What does it take to build a successful real estate career when you start during one of the toughest housing markets in history?

On this episode of the Mile High Success Podcast, Nick Elder sits down with Jesse Laner, co-founder of C3 Real Estate Solutions, to talk about Jesse’s path from growing up in a small community in Alaska to building a successful real estate business and investment portfolio in Northern Colorado.

Jesse entered real estate during the 2008–2009 housing crisis. Instead of seeing a bad market as a reason to stay away, he saw an opportunity to learn. He brought the same mindset he had developed as a college basketball player into his new career: work hard, keep learning, and put in the time.

Jesse shares why he believes real estate professionals need to balance finding new business with building long-term relationships. Rather than always chasing the next deal, he encourages agents to take care of past clients, build trust, and create a business based on repeat and referral relationships.

Nick and Jesse also dive into real estate investing and the shift from active income to passive income. Jesse explains why his early focus was on building equity and growing his net worth, and why cash flow can become more important later when an investor wants to rely less on active income.

They also discuss mentorship and one of Jesse’s biggest lessons: relationships are capital. A relationship Jesse formed when he was just 12 years old eventually became an important friendship and business relationship decades later.

For Jesse, success is not something anyone builds completely alone. Mentors, friends, partners, clients, and unexpected relationships can all change the direction of your life.

If you are building a real estate career, investing for your future, or simply looking for a more sustainable way to grow your business, this conversation offers practical lessons about hard work, patience, investing, mentorship, and the power of relationships.

What if the most important skill in a technical career has very little to do with technology?

On this episode of the Mile High Success Podcast, Nick Elder sits down with Craig Hollabaugh, a longtime engineer, consultant, programmer, and startup veteran whose career has taken him across industries including medical technology, transportation, petroleum, national security, and solar.

Craig shares one of the biggest lessons he learned as a consultant: doing great technical work is not enough. He says his work is about 5% technical and 95% human relations.

Craig learned this lesson the hard way. Early in his consulting career, friction with an internal team cost him a job. Looking back, he realized his role was not to walk into a company and become the hero. His job was to help the people already there become the heroes.

Nick and Craig explore what that lesson can teach consultants, leaders, and anyone trying to build stronger teams.

They also talk about the major changes AI is bringing to software development. Craig has been programming since 1979, and today he uses agentic coding tools to complete projects at a speed and level that once seemed impossible. But he also explains why decades of experience still matter when directing these tools and why younger developers face a new challenge: learning how systems work while AI can increasingly do the coding for them.

Craig also shares lessons from a career spent largely outside traditional employment. He explains how relationships have helped him move from customer to customer, why repeat clients can be so valuable, and why having a strong online presence can open unexpected doors.

For people starting their careers, Craig offers a simple message: build things, show your work, learn to talk comfortably with people, and focus on developing both compassion and competency.

As Craig looks toward retirement, he is not planning to stop creating. He hopes to combine engineering and art by building kinetic sculptures and one-of-a-kind vacuum tube guitar amplifiers that are works of art themselves.

Success in business often means making tough decisions when the outcome is not guaranteed. For trial attorney Adam Massaro, learning how to manage risk, prepare for different outcomes, and stay willing to fail has been a major part of building his career.

In this episode of the Mile High Success Podcast, Nick Elder sits down with Adam Massaro, a litigation partner at Reed Smith who helped launch the firm’s Denver office.

Adam shares how his career grew alongside Denver and how he went from building a broad corporate litigation practice to helping establish the Denver office of a global law firm. He also talks about the responsibility that came with bringing members of his team along for that transition.

Nick and Adam explore what separates great attorneys when technical skill alone is not enough. For Adam, one of the biggest differences is being able to connect with clients on a human level. Litigation can last for years, and clients often face major decisions with uncertain outcomes. Adam explains why strong, clear advice and honest conversations are so important.

They also discuss Adam’s approach to risk. Before going to trial, he thinks through multiple possible outcomes and builds different paths forward. That same idea carries into leadership: prepare for Plan A, but be ready for Plans B and C.

Adam also shares one of the biggest challenges he has faced as his practice has grown: learning how to scale without becoming the person who has to make every decision. He explains why leaders need to trust their teams with meaningful responsibilities so those people can grow.

The conversation also covers Adam’s daily habits, his decision to stop drinking alcohol in 2020, his use of cold exposure, and the role failure has played throughout his life and career.

Finally, Adam explains how artificial intelligence is changing litigation. Rather than using AI only to review documents or research case law, Adam uses it to test arguments, identify weak points, explore different scenarios, and “war game” cases before making important decisions.

Adam’s message is simple: if you spend your life trying to avoid every failure, you may also avoid the risks that create your biggest opportunities.

Change is happening faster than ever. AI is changing how we work, how companies grow, and what skills people need to succeed. So how do you keep up without losing sight of who you are?

In this episode of the Mile High Success Podcast, Nick Elder sits down with award-winning speaker, author, and workforce futurist Josh Davies to talk about thriving in a world of constant change.

Josh shares his journey from hospitality leadership to entrepreneurship and the creation of the Center for Work Ethic Development. His work has helped people build the basic skills that matter in every career: showing up, having a good attitude, taking responsibility, working well with others, and continuing to learn.

Josh also explains why the old ways of dealing with change may no longer be enough. Being resilient can help you stand strong, but standing still for too long can leave you behind. Being adaptable can help you change, but chasing every new idea can cause you to lose your direction.

Josh believes we need both.

He shares his approach to combining resilience and adaptability so people can stay grounded in what matters while remaining flexible enough to grow as the world changes.

Nick and Josh also talk about the impact of artificial intelligence on the workplace, why work ethic is not simply a generational issue, and why resilience and adaptability are skills that can be learned.

One of Josh’s most practical ideas is the “1% approach.” Instead of trying to change everything overnight, focus on getting a little better each day. Those small improvements can build on each other and create major change over time.

The conversation also explores entrepreneurship, imposter syndrome, self-doubt, the value of surrounding yourself with people who will give you honest feedback, and why investing in yourself may be one of the most valuable investments you can make.

Josh Davies is an award-winning speaker, author, and workforce futurist who has delivered more than 600 keynotes across four continents. He founded and later sold the Center for Work Ethic Development and now helps leaders and organizations develop the human skills needed to navigate rapid change.

Listen as Nick and Josh explore how to stay relevant, keep growing, and build the skills that technology cannot replace.

What does it take to build a successful career when the work is hard, the stakes are high, and every case brings a new challenge?

In this episode of the Mile High Success Podcast, Nick Elder sits down with Henry Baskerville, a partner at Fox Rothschild. Henry represents clients in complex commercial litigation, white-collar criminal investigations, and construction disputes.

Henry shares the story of his career, from starting out in Chicago to building his practice in Denver. He explains why communication, hard work, and being willing to adapt have played such a big role in his success.

For Henry, great client service goes beyond doing good legal work. Many of his clients are smaller businesses and startups facing disputes that could have a major impact on their future. That is why he works hard to stay responsive and make sure clients know their problems matter to him.

Henry also talks about what happens when a case does not go according to plan. During a trial, new information can change everything. Instead of sticking with the same plan, Henry believes in doing the extra work, studying the details, and changing the strategy when needed.

Nick and Henry also discuss an important lesson for people early in their careers: stick with it. Henry shares how there was a point when he wondered whether he wanted to continue practicing law. As his career grew and he developed his own book of business, however, he gained more control over the work he did and how he did it.

Henry also explains why he chose to become a strong generalist in litigation instead of focusing on one narrow area. That choice allows him to learn about different businesses, industries, technologies, and disputes while using his litigation skills to help clients solve difficult problems.

The conversation also covers the importance of staying organized when managing many cases, why Henry still prefers handwritten notes, and how regular workouts help him manage stress and perform at a high level for his clients and family.

Henry’s message is simple: communicate, adapt, keep learning, take care of yourself, and be willing to go the extra mile.

To connect with Henry Baskerville, visit his profile on the Fox Rothschild website, where his contact information is available. Henry also shares that he is happy to speak with people to see if he can help or point them in the right direction.

What if an old factory or abandoned industrial site could become part of the future of AI?

In this episode of the Mile High Success Podcast, Nick Elder sits down with Gabe Andrews, a data center veteran with 25 years of experience. Gabe has helped deploy data centers on six of the seven continents and in 49 of the 50 U.S. states.

Gabe shares how his career started after nine years in the military. What began as a search for his next job turned into a career that has taken him around the world.

Today, Gabe is helping develop data centers with a different approach. Instead of only looking for new land, his team looks for old industrial sites, including former paper mills, manufacturing plants, and other brownfield properties. Their goal is to bring these sites back to life and turn old factories into the factories of the digital age.

Nick and Gabe also talk about one of the biggest challenges facing data center development: getting communities involved. Gabe explains why developers need to listen first, understand what matters to local residents, and explain projects in simple terms.

The conversation also explores the growing interest in data centers because of AI, what investors should understand about the time it takes to develop these projects, and why access to materials and skilled people may become an even bigger challenge as demand grows.

For Gabe, education is a big part of the answer. He shares his experience with students from fourth-grade classrooms through college and believes knowledge becomes more valuable when it is shared.

Gabe also explains why he is excited about bringing new life to old industrial properties and creating data centers that can provide jobs, revenue, and new opportunities for communities.

What happens when you achieve success, do everything you thought you were supposed to do, and still feel exhausted or empty?

On this episode of the Mile High Success Podcast, Nick Elder sits down with Dr. Laura Schwindt, a former practicing dentist and practice owner who experienced severe burnout after years of growth, responsibility, and constantly doing more.

Laura shares how burnout changed the direction of her life and helped her discover that sustainable performance is about more than having the right strategies and systems. It also requires learning how to manage your energy, reconnect with what matters, and build the capacity to handle the demands of leadership.

Laura spent more than 20 years practicing dentistry and built her own dental practice from the ground up. As the practice grew, she hired more people, expanded, invested in equipment, and continued learning. But doing more eventually left her spread too thin.

A conversation with one of her favorite patients helped Laura recognize that something needed to change. She began working with a life coach, an experience she describes as transformative. That journey eventually led Laura to become an embodied leadership and heroic performance coach herself.

Today, Laura helps dentists, organizations, and other high-capacity leaders move away from cognitive overdrive and toward more grounded and sustainable performance.

Nick and Laura discuss why successful people can reach their goals and still feel like something is missing. Laura explains the importance of reconnecting with your personal “North Star” instead of measuring your life only by outside definitions of success.

They also explore how small daily choices compound over time. Laura encourages leaders to think about three areas: energy, work, and love or connection. Instead of always asking what else needs to be added, she suggests asking what can be removed.

Sometimes the most powerful step forward is doing less.

Laura also shares the value of conducting an “energy audit” by asking what gave you energy today, what drained it, and what you can change tomorrow.

The conversation is a reminder that success does not have to come at the cost of your energy, relationships, or ability to enjoy the life you are building.

What happens when you spend seven years building a business without making money—and almost everyone around you thinks it may be time to quit?

On this episode of the Mile High Success Podcast, Nick Elder sits down with entrepreneur Zach Garfias to talk about the long and difficult road behind building and eventually selling his real estate software company.

Zach’s path was anything but simple. He started in real estate at a young age, moved into distressed property investing, built a demolition company, and eventually decided to take on the real estate software industry.

What followed was seven years of persistence, uncertainty, financial pressure, and sacrifice.

Zach shares what it was like to keep believing in his idea when even the people closest to him were worried. He opens up about risking his mother’s home equity to keep the company alive, living out of his car, and reaching a point where he finally walked away from the business—only to realize he wasn’t finished.

That decision changed his life.

Zach eventually sold the company and went from worrying about basic expenses to facing an entirely different challenge: figuring out what to do with money after a major financial change.

Nick and Zach also discuss why entrepreneurs need smart people around them, the value of getting advice from several trusted experts instead of just one, and why happiness should come before money.

Zach also shares what he is building next with VNTR, a new consumer packaged goods company designed around his love of adventure and the life he wants to live.

At its heart, this conversation is about much more than business. It is about persistence, belief, guilt, gratitude, money, happiness, and having the courage to keep going when the outcome is far from certain.

What does success look like after more than 50 years of writing software? For Jim McMaster, it comes down to staying curious, solving problems, and never stopping the learning process.

In this episode of the Mile High Success Podcast, Nick Elder sits down with Jim McMaster, a veteran software engineer whose career spans an incredible period of change in technology. Jim shares stories from the early days of programming, his transition from IBM 370 assembler to Java, and his experience as the fourth person on the team that eventually produced Google Drive.

Jim also gives listeners a fascinating look behind the scenes at the early thinking that helped shape Google Drive. He explains why he pushed for a familiar files-and-folders structure and how the team thought about making file sharing simple for users.

The conversation then turns to artificial intelligence and the major changes AI is bringing to software development. Jim explains that AI can write code and research solutions much faster than he can on his own. But speed comes with a tradeoff. Instead of personally solving every programming puzzle, his role is increasingly about directing AI, reviewing its work, spotting problems, and making sure the final code is right.

Jim and Nick also explore one of the biggest themes of Jim's career: continual learning. Jim talks about studying at MIT, changing direction from chemistry to computer science, building knowledge beyond his main field, and continuing to learn even after decades of experience.

For anyone building a career in technology—or simply trying to stay relevant in a changing world—Jim offers a simple lesson: read other people's work, ask for feedback, keep practicing, and never assume you are finished learning.

What if you could use your W-2 career to slowly build the freedom to leave it behind?

In this episode of the Mile High Success Podcast, Nick Elder sits down with Mark Greer to talk about the plan Mark and his wife followed for nearly 20 years.

Mark spent much of his career at Zebra, eventually serving as Director of Manufacturing Innovation. As his career grew, so did his interest in real estate.

Instead of using bonuses for new cars or expensive vacations, Mark began putting that money toward rental properties.

His first investment was an older single-family home. It was not easy. It took weeks to find the first tenant, and maintenance costs quickly became a lesson in what Mark did—and did not—want in future investments.

Rather than giving up, Mark adjusted his strategy.

He focused on newer single-family homes close to where he lived. He looked for properties that would appeal to families, including three-bedroom homes with garages in growing communities. Over time, Mark and his wife built a portfolio that reached 15 rental properties before settling on 12 as their “magic number.”

But building the portfolio was only part of the plan.

Mark had to balance two careers at once: his W-2 career and his growing real estate business. He shares how losing focus at work almost put his larger plan at risk and why staying disciplined became so important.

He also explains why he chose not to keep buying properties simply because he could. Mark knew what he wanted his investments to accomplish. Adding more debt and more properties could have pushed his retirement further away.

Today, Mark is in a new phase of his journey.

He and his wife are selling their remaining rental properties and moving toward more passive real estate investments. For Mark, the goal is no longer to own more. It is to gain back something even more valuable: time.

This conversation is about much more than rental properties. It is about knowing where you want to go, building a plan to get there, and having the discipline to stay with it for the long run.

To connect with Mark, reach out to Nick Elder, who can make an introduction for those with a genuine interest in connecting with him.

Listen to the Mile High Success Podcast with Nick Elder on Apple Podcasts and follow the show for more conversations about success, investing, business, and creating greater freedom in life.