What we talked about
Healey Cypher is CEO and co-founder of BoomPop, a company using AI to help teams plan and host meaningful in-person events. A 4x founder, former COO at Atomic, and former Head of Retail Innovation at eBay, Healey has built and sold companies across commerce, retail tech, and event experiences.
Show notes
Healey Cypher describes BoomPop as an “anti-AI AI company”, one that uses artificial intelligence exclusively to get people together in real life. His motivation for founding it came from a striking statistic: 79% of 18-to-24-year-olds report feeling lonely, a number that crystallized for him what he calls the most important problem a company could try to solve.
What we covered
- Healey identifies loneliness as the core market opportunity behind BoomPop, arguing that despite digital connectivity, humans are more isolated than ever, and that coming together in person is “primordial”, the trait that made humans the dominant species. BoomPop’s AI agent handles the full event workflow: planning, negotiating, booking, building a website, and communicating with guests, so the friction of organizing an event never stops people from showing up.
- On breaking through transactional networking, Healey described opening a dinner conversation the previous night by sharing that he and his wife had struggled to have children. The other person immediately “sunk down” and they spent 30 minutes in genuine connection, his point being that vulnerability in the first three minutes sets the entire tone of a relationship, far more effectively than leading with accomplishments.
- His third company built the touchscreen ordering kiosks you see at McDonald’s, Burger King, and Wendy’s, he deployed them across the top 40 quick-serve restaurant chains before selling that business. He describes each company as “the ultimate form of creative expression,” funded by people who hand you money to build something you believe should exist in the world.
- On company culture, BoomPop runs a weekly “Unicorn Award” where one employee publicly tells a story about a colleague that connects to a company value, then passes the award on. Performance reviews formally rate employees on their values alongside their output, creating accountability that keeps principles off the wall and in daily practice.
- Healey’s personal decision-making compass is his son Theo. When he is unsure about a choice, he asks himself whether Theo, finding out about it later, would be proud of his father. He frames this as “full stack values”, company-level values and personal values should align, and if they don’t, he says, “don’t do that job.”
- He described doing a creative visualization exercise, imagining himself at age 80 or 90 at the end of his life, and realizing that what mattered most was his wife, his children, his parents, and his community, not his company’s milestones. He uses that realization to hold a hard line on not missing his kids’ recitals or his wife’s birthday, even while running an aggressive, VC-backed company.
About Healey
Healey Cypher is a four-time founder and CEO of BoomPop, an AI-powered platform designed to eliminate the friction of organizing in-person events. He previously served as COO at Atomic and Head of Retail Innovation at eBay, and his prior company built self-service kiosk systems deployed in the top 40 quick-serve restaurant chains across the US.
- LinkedIn: https://www.linkedin.com/in/healeycypher
- Website: https://boompop.com
Episode 138 of the PreVetted Podcast.
Full transcript
Federico Ramallo (00:00) Welcome back to the pre-Vera podcast where we spotlight extraordinary people and remarkable talent reshaping our world. Today, we are joined by Hailey Seifer, CEO and co-founder of Boom Pop, a company on a mission to bring people together through human experiences powered by AI. Hailey is a four-time CEO and founder. ⁓
former COO at Atomic, former head of retail innovation at eBay, and a leader who has helped build and scale companies across marketplaces, commerce, events, and technology. He also brings a thoughtful persona philosophy to leadership, grounded in doing the right thing and becoming someone his son can be proud of. Hailey, welcome to the show.
Healey Cypher (00:54) Thank you. Thanks for having me. Appreciate it. This is great. I’m excited to talk. That was a great intro by the way.
Federico Ramallo (00:58) Yes, I’m ex. Oh, thank
you. Thank you. Yeah. I’ll tell you a little bit about the intro because I think it’s important. We’re doers. We build stuff. We do stuff. Right. And then we don’t realize how much stuff we’ve done until someone somebody else pointed at us. Right. So that’s my intention with the with the intro is to, you know, set up the
the conversation by giving you the gift of sharing everything you’ve done and you accomplished. ⁓ So that’s why I do it.
Healey Cypher (01:37) It is a gift.
I love that. Thank you. Thank you very much.
Federico Ramallo (01:41) So tell us a little bit more about you, people meeting you for the first time. What should they know about you?
Healey Cypher (01:50) Yeah, thank well, thank you. First of all, thanks for having me. I’m from the US. I’m from a state in the middle called Nebraska. It’s a small one you probably haven’t been to or heard of. Warren Buffett famously is from Nebraska. So that’s that’s what we got going for us. The plot twist is I grew up in Saudi Arabia for 16 years. And after doing a short stint of consulting in New York after college, I got into startups and I just I haven’t looked back for the last, I want to say almost, almost 20 years now.
I’ve been in Silicon Valley building VC backed companies. I love it. This is my fourth one, as you mentioned. My third one, if you ever walk into a McDonald’s or a Burger King or Wendy’s and you see one of those touchscreen kiosks you order food, you ever seen one of those? We did all that for the top 40 quick serve restaurants. Yeah, it was great. We had some really fun, fun experiences there. And I was lucky enough to sell that and then I kind of…
Federico Ramallo (02:34) Right. Yes.
Healey Cypher (02:46) Looked at myself in the mirror and asked what I want to do in life. ⁓ Do I move to Oaxaca, eat crickets for a while? Turns out I don’t love crickets that much. Or do I get back into building a company? And I look around at the world and I try to figure out what are the long patterns, what needs to be built? And we have right now an absolute problem. And that problem is loneliness. Everyone feels even though they’re so connected on these devices,
They feel more alone than ever. It’s something like 64 % of people say they feel alone. gets bigger at younger generations. If you’re 18 to 24, 79 % say they feel lonely. People aren’t showing up as much or not seeing each other. Remote work is there’s all these tailwinds that are pushing people to this place. And what I realized was there’s probably no higher calling for me than to try to create a company that helps people to physically come together. IRL, we are human beings. I think it’s primordial.
to us. know, humans, we’re not the fastest animals. We’re not the strongest animals. But what have we always done to become the dominant species? We come together. That’s what we do. It’s in our bones. And so what better mission to be on than to pursue that? And that’s what Boom Pop is. Boom Pop is an anti-AI AI company where you use AI, but it’s all to get together in real life. ⁓ You talk to an agent, helps you to plan, negotiate, book the entire thing, makes a website.
Talks to your guests and the whole goal is that you show up and have a great time without ever being dissuaded from actually doing it in the first place because it feels too daunting of a task. So that’s that’s Boom Pop. We’re about three and a half years old. We’re VC backed. We just raised our Series A about a year ago. Things are good. We got a great team and we’re having a lot of fun.
Federico Ramallo (04:38) Amazing amazing ⁓ Yes, let me start by saying I agree that ⁓ People are feeling lonelier the it it’s interesting right the social networks are supposed to connect us, but It turns out that makes us feel long lonelier ⁓ it’s crazy the ⁓ Now with AI we have their companions that are you know kind of replacing human relationships both you know friends and you know
sexual social relationships as well. ⁓ that tendency of people are getting more isolated and lonelier. It’s problematic. I’ve seen that this happening in the US that people are not getting married, right? Or not building a family, right? Which is also I don’t know if a problem is the right word, for people makes them more ⁓ isolated, right?
Healey Cypher (05:19) It is.
for sure. There’s many layers to the conversation, depends where you want to go here, but it pulls the fabric of society as we know it. people aren’t social,
Long way of saying, I think there’s nothing more important that we could be doing than helping people to come together. We spend a third of our life asleep and while we’re up, we spend a lot of it at work. You may as well help those connections get stronger.
Federico Ramallo (06:05) Right, am funny enough. That’s one of the reasons I started doing podcasting because I’ve been going to San Francisco for, I don’t know, 20 years. My company has 10 and I realized I don’t I have a friend there, but you know, ⁓ beyond that, haven’t made any new friends in the last 10 or so years. Right.
Healey Cypher (06:34) Yeah, it’s hard. Yeah.
Federico Ramallo (06:34) in San Francisco, right?
And it’s because everybody’s in their own bubble, right? So, you know, and myself as well, right? So I thought I should do something about it, right? And this is, yeah. And you go to a lot of networking events and it’s so transactional, right? What do you do? What do you do? Blah, blah, blah. And that’s it, right? Right, right. And…
Healey Cypher (06:40) Yes.
great. I love it. It’s a great idea.
You got to break through it. Yeah. Yeah. Which I’m happy to talk about
tactics to do that if you want. I’m happy to share tactics that can help you to break through that if you want.
Federico Ramallo (07:09) yeah, absolutely. That will be very interesting to hear.
Healey Cypher (07:13) Yeah, well, mean, so there’s two things and the context, you know, this, we talked earlier is I run a podcast called don’t be a jerk. And the whole idea is helping people understand that one of the straightest and best path to success is just being a good person doing the right thing. And so one of the things early on that I, I kind of researched with, with some guests independently was what makes wonderful conversations and
It turns out that if you start a conversation, well the first three minutes set the tone of the whole conversation, but if you started out by doing some sort of chest beating, like bragging about what you’ve done, your accomplishments, whatever, it invariably now turns the other person to thinking how they can keep up. So if you talk about some beautiful vacation you just had and how you flew in a private jet and how it was amazing and luxurious, they’re gonna start trying to figure out how they can keep up and they’re in defense mode now.
where if you do the opposite of that and you open up with some sort of vulnerability, like this just happened and working through it, the ease off. And now they’re thinking, gosh, what was the time that happened to me? That was similar to that. And it leads to real conversations and authentic connections. I was at a dinner last night, a networking dinner last night. And there’s a guy that, he’s very fast to talk, supersedes, he’s like move by, move by.
And we sat down and I just hit him with a super vulnerable conversation about how we’d had trouble having kids. And he sunk down. Now we were in it. And we sat there for 30 minutes, just connecting. And as a result, we’re like, hang out. got it. You know, there’s, there’s ways I think to, move past the transactionality that I think, I think it’s only transactional because people don’t know how else to navigate it. And especially in time when people are craving humanity and being human.
you can open that door. A worst case scenario, they don’t lock in it, whatever.
Federico Ramallo (09:12) Right, right. The the the other issue that I’ve seen happening on those networking events is that they’re overcrowded. So you have you meet 30 people in a few hours. And it took me a while to realize that I am a an introvert that decided to become more extroverted. But every once in a while, you know, my my social, you know,
Healey Cypher (09:33) Mmm.
Yeah.
Federico Ramallo (09:41) battery drains very quickly when I meet too many people. ⁓ And ⁓ I end up at the end of those events, ⁓ drained, exhausted, and without the feeling of accomplishment because I met 40 people, 30 people, but have not established a more deeper relationship.
Healey Cypher (09:43) Yeah.
Mm-hmm.
Yeah, yeah, yeah. Totally, totally, totally.
Federico Ramallo (10:11) And this setup is more intimate and allows us to explore more deep conversations.
Healey Cypher (10:18) no question. Yeah. one of my favorite things I have on my pod is I get to invest or get to invite friends of mine onto the podcast. And I realized I never take a second to like interview friends. You don’t really have that scenario. so invariably, every person I brought on, I’ve learned so much more about their background, their belief set. It’s been so fun. So, you know, I think this is it’s a it’s a really fun, fun thing you’re doing. No question.
Federico Ramallo (10:46) Right, right. Yeah, completely agree. mean, I I met so many interesting people through the podcast. It led to my publishing my first book, which is something that I would.
Healey Cypher (10:57) Cool,
I didn’t know about that. Tell me about it. What book is it?
Federico Ramallo (11:01) So a coach, ⁓ he’s in Idaho and he’s writing a book about creativity. we talk about that on the podcast. I invite him to a podcast. We talk about that. And during the podcast, said, you should consider a translation to Spanish because the Spanish market is second biggest language.
You know, now Chinese is getting up there, but, you on the West, it’s one of the biggest. ⁓ So I kind of explain the differences between Castellano and Spanish and, know, and Mexico has a different Spanish than Spain. Right. I was explaining all that. My godfather is from Catalan, is from Catalonia. So, you know, different languages. So I explain all that. Right.
Healey Cypher (11:31) Right.
Totally.
Yeah, yeah.
Yeah.
wow, okay.
Federico Ramallo (12:01) and
Because of my comment, he said, well, ⁓ then you should do a translation. You’re in a unique position to do it. You’re a subject matter expert because you’re a creative. And I said, no, I’m a software engineer. But then during the conversation, I realized, yeah, but I create software and you write ⁓ computer instructions, which is a creative process as well. So we kind of get into it.
Healey Cypher (12:30) for sure. Yeah.
Federico Ramallo (12:34) It was was it was an unexpected invitation. And so I now I’m the coauthor of the book and we’re working on finishing the the version working on the drawings and we’re going to publish it soon. Yeah. And a of the things he writes on the on the on the book, I kind of apply them.
Healey Cypher (12:46) ⁓ that’s great. That was awesome, Cool. Very cool. I love that. I love that.
Federico Ramallo (13:04) eventually on the podcast, right? ⁓ Because, you know, creativity is about the flow, right? It’s about ⁓ he talks about rest. He talks about, ⁓ you know, many things, but it’s this idea of, ⁓ you know, rather than thinking about it is living it right. So through the questions, I kind of become the creative conduct of the guests. Right. Yeah. So, yeah.
Healey Cypher (13:06) Mmm.
Mm-hmm.
Yeah, that’s great. That’s great. I can’t wait. You gotta keep me posted.
Federico Ramallo (13:33) Yeah, I’ll keep you posted. And then the other thing I’ve done is the reason he said you should you’re going to be a co-author is because I start adding a lot of stories in the Spanish version, right? That some of them he you know, he are moving them back to the to the to the English version as well. Right. And the way I explain this is like this, you know, aliens always attack New York. Right. Except the stars.
Healey Cypher (13:53) Wow.
Federico Ramallo (14:03) start through, you know, moving from 1999 that they attacked Buenos Aires for whatever reason, right? But most of the time, you know, everything happens in the US, right? So I localize stories talking about Buenos Aires, talking about Mexico, talking about Spain, right? To make sure that the people that are reading in Spanish, they can relate because it’s the
It’s their places, It’s their journey. The story is their journeys, right?
Healey Cypher (14:34) Yeah.
Yeah. I mean, love stories. get it. That’s great. That’s exciting. That’s a wonderful, a wonderful thing you’re working on. It’s really cool.
Federico Ramallo (14:41) Right.
Yeah, yeah, yeah. So it’s it’s it’s very fun.
Healey Cypher (14:48) Yeah, yeah. Well, that’s a big commitment though too.
Federico Ramallo (14:51) Yes, yes. We were hoping to launch it sooner, but it’s taking a while.
Yeah, but I’m enjoying ⁓ the ride and working towards getting it done, right? Yeah. So at this point, it’s a sheer commitment of, we gotta get it done, right? Yeah, yeah, yeah. Yeah.
Healey Cypher (15:13) is willpower. I did it. Gotta get it done.
Federico Ramallo (15:21) So you’ve been founder and CEO of multiple companies, right? What keeps pulling you back to building more companies?
Healey Cypher (15:30) I was talking to my wife about this. I think there’s two parts of why I love building companies so much. The first part is the, it’s like the ultimate form of creative expression. What an amazing gift. People hand you millions and millions of dollars so you can build the thing you believe should be built on the planet and you get to work with people you really respect and admire.
And together you get to work on something. What an amazing privilege to do. So there’s something about the experience of it which is just so addicting. I think it’s very hard when you’ve been a founder to not do that actually. It depends on who you are and how long you’ve been doing it for but I love the job. I think it’s just the most fun I’ve ever had. And every challenge, whether you’re a millionaire or you’re 10, you’re a 50, every challenge along the way…
You’re learning a ton the whole time, which is fun. And then I also joke with my wife who asks me all the time, she’s a professor. She’s like, why do you do it? And I realized it’s also like the only job I know how to do at this point. I don’t really know how to do anything else. So guess I just keep doing the job, you know?
Federico Ramallo (16:36) Hahaha!
That’s very interesting. I ⁓ can relate with a lot of that. ⁓ we are where we are because we are the sum of all the decisions we’ve made, right? ⁓ And somewhere, serendipity, our own agency, we got where we are, right? ⁓ So.
One of the things I’ve seen about building companies is that we can change the world, right? In a small, hopefully bigger, but we can change the world. And the other thing that I’ve seen on my company is, that I like about building a company is…
Healey Cypher (17:22) Yeah.
Federico Ramallo (17:34) when we hire people and we see how we are changing those people’s life because at the end of the day, those two people, they decide to join us for one reason or another, but now their life is depending on the company being successful. Yes. So I used to think about that as a very big weight, but until I realized, well, yes, it is.
Healey Cypher (17:47) Yeah.
Your decision. Yeah. No, yeah. Totally.
Federico Ramallo (18:04) but also it’s a great opportunity because then we can help them change their life. So it’s not only changing the world, it’s changing people’s life. ⁓ When I see… Yeah.
Healey Cypher (18:09) Yes.
Totally agree. Yeah. And by the way, I just wanted to say too
for one second, which is that also shows that you’re just a great leader. The fact that you, you know, I always feel like being a CEO, being a leader, it’s kind of a sacred oath that you take.
to protect the people on your team and to lead them to things that are better for them. And to a certain extent, it’s because they also then take a sacred oath to their families to help provide. And so the fact that you said you feel the weight of it, it’s not the only feeling, of course, but it’s an important one. It’s actually, I think, like, it’s so easy to have people who are in these higher ranks, management or CEOs, to kind of be…
villainized, you know? And I don’t know that folks who haven’t sat in the seat truly appreciate that the best leaders, this is not because it means you get to drive fancy cars or go to cool dinners or networking. It’s like you’re willing to take the burden on and someone’s got to do it and you think it’s a sacred calling and you do it and you hold that in utmost importance.
I think.
Federico Ramallo (19:29) completely agree. I mean, the I think that pursuing profits as the only mean of the company or the goal of company, I think that’s not the best approach. think ⁓ it’s the more the more I get involved in my company, the more I learn about other people’s companies, the more I realize that having a company that it
Profitable company with a mission statement has a much deeper impact on the world. And yes, the profit is something that we need in order to keep the company alive and stable and pay everybody’s payroll. ⁓ But it’s different when you do it in this way, because now you have a purpose and you can give your team.
Healey Cypher (20:06) Absolutely. Absolutely.
Yeah. Yeah.
Federico Ramallo (20:29) a purpose to pursue.
Healey Cypher (20:30) Yeah, I completely agree. I said another way. If your team doesn’t have a mission and purpose bigger than yourselves.
when the times get hard or the trying is intense or things seem bleak, it’s gonna be a lot harder for them to make it through. Where if it feels like there’s a higher calling, it’s a lot easier. There’s an expression that someone gave me, which is you can have people who are mercenaries just in it for the money, or people that are missionaries in it for the mission. And it’s actually something in between. That’s where you kinda gotta live. You wanna be accomplishing the mission, but not doing it at personal expense.
Federico Ramallo (21:02) Right.
⁓ Right, right. ⁓ Definitely. And again, it’s a for me, it’s a journey of introspection, right? I mean, the more I talk about this, the more I’m realizing other things. But ⁓ I used to think about, I can help software engineers in Mexico to make good money, to have a good, good, you know, good career, which part of part of that it is. But
⁓
This year I realized that I am also trying to help them avoid the pain of migrating. I moved, it was my decision, but it’s a painful process. I wouldn’t change it for the world. I met my wife here in Mexico. She’s amazing. But there’s also the… ⁓
the detachment of, you know, your friends, your high school friends, your culture, your family, right? So there is a cause for that. ⁓ But my parents are still in Buenos Aires, right? So they come and go, we come and go. But, you know, still you have that painful distance, right? ⁓ So the more I think about that, the more I realize I am
Healey Cypher (22:16) Mm-hmm. ⁓
Totally. Yeah.
Federico Ramallo (22:41) helping other people to avoid that painful migration and being able to stay in Mexico and make a good living, have a great career, and things like that.
Healey Cypher (22:51) I completely
agree. It’s wonderful. Where I grew up, there was this massive population of immigrants from a lot of places in Pakistan, but specifically the Philippines. And they are so far away from their homes and they’re doing relatively menial labor and they would just ship the money back because that was what they had to do to take care of their family from afar.
On one hand, it’s very respectable that they did that. And on the other hand, you’re right, it’s heartbreaking. You’re like, gosh, I wish they didn’t have to be away from their family in order to figure out how to survive. So I agree, what you’re doing is a great thing.
Federico Ramallo (23:27) Right, Funny enough, when I was doing the migration, now I am a Mexican citizen, but when I was doing all that paperwork, they ask a lot of things, Like, you need a minimum income, you need a lot of things. But I was hired by my own company, right? And the legal representative of my company was my wife. So every time they ask for document,
Healey Cypher (23:46) Ha
Yeah, amazing.
Federico Ramallo (23:57) we will bring, we brought to the immigration office a printer and a laptop, right? So we need this document. We will print it, give it to them, right? This happened like three or four times in that same meeting. Until one point, the immigration officer got so angry and he said, that is not fair.
Healey Cypher (24:16) No way, that’s so funny.
Why was he trying to do it in the first place though?
Federico Ramallo (24:31) Yeah, I mean, what happens is that usually they ask you for documents, you know, and whatnot, and then you have to go back and go back again. Right. So but but we need the the signature of the legal representative of the company. My wife sign it. Here it goes. Right. Every time we ask for something, you know, and the stamp here is stamped. Right. And the the header, you know, the header with the company name. We had we had papers with the with you know,
Healey Cypher (24:38) Yeah, yeah, yeah. But that’s a great call.
Yeah, that’s right. That’s so good.
Yeah. ⁓
Federico Ramallo (25:00) everything was solved, right? ⁓ it was so funny. So, but it still, was a, you know, a long, you know, long process, right? ⁓ The Mexico is a very warming and welcoming to people. So it’s not an issue, but, you know, other countries are a little bit more hard on the immigration process, right?
Healey Cypher (25:02) That’s really funny. That’s a great story. That’s really funny.
Yes, yes, that’s right. The geopolitical landscape is very interesting right now.
Federico Ramallo (25:35) Yes. So you talk about trying to be a good person every day, right? How does that show up in business decisions?
Healey Cypher (25:51) thanks, man. It’s a great question. you know, I’m learning every single day. There’s a lot of layers that I and a lot of learnings I have as I do this podcast. I think the the North Star I have is the way that I my company to operate and the way I people to feel when they’re in the company.
I want them to feel autonomous. want them to feel trusted. want them to have mastery of worth. I them to have purpose. I want them to have full context, which requires all these things that I have a loving culture that is ambitious, that also is very transparent because it’s very hard to make the right decision. If you don’t know what’s going on, you don’t have context. How are you supposed to do it? So to me, one of the biggest indicators of a successful
internal communication culture is even at the fringes of your organization, everyone knows what the right decision is because they’re so clear on the North Star. And I think that’s part of how you have to operate in order not just to be a good company, but just to have people feel good. ⁓ We are definitely a high empathy question, which means, you know, be conflict seeking because the faster you can find a problem and attack it and solve it, that that speed of decision making typically indicates the speed at which your company is going to be successful.
But at the same time, when you attack a problem, make sure that’s what you’re doing. You’re attacking the problem, not the person. And if someone comes to you in disagreement, the first thing you should do, especially if you’re starting to feel charged, is respond with curiosity. Why do you feel that way? What’s happening here? What led you to this? And you’ll find very often, you’ll be able to get to the place where you understand how someone is seeing other two eyes. ⁓
You know, we have core values that we uphold every week during our All Hands. We have this gift we give called the Unicorn Award and one person in the company tells a story about someone else in the company and how it relates to the company values and how it’s what we’re going to win and they hand it off, which people love. But you know, we even, we’re so tied to our company values that during our review sessions, our like formal performance review sessions in the middle of the year and the beginning of the year, I guess the middle and ending.
Federico Ramallo (27:50) you
Healey Cypher (28:02) we rate people on their values and everyone else rates them. And whatever value is, do you have a great attitude? Do you do what you say you’re going to do? Do you always, there’s all these things that can help you to make it a good place. I think the prominent promise that I give everyone is I will always make the decision that is in the best interest of everyone at the company and gets everyone’s back. I will always get everyone’s back and this will happen in front of them. But more importantly,
it will happen when they’re not in the room. It’ll happen behind closed doors. When we’re in a negotiation with the board, when something’s happening with investors, when there’s some decision that I can make as a CEO, they should all rest confidently that Blake, my co-fan, and I will always make the right decision for the team. And they have to believe that because if that’s not true, then how can I trust that they’re gonna do the right thing for the company behind closed doors? And so that’s the, ⁓ that is the,
There’s a lot we could go into there, but that’s what we try to do. And by the I’ll also give you this one. This is one of my, and you mentioned this, which I loved. So thanks for the research, is if there is a decision where I feel on the fence, I’m not totally sure which way I should go, what the right decision is. I instantly go to my son Theo and I say, if he found out about the decision that dad just made, would he be proud of his dad or would he be disappointed?
And that single barometer has been very, helpful, ⁓ very, helpful in decision making.
Federico Ramallo (29:35) ⁓ I used to have values stick on the wall, work on them very hard and then we kind of set and forget. ⁓ So, yeah, and I realized we need to leave them, right? And the value should be our guiding principles to make a decision, right?
Healey Cypher (29:40) Yeah.
Yeah, don’t do it. Keep alive.
Federico Ramallo (30:00) But I love that your own value is would my son be proud of the decision I’m making.
Healey Cypher (30:09) Yeah, you gotta have full stack values. You gotta have values at the company level and you gotta have personal values and hopefully they’re not that far off. I feel like people are, there’s a movement now just kind of integrating your life into one place where you show up at work the same way you are at home and for the most part I think that’s a wonderful thing and you should make sure that the company you’re at, the values of the company are aligned with who you wanna be as a person. Otherwise don’t do that job.
Federico Ramallo (30:37) Right. Right. Yes, yes, completely agree. I am sometimes on on the podcast we had guests where their kids interrupt the interview or things like that. And, you know, people are I’m sorry, I’m sorry. You know, I believe in embracing the family into what we do. Right. ⁓ So you usually ask, you know, do you
Healey Cypher (31:00) Yeah, totally.
Federico Ramallo (31:06) Can I, you want me to cut out your kid from the video or, you know, it’s okay if we leave it. ⁓ You know, most of the people are okay, but I want to make sure. And then I work on the audio. had a real, a founder that was, ⁓ her daughter asking for attention. So we did half of the interview with her daughter asking for attention. So I work on the audio.
Healey Cypher (31:13) Mm-hmm.
that’s really cute.
Federico Ramallo (31:35) to make sure that the conversation could be listened correctly. ⁓ But I left her daughter on the video, right? Because I think it’s important that we ⁓ are, as founders and CEOs, we take care, we have a solid foundation of family, ⁓ coaches, everything, so we can be emotionally ready to tackle whatever challenge we have on the come.
Healey Cypher (32:04) Totally. We were in Toto Santos over the holidays, ⁓ which is a beautiful place north of Cabo, which I’m sure you know about. And I ran across this book at the Airbnb we were staying at that had this wonderful exercise they called creative visualization about the ending of your life. And it’s this idea that I think especially as a founder, it’s easy to pursue what I call resume virtues.
So what are the things I can do now to really stack up my LinkedIn profile, stack up the intro you made, you know, just feel like I’m accomplishing a lot. And then to query whether you want to pursue a life of resume virtues or eulogy virtues, which is basically by the time you die,
what is the most important thing to you? And this exercise, which was so impactful to me, was effectively, you go forward in your mind, all the way to age 80, 90, 100, as old as you think you’re basically gonna get. And you wake up and you ask yourself, across every aspect of life, learning, work, relationships, lifestyle, know, everything, career, money.
what has happened, that is your ideal life, that is the best possible life you can imagine. And the most fascinating thing is when you do this exercise and you then distill it down to what you think matters most in life, while in this moment in time, the most important thing might be get the company off the ground, make it successful, let’s get all these things going to unlock as a result.
At the ending of life, what became very clear to me at least, was that the most important thing to me was my wife, it was my children, it was my parents, it was my family, it was my community. And that’s who’s going to be around me in my death pet, I hope, if I’m lucky. And that’s who I want to build relationships with now, know, don’t sacrifice those things. Because I see a lot of people who, they put all of their life energy into certain things.
that end, know, companies can end, jobs can end, and then they have not much left. And those people that I’ve seen have done this, it’s been really, really hard to see them when they retire, because they’ve just lost their way. Where if you go, look, yeah, of course, I’m gonna work my butt off on this company, and I’m gonna be aggressive and I’m attack it, but I’m still not gonna miss my kids’ dance recital. I’m gonna be there for my wife’s birthday, and I’m gonna make sure that when I do Valentine’s Day, I’ve thought ahead about the card, whatever the things are.
You have to balance out those investments because otherwise I think it’s a road to, well, it what you want. But to me, that wasn’t the road that I want to get to. Of course, I want to continue to be a founder and be very successful and I want to the biggest company I’ve ever built, no question. But also, on my deathbed, I want to be with my wife. I still want to be with her.
Federico Ramallo (35:06) Yes, yes, I know what you’re talking about because it’s the story of the fisherman and the American, right?
Healey Cypher (35:16) Yes, that’s yes, that’s
the story. That is a story. Was it like the fisherman in the HBS grad or something, the Harvard guy? Yeah.
Federico Ramallo (35:24) Something like that, yeah, yeah, yeah.
I heard multiple versions, but it’s the same idea. Now, ⁓ that doesn’t mean that we have to live in a small shack with no water, right? Or whatever it is, right? No running water. But that doesn’t mean that we also have to work so many hours a day and just ⁓ put that on top of everything, right? ⁓ Yeah. mean, there is a, I mean, the most successful people,
Healey Cypher (35:29) It’s a great idea.
Yeah. Yeah.
Federico Ramallo (35:54) are working many, many hours, 12 hours a day, nonstop and whatnot. ⁓ So are willing to sacrifice a little bit of that? I don’t know if sacrifice is right word. Let’s maybe, but you are aiming a little bit lower, but you have a much more balanced life. And I think that’s a much richer life.
Healey Cypher (36:18) Yeah, yeah, well, yeah, there’s a lot to unpack there, but totally agree. Totally agree.
Federico Ramallo (36:24) ⁓ I feel the same. I am blessed to have the time to spend it with my son. I’m coaching him. We’re training on karate. So we go to train. ⁓ I coach him as well. And I can spend time with him a lot. My parents did something similar where they ⁓ quit their ⁓ corporate jobs to…
Healey Cypher (36:37) Nice, it’s great.
Wow, really?
Federico Ramallo (36:53) spend time with me and my brother. So, yeah. And they basically gave up a safe job, right, to spend time with us, because they would be out from 8 a.m. to 7 p.m., right? So we would never see each other, right?
Healey Cypher (37:06) Amazing.
Wow, this is working.
Yeah, yeah, yeah, I mean. And of course, you know, I think this is the also thing too, you have to recognize that.
Federico Ramallo (37:15) Yeah, so I.
Healey Cypher (37:26) Not everyone has the luxury of that decision either. There’s some people that they gotta work two or three jobs just to get by and they can’t. As founders, anyway, I just wanna recognize that for a second, that I think everyone can do what they wanna do in life and they can find their way, but sometimes the starting line really matters. Are you lucky enough to be in a, you know.
Federico Ramallo (37:35) Right.
Healey Cypher (37:55) a bountiful country when you were born or you not? And then how do get out of there? And what do do about that? you know, there’s it’s complicated. Being a human, turns out there’s a lot to it.
Federico Ramallo (38:08) Yes, yes. I mean, I believe we’re living a very privileged life that we design and we choose. I hesitated. I don’t know if this is the right word, we made the decision to stay in Guadalajara. We could have been in San Francisco. It was one of the options. We explored Ireland as another option. I’m a Polish citizen, so we could go there as well.
Healey Cypher (38:13) Yes.
wow, that’s cool.
Federico Ramallo (38:37) Yeah, from my mother’s side, she, so I’ll tell you the story very quick, but my grandparents from my mother’s side, they are from a small ⁓ town in Poland called Lodz, and both moved to Argentina when they were like three years old, four years old. And then they met in Buenos Aires and they got married. So, you know.
Healey Cypher (38:58) wow, okay.
Federico Ramallo (39:06) What are the odds, right? It’s a 5,000 people small town, you know, and they meet so far away, right? And they’re both from the same small town, right? ⁓ So anyway, the… ⁓
Healey Cypher (39:17) That’s really cool. It’s really cool.
Federico Ramallo (39:23) I thought about moving to the States in San Francisco. We kind of decided to stay in Guadalajara, right? ⁓ Sometimes I kind of second guess a decision. Sometimes I think it’s better, right? I don’t know. I still kind of waited, but what I’m trying to say is that we make that choice and that allow us to, you know.
to that and many other choices that allow us to have a privileged life, right? So we acknowledge that and we recognize it and appreciate it. And I see other people in Mexico and in the US, you know, going through hard times, right? Harder than us, right? So, yeah.
Healey Cypher (39:58) Yeah, it’s great.
Yeah, yeah, yeah, I respect that.
Federico Ramallo (40:09) Hailey, I truly appreciate you being here. Any final remarks before we wrap it up?
Healey Cypher (40:15) You know, I think ⁓ if there one takeaway that I hope someone has, it is the fastest and best way to be a successful person on the planet is just do the right thing for other people, support other people and give. And if you can do that, it is a lot, lot easier to get the right way to go.
Federico Ramallo (40:35) Amazing Haiti. Thank you very much for joining us today.
Healey Cypher (40:39) Yeah, thanks a lot, man. This is lot of fun.