Photo of Chelsea Clarke looking outhotel room window in Mexico considering the 6 Observations I made While At A retreat With Ultra-High Net Worth Entrepreneurs

7 Observations I made While At A retreat With Ultra-High Net Worth Entrepreneurs

I just got back from a private retreat in Mexico for 6, 7 and 8-figure entrepreneurs.

While there, I spent 5 days rubbing elbows with extremely successful thought leaders and ultra-high-net-worth individuals.

masterclass become a content creator


As an affiliate partner of various brands and sponsored content, HerPaperRoute may earn commission on qualifying purchases. Disclaimer | Advertise With Us


Immersing myself in the experience and energy of the group, I made some observations about these super-successful people.

Every business owner is feeling the pressure in the economy right now…I was surprised to hear how entrepreneurs at this level are handling it. Here’s what I observed.

1. successful people don’t pretend they know it all

Truly successful people openly express when they aren’t familiar with something and they ask to be shown/explained.

They see every interaction with every single person regardless of how successful they are, as an opportunity to learn from them and improve themselves.

Successful people know everyone can teach them something.

At times, I have felt self-conscious when speaking with CEOs who have achieved so much more growth than I have. I’ve felt like “What do I even have to offer this person that’s of any use to them?” and considered staying quiet.

But I was incredibly surprised by how engaged people were in having conversations with me, and even asking for my thoughts and advice. That sort of unpretentious openness is a lesson that had a great impact on me.

Photo of Chelsea Clarke at business retreat, exploring Valuable lessons I've learned from super-successful entrepreneurs

2. Successful People Are Aware of Their Ego’s Limitations On Growth, And Actively Work To Overcome It

As they are curious and want to grow/learn from others – regardless of that person’s accolades or “level” super successful people don’t let their ego stop them from personal growth.

They actively try to not let their ego get in the way of bettering themselves every day.

They don’t care about looking cool or looking smart. Instead, they have a strong curiosity and hunger for knowledge.

3. When A Team Member Is Slacking, Successful Leaders Take Action And Let Them Go ASAP

“Don’t wait to fire a team member who you’d be relieved to see go!” This was a sentiment shared by many of the people at the retreat, they all regretted waiting too long to make team cuts. 

I feel at some point as business owners, we’ve all held onto a team member longer than we should for multiple fears.

But having that uncomfortable conversation and firing those who are dragging down the team is crucial.

Ask yourself, will you feel relief when they are gone? If yes, don’t wait another moment.

4. There Are More Affordable Ways To Hire, Too

One of the CEOs in attendance, Andrew shared a great tip about how he hires “task coaches” at a fraction of what it would cost to hire them as an employee.

When it’s time to make a great hire, in some cases, you don’t have to hire that expert as a full-time employee, if it’s too expensive. Instead, you can hire them as a contractor to coach your team on specific tasks or skills.

5. Flow State Exists Within You

Getting into “flow state” as a creator and CEO is important.

Previously, I considered flow state to be something you have to “catch” by raising your vibration high enough to discover it.

But when one entrepreneur at the retreat (Jamie) said “flow state already exists within us we just have to practice letting it out,” it was a lightbulb moment for me.

Living in Flow State: Aligning the body, mind and spirit with the universal flow
  • Nelson, Dave (Author)
  • English (Publication Language)
  • 198 Pages – 08/05/2020 (Publication Date) – Independently published (Publisher)

6. get A Founders Card Membership If You Travel Often

if you travel for business often, especially if you are a creator who films content while traveling, I’d recommend ​getting this membership card​ which gets you major deals on flights, flight upgrades, airport lounges, and luxury hotels. 

That’s how I saved thousands last year while traveling! (No its not a credit card, its just a membership).

It also saves you up to $50,000 on Stripe fees in your business operations, among many other benefits. Check it out!

7. Business Owners Are Getting Back “In The Weeds” Of Their Companies

Business owners – even the 8-figure kind are feeling the pressure in the current economy. Many of the people I spoke with have lost millions of dollars in the past year alone, due to a failing economy, rising costs and slower buying habits from consumers.

This is something that was expressed by multiple people at this retreat multiple times. Interestingly, many also said that they felt they outsourced too much, and removed themselves too far from their businesses when times were good in 2020-2022.

As a result, now that sales are down (in all markets), they want to get back into the operations of their businesses like they did when they founded it originally.

They are working hard to get themselves personally “back into the weeds” of their companies, trying to muscle up the hustle and drive they had when they were building their company as a start-up years ago, in an attempt to try to revive their companies and get sales back up, at least to keep afloat until the economy picks up.

Observations I made While At A retreat With Ultra-High Net Worth Entrepreneurs – Conclusion

Now that I am home and rested, I am putting into practice what I picked up at the retreat.

Successful entrepreneurs prioritize value creation, continuous learning, resilience, strategic risk-taking, relationship building, long-term vision, financial discipline, and adaptability.

But there were a few things that surprised me, after studying the habits of ultra-high-net-worth people! Especially the more holistic and mindful considerations they shared.

What tip is helpful to you?

Read This Next:

Sunny day at business retreat in Mexico as Chelsea shares 6 Lessons I've learned about business from ultra-high-net-worth entrepreneurs

Follow along on Instagram!

entrepreneur planner profit business planner notion

masterclass become a content creator

Similar Posts

One Comment

Leave a Reply

Your email address will not be published. Required fields are marked *