Do you want to grow your business big, VERY BIG? Jordan Levin’s guest in this episode is Jon Dwoskin, a business coach, mentor, executive coach, author, speaker, podcaster, and founder of The Jon Dwoskin Experience. Tune in and discover what factors keep you stuck where you are. Getting yourself unstuck certainly won’t happen overnight. But you can elevate yourself to the next level with the proper goal-setting and coaching. The key is to leave your ego at the door and stay consistent in your progress. If you are ready to grow your business, people, culture, and most importantly, your mindset, then this episode is for you. Join in!



I have a special guest, Jon Dwoskin. He is a business coach, author, speaker and fellow podcaster. Thank you for being here, Jon.

Thanks for having me.

Speaking of podcasting, you’ve got about well over 500-plus podcasts coming up. You’ve had about 500 or so now.

I have over 850. I’ve been doing it for a while. I love it.

What is it about podcasting that you enjoy?

For me, Jordan, it’s a couple of things. One, it’s like a mini masterclass for me. I love talking to people. I love asking people questions and getting to know what makes them tick. As a business coach, I help people reach their potential. I work with people who are successful and stuck and help them get unstuck. I’m always interested in everybody’s story. How did they get unstuck? How did they grow? How did they become what they became?

Processes don’t happen overnight. Accomplish your goals one week at a time.

For me, selfishly, it’s like a mini masterclass. The way I learn is auditory. I love talking to people and learning from people. I love sharing that with as many people as I possibly can. If I can do my part in helping give others tools whether it’s through me, the questions I ask or the guests that I have, it’s great. From the time I was eighteen, I’ve been listening to books on tape of Brian Tracy, Jim Rohn and Tony Robbins. I could go on and on. I’ve learned so much from them. A podcast is a platform for me to do that for myself and as many people as I possibly can listen to it.

Speaking of Brian Tracy, when you were about eighteen years old, your father gave you a bunch of Brian Tracy tapes. I can’t imagine what you were going through at that time. What I’m curious about is what do you think your father saw in you at that time for him to say, “Jon, here are some tapes.” Keep in mind, most people at that age throw it away and forget about it. What was it that you think that he gave that to you?

He handed me those tapes. My dad was a dentist and he was huge into continuing ed. He was always listening to these tapes, reading these books and going to seminars not only on the dentist but business as well. He knew that school, scholastically, did not come easily to me. He handed me the tapes right before I started college and said, “Jonathan, not that you won’t do well in college but you will learn more from these people than you will college. If you get less than three-point in college, I’m going to pull you out and you’ll have to come back home. I do believe you’ll learn more.” From the moment I put it on my ears, it was music to my ears. I don’t think a day has gone by where I haven’t listened, read and done something. Now with podcasts, books on tape, YouTube and things of that nature, it’s been the greatest. He knew that my skillset would be in alignment with them versus how I learned in school.

As a father now, how do you take this on with the academic situation? I’m not sure how it is now but when you give them suggestions, what have you heard and seen here have gone the other way?

How to Win Friends & Influence People

Especially when the pandemic hit, I’m always giving my kids books to read and things of that nature. I will pay them to read books. There’s like a stack of books that I tell them if they read it and talk about the book, I’ll give them $50. There’s another stack of books and if they read it and talk to me about it, they get $100. I want them to read it and connect with it. They’re important. I’m okay with that. They’ve read a bunch of great books that I don’t think they would have read otherwise that have made an impact on them. Who Moved My Cheese?How to Win Friends & Influence People, I could go on and on. Those books have priceless lessons in them. Whether I say it or not, they read it or hear from somebody else. When it’s not their dad, it illuminates and raises their consciousness when it comes to things.

That’s a great point because it comes down to education. Education is important. Education should be in the form of school, college, but there’s so much more to life outside of school. When we grew up, everything was all about school. My parents tried to make sure that I had other opportunities outside of that. From that aspect, parental support is an important thing for us. When you were about 31 years old, you were diagnosed with dyslexia. It’s almost like you were able to see and hear things before they happened. Would you say that’s one of your superpowers?

For sure. I didn’t know I had dyslexia. I knew that I was learning differently my whole life. Through some things in business, this presentation I had where I couldn’t remember certain things that I knew well. I went to my therapist and asked him for an IQ test. At the end of it, it was a five-day, two-hour day test. He said, “You should buy the book Living With Dyslexia.” I thought, “For who?” He said, “You.” To me, it made sense because I’d always had to rely on other senses and other ways of learning.

I realized that I was more of an auditory than a visual learner. It made sense why I have connected to these audiobooks on tape and these audiotapes and cassette tapes my whole life because I could retain them much faster. Because I didn’t learn as other people learn, I did have to pay attention to things that maybe others didn’t. It’s a natural gift that I have. I pick up on things. My coaching world allows me to help accelerate someone’s growth, get unstuck and get to their next level because I can see and hear what they’re missing. Sometimes, ever slightly missing but something that’s been holding them back for a long time.

A lot of that is not just from that experience but all the books and tapes that you’ve listened to. You’ve pulled out different scenarios through those books that you read and added to your knowledge of being able to help businesses get unstuck. I can relate a little bit to what you’re talking about there. I wasn’t diagnosed until I was seventeen that I was ADD or ADHD. I was hyperactive when I was a kid. When I was seventeen, I was given Ritalin. I remember being in the kitchen and reading a book. Normally, when reading a book, I will be distracted. I will not be paying attention.

All of a sudden, I finished the book and there were zero distractions. When I was done with that, I said to my parents, “If I’d have known about this, I would be in Harvard by now.” I felt so smart. I was able to retain information. From there, everything became much easier. I was able to be better at writing and speaking everything I was able to read. That’s helping people to understand that a disability is not a disability. It’s a different word, an ability. A lot of times, that disability heightens that awareness. That goes right into my next statement. When you’re working with clients, how are you able to point out those abilities for those people who can’t see them? How are you able to put the information out?

I ask a lot of questions and then I’d be quiet. This isn’t mandatory but most of my clients start with a deep dive anywhere between 2 and 10 hours. Doing a deep dive depends on the size of the business. Doing a deep dive, I’m understanding every element of everything that they’ve ever done and how they got to where they are. I can pull out themes that they are overlooking that they don’t see. I can hear and see the patterns of how they do things. It’s like a puzzle. I help them put the puzzle together that accelerates the growth and get rid of a lot of the distractions that are getting in their way. I help them start creating the vision of where they want to go and then reverse-engineering the tools.

That process doesn’t happen overnight. Sometimes people say, “Can I do it in an hour?” No. It takes a long time. I’m a great business coach but I’m not a magician. I can’t make it happen overnight. It’s a process. An individual can only process so much at one time. Change is difficult. Some people can move faster than others. The key is consistency. About 80% of my clients, when they start, they don’t stop working with me.

Find the right coach to help elevate you to your next level.

They know that through weekly or bi-weekly coaching sessions with me, ranging from 15 minutes to 1 hour, they are getting what they need to accomplish the next week, the next two weeks, the tools, the mindset, getting rid of distractions, the hyper-focus, the accountability, the ideas. All of this is to help them get unstuck. As they raise their level of consciousness, they’re at a new level of consciousness. They see things from a different perspective with new lenses that they didn’t see the week prior, the month prior, the year prior. It’s a constant growth mechanism of working with somebody to evolve and see and experience change.

A lot of that has to do with treating the muscles of the brain to accept that information and to be able to act upon the information. We tend to get stuck. We tend to have our own perceived notions of expectations of whatever it is. You’re coming in and saying, “Enough of that. Let’s get back to the root of what’s happening.”

Most people trip over themselves when they resist what they need to do most. Their habits are not what they need to accelerate their growth. Their perspective is limited. Their board room all looks the same. They haven’t been coached. They’re not open to feedback. They hadn’t been and now maybe they are. Their ego is big that it’s affecting the culture and everybody that interacts with them. Coaching is hard work. Sometimes when you’re ready, you know that a coach is there. When you use a coach, there are certain things that you got to be ready and understand the path and the journey that the coach wants to take you on. Sometimes they can see things that you can’t see. Most of the time, that’s understood. Sometimes it works for people and sometimes it doesn’t. It’s all about finding the right coach as well that can help you elevate your next level.AGT 9 | Jon Dwoskin Experience

Jon Dwoskin Experience: You can be a very profitable, scalable company, and be a solopreneur working out of your house with a virtual team.

I’m thinking about different boardrooms, CEOs. They have a contract. Speaking of that, you have a history of working for corporations. From my understanding, you love doing that. You work in finances. You work at all these different things and then you said, “I’ve had enough. I’m ready to go on my own.” Why did you make that transition? What was the cut-off point that said, “I need to go on my own. I need to be my own person.”

I had a lot of ideas. I have a voice that I knew I wanted to use in a certain way to help as many people grow, get unstuck and grow their business as possible. I’ve been working since I was 13 but I started at 23. I started an internet company with my brother and a buddy. We sold that. That was great. That was exciting. I got into commercial real estate. I was a broker. I ended up taking my off over. I did that for six years successfully. I went in-house for one year and helped another company restructure. I wanted to build something that was creatively in my head since I was eighteen years old. It was time.

I didn’t want to work for anybody. I didn’t want to ask anybody if I could take a day off. I didn’t want to ask anybody if I could show up at 8:30 instead of 8:00, leave early. I didn’t want to miss any of my kid’s things. I wanted to do what I wanted to do in the way that I wanted to do it. I had such a strong vision in my head that I had been building since I was eighteen years old. It wasn’t a question of if. It was a question of when. I was ready. I was 42 and I remember thinking, “I’m not going to be 50 and do this.” I don’t want to look back with regret. I jumped and I did it.

We’ll talk about the entrepreneur mindset and controlling your destiny, in a sense. It’s risky. I can relate to that. I was my own boss about as much of the time that you had. For me, having that control, take a day off when I want. There’s a sense of satisfaction. There’s a sense of accomplishment with that. It’s not easy to overcome that challenge.

I don’t even take a lot of days off. It’s not even so much about that. It’s the option. I don’t like playing politics. In Corporate America, I always had to play a lot of politics. You’re always watching your back and making sure you say the right thing to certain people. It was exhausting for me. I was good at it because I had to learn how to play the game but I didn’t enjoy it. It wasn’t in alignment with my soul. I didn’t want to go to work every day playing this game of chess where you don’t even know what the real game is. That wasn’t for me. I knew I could start a business my way, my vision, have my team, set up the way I want to set up my team, hire the best of the class of everybody and I did.

When you were talking about that, I’m thinking, “That’s exactly what I want.” It’s the same thing. What I’m curious about is at the beginning, you were in the Silicon Valley internet age when you started this internet company. You showed your data. You’ve talked about it before you’ve spent hundreds of hours getting into this. What was it again that you did it?

We had a website company in June of 1995 that we started. It was great. It was right when the internet was in its infancy. Most people didn’t even know what it was. My brother and I and a buddy of ours had a blast. We grew it. We sold it two years later in 1997. We had grown it to 300 clients. It was great.

What I’m curious about is what was it about the internet? At that time, I remember getting on the internet going, “This is cool.” How were you able to foresee it and be able to say, “We could do something with this.” You talked about it and came up with a plan. There had to be something that caught your attention.

It was the brainchild of my brother and our other business partner, Scott. They were talking about starting this internet business. I had graduated from college. I had gotten back from a three-week trip to Israel. They were starting this business and I chimed in. Long story short, I said, “This seems like it’s going to be the future. I want to be an equal partner. I’ll do all the sales. I’ll lead the sales.” It was in my parent’s great room. That’s where the negotiating took place. There was nothing to build at that time. There was no industry.

I graduated from college. I didn’t have a job. I didn’t know what I was going to do. I wanted to get into business. I wanted to start my own company. I didn’t know what that was. They were talking about it. It sounded like the future and I said, “Give me a third of the company. I’ll run the sales and grow the sales team.” That’s what we did. It was like, “Boom.” We then started growing it relatively quickly at that point.

That’s the challenge of the unknown. It’s rare for people to see that and want to take on that challenge. That’s what the entrepreneur mindset is, take the risk and run with it. It’s the same thing with all the businesses that I’ve done. I appreciate the effort.

I didn’t know anything about the internet at the time but I did a ton of research. I would go to Barnes & Noble. I would get all these magazines and get whatever books were written. I read as much as I possibly could so I could educate myself. We created some brochures and some packages. I took a phone book and started cold calling. It was a ton of fun. I missed those days. They were fine. We were working on ping pong tables. It was fun. Those were good days.

It sounds like a version of Google. Google has all that stuff. You beat them to the punch.

Read as much as you possibly could to educate yourself.

I never thought about that. Our ping pong tables were used as desks and not playing ping pong.

When we’re talking about these businesses, we’re talking about digging a little bit deeper, understanding the client, the how and the why. We’ve talked multiple times about finding the client avatar. What I’m curious about it is what does that mean to grow a business? What is important about finding the avatar?

We must know who our ideal clients are, down to all the nitty-gritty. We also need to identify who our clients are not. When we know who our clients are, we understand how to attract them to us through our messaging. I’m a big fan of having a simple message. My tagline is, “Grow your business big, very big.” If you go to my website, you’ll see I work with successful people who are stuck and want to get unstuck and to think big. It’s simple steps that I can work with people to get unstuck. Those are my clients. They fall into categories where they are ready to get unstuck. Their ego is at the door. They’re ready to coach, to do work, to be consistent and do things on an ongoing basis.AGT 9 | Jon Dwoskin Experience

Jon Dwoskin Experience: Slow down, be present and enjoy the journey.

I remember I went to a meeting years ago and the guy said, “I’m happy where I’m at. I don’t want to think big.” I said, “That’s great. There’s no reason for you to use me if that’s where you are.” That’s not my client. For all companies and all clients, it’s important to know who your client is and how you’re messaging to them. What’s your ask and attract? How are you getting them into your funnel? How are you getting them to call you? How are you getting them to your website, your social platform? The messaging has to be repeated over and over again, up to 17, 50, sometimes 100 times before somebody maybe picks up the phone to call you. You want to be clear so the message is consistently clear and doesn’t confuse your ideal client/avatar.

That’s an important point because if you look at these bigger companies, most of the bigger companies out there are consistent with it. Particularly the medium and smaller-sized companies if you go to their website, you can see all these different things. You’re like, “What are they good at?” You’re not quite sure even if you see these different things. What I’ve learned through the years that I’ve made plenty of mistakes is, for me, I’m coachable. That’s what we do. We’re good at CrossFit. We have great coaching and that’s why I’ve been successful with that. I read your book, The Think Big Movement.

Thank you.

I want to touch on you about that book. I highly stress this book for anybody. The way that you wrote that book is eloquent. It’s easy to read to the point that it makes you think about a lot of things. Can you give us a different look?

First of all, thanks for reading the book. I loved writing it. I had a blast with it. It is about a guy who is in business. He’s stuck and can’t figure out why. Through the book, he comes across a series of a lot of guides that help him get unstuck. As a coach, I’m a guide. My client is the hero. My goal is to always make them the hero. I’m a big believer that all the guides and mentors that come across your path happen for a reason.

If you’re open to the feedback and the coaching, you can get unstuck, back to center, back into alignment and then you can see a little bit more clarity on what those next steps should be. That’s what happens to the main character, Jacob, in the book. He’s stuck and comes across all of these guys, mentors and gets introduced to all these different people, a business coach. He evolves to the level of where he wants to evolve and gets in alignment with his purpose, his soul, his business and his personal life as well. It’s a business book told as a parable because stories are easier to absorb and read.

That’s a short summary. I love it.

Thanks, Jordan.

Let’s talk about the pandemic. What do you think are the benefits of starting a business in the pandemic versus prior to the pandemic?

We’re seeing a lot of entrepreneurs pop up with the pandemic. We see people who are laid off and taking control of their own hands and starting their businesses. During the pandemic, working remotely, working in any room in your house with virtual teams is normal. Before, you’re working from your basement with virtual assistants and you’re not that real. Now, it doesn’t matter. It completely changed the game. You can be a profitable, scalable company and be a solopreneur working out of your house with a virtual team that’s quite extensive.

When we know who our clients are then we understand how to attract them to us through our messaging.

I interview people all the time on my podcast who are running major companies, multi-million and sometimes in the hundreds of millions of dollars with a team of 10 to 15 people, a majority of virtual people and support staff to help with things. The stigma of that is gone. There are a lot of new ideas that are coming to the surface because of how people learn and what people need. In the online space, everything is moving to eCommerce more so than ever before. Most people thought of eCommerce as a retail avenue but it’s for professional service companies. Everybody needs to figure out how to get and grow online for their internal people and attract new people.

You have experts that will start to pop up who have been experts in industries and corporations for 10, 20, 30 years. They’re going to start their businesses in niche specialty markets, helping other companies growing their HR, growing in recruiting, and most importantly, training. I do a ton of training and most companies do not train their people enough. One of the biggest issues I hear from companies is that our people don’t train us enough. Companies see a huge turnover when it comes to not training enough and not connecting with their people because they feel like they don’t matter. There are many opportunities in eCommerce and the virtual space in growing all of those areas. It’s huge.

For me, I grew an arm of my business during the pandemic that couldn’t have survived before because the market wasn’t as flush for it as it is now. My coaching is one on one, custom, high-end training. I never like turning people away. I created a group coaching model where those who can’t afford the custom one-on-one coaching can afford the $50 a month group coaching. It’s live every Monday. It’s me. There’s a private Facebook group. You’re going to start seeing a lot more of that from other people because it’s affordable and you get a ton of value. We’re going to see a lot of great new things pop up. Studies show that 85% of jobs that exist in 2030 don’t exist now and those are pre-COVID numbers. We’re going to start to see a lot of new things pop up.

I like that because you’re all afraid of starting an online business. I am one of them. For years, I’ve been trying to do something online but I’m not sure what that is. Now, I’m starting to get more in alignment. I’m starting to understand what that is. I’m not afraid to pick that up.

That’s a big thing, too. People are more in alignment with their values now than they were before because of COVID. People want to be in alignment with themselves. They realize that life is short. Life changes. They have these ideas they want to jump in. Whether it’s a full-time or part-time business or a side hustle, people want to have control instead of potentially being in a situation where they can get laid off.

What’s the greatest lesson that you learned on a client?

The common theme of the greatest lessons I’ve always learned from clients is to slow down. On my podcast, one of my questions is what’s the greatest piece of advice you ever received? A lot of it has the energy and the review to slow down, be present and enjoy the journey. That may sound cliché but it’s true. You have to slow down and enjoy it. I can never remind myself that enough.

That’s the whole point of this show.

It’s being in the moment.

One last thing, what’s the most important lesson you’ve learned from a mentor?

I had a business coach for about fourteen years, Jules Rappaport. He was the greatest. He passed away unexpectedly. I love him. He taught me so much. He always used to say to me that I needed to be more selfish. I was selfless. He would always say, “You got to be more selfish and know when to say no. Make sure you’re taking care of yourself and be a little bit more selfish.” I always would get irritated with him. He would say it because I never understood what he meant. The older I get, the more I realized what he meant which is you’ve got to focus. You’ve got to know what to say yes and no to. You don’t always have to be such a people pleaser. You can be selfish. You can say no. Take care of yourself and your family. That was great advice. I think about that all the time. My perspective and consciousness of it are always evolving as I think about that and him.AGT 9 | Jon Dwoskin Experience

Jon Dwoskin Experience: Take care of yourself and take care of your family.

I know what I know now. I can relate. I understand what that means. If you would’ve said that to me years ago, it wouldn’t have made any sense. Now that I’m thinking about it, it makes perfect sense. The last question I have for you is what brings you joy?

It’s my family, my kids, wife and dogs. First and foremost, my family always comes first before anything. That’s what brings me pure joy, my kids, my wife and our two dogs. Hugging them, loving them is what brings me joy. I love what I do. I’m passionate about my career. I love what I do every second of it. It brings me joy helping clients get unstuck, finding fulfillment and reaching their potential and next level. My family is the ultimate.

Jon, thank you very much. It was a pleasure to hear your story.

Thanks, Jordan. I appreciate it. Thanks for having me on the show.



AGT 9 | Jon Dwoskin Experience

Jon Dwoskin is a business coach, mentor, executive coach, author, speaker and podcast host.

If you are a business owner, executive, manager or salesperson who is successful, stuck, and ready to THINK BIG(GER), I can help you grow your business big. Very BIG!

If you are ready to grow your business, people, culture, bottom line — and most importantly, your mindset.accelerate growthauditory learnerbusiness ownercoachingdyslexiaideal clientHeidi Budaj – Assist. Dir. JCC Of Metro DetroitPablo Gonzalez

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