Are you trapped between being a visionary entrepreneur and a practical business operator? Do you struggle to balance your philosophical ideas with day-to-day execution? You’re not alone.
As a founder, you likely live with a persistent tension: the inspired philosopher within you who dreams big and sees possibilities collides with the opportunistic doer who needs to execute, analyze data, and make practical decisions. This internal conflict is not just common—it’s at the core of the entrepreneurial journey.
The Entrepreneur’s Dilemma
Most entrepreneurs are caught in a perpetual tug-of-war:
- The Philosopher: Deals in ideas, intuition, vision, and big-picture thinking
- The Opportunist: Handles operations, data, rational analysis, and tactical execution
When these two sides are at odds, we experience confusion, burnout, and stalled progress. The frameworks and methods that promise to fix this often lead to further frustration—because they treat the symptoms rather than addressing the fundamental disconnect.
“If we were 100% capable and confident, none of this would be needed. But the problem is that we don’t allow ourselves to go into the gap, and we want to jump over the gap because we lack confidence.”
Why Traditional Founder Coaching Fails
Traditional coaching approaches often force you to choose: be visionary OR be practical. But this is a false choice. Trying to fit into rigid systems can even be destructive:
The solution isn’t another “proven system” or “market-tested formula.” It’s a journey of alignment between your authentic self and your business approach.
What is Entrepreneur Coaching?
Entrepreneur coaching is a specialized form of business coaching designed to help founders bridge the gap between vision and execution. Unlike traditional business coaching that focuses primarily on tactics and metrics, comprehensive entrepreneur coaching addresses both the inner journey of the founder and the outer strategy of the business.
The 9-Step Founder Coaching Journey
Through years of coaching founders, I’ve developed a framework that bridges the philosopher-opportunist gap—not by eliminating either side, but by creating a path that honors both.
This journey isn’t linear. In fact, the most powerful entrepreneurial breakthroughs happen when we step off the line and embrace what I call “the gap”—that uncomfortable space between where you are and where you want to be.
Let’s explore each step:
1. RESET: Create Space for Transformation
The Challenge: Many entrepreneurs are caught in reactive patterns, constantly busy but never moving forward.
The Solution: A complete reset of your mindset, especially around work, money, and success. This often means:
- Questioning your learned business assumptions
- Addressing your money mindset
- Stopping activities that merely keep you busy
- Beginning a physical practice, even just walking
Key Insight: The work needed immediately is on mindset—the rest can come later.
“The entire tissue of society is set up for somebody who has money coming in on the 28th day of the month. How do you get out of that? You really have to rethink your worldview.”
2. EXPLORE: Accept the Chaos
The Challenge: Entrepreneurs want certainty and clarity before moving forward.
The Solution: Embrace uncertainty and make space for what emerges:
- Accept that things won’t go as planned
- Allow chaos to enter your thinking
- Resist the urge to immediately act on new ideas
- Observe without judgment
Key Insight: In this phase, you don’t get to decide—there’s not a lot of action, and ideally not a lot of reaction either.
“Where does my mind take me? Where do my feelings take me? It’s a surrender into the thing. In this phase, you don’t get to decide.”
3. LET GO: Embrace Creative Disruption
The Challenge: We cling to old patterns, ideas, and frameworks that no longer serve us.
The Solution: Make space for the new by releasing the old:
- Let go of business frameworks that constrain you
- Release limiting beliefs about how business “should” work
- Accept that going backward isn’t an option
- See this as creative disruption, not destruction
Key Insight: This step often involves a form of ego death—a willingness to be reborn with new approaches.
“In Tarot this step is represented by 13, the only major arcana without a name, that for its iconography we associate with death. But actually, in interpretation, this is just the ability to make space so that you can plant something. It’s really a creative function.”
4. SENSE: Access Your Intuition
The Challenge: We’ve been conditioned to ignore our intuition in favor of external advice and frameworks.
The Solution: Learn to listen to your gut feeling and inner wisdom:
- Quiet external noise to hear your inner voice
- Trust your intuitive hits about what feels right
- Recognize that your body often knows before your mind
- Connect with your “inner compass”
Key Insight: “Once I know who I am, therefore I know what to do.”
“All of the preparation that we did in reset, explore, let go allows us to do one thing: listen to yourself and listen to your gut feeling and listen to your intuition.”
5. REFLECT: Make Peace with Your Story
The Challenge: Unresolved patterns and conflicts from our past shape our business decisions.
The Solution: Review your life story with new perspective:
- Recognize and heal patterns that repeat in your life
- Make peace with your past
- Actively engage with avoided conflicts
- Begin telling your story with the wisdom of today
Key Insight: When you share your story—whether through a talk, writing, or conversation—you transform it from a burden into a gift.
“I started telling my own life story to myself, but like I never did before… I never recounted the story with the knowledge of today, thinking about all the things with the perspective of having lived the consequences and being here today.”
6. REGULATE: Discipline Enables Freedom
The Challenge: Distractions and unhealthy patterns sap your creative and executive energy.
The Solution: Get your life completely under control:
- Give up substances and distractions
- Disable notifications and media consumption
- Become disciplined about your physical health
- Create structure that supports focus
Key Insight: This step may feel boring, but it’s essential—it creates the stable platform from which you can take creative risks.
“This is the first moment where you open a computer in this kind of idea of finding yourself, to find your project, to find your calling, to find your mission.”
7. REVIEW: See the Market with New Eyes
The Challenge: We either ignore market realities or become enslaved to them.
The Solution: With your authentic core established, you can now productively engage with:
- Market conditions and opportunities
- Your unique abilities and strengths
- What your audience truly wants
- Potential partnerships and channels
Key Insight: With internal clarity, external strategy becomes simpler and more effective.
“Once you have the internal certainty, you just go ahead and start development, track progress. You think with confidence, you operate without confidence.”
8. DREAM: Expand Your Vision
The Challenge: Most entrepreneurs think too small or in conventional terms.
The Solution: Liberate your imagination completely:
- Allow yourself to dream bigger than ever before
- Connect with your true mission, vision, and purpose
- Let your imagination work at a level that feels almost scary
- See beyond immediate business goals to your true impact
Key Insight: This is where your entrepreneur journey connects to something larger than yourself.
“This is the moment where the experimentation, the review, the plan needs to become something bigger. This is where the destination becomes a bit more clear.”
9. BECOME: Embody Your Mission
The Challenge: Entrepreneurs struggle to translate their vision into leveraged action.
The Solution: With full mastery of both your inner landscape and business context, you can now:
- Choose your primary leverage type (ideas, people, systems, or resources)
- Implement with confidence but remain flexible
- Build your business as an authentic expression of your mission
- Create impact aligned with your true purpose
Key Insight: You’re no longer trying to become someone else’s version of a successful entrepreneur—you’re becoming the authentic expression of your unique mission.
“Now finally we are at a decent ending. But of course, we all want to go to Hogwarts. It is now that you have a mission, that’s what you’re becoming.”
The Four Types of Entrepreneurial Leverage
As you complete this journey, you’ll discover your natural orientation toward one of four types of leverage. Understanding your primary leverage type helps you focus your energy and build complementary teams:
The Myth Maker (Ideas Leverage)
- Strength: Building worlds, brands, and communities
- Focus: Symbols, rituals, and creating a sense of belonging
- Examples: Coco Chanel, Walt Disney, Oprah Winfrey
- Output: Transforming perception through powerful narratives
The Group Guru (People Leverage)
- Strength: Creating harmony, trust, and collaboration
- Focus: Building teams, partnerships, and client relationships
- Examples: Richard Branson, Reed Hastings, Brian Chesky
- Output: Creating organizations where people thrive together
The Logic Legend (Systems Leverage)
- Strength: Solving problems through systems thinking
- Focus: Efficiency, scale, automation, and optimization
- Examples: Bill Gates, Sam Altman, Mark Zuckerberg
- Output: Building solutions that scale exponentially
The Wealth Wizard (Resource Leverage)
- Strength: Managing capital and resources effectively
- Focus: Business sense, funding, and financial strategy
- Examples: Warren Buffet, Ray Dalio, Peter Thiel
- Output: Creating sustainable growth through resource allocation
Breaking the Burnout Cycle
What separates this approach from conventional coaching is its focus on alignment rather than optimization. Most entrepreneurs don’t need more tactics—they need integration between who they truly are and how they operate their business.
The most common pattern I see is entrepreneurs pushing through burnout, reaching crisis, and only then seeking transformation. You don’t have to wait for crisis:
“When it’s forced externally, it’s reactive, forced, and brutal. It makes the process even more painful because it’s one that you didn’t want. The work I’m doing is more like preventive care.”
Is The Entrepreneur Coaching Journey For You?
This entrepreneurial reset is most powerful for:
- Founders experiencing misalignment between their vision and day-to-day reality
- Entrepreneurs recovering from burnout or questioning their path
- Business owners whose growth has plateaued despite trying conventional strategies
- Leaders who feel they’ve lost touch with their original mission and purpose
- Executives transitioning to entrepreneurship who need to shed corporate conditioning
Your Next Step
True entrepreneurial transformation isn’t about adding more—it’s about creating space for your authentic business approach to emerge.
The journey begins with recognition: Are you trying to force yourself into systems that don’t honor your full entrepreneurial nature? Are you stuck reacting rather than creating? Is there a gap between who you know you could be and how you’re currently operating?
If so, it might be time for a reset—not just of your tactics, but of your fundamental approach to entrepreneurship.
About Matteo Cassese
After working in corporate at Warner Bros. and consulting for companies like Netflix, Matteo discovered something crucial: true leadership power comes from within, not from frameworks or best practices. Today, he coaches founders to become so vulnerable they become invulnerable, helping them turn chaos into opportunity.
Interested in exploring how this approach might transform your entrepreneurial journey? Contact Matteo to learn more about one-on-one coaching, group programs, or speaking engagements.