The Biggest Mindset Shift Your Business Needs Today, Why AI Is Shaking Up Every Industry & How To Scale | GaryVee Jobber Keynote

19 Mar 2025 · 38 min

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Episode Title

The Biggest Mindset Shift Your Business Needs Today, Why AI Is Shaking Up Every Industry & How To Scale | GaryVee Jobber Keynote

Episode Overview This episode features a keynote speech by Gary Vaynerchuk at the Jobber Summit, where he discusses essential mindset shifts for entrepreneurs in the face of rapid changes driven by AI, automation, and evolving consumer expectations. Gary emphasizes the need for self-awareness, effective leadership, and the importance of resilience in business.

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Key Topics Discussed

  1. The Importance of Mindset
  2. Quitting Too Soon: Most entrepreneurs fail not because of lack of ability, but because they quit too soon.
  3. Changing Landscape: The rapid evolution of technology, particularly AI and automation, is reshaping the business world.
  1. Entrepreneurship in 2025
  2. Perception of Blue-Collar Work: There’s an increasing respect for trades and blue-collar jobs, attracting more entrants into the field.
  3. Young Entrepreneurs: Many young people are now viewing entrepreneurship in home services as a viable path to financial success without the burden of student debt.
  1. Challenges in Leading Businesses
  2. Reality of Entrepreneurship: Many entrepreneurs face unexpected challenges, from entitled employees to financial instability.
  3. Self-Awareness vs. Grit: While perseverance is vital, self-awareness is crucial to recognizing when to pivot or shut down a failing venture.
  1. Leadership Insights
  2. Kindness & Empathy: Successful leaders approach their employees with compassion, which is essential for retention and a healthy work culture.
  3. Leadership During Crisis: True leadership is defined by how one handles pressure and adversity, not just during good times but particularly in challenging situations.
  1. Growth Strategies
  2. Maintaining Personal Touch: As businesses grow, leaders must find ways to stay connected with employees and customers without sacrificing quality.
  3. Employee Engagement: Regular check-ins and communication are vital for maintaining strong relationships with team members.
  1. The Role of AI and Technology
  2. AI as a Tool: AI can enhance efficiency and service delivery in industries, but business owners need to adapt to leverage it effectively.
  3. Training and Recruitment: AI can be used as a training tool to help new employees quickly learn skills they need to succeed.
  1. Consumer Expectations
  2. Change in Marketing Strategies: Businesses should focus on discoverability and personal branding through social media to retain competitive edge.
  3. Evolving Customer Service: Addressing customer issues effectively can lead to greater business growth.
  1. Long-Term Thinking
  2. Planning for the Future: Entrepreneurs are encouraged to take time to reflect on their long-term vision and prepare for potential changes in the market.
  3. Generational Business Planning: Preparing the next generation for leadership is vital for the sustainability of family businesses.

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Key Takeaways

  • Avoid Quitting: Persistence is crucial in entrepreneurship; don’t give up prematurely.
  • Embrace Change: Stay adaptable to the fast-evolving business landscape, especially regarding technology.
  • Empathy in Leadership: Kindness and compassion are not only ethical but practical in retaining valuable employees.
  • Utilize AI: Leverage AI as a tool to increase efficiency and improve training processes.
  • Long-Term Vision: Dedicate time to thinking about the future of your business and how to prepare for potential changes.

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Conclusion Gary Vaynerchuk's keynote stresses the importance of self-awareness, the need to adapt to technological advancements, and the value of empathy in leadership. Entrepreneurs are encouraged to remain resilient, embrace change, and prepare for the future to secure their success in an ever-evolving business landscape.

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Transcript

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0:00Yo, everybody, thank you so much for listening to this episode. it would mean the world to me if you could leave a review five star four star three star fuck it two star one star honest feedback's fine all right back to the show in today's episode of the gary v audio experience we're sharing a recent keynote that gary gave at jobber summit a conference dedicated to empowering home service entrepreneurs and small business owners he talks about the biggest mindset shifts entrepreneurs need right now like why ai is about to shake up every industry why small businesses are struggling to keep up and how to actually scale without losing what makes you great.

0:33He doesn't hold back on the hard truths about leadership, hiring, and marketing in a world that's changing faster than ever. If you're trying to grow your business, avoid burnout, or just get one step ahead of the competition, this is the conversation you need. To start the keynote, Jobber co-founder Sam asked Gary, what's changed in the last several years in the entrepreneurship and tech landscape? This is what Gary had to say. There's always change, and I think I'm very passionate to stay on top of it because I think ultimately if you're not adjusting to the truth, you become vulnerable. And I think I have a lot of empathy for the people that are on the other side here.

1:10You're doing your day-to-day gig, you know? And sometimes it's hard to pop up your head and see what's going on. And so I'm locked in. I'm ready to go, Sam. Awesome. Like my co-founder always says, you can't be so busy chopping wood, you forget to sharpen the ax. So everyone, I am going to get as much out of Gary as I can in the next 40 minutes. So let's dive right in. When we spoke first in 2021, Gary, you really drove home your admiration for home service businesses and how essential they are to the well-being of their communities, and especially given the COVID moment that we were in at the time.

1:47What are the biggest things that you think have changed since then? What do you think makes blue-collar pros vital in today's economy and how can they leverage that vitality to the benefit of their success? Look, I think, you know, the answer is not much. And in reality, I don't think much was different in 01 than 1991. I mean, it's not very complicated to understand that people that actually do things are important to the world. And so, you know, I don't think much has changed. Honestly, the biggest thing that's changed is I think more people understand the vibrant nature of the economic and entrepreneurial opportunities within the industry.

2:39I think more people in 2025 think about getting into this business than people did in 2021 and people did in 2015. And so potentially more competition for the people that are watching right now. You have a lot more 22-year-olds that are like, wait a minute, I'm not capable of starting the next Facebook, but I want to make a couple hundred thousand a year. And I love this stuff. I've done it around the house, or I'm interested in it, or I watch videos about it, or my dad did it, or my uncle did it, or my grandma did it. And so I think the biggest change that I see in the consumer data and popular culture is there's more respect for it, and there's more understanding, there's opportunity within it.

3:26Yeah, I couldn't agree more. I mean, we see that through our, we do some quarterly and annual reports that we put out at Java. We talk to young people to try and understand what is motivating them, what's holding them back maybe from pursuing a career in the trades. And a lot of people tell us, it's just maybe taking out a bunch of student debt and going to university is not maybe the right path to success and certainly not the most immediate path to entrepreneurship. No, and I think, I think nobody's gonna be confused by what I said here. Five to seven years ago, I think people were more bougie and would look down on a career in this, right?

4:09It's kind of like chefs, you're the help. I don't think that's the exact temperament anymore. And I think people have been educated on how lucrative this business can be if you, like any other business, are good at it. And I think that we've got a better collective point of view on the industry that's a little bit more elevated. And I think most humans are insecure and care about being a lawyer or doctor or entrepreneur. You know what I mean? And I think that there's more, we put more respect on the name of this game. And I think it's a very good thing. That's awesome to hear from. I mean, you have a vantage point on sort of what's going on out there that I think covers a pretty broad landscape.

4:51so that's really good to hear that you're seeing that too. We're seeing that. Yeah, to your point, just to educate everybody on that, I'm talking about like 18-year-old whiz kids, you know, who used to want to build an app getting interested in, like asking me directly, like what do you think about this industry? I hear I can make some money on it and I like it in theory. All the way to private equity leaders, the biggest in the world, sitting with me and being like, hey, Gar, I'm thinking about consolidating 15 or 50 of these or 100 of these. What do you think about the marketing plan? So you're getting it from every angle and even parents getting DMs.

5:27What you just spoke about, getting DMs from parents saying, hey, Gary V, I need your advice. My kid doesn't want to go to college, in parentheses, thanks to you, because I put out a lot of content of that. They're thinking about going into HVAC or plumbing or this and that. What do you think? No question. Do I feel it and I'm happy for it because it makes a lot of sense to me. Yeah, it's a good move. So we both, you know, huge entrepreneurship fans, love entrepreneurs. I know you'll agree that the entrepreneurs in the audience today should be damn proud of themselves. You know, they've taken the leap of faith, you know, really put themselves out there, chosen the harder path in pursuit of, you know, their own personal vision of freedom and success.

6:10However, you know, once you're in the day-to-day of running a business, it is usually not what you think it's going to be. It's just a lot of bullshit to deal with. and you're usually drowning in a bunch of TVs that you don't want to deal with. How do you deal with that? Less yachts and private jets and bottles and dudes with abs and pretty girls and much more entitled employees and losing a piece of business and sleepless nights if you're gonna have to go back to a job and look shitty in front of your friends and relatives because you talked a big game that you were gonna build a business. Entrepreneurship's incredibly lonely and very challenging.

6:50You know, for me personally, Sam, there was no choice. I've literally done nothing else. I genuinely believe what I'm about to say. I would be fired or quit any job I would have taken pretty fast, not because I'm a bad guy or I'm entitled. I am just truly someone who's incapable of breathing if he's not creating some sort of entrepreneurial venture for himself. So for the people that are like me, that are on this call, I would just say, you know, like, we have no choice. That'd be like asking us, how do you breathe oxygen? That would, literally you asking me, like, entrepreneurship, to me, the comp is oxygen.

7:37I don't know, because I would die, I guess, pretty quickly if I stopped breathing. You know, and so, So I think for the people that are half in, right? They have 50 % entrepreneurial tendencies, 50 % the fear that comes along with entrepreneurship and think about getting a good job. What I would say to them is just make sure you see it all the way through. Let it go out of business or right to the cusp of it because what you don't want to do is jump too early, go back into a job because you see your savings going down and then live with regret your whole life. Now, only God knows, I surely don't know if your business was gonna turn around in six months or you just would have wasted six more months of your savings.

8:23What I do know is that I've been a public figure in entrepreneurship for almost 20 years now and I've read unlimited emails and the people that jump too early then are always asking what if and regret for the rest of their lives and the people that went to zero knew that they weren't capable and went back to a job and lived their lives. And so, look, I don't like to talk about how another man or woman should spend their money and people have bills and responsibilities and I'm not sitting here saying, waste your savings to, you know, do play entrepreneurship for another six months. In fact, if you know that you're not an entrepreneur 18 months in now, you've been on this journey, you're watching right now because you're kind of hoping for a Hail Mary from me and this conference, But you're really sitting there and you're like, I've been doing this for 18 months.

9:14And you're losing money and you're tapping into your savings. If you're 100 % sure, shut down the company and get a job. But if you're not 100 % sure, fight as long as humanly possible because regret is much more poisonous than an empty bank account. To the soul of a human. Yeah, that resonates. I think probably there's a lot of nodding heads in the audience. It just really recognizes the fact that perseverance and tenacity and grit are some of the most important characteristics in entrepreneurship. You have to push. You have to fight. I'll give you another one, though. It's not, but I will say to balance grit and perseverance is self-awareness and lack of delusion.

10:07say I'm on the counter I've met kids and people that have come you know I'm a funny character I interacted with a lot of random situations on the street in my office sometimes I just say yes you can come for 10 minutes one out of every 100 emails or DMs or a thousand or now probably 10 ,000 and I've sat in many conversations where the person's completely delusional they're like Gary any minute now I'm like no I'm like you stink at this the way I stink at skiing and many other things. And so you really, really, really should shut down this company. And I'm not a dream crusher. If I see 1%, I'm an optimist and I'll push.

10:48So I think, yes, grit and tenacity and everybody should fight. But I implore and I beg everyone to really think about self-awareness. Look at the data. If you've been losing money for four years, there's somebody watching potentially who inherited 80K from grandma and has been like, you know, like deducting that every year because they're losing, you've got to be honest with yourself and self-aware and that's important. I want to talk about leadership a little bit, Gary. You talk a lot about this and I think, you know, empathy and kindness are themes that come up a lot. We are talking to a group of entrepreneurs today that are, you know, they're small businesses, you know, one to 50 employees, think about it, but you and I both know the vast majority of all small businesses are maybe just a couple or a few employees.

11:38Leadership means something very different. And I think, you know, these concepts of kindness and empathy, I'm just really curious to hear how you think that applies in the context of truly small business. What does it mean? Yeah, I've been involved very aggressively with multiple small businesses. You know, VaynerMedia, VFriends, VaynerSports, Wine Library. You know, most of my companies, all of my companies, I've never bought a company that had employees. All of my companies have started with less than a dozen employees. So I've only known this world. And obviously, I've built some companies that get bigger.

12:16First of all, I think kindness, empathy, compassion for your employees. One of the biggest mistakes, and this is gonna hit right, I'm about to put a spear right through a lot of people's chest. A lot of people on this call think these people are theirs. A lot of people think if I pay someone, I own them, they owe me, like they're lucky to have a job. Like they get very audacious. And so the first thing I would say is be a human being. Because what everyone here that's watching is looking for in their first 10 employees is continuity and retention. Right? Now, you as a boss, if Johnny stinks, you can fire them.

13:05You don't want to retain somebody bad. But the biggest vulnerability, Sam, to most of the businesses here, here's a good one. Let me bounce around a little bit. Close your eyes, everybody, right now and make pretend the person that you believe is the most important employee in your company quits tomorrow. I know you know this, Sam, because you're of this business. For a lot of people on this call, that is a mega blow. For some people, it's a death blow because their number one employee is actually more important than them. For a lot of people, it's a dent. Like in fighting terms, it's a knockdown and they might get up at nine and be blurry.

13:43For the best crew here, their number two and three can easily absorb that and it's a non-event. So the biggest thing I tell people is I don't think kindness and empathy and compassion is a, I don't think it's something altruistic or funny or like I want to look good. I think it's practical. Yeah. It's self-preservation. A hundred percent. You need to retain your best people. And by the way, there's a lot of words matter. You just said retain your best people. I think some people are good to their best person and then bad to everybody else. For most businesses, you need your worst employee too.

14:25Yeah. Your best people see that. Yes, and it becomes, and that becomes the culture. If you treat your weakest link similar-ish, because I think your best link deserves a little bit of extra love, but if you're in the same general ballpark of humanity, like you're not hugging your best guy and cursing out your worst guy. If you're in the same pocket, you're cordial, you're warm. You know, and I'll say another thing about leadership and employees and all this theme. I tell my direct reports and my top people in my companies, I don't need a peacetime general. I don't need you to be a leader when it's good, when it's prosperous.

15:10I'm not paying you or you're not my number one guy or gal when it's easy. I need you when it's hard. And so as leaders, a lot of owners that are on this call, they're fine when things are good but as soon as they feel stress they start to get nasty. They start to because they're scared and it starts to show up. The form of a leader is to take all the pressure and have it stop with you reformulate it and make it productive underneath you. That. If you're a leader and you're just passing through the anxiety of paying bills bad customers losing a big account being worried If you're taking that on and it's getting fully to your team in the same pure form, you're not a fucking leader.

15:59You're a losing player. People's true colors tend to show in those moments too. Adversity exposes. Adversity exposes, brother. It's a good lesson, I think, for people probably to pay very close attention to how they behave and how they react in those difficult moments. when things start to get tough, kind of take a beat and take a deep breath and consider that what you do next is going to define the culture of your business. Not only the culture, what you do next and how we're framing this, I think it's gonna help a lot of people, is probably the best indicator of how healthy and financially stable and how much money you're gonna make.

16:43Sure. What does this industry have without its people? Yeah. What do you guys sell? you're not right you're not you're not slinging sneakers to people if your people situation isn't good what are you on this call yeah your pipes are the same you the the replacement of the physical i can buy from anyone if ricky's or sally is a jerk when they're at my house doing stuff i don't like your company. Ricky and Sally are always going to be a jerk based on the owner. Here's why. If Ricky and Sally are good or they're reliable, that's a good one, Sam, for this industry, if they're reliable, but you know they're a jerk and you haven't fired them because you're scared to you can't find someone reliable, that's your fault.

17:36If Ricky and Sally are a jerk because you're a dick and they don't like who they work for and that shows up, that's also your fault. It's always your fault as an owner. Yeah, and that's going to hurt your bottom line. It's just a matter of time, especially based on how we started this call. New kids are coming into this industry. So let's talk about growth then. So a lot of people on the call, they want to grow. They've got growth goals. They want to grow, but they're worried about losing that sort of, you know, for the ones who have done it really well, they're worried about losing the personal touch that's gotten them to where they are with their customers and with their employees.

18:14So how should leaders approach the challenge of growth and the objective and the desire to grow without sacrificing quality and the connection with their employees and their customers and the quality that works so hard to build? Yeah. Let's start with connection with employees. Until you have 100 employees, you don't have that many employees that you can't do five minute check-ins with, texting, group dinners. I don't want to hear it. I've seen it 100 ,000 times, not just by me. So unless you have 100 employees and going to 500, I don't want to hear from you. And Sam, I'm going to assume a majority of people here are not close to 100 employees.

18:55so let's you're gonna if you want to Sam there's people here that have four employees that are not connected to their employees that are not taking them out to a Tuesday night dinner that are not texting them like happy birthday that are not like saying hi in the hallway I have 2 ,000 employees that do that shit so so that I don't want to hear about now same front on customers Sam what's your gut on how many customers you're gonna go very average here in guests but like how many customers are we talking about for somebody here that they're gonna interact with this year? Yeah, I mean, it depends greatly on the industry, but 50 to a couple hundred or a few hundred.

19:37I mean, I think I emailed 50 customers yesterday. Yesterday. I'm being serious. I'm not making that up. Yes, Monday? Yeah, yesterday. Yeah, talk about a facade of excuse. You know what's funny about excuses, Sam? Do you know that all of us are disciplined in the things that we prioritize or like? All of us, whether it's the gym or eating or parenting or work, everyone here is disciplined at something. You need to be disciplined with growth. You need to continue to, you know, you might not be able to do every job, You know, if somebody here is scared of like, they used to be the person hands-on doing the job and they're scared to hire Dustin and he doesn't do as good of a job, I respect that.

20:33But don't forget about the I'm sorry and the fixing it up. You know, like, people ask me a lot back in the day because I've scaled businesses fast. They're like, how? And I'm like, the power of I'm sorry. Like, if I hire people and they do a worse job than I would have done, I have the ability to the power of refunding. Every day of my life I think well if this goes catastrophic I could always give them the money back. I could. Small businesses you might not be able to afford it. I get it. But I think people demonize one bad you know like we hear this a lot. It's like not the issue isn't the issue how you address the issue is.

21:20Right? In fact, there was a time, I wrote a book called The Thank You Economy. I'm looking at it right now. I don't remember if I put it in the book or if I took it out at the last minute because everybody around me was freaked out by it, but I almost recommended as a business strategy to fuck up on purpose just for the I'm sorry. I felt the aggressive over the top I'm sorry to a screw up was actually more valuable than just doing the job right. That's really interesting. Getting some reps in, recovering, and doing what's necessary to get back to the good place. Let's talk it out. Anything is fixable if you have good intent.

22:00Anything is fixable if you have good intent. That's good philosophical advice. You're right. I think it's philosophical advice and I would use a different word. I think it's business strategy that if you then execute against that strategy, you will grow your business. You will not be crippled by... And by the way, let me go into very deep psychology of this industry and industries like it. A lot of, Sam, this is gonna blow your mind because I've spent a lot of time on this back in the day. It's fun to bring it back up. I haven't looked at this psychology in a long time. Do you know there's some people, Sam, here that don't wanna hire people that are better at the craft than they are because their self-esteem is wrapped up in them being better at the actual job?

22:46and so they literally have not built a bigger business because they don't even realize this. It's subconscious. They kind of razz on a guy who's doing a job. They find something that was wrong even though it was probably just fine. They need this belief that they're the best at hanging the shingle or fixing the fucking pipe or fixing the window or putting up the shingle or redoing the roof or fixing the faucet or replastering the wall. Like they have this, their identity is in their hands and craftsmanship and so they're sandbagging their business because they're not giving craftsmen and women the breathing room and the accolades and the trophies and the self-esteem boosts because they themselves want to feel like they're the best at it.

23:37It's wild. I see it all the time. 100%. And that will 100 % of the time limit your ability to scale. 100%. Of course you won't scale. All right. Let's talk about change. I mean, growth then leads to change, of course. And I think there's just dozens and dozens of forces pushing and pulling on consumer attention and preferences. This is an area of change that I think a lot of entrepreneurs, small businesses pay attention to and really want to deliver value to customers. So in what ways have you noticed consumer expectations changing the most over the past handful of years? And how should small business owners be thinking about and reacting to that?

24:15The place that I'm most interested in is how everybody here gets their business. You know, a lot of people here get their business word of mouth. And that's why we've been stressing for the first 25 minutes all the things we just talked about. Everything I just talked about, literally for the last 20 minutes, is to keep the word of mouth engine going. but there's also discoverability. And so, you know, the biggest change is, let's go back to when I was a kid. If my mom or dad needed somebody, yes, word of mouth was in play, but boy, oh boy, the yellow pages were in play too. Right? And that's why everybody called their companies AAA HVAC, AAA plumbing, AAA, you know, gardening and roofing, because you showed up first.

25:01Yep. I think some of the kids may not know that's why every company was called AAA because before there was Google search, there was that. Now, as everybody here knows, Google became a major engine, right? Now, need a plumber near me, major. I think the biggest thing in the world right now is AI is starting to eat up, chatbots is starting to eat up search. Sam, are you starting to use chat GPT instead of Google yet or not yet? Yeah, or other AI tools for search. 100%, yeah. Wild, right? Yeah. And how old are you? 42, I think. Right. So I say that because this is not a 15-year-old reality. I'm already, I mean, it was fun to be in the holidays.

25:40I was down in Florida, a lot of 60, 70, 80-year-olds, and I get to do my anthropology work, and I'm walking by, you know, any time I walk by on vacation, like I just did, you know, eight, this is the story I'm telling, eight 65 to 80-year-olds, sure enough, watching two, like I got to catch like 17 seconds of this. basically what I was able to gather two 60 to 80 year olds actually 70 to 90 year olds they weren't 60 showing the rest of the table how to use chat GPT and so I think one thing so let me say this very loud anybody here who gets most of their business from Google AdWords and SEO and SEM they better start hedging it's not going to be tomorrow but in three four years it's going to be a different environment the other thing is trust I still believe every person on this call if they themselves made one to two social media videos a day and posted on every platform and showed people tricks of the trade.

26:41My favorite, I always say this, I probably said it in 01, how not to hire me to help you because you could just fix this valve or anything that builds trust, I'm very hot on, personal brand continues to be important and what I like now is best tactics is if you post it and you normally get 10 views but this one gets 5 ,000 organically, but you're only doing business in North Dakota, you then take that video and you run a couple hundred dollars of ads in a 30-mile radius of your home or your home office or your office. And so now you've taken creative that works, but you make it localized, and that actually leads to business.

27:21Very interesting. I want to hear a little bit more about your thoughts on AI. I mean, AI is obviously one of the greatest change agents we've seen. And I mean, I just revealed I'm 42, like maybe in my life. I mean, it's amazing how much it has changed so far and how much it stands to change in the future. You've likened AI to like a tidal wave and you've talked a lot about the importance of being prepared for it. You just can't ignore it. I think blue collar pros are in a really great position to benefit from this tidal wave. In the first wave, I think the thing that I'm sure, you know, the first wave, yes, it makes you so much more efficient.

27:59Everybody here should start learning how to be a prompt engineer. Google that, prompt engineer. I'm sorry to jump in, but the one thing that I do want everybody to pay attention to is, I saw the headline, I didn't watch it yet, but like, did I see right that Elon's talking about like making a million robots in two years and you've got like, you know, the NVIDIA guy talking about this and that. Like, you know, look, I mean, do I believe in 10 years that the person that comes to build something in my home is a robot? There was that Megan Fox movie on Netflix, right? And all the workers of the job are robots.

28:33I think you've got to pay attention, brother. Yeah. Advances in robotics certainly will threaten on some time horizon. But I think it may be a long time. At least the AI that we see today. But Sam, I'm sorry to interrupt. I think it's important. And I'm not here to scare. and honestly I'm saying this because I think it actually can lead to offense. Let me ask you, let me reverse this. Sam, do you believe everybody here should think about how they build their business and what they do for a living and how they do it with the belief that 17 years from today robotics advancement will get to a place where a robot may come to the home and do the job?

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29:14I'm asking you, yes or no. Do you think 17 is a number, what would you say, yes or no to that? 17 years, I mean, gun to the head, yes or no. I would say a lot is going to change in 17 years. You should be thinking about building your business with as much optionality as possible and understanding that technology is going to dramatically change the way that you operate. I think it's valid. Yeah. I think people are hesitant. What do you do? I mean, there are. Yeah, man, I don't want a fucking robot to come into my house. Like, what if it, like, at first, there's going to be enormous amounts of fear.

29:51At first, it's going to be like, wait, so, like, you know, my kids are home with my girl, and, like, the robot comes over, and what if the robot fucking malfunctions? And, like, we're going to be scared of that. We're going to be scared of that. But for adoption today, I mean, people, you know, you mentioned some of these older folks who, you know, they're using ChatGPT. I agree. I'm amazed at how much people are, people who I wouldn't expect are really engaging. with it. But people are hesitant too. So how do you get them to cross that chasm? I could give a shit. I have no interest in convincing people.

30:23You know what's gonna make them cross the chasm? Pain. When they're getting outflanked by human beings. What do you think happened with search? Bro, I'm 49 and was at the forefront. Everyone told me search was silly. Why? I have a yellow pages. Literally, that's what they said. I'm not gonna... I remember one guy telling me that the computer was upstairs. this is a real talk 1999 Gary I'm not gonna use Yahoo the computer is upstairs my yellow pages is in my kitchen it's faster for me to grab the yellow pages than to go on and he wasn't wrong my counterpoint was do you think it's always gonna be like that even then I knew the even then I wish I was making videos in 99 this would probably be one of my biggest videos.

31:14In fact, I actually have a video. I actually have a video that says the phone and the flip cam are gonna be one. Come together, yeah. Right? Which, like, and so, there was a reason I bought the iPhone the day it came out. Even everybody said it was too expensive and the Blackberry was good enough. Anyway, that's a long-winded way to say, I'm not here to convince. I'm telling everybody when people are out flanking you, when, I'll give you an example. I can do a job in this industry right now because of AI and I'm the least handy person on earth but I know how to ask enough questions to ChatGPT and Gemini and Midjourney and I can literally take a video from YouTube post it in ChatGPT and say okay I've never fixed anything in my life this is what I would write here's a video of how to fix how to install HVAC I've never installed I've never hung a picture chat this is what I would write I've never hung a picture in my home.

32:14I'm completely incapable. I have two left hands. I uploaded this HVAC video. Break this down for me with the highest propensity for me not to make a major mistake step by step. I can literally get there. Yeah. It's pretty amazing. Yeah? It's pretty amazing. I think, so, I mean, what you're saying, if I'm hearing you, is like, this is an existential moment. People who don't or won't adopt will, either will fail or they will adopt because they'll experience enough pain to force it. That's right, Sam. And let's take the other side of the pillow. Okay, so now everybody's like, oh man, maybe some people got scared.

32:52Let me go the other way. What I just explained now becomes the single best training manual for everyone here to take a kid off the street and become a good employee. Instead of like what we're all frustrated with, like damn, gotta take the kid. Oh God, you just gotta learn from the OG, but the OG's got to do the job and the OG's not good at training. No, no. How about using technology to take a kid from curiosity with the belief that they could do this to building out a training mechanism for him the first week he's in your company using AI? Yeah. In a lot of ways, it's no different than it always has been with technology.

33:32Technology for hundreds of years, thousands of years, has enabled improved productivity and the ability to do more with less and it's always created a necessity to adopt and this is just more of that. Yeah, there used to not be tools. There used to not be jobber. That's right. I mean, look, I think finally, and I want everyone to hear this, before we talk about 15, 17 years from now, if you leave with anything, and especially if you saw me in 21, why are you not making social media content? It will grow your business. Okay, well, let's talk about 17 years from now. We've got just a minute or two left.

34:13I think it is important to think long-term. And as an entrepreneur, you often get bogged down in sort of the fires that are burning immediately in front of you or the opportunities as well that you want to chase immediately in front of you. But how can you change your orientation and force yourself to think 10, 15, 17, or 20 years into the future and increase your odds of enduring success over the long time, especially in this environment that's so unknown and dynamic? I want everybody to take one day off next week or next month and think about the next five years. Not 17, just too long of a putt for a lot of people here.

34:53But, you know, if you have a 17-year-old son or daughter that wants to get into the business, now they're 22. You know, if you've got an employee who's been your, let's go back to real life, It's your guy and he's 64 and he's been telling you he wants to go to Florida and every year you're like, no, no, no, don't go, don't go. I think planning is good, especially when the organization's health really dictates your entire life. And so, you know, I think in a five-year window is a very good way to think. I don't put anything on paper. I don't make a deck. I don't make a presentation. Some people will.

35:32I don't have a vision board. but I'm thinking constantly about what's in front of me today but also two steps forward and then 14 steps forward, right? I think it's just a good way to be because then nothing catches you off guard. Again, I think a lot of people here are putting their head in the sand. I like that 64-year-old guy story. Like they just hope, like they hope, they hope, they hope and then the thing happens and then there's the unexpected. I mean, what if your business was based out of the Palisades in LA. Some people, yeah, we have customers there. And so, you know, it's just life, you know, there's this Russian saying, and I know it's a saying because I say it a lot, and a lot of people say, no, that's a Persian saying or a Korean saying.

36:16Obviously, every language has this saying in nationality and culture. You know, the one that I was always told in Russian as a kid translates to, man makes plan, and God laughs. And so, I'm not asking you to think about a five year window because you're gonna actually fully execute that plan. I want you to be a human being that is always prepared for something. I think that is the perfect parting thought, Gary. Really thought provoking. I hope people sit with that one for a bit. Book a day off to spend the time thinking about the next five years. I agree, I think that's a good timer. I know we're wrapping up, but like including do you want to be out of business in five years?

37:03And not like I'm going to be a trillionaire and I have a boat but like hey you're tired and like you know back to that 17 year old like if you're dreaming that your kid's going to take over and you're going to go to Florida and nothing bougie just in a senior retirement you just want to rest. You've worked 44 years of your life. Well shouldn't you be getting your kid prepped? Because if your kid comes out of college or you know whatever at 22 and you're like all right take it over and they've never really worked in the business or a couple summers, a little bit here. Like, you may lose two, three more years.

37:35Happened to my uncle and aunt. They wanted their son to take over and it took three more years because he needed more reps and then my aunt's still involved kind of in the business. Like, and so, you know, I don't know if my aunt and uncle liked that. Maybe they liked it. That's perfect. But if you don't like it, so like, I just think planning helps. Yeah, planning is very important. You gotta dedicate the time. hard for entrepreneurs to do. There's so much going on right in front of you. You have to dedicate the time to thinking further afield. Gary, we're right down to the last second, just like last time.

38:08Thank you so much for spending the time with us today, and I hope that we'll see you back in another five years, 2030. Can't wait. I'll be ready.

From the publisher

Most entrepreneurs don’t actually fail—they quit too soon. And in 2025, quitting is easier than ever. The business landscape is shifting fast, with AI, automation, and changing consumer expectations redefining what it takes to succeed.

In this episode, we’re sharing a recent keynote from Gary at Jobber Summit, where he breaks down the hard truths about running and growing a business today. Whether you're a small business owner, entrepreneur, or leader, this is the real talk you need to hear.

💡 We talk about:
✔️ The biggest changes in entrepreneurship and tech (and what to do about them)
✔️ How to scale your business without losing what makes you great
✔️ The rise of AI and automation—what business owners need to know
✔️ Why most businesses struggle with hiring and leadership (and how to fix it)
✔️ How to stay competitive in an industry that’s evolving fast
✔️ The power of content and social media for business growth
✔️ Why self-awareness matters more than perseverance in business

If you’re trying to grow your business, avoid burnout, or just get one step ahead before the competition, this episode is packed with tactical, no-BS advice you can use right now. 🔥

🎧 Tune in and future-proof your business.

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