Meet Jenna Lee Dillon

We caught up with the brilliant and insightful Jenna Lee Dillon a few weeks ago and have shared our conversation below.

Jenna Lee, we’re so excited for our community to get to know you and learn from your journey and the wisdom you’ve acquired over time. Let’s kick things off with a discussion on self-confidence and self-esteem. How did you develop yours?

I can’t take credit for developing my confidence and self-esteem. My parents provided the foundation for that by empowering me to make decisions, giving me responsibility for my actions, and creating the space for me to make mistakes and learn from them.

I developed self-reliance naturally through being in situations in which I had to rely on myself. I got my first “real” job in 8th grade hostessing at a local restaurant. I babysat my younger brother and sister frequently starting in middle school. When wanted more money and additional restaurant shifts weren’t available, I started a house sitting business.

I left home at 17 and put myself through college with very minimal help from my parents.

The things that, at times, felt like unfair hardships were actually opportunities. I learned to be scrappy, to budget, to work hard, and to figure out exactly how much one person can get done in the 24 hours she’s allotted each day.

I have always said that self-determination is my super power. I’ve never accepted excuses – from myself or the world.

Great, so let’s take a few minutes and cover your story. What should folks know about you and what you do?

I cofounded Gutsy Money because I can’t stand the thought of the world missing out on the products and services of passionate entrepreneurs just because they don’t know how to manage business finances. But that’s the reality for the majority of small businesses that fail — it’s not because they have a bad idea, service, or product. It’s because nobody ever taught them how to manage their business’s cash flow. Especially for female founders, low financial literacy and confidence can be very limiting.

But it doesn’t have to be that way.

I co-founded Gutsy Money to provide female founders with everything they need to gain money confidence and give their business a strong financial foundation.

From accounting system setups for new businesses, books cleanups and monthly bookkeeping for established businesses, and business advisory and tax prep for all founders, Gutsy Money imbues all our clients with the data, education, and empowerment to master their finances. We are here for their maximum profitability, so they can make “gutsy” moves in their life!

If you had to pick three qualities that are most important to develop, which three would you say matter most?

The three qualities I’ve relied on the most and feel so grateful to have acquired are grit, agility and curiosity.

By agility, I mean the ability to change directions, to release beliefs or services or clients who aren’t serving my highest good, and to grow through my mistakes and challenges. Rigidity is debilitating to entrepreneurs. We must stay mentally and emotionally flexible.

Curiosity is another critical characteristic for an entrepreneur. Curiosity is the fuel for agility, as it enables us to ask “I wonder?” or “Why?” rather than reacting harshly or in self-recrimination. When we can be curious — about ourselves, about others, and about the world — we remain open to learning. The business owner who is constantly learning is able to run her business with efficiency and innovation.

Grit is my favorite. Angela Duckworth describes it as passion and perseverance for long-term goals. With rare exception, successful businesses aren’t created overnight. And they certainly don’t remain successful without perseverance. An entrepreneur must define her “why,” that is, the source of her passion for her business. This passion plus the quality of perseverance are what will keep her going on the 12-hour days, will keep her coming back to the drawing board when something isn’t working, will keep her head in the game when self-doubt or haters try to steal her confidence, and will allow her to define success beyond simply what the profit and loss statement shows.

Okay, so before we go we always love to ask if you are looking for folks to partner or collaborate with?

As my focus is on female founders, other professionals who serve women business owners make ideal referral partners. I am a huge fan of women — how they run their businesses, how they show up to their clients, and how they truly want to make an impact through their work. It is an honor to support them to higher levels of business optimization and profitability.

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