17 years of being an entrepreneur
This is a really meaningful week for me.
On May 9th, I celebrate 17 years of being an entrepreneur.
17! Like . . . what?! How on earth has it already been almost two decades?
Leading up to this week, I’ve been reflecting on all that I’ve learned over these last 17 years, and there’s one lesson that stands out from them all: The biggest thing that entrepreneurship has taught me is the power of trusting myself and trying things before I am “ready.”
To honor this week’s milestone, I thought about all of the times I said “yes” before I really knew what I was doing—and how those moments got me to where I am now. I want to share my reflection with you in hopes that it will inspire you to take risks and trust in all that you are capable of. We are so much more powerful than we can possibly imagine!
Are you ready? Let’s take a trip down memory lane . . .
SAYING YES TO MY FIRST CLIENT
Seventeen years ago, I was a directionless 19-year-old student at the University of Florida. I wasn’t quite sure what I wanted to do with my life, and as the story goes, I went to the mall one weekend and fell in love with a pair of jeans. I had no money to purchase them, but I desperately wanted the jeans, so I put an ad on Craigslist to clean one house to make enough money to buy them.
Even though I didn’t have any professional cleaning experience, I put myself out there. A woman responded to my ad, hired me to clean her home, and then paid me enough to buy the jeans. The funny part about this story is that I didn’t do the best job. In fact, the woman who hired me offered to teach me how to clean and then hired me to come to her house week after week. She told her friends about me, and that’s how my first business, Student Maid, was born.
Looking back on it now, if I hadn’t taken that leap, my entire life would be different. I might not have had a business at all.
SAYING YES TO MY FIRST BIG CONTRACT
Right before I graduated college, I met a property manager who told me about this three-week period in late summer called “turn,” when thousands of college students move out of their apartments, and all of those empty apartments have to be cleaned before new students move in. The property manager told me there was a need for cleaning companies that could handle a high volume of work and invited me to a meeting where I could introduce myself and my business to property managers and tell them about our services.
I had never had a contract like this before—and I barely had a team!—but I showed up to the meeting anyway. When I walked in, I quickly realized I was the youngest person in the room by far and one of the only women. I was intimidated and terrified, so I excused myself to the bathroom where I gave myself a pep talk in a stall. When I walked back into that room, I told each property manager about my services and left with several contracts.
That was the summer that changed everything for me. I hired a team of 60 students to help me with the work, and if you’ve read my book, you know that 45 of them quit just a few days in (but I got them back!). I decided I was so fascinated by the challenge of leadership that I made the decision to stick with Student Maid after I graduated from college instead of pursuing a job in finance. All because I went to that meeting and gave myself a pep talk in a bathroom stall instead of doubting myself and leaving.
SAYING YES TO MY FIRST SPEAKING GIG
As I grew Student Maid, my professor of entrepreneurship, Dr. Rossi, asked me to speak to his class about my entrepreneurial journey. At that point, I was not a speaker. I didn't think I even had a message to share. But still, I said yes.
I walked into his class with my speech written on a piece of paper, and I read the whole thing word for word, head down the whole time. When I think back, I cringe at how bad I was. But I got through it, and I must have said something right because Professor Rossi ended up inviting me back the next semester. This time, though, he grabbed the paper out of my hand and asked me to “speak from my heart.” So I did—and I felt something shift in me. I learned that speaking was something I really loved, and I started to speak for other classes on campus after that. Eventually, that led to speaking at community events, and before I knew it, my calendar was packed with speaking engagements. Had I not said yes to speaking for Dr. Rossi’s class, I’m not sure if I would have ever learned that speaking was a passion of mine.
SAYING YES TO MY FIRST SPEAKERS AGENCY
As my speaking work grew locally, I started to consider speaking outside of the community where I lived. At the time, I knew of someone who worked with a speakers agency called CAMPUSPEAK, which connects speakers to college campuses all over the country. The application process was really competitive, and I still didn't see myself as a professional speaker at that point. But I trusted myself and gave it a try anyway—and I got accepted to join the roster.
My work with CAMPUSPEAK put me on a path toward being a professional speaker. For a couple of years, I traveled to college campuses all over the country and gave talks about my experience with leadership and what I’d learned as an entrepreneur. That’s where I learned the most about how to engage audiences. (If you can figure out how to keep fraternities engaged, you can keep anyone engaged!). I remember feeling like an imposter filling out the CAMPUSPEAK application and like I needed a few more years under my belt to be considered, but I am so grateful I didn’t let that feeling stop me.
SAYING YES TO ASPEN
A couple of years into my professional speaking journey, my friend Simon Sinek invited me to join him at a leadership retreat in Aspen, Colorado. I had never been to a retreat like that so I didn't know what to expect, and while I was nervous, I went anyway. When I got there, I met all of these incredible people: a former president of Ecuador, the CFO of JetBlue, the founder of the Container Store, and many more. Simon asked me to speak about the future of leadership.
I was freaking out. What could I possibly have to say to a roomful of very powerful, connected, experienced leaders that they didn’t already know? But then, I thought, Simon must’ve wanted me there for a reason. He believed in me, so I decided to believe in myself, too. I trusted that what I had to say to them was important. When I got up to speak, I talked about Student Maid, my journey as an entrepreneur, and my generation: millennials. I talked about how we were unfairly criticized in the press as the “participation generation” and how we did want to work hard and be leaders; we just needed the right environment and the right tools. The CEO of Portfolio Books, which is an imprint of Penguin Random House, also happened to be at this retreat, and he heard me speak. That’s how I got my first book contract. Imagine if I hadn't gone?
SAYING YES TO FOLLOWING MY HEART
In the years after that retreat in Aspen, I moved on from speaking on college campuses and spent more and more time speaking to other businesses and organizations. I realized that my speaking work was where I felt the most alive. While I loved the cleaning business and was grateful for everything it taught me, my true passion was in the leadership development space—not in growing a cleaning company. I wanted to see what could happen if I went all-in on it.
So in 2021, I said yes to taking the biggest risk of my life and following my heart, even though I had no idea what the future would look like. I decided to sell Student Maid and fully embrace speaking and leadership development. And here’s what happened: Today, I'm a full-time speaker. I lead 200+ sessions per year and work with hundreds of leaders and teams all over the world. Three years ago, my team and I launched the Human Leadership Program, which now has thousands of alumni. Every day, I get to do what I'm most passionate about and make the kind of difference I want to make in this world.
. . . and as I sit here and reflect, I recognize that none of this would have happened if I hadn’t said “yes” to these moments. None of this would have happened if I had let fear hold me back. None of this would have happened if I hadn’t made the decision to trust myself even when it felt scary and like I had no clue what I was doing.
I think that the more we grow in our careers, the harder it gets to keep saying yes and trusting ourselves because we feel like we have a lot more to lose. It’s harder to take a leap of faith when you have farther to fall. And that’s why it’s even more important to remind ourselves that we have all survived 100% of everything we've ever been through. Not 99%. Not even 99.9%. 100%.
That’s a really powerful statistic. You are so powerful. It all starts with choosing to believe that you are.
I hope this post inspires you to think about your own “yes” moments and how you can create more of them. Thanks so much for being on this journey with me! Not one day goes by where I don’t feel tremendous gratitude in my heart that I get to walk alongside you as we learn how to be better leaders together.
Here’s to the next 17 years!
Big hugs,
