The Hidden Struggles of High-Level Entrepreneurs: A Conversation with Sascha Schlossberg

I recently sat down with my dear friend and brilliant entrepreneur, Sascha Schlossberg, the founder of the Infinite Wealth mastermind. In this candid conversation, we explored a topic that is often overlooked, but very real for high-achieving entrepreneurs: the hidden struggles at the top.

Sascha, who runs a mastermind specifically designed for elite business owners, highlighted something that’s rarely acknowledged in the entrepreneurial world:

“There’s something that happens to entrepreneurs once they’ve reached a certain level of success.”

From the outside, it seems like they’ve got it all—luxurious lifestyles, freedom, and businesses generating 6, 7, or even 8 figures. Their social media is flooded with snapshots of family, love, and carefree living. It all looks effortless, doesn’t it?

But that’s just one side of the story. Beneath the surface, even the most successful entrepreneurs go through intense personal challenges—doubts, fears, and struggles they rarely, if ever, talk about.

Table of Contents

The Unseen Challenges of Success

As Sascha and I dug deeper, it became clear that high-level entrepreneurs face struggles that most people can’t even imagine. These are the visionaries, the leaders, and the disruptors—people who appear to have transcended the usual challenges. But behind closed doors, the reality can be much different.

Here’s what we uncovered:

Unrelenting pressure: High-level entrepreneurs aren’t just managing businesses—they’re leading teams, driving innovation, and pushing boundaries. The higher you go, the greater the responsibility.
Heavy burdens: As businesses grow, so do the stakes. These entrepreneurs carry the weight of not only their own success but also that of their teams, clients, and families. Their decisions can affect hundreds—if not thousands—of people.
High-stakes decision-making: Pivots, scaling, and navigating high-risk situations become daily tasks. The margin for error feels smaller, and the pressure to get things right is immense.
Isolation: Perhaps the most painful struggle of all is the isolation. Sharing doubts or vulnerabilities publicly would not only invite judgment but could also jeopardize the trust of their teams and stakeholders.

Why High-Level Entrepreneurs Feel Isolated

Success at the highest level can be a lonely experience. The peer group shrinks as fewer people can truly understand the unique challenges of running a high-level business. When the conversations shift from basic business growth to managing teams, making million-dollar decisions, and supporting livelihoods, the pool of relatable peers dwindles.

This isolation comes with its own set of challenges. As Sascha pointed out, even asking for help feels daunting. There’s an old belief that once you’ve “made it,” you’re supposed to have all the answers.

The Trap of “Figure-It-Out” Mentality

The “figure-it-out-on-your-own” mindset is a dangerous trap. It’s an old paradigm that creates unnecessary stress. Even at the top, entrepreneurs need help, guidance, and perspective shifts—sometimes, all it takes is a conversation with the right mentor or community to get unstuck.

As Sascha shared with me:

“You don’t have to figure it out alone. Finding the right community changes everything. It provides clarity and support when you need it most.”

The Importance of a High-Level Support System

This is exactly why Sascha created Infinite Wealth, her mastermind for high-level entrepreneurs. In this space, elite business owners can take off the mask, be real about their challenges, and collaborate with others who truly understand the pressure of success.

In these exclusive circles, it’s not about venting or complaining. It’s about:

Collaborative problem-solving: Brainstorming solutions with people who understand the complexities of high-level business.
Exchanging high-level insights: Ideas flow more freely when you’re surrounded by peers who face similar challenges.
Receiving real, practical advice: The right mastermind won’t sugarcoat things—they’ll offer actionable strategies to solve problems and make decisions.

There’s something incredibly powerful about being in a room with people who “get it.” When you’re surrounded by peers who know what it’s like to run a high-impact business and still face personal struggles, it makes all the difference.

The Individualism Block

Another significant block for high-level entrepreneurs is the pressure to maintain a facade of perfection. The more successful they become, the more they feel they need to live up to an image that they’ve got it all together.

But this “individualism block” keeps high-achievers stuck. It’s fueled by the idea that once you’ve reached success, you should no longer need help. The truth? That’s when support is needed most.

Success doesn’t mean having all the answers. Even at the top, entrepreneurs need guidance, mentorship, and communities who can help them navigate the unique challenges of high-level leadership.

Final Thoughts

If you’re a high-level entrepreneur feeling the weight of isolation or facing struggles you can’t share openly, know this: you are not alone. The path to success doesn’t come with a handbook, and it’s okay to reach out for support.

Finding the right community—whether through a mastermind or a trusted group of peers—can be the key to unlocking effortless growth and deeper fulfillment. You don’t have to carry the weight of success on your own.

Cheering to your inevitable success,
Jeni Hott 🍾🥂

About Jeni Hott

Jeni Hott is a globally recognized business strategist and 8-figure, automated entrepreneur of nearly 30 years. As the creator of Time Rich Millionaire™, she teaches entrepreneurs how to build freedom-based businesses that scale effortlessly, allowing them to work less, earn more, and make a lasting impact. Learn more at Gettimerich.com.