We recently connected with Scott Clary and have shared our conversation below.

Alright, Scott thanks for taking the time to share your stories and insights with us today. So let’s jump to your mission – what’s the backstory behind how you developed the mission that drives your brand?

Starting the Success Story Podcast wasn’t a business move for me; it was a personal one. I kept seeing friends, family, and colleagues struggling with the same questions I had: How do successful people really make it? What can I learn from them? Is there a way to understand success without falling flat on my face first? That’s when I knew I had to do something.

Education & Learning – Why Should You Care?

You don’t need me to tell you that the world is changing at breakneck speed. It’s not enough to learn something once and call it done. We all need to keep learning, keep growing, and keep challenging ourselves. That’s where the Success Story Podcast comes in.

I talk to people from different backgrounds, who’ve faced different challenges, and I ask them the questions you’d probably ask if you were sitting across from them. How did you do it? What did you learn? What can you tell someone who’s still figuring it out? And guess what? They answer.

The Real Stuff – Wins AND Losses:

The podcast isn’t about painting a rosy picture of success. It’s about getting to the heart of it, the good and the bad. We talk about triumphs, sure, but we also dig into the mistakes, the missteps, and the outright failures. Why? Because that’s where the real learning happens. I’ve stumbled plenty of times myself, and those stumbles taught me more than any win ever did.

No Fluff – Just Tactics:

If you’re looking for sugar-coated anecdotes, you won’t find them on the Success Story Podcast. What you will find are real, tangible, “you-can-do-this-too” insights. We get into the nitty-gritty, the stuff you can jot down and start using today. It’s not about lofty ideas; it’s about real-world actions.

We’re in This Together:

Here’s the thing: I learn from the podcast, too. Every guest teaches me something new, every listener who reaches out adds something to the conversation, and together, we’re building not just a community but a support system.

It’s not just my podcast; it’s ours. It’s a place where we can all share, learn, grow, and cheer each other on. Whether you’re starting your own business, climbing the corporate ladder, or just figuring out your next step, there’s something here for you.

So, What’s Next?

I invite you to dive in. Listen to an episode that catches your eye or jump into a conversation on social media. Share your thoughts, your successes, your setbacks. There’s no judgment here, only understanding, encouragement, and a shared determination to succeed.

Thank you for letting me share this with you, and thank you for being a part of something that’s not just close to my heart but woven into who I am. Let’s keep building, learning, and growing together.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

My path to becoming an entrepreneur and investor was far from straightforward or expected.

I grew up in a very risk-averse family in Toronto, Canada. I was primed for a life of stability, security, and avoiding uncertainty at all costs.

Yet I always felt curiously drawn to startups, technology, and business – everything opposite of my upbringing.

Even as a kid, I was the black sheep who saw achievement as simply deconstructable building blocks, not some big mystery.

My origin story really took shape when I became an enterprise tech sales rep for telecom giant Bell Canada in my early 20s. I progressed to closing million dollar deals, overseeing massive digital transformations for Fortune 500 companies.

But I wanted bigger challenges, bigger learnings and more upside potential. This pushed me towards working with startups (as well as trying to build several of my own businesses).

I took a chance joining a promising startup. Within a couple years, I had built out their entire sales org from scratch and helped secure a very lucrative acquisition.

This experience showed me that with hustle, courage, and the right mindset, you can accomplish anything. I had gone from a sales rep to a revenue leader who delivered meaningful impact, simply by breaking things down to their core learnable elements.

Armed with new confidence, I co-founded an advisory firm with some colleagues. We worked with ultra-high-growth startups, helping disruptive young founders with sales, marketing, and scaling strategies. Getting an inside look at these innovative companies lit a fire in me.

Around this time, in my free time, I began building an audience based on these topics. I started a podcast interviewing successful leaders to deconstruct their stories and extract tactical lessons we can all apply.

Fast forward a few years of perseverance, and I’ve now amassed over 1.5 million followers across social media! My podcast continues to be a top business show featuring icons like Guy Kawasaki, Mark Randolph, Seth Godin and hundreds of others.

So what ultimately led me to become a full-time entrepreneur and angel investor? An insatiable curiosity, an underdog drive, and a core belief that most achievement is demystifiable, learnable, and accessible.

I wanted to spread that empowering message as far and wide as I possibly could.

These days I pour my energy into managing my own portfolio of ventures, making investments in passionate founders, solving real problems, and disseminating wisdom through my growing platform.

But I’ll never forget where I came from. My origin story as an unlikely entrepreneur drives me to humanize success every single day, and make personal growth feel attainable for anyone willing to put in the work.

Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?

One major insight that has shaped my mindset is that achievement of any kind can be deconstructed into learnable components. Success leaves breadcrumbs that we can trace back and model.

In my youth, I viewed exceptionally successful people as innately gifted – what I presumed was unteachable talent or intelligence. This formed a mental barrier in my mind about what I could realistically accomplish.

But over time, I discovered that all success can be unpacked and reverse engineered. The key is having the curiosity to unpack it and the diligence to model it.

The seeds of this belief were planted when I was first starting out in enterprise sales. I was mystified by the top performers who always seemed to crush quota. So I started studying their methods.

I found they simply did the fundamentals better than the rest of us – outbound cadence, probing discovery questions, objection handling, etc. Once I implemented the same rigors and tactics, my results followed suit.

Their success wasn’t magical or elusive – it was a formula. This showed me that achievement isn’t about genetics; it’s about knowledge, effort and the right strategy.

The more I unpack success this way across various fields – from fitness, to relationships, to leadership – the more I believe anyone can achieve excellence with the right framework.

We need to let go of the myths. Gifted isn’t born, it’s made. Mastery isn’t opaque, it leaves a trail to trace. But we have to shed our limiting beliefs first in order to see the breadcrumbs. Once your mind is open, you will find guides and signposts everywhere. You simply have to let yourself believe that the path is navigable.

My motto now is that if someone has done it, it can be understood and replicated. All success can be unpacked – we need only have the hunger to reverse engineer it.

How’d you build such a strong reputation within your market?

I never imagined when I started out that I’d end up where I am today. I was just a guy struggling through the ups and downs of life and career like anyone else. I battled impostor syndrome and confidence issues for years. I worried that putting myself out there would be met with a collective “who cares what this no name thinks?”

But I’ve learned that we all have wisdom to share from our unique journeys. And that vulnerability and sincerity tend to outweigh expertise and polish.

Gradually, day by day, small pockets of people started to tune into my message. They found some value in my perspectives and story. Over time, those pockets grew into a community.

And that community gave me the conviction to keep showing up genuinely, even when self-doubt crept in. Their feedback and encouragement taught me that we all have a purpose to fulfill if we have the courage to embrace it.

Looking back, a few key things enabled me to build a reputation that still surprises me to this day:

First – tons of consistency. Come rain or shine, I always showed up to share my thoughts and experiences. Was it always pretty? Oh god no. But putting in the reps over years, not days, is everything.

Second – keeping it real. Getting comfortable being uncomfortable. Opening up about my flaws, doubts, bad days along with wins. We can only connect through our shared struggles and triumphs.

Third – storytelling. I try to take boring topics and inject some life! Make people laugh, imagine “what if,” and go on an adventure through ideas. Facts tell, stories sell.

Fourth – being down-to-earth. At the end of the day, I’m just a guy figuring it out one step at a time like anyone else. None of us have it all mapped out. So I aim for humility and humor to make personal growth feel within reach.

And fifth – providing value. Not just pumping out content to hear myself talk but actually sharing hard-won lessons that can tangibly help people’s mindsets, goals, and lives. No BS.

That’s been my formula. But most of all, I just try to talk to people like a friend, not some “guru.” Always more room for me to improve on that front! Authenticity above all else.

Contact Info:

• Website: scottdclary.com
• Instagram: instagram.com/scottdclary
• Facebook: facebook.com/scottdclarypage
• Linkedin: linkedin.com/in/scottdclary
• Twitter: twitter.com/scottdclary
• Youtube: youtube.com/c/scottdclary
• Other: successstorypodcast.com