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EP 8: Jessica Dennehy - Pivot and Slay
Jessica Dennehy was raised in the Bronx, New York with aspirations of being a Fly Girl like J-LO, until she realized she didn’t have the skills necessary to do so. As a back-up, becoming an attorney was her next option.
At the age of 26, Jessica became a New York Stock Exchange Regulatory Attorney. This was fueled by her passion for reading, giving perspectives, and hearing perspectives of others. Ten years ago, she made a huge pivot leaving her prestigious position, generous salary, and corporate structure to pivot into entrepreneurship. She is the founder and creator of “Mad Men Barbershop,” and works as an independent attorney helping entrepreneurs avoid the pitfalls of being self-employed. She is an author and business consultant.
In this episode, Jeff and Jessica discuss what it’s like to work in an unwelcoming environment, coping mechanisms, mindset, and the tenacity required to navigate a stunted corporate world. They share the importance of having healthy habits, creating an ideal life, and making the most of the lessons learned along the way personally and professionally.
What You'll Learn:
- The truth about the treatment of youth in the corporate world
- How Jessica decided to jump from her well-paying corporate salary into entrepreneurship
- The mindset of an unfulfilled person not easily seduced by money
- Structuring your day to work for you and not you working for it
- The importance of keeping a healthy mind and body during the journey of entrepreneurship
- Thinking bigger than your 5-mile radius
- And much more!
Favorite Quote:
“The lesson is in the thing that got you to the win. I’ll bet you that whatever you just won at, it wasn’t just your first time trying that out. You tried a bunch of stuff. It didn’t work and you learned from it, which allowed you the capacity and potential to win. So the winning is just the prize, but the failures are really just lessons.”
- Jessica Dennehy
Connect with Jessica:
PivotAndSlay.com
Book: Pivot and Slay: The Ultimate Guide to Mindset Mastery
How to Get Involved:
Addicted to Winning connects listeners through stories that prove why mindset matters. Jeff Brekken was working a 60-hour week on his family’s farm by the time he was 10. When he wasn’t helping with the harvest, he was at the hockey rink. Jeff’s early life experiences taught him he needs to be either all-in or all-out.
In 2000 he started a single-family home construction business and by 2008 he was looking for his next big thing. Jeff founded the Blue Sky Benefit Solutions insurance agency on top of a lifelong passion for helping people. Through this show, Jeff will take that passion one step further.
If you enjoyed this episode, head over and visit us on Apple Podcasts - leave a review and let us know what you thought! Your feedback keeps us going. Thanks for helping us spread the word!
View all episodes
By Jeff Brekken
4.8
3434 ratings
Jessica Dennehy was raised in the Bronx, New York with aspirations of being a Fly Girl like J-LO, until she realized she didn’t have the skills necessary to do so. As a back-up, becoming an attorney was her next option.
At the age of 26, Jessica became a New York Stock Exchange Regulatory Attorney. This was fueled by her passion for reading, giving perspectives, and hearing perspectives of others. Ten years ago, she made a huge pivot leaving her prestigious position, generous salary, and corporate structure to pivot into entrepreneurship. She is the founder and creator of “Mad Men Barbershop,” and works as an independent attorney helping entrepreneurs avoid the pitfalls of being self-employed. She is an author and business consultant.
In this episode, Jeff and Jessica discuss what it’s like to work in an unwelcoming environment, coping mechanisms, mindset, and the tenacity required to navigate a stunted corporate world. They share the importance of having healthy habits, creating an ideal life, and making the most of the lessons learned along the way personally and professionally.
What You'll Learn:
- The truth about the treatment of youth in the corporate world
- How Jessica decided to jump from her well-paying corporate salary into entrepreneurship
- The mindset of an unfulfilled person not easily seduced by money
- Structuring your day to work for you and not you working for it
- The importance of keeping a healthy mind and body during the journey of entrepreneurship
- Thinking bigger than your 5-mile radius
- And much more!
Favorite Quote:
“The lesson is in the thing that got you to the win. I’ll bet you that whatever you just won at, it wasn’t just your first time trying that out. You tried a bunch of stuff. It didn’t work and you learned from it, which allowed you the capacity and potential to win. So the winning is just the prize, but the failures are really just lessons.”
- Jessica Dennehy
Connect with Jessica:
PivotAndSlay.com
Book: Pivot and Slay: The Ultimate Guide to Mindset Mastery
How to Get Involved:
Addicted to Winning connects listeners through stories that prove why mindset matters. Jeff Brekken was working a 60-hour week on his family’s farm by the time he was 10. When he wasn’t helping with the harvest, he was at the hockey rink. Jeff’s early life experiences taught him he needs to be either all-in or all-out.
In 2000 he started a single-family home construction business and by 2008 he was looking for his next big thing. Jeff founded the Blue Sky Benefit Solutions insurance agency on top of a lifelong passion for helping people. Through this show, Jeff will take that passion one step further.
If you enjoyed this episode, head over and visit us on Apple Podcasts - leave a review and let us know what you thought! Your feedback keeps us going. Thanks for helping us spread the word!