The Power of Being Prepared

In this episode…

Nic Cary interviews Samantha and they discuss the lessons learned during her career journey including:

• The importance of building strong, aligned teams that share a common vision to achieve long-term success.
• The value of identifying unmet needs and bringing proven solutions to new markets to create impact.
• The necessity of balancing profit with purpose to drive sustainable growth in both for-profit and nonprofit ventures.

Sponsor for this episode:

This episode is brought to you by Sky’s The Limit, one of the largest nonprofit programs for underrepresented young adult entrepreneurs in the US. Sky’s The Limit is a quick-growing digital platform that connects entrepreneurs with their peers, volunteer business mentors, training resources, and funding.

Our goal is to develop the social capital that founders need to chase their business dreams.

To learn more, please visit www.skysthelimit.org today.

Episode transcript

INTRO (00:04):

Welcome to The First Buck Podcast where we feature stories about entrepreneurs and the people who support them. Now let's get started with the show,

Nic Cary (00:23):

Hello and welcome to The First Buck Podcast, brought to you by skysthelimit.org. We feature stories about entrepreneurs and the people who support them. Today we're joined by Samantha Roady, CEO of Simply Business's U.S. operations. Simply Business is a leading digital insurance marketplace focused on small businesses. Samantha has nearly 25 years of C-suite experience, building, scaling, and managing highly complex, regulated global technology businesses.

A marketer by training, Samantha is highly knowledgeable in consumer and B2B marketing and building brand-driven businesses.

Prior to Simply Business, Samantha served as Chief Operating Officer of MoneyLion. Before that, she was President of Gain Capital, now StoneX Global's retail brokerage business, responsible for everything from commercial strategy to all revenue-generating activities, including sales, marketing, partnerships, consumer operations, and regional management.

So we are very lucky to have Samantha with us today.

Samantha, we have a little tradition here—we need to learn: How did you earn your first buck?

Samantha Roady (01:24):
Well, Nic, thanks for having me.

So, my first buck was babysitting. It's crazy to hear, but I made $2 an hour.

You might be able to guess my age from that answer, but it was before I was able to actually get a job with a salary. So I did that for a few years.

And then I think my first kind of official job was as a lifeguard.

I was a competitive swimmer growing up, and, at the local swim club, I got my training and actually had a great couple of summers as a lifeguard at the pool.

So those are, like, my first two jobs.

Nic Cary (01:59):

I like that. So it's so funny that sometimes people's first jobs actually entail a huge amount of responsibility. Being a babysitter means you're taking care of someone's life. And a lifeguard is exactly the same thing.

And so, I can see how those early sort of things probably led you to take on an increasing amount of responsibility in your career.

Talk to us a little bit about maybe what happens after your lifeguard job—go to school, or how your career sort of takes off from there.

Samantha Roady (02:25):

Yeah, sure. So after the lifeguarding experience, I did have a couple of other jobs. I worked, got a lot of good experience. I worked retail, I worked in restaurants, which I do suggest that everyone has some experience in the service industry at some point in their life—training for just basically dealing with customers and the public.

And it's obviously a good way to make money. So, went to college. After college, actually, I did get a degree in international affairs, and my idea was to actually work in DC, either on Capitol Hill or to get into lobbying, and ultimately just decided that Washington was not going to be the place for me.

So kind of retrenched and thought, what's next for me? Actually came to London and did an internship at Friends of the Earth. Got a lot of great experiences working in kind of PR marketing for the organization, helping plan their first Earth Day—again, kind of letting the people know how old I am.

But it actually kind of piqued my interest in that area. So when I came back to the States, I started thinking about what I wanted to do. And as it happened, actually had a friend of mine from the internship program who was moving to New York City. I grew up in Virginia, and all of a sudden I thought, wow, I think I want to move to New York City.

(03:37):
My parents at that point thought it was pretty crazy but supported me. Moved to New York City without a job and basically did a couple of odds and ends, did some bartending, worked in, did some public policy research, did all these things trying to figure out my spot, and ultimately landed at a really fast-growing financial software company.

I was hired in as a marketing coordinator and executive assistant to the president. It was a small company, wear many hats, which was actually a great experience because it was my first really corporate environment. I was able to get exposure to a lot of different types of roles within the company.

And of course, being part of a fast-growing company is just a really exciting kind of opportunity and environment to be part of. And that really put me on a trajectory. Really embraced the marketing function and really leaned in there and was fortunate enough to be given a lot of opportunities to continue to develop in that area.

A few years later, I took over responsibility for the department. I was the director of marketing. I was learning on the job, and it was scary but also super invigorating at the same time. And then progressed through that company, stayed another two years. I was there four or five years together.

(04:55):
And then the person who was the number two at that company actually had that idea to start this new business called Gain Capital and asked me at that time to come and join and be a founding partner and to lead the marketing function. So again, like, you had a little bit of a big leap of faith in terms of leaving a stable company, going to a startup that didn't actually even have any investors yet.

It was really just an idea. Helped put together. There was a business plan, but helped put together kind of the first pitch deck for us to go out and try to raise money and then was part of that process. It was just, so, yeah, we were able to get our first investors, we set up the business, and then I was actually at that business for 20 years. So it was an amazing ride.

I think maybe taking a step back, what I would tell the audience is that maybe one of the things that I really appreciate about my career is that I've been given amazing opportunities by people. But I feel pretty good about the fact that I've taken full advantage of them and kind of leaned into it and really kind of shown up and done the job and demonstrated my commitment.

And through whether it be hard work or a pretty healthy dose of curiosity and just grit, I was able to continue to develop through my career and kind of just take the next opportunity and the next opportunity as it came on.

Nic Cary (05:35):
I think if I just summarize you, it's definitely fearless in trying new things just through that story arc already.

Okay, so, amazing. We start off earning $2 an hour from a lifeguard.

You travel around the world a little bit—DC, London, New York. I mean, these are incredible cities.

And then you end up in an entrepreneurial environment that you stay in for 20 years.

So, now you're the CEO of the U.S. operations for Simply Business. Talk to us about what Simply Business does.

Samantha Roady (06:41):
So Simply Business is basically taking the process of buying for small businesses, taking them in the process of buying insurance online.

The traditional way that you get insurance—you call an agent or a broker, you tell them a little bit about your business, they go off, they figure out what type of insurance providers would write you a policy, and then you buy it either over the phone, through email, or through mail.

What Simply Business is doing is actually bringing that whole entire process online. So, if you are a small business owner and you need anything from general liability or errors and omissions, if you're a consultant, or potentially workers' comp, if you employ other people, you can come on our website.

You can tell us a little bit about your business. We have a form, and then we will present you multiple options for the insurance that you need, and you can actually buy it online and get covered immediately.

Nic Cary (07:31):
Amazing. Okay, very cool. Talk to us a little bit about your customers.

When you say you support small businesses, is it sole proprietors, is it growing companies? A little bit of everything? What are the customer profiles that Simply Business supports?

Samantha Roady (07:44):
Yeah, so it's really any Main Street business. It could be anything from, you know, any sort of tradesperson, contractor, or plumber through to a professional kind of consultant.

Anybody, you know—you mentioned something in an accountancy business or a marketing consultancy. It could also be, you know, a brick-and-mortar business.

It could be anything from a flower shop to a nail salon to an e-commerce business. So, I think over a thousand different businesses we support today, and a healthy percentage of them are sole proprietors.

And then we also support companies that have up to, say, ten, maybe as high as 25 employees, depending on the nature of the business.

Nic Cary (08:24):
Very cool. Let's talk a little bit about maybe some of your entrepreneurial experience, actually, and take a step back in your career.

So a lot of the entrepreneurs enrolled in the Skys Limit programming are in the early stages of trying to find product-market fit, and a lot of them get really excited about marketing their business.

But they think that maybe marketing is brand sponsorships or getting their logo on a sports team or something like that. Those are extremely expensive types of deals.

Talk to us a little about the kind of advice you might give to an early business, as a marketing expert, for how they can and should be thinking about the very earliest stages of their business.

Samantha Roady (09:01):
Yes, well, it would be different for, say, a local business than it would for an online business. But if you take a local business, really building word of mouth throughout your community through different associations or even just good old on-the-ground grassroots marketing efforts, making sure that you're taking full advantage of any referral business that you could get. If you get a customer, basically have them help you get the next customer.

So, I think in terms of that, I would say it's very specific if you are a local business to really tap into your local community and what you can do to build, again, word of mouth.

If it's an online business, yes, it can be very expensive to try to get customers. I think that's why platforms like Amazon have actually attracted so many small online businesses, because it gives you a massive distribution channel for your products, and they also have all the tools that you need to help potential customers discover your products.

And obviously, there are other platforms—similar platforms that are not as big as Amazon, whether it be Etsy or something else—where you can reach an audience without having to find each individual customer on your own.

Nic Cary (10:14):
That's super helpful. Thank you. So marketing is really maybe about helping build this awareness, like you said, and people can go use all the tools at their disposal, including online ones, or just hitting the pavement and actually spreading the word on a local level.

But it's really all about making that first sale. And I was wondering if maybe you had any memories of one of the first times you closed a big deal or you were involved in something like that.

So maybe you could share some lessons with our audience, yeah?

Samantha Roady (10:43):
I think what comes to mind for me is going out and trying to raise that first round of capital for Gain Capital.

Again, this was something that was a very new experience for me. Putting together the investor presentation, going out with the founder, sitting in front of potential investors, and not only really, you know, selling the idea of the company, but also realizing how important the team behind the idea was to people.

You know, people getting excited about the opportunity and willing to invest their dollars. So, being part of that and learning about that and then actually successfully being part of that fundraising, I think, was something that was really, it was great for my career to see it, and also it felt really good to actually be successful when we were able to raise that first round.

Nic Cary (11:38):
You just ticked on something that's going to make this transition perfect. So let's talk about teams.

It's one of the hardest things to do—recruit, retain, and develop talent in companies.

I would love to hear, having your experience hiring people, what is your maybe favorite interview question? Or what have been some important lessons you've learned in figuring out how to recruit and build a great team?

Samantha Roady (12:01):
That's a great question.

Because it is incredibly important to any successful business—the team that you build around and how well the team works together. So, when I'm recruiting, especially for a leadership position—but really, you can apply this to any hiring decision—I tend to look for four key qualities outside of the skills that you would absolutely need for this hire.

I look for grit, I look for rigor, I look for curiosity, and I look for evidence of their ability to be a strong team player.

You know, to me, those are going to be the success criteria for any new hire. And if I had to put maybe one question forward as my favorite interview question, I would always ask people, do you consider yourself lucky?

Because the reason that I want to hear their answer to that question is because it's actually really, you know, I don't really believe in luck. I believe that old saying, fortune favors the prepared. So I really want to hear people who can give me examples of how luck comes through preparation or hard work—going back to grit and rigor.

And you get really, really interesting answers to that question.

The follow-up is always for me to ask them, tell me something about you that I couldn't learn from reading your resume. I want to hear something personal about them, and it's also very interesting to hear what they choose to share.

Nic Cary (13:35):
Yep. I think those types of questions are perfect.

I have never—that one about luck is a really good one because it's a real insight into people's, I would say, reflection on how they've gotten to where they are.

And I think a more humble, less egocentric person would reflect carefully about how they answer that question. So that's a really good one. Thank you for sharing that.

So we're looking for grit, rigor, curiosity, and the ability to be a team player.

Very, very cool. Okay, so one of the things I wanted to ask you a little bit about—so many entrepreneurs and small business owners—they need advice, they need support, and they're looking for peers.

And I wanted to know, like, who in your career had been really important in helping you, taking those chances on you, giving you that confidence when you needed it, and maybe acting as an ear when you were not sure how to do something.

I'm interested to hear your relationship with people that were supportive of you in your business career.

Samantha Roady (14:31):
Yeah. So, I've been very fortunate to have some very strong mentors in my career. And interestingly enough, I can think of two, and they were both male.

And I actually think that it has been helpful for me as I came up in my career.

I was also coming up through financial services, which was a very male-dominated environment. I was often the only woman in the room, so to have a male mentor/ally who believed in me, who supported me, and who gave me opportunities was very confidence-building.

You know, again, I do think that I took full advantage of that, kind of going back to my earlier point about how it's really not what opportunities you are given, but what you do with them.

And I still, to this day, have very strong relationships with both of them and still consider them mentors. Not obviously as active, but they're only a phone call away.

Nic Cary (15:30):
When you say you took full advantage of those mentor relationships, just for the sake of our audience, what would you say? How did you do that? How were you taking advantage of it?

Samantha Roady (15:43):
Well, I did ask for feedback.

If I had questions about how to handle a certain situation or if I was at a crossroads in my career and was trying to make a decision, I'd reach out to them, lay out the scenario, and ask for their input.

So, again, being proactive was a big, big part of that.

Nic Cary (16:03):

Yeah. So, I think we all have those blind spots that are sometimes hard for us to acknowledge or see.

And, you know, sharing your opinion out loud with someone is just a great way of organizing your thoughts, especially if you've got some people you trust to do that.

I think it can be extremely helpful when you're at pivotal moments in your career. If you don't know how to deal with something, it's okay to ask.

There are a lot of people who are so happy to be helpful in those scenarios—people who have experienced things, made mistakes, and are hopeful to pass along lessons to help others avoid them in the future.

Samantha Roady (16:34):

I think it can be extremely helpful when you're at pivotal moments in your career. If you don't know how to deal with something, it's okay to ask.

There are a lot of people who are so happy to be helpful in those scenarios—people who have experienced things, made mistakes, and are hopeful to pass along lessons to help others avoid them in the future.

I think that's a key point, actually, for anybody who's listening, because sometimes you feel self-conscious about asking for help. But in my experience, people are more than willing to help if you just reach out. So it's just about raising your hand.

Nic Cary (16:51):

So, I want to know—you’ve had this amazing career.

How do you keep up with changes in the business climate? Do you do a lot of reading? What's your way of staying informed with what's happening in the world?

Samantha Roady (33:12):

Yes, I do a lot of reading, but more recently, I've been relying on podcasts more frequently.

It's just a great medium, especially since I travel a lot for work, and so it's super easy to pop in a podcast and listen for 30 minutes. You know, you can listen in multiple sittings.

I tend to default to more business and current events, but I also have a few go-tos that are more around leadership.

Ah, so there's one—Fixable by Frances Fry. She's an HBS professor. She has a great podcast. There's another professor named Adam Grant, who works at Wharton. He has a podcast called Work Life that I tend to listen to a lot.

I also like the Radical Candor series. It's always a great one because giving feedback is not easy, but obviously, very key for any leader. Doing that effectively is, of course, important.

I also like the Masters of Scale podcast with Reid Hoffman.

So, yeah, I mean, a wide variety. I'm always looking for new ones. I get a lot out of them. I take a ton of notes. My Google Notes app is frequently open, and I'm just typing away on things.

So, yeah, I do like podcasts.

Nic Cary (18:21):

I think, well, we're big fans of podcasts around here, and I know a bunch of the ones you referenced there.

I think they have amazing content. I think one of the things you said that was really a pearl of wisdom there is on the Radical Candor podcast.

One of the lessons that is really trying to be conveyed is that you can't improve if you're not facing the hard truths and the reality of things.

And, even though it's hard to hear it sometimes, feedback really is a gift. And you should take it on and work to improve the scenarios or situations that you may find yourself struggling in.

And hopefully, you find people that can give you that feedback who are worthy of providing it to you.

I think that's very, very valid.

Samantha Roady (19:00):
Feedback, positive and negative. I think people think about feedback as only opportunities to improve. But I think Frances Fry, when she talks about Scooby snacks and the ratio of positive to negative feedback—four to one, I think, is her ideal ratio—even things like that are important to remember.

Because I do think we tend to overlook when people do things well, just giving them a quick acknowledgment really does go a long way as well.

Nic Cary (19:26):
I found that my whole career is just acknowledging the right things, which is oftentimes even more important than just criticizing and being nitpicky about what somebody's done.

So, great reminder.

Okay, so let's wrap this up. I got a question for you. Entrepreneurship and starting businesses—or taking those leaps of faith in one's career, whether it's leaving a stable job to go start something new in New York City or something else—can really feel scary.

What tips can you give our listeners?

As someone who's traveled around the world, changed jobs, and then invested deeply in the ones you have spent a long time in, what tips can you give them to manage their stress and basically play for the long game?

Samantha Roady (20:08):
Yeah, no, that's a good question. It's been a bit of a theme during our conversation around this grit, rigor, resilience, and all of that.

Anybody going into entrepreneurship is probably under no illusions that it's easy, right?

But when you get into it, you may sometimes lose sight of the forest for the trees, right? You will have setbacks. You will have maybe some failures.

I think just kind of acknowledging that this is part of the process and trying to figure out if a setback is actually an opportunity—what can I do differently? Learning from everything that happens to you as you're building your business will help make it stronger in the long run.

Certainly, preparation. I talked about that—fortune favors the prepared. So, I think anybody going into it does need to be really committed to the level of work and commitment that they are going to have to put in to actually make a business successful.

So, that's good—keep reminding yourself. And then the other kind of axiom that I always try to remember is this idea of urgent versus important, right?

I think we all tend to get dragged around by the urgent matters, but as leaders and small business owners, you have to make sure that you're balancing the urgent versus the important every single day.

And so I always try to remember that.

Nic Cary (21:33):
Yep. I think you've hit on something that's so important, which is that being prepared—it's not about rising to the occasion every time. It's actually having all the tools in your kit for the moment.

And, basically having all of that preparation so that you can answer the questions in the interview, so that you can nail the pitch when you go do the fundraising, and really having command and mastery over the subject matter.

That's super valuable.

Okay, well, we have had a whole bunch to cover off here, everything from the early days.

I wonder how much a babysitter costs now. It's probably a great...

Samantha Roady (22:08):
I know, it's like out here on Long Island, and it's $25 an hour in 2020.

Nic Cary (22:12):
Wow.

Samantha Roady (22:13):
Pretty good. Pretty good. Yeah.

Nic Cary (22:15):
That's really good. The other thing I really liked is the opportunity to spend some time on the front line of a service industry, whether that's in retail or working in a restaurant or a bar.

It provides huge amounts of skills for you. You learn about customer service, you learn how to manage client expectations.

You can avoid a crisis by intervening in small and subtle ways, and you can really delight customers on a special day, whether it's their wedding, an anniversary, or a birthday.

All those little things go a long way. If you can scale them into an actual business that you take on your own, those lessons, you'll find, will pay dividends in the long run.

And I think I've noticed that in people's careers who have had a lot of different experiences in the early stages, those things compound and pay off really big in the long run.

When you really understand what motivates people's purchasing decisions, how they have a great experience, and when they're going to tip you extra because you've been extra attentive to them—all that stuff just escalates as the business gets more complex.

Samantha Roady (23:19):
Couldn't agree more. Well said.

Nic Cary (23:21):
All right, well, thank you so much for your time. We've been extremely grateful to have you on the podcast, Samantha.

Again, please check out Simply Business for any insurance needs, and then at skysthelimit.org, we connect underrepresented entrepreneurs with volunteer business professionals for free, one-on-one mentoring.

We also provide business guides to all of our members and monthly funding opportunities. You can sign up for free today, and if you like what you heard, please subscribe and share this podcast.

OUTRO (23:48):

Thanks for listening to The First Buck Podcast. Don't forget to join the community of underrepresented entrepreneurs and their supporters by signing up at skysthelimit.org. Click subscribe and we'll see you next time.