Driven Young with Byron Dempsey

September 14, 2021
James Whittaker

Check out this episode on the Win the Day Podcast

“To avoid criticism, say nothing, do nothing, and be nothing.”

Aristotle

Our guest today is Byron Dempsey who is doing some incredible work to empower young people and shake up the educational system. Through his Driven Young brand and the Driven Young Podcast, Byron’s amassed 600,000+ followers and 300,000+ podcast downloads. 

After learning more in two months as an entrepreneur than he did through all of high school, Byron initiated a movement where he teaches practical life skills that aren’t taught in schools so young people are equipped with all they need to succeed in a rapidly changing world.

If you’re on TikTok, you might have already seen Byron’s empowering work. Through two brands, he’s garnered 15+ million likes and is leading the charge for younger generations to take ownership of their lives. 


Check out the YouTube or podcast version where Byron Dempsey does the Win the Day Rocket Round, answering questions about his favorite quote, what advice he’d give his 18-year-old self, the one thing on his bucket list, and a whole lot more🚀


In this episode, we go deep on several topics, including:

  • The problem with high school
  • What young people can do to succeed
  • The #1 decision that catapulted his career
  • How to go viral on TikTok, and
  • Why mental health is the best metric of health and success.

Before we begin, remember that the right bit of inspiration can completely change the trajectory of someone’s life, so if there’s a friend or loved one who needs to hear this episode, share it with them right now. 

Let’s WIN THE DAY with Byron Dempsey!

James Whittaker:
You're making massive moves around the world with the Driven Young brand. What does Driven Young mean to you? And what's the change that you're hoping to inspire?

Byron Dempsey:
With Driven Young, the tagline I use is 'Practical life skills we didn't learn in school.' It's really aiming for the Gen Z audience, so people aged 15 - 23. It's trying to provide a lot of what I think school should be teaching us, such as soft skills like communication, money and finance, emotional intelligence, and relationships.

All these topics are universal and can prepare us for almost any job. For example, communication skills are going to benefit you in any career you go down, whereas advanced mathematical equations might only benefit you if you're going into a career path that requires that skillset. It's something I'm very passionate about.

Take us into the moment that you realized the traditional education system was broken and that something had to be done about it.

I always had inklings when I was in high school. For example, in biology, I had the most phenomenal teacher and I'd say, "Miss, why do we need to know this?" And she would say stuff like, "Well, you don't need to know this in the real world, but you need to know it for exam." It made me think, "Well, what's the point? Isn't school supposed to be preparing us for the real world?"

In high school, I quickly realized, I don't need an ATAR, because my goal was to be a filmmaker. I knew I didn't need good marks to be a filmmaker, so I just put a lot of time into making films for clients and for the school. A lot of the end of year projects I filmed and edited.

It wasn't until I got a job with a guy called Glen Carlson who runs Dent Global that everything changed. A lot of your listeners may have read his business partner's book Key Person of Influence, which is a best seller around the world and I highly recommend it.

I spent about a year with Glen almost doing like a Gary Vee style, following him around, shooting video content for his personal brand. And man, the amount of stuff I learned in that year was phenomenal. I learned about advanced marketing, Facebook ads, communication skills, presenting, creativity. Since I got to go to all of his business events and network and meet all these cool people, it really opened up my mind to the world of business and to, I guess, the real adult world. I knew very quickly that this is the sort of stuff I should be learning. I've learned more in a month than I have in 12 months at school.

I've learned more in a month than I have in 12 months at school.

And so that seed got planted and I started having conversations with people, like my dad in the car, and with anyone I met. I started having these conversations and I quickly realized that this wasn't just my opinion, and a lot of people agreed with me. That was the catalyst for starting the podcast.

The podcast, funnily enough, came through We Are Podcast in 2018. I'm not sure if you were involved at that point, but Ronsley Vaz hosted the event and I was one of the speakers. That allowed me to go to the speakers retreat with guys like Jordan Harbinger and Pat Flynn. And I had no idea who these guys were! As I hung out with them, I just realized how powerful podcasting was.

It made me realize I could marry up all my skills like video marketing and bring on experts to cover topics that I'm not an expert on. Podcasting sounded like a great way to build up my communication skills and grow my network as well.

Yeah, nothing opens the door like a podcast. And it can be started pretty much immediately for barely any financial commitment whatsoever.

What do you say to people who might feel that doing well on exams sets them up for better success in the real world, even if it's not directly applicable to adulthood at the time?

I was pretty average at high school because I didn't fit within the criteria high school sets for you. It can make you grow up and feel that you're not smart.

On the flip side, if you're naturally good — and I have friends who were naturally good at high school — they think they're really smart. And then they get hit like a brick when they enter the real world and go, "Well, these skills don't actually transfer over." So it's almost like a lose-lose situation, no matter what scenario you're in.

The people who are getting good grades, that's awesome and really valuable. It shows that you have a great skillset. However, don't think that's going to solve all your problems. You're still going to have to work hard and develop other skills as well.

And then people who aren't getting good grades, you need to make sure that doesn't define you. Whether you get the best grades or the worst grades, don't ever let that define you. I mean, how many stories have we heard of successful entrepreneurs who've flopped, or dropped out, or had all these horrible things happen and now they're living their dream.

There's a speech that I did once to a corporate audience that invited newly awarded OP 1 students to attend. From the stage, I felt that there was this smugness from most of them. And I just wanted to let them know that, in three months time, no one will care that you've got an OP 1.

I just wanted to grab them and say, "Look, life is going to absolutely kick you in the ass, over and over and over again. How you respond to that, irrespective of what's happened in your past, is the real indicator of how successful you become." I truly believe that the OP 1 doesn't quite have the impact that the school and most parents place on it, often to the kid's detriment.

Absolutely. One of my fantasies is to visit a private school and give them a bit of a wake up call, because you're spot on. And I think it's more important than ever because the world for Gen Z and entering the workforce is really difficult and less linear than previous generations.

It used to be kind of simple: you get a degree, then you can use that degree to get a job. Now you need to be looking at, "Is the degree I'm getting worthwhile? Is there a demand for that? Am I passionate about what I'm doing for it?" And there's so many variables and questions.

Whether you get the best grades or the worst grades, don't ever let that define you.

As much as I love the amount of opportunities there are, for the everyday person, it's really tough. For example, all my high school friends, they're great guys and I love them. But I don't think any of them are working in a career that relates to their degree.

Now obviously, we've got COVID right now in Australia, so that's a big factor. But a lot of people are really struggling and it's tough. It's really tough for young people to find a job. So I do think you've got to humble yourself when you enter the adult world. It's completely different to the one that we've grown up in.

With young people, is one of the big things you're focused on about providing broader exposure to the ideas of what's possible so they can insulate themselves from a specialization in a career that they might wake up one day and realize they're not suited to?

Yeah, it's a great question. And before I get to that, I want to comment on something you said, which was exactly that —  waking up at 35 or 40 and thinking, "Wow, this career isn't actually for me." I guess my dream with the podcast is to prevent that from happening and to help you realize that at 18 or 19 years old. To me, that is the most valuable thing that I can give to my listeners.

But in terms of specialization and generalization, I'm probably more of a generalist, but I have specialties within that. I'm a big fan of young people just trying as much as they can while they're young. Be a generalist while you're young. Through trying a bunch of things, you can find what you're great at and become a specialist.

Kerwin Rae did a video on Instagram where he said, "How do you figure out what your favorite ice cream flavor is? You try it. You taste it." And that's what life is. How do you figure out your passion and what you want to do in life? Taste and try.

How do you figure out your passion and what you want to do in life? Taste and try.

That's valuable for anyone, but when you're 18 to 25, you can taste things with very little consequences. Like me compared to you, if whatever I'm working on fails right now, I'm living in my parents' home right now. It's not the end of the world. But for you, you've got a young daughter, you've got a wife, and you've got a lot more responsibilities than me. So it'd be a lot more higher stakes if you were to go bankrupt or fail than me.

That's what I try and share with young people. There's a window of freedom they have and you need to use it wisely.

You work with a bunch of motivated go-getters who have big dreams and very little excuses. With the right foundation, is it possible for everyone to be driven young as you define it? Or is it only for those who come out of high school with a motivated mindset to begin with?

It's anyone. I mean, I've got people who are 35 that listen to my podcast. I had a guy, I forget his name, but he messaged me and was like, "Hey man, I love the podcast. I've just quit my job, you've changed my entire mindset."

Anyone can listen to my podcast, but I do to try to keep it relevant to young people. It really is anyone, but whenever I say this, I always get comments from people who say, "That's easy for you to say because you've got a level of privilege," which is totally true. Being born in Australia, I've always had food and water and all that sort of stuff.

But a comment one of my previous guests made was that everyone can make do with the privilege they're in. I can look at people who are way more privileged than me, and millions of people can point at me up here. It feels like an infinite loop. Everyone makes do within the privilege they're in.

No matter what circumstances you're in, find a way. Stop making excuses and start leveraging being young. Take those risks. I think everyone can be Driven Young, hence the name of the show.

When it comes to high school, there's really two things. There's the wider curriculum that we have little control over. Then there's individual accountability, which is definitely in our control. If you had your time again at high school — and you're certainly years ahead of me when I was your age —  what would you do differently from an individual accountability perspective?

I'm really glad with how I did high school because I guess I had the realization that I didn't need good grades. And so I'm really glad I didn't put all my focus on grades, and I was lucky because I wanted to do filmmaking which is something that really doesn't require traditional grades. So I was lucky I was going into creative field. And so I would just double down on that. That was more valuable for me than any exams or marks. If I had my time again, I'd build up my experience, grow my network more, and maybe be a bit more entrepreneurial.

I think it's crazy, because I know I've mentioned to you, I'm a head presenter at a program called Empower U. It's a life skills program and a personal development program for teenagers. I wish I did that when I was younger. I don't know how I didn't know about it, but I think researching and finding more stuff like that, because you can meet incredible people and get access to all this stuff. If I had my time again, I would say go to Empower U, become an assistant volunteer, and start building up my leadership skills in that.

If I had my time again, I'd build up my experience, grow my network more, and maybe be a bit more entrepreneurial.

There's a lot of stuff you can do outside of school that is really going to skyrocket you once you get into the adult world. And I think that just relying on tertiary education and not doing any extracurricular activities can be quite dangerous because you're almost putting all your eggs in one basket; then, then when you graduate, you have nothing to pad out your resume, which is important nowadays. It can hit you really hard.

Life is definitely a marathon, not a sprint.

From what you've shared with us so far today, it sounds like exposure and relationships have been key for you. Exposure to things outside your comfort zone, and relationships with people who have had real world success that you can learn from and be mentored by.

When I look back at what I learned in high school, I don't remember a single thing that I apply today based on what I learned in high school. And I know I'm a bit more further removed from high school than you are. But one thing I do have is a lot of friendships with people from high school that are still very strong today.

Toastmasters was one thing offered as an optional activity at my high school. That was really great, just to learn a few basics of public speaking and to develop that competence at the time.

But one thing specifically was the relationships I had with the teachers. It wasn't the content — I literally don't remember what they taught me. But I am still friends with many of those teachers today, despite having graduated high school in 2000, and I really value those friendships.

How do you feel about the role of teachers in the Driven Young awakening? And are they part of the problem or part of the solution?

Yeah, it's a great question. And I love the point you made, because I think, it's funny when you enter high school, in my experience, at least, in Australia, we've got, junior high school, which is the first four years, (year 7, 8, 9, 10), and then you've got senior high school (year 11 and 12). When you enter year 11 or year 12, suddenly your teachers almost treat you like equals, they become good friends, and it's a really cool experience. And so I agree, having those friendships is great.

In terms of, are teachers part of the problem or the solution? Absolutely part of the solution. In Australia, teachers aren't looked up to in society like they should be. It's not like you see someone who's an engineer and you go, "Oh wow, they're studying engineering" or "Oh, your daughter's studying to be a doctor."

Teaching seems to be more of an afterthought degree. And it's also a very low ATAR degree. A lot of people pick it as a backup plan and they're not as passionate about it. As a result, we get a lot of teachers who aren't doing it for the right reasons. And you can tell the teachers who are incredible and the ones who aren't. We all know those teachers who are like amazing and the ones who weren't.

The other thing is, I have a lot of teachers reach out to me saying, "Hey, I listen to the podcast, I love what you're doing. I totally agree with you, and we're stuck in a system just like you." To me, it's got more to with the education system. Because if a teacher goes, "You know what? Screw this. I want to teach you guys stuff that actually matters," and they teach a class full of kids stuff that really matters, they then bomb their exams and the teacher gets fired. So they're trapped.

And I'm starting to reach out to teachers. Like I spoke at a school, because she listened to the podcast and they're implementing a life skills program. And they really try to change it up as much as they can, but they're still stuck in the system. So I hope teachers are going to be part of the responsibility.

I also believe we should be putting teachers on a higher pedestal and making the requirements to be a teacher much higher than they are right now, because that way we're going to attract higher quality teachers. In my opinion, teaching is one of the most important roles in society because it's educating the next generation.

If you could design the perfect high school, what things would it include?

My mate, Joe, who is doing the Gap Year project with me, we've got a book coming out soon. He organized that entire project. He also created something called Gillage, and that's his perfect school. You have to take it with a grain of salt because there's so many moving parts, but primary school especially should be about having a good time first and foremost. Yes, we can teach how to read, basic multiplications and all that, because obviously that's important. But I think what's more important is just having a good time.

It's the same with high school. Hypothetically, we would have a school where you choose which class you want to go to. If you want to sit all day in the sun and read a book, you can do that. If you want to play sport all day and have fun, you can do that. If you want to go learn about science, you can do that. Or if you're going to learn about this one, you can do that.

Also, there wouldn't be as many exams. For example, in Finland — which I believe is the number one education system in the world — they don't have a single exam until you're 18 years old. They also call their teachers by their first name and the teachers work way less than teachers in Australia. It's like 850 hours a year for teachers in Australia and 600 hours for teachers in Finland. So it's crazy, they're doing less work, but they're getting highly revered. And they're getting better results.

In my opinion, teaching is one of the most important roles in society because it's educating the next generation.

So I think definitely remove a lot of exams, try to take the pressure off kids, and focus on giving them a good time. And really put a focus on mental health over grades. It blows my mind how much school prioritizes grades over their kids' wellbeing.

Obviously, if there was a way to measure their kids' wellbeing, maybe it'd be easier to see how everyone is doing. But there isn't really a way to measure and so they don't track things like whether a kid has depression. That's a whole conversation we could have.

Joe has written a whole article about his perfect school. It puts a big focus on developing experience and making sure they have a good time.

Elon Musk has a school concept where he actually puts people of different ages together, allowing the older ones to act as leaders and work on solving problems collaboratively.

I know you've mentioned this a bunch on your Driven Young Podcast, but getting people excited about coming to school needs to be the first step in overhauling the entire curriculum. For instance, my daughter is two years old, so we're going to reach a point with her in a few years where we have to send her to school for eight hours to sit at an uncomfortable desk and learn things that she probably doesn't want to learn.

If I had to really boil 'success' down to two attributes for anyone, regardless of age, it would be resourcefulness and resilience. How can we get those two attributes — resourcefulness and resilience — into the arsenal of young people as soon as possible so they feel equipped and inspired to rise above any adversity they face along the way?

Resilience is something young people lack. Man, we lack resilience. And it's not our fault. I'm not trying to blame anyone. It's just that everything comes so easy to us. Life comes so easy. If you want to talk to someone, just text them. If you want to get food, just order it online. You don't have to speak with anyone. We have no resilience.

I look at my grandpa who was one of 11 kids. They had no running water and they lived on a farm in New Zealand. It was cold. They had to walk 10 kilometers to get to school. There's actually a track called Dempsey's Track named after us because they walked it for like 20 years between his kids. Those elements developed a level of resilience. Same with my dad. My dad joined the army, and he believes that developed a lot of resilience for him.

Today, young people aren't really doing that, so I think we should put them in positions similar to what you said. My mate, Jack, did a leadership program in school where a bunch of them would get grouped up. They would say, "All right, these six of you, you've got three minutes to do this task. Go!" And then they have to figure it out. They've got three minutes and they'd analyze everyone and they'd have different roles and they figure it all out. That develops a level of leadership, resilience, and heavy resourcefulness. You have to think on your feet and work as a team.

Resilience is something young people lack.

My mate, Luke, we joke that our education would be dropping someone off in a Third World country with 50 bucks and telling them they have 30 days to find their way home! And that's kind of the mindset I want to push on young people — that you've got to put yourself in tough situations and figure the way out. I think we have way too many exits as young people, which then crushes our resourcefulness and resilience because we can just exit.

When you step out of your comfort zone, you've got two choices — you can either push through it or you can step back into it. And most people in life step back into it.

What decision has made the biggest impact on your life to date?

I don't know if you've heard me talk about the Thousand Doors concept, but the idea is that behind one door is potentially 1,000 doors. Most people see one person and see one door. That's an opportunity. But you never know —  there could be 1,000 doors and 1,000 opportunities behind that one person. For example, when Ronsley said, "Hey, can you jump on a call with James and talk about We Are Podcast?" and I said, "Yes," how many doors have been opened for me since then, just by saying yes to jumping on a call with you?

When I was 15, my mom made us go to a camp where we had to look after disabled kids for five days, rather than have five days of our holiday. I made the decision to say yes and enjoy the experience, and the ripple effect for that got me to where I am today. I met this person, who introduced me to this person, that got me into this, which got me listening to this person, etc. And here I am today.

Saying "Yes" to everything as a young person led to so many opportunities. They say a life-changing opportunity comes across your door every two weeks, whether you have the eyes to see it or not. When you put yourself out there, it's crazy what can happen.

On the Win the Day show, we talk about good habits people can implement to be successful and win the day. For you, I want to flip the script on that. What are the bad habits that young people need to eliminate if they want to be happy and successful and fulfilled long-term?

A real simple one is don't go on your phone first thing in the morning. I also run a company called 5:30 Club, which has about 25 clubs around Australia where people meet at the cafe at 5:30 every morning. And it's just been incredible. During lockdown, I can't do 5:30 Club at the cafe, but I'm still doing it in my lounge room.

Grabbing your phone immediately is a terrible habit. When you wake up, don't hit snooze. Get up straight away and do something to start your day. Even if it's reading or going for a walk or something, just start your day. Phones are a really bad habit you want to break.

Agree. When you sit down with someone for lunch or dinner and every 30 seconds they pull out their phone, "Let me show you this!" Drives me nuts. Can we please put our phones away!? They're glued to us constantly.

Yeah, and how does it make you feel when someone pulls a phone out while you're talking to them? I've been on the receiving end of that, but I've also done it and I've felt bad. I'm like, "Why did I do that?" Because you're not doing it intentionally, you're just pulling it out as a reflex. That's it. So admitting that you have an addiction is probably a good first step.

Also, just getting in the habit of gratitude and having perspective, especially during lockdown. I think we're approaching week 10 in lock down, which has been really brutal. And there's been a lot of bad things from it, but just trying to be grateful for the good things. The fact is it's not the end of the world, life will move on.

We've mentioned your awesome Driven Young Podcast a bunch already. And anyone who's watching this on YouTube or listening to the podcast, go and subscribe to the Driven Young Podcast.

How has your life changed since you made the decision to get into podcasting?

Oh man, how long do you have!? I mean, there's just been so many benefits and I could talk about podcasting for a long time.

One thing I underestimated was the networking you get from podcasting. And because I do all my interviews in-person as well, it's like a two and a half hour thing. They drive all the way out to me, we'll have a coffee for 30 minutes beforehand. We'll build a bit of a rapport, we'll have a chat, do a one hour podcast, then speak for another 30 minutes off camera. And then they'll go home. So I build really, really strong relationships with my guests.

It's just been such an incredible way to grow my network. And it's funny, all my friends actually have somehow come through the podcast. I had someone on the show, then she introduced me to this person and I've got a whole friend group from that. And so pretty much every aspect of my life has changed because of the podcast.

All my friends actually have somehow come through the podcast.

The whole reason I met Joe, who's my co-founder and a good mate of mine, we've got this book coming out and I'm one of the authors because I have a podcast and I got introduced to this person. It's not that he wanted to come on the podcast, but the only reason I had a connection to him was because I had someone on the podcast and it's just like infinite doors have opened because of it. And I almost can't explain it. It's just been incredible. And obviously, I've built a big following online, which has been opened up a lot of doors as well.

Also, the lives you can impact. I get messages every week from people who tell me how much they love the podcast and send huge paragraphs about how much it's changed their life. I'm not sure if I've shown you or not, but I screenshotted a message from a 14 year old girl from Canada who sent me the most beautiful message about how her and her parents listen to it together. It's crazy how much just saying some things can change people's lives.

The other thing, and I don't know if you've had this, James, the way I listen to the podcast, if I discover your show, I'll flick through the most recent 10 episodes, and maybe pick one or two. But I have had people go back and listen to every single episode! They'll go back to the start and go through every episode, which is like 70. That's not how I do podcasts and I didn't realize other people do that, but that was crazy to me. I don't know, do ever notice your listeners do that as well?

Absolutely. And I feel awkward saying this, but I don't even want to go back and listen to my earlier episodes! When you try something new, the finished product seems a bit elementary when you advance so much further into the pursuit.

My first episode was called 10 Tips to Handle the Haters, because I feel how we handle that negative energy from people around us is so important. I've thought about actually redoing that one because it was literally the very first episode I did in podcasting.

Yeah. I mean, my most listened to episode is episode number one, which I didn't expect. I wish I had known that at the time! But yeah, so it's just been huge. I can't even put into words how much has changed my life in terms of opportunities and growth.

It's great because I've learned from 70 people and then I edit the podcast and then I listen to it again. So it's like, this stuff just becomes who I am. It's also accountability. Like if I'm teaching people to do this, I need to be doing it as well.

Yeah, it's forced learning to consume the content of the person you're having on the show beforehand, it's the relationships, it's getting better at communication, it's great branding, and provides omnipresence on social media.

I didn't even mention the communication skills. So many people reach out to me and say, "I just love the way you do your podcast. It's super conversational. It's so easy to listen to." And that's, it's such a cool thing to hear, that I'm not just another guy with a podcast. I've actually put a lot of time and effort into mastering this craft, so it's very validating when people mention that. Even if you have no listeners, there's infinite benefits to starting a podcast.

Absolutely. The ROI of having a podcast — if you do it in the right way — is 10x the value before anyone even listens to the episode. Again, if you do it the right way.

Yeah. And the other thing I would say, if anyone of your listeners are wanting to start a podcast, but worried about the judgment or result, you have to understand everyone is starting podcasts, but very few people are actually maintaining them. Not many people are actually consistently doing it.

Even if you have no listeners, there's infinite benefits to starting a podcast.

Almost every time I come across someone who has a podcast, I look at the most recent episode and it'll be like eight months ago or a year ago. And I'm like, "Yep. Classic." Because not many people stick through it. If you just stick to it, you'll be in the top 20% of podcasters in no time.

You've also leveraged your podcast to become the king of TikTok! You're doing amazing things on there. You're inspiring me with all your TikTok stuff. You've got more than 300,000 followers on TikTok, with more than 10 million likes.

What specific steps should someone take if they want to dominate TikTok today?

Yeah, I've got a free TikTok training where I break down my entire strategy of how I've grown on TikTok. First of all, you've got to get on the platform and understand it, because it's completely different to any other platform you've seen before.

Start creating content, start putting yourself out there, and don't worry about the judgment. For me, I still I just do podcast clips. I just take clips from my episode and post them onto TikTok. And I've mimicked that strategy with a second account that now has 300,000 followers. So I've got 600,000 followers on TikTok. I've grown two podcasts to be quite successful through the platform alone. And it's just been incredibly beneficial.

So immediate steps I would say is get on a platform, make sure you fill up the whole video. So don't do like a square. You want it to look native on the app. Use TikTok fonts and titles, so it looks like it belongs in the app and it's not like an ad. You don't want to look like an ad.

Make sure that you have an engaging title and engaging half to one second. It's got to be bang straight into the content and remove any ums and ahs and remove anything that doesn't progress the story. Sometimes I'll cut out 20 seconds of the snippet because they make a really good point, but it doesn't progress the overall message. So cut it out.


Byron Dempsey's strategy to grow a TikTok following:

  1. Become a regular TikTok user.
  2. Start publishing content.
  3. Fill up the entire screen.
  4. Use TikTok fonts.
  5. Include an engaging title.
  6. Focus on a strong first 1-second of the video.
  7. Remove anything that doesn’t progress the story.

Peter Jackson, when he was making Lord of the Rings, had to condense a massive book into one movie each. His wife was one of the head writers with him on the project, and they said, "Does this progress the story of the plot? Nope, it's gone." Even if something was good, funny, or entertaining, if it doesn't progress the story of the plot, cut it out. And you've got to do that with your content on TikTok as well. It's a bit of a blue ocean for educational content. It's very difficult, but the ROI can be huge because your organic reach on that platform is insane.

What video have you posted on TikTok that's got the most surprising response?

It's interesting because I get a lot of hate on TikTok just for educational content. I mean, whether it's hate or people just always arguing, because you put out different opinions and stuff.

My most viral series was called Boys vs Girls Experiment. And it was a conversation with one of my guests about masculinity and how men struggled to show their emotions. It got received really well. It's had over 30 million views across the series, and that was my first viral video. It really got me on the map. And it was also very positive. It's kind of rare I get a viral video that's just positive. If I get a viral video, there's often a bit of controversy or there's some sort of differing opinions, but this one was universally received and that gave me a lot of confidence.

I've had videos go viral when I talk about the school system or I've had lots and lots of viral videos across a variety of topics. Some of them not very well received, some of them very well received, most of them in between.

But yeah, it's just a numbers game. Like my whole strategy is throwing mud on the wall and one will stick. If you look at my account now, most of my videos get 3,000 - 4,000 views. But because I post so often, if I post three videos a day, I only need one of them to do well. I only need one, I only need two of my 30 videos a week to do well. And I hit a million views a week. And so that's really my strategy.

Yeah, you can't go viral if you don't publish.

And it is interesting where you think that there's a video that's going to be an absolute smash hit, whether it's TikTok, Reels, whatever it might be, and you post it and it does nothing. And then you can post another one that you're almost reluctant to post and it just crushes it.

At the end of the day, you can't really validate it until it's put out there.

James, I cannot express how many times it's happened to me! Even recently, I had this great episode with a guy called Tom Nash, who's missing both arms and both legs. He's an incredible guy. I thought the clips were going to do so well, and we've some do really well, but so many of them have bombed.

Then there's been other clips where you post them and you're like, "Oh, this is all right." And it goes mega viral. I would like to think at this point, I have a good estimate — and a lot of time I do — but still some of them catch me by surprise. Some of them go mega viral, some of them don't. It's really a numbers game.

When creating content, removing your expectations is really important.

When creating content, removing your expectations is really important. TikTok can be really difficult to grow on because you get this hit of virality and you get this expectation that your video is going to go viral and you're going to keep having followers. But my account is mega growth and then almost nothing, and then mega growth, and then almost nothing.

And when you're in this almost nothing stage, you feel worthless because you've felt what it's like to be getting 1,000 followers a day or whatever. Unpacking the psychology of that is a whole other conversation. But this is why most people don't survive on TikTok. They give up because it's really difficult to grow on that platform because of the mental battle. But if you can push through it, it can be very beneficial.

You mentioned your Intentional Gap Year project. I know that's something you're very passionate about and have been working on a bunch behind the scenes. Can you tell us about that Intentional Gap Year and what people can do to get involved?

Yeah, look, I'm so excited about this, and I think this could be my biggest project. With everything I'm working on, this would the glue that brings a lot of stuff together.

I've had the idea for a while, but when I mentioned it to my mate, Joe, he was like, "Let's do it. I'll help out, let's do it. And let's tie it in with our book launch." So we've got a book launch coming this month and then we're launching the Gap Year project straight after. Basically, it's like a year between high school and university.

Most people know what a gap year is, but the one we're running is intentional and we're going to provide them with a whole community of young people. We've got our own custom social media platform, we're going to have personal development events, we're going to have lots of partying, outdoor activities, and festivals. Outdoor retreats where you can go into the bush for two days with an expert and they'll teach you how to survive and really become one with a bush and feel and get away from technology.

We'll be doing huge boat parties on the Sydney Harbor with drinks and everything. And then we'll be doing personal development events and monthly workshops and fortnightly mastermind so people can stay in contact and really gamify it.

So it's like a lot of fun and people want to do it. It's just supposed to be a really fun experience for a year. It doesn't matter how prepared you are, there's no harm in taking a year off between high school and university. When you're 80 or 90 years old, and you look back at your life, you're not going to think, "Oh, I was one year later at university." You'll look back at an amazing time you had when you're young.

It's really about a year of building good connections and friendships, having fun, traveling, getting work experience, getting internships, and self-improvement.

And as we mentioned, James — and you helped me come up with it — the three kind of pillars are to build great relationships, get access to great mentors, and most importantly, gain access to real-world experience. We're going to set you up with work experience opportunities and internship opportunities so you can begin to taste all these different careers and see which ones suit you. We'll also give you access to university students so you can question them.

If anyone is interested in getting involved, we're doing free information nights where you can learn more.

And the cool part, James, is we're running it in Sydney, but anyone could do it. If you're in the UK or if you're in America and you go, I want to take a gap year in Australia, come to Sydney and join us! Come do the program in Sydney. How cool would that be? So, yeah, it's very exciting.

We like to keep it pretty real from a mental health perspective on this show. Since you embarked on your entrepreneurial journey, is there a particularly dark day that stands out to you that you'd be open to sharing with us today?

Yeah, there was a day, it was the day I started journaling. Simultaneously, so much happened in my day. In the morning, I met Brent Williams, who is now my mentor. He runs Empower U, the program I mentioned, and he's been the most valuable connection to me. He's taught me so much. I had him on the podcast, and it was an amazing episode. I was so excited. So that was a great morning.

Then I went home early from the office, and as I got home, my sister comes out and she said, "Byron, grandma's in the hospital. She just had a heart attack. She's not going to make it." So I went from this immediate high to this immediate low.

We hopped in the car and drove to the hospital. This was still during COVID, so no only one person at a time was allowed in. Because she was in ICU, the expectation from the doctors is that she was going to die. It was very emotional walking up to her and she was very drugged up and you say your final words. It was very emotional and so sad.

To distract myself at the hospital, I pulled out my phone. And at the time, I was working on this project called the HSC Round Table Sessions, which is connecting a bunch of top university students with younger people so they can teach them. And this girl called me out publicly. She was saying, "Byron Dempsey is trying to rip people off by charging money. He's not even paying the volunteers." When everyone applied, it was a volunteer position!

It was the first time someone had hated on me publicly and called me out. It was like a dagger to the heart.

It was the first time someone had hated on me publicly and called me out. It was like a dagger to the heart. In the midst of everything with my grandma, I had this huge thing happen. And then my friends all went and backed up and commented on her post and it was supporting me, which is great.

Funnily enough, my grandma ended up surviving and she's still alive today. No one expected it. But that day was just like this emotional whiplash. To me, that almost represents entrepreneurship: there's a mega, mega high and then bang, straight into a mega low. That's been my whole journey. So yeah, that was a big turning point for me.

It's just a numbers game. If you're putting yourself out there enough — doing videos, publishing books, hosting podcasts — you will eventually face criticism. And they say to avoid criticism, say nothing, do nothing, be nothing.

You and I would much rather do something. We would rather be someone, even if it entails and encompasses some of those things, because we know that inspiring all of the people that we can along the way is much more important than an ill-conceived remark from someone without context. In fact, it usually says more about them than anything else.

I remember hearing people like you say that when I was younger and I was like, "I'll be different. I'm going to create this podcast with the best of intentions. I'm not making any money from it. I'm purely trying to help young people, so why would I get any negative comments? It doesn't make any sense."

TikTok has been great for me, but getting negative comments every single day for a year is tough. Obviously I get great comments as well, but often your brain focuses on the negative ones. I guess you really need to understand that you're getting a hate no matter what you do.

Then there are influencers like Jake Paul who do it because they knows they're going to get hate! That makes sense to me, but it feels bad to cop the hate when you have good intentions. And I was just like, "Well, that makes sense. But I'm not doing that. I've got good intentions. I won't get hate." But you do, and you just have to accept that.


Check out the YouTube or podcast version where Byron Dempsey does the Win the Day Rocket Round, answering questions about his favorite quote, what advice he’d give his 18-year-old self, the one thing on his bucket list, and a whole lot more🚀


On your best day, what's an affirmation that you would write on a flashcard that you could show yourself on your worst day?

Remember why you're doing it and focus on the positive. Remembering those things and seeing the positive messages brings me so much joy.

I've got a whole folder, and I screenshot every message. I've got about 300 screenshots of people saying that I changed their life. I had one guy send me an audio message saying, "Hey man. Next time I'm in Sydney, I'll buy you a coffee. I just landed a $20,000 university scholarship because of what you said in the podcast." It's crazy.

So I'd probably just write, remember the messages or remember Angela. And as soon as I think of that, I immediately feel like I'm in a better place.

Yeah, in Episode 33, John Assaraf (from The Secret) mentioned that rather than doing a vision board, he likes having an achievement board of all the things that he's been able to accomplish. It sounds like you need to create an impact board from all the lives you've been able to change?

That's something that I actually need to do. I've never had negative messages; I think I've only had one or two negative DMs. That's it. No one ever has the guts to actually message me negatively, so I need to focus on the positive rather than the negative. So yeah, I love that. I think I'll do that. Maybe even today, I might create a little collage and print them out.

Final question, what's one thing you do to Win the Day?

The 5:30 Club, and I understand the cringiness behind it! I totally get that. But it's changed my entire life, not just through productivity, but through the people I meet as well. At 5:30am, I go and meet people at a cafe. It's just been an absolute game changer for me, and I love it.

Yeah, the people who can motivate themselves to get up and do that, they're the people you want to be around!

Exactly. It self-filters out anyone who's not as motivated, so it's great.

Byron, always great to see my friend. Thanks so much for coming on the Win the Day show.

Thanks so much for having me. It's been a really fun chat.


Did you enjoy this interview with Byron Dempsey? Leave a comment on YouTube with your favorite takeaway.

Remember, to get out there and win the day. Until next time..

Onwards and upwards always,
James Whittaker


Resources / links mentioned:

🌎 Intentional Gap Year Project.

⚡ Byron Dempsey TikTok.

📚 ‘‍18 & Lost? So Were We’ by Byron Dempsey et al.

📖 ‘Key Person of Influence’ by Daniel Priestley.

🔥 Free training: How to grow your brand on TikTok.

✔️ Driven Young website / podcast.

📷 Driven Young on Instagram.

🚀 Win the Day group on Facebook.

🎙️ We Are Podcast: Learn how to scale your business using your podcast.

Back to Newsletters >

Ready to win the day™, every day? 

Actionable tips from James and exclusive interviews with the world's leading experts to help you win the day. Delivered to your inbox every two weeks 🔥
youtube-squareapplegooglespotifyfacebook-official linkedin facebook pinterest youtube rss twitter instagram facebook-blank rss-blank linkedin-blank pinterest youtube twitter instagram