Let's Get Real About Success (and Failure) on Substack
The truth is that it is hard. But it's OK!
In this exclusive interview,
dives deep into the courage it takes to build a business, embrace vulnerability, and share your voice in a public space. He'll challenge your assumptions about success, inspire you to take risks, and remind you that even in the face of failure, your story matters.This is a story about the courage to be vulnerable, the resilience to rise after every fall, and the unwavering belief in the power of sharing your voice, even when your hands are shaking.
Q: Tell us a little bit about your background
My bio reads ‘Serial entrepreneur, marketing strategist, and digital writer.’
I refer to myself as a digital marketer as this is where most of my background lies. I made my first dollar building and selling computers when I was a youngster. When I was in high school and college my instructors were outsourcing me web design and development projects as a freelancer. Almost 2 decades later, I am still self employed and have started/ran approx 7-8 businesses.
The largest spans of my professional career lie in web design and development, fitness, and digital marketing. And the skills and experiences from all of them have made me who I am today.
I spent approx 10 years working as a freelancer and building myself into what could be classified as a boutique “agency” where I had a small team of contractors. I was known locally as many agencies outsourced their overflow work to me. As a freelancer I build websites, stores, did SEO, built funnels, ran Google Ads, developed apps, from small mom and pop shops all the way to Government projects.
In 2014 I made a large career pivot when I became a certified personal trainer. I slowly closed my previous business while working as a PT and nutrition coach. My wife and I ended up open a small private personal training studio, then quickly expanded into a 5,000 sqf facility with a 500,000 loan. Which we closed in 2018 as we took our business exclusively online and I began to mentor fitness professionals in building an online business.
Today, my primary work is helping businesses sell their programs and products leveraging my business strategies and paid advertising services. When I’m not doing this, I am writing, building products, and experimenting on my own brand.
Q: Beyond the act of hitting "publish," what's the most courageous thing you've done as a writer on Substack?
As a writer, I would say the most courageous thing I’ve done is challenge the norm and deviating from the predefine path of people in my position. Writing about the real and authentic journey of someone who’s failed over and over again. Sharing the truth behind the journey, talking about topics that have meaning and purpose. When I know that if all I spoke about was making money, it would get more views, likes, shares, and potentially make more money. But that life left me empty–I needed depth and I pour my heart into my work.
Q: Many people dream of writing but fear judgment or failure. What advice would you give to those who are hesitant to share their voice on Substack?
All advice I’ve found is easier said than done. I don’t want to make it sound like there is a magically motivation quote from the Dalai Lama that will clear the decks and open you up to create without fear.
The truth? It’s hard. But that’s Ok.
We will fail more times than we succeed. Success doesn’t exist without failure. But my advice is to befriend it, as much as we can. To understand what is within our control–and what is not. My journey through self-work and therapy have been pivotal factors in me sticking with things. But don’t be fooled, I’ve considered quitting a lot. I’ve watched dozens of friends start after me and succeed faster than me leaving me feeling like a failure. I’ve had businesses that flopped. Posts with 0 likes. Hateful comments. But the more I can ground myself in the fact that it is Ok, that I am enough, that I don’t need to be perfect to impact someone’s life, the better.
My advice is to be patient and kind to yourself. You have the power to find meaning in difficult times and pull valuable lessons from each experience.
Don’t let 0 likes stop you from sharing your gift–it’s going to be messy, that’s the beautiful part.
Q: In your opinion, what's the most courageous thing a reader can do after engaging with your work?
Other than hitting restack, you mean ;-)
It takes courage to share how you feel. Whether that is in the comments or leveraging that emotion into your own work.
When my work touches someone and I see that translate into action from them it is the sole reason I do what I do. Not for the money but to leave the world a better place.
Sharing a piece of ourselves online is an incredibly vulnerable experience. We open ourselves up to all sorts of criticism, judgement, love, and hate.
The goal behind my work is to give people permission.
It takes courage to act upon it.
Q: Vulnerability is often a key component of courage. How do you balance being vulnerable with maintaining healthy boundaries as a writer in such a public space?
If I had to guess, we’re both Brene Brown fans.
I believe the balance is deeply personal. I read a quote once about writing from scars not wounds. And I liked how this resonated with sharing and viewing the vulnerability from a position of having been able to create space between you and it. So it doesn’t become a rant.
My goal is to vulnerability share my experiences without taking a ditchotomous view on circumstances. I want people to see themselves in my story. I want them to read it and know they are not alone. I believe I have to be vulnerable to do this.
I strive to avoid talking at people, manipulating people, or saying this is how it’s done. So that what I write helps shift perspectives as were on the same side of the table.
Q: Courage often involves taking risks. What's the biggest risk you've taken in sharing your writing or building your Substack community?
Seeking to carve my own path.
I have a reminder on my phone that reads:
“Remember: You do not need to take the traditional path or do what ‘everyone else’ is doing to be successful.”
I challenge many of the norms. I don’t have a specific niche, I don’t monetize with paid subscriptions, I don’t write 1,000 words per day, I post about deeply personal and challenge societies views on success.
When everyone goes left but it doesn’t feel right so I don’t, it’s a risk.
I trust in the path that I am on–most of all, I trust I can figure it out.
Q: What advice would you give to someone who feels stuck or unfulfilled but is hesitant to take the leap and reinvent themselves?
Are the choices we’re making expanding or enlarging us? Or are they contracting us.
We often stay in our current situation or cease to take action in fear or failing when even in failure that experience may be or lead to something more fulfilling.
We will never now the outcome of the decisions we are faced with all we can do is choose–and if we don’t the choice is being made for us.
I’ve re-invented myself multiple times.
From being a web designer to starting a gym. From a gym owner to a business coach. From a coach to a digital marketer. From a marketer to a writer.
I would not be here today without each decision that has lead me here. I would not be a writer, I would not be married to my wife, live in a cute little beach front town.
One of the hardest things we can do is choose to seek joy.
It’s scary and often feels easier to make no decision at all remaining in the comforts of our routine.
But if nothing else… These experiences make for really damn good Substack articles ;-)
Q: If you could go back and tell your pre-Substack self one thing about the journey ahead, what would it be?
To be patient and trust that I will figure it out.
There is no mysterious finish line where we are now “successful” and we get a trophy for our mantel. The pursuit of this leaves us moving the goal posts and completing tasks that lead to the next task to complete. A cycle that will never end.
We must stop, be patient, and challenge the way things have been done.
I am constantly reminding myself of this.
People often message me asking about how to grow and make money on Substack. I am happy to remind people that my publication shrunk for my first 8-months. And even when I had a viral moment, nothing changed. I went back to the simple routine of consistently publishing.
I seek fulfillment, depth, and joy in my work.
And I trust this is leading me down the right path.
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