Boss Up

Boss Up

Boss Up

Boss Up

Boss Up

Boss Up

Boss Up

The Boss Up Mastermind

Oakbrook, IL November 9, 2019

The mastermind for go-getters, dreamers, game changers, and trailblazing entrepreneurs ready to dominate in their spheres of influence and do it God’s way. Whether you’re a small business owner, someone looking to become a better leader, or you’re ready to take that leap of faith from employee to entrepreneur, this is the event for you.

This isn’t your typical empowerment event, where you leave, go home, and still have no idea what to do next or a conference of motivation where God is taken out of the message. This is a mastermind of instruction. In fact, those are the exact words God gave us. We’re giving you the nitty-gritty, real-talk, how-to so that you can think your way rich and master the inner game of wealth.

Meet Your Host

ASHLEY WINSTON is a multi-passionate entrepreneur, speaker, and breakthrough strategist. With over 15 years of experience in teaching and coaching in both personal and business settings, she helps people win and provides them with the necessary keys to unlock their peak performance.

Her gifts and unique skill set have landed her a wide range of opportunities both here and abroad. She has served on the mission field in Port Au Prince, Haiti and Hyderabad, India. She has been featured in commercials, films, and on television including the popular daytime talk show, Rachael Ray, and worked behind-the scenes of major productions. From classrooms to churches to corporations, Ashley Winston has worked with over 5,000 youth, 50 Chicago Public Schools, and more than 70 organizations including The Lyric Opera of Chicago and McDonald’s Corporation.

Ashley Winston is the Founder and Creative Director of BREAK FREE BE UNSTOPPABLE and the host of the Break Free podcast, where she teaches people how to show up, tell the truth, and do the work so that they can live God’s best for their lives. She is the author of Break Free: Unlock Your God Given Potential & Unleash Your Unstoppable, You Are Enough, and her most recently published book, 7 Secrets to Living Your Best Life, a guide to help you overcome your obstacles and create a life you love.

Meet our Amazing


Ashley Winston

Author and Breakthrough

Some people call me a preacher. Some call me a coach, but I’ve never been too big on titles. At my core, I’m a creative and I’m more focused on purpose, which brings me to you. I will help you transform your life and breakthrough to your best.

Niki Winston

Author, Minister, and Speaker

We all have unique personal styles and God designed each of us to operate differently. We will discover ways we can boss up in our love game (with ourselves and each other) while leveraging our gifts to help those around us, ultimately increasing our potential for growth and profit.​

Craig Burton

Financial Guru and
Business Consultant

As a leader in my industry and a well connected businessman, I am taking the Kingdom of God into the world. I want to enable people to have generational impact and help marketplace leaders fulfill their Kingdom purpose.

David Winston

Pastor of Go Hard for Christ Youth Ministry and Director of Bill Winston Ministries

I am passionate about teaching and encouraging people of all ages how to have victory through Jesus Christ in every area of their lives, and how to discover and pursue their God-given destiny.

Jackie Horbrook

Educator and Founder and CEO of Black Christian Influencers

Join me as I journey through challenges and opportunities that affect the educated Christian millennial. Together, we will wrestle difficult topics, learn from our collective failures, pose questions, and find comfort in the eternal truth of our living God.

Hanha Hobson

Author and Founder of
Transparency Ministries

I struggled with low self-image and having confidence, and then God radically changed my life! Now I help people overcome fear and self-doubt so that they can confidently believe who God has called them to be.

Tiffany Everage

Clinical Therapist and
CEO of Soul City Therapy

I am a proud Chicago-native, with nearly a decade of combined social service and clinical work. My personal mission is to help guide you into greater awareness and deeper healing, so you can make the best decisions for yourself.

Kelly McMath

Author and Leadership
Development Specialist

I coach business and ministry leaders to become game-changing, fruitful culture champions for their organizations. Together, we will connect-the-dots between your purpose and your performance.


Registration, Meet & Mingle Fun

A Moment of Inspiration

General Session 1

General Session 2

Small Groups & Activity

VIP Lunch Experience

Real Talk: Your Mental Health Matters

General Session 3

General Session 4

Small Groups & Activity

Cookies, Coffee & Conversation




Instant access to all speakers and general sessions from the Boss Up Mastermind on November 9th

Our Sponsors

Check Out SOME OF our

Boss Up Merchandise

Unstoppable Beanie


Boss Up Sweatshirt


Faith Tote Bag


Venue information

Le Méridien Chicago Oakbrook Center

2100 Spring Road, Oak Brook, Illinois 60523 USA

Parking is free for the event

Nov 9, 2019. 9 am-5pm

Interested in staying overnight? We are not offering any room rates, but check out the following hotels: Le Méridien Chicago, DoubleTree, Chicago Marriott Oak Brook, Hilton Chicago Oak Brook. You may need to lay down after your Boss Up Mastermind experience is over!

Frequently Asked Questions

When and where is the event being held?

November 9, 2019 from 9am-5pm. Doors open at 8:15 am. Le Meridien Chicago - Oakbrook Center 2100 Spring Road, Oak Brook, Illinois 60523 USA

Will you be recording the Boss Up Mastermind?

Yes, we will be recording the event and you will be able to purchase the audio replay.

If I registered, but I’m unable to make it live, will I get the recording for free?

The Boss Up Mastermind audio recording is sold separately for $47.

Is there childcare provided?

Childcare is not provided and we politely request no children as we are unable to accommodate them.

Will food be provided?

An amazing lunch has been prepared for you. However, there are a lot of nice restaurants in the area for your enjoyment as well.

What if I buy my ticket and can’t come anymore?

All tickets are non-refundable and non-transferable to any other product or program, including the Boss Up Mastermind audio recording. However, you’re more than welcome to transfer your ticket to a friend. The deadline to transfer tickets: October 31, 2019.

What’s the dress code?

Dress like the boss that you are! Please bring a sweater or jacket in case you get cold.

Are there any vendor opportunities?

There are no vendor opportunities, but we are accepting sponsors! Find our sponsorship registration here.

I’d love to volunteer! How can I sign up?

We would love to have you serve at the Boss Up Mastermind! Please email us at: support@

Additional questions?

If you have any additional questions, please email us at: support@


Boss Up


Le Meridien Hotel
OakBrook, Il 9-5PM

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