Today we’d like to introduce you to Jenna Lee Dillon.
Hi Jenna Lee, thanks for joining us today. We’d love for you to start by introducing yourself.Thank you for this opportunity! I‘m an entrepreneur born of entrepreneurs. From ranchers taming the early 1900s wilds of Colorado and Wyoming and my great great great grandmother owning a store in a time when women didn’t run businesses to most of my immediate family being self-employed today, entrepreneurship is my inheritance.
So it’s no surprise that I founded my first venture in high school, a house and pet sitting business called While You Were Out. Since then, I’ve founded or co-founded 6 companies and sold one while also building a marketing career.
After avidly soaking up everything I could learn about acquisitions and business brokering while selling the agency I co-owned, I had to face the facts: I wasn’t just a marketer with flair for operations. I am obsessed with business.
I am passionate about discovering what works and doesn’t work in business — from foundation, through scaling, and all the way to exit or sale. I cannot be in the vicinity of someone discussing a business idea without immediately beginning to strategize about their client personas, the pain point they solve, how to market it, who they’ll need on their team, whether they can bootstrap it or what funding they’d need and more.
Curiosity and a desire to learn are traits that serve me well as an entrepreneur and as the founding partner of my latest venture, Gutsy Money.
I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
Since childhood, I have thought fast, moved fast, learned fast, and made many act-first-think-later mistakes. In fact, I still do. This full-throttle approach has caused some challenges.
Despite that, I’d rather take action and make a mistake than miss out on something due to inaction. I am a living embodiment of the idiom “ask for forgiveness, not permission.” Instead of moving through life slowly, deliberately and carefully, I developed the skills of apologizing, taking ownership, and making it right. And a healthy dose of self-deprecating humor doesn’t hurt either!
With maturity, I’ve cultivated an ability to think before speaking, so that’s a win (everyone around me would agree). Thankfully I finally learned that untempered bluntness isn’t the best path to happy relationships.
I often say that everything works out for me — not because my journey has been smooth; far from it. It means that when I really want something I am willing to put in any amount of effort to attain it. When I don’t get it or when life throws a wrench at my head, I’ve learned how to view the missed mark, heartbreak, loss, or crazy left turn for what it is: an opportunity. At minimum, I learn a lesson. At best, the pivot usually makes room for something way, way better, even if it’s not apparent at the time.
I feel driven to alchemize life’s challenges. I strive to turn the difficult events in my life (and there have been a couple doozies) into something valuable. From a funny story to a platform to support others similarly harmed to a social media post that leaves readers feeling less alone, I do my best to use my life experiences to connect with, support, or empower others.
So…I don’t hope for an obstacle-free life; I just hope to gain something from each challenge that comes along.
We’ve been impressed with Gutsy Money, but for folks who might not be as familiar, what can you share with them about what you do and what sets you apart from others?
Gutsy Money is a bookkeeping and financial literacy firm that serves women business owners. But my founding partner, Terra Rose, and I also see our firm as an agent for change.
We strategically organize our clients’ books and teach them how to interpret their financial data. In doing so, we utilize a practical aspect of business to help change how female founders view themselves and their business. When women business owners take their finances seriously — by organizing them and using the financial data to make strategic decisions — they internally legitimize their business and themselves. This instantly builds their self-esteem and cements their sense of belonging in the world of business — a sense that is not necessarily inborn for many women.
What Terra Rose and I want to see more of in this world is women leading their businesses with boldness and knowledge-backed confidence. I want them, like me, to fall in love with the art and science of business and then leverage it for their success.
In addition to our passion for educating and empowering female founders, we also provide bookkeeping services. Whether a new business needs an accounting system setup or an existing business seeks a past books cleanup or ongoing monthly support, Gutsy Money’s bookkeeping services mean more peace of mind and profitability, plus faster, smarter scaling.
Our clients love that we offload the mental burden and massive time drain of bookkeeping, so that they can concentrate on delivering the product or service they’re known for and growing their businesses!
Our services include:
-Business Financial Health Checkup (find out how you’re doing & get actionable recommendations)
-Accounting system setup (for new businesses)
-Books cleanup/catch-up for existing businesses
-Ongoing monthly bookkeeping (including payroll, A/R, A/P, and more)
-Tax preparation and filing
If we knew you growing up, how would we have described you?
You’d have likely said I was “a lot.” However, the traits that made me a challenging child are now my entrepreneurial super powers. As a kid, I kept the adults in my life on their toes by challenging the status quo, questioning everything, dreaming big, and refusing to accept something just because “that’s the way it’s always been.”
I was very high-energy in my youth, and that has thankfully followed me into adulthood and entrepreneurship. Nothing will challenge energy levels quite like a business in its startup phase (except maybe when my daughter was in her “threenager” stage)!
I was an avid reader and writer growing up. The biggest dream in my little girl heart (other than becoming a mama) was to be an author. I realized that dream in 2024 when I published “Look Up! A Wild & Screen Freed Roadmap to Enjoying Travel with Kids.” It is the first of many books I intend to write. Every time I think about being an author, my internal seven-year-old gives me a high-five.
Achieving my own lifelong dream made me even more passionate about dedicating my life to helping others realize their dreams.
Contact Info:
- Website: https://gutsymoney.co/
- Instagram: https://www.instagram.com/gutsy_money/
- Facebook: https://www.facebook.com/gutsymoney
- LinkedIn: https://www.linkedin.com/in/jennaleedillon/
- Youtube: https://www.youtube.com/@gutsymoney
