How to achieve a life of financial freedom with Alisha Pennington of Pennington Perspective

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Describe your business in a few words?

Empowering, Dynamic, and Comprehensive.

What made you take the leap to start your own business?

I have been a business owner in a very niche industry (athletic training) for almost 10 years, so I have experienced the freedom and flexibility that comes with being a business owner. My husband and I started our coaching business to allow others to experience what we do: a life of financial freedom.

What was your background prior to starting your own business?

I have 2 science degrees in sports medicine and run a staffing company in the athletic training profession.

Did you always know you wanted to be an entrepreneur?

NO WAY! I knew I wanted to help people and make an impact. The idea of entrepreneurship came as a necessity to get work. I finished grad school at the tail end of the Great Recession and had to create work opportunities for myself. I started doing freelance work and turned that into a staffing company. Being an entrepreneur is a decision I make every single day, not a single decision I made years ago.

Take us back to when you first launched your business, what was your marketing strategy to get the word out and did it go as planned?

“Marketing strategy” haha — well, let me first say, this was in 2012. Before Instagram, before Twitter; the hottest online trend was Tumblr. Launching my business was based solely on word of mouth and emails. I had no logo, no website, no branding collateral. It was an idea that solved a problem, put forth by a well-networked professional, who was eager to make money. 

In starting our most recent business in 2020 with business coaching, we got all the “latest and greatest” which is a stark contrast to the beginning of our first business. We engaged a PR firm, brought on a social media manager, secured a copywriter, worked alongside an email marketing expert, and had professional branding photos taken. The only reason we were able to do all of this was because of the income we have from our first business, we have already seen a quicker startup as a result of having these pieces in place. 

We always learn the most from our mistakes, share a time with us that you made a mistake or had a challenging time in business and what you learned from it?

Within a year of starting my first business, I received a cease and desist letter informing me that the name I had chosen was infringing on a registered trademark. As someone who already struggled with Imposter Syndrome, this was a CRUSHING blow! The negative voices in my head told me I didn’t belong, that I was out of my element and that I didn’t have what it takes to be successful. Thankfully I realized that despite making this crucial mistake, it didn’t have to be the end of me or my business. We now use this as a lesson in every small business or aspiring entrepreneur we coach, to know where to research their name idea and how to secure it properly. We don’t want our mistake to be anyone else’s!

What is the accomplishment you are the most proud of to date?

Our goal is to start a business in every household. We know and have experienced the freedom that being self-employed allows and we want that to be available to as many people as possible. So, our proudest accomplishment is the dozens of businesses that have been started as a result of our coaching.

How has your business or industry been impacted by the COVID-19 pandemic?

Our coaching business has flourished as a result of COVID-19. Many people realized how insecure their ongoing paychecks were or suddenly had the opportunity to start their business idea with so much time at home. One report stated that new businesses were being started at a rate 4x what had been done in previous years, so we were well-positioned to help others!

What’s next for your business? What can we expect to see over the next few years?

We hope to grow the reach of our business deeper into the sports and entertainment industries because we know so many people who are doing self-employed work there who aren’t maximizing the benefits. We also want to develop higher touch points for our customers, ideally opening up VIP days or in-person mastermind sessions. Overall our goal is to keep empowering aspiring entrepreneurs to get started and consulting current business owners on how to scale their ideas.

What is the biggest lesson you have learned in 2020?

Slow down and be present. We welcomed our first child in June 2020, she has taught me so much about how to prioritize tasks and what is actually important in life. Society teaches us that “busy” is a badge of honor, being in the pandemic helped me realize that slowing down and being present is more valuable and creates higher productivity.

What do you know now that you wish you knew when you were first starting your business?

Things take a while to build momentum, playing the long game is worth it. It takes an entire year to really start gaining traction in a market and giving up too soon is detrimental.

How have you managed to stay grounded this year?

Taking time off and being present with my daughter and family. Checking out of the business mindset, not allowing myself to work deep into the night, and really shutting everything off has helped remind me that there is so much more outside of work.

Do you believe in work/life balance? What are some of your best tips?

I do believe in it. And furthermore, I believe it’s possible to have a dream career and a healthy family relationship at the same time. It takes years of intentionally building a business that works for you/your lifestyle coupled with strong boundaries. Training your coworkers, clients, and peers with how quick to expect a response or your overall availability is crucial in keeping balance between the two. Also, knowing when to step away from work knowing it will still be there when you return. That is the balance. 

What’s something our audience would be surprised to learn about you?

Despite having a million-dollar business, being a decade deep entrepreneur, and a mentor to others; I struggle with Imposter Syndrome. The feeling of not belonging is something that comes up often in new spaces for me, I have dealt with feeling like I have nothing to add to a conversation, and wanting to shrink myself to fit in. I (still) struggle with accepting the amount of success I have had and often downplay all that I’ve accomplished in order to not make others “feel bad.”

What does being an Entreprenista mean to you?

It means being an example to others. Giving permission for others to pursue their dreams and demonstrating that what they want is possible.

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