In this episode of Outside Insights, I sit down with Raymond Lee, founder of Careerminds, to explore his inspiring journey from HR professional to building a global virtual outplacement company. Starting his business during the 2008 recession, Raymond shares how he pivoted, embraced innovation, and ultimately scaled and sold the company—all while continuing to lead it.

We discuss the challenges of entrepreneurship, like the tough decisions he faced as a leader, including navigating his team through social movements like Black Lives Matter. Raymond opens up about what it takes to build a company culture rooted in action, empathy, and trust.

He also introduces his “Career Success Model,” a framework that’s guided him through change:

• Choice: Making intentional decisions about your path.
• Mindset: Embracing growth and learning from mistakes.
• Agility: Knowing when to pivot and adapt.
• Trust: Believing in the process, even in uncertain times.

On a personal level, Raymond shares how starting CrossFit at 52 has become a cornerstone of his daily routine, fueling his energy and focus. Whether you’re navigating a career transition, leading a team, or exploring entrepreneurship, his story is full of relatable insights and inspiration.

This is more than a story about business—it’s a conversation about resilience, growth, and making bold choices. I think you’ll find it as motivating as I did.

Listen to the episode here

Until next time, friends,

Chris

What does it take to lead with purpose and create meaningful impact in your community? Is it resilience, creativity, or perhaps the ability to connect with others in unexpected ways?

In the latest episode of Outside Insights, I sat down with Colleen Davis, Delaware’s State Treasurer, to uncover her journey from a small-town childhood to managing billions in state investments. Colleen’s path is anything but conventional—spanning neurosurgery, finance, and public service—and it’s packed with lessons on leadership, resilience, and the power of building connections.

I encourage you to listen to the podcast during your next workout, commute, or downtime to explore these key takeaways:

1. The Power of Resilience

Growing up as one of eight children in a family that faced financial hardship, Colleen learned early on how to rebuild from the ground up. Those experiences instilled a boldness and adaptability that have shaped her approach to life and leadership.

Her story is a reminder that setbacks don’t define you—your response to them does.

2. Leadership Rooted in Connection

As State Treasurer, Colleen oversees $11.2 billion in investments and serves on 33 boards, all while championing innovative programs like Delaware Earns, a retirement savings plan for workers without employer-sponsored options. But what sets her apart is her ability to connect people and solve problems through relationships.

Her approach highlights how collaboration and creativity can lead to impactful outcomes.

3. Breaking Barriers to Build Bridges

In high school, Colleen took on a leadership role early, petitioning to create her school’s first girls' soccer team—a move that not only changed her trajectory but also inspired others.

This spirit of determination and advocacy remains a central theme in her career.

4. The Importance of Financial Innovation

Colleen shared insights into her role as a steward of public funds and her efforts to create long-term financial security for Delaware residents. Her team’s work on Delaware Earns exemplifies innovation in public service—offering small businesses a free, easy-to-implement retirement savings option for employees.

5. Lessons in Vulnerability and Growth

From navigating personal challenges to running for public office, Colleen’s story underscores the value of embracing vulnerability and learning from every experience.

Her career path reminds us that success isn’t always linear, but persistence and adaptability make all the difference.

What does it take to build a life or career you’re proud of? Is it grit, a strong network, or maybe just a willingness to admit you don’t have all the answers? In the latest episode of Outside Insights, I sat down with Mark Doughty, founder of Looper Consulting. Mark assists leaders in making informed decisions, refining strategies, and developing leadership skills.

During our discussion, we delved into the unique perspective Mark brings to the table, exploring what happens when we embrace vulnerability, prioritize relationships, and commit to personal growth—no matter how messy the process might be.

I encourage you to listen to the podcast during your next commute to learn more about these key lessons:

1. Relationships Are Everything

Mark emphasized the pivotal role of relationships in both personal and professional success. Your network isn’t just a list of names—it’s the depth and quality of those connections that truly matter. He shared how his ability to forge meaningful relationships has been a cornerstone of his achievements—underscoring the truth that no significant accomplishment is ever a solo endeavor.

“Relationships are one of the most important assets we have in this entire world, even outside of business. When it comes to business, how strong your network is and how solid your relationships are dictate a lot of your success. No one does it alone.”

2. Leading with Vulnerability

If you’ve ever felt that showing vulnerability might be a sign of weakness, Mark’s perspective is a game-changer. As someone who’s navigated through depression while leading teams and growing businesses, he’s discovered that vulnerability, when coupled with confidence, is a potent symbol of strength. It’s about being genuine and approachable without losing sight of your goals.

3. The Toll of Entrepreneurship

Entrepreneurship isn’t just about the thrill of achieving milestones. Mark shared the stark reality of mental health issues that many entrepreneurs grapple with: anxiety, burnout, and depression. But his story also offered a beacon of hope—by prioritizing your physical and mental well-being, establishing routines, and seeking support, you can weather even the stormiest seasons.

We discuss this topic frequently at Outside Insights, I have shared my own personal struggles with burnout. Giving you the tools to conquer similar feelings is a passion of mine - you can check out related blogs hereand here.

4. The Value of Trial and Error

Mark’s path hasn’t been linear—it’s been full of pivots and learning as he went. He talked about the importance of giving yourself room to experiment and adapt, whether in business or your personal life. Small, consistent steps forward can create massive shifts over time.

5. Clarity and Communication in Leadership

Mark’s advice for leaders is refreshingly practical: explain the “why” behind your decisions. Whether you’re leading a team of three or 300, clarity builds trust and buy-in. And when you open the door to questions, you’re not just inviting collaboration—you’re building a stronger foundation for success.

6. Keep It Simple, Stay Patient

One of Mark’s most significant lessons was the power of simplicity and patience. Growth doesn’t happen overnight. By focusing on what matters most and giving yourself grace along the way, you create space for meaningful progress.

Mark’s journey is filled with valuable lessons about leadership, vulnerability, and the power of perseverance. But this is just