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The Greatness Machine

TGM Classic | Shirl Penney | Living the American Dream

The Greatness Machine

Darius Mirshahzadeh

Education, Entrepreneurship, Business

5.0 • 135 Ratings

🗓️ 29 December 2025

⏱️ 60 minutes

🧾️ Download transcript

Summary

How does one go from financial struggle to creating a platform worth nearly $100 billion?  This question encapsulates the extraordinary journey of Shirl Penney, founder, president, and CEO of Dynasty Financial Partners. Beginning in rural Maine where financial stability was difficult to come by, his story is one of grit and determination.  Although Shirl had to overcome early hardships, his desire for education and self-improvement led him to prestigious institutions and eventually to the competitive world of finance. Having navigated and overcome numerous obstacles led to the establishment of Dynasty Financial Partners, a firm he founded with resilience and an innovative mindset.  In this episode of The Greatness Machine, Darius is joined by Shirl Penney to share his compelling journey from the financial struggles of his upbringing in rural Maine to building a financial empire managing nearly $100 billion in assets. The conversation delves into the challenges he faced, the pivotal moments that shaped his career, and the innovative strategies he employed to revolutionize the wealth management industry. Shirl also discusses the importance of resilience, leadership, and maintaining a clear vision in the pursuit of success.  Topics include: Shirl looks back at being homeless to founding Dynasty Financial Partners Improving financial literacy and providing independent financial advice  The origin and motivation behind the creation of Dynasty Financial Partners The impact of Shirl’s upbringing and experiences on his approach to business The value of maintaining a strong corporate culture and significant growth And other topics… Connect with Shirl: Website: https://dynastyfinancialpartners.com/  LinkedIn: https://www.linkedin.com/in/shirlpenney Connect with Darius: Website: https://therealdarius.com/ Linkedin: https://www.linkedin.com/in/dariusmirshahzadeh/ Instagram: https://www.instagram.com/imthedarius/ YouTube: https://www.youtube.com/@Thegreatnessmachine  Book: The Core Value Equation https://www.amazon.com/Core-Value-Equation-Framework-Limitless/dp/1544506708 Write a review for The Greatness Machine using this link: https://ratethispodcast.com/spreadinggreatness.  Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0

Love gang, welcome to The Greatness Machine.

0:01.6

I'm your host Darius from Shazday.

0:02.9

I'm so pumped to have you here with me. Now listen, the greatness machine were about two things. Number one, people were living their passions. And number two, those who are creating greatness in the world and doing both of these things despite the odds against them. Each episode, we're going to feature interviews with game changers, business leaders, telling us their origin stories. What made them tick? what got them to where they are now.

0:22.9

Why?

0:23.4

So it can help you step into your greatness

0:25.2

within your life, your business, and your career. Occasionally, you might hear a few solo episodes

0:29.7

for myself, as I say, as I leverage my 20 years of entrepreneurship as a CEO and founder

0:34.8

to help you grow and level up in your journey to scale your life and

0:38.1

your business. So come be a fly on the wall, enjoy the conversation, and I'm stoked to have you hear with me. Guys, welcome today's episode of The Greatest Machine. I'm your host, Darius from Shaw's Day. Boy, do we have a special guest. My man, Cheryl Penny is in the house. What's up, Cheryl? Hey, Darius, great to see you.

0:54.8

Great to see you as well.

0:56.5

Oh, man, I'm so glad to have is in the house. What's up, Cheryl? Hey, Darius, great to see you.

0:54.8

Great to see you as well.

0:56.5

Oh, man, I'm so glad to have you on the show, Cheryl. Your name has come up in so many circles that I'm moving with in these days and I was glad to finally get you on here to get to talk to you about all the great things you're doing in the world. Before we get started, though, do you mind if I do a little bit of housekeeping for our new listeners to the show?

1:13.7

Absolutely. Go for it. So for listeners who are new to the show, the greatness machine, we're about two things. People live in their passions and those creating greatness in the world and do so despite the odds. My friend Cheryl here is neither short of passion or greatness. So yeah, so, you know, Cheryl, your name has come up in a lot of the circles. I mentioned earlier before the show that your name came up with my friend Russ Norwood. My business partner at Rise is Joe Duran, who I know you've known for a long time. A great friend of mine, Russ Norwood. I was just having dinner with him last night here in Austin, Texas. And you you know, you're a pretty well-known guy. People have spoken greatly about you in the RIA world. So kudos to you, my man. Like, you have a great reputation. And it obviously speaks volumes to the awesome work that you're doing, my friend. I appreciate that. Thank you, dearest. You know, I want to give your formal bio. So, you know, a lot of the listeners in the show know that I've now gotten into the world of the RAA world with Rise. And, you know, like I said, you're a big name in that industry. You're the founder, president, CEO of Dainee C Financial Partner. You guys are managing nearly 100 billion of assets under management. And on the entrepreneurial firm, we got a lot of entrepreneurs that listen to the show. You were recently named in 2023, the Florida entrepreneur of the year by the Tampa Pay Business Time. So, man, just awesome work, my friend. I'd love if you wouldn't mind, though, you know, here at the greatness machine, we love origin stories. And I would love if you wouldn't mind, you know, given some of your background, some of your origin story, how did you get to where you got to? Yeah, look, I think, you know, Darius, and it's great to see you and thanks for having me on. You know, we're all living our own unique version of the American dream. And, you know, my origin story is probably not your most typical journey to Wall Street, if you will. I'm from a

2:53.2

small fishing village in Maine called Eastport, Maine, and I was raised by my step-grandfather.

2:58.5

I was orphaned before that, and my step-granddad took me in, and we were homeless when I was

3:04.7

11, 12, 13, lived with different neighbors.

3:11.8

It turns out, you know, being homeless is actually great training to become an entrepreneur.

3:19.9

It forces you to do more with less, but had perfect attendance K through 12.

3:26.8

My granddad forced me to be president in school, wanted me to ultimately have a job where I work with my mind, not my hands.

3:29.8

He'd work manual labor, pretty much his whole life.

3:34.6

Fourth grade education was actually handicapped and overcome quite a bit.

...

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