CANCUN ENTREPRENEUR'S RETREAT

Live, Learn, and Play with coaches during this immersive dive into your business and life

Registration Deadline: August 3rd, 2025

Event Date: September 10 - 14th, 2025

Ignite Your Transformation

Imagine the thrill of breaking free from the shackles of doubt and uncertainty, stepping into a world where barriers and roadblocks dissolve beneath the brilliance of your own potential.

Craft Your Path to Success

Feeling stuck? Uncertain about your next steps in life or business? At the Cancun Entrepreneur's Retreat, Your Business Auntie,

Billie Olds, and her team are here to guide you through these challenges with personalized attention and focused coaching.

Intensive Coaching Sessions

Prepare to dive deep into the heart of transformation. Spend at least 5 hours per day in intensive coaching sessions, including invaluable one-on-one time with Your Business Auntie. This personalized attention is the cornerstone of the event, offering you unparalleled support and guidance as you chart your course to success.

Escape and Unplug

Unplug from the distractions of daily life and immerse yourself in the serene beauty of our jungle getaway. Here, surrounded by nature's tranquility, you'll have the space and focus to delve deep into your goals and aspirations.

Unleash Your Potential Through Adventure

Feel the rush of adrenaline as you embark on daring excursions and thrilling escapades.

With Billie by your side, every challenge becomes an opportunity for growth

Forge Lifelong Connections

Feel the camaraderie of shared adventure as you bond with fellow adventurers who share your hunger for growth and success. Together, you'll laugh, learn, and leap over obstacles, supported by a community of like-minded individuals who are as driven and determined as you are.

Living and Playing with Coaches

Experience the rare opportunity to spend five days living and playing alongside Your Business Auntie, Caleb Jones, and the team from BOSS Cooperative! From sunrise to sunset, you'll have direct access to their expertise, insights, and support, creating an immersive environment for growth and transformation.

Unique Experience

You will live, learn, and play with the coaches, and will get to experience the creative activities that only your Business Auntie can come up with! This unique setup allows for deeper connections, more profound insights, and unparalleled access to guidance and support.

Then let's goooooo!

Seize Your Moment

This is your chance to break free from the ordinary and step into the extraordinary. Don't let fear hold you back—reserve your spot now and prepare to unleash your full potential with Billie Olds' BOSS Cancun Entrepreneur's Retreat!

VERY Limited Spaces Available - Reserve Now!

We have a consultation option just for you if you are interested in Cancun Intensive

What's Included:

✅ Flights: Fly from select cities* around world that do not require a visa to visit Mexico.

✅ Airport Transfers: Shared van transport from the airport to the resort and back.

✅ Lodging: 5 night stay at a 4-star all-inclusive beachfront resort in Cancun, offering luxurious rooms with private bathrooms, beach access, multiple swimming pools, nightly shows, sports activities, a variety of restaurant options, several bars, live music, and themed parties.

✅ Meals: All meals at the resort’s diverse restaurants, except for the massive international dinner buffet at Xplor Fuego.

✅ Drinks: Wine and spirits at the resort.

✅ Excursions: Snorkel at the Underwater Museum and spend an evening at Xplore Fuego adventure park

✅ Transportation to Excursions: Shared transportation to excursion locations and back.

✅ Gratuities: All gratuities are included.

✅ Intensive Coaching Sessions: Two daily group coaching sessions hosted by different coaches each day.

✅ Work Sessions: Work directly on your projects and ideas for at least 4 hours per day with direct help and

guidance from the coaching team. Make REAL progress on your important projects.

✅ Actionable Advice: Return home with a plan of action that you have developed with the coaches.

✅ Access to Coaches: Enjoy unprecedented access to coaches during sessions, meals, adventures, and free time!

✅ Free Time: Take advantage of the fantastic resort facilities and get to know your fellow participants.

Coaching and Leadership:

Billie Olds - Whether you're an aspiring entrepreneur with a vision, an ambitious business owner looking to elevate your venture, or want to step out on your own as a freelancer, you need "Your Business Auntie" Billie Olds. A seasoned serial entrepreneur and business consultant with over 20 years of experience, Billie excels at turning dreams into thriving businesses, having guided more than 100 entrepreneurs from around the globe to location-independent income success. Billie's extraordinary set of skills, including her unique perspective as woman late diagnosed with ADHD and on the Autism spectrum, enables her to see solutions and opportunities that often remain hidden from others.

Caleb Jones - Well...we don't really need to tell you about Caleb from Unchained CEO - you're just lucky he'll be there.

Yan Guerif - Yan is a distinguished sales coach and consultant specializing in empowering solopreneurs to master the art of selling and achieve their business goals. With over 20 years of experience, Yan has crafted a unique coaching methodology that combines innovative sales strategies with a profound understanding of individual challenges faced by solo business owners. His approach is designed to help solopreneurs leverage their strengths, navigate their limiting beliefs, and achieve remarkable sales success.

Kristy Lake - A long-time seeker of life's wisdoms, Kristy has studied breathwork, Reiki, sound healing, medical massage, mindfulness practices, and Theda healing for over 15 years. In addition to owning a healing center, Kristy specializes in teaching mindfulness practices that result in real-world applications for entrepreneurs. With Kristy's guidance, identify the unconscious and subconscious programming that may be holding you back from achieving your business and lifestyle dreams

Matthew Samp - Over 30 years ago, Matt opened his marketing agency in Midwest of the United States. He's an expert a direct response marketing and known for creating breakthrough marketing ideas with measurable results. He's a nationally recognized leader in political, legal, and small business marketing and will helps his clients dig deep into unlocking their marketing. Never settling for the normal, Matt lives in the Atlantic Rainforest on the southern coast of Brazil where he's the CEO of HMG Brasil, a hospitality management corporation Samp founded just two years ago.

Jonathon M. Smith - Jonathon brings a unique blend of creative and business expertise. With over 15 years in the film industry, Jonathon started his career as a teenage model and went on to work in popular Disney TV shows. His journey evolved as he produced, wrote, and starred in his own feature film, now streaming on Amazon Prime, and appeared in major productions like The Mandalorian, Touch, and Greek. Beyond Hollywood, Jonathon is a seasoned consultant in content creation and its relationship to sales. Jonathon has worked with major influencers and corporate SaaS companies, driving results that blend creativity with business growth.

Peter Young - Peter can show you how to avoid the top three mistakes most entrepreneurs make, and guide you step-by-step on how to start a conversation with a total stranger and turn them into a long-term business partner. Peter works with clients to diagnose all the components of a business, map out a path to improvement, and then “herd all the cats” to get them aligned on strategy and hitting their objectives. In his 25+ year career, Peter has worked at multiple FAANG companies and several startups, being directly involved in both large product successes and catastrophic failures.

More coaches may be added based on the number of registrations!

Explore Last Year's Itinerary:

Day 1

» 3:00 pm – Check-in at our exquisite 4-star all-inclusive beachfront resort. Settle into your luxurious room with ocean views, a private bathroom, and access to resort amenities.

» 4:00 pm - 6:00 pm – Welcome Reception: Hosted by "Auntie" Billie Olds and Kristy Lake. Meet your coaches and fellow participants. Yan Guerif and Kristy Lake will lead the session "Why Are We Here?" Dive into networking, get a comprehensive overview of the retreat, and learn how to maximize your experience.

» 6:00 pm – Dinner at one of the resort’s diverse restaurants. Explore various dining options and engage in conversations with your peers.Resort Highlights: Enjoy beach access, multiple swimming pools, nightly shows, sports activities, a variety of restaurant options, several bars, live music, themed parties, and more.

Day 2

» 7:00 am – Breakfast at the resort’s restaurant, setting a productive tone for the day ahead.

» 8:00 am - 9:00 am – Mindset Mastery: Kristy Lake dives into strategies for overcoming psychological barriers and maintaining entrepreneurial focus.

» 12:00 pm - 1:00 pm – Lunch at one of the resort’s restaurants. Continue discussions from the morning sessions and network with peers.

» 1:00 pm - 3:00 pm – Participant-Led Working Time: Focus on advancing your projects with hands-on guidance from coaches. Tackle specific business challenges and progress on your action plans.

» 3:00 pm - 4:00 pm – Automations and Delegation Mastery: Cliff Taylor’s session on using automation tools and effective delegation to streamline operations and enhance productivity.

» 6:00 pm – Dinner at the resort. Free Time! Enjoy the resort’s evening social activities, including live music, themed parties, or relaxing at the pool.

Day 3

» 7:00 am – Early breakfast at the resort to prepare for the day’s activities.

» 8:00 am - 12:00 pm – Underwater Exploration: Snorkeling at the Underwater Museum. Explore sculptures in a beginner-safe environment, gaining new perspectives and understanding how unconventional ideas can lead to success.

» 12:00 pm - 2:00 pm – Return to the resort, change, and enjoy lunch at one of the resort’s many dining options.

» 3:00 pm - 5:00 pm – Participant-Led Working Time: Work on your projects with personalized guidance from coaches, aiming for actionable outcomes and measurable progress.

» 5:00 pm - 6:00 pm – Solution Engineering: Billie Olds leads a session on brainstorming and implementing effective solutions to your business challenges.

» 7:00 pm – Dinner at the resort. Free Time! Relax and engage in the resort’s evening offerings, whether enjoying a poolside cocktail or participating in a themed event.

Day 4

» 7:00 am – Breakfast at the resort’s restaurant, gearing up for a day of focused business development.

» 8:00 am - 10:00 am – Participant-Led Working Time: Advance your projects with the support of your coaches, ensuring significant progress on your business goals.

» 10:00 am - 12:00 pm - 12:00 pm - 1:00 pm – Lunch at the resort, discussing the morning’s sessions and connecting with fellow participants.

» 1:00 pm - 2:00 pm – Sales Success: Yan Guerif’s session focuses on enhancing your sales skills and closing deals with confidence.

» 2:00 pm - 3:00 pm – Tech That Converts: Cliff Taylor covers effective website strategies and tools to increase conversions and drive sales.

» 3:00 pm - 5:00 pm – Participant-Led Working Time: Continue making significant strides with your projects, benefiting from ongoing coach support.

» 6:00 pm – Dinner at the resort. Free Time! Enjoy the resort’s evening activities or relax in the comfort of the resort’s facilities.

This is fun, let's do it together!

Day 5

» 7:00 am – Breakfast at the resort, preparing for another day of transformative coaching and intense work sessions.

» 8:00 am - 12:00 pm – Participant-Led Working Time: Focus on advancing your projects with continued coach support, targeting specific challenges and goals.

» 12:00 pm - 1:00 pm – Lunch at the resort. Reflect on the morning’s insights and continue networking with peers.

» 1:00 pm - 2:00 pm – Outreach Techniques: Yan Guerif leads a session on effective outreach and communication strategies essential for expanding your business reach.

» 2:00 pm - 3:00 pm – Overcoming Imposter Syndrome: Kristy Lake offers strategies for building confidence and overcoming feelings of self-doubt.

» 3:00 pm – Prepare for the evening’s adventure.

» 4:00 pm - 12:00 am – Depart for Xplor Fuego Adventure Park. Experience zip lines, amphibious vehicles, and underground rivers. Enjoy the massive international dinner buffet at the park and return with insights on risk-taking and creative problem-solving.

Day 6

» 7:00 am – Breakfast at the resort, readying for a final day of creative sessions and practical work.

» 8:00 am - 9:00 am – Networking for Success: Kristy Lake covers strategies for effective networking and building a strong entrepreneurial network.

» 9:00 am - 12:00 pm - Participant-Led Working Time: Advance your projects with the support of your coaches, ensuring significant progress on your business goals.

» 12:00 pm - 1:00 pm – Lunch at the resort. Discuss the morning’s sessions and consolidate your action plans.

» 1:00 pm - 3:00 pm – Participant-Led Working Time: Finalize your projects with personalized guidance from coaches, ensuring clear, actionable plans.

» 3:00 pm - 4:00 pm – Scalable Operations: Billie Olds leads a session on scaling your business and creating sustainable operations.

» 4:00 pm - 5:00 pm – Creative Problem Solving: Cliff Taylor’s session focuses on finding innovative solutions and leveraging technology for business growth.

» 6:00 pm – Dinner at the resort. Free Time! Take a moment to relax, enjoy the resort’s amenities, and reflect on the week’s accomplishments.

Day 7

» Checkout and departure. Leave with renewed energy, actionable strategies, and a clear path forward in your entrepreneurial journey.

Departure Cities:

(we will help with other locations but there may be an additional fee)

Europe

  1. Amsterdam

  2. Athens

  3. Barcelona

  4. Berlin

  5. Brussels

  6. Copenhagen

  7. Dublin

  8. Edinburgh

  9. Frankfurt

  10. Glasgow

  11. Helsinki

  12. Keflavík

  13. Lisbon

  14. London

  15. Madrid

  16. Milan

  17. Munich

  18. Oslo

  19. Paris

  20. Prague

  21. Rome

  22. Stockholm

  23. Vienna

  24. Warsaw

  25. Zurich

South America

  1. Asuncion

  2. Bogota

  3. Buenos Aires

  4. Lima

  5. Medellin

  6. Santiago

  7. Sao Paolo

Central America

  1. Belize City

  2. Guatemala City

  3. Panama City

  4. San Salvador

Mexico

  1. Aguascalientes

  2. Guadalajara

  3. Merida

  4. Mexico City

  5. Monterrey

  6. Puebla

  7. San Louis Potosi

  8. Tijuana

Canada

  1. Calgary

  2. Montreal

  3. Ottowa

  4. Toronto

  5. Vancouver

  6. Winnipeg

United States

  1. Norfolk

  2. Albuquerque

  3. Anchorage

  4. Atlanta

  5. Austin

  6. Birmingham

  7. Boise

  8. Boseman

  9. Boston

  10. Charleston

  11. Charlotte

  12. Chicago

  13. Cleveland

  14. Dallas

  15. Denver

  16. Des Moines

  17. Detroit

  18. Fargo

  19. Hartford

  20. Houston

  21. Indianapolis

  22. Jackson

  23. Kansas City

  24. Las Vegas

  25. Little Rock

  26. Los Angeles

  27. Louisville

  28. Maimi

  29. Memphis

  30. Milwaukee

  31. Minneapolis

  32. Nashville

  33. New Orleans

  34. New York

  35. Newark

  36. Oklahoma City

  37. Omaha

  38. Orlando

  39. Philadelphia

  40. Phoenix

  41. Portland, ME

  42. Portland, OR

  43. Providence

  44. Reno

  45. Salt Lake City

  46. San Antonio

  47. San Diego

  48. San Francisco

  49. San Jose

  50. Seattle

  51. Sioux Falls

  52. Tampa

  53. Washington DC

  54. Wichita

Embrace the Adventure

Set yourself on the path to a future filled with success, fulfillment, and boundless opportunity.

Registration Deadline: August 3rd, 2025, Midnight CST

Join us for the Cancun Entrepreneur's Retreat and unlock the door to a future where anything is possible. Reserve your spot now and prepare to embark on a transformational adventure that will leave you forever changed.

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