The Daring Entrepreneur

Private coaching for Daring Entrepreneurs on a mission to make an impact

Want support beyond your brand and website?

I offer private coaching in 3-month packages for established, service-based entrepreneurs. My expertise best lends itself to supporting you in the following areas:

Packaging and Pricing Your Signature Program

I can help you break down your brilliance into a step-by-step system, then package and price it to position you as a sought-after and high-paid expert.

Building Your Tribe

Want to leverage the power of live community and events to grow your business and expand your impact? Whether you want to use Meetup or another platform, I can guide you step-by-step, using the same process I used build my Meetup group of over 2,500 members and over 600 events in the last 7 years.

Writing and Marketing Your Signature Talk

Speaking is a timeless and proven method to quickly attract new clients. If you’d like to add speaking to your marketing toolbox, I’d love to help you! I’ve spent countless hours over the past 10 years developing and honing my own speaking skills through multiple speaker trainings and hundreds of speaking gigs.

Organizing Your Business

If you’re on a mission to simplify your business and weed out the things that are causing confusion and dragging you down, I totally geek out on this stuff and would love to help. We can refine your offerings, processes and systems to ensure everything is optimized to save you time and money. 

Here's What You Receive in The Daring Entrepreneur Private Coaching Program:

One, 90 - Minute Kick-Off Intensive

We’ll use this time to evaluate your business, set some exciting goals, and establish your plan for reaching them.

Six, 40-Minute Private Coaching Sessions

As my private coaching client, you will receive a “bank” of 6, 40-minute sessions to use at your discretion over a 3-month period. You are responsible for using my calendar to book your sessions.

Unlimited Email Support

Never leave a question unanswered with unlimited email support between coaching sessions. Take advantage of this service to increase momentum and achieve maximum results in record time.

Unlimited Laser Calls

Laser Coaching Calls are limited to 5-minutes each…but you can use as many as you like! Have a burning question? Want to share a success? I’m here for you!



Full Pay: $5,000

*Save $500 compared to the payment plan option.

Payment Plan:

Secure your spot with a $1,500 one-time, nonrefundable deposit and divide the remainder of your investment into 2 equal monthly payments of $2,000.. *You will invest a total of $5,500 with the payment plan option.

NOTE: When you pair this program with my Million Dollar Brand Makeover or Ignite Your Website Program you will receive 10% off your total investment.

"Before I hired Jessie May as my coach, I was so focused on trying to make money that I made my business a one-size-fits-all service which prevented me from reaching the audience that would truly benefit from my service. But using the skills she taught me about how to get clear on my process, my ideal client and my brand identity, I was able to position myself as an expert in my field and grow my business internationally! I'm now the founder and host of an International Virtual Summit Series and I am frequently contacted to write guest articles and be interviewed as an expert in my field. She also taught me ways to automate key areas of my business so I am not constantly chasing the next post, newsletter or launch date. I have used the techniques that Jessie May taught me to ensure that my brand presence is constant, offers high value content and runs without my daily contact. "

Heather Debreceni
Divorce Coach

"If you are tired of being confused and unfocused in your business, wishing you could just have people understand what you do and who you are, then Jessie May will give you the value you are ready for. She is rich in ideas, experience, and knowledge. She is bold, assured, and kind in her direction pointing. Jessie May’s guidance and accountability has helped me accomplish some of the following things: 1) I tripled my income from last year in less than 6 months, 2) I hired my first assistant, 3) I believe in myself as a valuable player in the coaching community, 4) my husband and I are happier…because I’m happier, 5) I have more energy to play harder and enjoy my life!"

Kate Galt
The Breakup Expert

"Jessie May is a master at the creation and fulfillment of vision. In the time that I worked with her, she taught me how to daringly pursue a business and life driven from desire, and strategically led me through the creation of a solid foundation for my own business as men’s dating consultant. Most importantly, Jessie May profoundly impacted how I embody my being as a feminine presence. I am in awe of her gift for igniting the power and passion of women. She continues to inspire me to come back to my essential self and embrace a life of my choosing with joy and confidence."

Cynthia Kruse
Men’s Dating Consultant

Schedule a time to discuss working together!


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