Spark of Ages
In every episode, we’re going to do a deep dive with our guest about what led them to their own 'eureka' moments, how they went about executing it, and perhaps most importantly, how do they get other people to believe in them so that their idea could also someday become a Spark for the Ages.
Spark of Ages
Building the New Growth Workforce with AI/Jim Kaskade - Use Cases, Playbooks, Transparency ~ Spark of Ages Ep. 5
Ever thought about how Artificial Intelligence could transform the world of work and wealth? That's exactly what we're exploring with Jim Kaskade, CEO of Conversica, a trailblazer in the world of AI. With Jim's expert insights, we promise you a journey through the transformative power of AI, its potential to enhance human productivity, and create a new panorama of employment opportunities.
Our time with Jim Kaskade is not just about what AI can do, but also about the human side of the equation. We examine how AI is radically altering customer journeys and how this tech marvel supports the intricacies of team dynamics. Jim shares his personal journey and the crucial role of mentorship in his rise to tech CEO. Plus, get ready for our informative chat about the invisible matrix that executive teams use to evaluate their members, the importance of self-awareness, and the art of constructive feedback.
But the conversation doesn't stop there. We probe into the potential of AI to engage the younger generation effectively and how businesses can leverage this. Hear it straight from the horse's mouth as Jim shares how he systematized approaches to create impactful change within his businesses. All this while discussing the joys of hiking and how it influenced his leadership style. This episode is a gold mine of insights, stories, and a fascinating voyage into the world of artificial intelligence, team dynamics, and business growth.
Website: https://www.position2.com/podcast/
Rajiv Parikh: https://www.linkedin.com/in/rajivparikh/
Sandeep Parikh: https://www.instagram.com/sandeepparikh/
Email us with any feedback for the show: spark@postion2.com
Hello and welcome to the Spark of Ages podcast, where we're going to talk to founders, innovators, ceos, investors, designers and artists. I'm talking game changers about their big world shaping ideas and what sparked them. I'm your host, rajiv Parikh, and I'm the CEO and founder of Position Squared, a growth marketing agency based in Palo Alto. So, yes, I'm a Silicon Valley entrepreneur, but I'm also a business news junkie and a history nerd. Whether it's how World War I tanks were cleverly designed to defeat trench warfare or how today's digital health devices may help us defeat mortality, I'm fascinated by how big, world changing movements go from the spark of an idea to an innovation that reshapes our lives. In every episode, we're going to do a deep dive with our guests about what led them to their own Eureka moments and how they're going about executing it. And, perhaps most importantly, how do they get other people to believe in them so that their idea could also someday become a spark for the ages. In addition to myself, we have our producer, sandeep, who will occasionally chime in to make sure we don't get too in the weeds with Tech Jargon. He's a comedian, writer and actor based on LA who's been on some really cool shows like The Guild, Community, and Glitch Techs, but his most important credit is he's my little bro. Say hi Sandeep, hi Sandeep. This is the Spark of Ages podcast.
Rajiv Parikh:For our interview today, we have Jim Kaskade. Jim is currently the CEO of the private equity backed rocket ship Conversica. Founded in 2007, conversica is the pioneer and leading provider of conversational AI solutions. Consisting of a suite of AI assistants, aka digital team members, it's dedicated to helping revenue-centric organizations attract, acquire and grow customers at scale. Jim is the CEO of over 21 years. He's been part of 11 startups, seven of which he helped found, four of which he was invited into and five of which were sold. His startup experience involves in building high tech businesses ranging from artificial intelligence, security, cloud computing, enterprise software, software as a service or SaaS, online and mobile digital media, online and mobile advertising and semiconductors. He has another 10 years of big enterprise experience in data warehousing, analytical applications and business intelligence services designed to maximize the intrinsic value of data, servicing Fortune 1000 companies in telecom, retail and financial markets.
Rajiv Parikh:Jim is a close friend. He's a brilliant guy. He's a leading mind when it comes to the thing that's on everyone's minds today, which is artificial intelligence. We're going to dig into that as well as his journey as an entrepreneur, an executive and a father. We want to see what makes him tick. I knew Jim would be the perfect guest for this show, because I would sit with him many times and see him literally take over a room, especially when he runs workshops. He has this uncanny ability to just brighten up the room in real time, and so that's what I'm really excited about In having him come here and share with you how he draws these beautiful pictures in his mind and how he brings that out for his team, his customers, his friends and his circle.
Sandeep Parikh:Here's what I'm excited about. Real quick, Rajiv is learning what a SaaS company is. So it's like a very sassy company. Is that what you're trying to say? It's got like attitude, right, that's what that means?
Rajiv Parikh:Very sassy very sexy.
Sandeep Parikh:It struts, is that?
Rajiv Parikh:what SaaS is. When you buy from a SaaS company, that's exactly what you're doing. Isn't that what you do, Jim?
Jim Kaskade:Well, I know I don't strut, but yeah, it's everything as a service, right? What's the S stand for Software?
Sandeep Parikh:Software as a service, not as strut as a service. It's software as a service. It's not sexy as a service, fair enough.
Rajiv Parikh:What is more accurate? Will AI unleash human productivity unlike any other technology before? Or AI will end up putting everyone out of work? Well, I'll be like in Wally and it'll be overtaking humans as the dominant entity on earth. So it's not only Wally, but it's Wally and Terminator.
Jim Kaskade:Yeah, so it's going to unleash, right? So I mean, every time there was a transformative breakthrough in technology, whether you want to go as far back as the light bulb with electricity, or you want to look at self-driving cars today, you know You're in a situation you're like what's going to happen.
Jim Kaskade:Self-driving cars, it's mean you're not going to need anybody driving a taxi or an Uber or Lyft and there's always this initial response that you're going to replace people, and I think, at the end of the day, what you end up doing is you may be displacing particular roles or functions, but you're definitely not displacing people. You're unlocking them to become even more high value, so they need to reskill and actually do things that are actually more meaningful to them as employees, let alone the businesses and customers that they serve. So I think the quick answer is unlocks. I mean we are all going to benefit.
Rajiv Parikh:So let me challenge that a little bit, Jim. So like, okay, you go back to electricity, right, it took 40, 50 years, right? There's this really interesting graph that will show. I think it was put out by Singularitycom, it was an HB in Harvard Business Review and it shows how long did it take for something to penetrate 25% of US households, right? So if you look at electricity, it may take 50 years. If you look at radio, it'll take. It took 31 years. If you take the PC, it was 16 years. If it was the mobile phone, 13 years, the web seven years. But AI, I mean kids are using it.
Jim Kaskade:Kids are using it.
Rajiv Parikh:Adults are using it. I even got my uncle to give a speech. He's like Rajiv. He was like Rajiv, can you?
Rajiv Parikh:I'm going to be speaking in front of this insurance group of professionals in Washington DC. I'm going to be giving a speech. I don't like to speak a lot, so I only have about three minutes. What should I say? So I just jumped in the chat with GPD and said construct a lightly humorous speech to a group of personal finance professionals in the DC, virginia area, ensure it's only two or three minutes and make sure it ends in a positive note. And it wrote this brilliant two to three minute speech and then I asked for five versions of it and sent it off to my uncle. This is something that's like today and now. So on the positive side, that seems amazing, but on the side of fear, all those other technologies took quite a long time to permeate themselves, so you have time to catch your breath, like we had time to teach our parents how to work with their iPhone or Android device. Are we going to meet a situation where companies just start letting tons of people go because they can do this so much faster with AI or generative AI?
Jim Kaskade:Well, I think you know. First, to comment on the time it takes for adoption of 25% population in the US, of course, if you use television, you know the PC, mobile phone, that just meant you had to buy a TV and install it and get cable and then the phone. You had to have enough money to buy it. You know, and all these things required infrastructure, whereas these technologies, with AI, all the infrastructure is there. You just you know. Log in, establish your Barrett account. You know with. You know with Google or your chat GPT account.
Rajiv Parikh:It's basically free and available today. It's basically free.
Jim Kaskade:And I don't have to. You know, not to them Exactly. I don't have to buy a radio and plug it in, I don't have to, you know, pipe electricity into the house. You know those previous breakthroughs required a lot of plumbing. The plumbing's there, the cloud is there, so you know.
Jim Kaskade:So, of course, it took a very short time for this type of AI and the use case being a kind of chatty interface. It's almost like a new way of search, right, you're discovering things through an exchange that feels like a conversation, which is just the most normal than typing in you know a phrase and then seeing a list. It almost feels like search is 1.0. And now this, now breakthrough with AI is search 5.0. So I think adoption makes sense. And then you know what happens now that everybody's using it everywhere and you're inserting it into every use case.
Jim Kaskade:Again, I think just the level of productivity for every human out there just goes through the roof and a coder doesn't have to code the basic, you know functions, it just uses AI to generate and that coder can now think about kind of the actual use cases and what they want to do for the, you know, for the business and for the end consumer. And so, at the end of the day, people are going to benefit and us as end consumers of these product and services are going to benefit. I just think it's going to. It's going to cause more job opportunities and clearly now there's a class of prompt engineers, more you know, scientists that are thinking about how to apply the AI and various applications, and so you have a whole new workforce of humans springing up, you know, filling in where you know. I think those old job functions you know are now being replaced.
Rajiv Parikh:Right. So I think this is where you can, maybe. So what you're saying is hey look, people may be afraid, and fear is a natural thing when there's tremendous change. The game is to actually go and play with these tools because they're free. Actually, you've been using a lot of these tools anyways, but you just haven't seen it to the level that we see when you type into this new interface something very conversational, right, the new code is English. Right, it may not be running Python, or it certainly isn't C++. It's like English is the new code I could write something in, and it could generate code for me or give me directions on where to go, or tell me what I can do for 10 days in Barcelona, right? All kinds of cool things that I could do that I never could before, and so maybe I get more productive, and I get more productive than others. Let's go back a little bit like so this is all about interface, right? So from your point of view, is there something about AI, or even conversational AI, that really no one's asking about?
Jim Kaskade:Most people just can't be mindful of all the use cases that this could be applied to.
Jim Kaskade:But I think if you go Into any vertical and you just give yourself an opportunity to think about the processes that just don't work Whether it's healthcare and getting access to information you need, you know, helping you diagnose, you know something To?
Jim Kaskade:You know just understanding where you want to put your money and invest, you know in banking. So you just go through every vertical and there's there's things that cause friction, and if we could apply AI to automate tasks, to gain More efficiencies, access to information, insights, faster Actions that serve you more quickly, more effectively, boom, you know. And so I think there's not really Anything that you can't apply AI to at this point and now. It's just a function of what makes most sense, how much businesses are going to support it, and obviously you need to make sure that you're managing people's data privacy Regulations so that we don't get in, you know, into trouble. We have lots of issues Perceived around the use of AI that, where it, you know it may come with inherent biases and not serve you properly, and so there's still some scariness around the security data privacy. You know, and I think you know.
Jim Kaskade:Yeah and some terminator it might take over and take control kind of worries. You know that people start to think about because you know they've seen all the shows. But you know we could dive into any one of those. But I think it's really there's so much that you just won't appreciate until you do see it.
Rajiv Parikh:We then switch gears to talk a bit about Jim's journey as an entrepreneur. His path could have gone so many ways in technology, given his background and experiences. Right now he finds himself in the hottest space in technology, and it's something a lot of people are looking to break into. I asked Jim about what led him into the AI space and how he ended up taking the reins at Conversica.
Jim Kaskade:Well, you know, I'd like to think that you control your destiny, right, but I do feel like I bump into things that just feel like you're in the flow right, and I think some of that has to do with, you know, just being open-minded and you know, kind of doing the walkabout in technology until it just feels right. In this case, I bumped into Conversica and it wasn't something that I was literally searching for. It found me. But you know, I did do a lot of things to to kind of maximize my odds of falling into something so fantastic. And obviously, you know, in tech, we can all probably appreciate that AI is the fastest growing tech segment in the history of tech today, which is amazing. So my, my long story short is yeah, I think I was invited into my last company, which I had so much fun and Literally dancing out of that transaction, I immediately began to talk with private equity groups who I knew and who knew me, and the whole purpose of that was to to really just understand what investors were looking at and Somewhat directing it in terms of I have a natural passion for health care technology, etc.
Jim Kaskade:So I was doing some research and one of the private equity groups said hey, since you have a little time off, jim, why don't you, you know, take a look at this one portfolio company it's the jewel in our portfolio and Provide the CEO some advice? And I was like, yeah, sure, I'd love to and Note to CEOs out there. You know, if another CEO gets invited in to give you advice, you know you might lose your job. Now it's not what I was intending to do, but when I looked at Converseca, I absolutely fell in love with it, and the reason why I fell in love with it was because I was looking through kind of three lenses one Operational, you know I thought there were a lot of things the business had matured to but had so much more potential in terms of just playbooks around how to run the business, and those seem to be very low hanging fruit, things like Leveraging offshore, you know, talent, for example. They had a hundred percent onshore things like that.
Jim Kaskade:The second lens I was looking through was one that I just had previous experience in and that was Big data analytics. You know I had run a group of people who were, you know, I had run a group of a thousand data scientists, which sounds like a very large group, but it was a small segment of a larger business and we did about 800 big data projects a year and I remember from that experience so many great applications of machine learning and deep learning, which I have a lot of history in. With this experience I saw some amazing big customers doing, you know, trying to solve hard, hard problems. But what? What would always happen in that experience is we would apply these algorithms, we would do some segmentation and some really neat analysis and we would say, hey, here's what you should do. And then when the customer says that's a great idea, how the hell do we operationalize that? We'd always kind of bump into the wall. And how we take sophisticated analytics and incorporate it into your business day to day. So that to me was always a big issue. And so this business. At Converseica they took and have we have been taking really sophisticated algorithms and and and applying them. It's applied AI and so Operationalizing it, making an application and easily digestible, something that people can actually consume as a business, was very interesting to me.
Jim Kaskade:And then the third lens that I was looking through I ran a business of digital transformation and that was about 7,000 people, which just sounds crazy given that I'm a startup CEO. Neat thing about that was we did a lot of work with big customers to help them digitize right to make more applications that engage people digitally and every time you you were able to Make somebody connect with their end customers through digital better the rest of the business would tip over because it just didn't know how to field it. Simple, silly example would be you go put a chatbot on, you know a healthcare Site of a hundred products and a hundred different websites and that healthcare company, all of a sudden the call center tips over because they can't Respond to the chat for live agent. You know demand very simple applications Threaded digitally connect, tipping over because you don't have the people power. And I thought, oh my god, what if you could automate the kind of digital touch to your internal teams you know business and in human infrastructure and Make that experience scale.
Rajiv Parikh:So when I was looking at yes, you see all those three coming together, right, you saw, wow, I could take the collection of my experiences, all that I've done with Big data, and I could actually big data and automation, and I could put it together into this capability for people who are driving revenue for companies and Revenue is the last key, the thing that everybody listening should just think about for a minute.
Jim Kaskade:Most automation is for teams, internal, to try to operational, try to reduce cost, right, to be more efficient, and this was like a use case where AI was applied to Making money growth and we all know growth is hard, right and so and the idea of applying this Automation to revenue teams was very new in my mind. I was like this doesn't exist. This is impossible, right? You can't. You can't put your biggest and most important asset, your customer, in the hands of something like you know, whatever AI, however you define it, you have to put in the hands of a human right. That's the big question mark. You know, this is the. This is the thing that was really novel. That really piqued my interest.
Rajiv Parikh:So I mean, you have this, this concept. Now what you're saying hey, I want to apply all these great computing techniques, but I want to apply it to the Area of getting new revenue into a company was new, maybe current revenue. Now, how would you that? So how did that apply to Converse? Because Converse goes actually around for a little while? Prior to you joining this, people have been talking about AI since Hell. I even started a company back in 2004 on AI, and that was one of the ones that didn't go so well because I was way too early. Did you see this as? Wow, I'm just gonna have a bunch of bots talk instead of my salespeople talking to prospects. Is that what your thought was?
Jim Kaskade:Well, the first thing that did come to mind was this marketing use case, because revenue to me could be anywhere, right, it could be at the top of the funnel where you're just trying to get early interest, maybe even get an unknown person that's on your website to share their information who are they, what's their email address and that's probably where most minds go right the chatbot experience. But there's so much more that you can automate as a customer prospect has their journey, their revenue life cycle journey, right, so you can get all the way to the point where a salesperson's talking to you and then after you consume, after you buy something, then you have the whole customer success, account management kind of to advocacy on the other end of the revenue life cycle. So where do you apply AI in that journey? And most people, they just think, yeah, it's a chatbot, must be a better chatbot.
Jim Kaskade:And then there are those that naturally gravitate towards the use case that I believe AI was born into for enterprises, and that's customer support. So when you're an existing customer and you got to frequently ask questions, it's a very simple way of just automating well, ask it a few questions and it'll give you a few answers, and it doesn't have to be totally accurate and it doesn't have to be human-like. It's just an automated way to get access to information. Those two use cases are so let's just call it generation one of AI, in the sense that most people are frustrated they don't get what they want. Many of them will escape that experience and probably leave your website unhappy and you've lost that customer prospect. That's most people's experience.
Rajiv Parikh:It's like a thing on the phone. I can't even go, Representative, you press nine.
Jim Kaskade:You're screaming you're like zero zero, rep, rep.
Rajiv Parikh:Get me out of this hell. Yes, I bought from you and now you're gonna screw me over by walking me through your freaking menu.
Jim Kaskade:Well, the person will reach out to them and say what is it that you wanted? And then you got to repeat everything that you already provided. Right? How many times have you got through five handoffs and you had to start from scratch? Yeah, it's a horrific experience, I think-.
Sandeep Parikh:Just pulling it back. You sort of taking the 30,000 foot view, like, of what conversing is for those who are just not familiar, like, can you give us? So I'm kind of piecing it together based on your conversation that like, okay, it's essentially that's what you're solving for. You're solving for the problem of getting on the phone and screaming at the you know, screaming for operator using AI chatbots. Is that a fair way of saying what the Conversika and its mission is, or can you give us what that is from the top down?
Jim Kaskade:So there's a chance that everybody listening to this has engaged with the Conversika digital assistant and you didn't know. Yes, absolutely. We have so many big brands that use us and every interaction is so powerfully human right. So what you're experiencing as an end user is you'll go to somebody's web property and you might, you know, want to get a white paper that's on that website. So you fill out a form and you download it Immediately. You know Alyssa reaches out to you and says hey, reggie, you've noticed, you've downloaded this white paper. Is there anything else that you would like to have or anybody you would like to speak to? Do you have all the information that you need? Can I help? And Alyssa is a digital assistant. Now she's able to interpret Reggie's response, anything he says, she'll interpret it 98 out of 100 times, she's accurately interpreting you, and then she'll take the right, next, best action, which is to respond back to you and say, yeah, sure, reggie, I'll connect you with you know, a salesperson, or I'll give you a new piece of information. And so this digital assistant experience it's a persona that our clients have established in various business functions and in marketing.
Jim Kaskade:As Reggie said, it's early in your kind of brand awareness and you're just kind of doing discovery. So you just need more information. Later on in your life cycle you might be ready to get some pricing information. So we have digital assistants that act like salespeople. They're like inside sales, sales development reps, business development reps, you know, lead development reps they all have different titles in different industries, but they're basically people trying to qualify you and get you further to the point where your sales ready, right, you're literally ready to buy, and that's when you engage the human. But all the way through that process you may be engaging one of our digital assistants.
Jim Kaskade:I mean we sell cars, we sell airplanes, we sell boats, we sell software. I mean we give you banking services, insurance services. I mean there's every vertical you can think of. We have a client and numbers of clients using our digital assistants to essentially automate these mundane tasks that revenue teams have to do every day. And instead of doing the high value tasks, like actually having a deep conversation about the problems they're trying to solve, of maybe fine tuning the product offering that they wanna buy, they're down just doing the grungy work and doing very little of that high value work. So we just shift people's you know, the human capital to that high value work, unlock them, and we call that building a new growth workforce. I mean our term growth workforce is the combination of AI and human for growth right and optimizing that combination so that you have this beautiful harmony of mundane tasks that are repetitive and you need to work them at scale done by the AI, high value tasks done by the human.
Rajiv Parikh:Okay, so then, if you were to sum it up, so Converseka provides these when you guys not chatbots, these are digital assistants that help take care of people from the earliest, from the earliest stages, all the way through to a point where the conversation is getting more sophisticated and you need a human, and it does it in a super seamless way, and I think you guys have, is it? A couple thousand customers across a whole variety of industries.
Jim Kaskade:We have a couple of thousand customers and we have thousands of digital assistants speaking many different languages all over the globe, and it's just crazy.
Rajiv Parikh:If you were to put a number to it, like in terms of revenue generated for companies, what would that be?
Jim Kaskade:Oh, we're over 20 billion, easily over 20 billion, and I just wanna add, are all their names Erica and Alyssa?
Sandeep Parikh:Like do you have any? You know parvathis? Or like I'm Indian, I mean, I'm just I wanna make sure there's representation for my people.
Jim Kaskade:Well, we do focus on, you know, diversity when we're sitting down and naming, so you know every country has the appropriate, you know, cultural fit, you know. So, whether it's gender or race or what have you, I think it is important because you do wanna feel like you're engaged with a digital assistant that you know you can actually have a good conversation with, and these are like dynamic two-way exchanges.
Jim Kaskade:You would not know the difference between human exchange and digital assistant exchange. We even have humans prospect customers or existing customers asking our digital assistants out on dates. Okay, and then I continue to get in my employees that say I think I just fell into this. I went to buy a new car and I was having a conversation with the employee and then I had to. I looked it up back in the system and it was one of our digital assistants and I'm like phew, didn't even realize it.
Sandeep Parikh:I'm sorry. Some people are asking these digital assistants out on dates, that's how they accepted these dates.
Rajiv Parikh:It's very ex machina.
Jim Kaskade:Yes, they're very proud of the fact that they're over there.
Rajiv Parikh:Ex machina. Is that the right one? Yeah, that's it.
Jim Kaskade:That's it. Now we have like posters of the number one salesperson, ashley Garcia, for the Sun's you know basketball team number one seller. I probably should have said that because now if you engage with Ashley, probably, you know, might be somewhat biased, but you know that's another good topic. We have a lot of you know younger generation that has large wallet share. Right, we're moving into the millennials with the majority of the wallet share these days, and millennials and younger generation in general, they just don't want to talk to human that you know. They're on WhatsApp and Instagram and Snapchat, and so the idea of you know getting on the phone, forget it.
Jim Kaskade:And even if you disclose ethically that Ashley Garcia is an AI, I think the younger generation goes. Cool, now I feel even more at ease to engage. Right, it's a complete different mind shift versus the older generation that won't ever know if you don't disclose and if you did, might go. Eh, I don't know if I like talking to an AI, but, younger, I love talking to an AI. So I think we're moving into an AI era, right, so let's get started.
Rajiv Parikh:Jim has been a CEO for over two decades and has a ton of experience and wisdom to draw from to help lead his teams. I wanted him to share some of that with us, and I also wanted him to tell us about the early part of his journey, when his path was more uncertain about which direction to go, and how he made those choices, to find out what his spark was that got him to where he is today.
Jim Kaskade:You know, if I take it up to the highest level, I basically have three main pillars to how I approach business. The number one is I focus on the culture piece first and people. You know culture is pretty broad term, right, it's like the ping pong table and the snacks in the lobby and you know there's a bunch of things that my peers think equate to culture, which is a longer story for me. And then number two you know I obviously like to start with strategy. I like to think about five year plans and things that are broader, the vision, mission. You know the purpose of the business and kind of what are we trying to accomplish? You know, in the five year, three year, next year time frames and then last is execution. You know, clearly, I think, if I just keep it in those three buckets but you know, the key thing is you lead with the people. First part you know it's people over profits.
Jim Kaskade:Whatever kind of example you read that you've consumed that really does emphasize that, the fact that now every business has access to amazing amount of capital, there's a lot of investors with a lot of money, billions, invested every year and there's the same access to infrastructure. Everybody can get on the cloud. You know you have the same ass access to the problems that exist that customers want you to solve. And so how do you really differentiate? Well, you differentiate based on the people that you put into that, you know, into that business. So I lead with that. You know there's a whole management system kind of approach to taking and making sure you create change. But you have a framework that puts structure to the chaos. I like using that term because I do embrace business, chaos or constant change. So if there's anybody who comes to work with me and you don't like change, you're not gonna feel at home.
Rajiv Parikh:So this is something that's interesting. Like usually, when you start to rise as an executive or you start to pick a profession, there's a methodology that's taught to you as the general methodology. Right A lot of us who go to business school. They give us different frameworks of methodology, and I've read many books about becoming a CEO and being an entrepreneur, but I've never seen this playbook version like you have. What got you to do it?
Jim Kaskade:Well. So where I really kind of matured and packaged my idea of systematizing, you know approaches to creating change within a business, was the company before Converseca, my last business. We launched 170 playbooks in 11 quarters and the business was completely rearchitected and then successfully sold in that time frame and there was never any dust that settled and the culture was amazing. I mean, if you looked at the glass door ratings it was like a five, you know the CEO, five and all the you know employees were skipping into work and the acquisition was seamless and the integration was beautiful and the whole journey just felt like 11 quarters with nothing. I mean that 11 quarters a long time, right, but it just felt like it was so fast because we were constantly, constantly changing. 170 playbooks, you know, was just in retrospect.
Rajiv Parikh:Well, I'll say this, I think, when I see your, when you and I have had a chance. So Jim loves to hike, by the way, so maybe he learned it from Steve Jobs, or I think he just he just loves hiking, he likes being outside, and then he'll take you on these five mile hikes at Wonderlick, over in in Woodside. It's beautiful, it's the old Folgers farm and you just go out there and you sit amongst Redwoods.
Jim Kaskade:If you're in good shape, you're enjoying it.
Rajiv Parikh:Yeah, I took one of my friends from Jersey that ate a lot of steak and cheese and he had a really rough time. So, but, anyways, if you're in decent shape, you're going to love a hike with Jim, and so what I what I love about the way you think about things is the is the level of transparency you bring about and the change that you're open to. So when Jim sets about putting together his, his framework of multiple years, it's not set in stone, it's a thought piece, right. And then you encourage folks who join your management team or you recruit eventually, when you take over a company recruited your management team to think extremely openly. So maybe just talk about that, because I think there's a level of radical transparency that is not that we talk about, but that's not typical. Yeah.
Jim Kaskade:There's a, you know there was a. There was a book that I picked up back in 1999. When I first became a CEO, written by a management consultant that put this, this story you know, into a, or his framework, into a story about a startup in Silicon Valley, and the whole book was written from the perspective of the new CEO that came in and how this company was so well funded and it was the number one in its space and, you know, had this pedigree executive team, but yet it was failing. It started to lose its its competitive position, you know, became the number two, was starting to see decrease in decline and the board couldn't figure out why. And so they brought in this new CEO and she basically identified a really big dysfunction that you normally see in companies, in each person on the executive team. And so as you read this fable, you realize that what the writer, the author, is trying to get across is these massive, you know very common, dysfunctional, you know acts that people you know repeat over and over day to day in businesses, and she systematically kind of extracted that and changed it and made the team totally high performing.
Jim Kaskade:The authors Patrick Lecceoni, the books, five dysfunctions of a team. When I read that it was so simple that it was such an aha that I kind of applied the same business framework to my teams moving forward and I've been doing it now for decades when you, you know, the basic, fundamental layer of high functioning teams is having just an amazing amount of trust, to the point where you've you, you share as much with each other as you would with a close family member like your spouse. And to get to that level of trust you have to have kind of the cone of silence. What you say here stays here and it's always about that team. You know that. You know it's not like I don't want to call it team one, but this team first and then everybody else afterwards, so that you feel like you've got a place where you can cover the real issues.
Rajiv Parikh:One of the most interesting parts of how you manage groups is your 360 process. Every company's heard about this amazing way 360, you hear from not only your boss, your peers, the people who report to you, but the way you do it is, I'd say, like the extreme X games version of it. Maybe you can give me a quick sense of how that is different than what you've seen with others and why you employ that methodology.
Jim Kaskade:Yeah, I think it's definitely not for the week, right, and I think I've been challenged on even taking this approach by you know folks outside of my businesses, but at the end of the day, I haven't had a company and an executive team that hasn't appreciated the experience afterward. I think where I would start is you know, when, when any team is operating, whether as an individual or as a team, they're looking at generally two axes from their peers, two factors very basically, that kind of drives their perception of whether somebody on the team is doing what everybody would hope they would do for the team, and one of it is clearly just performance, right, Just, are you? Are you delivering on the things you promised? And then the second is do you have the potential? You know, are there the fundamental capabilities in your DNA that you can play the role that you're playing? And so a good example of that would be I'm a first time member of a team. I haven't even had a chance to hit the ground. So obviously, my potential. I got hired because I'm an A player, right, and I everybody thinks they got an A player when they hire them at the beginning. So the potential is super high off the scale, but the performance isn't there because they haven't had a chance to perform Well, no matter where you are in that performance and potential range. There are nine cells that we look at as an executive team. That kind of puts you in the places of where you are in that performance versus potential scale, and I call it the purple unicorn. But the far right, right, when the potential is off the scale, you can always overachieve because you're just aggressively trying to learn new things and really challenge yourself, as well as your peers and the team as a whole, and then you're delivering. You're over delivering on people's expectations. You're in the purple unicorn in the cell nine. We call it Well.
Jim Kaskade:My teams get together once a quarter and they rank each other including myself, on the scale of one to nine. It's a nine cell matrix. It's well defined. Each of the cells gives a description and it gives you kind of a directionally accurate view of how people think about you. Now, I don't care if it's perfectly accurate or not, it's just a way of getting people to tell you how they feel about how you're engaging as a team member.
Jim Kaskade:And so you get this anonymous list of ranks from one to nine, next to your name. You're also asked to rank yourself and again you don't know who gave you what score. You just come into this 360 and you may have all these ones, or you may have a bunch of fives, you may be a bunch of nines. You're killing it, Regardless of what somebody puts there, if your ranking of yourself is so much different than your peers. Think of the use case or the example where you ranked yourself a nine and all your peers ranked you a five. Oh my God, big difference. Right, that's usually game over, right, Game over. Your awareness is so far off. I'm sorry, this is gonna be a hard one.
Rajiv Parikh:You've got your head so far up your.
Jim Kaskade:So I haven't had that experience but once. But yeah, but you're astral, but you know, there's this now there's this tense room environment. Everybody's sitting down and they're like what's gonna happen next? I got these rankings and so on, and so I'll tally people's rankings over or, I'm sorry, under a number. So let's say, five is the number, how many people in five and below ranked you? You know five and below, you know. So you tally that and whoever had the most number of those five and below would start with first, and then we'd go to the next one and go to the next one, and maybe a bunch of others are like no problem, they're like clear. I'll always start open first, and so I'll start by.
Jim Kaskade:Basically, the rules of engagement are I have to tell you why I think my peers ranked me the way they did. So let's say you're one of those executives that got lower rankings. You've got to break the ice by telling everybody why you think they ranked you low. And it's such a great way to kick it off, because if you actually acknowledge and you tell everybody exactly what they're thinking, you've just totally chipped at the ice, right, you've melted it, you've diffused, because what happens next is I asked them, the folks that ranked you, to add, you know, to why they ranked you the way. But they have to do one other thing. They got to give some ideas of how they're gonna help you increase that ranking.
Jim Kaskade:So they can't just say I ranked you five because you really blow at doing this. They got to go. You know what? You had a lot of challenges. I didn't contribute much to helping you. This is how I'm gonna help you, so you get constructive support. Now, while everybody's giving you this feedback, you can't say anything. You just can say thank you. Now, how many times have you been presented with something that you disagree with? That you might just go, but you didn't understand. It's this context of this. You know, my car had a flat tire and I couldn't get into work and that's why I was immediately able to meet with that CEO and we lost that account. You know you just got all these excuses right.
Sandeep Parikh:So you meet every conversation with my wife.
Jim Kaskade:So you don't have to. You don't get to have that conversation with your spouse. Experience You're, because the whole function of it is to for you to listen. Perceptions, reality. Whether you've got some good excuse doesn't matter. Your peers think this way. You need to listen. And so at the end of the whole exchange, all you can say is thank you.
Jim Kaskade:It's super hard for people, but that's the rule. And then the ones giving you the feedback have to say, well, I think this, but this is how I'm gonna help you. It's not just criticizing, but if you know, if you're really really good and you're self aware and you tell everybody what they're gonna tell you, how fast does that conversation go? They're like, yeah, you nailed it. Now here's how I'm gonna help you. It's so much simpler. So you go around the room and you break you've broken all this ice down. And if the team's high functioning, they're hungry for this feedback, right, every quarter we kind of reset by basically putting it on the table. There's no longer this hidden. You know, understanding that somebody's struggling that you don't talk about in the workplace. So, yeah, they're really not doing their job well here. Don't talk about it. Let's just hope Jim fixes it, the CEO fixes it.
Rajiv Parikh:Now, this is an environment Because the boss knows everything, Because the boss knows everything and the boss is perfectly able, is omniscient and can just solve the problem. And the amazing thing is that everybody now yeah, most people deeper in the company are like the boss is an idiot, right? So it just depends where you are in that spectrum.
Jim Kaskade:Well, I can't say. You know that I'm always achieving the nines, but I do feel like everybody is now coming out of this with the axes buried right and there is the homework after the exercises. If now, if you want to go have a debate, go do it with your peers in a one-to-one, constructively. But you've now got the entire group to kind of give you some perspective. And if you haven't been listening to this already, you're going to listen to it in this exercise. And if you're not capable of creating change from it, you're just not going to be a team player, it's you're not, you know, they'll self-select out, probably right.
Jim Kaskade:They always self-select out. I've never had to make an executive team change with this process. They've made the change for me, so it's obvious that they're not a good fit and they're so uncomfortable with it they're gone, and so I think you know that's why it's kind of harsh. But then for high performers, you love it. You know you just like this is transparency at its core, right, and then you're going to hire other people like them. Then you've hired more good people.
Rajiv Parikh:You're going to have them go through the same thing and you won't, and even if you come in as more guarded because you come from a different environment, where the. Cya was rewarded or blaming other people was rewarded. You will learn that you'll have to change and you'll probably have to give them some time to make that change, but they'll eventually work themselves into it or self-select out, or be self-selected out or be helped out.
Jim Kaskade:Exactly, exactly, and it's a process that takes one to two quarters. It's amazing, we still do it every quarter and even with the team that I have now which is just amazing I've never had a team as amazing as I have today we still go through this process, because now, we're hungry for it.
Sandeep Parikh:You can always get better, jim. I'm curious what's your last rating on yourself? Where are you at right now?
Jim Kaskade:Let's see I got Cascade. I put myself at an eight out of nine and I had one two, three, four eights and three sevens.
Sandeep Parikh:Ok, so there you go, you're. Right on par, ok, great.
Jim Kaskade:You got room to improve Jim. Now, if someone gave you the one.
Sandeep Parikh:you're having a talking to that person, right? If there's one out loud, I'll give you the one I did something wrong.
Jim Kaskade:I did something wrong, that person's gone.
Jim Kaskade:Absolutely the seven questions what's your hometown, birthplace, where you spent the majority of your childhood? Second question family background what's your parents, siblings, significant other children, pets? So now you've got the baseline. Now the third question childhood challenge Like really truly impacted you Like deep. Bring it on and you'll get ones where, yeah, I lost my brother. That was huge and no one around the table knows this because you're not asking these hard questions, right. Or, yeah, my dad was an alcoholic. He used to hit me. You know you just get real answers right.
Jim Kaskade:Number four favorite hobbies outside of work. Now, you get a little bit of that. You know I love surfing big waves. First job, first professional job, not throwing pizza. And then worst job, and why. And then, lastly, you know what's your greatest strength, your superpower and your greatest weakness, or your kryptonite. But that childhood challenge won. So I lead it right and I kind of give the example and hopefully folks somewhere in the middle of that conversation will just give a big share, right, and so one and I've had several crying. So the one that comes to mind right now was a VP of alliances who shared with the team that he lost one of his kids out of three and no one knew that and he literally just started tearing out right down right there.
Jim Kaskade:Then, you know, and it was huge and everybody was like holy shit. So you get these personal moments if People are willing to share, and the beauty of that is that, and so this is it.
Sandeep Parikh:This is a. This isn't a group together that you're doing it, or is?
Jim Kaskade:this a group session.
Sandeep Parikh:Everyone's bonding everyone's kind of getting closer together. What when you reveal those secrets to each other? It's that kind of stuff.
Jim Kaskade:It's contagious, totally contagious and they, if someone will allow the team to know something personal out of the childhood, because that's where most of the shit happens. Then, when they get into first job, worst job, then you start, they start to open up and say, yeah, this is the shit that I really hate. You know, this is the stuff that's always. Yeah, they can be authentic and then finally they'll close with. Here are the things that I really suck at. Just so you know. You know I'm a sales guy but I don't know how to keep track of the numbers. You know, as an example, I'm just so they feel safe. They feel safe actually sharing that.
Sandeep Parikh:They feel safe because they felt the empathy from the folks in the room about what was what's really, you know, deep down, that totally makes sense. We actually do something really similar in our stand-up classes. We go around and share, share our deepest, darkest stuff, and that's actually where all the comedy comes from is from our being able to examine that stuff and Empower ourselves to go like oh, here's the comedic point of view on that. I mean, I've had people yeah.
Sandeep Parikh:People, people do. Is people doing sets on how they have herpes and how they feel outcast? Seriously, just like getting into or, or, or sexual assault or whatever, and then they end up doing the most Unbelievable vulnerable comedy comes out of that.
Jim Kaskade:That actually connect for sure, for sure. Well, that's the best way to do it, because you got to, you have to emotionally connect. I think you know the same thing goes with executive teams. If you can emotionally connect and you're just so much more high-performing, right. And then then I do a Myers-Briggs for everybody. I'm Certified, you know Practitioners, so I'll help analyze and I'll use that as a way to baseline people's personality types and then get the team to understand yeah, this person actually likes to do everything last minute because that's their personality type. So don't judge them, just know how to work with it you know, they're the ones that stay up ENT.
Jim Kaskade:ENTJ. Yeah, ENTJ.
Rajiv Parikh:Same as I am. Yeah, classic seat yeah for the last part of our interview with Jim. We wanted to explore what led him to his own personal Eureka moment. I asked him about what was the spark that lit things up for him.
Jim Kaskade:So you know, everybody has their origin story, I think, in terms of what drives them into a particular career direction. You know, obviously, as you're raised as a kid, your parents have a huge influence on who you are. There were two main things that you know, events in my life that Clearly, in reflection, see his inflection points for me. One was the one that drove me into tech as an engineer. So I started off as a double ECS, you know, engineer and I loved engineering. The second inflection event was what drove me into business. So the first one was Parents. Not a lot of money, christmas tree, one gift under the under the tree for me, which was great.
Jim Kaskade:And so one year I'm the age of five and I open up the, the Christmas present from my parents, and in it is one of these remote control transams. If you remember well what was the month, the move, the movie that had the transam in it, I forget, but anyway it was. I Thought remote control car, this is awesome. So I ran off in the garage and my parents were just envisioning me playing with it, you know, in the garage, and when they came out they saw me. I had taken it apart because I needed to figure out what made this thing work. I wasn't actually Using it. I was inspecting the pieces of it and what made it work, and I knew the electronics were gonna be an important part of my life, because I was so intrigued by that.
Rajiv Parikh:That's what you like. So it wasn't enough that you you got this really cool trans transam. You were trying to turn it into Kit from Knight Rider the David.
Jim Kaskade:I needed to advance it to AI driven cars. I just didn't know it at the time, but I was so enamored by technology and I still am like just I just can't help it. You know, I'm kind of one of these CEOs that just can't keep their fingers off the tech, so that's what's driven me to be a tech CEO. The second main inflection was was what caused me to become an entrepreneur, and that was in the same era. My dad was an army ranger and he was, you know, came out of the army after you married my mom and had me and didn't have a lot of money and they bought their first house, you know, here in San Jose, california, and I was. I can still visualize them walking up the cement, you know walkway to the front door it's a single story and my dad opens the door and the first thing I can notice is the smell Of dogs and cats. The previous owners had had so many animals in the house. It was just horrific right Wood paneling, it was dark, the carpets were thrashed and I looked at my dad like, dad, this place is a wreck. And he's like, yeah, we're gonna fix this up. He was very hands hands on right, ripped up the carpets, we pulled the paneling off the walls While I was helping my dad.
Jim Kaskade:I was asking him, dad, why didn't we buy a house that was kind of ready for us, you know, instead of having to do all this work? And he said, son, this is all I can afford and I go, well, why can't you afford more? He goes, well, my job, it doesn't pay as much, you know, as I, you know, would need to buy a more expensive house. I'm like, well, what jobs do pay more? And he rattled off, you know he could become a lawyer or airline pilot, and he goes.
Jim Kaskade:You know you could start your own company. I'm like, what does that mean? Starting my own company? Goes. Yeah, you know a lot of people to start their own companies. They're the boss and they, you know, kind of set the pace and you know many of them are really successful. I'm like that's what I want to do. I want to be able to run my own company, be able to have a culture that fits me, and then I can buy a house where I don't have to rip up the carpets when I first Walk into it. So that was a huge inflection point. Totally influenced me.
Sandeep Parikh:Combination of being an electrical computer science engineer, I went into tech and the rest is history how did I, from from perspective of you, know folks who are Executives now or man managers now and they want to make that leap? How did you make that leap right from from working for somebody? You didn't just jump right in, you didn't go Okay, dad, I'm gonna start my company right now, after I finish these these carpets. Right? How did you make the leaf no?
Jim Kaskade:I mean, like most, most people yeah, yeah, I mean most people will jump into a big company. You know Google, facebook, you know Twitter, name your web skill, success here in the valley You'll jump into a company that you're, you know, passionate about. You'll learn a lot there. I did my first ten years and then I realized, man, it's been ten years been working for this big company, this whole vision of trying to get in and become an entrepreneur. Then my next leap was into a startup.
Jim Kaskade:I went to work in a startup, an existing startup, and that was my first kind of you know taste of what small and nimble and you know Entrepreneurial really meant. But it wasn't my own. And that first company I spun out some technology and started my first. And when I started my first company, I didn't start it on my own right. I had an amazing set of co-founders when there was known chemistry which was really important and clear you know strengths that we augmented each other with. And then I had amazing board of directors, oh my god. And I was so lucky to bring in a, a mentor who became my chairman, who chaired in, mentored me as a CEO, gave me my wings as a CEO.
Jim Kaskade:So if I had like a message for entrepreneurs out there starting. It would be pick that first team like you pick your family members. You know if you're gonna go get married, you don't do it just in five minutes in Las Vegas and then make sure you've got a mentor that you aspire to be. I had the founder of terror data and His co-founder who decided to come work with me. It was just over-the-top pinch me moment. You know, anybody knows the brand terror data, the largest data warehouse company in the world. Data was everything for me. It still is everything to me in terms of what fuels technology and analytics now, and AI is really nothing without data. And so I had the data canes, the innovators on data, you know, basically jump in and say yeah we'll help you start your first company, which is just still a pinch me moment huge for me.
Rajiv Parikh:So you go from your nightrider moment to your home building moment, and that leads you to want to being the want to be the boss, and you put together a plan to get yourself there. Do you feel like it was a methodical plan? Was it a?
Jim Kaskade:This is the time a little bit of both. Right, I think you have to have the fire in you to say this is the time. Right, you can't go into starting anything. Where you're, you're somewhat conservative, reserved, you know, you don't have the resolve because it's hard, it'll be the hardest thing you do, and so you want to go in with all the energy and positive you know and come out that max because it's going to be challenged. And then methodical from the perspective of Sure, you want to kind of go with the flow, and everybody's flow is different, but you want to put some structure around it because you can waste energy and you could be the 999 failures to the one success, right, if you don't put a little bit of structure to your thinking. So you need a little bit of Passion, unless this is the moment, you know, fueled by some thought, you know, with others, not in the isolation that allows you to systematically kind of nudge yourself to success.
Jim Kaskade:You know you're gonna, you're gonna bump into things and this is how I run my businesses today. I think of it as agile. Everybody's heard agile. Right, you know, software isn't built In an environment of waterfall, it's all scrum. Now I think of business in no different way right. It's every quarter is a is a sprint and you know there's a systematic process of nudging the business forward at every quarter. You know boundary that I have, so it's amazing.
Rajiv Parikh:So it's awesome when you have that kind of situation in lifestyle and you're able to come to it and take the great leap. I know in my life and Many of our friends lives it is that moment where you think you can just go and not take salary for a while Is just one of those scary moments. It never goes as planned, but it's always exciting when you think about it afterwards, after that journey let's talk about let's do a few quick Closers things about you, jim, that I think people would love to hear. What's your favorite technological innovation or invention? What was the thing that that Gave you that feeling of magic that when you touch it, it sparked to life this notion of building tools for people.
Jim Kaskade:Wow, that's a hard question, rajiv. I mean, every one of my companies has been. Obviously, as an entrepreneur, one that you know has the promise of changing the world right. And so my you know crazy first business that I jumped into was developing new semiconductor packaging for microprocessors. Can you believe that? I mean, who remembers the semiconductor era that is now long past as an investment? You know that all VCs wanted to make and now it's just softwares eating the world.
Jim Kaskade:But I started off in semiconductors and that first company promise of building a chip package for Intel and AMD and TI was game-changing. I had investors who thought this was gonna be a billion-dollar business easily that wanted to jump in and the technology was so incredible that I kicked my first you know entrepreneurial, you know experience off with what I thought was just gonna make it and that's a story in itself. But it literally was. What you know is now in my blood. You know the experience of that technology that would have made Moore's law look like nothing to the board that I had. That was amazing to just the experience of the whole ride.
Rajiv Parikh:Building something from scratch that could change so many things. So, Jim, I wanna thank you. This was so much fun to chat with you like this, being one of my first guests. I always feel great knowing that I have amazing, caring, wonderful friends like you who are changing the world, making a difference, having an impact in a super positive way, and so I think anyone listening today can get that full breath of that life journey that you had and those sparks that drove you. And if they're growth-minded enough and I'm sure many of them would love to be they can just tap off of some of the work you've done and build from there, maybe even reach out to you.
Jim Kaskade:Appreciate that Rajeev Sandeep yeah yeah absolutely honored to be engaged with you guys today. Great conversation, so much more we could talk about till the next time.
Rajiv Parikh:Wow, that was really amazing. It was so great to have a person like Jim cascade working with us, chatting with us, telling him about his life, his journey, what sparked him, how he became an AI CEO of a really cool company, but really what motivated him to get there. And I'll tell you, the one thing that got to me that I really wanted others to learn about was how he leads a transparent culture and how these 360 reviews like you're like well, what the hell is a 360 review?
Rajiv Parikh:It's when all these people are interviewing, all these people are assessing you. It's like not just hearing from your teacher, but it's like the students and your peers, your other folks, and in the workplace, it's your boss, it's your workers, it's all the peers around you and it's like a personal experience. It's like a joint therapy session.
Sandeep Parikh:That's right and I think when that happens, when people get vulnerable around each other and they start to admit their faults or they talk about childhood traumas or whatever it is, you end up feeling closer to them and you wanna help them, Cause inherently, I think we wanna help each other and anything on the AI front that you gotta take away from.
Rajiv Parikh:I've heard so much about AI and with Jim I've had a chance to do seminars with him, with other folks, and so what I got out of it was that sense of optimism that these are tools that are so he was very optimistic, yes, so easily available, yes, so easily available to us that it's not gonna just yes, it might take over the world. This might be a terminator scenario, or it could be something that can help us tremendously today.
Sandeep Parikh:Yeah, I feel like the terminator scenario is far away. I'm less worried about that. For me it's the velocity that the change is happening, that like you talked about, like it took 50 years before we really adopted the light bulb and so we had all this time to kind of adapt to what that might who might be out of a job or whatever lantern lighters I guess, whoever those folks were like, who had to figure out a new trade and so but right now things are happening month to month. It feels like Day by day.
Rajiv Parikh:I mean, I think there's this whole notion of the disruptive nature of generative AI and we have to remember that it was just introduced in November of last year, of 2022. And it's just truly coming into the mainstream, like there's this. The latest version of their language model is so much better and but it's approachable in that you can. It's an interface question in which, just like original browser is to the internet when you, you know you had a chance to view things in a way that never viewed before or social media is to the message board conversations. Now you have this even easier interface. You could just ask this prompt anything you want in English and it'll figure stuff out for you.
Sandeep Parikh:Well, I just like to let you know that I've been in a chat bot this entire time and Sundeep is not actually here. So, I hope you've enjoyed this fake conversation with your fake brother.
Rajiv Parikh:All right. Thanks for listening. If you enjoyed this podcast, please take a moment to rate it and comment. You can find us on Apple podcast, Google podcast, everywhere podcast can be found. We'll catch you next time Story.
Sandeep Parikh:Number 3 you.