June 10, 2025

392 Section CEO Greg Shove on Leading Through AI: Rethinking Business Models, Talent, and Strategy

392 Section CEO Greg Shove on Leading Through AI: Rethinking Business Models, Talent, and Strategy

In this episode of Partnering Leadership, Mahan Tavakoli is joined by Greg Shove, CEO of Section and a serial entrepreneur with a deep track record of leading transformative growth. Shove’s leadership journey includes multiple successful pivots, and in this conversation, he brings a uniquely grounded perspective on how AI is fundamentally changing the role of leaders and the structure of modern organizations. From board-level decision-making to frontline productivity, he doesn’t just speculate—he shares what he’s doing inside his own company to lead through the change.

Greg originally joined Section to turn it from a media startup into a next-gen education company. But when he first used ChatGPT, he knew instantly that business education itself needed to evolve. That insight led to a bold pivot: transforming Section from an online business school into an AI-powered academy focused on accelerating performance and capability at scale. It’s a rare look at what it really takes to lead a high-velocity pivot—one grounded not in hype, but in strategy, execution, and conviction.

Throughout the conversation, Greg challenges conventional thinking on AI adoption, leadership credibility, and the future of knowledge work. He breaks down why many leaders are stuck in experimentation mode—and what it takes to move into actual transformation. CEOs and boards will find his views on performance, upskilling, and AI decision support to be especially compelling and uncomfortably timely.

If you're tired of surface-level conversations about AI and want to understand what the shift actually looks like inside a company, this episode delivers. Whether you're leading a small team or a global enterprise, Greg's insights on using AI as a leadership advantage—not just a tech upgrade—will spark new thinking and bold action.



Actionable Takeaways:

  • You'll learn why Greg believes the greatest leadership returns come not from better execution—but from catching the right wave at the right time.


  • Hear how AI is already matching 90% of the value delivered by human board members—and what that means for your next board meeting.


  • Discover why most corporate training is already obsolete, and how AI can turn learning into personalized, outcome-driven coaching.


  • Hear how Shopify’s CEO linked headcount approvals to AI productivity—and how that kind of thinking will soon become the norm.


  • You'll gain perspective on how to model AI adoption as a leader, and why failing to do so erodes credibility at every level of the organization.


  • Learn Greg’s approach to building AI habits inside leadership teams—and why small, visible systems often matter more than a “transformation plan.”


  • Find out what question every CEO should be asking before making a major decision—and why it might be time to invite AI into the room.


  • Hear why Greg believes business model innovation—not technology—will be the real competitive battleground in the age of AI.


  • Understand the deeper threat AI poses to entry-level jobs and talent pipelines—and why CEOs need to rethink how organizations grow their future leaders.


  • You’ll hear the provocative question Greg uses to challenge his own team—and how it might reshape your own strategy discussions.




Connect with Greg Shove:

Greg Shove Website 

Connect with Mahan Tavakoli:

Mahan Tavakoli Website

Mahan Tavakoli on LinkedIn

Partnering Leadership Website


***DISCLAIMER: Please note that the following AI-generated transcript may not be 100% accurate and could contain misspellings or errors.***

[00:00:00] 

Mahan Tavakoli: Greg shove, welcome to Partnering Leadership. I am thrilled to have you in this conversation with me. 

Greg Shove: Thanks, Mahan. Great to be here. 

Mahan Tavakoli: I can't wait to learn more about you both with respect to why you first got involved in section, then how transitioned it ai.

I think there is so much that my audience can gain from your insights on both the business pivot that you've led, but also the impact of AI on organizations. But before we get to that, Greg would love to know a little bit more about you, whereabouts you grew up, and how your upbringing has helped contribute to who you've become.

Greg Shove: I think my journey behind has always been about getting away from authority and finding opportunity. So I grew up in England and boy British boys private school kind of thing. And. Realized after I graduated, I did not wanna stay in England. It just seemed too rigid and too confined, not very entrepreneurial. I'd watched my [00:01:00] dad go from the mail room, literally the mail room, to the CEO of a public company, and I thought, okay, I want, I wanna work for myself. I want to be the CEO, I wanna be my own boss. I just felt like that'd be hard to do. In England, I went back to Canada where I was actually originally born, but went to college in Canada.

Met my wife in Canada. Also felt after about five years post-college, that was a little more closed than I expected in terms of access to opportunity, access to, networks and, and ways to make money. And so I, I then came to California. I just said, okay, I've gotta find somewhere even more accessible, more opportunity, more open where it didn't matter who you knew or who you didn't know, and frankly more merit based than maybe pedigree based.

So I've always been trying to move away from pedigree and into places where, or into a place where, you know your capabilities, your merit your ambition mattered the most in Silicon Valley to me seemed like the epicenter of that. So I got lucky. I got into school here and was able to stay afterwards on a [00:02:00] student visa and then converted that to a green card and so on.

Now an American citizen and still Canadian though, so no, we're not gonna be the 51st state. We're not for sale. 

Mahan Tavakoli: We aren't gonna go into that conversation, Greg. That will be a separate one. 

Greg Shove: . I couldn't resist. That's all. Sorry.

Mahan Tavakoli: Not at all. Greg. That's part of the reason I start out the conversation with a little bit about where about you grew up, because part of what makes these conversations.

Helpful for people is the insights that are shared. But what makes it enjoyable is when they are walking their dog or ironing their clothes or doing whatever they're doing, driving their car and hearing a little bit fun and banter. It's not just shoving content down people's throats.

Now , about five or so years ago, you got involved with section, I'm very familiar with section, but would love for you to first describe what section was before we talk about how you have led its transition.

Greg Shove: Section was originally actually a media company. So [00:03:00] Section was founded by a guy named Scott Galloway. You might heard of him. Some of your listeners have probably heard of him. Co-host a Pivot and his own podcast, prop G and so on. So Scott had founded Section actually as a business media company and had raised capital and it got started, but you really wasn't seeing a path forward, frankly.

And I've known Scott for 30 years and he, I was visiting New York. He said, listen, if you're in New York, come by the office, meet the team. Help me figure out what to do here. 'cause we've got something, we're good at some things. They're very good at making content. The team was great at making video based content as it should be 'cause it wanted to be a media company.

And so I met the team. I was really impressed with the team. Of course Scott's really brilliant. And I said, listen, Scott, it's a shitty business. It's digital media. It's hard to make a living. It's hard to build a company with a mote. I know a less shitty business, which is education.

It, that's, that could be a great business and it's a worthy business. It's needed. So let's really take our superpower, which is making [00:04:00] video, making really engaging smart video and turn that into lessons and case studies and teach management education, teach the next generation of leaders and managers online.

Obviously online has scale, online, has affordability and accessibility advantages over in-person management training. So that's what we did with section at that moment. And I became CEO and took over the company. And then of course two years ago, we pivoted. 

I first played with Chat GT Plus, and that moment I realized I did not want to be a business school, an online business school.

I really wanted to be an AI academy and a way for people to transform themselves and their teams and their companies  with ai. So that was the pivot that we pulled off a couple years ago. 

Mahan Tavakoli: You looked at the media business and you said Media is not the place to be transition pretty quickly to an education business, and I couldn't agree with you more.

You saw chat GPT and you said, [00:05:00] whoa, education or that type of education is not the place to be. To pivot it again, I am wondering. First of all, how did the team take it? How were you able to lead this organization to the pivot? Because  we might know that we need to pivot, but getting an organization to buy into it and actually do it is a different story.

Greg Shove: Yeah. Mahan is very hard to get organizations to pivot no matter what the size and section. Is small and was small back then pro, probably no more than 25 people. And by the way, I've pivoted so many of my startups. I could write a book about pivoting. My first advice is don't do it. My second advice is if you have to do it, you've gotta do it in a way that you can't go back.

The real sort the number one lesson about pivoting is you and the team need to know there's no going back. If gotta burn that bridge once you've crossed it, so you can't go back to the other side so that it's not easy. And frankly, my team was [00:06:00] skeptical. As any team would be like, is this the CEO's, over caffeinated brain fart from the night before?

Is it, is this something that came to him, as a dream or something, a fevered dream. That's what happens a lot of the time, right? CEOs wake up and they wanna pivot, and how well informed is it? How thoughtful is it? Is it really feasible? Where are we going with the pivot?

Is it gonna be a more valuable place? How bad is it? Where we are and when it's really bad, teams will pivot faster if it's, if you're okay. And we were okay at section. Our business wasn't falling apart. It wasn't growing at the rate I wanted it to grow, though it wasn't creating as much new enterprise values I wanted.

So I'd say the team was somewhat reluctant because what they felt was that we had something that was working, would this really work that much better? And what I had to explain to them and remind them was the only, and remind myself, frankly, the only time I've really made money in Silicon Valley really created outsized return for myself, for investors is when you catch a wave.

[00:07:00] Waves are amazing. Whatever analogy you want to use, whatever growth analogy, I use the wave analogy, California, think about waves, think about surfing. But you can execute in a mediocre way and do well in a wave in terms of a growth. If there's no growth, if your industry is mature, if your category's mature, you have to execute flawlessly.

You have to be like best in class to find growth if there's no growth around you, when there's growth around you. Yeah, get in the wave. You don't have to be the best surfer, you just have to be in that wave. So it's an overused analogy, but I think it's a good one. And listen, I had to persevere.

I had to keep slacking and texting and emailing. Hey, read this, watch this, check this out. Look what I did with chat GPT. I had to basically, be that relentless CEO saying no, we can see a better place here. We can go in this direction. And, it took a while.

I frankly probably didn't do some things I should have done. CEO. I'm impatient. [00:08:00] I expect people to follow my lead especially in a small organization, but. Some people were concerned about their jobs, people were concerned around where are we going, what is the business model? Is this gonna be big or is it like crypto and is this like the metaverse?

We, we all thought those were gonna be big and, nothing much has happened yet. I just felt it was so clear to me, so fundamental that it would change work. It wasn't just a technology, it was a change in how knowledge workers work. And I just realized for me, I'd be using AI for the rest of my life in terms of it'd be a cognitive edge, right?

A cognitive support. So if I wanted it, I assumed others would've as well.

Mahan Tavakoli: It is incredible. Greg, what you just mentioned, I have a client that has about 15, 16 employees and. He is frustrated at the fact that his team isn't really embracing using it. He gives example after example of him using it, asks them begs pleas, [00:09:00] and I have clients that have a little over a thousand employees.

Same challenges where you have. One or two people that have seen the future and are convinced that this is going to transform knowledge work, but everyone else seems to be dragging their feet. So I would love to know two why do you think people are dragging their feet, and what would be your advice or your thoughts to the CEOs of whether the 17% firm or the thousand person firm, how do you actually get people to believe in this transformation and embrace the technology?

Greg Shove: Yeah, that's a great question. Listen, I think there's two primary reasons people are dragging their feet. The first is they're anxious. All of the narrative about AI we get from media and all of all media wants to do is either is freak us out. 'cause that's how we get, that's how they get more clicks, right?

So all the stories about AI and media [00:10:00] are this super intelligence that will take over and put us outta work. And so I think, just think that's the reality. We are and I think it's fair to be anxious. We don't know how this will change how we work. It will take jobs, it will create jobs, it will take part of our jobs, freeing us up to do other things.

But we don't know any of that yet. It's all gonna unfold in the next few years. And I think most employees accept leadership are anxious about it. And maybe even leadership should too, be a little anxious. Maybe we can find better leaders that are younger with AI than these expensive leaders we currently have.

That's one second thing is it's not like software. When we deploy software, it works the same way every time. We can assess do we get value from the software, and if we do, then we keep using it. And if we don't, we stop using it. AI is not like that. It is very irregular or unpredictable in it, in its performance.

Some days it helps us a lot. Other days it fails, right? One day it answers the question really well, and the other, an hour later, five minutes later, it answers the question like, it's an idiot. Ai is this [00:11:00] PhD and summer intern kind of combined in one? It is tireless. I. And it makes a lot of mistakes.

So I think for most people, they don't get enough gain from it and they suffer from the unpredic unpredictability of its performance. And so the people that persevere with AI are the ones that get enough gain from it and learn how to use it in a way to capture the gain. And they tolerate the hallucinations, which is Silicon Valley, jargon for just make shit up.

And AI does that and that's not gonna change anytime soon. It's just, it seems like it's almost inherent in the technology in terms of how it works, that it will hallucinate and we can manage that and the AI vendors will manage that. So my point is there's good reason why people are hesitant. I think that 

Mahan Tavakoli: you can 

Greg Shove: take a two or three different approaches.

There's a lot of sort of heat in the system, in the AI system this past couple weeks. 'cause Toby Luck, who's the CEO of Shopify,  someone leaked, he probably leaked his PR team, probably leaked his memo. He's got 8,000 employees and if you read his memo, which I [00:12:00] have done a several times, it's clear what happened.

He's using AI all the time. He's getting a lot of value from it, and he was getting frustrated. And he's in a talk about an AI first business software companies, if they don't transform themselves with ai, they're gonna be in trouble. That is a business with the highest amount of human capital input, along with consulting businesses.

And any business with human capital input is gonna suffer from deflationary or price pressure in the coming years. Software is gonna become cheaper, consulting services will become cheaper. So Toby's the CEO of a big, very successful software company, and he's like your clients, he's, he was frustrated.

Why are not more people adopting and using AI across the organization, in engineering, in marketing, in sales, and in finance. So he mandated it. He basically said his memo included things like it's gonna be in every performance review. So if you run a large team, you're a client with a thousand employees, you have so many, only so many leverage points and points of influence with [00:13:00] your workforce.

For performance reviews are annual typically, and that's a point of influence. And so at Shopify, it's now in the annual performance review. One of the other things he did was said, if you don't ask for human headcount. More human headcount unless you can prove ai, can't do the job. So again, that's just a very clear sort of policy or stake in the ground around.

You can't come ask for head count unless you can show me that AI can't do it. So that's a mix of carrot and stick maybe. And I'd say that's probably the best approach. A little bit of carrot like, hey, we are gonna be more efficient. We can outsource some of the drudge work to AI and people like that.

And I can tell you from personal experience at section, a lot of the benefit we get is by outsourcing Drudge work to ai, repetitive analysis, repetitive tasks like, creating marketing briefs or marketing emails. AI can do that. The team doesn't save that much time, but they save a little bit of time.

And more importantly they save friction. They're a little bit happier 'cause they got AI to do work that they didn't want to do. That wasn't that interesting. In other cases, AI's going to [00:14:00] do more significant work and eventually it will replace certain jobs. I think that we've just gotta push through.

Leaders have to be consistent here. They ha they have to know this is a three to five year game, not a let's do cool AI stuff, for a couple quarters and then move on. This is a real change to how we work. There is resistance. We've gotta push through, use a little bit of carrot, use a little bit of stick and use it yourself.

I've got no tolerance anymore for leaders who run around talk a big game about AI and don't even use it themselves. So you've gotta model the behavior. I. That you want your teams to to adopt, you have to lead with some authenticity here. And that means you've gotta be using AI yourself as a thought partner.

I think a lot of leaders think, oh, AI is good for the, people who are doing the drudge work. But I, I think big thoughts and I set strategy and I don't need ai. I think if you think big thoughts and set strategy and make mediums to high stakes decisions, you should be using AI every day.

I think it's irresponsible for any leader who's making any decision that sub significance not to be consulting with AI first. [00:15:00] And we consult with coaches and mentors and thought partners and board members, people like you advising others. Also add in AI to that mix. 

Mahan Tavakoli: Couldn't agree with you more, Greg.

It's incredible how few organizations I see consistently use AI at the leadership team level. Including AI in the conversations or at the board level. One of the things I'd love that I would love for you to talk a little more about was your use of AI at the board level. So when you do that, it sets an example.

You mentioned a few things I wanna highlight before then getting your thoughts on using it at the board level and at the senior team level. You said there is anxiety and there is definitely anxiety that needs to be addressed. We are feeling that, but changing any habit takes effort. You can tell me all you want about the value of exercise, health benefits, longevity, [00:16:00] lifespan, whatever, but still doing it every day.

Changing habits is hard for most of us is hard, which is why. So few of us are getting enough exercise or proper diet. Same thing with ai. Even when you move beyond anxiety, making it part of the regular habits takes a certain discipline structure, maybe as you said with Shopify part of the performance review process.

So it takes a lot of effort. Now, you mentioned one other thing, and that was use and consistent effective use at the leadership team level. I love the example you gave me. About using it at the board level, which is outstanding and would love for you to share some of the thoughts of how you use AI as a cognitive partner in those conversations.

Greg Shove: Yeah for sure. Let me first talk about . How do you set these new habits? Some simple things might help. I used to use [00:17:00] a post-it note and all I wrote on it was Ask ai. I just stuck it on my monitor and it literally was there for the last 18 months just to remind myself, 'cause we're not AI native and likely most of your audience are not AI native.

We grew up in a different world, right? We grew up in a browser and Google and getting search results and using traditional software, right? Get, put an input, get an output back. Again, AI doesn't really work that way, so I just used a post-it note. Second thing, if you're a leader, every time someone comes to you and asks for anything or wants to talk to you about something, a hire or a project, or a request for money or whatever it might be, you need to ask as a leader, what does AI think?

And just pause. Don't pause, don't talk. There'll be an awkward silence because they, and then that's okay. You do that for a few weeks, depending on how big your organization is. You do that for a few weeks. Everybody will get the memo. You think they should be asking ai. Here's what I did this year though.

In January I bought a [00:18:00] third monitor, so here at my desktop where I'm talking to you from, I have a third monitor. It's on a vertical horizon. It's got one browser open with three tabs. My three ais, perplexity chat, GP, T, and clo. So it's in my line of sight. It's not directly, it's just off to the side, but I can always see it.

So I can always see that open chat bot encouraging me to, Hey, ask ai, consult with ai. So those are a few things I'd suggest to help people build that habit. Also, love AI on mobile, I converted a little bit of my podcasting listening hours to chatting with chat GPT. So use it using advanced voice mode for chatt.

So if I'm in a car or in the back of an Uber or in, in an airport, I'll just start a conversation with a chat bot and I'll learn that way. Or I'll explore something that's interesting to me, or, something that's on my mind, whether it be at home, like parenting or travel or medical advice, or of course, at the office in terms of in a decision at work.

So those are the things we can do to make it more natural for the kids in [00:19:00] high school right now in college who are being accused of cheating using ai. Of course, they're not, they're learning how to live and work in the age of ai. That's actually what they're doing. They're gonna be native. They'll come into our workforces in a year and they'll be using AI all the time.

They won't have to think about it. So you're right. We the rest of us have to set these habits so it becomes more natural to us, and that's, that includes board members and that includes getting ready for these infrequent, but high stakes decisions and conversations and board meetings are one of the highest stakes, right?

For, in my case, four times a year, two hour meeting. You were viewing the previous quarter, and of course, looking forward to the next quarter, we send typically a 30 to 60 page slide deck to the board, to the humans a couple, three days before the board meeting. It's never I never actually, honestly, I'm lying.

I never get three days before I, it's always like maybe 36 hours to be honest. And if the, and I never set board meetings on [00:20:00] Monday. 'cause if I send it Sunday night, I look like I'm really late. You need to have board meetings Tuesday, Wednesday, pro tip from a seven time CEO. Get your board meetings in the middle of the week and buy yourself some time anyway.

So we send the board deck hopefully a day or two before we also send it to AI at the same time. So we use the same input, the same content, and we ask AI to play the role of a board member. And we ask different ais 'cause we want to compare their performance and see how they do. Then what we do is we don't record, we don't record board meetings using a note taker.

That's just for governance and legal reasons. Our general counsel, I think every general counsel says, don't use, don't use AI note takers, but we do have someone in the board meeting, my chief of staff who takes faithful notes, takes really good notes of what the humans say. And then we compare after the board meeting, we compare the two.

And what's stunning almost from day one, we started doing this 18 months ago. We just did it recently. We had a board meeting at the end of April, almost from day one, 18 months ago. Ai, the best ai, which has been [00:21:00] clawed from anthropic, has performed at the level of 89 to 90% of the humans actually chat.

GPT jumped into the top of the leaderboard this past month. So with 90, 91%, meaning 90% of what the humans told us, that AI had already told us in our conversations with AI before the board meeting.

Mahan Tavakoli: You have a great board of directors. They have lots of experience, lots of insights, and by engaging with ai, Claude and GPT at different levels. I agree with you in some respects, Claude seems to be doing better, but both are coming. Way above 80% of the quality of what those very smart humans are contributing to you at that board meeting.

That is absolutely incredible. And that's why I think it's extreme negligence for us as the [00:22:00] executives, board members, board chairs, CEOs not to do that. 

Greg Shove: Yeah, I would agree. And especially if you're a first time or second time, CEO, I've been around the track a few times, so it maybe at some board meetings I can get away with less preparation.

But if you're doing this for the first or second time, if you're early in your career and you're in these high stakes conversations. High stakes meetings. Why would you not have prepared and role played beforehand? Like again, I think it's irresponsible not to have done that. It takes a few seconds.

It's free. It's virtually free. And if you know how to prompt, which is not rocket science, you can really push the AI to play these different personas. So we ask the ai, play an aggressive board member, play a venture capitalist who'd rather not be in this board meeting. He'd rather be golfing.

What would he be saying or she be saying, right? You can really have fun with this as well and get your AI to push you. By the way, I do the same with the board. When I send the board deck before the board meeting, I give them the prompts they should use [00:23:00] to prepare for the meeting with their AI to challenge me.

And my whole goal is both of us should be raising our game. So when we come to the board meeting, we're just that much better prepared. We get to the issues faster. We, we get to the stuff that really matters. A lot of board meetings are updates, quite frankly. We could talk about board meetings later.

Most of 'em are a waste of time because they end up just being updates. You wanna get through that faster and get to the real stuff that you wanna talk about and get advice from your board members on. And by the way, board members offer value that, that ai doesn't, at least yet, right?

Board members write checks, they fund companies, board members have networks and connections that you can leverage. Board members can recommend someone to hire, things like that. So I want more of that from my human board, basic feedback on my go-to market strategy. Frankly, I can get it from AI and probably better, faster, with less friction.

I. And no primadonnas on the ai. I got primadonna board members, I gotta deal with them. 

Mahan Tavakoli: [00:24:00] What outstanding insights. A couple of things I wanted to reflect on there, Greg. First of all Warren Berger and I'd love his more beautiful question, power of questioning. You are asking the AI and prompting the board members to ask the AI some beautiful questions.

Part of the challenge I've seen with some CEOs and executives is that they ask pretty simplistic questions to the AI and then they're disappointed in the responses that they get. So it's not the art of prompting. , You are not copy and pasting some weird prompt that social media promoter is talking about, but you are reflecting on deeper level questions that will get deeper level responses.

So I love that. And that is a. Outstanding point right there. Now, you mentioned board members bring additional value, so for example, whether it was Claude or GPT in the [00:25:00] latest version was coming up to 90% of the contribution of the board members, what were the insights? Obviously in addition to financial contributions, connections, what are the types of insights that you are able to get from board members that you are not getting right now from the LLMs?

Greg Shove: I think it's a combination of you're not getting them or getting them from a human that you respect and that has a lot of experience, is gonna have more weight with you as the CEO or leader than getting it from AI at this moment. And how much do we trust ai? How much do we think it's just a token prediction of the next word versus some sort of, reason judgment with humans?

You're getting reason judgment, you're getting opinion and you're getting it in the moment at context relevant. So I think where the AI fails often is that Im immediacy of the context. For example, right now we're in a, we're in or about to be in a recession. I board members [00:26:00] know that board members are in other board meetings.

They can see what's going on. So they can bring that perspective and really offer, as for me as a thought partner, what should we be doing in this moment? Should we be going more aggressively? Like when others pull back? Recessions usually mean people pull back. That's a time, often to play offense, right?

Counterintuitively, that can be a good time to try to grow. And so that, that's the kind of conversation you can probably have with a good board in this moment. You can't yet have that with ai. It doesn't have that immediacy and relevancy of context to the macroeconomic environment, to the competitive situation and so on.

So that's, that's where the humans are gonna really matter. And it's their judgment and their experience in this moment where I think we, we wanna rely on that. We don't want their advice on how to optimize our pricing. Ag again, that's just gonna be five opinions from a board.

I'm gonna get pricing strategy advice from ai from now on. It's going to be better. One more thing, Mahan, you said something really [00:27:00] important around prompting is just asking good questions. I think that many leaders and entrepreneurs aren't.

Prepared to ask questions that they don't want the answer to. The advice I give every entrepreneur with or without ai, really good entrepreneurs, great entrepreneurs learn that the questions that make them uncomfortable, the questions that they don't want to hear the answer to the questions where we're, they're not sure what the answer is going to be.

Those are the questions to ask, I think really in life, not just in work. I think in life, those questions, mahan have the greatest opportunity for development. They have the greatest opportunity for, learning insight moving forward. Ask AI those questions. The questions you don't want to hear the answer to ask them about ask AI about unintended consequences.

Ask AI what could go right, but also ask AI what could go wrong. 

Mahan Tavakoli: One of the interesting things I find, Greg, as I spend a ton of [00:28:00] time more with GPT than Claude, but I also love CLO for certain things, is that. If I had asked that same question to a human, I might have not been offended, but emotionally it's a little bit different.

If a human gives me that same feedback, but I don't get offended whatever chat GPT says, I don't get offended. Now if I don't push it, whether GPT or Claude, the latest iteration of GPT was horrible at this, it always continually tells me how brilliant I am. And when I disagree with it, it says, oh, what a brilliant disagreement with what I just said.

Yeah, absolutely. So we go back and forth. So it does require a deeper level of thinking and questioning, but I am much more receptive when I ask better questions. I am much more receptive to what I read or hear when I use the chat interface from chat GPT or Claude than I. [00:29:00] If another human being was giving me that feedback, I don't know what it is about it, but at least I find myself more.

I think 

Greg Shove: it's what you said. It's a really powerful insight. We're not invested we want the answer, but with ai, we're not invested in that relationship and we're not invested in what that person thinks of me. Or, and, it could be a spouse, a partner a board member, a co-founder. It's hard to disagree with those people.

It's hard to to hear it sometimes what they need to say. But you're right. I think it is easier to hear that at times from ai. It's easy to dismiss it too with ai and that it's not coming from someone maybe you respect, so to speak. So there's that balance. We're gonna learn how to interact with our ais in the coming years.

We're gonna learn as AI gets memory. Think about, a year or two from now, AI will know the questions we're not asking. AI will know, we don't ask tough questions and AI will prompt us to ask those tough questions. 'cause AI will have a memory of us. 'cause it will be working with us now for a couple, three years and be able to really adjust its [00:30:00] style to what we need.

So I, I just think we're just beginning here and scratching the surface of the capabilities of these systems. This idea that we're even having to ask questions. Google has in prototype available to developers this idea of screen share for Gemini 2.5 Pro, where you just basically turn on screen sharing with Gemini and then you can have a conversation with the AI about what you're working on.

'cause it sees what you're working on. It's clunky. It's not available to consumers yet, really. But when you play with it a bit as I have, you really begin to see where this is going. Expanded memory, working alongside you, watching what you do, interrupting you potentially, and saying, Hey, you're off track here.

You should do this instead. These are gonna be very powerful systems. And so we, I think we're gonna want them in our lives and we'll learn how to manage them and maintain our humanness. I hope , we learn how to do that, , in the [00:31:00] coming years. 

Mahan Tavakoli: It will be hard to both keep our humanness and take advantage of the opportunities if we are not playing around with it and spending significant amount of effort, time, mental energy as you are doing now, one of the things I want to circle back to is you have been transitioning section . But as I think about whether it's the Coursera's of the world or Udemy of the world, or almost any training organization, I think that entire learning space is going to transition drastically and we as executives and individuals need to start focusing on learning differently.

So would love to know your thoughts on that and therefore how your positioning section to take advantage of that wave. 

Greg Shove: Sure. I think learning goes away basically and becomes coaching. I think this is the idea of sitting down and watching videos, watching lectures online or [00:32:00] asynchronously. Sure. Some US will keep doing that, but when you think about it, it's a really broken product.

It's a broken product because you have sort of one size fits all training. The promise of AI is that it's immediately personalized to who you are. The job you're in, the, company you work in, the country, you you live in and work in. It's amazing. It's the first time you experience real AI based or AI powered learning, where the AI is driving and creating the learning experience real time.

It's magical. 'cause you all of a sudden see a different version of learning. And I think it's more like coaching. The example I always use is this idea of HR always wants to teach critical conversations or how to have difficult conversations, right? And that everybody's got courses in their LMS, that their company learning system or LinkedIn learning, or Udemy, as you said, called had difficult conversation.

What a dumb way in today's world to learn how to have a difficult [00:33:00] conversation. Watch a 30 minute video. Give me a break. It's a joke. What you're gonna do is have a role play with your ai. You can do it today. It doesn't cost anything. You tell AI to play the role, the person that you're gonna have the difficult conversation with.

You play the role that you're in. You're the manager, leader, whatever it is, have the conversation, have it several times. Have AI help you, guide that conversation, switch the roles you play, the employee. Let's say if it's a boss employee relationship, have the ai, play the boss role and see what it feels like to be on the other side of the conversation and actually develop some empathy.

So this is how we're going to learn. We're not gonna learn. We're really, we're gonna be coached by our ais in the moment based on what we need. And at some point, and this is, I don't think that far away, it might sound fantastical, but we're starting again. We're starting to see this happening. AI will know it's on our calendar.

So AI is gonna alert us five days before saying, I see you have a performance review with this person in five days on your calendar. [00:34:00] Do you need to get ready for that? And do you want me to help you prepare? That's absolutely how I want my AI working for me. So when I show up for that difficult conversation, I'm gonna be the best I can be.

The best human I can be. Yeah. I think if I was sitting on a mountain of of video library, asynchronous video like Udemy and Coursera, I think those companies, I short them all quite frankly, Duolingo just announced that they're gonna be AI first. One of the things they also announced, they got a lot of heat for this on TikTok and social media around, they're not gonna use contractors, they're gonna use ai.

They're definitely gonna, they plan to shrink their workforce, but they also, released about 150 new courses at once. So they've clearly been using AI to generate these new learning experiences much faster and efficiently than they could have before. And frankly, that's what we're seeing in section.

We built a platform called pro AI's AI powered, and it teaches you ai. So I expect in a couple years we will not be making any more AI courses at section. I hope we [00:35:00] won't be. I don't want to be teaching people by having them sit on Zoom for an hour and a half, or sit in front of a screen and watch a video.

I don't think that's the best way now that we live in the age of ai, now that we live in the age of ai, I want our students our customers using profit ai. 'cause as soon as profit AI knows who you are and knows where you live, knows what company you work for and what job you're in, it can start to teach you in a very personalized and much more efficient way.

It's just gonna be better. We're all gonna learn this way. 

Mahan Tavakoli: I would love to find out a little bit more about Pro ai. Greg. Before that wanted to give you a quick example I've been playing around with notebook LM quite a bit and one of the things I work with a lot of my CEOs on is storytelling.

And I've had a bunch of great guests on the podcast on storytelling. Paul Smith lead with a story and stories. Great leaders tell Tamson Webster , lots of them. So what I did is I entered [00:36:00] all of the storytelling episodes into Notebook lm, where the two hosts have the conversation, but the most important part is not that, the most important part is, I can interrupt, as I'm sure you've seen, I can ask specific questions to my needs. So in essence, I've made all of these people, my coaches, and they can be anyone's coaches in teaching them storytelling. So there is a lot of power to this. Now, what I wonder is, you mentioned pro ai, in what way is pro AI different or better than doing something like this, whether with Notebook LM or GPT at this point?

Greg Shove: I think it's better in that it's just been tuned for that use case. We have a point of view on how to use ai. We have frameworks that we use and essentially mental models. And so we've trained pro AI on our content, on our sort of frameworks and mental models.

[00:37:00] And then it leverages the power of GPT, or, and I think Notebook, l LM is a great example of something that is basically an off the shelf tool that's essentially free and can create, a pretty customized learning experience. As you said, you can interrupt with it and have a conversation with it and really have your storytelling coach in your pocket.

So yeah, pro AI has just been tuned for teaching people ai. We also built it so companies could customize it. So if you think about AI training inside of organizations, every organization has different AI policies and, different points of view around where AI is to be used. What is brand safe ai?

So we wanted an enterprise grade solution where our customers could deploy pro AI in a somewhat customized way for them, which you can get something similar from GPT in terms of doing it yourself, but if you want to establish a kind of a standard and a set of policies around AI inside of an organization, you're gonna need something that's a little more tailored to your needs.

But listen a lot of this can be done we call natively on profit on GPT directly or claw [00:38:00] directly, but I do think there's this need for people call 'em AI wrappers or AI applications that are tuned to the use case. I use something called Mind Tripp for my travel. I could do some of what Mind Tripp does on chat GPT directly in terms of travel planning.

But Mind Tripp's done a great job of offering kind of a travel UI and a mapping capability and so on. So I do think we'll see these amazing applications built on top of these models. And in fact, I would argue that chat GPT is in fact the first AI application. It's not the model. Obviously the model is or many models are underneath it, but it'll be the first billion user AI application.

Sometime this summer. When you think about that, it's just pretty staggering that they're around at 700, 800 million users already. That is the free version. But still consumers and small business love ai. That's what a billion, that's what that billion number tells me. That the world loves ai.

It's still slow in terms of getting into [00:39:00] our companies, but I think like a lot of software revolutions, they start with consumers. They start with small business and then they eventually come into larger organizations. 

Mahan Tavakoli: And I see it leveling the field in so many respects

so would love to know your thoughts, Greg, with respect to the impact of this on knowledge work. You posted about on LinkedIn as well. I love your perspective on it. I absolutely dislike the meme that went around and was popular for a while. You won't lose your job to ai.

You will lose your job to someone who uses ai. Absolutely. We will all use ai. But some people will lose their jobs to ai.  So would love to know your thoughts on the impact of this on knowledge work and organizations built and based on knowledge work.

Greg Shove: Yeah, there are so many impacts. I'll try to go fast and just touch on a few.  of the things we've learned with AI, quite frankly, is a lot of knowledge work is [00:40:00] repetitive. Output based work, , we're creating artifacts of work, slide decks, memos, financial analysis that's represented in some sort of Google sheet or Excel spreadsheet or, we're moving data or pushing data around and reformatting it and representing it, quite frankly, outputs.

And I really think that one impact of AI is, it will, it is devaluing outputs dramatically. Because AI can start to create those outputs itself with some human, currently, some human intervention and direction and presumably soon without, in terms of some agents that will hopefully work that means outcomes will matter that much more.

I think the knowledge workforce, those who stay in it and perform well in it, will really align their work to outcomes, business outcomes of some sort, whether it be marketing, sales and so on. So I just think this idea of highlighting it will shine a bright light on lower value outputs. And if you're in a job where you do a lot of relatively lower value outputs, they might seem high value to you, but are they really high [00:41:00] value?

I think that's gonna be a, frankly, a real challenge. I think another significant impact because of what you just said, is the deflationary impact on knowledge work. It will be less valuable. I. So anybody who makes a living, making a product or service where the primary cost of goods, the primary input is human capital, I think will face significant deflationary pressure over the next decade.

And this is really something I encourage your audience to reflect on in the coming year. I don't think it's happening overnight. I think in fact for software companies and consulting businesses that for many who sell time, AI will help in the short term. Make us more productive, allow us to handle more clients, allow us to create more outputs and charge for them.

So I think in the short term, I think consulting businesses, as an example, will benefit from ai. I think in the medium long term, it's very different outcome, a very different scenario. I think [00:42:00] it's gonna be deflationary. I think that lawyers are appropriately freaked out about, what is it currently a time and materials model moving to a outcome-based model, which is, something that's really you're charging for the completed work or even the client outcome in some respects.

So I think that is deflationary. And so I really think, and when you think about the best, greatest businesses ever built, they take. Product or technology innovation, and they bring a business model innovation. It's not obvious right away, they emerge later. But the business model innovations are really more important and more transformative to the industry than the technology.

'cause others can copy and chase you with the technology. But if you're the one that disrupts the incumbents with the business model change the Airbnb, the Uber, the AWS, whatever it is, think about those, how transformative the business model changes and the incumbents can't react fast enough. So I do want us all, [00:43:00] especially if we're in businesses that have high human capital inputs to, to contemplate this.

And what would two guys or a guy and a gal, an AI agent and a dog, what if they started in your industry, if they were a competitor to you tomorrow or next year, how would you react? Or what would you do if you were them? You'd think about as, I'd wanna make the product better, but I'm gonna want to innovate on the business model if I'm AI native.

'cause I'll have natural advantages, and that's gonna be really hard for incumbents. This is what, this is the next battleground I think we should be thinking about, if you will. It's, it is a technology disruption today. It's about to become a business model disruption. And I just want us all contemplating that and beginning to think about how we're gonna react.

Mahan Tavakoli: I love that challenge you threw down for the listeners, Greg, about the business model disruption. And it is. In my view, the most significant business model disruption that we have definitely faced in our lifetimes [00:44:00] and potentially in generations. So it's not just impacting one industry or one sector.

The potential for business model disruption in this case is across the board. And if people aren't really reflecting on it, they're gonna be hit a few years from now and be surprised with the implications. 

Greg Shove: Yeah., And I wanna give you a real life example too and also I think it's a good insight into entrepreneurship.

So we launched Profit ai, obviously as essentially a successor to our current AI academy, which is a course and workshop based academy, a lot like Udemy or Coursera, and so on. And we are essentially replacing our current product line with a new product line. But here's the reality about the new product line.

Pro ai, my cost to train someone on pro ai, which is my AI cost, my in once I built the application. My real cost per user, my per user cost is my AI cost, right? Also known as my inference cost. So for someone to be trained using pro [00:45:00] ai, it takes about an hour of conversations with pro AI to take someone who is not proficient and turn them into essentially an advanced AI user.

So that's fantastic. Very time efficient. Hopefully it's a fun and engaging experience for the student. For the employee, my cost is a dollar, my inference cost is a dollar. So by the way. We charge $750 a year for unlimited access to the AI Academy. So my current product, and we discount that for sure, so the net selling price to to individuals, to consumers probably closer to five, 600 right annually for unlimited access to this amazing AI academy.

It's great. And which includes live workshops, includes office hours, it has other things that profit AI does not. But still the core of that is access to an AI curriculum. Profit AI can deliver a lot of that value in terms of the curriculum in a different way. And my cost inference cost is a dollar.[00:46:00] 

So if I was an AI native company, if I'm not, I'm an incumbent becoming an AI native company. If I was an AI native company, if I was an entrepreneur today launching profit ai, I would not charge at seven 50 bucks a year for that, I charge 10 or 20 and have great margins, and that would be highly disruptive, which is what I'm gonna do.

To myself and everybody else, so Coursera and so on, watch out. 'cause AI learning experiences are not gonna cost $49 a month or $20 a month, which are the current pricing models of these learning platforms. That's not gonna work. That business model is about to be blown up. 

Mahan Tavakoli: Good for you, Greg. What you just mentioned, I wanted to underline how courageous that is and how hard it is

when you look at a lot of organizations that have been disrupted in different industries over the years as a result of technology, more will be as a [00:47:00] result of ai. It's not that they didn't know. They were going to lose their margins and the potential that they had. It said it is very painful to do it to yourself.

You're hoping that no one else does it and hold on as long as you can. So it takes a lot of courage to actually disrupt yourself

Greg Shove: yeah, absolutely. , I think it's the hardest thing to do in business for sure. If you've got something to protect and it's generating cash flow and, paying the bills and employing people and paying your own bills if you own the business, it's so hard.

But you, at some point, you will not have a choice. So there, there's a judgment there. When is that point? When is this disruption coming? How quickly is it coming? Where and so on. I don't think there's one right answer here in terms of you, you have to Detroit yourself tomorrow. Maybe you can wait two or three years.

But it feels like to me, again, with [00:48:00] capital human capital intensive businesses some of these disruptions are gonna happen quite quickly and we're beginning to see that, right? Meaning we're beginning to see examples. Chegg is one of those online learning companies. It's essentially it's for sale.

It's close to bankruptcy. I think at this point I think Udemy's for Udemy of Coursera, I think Udemy's for sale with a new CEO I think basically the investors were like, okay, we're done here. We, we need to find a home for this company.

And that was a fast growing went public and really viable business a few years ago. And now it's not. It'll come over time, I think to, to many sectors. I think consulting is one to me that feels like who's gonna build the McKinsey of AI or the ai, the AI enabled consulting firms.

You won't need to pay $500,000 to talk to a McKinsey partner not in the future. 

Mahan Tavakoli: As organizations do that, there's one other aspect of it, Greg, I would love to get your thoughts on  in that when I'm interacting with AI [00:49:00] and using it in coaching the CEOs or leadership teams, the questions that I ask come from a depth of experience.

And I say that with all modesty, but. Understanding that someone right out of school, even right outta business school, will not be able to ask the kind of questions that I ask, therefore get the answers that I get. And what I have seen is that AI enables fewer individuals to do a lot more and be very effective, including with the law firms that you were giving the example of,, you still will need very smart attorneys experienced, but those attorneys can get a heck of a lot more work done, a lot more efficiently with their AI agents supporting them, which is outstanding. For those folks on the mountaintop, what happens to everyone else?  How do people gain the experience and the insight  to be able to [00:50:00] then have their AI agents do the work for them?

Greg Shove: It's a great question, and the honest answer is, I don't know.  I think about this a lot. I've got. Young kid young kids, meaning they're early in their careers in the knowledge workforce. I've got one who just went to work at LinkedIn in one of those typical, starter jobs inside sales.

And you can see those jobs going away. I. Relatively quickly. And those are the jobs we use. Paralegals inside sales, drafting press releases on the corporate communications team or the PR agency, buying media, media buyers. It used to be very manual job. And it was a way to learn the business, learn advertising in terms of, planning campaigns, right?

Media campaigns, all those jobs feel like to me, they're going away. I don't know how we onboard people into the knowledge economy, quite frankly. It's gonna be something we need to figure out. Because we use college as a finishing school. 'cause we don't wanna send people into the workforce at the age of 18.

So we need to mature them, especially young men. [00:51:00] So we need to, we use college in that way, and then we use these starter jobs also as another way to mature them and give them some basics, basic business skills, communication skills, and so on. And presumably they're learning about an industry or a type of job, right?

That they can then get better and better at. So again, I don't have the answer. How I think about it and what I tell my kids is, be in the top half of your class in any team that you're on in the next few years. You really don't have a choice. Top half, top quarter, sure. Be as high as you can. Do not be in the bottom half of your team.

I just think that's just the way we have to think about knowledge work going forward. Teams will be smaller and what I say to this section, and I think most CEOs don't know what to say, so they say nothing, which is why anxiety is high. And I just don't, I don't think it's, again, a good way to lead.

I think we need leaders to talk about AI in a way that acknowledges the risk to jobs. Here's what I say to section, and here's what I encourage other leaders to say. In a year, some of our teams will [00:52:00] be the same size and doing more work 'cause they're AI enabled. Some of our teams will be smaller and doing the same or maybe even more work.

Some of the teams will be bigger. If there is a team that if you add AI to the team is that much more productive. You want more of those people. Sales is a good example. I always want more revenue, and if AI makes my sales team that much more productive, I'm not gonna lay off. I'm not gonna lay off salespeople, I'm gonna add salespeople.

So I just think it's, I think the honest sort of answer is, guys, we don't know. I think most teams will be a little bit smaller, some will be the same size and some will be bigger. And frankly, we have to approach this as an experiment in terms of. See how this unfolds. And as a minimum, be upskilling everybody on ai.

So if there isn't a role for them in your team in a year or your company, they are AI enabled and so they can get out there and, and apply those, their skills and their capabilities somewhere else. I just think we, that's the moment we're in right now. I wish there was a better answer.

It's the [00:53:00] same for schools I talk to. I talk to teachers and professors and school administrators every month and they ask me something similar, which is how will kids learn to think and how will kids learn in the future? And my answer is, I don't know. But putting your head in the sand and pretending that, we're not gonna deal with AI in the classroom or in the school makes no sense to me.

I think you should approach this as an experiment between you, the school the administration, the teachers, the parents. And the kids and go in it. Go in it to that experiment, eyes wide open, talk about it openly with parents and students. Otherwise you have what you have now, which is kids are cheating and they're getting expelled or getting sanctioned and things like this.

It makes no sense. I. We have to acknowledge there is no playbook yet, but it that should not slow us down. Beijing is mandated eight hours of training for kids in the Beijing school district, starting at age six. So we don't know how that's gonna work, but it seems to me a better choice than not [00:54:00] doing anything.

Mahan Tavakoli: Anything. Yeah, and it requires what you have said and what you have done, Greg, the willingness to be humble enough to say, I don't know. However, along with that, the willingness to learn and experiment along the way,  no one has the clarity to know whether it is with schooling or knowledge work, where things will be five years from now.

 But we do know that AI will play a significant role in it. Therefore, we might as well learn experiments and be open to it rather than try to close up. Whether the schooling or I know of organizations where they say you cannot use ai and people are using it on their personal digital devices. So experimentation and that humility has to go along with the learning that you talk about.

Greg Shove: think that's right. We just can't overinvest in these predictions think about some of the [00:55:00] early predictions on ai. For example, autonomous driving a couple years ago looked like it was dead, right? Crews had failed and GM was closing it down and now I go to San Francisco and there are Waymo's everywhere.

There are cars with no drivers all over the city. And I think I, I saw recently that they've taken 16% Waymo's taken 16% market share from Uber and Lyft in just the past year. The other prediction that everybody read about a couple of three, four years ago was there'll be no radiologists anymore.

All, all X-rays would be read by ai. That, that hasn't happened. So I think it just shows we can't predict this stuff. There's, we're, it's gonna unfold in ways that we can't imagine with a lot of good consequences and a bunch of unintended and not so good consequences. And we just have to step up and do our best, to, to work through it.

I think you're right. There's a level of courage, there's a level of resilience. There's a level of pragmatism. Let's not oversell it. Let's not overhype it. Let's put it to work and see where it really does add value. And be ready. 

Mahan Tavakoli: [00:56:00] And I appreciate the way that you have put it to work and the many examples you gave Greg, both with respect to what you're offering through section and the reinvention of section.

What a perfect example of disrupting your own organization and how you are thinking about providing value and constantly changing  in addition to how. Leaders CEOs and board members can engage with AI in their organizations and then seeing the implications and getting the organization using it.

So many great insights, . Where can the audience find out more about you, about section and follow your work? Greg? 

Greg Shove: Probably the best place to start is greg shove.com, G-R-E-G-S-H-O-V e.com. If you go there, everything else  links out from there.

Mahan Tavakoli: Greg, what a wonderful opportunity to learn more from you. And I love the fact that these are not theoretical insights about AI in [00:57:00] organizations. You are experimenting, you are doing it, you are learning along. So thank you so much for this conversation, Greg Shield. 

Greg Shove: Thank you for inviting me. I had a great time.