Greg Shove – Entrepreneurship Is More Like a Rollercoaster Than a Rocketship

In this episode of the Maker-Manager Money Podcast, I had the pleasure of speaking with Greg Shove, a seasoned entrepreneur and CEO of Section with over 30 years of experience in the tech industry. We delved into Greg’s remarkable journey, exploring the realities of building businesses in Silicon Valley, the myths surrounding startup success, and the invaluable lessons he has learned about persistence and resilience.

As we approach the end of the year, I asked Greg about his goals for 2025. He shared his aspirations to stay cancer-free, spend quality time with his newly arrived grandchildren, and ride the wave of AI innovation in his businesses. Greg is deeply involved in two primary ventures: Section, where he serves as CEO, and Machine and Partners, a company focused on developing AI applications for other businesses. He emphasized the importance of steering these companies toward sustainable growth and profitability.

We also discussed Greg’s personal life, including his family dynamics with twin daughters and a son navigating the challenges of a tech sales career. His reflections on the ups and downs of entrepreneurship resonated with me, particularly his analogy of the entrepreneurial journey as a roller coaster rather than a rocket ship. Greg candidly shared that while the tech industry often glorifies overnight success, the reality is filled with hard work, persistence, and the occasional setback.

Greg’s insights into the transformative power of AI were particularly enlightening. He discussed how entrepreneurs can leverage AI tools like ChatGPT and Claude to streamline workflows and enhance productivity. We explored the potential of AI in various sectors, including education and business, and Greg provided a roadmap for those looking to harness this game-changing technology.

As we navigated the conversation, I was struck by Greg’s perspective on the hustle culture prevalent in the tech industry. He acknowledged that while building a startup can be all-consuming, it doesn’t have to come at the expense of personal well-being or family life. He encouraged listeners to moderate their expectations and focus on creating sustainable businesses that provide a good living rather than chasing the elusive unicorn.

We also touched on the importance of understanding personality types, with Greg sharing his experience with the Enneagram system. He described his own type as someone who looks around corners, balancing optimism with a healthy awareness of potential downsides—an essential skill for any entrepreneur.

The conversation took a personal turn when Greg shared his experience with lung cancer, diagnosed just three years ago. He recounted how he navigated his recovery while managing the demands of fundraising for Section, highlighting the importance of self-care and perspective during challenging times.

As we wrapped up, we discussed the future of AI and its implications for society. Greg expressed his desire to educate and empower others to embrace AI, emphasizing the need for a balanced approach that considers both the benefits and potential downsides of this technology. He encouraged listeners, especially those from older generations, to engage with AI tools and explore their applications in everyday life.

This episode is packed with actionable advice, personal anecdotes, and a wealth of knowledge for entrepreneurs and wantrepreneurs alike. Whether you’re just starting out or looking to refine your approach to business, Greg’s insights will inspire you to embrace the journey and leverage the power of AI to enhance your entrepreneurial endeavors.

Links:

• Follow Greg on LinkedIn
• MBA Quality Online Education at Section
• From AI Hype to Working Prototype Machine & Partners
• Personal Math with Greg & Taylor
• Enneagram Institute (and Test)
• Greg’s Book Recommendation – The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers by Ben Horowitz
• Follow Kyle on LinkedIn

Kyle Knowles: Hello there, welcome to the Maker-Manager Money Podcast, a podcast to inspire entrepreneurs to keep going and wantrepreneurs to just start. My name is Kyle Knowles, and today’s guest is Greg Shove, CEO of Section, founder of Machine and Partners, and co-founder of Personal Math. Greg brings over 30 years of entrepreneurial experience and offers invaluable insights into building businesses that thrive even in the face of setbacks. We dive deep into his journey, the myths of Silicon Valley, and the hard-earned lessons of persistence. Greg also shares his expertise on the transformative power of AI, from leveraging tools like chat GPT and Claude to streamline workflows to the role of AI in education and the workplace. Greg provides a roadmap for how entrepreneurs can harness this game changing technology. Whether you’re new to AI or looking to stay ahead of the curve, this episode is packed with actionable advice. Welcome to the show, Greg. How are you?

Greg Shove: I’m good. Thanks for inviting me. I’m glad to be here.

Kyle Knowles: And where are you dialing in from?

Greg Shove: Menlo Park, California. So south of San Francisco, the heart of the AI gold rush, I think.

Kyle Knowles: It is. You’re in the right place at the right time for sure.

Greg Shove: I think so.

Kyle Knowles: So Greg, since it’s the end of the year, we’re heading into next year, what’s your biggest goal for 2025?

Greg Shove: Oh man, talk about starting with the heavy one. Okay. Lots, I guess. Stay cancer-free. Spend time with my grandkids. We have two grandkids that turned up in 2024, so spend some time with them in 2025. ride this AI wave for all the businesses that I’m involved in. There’s two primarily, of course, section where I’m full-time CEO. And then I started, but I’m not involved with every day, a company called Machine and Partners. And we’re building AI apps for others, helping other companies build their AI applications. So, you know, for those two businesses, I just want to help. you know, steer them or, you know, keep them in the wave, I guess, or keep them on the wave and find growth, find capital efficient growth, maybe even some profitability, right? That’d be a good thing.

Kyle Knowles: That’s always a good thing for business, isn’t it?

Greg Shove: Yeah. Hard to find maybe an AI, but I think we’ll get there.

Kyle Knowles: Yeah, for sure. And those are awesome goals. Congratulations on your grandchildren. You said you have two. Are these your first two?

Greg Shove: Yeah, first two. We have two kids who are twins themselves. They live in the city in San Francisco, so they’re nearby, which is great for us. And they each had a baby boy about seven, eight months ago.

Kyle Knowles: Okay, that’s awesome. So you have two twin daughters.

Greg Shove: Boy, girl twins. And then we have a 23 year old kid that’s in, a son that’s in New York in one of those typical hard tech sales jobs. You know, when you email and call thousands of people and no one answers.

Kyle Knowles: Okay. So he’s learning a lot of life lessons.

Greg Shove: He’s learning a lot of life lessons. He’s got, it’s exactly. So bottom rung of the tech industry, right? An SDR for, for a software company, not easy.

Kyle Knowles: Yeah, for sure. And that’s, you know, you got to start somewhere and getting used to rejection is really good for those life lessons right there.

Greg Shove: Absolutely.

Kyle Knowles: You’ve been through a lot. I mean, I see in your LinkedIn profile, you were a tech executive at AOL. So you were at the early wave of the internet. Now you’re heading up section as CEO, and then you’ve got You’ve got machine and partners as an AI company that you helped found and your partner in, and you’re doing personal math with, I believe, Taylor is the COO.

Greg Shove: She’s the COO, yeah. She’s an amazing kind of complement to me, operator, young executive. Really kind of has accelerated fast in terms of her career. And I tapped her as our CEO about a year ago. So that was a good call. So she and I write personal math, which is basically advice for other operators who are in the middle, in the thick of it, trying to advance their careers or advance their companies or their teams.

Kyle Knowles: OK, and so that’s a lot of a storied career, maybe in in tech, really always in tech. And you also founded a company that you were at for for 12 years or so.

Greg Shove: My last company, I was there for about 12 years. The company is probably now 16 years old, maybe longer. It was a battle. You know, listen, I’ve had a more typical Silicon Valley career. Everybody thinks or, you know, the mythology of Silicon Valley is start a company, four guys and a dog, you know, and then get acquired for a billion dollars five years later or something like that. You know, that’s that happens once in a while. That’s the exception, not the rule. The rule is more like my career, which was just hard work, right? A lot of persistence, a lot of failure, some success. You know, the rocket ship is usually more like a roller coaster. And so over 30 plus years, you know, I’ve had more roller coaster than rocket ship. But, you know, but a couple of good outcomes in terms of company exits. My last company was sold for $150 million. It’s probably worth two or three times that now. It’s owned by private equity. It’s an enterprise software company. But it just took a long, long time to build, a long time, you know, multiple pivots, and we burned too much capital. you know, made a bunch of mistakes, eventually figured it out, found product market fit. Now that company’s doing over a hundred million dollars a year in revenue, Section will break $10 million in revenue soon, annual revenue. And I think Section will be a long-term, very viable, profitable, valuable business. It just always takes longer. Kyle, it’s always harder.

Kyle Knowles: Yeah.

Greg Shove: You know, there’s always more kind of grief and disappointment along the way. Just the hard realities of trying to build companies, especially, especially new ones, right? New products or new markets or. new ideas. You just have no idea is the product going to work and then will customers buy it in some sort of repeatable way. As I say to every entrepreneur it’s pretty easy to get 10 customers. Like if you’re an entrepreneur and you can’t get 10 customers or maybe 50 or 100 depending on if it’s consumer business or enterprise business. When I think about enterprise businesses any good founder should be able to get 10 10 customers. You know they’ve got friends they’ve got family, they’ve got networks, they’ve got, you know, classmates, whatever, they can find a way to hustle to 10, maybe 20, 30 customers. But, you know, to get to a hundred enterprise customers and then to a thousand, that means you’ve got product market fit. It’s hard to find. And it’s where most companies basically fail. So, yeah, listen, my career has been, I’d say more typical, which is, you know, nothing that landed me, you know, a unicorn, but rewarding career with some good upside and some pretty miserable moments.

Kyle Knowles: I bet. And I love that analogy of a roller coaster, not a rocket ship. I mean, I think people just, AI, chat GPT is good at this. Anytime you talk about startups or anything, it will include the rocket ship for sure as a, as a emoji in, in, in the generative texts that it creates. But yeah, I think it should show roller coaster more often because I don’t think there are enough people that will take a chance on entrepreneurship because they think it’s going to be this one and done big deal. I mean, you have to grind it out. And the entrepreneurs I’ve talked to, that’s all it’s been is a grind. It’s not just overnight success. It’s overnight success after several years of hardship.

Greg Shove: Yeah, I think that’s right. And I think we set the bar too high for yourselves. And I think that keeps people what you said keeps people on the sidelines. I think they hesitate because they think they should have something inside of them that’s going to be amazing. It’s going to be a rocket ship. It’s going to be a unicorn or something like that. Or they’ll become millionaires or whatever the metric is. And it’s just, you know, it’s too much pressure and the expectations don’t need to be so high. How about make a good living? You know, how about start a company that doesn’t kill you, you know, that makes a good living for you? You know, that’s probably the… the right measure and doing something that not necessarily that you love. I don’t think you have to love what you’re doing every day as an entrepreneur. I think you have to care about it enough. Someone described to me what you’re looking for is a problem that really frustrates you. So you don’t like seeing the problem, but it also sort of interests you enough that you want to solve it. You need both of those sort of states, if you will, at the same time to give you the motivation that will power you through those moments where you got to figure it out, where it’s tough, where you might be running low on capital or when customers churn, all those things that you kind of bump into as an entrepreneur, you need to be able to power through it. And if you’re just focused on the outcome and a big outcome, I think that’s both distracting and in a way, demotivating. because your expectations are too high. And instead, sort of dial those expectations back, keep the ambition high, keep the expectations a little more moderate, I think is the way to think about it. And then as you get those wins, you know, they’ll pile up. It takes time, but those, you know, they’ll begin to kind of accumulate.

Kyle Knowles: So what are your thoughts on the whole tech bro hustle culture of, you know, tech startup? Is that, is that, does it have to be that way? Does it have to be 80 hour weeks? Can you have a family? Can you enjoy your life and take care of your mental health and your physical health?

Greg Shove: I think it depends on what you’re trying to do, what you’re trying to build, and at what scale. I think it’s a grind, and it can be all-consuming. And I think for many ideas and ventures, it will need to be that way. If you really want to tackle a tough problem, or a competitive market, or a product that hasn’t been invented before, or a business model, or a marketing model that hasn’t been tried before, yeah, you should expect this to be long hours. And not just hours, but sort of mentally and emotionally exhausting or consuming. I think that is appropriate. You’re trying to build something that doesn’t exist. And if you’re trying to build something in a way that will stand the test of time, really find product market fit, really keep customers happy, you know, that’s that’s not easy. And I would expect it to be distracting. I would expect it. I would expect you to be tempted to pick up your phone. while you might be at a family dinner. I’m not saying that’s good. I’m not saying that’s the behavior you should be aiming for. But this problem should be, in moments, should be so consuming to you, so interesting to you that, yeah, you might want to pick up your phone and check that Slack message. I certainly have. I’m not proud of it, so to speak, in these moments where I should be more present with my family. But these ideas or these challenges get inside you. and stuck inside your head and you want, you know, you want to work it and you want to see if you can find the solution. So not 24 seven, not seven days a week, not for, you know, years at a time, you obviously are going to burn out. And, but I would expect for some challenges and some businesses. The they’re going to be all consuming for others. You could, if you can moderate some of your expectations, moderate your income expectations, perhaps maybe you don’t have venture capital. which is probably a good thing by and large. I think most businesses don’t need venture capital and probably shouldn’t raise venture capital even though they do. But if you can manage your expectations and manage your sort of financial outcomes, then yeah, you can probably manage your time and manage that balance a little better. But it’s a, I don’t know if it’s a hustle, but it’s a grind and it should be at some level consuming a good amount of your energy.

Kyle Knowles: I want to go back to, so you’ve had the storied tech career. I don’t know if storied is too big if you’re going to call it.

Greg Shove: I’m not sure it’s storied, but I like it. I’ll use that with my wife, family this weekend. But no, I think it’s, as I said, I think it’s more typical. And so I think about myself, Kyle’s the Coach that wasn’t the best player, but makes a pretty good coach. You know, when you think about professional sports, often the very best players, right? The superstars, the world class players, they don’t typically make great coaches in part because I don’t think they have a sense of what it takes for everybody else. you know, to get to good, right? Because they’re naturally great. They’re the freaks. They’re the superstars. I think of myself more as I’m a good entrepreneur. I’ve worked hard, obviously, and had some moments where luck went my way. And that’s usually what is needed to get an exit or to get some sort of financial outcome. But, you know, again, I haven’t I haven’t had a 10 billion unicorn. So I think that makes me a better coach. And I do try to coach other entrepreneurs about the life they’re embarking upon and sort of how to optimize it. and have some success. So that’s kind of how I think about myself. Maybe not storied, but certainly well-practiced.

Kyle Knowles: Okay. And during this career, and you talk about you’re a good coach, maybe you weren’t the best player, but what is your number one skill?

Greg Shove: Yeah. Two, looking around corners. Which is both looking for upside and managing downside. I’m an Enneagram 6 Kyle. If you know the Enneagram, that’s a personality sort of classification system. 6 is someone that is a glass half empty kind of guy. I do worry a lot about the downside. I do try to manage my anxieties. by thinking through what are the downsides. So I think ahead and look for downsides, but I also maintain some ability to be a little delusional and a little too optimistic and think about those upsides. So looking around corners, I think seeing both the downside and seeing the potential upside, I think I’ll combine those into one superpower.

Kyle Knowles: Okay. And it was Enneagram

Greg Shove: Enneagram. Yeah. Enneagram is a personality system. Kind of, I’d say the next generation Myers-Briggs.

Kyle Knowles: Okay.

Greg Shove: And so Enneagram has nine types. I’m not an expert. My wife is actually, but I’m Enneagram six. Some of your listeners may know what that means. What it means for me is I look around corners and I worry a lot. So that as an entrepreneur that I think that can be mostly a good thing.

Kyle Knowles: Yeah, I like that. So I’ll put links to this personality test. I love personality tests, and Myers-Briggs and others. So yeah, check it out, and we’ll put a link to it so people can find out what number they are. Is there several numbers or just like how many?

Greg Shove: Yeah, one through nine. Yeah, so there’s lots of numbers. This test is sort of becoming the test in Silicon Valley. I think it appeals to Silicon Valley types. It’s a complex test, lots of different inputs into it, nine different types and different subtypes. It’s complex, Kyle. But people seem to like it, and I’ve got value from it. Again, mostly coached by my wife, who does this for a living. So yeah, I would check it out.

Kyle Knowles: Okay, I definitely will. So in this career, this roller coaster career, At what point were you in your career when you found out you had cancer? And how did that change maybe the trajectory of your life or your career?

Greg Shove: Oh, that was just three years ago. Okay, so it hasn’t really impacted my career yet. I’ll talk a little bit about that, though, in terms of how ventures can be all-consuming. So I, as you noted, I got cancer, it was lung cancer. I got very lucky. I was diagnosed really early, early stage, stage one. It was actually picked up, Colin, a routine scan for basically my sort of calcium and artery annual scan that I was doing because my father had heart disease. So my doctor said, hey, we should scan for this, you know, check out your heart. And so I was doing that and that picked up the lung cancer. So I was really fortunate because it was so early. So I had that removed surgically, no chemo, no radiation, which was, again, fortunate. The doctor at the time, the surgeon at Stanford said, listen, you know, you’ll be out of here in a couple of days at a hospital and you’ll be, you know, do an email, you know, probably tomorrow after the surgery and you’ll be back at work kind of, you know, as soon as you want. Two weeks later, I was fundraising for a section. We had started the fundraise, and I put it on hold so I could get surgery. And after a couple of weeks, I felt pretty good. I was back at home, and pain meds were way, way down. And so I started setting those meetings with those VCs to raise our Series B, our next round of capital. In hindsight that was insane. You know I shouldn’t. At my age I should have known better. Having been on this roller coaster for as long as I have over the last 30 plus years I should have known better because I you know I got through it. The fundraiser was not successful. The market at that point was deteriorating. Our sales, frankly, were deteriorating that section because the pandemic was over and a lot of that demand that we’d seen surge in 2020 and 2021 was beginning to contract. So like Peloton and Zoom and a lot of other companies have benefited from the pandemic we had, and then we were seeing that business contraction. So the fundraise was not going to work. And it took me a few more weeks to find that out. And then, frankly, I sort of crashed. I had sort of just got completely exhausted and depleted around Christmas time. When I look back, I realize what was I doing, right? Two weeks after lung cancer surgery, I was back, you know, kind of on the road, on the virtual road. I was doing this all over Zoom. You know, fundraising is intense. It’s hard. It’s all about rejection and being resilient and kind of getting up the next day and doing a couple more pitches. And so I should not have been doing that. I should have known better. I should have I should have either not canceled that fundraising. We didn’t need the capital. We wanted the capital, but we didn’t need it. So I probably should have taken a month or two. Kyle looked after myself better and, you know, my kind of mental health and emotional health after a surgery like that. But I didn’t. It was, you know, again, these startups in these moments can be all consuming. And I thought if we could get that capital, the business would be that much stronger in terms of our balance sheet. So yeah, you know, don’t don’t do that. You know, get some distance, get some perspective. And in that moment, I didn’t have it. You know, I really did.

Kyle Knowles: Well, it probably took your mind off of it as well a little bit.

Greg Shove: It could have been that. It was certainly something for me to do. I do like these intense experiences that startups offer. I’m good in crisis. I tend to do well, meaning I can handle them pretty well. It wasn’t a crisis, but it’s one of these moments where you got to be all in and really, really engaged to run a fundraising process. It typically takes anywhere from one to three months, and it’s mostly 99 no’s to get one yes. Yeah, yeah, these are these are moments where I do tend to perform better. So that’s probably why I was, you know, attracted to it, I guess, in terms of, you know, throwing myself into it. But yeah, maybe not two weeks after coming out of hospital.

Kyle Knowles: For sure. And so, thank God you’re cancer free right now, and you just have to go in every six months, every month, or how often do you have to go in?

Greg Shove: Yeah, what’s amazing, Kyle, now is that there are these technologies called blood biopsies. So in my case, my specific type of lung cancer, they’ve actually sequenced the DNA from the tumor. And there’s a company that they draw blood every six months and can detect if that cancer DNA is recirculating in my system. So basically, you can, you know, the noninvasively, it’s a blood draw. Get a quick read on is, you know, is this cancer coming back? So I do that every six months. I do a scan every year and I expect to be cancer free.

Kyle Knowles: That’s awesome. That’s awesome. I don’t know if I can ask this on a podcast, but how old are you, Greg?

Greg Shove: I’m 63.

Kyle Knowles: Which is amazing. You have so much energy. You’re so into AI. You’re teaching all these classes at Section. You’re a CEO of a company. You’re doing personal math with Taylor. You’re also a founder.

Greg Shove: Yeah, I am. Why slow down? I mean, first of all, I don’t golf. Or when I do, I suck at it. And frankly, I look around, I see some of my friends, I think they’re retiring a little too early. We’re all going to live longer. I think for some of us, if you can find a way to kind of find the off ramp and be happy and find ways to spend your time, that’s great. I just I don’t see that in the short term, not for me. So my goal, Kyle, is to keep working for at least 10 more years, maybe not at this pace, maybe not as a startup CEO, you know, with that level of kind of risk and responsibility and stress. But I would like to keep working for a good amount of time and create economic wealth for my family. So yeah, no slowing down. That’s why I got into AI. The bottom line is our cognitive abilities do decline. That starts at age 50. Our fluid or our processing cognitive abilities start to decline at age 50, and then they accelerate the decline after 60. So I’m in that zone. And so that awareness combined with when Chad TPT Plus came along, which was February the 1st, 2023 last year, I started playing around with that really more seriously. I was like, OK, this is going to be one way I keep working. These kinds of tools and technologies, AI, generative AI specifically, will be an edge for me. And that’ll allow me to keep kind of keep on my mental game. And I work in a place that’s probably the most ageist work environment in the world, right? Silicon Valley, if you’re not 28 in a hoodie, you’re an idiot. So, you know, I just thought, you know, this AI is going to be pretty cool for me. And that’s that, you know, that’s been the case.

Kyle Knowles: And so you mentioned GBT, what other AI tools and workflows have you adopted then?

Greg Shove: Yeah, my go-to are, like others, three, perplexity for research and more that sort of Google replacement. Not that I’ve replaced Google with perplexity completely by any means, but for what I call knowledge searches versus functional search. So functional search, I stick with Google. I keep using that, obviously, every day. But for my kind of knowledge search, I’ll use perplexity. And then for my everyday AI as thought partner, AI is kind of co-worker. I’ll bounce back and forth between GPT and Claude. I tend to prefer Claude, Anthropics, Claude Sonnet 3.5 is the actual model name. I prefer that AI for its kind of tone. I think it’s better at sort of collaborating, especially around business. topics. So I’ll tend to use Claude for that kind of use case and GPT for everything else. For big questions or high stakes decisions, Kyle, I’ll use both at the same time. So I’ve got both browser tabs open and I’ll just take the same prompt and drop it in both and go back and forth. and just see how each one will work with me on a specific challenge. And I think that’s, you know, it’s a little bit extra effort, but not much. And I get usually value from both of them when I’m doing that, because they’re different, you know, and they’re going to work with me in a different way, give me different answers.

Kyle Knowles: Yeah, I agree. And perplexity is my go-to as well for knowledge search. And I’ve continued to pay for ChatGPT and Claude. So $60 a month for those three. And it’s like, I’m bouncing back and forth as well. I find ChatGPT a little hypey when it generates content sometimes. It’s a little more like too much over the top. I like the way Claude writes things better. But I wish Claude remembered our chats, and I wish Claude also had a voice mode.

Greg Shove: You can see, I mean, OpenAI is a bigger company. They’ve got more engineers. They’ve got more researchers. They’ve got more of everybody, right? They’re a much bigger company. They have about 86% market share. So you’re really beginning to see the advantages of scale in that they are able to release more models faster. They obviously released 03 last Friday, the new reasoning model. So they’re able to release more models, more features. They were first to mobile with an app and so on. So I think that they’re going to be hard to catch. My guess is Claude will either need even more cash. They already got a bunch just recently. They’ll need to be bulked up even more in terms of resources. Anthropic will need to be. Or you might see them having to focus. to narrow down the focus of clause. So it’s really good at less things. But in terms of the Swiss army knife of AI, it seems to be GPT.

Kyle Knowles: Yeah, I agree. And I keep telling people don’t sleep on Google because Gemini, and I don’t know if you’re using Notebook LM or not, but I used it to do research on you for this podcast. It’s like a custom GPT out of the box, you know, off the shelf. And you know, I can throw all of all of your personal maths, all the writing you’ve done your LinkedIn profile, everything and just it will even generate a podcast, basically an AI, female and male voice. I listen to that I write down research and questions that I want to ask you based on that. Hopefully, there’s not too many hallucinations. We’ll find out as we go through a few more questions. But I just think Google’s sitting on a goldmine with YouTube and all the data they’ve collected for years and years. And all the sites they’ve indexed. I just think it seems like they could flip a switch and just continue to come out with things. NotebookLM, I just heard about it on a TikTok. And now I’m like, loving it.

Greg Shove: It’s pretty amazing, NotebookLM. I haven’t used it that much, Kyle. I’ve done a couple of those, like, hey, give me a podcast. out of this document, and it’s mind-blowing. So I’m waiting for Google too, but how long do we wait? You know, like, hey guys, you got all this money, all these advantages, all these engineers. You’ve got to bring it to market in a coherent way. And I think you’ve got to, you know, GPT stands for AI in the mind of consumers. That’s really what’s happened. That’s a hard thing to catch. But, you know, listen, more is better. These technologies are so powerful and we want more than just one or two or three companies as dominant. Even half a dozen is probably not enough. So at this moment I’m probably most concerned about the concentration of AI power in just a few companies, which means just a few executives. And if you think about, you know, Zuckerberg’s track record at Meta, not great in terms of managing the risks with social media. And so we just, you know, how much can we trust Sam Altman or Mark Zuckerberg or Elon Musk for that matter, to really manage these capabilities in a way that benefit all of us, you know, not just shareholders, you know, we’ll see. But I think, you know, the less concentration, the better in terms of kind of AI leadership and ownership.

Kyle Knowles: I agree. So Greg, how much do you use voice mode with chat GPT?

Greg Shove: Yeah, quite a bit. I’ll use it in the car a lot and or, you know, while walking or hiking. I think about it as basically replacing some of my podcast time. So I’ve probably taken an hour a week or so of time I would have spent listening to podcasts and essentially having a conversation with GPT. And of course, it’s a conversation you can steer, you can go in the direction you want and at what level kind of in terms of the topic you want to discuss. So yeah, I just think it’s, again, I think it’s game changing. It will be game changing for learning, for sales training, all kinds of use cases. And as I said, just casually, just a great way to kind of learn and be informed. It’s time efficient because you get to control the conversation because you’re, you know, the AI is following your lead, at least for now.

Kyle Knowles: Yeah. And I think people just don’t understand the power of it. People need to buy the app. They need to put it on their phone and they need to have a conversation with AI. That’s all. I mean, there’s nothing to be afraid of. I think a lot of people are afraid of, oh, my information is going to be out there. They’re going to use it. to their own advantage and something like that. But I’ll go on a walk with chat GPT, have a conversation about my plans for next year. Here’s the pillars I’m thinking about. The whole transcript is there when I’m finished. Plus, I’ll always end the conversation with, hey, can you summarize what we talked about and those kinds of things. And here’s the bullet points. And I’ve got it all documented right there. And I just went on a, you know, 30 minute walk.

Greg Shove: Yeah, I think we’re in this moment where A lot of people are getting their education about AI from the media, which is just the worst place to get it because, you know, they’re all either overhyping it, all the things that it can do and, or it’s scaring the shit out of us in terms of, you know, it’s coming for us, right? It’s coming for our jobs. It’s coming for what it means to be human. So I just think that a lot of people are, are understandably concerned. They are pragmatically concerned. Things like data privacy, which I think they don’t need to be as concerned as they are, but they’re concerned about that. And also just this kind of existential concern around, you know, what’s this mean and how’s it impact education and our kids? It’s easy to be alarmed about AI, right? And it’s easy to be, and I think one natural reaction is just to put your head in the sand or just sort of not really engage with it until you have to. And so, I think that’s a mistake, obviously. I engaged early, and we pivoted sections, so we would be the school for the age of AI, and so we could teach as many other people as we could as fast as we can. I’m disappointed at the pace we’re going, meaning I want to train more people faster. We trained 15,000 people this year. I’d like to train 100,000 next year and a million the year after. I want to get as many people as we can into what I call the AI class so that they’re able to use these tools and really not be scared of them, be confident, learn how to integrate them into their workflows. So, you know, we got work to do. But I think the media is not helping. And I think it’s somewhat natural human reaction, which is, you know, what is this stuff? It looks scary and unnatural. Therefore, I want to avoid it. You know, younger people, not right. I mean, the first AI native generation are now going to be entering our schools. Of course, there are our companies. Rather, they’re at school using AI. And of course, they’re being accused of cheating when they’re using AI at school. And then when they come interview in our companies, we’re going to want them to be fully AI native. And in fact, we’ll we’re going to want to hire those kids because they’re going to be that much more productive and more fluent with these technologies. So I think we’re all in for a little bit of awakening inside of companies and teams when we start to hire these kids out of college because they’re going to be 100% AI enabled. you know, because they are already, right? So there will be a, it’ll be different in terms of when they come to work and how they work, because they won’t think twice about consulting or asking or working with AI. They don’t, they don’t think it’s going to be cheating. They think it’s going to be smart. I can’t tell how many people, Kyle, tell me when I’m in person and in doing these lectures or workshops with other leaders, the most common sort of concern I get is, well, am I cheating by using AI? Am I cutting corners by using AI? Am I going to be viewed You know not favorably by my boss or by my team because I’ve admitted I’m using AI. So again it makes sense. We have these deeply held beliefs cultural beliefs almost about work. We know that we create value by working and that the ideas are our ideas and that working hard. You know it is a virtue all those kinds of typical beliefs we’ve had about work. They get challenged by A.I. It doesn’t have to be your idea. It could be the A.I.’ ‘s idea and maybe you made the idea better or maybe does. Again it doesn’t matter. You collaborated with your with your A.I. and you got a good idea and that’s the one you want to propose and move forward with. Doesn’t matter where it came from necessarily. But again, these are these are big changes, sort of big cultural changes or kind of belief system changes. You know, you’re not cheating with AI. You’re being smart by working with AI. You know, that’s where the I think the biggest challenges will be that we have to learn how to use the technologies. So the kind of the technical skills or the prompting skills, just kind of the, the, the tactics of working with AI, we need to, we need to train people on that, but mostly we have to train them to think about it differently in terms of their own, the way they work and that it’s okay to consult an AI and get help from an AI.

Kyle Knowles: So Gen Z, they’re going to be growing up with this and, you know, using it. What’s your advice for Gen Xers and Boomers regarding AI?

Greg Shove: I mean, just follow my lead, get on it. Like, you know, it’s what you said. Put GPT on your phone and you don’t even need a paid account anymore to get the best model. It’s great. OpenAI makes GPT-4, which is their, now they’re kind of the frontier model, which means the best current model. GPT-4, you know, you get for free. You don’t even have to pay for it. If you want the app and you want to get some other sort of features and no limit to your conversations, pay the 20 bucks a month and get GPT+, but just start playing around. If you don’t see a use case at work, start playing around at home. I just think that there And I think that’s kind of the Achilles heel of AI, Carl. It can do so much. We’ve never had something like this before. We’ve always had software apps that do a few things really well. And we love them because they do a few things really well. We love Google because it’s great for search and so on. We love Uber because a car turns up and takes us somewhere. And now Waymo. So apps and software have worked in that way. They do one thing or a few things very well. AI is the opposite. It does almost anything. but not great, right? So it’s got, it’s, you know, it’s, it hallucinates and it’s prone to mistakes and it can be, you know, the software is buggy or the, you know, the, these things are really early. And so I think for most people, it’s a little confusing. Okay. It does all these different things, but doesn’t do one thing really, really, really well. Not, not every time, right. It is, it’s an unreliable technology, but it’s, it’s got, it’s so capable. So I think that just kind of, It’s a hard thing for people to wrap their heads around. It does what? It codes, and it writes, and it creates images, and it makes songs, and it does strategic plans, and helps my kid with their homework, and it does bedtime stories. Whatever, what’s done that ever before in terms of software that we have had in our lives, whether it be at home or at work? It’s just a new thing. I think my advice is bring it home at least. If you don’t want to bring it to work, You know bring your eye home and start to do things like travel planning with your eye because travel plane to me is the obvious consumer use case where there’s so much friction for the consumer. We’ve all done travel planning for a trip. We all know that ends up with like 10 or 20 30 browser tabs open for Expedia and travel loss of the TripAdvisor and you’re reading the reviews. You know what it’s like. And really, when you play around with chat GPT for that, you realize this is the future of how we’re going to access our information. Something intelligent behind the scenes has looked at all the same information that are contained in those browser tabs that you opened, and from that can give you an answer in a really clean, crisp way where you don’t have to open all those browser tabs and scroll and all that stuff, right? So the way I think about that, Kyle, is interface friction. will not be tolerated in the future. I think it’s one of the biggest outcomes of generative AI. from the last couple of years, that when you play with generative AI, you realize the interface friction to our data, our content, our information is really being dropped by chat, that chat kind of interface to an AI. And we’re not going to tolerate opening up 10, 20, 30 browser tabs anymore. It’s just going to be, it’s too painful. People are not going to do it. They’re going to expect their AI to come back with the answer. And we’re going to want the right answer. So we’re not going to tolerate, we’re not going to likely tolerate hallucinations as humans. And obviously, AI needs to fix that over time. But I think that that to me is the best home use case. So when I get resistance, I tell people, go home and start planning a trip and use GPT and tell me what you think.

Kyle Knowles: So as far as AI goes, the fear that I have of it is us becoming maybe less human. You know, I like to write, I like to generate ideas. And AI, like we’ve talked about, seems like a cheat to that. But there are other ways that, you know, social media and being online and, and, and kind of living the second life online, make us less human too. We’re not present anymore. We’re sitting across from each other at a dinner party and our phones on the table, just always beckoning and waiting for us to answer it or whatever, right? So how can AI make us better humans and more human and maybe with efficiencies give us more time to do human things?

Greg Shove: Yeah I think it’s going to do both Kyle. I mean I think it’s it’s like like you said like social media. It brought us together in some ways and connected people that were unconnected in really meaningful ways and it isolated us at the same time. And I have the same sort of expectations or optimism and fears for AI. It will. create great benefit for humanity and have a whole bunch of unintended and unpleasant consequences. I don’t want my kids falling in love with, you know, sex chat bots or whatever. That doesn’t sound very human to me and doesn’t sound like a very satisfying relationship. So I don’t want that to happen. At the same time, Most of the planet can’t get access to a good therapist or a good coach or a good business advisor or a good mentor. And I think in those moments or a good doctor for a second opinion or even a first opinion. So I think, you know, in those moments, I was going to do a lot of good for a lot of people. And I think that’s just, you know, it’s two sides of the same coin. And the you know, how do we manage to a better outcome? That’s going to be some combination of us as users, Big Tech and their willingness to accept the responsibilities for these technologies. That’s I understand you know this cause not to be optimistic about that. Big Tech have shown what they’re all about is obviously making money. And they’ve raised huge amounts of money to fund this experiment. And so, you know, I think we’re clear what they’re going to do. You know, they’re not here. You know, the big tech companies, including OpenAI, I don’t think they really care about solving health care or solving, you know, fixing education or solving the climate crisis. They say they are. They say that, you know, maybe that will be an outcome of these technologies and it might be, but I don’t think they’re going to drive that change. I think it’s going to be entrepreneurs and people like us that use these technologies and try to solve those problems. Let’s be clear, big tech’s here to make a shit ton of money. They they see this as a huge wave of disruption and therefore spending by mostly enterprise consumer spending as well in terms of consumers paying for AI. But mostly who’s going to pay the bill here is going to be companies. And so yeah big tech’s excited about it and they’re all in because they see this as the next wave of basically IT spending enterprise IT spending in the U.S. and globally. And that’ll be trillions of dollars. And it will probably need to be to pay back all the money that’s going in to build these supercomputers and all that stuff. So you know I think that we need some combination of government. Hopefully, regulation that’s meaningful but not oppressive. Some responsibility amongst the big tech providers, the AI providers, and then us, you know, users and leaders of organizations that consume AI, you know, inside of our workforces to try to manage to hopefully capture the upside. But we’re going to get some downside, Kyle, and we’ll end up with some people spending too much time inside talking to their AI coach or their AI girlfriend. Again, I hope my kids don’t do that, but I also hope my kids use it when they need access to a mentor or to an advisor fast, or a coach or someone like that. That’s a great way to use AI.

Kyle Knowles: I love the idea of even therapists for most of the world can’t afford that. A lot of people don’t have insurance to pay for therapy, things like that. So uses of AI in that way are fantastic. And of course, for entrepreneurs, solopreneurs, I mean, the sky’s the limit. It’s astronomical what AI can do for one solopreneur. to help them run a business and launch a business.

Greg Shove: Yeah, totally. I think it buys us 25% to 50% or extends us 25% to 50% or buys us that much time. It’s something like that. It’s very meaningful. And that’s why, not surprisingly, OpenAI’s revenue in the early days, early days in the last two or three years, the company’s very young in terms of generating revenue, but most of it came from SMB and consumers. Makes sense. We’re the ones that need the edge. If you work in a big company, You know, you’re more risk averse and you have a lot more resources and you’re told, you know, don’t play with fire and AI looks like fire. But if you’re an entrepreneur, you’re a side hustler, you’re trying to get your own business off the ground. Yeah, it makes sense. You’re interested in finding new tools that help. And this thing came along and it’s 20 bucks a month. You know, let’s do it. Right. So I’d say three quarters of OpenAI’s revenue has probably been from SMB and consumer. That will change in the next decade. So enterprise will end up paying that, you know, the biggest part of the bill. You know, it makes sense to me that it is people like you and I using these tools because we, you know, we need the extra time back.

Kyle Knowles: Yeah. And it reminds me of, you know, the advent of sampling, you know, samplers and the rise of rap music and things like that where individual. people could lay down beats and record songs and blow up and make money and things like that. I mean, it’s using technology to their advantage to do that kind of stuff. And entrepreneurs can do that. Gray, I wanted to talk about the podcast. My podcast is called maker manager money. So you know, the Paul Graham manifesto about makers versus managers. And my belief is that, you know, you have to make something, then you have to manage it, you can’t just make something and then it’s going to sell itself, right? You have to manage the sales of it, the administration of it, the manufacturing of it. On the other side of making and managing or makers and managers is the money. That’s where the money is. You have to make and manage and then there’s money. So throughout your career, I know you as a CEO, obviously you’re a manager and you’re scheduled, you know, every 15 minutes or whatever it is every day. But then some of your other pursuits like personal math and machine and partners, are you more of a maker?

Greg Shove: Yeah, listen, I think I’m a maker everywhere a little bit, never as much as I want. Perhaps, although I’m not sure I have the best instincts around product, part of my job is to hire better people at product than I am. But at Section, we’re building something called Prof AI, which is going to be an AI coach to teach people AI. So it’s an app. It’s built on top of both the Cloud and GPT APIs. So we’re using those two AIs to power Prof AI. And I’m sitting in product reviews. every month with that team. I was on a review on Friday and I had a bunch of feedback for the product in terms of where I thought it was a little too heavy or a little too slow or too text intensive. It wasn’t fun enough. The UI to me felt a little heavy, a little serious. So listen, I think we want to always be making in some way. We need to know what we’re good at, I think, in terms of You know, where, where we can make or where we can help others who are making. So we sort of, I think we, we want to stay involved in the product. I think that. Yeah, that doesn’t matter where you are in the organization. I think you’ve got to as a leader, stay close to the product and influence it in some way. I do spend more of my time on distribution so that, you know, getting that product to the right people and getting them to pay for it. But if my job was just managing Kyle without any making, I’d probably lose interest faster in what I was managing, if that makes sense. I like to have a hand in the making of it, even as the company and product matures, because the product’s never done. And certainly these AI experiences are so unique and so new that I find that just fascinating. How will we use AI and how will we create the AI in a way that will incent our users to use it and use it a lot? Because that means they’ll be that much more loyal and they’ll pay for it.

Kyle Knowles: I agree. I love those answers.

Greg Shove: But what I will say is, as an entrepreneur, I’ve learned to pay a lot more attention to the money and specifically the plan. I’d say when you sort of unpack money, what you’re really unpacking is what’s the plan. on both the revenue side, obviously, and the expense side. And it took me a while, maybe longer than it should have. But over the last five, maybe 10 years of my career, I’ve become much more disciplined and much more relentlessly focused. on the plan, the annual plan, the monthly plan, the weekly plan. Really, I take a lot more satisfaction than I ever used to in just hitting the plan each quarter and just the discipline and the satisfaction of, it’s great to exceed it, but don’t miss it. You know, as I said, on both sides, the revenue and the expense. So that’s a big part of how to be a maker manager is to deliver the plan.

Kyle Knowles: Make a plan, manage the plan, deliver it.

Greg Shove: Yeah, make a plan, manage the plan, deliver it. Yeah, sure, it changes and you’re going to miss it some days, but not by surprise. I think what I’ve learned is that management teams and boards, if you have a board, most of us don’t have one, don’t need one, but if you have venture capital or investor capital, you often have a board, just manage the surprises. So there aren’t many. Manage your plan to manage surprises. at least to the downside. Surprises to the upside are fine, but not too many surprises to the downside.

Kyle Knowles: That’s great advice. So I just want to wrap up with a few personal questions. I’ve got one question before that. What’s the book that you recommend the most to people?

Greg Shove: For entrepreneurs, I still recommend it’s probably 10 or 15 years old. The hard thing about hard things by Ben Horowitz, the venture capitalist from age 16. It’s a, just a good, realistic view of the hard lessons and, and the things you’re going to have to do if you want to try to build a company. So it’s, it’s, I think it’s required reading for any entrepreneur.

Kyle Knowles: I love it. So here’s a lightning round of questions for you, Greg. What’s your favorite candy bar?

Greg Shove: Oh, Henry. But cold in the fridge.

Kyle Knowles: Very unique answer. Never had that answer. I’ve interviewed 40 entrepreneurs, and I know it exists. Have you heard? Maybe it’s Canadian. I’ve heard of O’Henry, yeah, but I’m going to try it now. I’m going to go try to find it.

Greg Shove: All right, try to find it.

Kyle Knowles: Yeah, I love it. Favorite musical artist?

Greg Shove: Springsteen, Bruce Springsteen. You know, I’m obviously aging myself, but my wife and I followed him a lot of places. Actually, this summer in Barcelona, which was amazing and on Broadway and a bunch of places. Yeah. So it’s Bruce. He’s a great American hero for me and a great songwriter. We should all listen to him or read him.

Kyle Knowles: For sure. And are you originally from California or are you from back East?

Greg Shove: No, no. I’m from Canada. I was born in Toronto, outside Toronto, and I was raised in England, London, England, and then back to Canada. And then I met a guy in Toronto and Canada, kind of a mentor of mine. He said, listen, what are you doing here? Do you want to be in technology? You know, you’re interested in this thing called the internet. You’re going to be, he said, there’s a grocery store in Palo Alto, Greg, it’s called Molly Stone’s. You go to Molly Stone’s on Saturday morning to do your groceries. You’re going to meet more people there in the store in tech than you’re ever going to. Then you’re going to be in a whole year in Canada. So get the hell out of Canada. Get out of Toronto and get to California. So I took that advice and came here and went to school here and then stayed.

Kyle Knowles: The rest is history. That’s great advice that you received. And so how did you pick up Bruce Springsteen then from being in Canada?

Greg Shove: I mean, he’s everywhere. He’s global. He’s global. He seems very American, but he’s American, but Canada, we were, we’re your next door neighbors. You know, we’re, we’re just, we’re just there.

Kyle Knowles: You’re basically Americans.

Greg Shove: Yeah, exactly.

Kyle Knowles: Well, exactly. Favorite cereal.

Greg Shove: My wife’s homemade granola.

Kyle Knowles: Mac or PC?

Greg Shove: Oh, Mac. I worked at Apple. Just for about nine months, I guess. Then I was fired. The only real job I was fired from was from Apple, but still love Apple and Mac ever since.

Kyle Knowles: Google or Microsoft? Google. Dogs or cats?

Greg Shove: Dogs, but I have to say I’m not a dog lover. My family are dog lovers and I don’t get cats.

Kyle Knowles: Phantom or Les Mis?

Greg Shove: Phantom.

Kyle Knowles: Okay, last two questions, Greg. What’s the worst thing about being an entrepreneur and what’s the best thing?

Greg Shove: The worst thing is The sacrifices I think you will have to make along the way that are not necessarily known to you now, but they will obviously reveal themselves to you. It might be relationships. It might be family time. It might be health anxiety and so on. So, just it’s a hard road at times. And it comes with a cost and. You know, again, no, no specific solution there, except kind of get through it. If the cost is too high, get out. So, I do think a level of awareness there. to know when to kind of pull back or dial it down. It matters a lot but it doesn’t matter that much. You know Kyle once I was driving home. This is my last company. So this is probably eight years ago now something like that. I was driving home and we had pivoted the business basically for one last time into this enterprise software What kind of mobile app, mobile communications app for companies. So, I was driving home on highway 280, if anybody knows the barrier, it’s a beautiful highway coming south from the city. The offices in the city, I live down on the peninsula. I was driving home and I said to myself, and I was usually the last to leave the office. The team back then was probably around 50 people. So I was driving home and I said to myself, and I remember saying this to myself, if I lose my marriage, that’s okay. I won’t lose my kids. So I remember sort of intentionally saying to myself, okay, I think this pivot is going to work. I think I can turn this corner and I think I can get this company, you know, on a path to growth and eventually profitability. And at that, in that moment, I was willing. Cause I knew here, here I was coming home, you know, it’s late, late night after late night, and this was going on for years. It was a real struggle. And I remember saying to myself, Hey, I, you know, if I lose my marriage, that might be an acceptable cause, but, but I won’t lose a relationship with the kids. Right. That’s nuts. That’s not so I even thought that. It didn’t happen, but I was prepared to, at least in that moment, at least I thought I was prepared to make that sacrifice. That’s how much I cared about the company and the business and my kind of role, even maybe even a little bit my legacy. So, you know, don’t do that. That’s a moment where you got to kind of step back and get some perspective. I didn’t have it in that moment. What’s great about being an entrepreneur is you get to create things that don’t exist. And I think that is a way of making a small impression or mark on our world is that you get to bring. to market or open a store, whatever it is, product, a new service that didn’t exist before. And I think there’s something just empowering about that and liberating and hopefully you can do it profitably and make a living and create some economic security as well. So I just love the idea of, I like to build things that don’t exist.

Kyle Knowles: I love that answer. So Greg, thanks so much for being generous with your time. I know I’ve looked forward to this conversation for over a year. I know we had to reschedule a few times. Thank you for your patience and thank you for being generous with your time. I’ve loved attending courses on sections school with you as the instructor. I love sections. focus on AI and even free webinars and things like that, talking about the moral issues surrounding AI, all kinds of different topics. I can’t recommend enough Section School. We’ll put links in the show notes. We’ll put links to machine and partners. We’ll put links to personal math, so they can check out your newsletter as well. Thank you again for being here, and I’ve just really enjoyed the conversation.

Greg Shove: Yeah, me too, Kyle. Thank you. And next time we talk, I want to hear about those two guitars that are behind you on the wall. So we’ll do that next time. It was really great to spend time with you. I appreciate it.