Hello and welcome to the Career Success podcast by Jason Connolly. If you’re a regular listener, it’s great to have you back, but if you knew, welcome to the show in this series. Every week we speak to the biggest names in business all across the globe. We talk about their career stories, the lessons learned, how they overcome challenges, and what success habits they practice. Practical advice to help you in your career if you have a passion for business, then this is the podcast for you.

In this episode, I’m delighted to be joined by Sean Sheppard from San Francisco in the US. Sean is the managing partner. You plus the world’s leading corporate venture builder, he’s a globally recognised thought leader with over 20 years of experience bringing new products to market, including as a five time sales founder with three exits, Sean was named as one of the top sales influencers. You should be following on social media, including LinkedIn. Sean is an active member, advisor and guest lecturer, global start-ups accelerator’s Innovation Conference is an colleges and universities, including NASDAQ 500 Start-ups Y. Combinator galvanised alchemist GSV labs. London Business School and the Owing School of Business at Vanderbilt University. Sean it’s such a delight to have you on the show. Thank you so much for joining me. Thanks for having me Jason. Your background is really interesting. There’s so much that you’ve done throughout your career but they tell us a bit about your career and how it all got started for usual and I appreciate this 20 years of experience here to unpack, but it sounds fascinating. Your career and backgrounds. Yeah, more than 20 years certainly. I I’ve always, I guess always been an entrepreneur. I didn’t, you know, I didn’t say I didn’t. I didn’t ask for it. It sort of told me that’s what I am and who I am. And I have that entrepreneurial DNA. I’ve always been fascinated by the future and especially around technology. And what technology promises to make the world a better place. I love working with people. I love, helping others get what they want. And I found that my real place in this world was to be able to bring new technologies to the world to make it a better place. And do that by working. Very closely with other humans who could utilize that technology to pursue that. That vision I started probably just like anybody did. Just finding ways to earn a living and make money as a kid. And I was very, very much into sport. I played everything but then chose to pursue a career in Professional Golf. What the University to play. Golf played professionally for a few years. What I loved about it. I think the most is that it’s a very honest sport by the golf ball never lies to you can only do 9 things out. You had it, and then if you understand those nine things, you can reverse engineer your way into doing it better next time and the feedback was instantaneous, which is something that I’ve carried through my entire career. That feedback is a gift and fastest way to learn anything is through direct experience. And I’m all about accelerating that path to that learning and along the way I just learned about the different things that that different problem spaces that exist in markets and try to just address some of the bigger ones, whether it was through new technologies or it was through developing people. Um and I went from being a serial entrepreneur to an investor to a frustrated investor. When I started to see that the reason companies were failing had nothing to do with their technology. It had more to do with people and the markets they were trying to address. And so I built global accelerator program to address the issue of product market fit, which is really the big problem that exists in in businesses. Most businesses fail because of lack of differentiation in the market. What makes you unique when you’re taking a product too? Marketer to a customer. You’re asking him to make some sort of a change, and your biggest competitor is in some other product or service. It’s changed, or the inability or lack of willingness to make that change. So how do you make it easy for people to change reducing barriers as the fastest way to do that? The other big reason is priming in the market. Is the market ready for your idea, your product, or your service?

I’ve seen many, many iterations of Uber, you know, over the last 15 years that didn’t make it, and I think most of that was due to the timing. In the market and the convergence of various technologies and user behaviours, that was a big difference for, say, a company like Uber and now I focus on helping large organisations move from physical to digital in their businesses, especially in the age of the pandemic. Digital transformation has been thrust upon everyone, whether they like it or not, and so the marketplace is adopting new ways of being served, let’s say, and their needs and wants and desires are more and more digital. In nature than they’ve ever been before, and so large organisations need to adapt to that quickly or they risk being out of business. You know, 52% of the companies that were on the S&P 500 index in the year 2000 longer exist. You know, people like Jeff Bezos who founded the most valuable company in the world is worried about whether or not Amazon will even be in business in 10 years because things change so quickly. And if we’re not adapting to the needs of the marketplace, we’re going to slot were going to die very slow in public death for a large organisation. Probably a quick and painless one if you’re a start-up, so my focus is around the idea of taking something someplace new. How you’ve obviously evolved a lot over the years and you know you’re still at the very much the forefront of what you’re doing. How have you made sure that you’ve always kept current and you know kind of a breast with what’s changing in the business world? How have you not got left behind? ’cause you, if anything, you seem to be on an upward trajectory moving very fast. I would say it’s simply fear. Fear of no longer being relevant. Fear of being left behind, never afraid of competition. I’m afraid of being the same person tomorrow that I was today, and so I’m very much focused on trying to always learn and develop and grow. ’cause if you’re not growing in my opinion you’re dying, and so it’s, I guess it’s part of my Napier, part of my own positive paranoia that keeps me that keeps me going in the direction that I’m going. But I’m also very much excited by the promise of the future, and so I very much stay in a vision sort of state. You know what’s the world going to look like in five years or 10 or what’s the new trends that are emerging in the market that that could be capitalised on every new change, or every new technology brings a whole new set of problems and challenges with it, and we don’t really see those until we actually start making that change. And so then that creates a whole new opportunity to improve and iterate on those things as well. It’s really interesting, I think especially what you say about the fear of getting left behind. I think that’s the way my mind kind of works as well. I’ve always wanted to be at the forefront of what’s going or not. At the back of the queue, kind of what’s being this sort of. You know you’ve obviously had a fantastic career, and you know when you started. Was it quite a quick trajectory, or you know, I’m guessing you’ve learned a lot of hard lessons along the way as well. Throughout your career, it seems that you know, you know, not this place where you are without learning a lot. Yeah, I mean, I’m a big believer that there’s no winning and losing. There’s only winning and learning, and it wasn’t a quick trajectory by any stretch. You know, people only see the end, and I think that that’s some sort of overnight success story. And then it’s a smooth, simple. You know up into the right hockey stick, sort of a trajectory. That’s not it at all. It’s a mess and it’s very confusing and it’s very chaotic and those that are curious enough and persistent enough to work their way through the chaos to find order. Or the ones that tend to win and then out of that I’ve slowly overtime found a formula I’ve been able to sort of step back and look broadly at the dynamic of doing new things and what’s required in order to be successful at doing something new and different and applying that. I founded for the companies that I’ve invested in or the companies that I’m serving now at you plus, and it’s a very it all comes down to what I call a stage relevant mind-set. So what I’ve learned about myself is that number one I’ve learned is that there’s various stages of development in any business. There’s the let’s just call it, you know, zero to one, and then the one to end, and then the management of N. And I’m very much a zero to one person, and that’s an area where I see most organisations struggle is they don’t have the right mind-set, skillset or experience to know how to take something someplace new or do something different than they’ve done historically. And big companies, especially you know there are driven by their core business, and that’s fine. I get it. But the people typically who did the zero to 1 to get that company going or dead or retired. That mind-set went with them. What makes somebody great with managing your optimising? Something that. Exists also makes them vulnerable at the idea of taking something someplace new and being innovative in their approach. So I think they need that help and so I’ve taken everything I’ve learned from starting my own companies and investing in companies and accelerating those two helping corporates do the same thing. ’cause I think that’s the future of innovation globally is to have a model to execute on trying new things to see what sticks and then being able to create an environment where that can. Very iterative cycle so that we can learn faster and get products and services to market cheaper than we might otherwise have done it. I mean, it sounds like your career is being one of very much kind of learning as you go, and I think you know it’s. It’s obviously the reason that you have a lot of success is because you’ve learned all these lessons along the way in the different businesses that you’ve been there, and that’s kind of, I guess, got you into that position of, you know, working in capital venture and so forth. And you’ve got to that position. But well, even what you’re doing at the moment, you’ve built over 80 businesses at venture Builder you and put those in the getting those in the Fortune 1000? That that’s that doesn’t sound like an easy feat. What type of businesses are these? It’s not doing this with, so you think about any business. Like I said that that isn’t. Isn’t lives in a physical world if they’re going to. If they’re going to stay relevant and survive in the innovation economy, they need to. Build different ways of service serving their customers through digital means. So we take existing physical businesses and we create digital versions of that for them. And we launched those to help them better serve their existing customers as well as enter new markets and work on the disruptive things that might put them out of business later. Like once again, what Uber has done to the taxi industry or the cab industry, for example. And so no, it’s not easy, but we do have a formulaic approach to doing it. We’ve got a framework and we bring the full teams to make that happen, and that’s. That’s based on the collective experience of our entire teams backgrounds. They all very similar backgrounds as me. They come from the start-up group. We have a start-up DNA. We have a stage relevant mind-set and skillset. We know how to learn quickly, cheaply and quietly. I always say that when your when your start-up, for example, you’re just a stranger in a strange place with a strange offering trying to talk to other strangers into doing strange things with you. And if you understand that, how you approach it is very is very different. So you need to be alert at all, not a know it. All you need to have a direct continuous engagement. End user customers to truly understand how they behave, what they want, what they need, and how it’s different than it used to be in order to serve them. And if you do that the right way, the promise of digital is that you can do it quick and cheap on your way to finding things that scale. And once you find something that scales, it can scale infinitely quickly, effectively and much more with much more and much more capital efficient manner than you can in the physical world. So helping those companies in that way is, you know it’s very rewarding and creating over a billion dollars in market value. Those 80 plus businesses has been very rewarding. Gratifying when you take a business on them. What is it that you’re looking for from the leaders? Because I, I’m guessing obviously you’re going to mentor them and get them kind of into you. Know the right places that you want them to be, but what? What is it that kind of makes an attractive business for you? Is it quite driven on the leaders of the business or is it the product? Or is there? Or is it just different in every case and circumstance so you look at team model market and product and those are essentially the four? Categories I think what’s most important certainly is the team. It’s like when I make an investment in a founding team, the top three things I look at are the founding team, the founding team, and the founding team. In the age of applied technology, most things that we bring to market defensible, they can easily be copied. So it’s about the team and how well they execute against that. And then it’s the how big is the market? Is the timing right in the market? And you create differentiation as you execute and then so those are the fundamentals we look at from a corporate perspective. I look for companies that have really strong. Existing ecosystems, if they have. If they have great relationships with their customers, we can leverage that to learn. And if we can do that then we can find new and different ways of serving them and creating value in around the entire organisation. Now from a stakeholder perspective and the business leaders, the technology leaders in the product leaders in these businesses we need them to trust our process and framework and our team to do our work in a safe, safe space where we’re not inhibited by the bureaucratic morass of the core business and we need that continuing support. And if we do that, we can get where we want to go. I mean, for me it’s always the same three things when taking a new product to market. I want to find the truth about where it fits in the market. If it does at all, and what to do about it. I want to create a learning organisation of the team of people who are responsible for pursuing that truth to get there faster and cheaper. And then I want to find profitability or impact whatever that KPI in the company. And if we can do those three things, we’ve been successful, how did you devise kind of your screening process and you know what it is that you’re looking for? Is this kind of from? Just experience that you’ve built up over the years. Or is it? You know what? How is it that you you’ve come to, you know, have such clear defined kind of parameters? Yeah, it’s from experience and experience is what you get when you don’t get what you want, so I’ve had I’ve had more failures than I’ve had successes. And in American baseball, if you fail 7 out of 10 times, you’re in the Hall of Fame, and so there’s nothing wrong with that. That’s where it’s come from. It’s come from that experience, and it’s come from figuring out what I don’t like or what isn’t a fit just as much as what I do like. In fact, it’s even more so the older I get, the smaller the circle is and the more narrow my criteria is around the kinds of people I want to surround myself with work with collaborate with. Kinds of businesses and the criteria of those businesses that de-risk the opportunities and give you a higher chance of success. You know of innovations failed to last three years in the market. 95% you know. Our failure rate is below 20% and it’s because we picked the right teams and we have a model that allows us to learn fast and cheap what works and what doesn’t. We can kill things before too much money is invested in them. Most people have an idea they go build something and then they take it out and go. What do you think that’s the wrong way to do it? You need to flip the script first thing you need to do is identify a big problem in a market that you think you can solve really well and then go to that market and start asking questions and start to validate either your ideas or iterate based on what you learn and be open to that feedback and then clearly define a problem set that has a real measurable value to it and then get those early customers to go on that journey with you to realize your vision together and then through the course of doing that then you can build on that. Keeping this the same in matters of opportunity Now, then they will say a decade ago. Or do you think it’s getting harder and harder and harder to think of new ideas for new products because you know you use the Amazon kind of example at the start, but I’m sort of left wondering what. What is it that we can have that we don’t already have now? Experiences, experiences that delight you. Why is Amazon the most valuable company in the world? Not because they make anything, but because they make everything easier. The future of any successful. Innovative business is about creating the right kind of experience for your customers and stop as a country. I do agree with you there no. But the whole point is that is that in the innovation economy, things change almost every day and if we’re not out in front of the way our customers think and act and feel and responding to that, then someone is going to replace us. So do I think there’s more or less opportunity now? I think there’s absolutely more opportunity we still have so much further to go. As a society, we’ve lifted a billion people out of poverty in the last 20 years, and we still have another 3 billion to go. And these people aren’t even in a state where they can actually leverage technology in a meaningful way yet. And we have no idea what that with the world’s gonna look like once. And as I said, every new innovation and every significant change, whether it’s legal, political, social, technological, all of them create a whole new way. A whole new series of opportunities. To serve people in new and different interesting ways. And so the key is to just always have your finger on the pulse of that. You don’t have to have your finger on the pulse of all of those things. You have to have it on the on the pulse of the things that you know and understand with the customers that you currently serve. Yeah, and I think that’s really good. I think what you’re saying is you make some really valid points, and I think, especially with emerging markets and adopters of technology, have you kind of when you’ve gone throughout the years. Do you see sort of the same? Things every time you go to a company is there kind of a similar thing that you tend to find, but you know what? What differentiates a company that’s gonna be successful versus a company that’s not? Is it just down to the team or is there something that you kind of? It just tends to be, you know, a thing that comes up again and again and again. Yeah, I always look to my favourite business book by Jim Collins called built to last, which analyses the most sustainably successful companies over the last 50 years or so. And the commonality’s there. And it starts. With the team and it starts with a team that can be honest with each other that trust each other that challenges each other. It doesn’t take things personally in the process, doesn’t play politics and is constantly driving itself to be better and it creates that kind of a culture. The second thing is that are they customer centric first by they problem focused instead of product focused. ’cause I’m here to tell everyone no one cares about our products, they care about their problems and whether or not you can solve them. And so the most innovative companies to me are the best. Two fine and what? What advice would you give to you? Know people starting out in the sales industry. Obviously you’ve been named as one of the top sales influences that you should be following on social media. What an accolade to have. What advice would you give to people starting out in the sales industry or people wanting to, you know, get to level of prestige, but you’ve got to in the sales arena. Yeah, so I would say there about four or five things. It’s kills the areas that every sales professional needs to continuously develop regardless of age or product or market or services. 1st is the mind-set you need to have a growth mind-set. You need to be alert at all and not a know it all. You need to be persistently curious and humble. In your approach. You need to understand that the whole reason you exists to help others get what they want and be wholly focused on them. The second is to have a sound business acumen. If you’re in sales, especially in business to business sales, which is where the most successful sales people end up, we need to understand how business models work and why your customers are in business to begin with. So don’t just understand your customer, understand your customers customer. Find a way to create subject matter experts and don’t just look at your customer as somebody who can buy from you understand who they are, what their role is, how they’re measured, how they think and feel it. Spend the time to do that. 80% of them don’t, and it’s reflected in how they talk and message when they’re in the sales process. The third is market act. How quickly can you become a subject matter expert thought leader or industry expert in a given segment based on the product and market that you’re selling into? If you’re selling into financial services. You should become a financial services industry expert. When I first got into sales, I used to get in trouble time for not making the appropriate number of dials and appropriate number of phone calls because I was spending my time doing research, I was reading quarterly reports and annual reports of my customers and listening to and watching and reading interviews with the CEO about where they want to go in the next five years and then doing my best to connect the dots between what I provide to them and that that strategy or that. Vision, ’cause that’s where the value is created. Don’t tell people what you do. Tell them what you do for them. It’s a big difference and then and then the other thing, the other two things. Our communication skills constantly work on your communication skills. I’ll give a wonderful example is I absolutely abhor filler words. When I hear someone say like 10 times and it has no context in a sentence, it drives me up a wall or they use things like R or something like that to connect words, reduce the filler words. Become a great order. Become a great listener. Active listener, because that’s where you’re going to learn the most. Become an amazing presenter. Pay attention to tonality and eye contact and posture and body language. Things that build confidence in your prospects because you are a stranger and when you’re a stranger, you have to build credibility and establish trust. The last one is emotional quotient, EQ. I meant I prefer EQ over IQ. Any day, and if you don’t want to reply to be replaced by robots in sales, need to have a strong emotional quotient. Empathy, understanding the ability to adjust and then think critically and be a problem solver for your customers because they don’t work. Again, they don’t care bout your products that care about their problems or whether or not you can solve it when you should constantly working on those things. And I think those are really, really great. I was actually scribbling some notes down when you was just talking, so for one sales person to another, I think you make some great examples and I. I 100% agree with what you’re saying about making sure you’re delivering and having the right communication, and I think a lot of sales people don’t get it right, but I think from what you said there you know testament to you about making sure that you actually understood the client, understood you done that. High levels of research and you really understood what it was. That was the pain point for those people, and that’s why you were successful rather than just hammering the phone for days and getting your dolls high, you know, I always look at that as a really old fashioned sales mentality. You know, get to the current day, and it’s not just about sweet talking someone on the phone and being good at talking and being nice. So I love that. I think that’s a really good set of rules there, and I’m sure lots of people find it helpful. What’s next for you then? It sounds like things are evolving quickly. What’s next in the world of Sean Shepherd and happening in over the next year for you? Well, it’s growing you. Plus I recently acquired a 50% stake in the company and I see the future of corporate innovation being in the portfolio based approach towards venture building. And so I’m now wholly focused on educating the market on this approach, building and coaching and mentoring an amazing team of people to support our clients. An looking at ways to grow the business, whether it’s through, obviously through revenue growth but also through additional acquisitions. Really interesting. So if people want to find out more about you or you plus where can they go to where they can certainly go to you dot plus online to see user technologies is the longer version. Usertechnologies.com or? Www.u.plus to learn more about you. Plus they can follow it. They can connect with me or follow with. Follow me on LinkedIn or Twitter or Instagram at Sean Sheppard. So thank you so much for your time. I think you’ve made. It’s been so fascinating to hear about your career all about your sales backgrounds, and I think you’ve given some really great practical advice. I think people are going to find really helpful, so thank you so much for sparing your time and coming on this show. It’s my pleasure, Jason anytime that was Sean Sheppard from San Francisco. I’m Jason Connolly. This is the Career Success podcast until next time goodbye.

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