about this. What should we do about it? It’s always about mitigating risk.

CL Exactly.

GT What’s interesting about this and something that I really have had to…I’ve thought about and struggled with a lot…is I think that I have this kind of survivalist instinct and this feeling like risks are always coming toward us and we have to constantly mitigate risk. But how you represent that to the company and whether or not you represent that to your employees, right? Because I want to create an environment where people feel like they can grow and do their best work and not worry about whether or not they’re going to get laid off because they’re not, and not worry about their next paycheck. And why I’m so kind of hung up on this topic is I think, I mean, we’ve talked about storytelling on this show before. I think that the stories that leaders tell themselves about what they’re doing and how they’re leading their business and the stories then that they tell their teams about what you’re doing and how you’re doing it really have a huge effect.

[11:10]

CL Completely agree.

GT So you know, we can get up in front of the all-hands and in front of everyone at the all-hands and say [doing a yelling impression] there’s an endless stream of risks that are flying at our faces every single day. [Chris laughs. Gina keeps doing yelling impression.] And everybody has to be just absolutely in their armor making sure that they are protecting their flank and making sure…we don’t do that.

CL Just imagine that all-hands for a second.

GT Could you imagine, right? You could create anxiety. You can be loud, you can say, we’re in a battle for market. You can say we’re in survival mode. But we don’t say that. Because that’s not an optimal environment for a company to grow and for people to do their best work.

CL I mean certainly for our company, I think for a lot of companies like us, it’s not motivating. I don’t think people would walk out of that all-hands thinking, Great, I’m gonna go write 20% more code or whatever. [Both laugh.]

GT Right.

CL It’s going to demoralize me more and it’s going to make me feel unsure. It’s probably going to make me look for another job. And look, the truth is, are we under a constant stream of risks? Yes. Are we also a stable company? Yes. And so we need to balance, I think, and put forward a healthy level of stability. I think you and I have tried, hopefully we’ve been successful, at focusing on the opportunities ahead of us rather than here’s where we’re gonna get overtaken and so we need to make sure we are doing something to stop it. Okay. So let’s go in a completely different direction. Another response that you got was from Chad Dickerson, formerly CEO of Etsy, well-respected in the tech community here in New York. And he said his metaphor for building and running a company is a band. Because there’s a lot of creative work, but also a lot of grunt work like practicing, making sure your gear is maintained, making it to the venue on time. Some people get the spotlight more than others, but each role is critical to creating a great product. I love this one. Very curious to hear what you think.

GT I love this one too. I mean, you and I both love music. And I love the idea of creating something wonderful that people can enjoy, right? This is very focused on the craft and the work and the product. That really speaks to me. And I like that this isn’t about competing or vanquishing competitors. But music, great music, in a band like it is competitive. [Chris laughs.] It’s about the artists that make the best music win out. Yeah. Tell me what your reaction is. Is this one your favorite? I’m curious.

[13:32]

CL I think this one might be my favorite, actually. You know what else came to mind when I read this response was we often say to people, especially candidates we’re talking to who we’re interviewing, that we do the movie model. And what that means is it’s like when you’re making a movie, you bring together a bunch of people, some of whom have preexisting relationships, some of whom don’t, you have to be sensitive to the dynamics between the lead actor and the director and the cinematographer, but everybody’s got to be performing at a high level and working together well for the output to be right. And the parallel is really good to software, right?

GT Yes.

CL If you’ve got a great design, but the implementation is not quite right. Or even if you’ve got a good backend implementation, but the front end doesn’t have the care and the attention to detail.

GT Doesn’t sing, yeah.

CL Doesn’t sing like the way that your designs did, or if you’ve got lackluster designs or if you’ve got a product manager who can’t figure out how to bring it all together, like these things all have to work in concert with one another. And to Chad’s point, which I think is really good, there is like the grunt work of it. Like making sure that on a movie set, you’ve got the AD, who’s making sure that the call times are respected and you’ve got people on set when they need to be. And you’ve got your locations booked ahead of time. All of that stuff has to be good too, for you to stay on time and on budget and make sure that the thing gets made. Again, to go back to the movie model for a second, you disband that team and then you put together a new team and you’ve got some overlap there, but you’ve got new people working together too. And you’ve got to make sure that your dynamics, your team dynamics phase is really good so that you can get to working to there as fast as possible. So I really connect to that. And I really like the idea that creativity is at the core of what we do.

GT Yes.

CL Because a lot of the work that we do is early stage innovative, Hey, I’m a client, I’ve got a problem and I need you to help me figure out how to solve it. There’s no roadmap ahead of you. You are literally creating something as you work with your client stakeholders. So that really speaks to me as what we do and how we are oriented as a business. And as a client services company.

[15:41]

GT I completely agree. Creating something is growing. It’s the opposite of dying, right? It’s subtle, it’s much more subtle, but it also speaks to that survival. Creating something of value, what you’re doing when you’re running a business, right? You’re creating value in a lot of different ways. We create value for our clients. And so I really like that. The focus on this act of creation, the team coming together and doing the grunt work and doing the tedious work in order to make something that is beautiful and lovely and enjoyable and—

CL Yeah. And something people love.

GT Kind of along this line, another response that I got that’s similar to the band metaphor is someone replied to me and said, I like to think of it as gardening. You can’t tell the plants how to grow, but you can construct an environment to influence them in ways that they thrive or not. And ultimately it’s up to the plants to bloom or grow fruit and you have to take care of the weeds. [Laughs.]

[16:33]

CL I get it. That makes some sense. I think this has been part of our growth as leaders is to think about setting up the structure more than setting up the bits within it.

GT Yes.

CL We have too many people now. We can’t spend one-on-one time meaningfully with every single person at the company to make sure that they are on the right path. We do have to think about the environment that people are in and how we set up the environment so that people can both feel personally fulfilled, but also doing their best work and making sure that our client output is the best it can be. I think from that angle, this makes a lot of sense to me thinking about the macro of gardening, as opposed to the micro.

[17:12]

GT Yeah. And I mean if you think about the environment as market forces, whether or not there’s enough sun and light and water, I mean this is about growth, right? The more that your garden grows, the more roots they put down, the stronger that they become, the more resilient they become. I like this a lot. I want to share a final response that I got that I really, really enjoyed, which is actually from the founder of Mailchimp Ben Chestnut, which full disclosure, Mailchimp is a client of Postlight. And Mailchimp recently was acquired by Intuit. Ben in my limited exposure to him through our work with Mailchimp—he really had been doing this for a long time, Mailchimp’s like 20 years old or something. You can tell that his narratives around leadership and around building a company are very well formed, but he responded—it was a very short response. I said, tell me some good metaphors for building and running a company that aren’t sports or war. And Ben responded: It’s a jungle. Tigers are mean. Be the monkey. Which I absolutely loved. [Chris laughs.]

[18:09]

CL It’s kind of great. It’s kind of great.

GT For those of you who don’t know, Freddy is the mascot.

CL Well loved.

GT And this be the monkey—I am sure that if I had Ben in front of me, he would have a whole speech about how the monkey survives, or how it behaves, the way that it collaborates with other monkeys and shares food and stays away from the tigers and all that. And I really, really liked this metaphor. Because it speaks to the survivalist thing. Like making it out there in the jungle, cause it is a jungle. There are days when it’s tough out there and there are tigers. And if you can figure out the behaviors and the collaboration and the creativity and the flexibility and adaptability of just a really great monkey who just wants to hang out in the trees, eat bananas and live to see another day, that’s a mindset I could really get into.

CL I mean, it kind of goes back to what you were saying before, right? The monkey is dealing with the constant stream of risks that it has to think about—

GT [Laughs.] Absolutely!

CL And have an answer for. But they do. They figure out how to survive. They figure out how to adapt and live their best lives swinging amongst the trees. This is just such a great visual also. You’re not on the prowl looking for who to take down. You are thinking about yourself and thinking about how to grow your little monkey empire among the trees. I love it. [Both laugh.]

[19:29]

GT Absolutely. Absolutely.

[Outro music fades in.]

GT This was really fun. It turns out there’s a lot of ways to think about running a business. And I mean, Chris, you and I get to talk every single day. We’ve really gotten to know one another in this process and I’ve really enjoyed it. We have very similar mindsets about how to run a business. And I think the truth is it’s complicated and, and requires a different mindset depending on the situation.

CL That’s right. My go-to now is going to be a band from here on out. I’m going to stick with that. This was great. I would love to hear if people are listening and they have their own way of thinking about their company or their group even if you’re not an entrepreneur, just how you think about growing a team, we’d love to hear it. And we’d also love to hear if you’ve got a particular challenge or something you’re trying to do and you’re having trouble doing it because we may be able to help. We are a full-service strategy, design, engineering product-centric firm with a real knack for actually shipping stuff. So if you need to get something to production and you’re having trouble doing it, reach out: hello@postlight.com and we’d love to talk to you.

GT We’d absolutely love to hear from you. This was a lot of fun, Chris. Thank you.

CL Let’s do it again sometime soon.

GT Definitely. But for now, let’s get back to work.

CL Bye Gina.

GT Bye.