Hard Hat to CEO with Chris Gilman

What if just 15 minutes could save you 25 years of headaches, wasted money, and burnout? In this episode of Hard Hat to CEO, Chris G keeps it real and shares six lessons he's learned the hard way, so you don’t have to. From knowing when to walk away from the wrong clients to making sure you’re actually making a profit (not just chasing big numbers), this one’s full of real talk. Chris also explain...

What would happen if you couldn’t show up to work tomorrow? Would your business keep going, or would things fall apart? In this episode of Hard Hat to CEO, Chris G chats with Pete Mohr, host of the Business Owner Breakthrough podcast, about why every business owner needs an exit plan, and no, it’s not just for retirement. Pete shares real-life stories of business owners who had to step away sudden...

What if you could make more money on every job while keeping your customers happier than ever? In this episode of Hard Hat to CEO, Chris G. talks about simple ways contractors can stand out, like offering extra services the same way a mechanic suggests new wipers or an air filter. He shares how partnering with designers, smart home pros, or financing experts can add value without adding more work....

What’s getting in the way of your goals, and are you really dealing with it? In this episode of Hard Hat to CEO, Chris G sits down with retired executive Jerry Fish to talk about something he calls the Black Dot Philosophy. It’s a simple way to spot the things holding you back and actually do something about them. Jerry shares his own tough story of losing family, going through a divorce, filing f...

Ever lie awake at night wondering how you’re going to cover the bills? Chris G. knows that feeling all too well. In this episode, he shares real-life stories and easy ways to take control of your cash flow. Whether it’s billing more often, using an escrow account, or making sure you actually hit “send” on that invoice, Chris breaks it all down in a way that makes sense. He also talks about how to...

Mobile Home Parks Might Be the Best Investment You’re Overlooking with Tim Woodbridge Ever wonder how to make your money work harder for you? In this episode of Hard Hat to CEO, Chris G talks with Tim Woodbridge, a former nurse who now owns 19 mobile home parks. Tim shares how one book, Rich Dad Poor Dad, completely changed how he thought about money and helped him start building real wealth. He e...

Have you ever come home from the hospital only to fix a doorknob that someone else was paid to install? That’s exactly what happened to Chris G., sparking a broader conversation about why many business owners become overwhelmed by doing everything themselves. In this episode, he shares what it really takes to step away from your business without fearing it will fall apart. From learning to delegat...

What really makes a team successful — having the best players or having real trust? In this episode of Hard Hat to CEO, Chris G talks with Mike Robbins, a former pro baseball player who now teaches leaders how to build strong teams and better workplaces. Mike shares his story of going from the pitcher’s mound to a career-ending injury, and how that shift led him to focus on people, culture, and le...

What does it really feel like to start over at 40? On this episode of Hard Hat CEO, Chris G chats with Dennis Mark Interdonato, a former contractor who left his family’s construction business to start fresh in real estate. Dennis shares what it was like going from digging holes to building a successful real estate brand, and how that journey changed his life. He opens up about his struggles, how h...

Are your prices helping you earn trust or pushing customers away? In this episode, Chris G. shares a story about a contractor who tried to hide extra profit in material costs and ended up losing credibility. Chris explains why honesty matters in business and how small changes can make a big difference. From slowly raising your prices, to cutting waste, to getting better deals from suppliers, he la...

What if your biggest cost isn’t tools or materials, but people quitting? In this episode of Hard Hat to CEO, Chris G talks with Francie Jain, Founder of Terawatt, about what really keeps good workers around. They get into real stories, including how one hospital cut its turnover from 24% to just 4%, saving millions by focusing on trust, communication, and team culture. Whether you’ve got a small c...

What really makes a contractor stand out? In this episode, Chris G tells a real story about meeting with a couple who wanted a truly custom home—not just the usual options. From swapping out a pricey fireplace for a better fire pit to helping them get financing, Chris explains how listening and offering honest advice can make all the difference. He also shares five ways contractors can set themsel...

In this episode of Hard Hat CEO, Chris G. talks with landscape architect Matthieu Mehuys about how nature can give you a serious edge, whether you’re building homes, developing land, or just want to cut costs. Matthieu shares how his journey from growing up on a farm to working on projects around the world taught him that smarter landscaping can mean less maintenance, lower costs, and way more val...

Ever get a phone call that just ruins your whole day? Chris G. knows the feeling, and in this episode, he talks about one of those moments that made him stop and think. If you're a busy contractor getting calls about stuff that should’ve already been clear, this one’s for you. Chris shares how better communication can save you time, stress, and money. He talks about his Amish crews and how they ha...

What if people wanted to work with you before you even made a pitch? In this episode of Hard Hat to CEO, Chris G. talks with Jerry Gennaria, CEO of Toky, about how contractors, builders, and engineers can build a brand that makes sales easier. Jerry breaks down how to figure out what really makes your business different, even if it feels like you’re saying the same thing as everyone else. You’ll l...

What do you do when things don’t go as planned, your order’s wrong, a delivery’s late, or a client’s not happy? In this episode of Hard Hat to CEO, Chris G tells some personal stories that show how the way you handle those moments really matters. Whether it's an Amazon mix-up, a fender bender, or a missing part from Lowe’s, Chris talks about staying calm, being kind, and not jumping to blame. Cust...

What if you could legally keep up to 90% of the money you're currently handing over in taxes? In this episode of Hard Hat to CEO, Chris G welcomes real estate investor and trust expert Sally Gimon, who shares how she turned a $94,000 tax crisis into a tax-saving mission that now helps entrepreneurs, contractors, and investors slash their tax bills. Sally breaks down how an IRS-compliant structure...

Ever feel like life hits you with everything all at once? Well, in this week’s episode of Hat to CEO, Chris G makes it as real and raw as it gets. He shares a week that tested every nerve. From a granddaughter’s broken arm and a daughter’s scary hospital visit to work chaos, missed meetings, and even losing a right-hand teammate. But instead of crumbling, he leans into prayer, sunshine, barefoot w...

What if your architect actually knew how to build? In this episode of Hard Hat to CEO, Chris G chats with Lance Cayko, an architect and builder from Colorado who’s done everything from tiny homes on HGTV to multi-million dollar custom builds. Lance talks about the real differences between commercial and residential work, how he handles change orders, and why being both designer and builder just ma...

What do you do when your business starts growing, but you're not sure how to keep up? In this unscripted episode, Chris G talks honestly about what he’s learned over the last few months. He shares how he went from doing estimates by hand to using new software that gets quotes out in hours. He also opens up about hiring the right people, learning to listen more, and why talking about what you do re...

What if your crew actually cared about working faster, doing better work, and showing up ready without you having to ride them? In this episode of Hard Hat to CEO, Chris G sits down with Michael Fortinberry, a contractor-turned-software-founder who figured out how to get his team to work like owners. He shares how he grew his NYC construction business from a small painting crew to 130 people in th...

What would happen if your business had to keep going without you starting tomorrow? In this episode, Chris G shares a raw, personal story about almost losing his life and the mess it left behind for his family. That terrifying experience became the push he needed to rebuild his business so it could stand on its own. From lying in a hospital bed with no systems, no plan, and no backup, to creating...

Ever lie in bed with your mind racing, even though you're completely wiped out? In this episode of Hard Hat CEO, Chris G chats with Irina Alexander, a former HVAC business owner who now helps people handle stress and build emotional strength. She talks about hitting burnout, how she turned things around, and what she wishes she knew back then. They get real about why sleep can be tough, how stress...

In this off-the-cuff episode, Chris G shares what the past few months have looked like, what’s worked, what hasn’t, and what he’s changing. From estimating jobs on his own to hiring full crews and investing in new software, he’s learning that as the business grows, he has to grow too. You’ll hear about tough calls, big wins, and small mindset shifts that made a difference. If you’re feeling overwh...

Got a piece of land but no clue what to do with it, or just no time to figure it out? In this episode, Chris G sits down with Eugene Gershom, a real estate developer out of Bellevue, Washington, who’s shaking things up. Instead of buying land himself, Eugene teams up with landowners to help them actually build on what they’ve got. He shares how most people dive into development thinking it’s simpl...