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

What if the key to success isn’t about what you achieve, but how much you give back?

In this week’s episode of Outside Insights, I sat down with Mike Smith, a public servant whose inspiring journey proves that leadership is rooted in service.

 Currently serving in Delaware’s House of Representatives for the 22nd district, Mike’s approach resonated with me on a deep level. We both believe that true leadership is about solving problems and making a positive impact on those around us. In other words, being a servant leader.

Mike’s journey is rooted in lessons from his grandmother, who taught him that a full, purposeful life is built on giving back. Whether it was raising money for those in need or simply helping out in the community, she instilled the belief that true success comes from service. That same philosophy has guided Mike throughout his career.

Here are a few of the most impactful lessons Mike shared during our conversation, but make sure to listen to the full episode for a deeper dive into his approach to leadership.

Leadership is About Helping People
Mike sees his role in public service as one of servant leadership. To Mike, it’s not about the title or recognition, it’s about solving problems and being there for others. He shared a great story about learning from Congressman Mike Castle, who taught him early on that politics should never get in the way of simply helping people.

Fulfillment Comes from Giving Back
There’s no greater fulfillment than making a difference in someone’s life. Whether it’s volunteering or stepping up to lead in your community, giving back is at the heart of living a meaningful life.

Engage with Your Community
Mike encourages everyone to get involved, whether by attending local government sessions or volunteering. Community engagement builds trust and understanding, and it’s a key part of being a servant leader.

Lessons from Sports and Coaching
As an endurance athlete and coach, Mike shared three traits that make a great teammate: dependability, skill, and selflessness. These lessons resonated with me because they apply not just to sports but to leadership and life. It's a reminder that success is about showing up for others, not just for yourself.

Mike’s journey and insights are a powerful reminder that leadership is about serving others, making an impact, and constantly striving to be better. Whether you’re leading a team, working in your community, or just looking to grow personally, these lessons can help you close the gap between where you are and where you want to be.

I encourage you to listen to the full episode during your next commute for more of Mike’s inspiring stories and practical advice on leadership. For more on servant leadership, you can also check out a past Outside Insights blog on the topic. 

I’d love to hear from you. How are you applying the idea of servant leadership in your own life? How have you been impacted by a servant leader in the past? How are you or will you give back to others? Reply and let me know.

Until next time, friends.
Chris

Check out the full blog here!

In life, there are assets and liabilities. An asset is a resource that brings value to others and a liability, on the other hand, is a responsibility or obligation. When it comes to your job, the question is simple: would you rather be an asset or a liability?

We all strive to be assets! But let’s acknowledge that no one is an asset 100% of the time—and that’s okay. There are moments when our performance doesn't meet expectations, and that’s part of the growth process. However, if we want to consistently add value and thrive in our roles, we can take steps to close the gap between where we are and where we want to be. 

How about a real life example?  An employee in an analytics role is looking to build a dashboard for key company metrics. To prepare, she takes a free course on the software needed to build the report before the project even gets the green light. The employee loves what she does, she wanted the knowledge anyway.  The outcomes helped the organization tie their outcomes to their strategy for employees, board members and even suppliers. She could have waited to be told what to do and when, this would have been good enough. Instead she added value in a visible way to the entire organization!

So, how do you become and stay an asset?

Creating value is at the heart of being an asset. The more value you create in a day, week, or hour, the more you contribute to the success of your team and company. But how do you consistently create value? Here are a few ways:

• Be a problem-solver: Don’t just identify issues—bring forward solutions. This mindset shows initiative and helps your team move forward.
• Engage deeply: Get involved in your work with purpose. When you find meaning in your tasks, you’ll naturally give more.
• Volunteer: Every meeting presents opportunities to step up. Be the person who takes on challenges and drives them to completion.
• Say "Yes": I once met a plant leader who shared that his rise to leadership came because, during the pandemic, he said "yes" when others hesitated. Sometimes, saying yes to new challenges can open doors.

Becoming an asset is a mindset.  It's entrepreneurial.  And it's a competitive advantage to a leader or business that can cultivate an asset minded culture. And an advantage to an employee that excels at the concept!   Being an asset is about engagement and awareness and about understanding the goals and future of your company.  Your actions, if asset minded support the company on its journey.

On the latest episode of Outside Insights, I had the pleasure of speaking with Sheila Bravo, president and CEO of DANA (Delaware Alliance for Nonprofit Advancement). Sheila’s career journey—from corporate marketing with brands like Vlasic Pickles and Godiva to nonprofit leadership—is all about adaptability, purpose, and lifelong learning. Her story holds valuable lessons for anyone, no matter their field. If you’re searching for inspiration or a reminder that career pivots can lead to more fulfillment, you need to add this episode to your list.

“You never make the plan the way you plan to make the plan.” 

​​Sheila didn’t always envision herself in the nonprofit sector. For years, she thrived in high-powered corporate roles, leading well-known brands and traveling the world. But behind the scenes, something was missing.

The long hours and constant travel meant Sheila was away from her family more than she wanted to be. “I wasn’t around much… the success was there, but the fulfillment wasn’t,” she reflected. The work that once energized her had become routine, and she began to feel disconnected from her purpose.

Sound familiar? It definitely did for me when talking with Sheila. I often reflect on the long hours I would spend locked in my office while my growing family made memories without me. Eventually, something had to give and I had to make a change. Sheila did, too.

She craved something deeper, a career that aligned not only with her professional skills but with her personal values. So, she made the bold decision to walk away from corporate America and seek work with greater meaning.

Nonprofit leadership wasn’t part of Sheila’s original plan, but it turned out to be exactly where she needed to be.

Meet DANA. The secret sauce behind nonprofits.

During our conversation, Sheila highlighted the tough realities nonprofits face: rising costs, staff turnover, and funding that isn’t keeping up with inflation. DANA, under Sheila’s leadership, is helping nonprofits navigate these hurdles. They provide essential training, consulting, and strategy to help organizations operate more efficiently. Their standout initiative is a nonprofit accelerator that helps smaller organizations, especially those serving marginalized communities, scale their impact. Sheila calls DANA the “secret sauce” behind nonprofits, focused on empowering them for long-term success.

Check out the episode on Youtube and learn more about Sheila on Placers website, here!

Our daily choices craft your life’s story — what will today’s chapter be?

I have a long list of goals, life ambitions, projects, and tasks I want to accomplish. I bet you do too. No matter the goals someone has already achieved, it’s human nature to crave more — to want to be better. That’s why everyone I speak with has at least one goal or idea that haunts them — a nagging sense that they just can’t find the time to do it all. Sound familiar?

The answer to doing and achieving more is actually pretty simple — perhaps annoyingly simple: Live intentionally.

Let’s look at an example. One of the most cherished parts of my day are the mornings and that’s because of the sacred morning routine I have carefully established for myself.

For most of my early working years, I sprinted out the door, putting on my tie at stoplights, and skipped breakfast entirely unless a meeting demanded it. While a younger me thought I was saving time and being incredibly efficient by rushing through my mornings, the fact was I was killing my mind and body — and I sure as hell wasn’t more productive because of it. I wasn’t living with intention.

Fast forward to the day we brought two Aussie puppies home. Just what my life of chaos needed, right? The two perfect cherries on top. Turns out, their presence in the home was just what I needed.

During the first few weeks, I kept the same old routine; the only difference was that my two wide-eyed and yapping puppies chased me around the house, adding to the morning dysfunction as I frantically looked for my tie and jacket. They knew I wouldn’t be home for hours and their puppy dog eyes instilled a new level of guilt in me — what’s a guy to do?

I begin waking up early to spend time walking Ziggy and Gracie. It wasn’t just for them; it was for me, too, I soon discovered. I started to appreciate the quiet space before the day’s chaos. It became more than a habit — it was a ritual. I learned to savor my coffee, move my body, plan my day, and enjoy the morning before everything else took over.

I love my mornings now. I walk the dogs, meditate, plan, and sip my first cup of coffee long before the younger me would have even thought about waking up. Yes, I get more done, but it’s not just about productivity. It’s like defragmenting my mind, resetting for whatever the day might bring. For me, it’s carving out intentional time so that I can bring my best self into the rest of the day.

While curating a morning routine is one way I live intentionally, I’m able to identify other ways by taking the time to review my progress towards my goals and holding myself accountable.

Read the full blog here: https://myplacers.com/building-better-days-impacts-simple-intentions

I believe the best ideas come from listening to people who see things differently. If everyone at the table thinks the same way, you’re not innovating—you’re just reinforcing the status quo. The spirit of this idea was a prominent topic in the latest episode of Outside Insights all about effective change management.

I had the pleasure of sitting down virtually with Miriam Dicks, the dynamic Founder and CEO of 180 Management Group. Miriam is the kind of leader who gets right to the heart of what makes organizations tick—and what holds them back. With over 20 years of experience, her firm helps businesses and nonprofits navigate change and achieve high performance by addressing the root causes that impact culture and operations. Whether you’re a leader, a team member, or someone dreaming of their own venture, Miriam’s insights on change, culture, and personal growth are for anyone ready to take their next big step.

1. Change Management: It’s All About the People

During our conversation, Miriam emphasized that change management isn’t just about managing tasks—it’s fundamentally about managing, and supporting, people. Projects and initiatives often fail when they don’t properly account for the human element. Successful change management brings people along on the journey, ensuring that changes “stick” and are sustainable.

2. Culture is the Apex Predator

“Culture eats strategy for lunch.” as the saying goes. Miriam deeply believes in the importance of culture in making or breaking strategic initiatives. If an organization’s culture is unhealthy or resistant to change, even the best-laid plans can fail.

3. The Challenge of Founder’s Syndrome

Although culture is the “apex predator”, there is something that can tank it: Founder’s Syndrome. A major organizational challenge is what Miriam calls “founder’s syndrome.” This occurs when a founder’s personality and vision dominate the organization’s culture, limiting diverse perspectives and stifling growth. To counter this, Miriam advocates for inclusive strategic planning that incorporates diverse voices and experiences.

4. Diverse Perspectives Lead to Stronger Strategies

Plans crafted by just a few individuals are often unrealistic or lack practicality. Miriam suggests that involving a range of voices—from employees to external stakeholders—ensures a more grounded and realistic strategy. This approach also increases buy-in and commitment from those who have to execute the plan.

5. Continuous Learning for Sustainable Success

Those familiar with Outside Insights know I believe knowledge is power. Miriam does, too. No matter your profession, continuous education is essential and Miriam stresses the importance of staying ahead of trends through certifications, learning programs, and engaging with thought leadership. I challenge you to take this a step further and also consider folks in your network you could act as a mentor in a new area.

6. It’s Nothing Personal

Toward the end of our conversation Miriam shared a valuable mindset for entrepreneurs: understand that the ebbs and flows of business are not personal. External factors will always affect business, it’s how you respond to them that defines your success.

While Miriam offers a fresh perspective on change management that is grounded in practical experience and strategic insight, her insights aren’t just for CEOs or managers—they’re for anyone who wants to make a difference, challenge the status quo, and build something that truly lasts. If you’re ready to think differently about change and the power of diverse ideas, be sure to check out the full episode of Outside Insights here during your next commute.

Until next time

I officially started my business 23 years ago — the morning of September 11, 2001.

Of course, history and our lives changed forever that day. It was certainly a challenging start for the business, but challenges have been a constant companion throughout my journey.

Today, I’m known as the guy who started a business from one dollar and scaled it to mid-market size without partners or investors. I bootstrapped it so that it could truly be my company. I’ve guided my business through thick and thin, through four recessions, 9/11, a pandemic, a fire, and even a flood (my building caught fire during the Super Bowl in the early 2010s). Through it all, we’ve adapted and evolved, always focusing on human resources, always maintaining a consultative approach, and always prioritizing culture.

Over the years, I’ve learned countless lessons, personally and professionally. Here are the 23 that stand out most as I reflect on 23 years in business:

1. Challenges are workout sessions: Entrepreneurs face challenges every day. These aren’t just obstacles; they’re opportunities to grow, get better, and solve problems.
2. The path and the goal are separate: Goals will change as you evolve, and that’s okay. You derive the most value along the way, as long as you stay true to yourself and know your values.
3. Play the long game: Business is an ultramarathon, not a sprint. Good things and bad things will happen along the way. Keep your eye on the prize.
4. Build your support system: Starting a business requires a strong support system. My wife and extended family of entrepreneurs supported me while knowing I had to learn on my own, even if it hurt.
5. Leverage change: Change is one of your most important assets. Markets, situations, customers, employees — everything changes. Embrace it.
6. Understand the phases of business: If you’re blessed to make it through the first few years, you’ll go through distinct phases — finding your market, building a small team, creating your first management team, and scaling processes and technology. Understanding this complexity and how you communicate as a business matters.
7. Accept team evolution: The people who join you early for the entrepreneurial experience may be replaced as you grow with those who seek stability and scale.
8. Be willing to work for free: Starting a business is hard. Be prepared to work for free to prove your idea. I did this for many months.
9. Scaling is about small experiments: Scaling a business is a series of small experiments. Try things, learn, and either fail or succeed quickly, then repeat.
10. Build a caring culture: I learned that I could build a culture where people truly care about each other and our community. Today, my business’ culture is the most important element to our success. Cue lesson #11.
11. Culture matters as much as strategy: Culture really does matter. A good strategy will only get you so far if you don’t have a strong culture to back it up.

To get the rest of the list click here. 

Thank you to everyone who has been a part of the Placers, Opposite the Crowd, or Outside Insights community these past 23 years. Your support has been invaluable.

Cheers,

Chris

Imagine transforming recycled tires into a thriving footwear business, then pivoting to reduce homelessness and run for governor. Sounds impossible, right? Not for Matt Meyer, this week’s Outside Insights guest. I had the privilege of speaking with Meyer to explore his approach to leadership, the impactful initiatives he's been part of, and his vision for Delaware's future.

Matt's desire to make a positive impact was strong even before his teaching and political career, starting with a move to Kenya. After serving as a diplomat in Iraq, where he was embedded with the army, Matt returned to the U.S. and—you wouldn’t have guessed it—began teaching sixth and seventh-grade math. 

During his time as a teacher, he became dissatisfied with the state's education system. Driven by a desire to create meaningful change, Meyer decided to run for office. Despite initial skepticism from his family and the challenge of facing a well-established incumbent, his grassroots campaign led to an unexpected victory. This experience underscored his belief in community-driven initiatives and the power of perseverance—both popular topics here at Outside Insights.

Matt's desire to make a positive impact was strong even before his teaching and political career and started with a move to Kenya. There, he co-founded a footwear company that created sandals from recycled tires.  This venture provided employment and economic opportunities in one of Nairobi's poorest neighborhoods and the challenges and successes of this endeavor gave him a unique perspective on economic development.

Today, as the chief executive of New Castle County, Delaware’s largest county, Matt Meyer oversees essential services such as law enforcement, emergency response, libraries, parks, and affordable housing. His leadership focuses on practical solutions that directly impact people’s lives over political rhetoric.

“We don’t make promises, we make plans, and then our job is to turn those plans into real progress.” – Matt Meyer

Meyer’s vision for Delaware as governor is focused on three key areas: improving education, healthcare, and housing. Drawing on his background as a teacher, he aims to elevate Delaware’s education system. In healthcare, he seeks to make services more accessible and effective, inspired by his wife’s experience as an emergency room physician. Additionally, he plans to tackle the state’s affordable housing shortage to ensure more Delawareans have stable homes.

To learn more about Matt’s journey and vision for Delaware, listen to the full podcast episode here. For more inspiring stories and actionable insights, tune into the Outside Insights podcast. You never know who our next guest will be!

Until next time friends,

Chris