Meet Jessie May

Brand Strategist

Hello Daring Entrepreneur!

My name is Jessie May and I’m on a mission to help you take your brand from confusing, boring and forgettable to captivating, professional and gorgeous so you can be seen, heard and hired for the amazing expert you are!

Through the power of archetypes and color psychology, my masters degree in Communications with a focus in New Media and Internet Marketing, my degree in Contemplative Psychology and my Coaching Certification, I help my clients identify their true brand expression, then create beautiful visuals and clear messaging that reflect their expert-level knowledge.

If you feel like your current brand (or lack thereof) is holding you back from taking your business to the next level, then we should definitely talk.

The sea of entrepreneurs is overflowing and it's only getting more crowded. A high-end brand that sets you apart is no longer an option if you want to stand out and be hired for your exceptional services.

My Philosophy

Most people don’t understand branding, so here’s how I like to explain it…

Your brand is a tree:


extend deep into the ground and represent the multiple facets of YOU: your values, opinions, purpose, personality, funky quirks, passions and more.


represent the PLACES where your business comes in contact with the world: social media, public speaking, networking, business card, website, etc.


represents your BRAND experience and connects your Roots to your Branches with consistent visuals and messaging: colors, imagery, textures, patterns, fonts, words, phrases, symbols, logos, sounds, smells, etc.

The mistake I see entrepreneurs make over and over again is they climb straight up to the branches and neglect their Roots and Trunk.

I get it, the Branches are where your business connects with future clients, so it’s only natural to think that starting with marketing activities and touchpoints is your fastest path to increasing your income and building your tribe.

BUT!!! Starting with the Branches will cost you TONS of time, money and energy in the long run because when you neglect your Roots and Trunk, your brand will look like it was designed by a first grader and sound like it has multiple personality disorder! You’ll end up confusing and repelling the very clients and followers you want to attract!

As a service-based business owner, you might think your clients are investing in your service, but actually, they can find a bazillion people online who offer something similar. Your clients are investing in a relationship with YOU.

They choose to work with you because they resonate with what you stand for and they want your personal guidance to help them solve their problem. And the only way they will know if they want this relationship in the first place, is if you bring more of YOU into your brand through clear, consistent and cohesive visuals and messaging.

That’s why working with me always begins with a deep discovery process to identify and unleash the intricacies of your personality before we ever jump into design, copywriting, or building your website.

Who is my ideal client?

My ideal client is a visionary entrepreneur who is the inspirational face of her business. If you have an important message that you need to spread through speaking, books, social media, online courses, etc. then we may be a great fit to work together!

Specifically, we’ll be a great fit to work together if:

  • You and your business have evolved over the years and you want your brand and website to reflect who you are today (and where you’re headed), instead of being a ball and chain to the past.
  • You’re eager to speak on bigger stages, partner with bigger names, and take your business to the next level in general.
  • You’re in the beginning stages of your business but you have a vision for the direction you want it to take. You just need support aligning your brand and website with that vision.
  • You are a vibrant, lit up human being with a positive outlook on life.

On the other hand, I have learned to become very selective with the types of people I take on as clients and will respectfully turn away those who I believe are not a good match.

We will not be a good match if you...

  • Are just starting your business and overridden with fear, money insecurity and self doubt.
  • Aren’t passionate about your business - I can do a lot of things for you, but I can’t give you passion.
  • Are extremely indecisive - you’ll need to be able to make a lot of decisions in a timely manner when we work together.

Why Choose Me as Your Brand Strategist?

I know you have many choices when it comes to having your brand and website designed, so here are a few things about me that might make your decision easier.

I’m not a graphic or website designer, I’m a brand strategist.

While I’ve searched the globe for the best designers to work on my team, and you will receive a gorgeous, high-class brand and website when we’re through; I’m not the designer, I’m the Brand Strategist. My background is in psychology, business development, communications and coaching and my work with you is all about strategically building your brand to attract clients and build your tribe!

If you want a logo, hire a graphic designer. But if you want a complete brand identity that not only looks great but reflects YOU and is profitable too… then you’ll love working with me.

I “get” your kind of business.

My specialty lies in supporting coaches and other visionary entrepreneurs who are the face of their brands. This is why it’s called it “Personal Branding” - I work with you to identify and unleash the brilliance inside into a brand built on your unique personality.

This is the kind of business that I myself have run for the past 10 years, and the type of business that I’ve helped hundreds of entrepreneurs from across the globe refine and scale.

I’m the founder of Daring Divas - the largest community for women entrepreneurs in Colorado.

If you want to build your tribe so you can expand your impact and income, your brand must send a clear signal to the people you want to attract… otherwise they won’t be able to find you. I learned this lesson the hard way in the early days of Daring Divas when my brand was so confusing that it repelled new members and kept my income and impact small.

But once I learned and implemented the brand strategies that I teach my clients today, I was able to grow Daring Divas to over 2,500 dedicated members, fill over 600 events in the past 7 years, and have a tribe that always fuels my coaching business with new clients and leads.

Today, in addition to my brand strategy work, I also coach clients on how to build their tribes through my online course, Meetup Mastery.

What’s My Experience?

  • I’m a Certified Professional Co-Active Coach. I received my certification in 2009 from the highly regarded Coaches Training Institute.
  • I have a BA in Contemplative Psychology from Naropa University.
  • I have an MA in Organizational Communications with a focus in New Media and Internet Marketing from the University of Denver.
  • I have a certificate in Organizational Development and Training from the University of Denver.
  • I have invested hundreds of hours and thousands of dollars into my own business coach and high-end mastermind programs, so I am up to date with the very best material and continue to grow myself and my business.

Ready to boom your brand and build your tribe?

Learn how I can support you!

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