Rich Oleck and Greg Cummings discuss why the future of the trades belongs to contractors who stay resilient, surround themselves with good people, build stronger support systems, and keep moving forward through change and pressure...
Rich Oleck, Building Trades Association President, joins Greg Cummings on Power100 PowerChat Outside The Lines to share why contractors must keep moving forward, face failure, build strong support systems, and lead with the right people through market pressure and change.
Power100 continues to bring fresh voices into the home improvement industry through PowerChat Outside The Lines, a special PowerChat series hosted by Greg Cummings, CEO of Power100. This series highlights leaders who may sit outside the regular home improvement company spotlight, but whose work still shapes the way contractors, builders, and trade leaders grow. In this featured conversation, Greg sat down with Rich Oleck, President of Building Trades Association, for a clear and timely talk about the mindset contractors need when business gets hard, markets shift, costs rise, and change becomes impossible to ignore.
Rich Oleck brings more than 40 years of building trades experience and has worked with more than 20,000 contractors across insurance, labor, service providers, products, and business support. His view reaches far beyond one company or one market. He has seen what helps contractors grow, what holds them back, and what separates the ones who keep moving from the ones who get stuck. That makes this PowerChat Outside The Lines episode a strong fit for Power100’s larger mission.
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 this conversation, Power100 brings a wider industry voice to contractors who need real insight, trusted guidance, and a clear reminder that the best trade businesses are built by people who keep going, keep learning, and keep good people around them.
This PowerChat conversation with Rich Oleck was part of PowerChat Outside the Lines, a special PowerChat segment that brings trusted leaders from outside the regular home improvement CEO spotlight into the room. The purpose of Outside the Lines is simple. Leadership lessons can come from many places. Sports, military, business, small company growth, and the wider building trades can all teach home improvement leaders how to think better, lead better, and build stronger companies.
For this episode, Greg Cummings sat down with Rich Oleck for a direct and useful conversation about what contractors need most right now. The talk did not center on quick wins or easy answers. It centered on the things that help a trade business last. Resilience. Good people. Better planning. Smarter support. And a steady will to keep learning when the market becomes hard to read.
Rich Oleck brought a view that fits the heart of PowerChat Outside the Lines. His work reaches beyond one company, one trade, or one market. As President of Building Trades Association, he has seen how contractors respond when costs rise, laws change, insurance gets harder, technology shifts, and labor stays tight. That made his voice valuable for home improvement leaders who want to understand what strong companies do before pressure breaks weak systems.
The industry relevance of the conversation came from how real it felt. Greg and Rich spoke about the pressure contractors face every day, from interest rates and service providers to AI, insurance, skilled labor, and long term planning. But the message was not heavy. Rich kept bringing the conversation back to a clear truth. Contractors who keep going, surround themselves with good people, and use the right support systems are better built for the future.
The scale and impact of this episode came from Rich’s wide lens on the trades. His experience with thousands of contractors gives the conversation weight because he is not speaking from one narrow view. He is speaking from years of watching what helps trade businesses grow, what holds them back, and what separates the leaders who adjust from the ones who freeze.
When Greg Cummings sat down with Rich Oleck, the heart of the conversation was simple. Contractors are facing pressure from many sides. Costs are moving. Laws change. Interest rates rise. Technology is shifting. Customers are slower to act. Labor is still hard to find. But Rich did not speak like a leader who believes pressure should stop a good contractor. He spoke like someone who has seen the building trades long enough to know that the best leaders keep moving, even when the road is not easy.
Through the interview, Greg guided the conversation into the real issues trade leaders face every day. Rich answered with clear lessons from more than four decades around contractors, service providers, insurance, labor, and business support. His view gave the episode a strong message for every contractor who wants to build a stronger company. Resilience matters. People matter. Planning matters. And no contractor should try to build a lasting business alone.
Rich opened the conversation by going straight to the mindset of contractors who win. He said the best ones are not the leaders who never fail. They are the ones who do not let failure stop them. That point became the emotional center of the interview because it speaks to what many contractors are feeling right now. A missed sale, a bad season, a slow market, or a wrong decision can make an owner question everything. Rich’s message was that failure can be part of the path, not the end of it.
He compared that kind of mindset to Thomas Edison, who kept trying even after many failed attempts.
Rich said, “Well, their mindset is basically that you can’t be afraid of failure because as what happened with Thomas Edison, he made 4,000 inventions, 4,000 patents to get 400 things that really changed the world.” Rich Oleck, President, Building Trades Association.
That quote gave the conversation a strong lesson for contractors. The work of building a company is not clean or easy. A contractor may lose a bid. A team member may leave. A supplier may raise prices. A new law may change how the business runs. But the leaders who last do not stop at the first hard thing. They learn, adjust, and keep going.
For trade leaders, this is also a reminder that grit is not just about working longer hours. It is about staying steady when the business feels uncertain. Rich’s point is not that failure feels good. It is that failure does not have to define the company. In the trades, hard seasons can teach leaders where the business is weak, where the team needs support, and where better systems are needed.
This is where Rich Oleck contractor business leadership becomes so useful for today’s market. His message gives contractors a way to see pressure with clearer eyes. The goal is not to avoid every problem. The goal is to keep building through the problem with the right mindset and the right people around the company.
Explore more contractor leadership conversations from Power100
Rich made it clear that resilience is not a solo act. Contractors need good people around them if they want to grow through hard seasons. That includes the people on the team, the vendors they trust, the advisors they call, the insurance partners they work with, and the service providers who help protect the business behind the scenes.
He said, “You have to get good people around you and you have to keep trying no matter what happens.” Rich Oleck, President.
This matters because many contractors start with skill. They know how to sell. They know how to install. They know how to manage a job. But as the company grows, skill alone is not enough. The business starts to need better support. It needs people who understand money, insurance, legal needs, labor, project flow, customer care, and risk. Without that support, the owner can become the only person holding the company together.
Rich’s point also connects to the reason many contractors look for a contractor business association for builders and remodelers. They are not just looking for a name to join. They are looking for help that makes the company stronger. They need resources that save time, reduce risk, and make it easier to run the business with more confidence.
Greg’s interview gave this idea more weight because it showed that leadership is not only about the person at the top. It is also about the circle around that leader. A contractor who surrounds the business with weak support will feel every problem harder. A contractor who builds with good people will have more room to think, plan, and act before pressure becomes a crisis.
For home improvement leaders, this is a simple but powerful lesson. No company scales alone. The partners a contractor chooses today can shape how well the company survives tomorrow.
Learn how Building Trades Association supports contractors
The conversation also moved into technology and AI, but Rich kept the message grounded. He did not say every contractor needs to chase every new tool. He said leaders need to stop resisting what they do not understand. That point matters because many small and mid size trade companies are still unsure about how technology fits into their business.
Rich said, “If you don’t know the technologies, you should probably hire somebody who does and become familiar with them.” Rich Oleck.
That line is important because it makes change feel practical. Contractors do not need to pretend they know everything. They need to stay open enough to learn and wise enough to bring in people who know more than they do. That could mean help with marketing, lead follow up, appointment setting, customer service, office systems, or better use of data.
Rich also made it clear that construction will not change in the same way as every other industry. Robots may not replace skilled workers on job sites anytime soon, but AI is already changing the back side of the business. It can help with leads, calls, service, and marketing. That means contractors who wait too long may not lose because they cannot swing a hammer. They may lose because another company answers faster, follows up better, or markets smarter.
This perspective fits the larger message of the interview. Keep moving forward does not mean running blindly into every trend. It means staying awake. It means learning before the market forces the lesson. It means asking who can help instead of pretending the old way will always work.
A contractor who keeps learning is better prepared for the next shift. A contractor who refuses to learn may only realize the market changed after the best chances have already passed.
See more PowerChat insights for contractors and industry leaders
Rich also gave a clear warning about the money side of the trades. He talked about outside forces that can change a contractor’s business fast. War, oil prices, supply chains, inflation, material costs, interest rates, steel, copper, concrete, HVAC equipment, and longer lead times can all affect job costs and profit.
He said, “The most successful ones are probably figuring out the impacts of some of these things because you have to plan for them.” Rich Oleck, President, Building Trades Association.
This was one of the most practical parts of the interview. Rich was not trying to make contractors afraid. He was showing them why early planning matters. If costs rise and a contractor does not plan, the business may be forced to absorb the hit. If lead times grow and the company does not prepare the customer, trust can break. If fixed price contracts are not built with care, a job that looked profitable can become painful.
Greg and Rich’s exchange made one idea clear. The best contractors do not just react to the market. They study what is changing and adjust before it is too late. That could mean reviewing pricing, checking contracts, watching material costs, talking to vendors, or setting clearer timelines with customers.
This is also where strong support systems become more than a nice idea. Contractors need people who can help them see what is coming. They need vendors who share updates. They need insurance partners who explain risk. They need office systems that show the numbers. They need trusted voices who can help them make better choices before pressure hits the bottom line.
Keeping moving forward is not the same as pretending everything is fine. It means leading with open eyes. It means seeing the risk, naming it, and building a plan around it.
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One of Rich’s strongest lessons came when the conversation turned to insurance. He explained that many contractors do not like buying insurance and often see it as a speed bump. For some, it feels like something they only do because the state requires it. But Rich showed why that mindset can create serious problems as a company grows.
He explained that insurance costs are tied to many parts of the business, including revenue estimates, trade type, claims history, and audits. If a contractor gives the wrong revenue number, grows faster than expected, or fails to plan for the end of year audit, the company may face a large bill later.
Rich said, “These are some of the things you kind of want to be aware of and possibly work with your agent or the insurance company directly with.” Rich Oleck, President, Building Trades Association.
That advice matters because many contractors are strong in the field but less trained in the back office. They may understand the work, the customer, and the crew, but not always the insurance rules that can affect cash flow. Rich’s point was that leaders should not wait until an audit creates stress. They should talk to the right people early and understand what their numbers mean.
This also shows why a contractor insurance association for general liability and workers can be valuable to trade business owners. Insurance is not only about having a policy. It is about knowing how that policy works, how the business is being measured, and how growth can change what the company owes.
For contractors, this PowerChat gave a needed reminder. Sales and installation may bring in revenue, but the business side protects that revenue. A strong company needs both.
Find contractor support resources through Building Trades Association
Near the close of the conversation, Rich turned toward the future of the trades. His view was hopeful, but also honest. He believes the industry needs more young people, more trade school paths, more hands on learning, and more skilled subcontractors.
He said, “Not everybody’s meant for college. Some people are meant, some people should go to trade schools.” Rich Oleck, President.
This point gives the whole interview a larger meaning. Contractor success is not only about the owner’s mindset today. It is also about who will build tomorrow. Rich talked about how high schools used to offer more shop classes, mechanics classes, and trade school connections. He believes those paths need to come back so young people can find careers that match their gifts.
Greg connected with that idea because hands-on learning can reach students in a way a classroom may not. Some people learn best by doing. Some young people may find purpose, income, freedom, and pride through the trades. But they need access, support, and a clear path.
Rich Oleck on the future of construction and skilled trades is a hopeful message because it does not treat people as replaceable. Even with AI and robots, construction still needs human skill. Homes, roofs, systems, repairs, and projects still need people who know how to build, solve problems, and work with their hands.
The future of the trades will depend on more than new tools. It will depend on new talent. It will depend on leaders who make the industry worth joining. It will depend on companies that train, support, and respect the people doing the work.
That made Rich’s closing insight a strong fit for the whole conversation. Contractors must keep moving forward, but they must also help the next generation move forward with them.
The value of Rich Oleck’s message is not only found in what he said during the interview. It is also seen in the work he has built around contractors for nearly four decades. As Rich Oleck Building Trades Association President, his role has centered on a clear idea. Contractors should not have to face growth, risk, costs, insurance, marketing, bidding, and business pressure by themselves.
That belief has shaped Building Trades Association since 1986. Under Rich’s leadership, the association has grown into a support network for thousands of companies across the building and construction industry. Its work gives contractors access to group level resources, trusted service providers, business tools, and member benefits that many smaller companies may not be able to reach on their own.
That matters because many contractors are skilled at the work, but they often need stronger help around the business. A remodeler may know how to serve a homeowner. A roofer may know how to lead a crew. A builder may know how to manage a job site. But as the company grows, the back office starts to matter more. Insurance, leads, contracts, marketing, payroll, compliance, collections, and vendor savings can all shape whether the company stays healthy.
This is where the work of Rich Oleck and Building Trades Association connects back to the heart of the PowerChat. Rich told contractors to keep going, but he also told them to surround themselves with good people. That is what the association is built to help provide. It gives trade business owners a wider circle of support so they can make better choices, save time, reduce stress, and protect the company they are trying to grow.
BTA’s reach also shows why its model is important to the industry. Rich’s career has touched construction, advertising, energy, insurance, sports, and digital marketing. He has also worked alongside high profile names such as NFLPA, NBAPA, Allstate, Home Depot Pro, and other major partners. That range gives him a wide view of how strong brands, strong partnerships, and smart member services can help businesses move forward.
For contractors, the impact is practical. Through one membership, companies can access support tied to health insurance, commercial insurance, lead generation, digital marketing, social media, project bidding, and other business needs. The association also offers a trusted directory of building and construction professionals, helping clients and companies connect across the United States.
At $299 per year, with membership positioned as a tax deductible business expense, Building Trades Association for contractors is built around access. It gives smaller and growing companies a way to tap into negotiated benefits and contractor membership benefits for forms, contracts, insurance, savings, and business support without carrying the full weight alone.
That is why Rich’s message lands with real force. When he tells contractors to keep moving forward, it is not just a phrase. It reflects a career spent building tools, partnerships, and support systems that help trade companies do exactly that.
Learn more about Building Trades Association and its contractor resources
As the conversation came to a close, one message stood above everything else. The building industry may keep changing, but the foundation of a strong contractor has not changed. Good leaders still need grit. They still need good people around them. They still need planning, support, and the willingness to keep learning when the market becomes uncertain.
Throughout the PowerChat Outside The Lines interview, Rich Oleck never ignored the real pressure contractors are facing. He spoke openly about rising costs, changing laws, insurance challenges, labor shortages, material delays, and the way technology is reshaping business. But even with all of that change, his view of the trades remained hopeful.
Rich believes construction still matters because people will always need skilled workers who can build, repair, solve problems, and create something real with their hands. He believes the industry still needs strong subcontractors, better support systems, and leaders willing to guide the next generation into the trades. Most importantly, he believes the contractors who survive long term will not be the ones waiting for easier conditions. They will be the ones who keep adapting, keep learning, and keep showing up when things get hard.
That is what made this conversation bigger than one company or one market. Rich Oleck’s message speaks to every contractor trying to lead through uncertainty. Pressure will always come. Markets will shift. Technology will continue to evolve. But the businesses that stay steady through those moments are often led by people who refuse to quit when the environment changes around them.
In many ways, the interview served as a reminder of what has always made the trades strong. The industry moves forward because builders, remodelers, subcontractors, and skilled workers continue finding ways to solve problems even when the path is difficult. They keep learning. They keep improving. They keep helping one another. And they keep building.
For contractors listening to this PowerChat, Rich’s perspective leaves behind a clear challenge and a clear hope for the future. Keep moving forward. Keep good people close. Keep building systems that protect the business. Because the future of the trades will belong to leaders who are willing to grow through pressure instead of running from it.
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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.
