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I’m 280 Pounds With an Anxiety Disorder. And I’m About to Build a Brand Like Gary Vee.

I used to think I needed to fix myself before I could build something. Turns out I was wrong.

Jason Weiland · 2026-01-26 17:12 · 310 claps · 6.8 min read paywalled
#future #dreams #content-creation #gary-vaynerchuk #personal-branding
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Wiki topics: PSY · Mental Health & Psychiatry BRD · Branding & Identity CNT · Content Marketing 🧠 · Mental Wellness

I’m 280 Pounds With an Anxiety Disorder. And I’m About to Build a Brand Like Gary Vee.

I used to think I needed to fix myself before I could build something. Turns out I was wrong.

My future self, or how I see me. Created with Nano Banana.

My future self, or how I see me. Created with Nano Banana.

I got my left arm fully sleeved a few years ago. Flowery patterns and butterflies in black ink and lots of color (because I like flowers and butterflies). Shoulder to hand.

And something weird happened. My confidence went through the roof. Not gradually. Overnight. Like flipping a switch. I don’t know why. Maybe because I finally did something just for me. Something I’d wanted for years but never thought I deserved.

Or maybe it was just seeing my arm in the mirror and thinking “that’s mine. I chose that. Nobody can take it away.”

Whatever it was, I stopped apologizing for taking up space.

And now I’m ready to take up a lot more space. On stages. In rooms. In front of audiences.

Even at 280 pounds with an anxiety disorder that makes my heart race before I even open my mouth.

Toolie Made Me an Offer

Last week, someone in my community named Toolie® Merchant said they’d help me get into speaking organizations. Real organizations. Real events. Real stages.

Toolie is a great friend I met right here on Medium.

Not “motivational speaker” nonsense. Real speaking. About real problems. To people who are struggling with the same things I’ve struggled with.

I said yes before I could talk myself out of it.

And then I thought about it and panicked.

Because I started thinking about all the reasons this won’t work.

The Fear Is Real

I’m 280 pounds. I know what people see when I walk into a room. I worry they’ll be distracted. That they’ll see my size before they hear my words.

I worry I’ll say “uh” too much. That I won’t project confidence in a body this size. That I’ll freeze up or stumble or look like I don’t belong on a stage. I know i’ve written about this before, recently. But the fear is real coming from a deep place of anxiety and panic, a place I usually keep hidden my pushing my feelings down.

The anxiety disorder doesn’t help. My heart races. My hands shake. Sometimes I forget what I was going to say mid-sentence.

I’m now encouraging these feelings to rise, so I can address them and doing things that take me out of my comfort zone. It’s easier to push them down than to deal with the demons inside.

And I’m 57 years old starting a new career path that most people start in their 20s.

So yeah. The fear is real.

But you know what else is real? My brain.

My Brain Is the Sharpest It’s Ever Been

I’m 57. I stand in the bathroom with my pants around my ankles and forget why I’m there. I walk into rooms and lose track of what I was doing.

But my brain is sharper now than it was at 30.

I can write. I can brainstorm hundreds of ideas in an hour. I can see patterns nobody else sees. I can connect dots across disciplines and experiences. I can take complex ideas and make them simple. I can take painful truths and make them digestible.

That’s my superpower. Not my body. Not my appearance. My brain.

And that’s what I’m building my brand on.

I Want to Be Gary Vee Without the Gary Vee Parts

I know I couldn’t be the next Gary Vaynerchuk. I don’t have his energy. I don’t have his hustle mythology. But I’d love to do something similar. Speaking engagements. Leadership. YouTube. Content. Thought leadership.

Just without the cringe or at least with my own kind of cringe. Without the F-bombs every third word. Without the “grind 24/7 or you’re weak” nonsense. But with honesty, grit, authenticity, and a tendency to to make people wonder “did he just say that out loud?”

His brand works for him. It’s not me.

I want to be the guy who tells you the truth about starting over. About failing. About being 57 and still trying to figure it out. The guy who says “this is hard, and you’re going to struggle, but here’s what actually worked for me.”

Not the guy screaming at you to to fill out 1000 applications because 200 iws not enough. The guy sitting across from you saying “I get it. Let’s figure this out together.”

Flora Helped Me See It

My wife Flora has been telling me for years that I’m stronger than I think I am. I didn’t believe her. I thought she was just being nice. Being a supportive wife.

But she kept saying it. “You’re capable. You’re strong. You have value.”

And slowly, I started believing it.

Not because my body changed. Not because I lost weight or fixed my anxiety. Because she helped me see what I was already doing. The freelancing for 20+ years. The raising kids. The surviving heart attacks and poverty and mental illness.

The showing up every day even when I didn’t want to.

That’s strength. That’s capability. That’s value.

And now I love myself. From head to toe.

Not because I’m perfect. Because I’m real. And I’m done apologizing for it.

I’ve Been Building This Brand for Years Without Knowing It

At first, I didn’t know what I was building. I was just writing. Trying things. Figuring it out as I went.

But slowly, a pattern emerged. I write for people whose lives have been destroyed by a terrible job market. People who are too old or too inexperienced to get hired. People who have sent out 1,000 applications and gotten zero interviews.

I write for people who need hope in freelancing and content creation. In starting businesses and hiring themselves. I write for people who are trying to realize their own version of success in a world that beats them down every day.

That’s my brand. And people are starting to know me for it.

Not because I’m polished. Because I’m honest.

Not because I have all the answers. Because I’m willing to admit when I don’t.

Consistency Beats Perfection Every Time

I built my brand through sweat, blood, and plain stubbornness. Posting every day. Responding to every comment. Showing up even when nobody was watching.

Not because I was confident. Because I was too stubborn to quit.

And slowly, people noticed. Not thousands at first. Just a few. Then a few more.

Now I have 13,000 followers on Medium. 500+ members in my community. People asking me to teach them what I know.

Not because I’m special. Because I refused to disappear.

Five People Showed Up to Coffee Hour

I hosted a coffee hour for my community yesterday. 500+ members. Five people showed up again.

A year ago, that would have crushed me. I would have seen it as failure.

But last week, I saw it as it was, a success. But also as practice. Practice for bigger stages. Practice for speaking in front of rooms full of people who don’t know me yet.

So those five people? They mattered. More than 500 silent members ever could.

That’s what I’m learning. You don’t need thousands of people cheering for you. You need five people who actually show up.

I’m Ready to Stop Hiding Behind My Keyboard

For years, I’ve hidden behind my writing. Behind my screen. Behind the safety of not having to show my face.

But I’m done hiding.

I’m 280 pounds. I have an anxiety disorder. I’m 57 years old and starting over.

And I’m about to build a brand anyway. Because I’ll lose weight. I’ll get my teeth whitened. I’ll start dressing like the guy in my daydreams, The guy I picture when my mind is quiet and I think about what future Jason will be.

This guy. Created with Nano Banana.

This guy. Created with Nano Banana.

That guy will be on stages. In videos. In person. But I don’t need to be him to get started.

Because my message matters more than my appearance. And the people who need to hear it will hear it regardless of what I look like.

The Takeaway: Your Brand Is What You Give, Not How You Look

Your brand isn’t your body. It’s not your weight. It’s not your age. It’s not whether you’re polished or perfect.

Your brand is what you give people. The value. The help. The honesty.

If you show up consistently and give people something useful, they’ll forgive the rest. They’ll see past your imperfections because they’re getting something real.

I’m not waiting until I lose weight and my teeth are perfect and white. I’m not waiting until my anxiety goes away. I’m not waiting until I feel ready.

I’m building now. With what I have. As I am.

280 pounds. Anxiety disorder. 57 years old. Tattooed arm and all.

And if that’s not perfect enough for some people, they’re not my audience anyway.

What’s stopping you from building your brand? Not the surface stuff. The real reason. Drop it in the comments. Let’s be honest about what’s actually holding us back.

I will be opening up the Medium Mastery course this week for new members. You know how you can know for sure when I’ll start? Join my Skool community, “Over 40 and Unemployed.” You neither need to be over 40 or unemployed, but be ready to engage and help others who aren’t having as much luck right now.

I also have a special lifetime offer only for members of my group. It’s free, and always will be.

Join here!

Also, if you are on LinkedIn or Threads and want to connect, let’s do!

One more thing…

If this post added value to your life, consider either joining my Ko-fi, or leaving me a tip. Every little bit helps when you are trying to make a living writing.

Click Here to support me.

Click Here to support me.


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