It's time for our Postscript segment where we dive deeper into a topic of etiquette. And today, Lizzie brings us an interview with entrepreneur extraordinaire Paul English. Paul is probably most famous for being a founder of the travel website Kayak.com and after many successes is now a founder at PartyClick.com. Lizzie and Paul sat down to talk about business etiquette. If you enjoy this conversation, join our community membership to hear the extended interview. Audience,

I am so incredibly excited to introduce our guest to you today. In fact, I'm so excited that we don't have enough postscript segments to fill up the amount of time I want to talk to him. This is one that will definitely go over into our extended content for our community members. But today, our guest is one that I am very proud, very honored, and very, very excited to have on the show. Paul English is an entrepreneur extraordinaire, and I truly mean that, Paul. You have worked at, built up, sold, built up and axed so many different companies while also teaching at MIT entrepreneurship. I am just blown away by your lifespan of a career, which started when you were very, very young. You are most famous for being a part of the team, a really integral part of the team that built up kayak.com and then sold it for an extraordinary amount of money. And I am just tickled pink that you are also an awesome etiquette fan. Like that, it blew me away. And in the times that we've gotten to talk since, you let me know that it was really important to you during the pandemic. And I just wanted to take a minute on the show in front of the audience to say thank you so much for letting us know that. It was a really wild time for us at Emily Post and for the whole world. And it really meant a lot to hear that from you. So thank you so much. It's

crazy going back in memory and thinking about, particularly the first year of COVID, how scary it was. I mean, my siblings and I, I'm one of seven. We grew up in Boston together. Six of us still live in Boston. One is in the West Coast. We got together on Zoom calls like every night, seven nights a week for the first two months of COVID. And we were all like really afraid. We were washing our groceries, doing all this cool stuff, like crazy stuff. But I'm telling you, your show was one of the things that got me through. I have always listened to podcasts since podcasts have been around. But I first discovered your show, you know, for me at the beginning of the pandemic. And I just listened to it religiously. And I just love it. And I love Daniel. And I can't wait to meet him in person. And I just love to be together. And your show is very entertaining. And I'm someone who didn't grow up with lots of like etiquette trained in my family. So Emily Post etiquette, but etiquette is something that's become very important to me. And I think a lot about not just in my press of light, but also in my business life.

Yeah. Well, I'm really glad to hear that because we find so often it's not about saying things with a certain type of voice or making sure that, you know, every single little formality in, you know, formality is a part of etiquette, but it's not all of it. where that conversation was like, okay, what's going away? What's staying? How are things changing? I felt like for you to catch us at that moment, must have been really interesting to kind of get introduced to that and exposed to it. But I was thrilled when we first met through your work with new company PartyClick, which is a party invitation communication service. I've used it. I've told the audience about having used it. It makes texting and emailing your invite so incredibly easy. I could basically fangirl all of your business ventures for a very, very, very long time. But because you're an AE fan, I am really bubbling over with excitement to talk to you about business etiquette. You have had so much experience in the world of business. Tell me, how would you define etiquette in the context of business? I'm

going to think about when I lecture on entrepreneurship. So I have started and sold six companies and I'm now running a venture studio and I have five companies under development. So I have a lot of experience starting companies. also started for nonprofits, which has been very interesting in thinking about what lessons are there in running a nonprofit from running a business, how they relate to each other, how they don't relate to each other. But when I lecture people on starting a business, one of the first things I tell them, in addition to having sort of a mission statement or like, what's your big vision? What's the long term goal of your company is really from day one, start talking about the culture of your company. And when you think about the culture of your company, people have written books about it. People put posters up on the walls of their company with, you know, remember the taglines of the company and all that. And that's all fine and good. But when it comes right down to it, the culture of a company is how people treat each other. It's how the employees treat each other. It's how we treat customers. It's how we treat business partners, how we do customer support. Like I used to have this rule at Kayak. Sometimes when you do customer support, you get a really challenging email and the engineers will say, you know, that stupid user, they'll use words more harsh than that. I can't believe someone can't figure that out. And I would always say there are no stupid users at Kayak. You know, no matter how bad our designs are, we're smart enough. We're going to figure out that for any user, they're going to figure out how to use Kayak. Like, you know, we're that smart and we aspire to be that smart. We're going to make it work for everyone. And we didn't let our team denigrate users, even though the users might've been sometimes like really, really technically challenged. Yeah. A lot of it to me, etiquette starts with just how you treat people. And a lot of it is, and I forget the, I can't believe I can't cite your, your tagline because it's been burned into my brain a million times, but a lot of it is around kindness and just, you know, be polite with each other. We all like when people are kind to us. And so a lot of business, again, this, this, you know, we can go, we can talk about this topic for eight hours, but there's things about how you do email, how you reply to email, how you run a meeting, how you call the meeting to order, how you end a meeting, how you give someone constructive feedback when they're doing something that's like not great for the team. But all of it to me roots on just being kind to each other. And when there are disagreements, as there will be in any group together, to always assume good intent of the other party and to try to steer to an outcome by coming to a shared understanding of what are our goals? are we each bringing to this meeting? Like, what's your learnings that make you think this way and make me think that way? And again, it just, it starts from kindness. I

love that. And I really love the example you gave of, you know, when an engineer or someone would, or even someone in customer service would hear about the problem from a customer and they might sort of disparage the customer, right? Like put them in a category of not being with it. That your whole attitude is instead, no, these are all individuals. We're meeting them. We're trying to provide the service. We don't judge the individual that comes up and asks to participate in that service. That in and of itself is pretty mind-blowing stuff right there. And I know it shouldn't be. It should be the way you're thinking. But for so often, it's easy for us to dismiss other people when what they're asking for is inconvenient to us, or it might take us a little extra time to understand and unravel what exactly it is they're having an issue with. And that's true for so many customer service relationships, but to have from the very top down, the message be each and every person matters. And we want each and every person to be able to interact with us well. That's such a place of inclusivity. And for me, it strikes, you were talking about the tagline consideration, respect, and honesty are the three principles. And to me, that speaks so highly towards or so closely towards that principle of respect, where we're really looking at each individual and saying, you breathe, you're you're a human being, you you deserve that respect. It doesn't matter where you were born. It doesn't matter whether you have tech experience. It doesn't matter, you know, sort of what you learned along the way. You're a person. And I love the fact that that mattered to you in the early days of some of these companies and really getting them off on the right foot. I

think about, you know, Lizzie, when you talk about the early days, sometimes when I'm in advance, people will say to me, what advice do you have for the 20-year Paul English? I'm a lot older than 20 right now. And I think about the famous Maya Angelou quote, which is that, I think it was Maya Angelou who said, no one's going to remember what you said, what you said or what you did. They're just going to remember how you made them feel. And I wish someone told me that when I was 20 or 25, when I first became a manager, because we want to leave sort of a good legacy, like a healthy legacy. And we want the people that we've interacted with to have enjoyed the interaction.

Yeah, no, absolutely. Absolutely. You're actually, you're, you're getting me right to my first question that I was, I guess, technically second question that I want to get to, which is if you don't mind a bit of self-reflection kind of over your career, you've you've had a wonderfully rich career. according to the book, A Truck Full of Money, which was written about you, that you were coding for a game. And the game didn't make it to market, but you still, as a young, very young person, got like five grand for it. I mean, it's a real job. Like, that's real money, you know? Especially back in 1980. In 1980. I mean, that was a lot of money in 1980. Yeah, there's

a game called Cupid. I built it for the Commodore platform. I licensed it to a company and the contract was they would pay me $25,000 plus a dollar royalty per cartridge sold. But then they wanted to go exhibit my game at a big gaming conference and they said, we know we're not done with the contract, but can we just pay you five grand bonus right now to give us permission to show your game at the conference? I have a brother who actually has a pretty amazing career in gaming. My brother, Ed English, he was the creator of the Frogger. And Ed Bay said to me, do not give in, do not give in. Don't let them demo unless they pay the full $20,000. But I was like 16 or something. So I said, sure. They paid me the $5, they went to the show and then yeah they went out of business i became so busy i was so busy as a teenager i played in like three or four bands i was playing sports a lot of things that i never got around to trying to remarket to another company sadly the game never saw the light of day but it was a very very fun game um all my friends and family used to play it. It sounded like fun. Yeah. But $5,000 was a tremendous amount of money for me. And it was truly the

start of your career. I mean, if you think about it.

It was absolutely the beginning of my career. And it absolutely taught me that this little computer thing that I play around with, maybe there's a chance to get a job doing something relating to this. And

you now work with your team at Boston Venture Studio. I mean, and there have been, as you say, six companies in between then and now. What changes and growth do you see in yourself with how you manage people, how you work with others? I mean, I know just at Emily Post in the almost 20 years I've been there, I can identify a whole lot of change. I am dying to know what someone with your career span thinks about themselves in terms of where you started and where you are now at managing people and working with others.

I think now just having the benefit of decades of experience in the tech industry and watching people grow in their careers and me learning how to be a better manager. And I think like, I don't think I'm like the world's greatest manager. I try to be, but I think I'm like above average. I think I'm a pretty decent manager. And now when I look at running my little venture studio, every time I bring someone in one of my companies, I'll always say, I'm going to make this your favorite job of your career. Like I really want this to be incredibly, incredibly fun for you. And I take that promise like very, very seriously. So being fun doesn't mean like dancing on tables, although that's encouraged. Being fun means you have an idea and you get to try it, you know, and people will help you and they'll collaborate with you and they'll give you positive feedback and they'll give you like reinforcement. And for me, I try to coach the team to be helping each other and having that fun and taking the, like a little seed of an idea and trying to say, how do we grow this? How do we turn this little concept into a full brand design and a few product design and an ultimate product? And I just have a lot of fun navigating that and sort of steering people along that journey, because some of the people on my team are like 23 years old and they don't have a decade experience building products they're doing for the first time in their career. And they work with other people in my team who might have 10 years or 20 years experience or more. And I love putting that together. You know, someone younger is incredibly bright with someone who might have 10 years, 20 years experience, and they can really learn from each other. And I try to just be a facilitator in all that.

It sounds like, A, like, I mean, the teams that were the sort of more mature mentoring position, I'm assuming these are all folks who must have a great sense of both patience and curiosity and supportive natures. The type of thing that I would think facilitates that kind of good business etiquette between those two generations sort of working together, one having the experience, one gaining the experience, that sort of thing. Yeah,

we have a team of 11 based mostly in Boston. We have a couple of people in New York. And then we have about 30 engineers that are offshore with a team that I've worked for 15 years. And I think about, like, how could I describe a member of my team? Like, what's one description that fits all of them, even though they have different jobs? Like, I've had a marketing, I have a head of design, I've had a product. So I have different roles, but if I had to pick one word to describe all of them, I would say I have 11 entrepreneurs because all of them have curiosity, as you mentioned, and they all want to figure out how to go from a concept to a product. And many times, some of the concepts are terrible. Like I have i think i own 500 domain names and with every domain name i have a google document with the business plan for that idea and i'm coming up with ideas for new businesses like at least once a week once or twice a week and i try not to burn out my team that probably roll their eyes every time i come in and say i have an idea that i had last night but um part of running a studio so running a little bench studio we work on only our own ideas is having the discipline to kill ideas when they're not that good. So I'll come in in the morning and I'll pitch an idea. And if they don't, like, jump on it and say, this is exciting, I want to work on it, I want to research this, check out this other thing which sounds similar. And if people don't work on the idea that I bring to them, I then kill the idea. we try to figure out of all the ideas that float across the group of us, which are the ones we decide to build an engineering team, build a marketing team and build a product. Now,

has that always been a part of how you've operated? Or is that something you really developed and leaned into as a business person throughout your, you know, like as you grew up in your career? Yeah,

I would say it's an evolution. And it's really been the last few years where I try to think about everyone as an entrepreneur. There's a woman on my team, Eliza, who's worked with me for, I think, seven and a half years now. I

have had the fortune of emailing with her. She's lovely.

Yeah, she started as an assistant, but now she's sort of direct operations. She's doing all finance and legal for the group, as well as a lot of IT for the group. And I do think of her as an entrepreneur and she has a lot of great ideas and she starts projects, builds communities. So all of us are trying to make something happen.

Do you find that in that moment where you're presenting an idea, have you gotten better over time at being less attached? Or have you always sort of been able to detach from an idea that people don't get excited about? Because that's, for some people, this is a really hard part of business to learn and to figure out is, you know, how much do I participate and give my two cents? And how much do I kind of hold back and read other people? Yeah,

I would say always speak your mind, like always give your two cents, as you say. But if what you're pitching doesn't resonate with anyone and the people around you are people that you really respect, then abandon and go on to the next idea. I probably have, you know, I've sold six companies now, so I've had some pretty good success, but I probably have ideas for another 60 companies that were terrible.

I

think to be successful, you have to try, you have to get up at bat and swing for the ball and you have to just try. And sometimes you're going to strike and sometimes you're going to get a hit. My first litmus test about whether it's a good idea or not is I have a really ridiculous team around me, very, very talented, very fun people. I pitch to them. If they like it and start working on it, I say, there might be something here. Now let's do some sort of more formal market analysis. But if no one on my team jumps on it, starts working on it, I say, that's probably a terrible idea. And

that's because you've really, you've brought in people who you trust and who you feel good about and you respect their opinions and you're willing to actually listen to them. I think some managers, some owners, some founders, they're the ones with the big idea, you know, or they're the ones that will direct everything. And to me, it's so cool to get to talk to someone who really believes in his team and is willing to hear the good, the bad, the ugly, all of it from them. Tell me something. What's like the best way, if you were going to put on the etiquette expert hat and deliver the advice of how to let someone know that idea isn't moving forward or isn going to fly, or, or if you don't want to go that route, how would you want someone to tell you they're not excited about it?

So I have a woman on my team. Um, she's an entrepreneur in residence running one of my products. She's incredibly talented. Um, not going to

name her right now. Totally understand and very respectful. Yeah,

she'll probably listen to this podcast. She'll know who I'm talking about. She's an incredible entrepreneur, but she pitched me recently on an idea that I didn't love. And when she pitched me, I said, I don't get it. I would never use it. And here's why I'm not sure this makes sense. However, I don't want to be the one that kills every idea. So basically what I said there is, go pitch these other two or three people on the team. If you can get any one of those three people to say, I love this idea. I'm going to start working on it with you. Let's build it. But if you're the only person in the company who believes in it and no one else thinks it's a good idea, we probably shouldn't pursue it.

I think that sounds really reasonable, like a show me I'm wrong, but not in a prove it to me kind of an antagonistic way instead in like, sounds more like the form of an invitation, like, like make me love this, you know, kind of a thing. I really like that strategy. You know, from listening to the show that Dan and I have worked together for almost 20 years now, and we're also cousins and we've formed a bond that I really appreciate and that we have grown over the years. And especially these last couple of years, like I feel like we're really hitting amazing places with our working business relationship. You've had some really incredible business partners over the years, and you called them need-to not just value adds to a company. And I thought that was such a great way to title someone who you really value working with as a need to have. I'm talking about Carl Berry, Paul Schwenk, Bill O'Donnell, and Steve Hafner. I'm curious, what makes relationships like these form the trust and bonds that happen in them where they become your need to haves? I

think it's a couple of things that I look for for these like exceptional leaders in a team. One is you want to make sure they're good at whatever it is they're going to assign them to do. So if you're hiring someone as a software engineer, you want to make sure they can write code and they're quick at writing code and they write good quality code and all that. The second one, which is the other 50% of the equation, you want to be someone that people enjoy working with because we spend more time working than we spend with our families, which is really kind of sad. So if that's true, unless you get to work with a family like you do, and I actually do as well.

True, true, true. But you

want work to be fun. And so you want people that are incredibly enjoyable, they laugh a lot, they enjoy working with each other and they improve each other's ideas. I'm a big fan of improv comedy training for entrepreneurs where you basically learn how to say yes. And someone says something crazy, don't argue it. Just say that's brilliant and you enhance it. And if your startup can operate like an improv comedy skit where you're just helping improve each other's ideas one, it makes it really, really fun. And two, you end up with better ideas that way if it's done collaboratively.

I love it. I absolutely love it. Do you find that you're easy to trust the people that you kind of vibe with when you meet that, you know, it's like when you, when you get a little bit of that, that energy from someone, you're like, I like you, I like your ideas. And they've checked all the, you know, the technical boxes of the things they would need to do for a job. Do you find that trust comes easily or do you find it really gets built over actually then seeing it prove out? So

I believe trust evolves over someone's life and it's four levels of trust. One is you don't trust someone even after they prove themselves. The second one is you don't trust someone until they prove themselves. That's called trust until. The third one is, oh, the first one's called suspicious still. You're suspicious even after they've done good things for you. The second one is suspicious until you don't trust them until they prove themselves. The third one is trust until. You trust people by default until they have, you know, done something to lose your trust. And the fourth one, and I'm kind of on the edge between three and four is trust still. You trust someone, even after they make a mistake, even after sometimes they hurt you, you still trust them a little bit. And I think if you are on the side of type three or type four, like just a very trusting person, it leads to a life with very little stress. And it also leads to, if you're a manager, building a work environment that people want to work at. They want to be trusted. There's two reasons people quit their jobs. Either they hate their boss, which unfortunately happens all too often, or they feel like the voice is not heard. They have ideas and they don't get to implement their ideas. If you're a manager with a lot of trust, not a micromanager who keeps notes and files and folders. And when they send an email, they ask you again tomorrow, Lizzie, where's that email that I sent yesterday? You haven't applied yet. Or you have a manager which sends you an email and then just trust you're going to know what to do with it. Sometimes I might send me an email at two in the morning and you'll get it when you wake up and you look at it and you say, Paul must've been drinking last night. Like this email makes no sense. And I trust you that you will decide what to do with it, whether it's a dumb idea or not. I think trusting people, it creates a more vibrant environment where we just like trust each other. So I really try to build companies where there's a lot of trust and a lot of openness and transparency. Definitely.

In writing the business etiquette book that we're working on, I find that we are constantly writing the words, business is built on trust, business is built on trust. And so many of our goals with etiquette in the line of business is to build that sense of trust so that the business can really happen. You talked about building teams and I was exactly where I had wanted to go. You've built many teams before and I've had the pleasure of getting to hear you talk about your admiration for really, really big companies that function on very, very small teams like Canva, for instance. There's stories about how you've made everybody participate in customer service at certain points over at Kayak, which I thought was brilliant. And I even remember from the book, A Truck Full of Money, a moment where the author talks about you actually removing your desk from a group of desks that were all grouped together because y'all were just having too much fun and not focusing enough on the work. And I love thinking about how someone who's had so much experience chooses to pull a team together. watched COOs fire whole slews of VPs and taken on marketing when you weren't a marketing guy. I feel like you've been all over the world of business and formed, managed, and changed many teams throughout your time. With all that experience, what do you really look for in a good team? How do you as the principal really drive, manage, and protect that? Because when you have a good team, you don't want it to fall apart. You really want it to stay in place. I think I asked you 10 questions in there. I

think of when you say, how do I evaluate a team? I'm also an investor and I've invested in about 60 startups. And when I meet founders, one of the things I look for is a team that kind of has the mojo, which means that when they present, you can just tell they enjoy each other. The same way that you and Dan enjoy working together. You want to meet a team that finishes each other's sentences. They laugh at each other's jokes. They're just like really working as a team, working together, collaborating. And when I meet teams like that that are like very, very bright and just enjoy each other, I want to write them a check even before I know what they're working on. And I've literally done that once. There's a company right now called Pilot.com, and they do bookkeeping services. It sounds boring, but it's actually a very cool company. And when I met the founders, I'm often the judge of the MIT 100K competition. Their team competed for a prize there many years ago for their first company, and I was involved in getting them to win that award, that company. And the company did well. But then when they told me they were creating a new company, I just love the mojo of these founders so much. I said, please, please, please let me invest before they even told me what they're working on. Now they're running this really great company. But it started for me on just when I met the team saying, these guys got the mojo. I

want to work with them. I just feel like you could tell. It's that sense that creeps in. When you think about building a team that you're going to work on, what are some of the things that you do? I mean, obviously, you said you like the energy. You want to have people that meet the skills. But once you've got them there, how do you protect that and keep that going so that it doesn't just die out, fade or change somehow? I

think there's a big difference between managing and coaching and you have to do a bit of both. But the best teams are teams where everyone is coaching each other just a little bit. And when someone comes to me, person A, and says, I'm really struggling with person B, I find they're not listening to me or paying attention to me. I'll say, have you had a conversation about it yet? And they say, oh, I don't know how to do that. And I'm not their manager. You're the manager. Can't you talk to them? And I'll try to train people how to have those uncomfortable conversations, but make them not uncomfortable. And so to train them how to give direct feedback, because I know in my career, I've been the beneficiary of managers that I've worked for, who are incredible at giving me really, really direct feedback. And in an office environment, people appreciate it so much when you're honest with them. And you tell them kind of what's going well, what's not going well to give, and they give you an opportunity to get better. I had a manager named Craig Carlson at Intuit who was always incredibly direct. And I try to model my communication after his. And I think people have really appreciated it. Now what I'm trying to figure out at this stage of my career is training everyone on my team to be able to do this with each other as well. Do

you find that, I mean, here at Emily Post, we talk a lot about how that how matters, the how of that conversation. It's like, yeah, you can say to anybody, I don't feel like you're listening to me or, you know, you're always not doing the full workload or something like there are problems to address, but we find that it is so important how you choose to do it. And that's not a skill we're all born with. It's something you do have to learn. And you have, it's one of those, a little bit trial by fires. You can listen to awesome etiquette. You could read etiquette books all you want. You can admire people who are amazing business people. But at the end of the day, have to hear how that feedback sounds coming out of your mouth for someone else to even come close to receiving it well. And that's even just a chance, right? Like the impact is something that I feel like we're really starting to pay a lot of attention to in the world of business etiquette, much like we have done in the world of our social lives, that just because I think something's a compliment, you might not hear it as a compliment or receive it as a compliment, you know, that sort of a thing. How do you encourage, I mean, you've kind of said you just do, you encourage them to have the conversation and be the person to address it directly. Do you find people go do it? Or do you have to kind of really shove them into that conversation or practice with them a little bit?

I will follow up the next time I meet person A. I will say, how did it go? Did you talk to person B? Can I help you? Do you want to practice with me? Do you want to think it through? And sometimes like one person's had me recently, but you are their manager. Can't you give them the feedback? I said, if someone was struggling with you, wouldn't you rather hear it it from them directly? It's a great gift to give someone feedback and hopefully you do it with some generosity and compassion. You're not trying to torch someone, you're trying to help them and you're trying to help the relationship. Again, I keep coming back to work should be fun. We want our work to be fun. And if that's really one of the key goals in running a company, one of the things of creating a fun company is like we're honest with each other. And we do it in a way that's loving. Can I say the word loving when I'm talking about business? I'm

all for it. Break out the heart emojis, friends.

But

I think what I love hearing you say that is that everything you've talked about, to me, registers as taking care with the people around you. Again, going back to that same customer service attitude that you talked about in the beginning with the customer's not stupid or dumb for not being able to figure out the website or getting stuck on a certain part of it. We need to make it easy for anybody. And it's to me that same care, like applied right directly to your own team of, you know, you want this to be an enjoyable experience.