The future of work, with John Winsor

Dive into the future of work with John Winsor, University of Denver alum and expert on Open Talent. In this episode of the Entrepreneurship@ DU podcast John shares his entrepreneurial journey from magazine publishing to disrupting the advertising industry, and offers invaluable insights on navigating the evolving landscape of work. 

Discover how the concept of Open Talent is reshaping traditional employment models and learn practical strategies for both businesses and individuals to thrive in this new era. John discusses the impact of AI, the importance of continuous learning, and the shift towards portfolio careers. 

Whether you’re a startup founder, a freelancer, or a corporate leader, this episode offers fresh perspectives on building organizations, leveraging global talent, and embracing a more human-centric approach to work.  

 

Joshua Ross:

My name is Joshua Ross, and welcome to the entrepreneurship at DU podcast.

John Winsor:

It’s been hard. I’ve been the prototypical rogue entrepreneur. I’m totally unhirable and I couldn’t get a job if I tried, but I love doing things. I love shaking up markets, and I think part of my personality, for whatever reasons, is just be provocative.

Joshua Ross:

Today I’m talking to John Windsor, a d alum who went from starting and scaling several businesses to becoming an author and an expert on the future of work and talent. John chairs his entrepreneurial story and insights from his book, open Talent on Navigating the Future of Work.

John Winsor:

So that’s the other mentality that needs to shift is instead of saying, I’m going to have one job at a time and be a hundred percent dedicated to it, they’re going to own my time. That’s little bs. It’s like your life. If it’s your time, they do what you want to do, pop into the projects you want to pop into, give the effort you want to.

Joshua Ross:

The concept of open talent disrupts the traditional employer employee relationship and leverages tools and behaviors that were accelerated during the pandemic. Empowering you to work on what you want and where you want to work from if

John Winsor:

You’re young and talented, is you need to figure out your life, right? It’s not about the work. It’s like where do you want to be? What do you want to pursue? How do you want to do it? And then have work fit into that.

Joshua Ross:

Here’s my interview with John Winsor, John Winsor. Welcome. It’s great to have a fellow DU alum on the podcast.

John Winsor:

Thanks, Joshua. How are you?

Joshua Ross:

I’m wonderful. So just to get started off, would you mind walking us through your entrepreneurship journey? And I want to put a timeframe around this. Okay. Post DU and up to the decision to write Open Talent, your book, which we’ll talk

John Winsor:

About. Oh my God. You have three or four hours to talk? I do, I do. Oh, geez. Wow. Well, I got to conclude, du, I got to give some props to DU because that was in Ron G. First Entrepreneur class. I think there were 15 of us. And the reason I attended DU is I had written a book called Fitness on the Road, and I’d seen a magazine called City Sports out in California, and I wanted to start that, and I thought, so I wrote this book and my editor said, oh, you’ve got nine months. And so actually it’s a little different than it is now in that I applied on a Wednesday and school started on Monday and was able to slide into the MBA program. I don’t think it was as popular as it is now, but what was interesting is one of the reasons I did it is I wanted to leverage my fellow students expertise with projects.

So all the projects I did at DU was to launch my first company out of du, and I did that my first year in the MBA program. And so it was called Sports and Fitness Publishing. It was a regional title, but I got super lucky. I mean, I think a lot of it was, first of all, finding something that maybe I wasn’t super passionate about, but I knew a lot of because my grandfather and my dad were all in the newspaper publishing business. So I kind of fell into the magazine biz after college, worked for somebody here in town, and then started my own magazine company. And it worked out really, really well. I sold that company to Conde Austin in 2000, but that was the seeds of the work I’ve been doing for a lifetime. And so how I got to open talent, it really started with the purchase of women’s sports and fitness.

Women’s sports and fitness was bankrupt. Our Time Inc was bankrupting it. And so I was nervous. My wife, Bridget, was a professional triathlete and a lot of her friends were professional, professional athletes. And so one of the things that I was really interested in was, and they were really interested in, is this disparity between the fact that magazines participants were 50% women, 50% men, but all the media was all men covers of runner’s world or bicycling or whatever. And so I thought there was an opportunity, and so I flew to Nike, Mark Parker, who eventually became the CEO and Tinker Hatfield, who’s a great creative leader guys. And I was like, what do you guys think? Do you think women will do sports? They’re like, yeah, yeah, yeah, you should go for it. And I told ’em it meant that I had to put every asset on the line, I had to put my house on the line, mortgaged my house and everything, and made that bet.

So I did it. But one of the things that really worked was reframing the basic model. Time Inc. Had 40 editors and writers in the way that it would work is that they would send a writer to Boulder and they would interview somebody like Lynn Hill who’s a really well-known and accomplished rock climber. And Lynn would, the writer and editors would go back to New York and probably not have much experience, and they would write this story that was really not super authentic. And so I thought maybe I could change the paradigm, save a lot of money, maybe I could have a couple editors. But then Lynn let Lynn write her own story and then let the editors edit it for the audience. And so got really lucky there. That blew up. Women’s sports happened. My economic model was the right one. And so sold that.

And then I was really intrigued. I felt, when I was in that magazine business, I felt a little disgusted by the advertising business. I knew that there was this big funnel and Bran said all this money and that all this money was being taken away by these intermediaries. And then by the time the ads would run in women’s sports and fitness, we’d get tens of thousands of dollars starting with millions to reach women. And I thought, well, instead of paying $10,000 to reach 250,000 women that were our readers, let’s take those readers and put them at the top of the funnel and then charge the companies a lot more money. And it compensate women in a lot better way by helping those companies design better products and design better marketing messages. And that worked out really well. I kind of, in my book, beyond the brand, I called that, so that was the seeds of this idea of working with many voices that led me to launch a company called Radar Communications.

And we worked with Nike and Levi’s and Intel and a bunch of other folks thinking about how do we bring more authentic voices into the process of building products and marketing. And that led me to merging that company with Crispin Porter Bogusky. And that was a crazy ride because at Crispin, I had written three other books on the subject of co-creation, but at Crispin, there were 45 of us, or 45 of them that had moved to Boulder from Miami and another 25 in Boulder, or sorry, another 25 in Miami, and there were 15 of us, and we merged companies and went from about a hundred of us to 1200 in two years, all with the idea of putting co-creation at the core of our work. So Domino’s Pizza, Microsoft Miller Brewing, $3 billion worth of work. And what happened was is that we had just won Creative Agency of the Decade and from Canada,

Joshua Ross:

Wait, a little boutique shop in Boulder, Colorado, I know Wins. Creative Agency of the Decade. Global. Global, yeah. Where did you win this? Where were you awarded

John Winsor:

At Can Of

Joshua Ross:

Course. Of course. Yeah,

John Winsor:

Yeah, for sure. It was crazy. But when we won that, we didn’t have any creatives to do this really interesting project with Bramo motorcycles. And essentially we decided to crowdsource the creative on a platform called crowdSPRING, and it just pissed off the whole industry. And we thought, oh shit, this is so awesome for a couple of reasons. One is the people we would love to work with, say from Sydney or from London, all of a sudden we could work with them because it was all digital exchange of information. It wasn’t, they had to move to Boulder, which probably they wouldn’t have, who wants to move from London to Boulder from the advertising business, but we could work together. And so Alex looked at me and said, oh, shit, this whole industry’s done. If we can connect digitally to anybody in the world and work with them, it’s over.

And so that really intrigued me. So I started a company called Victors and Spoils, and to me that’s the most interesting entrepreneurial journey that I’d love to just spend on. A couple seconds on. Go ahead. Yeah. So to me, the most interesting thing is we had this philosophy at Crispin, and what I think is really important for entrepreneurs to remember is that the cultural myth is like we need to analyze culture, and then we need to get ahead of culture and get in its way. And it’s like whether you’re working on film or you’re working on advertising, you’re working on products, so you analyze the market, you spend millions of dollars or tens of dollars, whatever, you have to figure that out and you run in front of it. Well, we had this kind of insight at Crispin that was just the opposite. We said, if you do the right thing at the right minute or at the right moment, you can change culture to your advantage.

And we did that with Domino’s Pizza. We’d done that with Mini, we did that with Volkswagen. We’ve done that with a lot of companies. And so I just kind sensed that this was the right timing. And so I made this deal with the New York Times and Stuart Elliot, who’s a writer, I dunno if you remember Stuart, but he wrote the marketing stuff, a lot of agency stuff, and he was kind enough to write a three quarter page article about victors and spoils. And so I had raised a little bit of money and there were three of us in my garage, and I was freaking out. I was running out of money and I had a website, but I couldn’t launch it. I told the New York Times, I wouldn’t. And literally on a day in October, October 29th, 2009, the New York Times article hits in the morning. And that afternoon, by that afternoon, by the time we closed six o’clock, we had 3000 people sign up to work for us.

And Dish Network Ira Barr here in Denver gave us the 110 million advertising campaign or advertising work. So we went from zero to about $12 million in revenue in 12 hours. This never happens, by the way, and this is a great story, and I love the fact that you did it in your garage. I know, right? Well, but I think it points to the fact that entrepreneurs, instead of spending all this time and effort trying to get it right, how do you figure out where the lever is in culture to leverage that to your advantage? I, it’s harder these days with social media and everybody having a voice, but I think that’s an opportunity. And so that kind of led me to, we had a lot of other successes that were just as intriguing. I think one that I just would like to point out for the entrepreneurs in the audience, again, it’s like always ask yourself, not why, but just why not?

To me, that’s the most important thing, right? It’s really be audacious. No reason not to be audacious if you’re young and entrepreneurial. And so we noticed a couple years in, we had about 10,000 people in our crowd by then that were doing work, and it was super fun. It was like these people, I just remember this mom from Cyprus who was a single mom. She was from France, couldn’t afford France, moved to Cyprus, and she was killing it. She made like $75,000 from us just doing graphic design. And she was really playing that value arbitration. She was living in a place she could afford doing global work digitally. And that really intrigued me. But one day we were sitting around our office and we noticed that Harley Davidson had just decided to put their work up for review, and they’d had an agency for 32 years, Carmichael Lynch.

And so Evan Fry, my creative director, and I went to coffee and we said, man, that would be super awesome if we got in that pitch. But we knew we’re not really a big agency. We’re really outrageous and we’re really well known globally, but we’d never do that because pitches are like a half a million dollar affairs for agencies, and there’s lots of whining and dining and dinners and golf and all that other shit. And so what we decided to do, Evan just kind of looked at me with a really funny smile. I was like, instead of asking permission, let’s ask forgiveness. So we ran back to the office and literally in 20 minutes we said, we made this little recording like we’re doing today, very hacked together, way less professional than this. And we announced to our crowd that we’re working on Harley Davidson and I did a little video going, we’re working on Harley Davidson.

I put $10,000 of my own money up. Let’s see if we can get a response. And so I had 10,000 people noodling on it. And then I wrote the CMO of Harley Davidson, Marcos Ricker. At the time, I had as many followers on Twitter or EX that they did because it was early days. And so I wrote this blog post that said, Hey, mark Hans, have a great time at those really great dinners and all those really fun wine parties. As you do that, I got 10,000 people working on your business. Give me a call if you want to see some work. And that hit Twitter. And literally 20 minutes later, mark ha’s record pings me back and says, awesome. I am tired of traditional agencies. Come to Milwaukee and show me the work. Two weeks later, we went to Milwaukee and we won the global Harley Davidson account, which was so crazy because the industry totally, it put the whole industry on its head.

Joshua Ross:

Those are great stories. And what I think is really important to understand is somebody from the outside is like, God, John got lucky on that one in his garage. Got lucky with Harley Davidson. But you make your own luck for sure, and you put yourself out there and you try things, but at the end of the day, you need to actually back it up with quality work as well.

John Winsor:

Oh, for sure,

Joshua Ross:

For sure. And that’s what you did. So, okay, that was a nice lead in. What I want to talk to you about next is the book. Love the book. Yeah,

John Winsor:

Thanks.

Joshua Ross:

But I also really appreciated the book. I thought it was really, really interesting. And one of the first questions I have though is what inspired you to write this book first, and who are you writing it for?

John Winsor:

It’s been hard. I’ve been the prototypical rogue entrepreneur. I’m totally unhirable and I couldn’t get a job if I tried, but I love doing things. I love shaking up markets, and I think part of my personality, for whatever reasons, is just be provocative and so well, because I found my way to Harvard and I have a lab at Harvard called the Laboratory for Innovation Science at Harvard that we’ve done a lot of deep research in this area. And what’s been fascinating is so the primary audience is really organizations. And yet the reason we targeted that was that we want to see freelancers thrive and survive. And we view the world as the future of work, as having portfolio careers that you have digital platforms that allow you to connect, that become kind of your business development platforms that connect you with work. And the issue that we see in the market is there’s not common language and common process around open talent.

And we defined open talent as using external talent cloud, so freelancers, high-end freelancers that could do work, and using internal talent marketplaces, essentially reinventing the HR arrangement with workers, the contract with digital platforms that allow workers to actually manage their own careers. And then open innovation competitions that we’ve done a lot of with nasa. And so those are kind of the three legs of the stool. And we feel like we need to digitally empower individuals to take more control over their careers and have opportunities. The problem is that that door isn’t all the way open. A lot of companies aren’t willing to hire freelancers yet. And so the purpose of the book is to really before the independent worker, before the freelancer, but do it in a way that creates more opportunities for them by creating common language and common process for large enterprises.

Joshua Ross:

Alright, so to table set for our listeners, can you give us a little bit of an explanation on the difference between open talent and a gig worker?

John Winsor:

For sure. So gig work in our mind, I think it is like anything, right? There’s so many terms that get kind of bastardized. Well, I think Gig was a great way to define the marketplace for a while. It really has morphed into a space that’s controlled by a few global companies, Uber and DoorDash. And it’s really people being managed by algorithms. You’re told where to go to work, Hey Joshua, go to the airport, pick up Betty and Driver to Colorado Springs, and then how much you’re going to get paid. And it’s a commoditized business. I think it’s good. And I think there’s less friction and there are some really great benefits, the ability to work side gigs and things like that. But really what open talent is, is the ability to take your skills that you’ve really been honing, take your passions, and then be able to find great work.

And I think one of the things that Covid really did and the Pandemic really did is it really shifted from this having work as a place that you identify with. My identity is I work at DU, or I work at Crispin or whatever those are, to being like, man, I re met my neighbors and I hung out with all these cool people. I don’t go to work every day. I kind of have these new relationships that I should have had 20 years ago. And so now it’s about having your life and being able to work when you want and how you want in a new way, but work’s still an important part. It’s just not the dominant part of defining who you are. And I think that’s the big tension in culture right now. I think so many executives think, well, why don’t people want to return to work? Well, they don’t identify with your company. They’ve got other lives. They want to be filmmakers, they want to ride their bike, they want to work, but they’re not going to spend two hours a day commuting, hanging around the water cooler, all those kinds of things. That used to happen a lot.

Joshua Ross:

Well, that’s a great lead into next question. So the third person in the room right now is our amazing producer, filmmaker, engineer, Sophia Holt. And this really speaks to her because totally. When you look at these young adults coming up and they’re looking at this idea of open talent, what kind of skills do they need to have? Do they need these hard skills like graphic design, analytics, filmmaking, or is it more on the leadership critical thinking collaboration, or is there a combination of both that they should be working for as they’re marketing themselves to business? Right, because there’s still going to be competition in this open talent. Yeah,

John Winsor:

Yeah, for sure. One of the things I find really interesting is Korn Ferry says that there’s 85 million tech jobs that won’t be filled before 2030, and that even includes the gen AI stuff. And so that’s going to cost companies $8.5 trillion. So the idea that if you’re a company, you’re going to go find a Sophia to be on a film like crew. I mean, she’s got other things in her life she wants to do, probably just guessing. And so I think what we’re talking about here is how do you do that? Well, there’s a couple of things. One is you have to put learning at the core of your existence. One of the things we’re finding in this kind of gen AI that’s starting to really take hold is that inside companies, the average company gives the employee 0.3% of their salary to do job specific training per year.

Whereas the average freelancer spends 15% of their time doing new skills because they know they need to be able to market those. And for me, I would much rather always go with the learner. And so I think that’s one of the core, how do you learn? So that’s the second step I think if you’re Sophia, how do you use it for yourself? How do you become adapt at having all this great talent? One of the things that’s a misnomer I think, is that we’ve given everybody the same computers and the same technology and broadband connection globally, and then we expect people in the US to be paid $50 an hour and somebody in India to be $10 an hour and they’re competing now. Right? That’s the thing. I have a new assistant from India. She’s the best assistant I’ve ever had. She’s a rock star and for her making less than somebody in New York, she’s living a great life.

She’s supporting her mom, she’s supporting her family, and I really enjoy it because she’s very adept. She’s really into learning. If I have a question about a new software package, she’ll go out and learn it on the weekend and get back, and there’s this kind desire to win. And I would suggest that’s the second thing, or the third thing is that one of the things I love about entrepreneurs is nobody wants to screw around. Everyone wants to get shit done. I don’t know about you, but I work with so many entrepreneurs and so many large companies, it just kills me that a length of time it takes to make decisions, everybody gets to cover your ass to check with somebody else, and it’s just horrible. Whereas you talk to an entrepreneur, let’s do it today. I’ve got a few hours before I run out of money, I got to get it done. And so that kind of creating a culture around that of fellow entrepreneurs is super important.

Joshua Ross:

So just one point of clarification though is in terms of those kind of soft skills, I don’t like to call ’em soft, so we’ll call ’em human skills. How do you highlight those to organizations that I am a critical thinker, I’m a problem solver. I am great at collaborating things that you can say in an interview, a lot of these hard skills you can actually prove in some type of assessment test or you can show your portfolio.

John Winsor:

Yeah, I mean, I think it just turns to the cycle. I mean, I think what we’re seeing is, and what’s going to happen, I was just with a platform called braintrust last week, and they’ve created a new platform called air, which is AI recruiting, and they’re kind of built a software that all the first round of interviews are done through ai, even the face-to-face interviews. And you say, oh my God, how horrifying. And it is terrifying in some ways, but what I find super interesting is that you do a dialogue with ai and it not just gives the company a rating on how you did, but it gives you that rating and it says, Hey, Joshua, here’s some skills that you can improve on and here’s some things you can upskill. And so it gives you that direct feedback, that learning feedback, and I think that’s something that’s going to be more nuanced.

One of the things I also love about platforms is that if I hire Deloitte and Deloitte assigns me, Sophie and Sophie does some great work, I don’t know that. But if she works on a platform and then I go out to that platform and say, huh, I wonder who can do my film work for me? It’s like, there’s Sophie, she got a five star rating. Here are the things she’s really good at. Here are the customer comments exactly about what that is. And that kind of level of knowledge and exposure is really important. And so I would suggest that’s where the soft skills come, what you’re looking for, just like with LinkedIn or any other platform that you’re looking for, those kind of critical soft skill references, those kinds of things. Like man, she was a joy to work with. It was super easy. She’s always so happy.

Those kinds of things. I mean, my feeling is that, like I said earlier, freelancers are going to learn more and they’re going to be up to date. You just have that curiosity. You’re like, wow, I know what the new program is. I’m going to play for a couple hours tonight and get certified so that or whatever. Just get knowledge on that. People just don’t do that. They talk a lot. I was just at this conference we ran at Harvard on ai and Ethan Head of entrepreneur program at Wharton was talking about just by being in the room that we were in, and his kind of demarcation is if you spend 10 hours of time on a LLM, like chat, GPT or GPT-4, you’re like miles ahead of anybody else that everybody talks a good game, that they’re using it a lot. But so to me, that’s the real skill is being curious, is being open, trying to do that.

And I also think that one of the things I love about this era is that there’s no penalties to fail. I mean, that’s what I love. The Silicon Valley attitude of failure is not a problem. It’s like a learning opportunity. And I think there’s that. But I also think there’s no better way than to be a beginner. And I have this crazy friend, and this is kind of an old story now, but I think it’s so applicable even more today than it was, but he graduated from University of Michigan. He went to Steamboat to be a ski bum. He had a shitty job in a bank and he just hated it. And at night he started learning Python and it was super early days of Python. And so he actually blogged about the experience of being a beginner at Python. So he just, every day, I don’t know what I’m doing, anybody have any ideas? I’m stuck here. Like, oh, I learned this. Here’s some ideas for you guys. It blew up. It blew up for millions of people. And he wrote this book and he has a very successful software engineering company now. But because he was just vulnerable and he was the beginner and he is like going, can you help me and I’ll help you? And it’s this community. He was just so far ahead of the curve.

Joshua Ross:

You hit on two important things right there, being vulnerable, putting yourself out, they’re asking for help. And the second is leaning into whatever community is. So many communities are so giving, but you have to put yourself out to do it.

John Winsor:

Yeah, there’s no doubt. No, I think that’s it. I think we need to figure out in business how to be more vulnerable. I was with Mike Tushman, who’s a professor at Harvard teaching a class on corporate renewal and to a bunch of 170 global CEOs, and he was talking about personal renewal, and that kind of got me riffing about my own experience and my background. And then I connected with my editor at HBR Harvard Business Review, and we were talking about what are the most popular articles that have ever been written in the context of personal renewal? And he said that there was an article right at the beginning of Covid on Grief that by far, that’s the number one article HBR has ever written. And it kind of blew me away. And I started thinking about one of the things that’s interesting in life, we’ve created all these rituals and methodologies for overcoming obstacles, whether there’s a death in your family and there’s a funeral, there’s therapy, there’s coaching, there’s all these other mentalities. But when there’s any kind of disruption in work besides kind of the Silicon Valley view of the world, but most times it’s get back on the horse tomorrow, no problems. You go forward always everybody, and it’s not the way the world works. You need time to kind of sink in, go through the grief, figure out how to be vulnerable and be more human. And I think that’s what’s really missing a lot in work. Now it’s like, how do we be more human? What does that mean?

Joshua Ross:

Well, that’s a great question because with open talent, the idea you really have a distributed workforce and you’re communicating over these digital mediums. How do you do that? How can you show empathy and emotion?

John Winsor:

That’s a great question, but I think we’ve got to lean on millennials and Gen Zs. There’s so much more adept in the digital world. And what I’m finding, I dunno about you, but I’m figuring out that, hey, I can have a pretty decent empathetic conversation with somebody through Zoom. It’s a skill. It’s something I’m trying to learn. It’s not as good as human connection, but the rapidity and the repetition and the ability to connect with amazing people and the willingness for those people to connect with you. I mean, it’s super cool to see these kinds of little platforms that allow for micro engagements with the world’s experts. I just noticed on Instagram there’s something called intro. And you can go to intro and you can say, I want to talk to some famous Hollywood producer for 15 minutes. Maybe it’s 200 bucks. But you get that insight and that accessibility. We can say, oh, that’s crazy, and it’s exploitive and all that stuff. But it was like 25 years ago, how the hell would you do that? If you’re a film student at du, you’re never going to be able to get into a door. But now you just go online going, either that or you go to LinkedIn and going, Hey, I’m doing this work. Can you give me some feedback?

Joshua Ross:

I want to move this conversation a little bit to the business side of open talent and really kind of focus on the small business because I’ve owned my own companies and they would be classified under small business and talent is so important. And I always remembered at the very beginning, it was very hard. We didn’t have a lot of cash to get A players, so we usually got C players and hopefully we’d be able to buy and hire B players. And towards the end, once we had success, we got a players, but each one had a very critical role. And if they left, they also took a lot of institutional knowledge and a lot of institutional value. So how do small businesses really leverage this open talent with the understanding that they need it to compete and that at the end of the project or whatever the deliverable that talent leaves,

John Winsor:

It’s a whole new way of thinking and working. And so from a company’s perspective, when you’re young and you’re not experienced, you always need better talent than you can hire. That’s just a given. You always need the next level to get to the next level. And so instead of having people kind of come in and out of the company, or this is my favorite team member, but the company’s just outgrown them, I’m going to have to kind of offload them. Why not have a situation where you can taxify the work and be able to figure out who can work on what and be really open like, Hey, go get a side gig. Everybody here should have a side gig. Those are kind of the mental models of thinking about it, not as an organization, but as we’re talking about in the book, more of a networked organization. How do you have networks that include external talent, clouds, internal talent folks that are curators, right? What’s the intellectual property in your company who really drives that? And then let’s get other folks to surround those people with the very best people in the world to be advisors, to be consultants, to do the work that that vision is set on, and how do we solve those problems? It’s a big mindset shift.

Joshua Ross:

So I get looking forward into the future and saying, all right, we’re going to build this kind of organization to go solve problems using open talent, and this is the way we’re going to structure it. And I can really think through that distributed model in my head. But if I’m a small business that is like, alright, we want to move to this. How do we also do that culturally, getting people to shift their minds set. Yeah,

John Winsor:

I think that’s huge. So I think it starts with deconstructing what jobs and roles are and really getting into tasks. What tasks are you good at? How do we match? How do we take the work, the outcome that we want for a client task, justify that work, and then be able to get that work done? Whether it’s the expert at this or you’re up and coming, you’re going to take some off hours to learn this skill and then fill in those gaps that aren’t done. So it’s not threatening to people. It’s not like, oh, they’re going to take my job. It’s like, wow, we’ve got a hundred tasks to do and we’ve got 50 dialed in house. How are we going to do the other 50? Let’s find the experts to, you’re going to manage, but they’re going to help you build the skill. You just think about.

I mean the paradigm that I’ve been talking about a lot in speaking with big companies is say, Joshua, you just became CEO of a Fortune 500 company and your board just mandated that you come up with an AI strategy. So there’s two ways to do it, right? The first way you could do it, the old school way of say, okay, I’m going to call my CHRO into my office. Oh, it’s going to take two weeks to get that meeting both busy. I’m going to say, Hey, hire me an SVP of ai. Well that’s going to take eight to nine, 10 months now to do that. And then you find that person and she’s going to say, oh, I need six months to hire my team, and then it’s going to take two or three months to do the strategy. Everybody’s onboarded, ready to go. But in today’s environment, 18 months to get a strategy, you’re dead.

The other alternative is to say, okay, I’m going to invite the best people in the world to Denver on the DU campus. Let’s say there’s 10 people who really are good at ai, AI strategy and educational institutions. Bring ’em here, bring your team together, two day workshop. What are the a hundred tasks that need to be done to get the outcome of the strategy? Assign those what outside expert can team with one of your people that want to learn, that have the ability to learn. And literally, by defining that, that way, and using talent, very task oriented, you can get a strategy done in a month. And so let’s not let great be the enemy of good.

Joshua Ross:

Using that example of that senior vice president too in the 18 months to get that person up to speed. I mean, I think we’re now 20 months in since that Chachi BT hit the wire. So you think about how fast technology moves and what if that person actually isn’t the right hire too. I know then what has happened in terms of time, cost, market position. So that makes a lot of sense. Alright, so I have a few final questions for you. Yeah, man. Are you

John Winsor:

Ready for them? I am. Okay. ’em,

Joshua Ross:

You’re going to have this little crystal ball,

John Winsor:

Crystal ball. I love

Joshua Ross:

Crystal ball. You even need a crystal ball because it seems like everything you’ve done, you are always thinking into the future. I

John Winsor:

Dunno

Joshua Ross:

About that. So how do you see the role of talent evolving in the future? Particularly now we’ve got generative artificial intelligence, we’ve got these changing work environments. I was just in downtown Denver a couple days ago and there’s nobody down there I know. And so where do we go with this role of talent? And I read about digital nomads and certain countries are giving extended work visa, which I think is the

John Winsor:

Coolest thing in the world. Me too. Me too. I wish I was

Joshua Ross:

A little younger. Take advantage of one.

John Winsor:

Exactly.

Joshua Ross:

So where does John Windsor see talent evolving?

John Winsor:

Well, I’d say don’t get into commercial real estate. That’s the first thing. No, I mean, I think what you need to do if you’re young and talented is you need to figure out your life, right? That’s not about the work. It’s like where do you want to be? What do you want to pursue? How do you want to do it? And then have work fit into that. So if it’s like, oh, I want to live in Greece and Greece has these kind of golden passports or this kind of digital nomad stuff, then post up in Greece and play that value arbitration. How do you want to live your life? Who do you want to live your life with? And then knowing that that’s the basis, then how do you construct a work environment? All of us are going to have portfolio careers, right? We’re going to do a little of this and a little of that, and we’re going to do this project over here and we’re going to find, wow, two people are going to go launch this new thing.

I want to be a part of that. Maybe it doesn’t pay a lot, but man, I’m going to get tons of experience that can apply to these three other things I’m doing. So that’s the other mentality that needs to shift is instead of saying, I’m going to have one job at a time, I’m be a hundred percent dedicated to it. They’re going to own my time. That’s little bs. It’s like your life. If it’s your time, they do what you want to do, pop into the project you want to pop into, give the effort you want to. And so I think that’s the real call to action is don’t get stuck just because your parents or your uncles or your aunts or your sister or brother that’s 10 years older than you live their life one way. The world’s your oyster. Go explore, go blow things up. Try things. That’s the key.

Joshua Ross:

So I love that. And if you have the worker taking that approach, how should the businesses be thinking out five, 10 years in terms of even silly little things like an office

John Winsor:

Space I know and

Joshua Ross:

Building culture in these different things.

John Winsor:

Yeah, I mean, I think they need to change too. I mean, I think the commitment is we’re going to be radically, radically focused on outcomes. A lot of times it’s like, what do our customers want? How are we going to do that? And then how are we going to deliver that with the least amount of friction? And I’ll guarantee you, it’s not about onboarding a thousand employees and putting ’em in an office in Houston and taking six weeks or two months to onboard those folks before we can even start working. The deal is companies need to think radically about what are the customer needs? What are the outcomes that we need to do? How do we task find that work? One of the companies that I’ve had the good fortune of working with that are just blowing up right now is called Invisible. And they had this good fortune luck that in 2020 they decided to aggregate all the, or least everybody they could find AI software engineers, freelance around the world.

And so you start doing this in haphazard methodologies and then all of a sudden open AI calls and says, Hey, we’re building this LLM, and then Microsoft calls and Google calls and anthropic calls, and now they’re just exploding. And one of the things I love about what they’re doing, and I would recommend for any individual is that you take where your outcome needs to be and then you task justify it. And then what they’re doing is they’re deciding which projects, which tasks need to be done by AI or machines, and which ones need to be done by humans. And how do I balance that? I think anybody that’s not using generative AI at school or in their work is cheating themselves. They need to explore this stuff. They need to be able, not just Joshua, it’s like super Josh. How do you make yourself into that and how do you empower yourself to really be successful as Kareem LA and some other people say in the context of ai, it’s not. AI is not going to take jobs away. Somebody that really knows ai, that uses AI is going to take your job away. That’s going to be the deal. Humans with AI versus humans without.

Joshua Ross:

Yeah. I truly believe that different areas where people are saying you can’t use ai, they’re actually missing it, and they’re causing a huge disservice to whomever they’re telling that to. And I think you have to lean into it with certain requirements and guardrails around what you’re allowed to do. And I’m speaking more in kind of the educational setting.

John Winsor:

Sure.

Joshua Ross:

So as an entrepreneur and thinking about open talent, and you’re talking about these distributed networks and different ways to communicate, I’m also looking at, all right, if you’re doing all these tasks, you’re going to have to measure things and also say, alright, the talent we brought in for these three things we need to measure to see if we want to bring ’em back. Were they actually worth the cost? So what are some of the things an entrepre should be thinking about in terms of creating ways for open talent to evolve?

John Winsor:

Yeah. I mean, I think first of all, you’ve got to be really tight with a few platforms that can do that. One of the things that in that context, one of the things that’s blown me away is the idea of the annual or the quarterly review. What a ridiculous thing. Shouldn’t it be that we have this podcast and Sophie’s doing an awesome job, and you say, how did Sophie do? She fills out a form. You fill out a form, it’s like, oh, these 10 things. Sophie kicked ass on six. A couple things that she could be better skills at. A couple of things. She doesn’t do well with those things, those four things below, she should get immediate feedback on what are the upskilling opportunities? How do you do that? And then all of a sudden you as a user should say, Hey, Sophie got the upskilled. She’s ready to go to the next level. And I think that kind of feedback, the kind of openness and transparency of the work that’s done, that’s what we need, that we need more trust instead of like, oh my God, I got my quarterly review. This person’s in a bad mood. I don’t really get along with them very well. They’re going to ding me on a bunch of stuff. It’s just such bullshit. We should be very focused on how we do on the tasks. I think that’s the future.

Joshua Ross:

What I love for that, instead of getting that feedback form and having to sit at my desk and fill it out based on what Sophia did and what she hasn’t done is this to have these kind of neural transmitters and I’m driving home and it automatically just transmits it and fills out the form, and AI makes it, puts it in a kind of cohesive, structured way. And then Sophia gets it and she could read it. She could have it read to her all these different ways. Because I think the other thing, these roadblocks is we’re all at our computers doing input. Yeah,

John Winsor:

Exactly.

Joshua Ross:

What’s a way to do it with less friction?

John Winsor:

Neuralink.

Joshua Ross:

Neuralink. Yeah.

John Winsor:

That’s terrifying.

Joshua Ross:

John WinDor, you’re 18 years old again. What do you tell your 18-year-old self?

John Winsor:

I’ve got 2 22 year olds. One Charlie’s sitting in the room right beside us, right? He’s studying for the finals for this quarter.

Joshua Ross:

Marjorie Rehaul, for all of you out there went to the University of Denver.

John Winsor:

Exactly. Exactly. I mean, I’m a bad dad. I just am so optimistic about the world and the opportunities. I always just tell my boys two things, like blow shit up. That’s the first thing. And just become the very best person in the world at whatever you’re passionate about. And I get such a kick out of listening to Mr. Beast or some of the guys online and what I love about Mr. Beast and some of the other folks, but the whole idea that Mr. Beast is people think we did something magical. It’s just like we connected with a bunch of people that really like making videos. And we did this way more than anybody else has ever done in the world. We’d stay online 20 hours a day talking about what are the best thumbnails? How do we get it done? It’s just the that Mr. Beast has done way more cycles and become the best in the world because he’s done it way more. And so that’s what I always encourage people is like, be provocative. Try to blow shit up. Ask why not instead of why. And then do the work. Find whatever you’re passionate about and just outwork anybody else, and you’ll emerge as the best person in the world at it and create unfathomable value for yourself.

Joshua Ross:

Can I add on to that, even though I asked you?

John Winsor:

Yeah, man. You answer

Joshua Ross:

It. Take risk. Right now. You have almost

John Winsor:

Nothing to

Joshua Ross:

Lose. You don’t have, well, you may have a mortgage, but your risk

John Winsor:

Profile is so low. I know. And at the

Joshua Ross:

End of the day, you may have to move in with your parents for a little while. Who cares? Who cares? You know what? They don’t really want you to move in anyway. I know. Just go out and try stuff. Blow stuff up.

John Winsor:

I love it. Yeah. Blow shit up. That’s what I mean. Don’t be afraid of risk.

Joshua Ross:

Well, John, thank you for joining us on the podcast today. Thanks

John Winsor:

For having

Joshua Ross:

Me and making me a little bit smarter.

John Winsor:

I don’t know. You always make me smarter, so we do it together.

Joshua Ross:

I appreciate it.

John Winsor:

Thanks.

Joshua Ross:

The entrepreneurship at DU podcast was recorded in Marjorie Reed Hall on the University of Denver campus. You can find us on Instagram at du Entrepreneur on Twitter, X at DU entrepreneur, and on Facebook at entrepreneurship at du. This episode was engineered, edited, and produced by Sophia Holt. Entrepreneurship at DU is part of the Daniels College of Business, which has its own podcast. Check out Voices of Experience wherever you get your podcasts.