Q&A #1 — My origin story, how to grow on social media, destroying laziness, and more

This past Sunday I threw up a Q&A on my story for the first time since starting the pages (@historyofwinning & @winning.therapy). Wasn’t sure if I’d get any Qs, but the response was crazy. Questions poured in, and I spent the first 4 hours of my day yesterday answering them all. In case you didn’t see it, I’ve put all the best ones in this post for you to browse through (with expanded answers). If you have any of your OWN questions, drop them in the comments of this post, I’ll reply to every one.

What were you expecting? Do you keep laughing for hours after watching a comedy? Do you feel sad the day after watching a sad movie? Obviously not.

The problem isn’t that “the motivational content didn’t work,” the problem is that you ever expected it to.

Once you stop trying to paper over the real problem with hype videos, you can focus on what’s real.

These are the questions you need to be asking. Motivation is entertainment. Put it down and fix the root cause of your inaction.

I think a lot of people see this page and think I’m some history scholar. Not the case whatsoever. I started with ambitious goals, solved a ton of my own problems to figure out how to win, and then realised there was an untapped wealth of REAL lessons and insights in the stories of great men and women (not the bullshit you see on IG all day from gurus with rented cars).

These stories filled me with energy, ideas, and drive to aim higher and execute my own mission with more ferocity and ingenuity. So I started posting them on @winning.therapy.

When I wanted to post more, and go further back through history, I started this page (@historyofwinning). I thought it would do well, but I NEVER expected it to grow 300k followers in less than 3 months. It’s been a wild ride, and I’m super grateful for everyone who’s here—especially those of you subscribed to these emails.

I’ve always been ambitious, but I come from a tiny farming village, so I never had any mentors growing up.

For years, I read books, tried things, ran my own experiments, paid many thousands of $$ for coaches and suffered a few heartbreaking failures. After a while, I began to “figure it out,” and things started to click. When that happened, I realised that all the “success advice” I’d read online was mostly surface-level bullshit that led me astray. People saying all you need is “consistency and hard work” when that’s literally just the entry ticket to the game.

With everything I learned, I built a 5-figure/mo freelancing business, then landed a role as the CMO of a 7figure coaching company where we helped people grow their personal brands on IG and Twitter. My role was 90% front-end marketing, and 10% coaching our clients.

This was EYE OPENING. I got to work with a ton of people, see inside their minds, see the things that held them back from winning, even though we’d given them the EXACT playbook to make it happen. I noticed patterns in the winners and losers, which added to everything I’d been learning from my own experiments. During that time I created a TON of viral content for our business, and helped one guy inside the group go from zero experience on social media to building a 250k follower personal brand in 12 months, making $15k+ a month.

Around the middle of last year, I was staying in California for a month with the team, and realised it was time to move on. I wanted a way to share what I’d learned, to add more depth to the discussion around winning & success and share my love for the stories of great men and women. So I launched @winning.therapy.

In the beginning, it was just a passion project, and it took a while to gain any momentum because I wasn’t actually leveraging my unique skills. As soon as I did, it started to take off (@winning.therapy only had 25k followers in December last year).

Then I started @historyofwinning in January, and it took off like a rocket ship, hitting 100k followers in 13 days (now 300k in 74 days). At that point, I knew I’d found something special and went all in.

Just to reiterate again—I’m infinitely grateful to everyone who’s along for the ride here, especially all of you who are subscribed to the Substack. We’re only just getting started. 🙏

Like I said before, I’ve coached 100+ people to build their personal brands. The #1 thing that holds people back is not posting enough content, which is downstream of FEAR. They’re afraid of what people will think of them, afraid they don’t have the authority to talk about their *thing*, afraid of what the low engagement says about them as a person. They experience all this fear, and allow it to CRIPPLE them. The people who win don’t do anything special. They just do the f*cking thing. The guy I mentioned before who I helped grow his brand to 250k followers in 12 months, his “special talent” was posting 3x a day, and NEVER missing a day. That level of volume allowed him to LEARN what works and what doesn’t 10x faster than everyone who was just posting when they felt like it.

When I started building my pages, I had the advantage of having seen all the pitfalls and mistakes that hold people back from winning. I also had the advantage of 2+ years creating content & coaching people on their content. All I had to do was follow the playbook I’d been teaching for so long.

All that said, it definitely wasn’t easy. It’s 1000x easier to give advice to someone else than yourself, and it took me a few months to figure out my “lane”. But once I did, I tripled down, and the result is over 500k followers gained in the last 3 months.

This is 100% part of the plan, but all the content on @historyofwinning, @winning.therapy, and The Winner’s Almanac (this Substack), as well as all the messages, stories, comments, etc, is all being done by a one-man team (me). It already takes all of me to create and publish the quality and quantity of content I want to put out, so YT will have to wait for now.

Ski, skydive, surf, ride dirt bikes, read old books, pick up heavy things (and put them down again), go down research rabbit holes, plot & scheme, discuss plans with associates, walk in nature, travel to obscure places, help old ladies with their shopping.

But mostly, I work.

The fact that you’re asking this question at 16 y/o means you’re already WAY ahead.

Remember that time is your biggest asset. Put in the work, follow your curiosity (take this seriously, treat your natural curiosity/inclinations as a compass), take your life seriously but don’t take life seriously.

Find something you have aptitude for, strive to give your GENUINE best effort in everything you do, take your health/vitality extremely seriously (research bioenergetics, lift heavy, eat clean), become more aware of your habitual patterns of thought and eliminate the negative, read biographies of people who inspire you, eliminate as much cheap dopamine from your life as possible and develop your attention span, play around with AI tools, learn how they work and how to get the best out of them, find hobbies that set your soul on fire and allow you to detach, find great teachers/mentors and show them that you’re willing to learn, work, and find your own answers.

Find friends who are ambitious (like you) and have the work ethic to back it up. Always honour the gut feeling of “this ain’t it” and REFUSE to settle for anything less than your highest vision.

In summary:

This is an impossible question, but the first person who came to mind is Felix Dennis.

Infinite REAL knowledge on acquiring abundant resources and has insane stories that he tells with poetic finesse. I think it would be an incredible time.

– Mihaly Csikszentmihalyi, Flow

You don’t. Having a powerful enemy makes you more powerful.

My favourite battles are all ones where the leader used extreme ingenuity to overcome impossible odds:

Some people are interested in events, i’m only really interested in INDIVIDUALS. That’s what my entire page is about. Who were the “great” men and women of history? What did they do? How did they do it? How did they overcome adversity? How did they make decisions? What was their path from underdog to winner? How did they think?

That’s what I’m interested in, because a) I find it fascinating, and b) that’s what I can USE to create winning outcomes in my own life.

I love this question because I think it’s a “make or break” issue for our generation. I’m lucky in that the hyper addictive apps & social media formats didn’t come out until i was 16-18. I was one of the last generations to enjoy an “analog” childhood. Kids these days are being sat in front of an iPhone from the moment they can pay attention to one, and it’s crippling. It breaks my heart because it’s not their fault, they have no agency, it’s the parents’ lack of knowledge as to what it’s doing to their child.

The other side of the coin is the adults who’s lives are being stolen and crippled by social media algorithms and cheap entertainment. We treat it as “normal” because everyone does it, just like we treat alcohol as “normal” because so many people drink. But social media is worse because it’s not something people do once or twice a week, it’s everyday for HOURS. Imagine if 9 out of 10 people were alcoholics. That’s the world we’re living in with social media addiction.

“Oh but it’s not as bad as alcohol!” — isn’t it? What’s okay about wasting 4-6 of your waking hours EVERY DAY? That’s 2 years every decade you just lost. What’s okay about eroding your attention span to the point where you can’t read a book? What’s okay about filling your head with brain rot until there’s not a single insightful thought left? It’s a parasite that’s eating away at our minds and stealing our lives from us.

As to the solution, I see pages on IG that think they’re helping people by telling them how bad scrolling is or educating people on why they’re scrolling, but it never creates lasting change. People buy cigarettes every day with death warnings on the packet. Why? Because they’re ADDICTED. You know who actually stops smoking? The guy who starts RUNNING. He’s found something he likes more than smoking. And smoking would ruin that thing. So quitting is easy.

THE POINT: The key to removing a bad habit isn’t getting rid of it, it’s REPLACING it with something better i.e. winning. Once I found a mission with massive upside potential, a chance to prove myself, develop skills, and earn respect/money, I suddenly found that scrolling & cheap entertainment got in the way. I had a REAL CONSEQUENCE for scrolling, so I naturally stopped.

“People don’t change until the pain of staying the same is worse than the pain of changing”

That’s the secret. Don’t try to remove anything or convince yourself how bad it is. You’ll just end up drowning in shame & guilt and the problem will get worse as you attempt to escape the negative emotions. Instead, find something better—something that can’t coexist with the bad habit. Then go all in.

Solve the root cause. Why are you burnt out? What’s making you depressed?

In my experience, the 2 biggest culprits are:

Both easy to fix if you educate yourself.

Side note: I’m also a big believer that what most people call “burn out” is really just a lack of winning (when the effort:reward ratio falls too low). In other words, the problem isn’t that you’re working too much, it’s that you’re winning too little. Identify what’s holding you back from success, come up with your “best guess” as to a solution, execute it aggressively, iterate, and repeat.

Also, realise that “my anxiety is stopping my business from reaching success” is a STORY you’ve created in your head to make sense of something you didn’t have an answer for. You’ve taken the fact that you feel anxious and the fact that your business isn’t succeeding, and you’ve DECIDED that one is causing the other. This simply isn’t true.

Businesses don’t fail because of “anxiety”. They fail because you didn’t do the work, you managed your cashflow poorly, you didn’t prioritise your customers, etc etc. Those are REAL reasons why businesses fail. “Anxiety” is an excuse for not doing the things that are required to grow your business. It may be a VALID excuse, but if you want to succeed, you need to focus on what’s REAL and TRUE.

“I need to do X, Y, and Z in order for my business to grow”

“This thing is getting in the way of me doing X, Y, and Z”

Now you’ve identified the REAL problem, you can come up with a METHOD to work around it. This could include taking measures to eliminate your anxiety (e.g. fixing your physical health, meditating, etc), as well as finding a way to DO THE THING even though you feel anxious (you might even find that doing the work removes all your anxiety).

But you have to genuinely WANT to win. If you care about your excuse more than you care about getting the result, it’s never gonna happen.

The easy answer = create and publish content daily, make each piece better than the last, repeat what works, ignore engagement metrics until you’ve published 100 videos.

The real answer is think long and hard about why you want to build a personal brand. Then think about whether you’re in a position to build one successfully.

Do you have ideas worth sharing? Do you have accomplishments to back up those ideas? Do you live an aspirational lifestyle? Why would people follow you?

"Everyone should have a personal brand" is a marketing line they use to sell you courses. Having a personal brand is one of the best ways to stunt your development because it locks you into being one specific version of yourself and introduces massive negative reinforcement for changing. But no one will tell you that because it doesn’t fit their course-selling narrative.

The key thing to realise is that almost everyone who’s achieved a substantial level of success WANTS to pass on what they’ve learned and help other people. But they don’t want to waste their time on unserious people. If you ask them a simple question based on action you’ve ALREADY TAKEN, you’re not demanding a heavy time investment on their part and you’re proving you’re somewhat serious. If/when they reply, and you implement their advice and come back to them with the results, you’re now GIVING BACK to them in the form of positive emotions. They feel good because they made a real, tangible impact on your life, and it makes them want to help you even more. Over time, this will snowball into a mentor-mentee relationship.

That being said, think long and hard about WHY you want a mentor. What is it that you need from them that you can’t find online? Have you actually gone looking for answers to your questions? Are you taking action? Or are you hoping that having a mentor will be the final “fix” you need to stop being lazy and finally so something? If it’s the latter, you’ll never find what you’re looking for.

The irony is that the people most likely to find a mentor are the people who need it the least. Applies to many things.

Literally just realize it’s a fiction you’ve created in your head. You’re comparing yourself to the people you see online with brands who are literally the top 0.1% and oftentimes not doing nearly as well as they make it look.

This is YOUR life, YOUR path, YOUR unique adventure. To feel like you’re behind is to spit in the face of the universe that’s brought you this far and set you off on this path.

Most people do nothing. They’re unhealthy, chronically addicted to entertainment, stuck in a void of learned helplessness.

Doing ANYTHING that’s self-generated with genuine effort automatically puts you in the top bracket. The only thing worth focusing on is your ‘inner scorecard.’ Live up to your own standards, eliminate any behaviour that makes you feel weak, and focus on doing everything that you ALREADY KNOW you should be doing.

When you’re living like that, you couldn’t give less of a f*ck how you’re doing relative to other people. Your own path is so exciting and invigorating that you wouldn’t trade it for the world. Focus on getting to that point, which is 100% in your control.

The paradox of happiness is that the more you focus on it, the more deprived of it you feel. Find something you’re willing to suffer for. Chase goals that would break your heart if you failed. Surround yourself with ambitious, earnest people who genuinely want the best for you. Do things to make other people’s lives better. When I do all those things, life is amazing. Winning also helps.

Freakonomics by Steven D. Levitt & Stephen J. Dubner.

The information didn’t change my life, but it was the first book I’d CHOSEN to read after leaving school (I was 17). This book ignited my curiosity and thirst for knowledge, and I’ve been reading voraciously ever since.

Those are all the things I do daily. The order I do them in changes, but the habits stay the same.

Winning = achieving the things you set out to achieve.

What you fear other people think of you is what YOU think of you. Accept the things you can’t control. Fix the things you can.

If you have any questions, drop them in the comments below. I’ll reply to every single one.

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