Inspired Execution

A leadership podcast With Chet Kapoor
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Season 7 · Episode 4

Building Tomorrow: Jeff Frick's Take on Startups, AI Governance, and Remote Work

Join us for a riveting conversation with Jeff Frick, host of "Work 20XX" and "Turn the Lens," as we explore the intersection of entrepreneurship, AI governance, and the future of remote work. Whether you're a startup enthusiast, tech aficionado, or simply curious about the future of work, this episode is packed with thought-provoking ideas and practical advice from one of the industry's leading voices.

Episode Transcript

Chet Kapoor: Jeff, welcome to the Inspired Execution. This is going to be a really unique kind of episode. Excited to get started. Thanks, Chet. Really a huge fan of the show and excited to be here. As we were talking before the show started, I said, you know, Jeff, this is going to be unique for me as I was preparing for this. Is it, are you going to be, I do an interview as an entrepreneur, as a podcaster, and my conclusion was, it'll be more like an entrepreneur, but we'll definitely touch on, you know, your podcasts because they are actually phenomenal. Thank you. 

Jeff Frick: And they're intimately intertwined. So it's kind of hard to tear them apart, actually. 

Chet Kapoor: Yeah. Let's talk a little bit about that. You've been in the media space for many years and you have two podcasts of your own. So tell us a bit more about yourself and how did you get here? 

Jeff Frick: So I had a long and crazy journey. I don't want to give you the whole thing, but I basically grew up in the retail business. When I was growing up, my stepfather worked at a store. So it was appliances and TVs and furniture and these types of things. So when I got out of school, I ended up in San Francisco cause I got a job with the Macy's Management Training Program, which back then was a pretty great program. And that's what brought me to the Bay Area. And then I said, you know, I'd rather do wholesale than retail. So I worked for Mitsubishi Consumer Electronics for about a decade selling TVs wholesale to basically everyone who sold consumer electronics. Gave me a really good feel because in that position, you really weren't supposed to go sign new accounts. You had to try to grow your business with your existing accounts. And so you really had to get to learn your customer's business and what you could do from, you know, working on the floor to working with a CFO to help them get more of your business.

It's about 1998 or so the yen got upside down and it was before DVDs and it was before HD. So I left, I got a MBA and then said, well, we have a house in San Mateo, we're going to go back to the Bay. I guess I have to get into tech. And I ended up at Intel on the IA-64 program, Merced, the very first 64-bit microprocessor, which was just, you know, I didn't understand anything anybody was saying. I couldn't understand the vocabulary. It was quite a learning process. Fast forward, it wasn't a great fit, but then literally like an angel one day on the internal intranet, which we used to call it, they launched a 50-50 joint venture with SAP called Pendesic. And really it was the precursor to what Amazon is doing now. The whole idea was we use a shared instance of our three and we'll sell it to retailers and instead of charging them, we'll just charge them a percentage of the transaction. I was the only guy that wasn't either an enterprise software head or a chip head who'd actually worked in retail and wholesale. So that was a really great experience. And at that time there was this new thing called XML. So you know, the opportunity to plug and play different applications in. So, you know, who had best of breed shipping software, who had best of breed tax software, who had best of breed auction software. So it gave me this great introduction because I left sales and got into biz dev. So I got to meet all these companies, which was really cool. It didn't work out for a number of reasons, starting with the culture clash. I mean, literally a 50-50 split of people, you know, Hosso Plattner would roll up for board meetings in a chauffeur driven limousine and Craig Barrett would have a rented Toyota Tercel. And we're like, Craig, you could get a better car. As an investor in Intel, I think you should have more steel wrapped around your melon. So that didn't work out. But then we did a B2B version of the same thing, which was called Acera. And this was Kleiner Perkins, Vinod Khosla, really trying to model what Cisco had done early on in terms of using the internet. Not so much on the supply side, or even other people were doing that, but more on the selling side to manage your channel. And so we, again, tried to build an internet version of Cisco Connection Online, 2000 comes, everything crashes, and that kind of all settles for a while.

So I did a bunch of things. But about 10 years ago, a friend of mine introduced me to this Cube thing. And I went and actually my very first Cube event I ever attended before I started the company was Cassandra Summit 2012 at the Santa Clara Convention Center. Wow. And I sat and watched Billy Bosworth get interviewed by John Furrier. And I left and I said, you know, to your point earlier, everybody has a story to tell. Most people don't get the opportunity to sit down in a professional setting and tell it. And so I joined the Cube and did that for about eight years. And we would go out to basically trade shows, set up a mobile TV studio and interview execs. Cube is legendary. So that was a great experience. I learned a lot and formed a lot of my kind of opinions about this business and how people work in this and that. 2000 comes, no more events, we're in the event business, that was kind of tough. But I helped the company transition into remote. And then concurrent to that, I was getting involved in electric skateboarding and that kind of sucked me into YouTube and then that kind of sucked me into the whole world of asynchronous media consumption. And now that we were not at events anymore, it really started to make me think about the modern way that we consume media, which is not appointment based, right? It's whenever it's convenient for me to tune into your podcast. And I wanted to get into some other topics as well beyond just enterprise tech. So that's when I left.

And the final piece of the puzzle was hypothesizing on how do you use AI in platforms as your partner when you're trying to get your content out to the people that matter to you. That's really why I created Turn the Lens as a test bed platform that I could test my hypothesis around building connection inside of LinkedIn because I didn't have my own media company anymore. I'm one person, you know, sitting here in my own studio and I use that to basically drive it. And then shortly thereafter, a person I worked with before WebEx said, hey, we're starting this thought leadership thing around the future of work because everyone is trying to figure out what to do. I'd love to have you as our podcast partner. And so they sponsored and we created the first season of Work 20XX. Again, great opportunity to test the hypothesis because I had no connections, Chet, in all my career in like corporate real estate or facilities. So I literally started from zero in that space in terms of presence and was able to, again, kind of prove the hypothesis, build the show, build the audience, build the voice in this world that I hadn't even really played in before. So that's been, that's kind of how I got here. I still love Turn the Lens because I do all kinds of fun stuff. It's completely unfettered in terms of topic areas. So like you, it's just fun to get smart people on and explore cool things. 

Chet Kapoor: I know. I know. And by the way, I've not thought about Pandesic or about Acera in a long time. Right. There was a company around that same time called Corio. And so there was a lot going on and they were all infrastructure as a service is probably the best way to put it, old style, not like, you know, utility style. But I think that's awesome. That's awesome. 

Jeff Frick: Yeah. Well, and the other thing, if you remember, the only retailers back then online were selling computer components for people that didn't have fries in their neighborhood. And so those were super low margins. And we made the, one of our many mistakes was pricing based on the total transaction. So it was low margin goods. And so, you know, the people could really afford for us to take a piece of it. It's also where I learned a really critical lesson about real time, what real time means, because that was our whole shtick, right? We're running on R3. The problem was, these are early days, right? The catalog would load the entire database every time the front page loaded. And we had this customer that had every kind of logo wear on anything you can print on. And every time someone came to his front page, it loaded in the back. God knows how many permutations of t-shirts times colors, times sizes, times printing, and we just destroyed the guy's business. It was really, it was kind of rough. But anyway, a lot of great learning though, a lot of great learning. Awesome. 

Chet Kapoor: It is. So you're also an entrepreneur, you've seen a lot of companies, Acera was not a success, right? Bendisec was not a success. So you've seen, now you've talked to a lot of people through your podcast. What advice, what one piece of advice would you give to someone who wants to start the journey as an entrepreneur today? 

Jeff Frick: No, somebody asked me that question early on another podcast that I just said, you got to feel like you have to do it. I mean, there's so many barriers. It's like, you have to do it, you can't not do it because if you have any type of concern or you have any type of, you're just not that interested, you're going to get tired and you're going to get worn out and you're not going to be successful. So it's got to be something you're just super passionate about. And as you know, you've got to talk about it over and over and over and over and over and you're going to get tired of hearing yourself talk about it over and over. But if you don't bring that energy to it, then it's just not going to work. That said, the probability of success is still very, very small. There's a whole lot of luck that people don't give enough credit to and I think you can increase the surface area of luck and the probability of falling into some situations by putting yourself out there. But at the end of the day, you just do the best you can and sometimes it works and oftentimes it doesn't. 

Chet Kapoor: No, I couldn't agree with you more. I just, the rule of thumb, and I do this, is it's not literal, but I ask people, would you take 80% of your life savings, you know, college funds and everything, and actually fund your startup? Because if you can do that, if you can rationalize, because a lot of people you notice, like they finished three and a half years of college and they still quit and they don't get a degree because they can't wait. They just can't wait. And so the same thing applies later on in life. Can you take, you've got X amount of money saved up, kids, college education, are you ready to put it all in? Right, or 80% or 70%. And not that you need to do that, but you need to carry that conviction and passion to the idea because you'll have to not only believe in it, but inspire a bunch of people and then go off and make something happen. And the inspiration will come through your passion and urgency that you want to do it today. 

Jeff Frick: Yeah, I agree. Completely. You just, it was funny, there was a lot of that going on in 96, 97 when I was in business school and people were struggling because things were just going bananas. Do I stay or do I go? Do I finish or do I go join? There's certainly, there's good arguments on both sides of the equation. You can point to plenty of stories where it worked out well or didn't work out well. But the other thing I would tell people is at the end of the day, you don't know where you're going to be. I don't think anyone who's got gray hair like you or like me, did you ever think you would be in this spot when you were 20? So don't worry about it. Just learn as you go. You're going to take something from every experience you have if you're just paying attention. And when you look back, it actually kind of maybe, there's maybe a thread there that looks more consistent than you thought when you were kind of looking forward. So my thing is just don't overthink it. Look for good opportunities. Look to work for great people more than worrying about what they do or what they sell or if you're getting started, because that's where you're going to learn. You're going to learn from great people. And those are the things that will hold you regardless of the industry or role that you get down the road. For sure.

Chet Kapoor: For sure. So one of your podcasts is called Turn the Lens, as you just mentioned, and you've talked about the fact that it's a show for the curious, right? What's one learning from a recent guest that changed your perspective? 

Jeff Frick: Well, I'm kind of going down this whole robotics rabbit hole and the open AI rabbit hole right now. And we just had a guest on, Eric Law from Urban Machines, who built a robot to pull out nails and screws from construction throwaway wood, which I learned that, and you've seen on the side of the road, there is a recycled path for cement. You see, they grind it up and stick it back in. And there is a recycled path for steel, but there was no recycled path for wood. So it's this huge problem. We throw away like 50% of the wood that we harvest every year. And this is stuff that creates forms around concrete and this and that. And it was all just literally being ground up and thrown into the landfill or being burned for power. So that was pretty fascinating. The other thing that came out of that is the price of solar energy and renewables is getting to the point where the guys that were getting the free wood chips to burn in incinerators to generate electricity, they can't afford to do it now because the upkeep on those old machines is actually more expensive than somebody just buying renewables. So I thought that was pretty interesting and pretty hopeful. I'm doing a robotics panel this week. One of the big questions is general purpose versus specific purpose. And I think we saw Jensen with all the humanoid robots on stage at the NVIDIA thing. And I think the robotics thing is pretty curious. 

Chet Kapoor: Yeah. No, that's awesome. That's awesome. So let's talk about your other podcast, which is Work 20xx, right? So Gen AI is, you know, I'm very passionate about it. I think it's going to change our lives. It's going to change our lives on a personal level, professionally, in all kinds of ways, robotics being one of them. So can you, for all the podcasts you've done around Gen AI, can you share a couple of key takeaways from your audience, like what are some things that you've learned? 

Jeff Frick: So I think first and foremost, we always have to separate where we are today from where it's going to be. And then some of the problems around hallucinations and accuracy and this and that, we just have to presume we're going to get better over time. And if you look back to the PCs when we first got started or pick any technology where we first got started, it's going to be a lot different. I was also really taken by Jensen's description that if you go to the library and ask for a book on Paris, you get a book on Paris. Computing was always retrieval versus asking the librarian based on all your experience, travels, and books you've read, tell me about Paris, which is a new generated answer that's never existed before. What concerns me is really at this point, just audit and explainability, I have a real hard time understanding how we're going to get to explainable AI if the models are constantly learning and evolving and the number of inputs are so, so large and dynamic. I don't know how that gets resolved. So I'm a little bit concerned about that and then the whole governance thing, right? If you use our experience around governance and regulation on the privacy side, Europe can do GDPR as a continent of countries and come up with a unified standard. We in this country are still sometimes hamstrung by our state and federal, that constant ying and yang. And if you're in the privacy space, you got to worry about the regulations in every single state being different. So to me, that doesn't bode well for what we're going to do around governance for AI and gen AI. And that concerns me a little bit because the technology is usually way out in front of our ability to kind of understand and add those governors. I had a great interview with Ruben Chowdhury, he used to be the ethicist at the center. She had this great line, good breaks allow us to go faster. I was like, oh, you're right. So people push back on governance. There's a lot of unintended consequences is not insignificant in this stuff. So I think we just have to be careful. So I get conflicted, I'm positive and enthusiastic, but at the same time, I try to be a little realistic and we have some challenges to overcome. 

Chet Kapoor: I've been recently participating in the World Economic Forum and as somebody who goes off and loves building great products and product businesses, this is the first time, this is my fifth wave, right? Client server, web, mobile, cloud, and now gen AI. This is the first time I feel that we need to make sure we get some governance earlier than later. Because on the internet, it was very clear. People were like, you're not going to cash checks on the internet. That's bullshit, it'll happen. Tech catches up, all that, right? All that stuff happens. But this time around, I think there needs to be some guardrails. And the problem is people don't know how to define some. And it is the definition of some and the definition of who, right? So it's like, who's doing it? You need to make sure that the people who actually have relevancy to this technology and are thinking about the next hundred years, not people who've actually said, I come from mainframe era or client server era that's going to do this. So that's one, the profile of the individuals making the decision. And the second thing is, what is some? Because if you do this the wrong way, you're going to kill this. It's just not, the innovation will not happen, right? So that combination is something that I worry about, but I feel like there's enough dialogue happening to make it happen. I think that's the good news. 

Jeff Frick: And I tell people too, still a surprising amount of people haven't tried it yet. It's like, come on, treat it as a calculator today, treat it as a calculator, open it up on your desk and ask it questions. I always tell people, start out with, ask it to write a 200 word bio of you and see what comes back. And like I had to do it, that was the first thing I ever did. And it just got my call just completely wrong. So I immediately could feel kind of where the limitations were and it clearly hadn't crawled LinkedIn or it wouldn't have made those mistakes. The other interesting thing, Chet, is this demographic trend that we're in the middle of and going to continue, which is decreasing population in Western nations. So we're going to have a labor shortage at the same time. People are worried about their jobs and they are taking their jobs. So who wants to be a truck driver when there'll be autonomous trucks in the not too distant future? Who wants to be in some of these dirty jobs that are going to be taken by robots before the robots get here? And I think there's going to be a real interesting thing to watch turn out, peer and intern from the former CEO of Accenture, a great talk one time. And he's like, the demographic trend trumps all. Everything else follows the demographic trend and the demographic trend is going to be challenging for the labor market. 

Chet Kapoor: For sure. So let's talk about the future of work and I'll give you a little caveat. DataStax has been a distributed company and we specifically use the word remote long before I joined. DataStax was in fact the first company in my 30 years where I've actually led a distributed company. It was an adjustment for sure. And so the good news is I was getting used to it, the company was already used to it and then the pandemic hit and we didn't miss a heartbeat because we were already doing things on a distributed basis, including all hands, right? So we just had a way of doing this. And so what do you think, given the podcast, what's your point of view on the future of work? 

Jeff Frick: So I think there's three or four big words. What is intentionality? I think we had a lot of lazy managers that were managing by presenteeism before and no one could actually answer the question, what do you want me to do and what's important? So I think it exposed a lot of that. I think agency and flexibility are important words in the conversation that you hire people that you trust to do their jobs and then you give them direction and then you get out of the way. And then you get a different leadership, right? Which is, what can I as Chet do to help you get your job? What roadblocks can I remove or resources can I bring to bear to help you complete your job? What's going to be interesting over time is as new companies that grew up in this world and never had real estate on their balance sheet or their expenses and their income statement are going to start challenging incumbents in that particular industry and at some point Wall Street's going to go, how do you justify this real estate expense? I think there's going to be pressure to adjust that. That said, if you talk to the greatest, some of the greatest, like I just had Chase Warrington on from Duist, or even Brian would say, distributed doesn't mean never together. So, you know, in fact, Duist spends, they don't do remote to save money, they do it as a different way to execute. And they bring everybody together, at least twice a year. Atlassian was another one who was kind of out front that's got this hybrid. And so the role and the function of the physical space will be different. It won't be to go sit and do Zoom calls and email, it's to go and collaborate, build trust, get together, you know, move more crappy work to async on these digital platforms so that the time you are together and you can intentionally spend it investing in those relationships and that's trust building so that when the proverbial, you know, it hits the fan, you can call out and people are going to respond. So I think it's just a different way to think about it and leverage these digital platforms for the crap and use your time together to build the trust. The piece that doesn't get talked enough in the whole discussion is meetings and bad meeting etiquette and bad meeting procedure. And still people talk about work in terms of meetings. It's like, no, work is not meetings. Meetings are an action. And actually, if you do really good meeting etiquette, the people involved in the meeting are going to be super engaged, super informed, very interested in getting to a good outcome and you're going to have a lot better meeting. So I think that's a big productivity gain that's just sitting there waiting to be picked up that most people just completely ignore and just do it because we've always done it that way. 

Chet Kapoor: You know, it's really interesting as you're going through this. I'm like, check, check, check, check, because we do almost all of it. The one piece you didn't mention, and maybe it's embedded in one of those, is people, when you're working in person together, the one thing that you do is escalations work really well, right? Because you can walk over to somebody's desk and say, I need this now, I'm stuck. And that concept in a distributed work environment starts by, let me put a meeting on your calendar that is now generally busy because you're working, rightfully so. And the concept of escalations is always viewed as a negative concept, not as something that's positive, where you're helping a coworker who is also on the same mission as you. Has that come up in your discussions? 

Jeff Frick: Yes. Brian Elliott specifically says escalations are positive. We need to remove the stigma around escalations because escalations are about getting things done. And then the other really key piece to that is the trust factor. Because if I'm worried that I admit that I'm having a problem with something, you know, am I worried that now you're going to consider me in the bottom 10% and I get lopped off on the next round of layoffs? So, the trust is fundamental to actually say, I need help. And then, you know, the other word that's a horrible word is postmortems, generally most of our businesses, nobody died. So, let's have a retrospective. Let's have a blameless retrospective so we can figure out what happened and learn. And since we're not going to blame everybody, hopefully everyone will be more forthcoming with information so we can actually make a better decision. Because at the end of the day an organization is a decision-making machine. So, how do you increase the frequency of decisions and how do you reduce the friction in decisions and then, you know, push it down as much as you can to the people that are closest to the problem, which is another kind of key tenet to this whole thing. 

Chet Kapoor: No, no, this is awesome. This is gold. Thank you very much, Jeff. This is, I think the listeners will really like this. All right, one last question before we go into rapid fire questions, which is, what is your secret to a really engaging episode, a podcast episode? 

Jeff Frick: Be real. I think just talk to people. One of the things I learned, too, at The Cube is you talk long enough to get past their talking points and then people start to be real. So, it's kind of a dirty little secret, right? The whole idea of a 45-minute podcast is they get them in at 37, which is when they just completely open up and say all the great things. But I think it's just being honest with people. I think the open-source ESOS that came out of technology is a really special thing, this idea that, you know, there's lots of places that we can help each other and share best practices. But I think, and do your homework. You know, one of my favorite interview shows besides Inspired Execution, obviously, is Sean Evans with Hot Ones. And if you've ever watched Sean, you could tell by his questions and you can tell by the guest's response that he did his homework, he knows what he's talking about, and people are touched, right? Because everybody wants you to be interested in their story. So, if you actually listen, plus most people do have kind of interesting stories if you let them tell it. 

Chet Kapoor: That's awesome. Thank you. All right, rapid fire. Now you're scaring me. Rapid fire, here we go. What's one thing in your day-to-day life that you would want AI to automate? 

Jeff Frick: Closed captioning. It's still not good enough. I spent hours on closed captioning. 

Chet Kapoor: That's actually pretty good. Not a lot of people have answered it that way. That's really good. What's a problem humanity is facing that you would want AI to solve first? 

Jeff Frick: I don't know if it's healthcare or wealth distribution, but I think those are two really, really, really big problems that are getting worse. Healthcare. And they  shouldn't. Let's take healthcare first. 

Chet Kapoor: Okay. Who is your dream podcast guest, dead or alive? 

Jeff Frick: I’m just going to go with alive because I thought about this. I think I got to go Arnold Schwarzenegger. I was a huge fan of him growing up and the fact that he has been so successful in everything that he's gone after, which are all completely different than the thing that he was doing before, including being a Republican governor who marries into the Kennedy family. I think there's a lot there and he's a big personality and I would love to have Arnold on. I'll have to keep working on him. I don't know. He's got that donkey that he's always hanging out with now. So maybe I have to go down there and feed the donkey or something. What podcast should everyone listen to besides yours? Oh my goodness. I'm just like all over the map. Just one. Oh, you're tripping me up here. What have I been listening to lately? Well, I've been listening to too many political ones lately, which is probably not very healthy for my wellbeing. 

Jeff Frick: Yeah. Not very healthy at all. It's called the Midas Touch that I've been listening. I try to avoid most of that stuff most of the time, because it doesn't help me be productive or put me in a good space or help me get some posts out. But that is what I have been listening to recently. And as we head towards the election season, that whole world is just going to get crazier and crazier and crazier. So I think it's important. I also listen to actually a couple of guys from Ukraine. So it's not really a podcast. It's more of a YouTube. There's one called Reporting from Ukraine. There's another guy, Dennis Davidoff, who gives daily updates on what's going on. And I don't listen to any kind of big media on what's going on over there. But these guys, they give a kind of a European perspective because they're based there. They give you a lot more information about what's going on locally. So I spend a lot of time on YouTube. I think YouTube is an amazing thing. I would agree. Old Dick Cavett interviews. He's an amazing interviewer. Old Johnny Carson interviews. Johnny Carson. I love the format. So I actually watch a lot more YouTube videos than I do podcasts. And even if it's a podcast, I prefer to watch the video than listen on Spotify. 

Chet Kapoor: What three qualities describe the best leaders that you have read about or interviewed in or the ones that you watched? 

Jeff Frick: Any of the above. But three qualities that best describe best leaders.I think curiosity is a big one. I think empathy is a big one. And I think enthusiasm. I think those are three pretty critical ones. . 

Chet Kapoor: That's awesome. That's awesome. So, Jeff, this has been great. As I said in our talk before, I was like, this has never happened. You've made it really easy. I was like, you know, this guy is like a professional. Like, what am I doing interviewing him? Right? And so you've made it really easy. I think our guests are going to find this an awesome, an awesome time. And we'll have you back soon. And actually, I would love to go back into talking a little bit more about the future work, because I think it's changing a lot. There's a lot we can talk about how you land up using generative AI tools in the future. And so we will definitely have that conversation. You're obviously not neck deep into it. You're like, you know, you're underwater thinking about all this stuff. Right? So it's in a good way. So thank you very, very much for joining the podcast.

Jeff Frick: Thank you, Chet. It's been a real treat and glad We got together.