We sit down with the founder of TSO – Tree Service Owners, a free community of more than 11,000 companies growing 5% every month. Built by a 26-year industry veteran, TSO is a vendor-free, owner-only space designed for real questions, constructive conversations, and shared learning. With hundreds of posts and thousands of comments each month, plus webinars on growth, hiring, and operations, TSO has become a trusted place for tree service companies to help each other succeed, competitive, but united in wanting everyone to get better.

Shayna Shadowen grew up a third-generation electrical worker, and Jason married into the trade. After years in new construction and eventually running a service company, they discovered a need for better office support in small rural trades businesses. That led to My Office Help—an outsourced back-office and CSR solution built around powerful systems, including multiple CRMs, custom mapping, scheduling, QuickBooks Online bookkeeping, and even AI-powered phone answering. They now help small to mid-sized companies (up to ~10 trucks) handle calls, permits, dispatching, and more so business owners can “do what you do best and let us do the rest.

Caelan Newton grew up in a small town in Maine, discovering early on that sports weren’t his passion but hard work was. From summer deckhand jobs at 15 to concrete work, manual labor, and running around his dad’s crane shop, he developed a deep love for gear, machines, and the trades. After joining Lucas Tree, earning his CDL and Maine Utility Arborist License, and taking on major crane projects including one of the largest maples in the state, Caelan dove into residential tree work and expanded his skills across equipment and climbing. With just under five years in tree care, side work picking up, and a clear passion for the craft, Caelan is all-in on the industry and excited for a future filled with cranes, climbing, and continual growth.

Born and raised in California, Hank Ortiz built his career in sales and marketing before spending five years in Europe, where he met his wife and deepened his love for food, farming, and the outdoors. Combining his background in tech with his passion for agriculture, Hank set out to create software that made a difference. After realizing the challenges of selling to farmers, he pivoted to the landscape and eventually the tree care industry, where mapping, sensors, and data could truly shine. Out of that journey came Arbornote, a powerful yet simple tool for managing trees, proposals, sales, and workflows. Hank shares how he built software around three core principles: helping businesses stick with their customers, keeping it super easy to use, and offering unmatched support.

Join the Two Tree Guys for an Innovation Talk with Andy Jones, co-founder of Rooted Arbor Care, as he shares his real-world journey leading a tree care company into the battery-powered era. Andy dives deep into testing top brands like Milwaukee, Husqvarna, Stihl, EGO, Makita, and Greenworks, revealing what worked, what didn’t, and how his team optimized power management, charging setups, and crew efficiency in daily operations. Learn how Rooted Arbor Care achieved its best financial year yet while cutting fuel costs, improving sustainability, and proving that battery power can outperform gas in professional arbor work. From mobile charging systems to smart tool selection and scaling strategies, Andy’s insights redefine what’s possible for the modern tree care industry. ⚡🌳

Phil shares how Skylotec, a family-owned German manufacturer and Europe’s largest carabiner maker, has grown from its mountaineering roots into industrial fall protection and tree climbing innovations. With brands like Climbing Technology, Skylotec develops ascenders, fall protection systems, and rope-friendly gear designed to make climbing more efficient and safer. Their Colorado presence continues bridging sport and industry, backed by a strong R&D team working with climbers in the field to solve real-world challenges.

Rob Totaro, second-generation arborist and CEO of Tree Craft, shares his powerful story of resilience—from early struggles and addiction to recovery and rebuilding his life through tree work. With roots in a family business and a passion for safety, Rob is dedicated to professionalizing the industry while giving others a chance to start fresh.

Ian Lewis shares his journey from an unexpected start in Durango with the Conservation Corps to becoming a skilled climbing arborist. With early lessons on white pines in New Hampshire, mentorship, and a drive to self-educate, Ian built a career in technical removals and rigging—while passing knowledge on to other crews.

Jamie Mairs of Green-Tec shares how Terex entered the growing tree and vegetation management industry, focusing on mechanized arboriculture, safety, and efficiency. From tree handlers to spider lifts, Jamie highlights product innovation, dealer support, and the future of equipment shaping modern tree care.

Jason Pinegar shares his 30-year journey with West Coast Arborists, rising from a young snowboard bum in Big Bear to Vice President of one of the largest tree companies in the West. He reflects on his early break into the industry, lessons in safety and customer care, and a career dedicated to serving communities that value their trees.

An inside look at Tree Circus, the interactive traveling show inspiring kids and communities to connect with trees. From teaching everyday people how to climb, to planting the vision of big trees in parks across the world, the crew shares their journey as modern-day Johnny Appleseeds—bringing education, fun, and advocacy for trees to towns everywhere.

From welding to web development to equipment sales, Kyle Biancardi’s journey is anything but traditional. After breaking into crane safety training, he found his place in the tree industry and now sells BIK boom trucks and grapple saw trucks in the Northeast. Kyle shares how he’s helping revolutionize the industry by bringing new ideas and real value to his customers.

Wister Dorta shares insights from his journey through NYC Parks, California forestry permitting, and plant health care, bringing a unique perspective on balancing tree preservation with construction. He discusses helping arborists, architects, and contractors navigate permits, streamline paperwork, and follow best practices so projects move smoothly while supporting healthy soil and long-lived trees.

Jake Tietler shares Milwaukee’s journey into the tree care industry with their groundbreaking battery-powered saws. From four years of ground-up development to unmatched torque, power, and durability, Milwaukee is aiming to replace gas saws entirely—bringing safer, more productive tools to arborists worldwide.

From the mountains of northern Spain to the snowy forests of Germany, Vanesa Tilan’s journey is one of grit, passion, and breaking barriers. A lifelong athlete and adventurer, she traded nursing school for forestry, mastered the art of tree climbing without knowing a word of English or German, and stepped into international competitions to learn, connect, and inspire. In this episode, Vanesa shares how she’s encouraging women in Spain, educating others about the importance of trees, and living her dream among the treetops.

From climbing trees as a kid in Colorado to becoming a contract climber and business owner, Kyel Ciufi shares his wild and inspiring journey. After some rough patches and four years in the Army, he found his passion in urban forestry. Kyel talks about learning the ropes with Bartlett Tree in California, becoming a foreman with Davey in Colorado, and eventually launching his own company—Elevation Tree Service. Now a father of two, Kyel focuses on big prunings, safety education, and working for himself on his own terms.

Started in 1997, this Atlanta-based ISA-certified arborist and licensed insurance adjuster shares how he combined his experience to launch 707 Arborist and later, Clarity Market—a platform built to streamline tree service pricing, contracts, and disaster response. From crane deployments to pushing back on insurance adjusters, he’s redefining how homeowners and pros connect after a storm. Think eBay meets Uber, but for emergency tree work.

Greg Parsley grew up in Silver Spring, Maryland, where he launched into the green industry by fixing up discarded lawn mowers. After a brief brush with college, he followed his passion into remodeling, landscaping, and eventually tree care. In 2019, inspired by a friend in horticulture, Greg shifted his focus to arboriculture—earning his ISA certification and Maryland Tree Expert License. Now on his second tree service venture, he shares how he built his business from the ground up, one job and one license at a time.

Tom and Sonia dig into the power of handheld trenching with the GeoRipper and the impact of smart root barrier installation. From minimizing trip hazards in public spaces to preventing costly foundation and sidewalk damage, they share real-world insight on root control, equipment innovation, and what actually works in the field.

From dirt tracks to dive bars, Jennifer and Laura share their unlikely paths to Schaeffer’s, North America’s oldest lubrication company. Hear how a 19th-century candle and soap maker evolved into a modern lubrication powerhouse—and why they’re finally embracing marketing after nearly two centuries of boots-on-the-ground success.