Roy Rubin. Magento’s Exited Founder: Globetrotting and the Search for Purpose

Written By Anastasia Koroleva

Episode - 42

Roy Rubin. Magento’s Exited Founder: Globetrotting and the Search for Purpose

 
 
 

Roy Rubin the visionary founder of Magento, built the open source e-commerce platform from the ground up, leading it to a remarkable exit to eBay in just four years.

He then stayed on at eBay for two years, but felt suffocated by corporate walls.

That's when it hit him. He barely knew his family anymore. So he and his wife pulled their kids out of school, packed up and set off on an open-ended journey around the world. For 14 months, they traveled without a plan, letting each destination choose them and discovered what freedom really meant.

When they returned, threw himself into the challenge of cycling and completed an Ironman. He also started an angel investment firm to stay intellectually engaged.

He has built a beautiful life, but now 13 years post-exit, he is still looking for a new purpose.

Roy is torn between the urge to build something big again and the fear of sacrificing his family and lifestyle.

Roy is disarmingly open and witty in this conversation. His ideas on personal growth, leadership and fulfillment are fresh and thought-provoking.

What We Discussed:

00:00:00: Introduction and greetings

00:00:08: Roy's background and introduction to Magento

00:00:52: The founding and growth of Magento

00:02:06: Why Magento was sold to eBay

00:03:58: Reflections on selling Magento

00:04:43: Period after selling: Working at eBay

00:06:11: Challenges and experiences at eBay

00:09:38: Frustrations and limitations at eBay

00:10:07: Difficulty in leading within eBay

00:12:39: Reflections on regret and learning from the experience

00:14:53: Pain of working at eBay

00:17:04: Changes in the leadership team post-acquisition

00:18:25: Leadership style and inspiration

00:21:07: Transparency and leadership approach

00:24:24: Personal reflections post-exit

00:24:48: Reflecting on leaving Magento in 2013

00:27:03: Deciding to leave eBay after Magento's Imagine conference in 2014

00:28:15: The decision to travel with family for 14 months

00:29:00: The travel route through Central America, South America, Asia, and Europe

00:30:03: The travel experience and its impact on family dynamics

 

00:35:04: Encouragement to other founders to take time off and travel

00:42:02: Discovering new passions post-travel, specifically Iron Man and cycling

00:44:59: Introduction to Personal Journey

00:45:26: Discovering Passion for Sports

00:46:10: Reinventing Post-eBay Life

00:46:44: Starting the Fund During COVID

00:47:04: Transition to Angel Investing

00:50:27: Managing Wealth Post-Magento Sale

00:53:03: Investment Philosophy and Public Equities

00:55:45: The Non-Financial Rewards of Investing

00:57:17: Search for Purpose Beyond Business

01:00:27: Reflection on Purpose During Magento Years

01:02:33: Balancing Life with Current Ventures

01:05:12: Discussing a life of 24/7 dedication

01:05:47: The search for purpose

01:07:01: Meeting new people

01:09:00: The intense journey with Magento

01:11:56: Coping with the transition post-acquisition

01:15:07: Being a creator versus an operator

01:18:11: Future impact and legacy

01:21:10: The desire for more meaningful work

01:25:21: Closing remarks and goodbyes

  • Anastasia Koroleva: [00:00:00 - 00:00:01]

    Hi Roy. 


    Roy Rubin: [00:00:01 - 00:00:02]

    Hi there. 


    Anastasia Koroleva: [00:00:03 - 00:00:05]

    Thank you so much for joining me today. 


    Roy Rubin: [00:00:06 - 00:00:08]

    Happy to be here and thanks for taking the time. 


    Anastasia Koroleva: [00:00:08 - 00:00:59]

    So Roy, you've built a legendary company which I'm sure everyone in my audience is familiar with. And you've given quite a few fantastic interviews. And I encourage everyone who is listening to go and listen to the story of how Magenta was built. It's absolutely fascinating. But on this spot today we're going to focus on what happened after and I want to dig very deep into your soul and figure out how you felt afterwards and why you made the decision you made and where you are today. What is it now, 13 years after your exit? So if you don't mind, I'd like, I'd like us to start with you just, just quickly talking about Magento and why you sold it. 


    Roy Rubin: [00:00:59 - 00:04:02]

    So you know, Magento came out of a consulting business that I, that I had. I started a freelance web development business just as a starving student in my early 20s that needed to pay rent. And I've always had this interest in computers and programming and was largely self taught. And when I started the consulting business I was at UCLA and that led me to really understanding the opportunity with commerce. We specialize in bringing online merchants online using open source tools. And as our business grew and it grew to about 25 full time people while I was still at UCLA, I went to UCLA and you know, Magento came, came out of that experience, came out of the opportunity that we saw to kind of build this next generation platform and the question of why we sold it, you know, Magenta was a rocket ship. It was, it was just, you know, from day one, it became something, know, very big unexpectedly. I have to say I, this was not by design per se, although of course every entrepreneur wishes for it to happen. I think that it, you know, cut us all by surprise. But listen, I sold it because I felt like we, we have an opportunity to do something bigger with, we sold it to ebay with, you know, with ebay and really build, you know, a monumental company as part of a bigger, of a bigger ship. You know, we'll talk about this I'm sure in the next few minutes. Didn't quite happen that way, but I think as an entrepreneur that is, you know, a first time entrepreneur having such a great validation by, you know, at that point in time, an established player, express interest and what you felt, you know, something that we, you know, we gravitated towards. I have to say also this was in, in 2011 when the exit happened. You have to remember that Magenta was largely built through the great financial crisis. So we also, I think, had a bit of trauma behind us and needed to really take these opportunities into consideration. You know, having come out of what was a relatively difficult macro environment in time, this was also life changing. Right. So for me to sort of go through that process was very natural because I felt like, you know, I would be comfortable and my life would, you know, would obviously look different and change and. Yeah. And I just felt like that was the right thing to do for us at that moment in time. 


    Anastasia Koroleva: [00:04:03 - 00:04:07]

    Do you still feel that way? Have you ever regretted selling? 


    Roy Rubin: [00:04:08 - 00:05:41]

    I've never regretted selling. I have a wonderful life and a wonderful family, my wife and my children. And I think when I look at what I have gained by selling at that moment in time, I think that I gained, you know, quite a lot. And I never look back. A lot of people ask me that. They ask me that because there is this other great e commerce platform in the market today that has done exceptionally well following Magento's sell to ebay. And many assume that I will have some regrets, but realistically, I've never looked back. I think that there was, you know, quite a bit of uncharted territory still ahead of us and opportunity ahead of us. Absolutely. Actually look at it from a different angle. Not from regret, from a loss of opportunity, but, you know, I think that I have moved on right from that moment after I sold and said, you know, there's a new chapter in my life and, you know, I'll explain, explore that and continue to discover who I am. But I think it's unhealthy to look back and for me, at least, it was very not. It was very unhealthy to sort of spend the time to regret things. I think I would have just been miserable if I did that, and that's not what I want in my life. 


    Anastasia Koroleva: [00:05:41 - 00:06:02]

    No, I absolutely hear you. So you moved on and the following two years you spent on ebay, how did that feel? That must have been a shock to the system because you had never worked in a big company as an employee in your life. Right. You started Magento from the university. 


    Roy Rubin: [00:06:02 - 00:07:27]

    Yeah, I had a couple of jobs earlier in my career, but they were, you know, there were college type jobs. They weren't really serious, you know, from that perspective. And yes, I spent about three years under three years at eBay, just over two years. It was absolutely a shock, a shock to the system. You know, in many ways. You know, we came into ebay at the time and there were a lot of acquisitions that ebay made a lot of really interesting and young talent. Many have gone on to build incredible companies. You know, following, following this, this endeavor. So there's, there were the right people around the table. But I think ebay as an organization wasn't really a technology company. And we struggled really to get the attention, the mind share. There weren't really any visionary leaders in the organization. There were really strong operators in the business. And we came in as a young team that is hungry, that is driven, that continued to believe in the opportunity to build developer first commerce solutions. And we found an organization that just lacked that, that vision and that excitement. So I spent like almost three years just making sure the product wasn't killed by them. I also felt. 


    Anastasia Koroleva: [00:07:28 - 00:07:36]

    Yeah, go ahead. No, you're already answering my questions. Question. Because I said, how did it make you feel? 


    Roy Rubin: [00:07:38 - 00:11:51]

    It felt like it was mostly about survival rather than about executing and building. Right. I was really there to make sure that the organization continued to prioritize the product, continued to take advantage of the opportunity I had to sell it internally from the CEO downward. And you know, it was largely an, you know, a risk averse organization. And that was, that was tough for us because we wanted to take bold risks, we wanted to take big steps. We had a lot of product to build and a lot of opportunity ahead of us. And we needed, we felt like we needed a party that would be there right alongside and you know, and help us execute, giving us the resources we need to do so. And we found something very, very different. We found an organization that restricted our resources, limited our vision, was very risk averse, didn't really have anybody on the inside that could champion us. I tried to do that. I reported for a while to the CEO and the cfo and I wasn't shy about my opinions to them. And I felt like for quite a long time I had to really up until I left and I left out of frustration. I think that if there was an organization on the other side that would have supported what we had wanted to do, I would have stayed much, I would have stayed much, much longer. But I felt like I had to fight my way through. And that is, you know, as an entrepreneur, somebody's kind of built things with my own two hands and you know, great team of course around me, it didn't feel like that was where I wanted to spend the rest of my life or at least the next few years of my life. So I, you know, I ended up being frustrated. You know, what was also very difficult was that, you know, As a leader in your own company, people look to you to have all the answers. Right? You are ultimately the decision maker in the organization. And I came into, you know, into ebay and I felt like I was not driving the ship of my own business. I was subject to a lot of other people's opinions, opinions from the CFO that was right there instilled by ebay to make sure that we were on budget. Now we had budgets before, but this was a whole different level where you really couldn't make an investment without running it through quite a lot of people and then getting a buy in for people that just don't even understand your business. But from the CFO to the people on the HR side, there was a lot of, you know, institutional organization that was brought into, you know, a young Hungary startup. And for me as an entrepreneur to navigate across these roles, even though they had, I'm sure, all the best intentions, they were just working within an organization and a framework that was very limiting in the way that they, you know, allowed a company like ours to really thrive. And putting these handcuffs on us, I think was really limiting and really just created frustration to the point where my team would come to me asking questions and I just didn't have the answers. And I felt a bit decapitated. Right. Not having the ability to formulate a straight answer to people was new to me. I was always very transparent and open with my team and here I just lacked the answers and it felt like I was leaving. I mean, I've used this before, I've used this statement before. I felt like I was leaving my soul at the door every time I walked in because I had to put this Persona and provide answers to people that I wasn't fully comfortable with. 


    Anastasia Koroleva: [00:11:53 - 00:12:10]

    It sounds like hard time for you because you had to pretend and it was suffocating probably for your creativity, for your vision. You were restricted. And entrepreneurs don't like being restricted. We are freedom loving animals. 


    Roy Rubin: [00:12:12 - 00:14:15]

    That's right. I mean, look, I think that I was perfectly happy to take into consideration a broader mandate than Magento per se. Right. I wasn't blind to being part of a larger organization and the needs, the wants, the constraints that a large organization would bring on a, you know, on a, on a small business ultimately for that organization. Right. Magenta was small in comparison to eBay, PayPal, StubHub. I mean, there were other businesses that were massive, right. That were being run there. So I wasn't blind to that. But we had such a huge opportunity ahead of us. We all knew that I think that's largely why this acquisition was made by the team. Yet from the first moment, they really suffocated us. They put constraints on us, they began to extract resources from us. And that was very difficult to do at a time when the industry was growing so fast. Maturing competition was coming online. We had a strategy that we really believed in, wanted to execute towards. And when the team comes to you and asks you questions about is this going to happen? Right. Should we still be here? Because, you know, we're not seeing quite the same energy and drive that we saw before. Keeping that face straight for two and a half years and not you, you know, was let me start over. Keeping that perspective and that and that and that leadership mentality where you can straight, when you can look somebody straight in the face and be confident in your answer was very difficult for me to do because I honestly did not know what tomorrow would bring. I didn't have that transparency and that visibility from the organization that we were part of. And that was really, really difficult for me to deal with. 


    Anastasia Koroleva: [00:14:16 - 00:14:18]

    But you still don't regret selling? 


    Roy Rubin: [00:14:20 - 00:14:52]

    I don't, because it's changed my life and I've taken away all the positive qualities of it. Less my time there, more of what the financial outcome has allowed me to do and to become. Yeah, and I focus on that and I try not to focus on that period after the acquisition, which was probably the hardest period of my life. 


    Anastasia Koroleva: [00:14:53 - 00:14:59]

    Yeah, I can hear that. I think there is still frustration and pain in your voice. I can hear it a little bit. 


    Roy Rubin: [00:14:59 - 00:15:33]

    But listen, I'm friends with a lot of the folks there and I don't blame them for anything. I think it's just, you know, it's, it's a, it's the reality of large corporate organizations and the way that they operate, their cadence, their risk averse, you know, orientation. So for me, I actually look at it and say I learned a ton from that experience. It wasn't a good experience, but you sometimes learn from lots of positive experiences as much as you do from the positive ones, or even more you can argue. 


    Anastasia Koroleva: [00:15:33 - 00:15:37]

    But would you say you underestimated how difficult it would be? 


    Roy Rubin: [00:15:39 - 00:16:12]

    Yes, I think so. I think, I think that that was something that I never took into consideration. I never took, you know, into consideration that becoming into an organization where the incentives of the people that I collaborate with would be different than mine. Right. I had one focus on my mind and that is to go win a market. Right. To go really have a positive, meaningful impact in the space that I operate within. And I think what I found was career employees, that this was a job for them. 


    Anastasia Koroleva: [00:16:12 - 00:16:13]

    Yeah. 


    Roy Rubin: [00:16:13 - 00:16:37]

    This was a job that would lead them to their next job. And for them to take risks and to have, you know, a bit of. Of uneasiness and work in an environment that was unpredictable was not something that they wanted to do because it may hurt their career moving forward. I was willing to risk it all. 


    Anastasia Koroleva: [00:16:37 - 00:16:38]

    Yeah. 


    Roy Rubin: [00:16:38 - 00:16:43]

    So they weren't really, really willing to risk much. 


    Anastasia Koroleva: [00:16:44 - 00:16:52]

    So by the time you left, almost three years later, what percentage of your team was still there? 


    Roy Rubin: [00:16:54 - 00:17:34]

    I would say from my leadership team, most left by that point in time. And we had new leaders come in largely from the ebay organization. Again, great people, but career corporate people. Right. Not founders. Right. Before, we had people that were. Were so committed to the vision, to the business, to the opportunity that they would give it everything they have. Just like myself. 


    Anastasia Koroleva: [00:17:35 - 00:17:36]

    Yeah. 


    Roy Rubin: [00:17:36 - 00:18:02]

    We had people in the organization that slept in the offices for days. You know, when we were building Magento, they wouldn't even go home. Obviously, I wouldn't expect that later as a business matures and grows. But, you know, there was a. There was a shared mission, there was a drive, there was a passion for what we were doing. Beyond just myself and my immediate team. The employees felt like they were changing the world. Right? 


    Anastasia Koroleva: [00:18:02 - 00:18:03]

    Yeah. 


    Roy Rubin: [00:18:03 - 00:18:24]

    And I think for many years that kind of pushed us forward. Right. Culturally, and we came into a very different organization. Again, these are career athletes that, that have, you know, a life and their next job and their career progression to think about. And that was just a very different, very different mindset. 


    Anastasia Koroleva: [00:18:25 - 00:18:50]

    But it sounds like you must be a truly inspirational leader if your people wanted to sleep in the office and had that sense of urgency. So what do you think was the sort of core essence of your view as a leader on how to do it? Was it inspiration? Am I right? 


    Roy Rubin: [00:18:50 - 00:19:13]

    I think, yeah. I mean, I think people. People really gravitated. I mean, I listen, I have a hard time talking about myself, to be honest. But I'll tell you that people really resonated with what we had wanted to achieve. I think that for many, especially seeing the early traction for what we were doing was incredibly inspirational for the team. 


    Anastasia Koroleva: [00:19:14 - 00:19:14]

    Yeah. 


    Roy Rubin: [00:19:14 - 00:20:37]

    And I think we were very good at recruiting people that were not only highly capable, but also were great team players. Worked well when they're given quite a lot of lead way to. To lead and drive. We trust other people. We wanted their input. We did not consolidate decision making. In fact, we. We really appreciated a lot of opinions. I wasn't the smartest person in the room. And I let them know that. Right. So I was very humble about what I knew and what I didn't know. And we found, you know, incredible people that drove myself and the leadership team to be better leaders, you know, by, by, by having strong willed people around us. And this was a moment in time in the market where, where, where you could really paint this really amazing picture and, and people believed, you know, myself included, that we can go and know and deliver it and win it and really make a name for ourselves. And we ended up doing that. 


    Anastasia Koroleva: [00:20:38 - 00:20:54]

    So now you've had enough years to process all that experience. What would you say you were bringing to the table in Magenta? What talents, what skills? And I guess you were very young, so talents probably more than skills. 


    Roy Rubin: [00:20:56 - 00:20:58]

    You're asking about myself? 


    Anastasia Koroleva: [00:20:58 - 00:21:02]

    Of course, I keep talking about you, so you have to get used to it. 


    Roy Rubin: [00:21:07 - 00:23:44]

    Look, I think the talent and skills that stood out and I think this is largely why Magenta was an open source product. We gave away our iPad, we not only gave away our IP before launch for Magento, we actually shared the wireframes of what we were building. We were incredibly transparent and open about what the vision was and where we were going. I think it speaks a lot about the qualities of the leadership that I had brought in. A very open, honest, transparent leadership. A leadership that values the people around the table, doesn't just see them as execution machines, sees them as contributors that are critical to the success of the business. I had set very aggressive deadlines along with the team we delivered every single time. One of the most important things for us at the time was to build credibility with the open source community. And one of the issues was that, you know, dates and deadlines in open source was something that continued to move because it was oftentimes deliverables by individual contributors, volunteers. There wasn't real transparency and sort of commitment to timelines. We had wanted to set a whole different standard, one that when we set a deadline and a date, we deliver it and we thereby build credibility with our audience. So we were aggressive. We had a big vision. I gave a long leash to our people to go and execute, to come up with creative ideas. I wasn't the smartest person around the table and they knew that. And I was very humble, you know, in, I mean, hopefully still am, you know, to some extent I try, but that was just something that for me was very natural in terms of how to build a business, how to be a leader, how to build a team around you. I knew exactly, you know, the type of business that. That. That I wanted to build and the type of people that I wanted around the table. And we were fortunate to just have this collection of individuals that coming together really made, you know, an incredible effort and a positive one in, you know, in delivering towards the vision that we had set. 


    Anastasia Koroleva: [00:23:44 - 00:24:02]

    Roy, there is a great pattern in our conversation. I keep asking you questions about you personally, and you keep saying we. Is it because you're such a fantastic team player and you're humble, or you actually avoid talking about your own feelings? 


    Roy Rubin: [00:24:06 - 00:24:12]

    It's a. It's a. You know, it's a good point. You know, I. I was going to say we, but I caught myself. 


    Anastasia Koroleva: [00:24:12 - 00:24:13]

    I know. 


    Roy Rubin: [00:24:14 - 00:24:20]

    No, I think when I. When I speak about the business, it's very difficult for me to say I. 


    Anastasia Koroleva: [00:24:20 - 00:24:59]

    Okay. But I am interested in you personally right now. So let's leave, Magento, because now I want you to be alone and I want you to tell me how you personally. I don't want any more we. I want. I. If you don't mind, how you personally handled that initial period after you exited. And I'm talking about your complete exit after you left ebay. So I guess 2013, how did it feel initially and how your feelings about not being a founder, not being with Magento, evolved over time? 


    Roy Rubin: [00:25:02 - 00:25:05]

    Can you. Okay, can you ask more specific? 


    Anastasia Koroleva: [00:25:05 - 00:25:06]

    Absolutely. 


    Roy Rubin: [00:25:06 - 00:25:07]

    Broad. 


    Anastasia Koroleva: [00:25:07 - 00:25:16]

    Yes, of course. Let me. Let me break this up. Fair enough. So right after you exited completely, how did you feel? 


    Roy Rubin: [00:25:19 - 00:26:08]

    I felt very proud of what I accomplished. Very proud of what the team has accomplished. I felt that this is a new chapter in my life. You know, I celebrated this, you know, in very simple ways. Right. We lived a modest, relatively modest life before, my wife and I, and, you know, not much changed. Right. Following the exit, but I felt very, very accomplished. I felt like there was still a lot in me to go and execute. And I showed up to work the next day. 


    Anastasia Koroleva: [00:26:11 - 00:26:12]

    What was the work? 


    Roy Rubin: [00:26:14 - 00:26:15]

    Well, at ebay. 


    Anastasia Koroleva: [00:26:17 - 00:26:25]

    Ah, no, I meant after you left ebay, when you have no work to go to that 2013. Yeah, yeah. That's the moment. 


    Roy Rubin: [00:26:26 - 00:26:29]

    Okay. So I leave ebay. Yeah. 


    Anastasia Koroleva: [00:26:29 - 00:26:32]

    When it's finally you as an I, not you as a we. 


    Roy Rubin: [00:26:33 - 00:26:34]

    Yes. 


    Anastasia Koroleva: [00:26:34 - 00:26:39]

    How did that feel? Somebody still merged with the team. 


    Roy Rubin: [00:26:39 - 00:27:43]

    Yeah. So I leave in 2014, and this is after a period of time where, as we said, I leave my soul at the door every single day. I come in for two and a half years working for eBay. So I leave in 2014, and I leave following Magento's annual big, big conference where we bring in 3,000 people. So very, very high. At the peak of the peak of that year, I decide to leave right after Magento's Imagine conference. Okay. And I knew that period of time would have been very difficult for me not to have that continuity. We're now talking about 12, 13 years after I started that original consulting business. So this is going to be a whole new chapter of my life. And what I do is I, along with my wife, we talk about this in advance, of course. We decide to go and pull the kids out of school and we go traveling for an indefinite amount of time. 


    Anastasia Koroleva: [00:27:44 - 00:27:45]

    Awesome. 


    Roy Rubin: [00:27:47 - 00:28:37]

    And I do this for many reasons, primarily because I need to rediscover myself and I need to get reacquainted with my family. And at the time, I had a 4 and 7 year old and I wasn't home much all through this period of time beforehand because I was traveling a ton and the business was growing and I had a lot of responsibilities and a team, of course. And I say, you know what, if I'm going to rediscover who I am, then I need to go spend time and disconnect from my previous life. And we ended up traveling for 14 months. Only had the first couple of weeks planned. 


    Anastasia Koroleva: [00:28:38 - 00:28:39]

    Yeah. 


    Roy Rubin: [00:28:39 - 00:28:57]

    And went on this journey, journey to get the family back together and reacquainted and, you know, for me to spend time, of course, with the kids. And that was something that I've always wanted to do and had that moment in time in life to go and do it. 


    Anastasia Koroleva: [00:28:58 - 00:28:59]

    Where did you go? 


    Roy Rubin: [00:29:00 - 00:30:02]

    We started in Costa Rica and we went north from there to Nicaragua, to Guatemala, to Mexico. And everything was centered around the kids. If the kids had some time to meet friends, local friends and where we could find some schooling for them for a period of time, we would, we would stop and take as much time as needed for that, for that, you know, to happen. So we did Central America, then we flew down to South America, Argentina, Peru and Ecuador. And then we embarked on an Asian trip to Thailand, Cambodia, Sri Lanka, Vietnam and Laos, and then finished off in Europe for a few months in the spring and summer of 2015. 


    Anastasia Koroleva: [00:30:02 - 00:30:15]

    That's a lot of countries. For 14 months. How long into the journey did you feel super tired and frustrated? 


    Roy Rubin: [00:30:20 - 00:31:28]

    I never get frustrated. I never got frustrated. There were countries we stayed in for, for a long time. There were other countries that we just passed through. Again, it was all a matter of our comfort in the country and enough activities for the kids. You know, what's, what's interesting is that every Single morning. We had to reinvent ourselves. Yeah, right? You kind of wake up in a new place. You have to figure out what to do, Right? You want to be productive. You can't just. Just not do much. Right? But it ended up being 16 countries. You know, in 14 months, we had. Again, we had no agenda. So, you know, it could have been 30, it could have been 5. Who knows? We. We met people along the way. We had a great time discovering ourselves, putting ourselves in uncomfortable situations and scenarios almost daily. We saw the kids grow and mature and develop skills, and I feel like it's been one of our greatest moments as a family to go through that experience. 


    Anastasia Koroleva: [00:31:28 - 00:32:07]

    I absolutely love how you just decided to go with the flow. I think it's such a beautiful way to unwind. It's fantastic. We did something similar after the first exit. I think it was absolutely awesome. You do learn a lot. Our kids were much smaller, so I don't think they remember anything. So it was probably more impactful for us, really, than for them. But you said your older 1 was 7. That is already a different age when they would remember quite a bit. Would you say your kids were more happy or more stressed about the whole experience? 


    Roy Rubin: [00:32:08 - 00:35:41]

    I think they loved it. I think they naturally thrived in this kind of an environment. They woke up excited every morning. I think, you know, look, first and foremost, they got their father back. That's huge, right? Because I wasn't there for most of their early years. And it bothered me. It really, really bothered me. Right? That's not the type of father that I wanted to be and the type of family, you know, person that I. That. That I wanted to be. Obviously, my wife was great, and she was understanding, and she was, you know, incredible. But when I looked at my life, I said, you know, this is not. This is not. This is not my future. My future isn't to be. To be a corporate, you know, executive that shows up every once in a while and has quality time with the family. That's. That's definitely not what I envisioned my life to be. So, you know, the fact that we could wake up in the morning, have these shared experiences, you know, sit down with the kids, have really, really quality time with them, is something that we appreciated. And, you know, we did things that were, you know, outside the comfort zone. Right. We went hiking and camping and. And then sleep in luxury accommodations for most, almost every night. We slept in very, you know, modest accommodations. We felt like this was a journey for us. And I think the kids really took a lot away from it, you know, to this day I've got a 17 year old now high school senior, you know, he'll tell you like that was one of the greatest things, you know, in his life and it's now 10 years later. So I highly encourage, I mean a lot of founders that I speak with that exited. I'm a big believer in this get outside, get outside of your comfort zone experience this time with the family. And you have to remember I left ebay with no hobbies, no passions and largely no friends. And I said, and a very limited knowledge of my family. And I said, okay, well you know, this is no way to live. Yeah. And I was on a mission of self discovery, starting with the family, which I think is the most important thing. And I figured if I want to do this the right way, I have to take us all out of our day to day and you know, and get, you know, and get to be together and you know, shared experience to this day. By the way, we are avid travelers and we try to get out as much as we can. We go off the beaten path as much as we can. And you know, my kids have been fortunate to, I think, I mean, hopefully right to have a father that isn't quite, quite the norm when it comes to this and looks for crazy adventures to put us all through. Luckily, I have a willing partner in my wife here that's willing to go on these, on these, on these crazy experiences. But you know, I love being uncomfortable and I think that the kids have grown largely to appreciate that. And I have to tell you, my son for the first time last year took friends to go camping on his own. He drives of course now, and he took our truck and he loaded the back with firewood and tents and everything and grabbed few friends and they went and drove, you know, a couple hours north of us here in la. And for me as a father to see my son go camping on his own, of course being prompted by me was, was like, that's huge. 


    Anastasia Koroleva: [00:35:41 - 00:36:22]

    Yeah, yeah. I, my, my oldest just turned 18, so I can absolutely relate to that. When you see them doing these things all by themselves, it's just so exciting and so wonderful, so rewarding. Roy, I'm so happy that you told us this story because I come across lots of people who post exit would love to do that, but then they say, oh, but I can't possibly take my kids out of school because that will destroy them. And I would love to travel, but we'll sit here until they grow up and we're not going anywhere. And Then we'll travel. What would you tell these people? Like, why? What are the most compelling reasons to try to do what you did? 


    Roy Rubin: [00:36:24 - 00:39:14]

    So let me tell you a little something that I use with my little trick that I use with my wife, because my wife also had, I think, a lot of reservations and concerns about this. I said, listen, let's leave. And whenever you're unhappy or the kids are unhappy, or we feel like we've gotten to a conclusion, within 24 hours, we'll be at home. And I think when you reframe the question of we're not going for 14 months, actually, we wouldn't even know how long we were going for. Right. But when you reframe the question and you say, listen, we're going to go until we feel like we've exhausted this, until this becomes a burden, like you said earlier. Right. And you know what? After some time to settle, a few weeks, it became our life. You know, I could see a world that we would never come back. I mean, obviously we did because we wanted the kids to go to school and sort of have that know, component, but it becomes a routine. And just reframing the question really helped us both. I think largely for her in the beginning, but I think for me also to say, listen, if we're unhappy here, we simply walk away. And we get to do that and be 24 hours away from home. You know, we were in Sri Lanka. I'll tell you a quick story. We were in Sri Lanka and we're there for three weeks by that point, and. And we just got sick of it. So everything was hard for some reason, you know, and, you know, the kids, and it was just hard. Very, very busy country. There's a lot going on, and it wasn't as easy as other countries. We, you know, we had been traveling to, and my wife and I got frustrated and we literally just pulled up a flight booking app and we said, let's go right now. Let's just leave. And we could have stayed for another two weeks. I mean, we didn't really have a plan. We just said, it's time to go. So, you know, 12 hours later, we landed in the south of Spain. Yeah, right. Having that, you know, I think flexibility and understanding that you're not married to any decision, you know, and you can, you know, reverse course or, or pivot at any point in time, much like a business, you can pivot and you can, you can go and explore, you know, other things. We land in the south of Spain, and it was beautiful and, you know, Europe is so, so easy. So it was familiar because, you know, we live here in the Western hemisphere. Right. All this stuff really matters, and it kind of got us to reboot and to look at things much, much differently. 


    Anastasia Koroleva: [00:39:14 - 00:39:59]

    Yeah, that's great. I think so many of us have this idea of freedom as a dream when we build our businesses, and it pushes us through the most difficult challenges, but then we get to an exit, and so many people don't actually experience that freedom. And I think when you let go, you go with the flow, you travel. This is when you understand what freedom actually feels like. That you can be in Sri Lanka, buy a ticket, fly to Spain. The world is small. The world is actually welcoming, and all of these things are possible. And this is exactly the essence of freedom. And if we don't experience it and we immediately move into yet another business, what's the point? 


    Roy Rubin: [00:39:59 - 00:40:47]

    Yeah. And I will even take it a step further, and I would say the exit. If I. If I look and I say, what did it actually give me? I think it's freedom. 100% right. It gave me the freedom to make any decision that I want to make. Right. Without having some. Some other responsibility sit on top of it. You know, that takes me on a different path. Got me freedom. It got me time. Right. Time to sort of pursue whatever it is I want to pursue, you know, beyond the monetary stuff, which. Which is like, you know, you look at it for a second, it's great, but then you move on. Okay, well, what do I do with this? Right. And I think for a lot, it's really confusing. Right. And they just go back to work. 


    Anastasia Koroleva: [00:40:47 - 00:40:48]

    Yeah. 


    Roy Rubin: [00:40:48 - 00:41:13]

    For me, it was never, you know, that was never the first place I go to. Right. It was always, well, now that I have time and freedom, what do I want my life to be? Right. I don't think. I don't think many founders ask themselves that question. Right. They immediately go towards what they know versus trying to be a bit uncomfortable. 


    Anastasia Koroleva: [00:41:14 - 00:42:19]

    Yeah. But it's. And we don't. We don't want that. And actually, we naturally don't want that. We are hardwired to avoid difficult decisions and difficult situations. So it's very understandable that people are exhausted already after having spent over a decade building a business, and they don't want a difficult decision, which is actually such a paradox in a way, because you would say it's very hard to properly relax after an exit because very soon, it doesn't feel very comfortable. We're not used to it. We're actually comfortable working very hard Having a structure, having clear goals, being in an environment we're used to. So, Roy, that brings me to the next question. So, okay, you are back from 14 months of globetrotting. What's your thinking? Like, what is it you want most at that point? You've satisfied your desire to experience freedom around the world. 


    Roy Rubin: [00:42:21 - 00:43:10]

    So I come back. Yeah. I mean, I come back, right? The kids go to school, and for the first time, I'm sitting alone thinking, right. Because 14 months. I didn't have to answer that question or really think about it. So I come back and, you know, it takes. We actually moved to a different place, and it takes us a few months to settle in. But after I finally have this time to sit down and think, I'm still not sure. Right. And I discover some people that I met through just going outside and running and getting on the bike and cycling, and there's these people doing Iron Mans everywhere around me. I didn't know anything about it, by the way. Nobody around me has ever done it. And I see these guys with bags, and I'm like, what? 


    Anastasia Koroleva: [00:43:10 - 00:43:13]

    How would you know? You were in the office. How would you know what? 


    Roy Rubin: [00:43:13 - 00:46:46]

    I was in the office, right? I have time for this. So. So I see all these guys doing Iron Mans, and they're swimming and they're, like, active. You know, they're older than me because, you know, I'm. How old am I? 41. 42, maybe, at the time. And. And I said, oh, I can do this, you know, So I literally learned to road bike. I learned to swim. I've got. I used to run a little bit, so. So I've got that, you know, but, you know, a marathon is, like. Was crazy for me, but I discover how to do it, and I spend the next couple years just. Just hanging out with them and, you know, ultimately doing. Doing, you know, half Iron man and then full Iron Man. Cool. And discovering that I really love cycling, like, that was something that I really didn't really know. Yeah. So. And I still do. And this is still a huge part of my life. And. And I, you know, I spent quite a bit of time, you know, doing it. I find that cycling is just the perfect sport that combines individual goals and targets. And it's. It's. You know, it's hard. It can always be hard. There's. You never really conquer it, but it's also very social, and I've met incredible people and incredible friends through cycling, and I do that to this day, traveling the world and going on different trips and experiences, you know, all Started in that moment where I. I sort of had to figure out what's next for myself sitting at home, you know, and that. And that was, you know, was. That was a big part of my life. I. I don't do that as much today because I'm. I'm busier now, but. But I honestly look back and I say that that was really, really great. Remember, I. I had no passions. I. I didn't really have any. You know, when I left, I had nothing. Right. I mean, if it wasn't for this trip, I probably wake up in the morning and figure out, like. Or not figure out what I wanted to do with myself. So this was great. I discovered that I love sports, that I love the outdoors, that I love to cycle, that I use cycling as a way to meet people and to build social relationships. That was really, really big for me. And that kind of brings me to sort of COVID era. That was that bridge between, you know, time that we got back, adjusted. I did some competitions and was focused on, you know, on that. On that side of my life. And that brings me now to sort of COVID and, you know, us, my partner and I, starting the fund, which, you know, which is occupying me, you know, a lot more these days. But I think that when I look back, you know, I've had to reinvent myself a couple times since I left ebay. Right. First was taking that trip, that long trip, and getting reacquainted with the family. The second is finding passion in sports and athletics and really, you know, really finding a lot of purpose in that. And now, you know, with the fund and what we do as early stage investors at R Squared, that's been absolutely a blast, and I'm really, really enjoying that as well. And we'll see what's next. I don't think this is the end for me. I think this is the beginning. So the great thing is that with time and freedom comes choice. Right. And I think that there's still a lot of choices ahead of me. We'll see what those are. I'm not sure, but there's still probably some things ahead of me. 


    Anastasia Koroleva: [00:46:47 - 00:47:02]

    Okay. But I don't want to jump through your decision to start R Squared, because I'm very, very interested in it. How did you get to that? Why? What problem were you solving when you decided to start it? 


    Roy Rubin: [00:47:04 - 00:49:27]

    So I think after three, four years of being on the bike and running, what I found was that my brain was rotting a little bit. Right. I think that it's. It takes, obviously, a different side of the brain and there's a lot of meaning and purpose in it. But to exclusively do that was not enough. And I had done some angel investing with a very close friend who I met when I invested in his company and he had a successful outcome as well. And he sold this company and he left. It's my partner now in R Squared. And he called me and said, okay Roy, get off the couch, let's do this now. More, more institutionally. And you know, I was leaning towards a lot more of that. I was really, you know, gaining a lot by, by spending time with the entrepreneurial teams that I backed and I really enjoyed it. It kept my, my brain working it, you know, I was, I was curious, I was learning. I was able to provide feedback and have an impact on these companies journey. I didn't lose my sleep over it. I mean, I keep saying that Magento is what is why I lost all my hair. Here's a different, here's a different scenario here where you, you don't really lose sleep. You know, for me at least I don't really lose sleep as much. Right. I obviously care and I'm passionate. I want these companies to do well and succeed, but it's a very different type of responsibility that you have as an investor. So, you know, I gained, you know, I gained a lot from it. I loved it. You know, we have a little bit of a different model in, you know, in R Squared than I would say most funds and don't have an aspiration to go build a massive platform. But we love spending time with early stage teams and, you know, and spending, you know, providing a lot of value. And I found that to be, you know, incredibly meaningful. I can still bike, I can still spend time with my kids, I can still pursue other passions and hobbies. I can still meet incredible people around the world, which has been something that I wanted to do all through the last 10 years of my life and hopefully continue to do that. But I also get to use my brain a little bit so I feel like that's a benefit. 


    Anastasia Koroleva: [00:49:27 - 00:49:34]

    So for how long you've been doing it now? I wouldn't say full time, but institutionally. 


    Roy Rubin: [00:49:35 - 00:49:42]

    Angel investing, we started in 2021, so I think it's going to be just over three years now. Yeah. 


    Anastasia Koroleva: [00:49:43 - 00:49:56]

    So I assume it's too early to say if it was a good investment or not for you. Sorry, so it's, it sounds like it's too early for you to know if it was a good financial investment for you. 


    Roy Rubin: [00:49:57 - 00:50:26]

    Yeah, it's, yeah, it's Too early to tell. You know, I think we'll know only, you know, in a few years if the outcomes. We feel like we have great companies, but we'll see obviously what happens. I have a lot of history. I started angel investing in 2012, so there's already a 12 year track record. And it's been actually phenomenal for me personally. And I hope that we're doing our job selecting the right teams and the right companies. We hope so, but time will tell. 


    Anastasia Koroleva: [00:50:27 - 00:50:32]

    So when you sold Magento, was it a life changing event for you financially? 


    Roy Rubin: [00:50:33 - 00:50:35]

    Absolutely, yeah. 


    Anastasia Koroleva: [00:50:35 - 00:50:39]

    How since then you've been thinking about managing your money. 


    Roy Rubin: [00:50:42 - 00:51:26]

    So at first I decided not to think about it and I hired people to help me do that. We worked with Goldman Sachs and Merrill lynch and I punted that decision. But I didn't sleep well at night because I need to have, especially with money, it's very emotional, as you know. I needed to have clarity and transparency and really understand what's happening. So I started working with them as a way to just get through the first bit of time and not have to think about it. But later on I decided to take this on to myself and ended up moving away from them and now, now manage all of it on my own. 


    Anastasia Koroleva: [00:51:26 - 00:51:35]

    Okay, and what's, what's your philosophy, if you don't mind me asking, like, are you, are you going after safety or you are? 


    Roy Rubin: [00:51:35 - 00:52:03]

    Yeah, I think, I think I'm a rather conservative investor. I've learned that for me to sleep well at night, I need to fundamentally have a very simple approach and portfolio. I'm really not looking to have anything super complicated. I think what I found in the other investment professionals that I've worked with is that it's incredibly complicated. The strategies that they execute and the products that they like to put people into, largely to show their value, they. 


    Anastasia Koroleva: [00:52:03 - 00:52:05]

    Still can't beat S P. 


    Roy Rubin: [00:52:06 - 00:52:07]

    Say again? 


    Anastasia Koroleva: [00:52:07 - 00:52:12]

    And they still cannot be beat S P. Exactly. 


    Roy Rubin: [00:52:12 - 00:52:43]

    So I listen, I mean, I did a lot of testing and research and measure them for a good number of years to understand because I thought I was kind of stupid in this. Right. Not having that background. I said, these guys are so smart. And what I discovered was that the simple strategies, the ones that I gravitated towards because I could understand, outperformed the more complex strategies where fees are a big portion of the drag on performance. 


    Anastasia Koroleva: [00:52:44 - 00:52:44]

    Absolutely. 


    Roy Rubin: [00:52:45 - 00:53:53]

    So today I, you know, I manage it on my own. It's very, very simple. I, you know, I'm largely exposed, you know, to public equities and, and I do you know, some real estate investments on the side as well and, you know, and invest in startups. But largely, when you look at everything that I have, it's, it's a very conservative approach. I'm, you know, I'm not looking to have home runs in every single asset class that I invest in. And you know, I want, I want to be able to sleep at night knowing that we can, we can grow it, you know, at a very slow pace, but grow it over time and, you know, maintain, you know, quality of life, which, you know, we live, I think, well below our means, just because that's where we're comfortable with. We, you know, we don't really, I mean, beyond my bikes, I don't really need anything else. So we, you know, we're happy with where we are and have largely simplified, you know, a lot of this so that we can sleep easier at night. 


    Anastasia Koroleva: [00:53:53 - 00:54:03]

    Yeah, no, absolutely. So what percentage of your net worth would you be comfortable spending? Angel investing. 


    Roy Rubin: [00:54:06 - 00:54:19]

    I mean, investing in terms of the stock market. You're, you're asking. A very small percentage of my net worth is in startups and technology. Very, very small portion of it. 


    Anastasia Koroleva: [00:54:19 - 00:54:19]

    Yeah. 


    Roy Rubin: [00:54:19 - 00:54:22]

    You know, a larger portion is in real estate, but the bulk of it is in public equities. 


    Anastasia Koroleva: [00:54:23 - 00:54:27]

    So would you say you're doing it primarily for non financial reasons? 


    Roy Rubin: [00:54:29 - 00:55:21]

    The investing side of my life, absolutely. That's. I'm not doing this for financial reasons. No. No. I'm doing this because I love spending time with these teams. I love getting to know new people. I love learning. And I think that's if I have to. Actually, that's probably the number one thing. Every single call that I have, I learn something new. Right. And I love that I can be challenged, you know, by a lot of really early stage teams that have a different philosophy or mindset or go to market approach, you know, and I'm privileged to sit down and like, have all these guys tell me what they're thinking about. Right. Much like you. Right. This podcast, I'm privileged to just learn every single day and be exposed to really smart people that are willing to give their time and share with me what they're thinking about. 


    Anastasia Koroleva: [00:55:21 - 00:55:51]

    Yeah, no, absolutely. There are so many different ways to solve that need of ours, to talk to interesting people and to learn. Absolutely. Angel investing is one of them. I'm asking because some people do do it for financial reasons and it's obviously a very risky type of an investment. And so I was curious. So can we switch to a completely different thing? Do you have a sense of purpose. 


    Roy Rubin: [00:56:00 - 00:56:02]

    I think I'm still searching for it. 


    Anastasia Koroleva: [00:56:03 - 00:56:11]

    How would you define what is it you're searching for? How do you define purpose? What is it you're searching for? 


    Roy Rubin: [00:56:17 - 00:59:35]

    This. You know, it's a really hard question for me to answer because, you know, I want to look back at some point of my life and say I have accomplished beyond Magento, because Magento is a business. I don't think it's, it's. My purpose wasn't to go build a startup. Right. I, you know, that, that was something I did along the way. But I think, I think there's more to me and to what I want to be remembered for than just that. Now I don't have an answer for what that other side is. Right. And that's what I'm still, you know, searching for. You know, when I, I'll give a quick anecdote. When I left Magento, I, you know, I wanted to, to be involved in some philanthropic. Philanthropy is a big part of our, of our life now. And we, we work with a number of organizations. But for years I couldn't find anything that I gravitated towards. I didn't just want to write a check. Like to me that wasn't enough. That didn't really solve what I was looking for when trying to be involved with an organization. And it took me a few years to find these things that are really meaningful and play, and play a big role for us. And you know, we contribute and we're involved and you know, we help out and the kids are involved as well. But we want to continue seeking for what that next thing is and what that, what, you know, what we really fully get behind this is still sort of on the side. It's partial, it's not, you know, we write a check, but we're involved. But it feels like there could be a whole lot more out there for us. And when I think about the next stage or two of my life, I feel like that is a big part of it. Now. I can't tell you what that is because I've been searching for it. When we travel the world, I would meet with a lot of non profits in the various areas that we would travel to. I would seek them out. Right. We're in Guatemala and in Costa Rica and in Ecuador. We would try to find these stories in these organizations that we could really connect with and we, you know, we ultimately, you know, write a few checks, but we didn't really connect with, with, with what that is. I think as I'm becoming older and I'm seeing, you know, I'm seeing more around my community, around here. You know, we're Jewish, so we're. We're involved in the Jewish community. You know, these are things that we think we. We can gravitate a lot more towards. But my wife and I have. Have these conversations often. We want to play a positive role, you know, in people's lives and, you know, and do something that's meaningful both for. For us and more importantly to those that we try to try to help and. And be involved with. But we're. We're still in search, I have to say. It's been. It's been, you know, 13 years, 14 years since we sold the company, and we're still on that journey of discovery. I wish it was easier to find, but it does take a lot of time to do so. 


    Anastasia Koroleva: [00:59:35 - 00:59:39]

    Roy, when you were in Magenta, did you have a sense of purpose? 


    Roy Rubin: [00:59:42 - 00:59:54]

    I think when I was in the business, my sense of purpose was to go build out the company. Absolutely. I felt very motivated, very passionate. I knew what I wanted to achieve. It was very singular. I didn't really know anything outside of it. 


    Anastasia Koroleva: [00:59:54 - 01:00:07]

    Would you say, if you try to remember that, did you realize the business was giving you purpose, or you only realized it after you sold the business and started? 


    Roy Rubin: [01:00:08 - 01:00:25]

    You know, at that moment in time, I felt like I was 100% focused with a great sense of mission and purpose on building out the business. I didn't feel like I needed something from outside of it. 


    Anastasia Koroleva: [01:00:26 - 01:00:27]

    So what do you think? 


    Roy Rubin: [01:00:27 - 01:00:30]

    However, Go ahead. 


    Anastasia Koroleva: [01:00:31 - 01:00:34]

    I think we have a bit. Yeah, go ahead. 


    Roy Rubin: [01:00:34 - 01:01:08]

    You know, I mean, I knew that, that, that. That I was missing some things in my life, primarily my family. I didn't see my family. Right. And so there was a cost, There was a direct cost to what I was doing, and that always bothered me. Meaning that I wasn't fully fulfilled because I knew that there was a side of what I was doing, you know, a side of me that just wasn't. Wasn't around. Right. And. And is missing the opportunity to be the kind of, you know, the kind of father and husband that I. That I. That I always wanted to be. 


    Anastasia Koroleva: [01:01:09 - 01:01:09]

    So it sounds. 


    Roy Rubin: [01:01:09 - 01:01:11]

    That was what I needed to do at that moment in time. 


    Anastasia Koroleva: [01:01:12 - 01:01:24]

    So it sounds like you are telling me that you had a sense of purpose, but you didn't feel fulfilled because that family side of your life was missing. 


    Roy Rubin: [01:01:25 - 01:01:28]

    Yes, I think it's a very fair way of characterizing it. 


    Anastasia Koroleva: [01:01:28 - 01:01:42]

    So if you were putting your life together as a puzzle today, you would say, today the family part of my life is here, but now my purpose is missing. And you're looking for that now? 


    Roy Rubin: [01:01:43 - 01:02:15]

    Yes. Yes. I think, I think you've described it well. I think that, that when I look at what I do today, I enjoy it. Do I wake up and saying, this is the rest of my life, where I will fully get behind. Behind it? No. I think that I'm in search of what that next chapter is. I've been good at reinventing myself a few times. Times. And I know that there will be more reinventions to come. I'm not fulfilled from that perspective. 


    Anastasia Koroleva: [01:02:16 - 01:02:30]

    So. You also mentioned that you are involved in philanthropy, and obviously you have R Squared, which is an angel investment firm, and they don't give you the kind of sense of purpose you had back in Magento. 


    Roy Rubin: [01:02:33 - 01:03:42]

    It's hard for me to measure the two. You know, we're building a company. There's, there's a different level of tension and momentum and passion. You know, when you're building a venture capital firm, I think, I think it's a little bit different. Right. You take a much more passive role to the investments as we're pretty active. But still, it's, it's nothing in comparison to what we were, both my partner and I, as operators. I enjoy the balance that it gives me today in life. Because today in life, I have other passions, I have other interests. Right. Starting with a family to my, my community and my, and my friends and my time to be outside in the mountains here and bike and hike and do everything else that I do. These are all important things in my life. Yeah. I couldn't do it quite at this level if I was still an operator running a business. So when, you know, a lot of people ask me, why didn't you start another business? 


    Anastasia Koroleva: [01:03:43 - 01:03:43]

    Yeah. 


    Roy Rubin: [01:03:43 - 01:03:46]

    And my simple answer is, because I know the cost. 


    Anastasia Koroleva: [01:03:46 - 01:03:47]

    Yeah. 


    Roy Rubin: [01:03:47 - 01:03:52]

    Right. I would have to give up a whole lot of what I am today to make that happen. 


    Anastasia Koroleva: [01:03:52 - 01:03:53]

    Right. 


    Roy Rubin: [01:03:53 - 01:03:55]

    And I'm. I'm not willing to pay the cost. 


    Anastasia Koroleva: [01:03:56 - 01:04:17]

    So help me understand. What's the difference between your investment firm and Magento, where your sense of purpose is lacking. Why in Magento, there was sense of purpose, and now you're clearly enjoying your new venture. But it's not quite given you a sense of purpose. What is missing? 


    Roy Rubin: [01:04:19 - 01:05:38]

    I don't know if anything, you know, is missing. I think I have additional perspective to life. You know, when Magenta was happening, that was very different. I had no money. Right. I was broke. I, I, this was the only thing that I had going for you know, I put everything I had into it. I think when I think as an investor today and maybe other investors, you know, will say the same, you know, there's a different. There's a different dynamic here where you're doing this at a later stage in life. I am doing this at a later stage in life. I have other things that run in parallel to it. The way that I've approached it is from a very different angle. Right. Where this is maybe the bulk of my day, but it's not my entire day. Where Magenta was, everything was, you know, from. I mean, it was 24 hours for 10 years. Right. It was 24 hours. This is very, very different. This is part of my day, and I love that. This part of my day. But I have. I have so many other, you know, other responsibilities and things that I love to do in life today that are also very important part of my day. So I'm not sure if this answers your question or not. 


    Anastasia Koroleva: [01:05:40 - 01:06:05]

    It is. It is. I'm just trying to figure out what purpose is for you and why. You had it in the past, you want it today, you don't have it today, even though you've experienced so many other different things and your life is much richer and maybe much more fulfilling. Would you say it's more fulfilling or less fulfilling? 


    Roy Rubin: [01:06:05 - 01:06:06]

    It's 100% more fulfilling. 


    Anastasia Koroleva: [01:06:07 - 01:06:21]

    Exactly. It's more fulfilling. You still are hungry for that sense of purpose, but you can't find it. So I'm just trying to pinpoint what it is that you're missing in your life that would have. Would be. Given you a sense of purpose. 


    Roy Rubin: [01:06:22 - 01:07:18]

    Listen, I think it's a fair question, and I don't have a clear answer because I don't think I've yet discovered it. Right. I can tell you what I enjoy to do, what occupies my day when I'm. What I'm having a lot of passion for. But is it. I think purpose is that next level thing that for me, as I said, I'm still in the process of. Of discovering, you know, I found myself. I mean, I'll tell you another example. I found myself leaving Magento, as I said, with largely no friends, A lot of colleagues, tons of colleagues. But who do I call in the middle of the night if something goes bad? Right. Yeah. And I've been on a mission to meet people. That is a high priority for my wife and I to expand. Yeah. Because we said, you know what, we. We have lost 10, 15 years of our life in meeting people. Now we have to, you know, to kind of make it back. 


    Anastasia Koroleva: [01:07:18 - 01:07:20]

    How do you go about it? 


    Roy Rubin: [01:07:21 - 01:07:40]

    I really make an effort. I invite people over, I open up my house, I reach out to people and you know, people that are interesting that I, that I, that I know I'll have something in common with. I put myself out. It's work. I put myself out there and I have no shame. 


    Anastasia Koroleva: [01:07:40 - 01:07:41]

    Amazing. 


    Roy Rubin: [01:07:42 - 01:07:45]

    And it's not natural to me, by the way. 


    Anastasia Koroleva: [01:07:46 - 01:07:47]

    I'm sure it's not. 


    Roy Rubin: [01:07:48 - 01:08:47]

    Yeah. No. But you know what? I do this over and over again and I've made some incredible friends. I go on these cycling trips. Cycling is the best way to meet people because you have them hostage next to you riding a bike for hours. And it's, I mean, hostage is funny. Right. Because we all want to be there together. But people are very open. It's a very, it's a very, you know, it's a great community. And I've met people just riding bikes, even randomly. Like I'll go on a bike ride right now and I can meet some interesting people that are already like. So it's not planned but, but it's been, it's been, it's been amazing. It's opened up my life in so many ways. I have friends from all over the world. I'm not done. I want more friends. I want to have more colleagues. I want to, I want to learn from people and, and it's a job. It's like we've taken this as something that is very important for our well being. 


    Anastasia Koroleva: [01:08:47 - 01:08:48]

    Yeah. 


    Roy Rubin: [01:08:48 - 01:09:25]

    To build communities and to have, you know, to have people that we can spend time with. And we think it's really, really important. Another thing that was interesting, Magento was like this rocket ship. From the first minute, it was absolutely just such a fast moving train that I was caught unprepared to really deal with it. Didn't have the right team. Had a lot of demands from partners and from customers and from the ecosystem at large. 


    Anastasia Koroleva: [01:09:25 - 01:09:25]

    Yeah. 


    Roy Rubin: [01:09:25 - 01:10:41]

    And it was very hard to keep up. Right. Which was very, very draining for me as. Because I always felt like I wasn't delivering. I always felt like I was coming up short. Really up until the end. Right. We never had enough people, resources. The demand was, was all. Or I've never spent a dollar marketing. It was all organic, amazing. And. But we would put these conferences together and in Vegas and 3,000 people would come and I couldn't even walk the halls because people would come to me with asking for things, feedback, wanted to shake my hand, wanted to take some selfies. All that kind it got to the point where I needed a posse with me just to follow me because I could not make it from one meeting to the next. So what I would do in future years with these events, I would literally just hide in my room. And I still to this day believe that there's a part of me that wanted to be just in a cave. 


    Anastasia Koroleva: [01:10:42 - 01:10:43]

    Yeah, I can see. 


    Roy Rubin: [01:10:43 - 01:11:04]

    And just weather the storm because I could not deal with the volume that was coming my way and the way that I dealt with it. You know, everything, any type of feedback that somebody would give me, I would take to heart. Of course, it's not like I was this, you know, it. Always able to be brushed off me in a second. 


    Anastasia Koroleva: [01:11:05 - 01:11:05]

    Yeah. 


    Roy Rubin: [01:11:05 - 01:11:12]

    So it sat in my head and I couldn't sleep if things weren't right or weren't perfect or could be optimized. 


    Anastasia Koroleva: [01:11:12 - 01:11:20]

    Yeah. Must be so overwhelming. Yeah. Draining and overwhelmed. And I can see that you're quite introvertish. So. 


    Roy Rubin: [01:11:21 - 01:11:21]

    Yeah. 


    Anastasia Koroleva: [01:11:22 - 01:11:28]

    All these activities would naturally be draining for you. They wouldn't be energizing. I can see that. 


    Roy Rubin: [01:11:28 - 01:11:30]

    You're right. You're good. You're good. 


    Anastasia Koroleva: [01:11:33 - 01:11:53]

    Fantastic. But Roy, now I'm really curious. So you had all this attention and maybe you didn't want it, but you had it. But when the company was sold, how did you deal with not having that identity as a CEO, founder, all this attention, how did you deal with it? 


    Roy Rubin: [01:11:56 - 01:12:08]

    It was in some ways a relief, I have to say, because it became, not. Not immediately, but it became somebody else's problem. 


    Anastasia Koroleva: [01:12:08 - 01:12:09]

    Mm. 


    Roy Rubin: [01:12:09 - 01:12:34]

    Right. Growth is often seen. I mean, you know, it's interesting. It's almost like the, the wrong answer to give or not the expected answer to give. But this was so draining on me and this was so, so fast and so quick and, and it became such a, Such, such a, such an onus on my, on me personally. I don't think I slept for 10 years that I was 45 pounds heavier, by the way. 


    Anastasia Koroleva: [01:12:34 - 01:12:35]

    Yeah. 


    Roy Rubin: [01:12:35 - 01:13:12]

    Right. And when this was over, I felt a sense of relief that I could finally sleep at night, that there's more resources, more people that cared than just me. Although obviously my team cared, but, you know, still at the very top as the leader. This became something that was on my shoulders. There were other shoulders, so this could follow. Issues that could fall on. And when you have a high growth, fast growth company, there are tons of issues. Right. Maybe from the outside it's hard to see, but, you know, this is an entrepreneur yourself. 


    Anastasia Koroleva: [01:13:12 - 01:13:13]

    Yeah. 


    Roy Rubin: [01:13:14 - 01:13:19]

    You don't want to see sort of, you know, beyond you Know, under the table. What's. What's going on? 


    Anastasia Koroleva: [01:13:20 - 01:13:41]

    Yeah, of course it's overwhelming. It's huge responsibility. It's stressful. Absolutely. But it's interesting that I guess your ego was not quite as big as most of us. If you didn't. If you didn't feel the need to find a replacement for your prestigious status. 


    Roy Rubin: [01:13:42 - 01:13:52]

    Maybe I don't even think I wanted the status. Right. I don't think I even wanted the status. You know, it's funny, I. Huh? 


    Anastasia Koroleva: [01:13:52 - 01:13:55]

    Was it a burden most of the time? 


    Roy Rubin: [01:13:55 - 01:14:38]

    Look, I loved it, right? I loved it in many ways, but it was absolutely a burden. You know, it was. It was. You know, when I went home, you know, I wasn't thinking about my status. I just wanted to be with the family. Right. And. And yes, I, I think I don't, you know, I. Or at least I like to think that I don't have an ego. And it's funny because when, when I sat down with. With the folks at ebay, when they acquired the company, they asked me what I wanted to do next at ebay about my career. And I looked at them and I said, whatever you need me to do, right? Whatever you think is going to be the right place for me to add value to you. 


    Anastasia Koroleva: [01:14:39 - 01:14:41]

    They probably didn't believe you. 


    Roy Rubin: [01:14:41 - 01:15:20]

    They probably, I swear to you, they were shocked. And I remember this and said, well, wait a minute, wait. That's not the typical answer we get. I said, well, I love what I do and I just want to continue adding value. You know, I also. Side of me knew that I probably wouldn't stay there forever, but, you know, they're used to working in environments where people have aspirations to grow and to become, you know, meaningful stakeholders. And, you know, for me, I just wanted to build. Yeah, it was an accidental story, Magento. It wasn't something that I planned for years. 


    Anastasia Koroleva: [01:15:21 - 01:15:32]

    So was it. Was it the creative bit that was the most fulfilling for you, or was it more the operational side of things? 


    Roy Rubin: [01:15:33 - 01:16:42]

    100% creative? I don't think the operational side was actually. Was actually a strong suit of mine, and I had great operators underneath me. And that saved, I think, a lot of what we were doing because, you know, and I. And I realized this, and this is why I brought. I brought those people on. I've always believed that I'm a creative trapped sort of in a. Either an engineer or a business person's body, but I love the creative side of it. Magento is a creative story, if you think about it, right? Of course, yeah. How do you scrapped. Yeah, I mean there's so much of what we did that we had to be creative and engineer our way through different models. This was a non standard company by many, many means. Yeah. And it achieved non standard outcomes by many means as well. Right. But there was a lot of creative process in there. And I've always been, this has always been the side of me that I've always wanted to explore more of. And I knew that there was, you know, something there and this was the man. So this is how it manifested right through building this technology company. 


    Anastasia Koroleva: [01:16:43 - 01:16:46]

    So how do you channel your creativity now? 


    Roy Rubin: [01:16:55 - 01:17:56]

    I mean, I've done a few things over the years. Whether it's, you know, to paint or to draw or to even know, even play around with wood shop. I can't say that I found yet what, anything that, that, that is sticking. But there's always the lens that I look the world through which is, you know, which is creative lens, our home, the way that we approach different opportunities and problems. But I think it's still an unfulfilled part of my personality and I've known this, this is part of me from a very young age. And there's still more on this front, I hope to some extent if the right things line up. But it's definitely part of my Persona that I think about continuously. 


    Anastasia Koroleva: [01:17:58 - 01:18:51]

    Brilliant. Because I found that it's very helpful for people after an exit to have clarity as to whether they are creators, operators or investors. Because if you don't have that clarity, this is where you see people who are very creative trying to do very uncreative work which they don't find fulfilling. They are not motivated a few years later and they just want to correct their course because they went into the wrong direction early on. Happens all the time. So I'm very happy to hear that you had clarity on that, Roy. I always ask the same question at the end of an interview, but you actually started answering that question early on. But I'll still ask it ask you how do you want to be remembered? 


    Roy Rubin: [01:18:58 - 01:19:52]

    I think when looking back, I want to play a role and make an impact. And I'm not talking about the business side of things because I think that's less interesting. Right. I think for me it's about having an impact in my community, you know, having something that, that helps our, you know, our people, our community that the kids can, can be part of that the kids will want to have, you know, in their life. So it's not forced, it's something that they are part of from the very Very beginning. And, you know, something that will define the sense of purpose for the rest of our lives. 


    Anastasia Koroleva: [01:19:55 - 01:20:23]

    Beautiful. Thank you. I can't finish the interview, though, because you just said something that makes me keep asking you questions. Why are you saying that a business cannot have that kind of impact? You want. Because Magento changed the world for the better for so many people. What's wrong with that? 


    Roy Rubin: [01:20:30 - 01:20:47]

    Magento has. And, you know, Magento has transformed many people's lives, but it doesn't. It's not enough for me. It's not enough. I. I actually want more. 


    Anastasia Koroleva: [01:20:49 - 01:20:49]

    Good. 


    Roy Rubin: [01:20:49 - 01:21:50]

    And. And I think. Okay. And I think I'm capable of it. Right. You know, now with the means. And. And I think the experience. And. And I want to say the gray hair, but. But the age. And, you know, I'm obviously very proud. You know, people still to this day reach out and, you know, and share how much Magento is, you know, meant for them and change their lives. But. But I feel like I can do that over and over again. Right. In terms of the ability now to make an impact, you know, through other channels as well. So maybe it's because it came at a much younger, you know, place in my life, and maybe. Maybe many would say that's enough. We've made an impact. We're. We're good. But I. I don't feel fulfilled there. Right. I feel like there's a whole lot more there ahead of us. 


    Anastasia Koroleva: [01:21:52 - 01:22:12]

    I love it. To me, it looks like you're really ready to start that new chapter in your life where you find that real impact that's truly yours, uniquely yours, and comes from who you are and from understanding who you are and what you want in life. That's wonderful. 


    Roy Rubin: [01:22:12 - 01:22:14]

    Thank you. I appreciate it. 


    Anastasia Koroleva: [01:22:14 - 01:22:32]

    All right, Roy, thank you so very much. I could be talking to you for hours and hours. I hope we'll do it again, and you'll update me on your continuous search for purpose and fulfillment. And in the meantime, just. I'm super grateful for this. 


    Roy Rubin: [01:22:32 - 01:23:16]

    You. Thank you. I share a podcast with as many founders as I possibly can because I know this is an issue. You know, we have friends that struggle with this, and it's a real issue. And you've picked. I think you're the first one to really pick up on it and talk about it. Right. And it's something that I've thought about since the minute I left. You know, part of this trip for me was. Was escaping this eventual reality of having to deal with. Right. Of course. That's how I dealt with it. Not everybody can deal with it in these, you know, in this way for various reasons. But I think what was unique about me is that I understood that this is a problem. 


    Anastasia Koroleva: [01:23:17 - 01:23:18]

    Yeah, sure. 


    Roy Rubin: [01:23:19 - 01:23:27]

    And I said, okay, well, how do I deal with this problem? I deal with it by hiding in a cave for a little bit. Right, by stepping outside. 


    Anastasia Koroleva: [01:23:27 - 01:23:50]

    Yeah. Well, though, you didn't just hide in the cave, you were out there interacting with the world and learning about yourself by interacting with the world, which is super important because, yes, we do need to sit alone in the room and think about, you know, what's inside, but we also need to interact with the world as much as we can. So we have all these experiences helping us move forward. 


    Roy Rubin: [01:23:50 - 01:24:03]

    I think it's both 100%, but the cost for me, by the way, we didn't talk about this in the thing, but the cost for me was that at my peak, I ran away. 


    Anastasia Koroleva: [01:24:04 - 01:24:05]

    Of course. 


    Roy Rubin: [01:24:06 - 01:24:43]

    And not only that, I never came back to LA. I live about 30 miles north of LA. So as this ecosystem here was beginning to really grow, I. Many people don't know me here in la, and they should, because I probably had one of the biggest exits in LA's history. Of course, Definitely. And, you know, every time I come back now, as an investor, I have to develop relationships. So I come back and I meet with people and, you know, we go to dinners and they're blown away. They're like, I've never heard this story. And I say yes, because I left. 


    Anastasia Koroleva: [01:24:45 - 01:24:46]

    Because you left. 


    Roy Rubin: [01:24:46 - 01:24:59]

    I left. Right. No, because I needed to leave. I needed to get away. Right. Because it was just. There was. It was absolutely nuts, you know, for me having to deal with it. Of course, yeah, yeah. 


    Anastasia Koroleva: [01:25:03 - 01:25:19]

    But I'm really excited to see how, you know, your thinking will. Will develop in. In what direction? What you find deeply fulfilling for you, for yourself, whatever it is, it may be very different from what anybody has in mind. Right. Because it will be truly yours. 


    Roy Rubin: [01:25:21 - 01:25:22]

    That's right. That's right. 


    Anastasia Koroleva: [01:25:22 - 01:25:23]

    Thank you so much. 


    Roy Rubin: [01:25:23 - 01:25:27]

    All right, well, listen, this was amazing. You're so great. Thank you for all that you do. 


    Anastasia Koroleva: [01:25:27 - 01:25:29]

    Thank you, Roy. Talk to you soon. 


    Roy Rubin: [01:25:29 - 01:25:31]

    We'll be all the best. Bye. By.



 
Anastasia Koroleva
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