Make It Happen Mondays Podcast

AI Is Changing Sales How Salespeople Can Stay Valuable in 2026 with Tim Sanders

September 28, 2026

This episode of Make It Happen Mondays features a longtime sales and innovation leader who explains how large language models like ChatGPT and Claude are reshaping how B2B buyers build shortlists before ever talking to a salesperson. The conversation covers why BDRs have become critical intelligence gatherers for marketing teams, why closing deals is now an act of helping indecisive buyers move forward, and how salespeople can build lasting value by developing domain expertise AI cannot replicate. It also traces the guest's personal background, from a difficult childhood in special education to early work with Mark Cuban, and connects those lessons to how sales professionals should adapt in 2026.

What you can take from it

AI and buyer behavior in B2B salesThe evolving role of BDRs and SDRsSales fundamentals in an AI-driven worldPersonal resilience and mindset in sales careersAnswer engine optimization and AI search

Questions this episode answers

How is AI changing the way B2B buyers choose software?

Many buyers now start their research inside tools like ChatGPT or Gemini and receive a short list of recommended vendors before contacting anyone. Because a large share of buyers end up purchasing from that AI-generated shortlist, companies need to understand the prompts buyers use so they can optimize their content and third-party evidence to appear in those results.

Why are BDRs becoming more important instead of less important because of AI?

BDRs are often the first people to hear directly from a prospect which AI tool referred them and what exact prompt was used, information that marketing teams cannot get any other way. Capturing that intelligence lets companies see how AI search is actually influencing purchases and adjust their content strategy, making the BDR role central to marketing rather than just a meeting-booking function.

Will AI replace entry-level sales jobs and how should new salespeople prepare?

The episode argues that repetitive early-career sales tasks like scripted cold calling are likely to be automated, but judgment and domain expertise remain uniquely human advantages. New salespeople are encouraged to experiment, build their own tools or systems, get real feedback, and develop deep knowledge of their customers and industry rather than relying on a slow, traditional training path.

Is closing a sale still necessary if buyers can get answers from AI?

Yes, because easy access to AI research can leave buyers stuck comparing endless options rather than actually deciding. A skilled salesperson still adds value by creating urgency, guiding the buyer through a clear decision process, and helping them commit to a choice instead of continuing to research indefinitely.

Read the full transcript

A conversation between John Barrows and his guest, recorded September 28, 2026. This transcript is machine-generated and will contain errors. Where it disagrees with the audio, the audio is right.

Hey, everyone, welcome back to Make It Happen Mondays, where we talk about sales, business, entrepreneurship, personal growth, mental health, and everything in between with guests who I truly respect and I think make a positive impact on the world around us. Today's guest is Tim Sanders. He's the chief innovation officer at G2. He's written five books, including Love is the Killer App, and he was one of Mark Cuban's early salespeople at Broadcast.com back when the internet streaming didn't even work yet. And he's 64 years old now and probably more fired up about AI than anyone I've talked to this year. But here's the part that really got me. Tim spent first grade through sixth grade in special education in New Mexico in the late 60s.

No teachers, no real curriculum, and the only way out was to finish everything that was on the wall. So he taught himself, basically. And that skill, learned on his own with nobody teaching him, is the exact thing he's using right now to figure out how ChatGPT and Claude decide which software companies to make the shortlist. We get into his grandmother, Billy, and the seven principles she raised him on, the Mark Cuban, did you pick up a check today era, and then we go deep into the future of the sales profession. His argument is that BDRs are now the most important player in the marketing team, not because of the meetings they book, but because of the intelligence they capture. He has a $100 spiff story that'll change the way you think about inbound.

We also get into why closing someone is a favor in a world of infinite AI answers, why the B2B buyer is about to get very technical again, and why he told his own son, who's in cybersecurity sales, about how to build your own systems instead of accepting the ones you're already given. So I hope you enjoy this conversation as much as I did. Let's make it happen. Tim Sanders, welcome to the Make It Happen Monday podcast, my friend. How are you today? I'm doing better hanging out with you, John. Nice to see you. Good to see you, too, man. We were talking right before we got on. It's been a minute. It was before COVID. It was when we were at Upwork, and I remember doing some fun work with that team over there.

That was a good time, and I'm glad to reconnect here now that you're at G2. So you're down. Man, you've got a lot going on right now. You are, like, neck deep in the world of AI with the insights and the research and everything else, and we're going to get to this because I have some really specific questions for you about the future of sales, quite frankly, the future of the sales professional, not necessarily sales because there's the Terminator stuff that everybody talks about, but I think there's a really unique opportunity for the right type of sales rep to thrive in this environment, and I want to get to that. But before we do that, my friend, you have a very interesting background that I have to talk about.

You've got books, you've got Mark Cuban, you've got all sorts of different cool experiences that you've been through. So can we back up a little bit? I've got to hear about your, was it your grandmother? I've got to hear about your grandmother and the influence that she had and the massive optimism and then the book with the seven principles. I've got to hear that. So walk us through kind of your grown-up and some of the influences that made you, you, and then let's get into kind of the stuff with G2 and the reports and all that fun stuff. But I really want to kind of unpack because I think there's a lot of learning lessons along, especially your sideways years and everything else here. So talk us through some of that.

Oh, thank you. Thank you. Thank you. So I was born in Lubbock, Texas. I was raised in Eastern New Mexico. My grandmother, Billie, adopted me at the age of four. And I was, I don't want to say I was a problem child, but let's just say that I survived about six weeks, uh, in, in, in, uh, first grade before they put me in special education. I was in special education, uh, until the end of my calendar sixth grade year. I had finished high school curriculum by that time because special ed back in the late sixties, it was a study as you go. So they basically had all the stuff that went from like, you know, K through 12 and you just kind of like, you finish the thing, you do the next thing. So they ended up, you know, I guess, I guess the choice was parole school or general population.

They put me into general population and my grandmother, you know, raised me to understand how to be confident and successful, even when you're different. So I guess in, in today's more modern language, you would say I'm neuro spicy, but she taught me, um, how to get off the short bus, make friends and, and, and figure it out. And I was raised, uh, by principles around what it takes to be confident by design, not by outcome, which was fascinating. And, and she came through this belief, not just because of her religious upbringing, but because of influences like Napoleon Hill, who wrote a book called think and grow rich based on some super successful people. He interviewed the magic of believing as a man thinketh, um, uh, psycho cybernetics by Maxwell Maltz, fantastic book.

Your mind is a machine. You point it in a particular direction. And then of course, Dale Carnegie's work, Dr. Norman Vincent Peale's work. So she was steeped in all of that, but she passed it along to me. And I got to say, John, it like really helped. It helped me gain the confidence to fit in with the kids. It helped me gain the confidence to figure out what it is I wanted to do. I wanted to be on the speech and debate team. I was very successful with that. Um, and it gave me confidence throughout my entire adult life, inclusive of when, you know, as you mentioned before in the opening, I went through a bad decade when I had a personal tragedy and I managed to dig my way out. And so some of those principles she taught me, the most important principle, number one, boy, is it relevant today?

Feed your mind, good stuff. You know, she taught me that the things you put into your head eventually become your thoughts, your beliefs, and your actions and your consequences. So I edit heavily. I created a mastermind group of sources that I trusted and relied on. She taught me not to read the newspaper. And she taught me to be very careful about the people that I take on as friends because they are my conversational circle. And, um, it was very helpful. And, but she also taught me, you know, the other one and that's prepare thyself. So it's not that you stick your head in the sand and you're not aware of the world. It's that you find the things you need to get smart at and you get brilliant at those things.

And you don't need to know everything that's going on in the world, but the things you need to know, you need to know better than the next person because, because life is competitive. Um, she taught me to exercise my gratitude muscle every day. She taught me it's a muscle, not a feeling. If it was a feeling, we'd feel it all the time. It's a muscle and it gets flabby and you got to exercise it. It's, it's a real anecdote to scarcity thinking, um, which for those of you that know Dr. Stephen Covey, you know, this idea of not enough to go around. She taught me to give, to be rich, which I thought was really important. Um, that, that structured charity, um, gives a person a sense of abundance, gives a person a sense of wealth.

And she taught me there's two types of rich in the world. There's money rich and there's rich in spirit. And the second one, no one can take away from you. Um, she taught me promise made, promise kept. She explained to me that my reputation would come down more to the things I finished as the first impressions that I made. And so she really taught me like, be a person of execution, be a person who writes down everything you say you're going to do and does the thing, um, punish yourself when you miss deadlines and, and fail people, um, and you'll build more character. And those are some of the things, uh, that she taught me that helped make me a very successful person, um, in her eyes, at least.

Um, she was, uh, when she passed away, she passed away in 2012, right when the book was coming out, by the way. And, uh, she was very excited to see that book and, and, and know that, um, uh, as, as one of our family members said that she'd been commercialized, memorialized, um, forever in that book. And, and I just think there's a lot there. And so for, for the people that read my most popular book, which is love is the killer app that book about my grandmother today, we are rich is really kind of the prequel. It kind of explains like when I went to work for Mark Cuban, why I was just so stupid, generous with all the knowledge and why I looked at networking different than most people. I looked at networking as a gift we give, not, not some shortcut for us to accomplish things in life.

And all of that, honestly, John came from these philosophies that Billy raised me with. Oh man, what an incredible, she sounds like an incredible person. What was her background? What was like, where'd she come from? Well, she came from Dripping Springs, Oklahoma. Her dad, Tommy King, uh, was kind of the founding farmer in the city where we grew up, Globus, New Mexico, uh, during the great depression. He was the, he was the guy that actually accepted the circular farming, which is the crop circle approach to irrigation. When they came in from Nebraska, we're talking to all the farmers about, you know, if you do this, you're not going to be dependent on rainfall. And they were all like, Oh, it's what is this?

So these, this is the devil. And, and, and, and, and Tommy was like, I'm going to try it. It's not, it makes sense to me. And of course, when the dust bowl happened, he's the only farm left standing. So he ended up giving micro loans. We call that now $10 or $20 there to a lot of people down on their left to rebuild their farms. And he became a father of our community and she was his daughter and she lived through that great depression. She lived through two really disastrous marriages, which taught her a lot. And, um, she was a person of faith and, and all of that together made her pretty resilient. Her, her born name was Willie May Kaufman. Uh, and she went by Billy and she was, yeah, she was, she was, she was good time.

You, you didn't want to get in an argument with her because she, she would have done her research. I would say so. And probably, and especially, uh, it's always interesting getting, uh, in a debate, a skillful discussion with people who have such strong values, um, because it's really hard. You, you, you combine the values with the preparation and that's kind of hard to debate against. So I imagine she would be a formidable person. We used to watch Raymond Burr and Ironside. And when he would win the case, she'd slap the chair and say, evidence, it's always the evidence. Nice. That's what I say now. I'm a G2A. I'm like evidence. Evidence. Show it to me. Citations. It's always the evidence. It's always, love it.

Uh, I want to ask one more question as it relates to that, which is, um, you talk about like the positive self-talk, right. And, and what you feed yourself, um, from a positivity standpoint, where do you fall on, you know, optimism and, and like blind optimism and blind positivity versus reality. So, you know, I'm always trying to stay optimistic, but there's always the reality that is there. And then, you know, there's the positive affirmations and keep self-talk. So are you one of those, like, you know, keep staying positive no matter what, or where is the balance for you of, of maintaining that optimistic and positive view? Yeah. So, um, the great comedian, Stephen Wright often said, I always want to borrow money from a pessimist because he doesn't ever think you're going to pay him back.

I love it. No, I think about this a lot. Like there's, there's, there's, there's, there's blind optimism. There's grounded optimism. There's learned optimism, blind optimism. Things are going to turn out. Okay. Really? Not always. I don't believe that. Grounded optimism. Things can turn out. Okay. I'm going to do a lot of work. Things probably have to fall just right, but things can go. Okay. You get a lot of hope out of that. That's good enough. It's good enough to move forward. Right. Learned optimism. This was taught by the professor Martin Seligman wrote a book on this called learned optimism is about the practice of gratitude, which reinforces what you have, which squelches what you lack and is a critical component in a crisis.

Right. So learned optimism is this ongoing awareness of the things that are going right. In sales, we call it green shoots. Right. So, so learned optimism is one's ability to focus their attention in a particular direction. Cause here's the problem. Human beings that don't have learned optimism develop default pessimism because where your mind goes. So let's say you're an employer and you got a bunch of BDR and salespeople. You've had a couple of cutbacks, but guys, well, you're private equity owned and you go on glass door. Do your eyes go to the one star reviews that say our CRO is an idiot or do your eyes go to the five star reviews to say what a winning culture, what a great product, what an incredible value system the company has by doing right with the customer.

Your eyes go to the one star reviews. If you're not in control of where your attention goes, because human beings catastrophize by default. I've written books, like you mentioned that five books. I trained myself to look at those four and five star reviews and take away inspiration from those. Do I ignore the one star reviews? No, I just don't give them PhDs. Well, we always say that like, like the problem with people is you give your critics a PhD and you take your fans and you think they're idiots. Right. And so I think again, you know, learned optimism is the, is the control, uh, over your attention to focus on the things that go right. One of the things that Seligman used to talk about is like for the mentor in your life.

Like, I don't know who yours was in your life, John. I've had mentors. You've had mentors. Who? Uh, a good friend of mine, Jeff Hoffman. He was actually the guy who started that show. Okay. Well, you probably already done this, but Seligman taught people to create what's called the gratitude letter. Gratitude letter. You're going to take your time. You're going to write it out and you're going to let Jeff understand not only the things he did for you, but the way those things made you feel and what those feelings enabled you to accomplish and, and how long those feelings will remain regardless of what happens to Jeff and you're going to write it all out. And you're going to say, Jeff, I want to sit with you.

This was like Seligman did with people. And you're going to go sit with Jeff and you're going to read that letter to him live. You're going to give him that letter. Seligman studied both participants and it's a toss up of who is more emotionally moved. The giver of gratitude of the receiver. The answer is the giver usually had the most incredible increase in like DHEA and dopamine production. But, but it was an incredibly rewarding experience to obviously for the receiver, but the act of expressing gratitude in such, in such a way like the gratitude letter is just a transformative exercise. So anyway, learned optimism is the aspirational one. I try to get better at it for now. It's grounded.

Things can turn out. Okay. I bust my ass and everything falls in place. So it's good enough. I love it. You know, I just did a, I did a keynote recently. It's, um, it's called continuous growth mindset and there's four pillars of things that I learned. And one of them is, you know, alignment with your, why your values, your goals, and your energy. The second one is execution. And the third is gratitude. And what I, what I try to share with people is the act of giving gratitude is obviously very fulfilling, but also receiving gratitude. You know, it's interesting to me is very few people are good at receiving gratitude because we diminish it quite a bit, right? Like, so say I was lucky. You say I was lucky.

It's the most disrespectful thing you can ever say. Well, it, it, or it's just, it's also disrespectful to the person that's giving you gratitude. Right. So it's like, if I do a favor for you and you come back and you're like, oh my God, John, thank you so much. And I'm like, oh, don't worry about it. It's no big deal. Well, not only am I denying myself that the, the, the pleasure of receiving that gratitude, I'm also diminishing what it took for you to give me that gratitude. So either you're not going to want to give it to me, like either you look at it and say, well, okay, I guess it wasn't really that big of a deal. So next time I'll just, I won't even say thank you. I'll just take it. Right.

That's right. I mean, yeah, the researchers say like when you express gratitude to another person, you reinforce your feeling that you are not alone in this world, right? Validation. So you got to, you, have you met Scott McGregor by any chance? I've heard of Scott McGregor. I have not met him. You, you, you, you two have to talk like not even on a podcast. You just have to get together because he's wrote a book or he helped write a book. He's one of the most giving people I've ever come across, but his book called Standing O. It's called Standing O. And it's, you write a letter to somebody that hasn't gotten the recognition in your life that you've wanted to. So it's a whole book of gratitude of, you know, individuals.

I'm in one of them, just thanking my mom and dad for everything they did for me. And he's got a second book. And so I, after this, I absolutely have to introduce both of you. You do that. I do want to go back to your first thing. I'm aligning on your values. So I do want to tell you that I don't want to go Dr. Sheldon Cooper on you here. That's big, bang, big, bang reference. But I want to dig into what that scientifically, like if I was a positive psychologist, which is literally a discipline, I would say, you know what you've struck here, John, is a core technique of cognitive behavioral therapy. So cognitive behavioral therapy allows you to disrupt negative thinking with restructuring amongst other things.

So CBT can completely change around a very negative person, very positive person. A core component of CBT around restructuring is the idea that when you're in a negative state about something. So let's say you are at work and you're a salesperson and they've changed the comp plan. Now they've changed the comp plan because there's this thing happening above here around budgeting and around the company, getting to the next tranche of financing and these other such things that, you know, you really don't care about as a salesperson, but it's filtered down into your world because now they've moved the goalposts a little bit and you're pissed and you can't not be pissed. You're like, man, I'm so upset.

They changed up, want to make less. They didn't confide in us. They told me this would never happen. You're mad. That's not going to help you with your leaders. That's not, you know, you can't be upset enough about the comp plan to make them think promoting you 1% more. So CBT would say, listen, what are your values? Well, one of your values may be, I am a very agile, flexible, understanding person. I've always been. I know how to adapt to situations. Challenge yourself in that way you're thinking about the comp plan. You can challenge yourself to say all of your negative reactions, all of your anger, all of these negative feelings are literally a contradiction of your claim that you're a flexible, agile person.

Dude, be flexible because every comp plan change takes away and gives something, right? They're never, they're never negative. They're, they're always zero sum. It's just, they took away a thing you were getting now and dangle a carrot you could get in the future. Aligning with values is a great way to get back to this idea of structured, positive thinking. So yeah, I do that all the time. I never thought of that getting in that way, but it's, it's the first exercise I tell everybody to go through when they're trying to make a career decision or anything big in life. It's like, before you do that, go through that core value exercise. And I even created like a little prompt pack to guide people through it so that they can really, cause once you, I told them, once you get really to the core and don't just say, honesty is a value of mine.

Like, what does it mean to you? And, you know, fairness and all those other things, because once you are concrete on those, well, then your decision lens becomes pretty damn easy because now you look for opportunities and people and jobs and everything else that align with your values. And to your point, your reaction, you can always go back to them and say, am I living these values? Because if something does have that much of a dig to you that you are that pissed off, it's probably because it's crossing one of your values. Yeah. And if it's not, then you should relook at your values. Cause if you're that mad at it, then agility might not be your value. You know what I mean? Like you might, you might've done like a surface level thing of, oh yeah, I'm agile.

I love agile. It's like, do you? Cause you're pretty pissed off at that. Yeah. I love that. That's great. That's cool. It's an interesting, even, you know, SDRs and everybody, I, the why is the part that I'm like, I think you need a little bit older and you're like the Simon Sinek stuff, right? Like I don't think, you know, in your twenties and stuff like that, you don't know what your why is. Like, I think maybe a little bit later in your career, but man values, I've been teaching those to my daughter since she was 10. So I love it. The criteria by which you allocate resources and make critical decisions. The game monopoly, the cover, you turn it over, the rules. Those are your rules. Your values are your meta rules.

So let me, I'm definitely going to get to some of these data points, but I'm very curious. So you were in special education, but back then I think they just kind of, if you were rambunctious, if you had ADD or if you, you know what I mean? Like they would put you in these, what from that did you pull as your superpower today? Right? Because I think that, that might've did, did you have the confidence from your grandmother that you knew like, okay, I'm a little different, but that, that doesn't mean it's bad. It's just means I'm a little different. Or did you kind of learn from that experience and say, wait a minute, my, my weaknesses that they think are my weaknesses are actually my strengths.

And, you know, going into debate and going to all these other things, I'm just kind of curious what that phase from a rooting standpoint got you. Like, cause I mean, if you think of special ed, when I was there, it was like kids who actually had, you know, development, developmental problems and all those other things. But I don't think we were educated enough to know, but I'm just curious where they, that came from, from you. Was it just because you were rambunctious and was it ultimately a superpower for you when you figured it out? I was very depressed. Okay. I was very depressed. I would disappear on campus and they'd find me like inside a bucket that I could fit into a 20 pound bug as a little kid.

Um, I was very depressed. Um, I didn't speak, didn't speak to a lot of people. Um, my mother had abandoned me in a hotel room. It's a long story, but, but I just took it very personal as a four-year-old. And so like, I wasn't much better at five by six. I had a chip on my shoulder. I was very depressed. Um, I acted up too much in class. Um, I got absolute zeros on everything cause I thought school was stupid. Um, so, so all of that happened and what I kind of figured out, like the first year of special ed just really sucked. You know, I focused more on the fact that they've been fun of us. My nickname at church was short, but it's kind of just like you, you deal with all the change, but what I kind of clicked with year two was the only way out of special ed is to finish everything on that wall.

And once I figured that out, then, then that was it. It's like, you want to get out of this place. It's great. Just finish high school. So, um, I learned how to study on my own cause I never had teachers cause they don't have teachers in special eds in the 1960s in the state of New Mexico. They got a, they got the equivalent of like a study hall guy. And this is TMI, a study hall guy with like a car battery and some, some jumper cables that he rubs together with sparks and says, yeah, you blankety blanks. I won't even say the R word, you know, do your work or else. So, so that, you know, so I didn't have teaching, but I had to finish. So yeah, I learned how to study on my own and I do it all the time.

Like when I think about like answer engine optimization, this AI search thing, I researched now, dude, you should see some of the self-study. I do to understand how these large language models have been programmed and fine tuned to avoid making a bad purchase recommendation. And I've learned all that on my own. A lot of other people will be like, you need to take trig. You need to take computer science. It's like, no, just put me in a room and say, the only way out is to learn everything on that wall. I'm pretty good in that environment. So that's the main thing. I learned how to study on my own and, and in Excel. I love that. And I think that, and the reason I asked that is because I think that brings a lot of hope to some parents out there who, you know, are thinking their kids, because I have a lot of friends who are worried about their kids in school and that type of thing.

And ultimately school is an interesting construct in general. And I would be diagnosed as autistic. I mean, I don't want to skirt that for, for those that know me well enough. No. Yes. As a child, I was probably a one, a level of autism based on a lot of other things that a lot of other physical signals and signs, but you get better. And so I tell people all the time that have children who might be special education, they might be neurodivergent. It's like, Hey, you get better. You grow up. Good things happen in your life. You could have a huge leap. I've seen it all the time. I used to not communicate very well. I communicate well now. It just gets better. It's not always that way, especially when you've got great parents, you've got great people surrounding you.

I love that. So now let's, Mark Cuban, how did this opportunity come up with broadcast, right? This, cause this was before he sold it off. So you were early there. You talked about the positivity and everything you gave to that, right? And made an impression. Where did that opportunity come from? Was it, was it circumstance? Was it deliberate? How did, how did you get introduced? Kind of a combination platter, kind of a combination platter. So I was working, um, at, uh, Pat Summerall studios. He was a sportscaster, but he also had a production studio in Richardson, Texas. We made content for the discovery channel that ran at two in the morning and around 1995 ish, I'd started, you know, the internet was starting to get used.

And there was a couple of early video players in the 1996, I, I read an article about somebody that had put a program on the internet and like 10,000 people watched it. And I'm like, that's going to be the secret to all of our problems at two in the morning. We'll just put it on the internet and people can watch it during the day, you know, or we could get better distribution with the internet. And then I read an article. I want to say like early 1997 in information week, because what I was doing, John, is every day when I'd get off work and I was a sales manager and I was a salesperson and a salesperson my whole life on the way home, I would stop at the Richardson public library and read whatever they had about the internet.

I'd read all the articles, all the publications. I read the book. I got it behind me. I read some of these ones like the diffusion of innovations. I read the being digital, which came out in 1995. So I'd read anything I can get my hands on because I was trying to like wrap my head around the internet and like, I think I can learn this. I had no idea there was an economic opportunity. I read an article early 97 information week. I believe it was about Mark Cuban audio net in Dallas. He was streaming back Indiana university basketball games. He was streaming it over the internet because he, they weren't broadcasting it in Dallas where he lived and he'd had a, a, a PC startup before I'm like, man, I want to work for him.

My wife, Jacqueline, one of her customers, she, she was a hairstylist was the lead investor or one of the lead investors in audio net. He got me an interview. I went in there and I, and I showed them all I'd already learned about internet, that the future of traffic, the way that internet packets would be translated over video. And I even had a vision in the interview. I was like, this is like 1997. I'm like, you know what you think talk time is going to be big for phone. Wait till people are watching things on their phone someday. Then they're going to pay for data. And I'm like, Oh, this guy's kind of, kind of spicy. And 90, hold on a second. 1995, sorry to interrupt, but in 1995, you had, you saw you, you could envision people watching on their phone.

Oh no. In, in 1997, I went to prime co, which was a carrier and Ericsson, which was a handset maker and pitched to them on behalf of Mark Cuban that we had 400 different games under contract to stream. And I pitched them on a concept called listen time where they would charge listen minutes, which would be a discount version of talk time. Cause at the time cell phones were sold based on packages. You would buy so many minutes of talk time. So I pitched prime co on listen time where if you were at the game with your kid watching some stupid baseball game that you didn't care about, but you were missing Notre Dame playing, you could listen to it on your phone and pay a discounted minute. So yeah, that was one of my early, my early ideas is that, you know, I think, I think there's more, more money to be made on phones than just us talking on the phone.

I think we'll listen to games. And then Mark's like, yeah. And we'll watch our kids will watch everything on phones. And that was his vision because he was bigger vision guy than me. Um, but it was a great experience because I learned to sell something that didn't work, which at the time, 1997 was internet streaming. When I, uh, 19, a year later, I, I, um, had, it had a great deal. I cut with, um, the limited their division, Victoria's secret. I sold them a six figure deal to, to stream the victorious, Victoria's secret fashion show. It broke the internet too. I remember that failed. It failed and I still got them to buy a renewal to do it again the next year from the can film festival, convince them not only to go big on it, they took the concord.

Remember the concord before it crashed? They painted it pink for Victoria's secret. We did a live chat because Yahoo had bought us by this point. We did a live chat. I think it was 1999. And, uh, with the models as they're flying on the concord on their way to the can festival where we did Victoria's secret fashion show too. And it worked the second time anyway. So I had fun, I had fun selling for him. He was a great guy to work with, but I tell you something from a sales standpoint, if you were ever like, cause we had a, like a broadcast.com, which was what audio and that became, it was this warehouse in Deep Ellum. And if you, when Mark would get back from meetings and he'd be walking the halls, walking the cubicles.

If you are standing around talking to another salesperson, Mark would walk up to you and famously say, did you pick up a check today? When are you going to go pick up a check? What are you doing? You must've just picked up a check as you're standing around talking. And he was just so focused on that. I remember I was telling the story recently too. He, I remember he had all the salespeople in up and up in the, we call it the crow's nest, which is our little room. We'd meet in and show them all the deals in progress. And he'd say, man, I love this country. He says, um, you, you sell a dollar. I give you a dime commission and the stock market used me 60 because the multiple for them was 60 to one.

I'll never forget that. And he said, someday I'm going to call you from my plane and we're going to talk about this moment. And we were all like, that's so cool. And then years later at a reunion, we said, you know, he never said we're going to have a plane. No, no, he was great. He was great. If you did your homework, you had an idea and he asked you what your research was and you'd done your research. He was the coolest guy in the world. If you had an idea and you were just making it up as you went along, he was Bobby Knight. It would piss him off. You, the last thing you want to do with Mark Cuban is waste that man's time. I love that. What was your, what was your kind of one of your biggest takeaways from that learning, uh, from that segment in your life?

Read long form books. Like your life depended on it. Cuban said people are getting lazy. They're not going to read anything long form in the future. Reading books gives you depth where everybody else is shallow. I learned from Mark that it's not the pitch. It's not the PowerPoint deck. It is the freestyle conversation that makes you a rockstar salesperson. Like how do you do in the freestyle? The only way you do great in a freestyle as a salesperson is being well read. Being prepared. I love that. I love that. All right. So let's get through the, cause where you and I met up was Upwork and you were brought there, um, kind of change agent. Right. And the future of work was that like three years into my AI obsession when I met you in 2019.

That's about three years into that. I was like, are into AI at that point. I was already pilled and it was machine learning the nickel back of AI at this point. Um, but I was pilled at the time, 2019. A blue pill, right? Dude. So that was, and that was before almost any of it. I mean, I remember in 2017, I was introduced to it briefly by somebody who created an AI. Auto-completion suggestion. Yeah. And it was like, it wrote an email that was super personalized. And I went and talked to Gary Vee and I was having a heart attack. Cause I was like, I just saw a robot write an email better and more personalized than I could ever write. Uh, what does that mean? And he still said something to this day that sticks with me.

He's like, you know, just be the last mile. He's like, let it, let it do all the heavy lifting. Just make sure that that's. And look at us now. Most people watching this, you are the API between Claude and your sales manager. Yes. That is the last mile. We are. And hopefully we'll stay there. But, um, again, um, Upwork did the future of, I guess, what attracted you to that? Knowing AI, because Upwork was a lot about outsourcing human, uh, capabilities. Freelancing. It was a freelancing platform. Um, I, I got interested in it because of Eric Gilpin. Like, like I still were, I worked for Eric at GM. I'm gonna follow that guy around until I guess I'm just too old to work. Um, so I have to just give credit where credit's due.

I, I'm one of Gilpin's people. So, so that, that's it. I mean, he hired me to do consulting. He hired you to do consulting. I fell in love with what Upwork's potential was, especially helping companies be faster at adopting AI by using freelancers. Because it's such a, so many specialized talents you have to get. And you know how slow companies are at hiring even general talent people. So I'm like, hmm, Upwork can really help people go faster with AI. Um, and so that attracted me. And then Eric's like, ah, have you ever thought about going back to work? And at that point, John, I was like 12 years into owning my own business, writing books, speaking at conferences, doing consulting gigs here and there.

And I'm like, you know, I'd like to take another dip here into corporate life and work on a team. And that's when I went back to work for him. And like I said, when he went over to G2, I liked that even better. And that's where I'm at now. I love it. Cause you're the first, uh, was it chief innovation officer, right? Exciting. Yes. And, um, my job is not only to help G2 innovate how it solves problems for customers, but to help our biggest customers, leaders think about how they can innovate too. And what I really think a lot about is this transformation of companies, um, from being software companies to becoming agent providers. And I think a lot about that. And for marketers and salespeople, how, how can you transform, you know, transform yourself from being very appealing to humans to very, um, uh, readable by machines.

Well, and that's where, um, fascinated, right? I mean, there's a lot of data and points that we can point here, like 82% of buyers use it, uh, source software recommendations from AI, 49% of finance leaders, all these different stats that we can dive into. But my, my bigger picture concern is that, uh, you know, as part of my keynote, I talk about, you know, uh, age, the agile sales org and how I think between 2010 to 2022 was the golden age of sales. And I even did another presentation at Pavilion called the, um, uh, anything but predictable and how predictable revenue in my mind, in a lot of ways ruined sales because it turned it into this assembly line. And we spent years focusing on process and the tech and everything else.

And really the skills side of sales, the softer side of sales was ignored in a lot of ways because it was such a machine that worked for so long when interest rates were nothing. And so my fear now is that we've turned a bunch of this, like a whole generation of sales professionals into robots. And now they're getting replaced by robots. And, and there's still this old legacy model of like, you know, doing the discovery and everything else. When your data suggests very clearly the discovery isn't the issue anymore. It's the evaluation piece because people are doing that discovery. So how do we need to retool? Cause this is my big, and actually you're probably the best person to answer this question.

Okay. So here we go. Um, but I'm going to start, I'm going to start like a non sequitur. First of all, my son is in sales. He's in cybersecurity sales. Believe me, I, I, I feel this pain. Okay. But let me start with something. You've heard of Fred Smith, FedEx, right? Did you ever hear Fred Smith talk about the idea that the information surrounding a FedEx envelope of paperwork was worth more than the paperwork in the envelope? And he was talking about the value of information. So all the information around the FedEx, the scan code, the destination, all that stuff, that data that they were capturing was more valuable than the average package they were moving. And that turned out to be true in terms of the value FedEx ended up building on top of its information empire.

Okay. Here's what I want to tell you. Salespeople don't just sell stuff in the new economy we live in now. Salespeople are the frontline of business intelligence in a world of black box, open AI, Google, Gemini, and Claude. Okay. Here, let me just kind of unpack this for you. Half of all, and I can, I only research software buying, but you can, you can just apply this to everything else. Half of all software buyers now start their research in chat GPT or Gemini, and then maybe a little bit Claude. But half of them start in the chat and they one shot a short list. Hey, I work at a hospital medium size. I'm looking for some like scheduling and patient management solutions that also work great for community outreach.

I need month to month billing. I can't do a one year deal. And it's got to work great on phones because most of my people are doctors walking the floors. And then they get back, oh, these are the three CRMs that we recommend. Oh, it's called CRM. Cool. And then that short list, six cents would tell you nine times out of 10, that person's going to buy off that short list. So that's it. That's the short list. And then so you're like, you go to review sites, you do some research, you get it. And then you go like, hmm, number two, I like the second one, Pipeliner. That sounds like the one for me. And then you Google Pipeliner contact. Fill out a form. You need to talk to a person, okay? You're 80% through the entire purchase journey.

Rep now talks to you. Tick tock, tick tock. The issue is oftentimes I like two and I like three. So I'm doing them both. So I'm like, Google contact number two, that goes first. And I'm like, yeah, how about number three, too? Let's talk to them, too. Maybe all three, but let's just say then. So responsiveness has never been more important. So your ability to seize the moment, because this person is 80% through the journey. But this is the fascinating part, John. They're fresher to the experience. What I mean by this is that just creating the short list for buyers, we've researched this at G2 for almost a decade. It was seven to 12 hours. It was multiple days. You went down the Google rabbit hole.

You talked to your peers. You read analyst reports. You were kind of tired of that shit. And then finally, you talk to a salesperson. They're going to move you through the process. And you don't want the demo. You don't want this. You're just like, oh, you're so tired of it. This person is talking to you just a few calendar days into their journey, but they're 80% done. They actually enjoy the demo. I hear this all the time. They enjoy the sales process. What corporate executive board would tell you, those guys, remember them? Challenge yourself before they went off to partner to talk. Remember them. And they talk about the harder the purchase was in terms of hours you put in, the more likely you were to be dissatisfied with the product.

I thought that was a fascinating insight. You have an opportunity as a salesperson to engage a person, you know, at the end of the process, but the beginning of the calendar journey when they're fresh, educate them on how to distinguish you from number three. But most importantly, along the way, gather intelligence to help your marketing team get you on the shortlist. Let me explain. The secret to winning an AI search, like the secret for a software company to get on that shortlist for that prompt for the hospital, is for them to understand exactly what real human beings are putting into the prompt and chat GPT so they can write the content and then build all the third-party evidence for the model to say, this is the CRM, but they can't.

Most software companies, they're blind. Their vendor says, well, let's just comb your website and take all of your words you use and then create questions around those words, and that's your prompt panel we're going to study. And it's like very fuzzy. So everybody's like, where do you get the prompts? Because OpenAI won't release the prompts. Google won't release the prompts. You say, well, we listened to some gong calls from BDRs. Yeah, that's not the prompt. Maybe there's some language there. Where do you get the prompts? Well, I know for the last six or seven months, the big smart software companies, you know what they do, John? They give the BDRs a spiff, call it a hundred bucks a capture.

So when you've got an inbound call, one of the first things you ask is like, what caused you to reach out to us? What recommended us? So if they say chat GPT, the BDR stops because they've seen some of these calls. The BDR goes, fascinating. I'm always trying to be better at prompts. Like, what prompt did you use? I'm just dying of curiosity. And they know they're going to get a hundred bucks. Because remember, the BDR is supposed to set the next Zoom call. You can't just tell them capture the prompt. They won't do it. They're trying to get the call. But giving them an incentive, their information capture. So I've seen it. So the prospect will go into their open AI library and take the prompt and copy it, put it in the chat.

BDR puts it in Salesforce. I've had CMOs at big software companies say, Tim, you get a hundred of these, you see the light. You get 200 of these, you change your marketing plan. And all of a sudden, you start to see the traffic coming via Cloudflare from the bots going right to contact and pricing and key feature pages goes up. Because now you're calibrating. What's the secret? BDRs are the secret because they're the ones that are talking to the prospect. And additionally, if the BDRs are documenting last touch, because this is the other thing that's fascinating. If the BDRs are being incentivized to flow through, you know how bad we've been at closed one loss on Salesforce. What if we were great on reason for form fill?

If we knew that X percentage of form fills were happening because of chat GPT six months ago, but after we made the investment in this content and this review campaign, now it's why the numbers tripled in terms of inbound saying, I came to you from chat. Now BDR can close the loop. So marketing becomes a machine. So I'm telling you in this world now, these marketers, they can't succeed without the BDR. This is crazy. Everybody's like, oh, agents are going to replace BDR. Agents ain't going to capture the problem. Agents aren't going to track this stuff. BDRs are actually the most important player as far as marketing is concerned in a world where we think, no, it's the AE. They're important too.

They're the killers. I get it. Well, I mean, I've said that for a while now that I think the BDR role should be looked at as more of a marketing role than a, because they're, they're, yes, they get meetings, but one of the things that they're great at is the frontline role. It's the front. It's the first impression. It's the first insight. It's the sourcing. I'll give you an example. If you leave it up to marketing and all they do is look at last click. I've read this statistic. It comes from air ops, the study that air ops did. If they just look at last click and marketing, they're going to underestimate the impact of AI search on your business. 10 X, 10 X. So like, where do you measure it?

You measure it at the frontline. Who's picking up that inbound call. So, so that's that inbound form. So that's the value, right? That, that, the SDR, BDR, whatever, a value. So what's, so that's, that's for the company collecting information. I've always said that, you know, in lieu of a meeting, gathering any type of insight so that we can enrich and make better decisions is, is primate, right? What value does the BDR in that scenario bring to the 80% client that lands on there, that lands in their thing, right? And I'm talking very careful because I, yeah, I thought about that. Now I'm going to, oh my God, I'm going to quote Grant Cardone. Are you? Oh, shut up. I'm going to hang up on you.

No, don't do it. Don't do it. Don't do it. Listen, closing people is a favor because, because, you know, we live in a world where they're, they're getting such fast answers from chat GPT and such a wealth of information in the citations that the, the, the prospect becomes their own worst enemy of indecision because they can keep going back and keep going back. And so it's like, whether it's the BDR knowing how to put them in front of the right AE at the right time, or whether it's the AE just convincing them to stop thinking about it and do it by showing them the, the med pick, right? I think that today's AE is the sommelier, like, like there's a book I read called Reshuffle. I love this book.

And it's about like how everything changes when AI restacks the knowledge economy, but it talked about the idea that for every problem AI solves, it creates a new problem to be solved. And like your job is to solve a constraint in the system. Okay. So AI, so the example he uses is sommeliers. In 2026 sommeliers are in demand. They make more money than ever. You would think that agents had eliminated sommeliers. Just ask chat GPT. No, it's exactly the opposite. We are so overwhelmed with options from chat GPT that human sommeliers like it's this bottle. Well, wait, hold on. I think that's fascinating. But I'm going to push back because we've gone from this search engine to an answer engine. And that's the problem with AI that I see that it gives you the answer.

And it doesn't even give you three at this point. It literally, at least Google, it was the perception of choice where you did have to read a few things where now it gives you three. The entity update, it won't give you one. It'll give you three. If you say make a recommendation, it won't say this one. It'll say these three. Again, they don't want to give you, they don't want you to make a regrettable purchase. Like the North Star of programming at OpenAI, avoid regrettable purchase. They call it your money, your life. When AI makes a your money, your life claim, it must lead to a good outcome. So we could get into that's why a company's website cannot win the answer in ChatGPT. You have to get third-party proof.

You have to have receipts because it's programmed for that. So it's going to give you three. And there is a likelihood that your company can make those three if they know what the prompts are, can optimize for it, go get the evidence and figure out how to have those attributes. But the last thing I tell you, though, it's like the conversation is never ending. In other words, it's almost like building a custom suit. You keep going back to the tailless. Should I have it blue? Should I have it tight? Should I have it stitched? Should I have embroidery? Should I make it plastic on the end? People keep going back over and over again to ChatGPT, and they don't necessarily close on the one. They do contact sales further in the process, but that doesn't mean that they have a solution in place faster.

So there's other procrastination that comes by their ability to keep going back to ChatGPT and uploading the Cronulla notes from the sales presentation. What do you think? Do you think he's telling the truth? They can be very indecisive in a world of GPT where they feel like they're just going back to their confidence over and over again. So I still think today an AE is doing a favor for people by bringing the human urgency, pressure, med pick, you know, methodology to the table. Like, you're wasting time. You're losing money. And I couldn't agree with you. And I think the right, you know, the top tier sales reps are going to be even more valuable moving forward here, right? Because I think I saw a Gartner stat about how, you know, 67% don't want to talk to a sales rep, but 69% want to talk to a sales rep to validate what they learned through AI.

So they don't trust it. And I think the other thing to think about, too, is your ability as a salesperson to build your own propensity model out of your book using AI. Run expected value against every minute you spend and to be able to take whatever systems you have and append them to give you the best propensity. Like, I meet some salespeople today that, like, they are getting a higher percentage of outbound meetings set because they're able to use AI to manipulate the options they have to talk to the ones that are the best based on a variety of different factors that save them a bunch of time. I mean, when I started out in sales, I was selling newspaper subscriptions in college. You know what they gave us, John?

They gave us, like, 323-393, and then you dial 00 all the way to the end of that block, okay? It's exactly the opposite now with AI. You can personalize. You can build your own propensity model. You can scale by using something as simple as voice keyboards. Like, I don't type anymore. I press the function button. I speak. I'm three times more productive than I've ever been. It's like there's just different ways a smart salesperson learns, like, win the machine and win the human and, like, really wins. With that secret sauce. So then how do you build those muscles? Because here's the kind of big question I'm wrestling with right now, which is for people like you and I, right, I think AI is an absolute superpower because we have the context, we have the experience, and all the stuff that we did early in our lives and our careers kind of gave us that context, gave us that experience.

So we can call bullshit on AI when it gives us an answer. We can ask it questions and be curious, understanding that the answer isn't always the answer and go from there, and use it to outsource the admin-y stuff that we know we used to do so that we can be present. But for that kid coming out of college, now that AI can do the vast majority of entry-level stuff better than, and I'm picking on sales here, but you pick profession law, any of it, where, I got two questions. One is, where do the fundamentals come from anymore based on the fact that AI can do a lot of that entry-level stuff better? And two, which is more important to me, which is, are very quickly, are we going to have to shift what the fundamentals are?

Are we going to have to, because we're in this transition phase, my question is, are we going to have to fundamentally change the way we teach, the way that we educate people in this world of AI when knowledge is a commodity? Yeah, we're going to have to change. I mean, they changed how they train bank tellers. Bank tellers are like concierge to loan products now. Like, when I was a kid, they counted money, right? So, yeah, we're going to change. But let me kind of get to the sales question, though, really. So, here's what I think. I don't think you became good at sales. I don't think I became good at sales because of the rinse and repeat work that we did. Cut, copy, put into a sheet. Read the same script 500 times.

I didn't get any better at sales from that. You know what I got better at sales from? Trying stuff in front of real people and failing and getting feedback. So, the quickest way to build your judgment muscle is to put stuff out in the world and make it available for feedback. Entrepreneurs have never been more important. I tell people in college, like, build an app, launch an app, get your dad to give you $1,000 and go lose it and get feedback. You know who did that and became the greatest example of the judgment layer? Rick Rubin. Rick Rubin formed Def Jam in college. Wasted his student loan money. First few records failed. How did he deal with failure? He went to the record store. So, I put it on consignment.

Nobody picked it up. They explained to him what was missing. Go to the radio station. You never played my song. They explained to him what was missing. Then he realized, oh, watch the charts. Develop a nose for things that work on the charts. Sees the Beastie Boys frat band. A rock jazz frat band. And has a nose for what would happen if they reformat to rap. Makes the Beastie Boys who they are. Goes on to, what did he do? Nine Grammys, 30 platinum records. What does he say? I have judgment about what I like and I don't like and I have conviction and that is proven to be useful. That's what you've got to build up, right? He didn't get it working at some studio doing batching and Mike Cable rolling up for 15 years.

He never worked in a studio. He put stuff out. He got feedback. He obsessed about where do you get the special information, the answer key. So you talk about AI. There's a concept in AI called Verifier's Law. Verifier's Law says if the AI can verify its work, then AI can conquer the job. That's why there's things like writing sales pitches really hard to verify. Because you don't know if that sales pitch is on brand, on voice, or for that matter, accurate. So as a result, not a lot of us are going to let AI do all of our sales outreach. We really like to put it on a short list. But what if you had the answer key? What's the answer key? When you look at stuff that works coming out of companies like Clay and Dust or whomever, it's a corpus of perfect emails and a big corpus of them for the AI to be trained on what works.

So what I tell human beings is in this world of AI, you need to find the answer key. You need to know your customer more than anybody does. You need to know more about your customer pain than anybody does. You need to know more about the domain. Like if you work in the legal industry selling legal industry software, you'd better know everything about the legal industry, everything about the ICP. Because the thing that AI doesn't have is domain expertise. It is a generalist. All of its answers are by nature average. It is the human that makes the artificial intelligence effective by lending domain expertise. So I tell people, not much different than my career started for Mark, go be a student.

But don't think that going through a 20-year sales cast system where you start out by making 800 smile and dial calls a week to set one Zoom call is going to make you a good salesperson. I say, put something out, make it fail, build a system. My son built a couple of sales propensity models for the cyber company on his own time on Saturdays. And when it worked great, he showed a manager. The manager showed his grand boss, showed his great grand boss, kids going places. He tried something. He operated at an entrepreneurial level. He didn't accept the systems they gave him because the systems didn't value his time. They valued the old way of thinking of it's a numbers game and it's no longer a numbers game.

Hey, I can do those numbers. You don't have to go to, like if you lived in London, want to be a cab driver, you had to go to school four years. It's called the knowledge to drive a London cab. Today, you can be an Uber driver if you have a phone with Google Maps. Doesn't mean that driving is not any longer a matter of judgment. It still is. So I said all this to say, if I'm in sales, I'm going to do what my son did. I'm going to be entrepreneurial. I'm going to try to make better systems. I'm going to get feedback on them. And then I'm just going to obsess about who's my customer. What is my industry's goals? And I'm going to have more domain expertise than the AI I'm competing with. And I'll differentiate.

And I think that's, I mean, that's why I am insanely optimistic these days for people who are creators, for people who are curious, because the world is yours. I mean, you have a tool now that can literally build and create, I don't answer anything. Yeah. Like I don't type anymore. I think about like how LLMs. I don't know if you use Willow Voice or Whisper Flow. I would whisper. LLMs. Whisper. I mean, I didn't realize, John, how much I clicked delete, return, space, and fiddled with formatting. Oh, my God. So I don't do that. I don't really do anything repetitious anymore. All I do is think. I mean, how cool is that? So it's like I have a different type of job. I work harder than ever. But I'm not doing repetitive work.

So I try to look at the glass half full, one third full. The engineers would say this glass is over-designed by a factor of 64%, but they're geeks. I try to take a positive view because what else are you going to do, bro? This thing's not going to get stopped. Bernie ain't stopping AI. That thing's going to happen. So I try to ask myself, like, how's my world going to be better in our world of AI? And I live it every day, bro. I'm 64 years old. I should be like the most afraid of AI of anybody you've met. Look at me. See, and that's what I'm saying. Like, I think my optimism is high for that. But my pessimism, though, is on the other side is the vast majority of people that are not driven creative, you know, that have been fit into a system where they are a cog in the wheel, per se, if you will.

And are just want to kind of do their job, right? Not anything more than their job. They just do their job. And I think historically as a society, we've been able to tolerate that because that's the way that we built this. Moving forward, I don't know where those people live. At this point in this system, in this new system that we're moving into. Yeah, there'll be externalities, to your point. There'll be externalities. There's no way to sugarcoat it. I do think that we will see people moving to the industries where AI is the weakest, and that is driving cars and doing things with your hands. You go, wait a minute, there's Waymo. Dude, I wrote my first Waymo eight years ago. I thought it was going to be everywhere.

It's like, show me two TikTok videos of a Waymo running over somebody in a crosswalk, and they're not going to let it launch in Cleveland. What do we have, seven cities now or eight? So there's still stuff. I hate to say this, but there's plumbing. That's a really good profession. There's construction. Electricians. So I do see people saying, well, I wanted to be an information worker. I work with my hands. That's a piece of it. Will there be people that have long-term unemployment? Absolutely. And we've seen this in other economies. I think about the unemployment of the United Kingdom after coal. I mean, there's like, yeah, there's externalities AI creates, and I hope that some of the upsides create even more economic opportunity to cover for that.

So all we can do is teach the kids, be entrepreneurial, be Rick Rubin. It's funny because I just started. My daughter wrote a book with her called I Want to Be in Sales When I Grow Up, and it was when she was eight years old. She's 15 now, and we have all these boxes left over, and she's got two years left before she graduates high school. Wow. I don't even know if college is going to be a thing by the time you graduate. So what I want to do, but I truly believe in the social education of college, maybe not the traditional education of college, but what I'm trying to show her is how to build, like your son, create something so she can create a revenue stream so then she doesn't have to rely on the degree.

She doesn't have to rely on the job. And so we're taking these boxes, and we started this company called the Future Founder Project, where boxes of books go to kids between the ages of 7 and 12, and we help them start businesses with the box. And so I'm teaching her how to build and then trying to teach other kids how to build as well with it because I do believe you that – I agree with you that entrepreneurship is the future, I think, for a vast majority of people if you become really good at something. Yeah, even inside your own company. Like, I keep thinking about my son's approach, like, you know, he took his own time, used his own tools, used his own instance of Obsidian, his own subscription to Claude, and rebuilt a better customer prep princety model, and got deals out of it, and then, you know, basically was able to show and tell.

And, I mean, like, had it been a piece of crap, he still would have learned something. But he took – it's a tremendous risk, but he felt comfortable that the culture would be okay with it, and it was because they bootstrap this particular company. They don't like to waste a lot of money. They appreciated him doing it, and they're going to reward that. And the research is good for this. I researched, you're three times more likely to be promoted at work if you demonstrate AI entrepreneurism, if the leadership of that company thinks that AI is their future. So, you ask yourself that as an employee, like, are we hearing this from your CEO? Go out there and get some, because it's the surefire way to signal to them you're part of the solution, not part of the problem.

I love that. I could talk to you forever. Question, let's – because we're coming up on time, we're going to have to do a part two on this. Out of all the research that you did in the most recent reports here, what was the one thing that stood out to you the most? What was the one that you were like – that you were most surprised by, I guess? I find that for B2B sales, the buyer is going to get increasingly technical, and the traditional buyer who feels the pain, if you sell – like, say, you sell to the CRO, you sell to the CMO, you sell to the head of customer success, you sell to the product. We're heading to a pre-SaaS world, John, very soon, where all of those ICPs become internal customers to the new buyer, which is IT.

So, I think what I'm recognizing is, like, whatever you sell in B2B, you're eventually going to be selling to the technology department again. And, by the way, that's where it was when I started. And that's fascinating. So, we're all going to have to learn how to resonate with technical people more. A lot of the things we did with business leaders that resonated won't work. So, I do think that's fascinating, that the buyer of B2B is getting very technical, very, very geeky. So, thankfully, I grew up with a bunch of nerds. My first job was IT services, and I was one sales guy within 50 engineers. And 10 of those engineers were Linux engineers. And, man, if you ever hung out with some Linux engineers, there are different crowds.

So, learning how to communicate at those levels is a powerful tool. So, man. Yeah, you know what they say when a Linux engineer gets in a fight with his mother? You know what they're calling? No. Single. No, I'm just kidding. It's a terrible joke. It's an old joke. It's a boomer joke. It's terrible. Here's one. Because their mom's the only one that ever goes to eat with them or anything. The one that I was told by a Linux engineer is, how do you know, if you're talking to a Linux engineer, how do you know a Linux engineer likes you? And so, they look at your shoes instead of theirs when they're talking to you. Oh, that's good. I love that. Yeah, that's good, too. That's even better than mine.

That's even better than mine. Cool. Awesome. Well, look, I've been really enjoyed this conversation. Like I said, Tim, I think we need to have another one because there's so much to unpack with these reports and what you're working on right now. What are you excited about next? Like, to tie this up, what's kind of got you fired up next? I'm going to have like three or four executive assistants that I'm going to have a chief of staff. I'm going to have a person that's head of calendar. I'm going to have a person that's head of proactive research. They're all going to live inside GrokBot or Claude Cowork. And I'm going to be able to delegate a lot of like repetitive work that, you know, I kind of get behind on, but I'm still going to get to do the most exciting work.

So I stood up my first agent, which is my head of calendar management, who just kind of stays ahead of my calendar with me and be like, that's a conflict. You need to do the thing. Have you read the thing? I'm going to schedule the thing. And I see that. And I'm kind of playing around getting that skills in V file built. I'm like, that's cool. Can't wait till I get a person that does my research, a person that does this, my travel. And then I get a chief of staff who manages those agents. I think about that because then it's like, I'm starting to get really strategic. Like, yeah, but I still get to synthesize the research, do the outlining and write the long form stuff. I still get to create the, you know, this, that.

So it's exciting that I'm going to have an army of EAs because I don't have an EA. I've never had an executive assistant because I didn't want them to spend that kind of cheese on, on, on, on having headcounts. Same here. Awesome. My friend, well, where can people find out more about you, what you're working on and all the fun stuff? Ah, just visit timsanders.com or just hit me up on LinkedIn. Just put in Tim Sanders G2. I love it. Awesome, Tim. Well, it's been a pleasure to reconnect here, man. I love what you're working on. I love your, I love the optimism that, that your, that your grandmother, Billy instilled in you and those values because they come screaming through and, and your work and everything that you're doing.

So thank you very much. I appreciate it. Absolutely. Great to talk to you, John. Likewise. And everybody hopefully enjoyed the conversation as much as I did. And like I always say at the end of all these podcasts, go out there and make somebody smile today. Cause no matter how bad your day is going or how bad you think it went, if you make somebody smile today, you know, you had a good day and the world needs a lot more of that right now. So thank you all very much. And I will see you on the other side. Hey, thanks again for listening to the show and for all your support throughout the years. This is one last reminder to check out my training programs at jbarrows.com or leave a five-star review on your favorite podcast platform or G2.

If you've already gone through my training or sign up for my newsletter, any of those will help ensure I can continue to bring you free content and great conversations like the ones you just heard without having to know you with sponsors. Again, let's make it happen in 2026 together.

More from the show

All episodes