Trevor Traina, MBA 96, co-founded comparison shopping service CompareNet, his first startup, while at UC Berkeley Haas. Microsoft acquired CompareNet in 1999, marking the launch of Traina’s successful career as a serial entrepreneur—serving as a U.S. ambassador in along the way.
“The weirdest thing for me about being a young CEO was I thought I’d be creating stuff all day long,” he said during a recent Dean’s Speaker Series talk at Haas. “But a lot of what I did was just get inbound queries from my team. Being a first-time entrepreneur was just learning how to channel my own conviction.”
Watch the video of Traina’s talk:
Three steps of effective decision making
Traina credits those experiences with shaping a leadership style that later guided him as U.S. Ambassador to Austria under President Donald Trump’s first administration, and in his current role as chief business officer at Tools for Humanity. Cofounded by OpenAI CEO Sam Altman, Tools for Humanity created the Orb, a device that uses iris scans to verify a person’s identity as human..
Across both startups and government, Traina said effective decision making comes down to three steps: listening, deciding, and communicating—the last of which, he said, is the hardest to master.
“Leading a team means being decisive,” he said. “You have to explain what the decision is and why you came to it … because people can be upset that you didn’t choose their suggestion. But they can’t say you didn’t listen to them.”
It’s a philosophy that has guided Traina well beyond the startup world. After two decades in tech, Traina brought that mindset to diplomacy when he was appointed in 2018 as U.S. ambassador to Austria—the same post once held by his grandfather. At the time, he was leading IfOnly, a digital marketplace providing access to exclusive events and people that donated 10% of its sales. Viewing the ambassadorship as a chance to take those values beyond the private sector, he finalized IfOnly’s sale to Mastercard and stepped into diplomacy.
“I really believe if you’re going to be an interesting person, every five years or so, you have to figure out how to reinvent yourself or learn something new,” he said.
A drive to reinvent himself
As ambassador, he worked closely with 13 branches of the U.S. government from the Department of Agriculture to the CIA, making decisions on economic diplomacy, cultural exchange, and national security. He said the key was learning fast, comparing the experience to “The Matrix”: having to instantly download whatever information necessary.
Since his ambassadorship ended in 2021, Traina has returned to his entrepreneurial roots, founding Kresus Labs in 2022, a next-generation crypto wallet designed to make buying assets safer and easier. Two years later, he joined Tools for Humanity.
Looking back, Traina said what’s defined his career isn’t a single role but the drive to keep reinventing himself. From entrepreneurship to diplomacy to AI, his experiences have taught him how to evolve alongside the world—learning quickly, adapting to change, and spotting opportunities for innovation.
“If you’re doing something that you like and is worthwhile, keep doing it. If it isn’t, wake up, realize it, be honest with yourself, stop, do something different. Because you only have one life, and everyone is in charge of their own,” he said.
Listen to Traina’s talk on the DSS podcast
TRANSCRIPT:
DEAN JENNY CHATMAN: Good afternoon. How are you? I’m Jenny Chatman, the Haas dean. Welcome to today’s Dean’s Speaker Series. I’m absolutely thrilled to welcome back to Haas Ambassador Trevor Traina. The first thing I have to tell you is that he was my student in 1996. Well, graduated in ’96. Is that right? So you started in ’94. He was ’2 and I was ’4. I think that’s how I remember it. Standout student, of course. Ambassador Traina is a serial entrepreneur, starting his first company, CompareNet, while an MBA student at Haas. He sold that company to Microsoft. And since then, has been a founder of four companies, all acquired by leading global businesses, including Intuit and Mastercard. In 2018, he took a pause from the tech industry when he was confirmed as U.S. ambassador to Austria. Ambassador Traina served in that role for four years. As ambassador, he led efforts to deepen Austrian-American relations and is credited with ushering in an era of new closeness between the two countries. And I got to learn about this a little bit last year when we had lunch. He did some really fascinating things there. Ever the entrepreneur, Ambassador Traina recently founded another tech company, Kresus Labs, which aims to be the ultimate hub for managing digital assets. Ambassador Traina also serves as chief business officer at Tools for Humanity. Super interesting company. He served on several boards, including the Fine Arts Museum of San Francisco here and here at Berkeley Haas for a decade on our advisory board, and at his other alma mater, Princeton University. Entrepreneurship is a cornerstone of the Haas experience, as you all know. And we no doubt have many entrepreneurs in the room today who are aspiring entrepreneurs themselves. I’m so grateful that you’re all here. And welcome to Ambassador Traina.
So some quick housekeeping. You should all have a note card at your seat. If you have a question now or any time during the event, be sure to jot it down. Include your name and program, if you would. And my colleagues will be collecting them throughout the event. Then at roughly 1:10, 1:15, we’ll stop the formal interview part of the program and start answering your questions. I’ll now turn it over to our MBA students, Aman Tiku and Cecilia Beltranena, who will lead today’s discussion. Welcome.
AMAN TIKU: Great. A quick introduction. My name is Aman Tiku, as dean said. And I’m a full-time second-year student here at Haas. And Ambassador Traina, it’s a real honor to have you here with us today.
CECILIA BELTRANENA: Yes. My name is Cecilia Beltranena. I’m also a second year full-time MBA student here. Really excited to hear all your experience around tech and entrepreneurship and your ambassador experience here. It’s also a real pleasure to have a Haasie on stage today.
TREVOR TRAINA: Well, thanks for having me. I haven’t been back in a little while. It feels like every time I’m back here, there’s another building. It’s probably a good thing.
TIKU: Great. So let’s go ahead and get started, Ambassador Traina. So you studied politics and international relations a little bit before you went through MBA, as did I before my MBA. And so, it’s really awesome to have a former ambassador here with us for this event right now. And so, for people in the audience who aren’t as aware, you were named U.S. ambassador to Austria in 2018 after decades as a tech entrepreneur. And so, we wanted to understand what intrigued you about taking that role and how your leadership or management style had to change in that role, and things that you learned about leadership from that experience.
TRAINA: Well, everything I learned at Haas. That’s the long and the short of it. No, so I actually grew up in the Bay Area. I grew up in San Francisco. I did my undergrad at Princeton, and then I got a graduate degree from Oxford in international relations before I came to Haas. So I was arguably overeducated in some ways, maybe not. And then, when I was at Haas, I had a deep passion for entrepreneurship and was really hungry to pick up everything I could here to prepare myself for a career as an entrepreneur. And I was lucky enough to be able to indulge that career. So I founded and sold five companies—my first company to Microsoft, my most recent company to Mastercard, a company to Intuit. But I’d always had other dreams. And I really believe if you’re going to be an interesting person, every five years or so, you have to figure out how to reinvent yourself or learn something new. Otherwise, get old and stale. And no one wants that. And believe it or not, my grandfather had been a diplomat. He had three ambassadorships, one of which was also Austria. So I’m the first American in history to take his grandfather’s ambassadorship. And when I was a little boy, I went to Austria to stay with my grandfather, who was the ambassador. So I had a personal connection. I even had stayed in the house that I would end up living in as the ambassador. So that work interested me. And also, I love America. And I believe in the original tradition of America, which is, if people have skills or talents, at some point in their life, they should step in, serve their country, and step back out again. Nothing against careers in government, but I just feel like private citizens should all contribute something to the country. And that was the way that I could give something back to my country. So when that opportunity arose, I just couldn’t say no. And I was running a company I had founded here in San Francisco, a really interesting company; but luckily, we were already working closely with Mastercard. So I was able to replace myself and then sell the company and give it a positive outcome, while I moved on to another adventure.
BELTRANENA: That’s such an interesting and inspiring story. Having led all of these startups and even teams in the U.S. embassy in Austria, how do you define great leadership across all of these contexts? And was there anything during your ambassadorship that fundamentally changed your view of how to manage people or motivate people?
TRAINA: Well, I think some things are constant, and some things are context relevant. So it was a funny thing because I started my first company before I left Haas. And the day I graduated from Haas, I was a CEO. Now, I had a dozen people working for me, and most of them had just gotten out of college. It wasn’t like we were General Motors or anything, but I was a CEO. And that was an interesting challenge for me because I was not much older than them. I was young when I was at Haas and young when I started my first company. And I had all these people coming to me all day long wanting decisions, and I realized a lot of being a leader is giving people decisions that they can use to operate against. Leading a team means being decisive because your employees need certainty in order to be able to perform their tasks. And I remember that was maybe the weirdest thing for me about being a young CEO was I thought I’d be creating stuff all day long, or inventing or coming up with marketing campaigns or whatever. But a lot of what I did was just get inbound queries from my team on blue or red, 10 or 20, this or that. All day long, they needed decisions. And so, I had to learn how to tap into my own compass or certainty because I was the founder of the company. And I actually did have a vision. And one of the weird things, positively weird things, for me about being a first-time entrepreneur was just learning how to channel my own conviction that I somehow had a pretty good sense for what was the right answer. And so, throughout my times building companies, every single one of the businesses I built was incredibly challenging. And all of them had dark and rough moments. It didn’t matter how well known I became or successful, they all had terrible challenges that had to be worked through humbling things. But learning how to channel that was critical. And then transitioning into a government role was really weird. I took Dean Chatman’s class, and I learned about matrixed organizations and talk about the ultimate matrixed organization that is the United States government. It’s in the most-wanted list with its photo. And as a U.S. ambassador, it turns out I held the rank of a four-star general. I was the most important American in Austria, and I had 13 branches of the U.S. government that reported to me, including everything from the Department of Agriculture to the CIA. So I had to understand all of these organizations. What were their objectives? What did they need? How could I be a good leader for them? What was my task in order to allow them to do their jobs?
And you think about an ambassador as being State Department because it’s diplomacy and diplomats and whatever. But I was the most senior American, and I was dealing with everything from drug cartels to UN votes to antisemitism to big economic deals, et cetera. I had to know all of that. And so, it was the same set of skills but applied differently. So I always say, I don’t know if any of you have ever watched the movie, “The Matrix.” But that’s what being an entrepreneur or even a leader is like. You can’t know everything. So it’s like you find yourself in these situations, the guy from “The Matrix,” who steps into a helicopter and he’s like, ‘I need to download the program for how to fly a helicopter because I have to fly it right now.’ And that’s what those jobs are like. You have to instantly be able to learn what you need to know in order to do that role at that moment. I didn’t know much about the Department of Agriculture or genetically moderated foods and why the Europeans don’t want to buy them and how we can get them—that they’re not Frankenfoods. It was all very new. So I had to quickly learn how to do it. And one of my good friends was the CEO of Twitter until a few years ago. And he taught me something really valuable that I’ve always used, which is that he would agree with me that being a good leader is, ultimately, about decision making. And decision making is really important, particularly when you have a big organization and there is disagreement. He said, ‘Trevor, there’s three steps to good decision making. It’s called listen, decide, and communicate.’ So the listen is first. You have to gather everyone around and get all the data. That’s not that hard, but it’s still important. Then you have to decide. For a lot of people, that is hard. You have to munch all this data and come to a decision. And then the last part is what most people fail at, which is to communicate. So you have to go back out to the organization, to all of the people who provided inputs. And you have to explain to them what the decision is and why you came to it. And it’s that step that brings closure and brings the ranks back because people can be upset that you didn’t choose their suggestion. But they can’t say you didn’t listen to them, factor in what they wanted, and ultimately decide. And if you do that well, it’s very hard for them to be out of orbit. People tend to say, ‘Well, I tried. They listened, et cetera.’ And I had a situation in Austria where I had State Department people wanting one thing and the CIA wanting another thing, and I had to ultimately make the decision.
So I did exactly that. I got everyone around the table. I never said what I thought. I just asked them, ‘Tell me your inputs.’ I let them see me writing everything down. And then I came to a decision. And then I communicated it back out. And so, the role was a bit different, but the leadership skills were pretty similar.
TIKU: That’s awesome. Thank you for sharing your insights with us, ambassador. I want to take a further deep dive into your tech experience and, in particular, innovation. So you’ve built companies across three major waves of tech starting in the late ’90s with CompareNet during the early Web1 era. Then in 2012, with IfOnly, in the rise of Web2 and online marketplaces. And now with Kresus and Tools for Humanity in the Web3 space. So how has your definition of innovation in technology and in the world changed across these three decades?
TRAINA: I’m just so glad you didn’t ask me a question about the CIA. Well, let me just see how many people here think you might be an entrepreneur or might be interested in being an entrepreneur? Let me just see, a show of hands. That’s a pretty good percentage of the audience. I was telling the dean, I came here knowing that I wanted to do my own thing, that I wanted to be an entrepreneur, but I had no idea what or how. I didn’t have that great idea. But I think that the process is the same no matter what. And I was here shortly after the dinosaurs all expired. So Web1 was the big deal, the internet. And I don’t love technology, even though I’ve worked in technology my whole career. But it was obvious to me that the internet was a really big deal and that if I wanted to do something with a lot of effort and attention, I should do it in an area that had the most opportunity. Or put another way, you always want to work with a rising tide or the wind behind your back, or pick your natural analogy of choice. It was clear to me that was the thing. And so then, it was just a matter of OK, what is missing? What is something the market might need, maybe they don’t even realize they need, in that area? And how can I realize that? And that’s how I look at all moments. And at every moment, there’s a thing. So right now, obviously, what’s the biggest thing? AI, but also blockchain or quantum. There’s always multiple trends, but it’s not hard to know what the big trends are. What’s hard is knowing, OK, what hasn’t been done yet? Or what will the market want in 24 months? And how can I bring that to market? So whether it was Web1, Web2, or Web3, I always knew where that wave was coming from that I wanted to surf. The question was only just, ‘How will I surf that wave?’ And then as a matter of what ideas are interesting, and what I often found when I wanted to start a company is, I’d usually have two or three ideas at once. That’s not atypical, but I would—wherever I was, with people, it doesn’t matter who, relatives, friends, standing around a keg, whatever, I would just pitch ideas to people. And then I’d listen to myself talk about it. And I would, in my third-person voice, go, ‘Am I convinced by what I’m hearing or not?’ I would say—OK, my previous company was called IfOnly. And IfOnly was predicated on the realization that people were tired of buying stuff and everyone had enough cashmere sweaters or handbags or whatever, and that people were yearning for experiences rather than things that they wanted stories to tell, things to share with their friends, enriching experiences, and that there are all these marketplaces for stuff where there was eBay or Shopify or whatever. But no one had ever built a marketplace where you could go and shop for amazing experiences, large and small, from ballooning over Mount Everest to an hour of chocolate making or tequila education with a bunch of friends or whatever. And so, I thought that sounded like a great idea that hadn’t been done. So I’d go to parties. And I’d say to people, ‘What if there was a place where it doesn’t matter if you have $100 or $1,000 or whatever? You could go and see dozens of really cool things you could do. Would you pay for that?’ And I would just listen to myself pitch it and decide whether I liked the idea or not. The easiest thing and the hardest thing is being honest with yourself. It’s actually not that hard because most of us know in our hearts if something rings true or not, but we have to learn how to listen.
BELTRANENA: Perfect. And talking about trends. And specifically mentioned AI right now. Let’s dive a little bit more into Tools for Humanity. We would like to know, what is it that Tools for Humanity is actually trying to solve today? Why is personhood so important in this era of AI and digital impersonation?
TRAINA: I’m lucky enough to be friends with Sam Altman. And I was working on Kresus, which still exists and is still a very cool app. And that’s like a next-generation crypto wallet and way to buy crypto assets, that’s safer, easier. But I was working on all this. And then Sam took me aside and pitched me on Tools for Humanity. It’s typical of people who are very technical, where they come up with three different names, and they can’t just pick one easy brand name or whatever. The protocol that Sam and his partner, Alex. created is called the World or Worldcoin. And then Tools for Humanity is a company that develops to the world protocol. But the way I like to describe it is, imagine from the same brain that is ushering in the era of AI, the brain of Sam Altman, came the realization that, in this era, we really won’t know what’s real and what isn’t. And even today, by a lot of estimations, half or more of all the activity on the internet is bought or spam-generated, whether it’s comments on social media or product reviews on Amazon or whatever. It’s not real. And so, that will get way more tricky as AI gets more and more powerful. And so, Sam had that intuition. And he figured out that in the age of AI, we’ll need a stronger building block, a stronger tool for building out our networks. And that the most fundamental tool is proof of personhood, proof that you’re a human and not a bot, and that should be ultra-high signal, meaning you can’t fake it or whatever, and that it should be anonymous, that you don’t necessarily have to say your name or where you live or your gender or anything, but that you could prove that you’re a unique human. And both of those things are important. Prove you’re a human, not a bot. Unique means that you’re a one of one. So it turns out there’s only a couple ways to do that and at very high scale, meaning hundreds of millions or billions of people. And that is either your DNA or the unique pattern of your iris. And it turns out that even identical twins have different irises. And so, after several years, Sam and Alex and the team developed this extremely sensitive camera—it was engineered in Germany—that establishes that you’re a three-dimensional human being, not a photograph, whatever. And that photographs the irises and turns the unique patterns into a long, alphanumeric, anonymous string that is used to issue everyone who does it, something that they control on their phone called a World ID. And this World ID is being used globally to build out a network. Now, it’s over 40 million people, where the network is free of bots and free of fraud, and everyone verified in the network is a real human. The cool thing is—I would encourage particularly all the students. You can download the app in the App Store. It’s called World App. And it’s like a black circle with white whatever. And everyone who joins the protocol is given a cryptocurrency called Worldcoin. So it’s almost like—Sam felt like the concept of proving your human is so important that no one company or country should control it. It should be a decentralized protocol. And in giving these tokens to everyone who joins, he’s effectively giving almost equity in the project to everyone who joins. And so, I don’t know what the allocations were today, $100 or $140, something like that, everyone gets just for joining. So it’s a very world-changing idea. I’m at a point in my career, where I think doing things like that are really world changing, that’s what really interests me.
TIKU: Awesome. And ambassador, so you’ve mentioned, AI is the next big technological transformation we’re experiencing. What advice do you have for the MBA students here and other Berkeley students who are interested in AI and want to get involved in this space? What advice do you have for them about how to responsibly participate in this next wave of transformation without getting lost in the hype?
TRAINA: Well, the age of AI is a little different than Web1, Web2, because those were big trends that one could profit from, if one, as I say, surfed those waves. Well, AI is a little different because it is absolutely like a historically large opportunity. I think you actually have to go back to the first Industrial Revolution to find an opportunity of such world-changing magnitude, but it also directly affects employment. So those of you who are thinking about your careers, you should think not only about well, ‘How can I leverage profitably, et cetera?’ But also, ‘What will AI do to change what job functions we currently are aware of.’ Because more routine job positions, like a general doctor, or a general lawyer, or an accountant or whatever, it’s very likely those positions will go away because of AI. So that means for those of you thinking through your career choices, you want to either do something more specialized that can’t easily be replaced by AI or, like the classic cliche goes, you’re either usurped by it or you’re using it, meaning the positions and careers where you’re deploying AI, where you’re the one using the AI, those will be powerful positions to hold in the future.
BELTRANENA: That’s super interesting. Can we go back to your venture around IfOnly, where you tied it back to the philanthropy and these experiences that you were talking about? We also know that you’re on some nonprofit boards. And I know a couple of people here are into social impact and entrepreneurship. So do you believe that business can authentically serve both purpose and profit? Or is this still an ideal we’re trying to chase?
TRAINA: Well, all these things have to be authentic, but I always used to reassure my investors that don’t worry, this is not the nonprofit. If you put money in, hopefully, you will see profit because that’s what investors are owed. But I think that when it is integral and authentic, giving back is a wonderful enhancement to a business. He’s been in the headlines recently. But a dear friend of mine is Marc Benioff. And Marc really did pioneer a lot of this model in the way he built Salesforce. And a certain percentage of both time and money, time of the employees, money of the business, go into making the world better. And it was so ingrained and earnest that I think it works really well. What doesn’t work well is when companies just decide that—their marketing department decides—we need to look different. So let’s talk about being a company that gives back when it isn’t authentic. In the case of IfOnly, we had a model where I mentioned, we were offering amazing experiences, large and small, to the market. And so we said, ‘At least 10% of the value of the experience has to go to charity, and it could go to any charity chosen by the donating organization.’ And so, we work with everyone from Madonna and Lady Gaga to the San Francisco Zoo. And we ended up supporting over 200 different charities and causes. And in some cases, we raised many hundreds of thousands of dollars for very worthwhile causes. But it was extremely integral to our product, so it never felt dorky or faked. It was a great way to promote many causes, and it enhanced the product, and, in many cases, was the only way we could actually get the experience donated. Because the Madonnas and the Lady Gagas of the world, they really don’t need the money, but they have causes they care about or want to raise awareness for. One of our biggest people was Shakira. She had all these things she cared about. And Chris Hemsworth—I got to spend a lot of time with him. He’s a very intelligent guy, has a great cause. So it was very integral to the business. And I think that’s where it works well is when it’s not contrived.
TIKU: Great. Ambassador, you’ve lived many professional lives, as we’ve heard about in this last 40 minutes or so. Tech founder, diplomat, art collector, investor. How do you keep reinventing yourself and staying curious?
TRAINA: Well, part of it is innate. And I think part of it is learned. I’ve always been extremely curious. So I look at the world with wide eyes, and I’m always wondering why, how, whatever. And I think that’s partially what keeps me young is that I’m always approaching life with a yearning to learn. Not everyone is that way innately. But you can train yourself to be that way. And I think it’s really important because we, as human beings, we can grow stale. And it’s like, if you do the same thing year after year after year, it gets a little bit boring—boring for ourselves and boring for the people around us. It’s like, you have to be able to talk about something new or different. I’m the type of person where my mind is just always swimming with ideas and possibilities and potential. And I often think about when I die, what will my Wikipedia page look like? How many different interesting things will be said about me? No one wants to be boring. So I still have a laundry list of things I want to achieve in my life. And I’m half baked. I have hopefully many more years of doing different stuff.
BELTRANENA: That’s amazing. I feel like we all feel that same way and especially right now where we’re all standing at Haas, looking at our future right now with open eyes. We would love to ask you what lessons or mindsets from your MBA experience still influence how you lead or how you make decisions today?
TRAINA: Well, we were talking about this a little bit earlier backstage, but I approached Haas in a very deliberate way, which was, I didn’t know everything about my future, but I knew essentially what I wanted. And I knew I really wanted to be an entrepreneur. I didn’t know what I’d be doing. I just had a sense for what was me and what wasn’t me. And what I give myself credit for is I was brave about that. Even when it seemed like everyone was going to this career fair thing or going to that, whatever. If it wasn’t interesting to me, I just didn’t do it because the only person who I went to Haas for was myself. So with every opportunity at Haas, I was like, ‘Will this help me? Will this be something I want to know later? Will this be additive to my personal adventure or not?’ And if it was, I did it. And if it wasn’t, I didn’t want to work for other people. I didn’t want to work for another organization. I never went to the Career Center. And it felt like everyone was ironing their suit for the Bain interview or whatever. And it’s like, I didn’t want to work for Bain or McKinsey, or I just didn’t. And so, I felt like the odd man out when all my friends at lunch were talking about what interview slot did you get. And I didn’t have one. But you have to be true to yourself. And I did some things here that were a little unusual. So I knew, in the end, I wanted to have my own company. So I designed my own course. And I got credit for my business plan. In my marketing class, I designed the marketing plan for my business, and I got credit for that, too. And the administration was really flexible about allowing me to chart my own path here and to give me credit for that and to give me resources to allow myself to do that. And so, I was brave, and I just took advantage of everything here. When there was someone coming to talk that I thought was interesting, I’d go. And if there wasn’t, I didn’t, just like probably a few are like, ‘Oh, my God, the lunch was free. But why do we have to listen to this guy talk on and on?’ But that’s my advice. And you’re your own advocate. And that doesn’t stop when you leave Haas, whether it’s in your own career or whatever. If you’re doing something that you like and is worthwhile, keep doing it. If it isn’t, wake up, realize it, be honest with yourself, stop, do something different. Because you only have one life, and everyone is in charge of their own. So shame on them if they don’t stay true to that.
TIKU: Great. Ambassador, as we close the moderator session of the Q&A here, or move to the audience Q&A, we want to end every speaker series this year with the same question. And it’s designed to end on a personal human note and really help the audience understand what matters most to you and why. And so, you mentioned there’s a laundry list of things that you’re still looking to accomplish in your remaining years. And so, we wanted to understand here, if you had an extra week just dropped into your life, what would you want to be doing with that time and why?
TRAINA: Well, I’d go back to Haas, of course. Learn everything that I missed out on the last few years. No, honestly, if I had one more week, I would spend all of it with family and close friends. I’m very proud of my career, and I’ve created many jobs, and I’ve made investors lots of money. And I’ve served my country, I think, probably, hopefully, admirably, and successfully. But at the end of the day, family and friends are the most important thing. More than business or money or anything else.
BELTRANENA: Thank you so much, Ambassador Traina. That’s basically all the time we have for now, but we truly appreciate you sharing your experience today. And we’re now going to follow up with the Q&A section.
CHATMAN: Great. Thank you, all. So I have some great questions here. Some were anonymous. I’m not sure if that was intentional.
TRAINA: Those are the ones about the CIA.
CHATMAN: Yeah. This is an interesting one that we started to talk about actually, when we were in the green room there. As a young entrepreneur, how did you feel sitting across from Microsoft on the negotiating table? And did you—I can’t read the rest. That’s interesting enough right there.
How did you feel? And how did you manage that process? You said your negotiating class was helpful.
TRAINA: Yeah. There are a few classes that really stood out for me at Haas. This is unprompted and unpaid, but the dean’s class was one of them I really, really enjoyed.
CHATMAN: I’ll write you that check later.
TRAINA: Yeah. I really enjoyed it a lot. But I took a negotiations class here. And it was one of the most useful and valuable classes that I took at Haas. And our teacher, she used to say to us, negotiate everything. And I found myself at the grocery store being like, I’ll give you $2 for that milk because that was part of our homework, because we had to negotiate literally everything. That doesn’t mean we were successful all the time, but it’s that mindset. And we were taught this thing called your BATNA: best alternative to a negotiated agreement, or arrangement, or can’t with the As. And so, I had been trained literally in that mindset, anchoring, throwing out a high number. And all those things I learned at Haas. So I was in a situation where I had this company. It was growing really quickly. We’d raised a little bit of money, but only one round. I still own the majority of the company. And I could see A: I was going to have to raise more money, which would dilute me. And B: It was the dot-com bubble. And it felt to me like the valuations were silly. And I was like, if I could style this company right now, I would make a lot of money, I’d make a lot of money for my investors. And it would be just a really cool thing. And so, I just set out with great determination to find a buyer. And it was very complicated. We could spend an hour and I could tell you the harrowing stories. But eventually, through a lot of butt kissing, et cetera, I got Microsoft to the table. And we had flirted a lot. And then, finally, they sent a group down here. And we had this all night negotiating session. And my lawyer was a really important guy. And he was my friend’s dad, which is how I was able to get him to represent our company. Otherwise, I wouldn’t have been able to. But he was like, ‘Yeah, I’m busy or whatever.’ And I was like, ‘This may be only one negotiation out of many things.’ But I was like, ‘This is my entire life here. I need you.’ So he’s like, ‘OK, I’ll make the time.’ We go to the Microsoft office in San Francisco. I had anchored. I’d done all these things. I’d whispered numbers, whatever. And they come in. And we had a whiteboard, and they write this number on the whiteboard. And it was not my anchor number by a mile. And I was so bummed out and very dispirited. And obviously, it showed on my face that I was very disappointed. And that was like 7:00 at night or whatever. And anyway, we ended up with all sessions of people clustering and then coming back to the conference room, whatever. And it went until—at midnight, my lawyer had to go move his car out of the garage because it was closing. And finally, around 1:00 in the morning—I had a co-founder, he and I were there. And we got to a number that was not my anchor number, but it was pretty good. And I had agreed that it would be an all-stock transaction. So there’d be no tax due. Luckily, the stock went way up after we agreed. But before we closed, aha. One thing that I’d also learned, and we did the negotiations, but someone said to me, ‘You don’t really’—actually, it might have been my lawyer, then, said, ‘You don’t really have a deal until both parties are a little bit queasy.’ And so, I was a little queasy because it wasn’t that magic number that had me living on a Caribbean island with my 700-foot yacht. But it was still really good. And I think Microsoft was a little queasy. And so, we shook hands. But I really did use those negotiating skills.
CHATMAN: Yeah. I’m thinking of we bought a house in Lake Tahoe. And I knew we got to the ultimate number because the sellers, when they left, they also took the toilet paper. I knew we had gotten everything we were going to get. So anyway, good work.
TRAINA: Hopefully, you replaced it.
CHATMAN: My real estate agent did before we got there actually because she didn’t want us to know that. But we found out. It’s an interesting note about your network, too. You hear how often Ambassador Traina’s network comes up as a critical asset in his various curiosities and deals even. So I love the way you leverage your network really deliberately. OK. Here’s another question. This is Jonathan Chen from our Evening & Weekend MBA Program. And he asks, ‘As reality and unreality become more deeply intertwined, what habits or disciplines should we cultivate to preserve our sense of what’s real?’
TRAINA: Wow.
CHATMAN: Good question.
TRAINA: That’s a good one. It’s very interesting. I look at Sora and some of these new videos and stuff. And what’s possible? OpenAI, I think, recently announced, you can put in prompts and create music. So our senses will trick us, our eyes, our ears, what we see, what we read, what we hear. But I think that internal conviction remains, meaning at the end of the day, you’ll know what’s real and what isn’t, just instinctively. I think the future of education is actually helping people to listen to that inner voice. Every day, I read The Wall Street Journal and The New York Times. They’re ideologically opposed to each other, and they report often the same facts in different ways. But I find reading them both allows me to arrive at what’s probably the truth. And so, I think a big part of skill in the future is getting your own data from multiple sources, and then trying to figure out what the actual reality is. And I think that will continue to be a really important skill. And then there will be some tools. So I think just foods or whatever, there’ll be a labeling in the future for content to help guide us on what’s human-generated or not. But it will be challenging.
CHATMAN: Great. Here’s another anonymous one. As a serial entrepreneur, how do you know when to tap into a market and when to move on and exit?
TRAINA: That is one of the hardest things. As I said, having done a number of companies, having the wind at your back is a lot better than having the wind in your face. You work just as hard and put in just as much effort. But your return depends tremendously on whether the tide is rising or sinking. And one of the hardest things to do is to know when to walk away from something because the tide is going out. And no matter all the effort in the world, it might just not pay off because you’re always wondering, ‘Well, maybe I just need one more pivot and then it will.’ Often, it will. Most of my companies had bleak moments where I could have walked away. And I actually think the most important element of being a good entrepreneur is pure stubbornness. It’s more important than knowing your field perfectly or whatever because where I’ve seen most entrepreneurs fail is they don’t have the fortitude to literally walk through a wall when they need to walk through a wall. I don’t how it happens, or I can’t explain why, but I have walked through a number of walls in my career. Just didn’t quit until I did. And that’s what made me successful. But you have to also be honest about whether an opportunity is worth that or not. And that’s a tough one. And I also say, people have always said, ‘Why did you sell so many companies? Why didn’t you go public or whatever?’ But I always say if you’re an entrepreneur and you’re building a company, it’s a little bit like blowing up a balloon. You want to make that balloon as large as you can and tie it off before it pops. And if you go too far, it could pop. And I’ve seen that. A lot people who had very promising companies and they either got greedy or overconfident and they missed the market, or they ended up with nothing. So it’s always a complex dance.
CHATMAN: Here’s one from Sarah Tay, full-time MBA student in her first year. She asks, ‘When transitioning from diplomacy back to business, what was something you had to actively unlearn or stop doing?’
TRAINA: Well, I spent a few years in Austria, wonderful country, wonderful to be in Europe, wonderful to be able to serve my country. And I loved every moment of that. I think the hardest thing was I had lived most of my life in Silicon Valley. And what you realize is in tech, things change like month to month, week to week. And being here and having that exposure keeps you sharp and keeps you fresh. You can read about stuff and all that, but it’s the conversations you have over a cup of coffee, or at a bar on the weekend, or whatever that give you a palpable sense of what’s going on. And when I returned, I felt unplugged from that stale. And I had to reconnect and do some thinking and do some networking. That was critical. And the other thing is, when I was an ambassador, I rode in a bomb-proof car. I was not allowed to drive. I had, at all times, three armed bodyguards. Everyone called me sir. My U.S. marines saluted me every time I walked by. It’s a very different modality than wearing jeans and Allbirds at a coffee place somewhere without your bodyguards. It’s not that it’s good or bad; it’s just different. I guess what is the same to a degree is when you’re leading an organization, you are a symbol. The dean is a symbol. I was a symbol as an ambassador, and even as a CEO. And you’re a person, but you’re also playing a role. And when I was ambassador, I would get a call from the embassy. And they’d say, ‘Well, you don’t have any important meetings today, or there’s no one visiting, so you don’t have to wear a tie today.’ And my answer was, ‘I am the president’s personal representative to the Republic of Austria. I am a symbol. Of course, I’m going to wear a tie today, even if no one sees me.’ It’s like you’re playing the role and you have to know the role that you’re playing.
CHATMAN: Yeah. That’s great. It makes me realize I should dress up more often, I think. Today, I’m OK, I guess. We have another question about your time as an ambassador. This is from Michael Bijesse in our Evening & Weekend—thank you—MBA Program. Michael asks, ‘Did your time as ambassador influence you to get into digital assets in such an opaque regulatory environment?’
TRAINA: Well, I guess my time as ambassador helped me feel comfortable with navigating government and regulatory stuff. But I definitely would have loved if the regulatory environment had been a little bit less opaque. And it actually got worse once I’d started a Web3 company. There was definitely such a thing as the crypto winter. That was not fun. And I’m not a big advocate of speculating with Solana altcoins and stuff. People make money doing that, but I’m actually a lover of the blockchain and what it represents, this universal ledger, immutable, and what it unlocks, tokenized assets like stablecoins. I actually think the blockchain is, in some ways, a more interesting space to work in than AI. AI is more world changing, but there’s a lot of hype and a lot of money and crazy valuations and whatever. Whereas, the blockchain is almost as world changing, but it’s been a little out of favor. So in some ways, you can have more impact with less money and whatever. But no, the regulatory uncertainty has not been fun. One of my dear friends is David Sacks, who is our current crypto and AI czar. And he and others are working really hard just to set the rules of the game. So people can know how to play the game.
CHATMAN: I think this is going to be our last question. It’s a good one. This is from Dante Gomez, who says, ‘Thank you, Ambassador Traina. You mentioned being at a point in your career where you want to focus on world-changing projects. Do you feel like this has always been a priority that is now surfacing? If so, why? If not, why now?’
TRAINA: Well, to a degree, yes. But I think that my first success with Compare.net. made a lot of other things possible. Obviously, I started my first company here. I sold it while I was still in my 20s. I sold it well. It was somewhat well known that I did it. I was lucky to come from a pretty advantaged background. But I sat my parents down after I sold it. I was like, ‘You’re now free to live as long as you wish because I’m not waiting around for you. I can pay my own bills and whatever.’ But I think that having had that first success emboldened me so that I didn’t have to prove anything of that sort anymore. I could look at loftier goals and even do things that didn’t involve profit, just maybe make—one of the first things I did when I sold that company was, I was like, I really want to give back in a big way. And my mother had worked with these Dominican nuns who ran eight inner city schools in California—San Francisco, Oakland, and LA. And there were high schools. And I noticed that there were grade schools and high schools, and they were doing an incredible job of educating these often very poor kids, inner city, who did better than in the public schools. They went on to become doctors, nurses, policemen, whatever. And I had learned that the church was going through some really bad stuff and had no money, and, therefore, couldn’t support these schools. And they didn’t have consistent income. And so, the first thing I did when I sold to Microsoft is I worked with these Dominican nuns, and we set up an endowment that funded each of the eight schools and development directors for them. And I gave a bunch of my stock to help. And the nuns sold it. And then there was a big—I think it was a Wall Street Journal story saying, ‘Nuns give up on Microsoft’ because they were dumping the stock. I got a little comment from Microsoft. But to be able to do things like that, that was cool.