86: {Interview} Hiring and Scaling: Tips for Entrepreneurs with Kasey D'Amato

Attention Business Owners: Are you in growth mode? If so, this episode is for YOU. Whether you are under $500K in revenue or scaling over $2M Kasey offers great advice on exactly where you should be focusing your time. 

Kasey D'Amato shares her career journey, from starting in sales to becoming an executive business advisor and life coach. She discusses her experience in managing a medical practice and launching a skincare company. Kasey emphasizes the importance of understanding and adapting to different leadership styles when managing a team. She also highlights the challenges that entrepreneurs face, such as sales and marketing, building a team, and self-care. Kasey provides insights on when to hire and how to achieve balance in business and personal life. 

Takeaways:

• Understanding and adapting to different leadership styles is crucial when managing a team.
• Entrepreneurs face challenges in sales and marketing, building a team, and self-care.
• Hiring a virtual assistant and freelancers can help solopreneurs scale their business.
• Traveling and experiencing new things can fuel creativity and innovation.
• Reading, learning, and meditating are essential for personal growth and balance.
• Building a team and focusing on sales and marketing are key to business growth.

Kasey D'Amato is an executive coach dedicated to guiding business leaders in achieving holistic success—both in their businesses and personal lives. 

More on Kasey HERE and you can connect with her on LinkedIn HERE 

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Transcript

Caroline (00:00.23)
Welcome, Casey.

Kasey (00:02.52)
Thanks for having me.

Caroline (00:04.914)
So tell me about where you are right now and how did you get here? You and I met previously and you shared your story with me and I'm just amazed at everything that you've done. So start from the beginning.

Kasey (00:15.618)
Yeah, I'd happy to. So today I am an executive business advisor and life coach, but this is not what I've done my whole career journey. So my career has been very interesting. A lot of people kind of call me the queen of pivots because I've had quite a different vast experience as many people have. And I started in sales. That's where I very first started in a wholesale pharmaceutical company. So we sold...

injectable drugs to hospitals and it was based in Miami. I was right out of college and I learned from the ground up, you know, how to make cold calls. And that was my very first dipping my toe into the world of business was on the side of sales. And soon after that, decided I really was more of a service provider and I decided that I wanted to pursue a career in medicine. And I went to PA school in California and got a great career as a dermatology PA. I joined a fantastic practice in Santa Monica, California.

And soon into that career, I launched the aesthetic division. was general dermatology when I joined it. All the physicians practice just general dermatology. I launched the aesthetic division and grew that business by close to seven figures. And then soon after that, became part of the management team. And so I started managing a team of about 18 people. And that's when I really first learned my leadership skills. And I was probably at that point just about,

my late 20s and I started to learn how to lead people, many of which had been there a long time, much older than me, and had different levels of experience. And so I learned sort of the hard way how to manage people and what it takes to run. know, at this point, this was a multi seven figure medical practice. And I learned a lot of the operational things and some of the financial systems that go into place into running a small business of any kind. This happened to be medicine, but I started to understand how things worked.

At that point, I started my own small side business, a consulting business I still have today. One of my businesses, I typically always own a few at any given time, but one of my businesses is a consulting business for medical professionals to help them with salary negotiation and career coaching and to really understand the business side of medicine and how to use that in your career trajectory. And it's very fulfilling. have a team

Kasey (02:28.612)
But of course, as those of us who are serial entrepreneurs, we're always sort of, what's the next business I'm going to start, right? So now at this point in time, I've been practicing for probably about 10 years as a clinical dermatology PA, launched the aesthetic division. I had a very high profile patient following, lots of celebrities and high profile people in Los Angeles. I had my side business consulting and coaching medical professionals.

and managing also the dermatology practice as one of the senior managers and decided I was going to launch a skincare company because you know, why not? That was going to be easy, right? That did not prove to be an easy venture. That was something that proved I had to raise capital. That's not the type of industry that's easy to break into and bootstrap. So I had to raise capital and take on shareholders and it was very, very fun and sexy and glamorous. We were on the cover of New Beauty Magazine.

And oh my gosh, we were in so many press mentions. This was back in the kind of 2013, 14 era. And we became the first natural medical grade skincare. And it was really a fun ride. We ended up launching overseas in Europe and South America, but there was a lot of overhead in running a business like that between inventory, marketing, sales, and the pandemic hit. And there was just a lot

There was a lot of moving parts I think that I didn't realize in that venture. And at that point I was juggling it all. I was doing the skincare, seeing patients, managing the practice and doing the medical consulting and I just burned. completely, I hit a wall. I found myself in my doctor's office. You I'd only slept four hours a night probably the last three or four years. And, you know, she said, if you continue like this, you're 35 years old going on 36. And if you continue like this, you will have a heart attack.

before the age of 40. Like this is not humanly sustainable what you're doing. And I thought I wanted all the things. And at that point I had to make some very difficult decisions and make some hard moves and decide to exit. And so that company, ultimately we exited, we sold that company and I took about a two year sabbatical. I lived overseas. My husband had a project there and I just really thought

Kasey (04:44.952)
what I wanted to do because at that point I pretty much shut everything down. I stopped it all. I retired from clinical care. I sold the skin care company, you know, and I obviously wasn't managing the practice anymore. And I had to really hit the reset button and reflect on what was good and what was bad about my experience. And mostly what did I learn and how can I help others? And fast forward to now as you know, I am an executive coach and I help people.

advance their life. I help people scale their business and do it in a way where they can have balance and it's holistic and they can use simple systems and framework to grow and accelerate their business and at the same time improve their quality of life at home with family and travel and self -care so that they can they truly can have it all and help people avoid hitting that wall and that you know dark time the lonely dark times when you think you have everything under control and you really

And that's what I experienced. And I really want to help people navigate around that because, while I've had a lot of successes and I've learned tremendous amount, everything from startups to massive companies raising capital, selling a business. I consulted for billion dollar pharmaceutical companies along the way. I really want to take all of that experience and help others. And that's my mission and passion is

help other people accelerate their business and not experience to overwhelm the burnout and hit that dark time. And it is possible. It is possible.

Caroline (06:12.744)
Okay. I want to back up and dive deeper into those two positions that you had one being you were the leader of the medical practice. You're managing 18 people taking on patients yourself and managing the staff reporting to you, which that alone is a full -time job. And then you just casually created a skincare company, which I know it's not casual as someone who has my own product that I've invented. It's not an easy thing. So let me back up to when you went to the management seat, what was your biggest challenge

the leader of that medical

Kasey (06:45.102)
By far my biggest challenge, I managing people, right? We all say like the hardest thing of managing people is managing people. I think the absolute hardest thing for me was to understand that people are going to react different. Not everybody thinks the way I think or not everybody has the same goals for their role. And so to adapt my leadership style in a way that made everybody on the staff feel comfortable.

feel excited, feel energized, increase the morale, and at the same time balance having a level of authority without being a dictator. And I think that is the hardest thing for most people in a leadership role. People will swing into the friend mode and then the lines get blurry about, who is really the boss here? Or people swing very far into kind of that dictator, I'm the boss mode, and that's not a good way of leadership.

either. That's not an effective way to lead the team. And I always equate leadership to the really famous coaches of sports teams. And I'm not a sports fanatic at all. But if you look at the leaders of sports teams, they have an air of calm, confidence, and there is authority and there is respect because they can see the whole landscape and they're looking at all perspectives. And that's what I try to do. And that's what I do to this day is I try to really put myself in the other person's shoes.

And I think that is when I started to shift, become a stronger leader was when I really started to think about if I was them, how would I be responding to this situation, this conversation, and what would I want the outcome to be if I was sitting in the other seat. And that was the biggest shift for me and the biggest learning point early on to be an effective leader of an 18 person team.

Caroline (08:29.426)
That's pure gold right there because it takes a lot of self -awareness and emotional intelligence to be able to do

Kasey (08:36.972)
For sure, yes.

Caroline (08:39.354)
Okay, so back to the skincare product. Did you have to hire a chemist? How did you know what skincare product to start with? And did you go with a whole line or did you just have one product in your portfolio?

Kasey (08:51.645)
Great questions. for the record, right now I coach primarily service -based businesses because inventory tracking, holy moly. So yes, we did work with a chemist, myself and a colleague of mine from medical school. We created all the formulas ourselves. We actually created the proprietary ingredient from blueberry extract called Berry Matrix. We studied it in a research facility in Germany and we proved

our particular blueberry extract that we created would protect from infrared radiation to help prevent wrinkles from forming. So we published our research in a medical journal and that was very prestigious. That had never been done before for a skin for natural skincare company to publish their research in a medical journal. So we did

But we did have a local formulator, right? Like we weren't making the products in our bathtub at home, right? Things kind of started that way, but very soon we had a local facility in Southern California that was manufacturing, but we created all the formulas. So we had a manufacturing facility and a storage facility and all those things in Southern California. And then we were distributing mostly through physician offices to start. Our model started as a pharmaceutical model because that's what I knew. That's where I started before

I went to medical school and that was the arena that I knew very well. So we started with a sales force on the street, calling on doctors offices, knocking on the doors to be physician dispensed. That distribution model proved to be a bit too costly, right? We had to hire a sales force, give them cars, give them all these sample products. So ultimately we pivoted that to go online and ultimately we also pivoted

established a partnership with a company, network marketing company that had global distribution. And that's how we ended up launching internationally. We sort of joined forces with a company that had a whole portfolio of products and we went under their umbrella as one of their products and launched international. So it was quite a venture. It was about a 12 year long venture, multiple rounds of capital raising and a lot of moving parts.

Kasey (10:52.696)
We exited, like I said earlier than we wanted. So it was not the exit that we were anticipating. And that was a very hard decision to make that judgment call. Were we going to stay in longer or in trying to hit the marks that we wanted versus kind of lick our wounds and say, this probably is time. And I think for me, my mental health status and physical health status was at the point that I couldn't keep going. And one last thing about that venture was

I always knew that that venture was going to be 10 years of my life. When I started that product -based business, my goal was to grow it, scale it, and bolt it on to another company, ideally a pharmaceutical company. That was my vision. That's not what ended up happening, but I knew it was a 10 -year plan. It ended up being about 12 years, but I always knew exactly when I wanted to get out and how I wanted to exit. Now, was it the exit that I wanted and the time I wanted? Not exactly.

but I had a vision for an exit. And that's a mistake that a lot of people make in business is they start something and they're not sure where they're going with it. And then they feel at times stuck in ruts or they feel maybe the overwhelm or the burnout or they're not sure their next step. And their next step is directly proportionate to the stage they're at related to their end goal. And so if you're not clear on what the end goal is or the timing of the end goal, then the next step gets very hazy and blurry.

And so that's a big, big mistake that a lot of people make both in product and service based businesses is they're not sure where they're going with it long term. What is the ultimate exit plan? What timeframe are they going to sell it? Is it a legacy to pass down? So that's another thing that was very mindful about with that skincare business.

Caroline (12:36.114)
So as an executive coach, what's the biggest challenge? mean, you just mentioned a huge challenge that I agree with you that a lot of entrepreneurs get into starting a business, they grow it and then they don't know what to do with it. But in addition to that challenge, what else do you see entrepreneurs or business owners struggling

Kasey (12:55.064)
my gosh, I mean, there are so many different things, right? So I sort of classify areas of business like in red zones. And, you know, if you're not growing fast enough, then your red zone is more related to your sales and marketing. And almost always it's that you're not looking at your metrics in a strategic way. So almost always there's something that you're not tracking exactly your awareness, your trust, your acquisition. When I say acquisition, I mean how you're getting contact information for your prospects.

and you're not delineating your marketing from then your sales. So there's a six step process. And if you're not looking at the metrics of each step, so there's three in marketing and then they switch to three, they're kind of more sales, sales and marketing. it goes awareness is number one, how are people hearing about you? Trust is number two, how are they trusting you? Acquisition is number three, how are you getting contact information? How they reached out and said, I would like to learn more. They haven't bought, but they're now coming into the ecosystem. They would like

learn something, they would like to engage in some way, consultation or whatever it might be. Then it switches to the conversion. So now you're in a sales conversation in some way, then you're into a retention. You know, how are we keeping those, those people in our community and continuing to serve them? And then as referral, ideally they're spreading the word and they're becoming raving fans. So people that are stuck in a growth, typically if they're, if they don't have their metrics dialed in, in that six step process and differentiating between marketing sales, they'll get stuck there.

And that's red zone number one. Red zone number two is where people get afraid to build team. Because if you do not surround yourself with people, you will get stuck. I always say that if you are a solopreneur forever, you have the worst job working for the worst boss, you. Because you're doing all the things and you're burnt out. So solopreneuring is designed to be, in my opinion, for a very short period of time.

You are just bootstrapping quick. This is a matter of months, less than a year. And then your number one goal is how do I build this machine so I can bring somebody onto it? And so if you're not doing that in your business, in my opinion, you don't have a business, you have a tiny little embryo of something, but it's not going to get any legs. It's not going to be able to crawl and walk. And so that is the other area of red zone is if you're not building something with your number one intention of how do I build a team around this thing?

Kasey (15:15.298)
then you're gonna burn out and you're gonna get stuck in red zone number two. And the last red zone is self -care. How are you balancing what you're doing with your business activities? So whether you've got your sales and marketing or whether you're doing your teams and systems, depending on where you're stuck there, the third one is, are you balancing things? Are you balancing your self -care? Are you prioritizing your workout? Are you stimulating your mind in other ways? Are you learning something new? Are

networking with people, are you expanding the way you're thinking? Are you taking downtime? You know, enough downtime. Most people do not. They way underestimate just thinking time. It's time. The more time you disconnect, people don't realize your brain will be triggered to get new inspiration, especially if you travel. I always travel to new cultures and new countries because when you disconnect from business and your brain is stimulated to maybe speak another language or try another food, your brain opens.

It opens its mind's eye into new opportunities. When you come back, you'll be amazed and you'll be flooded with new innovative ideas for your business.

Caroline (16:18.898)
So if someone's listening to this podcast now and in one of those red zones you just mentioned, which one is priority to focus on to help move the needle?

Kasey (16:28.708)
Depends on what stage you're at. If you are under 500K in gross revenue, marketing and sales is your priority. Like you've got to get the cash flow. Cash flow is the bloodline of your business. So if you are under 500K, but marketing and sales, dialing that into understanding the key metrics so that you can replicate what you're doing is critical. If you're getting over 500K, if you're between 500K and 2 million, there's a big red zone right there because that is all about building your team and systems.

And at that point, you're starting to even build some management levels. You're starting to layer your team a little bit and you want to build your team in a way that the team is making you money, not costing you money. So a lot of people can make mistakes in that 500k to 2 million mark where they're building the team. You you might be listening to this right now and you're saying, I've done all these things, Casey, but I'm losing money. That's why there's a big red zone right there that you want to be very careful how you're building your team because

We only have so much cashflow in the 500K to 2 million market. People are expensive. Teams always going to be the number one most expensive on your income statement. it's very, it's a very delicate area to build a team there. And then once we get over 2 million, then we want to increase team morale. We want to optimize and we want to start innovating. We want to start doing things a little different. And so depending on what stage of business you're at is where you want to be focusing the bulk of your energy. You're always focusing on all of these things.

but some of them become more in the forefront depending on what stage you are in your business

Caroline (18:02.344)
So how do you know when it's time to hire? You talked about building your team around you and yes, people are expensive. I used to be an executive recruiter, so I'm very aware of what people cost and it's not even the cost of the actual salary. It's like, you have to train them, you have to do all these things and onboard them. So there's a time piece in that too. If I'm a solopreneur listening to this, or let's say I'm running a million dollar company, who do need to surround myself with? Do I need to outsource? Do need to 99 people do contractors

Do I need to go all in and hire W2 employees?

Kasey (18:34.564)
Great question. So if you're in that stage where you're under 500K, so you've been in that solopreneuring, let's say you're even under 100K, you've been solopreneuring and you're building your small and mighty, I'll call it the embryo of the business. Like it's starting, it's got a heartbeat, but we want to get it to get legs and start to be able to crawl and walk and run. So as soon as you can, I would bring on at least a part -time VA with the intention that you are looking at your schedule and you are time blocking. If you are under

60 % of your calendar should be related to sales efforts, 60%. And if it is not, then you can't guarantee that we're going to be able to expand the hours of this person and on bringing another person or pay yourself. So if you are under that 100K, then the bulk of your energy is on sales and the service providing. In any bit of marketing that you're doing has to be specific sales related marketing, not branding,

the sales related marketing, because there's a big difference in marketing efforts and people can get stuck in the creatives and that may or may not bring in the leads and bring in the new clients. So as soon as you can bring on that part -time BA, scale that person up, but make sure that you are paying attention to your energy and that you are building the machine so that that person is freeing up tasks that free you up to be doing more

the sales or the marketing that is directly related to the sales activities. So very clear path. You take two hour block off your calendar, you give it to the VA and that two hour block goes to sales activities. That's how it works and how you build the business in those early stages. By the time you're at, you know, a couple hundred grand in revenue, you should be able to have a VA and at least one freelance person. If not two, I would start in this order. So VA.

and then freelance, some freelance teams. So now you're bringing in some industry experts, but you're not having to go through the W2 process. But there are people that are very good in what they're doing and they can help alleviate some other things. So at this point, you're probably gonna be thinking about bookkeeping. You're probably gonna be thinking about potentially some support on the marketing side of things, or depending on the business that you have, could be project management. But the critical piece of the puzzle is in these early days,

Kasey (20:50.712)
The effort needs to be on the sales machine and the marketing machine related to sales. So every hire either needs to be in that role or free up your time to do more activities in those roles.

Caroline (21:04.296)
That's a great breakdown because as you scale, even if you're solid, we're in less than a hundred K of virtual assistant. mean, you can go on Upwork or Fiverr and hire someone good for less than $20 an hour. And you don't even have to hire them full time. You could do start with 10 hours or 20 hours and then see how comfortable you get with them and how good that they are and how best they serve you and go from

Kasey (21:27.556)
That's right. That's right. So that's exactly right. And then you start to get used to leading a team. You start to get used to building your level of who's, you know, I always recommend three levels of who's, a team supporting you, a team of collaborators that are your equals and peers that you're cross pollinating and sharing, and then a team of people who are your mentors and coaches. And when you bring on even that VA, when you're starting, you start to develop your communication skills, some of your internal processes, and these are the fundamentals that you need as you're going to be building

more more layers. So VA, freelance, and then you're going to get to the point when you're in the kind of low to mid six figures, you're going to start to be bringing on those, you know, your first W2 most likely.

Caroline (22:09.512)
So you talked about travel being essential with creativity and innovation in your life or in your business. What are some additional things that entrepreneurs can be doing to help fuel themselves personally or achieve some kind of balance in addition to travel?

Kasey (22:26.02)
Mm -hmm, yep. I love travel, especially if you go someplace new. Again, and it doesn't have to be international. It can be someplace new in your backyard. Sometimes my husband and I will say, let's find a new hiking trail or something. Or we're gonna have a new experience. It's only a 30 minute drive away, but something new and different, not just the same old things that you're doing, whether it's activities with your kids or family or your same favorite restaurant. Start to integrate something new into your routine at least once a

Now, if you can do something bigger and more grand like international travel, that's even more amazing, but that's not realistic for some people and that makes total sense. So even things that you can do in an afternoon that are new, new experiences in your backyard, things that are less than an hour drive away, that will help stimulate your brain. And when you come back, you will be amazed at how refreshed and invigorated you feel on Monday morning after you've done something new and different the day before. So that's number

Definitely reading something, always be reading or listening to an audio book and learning something. And it doesn't have to be directly related to a skill set. So some people will be always focused on, need to learn social media or I need to learn LinkedIn. They're focused on that one skill set. But read things that are related to success, to autobiographies of successful people are fantastic.

These also open our minds up. It helps us realize the struggles that other people have been through. We're not alone as entrepreneurs going through the struggles, the roller coaster ride that we're on. so reading and listening to other people, I think is really cathartic. helps us feel that we are in a community of people that are pushing and driving and success driven.

you know, overachievers to some extent, but yet it's never perfect. And it's a series of micro failures and that's totally normal. And the third thing is meditating in downtime. You know, I have a sauna here, my beach house in Maine. I live in Florida, primarily part of the year. And I spend time in the sauna. I spend time just sitting looking at the ocean. Something where you can just be quiet and still.

Kasey (24:37.032)
And if you're in natural beauty, that's even better. But just quiet your mind, just breathe and quiet your mind. Because again, that stillness is when your mind slows down enough to allow the new ideas and the solutions to come to the forefront. And when we're running, running, running and hustling and hustling and hustling, we're not allowing the time for our brain to think in those creative ways. So those are some of the things that I really suggest.

for people to keep that balance and keep your mind as strong as your body and as strong as your business.

Caroline (25:14.672)
those three. So what is lighting you up with some of the clients you're working with right

Kasey (25:20.548)
What is, what was that question? What is, oh, look, I need to, yeah. Oh my gosh, okay. So many things, oh my gosh. I love what I do, it's so rewarding. You know, I work with 10 clients at a time, so it's a very intimate process. I am gonna be launching some small group programs later this year, but I really get to know my clients and their business inside and out. And I think, you know, the most exciting, the most exciting part of the process is when I'm working with somebody and we get a

Caroline (25:22.674)
So what's lighting you up with some of the clients you're working with right?

Kasey (25:49.636)
complete breakthrough. We sit down, we have our 45 minute to one hour session a couple times a month, and we're typically on a Zoom, and we're having a chat just like this, and we're talking through things like metrics, and then we'll talk a little bit about what's going on in their life. We'll talk a little bit about what's going on in their team, and then we'll ask a question about what if things could be this way? What if things could be a little different way? What if we adjusted this one thing in the business? How would that feel? And the light bulb might go off, and they might say, oh my gosh,

would be amazing. And then, know, it's sort of, well then what happens if we start to implement that? We start to do it. And, you know, in a matter of a few weeks, a few months, we can see the team operating smoother beneath them. We can see revenue starting to uptick. You know, I have a client that's increasing by over seven figures per year because we are continuing to improve the team, the morale.

expand the team, improve the systems, the long -term vision is laser clear where we're going with this business, laser clear. And so, you know, that is extremely rewarding because, you know, if I can be a small part of this person's journey and guide in a certain way and, you know, just ask two or three questions related to my vast experience that is going to help the clarity get even sharper on that next move.

And then we see these massive results uptick more family time. This particular client has more family time, you know, super strong, fast growing business. And that's when that's when it's perfect. That's when, you know, those are the days I absolutely love what I do, which is most of the time, because when it clicks, it's magic.

Caroline (27:32.392)
So how can our listeners find you?

Kasey (27:35.042)
So I am primarily on LinkedIn and Instagram. So you can find me at Casey DeMotto on both of those platforms. I'm also on Facebook and some of the other platforms as well. But if you connect with me on either LinkedIn or Instagram, you will find me there. Soon to be launching a YouTube podcast that's coming very, very soon. So keep an eye out. It will be my name, Casey DeMotto. I'm not that creative. I don't claim to be a creative type,

If you look for me, you will find me by my name at Casey DiMato on most platforms, but I hang out on Instagram and LinkedIn primarily. I would love to connect. I would love to learn about your business. Shoot me a DM. Let me know where you're stuck, what red zone you're in, what break point you're in. I'd be happy to bounce some ideas around in the DM and brainstorm a little bit virtually and help you get to that next level.

Caroline (28:20.018)
Thanks, Casey.

Kasey (28:21.71)
Thank you.