Best-selling author Heather Monahan on solving the problem of self-doubt and how to keep going after a setback

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Describe your business in a few words?

Solving the problem of self-doubt.

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

I got fired!

What was your background prior to starting your own business?

I was a Chief Revenue Officer in media and had just been named one of the Most Influential Women in radio when I was fired 3 years ago. Prior to that I had been an equity partner of another radio group and a VP of Sales and Executive Vice President. 

Did you always know you wanted to be an entrepreneur?

NOOOOOOO!! Had no idea.

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?

My entire career in Corporate America over a 20 year span was specialized in sales and marketing.  That is the one thing I knew I would be able to do as an entrepreneur. My problem was I didn’t know what product I would bring to market. I decided to write a book as  my first move. What I found out is there are millions of great books but few authors that know how to market. My book took the #1 position in the Business Biography category on Amazon and bumped Donald Trump to position #2. I took that screenshot and leveraged it for all that it was worth. Marketing my book was a success and led to me stumbling into my speaking career which was amazing until the pandemic hit. Then I had to launch a new product offering: executive coaching and consulting. 

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?

When don’t I would be the better question! I partnered with Perry Ellis to launch a clothing line and that initiative failed. I partnered with a skin care company to launch my own line and that fell apart before launch. I pitched myself 14 times to my literary agent and she said no 14 times until I finally got a yes on lucky number 15. My journey is full of failures and a few wins. 

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

My son! I am such a proud mother of a wonderful 13 year old boy who is surviving zoom school. In business I am incredibly proud of my resilience and tenacity to launch a podcast, write a book, launch a speaking career and land a spot at Harvard teaching Professional Selling in my mid-forties.

When hiring for your team, what is your go-to interview question? Please share any hiring tips you can share from your experience?

Examples are the key to my hiring strategy, I need to hear stories and I need references to back them up. If I am speaking with someone and their theme is their commitment to never giving up and going the extra mile to do the right thing that will always be my person. I can teach them the others stuff but intrinsic motivation and character cannot be taught. 

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

My speaking business was crushed with Covid and forced me to launch a consulting business and an executive coaching business that was rather unexpected. 

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

My new book with Harper Collins Leadership is coming out in November! I am so excited for you to read Overcome Your Villains! Beyond that your guess is as good as mine! I have come to realize that being an entrepreneur is not something clear and decisive rather it is something that is constantly evolving which is so exciting. I know the next few years will have my company expanding, serving others, doing good in the world and making millions. 

What is the biggest lesson you have learned in 2020?

Constantly challenge yourself to answer the question: what problem can I solve for my community?  What other product or service can I introduce to add value to them that they would pay for? 

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

It is going to be a very bumpy ride but don’t give up because unexpected blessings will arrive that will make this all worth it! If success was easy, everyone would have it!

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

I don’t believe it exists. The last year I have had to give so much more to my son as he has been virtual almost all year. You go where you are needed. You adjust and do the best you can. Has it been ideal? No! But we have pushed our threshold for what we can handle and it has made us stronger as a result. For that I am grateful. I will appreciate travel and meetings and live events more than ever which will make the future so bright and exciting. Sometimes I am in the moment at work and sometimes I am all in with my son other times I am fully present in my workout. I do not believe in a work life balance; it is more of a constant evolution. 

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

Self-doubt still creeps into my mind even though I preach about being my most powerful and confident self everyday. Here’s what I know: the more uncomfortable you are the more you are growing!  I keep trying to remind myself of that when I become fearful or doubtful again. 

What are your top 3 tips to stay productive each day?

  • Write down your goals.  
  • Take massive action and cross things off on your to do list.  
  • Exercise to increase your energy and sleep.

What does being an Entreprenista mean to you?

Being a complete badass!

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