#68: Katelyn Hamilton is the Online Business Manager Setting YOU Up For Success
4 Nov 2025 · 62 min
Katelyn Hamilton, an Online Business Manager, walks through how to hire and systematize your business. She covers the hiring sequence from generalist VA to specialists, tools like Asana and Dubsado, and the mistakes entrepreneurs make when scaling. Heather also shares reflections on turning 46 and stepping into fear.
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Come on this journey with me each week. When you join me, we are going to chase down our goals, overcome adversity and set you up for a better tomorrow.
I'm ready for my close up.
Hi and welcome back. I'm so glad that you're back with me today. Thank you so much for joining me. So when you hear this, it's going to be a few days after, but I'm recording this the night before my 46th birthday and I always love to reflect on and I've been doing this for so long. I, I did this the whole time I was in corporate America, which was super boring because I wasn't growing very much for at least a decade. I was essentially doing the same things over and over again and not taking chances, not, you know, moving into fear, not growing. So my life is very different now, as you know. So anyhow, I, oh gosh, today has been a crazy day to start it off. It's just the hits just keep on coming. I swear, during this pandemic, people are just so angry and on edge and the haters are coming left and right, it seems. I just see trolls everywhere on social media. It's, it's just this negative rush that I don't know if you're running into that too, but I definitely am. Not from everyone, thank goodness. But you know, the more you put yourself out there, the more you open yourself up to people attacking you and feeling that it's their right to attack you, which is so weird because they're hiding, you know, it's not like they're standing in front of you. Not that anyone can stand in front of anyone anymore in this pandemic, but that's a whole nother story. So oddly enough, I, I received a phone call today from my ex husband's wife yelling at me because she had heard I had shared on social media that my son's dog had died, which was a really. It was the worst day of my son's Life. My son's 13 years old and watching that experience and being there with him and going through that was something so hard. It impacted him so much. I mean, he still has anxiety now and definitely is not back to himself entirely, but he's doing so much better now. And thank you for all the well wishes for everybody who reached out to support him and support me during that time. But it was important to me, number one, I learned so much through that experience. It was so scary on the front end of it, going through it and then learning what was working to help him and what wasn't working. And, you know, I feel like it's my job when I go through something new, when I go through a new experience, when I go through something scary to share it with you, that's, you know, what my brand is all about. That's what I built, and that's that level of transparency is important. Those are the things that I get feedback from you guys on that you want to hear more of. So listen, is it comfortable all the time to talk about hard things? No, of course it's not. If it was, everybody would do it, right? It's hard to talk about hard things, but those are the things that I wish I had access to when I was younger. I wish somebody was telling me about these things before I'm experiencing them so I'm prepared. But they weren't right. And that's the whole reason why I launched my personal brand four years ago and then ended up getting fired and have been stepping into all of these really uncomfortable situations. And is it always perfect? Nope, it's not. And does it make everybody happy? Clearly, we're clear on that today. No, it doesn't. You know, one thing that I was reminded of today that I want to share with you, that I think is an important takeaway, is that when you're screaming and swearing and yelling at someone, you're giving all of your power to them. I learned this lesson a while ago in corporate America, and I really have never forgotten it. The day that I got fired and that woman flipped out when I didn't sign the release, she gave me all her power. And please remember the next time you feel yourself angry and hot under the collar and wanting to attack someone, if you're doing that, you are giving them all of your power. And who wants to do that? I took the high road today when she attacked me. I thought to myself, clearly you are feeling guilty. Clearly you are feeling upset. And clearly I can tell why you're acting the way that you are. You're angry because, you know, for whatever reasons that are about yourself. However, for whatever reason, she wasn't able to manage herself and she lashed out. Of course, I had thoughts while on the phone of lashing right back out and calling her out for that and telling her what I thought the driving force was. But I didn't do that because I remembered what I've learned, which is always stay in control of your emotions. Never give someone else your power. So I had some nasty things that came to mind that I was considering saying. But I would like to let you know I'm very proud. I did not say any of them, and instead I listened. And then ultimately, after a while, it gets to the point when someone's attacking you and yelling and swearing, that's inappropriate. There's no place for that in this world with adults. I don't, you know, maybe for a child and you don't know any better, but for adults to behave that way doesn't make any sense. There's no rational thinking behind that. And what's the goal of the conversation? Right? I'm just supposed to sit there and let someone scream at me? No, that's not going to happen. And one of the things I learned from working with a bully, from working with a woman who really grounded herself in bullying others, is that you have to stand up strong back. You don't go whimpering away because people will treat you the way that you allow them to treat you. So in a very calm and serious fashion, I said, there is no point to this conversation. There is no end goal. Obviously, you're calling to yell at me and swear at me, which is inappropriate and not effective. You're not asking for some resolution. There's no end goal. So this conversation's over. There's no point. I'm not sure why you even phoned me. There's nothing else to say. And so it's important to stand up for yourself and not be a punching bag for people because they're angry or hurt or whatever they're going through. And listen, everybody's going through so much. I get it. I'm going through a lot. There's no part of this pandemic that is a cakewalk for me. And I really want you to know that. It's hard. However, I won't be bullied by anybody. I will stand up to bullies. And when the haters come, I'm standing strong. So remember, don't give your power to anybody else. Keep your cool, take the high road, be classy, and stay strong. Anytime you find yourself in an encounter similar to that, which hopefully you won't. Gosh, I hope you won't. So sitting here tonight and thinking about my birthday tomorrow, one of the things that I. I like to do is I like to reflect on the last year. So the year of 45 for me, which is my last day being 45, wow, so much happened, right? It's unbelievable. Went July 1st before I turned 45. A month before I turned 45, I broke things off with my fiance, which was a huge deal because we'd been together for almost eight Years. And I decided to stand up for myself because he had asked me to marry him, but never would pull the trigger, never would, you know, make me the priority, never would move forward with things. And I. I got sick of hearing, yeah, yeah, yeah, yeah, it's gonna happen or it's gonna happen, but the action not being there, and it just kept hitting me over the head that people can love you so much, people can give you the right words, but if the actions are not there to back it up, you've got to pull the rip cord. And it's super hard to do it right. Cause you're like, I've been in this situation for so long. But I pulled the rip cord July 1st of last year, and that was a really hard time. So looking back on where I was In August, turning 45 versus turning 46, I've learned so much and I've accomplished so much. While none of it has been easy. Because who wants to be single at 45 years old with a son and then be single in Pandemic, by the way, too? Which is a complete other nightmare because it gets very lonely and it's hard. Thank goodness I have my son. Otherwise, you know, I can't even imagine. For the people that don't have kids and are single, it's exceptionally isolating. So through all of that, I'm very proud of the things I've accomplished. I'm proud of my strength. I'm proud of stepping out into fear. Cause that's really what it's all about, right? And I'm proud of this show. Because a year ago, this show was only two months old, right? And I completed a full year. And now. And evolving and growing the show. And I believe the show's getting better. If you believe that too, please leave me a rating and review. I would so appreciate it and share it with your friends. But I really believe the show's evolving and getting better. And that's the feedback I'm hearing. And I'm really proud of that. Because a year ago, it was brand new and I had no idea what I was doing. Just like anything, when you're new, you're a rookie and you have to figure it out. So I'm really proud of that. For my 45th year, I'm proud of. During my 45th year, I gave my first ever TEDX talk, which was so freaking scary, I cannot tell you. I know I always say, step into fear. Fear is a green light. That means go. But that was a who. That was a hard one. And I'm super proud of the end result and that my TEDx talk got promoted to TED and translated to five languages. I'm so proud of all of that. So that's really been amazing. What else happened? Oh, I signed with HarperCollins leadership to publish my second book, which is coming out next year, Leapfrogging Villains. I'm so proud of that. That was a really long process, that whole process. Finding my agent, tackling her, not letting her escape, and then getting the book proposal done for her, and then going out during Pandemic and pitching the book proposal to all of the various publishing houses and then settling on HarperCollins leadership, which I'm super proud of. That was almost a year in the making, mind you. When I wrote and self published my first book, it was under six months from A to Z. You know, it moved so much faster. So that's been. That's been a challenging process, one that I'm super, super proud of. But the funny thing is, I look back over those 14 years at my last company in corporate America, and I look at those years. There was never a window of time where I was accomplishing massive things like I am new, new things. Stepping into fear, growing, learning. It wasn't like that. It was sort of, you know, the same Groundhog Day over and over again. Run the company, make the rich people richer, make the founder richer. You know, show up and drive revenue. Get your head beaten when things aren't going well. Get blamed for how things are going when you're not given resources and you're frustrated and you're going crazy trying to find ways to drive revenue to make rich people richer. So it's so interesting because I knew that I was just somewhat stagnant at that time, you know, for that decade, and that I wasn't reflecting and having moments like this where I'm saying, oh, my gosh, this is amazing. But I accomplished it in my 45th year, but I didn't do anything about it. I was frozen by fear and fear of the unknown. That's the big thing I look at when I look back over those years back in corporate America was I was frozen. I wasn't happy. I knew I wasn't growing. I knew there was more for me out there, but I was so fricking scared to go after it. And I don't want that for you. The key's always going to be, as hard as it is to say, stepping into fear will always be the answer. Some days it's a little bit easier than others. But I gotta tell you there's really no day that it's a layup, at least not for me yet. There are people out there, I guess, like Gary Vee, that do it on the regular and they've been doing it their whole life. So they're conditioned to it. I hope at some point I'll become conditioned to it too. But until then, I will continue to step into fear relentlessly, reluctantly, but pushing myself forward because I want to continue to have really big growth years and experiences like I had during my 45th. So cheers to 46, because I'm telling you, this is going to be a huge year. My new book's going to be coming out. My executive coaching business is taking off. My mentoring program's been solidified and is doing so fantastic. The testimonials and impact I'm having on people's lives let me feel so good every day about the job that I do and bringing good to the world. And for that I'm so, so proud and I'm so proud of the show. I'm so proud and grateful for you showing up every day. So that's the birthday gift to me is showing up and supporting my show, supporting me, encouraging me. It means the world to me. I can't even put it into words. I used to have to work at nights, on the weekends doing charity work when I was in corporate America because I never felt like I was living a purpose driven life. And every day now I get the most amazing messages from people on how I'm impacting them and helping them. And it's not charity work, it's my company, it's my business and I'm not making the rich people richer. I'm investing in and delivering for myself and that's a pretty cool experience. So hang tight. We will be right back And I hope you are going to love my next guest because she's dropping a lot of tactical knowledge that I definitely was in need of. Hold tight. A different guest each week. Hi and welcome back. I'm so excited to share something interesting that happened. I get on lot of people submitting to come on the show and I typically don't take most of the pitches that I get. However, I got this really interesting pitch and number one, the way it was pitched was very smart because, well, you'll see I'm going to read it to you in a second so you'll understand why it's smart. But so I like the approach and I just tend to value when I see people doing things well. So that caught my attention and then in Complete transparency. There is one thing in life that I'm so freaking weak at and it is organization. It is my arch nemesis, always has been. And in corporate America, I had assistants that would support me in everything. And it was, you know, it wasn't a blind spot. It was handled. However, when I left corporate America, it's become a real headache for me. So this I. Every one of my episodes I do for you. But I swear, today I'm doing this for me. But I hope you still get value out of it. Okay, so here's the email. On average, business owners who don't have support spend about two hours a day doing the administration and support work on their own. This adds up to be close to 10 hours of lost time per week. And Science says another 40% of productivity is lost when we multitask. So 10 hours of lost time a week turns into 60. My name is Kaitlyn Hamilton and I'm online business manager. P.S. i'd never heard of this. Also known as the get your shit together strategist. I help entrepreneurs organize, strategize, and prioritize their businesses to go from overwhelmed to out in front. So I'm so excited, Caitlin, that you could be here with me today.
Thank you so much for having me.
So tell me, how did you, I mean, how did you end up where you are today? Give us a little insight into your background.
Yeah, so I, like many others, started out in corporate America. I was chasing sort of that big role of working for a big PR firm. Actually, I went to college. I majored in advertising because I actually didn't get in for PR to the journalism school, so made lemons out of lemonade. I actually did a ton of internships in PR because I knew that that's what I wanted to do and nobody was going to tell me otherwise, so. So I ended up scoring an internship right out of college, a paid internship in Atlanta. I went to school at the University of Georgia and then I ended up moving to Nashville, which is where I'm located now because I took a full time job in PR and marketing. And so working in pr, really the goal for me was just to climb that corporate ladder, to get from one position to the next, to grow, advance in my career. And I did that. I worked at my first job for about three years. I transitioned into working really as a publicist for celebrity chefs and entrepreneurs. And then I transitioned to an agency, working more on the account management side of things for a digital agency. And that is where I thought this was going to be, the takeoff of My career, so to speak. And I loved my job. I loved my clients. But what I didn't love was sort of the corporate politics that came into that. And I'm like, over high achiever, go getter. You know, again, nobody is one to tell me that I can't do something. I will go out and prove you wrong. But what I found was I had a boss that was holding me back, keeping me small. And when I was trying to just advance and grow and prove myself, you know, I'm a person. You'll learn through the organization. I have love to do lists and check things off right, and you move from one area to the next. I felt like I was doing that. I was accomplishing, I was going over the top, like, I was kicking butt, and it wasn't being recognized. So I actually went above her to my boss's boss, and we had set a meeting to chat. And that's where, you know, the corporate politics comes into play. I was let go. And I use the word let go, you know, in air quotes because we all know that I was really fired for, you know, trying to essentially go above and beyond. And I took my severance check, and I was like, it was just. It just totally took me by surprise. I was not expecting that. And I had about six months before I took another job to kind of sit in that, be like, where do I go? What do I want? And so I looked back at what I valued and what I valued at that job, what I loved, and it was the freedom and flexibility that I had, the ownership that I had, because, like I said, I was excelling and taking ownership and doing all those things. And I wasn't micromanaged by any means. So it led me to realize, like, I'm actually really freaking good at what I do. I had completely reorganized a multimillion dollar project portfolio and created so many efficiencies for that, for the stakeholders of the large corporate client. And it just continued to blow my mind as to why I wasn't being praised for that and set up for that. So during those six months, I will tell you, entrepreneurship was not something that originally thought about going into. You know, like, I was held back by those common beliefs that society tells you. My parents were telling me, you know, you have to get a job, and, you know, you work 50 years and you retire, whatever it is, and you climb that ladder and you pay your dues. And so the thought of starting my own business really wasn't on the forefront of my mind. But when you have six months off you kind of start to dabble and explore. And, you know, I wasn't one to just sit back and be like, okay, I'm going to take my unemployment. I went and found work. So to me, that's where the power of networking and relationships comes into play. I've always thought that that was such a priority. So I reached back out to my old contacts from previous jobs, high school, college, et cetera, and I started gaining freelance work in marketing and pr. And as I was doing that, I ended up getting a job offer. And I took it because I was like, oh, it's safe. It's a paycheck, right? Like, it's a consistent paycheck. So my plan was to work that job for a year or two, save up enough money, get enough clients, and go out on my own and start my own marketing agency. Well, things don't ever work according to plan. Six weeks in, when I launched my website, my CEO pulled me into her office and told me I either had to take my website down or I was fired. So frantically I was like, okay, I'll take it down. I went home, talked to my now husband, then boyfriend at the time. He's like, what are you crazy? Like, you've worked this job six weeks, you don't even like it. Like, what are you doing? So I actually checked into one of the entrepreneurship Facebook groups I had become a part of, and with their support and encouragement, my then boyfriend's support and encouragement, I was like, you're right. Like, I am doing this already. I am. Like, I have clients. But it was the scariest decision I ever had to make because I was now choosing to walk away from a steady income, steady paycheck. I mean, I couldn't even tell my parents I was doing this. It was like, you know, here's me at 27, yet I'm still so concerned about, like, what my parents are going to think, what my, you know, people are going to think.
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I walked in and I said I can't take my site down and I walked out. And that was the start. That was like the fire that just lit me up inside to go all into my business. So I did. I left. I freelanced for the clients that I found. I actually again continue to network and reach out to Other people. I shared my story, I found more clients and I was starting to build a successful corporate marketing agency and business. As I'm dabbling into the entrepreneurship space, as I'm kind of growing my business and making connections with entrepreneurs, I'm like, man, these people are my people. These are the people that I want to work with. This is the kind of work that I want to do. I saw people creating these life changing businesses through business coaching. I had never been exposed to that before and truly understanding what that was. So through that I am noticing that there is a lack in the entrepreneurship world of organization structure, processes, systems, all stuff that I was doing my own business while I was growing my own business on the agency side. But I was realizing that six and seven figure business owners weren't doing.
And here I was also. I'd just like to interject for one minute, that also happens in corporate America as well.
Yeah, 100%. So as I'm creating these systems and I'm noticing other people aren't doing that, I got turned on to the phrase OBM online business manager. So I actually went to the business coach I was working with at the time and I was like, I want to be an obm. That's what I want to do. I think that this is how I transition from my work in like the freelance marketing world, agency world, over to entrepreneurs because I was trying to figure out how to bridge that gap, how to pull that experience in and I realized that that was it. So when you work in the corporate world doing account management, project management, that work, you're doing all of those organizational things, you're putting schedules in place and systems to make sure that your projects launch on time or you're not missing any parts. There's a total sense of organization there. And it wasn't until I could dive into that entrepreneurship world a little bit that I was seeing that that's what a lot of people were lacking. So once I launched my OBM business, this was two years ago this month, that was, you know, that was it for me. That was what I wanted to do. That's where I found my passion. There was 100% a need for it in the industry. And I've grown my business more than doubled it over the last two years, each year alone because of the need and the people that I've been able to reach and network with and grow. So that's what's led me to kind of where I'm at today.
So tell me, what is this magic sauce that you delivered? And again I don't see what you do. I've never seen anyone, I've never heard of an obm. I didn't know anyone was even in this business. So I'm really trying to understand and wrap my head around exactly how is it that you get people organized.
So what I do when I start with every single entrepreneur, no matter if you've just started in business or again, you're running a multiple seven figure business as we kind of sit back and look at your business as a whole. So I have my framework which is organized, strategize, prioritize. So those three pillars of my business is really what I start with when I begin work with anyone. So we have a brainstorming call, like a strategy call, 90 minute call, where I take a look at the back end of their business. So I look at what systems they're using for invoicing, contracts, how they onboard new clients, what does that process look like? Emails, how many emails are you sending out? Are you doing them all? Is your assistant doing them? Do you have a sort of a structure, routine? What project management tool are you using? There's a ton out there. The one that I work with the most and recommend the most is Asana. And that's really just helping you kind of manage your team, your tasks. I mean a lot of these business owners have so many moving parts that if you don't have a tool to manage that, it's so many things get lost in the cracks. We also look at your content strategy and that's I think what makes me a little bit different as an OBM compared to others you may find in the industry. Having that background in marketing and PR is really what helps me help my clients be successful because I can take a look at their marketing strategy and their content strategy and see where the gaps are and not only help them be more efficient, but really amp up their voice, you know, through their marketing platforms, whether it be social, email marketing again, networking groups, et cetera. And so I look at everything that they're doing as a whole and we break it down and as we do that, I find where those gaps are or where those inefficiencies are, where they're spending more time than is needed. And I also align that to what their long and short term goals are. So we kind of essentially look at, okay, what's your current focus? What do you want the focus to be three months from now and where do you want to be and what are those long term goals that are more in like the 6, 9, 12, month range, and we reverse engineer that. So in order to get you here, these are the things that we need to put in place now, the systems we need to set up, the strategy we need to create. A lot of my clients do launches, whether it be for courses or coaching opportunities and things like that. So I'm looking at, okay, what's that launch timeline look like? And what are all of those moving parts that need to go in it? Do we need to hire out a copywriter? Do we need to hire somebody to do the sales page? Do we need to hire somebody to do the graphics? Do we have people on the team that are already doing that? I also do a ton of team management, so I'm looking at those players on the team and what their roles are. So is somebody taking on too much or doing something that they're not truly good at that we could replace and be more efficient with? Or are there too many people on the team that we need to really silo down to, you know, these key players that are going to make the most impact? So it's kind of breaking down the business and figuring out, like, okay, we sort of essentially do a brain dump. That's one of the first things we do, too, is like, tell me all the things that aren't working. Tell me all the things that you're spending too much time on that you shouldn't. Because to me, there's a time and place for what you're good at, right? So I like to say, you know, I want you to stay in your zone of genius. So if your favorite thing to do in your business and the thing you're good at is creating content and working with your clients, you don't need to be spending the time breaking down the content, scheduling it to your platforms and things like that. So I look at all of that stuff, like, what is the stuff that is currently on your plate that we can take off so you can be doing more business, building activities, things that are bringing you money that only you can do, and me or the team is gonna take care of the rest.
So do you see that there's a certain mistakes that are just standard that you're running into a lot with people?
I think for me, when I look at people's business, lack of consistency is something that I see often. So creative entrepreneurs love, have so many ideas, and they love to get all those ideas out there, right? But to me, there has to be some consistency there. So whether you want to focus on doing video and getting video out there, podcasting, creating some sort of again, consistent content strategy. You don't want to be bouncing around to doing so many different things. So I kind of like silo people in same thing with coursework. Rinse and repeat, right? You have a signature offer, signature program. How can we then. A lot of people don't take the time to then analyze that. So you have a prelaunch phase and you're gearing people up for what you're going to offer. They offer, they do the offer. Maybe it achieves the results they want, maybe it doesn't. Regardless, so many times people are like, okay, I'm going to move on to the next thing versus taking the time to go back and think about what went well, what didn't go well, what could we do better the next time? Looking at the analytics where people dropped off how many sales emails went out, what was the sweet spot, you know, kind of fine tuning those things and then doing it again and then seeing those results grow and change. So I think the consistency of, you know, whether it's again doing a program again or putting consistent content out there and sticking with it, I really have to get people to kind of slow down and just stay in it a little bit and know that the next thing is going to always be there, but really fine tuning what we have now before we get to the next thing. So I think that's the first thing also sometimes during that time period, they use all their energy for that one thing and then when it launches, they're out of energy and they're depleted. So I try to make that process easier. And so that's what so many of my clients, when I come in, I take all of that stuff off of their plate and allow them to just be in their energy of the launch or the program or whatever. And what they notice is that they achieve so much higher results because so much better results because they're allowed to really just be. And that energy is what shines through. I mean, people hire you, right? They don't always care necessarily what the details are of your offer is they want to work with you. And so you're essentially selling them on yourself and the results that you're gonna get for them. And if your energy's drained, that's gonna come across to your audience. So having somebody to take like the back end work and get those emails out and get the social content out and enroll the people and answer the questions in the inbox and allowing my clients to show up, that's the energy that they bring to the table which gets them better results.
So those are all great points. And I mean, I completely agree with you. In a perfect world, however, as you know, especially when people are starting out in business or maybe they're transitioning from corporate America, you know, starting a side hustle. And I've been there too. You know, the challenge is the current amount of time you have and the current resources you have and where to invest them. So it sounds. Yes, you sound right. I agree with everything you said. However, when you're actually knee deep in it, it's so hard, there isn't time to analyze the data. Yes, I know I need to analyze the data so I can optimize and improve and learn and grow from it. However, there isn't enough hours in that week. So you're just trying to get through the things that are absolute priorities and you're not at a revenue standpoint yet where you're ready to reinvest in this or that and people are telling you you're getting options for, oh, a high level graphic designer or a great copywriter show. Where is that right place to make your investment?
So I think there's a couple things to point out there. One, I think you either have a surplus of time or you have a surplus of money. So when you're just starting out, it can feel like you don't have either. But that's not necessarily true. I mean, you definitely have more time when you're starting out than you do money. So you're doing a lot more of those things, right? You're investing a lot more time into that launch, that growth, whatever it may be. And the good news is that whatever you're offering, whatever your offer is to support your clients, you only have to be one or two steps ahead of the person that you're trying to serve. So as long as you're kind of, you're at where you're at and you're not trying to, you know, my first launch, I wasn't trying to make a million dollars, right? Like, I'm trying to kind of set realistic goals. I have a good, better and best goal and I know that. And then I can build on that for the next one. And guess what? When I make a little bit more money, I can outsource some of those things, right? So I kind of just start, I would say start with where you're at. Invest the extra time that you have. I mean, it may be like, so my end goal, you know, is to work 20 hours a week and have extra time to spend with my kids or travel or whatever it May be, but in the beginning, you're not necessarily gonna be there, Right. Like, you're gonna have to invest more of that time because eventually you're gonna be able to outsource more because you have more money, which will give you back more of your time. So I think part of it's like starting with where you're at and recognizing that you don't have to, you know, you're not going to make a million dollars right off the bat.
Right.
But to me, that also goes along with, like, comparing yourself to other people. And, you know, when you get into this space, you see, you know, Sally and Sarah doing this, this, and this. But you have to just remember where you're at and what you're doing. So I think that's the first thing I would say. The second thing is start small. I mean, I have personally a team of five, but I worked the first year in my business all alone. I didn't hire. And then I hired a virtual assistant, a va, and she was more of a generalist. So she could do, you know, my. She could break down my social content and schedule it. She could schedule my blog post. She could take a little bit of client work in terms of client engagement or setting up client emails or funnels. So she could kind of do all that stuff. As I again continued to grow, that gave me more time back in my business, I was able to hire a little bit more specialized people. So somebody that really focused on social media, somebody else that helped with publicity, somebody else that could really focus on project management. So I think that you have to. You don't have to make all those hires or decisions first. You just, I would say, start with a generalist before you move to a specialist, so to speak. And also, as you're doing that, think about the things you don't like doing in your own business. I mean, we all start businesses to create the life and freedom that we desire, but there's always going to be things that you don't like doing. Like, I hate accounting. I'm not going to be one to do accounting. So I outsourced that, Right. So when I grew to a point that I didn't want to do, that I paid somebody to do it. So I think those are two really good places to start, is really just start by thinking about hiring somebody that can help you that's maybe a little bit newer in the industry, that maybe doesn't cost as much, and then you can grow from there and start by outsourcing the stuff that you don't love doing because again, that will give you back energy that you want and you can dive into and add to your business.
At what point did you know? So you brought on the virtual assistant first and were you nervous even then making that investment or you felt comfortable doing that? And how did the remaining employees play out? From a timeline standpoint, it's always nerve.
Wracking to, I feel like invest in your business. But that's where change happens. That's where you level up. I would say I am a planner. I'm super type A. So being spontaneous is really hard for me. I like to make calculated investments and decisions. But I've learned that in entrepreneurship you have to take a risk. There's always going to be a risk in doing that. And so for me, I made the best decision. It was really when I started to get overwhelmed and I realized like, I can't do this all alone anymore. I'm also being type A. Letting go of control is something that's hard for me. But I also was watching just listening to some free trainings from my now business coach and you know, the one thing that she consistently said was like, you're going to have to invest before you're ready because you're never going to be ready. You're never going to be 100% ready. So that was kind of what did it for me. And I kind of again calculated it. And as if she can help me get 10 hours back of work a month, I can get a whole new client. And from a financial standpoint, I'm only paying her this amount. But if I get a new client, that cancels out and that actually makes me X number of dollars more a month. So I was looking at it from that perspective too. Not only the time I'm getting back, but then what does that allow me to do with that time? That can allow me to bring on an entirely new client, which will thus increase my revenue. So I think I worked with her with my first virtual assistant for nine months before I brought on somebody else. I also ended up hiring a larger, more expensive business coach and that has catapulted my growth immensely. And that was such a scary decision for me to make too. But I knew if I wanted to get to the next level, I needed the support and guidance from somebody that was going to had been there that could help get me to that next level. Because I truly believe you need support in your business to be successful. So that goes along with outsourcing your work and prioritizing your time and energy and really just helping you to grow. So I hired the business coach beginning of this year and I brought on she actually was one that suggested to bringing on more specialized people. And so I actually hired three or four new people in month and a half timespan and it's worked. I mean it's been great. That was three months, four months ago that I've brought on all of those people. But it allowed me to bring on an additional client. It allowed me to have more time back to work on future courses and work that I'm trying to create for my own business. It's allowed me to take on work to coach others on how to start a business. So it's opened up that timeline. But I feel like I am such a good example of and my business is a good example of the slow and steady and consistent growth over time. And I think a lot of people when they're starting out in business, it feels like an eternity before you're going to get to a point that you dreamed of, right. That you like start the business for in the first place because there's so many things to do. But I think what I just do is focus on consistently taking that next step.
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It'S allowed me to have this thriving, successful business. And of course I still have goals and places that I want to be and revenue goals I want to hit. But looking back, I didn't just become an overnight Success. And I've really built my business on a strong foundation, and that's what I preach to a lot of my clients and the people I work with is really the importance of building that foundation. Because that's a problem when I come into so many people's businesses is they don't have the foundation. They've maybe launched or been super successful. And I don't want to say overnight, but quickly. And they've scaled quickly, but they don't have the systems and processes in place to continue to support that and to do that for the long haul. And that's what's led them to kind of this state of being frazzled and almost burn out in a way. And so I come in and I'm able to give them that foundation and support that they needed and will allow them to continue to scale and grow.
It's so interesting. When you were explaining that story, it reminded me of a good friend of mine who had been wanting to be an entrepreneur for a long time and said, you know, when I do it, Heather, I'm not going to have to work as hard as you. I don't have as big of goals as you. You know, I'm doing it for like a luxury and time. And she had this dream idea. And then she said to me, last month, I left one boss to now I have seven bosses because she has seven clients. And she says, and I'm going crazy, and I'm running around in circles. And it's that same frustration that she doesn't have anything automated. She's overwhelmed by the amount of work. And it's just. It's so true, no matter who you are. And like you said, some people, you know, I remember my book took off when I first launched my book, and that was going crazy, people. But because I had nothing else built out, you know, you're chasing that one thing in the moment, and then you end up stepping back months later saying, oh, my gosh, I've got so much other that I have to work on, not just this one product or service or, you know, and I also believe, too, some of it you don't figure out until you're stepping into it. The wrong way to figure out. Wait a minute. There is a better way to do this.
Absolutely. I think so much of it's trial and error, too.
Right?
Like, you don't, you know, you don't know what you don't know, and you try something and then you fail, and that's okay. You pick back up. What I like to do, though, is I think I'm in the business of one, supporting the people and the entrepreneurs that are extremely successful already and helping them to build that foundation to grow. But also I want to educate people that are just starting out in business. And while it's not the sexiest thing in the world to set up systems and to spend your money and your time on getting those things set up, it will serve you so well in the long run. And I think people don't think about that because it's not cool, it's not fun, it's not the stuff you want to necessarily be doing. But when you build that foundation just like a house, you are truly setting yourself up to have strong bones for when you do get to the place in your business you've always wanted to be. Otherwise, you're backtracking and it feels overwhelming. So I think that that's part of my mission now too, is to help. I want to help so many people start and grow online businesses because it's the best thing that's ever happened to me. It's given me the freedom and flexibility that I have desired. It's helped my mental health, my anxiety. Granted, entrepreneurship is not for the faint of heart. You definitely have to be ready for that roller coaster. But I used to be so afraid to ask my boss if I could take off an afternoon to go to the doctor or to take off vacation. And now that I can run my business wherever and on my own terms and I have again a team of support, it's magical, right? Like it's given me that. So I want to help other people do that, but I also want them to get started in a way that is going to give them an even greater chance at success and truly being organized in how they do it and having those systems set up that are going to just cultivate even better habits as they grow.
So one of the things that I saw on your site that I was completely not familiar with is Dubsado. What is that?
So Dubsado is essentially a CRM tool. The way that I like to use it in my business, my clients businesses is really as an onboarding tool for your clients. So it manages your contracts and your invoices. You can automate just about everything in your business in the back end, beginning parts of your business, all the way from a lead form. So if somebody were to come on your site, they're interested in working with you, they can fill out this form. What it will do is it will trigger a notification in Dubsado to send them out an email you can also set up a call. They have their own online scheduling platform. You can send them your scheduler to book a call. You can send a contract, invoice, welcome, email, onboarding email, sort of getting started email. You can set up recurring payments, all of those things. And it's really a great way to nurture your clients and give them an amazing experience without having to do any of that yourself. Because what you can do is go on there and set up workflows on the back end so that again, as soon as that lead form comes in, or you don't even have to start with the lead form, you can, you know, just when you're starting to work with someone, you can set it up to start with the contract and invoice, etc. It does it all for you essentially by the touch of a button. So I love that it simplifies that for my clients and my business. And also it does keep track of all of your projects. If you do a lot of project work or coursework, you can just keep everybody in there based on the project that they're sort of signing up with, so to speak. So it's a really great tool that will give you so much time back in your business and to not have to worry about messing anything up, missing anything, or manually doing any work yourself.
Wow, I needed to know about that three years ago. So where were you, Caitlin? So one of the offers that you have is your course that teaches people how to automate workflow. And can you tell us a little bit about that? Because I know that you said you were going to offer everyone a discount on that.
So my course is actually called Automate Everything because it literally automates everything in your business. It's a hour and a half from start to finish. I really teach you how to set up Dubsado easily. Well, it is not the most intuitive platform, so to speak, but what it will do for your business is a total game changer. I have worked with clients all across all industries, so it's not just specific to one industry. I mean, I have a client who works in the wedding industry. She does custom wedding invitations. And I set up her entire Dubsado platform, start to finish, to automate, so that she, you know, you can imagine how many inquiries she gets on a common base, you know, on a frequent basis. And so she doesn't have to like, essentially touch it unless somebody wants to work with her. And then it's. What it's done is it's simplified the whole steps moving forward so she doesn't have to do so much back and forth. So that's one example. I've worked with a woman who runs a modeling and talent agency, worked with coaches, you know, sort of everybody across the board. So if you're looking for something that will automate your onboarding process, this is for everyone. And so this course will teach you how to set it up in a super simple, easy to understand way. So it's only an hour and a half long from start to finish. All the videos are about 10 minutes, I would say each. And I'm offering a 50% off. So I think it's like $49, $47, something crazy inexpensive like that with the code. Confidence. So if you just put confidence, you will get 50% off the program and it will truly transform your business.
Oh, my gosh. So how does everyone find you? Caitlin, they're gonna want to talk to you.
Yeah. So you can find me online. You can go to my website. It's www.kaitlyn k a t E L Y N E Hamilton H A M I L T O n dot com. Same thing on Instagram. I hang out on Instagram a lot. It's probably my favorite platform. My handle is Aitlenehamilton. Those are probably the best places to find me. My course information is all on my website, so you can just pop on there and put in that discount code.
So don't forget the code is for 50% off Caitlin's Automate everything course. It's confidence. And Kaitlyn, thank you so much for giving that opportunity to all of our listeners today. And thank you so much for being here and teaching us so much.
Of course. Thanks for having me.
All right, hang tight. We'll be right back. I asked you to try to find your passion. Hi and welcome back. I've got a couple of questions that I wanted to answer for you. They're very similar and I'm interested to hear from you if you believe they're similar. I find them very similar and I get a lot of these kinds of questions. So different themes, topics, but sort of to me it's the same question. Okay, so. So both of these came from LinkedIn. First off, Heather, I'm a big fan. I followed you throughout your success and appreciate you sharing your trials and tribulations with everyone. It's humbling yet amazing to see you break out of the mold. You knew you had it deep within you and you executed. So great to see, so super nice. Thank you. Similarly, I have helped to build out others dreams and made millions of dollars for them. Hello, me too. And now I find myself at the pivot point where you were with when you were fired. What is your best advice or connections to people groups like yourself? To involve myself, to make the jump, to actually make it happen or potentially as you did, start creating a story of your failure to success in social media throughout LinkedIn, Instagram and the like. To start a base through personal specific business success. Content just goes on to say more really nice things. I would love to hear or be a part of others who are doing the same. Okay, so first of all, obviously I responded back. You should join my mentoring program. I mean that's what we do is we push each other to the next level every single week in our group coaching. Everyone there is like minded. You want to surround yourself with like minded people, right? Because they're going to be the ones that are cheering you on and pushing you instead of holding you back. Remember, fire your villains and surround yourself with people who are there to stretch you. They're ahead of you and they're holding you accountable. It's really key. So that was the first thing that I said to this person was you need my, my mentoring. A group coaching accountability program. Sign up for September. So that's one, but two is is this. Listen, there is no magical roadmap. Start posting. You're thinking of creating a brand on LinkedIn. Start doing it. Do you think that I had some master strategy in place? No. I posted and then I learned and then I changed it and then I posted and then I learned and then I changed it and then I evolve it and then, then I. And the same thing with my website and then same thing with the podcast. Right? You just have to start. People get so frozen with what is the big plan or the big answer. If you can join a mentoring or a group coaching program, do it. It's gonna hold you accountable, it's gonna push you to the next level and it's really, it's gonna encourage you that you're around like minded people. That is for sure. Fire your villains, but start taking action. You can't just sit on the sidelines and acknowledge that other people are doing things. I'm stepping into fear every freaking day. It's hard, it's scary, but you just do it or you don't. And you know, for a long time I didn't. So that's your choice. It's on you. You've got to show up. If you can do it. Get in the program. Encourage yourself. Hold yourself accountable. If that's not for you, just Start posting, start building, start doing something. Take action today, no matter how small the step, hold yourself accountable to take that bigger step tomorrow and keep moving fast and breaking things. It's what I do. Okay, then this is the other question I got and I see these as very similar. Hey, Heather, since following you on LinkedIn, you've inspired me in certain areas of my life. You mentioned you had gone through divorce. I have two. Mine was not easy. No one's divorce is easy. P.S. now I am co parenting with someone who is not nice to my kids, et cetera. I so desperately want to help women like myself who to are able stuck in a relationship or exiting one and co parenting like this. I feel like God has led me through this path to help others and I'm not sure where to start. Do you have any thoughts or suggestions? I'm curious as you're an advocate for women like me. Okay, this is really the same question, right? So number one, if you can get yourself in a group mentoring program where people are going to hold you accountable to get yourself to the next level and take action and move and level up, and you've gotta show up and push yourself, do that. And I believe, I hope I sent this person a link to my mentoring program as well. So that's number one. If you can do that, fire your villains, get negative people out of your space, and get people who are ahead of you around you to encourage you and challenge you to grow. It's really, really important. For me, that was hiring my editor back when I was first fired and writing my book. He'd written 19 books. So suddenly, you know, he was saying, oh, how you feel is normal. Don't worry, just keep going. You know, we'll keep making mistakes, we'll figure it out. And so that was really encouraging. He was my mentor when I first started out, but I invested in him, right? I hired, I hired an editor and that really accelerated my progress. And if you hire someone who's beyond you and invest in yourself, it holds you accountable to take that action and get the ball rolling. And momentum is such a big part in things like this. You have to take those first steps to get yourself moving. And then once you start building some momentum, you'll eventually take off. So same thing I see here with the other question. It's basically like, I have this idea, but what do I. I don't know what to do. You just do, right? So if you're saying you have an idea service that you're going to provide a problem, you're going to solve. You're going to help people who are getting divorced. Start posting about that. Why wouldn't you just put that out there? It's not going to be perfect at first. It's going to change, it's going to evolve. But nothing will happen until you take action and post something. Until you speak to your community, you're following your potential clients. You have to reveal what it is you're doing. And if you've never done it before, do it for free. First for someone, Work with someone for free so you can establish social proof and create testimonials, and then that will promote your business. But you just need to take action. My first recommendation is always going to be join a mentoring program, Hire a mentor or coach. Someone who's ahead of you, that can hold you accountable and push you to the next level and force you to take action. When you're scared to step into fear, because that's usually the hardest part. And that's really what I see with both of these people, one being a gentleman, one being a woman, is that they're. They're both kind of frozen. They have an idea, but they don't know where to go. I didn't know where to go either. I just took action. I moved fast. I kept breaking things, things, making mistakes. I built momentum. I hired someone light years ahead of me. I invested in myself, I held myself accountable, and I just keep going. And that's exactly what you need to do, too. Thank you so much for being here with me. If you could please rate and review the show, it would mean the world. And until next week, I'll be here creating confidence, hopefully right alongside you. I decided to change that dynamic. I couldn't be more excited for what you're going to hear. Start learning and growing. Inevitably, something will happen. No one succeeds alone.
You don't stop and look around once in a while. You could miss it.
Come on this journey with me.
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