From Where I Sit: Season 2, Episode 7 with Randi Zuckerberg, Founder & CEO, Zuckerberg Media Transcript

Randi Zuckerberg:

Every single one of us should consider ourselves an entrepreneur and be thinking like an entrepreneur because you never know when an idea you have might be the next thing that's used by billions of people around the world.

Tom McGee:

Welcome to From Where I Sit, the podcast where we explore the forces shaping America's built economy. I'm your host, Tom McGee, president and CEO of ICSC. In discussion with prominent leaders and innovators, we cut through the noise to explore the trends and innovations influencing the future of our communities.

Welcome to the latest episode of From Where I Sit. I'm excited to be joined by a leader who has built a remarkable career at the intersection of technology, entrepreneurship, and the arts. Randi Zuckerberg is an investor, author, and founder of Zuckerberg Media and HUG, two ventures that have allowed her to combine her passions for tech, media, and the arts. Before founding her own companies, Randi was an early employee at Facebook, where she led the creation of Facebook Live and played a crucial role in shaping the growth of social media.

Randi is also a prominent voice for women in business, using her platform to champion women founders and create pathways for women to lead and grow. Outside of her impressive career, she's also an ultra-marathoner who has performed on Broadway and is an advisor to entrepreneurs.

Randi has a special connection at ICSC. I'm pleased to share that she will be our keynote speaker at ICSC+PROPTECH, taking place during ICSC LAS VEGAS in May. ICSC+PROPTECH is a new event connecting CRE decision makers and buyers with tech innovators. And with Randi’s passion and support for women in business, we'll also invite attendees of ICSC+WOMEN IN CRE, also taking place for the first time during ICSC LAS VEGAS this year, to join her keynote as well. With years of experience in the tech sector and as a successful entrepreneur, Randi has a unique ability to share leadership lessons and to translate emerging tech into real life applications. Her perspective will offer valuable insight to our members as they think about what's next for retail and commercial real estate.

Randi, welcome to the show.

Randi:

Thank you so much. What an introduction. It's a delight to have this conversation with you.

Tom:

Well, I'm really looking forward to talking to you and the introduction is well deserved. You've had such a diverse career and have touched so many things in your career. And I want to kind of start with that. I know I've heard you talk about your passion for the intersection of arts and business and technology as well. And your career journey has been quite unique. So let's talk a little bit about how you've been able to kind of combine those two interests of yours around arts and business together.

Randi:

Absolutely. And I actually think those two skill sets go so much more hand in hand than people think. I always like to say that the best entrepreneurs have an artist’s heart and a business brain because you can't ignore data. You need to be organized and thoughtful and have process-driven thinking and strategy. Things change. We are in a very rapidly evolving world. You need to be able to pivot on a dime. You need to be able to think on your toes. And so you need that kind of artist’s heart in order to just be really creative and not get stuck in one way of doing things.

So I feel really lucky. I was a theater kid growing up. I loved the theater. I actually think that served me well in business later in life because I had a lot of experience getting rejected from things early on. You learn when you show up for an audition as an 11-year-old and you hear no, and then you wake up the next morning and you realize that the sun still rises, it really kind of sets you up to be able to experience failure and not get shaken by it later in life. And so I feel like I owe a lot of my ability to think on my toes, handle rejection, work well with others for my background in theater. And I've always had a huge respect and love for the arts. And I think it's really fun in this stage of my career that I'm in. Now that I'm more supporting other entrepreneurs, advising, sitting on boards, I feel like I'm a patron of entrepreneurship, just like people used to be a patron of the arts. And that's just as important in today's world.

Tom:

That's fascinating. I mean, I love that term, patron of entrepreneurship. You know, some of the things you talked about, the resiliency, you know, that came from your early lessons in the arts. Actually, the creativity, right? If you're an entrepreneur, by definition, to be successful, you have to differentiate yourself in some way from the competition, tying into your creativity.

Looking at you behind you is a bunch of race bibs and medals from your racing and you're also an ultra-marathoner. You're into endurance. We had a little conversation about that before we began the podcast. Talk a little bit about that. I mean, the lessons you've learned being an entrepreneur. I think you've run something like 11 marathons and seven ultra marathons in the last couple of years. I mean, that has had to—talk about resiliency and, you know, kind of having a sense of commitment and competition. So talk about that.

Tom:

Absolutely, and I love that you and I are fellow endurance athletes. You really bond with other people over doing hard things. This has been a new journey for me, actually. It was not on my life bingo card thinking that I was going to be an ultra-marathoner, but about three years ago, I would say I couldn't even run two miles. And I started getting into running a little more. I live right on Central Park in New York City, which is a perfect place to run. And I entered a 10K race in Central Park, which is six miles, and it was all women. And the race, it was so cool. It was like 10,000 women, all ages, all body types, all abilities in this race and I just thought, wow, if all of these women are showing up for themselves this way, maybe I can show up for myself a little more in my life.

You know, I feel like, especially for a lot of the women out there, women are really good at having supporting character energy. I worked for my brother, supporting his vision for a decade. I’m Asher, Simi and Shira's mom. I've kind of stood by and supported my husband as he's had this incredible career at Peloton and other companies. And I kind of realized, I was like, okay, I'm a great supporting character and that is a very important role to play in the world. You need the people who are right next to the entrepreneurs and the leaders. I was like, but I deserve to have a little main character energy too.

And I, you know, I remember when I crossed the finish line of my first marathon, I felt that main character energy. I felt, you know, no one can attribute this to who my brother is or who the men are in my life or anything. This is my own hard work and grit and resilience, and no one can ever take that from me. And I think that has really driven me to kind of push the boundaries in running.

And just this past year, I ran a 250-mile ultra marathon through Arizona from Phoenix to Flagstaff, Arizona. It was one of, there were fewer than 150 women in the world last year that ran that distance. So it's really exciting to have been on this journey and to be able to, know, step, walk through the world in a new way, knowing that I can do these hard things just on my own.

Tom:

I mean, that's 250 miles. That's just, that's insane. That's crazy. But I love it. What was the, you did that over the course of how many days?

Randi:

So took me 113 hours. I ran straight, for four and a half days. So the race started on Monday morning at 5 a.m. and you had to finish by Saturday afternoon. That's the cutoff. I finished on Friday evening. So I had a full 12 hours ahead of the cutoff, but that still was four and a half full days of running. I think I slept for six total hours during that time.

Tom:

Sleep deprivation. You're fighting not just—the sleep deprivation that does a lot to you.

Randi:

Yes, sleep deprivation, I ran the first 80 miles, you have to be alone. So I ran through a full night in the desert, in the pitch black by myself. But I will say that you show, it is impossible to do something that difficult and be the same person on the other side of it. And I show up in the world differently from doing that. And I show up in my family differently. And I think even my children, my sons who are teenagers, I think the way they think about hard things and pride in yourself is different from seeing that. So for me, that was a real incredible life accomplishment and moment.

Tom:

Well, congratulations, because it really is. I mean, and to accomplish that is just unbelievable. I mean, not just the physical aspect of it, but to your point, the mental aspect of it, dealing with running alone in the middle of the night. I mean, you do feel like, I presume, and I've run a couple of marathons and did some triathlons, nothing like what you just did.

Randi:

No, you've done incredible things. But don't you think that the mental toughness, entrepreneurship and business and leadership, like those skills go so hand in hand, that mental resilience. And so I actually think my Silicon Valley startup experience was probably the best ultra marathon training that I could have had in learning that resilience.

Tom:

Well, you're so, you're so right. And it is, you said a couple of things that just immediately as somebody who, you know, enjoys endurance sports, just resonated with me. One, you know, just the doing something hard. And sometimes people say, you know, why do you do it? And I said, well, I'm not really a runner, but I just like to do really hard things. Yeah. I just like to really challenge myself. And then that sense of confidence that comes with it, you know, you've crossed the finish line. You don't feel, at least I've never really felt great immediately, but 15 minutes later, I felt like I could conquer the world and it just kind of that muscle memory of confidence that comes with that. You had talked about your first 10K in Central Park and that it was a group of women that were running. And I know one of the things that you're passionate about is women in leadership, women in STEM, women in entrepreneurship, commercial real estate and technology. They're often viewed as male dominated, let's put it that way and changing clearly, but still viewed as male-dominated. What are some of the challenges that a woman faces that are unique to them when they try to progress in a male-dominated field like that?

Randi:

I really appreciate you bringing that up and this is such a passion area for me. It's interesting, I always ask myself, I'm like, Randi, why couldn't you have one area of your life doing things like with other women? Because even the ultra-marathons that I just talked about, there's barely any women that are on the start line of those races. So I worked in tech, which is incredibly male dominated. All of my hobbies and passions are male-dominated. I think there's a few challenges and there's a few beautiful opportunities there. I think that the challenge, of course, is mentorship. When you're the only woman in the room, you look around and you see the men are constantly helping one another and discussing things, and you just don't feel like you have that support network. And so I've learned to actually find peer mentors in other industries. So maybe I couldn't quite find a peer group early on in tech, but I found my women in finance, in media, in other areas where women, or in law firms, where women were also feeling the same way as me and we could connect and rise together in our fields.

I think, you know, one thing we all need to do a little better as a society is we need to double down on not losing girls, especially at kind of a pivotal time in their preteen and teenage years. We need to do a much better job at communicating that STEM is for everyone. It's not just for boys, that, you know, there are a lot of incredible careers in design and in different parts of tech that I think people have a vision in their head that there's kind of one role in tech. And so I think we can all do a better job in making sure we don't lose girls in tech before they've even started. So that's something I'm passionate about. But I think the exciting opportunity is, just like in running, women were actually only allowed to run the marathon about 50 years ago.

Tom:

I just learned that, that's crazy, isn't it?

Randi:

Because scientists thought that our uteruses would fall out of our body if we ran that distance. It's so new that women are even allowed to run the marathon distance. Any time that you're at the cutting edge of something, you get to write the playbook. I feel that way with my ultra marathons. I felt that way being the only woman in the room in tech. It felt a little lonely, but at the same time it was exciting because I knew that the women 30 years later would be studying what I did. And they'd be studying the playbook that I was writing. And there is something so beautiful about having that opportunity to be a trailblazer like that and to write the playbook. And so, you I encourage any women who are listening to this or feeling a little isolated or alone in your career to just think about all of those women in future generations that are going to be studying what you did and boosting their career by learning from the trails that you paved.

Tom:

Well, thank you for that. I mean, what you're doing is so important. I'm a proud girl, dad. I have a 28-year-old and a 25-year-old. One's in the STEM field. She's getting her master's in neuroscience and one's a documentary filmmaker. So in the arts field, but having, you know, female or women mentors to look to that is so important. And I also think one of the things that you said that resonates with me as a father, you have two daughters, you see things that you never observed before and in regards to some of the challenges that are specific to trying to advance your career as a woman. So having mentors like you and role models like you that they can look to, I think is super, super important. Particularly when you're doing the amazing things that you're doing, kind of breaking boundaries and leading industries and running ultra marathons and all that kind of things. It's quite inspiring.

You mentioned mentorship and you look to mentors not just in the technology field, but in other fields, but you also mentor a number of, and have been a mentor to a number of women business leaders. Talk about some of the strategies or advice that you've given them to help them advance their career.

Randi:

Yeah, that's something I really love doing. I like to say that I'm an amateur mom to my own children, but I'm a professional mom to all of these entrepreneurs. And I'm a little too exhausted to go back into the fold myself and build a startup from total scratch. But I love handholding the next generation of entrepreneurs through building their dreams and the next big companies. And I think especially, I especially love working with women because I think women are taught from a young age to be small and not take up as much space in a room or downplay their achievements. And so the first place that I like to work with women is on their investor pitch decks, how they walk into rooms, how they sell themselves and their vision, because you sort of have to go against everything that you've been taught as a woman in society in order to pitch a startup and kind of show up in the way that you need to lock in partners and investors and employees. And so that's kind of my favorite area to mentor young women in because you can really see an immediate ROI in how they show up in a room and then how that affects their business. And of course, I love shepherding them through the ever-changing world of tech and thinking through how to pivot, how to make big decisions. But there is something beautiful about watching a woman take up space in a room and kind of into her power in a way that really benefits her business and her community.

Tom:

Building the confidence and I think building your brand and selling your vision. Talk about, obviously, you were at Facebook in the early days and you watched a business that really was a true startup at that point. I think you were employee 10, is that correct?

Randi:

Yes, 10, such a tiny little startup.

Tom:

And today, obviously, it is what it's become, which is one of the largest companies in the world. The lessons about scaling a business, whether it's just scaling it from one employee to 100 employees or scaling it from one employee to what Facebook is today, I'm not sure how many employees it is, but it's obviously one of the largest companies in the world. Lessons for entrepreneurs as they try to, you know, basically take that vision and build it, scale it into something that's a repeatable business model.

Yeah, I mean, I think there's a lot of lessons that I've learned, but I think the biggest thing is that it's just, never too early to start thinking about your company culture. I think a lot of people think, okay, you know, I'll build something and then when we hit a certain size, I'll think about culture or we'll think about the dynamic of our team or our business. But one thing that I think we did really well at Facebook was we kind of locked in this culture of innovation and entrepreneurial spirit very early on, even as a tiny company. And we stayed true to that. Even as we grew to be a public company and have tens of thousands of employees, we were still doing these, you know, all day hackathons where we were inviting employees to, you know, build something totally out of the blue. And there was still always these full company sprints where it was like a few weeks where we're all going to relearn mobile coding together, we're all going to deep dive into AI. And I think having, keeping that spirit made it feel like it was a tiny startup, even when it was a multi-billion dollar company. I really think that more companies could learn from that and building that kind of culture very early on so that it's in every fiber of your company as you scale.

Tom:

It's interesting. I mean, there's the old saying that culture eats strategy for lunch. I mean, you can have the greatest strategy in the world, but if you don't have a great culture and people that are inspired and motivated to implement a strategy, the strategy is just words on a piece of paper.

Randi:

Absolutely.

Tom:

You mentioned the hackathon and I believe it was in a hackathon or something similar that Facebook Live came to be. Is that true? Talk about that story of the creation of Facebook Live, which has obviously become really an inspiration, not just what Facebook Live became, but an inspiration for what's happening all across social media and the web.

Randi:

Thank you. So for me, I mean, the emergence of the iPhone was such, I think, a game changing moment for society. I mean, the fact that we went from doing everything on desktops and laptops to suddenly having the computing power of spacecraft in the palm of our hand. And so for me, as someone who's always been a theater kid and an artist, my first thought was, okay, how do we harness this power to make everyone into a media company and give everyone the power to be their own television network and their own radio broadcaster. So one of these hackathons, you know, unfortunately the computing bandwidth was not up to par in 2010 to be able to go live from a phone to millions of people. So we had, I had backpacks full of equipment, but I was able to kind of go live from one of our hackathons and it was just really interesting to think that people kind of all over the world wanted to tune into this very technical developer hackathon that we were doing. I was like, who are all these people? Why are they interested in just seeing a bunch of engineers sitting around coding? But it was so eye-opening to me because I realized that we really all do have stories to tell and platforms to reach other people. And from then on, over the next few months, I worked on Facebook Live as a side project. I was running consumer marketing at the time, and then as a side hustle, building Facebook Live. I think today there's, you know, hundreds of people who just work on live streaming as inside of Facebook as their main job. But I was doing it as like a little side project.

And four months later, President Obama asked to use Facebook Live to go live to the entire country. And that was a wild experience for me because I always thought of myself as a marketer, as someone who was a little more behind the scenes supporting the product and the engineer folks. And that experience taught me that every single one of us should consider ourselves an entrepreneur and be thinking like an entrepreneur because you never know when an idea you have might be the next thing that's used by billions of people around the world. And that was just probably one of the most exciting moments of my career.

Tom:

I mean the speed of that because I think I my recollection having heard you speak one other time about this that the first broadcast of Facebook Live you said there were two viewers: your parents, your mom and your dad.

Randi:

My mom and dad were the only two people who tuned in and even my mom was like, this is really boring content. And so I do also think that, I think people have very unrealistic expectations that things are overnight successes and people try something once, they post something on social, they try something with marketing, it doesn't work, they give up. you know, I worked on Facebook Live for almost seven years before it was ready to go out to the public. So of course, you it looks like one day Facebook launches this go live button and suddenly, you know, like magically people can go live. But what they don't realize is it took seven years to be an overnight success. And I think a lot of people just give up way too early.

Tom:

Well, that's the endurance athlete in you too, right? Nearly the seven years is, you know, like the running 250 miles. You just have that sense of resiliency and, just keep going, put one foot in front of the other.

You started your career at Ogilvy. So you started in marketing and, and, you know, that foundation of, and you mentioned the importance of selling your vision, you know, communicating your brand proposition and so forth. When you talked about, you know, women starting businesses, trying to generate and obtain seed capital. How important were those lessons you learned early in your career to where you are today in that, you know, concept of brand building and storytelling?

Randi:

Incredibly important. I will say that Ogilvy was the perfect place to start my career for a few reasons. The first is there's a female CEO, Shelly Lazarus, who had worked her way up from a junior role in the company to CEO. So that was incredibly inspiring to be, to see that as the leader of the company in my first job. Also, at that time, they had an incredible training program for entry level, which is in addition to your day job,

you got paired with a nonprofit. And so that nonprofit got free marketing and you got the opportunity to kind of learn on the job as a marketer. And so I got paired with the Special Olympics New York chapter. And for a year, myself and a team of a few other entry level colleagues for a year, we basically ran the marketing for that organization. And I truly can't imagine, it was almost like being in a startup, really. I can't imagine a better way to learn a skill than just being thrown in the deep end and having an organization rely on you to do your job. So that was an incredible experience. And the third part of that was that almost everyone else in the entry level program was put on these very traditional marketing campaigns, television shows, the Super Bowl, you know, all of these things. And I got staffed into this brand new team inside of Ogilvy that was digital marketing. And I remember I cried. I was so angry. I was like, I want to be on the television sets with everyone else. I don't want to be, what is this like dead end thing that they're putting me into? And then fast forward two years and digital marketing was like 50% of the company's revenue and all of my other friends were still getting cappuccinos on television sets and I was running a team inside the company. And that ended up actually, I think, being the luckiest thing that happened to me early in my career. Sometimes things that seem awful and unlucky end up being the greatest gifts to your life or your career.

Tom:

Gosh, that's amazing. And there's such an intersection with a couple of things. The Special Olympics, I mean, what a privilege it is to work on that mission and also the relationship that has to you and your interest in sports and athletics and so forth. And then digital marketing and what you've built with Zuckerberg Media and earlier Facebook Live. I mean, how, to your point, I mean, you never, things that might seem like a bad break could end up being the greatest break, right?

Randi:

Yeah, I look back on that and I feel that that sparked my entire career in technology and I never would have voluntarily put my hand up to be on the digital marketing team. Sometimes I have found in life that all the best opportunities happen when everyone else is going left and you go right.

Tom:

Yeah, yeah, so true. So you're, you're knocking it out of the park at Ogilvy, things are going well. And then your brother calls you and says, hey, I have this idea. Why don't you join me at Facebook? What prompted you to say yes? I mean, I got the family connection and all that kind of stuff…

Randi:

I tried to say no. I wish I could tell you that I had the foresight at age 22 to think that, you know, this is going to be a multi-trillion dollar company. No, I was living in Manhattan. I was working at an ad agency. Like I was going to fun parties. I had a great life in New York City. The last thing that I ever thought I would do was move to suburban California and like work with my little brother on like his stupid business. Like that's the last thing that I ever thought. And finally, he was like, I'm going to buy you a plane ticket out to Palo Alto. Just come see what we're doing. Come out for a weekend. I could really use some digital marketing advice from you. So just come out for a few days. And I was like, sure, yeah. And I completely fell in love. I had never been in a startup environment before. I'd only just been in corporate America. And just the fact that you got to make all your own decisions and own your successes and failures and just seeing these guys coding around the clock with this. Like they truly believed they were going to change the world. It was so exciting that by the end of that weekend, I kind of decided to stay forever. And so, but believe me, I tried to say no a lot of times, and I'm really glad that he didn't take no for an answer, because that ended up just being the most incredible life-changing experience to be part of that rocket ship.

Tom:

By the way, how proud must your parents be? I mean, to see all their kids be so successful, you and obviously Mark, but your other siblings as well, all built great careers.

Randi:

You know, what's so awesome about my parents is like, first of all, I think if you met them, you'd be astounded by just like what normal down to earth grounded people they are. But like, you know, I have like my brother over here who's like built one of the most successful companies in the world. But yet like my parents are still on the finish line of every marathon that I run still. They're still, you know, like going to my sister's retreats for her venture capital firm that she's building. Like they're still, they treat every goal and dream, like it has equal significance and meaning. And I think that's like a really beautiful lesson that I've tried to bring into my own parenting.

Tom:

I mean, in addition to obviously talent, I think that sense of knowing your parents were always there and proud of you and supporting you also contributed to your guys’, obviously, your guys'…

Randi:

For sure. This is a realization that I've only come into recently as a parent myself, but I think when you come home to a safe space where you feel like people have your back, it gives you the permission internally to take more risk when you go out into the world. knowing that my parents had had my back that way, whether it was a marathon or whether it was in business and having that safe space in my own husband, in my own family now, I think has really enabled me to dream big in a way that I never used to dream for myself. And so I think that, you know, that's why family and the family you choose or the family you're born into is perhaps one of the most important decisions that any of us make.

Tom:

Yeah, for sure. For sure. So you're at Facebook for how long were you there, Randi?

Randi:

Yeah, I was there. Well, I meant to be there for one weekend and then I was there for 10 years.

Tom:

Ten years. Okay, so you really, I mean, in that 10-year period, from that one that first plane ride where you were going to spend the weekend to 10 years later, I mean, what a change in the organization to-

Randi:

Yes. When I started, we were this tiny little startup. It was a small office above a Chinese restaurant in Palo Alto.

Tom:

Is that where the office was, above a restaurant?

Randi:

Yes, it smelled great during those hours. It would make you so hungry because you'd be sitting there working and then you get these like delicious smells. When I left, I mean we had purchased Instagram for about a billion dollars and then became a public company. And so I got to see this journey from teeny tiny startup to a massive acquirer and a public company in its own right. It was just, you don't really get opportunities like that really ever. And if you do like once in a lifetime at most, so super blessed and lucky to have gotten that so early in my career.

Tom:

I mean, that's really the epitome of, you think about the story of the American dream and so forth, you know, somebody started, the stereotypical story, somebody starts a business in their garage and then grows it into, you know, a global icon, which is what Facebook and Meta has become. I mean, you know, above a restaurant and it becomes what it is. I mean, that's really the kind of the American dream, isn't it?

Randi:

Of course, I think actually the coolest thing for me, even beyond just being part of that and seeing that from the inside is when I go to lecture, guest lecture at universities now, and there are social media majors. That is a field of study in colleges and talk about, like I was saying before, talk about writing the playbook that other people go on to study. It is so cool to have been part of something that is now like an entire career path for millions and millions of people and to have been on the front lines of that is just, it's really even hard to put into words what that feels like.

Tom:

It really, I mean, that's an interesting point I didn't think about, but yes, I mean, social media didn't exist that long ago and now it's just so present in our lives. And it speaks to kind of the speed of change and just how quickly things accelerated. I mean, just that 10-year time period you were at Facebook from startup to public company acquiring Instagram, to one of the most valuable companies in the world.

To that point, someone who's lived through that kind of change and that trajectory of speed, how do people keep up with it? If you're a business leader and you're trying to run a business, but all the things around you are changing so quickly, are there lessons or advice for folks?

Randi:

You know, I wish that I had a definitive answer for you, but in some ways I'm still learning because the world keeps changing. But what I will say is that, you know, I saw a few instances along my journey in Silicon Valley where the world changed and some companies were open to it and some were resistant. So I mentioned the iPhone and kind of how that gave me the idea for Facebook Live. I think that's the clearest example though of how I got to see through my own eyes that some tech companies evolved with mobile technology and some were so resistant and it ended up being the death of the company. We realized almost overnight that pre-iPhone, almost 100% of Facebook usage was on desktop and mobile computers and almost overnight, like 50% of that changed to the mobile phone. And I feel like a lot of companies in Silicon Valley were saying, it's just a temporary thing. Things will go back to normal. And we were like, no, I think this is the new normal. I think the new normal is all mobile. And we ended up retraining all of our engineers, all of our staff. We took a massive hit to revenue in the bottom line by retraining our whole staff in mobile. Got a lot of pushback from investors and advertisers on the platform. But at the end of the day, that refocus saved our business and other companies that didn't do that, like Yahoo and a lot of the other companies that we saw around us, could never recover from not shifting their focus. So I think we're, sometimes it seems like you need to do that and you don't. There was a whole craze around VR and augmented reality and it never really caught fire. But I do think with artificial intelligence and everything we're seeing, this will be another mobile phone moment where the companies that can embrace and make the best use of AI, either in their internal operations with their processes or how they use it to work with outside clients. I think this is another kind of game-changing moment like that that we're on the precipice of.

Tom:

You know, just the, how right you were in making the decision around mobile, right? I mean, now it seems kind of, can't even imagine a world where you're not walking around with your phone is basically extension of its appendage at this point. It's like your hand, you know, in our world, just as an example of that, in the retail world, 30% of Americans made a direct purchase over the holidays through social media. I mean, they bought a product from something they were watching on a video and then they decided to just hit the buy now button and click and buy that. So outside of just traditional e-commerce and just that convergence of social media, mobile technology and so forth, AI.

So we can't talk about technology and not talk about AI. To your point, I mean, and I'm with you. I don't really know, have any sense of where this is going to end, but I know that we're at the beginning of something that's hugely transformational for business and for society in general. Just your, you know, I mean, I could talk about AI for hours, but your initial thoughts about artificial intelligence and where this might lead in the next five to 10 years at a high level.

Randi:

I mean, first of all, I'm so excited about everything that's going on with AI, but I also, having been on the front lines of new technology, I know that with any new tech that's getting introduced to society and at this speed, there are massive opportunities and massive challenges. I mean, just to be very vulnerable about some of my own experiences, I mean, you know, when I was kind of creating Facebook Live at that hackathon, I was thinking of all of the amazing use cases of live streaming video and 99% of the use cases are amazing and are like harmless. But I also watched as someone live stream themselves going into a church and shooting people and never, never in a million years when I was building that, did I even have like one glimmer of thought that people would use technology to be so evil. And I wish if I could go back in time and talk to younger Randi, I would say, know, keep innovating, keep building, like hurtle into the future at the speed of innovation, but also like take a few pauses along the way and really think through everything that could happen, the good and the bad and be a responsible leader as you push the technology forward. And so now when I work with entrepreneurs and I think about AI, I think about it from that lens. I think about how exciting it is to move forward at the speed of light and the possibilities that AI gives us. But I do think a lot about AI in the wrong hands. And I do think a lot about some of the high stakes costs to society of outsourcing some of these things. And I think all of us as responsible leaders need to constantly be thinking about both sides of the coin.

Tom:

Well, thank you for that. I think that, you know, particularly coming from someone like yourself who's lived through, you know, a technological revolution and now we're on the verge of another one to have that voice of, we need to have a sense of responsibility. I mean, it is, because you, it's that sense of responsibility, but also that push towards we need to keep going and we need to be faster because there's so much opportunity out there and balancing those two.

Randi:

You cannot let fear hold you back. I mean, just like the companies when the iPhone was coming out, the companies that were afraid of change and afraid of rocking the boat with current investors and clients suffered in the end. We are at a similar moment right now where it's okay to feel some fear of change and it's okay to know that the next few years might be a little bit of a messy middle where we're figuring out what the world looks like with some things managed by robots and still some things by humans and overlap. But then ultimately we come out the other side having developed new jobs and new skill sets.

And I was having a funny conversation with my son the other night because he's in a very demanding high school here in New York City and he was complaining to me about all the hours of homework he has. And I also went to a demanding high school in New York City and he was asking me if I had similar homework. And I was like, yes, I did, except that I was doing different things with my time. I had the same amount of hours, but I was handwriting my essays. Like I had to hand write essays and I didn't have like the nice calculator that calculates, like I was doing all of this. And I think like, what a waste of all of those hours that I was doing because computers do that stuff so much better. How much further would I be in my education if I didn't have to spend four hours a night in high school handwriting essays and doing the computation that a TI-84 can do in seconds? And we are better as a society that our children have graduated and can now spend the same amount of hours of homework but like in a wildly different way because of tech.

And so I don't think we need to be scared of the tech. I think, yes, things will change and society should change and should move forward.

Tom:

It's fascinating because we're at kind of a unique inflection point in history and you know, people will ask, well, what do I think about AI? And I said, well, I guess it's kind of like trying to predict what the internet was going to be like in 30 years in the mid-1990s. You kind of knew it was going to be a big deal, but if you would have made predictions as to specifically what would have happened, you'd probably be wrong because it ended up being, it developed into something much different. I suppose AI will be like that as well.

Before we leave AI, just to your point around how your son's example is a very good one and the comparison of your homework experience and his homework experience and the speed of change and what happened in Facebook in such a short period of time. Are there just advice for either companies or people that are interested in AI and engaging in it, but just don't even know where to begin?

Randi:

Yes, absolutely. And actually one of the most fascinating things that I've learned as I've studied AI is that when I went into it, I thought that all the biggest use cases for AI were going to be around productivity and copywriting and things. No, by far the top 10 uses of AI are things like helping people find meaning in their lives, combating grief and trauma and loneliness. Like people are using AI like a therapist, like a friend. People are using AI for very human things. And I think that was the biggest surprise to me when I started deep diving into AI was like just how human we are engaging with this technology.

So I think for anyone who wants to start with AI, I would say, you know, take a very low stakes part of your life and just start experimenting. So for example, like I started, my first use case with AI was bedtime stories for my daughter who's six. And I found an app that lets you, within seconds, put in your kid's name and their interests. And then the AI generates a bedtime story that puts your child as the main character.

Tom:

So cool.

Randi:

So I got to seem like a hero mom because every night I had a new bedtime story that put my daughter as the main character and it took me four seconds to get it with the AI.

So just an example like that, like I use AI for my running a lot. I recently just came off an injury and so I will start a chat where I'll be like, okay, here's where I am with my injury, here's my symptoms and my pain level. Here are the last eight runs that I did and how fast I went. What pace should I run my race this weekend? I will, like the AI will give me a play by play of mile by mile and it doesn't get sick of talking to me about it the way some of my family members get tired of me. And the recent marathon, I just ran a marathon on Sunday, two days ago. And the-

Tom:

How you feel?

Randi:

Yeah, pretty sore. I'm glad to be sitting down. AI guessed my time within 10 seconds of what I ran. So I would say, you know, pick some kind of low stakes, but passion areas of your life to start playing and experimenting with AI. And then little by little, I think you'll see that it starts to work its way into bigger areas of your life, your business, other tools and as you get more comfortable with it and you see that it can actually be a co-pilot and a thought partner for you rather than something to resist or be afraid of.

Tom:

Build that muscle memory and confidence with it. Did you, by the way, does your daughter know that back when she was four that you were using AI or does she still think you made mom made up these stories?

Randi:

I did actually tell her there was AI and now she likes to write the prompts for the story with me. And she has kind of learned, okay, like this kind of prompt gets me a good story, but this kind of prompt doesn't get me a good story. And that's sort of, that's the skill set that kids need is almost, we are spell casters and the skills of the next generation will be like, how do you learn the right spell to get the outcome you want.

Tom:

Fascinating. We're almost at the end of our time. A couple of things I wanted to get your perspective on. Just quickly retail and this conversation around AI. I know that's not necessarily your industry that you invest in. It's a significant amount of time, but you certainly touched it. Do you have any views around thinking five, 10 years out around the future of the store as it relates to technology or retail in general?

Randi:

Absolutely. And actually I have been spending more and more time thinking about retail because now that I've gotten so excited about running, I think for me as a business person, I'm always thinking, okay, I don't want to just play in the casino. I want to own the entire casino. So I've started investing and advising companies in all areas of endurance sports, which includes several major retail companies and thinking through that.

So a few thoughts I have, I think, certainly COVID catapulted commerce many years into the future over what we thought and got people comfortable with it. Right now, I think commerce is so much about storytelling. It's so much about content and the emotional connection with consumers. And so I see that, I'm advising several apparel and shoe companies in the endurance space right now. And it's like all comes down to the athletes they work with, the storytelling, how good they are at touching people's hearts and emotions. But I also think going back to the AI conversation we were just having, as the AI takes over more and more of our lives and screens, I think there's an equal demand for human experiences. And I think those things rise side by side. And I do think that we are going to see more and more demand for in-store experiences, just like we're seeing people want to go to concerts, they want to go to festivals, they want to run marathons, they want to do things that are uniquely human in this world of rising AI. And I think the brands and retail companies that can lean into that and figure that out will have a huge advantage.

Tom:

You know, it's fascinating you say that. We've done a bunch of research on generational differences and Gen Z, which is obviously a digitally native generation. But to your point, I mean, they really place a high value on human interaction, personal experiences, connectivity, going to the mall even. mean, those things that are, you know, very about networking and coming together because they have the digital part of their life, but they want the human connection. It's also a generation that was heavily impacted by COVID. And so they know what they missed when they didn't have that human interaction.

Randi:

Yeah, so it's been really cool to see that. I feel like in some ways the screens are bringing us back together in person, which is a full circle moment.

Tom:

It may have been counterintuitive, but it's kind of what's happened. Randi, I could speak to you for another five hours easily, but I want to be respectful of your time. Any final thoughts for our listeners on any of the topics that we spoke about?

Randi:

Gosh, I think we covered so much, but I just, I think this is such an exciting time to be alive and to be in business. You know, I said earlier in the podcast that I felt like with Facebook and being on the front lines of social media, I had a once in a lifetime opportunity to have a front row seat to the world changing. And now that's not true because we're actually all going to get it again now with AI. So it, for me, I have a twice in a lifetime opportunity to be on the front lines. And all of us get to write this playbook. All of us get the experience of being right there when the entire world changed. And I think truly it's a rare opportunity and a blessing to be right in the middle of a renaissance. And we all get to do it together. So I'm incredibly excited.

Tom:

We're right at the forefront of history, for sure. I'm so looking forward to having you at ICSC LAS VEGAS and having all of our attendees get a chance to hear your wisdom and perspective. So look forward to that and thank you for being on.

Randi:

I will be coming right off my next 250 mile race.

Tom:

How many days before that?

Randi:

I think it's the next week after. We'll have a lot to talk about.

Tom:

Yeah, absolutely. I can't wait to talk to you about that. And we will make sure that we have all the therapeutic things you might need. So see what comes up at 250 mile run. So, well, I look forward to it. Randi, thank you for being on today's show.

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