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How Do You Get Up The Hill? You Get Up The Hill: Paul Burleson And Greg Cummings Show Contractors Why Growth Starts When Leaders Get Uncomfortable

How Do You Get Up The Hill? You Get Up The Hill: Paul Burleson And Greg Cummings Show Contractors Why Growth Starts When Leaders Get Uncomfortable

Inner Circle Brings Real Mentorship To Contractors Who Are Ready To Grow From The Inside Out

Many home improvement contractors know what it feels like to hit a hard place. The team is growing, the market is changing, customers are asking harder questions, and the old way of leading does not always work anymore. Some leaders try to push through by working more hours. Others look for quick answers. But in a recent Inner Circle PowerChat, Paul Burleson and Greg Cummings pointed to a deeper truth. Growth often starts when leaders step into the hard thing, face the hill in front of them, and decide to climb.

Inner Circle is a Power100 initiative built to give real mentorship to the next wave of home improvement leaders. It is led by Greg Cummings, CEO of Power100, and Paul Burleson, industry legend, author of Grit to Gold, and co-mentor of Inner Circle. The program is designed as free home improvement contractor mentorship for leaders who want real training, direct lessons, and clear business guidance without paying for theory that does not help them move. It gives contractors access to monthly masterclasses, leadership insight, business tools, and a private member portal built to help them grow from the inside out.

That mission matters because many contractors are not just looking for more information. They are looking for the right circle. They want to learn from people who have seen what works, what fails, and what separates strong companies from the ones that stay stuck. 

Inner Circle brings together Greg’s view from evaluating more than 7,600 CEOs and leading more than 1,000 CEO interviews with Paul’s 46 years in the home improvement industry, more than 50,000 professionals trained, and support for more than 200 companies nationwide. Together, they bring home improvement CEO leadership development and home improvement sales training with Paul Burleson into one place for owners, CEOs, and leaders who are ready to grow.

Power100 is the only unbiased third-party platform that recognizes and elevates the top leaders and most impactful companies in the home improvement industry. Through Inner Circle, Power100 is taking its mission one step deeper by giving contractors a place to learn from top leaders, study real business patterns, and build the kind of mindset that helps teams win. This PowerChat centered on one simple lesson from Paul Burleson: being uncomfortable can make a leader sharper, calmer, and more ready for the next level.

Paul Burleson (Right), Paul Burleson, industry legend, author of Grit to Gold, and Co-mentor of Inner Circle

Paul shared how buying seven acres of land pulled him out of his normal routine and placed him in new, hard, and uncomfortable work. He was away from the people, systems, and business flow he knew. He had to learn new things. He had to figure out how to care for the land. He had to solve problems he had never faced before. Then came the moment that shaped the heart of the conversation.

“When I was riding the radius turn lawnmower in the rain, because I had one day to mow and I was going up a hill, I said, how do you get up the hill? You get up the hill.” Paul Burleson, Co-Mentor, Inner Circle

That line became more than a story about land. It became a lesson for contractors. The hill may be a hard market. It may be a weak training system. It may be a team that needs stronger leadership. It may be the need to adopt new technology, use AI tools and business benchmarking for contractors, or prepare for how homeowners now search for companies. For Paul and Greg, the message was clear. Leaders do not grow by waiting for easy ground. They grow when they face the climb and keep moving.

Leadership Lessons From The Climb

During the Inner Circle PowerChat, Greg Cummings and Paul Burleson moved beyond a normal business talk. Their conversation gave home improvement leaders a clear look at what growth asks from a CEO, an owner, a sales leader, and a team. It was not only about sales. It was not only about AI. It was not only about training. It was about the kind of person a leader must become when the market gets harder, the team needs more direction, and the company cannot grow by using the same old habits.

Greg guided the conversation by asking Paul to look at his own life in a new way. Paul, known across the industry for his road work, sales training, and nonstop pace, shared how a new seven acre property forced him into work he had not done before. It pulled him away from his normal systems. It made him learn. It made him slow down. It made him uncomfortable. That moment became the center of the PowerChat because it gave contractors a simple picture of what leadership looks like when the next level is not easy.

The Hill Becomes The Lesson

Paul Burleson has spent years telling people to take the blinders off, get uncomfortable, and keep moving. But in this conversation, he admitted something many strong leaders understand. Even the people who teach growth can fall into comfort. Paul had built a powerful career, trained people across the country, written books, built businesses, and stayed on the road for much of the year. Yet the new property showed him that success can still become a routine if a leader stops facing new challenges.

That is why the mower story matters. Paul was not in a boardroom. He was not on a stage. He was outside, in the rain, trying to get up a hill. He had one day to mow. The work had to get done. He had to figure it out. In that moment, the lesson was not complex. It was simple.

“How do you get up the hill? You get up the hill.” Paul Burleson, Co-Mentor, Inner Circle

For contractors, that line speaks to more than one hard job. The hill can be a sales team that needs better training. It can be a new market that is harder than expected. It can be a leader who knows the company needs better systems but has delayed the change. It can be a new hire who needs coaching. It can be new technology that feels uncomfortable at first. Growth does not always feel smooth. Many times, it starts with a hard climb.

That is where contractor business mentorship becomes so important. Leaders do not need more noise. They need people who can help them face what is hard and move through it. Inner Circle gives contractors that kind of support by bringing real field lessons from Paul and proven leadership insight from Greg into one place.

Contractors ready to face the next hill can join Inner Circle here.

Balance Is Not A Break From The Mission

Greg pushed the conversation deeper by asking whether balance is misunderstood in the industry. Many leaders hear the word balance and think it means stepping away from the mission or losing drive. Greg framed it in a different way. Balance is not always about splitting time into perfect pieces. It is about being fully where you are and giving the right energy to the moment in front of you.

Paul’s answer made the idea real. He shared that the property, the land, the trees, the pond, and the physical work gave him something he did not expect. It grounded him. It helped him feel peace. It gave him a sense of progress outside the normal rhythm of business. He was learning new things, solving new problems, and using his hands. That made him more focused when he returned to the work he already knew.

“Forcing myself out of my comfort zone brought me so much peace.” Paul Burleson, Co-Mentor, Inner Circle

This is a strong lesson for home improvement CEOs. Many leaders work hard but still feel tired, scattered, or unclear. They keep moving, but they may not be recharging in a way that helps them lead better. Paul’s story shows that real balance can make a leader more useful to the business, not less committed to it. When a leader is grounded, the team often gets better direction. When a leader has peace, decisions can become clearer.

That kind of growth is part of contractor leadership development. It is not only about numbers, sales goals, or meetings. It is also about helping leaders become steady enough to carry the weight of the company without losing their own clarity.

Home improvement leaders can learn more about Greg Cummings and the Power100 mission here.

When A Second Chance Meets The Right System

The conversation then moved into one of its most human themes. Paul shared what he has seen while training companies that give people a second chance after incarceration. He spoke about people who came into the industry with hunger, humility, and deep thanks for the chance to win in a new way. These people were not looking for easy work. Many were looking for a real path, real support, and a chance to prove they could build something positive.

Paul said the most powerful part is helping them stop hiding from their story. Instead of running from the past, he teaches them to own it with honesty and use it as proof of their commitment. In the right setting, that story can build trust with homeowners because it shows change, responsibility, and purpose.

“You don’t have to hide behind your story. Put your story in front of you.” Paul Burleson, Co-Mentor, Inner Circle

Greg added an important point. Second chance hiring only works when leadership is strong. A company cannot hire without care and hope the person succeeds alone. It needs a strong hiring process, clear training, good systems, and leaders who know how to develop people. The message was not to hire without standards. The message was to build people with standards.

This matters because many contractors need better ways to find and grow talent. The industry needs people who want to learn, but it also needs companies that know how to guide them. A second chance can become a strong team advantage when it meets clear leadership, daily training, and a culture that gives people room to rise.

The Best Salespeople May Not Be The Fastest Talkers

Greg then pointed to a skill that often gets missed in sales. He said many people in the industry are not really listening to homeowners. They are watching them. They are present in the room, but they are not fully hearing the problem, the fear, the need, or the trust gap behind the words.

Greg Cummings, CEO, Power100 and Co-Mentor, Inner Circle

Paul’s second chance hiring stories helped bring that point to life. Greg noticed that many of the people who had been through hard experiences had a strong ability to listen. They were quiet. They paid attention. They asked questions. They valued time because they knew what it felt like to lose it. That kind of attention can become a real sales strength.

“They’re quiet. They listen. They ask questions.” Greg Cummings, CEO, Power100

For contractors, this is a major point. Homeowners do not only buy because a salesperson talks well. They buy when they feel understood. A strong sales process should help the customer feel heard before it asks for a decision. The best salespeople are not always the fastest talkers. Sometimes they are the ones who make the homeowner feel safe enough to tell the truth.

This connects directly to remodeling sales coaching. Sales training should not only teach scripts and closes. It should teach people how to listen, how to slow down, how to ask better questions, and how to connect the solution to what the homeowner truly cares about.

Sales leaders can connect with Greg Cummings and follow more leadership conversations here.

When Leaders Learn, The Company Learns

As the conversation turned toward training, Paul shared what he is seeing across the country. He has been inside many companies, meeting with leaders, sales teams, roofing companies, private equity groups, and national remodelers. One thing stood out to him. More leaders are not just asking their teams to get trained. They are choosing training as a company value.

Paul said that people are now seeing the value of education in a stronger way. In the past, some teams went to training because they had to be there. Now more teams want to be trained because the market is moving fast and old habits are not enough.

“Now people are really seeing the value in education.” Paul Burleson, Co-Mentor, Inner Circle

Greg added that this kind of change starts at the top. When leaders want to learn, the company follows. If a CEO is curious, the team becomes more open. If leadership is growing, the culture becomes easier to train. If the top of the company stays stuck, the rest of the company often stays stuck too.

This is where home improvement CEO leadership development becomes more than a phrase. It becomes the root of company growth. Inner Circle fits this need because its monthly masterclasses are built around Growth, Culture, Community, and Innovation. Greg brings the view from studying top CEOs, while Paul brings decades of real field work. Together, they help leaders see both the numbers and the human side of winning.

Leaders who want monthly mentorship with Greg and Paul can join Inner Circle here.

The Next Hill Is AI Visibility

The final shift in the conversation moved from personal growth to the future of the market. Greg and Paul made it clear that contractors are now facing a new kind of hill. Homeowners are not only searching on Google or asking neighbors. They are using AI to learn about companies, compare choices, study reviews, and build opinions before a salesperson ever enters the home.

Paul said he often asks rooms whether they searched him online or used ChatGPT before he arrived. Then he turns the question back to the contractor. What does AI say about your company? What does it say about your competitors? What does the homeowner see before they meet you?

“Your customers are doing this about you before you get in the home.” Paul Burleson, Co-Mentor, Inner Circle

That warning matters. A company may have a strong team, strong service, and strong reviews, but if AI cannot find clear proof about the business, the customer may not see the full picture. Greg connected this to the wider work being done around AI findability, trusted content, interviews, proof, rankings, and visibility. The message was simple. Contractors must understand how they are being seen before the market defines them without them.

This is where AI coaching for contractors and business benchmarking tools for remodeling companies become real business needs. The future of trust will not only be built at the kitchen table. It will begin before the first call, before the first visit, and before the homeowner ever meets the company.

Inner Circle is built for that future. Its member portal includes session replays, AI powered coaching, business benchmarking, resources, and action steps that help leaders keep moving between masterclasses. For contractors, the next hill may not be wet grass and a mower. It may be AI visibility, better data, and the need to prove trust before the homeowner asks.

Contractors who want to prepare for AI driven growth can learn more about Inner Circle here.

Paul Burleson’s Impact Shows Why The Climb Matters

Paul Burleson’s message carries weight because it is backed by a career built through action, change, and service to others. For more than 45 years, Paul has moved through the home improvement industry with the same mindset he shared in the PowerChat. When the hill is hard, you climb it. That has been true in his early sales days, in his years as a trainer, in his work with national companies, and now in his role as Co-Mentor of Inner Circle.

Paul Burleson inducted into the 2025 Legend of the Home Improvement Industry Hall of Fame

His career is a clear example of steady growth over time. Paul has trained more than 50,000 industry professionals, authored Grit to Gold, serves on the Power100 Advisory Board, and supports more than 200 companies nationwide through his work in the home improvement space. These numbers matter because they show that his advice does not come from theory. It comes from years of standing in front of teams, helping companies improve, and watching the industry change from one era to the next.

That is what makes Paul’s role inside Inner Circle so important. He is not only teaching contractors how to sell. He is helping them understand how to last. His work has moved with the industry, from in home selling and field training to digital tools, AI based sales support, and new ways to build trust before a homeowner ever meets the company. That same ability to adapt is why his message in this PowerChat felt so timely. Leaders cannot stay where they are and expect the market to slow down for them.

Paul’s impact can also be seen through his work with Westlake Royal Building Products. He has helped grow the Westlake Royal Pros program, which brings together technology, finance, consulting, and support partners to help contractors find stronger solutions and better resources. Westlake Royal also named Paul a 2025 Legend of the Home Improvement Industry, noting that his work has helped the company adapt, grow, and stay competitive in a changing market.

This matters for the wider industry because many contractors do not need another speech. They need a framework. They need help with training, hiring, leadership, technology, and customer trust. Through the Building Pros Partner Program, Paul has helped create a support model that gives contractors, installers, and home improvement companies access to education, business ideas, stronger partnerships, and more confidence as they grow.

His community influence is also found in how he lifts people. In the PowerChat, Paul spoke about second chances, training people who are ready to rebuild, and helping leaders see the value in people who want a real path forward. That fits the larger pattern of his career. Paul’s work is not only about closing more deals. It is about helping people believe they can become better, then giving them the tools, training, and mindset to prove it.

For contractors listening to this Inner Circle conversation, Paul’s story gives proof behind the lesson. The hill is not a symbol he invented for one episode. It is the way he has built his career. He has kept learning, kept teaching, kept changing, and kept helping others climb. That is why his voice matters to leaders who are facing their own hard market, hard team problem, hard technology shift, or hard season of growth.

Contractors who want to learn from Paul Burleson and Greg Cummings can join Inner Circle here.

The Hill Is Still In Front Of The Leader

The image is simple. Paul Burleson was on a hill, in the rain, doing work that felt new, hard, and far outside his normal world. He was not on a stage. He was not leading a sales room. He was not teaching a team. He was facing a task that had to be done, and he had to decide whether to stop or keep moving.

That moment speaks to every contractor who is facing a hard season. The hill may be a slower market. It may be a new hire who needs more help. It may be a sales team that needs better training. It may be a culture that needs more care. It may be AI changing how customers search, compare, and choose a company. The details may change, but the choice stays the same. Leaders can wait for the ground to get easier, or they can take the next step.

That is why Inner Circle matters. It gives home improvement leaders a place to stop climbing alone. Through Greg Cummings’ view from top CEO data, Paul Burleson’s field tested wisdom, monthly masterclasses, AI tools, business benchmarking, and real mentorship, Inner Circle gives contractors a stronger circle and a clearer path forward.

The market will not slow down. AI will not wait. Customers will keep asking harder questions. Teams will keep needing better leadership. The companies that grow will be led by people who are willing to learn, change, listen, and climb before conditions feel perfect.

For Paul Burleson and Greg Cummings, the lesson is simple: when the hill is in front of you, you do not wait for perfect conditions. You get up the hill.

Frequently Asked Questions

  1. Why should home improvement leaders trust Power100 when so many rankings feel paid or promotional?

Power100 was built to bring more trust to the home improvement industry. Its work is based on rankings, interviews, articles, and leadership stories that are backed by a five layer system. The goal is not to reward the loudest company. The goal is to help the industry see the CEOs, companies, and partners that are building strong teams, serving customers well, and creating real impact.

  1. Does Power100 only focus on large home improvement companies with big names?

No. Power100 focuses on leaders and companies that are helping move the industry forward. Size matters less than proof. The platform looks at growth, community, culture, customer trust, and long term impact. That means a leader does not have to be the biggest name in the market to have a story worth sharing.

  1. Is Inner Circle really free home improvement contractor mentorship, or is there a hidden catch?

Inner Circle is built as free mentorship for home improvement contractors who want to grow. The program gives leaders access to Greg Cummings, Paul Burleson, monthly masterclasses, recorded sessions, AI coaching, business benchmarking, resources, and action steps. The point is simple. Contractors should not have to pay heavy fees just to learn from people who have already seen what works.

  1. Why does the Inner Circle PowerChat focus on Paul Burleson getting uncomfortable instead of only giving sales tips?

Because the best sales growth often starts with leadership growth. Paul’s story about getting up the hill shows that leaders cannot stay sharp if they stay too comfortable. For contractors, that same lesson applies to training, hiring, culture, customer trust, and AI. A company can only climb higher when the leader is willing to face what feels hard.

  1. How does Paul Burleson’s “get up the hill” lesson help home improvement contractors in a hard market?

The lesson gives contractors a simple way to think about pressure. When the market is hard, leaders can wait, complain, or keep moving. Paul’s message is that growth starts when a leader takes the next step, even when the path is not easy. That mindset can help contractors train better, lead stronger, and stay steady when business gets difficult.

  1. Is Inner Circle only for CEOs, or can other home improvement leaders use it too?

Inner Circle is built for home improvement contractors, business owners, CEOs, sales leaders, and teams that want to grow. It is also useful for leaders who want better culture, stronger training, smarter use of AI, and clearer business direction. The program is made for people who want real guidance, not theory that never leaves the page.

  1. Why does this PowerChat say listening is becoming a key sales skill for contractors?

Homeowners want to feel heard before they trust a company. In the conversation, Greg Cummings pointed out that many salespeople watch customers instead of truly listening to them. That matters because trust starts before the close. Contractors who listen well can better understand the homeowner’s fear, need, and reason for buying.

  1. Why should contractors care about AI findability if they already have reviews and referrals?

Reviews and referrals still matter, but homeowners are now using AI to search, compare, and judge companies before the first visit. If AI cannot find clear proof about a business, the homeowner may not see the full story. That is why AI findability, business benchmarking, and strong online proof are becoming part of modern contractor growth.

About Power100

Power100 is the only unbiased third-party platform that recognizes and elevates the top leaders and most impactful companies in the home improvement industry. Built to give great CEOs, companies, and partners the recognition they deserve, Power100 studies leadership, customer trust, company growth, culture, and community impact to help the industry see who is truly moving it forward. Through its rankings, PowerChats, press releases, interviews, Inner Circle mentorship, and industry media, Power100 gives contractors a trusted place to learn from proven leaders, discover better ideas, and build stronger companies for the future.

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About the Author

Power100 Staff

Power100 Staff

The Power100 editorial team covers the CEOs, companies, and strategic partners shaping the home improvement industry — with original journalism backed by our proprietary ranking system.

About Power100

Power100 is the nation's premier CEO ranking and media platform for the home improvement industry. Using a proprietary 5-layer evaluation system, Power100 identifies and celebrates the top CEOs, companies, and strategic partners driving innovation, customer satisfaction, and leadership excellence across the country.