How to Win | 12 Entrepreneur Lessons from Steve Jobs

In this motivational talk, the speaker weaves together inspirational quotes from Steve Jobs, Isidore Sharp, Donald Trump, Marriott, and Chip Hawkins to emphasize the importance of belief, giving 100% effort, and relentless persistence for entrepreneurs. He warns against the regret of half‑hearted effort and urges listeners to work daily at their full capacity, even during dark periods when quitting feels tempting. The speaker highlights the role of mastermind groups and peer support in navigating these challenges. Transitioning to practical advice, he introduces a concise three‑step pitch framework: (1) define who you help (niche market), (2) articulate the client’s frustration (pain point), and (3) describe the relief you offer (unique solution tied to passion). He provides guidance on tailoring each step, using examples, and stressing the need for clarity and differentiation to quickly convey value in conversations and emails.
Chapters
And Steve Jobs: "Believe that things will work out. Follow your intuition and curiosity. Trust your heart even when it leads you off the well-worn path. You have to trust the dots will somehow connect in your future." I really like this one. And it's hard and scary and bold to do things when you're not sure if it's gonna work out and when people are doubting you and when you don't have a support network around you. But if you really believe that what you're doing is right and you're helping people and you're seeing that even in early results, then you owe it to yourself to keep on doing it and take, you know, go one more day. Each time go one more day. Number 12, give it your very best. And I like this picture because there's always work 100%, but then it breaks down how much you're working every day. And what you need to do if you're an entrepreneur, you owe it to yourself to really give it your all. I think a big challenge a lot of entrepreneurs face is they don't really give it 100%. You know, on some days they might, a lot of days, you know, they might slack off a little bit, they might be hanging out on Facebook or whatever it is, they don't really give it 100%. And a lot of those times, those companies fail. And what they then come back a couple years later, they really regret it. They're now back in their corporate jobs that they don't like, and they really wish they had given it their all. And I don't want you to end up in that situation. I don't want you to— I don't want to say coasting. I know you guys are working hard, but I want to make sure you're giving it everything you got. If for whatever reason the business does fail, I don't want you to think in 2 years, "Ah, you know what? I really wished I did it differently. I really wish I gave it my all." Because it is a very common challenge and you don't want to live with that regret for the rest of your life. You want to make sure you're giving it as much as you can. Put it all on the table. Your odds of success will go up dramatically. But even if it doesn't work and you end up doing something else, you will be able to live with the fact that you left it all on the table that day. You put it all out there, and if it works, that's great. If it doesn't work, you don't have any regrets. You don't want to live the rest of your life with regrets. Izzy Sharp, Isidore Sharp from Four Seasons Hotel: "Whatever you do, don't ever use a crutch, and don't ever think of having an excuse for not having said, 'Yeah, I did my best.'" You gotta do your best. One more, Mr. Trump, "I was relentless even in the face of total lack of encouragement because more often than you think, sheer persistence is the difference between success and failure." So even just taking one more day, one more day, one more day, even if people are not giving you the feedback that you want, believe in what you're doing, know that you can help a lot of people, and give it 100%, as much as you can every day. And the last one is the bonus one: don't quit. Constantly you'll find the successful entrepreneurs all went through really dark periods of wanting to quit, but they didn't. Times were so dark, you know, they may have lost their house or whatever it is. There's a million reasons to leave their business, but they didn't do it, and they came out on the other side. And the dirty little secret about entrepreneurship is is everybody, everybody at some point thinks about giving up. Nobody's ever going to talk about it. Because when you go and talk to entrepreneurs, "Yeah, things are great. We just signed whoever as a customer and we just hired our first person." You're always talking about the good things. You don't ever go up to somebody and say, "You know what? I think I'm going to close down this business. I can't take it anymore." And it's such a common theme amongst entrepreneurs that everybody will have to go through it multiple times often. Throughout their career. So you got to work your way through it, you know, and again I go back to that first goal, is this something you're really passionate about? That's going to help get you through these really dark times. Again, if you're not really excited about it, if you're just doing something to try to make a lot of money, you're probably not, you know, you're going to quit because you don't have enough core passion for what you're doing to want to get through those humps. Making money just isn't enough of a motivator when you see all the challenges that are ahead of you very often. It's got to be something that you love doing and you really want to help people and you see that passion coming through. So again, everybody's gone through these really dark times and looking at famous entrepreneurs and also connecting with other entrepreneurs who are local or online and just sharing, you know, what you're up to and getting there. Positive feedback. In our forums, we have a section where people are sharing their goals, and we'll talk about a potential option later on today to be able to connect with each other as well. But I find this essential. When I think about my mastermind groups here, it's happened a number of times a year with the different members where they'll come up saying, you know, maybe, maybe I shouldn't do this anymore. And they get the encouragement from the other members, and then next month they're rocking and rolling again. And it's going to happen. So it's getting through those dark times and coming out on the other side. Don't quit. Marriott, founder of the Marriott Hotels, successful people keep moving. They make mistakes, but they never quit. And then Chip Hawkins from EA Sports, one quality of entrepreneurship is just persistence, not giving up because you have roadblocks, and also not giving in because other people tell you that you're nuts. You are nuts, and you should be proud of it. Stick with what you believe in, and that can also help you get through, you know, the hard times. Reading Successful Entrepreneurs, if it's these guys you look up to, or finding your own group of famous entrepreneurs that you look up to and reading their words of advice and their story can help you get through those dark times. Now, this is the guy from EA Sports, huge company, and people told him he was nuts. You know, and that's— it's going to happen, but he didn't give up, he didn't quit, you know, he kept taking steps every day to move that business forward. Now, what I want to go through— I'm just checking the time, good, we still got some good time here. Creating your pitch. This is so important, and you want to do this anytime somebody asks you, "What do you do?" You have an opportunity to either win business either from them or from a potential referral from them. If people can clearly understand what you do and what makes you different, it's easy for them to understand if they could use your services or if they can give somebody to you. And I believe that people want to try to help each other out. And I find that when somebody tells me what they do, I'm often thinking, "Okay, could I use this person, or do I know somebody who could use this person?" I'm trying to help that person out. So it all starts with creating a good pitch. Most of the emails that I get, or, you know, when I'm talking to somebody in person, they either don't tell me really what they do and how they're different, or they tell it in such a long, you know, huge paragraph, or if I'm meeting them, it takes 5 minutes to get out their pitch. By that time, people aren't interested anymore. So you have to be able to quickly get to the core message. So I'm going to work through this with you guys, and we'll go through it quickly here, and then hopefully you guys can take the next little bit offline and go through it and create your own pitch on your own. I love this picture too, "An assembled snowman for sale cheap." I think that's a great pitch, and so I wanted to share that. I'll find a way to put that picture into the slides too sometime. Okay, so step 1, who do you help? So you want to clearly define the type of company or person that you help, and there's a number of different ways to do it. I showed a couple of examples here. So it could be the industry, it could be their location, if you are location-centric or not, how big they are, how many employees they have, what stage of growth they're at, what kind of demographics. There's a lot of different ways to slice up your customers, but you don't want to be the person who sells to everybody, right? That's not a recipe for success. You gotta, you gotta niche out your market to start with, and then if that hits it big, then you can start expanding from there, but your success will come from having strong niche. So knowing from the beginning, who do you help? And you may know it, but I almost never get people writing to me to say who they help as part of the pitch. So you want to definitely think about it and put it in. The next thing quickly with this is you can also provide examples. So if you're brand new, then you may not be able to say anything, but if you do have some customers, especially somebody that somebody might recognize the name, you can say we help "these kinds of companies like," and then give one or two names of companies that you have helped. So that can add to the pitch and again also make it easy to understand who it is that you're going after. Okay, so this is the exercise, fill in the blank, you know, "I help these type of people," and then "like," that would be company name, and company name. So the company names are optional, but you definitely want to have the who you help as that first blank. Step 2: What's their frustration? A lot of entrepreneurs, they're just talking about what they do, but your clients, they want to hear how you can help them. Alright, so you want to focus it around problems that they're facing. So you're not a real estate agent here, you sell people's homes. You're not a clothing designer, you make people look good. Tie it into your customer and the challenges that they're facing and whatever frustration they're going through right now. If you can tie it into a pain pain point, then you're much more likely to get a decision fast. People want to heal their pains, so you want to tie your marketing message around the frustrations that they're feeling. So think about whatever customer you have, you know, what are they doing that makes them bite their computer like this woman, right? What gets them so frustrated and how can you tie that into your marketing message to them? And at the end I'll give you an example too of what I do, so maybe give you a little bit of guidelines as well to move forward. So here, the biggest frustration I help my clients solve is blank. This is huge because when you're presenting to somebody, somebody emails me and says, I help these type of people and the biggest frustration I help them solve is this. That gets me thinking, right? I may not be able to, I may not have that frustration, but I may know somebody who does, and just by you telling me that, I can easily pass them on. So whatever business you're in, you probably have a lot of competitors, right? If you're a real estate agent or if you're in network marketing or you have a t-shirt company, whatever it is, there's a million guys out there doing the exact same thing as you. So why would I pass somebody on to you versus somebody else who I may also know, right? So the difference is going to be specifically explaining to me who you target, and how you help them, what frustrations you solve. That gets me thinking and it also lets me give you more qualified prospects because I know exactly who you're looking for and how you help them. This alone will solve a lot of your challenges, but I want to take it a step further. Next, what relief do you offer? So what do you do that's different or that's better than everybody else? As much as you can, if you can tie that into your passion again and your story we talked about the first rule from this slide was about, you know, be different and be you, tie that into your message, the type of relief that you can offer, then again you're making it believable, right? So if you say, well, I help, you know, high net worth individuals XYZ, whatever you need them to do, there's a lot of people again who may have similar messaging, but if you could tie it into why you're unique and why you started the business and how passionate you are about it, it makes it more believable. So you want to mention the step 3, the relief you offer. So fill in the blank is your exercise, the relief I offer my clients is, and usually it's related to the pain, right? The frustration and pain they have, it's the opposite. How do you actually go about solving that frustration or pain that they have?
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