Chapter 1 - 20 Lessons from 20 Years in Business

Chapter 1 - From Startup to Grown Up: How real, sustainable growth happens

This year, 2025, marks 20 years since I started my business! Saying it out loud, writing it, seems surreal, but that’s where we’re at and I couldn’t be more grateful and proud of this milestone. I want to share this celebration and anniversary with you because this is not only about me, but about all of you, my clients, colleagues, team members, supporters, friends, family, teachers, coaches, students that have been with me on this journey. 

So, as my 20th Anniversary gift to YOU, I’ve decided to dedicate this entire year of 2025 to pulling out all the greatest lessons I’ve learned and best stories that I want to tell that will help you (and me) grow to the next level, as a CEO, an entrepreneur, a woman - with more simplicity, joy and fun! 

I invite you to read along here on my blog, listen to the special podcast episodes, and stay tuned for any special pop up masterclasses that come up as a result of this project. Of course, I’d love to hear from you what you’d like to hear more about or questions you have or subjects you’d like to see me expand on! This is my gift to you!

And at the conclusion of 2025, I will take all the stories and lessons we’ve shared and I’m going to edit them into a book! Another unimaginable declaration for me today…I'm going to write a book. I'm going to write a book. Probably about a year ago I knew I was being called to write a book and the other night during my journaling time it hit me. And the feeling in my body when I say that is just amazing. It's a really good feeling. 

I've known my whole life I would write a book, but I always felt like I had to wait till something happened to me before I wrote a book. Something exciting, right!? Well, this New Year is exciting, and celebrating 20 years since founding my business and sharing everything I’ve learned along this crazy journey is just about the most exciting thing I can think of writing about.

And so I'm going to be writing a book, a story of being a female entrepreneur over the last 20 years - the wins, losses, tears, and joys - specifically around founding and running my own company, growing up, and growing a family and a life too. So, if you are an entrepreneur, or aspire to be one, we can commiserate, and I also want to inspire and share my story so that it normalizes the entrepreneurial journey.

My entrepreneurial journey is likely much more like yours and what you might be experiencing than some of the other books and stories that I see out there with stories of hitting it big and getting rich quick. That’s not my story.

I've had a slower, consistent growth trajectory over the 20 years of my business. And I am not ashamed of that. I am so very proud that I’ve continued to run, grow and make money over the last 20 years of my life including, 1 wedding, 2 kids, 2 dogs, 4 moves, hundreds of clients, projects and countless amounts of blood, sweat and tears. I’ve grown up as a woman and a CEO on this journey. 

But also, I think we don't often hear the stories of the resilience of women entrepreneurs and what the journey is really like. It’s so easy to compare and despair when all you see is others’ Instagram worthy portrayal of entrepreneurship and meteoric growth. The truth is, when I founded my business in 2005, the average women-owned, service-based small business in America with 1-4 employees had revenue of $25k to $75k per year and only 28% of businesses were woman-owned.

I was right in line with what most businesses like mine were making, (I closed out my first year in business, 2005 with $28,298) but typically thought of myself as a failure and that I was doing entrepreneurship wrong. Yet, I was a typical entrepreneur and small business owner here in America, but didn’t have a community of fellow women to share with and learn from. 

This is why I want to share my story here because in the early years of my business I was always looking for that big thing, right? That big hit of the one magic thing I could offer that would make business so much easier. I thought, “I'm going to get discovered and all the money will come flowing in.” But that's not how growth happens. 

And that's the first lesson, that real growth happens day after day, decision after decision, step by step, one foot in front of the other, when we decide we want growth, then we decide to grow a little bit each day.

One of my mentors, Sandra Yancey, the CEO and founder of eWomenNetwork, says she runs her business every day, on three things. Number one is making the cash register ring or bringing in revenue. Number two is moving the business forward. and number three is meeting a looming deadline or serving a client. So if you think about that and you think about getting one percent better each day, that's really how a million-dollar business or a highly successful, sustainable business is built. Don’t get me wrong, bigger, bolder moves can make it happen much faster, but because of what I went through on 9/11, I was fine with not putting all my energy I had into my business. I chose to work less and grow slower. And I haven't made it yet, even 20 years later, to make a million dollars in one a year in my business. But that’s my intention and I’m on my way. Each year I improve and make money faster and faster, so I know it will come. 

When I started my business 20 years ago, the goal was to make enough money where I could live comfortably in the mountains with my then boyfriend, who's now my husband of 18 years. We had been dating for about a year and a half and we really liked each other. We saw a future together and so we wanted to be closer together. 

I was living in Boulder, Colorado at the time and he was working a corporate job in the mountains near Vail. I had never lived in the mountains and I didn't see any reason why I wouldn’t like to try it, so one of us had to move and I decided I wanted it to be me and so that’s what I did. 

I was really excited about the move. I was born and raised here in Colorado and lived mainly on the plains and grew up a farmer's daughter surrounded by lots of flat land. So the thought of living in the mountains was very exotic and attractive.

Shortly after moving, I decided I was going to start my business. I had been working as a marketing manager and office manager for a mortgage bank in Boulder who had a home office in Fort Worth, Texas. It's kind of funny how I got that job. 

I had moved to Boulder in 2002 after 9/11 happened in 2001. I lived through 9/11 in the New York City area, and it was obviously a very traumatic experience. It was a real wakeup call for me where I really had to ask myself, “if I go to work tomorrow and I don't come home, is this how I want my life to end?” I had just turned 30 that year in 2001 and was working for an Internet software company. This was during the internet boom, and I was a newly minted MBA graduate working in the internet industry in New York, and there was so much excitement and opportunity. I was constantly running around a five-state territory working in business development and marketing for various start-up companies. It was awesome, I was doing lots of very exciting things but just working all the time. I’d be working and then going out partying and having the time of my life, but I was also exhausted, and I knew that that life wasn't sustainable for me. I felt like my spirit wasn't being fed. 

I was also working in a male-dominated industry, and I did not like the chauvinism and how I was treated. Fortunately, the company that I worked for at the time was an amazing group of all men, they were very respectful, very great people to work for. But the industry in general, like going to trade shows or meetings or whatever, I was often one of the few if only women in the room and treated differently in a not so respectful way too often.

Then 9/11 happened, the internet bubble burst, I got laid off from my job and I decided I needed a big change. 

When the World Trade Center went down, so did much of the area’s communications because most of the cell towers were all on top of the World Trade Center. The landline phone systems were jammed up and I couldn't get word to my family, and they couldn't get through to me to know if I was alive. I know for so many families it was much, much worse but it really shook me up. I didn't want to be apart from my family anymore. I didn't want to be separated like that from them again. 

And so I decided I was ready to leave New York, which was heartbreaking because being in New York was a childhood dream of mine. And let me tell you, the time I spent there, I loved every second, I lived every minute to the fullest and I did every fabulous New York thing I wanted to do. I met and worked for and was mentored by some of the most amazing people (that’s a whole other book!). By the end of 2001 I was ready to leave and so in 2002, I pulled up stakes and I came back to Colorado - where I’d been born and raised - and moved into a townhouse in downtown Boulder with a girlfriend of mine from New York who had also left New York after 9/11. She needed a roommate, and we knew each other and so it was nice to have that connection and that friendship, and I moved in with her and went about looking for work.

The first thing I did was to sign up with a temp agency because I had a lot of administrative office experience, which no matter where you go, you can find a job doing that. I started getting some office work and one of the places I was placed was this mortgage company and I really liked them. I liked the people. The owner was an amazing man, very entrepreneurial himself, and owned a few businesses. In March of that year, I remember it so distinctly because it was right around my birthday. We got this enormous snowstorm. I lived in downtown Boulder, so we walked and rode our bikes everywhere. So, big snowstorm, no big deal because we could walk or ride bikes. There was so much snow, everything was shut down and the next day they needed someone to come in to answer the phones and no one else could come in so they called me. I said “sure, I can come in,” because their office wasn't far from where I lived, and people still weren't able to get around. 

I went in to work that snowy day and from that day on I started working there regularly and eventually they hired me on staff. Then when they found out I also had an MBA in Marketing, they wanted me to take over that too. And when I decided to resign and move to the mountains, they became my first client and remained my client for 14 years! It was a really great working relationship, my boss was an amazing man, and so were my colleagues. I learned a lot from them and my boss taught me a lot about entrepreneurship and successfully marketing in the real estate and mortgage industry. He and his support became a very integral part of the founding of my business and a big part of the reason that I'm still here 20 years later!

Ready to Take the Next Step on Your Journey?

Thank you for letting me share this piece of my story with you—it’s such a privilege to reflect on these 20 years and offer insights that might resonate with your own entrepreneurial path.

If today’s story struck a chord with you or sparked curiosity about how to navigate the twists, turns, and triumphs of growing a business your way, let’s connect.

Here’s the thing: You don’t have to figure it all out alone. I specialize in helping women entrepreneurs like you build sustainable, joyful, and profitable businesses—one intentional step at a time.

✨ Curious about what working together looks like?
Hop over to www.melissamkellogg.com to see how I help women turn their big dreams into beautiful, step-by-step realities.

Or better yet, let's get together and talk—I’d love to hear about your dreams, challenges, and how I can support you. You can view my calendar and schedule here: calendly.com/melissamkellogg/60min

Here’s to growing together,
Melissa 💛

P.S. Keep an eye on my blog and podcast for more lessons and stories, and don’t hesitate to send me your requests for topics you’d like me to explore this year!

Author’s Note: This is a true story, as I remember it, except for the parts that are made up.