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

Heather Monahan_Blog Header

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!

Share it!

Posted in
Tags

Leave a Comment





Alenka Kyslik’s Business Matches Users With Holistic Providers

A brief introduction about Alenka and her business: A Canadian, now living in Los Angeles, Alenka has spent almost 15 years in the corporate world as an overachiever. Eventually it caught up with her and she burnt out. A year later, just as she was recovering mentally, she tore apart her ankle and has spent…

Lana Wear’s Journey to Founding a Real Estate Flipping and Staging Company

A brief introduction about Lana and her business: Lana is Founder and CEO of HomeWear Designs, a real estate flipping and staging company in New York City, the Hamptons, and St. Petersburg, FL. Lana’s career began in Sales, first as a Real Estate Agent in NYC and later as a Sales leader for multinational corporations.…

Addie Gundry is Innovating Diaper Changing for Parents on the Go

“My biggest regret is [that] I kept this so close to the chest for a while, because a lot of people think, ‘Someone will steal my idea. People think it’s a bad idea.’ You almost want to wait to announce what you’re doing until it’s totally complete. And I always say, ‘If you’re not embarrassed…

Cindy Dodd Connects Companies With Key Decision-Makers

A brief introduction about Cindy and her business: Cindy Dodd is an award-winning marketer and global speaker who has emerged as a trailblazer for Black women in the lead generation industry. As the Co-Founder and COO of PEMA.io, Cindy has transformed the company into a global powerhouse, executing over 100 million reach-outs and serving over…

Kathryn Shah, Spring & Mulberry, is Making the World a Sweeter and Healthier Place

“I don’t know that we’ve cracked the right mix yet, but gifting has gone a long way, and I think the more you gift, the more people see your product, and the more you can collaborate on content, the more views you’ll see on your content. And ultimately, what you’re wanting is just this feeling…

Rita Richa Helps Businesses Tell Their Stories Through Podcasting

A brief introduction about Rita and her business: Rita Richa is the founder and executive Producer of Reignite Media. Rita has an extensive background in developing B2B podcasts, content-based networking, and brand strength capitalization. Her clients have been known to classify her as an innovator/visionary, passionate about developing podcasts, scripts, storyboards, social media content, and…

Courtney Todd’s Marketing Agency Increases Brand’s Visibility

Hi, Courtney! Please share a brief introduction about yourself and your business: Hi, I’m Courtney, Fractional CMO + Creative Director of Umlaut Agency. I help brands drive top-line growth and reduce cost per customer by increasing brand visibility and building stronger customer relationships. I also run a creative agency that focuses on branding and website…

Amy Rees Inspires Women Through Art With Personality Plates

“Find somebody to work with as a small business owner. I’m not taking out loans. I don’t have big funding. You really have to pick and choose where you want to invest in your business, but you do have to invest somewhere.” Struggling with feelings of neglect and loneliness in an unhappy marriage, Amy Rees…

Ramy Brook Sharp’s Journey to Building and Scaling a Fashion Empire

“As the leader, it all starts at the top. If you want a culture where people are kind to each other and people are understanding, you have to be that person.” Ramy Brook Sharp is the founder and CEO of Ramy Brook, a contemporary women’s fashion brand known for its chic and versatile designs. Launched…

Sharon Ringier’s Magazine is Curated Exclusively for Women Entrepreneurs

A brief introduction about Sharon and her business: Sharon Ringier is a highly accomplished and influential entrepreneur, speaker, mentor, and philanthropist who has dedicated her life to empowering and supporting women in their personal and professional pursuits. With over 20 years of experience in the events planning industry, Sharon has become widely known for her…

Beth Nydick Amplifies Media Exposure Into Profitable Opportunities for Businesses

A brief introduction about Beth and her business: Beth Nydick, the founder of The F.A.M.E. LAB, is the go-to media expert for coaches, experts, and authors seeking to amplify their brand presence. Known for her strategic approach and media expertise, Beth transforms media exposure into lucrative opportunities, ensuring her clients don’t just shine in the…

Michelle Hsiao’s Consultancy Firm Helps Product-Based Businesses Thrive

A brief introduction about Michelle and her business: Michelle Hsiao is the CEO/Founder of Revenue Growth Advisors, a consultancy for product-based businesses in retail, e-commerce, and wholesale/DTC brands. Previously she led merchandising teams as a Senior Vice President with Boscov’s Department Store, Group Vice President for Macy’s and Chief Merchant/Head of E-commerce for an online…

Networking Without the Nerves: Tips for Authentic Connections

“The power of networking, you never know. There could be just that one person that you connect with who then has somebody else that they know and it’s a snowball effect.”- Richelle Pena  Today’s Startups in Stilettos has a very special minisode dedicated to the power of networking. Tune in to hear Carlyn Bushman and…

Mary Seats Fosters Community With Her Co-Working Space for Women, The Bakery CoWork

“I needed support, community, someone to reach their hand down and pull me up. And now I’m always reaching my hand down to pull someone else up.” Mary Seats is the founder of The Icing Agency and The Bakery CoWork, a co-working space designed for women entrepreneurs. From a young age, Mary showcased her entrepreneurial…

Masi Chukwuemeka’s Businesses Are All About Social Media Management and Storytelling

Hi, Masi! Please share a brief introduction about yourself and your business: My name is Nmasichi Chinenye Chukwuemeka, but I go by Masi. I am the founder of Masi Brands and TribesAndHistory. Masi Brands is a digital branding agency located in Atlanta and our services include web design, social media management, and graphics design. Our…