What I’ve Learned in My Five Years of Business


Succeeding Small is officially five years old. 

Oh my gosh, I cannot believe I have crossed that threshold into my fifth year of business, and what a journey it has been. 

Just looking back at every stage of my journey, starting as this solopreneur with this beautiful passion and skill that I love to practice, and really just watching it turn into this six-figure company and becoming a CEO and running this team of incredible people and being able to support and serve my community. It has been such a humbling journey going through so many challenges, having so many amazing wins and life lessons learned, and just continuing to build my business to reflect the kind of life that I want, that I want for my team, that I want for my clients. Really just building this company into this greater vision that I’ve had for myself and seeing that evolve over these past five years has been just really exciting to be in the driver’s seat and be able to reflect back in hindsight and just see what the heck happened in those past five years and how did we get here today. 

So I have been thinking about what to do for this podcast episode for eternity. I have been wondering how I am up all of this time and all of these lessons learned to really be able to serve you guys and give this example of just what this real journey looks like from a very raw and authentic standpoint. 

You know, I think growing small businesses is so isolating. We are alone. We feel alone as CEOs, entrepreneurs, and small business owners. We’re trying to carve and pave this life for ourselves and build a business from the ground up. Whether our experience is rooted in business or whether it is rooted in our trade or rooted in our passion, it is hard growing a company and being able to lean on one another and have this community of small business owners to lean on, to talk to, to listen to, to hear their stories and how they grew and how it can impact you and help you move forward, I think is just really powerful. 

This is a powerful aspect of this platform, of this podcast that, you know, it’s why I created this in the first place, was to serve small businesses in their journey. And I think one of the best ways to do that is to reflect on my own and share my mistakes and my successes and how I got to this point. So I hope that this is helpful for you. It sure is therapeutic for me,  to be able to go and reflect on this journey. But what I really wanna emphasize in this episode is just that everybody’s journey is different, and that’s what is beautiful about it. That’s what’s beautiful about entrepreneurship is that we all get to these same places in such different ways. And so I hope you enjoy this reflection on my five years in business. What I’m gonna do is I’m going to just sum up the lessons that I learned each year. 

So starting with 2017–year one–and going all the way up to now (this fifth year of my business), and just talking about what the main takeaway and really focus and prioritization of my business was, and walk through just a few steps and lessons learned that I’ve gotten through this place. So here we go. 

Year One: Passion

Year one, passion. This was really the best word to sum up this first year of business, just pure joy and love for what I did and finding this identity rooted in this business of mine that I wanted to create and build. I cannot express to you just how amazing this first year of business truly was and how good it felt to be doing something. I loved to feel like I found my place in the world and to build this business, to put together all these different puzzle pieces and create this structure that I could not only call my own but I could use to serve other people and serve my community and serve my family of small business owners. 

They really started this passion of mine that I had growing up in this small business community, gave me this love for hard work for family, for creating a service that benefited the people around us to be able to create something bigger than ourselves and use our small business to create the life that we wanted. I drew a lot of inspiration from my family history of entrepreneurship, and I knew that I always wanted to be an entrepreneur starting at 16 years old, I started an online clothing boutique. That was my very first business, but I didn’t have the same type of passion that I had for that, which I found with Succeeding Small. I liked owning a business and experimenting and doing marketing and building websites and you know, putting together all these different pieces, but I didn’t have a passion for setting up trade shows every weekend and the labor that it took to run and operate that. 

And the subject itself was something that I wasn’t, you know, I wasn’t as passionate about as I was passionate about running a business. And so when I discovered what I wanted to do when I found search engine optimization, when I put together the pieces of digital marketing, being able to write for businesses, using the college degree that I was getting and apply it towards growing businesses like my families, that was the real spark that just put everything into perspective for me and gave me this baseline passion that skyrocketed me into my future. Literally, it was the best feeling. I wish I could always return to that, and I always try to remember that feeling of that initial passion when I was starting my business in year one because that is what wakes me up in the morning. That’s what keeps me going. That’s what gets me through all the challenging times, is just remembering how much I love what I’m doing. 

And I want that for everyone because running a small business is hard, and if you have that passion backing you up, then it just makes those days a little bit easier and it makes you look forward to walking in those office doors or getting up at your computer each day because you’re reminded, this is who I am, this is what I’m meant to be doing, and revisiting the, the feeling of that first year really does that for me. So, other lessons that I learned within that first year, I was really just developing my business. I was coming up with the services that I was gonna offer, and what I was gonna do in all of those. It was so much education time, of doing competitor research, of experimenting, of. This is gonna sound really bad and should be one of those lessons learned, but undercharging my services in order to really experiment led to overworking and undercharging, which I do not recommend, but you know, it’s, it’s what I did with what I knew and really helped me get to the point that I am today. 

So I remember the days, and this is gonna, this makes me just laugh and we’ll probably make you all laugh too, but, I remember charging, I think $150 a month for search engine optimization, which is, if you know anything about search engine optimization and if you’ve ever started out in your business charging a just astronomically low amount, you will understand and relate. But you know, it’s what I knew and I started my business because of my passion. I didn’t start it for the profit, even though that really came back to bite me. And I’m gonna explain, I’m gonna explain why in year five because that’s what I’m doing now, but I started it with all of this passion in zeal and just love for what I was doing to really build and perfect my systems, my internal systems of this is what I do, this is what I offer, here’s how I do it, here’s how I can get results, here’s how I can measure results. And really just piecing that together, which I think is a part and a stage in every small business owner’s world, is just, you need to feel confident in what you are doing before your prices can match that level of confidence. And, you know, it probably should be flipped, so don’t take this as solid advice for what you should do because I’m sure there are many, much better ways to do this. But just in terms of my own journey, that’s what it looked like. I was just finding my own passion and my own stamp on what I wanted to offer and then building and growing from there. It was also this first year that I taught myself more things based on the business that I was creating. So I started as a digital marketing agency serving small businesses. It’s what I am today. But as I was doing things like networking and talking to prospective clients, I realized that small business owners had other needs that I could fill, one of which was web design. 

So part of that first year was me learning how to build websites, learning how to build them on WordPress, learning the technical aspects of what is a domain, what is a hosting provider, and how do these three things all come together? I remember spending countless hours on tech support with companies like GoDaddy and HostGator and Google Domains trying to figure out why I just broke my website, how do I make this work and what does this look like? Doing so much research and building, again, building my own philosophies and really developing the services and seeing what I personally was capable of. That was a lot of the first year of my business was really just finding my place amidst all this passion, having, having the passion drive me forward, but really just figuring out who is succeeding small and what am I, what am I capable of, what else can I do and how do I take this joy and love and turn it into an actual profitable business? 

How do I take all of this and not just, you know, make it a fun hobby, but build a solid foundation to grow on? So that was year one was just a whole lot of love and a whole lot of learning. 

Succeeding Small team gathered around table

Year Two: People

Year two was all about people. So this is where I first brought on other people under the succeeding small umbrella first really from just a love of teaching and I didn’t know I had that desire. I didn’t know I had that love of mentorship and teaching others until I did it. So this was very happenstance, my first person to come along on my team, but it taught me so much and gave me a picture of what my future could look like, having a team and having other people doing work beside me. So I remember getting my degree in English in college and thinking to myself, there have to be other avenues than being a high school English teacher. 

I do not want that for my life. That is not for me, and I have to do something else. That’s what ultimately led me to minor in marketing and think about what it meant to write for businesses and later drew me to search engine optimization and digital marketing as a whole. But it’s so funny and ironic thinking about how adverse I was to teach, which it wasn’t thinking back, it wasn’t that I wasn’t opposed to being a teacher, it was just opposed to that being a lifestyle choice and a career path. Because when I got into having people on my team and being this mentor and sharing the love of my craft with other people, it became such a point of passion for me in a whole different sense. I loved being able to share this journey and see the light bulb go off in someone’s mind and share just the amazing results that digital marketing could have for small businesses. 

Being able to share that experience with other people, of connecting the dots between hard work and results. It was just, it was so rewarding being able to do that process. And that’s what really led me into creating my first internship program. So I started putting together a formal program and arrangement where I could have interns. I partnered with UCCS, which is a local college in Colorado Springs, where I’m from, and was able to build an internship program and serve students in a formal sense. I also had more people that I mentored and just casually took under my wing to be able to get some work done and then also teach them what I was doing. So this was really just a year focusing on what does this look like if I have someone else on this team, how do I communicate what I do for people and tell that to someone else to be able to execute? 

Year Three: Systems

So this brings me to year three, which was really about systems. Having people under me that were carrying out my services meant that I needed to standardize and systematize what I was doing. I needed to have documentation and processes in place that other people could replicate. This is also just business practice anyway, and I wish I had done this literally in year one, but year one, again, was all about that learning phase. So it was, it was more about, I, I knew what I was doing myself and had everything mapped out perfectly in my own mind, but that doesn’t help my employee or my intern or anybody else on the outside stepping into my business and being able to carry out what is in my brain. Also, having all that in my brain meant that the success of my business, the success of my services, everything was reliant on me. 

So if I, you know, got a cold, I couldn’t count on this person knowing what to do because it was all in my brain and reliant on me. So this became a year of just documentation of systematizing, putting the things that I did into steps that other people could follow, and several things really led me to do that. The first of which was my very first business coach, and I’ve got a podcast episode on several things I’ve already mentioned here in this podcast. The first of which is I have a podcast episode about how I built my internship program, in case you’re curious about that. And the second one is the three lessons I’ve learned from my business coaches. So that one, I dive into my history with business coaches and what I took away from each of them. And that very first one was all systems based. 

So that’s where I really got into this mindset of what is an SOP (standard operating procedure) and how can I be more efficient and productive with my time using systems. This was the point in my business where I got really busy. I got really busy because I was the only one doing things, and everything was in my brain and it was damaging my business that was hard to manage. Having a rapidly growing business is amazing, but it also comes with a lot of challenges and needs some sort of foundation to be able to rest on and capture all that growth and make sure that it doesn’t all fall apart. So year three was tough. I was maxed out on my time, I was way burnt out. I was working, gosh, 80-hour weeks, this was not a healthy time for me and it was really, really important and imperative to do this systems-based work to help me out with that. 

I also had a really big revelation during this time period that I was out of time, and I had a million things to do, but I had a little bit of money, and I used that to go and hire my first executive assistant. And let me tell you, that was the turning point of my business that saved me from burnout that gave me so many different solutions to solve my time, and capacity problem, to complement my visionary brain with a systems-based person, to be able to have that laundry list of, to-do items actually accomplished and really start building this infrastructure with someone to help me out. So I’ve got another amazing episode with my operations manager, Madison, where we talk about what it’s like to hire an admin assistant and when to do it in your business. And I talked about my journey with her there. 

So go listen to that one, if you’re curious about wanting to maximize your time and outsource the things that you hate because it will make you so much more productive. It brought back the love I have for my job, and it solved so many problems that were very close to breaking because I didn’t have enough time anymore. I couldn’t be all the people anymore, even though that’s very much my personality and my mindset, and my work ethic. But with a growing company, it was not possible. It was not smart, and it was not profitable. So year three was a ton of hard work, but it laid the foundation for me to be successful in the future. So my takeaway for year three is that I should have been doing that in year one. 

So if you are listening to this now, look into SOPs, start documenting your processes, and build systems yesterday, right now. Do it. It is so important, and it will save you so much time in the future. 

Year Four: Scaling

So that brings me to year four, and as I was dealing with this growth and experiencing the just amazing opportunity that my clients trusted me to grow their business, I was networking, I was getting clients, I was growing this relationship base. It was so humbling, and I feel so honored to have been granted all of this growth that I experienced. But it ended up and resulted in a really hard question for me, and that was, did I want to scale? Did I want to get bigger? And how big did I want to grow? Because I was coming to a point in my business where I was absolutely at capacity, and it was either that I hire more people or that I start turning people down and saying no and putting people on a waiting list. 

And I had to ask myself what I wanted, and I truly didn’t know because scaling scared me. It scared me thinking about the fact that you know, I would have to be a boss to people, and how can I be in control of everything if I can’t be in control of everything, and what would this look like for my life? And it was a real emotional decision and journey for me, looking back in the history of my business this is the hardest decision I had to make. And I don’t quite know why. I don’t know why it was so scary. But I literally remember thinking about this question and just breaking into tears because I didn’t know. Like that was a really scary unknown part of my future. But I had to think about why I started my business going back to that passion that year. 

One passion and mission and remember that it was to serve small businesses. That’s what I wanted to do, which was to serve my small business community. And if I told people no, then I felt like I was doing a disservice to myself. I felt like I was doing a disservice to my community. I felt like this is not who I am. I don’t want to put a cap on what I’m capable of because I know I can do so much more. I know that this business is capable of amazing things and I know that I can have a great impact on the small business community that I am so blessed to be a part of. So I told myself, let’s do it. Let’s scale and figure out what that means. How do I grow at a faster pace and build the infrastructure to be able to let me do that? 

How do I multiply my time efforts? How do I get a staff? What does it mean to be a boss and a leader of people? What does it mean to be a CEO? How do I, how do I scale this business and take it to the next level? So part of that journey was once I made it past that emotional block and past that point of just embracing the growth that I wanted, it was, it was really cool. I was able to set some really big-picture goals for myself and think about this much larger future and vision that I had. I was able to think about what it would take to get there, and that’s what led me to some really fundamental decisions that I made for my business that I’m gonna share with you guys. So in year four, this is where I rebranded my company, which was so much fun. 

It was so much fun because when I started my company, I created this little tiny logo on PowerPoint and it did not represent me. It didn’t even represent me when I created it, but it was the best I could do at the moment, and I just wanted to start my business. I just needed to get out and do it. So I created this hodgepodge of a brand when I very first started, and it just was not serving me. And it felt like it was holding me back from the scaling journey that I wanted to make. Because every time I thought about marketing my own company, for example, I didn’t like the identity that was tied to it. I, it didn’t feel like me or what I was capable of. It felt, it felt just old and that past version of myself. So rebranding was the smartest decision I could have made that year. 

And I, so I hired a team of professional graphic designers to be able to do this. I actually interviewed those people on a podcast episode called Small Business Branding 1 0 1. So go listen to that one because they are amazing people and they are responsible for my brand and I’m so grateful for them. This really gave me the freedom to go and market my business for myself, which is kind of ironic being that I am a marketing company, but you know, the thing is that the cobbler doesn’t have any shoes, that is what it was equivalent to. I was so busy marketing for my clients that I had no time to market for myself until you’re four. That’s when I started to make that change and transition to marketing my own business. And that did really, really cool things for my lead generation. I started getting leads from my marketing efforts that weren’t reliant on my time in the past. 

I had gotten my clients from networking, from physical networking, attending in-person events, and making relationships all myself. I was the only thing driving revenue in my business, which served me to that point. It got me this far in my business, but again, I’m trying to be careful with my time and figuring out how I can grow and scale my company, and in-person networking was not scalable for me. It was purely in exchange for time in order for a small bit of results, and I wanted to maximize that. So I invested in my own search engine optimization. We built a new website, we started doing content marketing, started doing social media marketing on all these different platforms and it really made a giant impression on my brand awareness and it brought me in leads from the internet. And now to this day, that’s how I’m growing my client base through my digital marketing efforts. 

I have clients that I’ve never met, and I’ve never heard their names. They’re in different cities, different states, different countries because they’re all finding me online. That’s the power of digital marketing and why I love what I do. But you know, that is a side note. The third and final thing that I did in year four was get out of the day-to-day operations of what I was doing. I really wanted to become the CEO of my business because I was pregnant and I was about to have a baby, and I did not want my company to stop running when I couldn’t be present. I wanted to have my child and be able to go on maternity leave and have my company still flourishing and functioning and not go down in flames. So this part of my scaling journey was really about documenting, again, systematizing everything that I do and figuring out what to do with that. How do I take what I do and how do I hire for it? How do I create this role for it? How do I delegate it? How do I get rid of it if it’s not serving me, what do I do on a daily basis, and how can I systematize it? 

Year Five: Stability

So that brings me to year five and my word for year five is stability. And let me tell you, this is not what I thought it would be at all. I had really big goals for this fifth year of business about diversifying my revenue stream and adding things like products into my service-based business. I wanted to create a whole bunch of things that I still am going to do. But that’s what I thought this year was gonna be about. And it wasn’t until I invested in a business coach that I realized that I couldn’t do that type of creative diversification when I still had a foundation that I needed to build. 

I realized that I had a lot of little teeny tiny holes in my profitability and my business model, and the systems that I had built. You know, starting in year three and then leading up to this point, I have been dedicating this year to really patching those holes and building a more solid foundation for me to take that next stage of growth. So it’s been, it’s been a really hard year. It’s really centered around where I want to be and where am I right now, and how am I going to bridge that gap to get to that next level of business. And a lot of that is not fun work. It is absolutely necessary work, though. What I’m doing and the way that I tell myself it’s all worth it is that this is what this work that I’m doing right now is what is going to propel me into that next stage of business. 

The next goal that I really want to achieve for myself, is the needed work that it’s going to take to make sure that my business is profitable, it is sustainable, it is scalable, it is optimized, it is efficient. All of those very, very important things to creating a business that lasts. And I feel like this is what year five is about, is a business that will last. I think a lot of small business owners when they get to this point of business, it comes down to these, these very serious discussions of what am I doing right now and is that going to work? Is that serving me, and how can I reach my goals? So just to give you an example of some things we’ve been working on this year, we have been evaluating all of our services and making sure that we are staying in scope for what we are getting compensated for. 

So me being this passion, a heart-led person, and overworking and undercharging in year one is still very much happening today. And I didn’t realize it until we actually got into very systematic numbers based on putting everything on a spreadsheet and realizing, oh yeah, that’s the problem. So we’ve been analyzing things like that. We’ve been talking about how we can systematize our communication, and our client relationships, how can we improve customer experience? How can we optimize and understand our sales process? All of these little tiny pieces of things that we’ve been doing up until this point, but taking it to that next level of systematization and really evaluating everything we do in our business and making sure that it is those, those things that I mentioned, profitable, sustainable, efficient, all of those things. So it’s been a lot of introspective work and a lot of little teeny tiny holes and things that add up to sustainable stability. 

So it’s been an interesting year, and I’m sure once I’m out of it, I will have better reflections on what just happened this year. It’s been a rough year, but I know it’s going to be crucial and substantial to my growth going forward. So I’m excited to revisit this next year and tell you all the great lessons I learned from it when I’m not knee-deep in the trenches. 

There you have it guys. Those were my first five years of business. I learned so much. 

And just to sum up:

      1. Passion

      1. People 

      1. Systems

      1. Scaling 

      1. Stability 

    What a journey it has been. 

    And I am just so grateful that I can share this with you and that I can continue to serve small businesses and live out that passion that I found in 2017 still today. 

    So thank you for coming along on my journey with me and for listening to this podcast. This is one of my major, major goals and the original vision that I had for my company was that I wanted a podcast. I wanted to be able to share small business advice and marketing strategies and help other people grow. I wanted to be able to expand my reach and fulfill my mission of serving small businesses. And that’s what this podcast does for me. 

    So I hope you feel it too. 

    Thank you guys for coming along with me and until next time, keep succeeding small.

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