#18: Paul English, Boston Venture Studio

Welcome to From Startup to Grownup, the podcast. My name is Alisa Cohn. I'm an executive coach, an angel investor, and the author of From Startup to Grownup. Each week I talk to founders, creators, advisors, investors, and builders of all kinds about their insights and experiences in going from startup to grownup. This is episode number 18, and I'm thrilled to welcome Paul English to the podcast. What can you say about Paul English? He's like an 8-time founder, possibly most famous for co-founding Kayak. And we talk about how he met his co-founder Steve Hafner and how they decided to co-found the company together. Paul is also known as an incredible hirer, and we go step by step through his process and specifically about how he figures out how to hire somebody within 7 days of hearing their name. There's all that and more in this discussion, so please enjoy my incredible conversation with Paul English. Paul, welcome to the show. I'm so happy you're here today.

Alisa, it's great to be here. Thank you.

Well, you know, we talked about this a little bit in our pre-chat that we have a few things in common. We're both from Boston. We both got our start in the startup scene in Boston, actually. And we actually both have face blindness. And I'm wondering if you could share with people what face blindness is and how that's kind of affected you.

Oh my God, it's, um, it's so bad. I think it's some combination of face blindness and social anxiety. But like, when I go to an event, which I don't really like cocktail parties, I'm great one-on-one. Like, I like meeting people and hearing their story. But if I go to a cocktail party and someone walks up to me and they start talking to me as if they know me, but I don't recognize them, I panic. I always feel like, oh my God, I'm such an idiot for not remembering this person, who they are. But I do often remember sort of elements of conversations. And so you can jog my memory quickly back to a conversation we had because I'll remember the conversation. But I don't know what it is that I don't always remember faces. I feel bad about it.

I know. Well, I can relate to that. I mean, when I found out there was a thing called face blindness, it made me feel so comforted. Like, oh, that's why I don't recognize people. In fact, I've had an experience. I've been talking to someone at a party. They circle back 20 minutes later and I reintroduce myself because I forgot who they looked like.

I've totally done that. I've totally done that. And then I mean, I've even— like, I've gone to parties and I'll say to someone, oh, it's nice to meet you. And they'll say, meet you? I had dinner with you a month ago.

I'm like, oh my God.

Totally. Right.

I can relate to that. And I've also developed strategies to deal with it. Data. I'm really good at data. So they'll refer their conversation, I'm like, "Oh, right, we had dinner that night of that thing." And it's like helpful to, like, for some reason to have that element. Have you— I'm just curious if you found any silver linings in having face blindness.

Maybe it makes me more childlike. I love how children look at the world. Children are curious about everything. Like, they want to know everything. They ask a million questions. And so maybe having face blindness means when I walk into a room, there's something to discover, like who did I meet, who didn't I meet? So maybe there's that discovery thing that happens.

Yeah, yeah, I think that's great. Right, so every sort of new event is like an adventure, like an anthropological adventure kind of. That's great. Now Paul, you grew up one of 7 kids. This is like an oft-told story. You had 15-minute increments to go to use your one bathroom. And you were sleeping in the attic at various times with, you know, with your brothers with no AC and no heat. So that's like a thing. I guess I'm curious with your, your family background, were there entrepreneurial roots in your upbringing? Cuz you really grew up with modest means. I'm just wondering if you saw entrepreneurs or if you had an entrepreneurial spirit early days.

The only thing I can say is, um, my dad was a pipe fitter, so he worked on heating systems. And he worked for the same company for 49 years. His only break was in the middle when he, um, fought in World War II in Germany in the American Army. But aside from that stint in Germany, he worked for one company for 49 years. I think he ended up at the end of his career there. He was running customer service. And then at one point he was superintendent for all the buildings and construction. And through my dad, I learned the trades. So electrical and carpentry and plumbing and automotive, because he could do a lot of stuff. So he taught me and one of my brothers all that stuff. Stuff, but he was very scrappy in terms of, um, he would always say, oh, anyone can get that done with the right tools, but it takes a real mechanic to figure out how to do it without the right tools. And I liked his creativity in that way. And he also was a negotiator. I used to go with my dad to garage sales a lot on the weekends, and almost as a hobby, he would buy and sell air conditioners. So he would take someone that had an old window air conditioner that they're selling, and maybe it didn't work And he would buy it and fix it and sell it. He'd buy it for $20 and sell it for $100. He'd be so proud of himself. And I would watch him negotiate, you know, and talk them down on the price. One day when I sold my first company, this back in '99 or something like that, during the dot-com 1.0, I sold an e-commerce company for $33.5 million. And when I told my father that I'd sold the company, it was a company that I bootstrapped with no investors.

That was Boston Light.

Boston Light. Exactly.

Boston Light.

Exactly. Yeah. Yeah. And when I told my dad I sold it, I was like, you know, kind of proud of myself. Hey, I just made $30 million. And my dad said, did you have lawyers negotiate for you? And I said, no, I negotiated. And he said, how did you learn how to do that? I said, dad, I've been going garage sales with you my whole life. I just watched how you negotiate. I added a couple zeros, but I literally used all the same techniques you use in garage sales.

That's amazing. Was he happy to hear that?

He was very happy. He smiled.

So proud. Yeah, that's, that's really great. And I love how you were, you sort of learned at his knee how to negotiate. And also it sounds like you appreciated his scrappy spirit.

Absolutely. He, um, he was fearless. He was kind of a tough guy. He could fix anything, even if he didn't know how to do it, had figured out along the way. And I definitely learned my work ethic from him and my scrappiness that I don't care if I don't know something, I'm going to learn it. That reminds me, my funniest, that just triggered a funny memory from the movie The Matrix, the original one, when Neo says to Trinity, do you know how to fly that thing? And she says, not yet. I don't know if you remember that scene. And then they download the program into the Matrix and then she flew that helicopter.

Yeah. Yeah. I love it. That's so great. Well, actually, on that same sort of make-it-up stuff, you went to Boston Latin and UMass and then ultimately to your first job at Interleaf. And you were an engineer. But when the new CEO came in, he said, "Which department do you want to run, marketing or engineering?" And you said, "I don't know anything about marketing." And he said, "Congratulations, you're the new head of marketing." Is that the true story, the way it goes?

That's a true story. And the marketers were running in the halls going, "Oh my God, what are they doing? They put a programmer in charge of marketing." And I feel bad that I was not a good manager to them because I had developed my skills in product design and user interface design and building a product. And then I didn't know what marketing did. And so I said to myself, okay, I know how to design products. Maybe now what I should do is hang out with the sales force to learn how to sell product. And once I learn how to sell it, then I'll learn how to market it. Maybe my journey was backwards, but I spent a lot of time with the sales force. Innerleaf had a direct sales force. A typical sale was $100,000 for our software. Some sales as much as $1 million. And so I spent a year, you know, traveling a lot with the sales force and learning how they sold the software. And then I learned how to tell a story and how to give the salespeople better tools and better presentations that they could craft a message that was driven from the problem statement, the customer environment, what our technology did. And that's where I started to learn about marketing. I had some great marketers. At the company that I learned from. Uh-huh. This guy David Weinberger who ran marketing at Innoleaf at one point. I learned a lot from him. And yeah, that was the beginning of my journey.

So how— what did— I guess when you said you weren't a great manager for the marketers and it certainly took you some time to figure all this stuff out, how did you approach managing them when you did nothing about their function?

We would have our weekly staff meetings and I would say, what programs have you guys been working on? And we would just kind of brainstorm as a group saying, does it make sense to continue that or should we try something different? And I was a fan. I was doing this balancing where I was a fan of rapid testing because when you do software design, you can build software tests that get feedback immediately and then change the software. Marketing doesn't work quite that well. I mean, some demand marketing, online marketing does. You can buy ads on Google and see if people click on them or not and then change the ad and change the ad and change the ad. But a lot of marketing, particularly brand development, which is something that I have studied now for a long time, takes months and quarters and longer to see if your brand work actually syncs with people, lands with people. So in these staff meetings, I would say, what are the programs we have we're working on right now? And we'd kind of collaborate as a group saying, does this make sense? Does that hunt? Is that a good idea? And we'd try rapidly changing different ideas and different programs. And just through a lot of experimentation, I learned. And I had some great people on the team who taught me a lot.

Yeah. Did you have to gain credibility with them? I mean, you know, I guess I'm just curious how they reacted to you as a manager.

Yeah. The day before, you know, on the Friday, I was Senior Vice President of Engineering, and on Monday I was Senior Vice President of— I think it was product management and marketing. So they knew that I was the guy who could build the tech. And so I had cred that I was technically stronger than anyone in the marketing team, and we were a tech company. So I think they respected that. And hopefully I had a sense— hopefully, I had a sense of humor about the fact that there's so much I didn't know. But I'm a fast learner. And I like working with teams. I like collaborating. And I think I contributed. I'm not saying that I'm the one who came up with all the great ideas. But I contributed. And it was a really fun year for me.

Yeah, that sounds great. I love the collaborative approach. And I'm just curious if you think about, as you know, founders, and really all leaders have this experience of having to manage functions or hire for functions and manage functions that they've never done before. So, like, what would your top piece of advice be for someone who's a founder who is, you know, trying to manage people that they don't know what they do?

So, there's a number of skills that you look for that are generic across any function. If you look and hire leaders, You want people that are charismatic. I'm going to say more about that in a minute. Charismatic, confident, humble, funny, direct, transparent communicators. There's sort of some generic leadership skills you want all your leaders to have, even if they're running a function you don't know about, because those are the attributes which will galvanize a team, which can— like, you want them, all your leaders, to be good storytellers. And becoming a good storyteller is really important in tech. If you're a good storyteller, it means you can recruit. You can get reporters to write about you because you can connect with the reporter. You can raise venture capital. A lot of it begins with that, is crafting the communication and the messaging. So you look for that in all the leaders you hire.

That's great. And so it sounds like you were able to more use the leadership traits that you had to also engage with them And that's kind of how you built up your own profile as well as like the leader of marketing.

I think so. Yes. Yeah.

Yeah. So at some point you left Interlead for this hot startup named Netcentric. And what I've heard you say is that you learned from that experience how startups shouldn't run. So I'm curious how startups shouldn't run as, as evidenced by Netcentric, the general department of Netcentric.

Yeah, that was a, that was a formative year of my life. I worked a million hours a week. I was working 7 days a week, nights and weekends. Um, it was a bit of a crazy place. I mean, the two founders were brothers and they did not get along. And it sort of created a toxic culture to have the CEO and the CTO fighting all the time and not talking to each other. And so the first thing I learned is, whoa, like, you need— if the founders don't get along, how's that going to create a culture where the rest of us can have fun and execute and trust each other and be open with each other? And so that told me that when I go start my own companies, I'm going to invest a lot in the relationship. I've often said that tech companies fail for one of two reasons. They don't fail because their tech didn't work. For the most part, You know, if you decent hire decent engineers, you can build tech which mostly works. The reason tech companies fails is either there's a founder implosion and a toxic culture, which happens all too often. It's really sad. And we could spend time talking about that. Or they build good tech for a problem that no one cares about. And we could talk about that as well, like how to avoid both of those things. But in— I'm also a pretty active investor. I've invested in, I think, 50 companies now, and some have been done extremely well. Many have failed. But when I do pattern recognition across my investments, one of the things that rings true with the ones that were most successful is the founders really invested in their relationship.

Well, I'd love to double-click on both those things. It's like the sort of toxic culture that comes from count co-founders not getting along. What, what else, what else can you share about that, about what you've seen, and then also how to avoid that?

I think the biggest thing is to be— is to realize that the relationship is really, really important. It's not just, can you run engineering and I run sales? It's more like the, the first thing you have to manage is your relationship. It's like a marriage in some ways. I mean, it's not at all like a marriage in many ways, Thank God. But it has some similarities to marriage and families. And you have to invest in it. I've often said, like, when you run meetings, every meeting has only two goals. Number one, to come to good decisions quickly. And I almost want to put quickly before good. And number two is to improve the relationships of the people in the room. And as a founder, if you say one of the products I'm building is I'm building a culture, I'm building relationships. And if you take that really seriously, I probably spend 5% of my time as a psychologist kind of debugging relationships. And if you pay attention and you watch relationships and you— when you see an email where someone is passive-aggressive, don't let that ride by. Like, jump on that and say, what's going on here? Why are we passive-aggressive? This is this This is going to not get you what you want. Um, if you pay attention to meetings, you'll notice things like men interrupt women more than women interrupt men. That's obviously a really shitty thing. But if you're— if you care about the first product a company builds is the culture, is the relationships, if you're serious about that, you don't let stuff like that exist. When you see something that's dysfunctional, you fix it. You know, you go to therapy, you go to counseling. And I've had some great mentors who've helped me with founder relationships. I know Steve and I at Kayak— Steve Hafner was my co-founder. I was the CTO, and he was CEO. He's an extraordinary entrepreneur. And we mostly had a fabulous time working together. But we had our fights as well. And we would get someone to intercede to try to fix it every time we fought.

Can you tell a story about maybe one of the bad fights you had and how you got— help and get it fixed? Was Steve Hafner your co-founder and CEO of Kayak?

Yeah, he was my co-founder. I don't know. Well, we had this agreement that whenever we fought, we said, let's ignore the roles. Let's ignore the fact that I run product and he runs sales and marketing. Let's just say whoever feels more strongly about the issue will win. So if he felt really strongly about a product thing more than I did, even though I disagree with him, I let him win. And he did the same thing for me, for marketing in particular. We would argue, like one time he wanted to put display ads on the site. So graphical ads that showed a picture of a beach. And I didn't want that because I wanted Cocked to be stripped down and really fast and clean and simple. I didn't want to distract our users with display ads, but he just kept asking me to do it over and over and over again. I kept saying no. And finally we came up with a, we negotiated and said, all right, I'll put display ads on the website. As long as under the display ad, there's a little text link that says hide display ads. And when you click it, the ads go away. And he said, that's insane. Why would I do that? Because we're going to lose all the ad revenue. Everyone's going to click that. I said, nope. I predict 2% of people will click that link and they're going to be really happy. We'll lose revenue from those 2%, but they're going to love us that we made it that easy to hide ads. And, um, you know, we found a path that got him what he wanted, got me what I wanted. And it worked really well.

Was there a time where you really got into a difficult altercation, a little kind of a fight, and really had to find someone else to help you solve it?

Yeah, I'm trying to think. We had a phenomenal chief architect at Keck named Bill O'Donnell, or he went by the term— we used to call him Billo. And he was not only our chief architect, he also was in many ways like the third founder of the company. He was very involved in not just technology, but strategy. And sometimes when Steve and I would fight, I'd go to Bill to get him to interpret what's going on between us. And he definitely had Steve's ear and my ear, so he could intercede. But for the most part, the relationship worked. Phenomenally well. And Steve and I, he's still at Kite and we still are pretty close friends.

Yeah. You know, you just mentioned that you've had one kind of guideline or ground rule for how you decided. And what it was, was when you disagreed, that even if you put aside your roles, you know, that he ran marketing and that you wrote technology, and that you would decide, you would kind of give in to the person who agreed, who felt the most strongly. You both kind of worked on that. Were there other ground rules or guidelines that you informally had or formally had that helped you keep your relationship good with Steve?

I think the main thing was the main rule that we deployed, which I don't know that we were ever explicit about it. It was kind of an unwritten rule, but we took it really seriously. And I've been explicit about it in my companies after Kayak is to be 100% transparent with each other. And to go to each other first. Like, I didn't want to hear that he's upset about something through someone else. If he's upset at something, he needs to come to me, and vice versa. If I'm upset at something, I need to come to him. So I think the founders need to just be on the same page all the time, because you don't want the employees playing mom versus dad. Like, one founder says this, the other one says that. You want the founders to be on the same page. So we would, you know, instant message each other constantly throughout the day. Steve worked mostly in Connecticut where we built sales and marketing. I worked mostly in Boston, but we would each go back and forth to spend time together. But in the days we were not together, we would be, I mean, it was sort of the equivalent of Slack, but this is back in 2004 and on. So it was pre-Slack, but we would instant message each other during the day and we were very blunt with each other. And, um, I think it made for a good trusting relationship.

Yeah, I can see that. I think it's important to be able to count on the people. Like, like you said, the relationship with your co-founder is like a marriage and you wanna be able to have that open, those open lines of communication.

Yes, exactly.

So we, you know, we got here a little bit earlier than I thought we were going to, but I wanted to talk more about your relationship with Steve and, and the way you, met Steve Hafner and how you decided to co-found with him. So could you tell that story?

Yeah, it was a crazy story. Um, I had sold my little company, Boston Light Software, to Intuit. I served as VP of Technology for them for almost 4 years. And then after my mom had passed away, she asked me to take care of my dad who had early-stage Alzheimer's. So I ended up quitting my job at Intuit to take care of my father. And I got a lot of help, you know, from my family, but I was kind of the main person on that. But then ultimately my dad passed away a couple years later. I then felt a little bit lost. I was still trying to figure out how to deal with the money that I had made and trying to give away more money. I went to Haiti at the request of a mentor. Saw some difficult things there, came back and basically said, I need to make a lot more money. So I called the only venture capitalist I knew, a guy named Bill Kaiser at Greylock. He set me up the next day as an EIR at Greylock. And my job there was to look at companies for them and to kind of collaborate and brainstorm on ideas. But then one day I got a call from an old boss of mine, a guy named Larry Bond at General Catalyst. And he said, can you come over and look at a company for us. We want your opinion. And I went over, I looked at the company, and on the way out, one of the other partners there, Joe Cutler, saw me. He said, what are you doing here today? I said, I'm meeting with Larry. And he said, there's a guy here named Steve Hafner. He's one of the founders of Orbitz, and he wants to start a travel company. I'd love you to meet him. So he then introduced us. We went downstairs to Legal Seafoods in Harvard Square, and I think we had a liquid lunch. I think we had 2 or 3 gin and tonics, but literally he gave me the pitch. I said, it sounds exciting. He basically said 70% of people who use Orbitz, when they find the flight they want, they then leave Orbitz, go directly to the airline and buy it. And Orbitz made no money. He said, what if we built a website where we didn't let people buy anything? We literally just were lead gen. I said, I thought it was a really good idea. He said he's looking for a CTO. I said I'd find someone for him. I ran informally a group called Boston CTO, which is a bunch of CTOs in the Boston area. And I remember I asked him, how much are you going to pay? And he said $1.50 and, what'd he say, $1.50 and 4%. So $150,000 a year and 4% of the company. I said, that sounds reasonable. I probably can find someone for that. He said, why don't you do it? I said, no, I just sold my last company. I want to create my own company again. And he said, what would it take to have you do it? I said, I don't know, at a minimum 50-50. And he stuck his hand across the table and says, deal. And I just liked how impulsive and reckless he was. I like entrepreneurs that are willing to make decisions really quickly. And I said, yeah, I'll do this. Let's do this. And we had had, we were together for less than an hour, but it's clear that he was really, really bright and very fast.. And we had this really high-speed conversation, high bandwidth. And I think we got, you know, we hit it off immediately and we're both quick. And I think the fact that we, after less than an hour meeting, decided to co-found a company together just meant that for the next 10 years working together side by side at Kayak, we were going to continue to make really fast decisions like that and take risks. And in the case of us being co-founders, I mean, that risk turned out really well because we got along really well.

That's amazing. So I just want to say that in my book, From Startup to Grownup, I have a whole chapter on co-founders, chapter 9. And what I recommend co-founders do is do what I call a co-founder's prenup, which is to talk in advance about how it's going to go and our vision for the partnership and how we handle conflict and all that stuff. So you have just given the lie to, you know, my whole mandate on co-founder prenup. So instead, like, you went off to Vegas and got married to your co-founder. So I'm just curious, tell me, I guess I'm just curious, do you think that sort of thinking in advance and talking in advance to your co-founder about their values and about how they handle conflict is in general a good idea? And just for you, it kind of worked out, or would you say, nah, that's not really necessary, Alisa?

No, I think it's a huge idea. I think Steve and I just got very, very lucky. Yeah. You know, we didn't start working it that day, but I went home that night. I remember I spent not much time, but I spent some time on Expedia because they were the market leader at the time, just saying how hard is it going to be to compete against these guys? So I did a little bit of research on that. I wrote up probably a 5 or 6 page document on how I thought we could compete against Expedia. And then we worked together over the next week and coming weeks to try to form what's the vision for the company, how are we going to structure it, who are we going to hire? And it was during that process of the next— let's just say the next month that we said, yeah, this is going to work. So it's not like we committed over drinks that we're definitely both going to work. We both had been unemployed at the moment. I guess he was actually still at Orbitz in the process of leaving. I was quote unquote unemployed. I mean, I was an EIR at Greylock. But we weren't quitting jobs to do this together.

I see.

And I think the first month of working together just validated that, yeah, this is going to work. You know, we're both good. But I think the thing you said about values, I think is really, really important. I would always say at Kayak, the way I organized my day was, as I thought about how I prioritize my day, it was always team first, customer second, profit third. Which sounds really backwards, but I just really believe that strongly, that if you try to be— if you aspire to be a world-class recruiter and build this magical team, magical teams build magical products, and magical products build profitable companies. So that's kind of my order of thinking. And a lot of the decisions we made along the way, we'd try to optimize for the team first. You know, if a lot of companies say the customer's always right, I think I'm more customer-oriented than most CTOs I've met, but I didn't believe that, that the customer's always right. If a customer got in a fight with one of my employees, I'd defend my employee first and I would read their chat session. And, you know, we didn't let customers be rude to our employees, for example.

Yeah. So it sounds like you and Steve shared that value of thinking that the team was important, that the culture was important, and that you were able to stay in sync also, as you sort of said, even though you lived in different locations.

Yeah.

Using just good communication and being raw and honest with each other.

I think so. Yeah.

Yeah. One thing that you've said a few times now is fast, right? That he was fast, that he was sort of a quick study. You talked about meetings, making fast decisions. And you're known as being a very fast, and I would even say aggressive recruiter of people. In fact, Mike Volpe, the CEO of your current company, Lola.com, he said you're like a python. You just keep squeezing until your prey says yes. You say that you want only 7 days to go by from the time you hear someone's name to the time you make an offer. Can you double-click on that for us?

Yeah. Many people will say, if you move that fast, you're going to make mistakes. You're going to hire terrible people. But what I would say is speed is not the opposite of good. There are many things in the world where you have to go fast. Like, for example, if you work in a Formula 1 pit crew and your job is to change tires, you have to do that really fast, right? Because there's a race going on. If you make a mistake, someone could die. Now, the way that those pit crews run is they're unbelievably disciplined. They're so process-oriented and they've anticipated everything. They have checklists. Each person in the pit crew has a role. And so for recruiting, I think the way to go fast is be disciplined about it. Have a process where you define exactly everything from how you convince someone to meet you And I'll frequently say, I've heard amazing things. I want to meet you. Can I come meet you today? And we can meet at a Starbucks near you. I'll come to a Starbucks near your work or whatever. So getting that first meeting and then everything from when they first show up at your company, we train people how to pass someone in the hallways. I do a lot of work on racial justice. And one of the things I learned many years ago when I took classes on unconscious bias is that in a corporate environment, white people do not make contact with people of color when they're walking down the hall. It's like really awful. And so I'll tell my team that. And I'll say, you know, I took this class on unconscious bias, and I learned this terrible thing. So we need to make sure we engage every single person that comes into our hallway. And even if you're not on the list to interview that person, you are on the list. We're all on the list to impress that person and make them feel home. And so we had rules about how to greet someone in the hallway. And we're very disciplined about the whole process end to end. And I think by being disciplined about it, it allowed us to move fast. And we didn't make that many mistakes.

Can you talk about maybe in real detail the sort of the 7-day process that you recommend, or that you actually went through yourself when you were talking about early days? Like, can you give us an example of a person that you identified and how you recruited them?

Yep. So when I first hear of a candidate, it might not even be the first time I hear their name. It might be the first time I hear them described. I've had someone say to me, oh yeah, there was a woman I worked with back at Google. She was like a director of marketing. She was unbelievable. I forget what her name is, but the fact that they said like she's a director of marketing at Google, she was amazing. I have some competitive thing, like the clock starts ticking. I'm like, I must meet this woman. I must meet this woman. And so I'll be on LinkedIn trying to figure out who she is, or maybe the person will remember the name. And then I try—

Is that a real example? Is that like a real example? Like, did you actually go on LinkedIn to try to find that person?

Yes, absolutely. Many cases I'll be in a meeting with someone like on Zoom, you know, video chat like you and I are doing right now, and they'll be talking about someone and I'll say, can you do an email intro? Because I want, like right now while we're in the meeting, so I want to meet them.. But sometimes people don't get doing that in real time. So I'll be on LinkedIn, I'll find them, I'll connect to them, I'll send them a message. I'm like, that's right. I already sent them a message. Like, I'm really focused on finding people and getting them to meet. And that's my first meeting is I'll always say, I'll come to you, just pick a Starbucks. And then when that meeting goes well, how does that meeting go?

Like, what's your, what's your process for that meeting? Or how do you think about that meeting? How do you approach it? Can you walk us through it? Like an example of that first meeting?

Yeah, there was a guy who was an MIT student named Vinayak Ranade that I heard amazing things about. So I went to MIT to meet him. And first, I want to see if we bond. So I try to be— I'm actually naturally a little bit of an introvert, but I'm so driven in business that when I'm trying to get something done, I've learned how to be a little bit extroverted. So I'll try to be a little gregarious with them and have some fun and be punchy and say outrageous things. And try to connect with them and see if I can make them laugh and just have a good time. And so I met Vinayak, and he's incredibly sharp, and we really clicked. I really liked him. And I thought to me, like, I must hire this guy. So in the process of me recruiting him to convince him to come in the next day and meet my engineers, he happened to mention this other student at MIT. Maybe I asked him— maybe I said, who's the smartest person you met at MIT? And he said, there's a woman named Lanthe Cronus who's like crazy smart. He goes, but you can't get her because she's starting a company right now. And I said, can you introduce me to her right now? And I was in the middle of recruiting him, but when he mentioned Lanthe, I'm like, I must meet this woman. I go, please introduce her to me right now as we're sitting at this Starbucks. So he sent an email to her. And then while I'm convincing him to come and meet my engineers the next day, I convinced her to meet me the next day as well. And I ended up hiring both of them. And my formula is basically there's a Starbucks meeting, call that— so day 1 is you hear someone's name. Day 1 or day 2 is Starbucks. Day 3 or day 4 is first round interview, getting the guy to actually come to the company. And there's a discipline about when they come to the company. Like, the people I put on interview teams, I train them all how to be recruiters, how to energize the candidate. I said, even if we don't like someone, we want them to love us. We want them to be spellbound by the experience. And when they leave, we want them telling their spouse— I once hired someone's spouse that I didn't hire them, but I hired their spouse. But we want them going home and telling their friends and family, I met this amazing company today. So we train people how to get that reaction. And then if that first day interview goes well, I do backchannel. And I have a whole system for how I do backchannel references.. And then I try to get an answer to that within 24 hours. And then we convince him to come one more time. We try to get him to meet 8 people in total for the first day, for the second day. We give every, all 8 people veto power. Like, why would I waste your time interviewing someone if I don't give you veto power? So I shouldn't let you interview someone unless I trust you enough to give you veto power. But if it goes well the second day, we make him an offer on that day. We hand it to him in writing. I basically, when I, when I try to close on someone, I will say, look, you blew our team away. Everyone's excited. Everyone wants you here. We think you'd be an unbelievable fit for this culture. We're excited about what you've done in the past. We think we can do great things together. Clearly, you could work anywhere you want because you have an amazing track record. You interview incredibly well. Of all your opportunities in front of you, do you think— is Kayak the one you want to work for? Like, would you drive a little faster to work in the morning because you work at Kayak? And I try to get them to accept the job before I talk salary. And I'm going, so what do you think? You gonna join us? And they say, are you gonna make me an offer? I'm like, yeah, yeah, yeah, yeah. There's even gonna be like, there's gonna be a salary, there'll be a title, there'll be a boss. Ignore that though. Do you wanna work here? Like, we want you. Do you wanna work here? I try to get them to psychologically commit. And then of course we pay people as well as we can. But yeah, I try to have it done in 7 days and I use a database and every morning I see how long people have been in queue. If someone's been in queue for too long, I'll walk up to the manager and say, why is this person in queue for 8 days? Like, what's taking so long? And we try to outperform our competitors by being better at interviewing. We want to excite the candidate, and we want to move faster. Uh-huh.

You said you train the team on how to energize candidates. So what if I was going to ask you to train the audience right now on how to energize candidates? How would you train us?

First thing you do is when they walk into the room, You shake the hand, make direct eye contact, and just say, I'm excited to meet you. I love this thing XYZ that you did before. And pick something out of their LinkedIn profile, their resume. And it doesn't need to be the thing that made the most amount of money. It means something that you're actually interested in. And just tell them, go, I think it's so cool that you worked on an autonomous vehicle when you were at MIT. That's amazing. How did that work? So find something amazing about them and tell them they're amazing. And then try to be gregarious and fun, like joke around a little bit. Try to be fast. Try to get a really good repartee going with the candidate, sort of back and forth. And there's things we could also double-click on how to become charismatic. I love it.

Please do.

Okay. Okay. Because charisma can be taught. And storytelling, storytelling can be taught. And in an interview, we want my team to come across as very charismatic. And a lot of people in engineering are shy and introverted. Maybe a lot of us even on the spectrum a little bit. But there are still ways you can treat them how to be you can train them how to be engaging with candidates. I often do pair interviewing, and there's two reasons I do pair interviewing. One, if I'm interviewing you, Alyssa, I'm trying to get you to join my company. So right now I'm running a venture studio called BVS, Boston Venture Studio. Let's say I'm trying to recruit you to come run HR at the venture studio. Um, I will interview you, and I'll have someone else on my team join me in the interview. So let's say Alisa She's a producer at the studio. And so, Eliza and I will interview together. There's two reasons you're meeting two of us. One, I want you to see how Eliza and I work together during the interview. I want you to say, "Whoa, these two play off each other really well. They seem to like each other a lot. They get along really well. Maybe that's what it's going to be like if I work here." So we try to demonstrate in the interview what it's like to work here by having two people. The second thing is we use peer interviewing to train people how to interview. So in all my interviews, I have one person that's known as a great recruiter. They might be an engineer, they might be a little nerdy, but we know that they can recruit and excite people. And then we have a person that we want to train to excite people. And so I do this training thing that makes sure that everyone can ultimately have the goal of electrifying candidates.

Electrifying candidates. I love it. So it's also like almost like a mentorship, like part of the pair interviewing is to like apprentice under a master energizer, an electric—

completely electrifier.

I love it.

Completely.

And, and then you said you had a, a process for backchannel. Tell us your process for backchannel.

So, um, I'll ask people for references, and when they give me their references, I usually don't want to call their references because their references are very curated. It's the people that they know are going to say good things about them. However, one of the reasons I ask them for references I'll say, give me 3 people that know your work best and that you think were really impressive. And sometimes they'll give me a reference. I'll say, whoa, that person does sound interesting. I might want to hire them. And then when I'm doing the background check, I'm saying, you used to work with Alisa. I know that you and Alisa worked together at Apple. Tell me about her. But if during that reference check, I like this person that used to be your boss, I'll try to hire her. So I'm always like looking for the next talented person. And there's a trick. If you, if you give me the name of someone, let's say it's your boss and you're friendly with her outside of work, so you guys are really close and you know she's going to say good things about you and she's been prepped. You've told her, say good things to Paul. So the reference check could be a complete waste of time because you pre-programmed her what to say. So I'll tell you a trick. You can say to the friendly reference check to get them to be honest. At the end of it, you say, so you talk to them for a while, blah, blah, blah, blah, blah, blah, blah, blah. Then the last question you say, this has been amazing. I'm so excited about Alisa Cohn. We're going to make her an offer. Can you give me, if she joins us and let's say she comes and runs HR at my company, can you give me a piece of advice? Like, how can I make her stronger? If I'm her manager, what can I do to make her stronger? And then they will tell me your weakness.

So then they'll tell you the weakness, and then are you doing that legitimately to, to make me stronger and support me, or are you also just trying to like find, find the holes?

It's both. It's a fishing expedition. If they say— if they— if that uncovers a weakness, it sounds really scary to me. Like what?

What would be scary? What would be a deal breaker for you?

Uh, if they'll say something like you know, she can come across a little duplicitous sometimes, or she can be a little bit passive-aggressive sometimes, or sometimes she's a microman. She doesn't trust people. There's things like that, those enormous red flags that if I loved you during the process but I hear something like that, I'll then call you again and we'll dig into it. And sometimes, like, I had one woman I hired— I'm not going to name her because I'm going to say something negative about her, but she turned out to be an extraordinary hire.. And in that final question of her boss, her last job, I said, can you tell me how I can make her stronger? He said, well, she tends to work really hard. She, her work quality is good, but she gets really stressed a lot. And the stress level can carry through the office. Like when she gets stressed, everyone else gets stressed. So I said, okay, that's a, that's a real concern. Cause I do not want people to burn out. Like I don't want, I don't want people working a million hours a week. I want them to have great personalized family lives and work life. So I met with this woman again. I said, I just talked to your references and I have this thing. I think you have something where you say name it. I forget what that is. There's something in the interview I just heard about you that you and Tim Ferriss talk about naming something, naming a weakness.

Maybe labeling it. Yeah.

Labeling, labeling it. Okay. So I have something that if you have a deficiency in one area and we want to improve it together as partners, the first thing I do is I name it. So I went to this candidate. I said, I did background reference checks on you. Everyone loves you. Like, we really want you to work here. However, they uncovered one thing which I want to just put on the table. Just name it. It's called you stress out and you stress people around you. We don't want that to happen. We don't want COG to be a stressful place for you. So I'm just naming it now. And if I see it a week from now, a month from now, 3 months from now, I'm going to remind you of this conversation. And by naming it up front, you can short circuit what can become an awkward long discussion because it's hard to give people constructive feedback. But by naming it up front, then when it rears its ugly head and you say, hey, is this a case of you getting like too stressed out? How can we help you remove stress here? I don't want you stressed out. And because you've already named it, you already have permission to talk about it.

We talked earlier about how you sort of just tell everybody, "Here's all my weaknesses." That's also a part of naming. And what it does in all these cases, it takes taboo topics off the table. Like, this is not taboo.

Completely.

We can talk about it. It's normal. Yeah. And it sets you up for a future conversation that you can actually say, "Remember that thing we talked about?" It's super normal because, yeah, we just want to work through it.

Yeah, that's exactly right.

Now, have you ever made a bad hire? You know, I, I, like, you're known as a great hirer. So what's— what, what goes wrong when you make a bad hire? What's an example of a bad hire that you made?

So it's rare that someone makes it through our filter because we tend to be pretty good. Like, we read books about interviewing, we listen to podcasts, we read blogs, we talk about it. Um, so we tend to try to get really better. Every company, I want to become a better recruiter.. And I want to learn even from our new employees. They'll have ideas that I don't have. And so I always try to get better at— we have this hunger to be really good recruiters. And it's rare that someone makes through our filters and they're incompetent at the job. Like when we hire people as engineers, we know they can write code because we know how to test that. The thing that we don't read is the culture fit. Now, there's something I have to say about culture fit. Culture fit, I think, is really important, but it also can be a bad thing because culture fit can also mean they need to look like us and think like us and all be like, you know, middle-aged white men. Hopefully, that's not the case. But culture fit is a good thing if it means we have some common values. Like one of our values is complete transparency. And if you operate in secrecy and you hoard secrets and use knowledge as power and you become political, that's not going to work at one of my companies. So I have discovered that with a candidate. And after we hired them and we tried to talk them through it, and in case where you can't get someone to change, you have to separate because When someone joins my company, I'll always say, okay, yeah, there'll be an offer letter with a title and all that stuff. But for me, as the founder of the company, in addition to your offer letter, there's also a psychological contract between you and me. So let's say, Alisa, I'm hiring you as director of marketing, director of product marketing. I'll say, okay, you have to promise me two things and I'm going to promise you two things. The two things you promised me is one, I'm going to be the best product marketer in the US. Like, I want that hunger. I want everyone to be really good at their craft and to know that they're going to get better and better and better at it. They want to continuously learn. And then the second thing is you have to promise me that you'll be an energy amplifier. I'll say more about that in a second. The two things I promise you as the founder is I'll say, one, you'll have more fun working at my company than any place you worked before. And I don't mean fun like dancing on tables. Not that there's anything wrong with dancing on tables. I mean fun like there's no stress around you. You have an idea, you can build it. You have an idea for new product, you can launch it. Like, give people incredible freedom. And then the second thing I promise them is their skills will accelerate at a faster rate than any place else, because I try to build learning machines. I actually learned a lot from Mike Volpe about that. We worked together at Lola, and he, he was amazing at building learning machines. But, um, on that first one, on that you have more fun. Now, if I hire someone who ends up being like really political and secretive and they use knowledge as power and they try to take people down, what if I keep them employed? What I'm doing is I'm destroying my promise to everyone around them that I promise them that I have more fun working. So how can I honor that promise, that psychological contract, by keeping this person? So if you can't correct people you have to separate.

So true. So walk me through what that separation looks like because of everybody I work with, founders, all leaders, a big difficulty is firing people. They'd much rather look away. They give people another chance. They don't want to admit that we need to part ways. Walk me through what that looks like from the moment you think, huh, by the way, the person could be doing a good job, but feels political and maybe duplicitous and is hoarding information, how do you sort of think of that and see that? And then how does that move towards firing them when necessary? How do you try to correct it? And then how do you fire them if you need to?

The first thing I will do is I'll validate my opinion with some other people that work closely to this person. Like maybe it's just me, but if other people are seeing the same dysfunctional behavior, then I'll take it on with the person. I'll sit down with them and I'll say—

How do you, wait, how do you validate that? Like specifically, what do you do?

It depends how trusted a relationship I have with the— I'm going to say the third party, the third person in my company. If it's someone I trust completely and they know we've worked with— yes, we know we have good intent. We know our job is to protect employees. We both want the same thing. I'll go direct them and I'll be very blunt. I'll say, OK, this new person we just hired seems kind of passive-aggressive to me. It's causing tension. In all the meetings. Do you see this as well? So have the shortcut, be able to go bam, go right to the issue. If it's someone I don't yet have that tight relationship with, but they work really closely with this candidate, I won't name the issue, but I'll say, how's it been for you working with this person? Like, how do you think it's going? What do you think his strengths are? What do you think his weaknesses are? And I'll see if they are observing what I'm observing. So I try to corroborate that the weakness that I have fear over, that, yep, that's a weakness that other people see too. Once I get some corroboration, I then will pull the person aside one-on-one and say, you know, we talk a lot about the values of the company. You know, one of our values is transparency. I just see that you're not transparent with your team. And I can give you a few examples that happened this week. And you always try to give people very, very specific examples. So be prepared. To be specific. And I'll say, we got to change this because you're causing all kinds of stress with the way you're managing your team right now, and this isn't going to work because I can't stress everyone out. And if you can't get people to change, you separate. And I kind of have my script. I know you have scripts in your book about giving people kind of recipes for difficult situations. Yeah, it's basically, I will say, let's meet Friday at 10 a.m. We'll come to meet. I'll have another person in the room. So there's a witness to witness what's about to happen. You'll walk in and I will basically say, Alisa, as you and I have discussed, I've become concerned with your work and your fit here. You know, we talked a bit about this. I have some unfortunate news that today is your last day at the company. I have a package of information here about your severance. We're going to give you, let's say, 2 months severance. I have information here about your health insurance. I'm happy to meet you next week and kind of revisit what got us to here, and I'll spend as much time with you as you want. I don't want to have the discussion today. For today, I just want to let you know that today is your last day. It's non-negotiable. Here's information with your severance package and your health insurance. I wrote down my cell phone number on this document, you can call me anytime and I'm happy to meet you offsite and we can do a post-analysis where I can give you feedback. If you want feedback from me, I'll give you feedback. And in many cases, I'll actually help them find the next job because it's not like they're a bad person. They just don't fit the way we run, but they might fit really well the way another company runs. And so they have been cases where I fired someone and yet I've represented them as a good candidate for a company which is very different than us. Like, for example, little companies and big companies operate very, very differently. There are people who thrive at a big company who would fail miserably at a startup and vice versa. And I've made those hiring mistakes sometimes.

Yeah, by thinking that somebody who is maybe coming from a big company will be able to handle it at your little company, but it not being— that not working, you mean?

Yeah, exactly.

Totally. Yeah. You know, Paul, you are such Obviously, you and I both share a religion of transparency and being direct. And I could totally get that. And I know you look for that also in your interviews. I'm sure you've noticed that when people get into companies, talking truth to power, being direct with the founder, the leader, it's hard for people. How do you insist and make sure that people tell you the raw, unvarnished truth? Even after they join the company and they probably don't want to tell you what's going on?

Well, I would like to be able to get everyone to be able to tell me the unvarnished truth. The reality is some people are going to be better at it than others. There are certain members of a team that will be the truth tellers. And you have to figure out who they are. And the truth tellers are the one that when you have an all-hands meeting, they're the one that asks the tough questions in front of everyone else. And they're the ones that make you squirm because they ask such difficult questions. But everyone in the company respects them for being a truth teller. And so you need to win over the truth tellers first. And you need to make sure they're comfortable to always go with you. And they're a little bit like the canary in the coal mine, that if there's something unhealthy in the company, you want them to come to you and tell you what's going on. And so you need to cultivate your relationship with the truth tellers. Because often those are the opinion leaders in the company. And it doesn't matter where they sit in the org chart. They don't have to be a VP. They might be like, quote unquote, just a programmer, but the programmer who's very influential in the culture. And get really close to those people. But as far as getting everyone to trust, I think I said before, people follow confidence, but they're loyal to vulnerability. If you are vulnerable, people will lean in, and they'll see you as a human, and they'll want to help you. So I think by demonstrating that you're comfortable talking about your weaknesses, people will say, "I feel safe here. I feel safe talking to this person." Right.

And that's a human being there. It's not just quote unquote the founder. It's like there's a human being. Is there an example of maybe some— because by the way, when people stand up in all hands and then tell the truth, as you say, and it makes you uncomfortable, that's an unfun moment. And any normal person can lose their composure. And not know how to handle it. Is there a time where someone gave you unvarnished feedback and was a truth teller, either one-on-one or in a meeting, that made you actually really uncomfortable? You didn't know how to handle it?

There's a guy, I'll name him because he's extraordinary. He was an engineer at Lola. His name was Matt Bachman. And he was a truth teller. And he was the one that, when we had company meetings, would be rah-rah, try to get the troops excited. But something, you know, the numbers weren't right, or there's something that wasn't right. We, we said we're gonna do one thing, we didn't get that thing done, and he would always call us on it. And when Matt grabbed the microphone, I was like, oh shit, what am I going to get hit with this time? But I just really liked the guy, and he was just being honest about what the concerns were. And if he hit me with something that was Like many times I'd say, you're right, we failed, we failed there. We didn't meet our objective. Or I don't know the answer to that. Or that is a very difficult issue. Like we, you know, we have two competing values. They're at conflict and we're trying to decide how to manage that issue. And we're not sure how to do that. How would you think about it? What do other people think we should do here? And so we'll turn it into a collaboration session. Because one, um, sin of a leader is to think that you need to have all the answers. And I think really good leaders will demonstrate that they're good collaborators and that they can— if they're transparent about the problems of the company, they will open those problems up and have the company help work on it. Rather than thinking about this, the founders on one side of the room and all of these employees on the other side of the room, like the opposite side of the room. It's really like we're all sitting around the same table and we're all trying to make the right thing happen here. And if you have really good values and you're clear about them, you can use your values as a guide to help you make your decisions.

Mm-hmm. Yeah. Actually, can you repeat your phrase? You've said that a few times and I love that phrase.

Yeah.

Yeah, go ahead.

Yeah, so people will follow confidence, but they'll be loyal to vulnerability.

Right. How did you learn that?

I think earlier in my career when I was at Interleaf, I had massive imposter syndrome. I was 29. I was a VP or senior VP running a team of 200 engineers, maybe. I don't remember the exact numbers, but it was a big organization. And I was not qualified for that job. And so I had massive imposter syndrome and I used to have chest pains. Like I felt so like I'm in over my head here. And I had certain skills that I felt confident in. Like I was confident in design and technology, but the management stuff was very tricky for me then managing multiple levels. I had never done it before. No one taught me how to do that. So I had to kind of learn on the job. But one day I started being open, initially just one-on-one to a few selected people, about my imposter syndrome. And I found that when I was vulnerable, people would lean in. You literally could watch their body language change, and they suddenly would become your ally. And they would say, wow, this person, this leader is being vulnerable with me. I want to help them. And I learned that early in my career. And then I've tried to model it ever since then. And I've trained other people, particularly if you get promoted a lot young in your career, imposter syndrome is likely. So I train people, this is a technique that can get rid of imposter syndrome completely. And I think it's pretty effective.

Very effective. And since so many founders have imposter syndrome, Also, because, you know, when you think about it, the entry-level position of, uh, as an entrepreneur is leader, the entry-level position. So it doesn't matter how much training you had as a leader before you got there, you're the founder and you're a leader. And imposter syndrome is almost a natural outgrowth of that. Do you find that in the founders that you, uh, invest in and advise and mentor?

I found that in particular with young founders. If there are people who start companies out of college and suddenly they end up hiring people that have more experience than them, they sometimes will feel insecure that, wait a minute, my head of sales has been doing enterprise sales for 10 years and I'm a college student. So I have one of those investments right now that I've counseled that person on. How to deal with it, that his staff has more experience than him. But again, it starts out with— I love the comment you made at the beginning of this discussion about confidence allows— what was it?

The confident can afford to be vulnerable.

Yeah, I love that. So it does start with confidence that hopefully you're in a leadership position because of something you did well. Maybe you never ran a company before,, but there's something you did prior which got you— which set you up to then where the next step is to run a company. And you should have confidence in that, the thing that you did before that made you successful. And you should use that confidence to make you feel safe to be vulnerable about the things you're not good at. And if you're a good collaborator and you study collaboration and you can get other people to help you solve problems, do not take on the burden of solving every problem on your own as a young founder. You know, you need to represent the values of the company. You need to represent sort of the vision for the industry, the mission for your company. But beyond that, you can have people that are more experienced than you and that are smarter than you, and they can help you solve the problems.

That's beautiful and beautiful advice for sure. And, you know, so we're talking about vulnerability. And one thing, Paul, that you have done is you've been very vulnerable yourself and open on the topic of your bipolar. And I would love it if we could maybe explore that a little bit. When did you first recognize that there was something you needed to go— like somehow you needed to go fix something or you need to go see a doctor because you were having experiences that turned out to be bipolar? Like, what was the, what was the marker for you?

So I was 25 years old. I had just been married. It was an intense period of my life. I think Within 1 month, I bought my first house, I got my master's degree, I got married, and I got a new job. All 4 things happened in 1 month. And I was working as an engineer, and I was working a lot of hours, 7 days a week. And I was becoming manic at that stage of my life where I would dream about code. I'd wake up, I'd do designs. I'd write specs in the morning. I'd go in and I'd start. One of the things about when you're manic or hypomanic is you get this grandiosity, this false sense of confidence that you think that you're curing cancer. You think that you have, you know, the next great invention and you start dismissing input from other people and you perceive other people to be slow. So you end up cutting them off and you end up not connecting with people. You become completely disconnected. From your friends, from your family, from your colleagues, because your mind is racing so fast. And I recognized this, that I was disconnecting from everyone, and I was having panic attacks at the time. So at one point I went to my local hospital in Boston. I was having a panic attack, and I talked to them about this. I knew that my mind was racing and I was sleeping very, very little. It was not unusual to go like 3 or 4 or 5 days with only 2 hours sleep.

Wow.

And that's clearly very unhealthy. Like, you cannot sustain that. And it was the mania which pushed me to do that, but I knew it was unhealthy. And so I was diagnosed bipolar at age 25, and I was put on lithium, a drug which helped with the mania but had other reasons it didn't work for me. But then I began this journey of reading books, and there were not a lot of books out then about bipolar or manic depressive illness, as it was called back then. Um, but I began this journey to try to learn, and I'm lucky. People who are first diagnosed today in their 20s and they're bipolar, they're lucky that there's so many resources online right now. There were not that many resources online when I was diagnosed. There was no web, so I couldn't go online to read about it. But I did learn, and it took me 15 years, maybe longer than that, to completely manage illness. And I learned through a series of finding one person I could trust and tell them exactly what's going on and be really vulnerable about telling them about the crazy thoughts you're having. And then I think ultimately you should find one family member, one friend, and one colleague. So find 3 people. And trust them completely and open up. And then knowing that they have your back will give you the confidence. Then you have to find other people with your illness so you don't feel alone and watch documentaries or movies or these days podcasts or books to learn about your condition. And then for me, I experimented with different meds over the years until I found the cocktail that worked really well for me. But it's a combination for me of our meds, Being open, doing years of therapy, and then also my meditation practice and study of mindfulness has helped me quite a bit. So it's all of those things, but it took me a long time. I'm actually starting a new nonprofit now called Bipolar Boston, where I'm trying to accelerate that path for other people who are newly diagnosed bipolar in Boston. We're going to be doing in-person meetings, doing a video series. We're trying to destigmatize. But it's all of those things. Yeah. If you have mental illness, you need to take it on like a project. And I was very good at work. I could tackle a complicated project and aggressively solve it. And you need to take your healthcare like a project that you have to solve and you got to put in the time.

Yeah. Oh, that's— I think that's very wise. That's so wise. Also disclosing it to people, you know, um, when we hold on to our secrets and we have shame, like that's where shame festers. And that's where things get in the way when we have this sort of secret that we feel we can't tell anyone. So I think part of the healing always has to be finding people you can trust and talk to about it.

I have a brother who's a therapist, my brother Tim, and he says secrets are the opposite of healing.

Oh, that's— yeah, that's another good quote. It's so true. You know, Paul, let's be honest, that was a difficult journey. I mean, it has to be when you find out you're bipolar and then you've got a you know, as you said, treat as a project and take 15 years as a slog to heal yourself and to find ways to come to terms with it. Are there any silver linings that you think that come out of that journey for you?

Yeah, I think as you meet other people who have your illness, sometimes it's easier to be compassionate to another person than it is to be compassionate to yourself. There's a type of meditation called tong len It's something I learned years after I started studying meditation. I learned it from a teacher named Pema Chödrön. And with tonglen meditation, what you do is, let's say you have cancer and you have a lot of anxiety about this. Most people think meditation is about you breathe in the light and you breathe out the darkness as a way to like heal and get better. Tonglen is the opposite. It sounds bad, but this is the way it works. Let's say you're struggling with mental health. What you do is you close your eyes and you visualize another person with that mental health issue, and you breathe in their pain, and you breathe out light towards them. And then you think about, you think about a specific person, and then you think about a group of people, and then think about a big group of people, and a big group of people, maybe a million people, and you breathe in the pain of a million people. And you send out light to heal them. And what you're doing with Tonglen meditation is you're tuning your compassion muscle. And when you learn compassion for other people, you can learn compassion for yourself.

Hmm, that's, that's so, um, it's so useful and so beautiful. And I so appreciate that it's, it's so clear that the connection between compassion for other people and compassion for yourself, they're, they're intertwined. You can't you can't escape them, right? It's all the same thing. So it's a good way to train yourself in having compassion for yourself. Yeah. That's lovely. You know, just a few more questions, Paul, before we break here. What do you wish you had known earlier on your entrepreneurial journey?

I keep thinking about this quote you gave me that I keep— the confident can afford to be vulnerable. There's also this analogy that— so I've been very lucky that I work in an industry that if you do well, if you have good teams around you, you can make a lot of money. And you say the confident can afford to be vulnerable. There's also something that the successful can afford to double down on values. And what I mean by that is if you've been successful and you have confidence and you have resources, what— just focus on the next phase is becoming a kinder person, becoming a more compassionate person. And I wish I had learned that. I think I was a compassionate person as a child and as a teenager, but I wish I was even more compassionate. I had a guy that I worked with 30 years ago who reached out to me on LinkedIn last year, and he said, I don't know if you remember me. We used to work together at Interleaf. And one day we were in a meeting and we were arguing and you said, you're irritating me. You need to just do this or I'm gonna fire you. And I, I maybe I even said he was incompetent or something. And when he said that to me, I was horrified. It's like someone stuck a knife in me to be reminded that of a cruelty that I had done to another person. And I apologized profusely and I said, I have no negative memories of you whatsoever. I do remember you and I have positive memories of you. And I don't know what possibly happened that made me be cruel to you that day, but I deeply regret it. And I wish what people had taught me earlier in my career was, is it Maya Angelou who says, people will not remember what you said, they'll remember how you made them feel?

Yeah.

I wish someone had pressed that upon me. And I wish someone said to me, The most important thing you have in your entire life when you're on your deathbed is your reputation. You know, were you a good person? And you earn that every day and you can screw it up. So don't screw it up. Like, be kind to people.

Yeah.

I feel like I've been studying kindness and compassion with a— there's a Buddhism school that I go to in Cambridge. And I feel like through my studies there, I'm learning a little bit more about compassion. And I wish I had learned that stuff when I was 20.

Mm-hmm. That's so well said. And this may be a similar answer, but I am going to ask you this last question. What advice do you have for other founders as they embark on their own journey to turn into leaders?

I would say the first thing is whatever time, the number of hours you spent last week recruiting, you should double that next week. Like spend more time recruiting. It will pay off. I meet so many people from my venture studio right now. I'm constantly interviewing founder candidates and it's exhausting. And a lot of the meetings don't work out well. Like they're not a match for whatever reason. It takes a lot of work, but I've always said magical teams build magical products. So build that magical team. That's my biggest advice.

Paul, I could talk to you forever. Thank you so much for joining me today. You've added so— this has been such a rich conversation. I know people are really going to benefit from it. So thank you so much.

Great. I really enjoyed it. Thanks a lot.

Thanks for listening to From Startup to Grownup. If you like what you heard, give it a review on Apple Podcasts so other people can find it. Find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website, alisacohn.com.