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From Harvard Law to podcasting powerhouse: Accidental entrepreneurship with Ashley Menzies Babatunde

Did you know that 72% of independent business owners didn’t know that they were going to become entrepreneurs when they started their careers? Today on the podcast, we’re speaking with Ashley Menzies Babatunde, a Harvard law graduate who became an accidental entrepreneur.

Ashley is the host of the No Straight Path podcast, a career coach, storyteller, and extraordinary entrepreneur. She’s giving us a behind-the-scenes look into her nonlinear career path, along with the lessons she’s learned from hosting a highly successful podcast.

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Ashley’s nonlinear career path to accidental entrepreneur

Even during her childhood, Ashley loved to color outside the lines. She was a classic overachiever with huge ambition. At ten years old, she wrote a letter stating she wanted to go to Stanford for undergrad and then Harvard Law School. She eventually did both of those things.

For most of her life, Ashley thought her path was linear, and that she would continue to achieve her goals as long as she worked hard. The first major roadblock that challenged this belief came when she was taking the California bar exam. When she failed the exam, she felt like she was a failure as a human being. 

This experience triggered a period of self-discovery for Ashley where she learned to decouple her identity from her achievements. It was a lonely time for her because no one else was talking about their failures, especially in overachieving spaces. She vowed to share her story, so she started a blog. 
As she also began her career as an attorney, practicing law, she also launched her podcast, No Straight Path, as a passion project. Her podcast quickly grew into something bigger than she ever anticipated, funneling her into accidental entrepreneurship.

The mindset shift from passion project to entrepreneur 

Just three weeks after Ashley released her podcast trailer, Hubspot asked her to join their podcast network. Ashley felt overwhelmed by her passion project turning into something more serious so quickly, and she had to learn the unknown language of marketing and branding right away.

It was a challenge for Ashley to switch to a business mindset instead of treating the podcast like a passion project. She took several classes, created an LLC, and went through the trademarking process for No Straight Path

Ashley wanted to improve her public speaking skills, so she started to pitch herself to speaking opportunities. 

All of these steps helped Ashley build confidence as a new entrepreneur in an unfamiliar industry. However, one of the best things she did was build a community around her podcast that reminded her of her purpose.   

The benefits of taking a leap of faith before you’re ready

Ashley’s experience was very much an example of taking a leap of faith before you’re “ready” and learning as you go. In some aspects, she’s thankful that she was naive about the industry when she got into it. If she knew more, she may have been too scared to try.

Did you know that 74% of adults who are not business owners say that fear of failure is what holds them back? For Ashley, the greater fear is not fear of failure, but fear of staying stuck and not doing things that are in alignment with who she is.   

Since she was new to the entrepreneur space, she also wasn’t intimidated by the big names she met early on because she didn’t know who they were. This allowed her to be herself instead of feeling overwhelmed by self-doubt.

Ashley’s favorite stories from her podcast

Through podcasting, Ashley has learned to lean on her guests for inspiration, insight, and advice. In her episode with Spencer Paysinger, the pro football player turned television writer and producer, Ashley discovered the power of a simple mindset shift. Instead of ruminating on the fear of failure, Spencer learned to focus on the desire to succeed. Additionally, in her conversation with Kristen Turner, a friend from law school, she shared how she turned down a job offer from a huge law firm because it didn’t feel like it was in alignment with her life. Ashley learned how to trust herself with her own life and decisions.

Throughout her podcast interviews, Ashley has seen several common themes, including:

  • The understanding of self and self-awareness
  • Knowing what lights you up, what gives you peace, and what feels good to you
  • Defining your goals, dreams, and aspirations
  • Understanding your weaknesses and acting on them
  • The bravery to listen to your inner knowledge

Ashley has learned that to become a successful entrepreneur, you have to embrace your strengths and be aware of your weaknesses. 

Ashley’s advice for starting a podcast

Ashley would first tell you to pat yourself on the back for having a dream and pursuing it. Next, it’s time to take some action. Surround yourself with like-minded people and ask your community how they achieved their success. Find an accountability partner that you can check in with on a regular basis to push each other forward. 

Ashley’s advice for people who are unsure of their path

If you feel like you’re in the “messy middle” or are unsure of the next move in your career, Ashley encourages you to take an inventory of your life. Think about the things you are interested in and curious about, and that light you up.

For Ashley, she realized she loved telling stories ever since she joined her high school newspaper. She pivoted into career coaching because they realized she loved mentoring other people all throughout school. Connecting the dots of your life can help you find your way forward.

The biggest differentiator between the businesses that succeed and the ones that fail

Ashley believes that businesses that succeed are driven by people who don’t give up and are intrinsically motivated by the work that they’re doing. Instead of being motivated by the numbers, influence, or awards, but the passion for the work.

Important sections of the conversation:

  • [1:53] Ashley’s story from the beginning
  • [4:51] The challenges that Ashley has overcome
  • [12:45] Learning as you go in entrepreneurship
  • [16:12] The fear of staying stuck
  • [18:32] Ashley’s favorite stories from her podcast
  • [24:35] Embracing her strengths and weaknesses as an entrepreneur
  • [28:32] Ashley’s advice for starting a podcast
  • [30:45] Ashley’s advice for people who are unsure of their path
  • [39:38] The biggest differentiator between the businesses that succeed and the ones that fail

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