Lessons in Entrepreneurship from "Inventing Anna"

The tagline for “Inventing Anna” is: “Inspired by the true story of a total fake.”  Of course, I was instantly hooked, along with millions of other Netflix subscribers.  Within a week, several of my clients, friends, and family members were messaging me, excitedly asking “Are you watching Inventing Anna?”  and I am pretty sure I know why.  

First of all, I was a licensed therapist for many years before becoming a coach, I am attracted to complex and complicated characters, and I am known for having really good instincts about people.  They know I am especially fascinated by women who step out of the shadows and shine brightly, one way or another. I had never even heard of Anna Delvey before seeing it in the top series section on Netflix but became pretty obsessed with her.  

After binge-watching the Netflix series, I read articles, watched interviews and documentaries, and scrolled through all the IG accounts that may or may not be hers.  But this episode is not about my psychological assessment of Anna’s character, motives, or personality pathology.  It is about my thoughts on the skills and mindset that almost made her a very successful founder and entrepreneur, someone I think we can learn from, regardless of what we think of her motivation or methods.   

So, what ARE those lessons? 

  • Manage your image
  • Network with the right people 
  • Project unshakable confidence 
  • It takes money to make money
  • Develop resilience 

This episode includes a clip from my interview on “The True Fiction Project Podcast’ with host Reenita Hora.  If you want to hear me speculate about what drives Anna Delvey, whether she was/is a narcissist or a sociopath, did a history of childhood trauma leave her incapable of empathy, and more, check it out!  


There was very little holding Anna Delvey back, and she didn’t let “little things” like a lack of money, connections or influence stand in her way.  At least until those four years in Riker’s Island held her back in a very big way.  But what about you?  Chances are there is a single habit that if you could identify and change would help you realize your entrepreneurial dreams without breaking any laws! 


Take the quiz and get your personalized result, along with lots of strategies for what to do about it! 

Take the “What’s Holding You Back?” Quiz today by clicking on this link:



Did you LOVE this special 100th episode?  Have you been a regular listener and never left a review?  Well, this time, I am going to incentivize it!  Leave a review on this episode (or the show in general, it’s up to you) and before you hit submit, take a screenshot and DM it to me on IG @coachdiannwingert - you will then be eligible to win the Anna Delvey “Iconic” T-shirt from Rosies Tees! 

Apple: https://apple.co/2BZDFzc

Android: https://www.podchaser.com/podcasts/the-driven-woman-1194485


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If you need the focused attention on your business & life that is only available through 1:1 coaching, click here to schedule a free 30-minute consultation with Diann to see if her 12-week private coaching program is right for you. 

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I just started doing weekly FB Lives in the group on Fridays to chat about the podcast topic of the week, or whatever we feel like at the time.  It’s a private group, so do join the group, then join me on Friday Live! 

Let’s connect on Instagram: https://www.instagram.com/coachdiannwingert/ 


If you are getting a lot of good tips from The Boundaries Series, don’t forget to join us next week for another kickass episode, the last one in the series.  It is episode #101 and the title is:  “Boundaries are Self Care”.  A lot of female solopreneurs have been feeling a bit defeated or depleted lately, so this one is for you!


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