Business Lessons from Matt Reynolds

Picking up from where the first half of this interview left off, Matt Reynolds shares his reflections on building and scaling a business in the coaching industry. This is the second half of a practical roadmap for sustainable entrepreneurship, diving into the importance of community, strategic delegation, authentic relationships, and embracing pressure and uncertainty as crucibles for clarity and growth.

The Power of Networked Hiring

In the early stages of a business, who you work with is as critical as what you do. Rather than relying on resumes and cold applications, Matt built his initial team through trusted personal and professional networks. These relationships, already grounded in familiarity and shared values, enabled stronger team alignment and reduced turnover.

This approach is not just about hiring. It is a philosophy that extends to client acquisition and partnerships. Referrals and warm introductions, rooted in credibility and shared culture, outperform impersonal marketing strategies. In an industry built on connection, trust is not a luxury. It is the foundation of excellence and success.

Delegate to Elevate

A pivotal turning point in Matt’s journey was learning to offload tasks that drained his energy or fell outside his strengths. Whether it was customer service, payroll, or scheduling, he recognized that doing everything himself was not sustainable—and worse, it limited the business’s growth.

Delegating to people he trusted, like his first hire Nikki Sims, not only freed him to focus on higher-level strategy but also improved the client experience. By empowering team members with clear roles and ownership, Matt scaled smarter, not harder.

Pay attention to the tasks you dread. That is where your first delegation opportunities lie.

Motivation Comes Before Skill

Leadership is not about handing someone a playbook and expecting excellence. It starts with enrolling people into a shared vision and mission. Motivation must precede training.

There is a clear line between procedural knowledge and buy-in. When people understand why they are doing the work and see themselves as part of a larger purpose, they are more receptive to feedback, training, and iteration. Especially in fast-evolving industries like online coaching, this alignment and adaptability are essential.

Networking That Matters

Traditional networking events often feel forced, performative, and overhyped. Because of this, they are also often unproductive. Instead, Matt favors organic, value-based relationship-building.

The best professional connections, he says, happen when people are simply doing meaningful work in proximity: sharing ideas, helping each other, and creating mutual value. For founders trying to grow their influence or client base, this is a powerful reminder. Depth beats breadth.

Pressure As a Catalyst, Not a Curse

One of the most distinctive parts of Matt’s mindset is his comfort with pressure and uncertainty. Where others see crisis, he sees clarity. He likens risk-taking to poker: focused not on emotion, but on odds, outcomes, and controlled aggression.

This ability to make quick, firm decisions under stress is a cultivated skill that defines resilient leadership. In moments of chaos, Matt does not freeze. He executes. Failure is simply not an option. It is not a denial of risk, but a mindset of committed problem-solving.

Certainty as a Leadership Superpower

People do not just follow instructions. They follow confidence. While some make the mistake of floundering in ambiguity, Matt leans into certainty. Because he has clearly defined values, his decision-making can be rapid. This creates psychological safety for his team.

Certainty does not mean recklessness. It is clarity rooted in knowing what matters, who you serve, and why your work exists. For entrepreneurs who lack this disposition, Matt suggests partnering with someone who has it, because when the road gets tough (and it will), certainty is an indispensable stabilizing force.

Sustainable Performance Requires Recovery

Despite thriving under pressure, Matt is keenly aware that being on high alert all the time is unsustainable. He draws parallels to athletes who peak for key performances and then rest and recover. Business ownership requires the same rhythm.

Matt admits that in seasons of deep business focus, he has let personal health and family time slide—an honest acknowledgment many founders will relate to. The lesson is that high-performance leadership requires intentional decompression. Without it, burnout is inevitable.

Lessons from the Trenches

Matt does not romanticize entrepreneurship. He talks openly about the hard moments: firing employees, raising capital, dealing with lawsuits, navigating board politics. These are not signs of failure but rites of passage. Each stage of business growth comes with new, complex challenges. What keeps him going is a kind of relentless optimism: believing in the mission even when the path is unclear. He views these trials not as obstacles, but as proving grounds.

In an era where business advice is often shallow and success feels manufactured, Matt stands out as a voice of substance. His model of entrepreneurship is not built on just tactics and systems, but on values, vision, and trust.

His story reminds us that building a great business is not about avoiding risk or hustling endlessly. It is about knowing who you are, aligning with people who share your values, and moving forward with clarity even when the road is uncertain.

This material was recently covered in the Business of Coaching Workshop, a series designed to help coaches grow their businesses by mastering key principles like trust, pricing, and delivering value. Each session dives into actionable strategies to build better client relationships and drive success. Want to take your coaching practice to the next level? Join us for the next workshop—it’s free.