Roofing Owners: The Builders Behind Aaron Christy, Bob Schober, Brad Strawbridge and Dustin Gutkowski

Aaron Christy

Founder and President, Indy Roof & Restoration — Indianapolis, IN

Official links: Website · LinkedIn · Facebook

Aaron Christy did not set out to be a roofer. He spent most of his professional career in his family’s educational publishing business, joined a small roofing company, then left to open a furniture store — and the roofing work kept finding him anyway, as real estate agents continued calling for help with closings that had roofing issues.

In 2018 he opened his own roofing company, discovered he liked it far more, closed the furniture store and went all in.

What he built next is the part other roofers repeat: he swapped a $50,000 salary, reinvested every penny, and hit nearly $10 million in revenue by year three — then had to learn, in public, how to build operations that could carry the sales.

“We hire on culture first. You can teach almost anybody to do just about anything. But what you can’t teach is culture and I think that’s the most important thing to hire on.”

The culture came first because Christy knew the alternative from the inside: an earlier job had left him dreading each workday and counting down the hours, and he set out to build a workplace where people genuinely wanted to be.

He hired an integrator partner to complement his visionary drive, overhauled systems so the team could handle $15 million in annual volume, built reserve accounts that cover monthly payroll, and made “inspect what you expect” his mantra.

Underneath the growth sits an old family-business discipline he carried over from publishing: show up when you say you will, deliver what you promised, and stay in constant contact — he even wrote a short book to walk homeowners through the insurance-claim process. Growth, in his telling, was never the hard part. Growing up as a company was.

No Suits Allowed (Listen Notes) — “Breaking the $10M Ceiling: Aaron Christy of Indy Roof & Restoration”
People Forward Network — “Building a Culture of Growth”
Roofing Contractor — “Contractor Profile: Indy Roof Company”

More from The Bourgeois Society: The full list  ·  Tracy Bookman  ·  Bob Schober

Bob Schober

ProWest Roofing — Mesa, AZ

Official links: Website · Facebook · Instagram · X

Bob Schober ran away from home at 15, went through rehab young, and spent years drifting across the country following the Grateful Dead — living out of a Volkswagen bus, showering in public parks and selling food stamps, yet still reading Think and Grow Rich in the middle of it.

The turn came in stages: rehabs, false starts, and a moment in Los Angeles when an old friend threw his towel in the trash after he showered and told him he was disgusting. He did not get sober that day, but the mirror had been held up.

By May 31, 1997, he had taken his last drink — and sobriety became the foundation for how he would build, lead, hire and give.

“The only thing I never really let go of was hope.”

Schober helped grow ProWest Roofing from a modest acquisition into a company that sold for $51 million in 2022; the operation went on to report $189 million in sales in a single year, across 20 states with roughly 600 salespeople.

The most revealing part is who he bet on once he had power: many of his sales reps are in recovery, and many have served time in prison.

With Adam Tronnier, whose idea it was to bring roofing-sales training inside prison walls through apps inmates can use, he co-built From the Yard to 100K — a program that lets people still serving sentences learn from former inmates who rebuilt their lives in roofing sales, and even practise their pitches before release.

Some of those hires have become top performers earning hundreds of thousands a year. His giving runs the same way: after winning $10,000 at baccarat, he gave it away on the roadside to strangers who honked — the seed of the 9 Figure Roofer kindness movement he now leads.

LA Weekly — “Bob Schober: The Roofer Who Built Second Chances”
9 Figure Roofer — official site (Bob Schober)
International Business Times (via FinancialContent) — “One Video, One Friend, and $50,000: The Holiday Act of Kindness That Started 9FigureRoofer”

More from The Bourgeois Society: The full list  ·  Aaron Christy  ·  Brad Strawbridge

Brad Strawbridge

Founder and CEO, Capital City Roofing; Co-founder and CEO, BuilderLync — Alpharetta, GA

Official links: Website · LinkedIn · Facebook · X

Brad Strawbridge came to roofing with a decade of executive leadership behind him, including senior roles at Lowe’s overseeing large-scale in-home services — and then scaled Capital City Roofing, his Alpharetta residential, multifamily and commercial roofing company, to a multimillion-dollar operation in about a year.

The speed came from systems, not shortcuts: he trained AI on his own pricing until seven to ten days of commercial estimating became a one-day job, on the belief that the point is to let one trained person do what used to take a whole team.

He serves on the board of the Roofing Technology Think Tank (RT3) and co-founded BuilderLync, an AI-driven CRM and operating platform for contractors. And he founded the Feeding the Future Project, a nonprofit funded by his roofing operations.

“You’re just adding members to your team to make your existing team members more productive,”

Strawbridge is now trying to hand his playbook to the whole trade.

Capital City’s licensing platform lets established roofers operate as “powered by Capital City Roofing” on franchise-style economics he argues are fairer: a $15,000 buy-in against the typical $50,000 franchise fee — with the buy-in going to the Feeding the Future Project instead of to corporate — and royalties of 5% against the usual 10%.

The company describes running roughly 80 in-house AI agents across lead intake, scheduling, customer communication and back-office work, and the nonprofit channels a minimum of 1% of Capital City Roofing revenue into school partnerships and student lunch programmes across metro Atlanta.

A roofer who automated the estimating desk, in other words, spends the proceeds feeding schoolchildren — and teaches other roofers to do the same.

The AI and Marketing Show for Home Service Pros — “How One Roofer Bids Commercial Jobs in a Day With AI” (guest bio)
Roofing Contractor — “The Race to Own Roofing’s Operating System”
Local Service Spotlight — “How Brad Strawbridge Scaled Capital City Roofing to $10M With AI”

More from The Bourgeois Society: The full list  ·  Bob Schober  ·  Dustin Gutkowski

Dustin Gutkowski

Founder and CEO, Results Roofing — Dallas, TX

Official links: Website · LinkedIn · Facebook · Instagram · X

Dustin Gutkowski grew up outside Austin never knowing his father, in a house filled with drugs and abuse, and ended up homeless at fourteen. He tells that story in his own words, without softening it — and then tells you what it built in him: a determination to become the husband and father whose example he never had.

He left a career in fitness to build a business that would let him grow and give his family more of his time, and founded Results Roofing in Dallas. Within four years he had built it to around $100 million, on a guiding principle his podcast hosts quote back to him: impact over income.

“Our goal has never been to simply become the biggest roofing company in the country.”

Results Roofing, founded in 2019 and headquartered in Dallas, is now a TZP Group portfolio platform serving homeowners across Texas, California, Georgia, North Carolina and South Carolina, with an in-house claims team and a proprietary sales-training programme.

Gutkowski grew it the people-first way — focusing on hiring well and keeping his team happy and motivated — and his own explanation of the work has stayed constant as the map widened: every acquisition starts with culture, and the aim is a company where people can grow, become owners and change their families’ lives.

The boy who was homeless at fourteen now says, plainly, that being a father is the thing he is proudest of in the world. The empire is second.

Shoutout DFW — “Meet Dustin Gutkowski | CEO — Results Roofing”
Rental Property Owner & Real Estate Investor Podcast (Listen Notes) — “EP436: From Homeless to $100M with Dustin Gutkowski”
TZP Group — “Results Roofing, a TZP Group Portfolio Company, Acquires Journey Builders”

More from The Bourgeois Society: The full list  ·  Brad Strawbridge  ·  Eric Oberembt

Eric Oberembt

Owner, D&M Roofing and Siding — Omaha, NE

Official links: Website · LinkedIn · Instagram · Facebook

Eric Oberembt was on roofs at ten years old, working and selling tar roofs alongside his grandparents. By his mid-twenties he had taken over half of his grandfather’s business, and when his grandfather passed he bought the rest — a third-generation owner of the family company in Omaha. He was also an alcoholic.

After two failed marriages the wheels came off: deeper addiction, cocaine selling at twenty-eight, and up to five years of jail time facing him for a fourth-offence DUI. On his lawyer’s advice he chose a 30-day rehab to avoid jail, got sober, relapsed — and then changed his life completely.

Today he runs a multi-million-dollar roofing company, and the recovery that saved him became a mission aimed at the whole trade.

“We helped them and sent them into treatment, and then all of a sudden the phone kept ringing,”

Oberembt co-founded Roofers in Recovery with fellow roofer Raymond Wendell Little, and the founding story is disarmingly small: two sober company owners on the phone, each throwing in his own money to send one roofer in the industry to rehab. It worked — and then, as Oberembt tells it, the phone kept ringing.

Roofers in Recovery is now a nonprofit that pays 100% of rehab costs for roofing contractors battling addiction and gives practical help to their families, so the person in treatment can devote everything to getting well.

Oberembt, who also writes and speaks on authentic leadership, puts the reason plainly in the organisation’s own telling: at some point in their own recoveries, someone stepped up for them. This is them stepping up, at scale, for everyone still on a roof and struggling.

The American Reporter — “Learn How Eric Oberembt Beat the Odds to Become Successful, Sober, and Help Others”
Disrupt Magazine — “How Eric Oberembt Went From Jail to Inspiring Others”
Roofing Contractor — “Roofers in Recovery Offers Roofing Contractors Help”

More from The Bourgeois Society: The full list  ·  Dustin Gutkowski  ·  Skye Williams

Skye Williams

Founder & CEO, Samurai Roofing Services — Houston, TX

Official links: Website

We’re inspired because Skye Williams tells the unvarnished version on purpose — no pink, no pretty — so other women facing the same diagnosis feel less alone. She kept her company standing through the hardest year of her life and came back to national recognition, and she still personally supervises jobs so homeowners deal with the owner, not a stranger.

“Breast cancer was not soft with me. It hurt. It scared me. It changed my body.”

Williams founded Samurai Roofing Services in Houston, serving the city plus 13 surrounding communities as an Owens Corning Preferred Contractor and a Houston Chronicle Best of the Best top-3 finalist.

Then the founder who climbed roofs 40–60 hours a week was told she had Stage 2B triple-positive breast cancer: twenty-one infusions, 33 radiation treatments, surgeries and lymph nodes removed — at her weakest she needed a wheelchair.

She kept the company standing anyway, and was named a QXO Female Roofing Professional of the Year finalist, one of five chosen from more than 1,000 nominations across the U.S. and Canada. Her first-person account is titled “I Became The Awareness.”

BusinessWire — “QXO Announces Five Female Roofing Professional of the Year Finalists”
Roofing Contractor — “QXO Announces Five Female Roofing Professional of the Year Finalists”
Skye Williams — “I Became The Awareness”

More from The Bourgeois Society: The full list  ·  Eric Oberembt  ·  Justin Escajeda

Justin Escajeda

Owner, Escajeda Holdings — Pittsburgh, PA

Official links: Website · LinkedIn

Justin Escajeda tells his early life without decoration: drawn to the street life young, he spent roughly fifteen to twenty years doing illegal things, became addicted to drugs, and hit the bottom the word actually describes — homeless, no money, every relationship shot, walking the train tracks with a bag holding all his belongings.

Getting clean and going legitimate, he has said, was very difficult — doing things the correct way, by the book, after years of doing them the other way. What he did with the second chance is the story: he became a union bricklayer, then built his own company doing niche masonry work, starting from side jobs in his native Pittsburgh.

“Bringing Alex Restoration & Masonry Repairs under the Escajeda Masonry & Concrete umbrella is a strategic move that aligns seamlessly with our long-term vision for growth,”

About five years into the masonry company, a local roofing owner named Al, ready to retire quickly, asked Escajeda to buy him out: $600,000 of seller earnings for a purchase price of $846,000. He took the deal, it worked, and it opened his eyes to a whole model of growth.

He now owns eleven companies, going on twelve — masonry, roofing, remodeling and more — with 250 W-2 employees plus dozens of contract workers, no outside investors, and, in the Acquiring Minds host’s estimate, revenue easily clearing $50 million a year.

His method is restraint: he keeps the acquired companies’ names, logos and teams, and lets them keep running the way that made them worth buying — as with the Alex Restoration acquisition, which deepened the group’s historic-preservation expertise. A dozen companies, owned outright, by a man who once owned a bag on the train tracks.

Acquiring Minds — “Bricklayer to Blue-Collar Empire” (Justin Escajeda, Escajeda Holdings)
BiggerPockets Podcast (Ep. 123, transcript) — “Overcoming an Ugly Past to Become a Cash Flow King with Justin Escajeda”
BusinessWire — “Escajeda Masonry & Concrete Grows Footprint with Acquisition of Alex Restoration & Masonry Repairs”
Roofing Insights (YouTube) — “13 Companies. $50 Million. This Is NOT How You’re Supposed to Build a Construction Empire!” (video)

More from The Bourgeois Society: The full list  ·  Skye Williams  ·  Miguel Taveras

Miguel Taveras

Co-founder, Blue Hammer Roofing — Dallas, TX

Official links: Website · LinkedIn · Instagram

Miguel Taveras started in a different kind of precision work: an electrical engineering degree from the University of Florida, a background in tech consulting and time at the U.S. Patent and Trademark Office. He sold his tech consulting company — and then, by his own account, he was bored.

So he joined a roofing company, started his own, and set an outsized goal: to become the number one player in insurance-based re-roofing, in an industry with a bad reputation, by doing the opposite of what earned it that reputation.

He worked seven days a week with an all-in mentality, wearing every hat in the business until he learned which people to hire for each one.

“You just have to do what you say and say what you do.”

Blue Hammer Roofing, founded in Dallas in 2019 by Taveras with co-founders Nehal Kaiser, Maria Nguyen, Christian Jimenez and Freddy Murphy, became the fastest-growing roofing company in the nation: 15,911% three-year growth, earning the No. 17 spot on the Inc. 5000 list.

Under their leadership the company completed more than $150 million in roofing sales and helped approximately 10,000 homeowners with storm-related roof repairs. In 2023 Blue Hammer was acquired by RAFTR Roofing + Exteriors, the multi-regional platform built around insurance-claim work — and Taveras stayed to run the playbook at national scale, becoming RAFTR’s Chief Sales Officer.

The engineer who left patents behind did not leave the precision behind; he just pointed it at an industry that needed it.

Business Legacy Podcast — “Ep 116: From Patents to Roofing: Miguel Taveras’s Journey to Business Expansion”
BusinessWire — “RAFTR Roofing + Exteriors Names Miguel Taveras Chief Sales Officer”
Roofing Contractor — “2022 Inc. 5000 List Recognizes More Than 40 Roofing Contractors”

More from The Bourgeois Society: The full list  ·  Justin Escajeda  ·  Raymond Wendell Little

Raymond Wendell Little

Co-founder, Perimeter Roofing — Duluth, GA

Official links: Website · Facebook · Instagram

We’re inspired because Raymond Little argues — with his own life as the evidence — that roofing is the best second-chance industry in America. His companies run a strict no-drugs, no-alcohol, fitness-first standard that turns his recovery into company policy and a hiring pipeline for other people rebuilding their lives.

“Don’t focus on selling. Focus on building something great.”

Released from prison, Little went to rehab, then swept floors and cleaned bathrooms in a warehouse — sober. Roofing gave him a ladder: door-to-door canvasser, top salesman, then co-founder of Perimeter Roofing with partners Todd and Lance.

The company grew from roughly $4 million in year one to tens of millions a year — over $200 million in cumulative sales as a platform, 10+ branches across the Southeast — and sold to private equity for $38 million.

Twelve-plus years sober, he now coaches roofing owners through Storm Ventures Group, and a video of him fighting an insurance adjuster for a homeowner has passed 25 million views.

Roofing Success Podcast, Ep. 291 — “Roofing’s Second Chance”
Contractor Marketing Pros — “Scaling Perimeter Roofing: A Leadership Blueprint”
Buzzsprout — “Why Roofing Is the Best Second-Chance Industry in America, with Raymond Little”

More from The Bourgeois Society: The full list  ·  Miguel Taveras  ·  Tracy Bookman

Tracy Bookman

Owner, Homestead Roofing — Colorado Springs, CO

Official links: Website · LinkedIn

Tracy Bookman built his marketing engine out of the thing most roofers will not give away free: honest answers.

Instead of chasing storms, the owner of Homestead Roofing in Colorado Springs spent years building a homeowner-education library on YouTube — videos on roofing-scam prevention, shingle education, colour guidance, insurance navigation and his in-depth “how to choose a roofer” series — answering the real questions homeowners actually ask, including the ones from people who will never be his customers.

The library did what advertising struggles to do: it made Homestead one of the most trusted names in its market before the first phone call, and turned inbound leads into the company’s primary means of marketing.

“All of our videos are designed specifically for the homeowner to answer their questions.”

The strategy compounds, and Bookman is candid about the mechanics: six of his top ten performing videos are about shingles, because that is what homeowners are searching for at midnight before a big purchase.

The podcast that profiled his channel credits the library with seven-figure revenue impact and a durable trust moat around a local brand — in an industry where, as his episodes discuss frankly, storm chasers and commission-only sales models have taught homeowners to be suspicious of anyone who knocks.

Bookman’s answer to the suspicion is a paper trail of free help: the same educator’s voice runs through Homestead’s own blog, where he unpacks questions like what “certified” even means for a roofer and the five questions every homeowner should ask. Trust, it turns out, is a building material.

Roofing Podcast: Hook Better Leads (Listen Notes) — “How to Use YouTube to Help More Homeowners” (Tracy Bookman)
Roofing Podcast: Hook Better Leads (Podscan, episode transcript) — “How to Use YouTube to Help More Homeowners”
Homestead Roofing (company blog) — “Is Your Roofer Certified?”

More from The Bourgeois Society: The full list  ·  Raymond Wendell Little  ·  Aaron Christy