Pushing Through the Challenges with Break-Through Mentor Winston Henderson-EP029

Tony Robbins once said that we are thrust into action out of inspiration or desperation. And sometimes it’s a little bit of both! Entrepreneurship can be overwhelming, and it isn’t always as easy to stay driven day after day – especially when the end goal seems so far away. Today’s guest shares his story of working through those challenges and developing the grit to continue. 

Winston Henderson is the Chief Visionaire at 5 Years 2 Mastery, an enterprise that seeks to equip and empower others to overcome the limiting beliefs that are holding them back as they work toward their goals, creating the life they’ve always wanted. He was introduced to entrepreneurship by his cousin at the age of 18. After several failed attempts to establish various businesses, Winston studied IT at university – and hated it. But the blessing in disguise was that he also discovered a love of marketing and a renewed interest in business. At 24, Winston spent a year and a half working a traditional job in sales before starting his own home-based hot beverage business.

Though Winston’s venture was doing well enough that he could quit his full-time job, he struggled to develop the necessary discipline to run a successful business on his own. As things fell apart and Winston entered a state of depression, he took a look at his options: He could either go back to a full-time job, or he could dig in and make it work. The birth of his daughter in 2011 motivated him to choose the latter, and Winston has built a business that serves ten countries and brings in a monthly revenue of $130,000.

Inspired to share his systems and help others reach their full potential, Winston has expanded his work, adding Digital and Content Marketing Strategist and Break-Through and Consistency Mentor to his job title. Listen in as he explains how consistent daily activities lead to big wins and how ‘celebrating the process’ keeps you moving forward as you grow into your most powerful self!

Key Takeaways

The challenges of entrepreneurship

  • Mental and emotional discipline
  • ‘Dig in and make it work’

How Winston shifted his mindset to acquire the necessary discipline

  • Desperation for financial independence
  • Strong, emotionally compelling reason to push through the challenges
  • Pain of regret stronger than pain of developing discipline

How Winston selected the products he promotes

  • Saw a demand/need
  • Capitalized on service aligned with that demand

Winston’s advice for building a lucrative business

  • Consistency
  • Start small
  • Visualize the end goal
  • Focus on daily activities
  • Refuel by celebrating the process

Winston’s secrets to success

  • Faith
  • Figure out what’s holding you back
  • Develop your communication skills


Connect with Winston Henderson

Winston A H - Headshot.jpg

Winston is an Entrepreneur, Marketing Strategist, and Break Through and Consistency Mentor, that has built a home based business to over $130,000 per month in revenues, across 10 countries. His obsession is to inspire and help others realize their full potential, create their most powerful self, so that they can create the life they've always wanted rather than settling for the life they have.


Full Transcript:

Laura Pennington (Host): Welcome back everybody to the Better Biz Academy Podcast. Today my guest expert is Winston Henderson. He is an entrepreneur, marketing strategist and breakthrough and consistency mentor who has built a home-based business to over $130,000 per month in revenue across 10 countries. His obsession is to inspire and help others realize their full potential, create their most powerful self so they can create the life they've always wanted rather than settling for the life they have. Welcome to the show.

Winston Henderson (Guest): Thanks for having me, Laura. I'm happy to be here.

Laura: Yeah, I'm excite to hear more about your story. So, did you have a more traditional job or something before you started out as an entrepreneur? I'd like to hear about how you got into business ownership and entrepreneurship?

Winston:  Well, I guess you can say yes and no. To really get an understanding of my journey we really need to start from I was about 18 years old and I was introduced to this whole amazing concept of entrepreneurship from my cousin, this idea of being your own boss, working for yourself, determining your own hours and creating your own time and financial freedom. And I was just immediately hooked on the entire idea of it form that early age with the guidance of my cousin. We started a few businesses that I can honestly say failed terribly. I'm sure many people have had that experience. We started a promotion - well, I started a promotion company. Then we started an event planning company. There was supposed to be like a marketing firm as well and a pastry business that I was about to start with someone else as well but that didn't pan out the way how we wanted. So, during that time probably I would say I was about 20-21, I started university and something really - I think that's really where I found myself and what I mean by that is I was doing information technology, computing, and to be honest with you, Laura, I absolutely hated it. I hated every second of it. But the blessing was that was actually a blessing in disguise because by figuring out what I hated that's how I really discovered my true love for marketing and business. And along the journey, I still started a few businesses along the way. I went into a traditional job probably when I was about 24-25. I've had like a few - I wouldn't necessarily call them jobs, they're more like, I guess you can call them hustles or whatever they may be. But my real real job started at the age of 24-25 and I was in that for a year and a half doing sales but just quickly realized that this whole concept of working for someone else is just not for me. It's not that there's anything wrong with it, it's just that I value my time more than I do even money because I know with my time I can create whatever mode of income I want for myself. So, that's when I started my home-based business, the one you mentioned. It's a hot beverage, so we're talking about coffee, tea, hot chocolate but healthier alternative to I sold there. And the first six months of the business were just amazing. I was earning twice in terms of income doing that business and I was on my full-time job. So, I decided to walk away from that job, which in retrospect probably wouldn't have been the best idea at the time. I thought it was, one of the things about entrepreneurship and for anyone that's listening, is that a lot of people think that when you own your own time it's easier, it's not necessarily so because when you work for someone then you're automatically disciplined - just show up at work, do the work you're getting paid to do. But when you're an entrepreneur where you're pretty much in charge of your own time, have the freedom that you want, then you pretty much have to discipline yourself. A lot of people at that level mentally or even in some cases emotionally, to be able to do that and I was one such a case. But then that was 2011 that I started that business so I got to that level 6-8 months. 2-3 months after, it just completely fell apart and I was in a state of depression for about 2-3 months following that. I was just in a crossroads where I said to myself, listen Winston, it's either you're going to give up this business and go back and get a job, find something to do with your life or you're going to dig in and really make it work. And that's what I did. That was 2012 but it really took me about two years to bounce back from that setback in that business to where I am today.

Laura: Wow! What a story and you exemplify this idea that a lot of people will see a story and it seems like an overnight success, it seems like it's been an upward trajectory for them from day one, and you talk about the real behind the scenes of the fact that entrepreneurship especially is an up and down rollercoaster and there are some real down moments where it's hard to push through challenges. People who have a successful business, they probably have 2 or 3 more that were not successful, they tried with. But the important bottom-line there is that you stuck with it. Now you talked about some people are just simply not cut out or would really struggle with the discipline that's necessary to be an entrepreneur. How did you shift your mindset and your habits with that so that you could become as disciplined as you needed to be?

Winston:  That's an excellent question, Laura. Really it was, I would say, I guess you can call it fear or probably it was the pain, it was two pains. We always hear people or I've heard it somewhere but I can't remember where right now but either the pain of discipline or the pain of regret; and that simply means either endure in the pain of disciplining yourself to go there and do what you know you have to in order to succeed or you decide not to but in your later years you have to live with the pain of regret that you didn't go there, you didn't make it happen. And for me, this is just me personally, like I've set a certain standard and expectation, not just for myself but also for what I believe my life should be, my lifestyle should be for myself or my family and it's just something that I refuse to compromise on. Like I just cannot see myself living an average life, living a life of someone who is just okay going to a job, paying the bill. And I'm not saying anything is wrong with that. Nothing is wrong with that but it's just that for me personally, I've always seen myself as someone who wants so much more. So, it was just a matter of which one is more painful? Is quitting this business and going back to work, not developing those habits more painful or is spending the next few months, even few years if necessary, to develop the habits more painful. Which is it? And knowing that you may possibly, if you don't develop the habits knowing that you may possibly lose out on something amazing. So, the advice I would give for anyone is you need to have a strong emotionally compelling reason why you're doing what you're doing and it can't be money. If it's money, it's not going to last because when the challenges come, when the emotional rollercoaster moments come, you're going to not have to, but you need it the emotional and mental toughness to really push past those moments. And if money is the reason why you're doing it, it's not going to be a compelling enough reason for you to keep going on and keep pushing through the obstacles and the challenges.

Laura: I like the way that you talk about can I just get uncomfortable and push through these habits now or do I want to do it over the course of several years? And I also think that keeping the big picture in the back of your mind helps you push through some of those greater challenges. Now, you've done something that's a little bit different than a lot of the guests that I've interviewed; a lot of them are service based providers and you have developed basically a product or a line of products. So, I'm very curious to know how you got started with that and what was necessary to have in place to launch a business like that?

Winston:  Well the wonderful thing about what I do is that I'm not actually one who manufactures the products. I'm simply a person who distributes and sells those products. So, a lot of the systems I learned in terms of entrepreneurship weren't probably someone else who had to start from very beginning and create the systems, create the product from scratch. Fortunately, I didn't have to go through all of those challenges with this particular business because I had businesses before where I had to focus on doing that, but for this particular business I didn't have to do that. So, the only thing I really had to concern myself with is really marketing or promoting the product, getting it out there, and creating sales and revenues for a distribution system.

Laura: Wow, that's so interesting. I'm always curious about people who start a business like this because I don't even understand level one where you're finding these products to distribute. I can see how it would be a lot easier to start a business that way than say, I've got to develop a product and now I've got to fulfill all these other parts of the chain before I can get started. But how did you come to the conclusion that you would do the products that you do? Did you already have a relationship with somebody who had developed those? Or did you do a research project?

Winston:  Well, the interesting thing about it is that my aunt, I have my family members, they were already aware of the product. As a matter of fact, I was aware of the product even years before I actually got started but it's just that at the time I wasn't interested in it because I was focusing on, at the time, starting my own marketing firm - because as I said, marketing is something I'm passionate about - and pastry business as well. So, I wasn't really focused on it but I can be honest with you Laura, I'm trying to remember who said it, I think it was Jim or Anthony Robins, it's one of the two that says we either take action or we're thrust into entrepreneurship by two things; either by desperation or inspiration. And I guess desperation pretty much speaks for itself. Inspiration is you see someone else who is successful and you decide, hey I want to do what they're doing. I honestly wish I could say that it was inspiration for me but it wasn't. It was desperation because my daughter was about to be born - at that time it was 2011 - and even though I had a job, I had a secure income, one of the things for me has always been that if I decide to have a child, I want to ensure that I'm financially not just secure but independent before that happens and it didn't happen the way how I planned it or expected it to. So, for me, it really kicked things into high gear for me where I said to myself, listen you need to figure this thing out. Yeah, you have a job, that's all nice, that's all well and good but you need to figure out how are you going to now provide the type of life that you want for your daughter. So, that's when I kind of soften up to the idea that okay because the irony of it is, and I can say 'is' and not 'was' because I'm still not really is that I'm not really a coffee drinker. I drink tea but I'm not really a coffee drinker. I might need to quote what Warren Buffet say that things that you like to do should be a hobby of yours but things that the world does, those should be your business. And even though I don't drink coffee necessarily, I'm willing to bet that's at least 80% to 85% of the world drinks coffee. So, I was looking on it from not a consumer standpoint but a business standpoint and from a business standpoint it just made a lot of sense to me. So, I just decided to go all in with this business and this product.  

Laura: A lot of the most successful business people seem to be the ones who see a problem or see a tremendous amount of demand in the market and then they create a product or a service that is directly aligned with that. So, you're a great example of the fact that you don't have to necessarily like the product or use it on a daily basis but if you can understand the people who do and what they're looking for and something like that, you can be successful. Now you built this business relatively quickly and brought it to a very high revenue point per month quickly as well. I'd love to know if you have any secrets behind how you got to do that?

Winston:  Well, if I could use just one term I would say consistency. It seems so simplistic but usually the most simple things are the most powerful and profound but it's just consistency and I personally have struggled with consistency for almost all my life and really when I looked on both time periods when my business really started to generate tremendous amount of income and revenue, it was during the periods when I was most consistent. So, that 6-month period that I mentioned when I first got started is when I was most consistent. Later on, in 2013 when I within 10 months generated about $130,000 in revenue is because I was most consistent. And then I looked in between and every single time in between when I wasn't doing as well as I should have was because I wasn't consistent. So, it's no secret really. To be honest, Laura, and myself included, all of us know what we should be doing. We know the "secrets" what something that Brendon Burchard says, "there's a difference between knowing something and doing it." And a lot of us know what to do but we're just not doing it, we're not doing it on a consistent basis. So, that would be my advice. Just start small, don't try to do too much too soon and that's something a lot of us as achievers and entrepreneurs suffer from because we even want to do it all right now. We just want to sleep for an hour or two per day and work ourselves into the grave hoping that we made this thing work. But I would say start small. It's not a matter of how much you do in a short burst or space of time but it's really about being consistent, being disciplined with the simple activities that lead up to the big wins.

Laura: I love that advice. It's really really powerful and it's something that I've seen in my own business as well as far as consistency. It helps prevent a lot of problems. Now one of the issues that a lot of business owners have is when they first start their company or when they branch out into something new, they have all the momentum in the world because the motivation and the passion is there. But like you said, it drops off after a while and then it just gets to be all about grit and hard work. So, once you lose that initial motivation, what tips do you have for someone who needs to pick the pace back up again in order to become consistent?

Winston:  Well, that's a good question, I like it so much. Let me see if I can pick some of the best ones. Well, it goes back to what I just said about starting small because one of the things about starting small is it's easy to start small and build from where you are because that's what really prevents burnout. So, I guess the greatest tip I could give in terms of what happens when you lose that initial motivation is to focus on the daily activity instead of the achievement. And I know this probably goes counter to probably what most people are used to hearing because what I used to hear, you know, keep your eye on the prize and so on. I'm not against that but I believe that it's more important to focus on the daily activity rather than the achievement. I mean, still visualizing, I'm assuming based on your audience, if a body should at least have an idea of what it means to visualization, law of attraction and so on. So you still want to visualize and keep in mind your end goals but you don't want to focus on it, meaning you don't want to spend every single waking moment thinking about it because what that then does is it actually overwhelms you because if you're going out there every day and you're taking action, doing the activity, you're not seeing how your actions are leading or helping you progress to the end result in terms of you're not seeing that immediate gratification of getting results right now. Then it's easy to become overwhelmed and feel as though your efforts aren't making much of a difference in terms of your achievements. So, the best thing to do is to focus on a daily activity; so, if you have a business, and you know you're supposed to make phone calls, if you know you're supposed to send an email, it doesn't matter how small it is, if you send one email today, if you make one phone call today for your business, that's going to help it progress even one step closer to your end goal, celebrate yourself for doing that. Celebrate that moment. Say, hey, you know, I did awesome today. I completed this task. I said I was going to do it and I got it done. And you celebrate that moment because what it then does is that that need for immediate gratification, that all of us have as human beings is now fulfilled on a daily basis and that can - I guess you can call it your refueling to keep you going to ensure that you continue to have that good feeling of celebrating and congratulating the process instead of waiting to the actual achievement of getting what you want.

Laura: Really important advice for anyone who's starting or growing their business there. Do you think there have been any secrets behind your general success aside from consistency? Has there been anything else that has helped you bring in results month in and month out?

Winston:  I would say faith is one, definitely. I'm a huge believer in faith, huge believer in god. I know most people are probably looking for more technical how-to and how-to is very important and developing the skillsets is very important but every single time I see tremendous success in my business wasn't because I did necessarily know what to do but it has to do a lot with faith. You have to believe that is going to help with even when you don't see it happening. In terms of behind the scenes, for those who would like the technical know-how, I would say figure out what it is that's holding you back from being successful in your business. For me, one of the major things for me was about I had a fear of rejection and also a fear of success - the latter I didn't even know that I had that one, it's recently I discovered I had that one - but that fear of rejection is a lot of the reasons why - not necessarily just fear of rejection but just fear on a whole is a reason why a lot of people aren't progressing as far as they could because they are for some reason whatever fear they have is holding them back from really putting themselves out there. So, if I could give any sort of advice in terms of technical skill, I would say the best skill to learn that has been a tremendous help for me is people skills and communication skills. Because at another day and no matter what business you're in, unless you're living in a cave by yourself, you're going to have to deal with people, whether it's your customers, it's your clients, people who you work with or people who you hire to be a part of your business - at some point in time you're going to have to deal with people so if you're not good with people then you need to learn how to develop that skill.

Laura: Talking about fear and being aware of your weaknesses and strategies is really really valuable for anybody who's in business because you can't allow yourself to get into a rut of just assuming that everything is fine and that you'll be able to work it out. Sometimes it's more important to be really honest with yourself and acknowledge that it's going to be hard to change things or to set a new goal that seems a little bit out of reach but it's also so worthwhile. Well, I just want to thank you for being on the show today. I know I've learned a lot from you and certainly been inspired by your story.

Winston:  Alright, thank you so much for having me, Laura. I mean, it was just an absolute privilege being able to share with you and your audience and I really hope I was helpful enough and provided enough value for your audience because that's always my biggest aim.

Laura: Oh yes! You were so helpful and I love all of your advice and hearing about your story. Remember listeners, that you can catch me every week on iTunes and on Stitcher Radio.

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