Grit With Grace Podcast: The Entrepreneur Sessions

Grit With Grace Podcast: The Entrepreneur Sessions

PODCAST – Randy: Hello, this is Randy Kaufman from Aker Advisors. Welcome to the third episode of season two of “To Grit with Grace,” stories of perseverance to jumpstart your month. This year, we’re hosting “To Grit with Grace: The Entrepreneur Sessions.” Each month, we release a podcast. Please join for the stories, the music, and the lessons learned.

The road of a successful entrepreneur is never a straight line. It is long, it is winding, and it is lonely. Not only at the top, but all along the way. Through this podcast, we hope to lend helping hands to entrepreneurs along their own particular journeys.

I cut my teeth in wealth management by working with entrepreneurs. It was the heady, go-go years of Boston, and rags-to-riches — and I mean big single-stock riches — were very commonplace. My job, then like now, was to help with planning — be it estate and tax planning, philanthropic tax planning, how much can I spend, can I spend more, whatever came across my desk. I gave much, and I received much more. 

For it was in those years that I learned what true grit means — that part of grittiness is the ability to keep going, to write your internal narrative in hard times, and to persevere, as Michael O’Brien explained in our last episode. To become successful, often against all the odds, you have to believe in one thing, and that thing is that you can and you will do it.

Today’s guest, Erin Ardleigh, shares her remarkable story: from starting as a starving artist in New York City, to working as a salesperson, to becoming the CEO of her own thriving independent insurance agency, Dynama Insurance. I believe no one describes a company better than the CEO/founder, so in Erin’s words: 

Erin: I’m Erin Ardleigh, I’m the Founder and President of Dynama Insurance. We’re an independent insurance brokerage based in New York City, but working with clients nationwide. Our focus is on providing life, health, disability, and long-term care insurance, with an emphasis on transparency and education. We’re always happy to help, to answer questions, or to give a second opinion. Our website is

Randy: Erin speaks of her struggles — facing rejection, learning how to move on, having the courage not to do the “smart” thing. Of course we now know, and I knew when I met her as she was contemplating launching her business, that she’d do more than survive. She would thrive. 


Erin: So, I first moved to New York City when I was 18. I had a dream of becoming an artist. I quickly learned that being an artist was not going to make me any money, and that New York City was very expensive. 

At the age of only 18, I was on my own in New York, trying to figure out how to fully support myself, pay for school, and buy food. I soon realized that I could get paid by the hour, or I could do something where I got paid bonuses or commission. I found a job where I could simply set appointments for salespeople, but the more appointments I made, the more money I’d make. And so, I learned to hustle. 

When you start out in sales, anybody who’s old enough will remember cold-calling. You get a lot of rejection, a lot of people slamming a phone down or yelling at you, and you just learn to get over it. You learn that you hang up the phone, smile, and make the next call. 

Moving to New York, having it be much tougher, much meaner than I expected it to be, made me scrappy, made me realize that no one was gonna take care of me but me. 


I did start an early company where I was doing outsourced marketing for small businesses. One of the people that hired me was an insurance brokerage. I ended up working with them as a consultant, eventually going in-house, and eventually becoming a partner at the firm. 

I was 35. Of course, the financial world and the insurance world are very male-dominated. I was working with mostly men, and I really just hit a point where I didn’t see that as my future. But I didn’t know what my options were. Instead of doing the smart thing of putting out my resume and lining up a new job, I just quit.

A couple things had happened to me that really influenced my decision. I was frustrated professionally, but I also had a very dear friend die suddenly. It really shook me to see someone that was full of life, and then all of a sudden was gone. He did tell someone when he was sick, “Don’t feel sorry for me, I’ve lived the best life, I’ve had so much fun.” 

I thought, If I were in his shoes, would I say that? Would I say, I did everything I wanted to do? 

I looked around me and everyone that had those good jobs wasn’t traveling, wasn’t taking vacation, wasn’t doing anything other than work. And I thought, do I want to go get this job where I’m tied to a desk again until I’m 65? No matter how logical it sounded, I couldn’t make myself do it. 

I thought, somehow I’ll make this work, I’ll take money that I could’ve saved and maybe been more responsible with, and spend it.


I decided to take a year off and travel the world. I purposely went places that were further away, the least known to me, that I thought would be challenging, and that I wouldn’t be able to fit into those corporate vacations I thought I might be dealing with in the future. 

One of my favorite places I visited was Myanmar, shortly after the country had opened to tourism. Unlike so many places you go, where they know exactly how to get tourists here and there and make them spend money, Myanmar’s people were as curious about me as I was about them. 

I remember walking through a small village. A woman was sitting outside hand-rolling cigarettes. My guide went up to her and asked if she’d be willing to talk to us. Again, she was just as curious as we were, so she said yes, and my guide served as a translator. 

She was telling me that she had started her own business, rolling these cigarettes, but she was disappointed that people weren’t smoking as much as they used to. I told her that women in America would be very proud of her for being self-sufficient and owning her own business. She was very skeptical that this was true — she thought I might just be pulling her leg, but I told her no, that was very admirable. 

She told me that she wished she had very light skin like mine. I said, “No, everyone in America wants to have a beautiful tan, like you.” Again, she looked at me very suspiciously, like she wasn’t quite sure if I was feeding her a line. But I said, “No, really.”

She invited me into her home. It was very humble. She showed me her altar — it was a good reminder of appreciating what you have, and that women everywhere always want what they don’t have. It was a great exchange because it allowed me to see into someone’s life and see how simple her life was, but also how much we had in common. 


Working in the insurance world, you see that so much of that world is designed and created by men. You see men creating the products, creating the materials, creating the sales pitch. It’s a very one-directional type of messaging and communication. 

I definitely saw times where women were in meetings, and I was in the meeting, and women weren’t being communicated to the same way that a man was being communicated to. And it wasn’t that the woman was being intentionally ignored or left out, but no one was speaking her language, no one was asking questions that were directed at her, no one was bringing up her concerns, her fears. 

There was something more that could be brought to the table by having a woman lead these discussions. 

When I started my business, I always say I had nothing — a little bit of savings, not much — but I had a network. And I had a lot of people who wanted me to succeed and were willing to go out of their way to help me.

Early days in starting my company were challenging. I was always trying to figure out what was the best way to do everything. Thankfully, I had a good support network. I had referrals coming in. But I had to build the entire support system from scratch. I had to figure all the back-office support that I needed, whether it was an accountant, a bookkeeper, administrative staff. 

Figuring out all those people, finding the right ones, and getting them in place was a process. I think I’m on my fourth bookkeeping service. I went through a couple different administrative firms. There was a lot of trial and error, and of course with every failure you learn something, but it was expensive to learn some of those lessons. 

I didn’t get any outside investors or outside funding, so I really just used my savings to build the business. 

For 2015 and 2016, I was working but I wasn’t really developing the business. It was more that I had my business that was coming to me, but I wasn’t really in a scaling mode or a growth mode. I didn’t ever have that moment of, “I’m not gonna make it,” but I definitely had at least a year of, “Why is this not further ahead? Why am I still struggling with A and B?”

I think with every business owner, you hit a point where either you’ve grown too fast and don’t have the resources, or you’ve got some resources, you’ve made some investments but you haven’t yet grown enough, and you’re just in that pain point where you wonder, “Is this all gonna go the way I want it to?” 

I definitely had a tendency to beat myself up, to have higher expectations than were realistic. I really wish I’d started my business and immediately had a business coach to be giving me that outside perspective. I do think most people wait too long to hire help. Even if it’s just a VA to take some basic tasks off your plate, sooner is better. There’s always things as a business owner that you shouldn’t be doing, and it’s so easy at the beginning to say, “No no, I’ll do it all, I’ll save money.” Spend money, invest in your business, give work to other people, because that allows you to have time to be the business owner.

Even if I was beating myself up that I didn’t launch a marketing campaign or hire that bookkeeper or whatever it might have been, what I’d always go back to was my why. Why am I doing this? Is it meaningful to me? Is there an alternative that makes more sense? 

For me, I always felt like, I’m doing a good job for my clients, I’m helping them, they’re getting a better experience than they’d get elsewhere, and they’re ending up in a place where they have insurance, they’re protected, and that always made me feel good. 

Then, I’d say, in 2017 is when things really took off.


A lot of people say, when you start a business, it takes five years to be successful. I thought, No way, that won’t be me, I’ll be rolling in dough in a year. Now, I think that five years is a really good timeline for most people. I really feel like it took me 4-5 years to feel like everything was humming. 

I’ve just slowly added people to my team over that time. We now have four client-facing people on our team, all women. 

Certainly, in insurance and finance, you don’t see anywhere near as many female-led firms as male-led firms. You see a lot of women in marketing, business development, customer service, but you don’t see women as at the top salesperson or the owner of the company. We know women aren’t being offered as much VC funding. 

I think it’s because like begets like. If you look around and all you see are men running these companies, you may not feel comfortable going into that marketplace. 

What I learned as someone who came from essentially nothing and had to create my own world, created a successful business, traveled to seven continents, am happily married, and am really very happy with life, I’d say that you really can design the life you want. Don’t hold back out of fear. If you love something, and you think you have the ability to run a business, you have the stamina, you have the life support, do it. Try it. It’s okay to try and fail. It’s okay to try and change and pivot. It doesn’t mean that you just get one shot. 

Randy: Erin, thank you for sharing your remarkable story. Thank you, Dustin Lowman, my marketing manager, for producing and editing. Thank you Aker Advisors and Heron Wealth for their financial support. To all of you, our listeners, if you like what you hear on “To Grit with Grace,” I encourage you to share this with others. We’ll be back next month with another speaker’s tale of entrepreneurial struggle and perseverance. Until then, with grit, with grace, with growth, and with much gratitude.