Guest: Jon Brown — Executive Pastor, Journey Church (Kenosha, WI) Guest Links: Instagram: @PJon | YouTube: JRNY Church

Jon Brown has spent 25 years at the same church, working his way up from youth pastor to executive pastor overseeing 36 staff pastors, 75% of whom he developed from a young age. In this episode, recorded in Italy, he breaks down the universal leadership principles that apply whether you're running a church, a roofing company, or a marketing agency: how to actually grow yourself before you grow others, why your competition should become your allies, how to handle the pressure of perfection when everyone expects you to have it together, and the Sabbath discipline that keeps high performers from burning out on the long haul.

You'll learn:

• Why leading yourself is the hardest leadership job you'll ever have
• How to build a personal growth plan that targets your actual blind spots
• Windshield time: turning drive time into learning time with audiobooks
• "If you want to go fast, go alone. If you want to go farther, go together"
• How jealousy of competitors reveals your own insecurities (the Joseph Kellogg story)
• Why you should reach out and encourage the person you're most jealous of
• Treat people like they love you, and eventually they'll start to believe it
• How to handle critics who question your motives and character
• Why leaders don't get to have a bad day (chug the Red Bull in your truck)
• Complain up, never down: why you need someone above you to vent to
• If you don't heal what hurt you, you'll bleed on people who don't deserve it
• John Maxwell's 5 levels of leadership: position, permission, production, people development, pinnacle
• Why 25 years in one place creates compounding mastery and generational impact
• The Sabbath principle: one day a week fully unplugged (and the auto-text that protects it)
• Why hobbies and play make the other six days more effective

Guest: Tony Vincent — Owner, Ultimate Roofing | Ultimate Properties | Ultimate Tree Service | Ultimate Equipment Rentals Guest Links: Website: https://getultimateroofing.com | Facebook: Ultimate Roofing WV

Tony Vincent runs four businesses out of West Virginia and has built Ultimate Roofing into a $20 million operation with 100+ employees across 5 states, while quietly stacking $9 million in heavy equipment and 70 rental properties on the side. In this episode, he ranks the most lucrative home service industries for 2026, breaks down why he stopped chasing top-line revenue at 16% net, and pulls back the curtain on the systems that let him manage 100 people without losing his mind. The conversation also dives into the financing playbook that gets him to 90% financed jobs, why blown-in insulation and gutter guards are the secret weapons for landing premium roofs, and how a single $1 door hanger incentive turns laborers into canvassers.

You'll learn:

• Tony's ranked list of the most lucrative home service businesses for 2026
• Why tree service has 75-80% GP and is one of the best businesses to add to roofing
• The "less saturated = more lucrative" rule for picking your next trade
• Why he killed the fencing offshoot after 100 jobs
• The 5-or-6-manager hierarchy that lets him run 100 employees from a distance
• Why titles motivate people more than monetary compensation
• The low-base, high-KPI compensation structure used on every single employee
• How a $1 per door hanger incentive generates real referral jobs
• Why he stopped chasing $50M revenue and dialed in at $20M with 16% net
• The "control the supply chain" rule that drove his decision to drop fencing, gutters, soffit, fascia, doors
• Why his ad spend is $80K on Google for roofing vs $1K for equipment rentals
• How to use Service Finance for 90% financed jobs (and why Foundation is the wrong primary)
• The "what's your budget look like?" frame that closes more roofs like car sales
• Why blown-in insulation and gutter guards at zero margin land $25K roofs
• The 55% close rate that comes from giving away promotional items
• Why most contractors should be financing every job over $10,000
• How his real estate portfolio (70 properties) became his retirement plan after stocks

Guest: Kris Werner — President, Werner Roofing | IHS Group (Infinity Home Services) Guest Links: Website: https://www.wernerroofing.com | Phone: (616) 638-4662

Kris Werner runs Werner Roofing in Grand Haven, Michigan, a "five mile famous" brand he built slowly from a one-man job into a multi-trade home service operation now partnered with Infinity Home Services. In this episode, he gets practical about what actually changes when you join a private equity backed family of brands, why best practice sharing with 25 other roofing companies is the unfair advantage most owners don't have, and the operational details that separate a $4M roofer from a $10M+ company. The conversation also goes into adding trades the right way, why Werner doesn't chase storms, how Castle and Diamond metal shingles compare, what's actually slowing down GAF solar shingle adoption, and why a "divine discontent" customer expectation curve is reshaping the entire industry.

You'll learn:

• Why "five mile famous" beats trying to be a regional powerhouse
• How to add metal roofing, gutters, siding, and windows without breaking your ops
• What private equity actually changes (and what stays the same)
• How 25 brand presidents share best practices daily across IHS
• Why collecting accounts receivable matters more in winter than you think
• How to pick a second location and the first two hires that matter
• The "law of the lid" that keeps owners stuck at $3-5M
• Why retail roofing beats waiting on storms (even in storm markets)
• How to treat roofing crews so they stay loyal to your brand
• Just-in-time material delivery vs full roof load: pros and cons
• Why the synthetic roofing market is only 2% (and what could change)
• The new GAF, Castle, Diamond, and Tesla metal products worth watching
• The Jeff Bezos "divine discontent" effect on customer expectations
• Why reading the same business books 3 times beats reading 30 new ones

Guest: Pedro Rodriguez — Production, Owl Roofing Guest Links: Instagram: @P1Rodriguez | Website: https://owlroofing.com

Inside the real tension between sales, marketing, and production at a brand-new roofing company. Pedro Rodriguez runs production at Owl Roofing, the new Minneapolis venture that hit nearly half a million in sold revenue in its first real month. In this episode, the conversation gets raw about the friction that comes with going aggressive on marketing out of the gate: lead overflow, the sales-to-production handoff, scrambling to fulfill what marketing promises, and why most roofing companies stay stuck at $2-3M for years.

You'll learn:

• Why aggressive marketing creates production tension and how to manage it
• The sales-to-production handoff problem (and the document that fixes it)
• Why 200 pictures per inspection isn't excessive, it's the bare minimum
• How to spend 10% on marketing without breaking your company
• The choice between hiring veterans vs training from scratch
• Why they're recruiting $1M reps to turn into $2M reps (not chasing $3-5M superstars)
• How to build master networkers, not just master door knockers
• Why manufacturers (GAF, Iko, Owens Corning) will determine the future of roofing
• The bottleneck every new business owner hits and how to delegate around it
• Real numbers: $487K in month one, 25 leads a week from marketing alone
• How to keep retail roofing healthy without depending on storms
• Why the right culture reinvigorates burned-out reps from bad ownership

Guest: Tim Brown — Founder, Hook Agency | Co-Founder, Owl Roofing Guest Links: Website: https://owlroofing.com | https://hookagency.com

The marketer who built Hook Agency advising roofing companies for over a decade just started one of his own. In this episode, Tim Brown takes the guest seat to break down Owl Roofing, his new home service venture in Minneapolis that hit $480K sold in its first real month of business. He covers what actually transfers from running a 10-year-old marketing agency to launching a roofing company from scratch, what's working faster than expected, and the mistakes he's actively trying to avoid based on a decade of watching other roofers make them.

You'll learn:

• Why he started a roofing company on top of running Hook Agency and raising two kids
• What it actually feels like to step away from the company that made your name
• How $161,000 of starting capital changed the entire game vs. starting from $20K
• Why Google Organic and Google Paid are crushing every other lead source out of the gate
• The "lead babies" problem: why giving reps too many leads kills their hunger
• Cash flow trap most new roofing companies fall into (the bank account isn't your money)
• Why a short, iconic, emoji-friendly brand name compounds every marketing dollar
• The full court press strategy: take every conceivable advantage from day one
• 350 yard signs in one market and the police calls that came with it
• Why brand effort lowers cost per lead on Google Ads (the Monarch Roofing case)
• Pre-revenue marketing: what to do when you have no budget percentage to work with
• The two sharpest tools in his roofing toolbox right now (sales enablement + weekly role play)

Guest: Raymond Little — Founder, SVG Roofing Coaching | Contra Shoes

Guest Links: Facebook: Raymond Wendell Little | Instagram: https://www.instagram.com/rwl612/

Raymond Little built a roofing company from zero to nearly $100 million, exited to private equity for $40 million, and now runs SVG helping owner-operators between $1M and $10M break through their plateaus. In this episode, Raymond gets raw about what actually works in roofing sales in 2026, starting with storm vs retail in today's market, why wind claims are getting harder everywhere, and why the four-to-eight knocking window beats the nine-to-five mindset most new companies are still stuck in. He breaks down why you should never poach million-dollar producers from other companies but instead build them yourself, why a hefty override or ownership needs to be in the field driving the team daily, and his rule that you can't develop anyone greater than yourself. The conversation digs into Raymond's hiring philosophy built around second-chance people, team players, and good energy over credentials or personality tests, his 90-day ride-along system where new reps work the first 4-5 deals in the truck with him from knock to build, and the sales tactic of using the adjuster and homeowner as "teachers" to elevate new reps while making the process fully transparent. Raymond also shares why personal development around physical health, clean living, and healthy relationships is the foundation his entire company was built on, the real numbers on what 1099 reps should earn per lead, why one roof a week pays the bills and three a week means you stop checking price tags, and his mentor story of following Kurt the Nintendo and hitting half of what that man accomplished as his own definition of success. He also gets into Contra Shoes, the lightweight flexible roofing shoe a quarter the weight of Cougar Paws, designed for reps who knock and climb all day.

Guest: Ryan Fitzgerald — Plumbing Department Leader, Fitzgerald Heating Air and Plumbing (Las Vegas, NV)

Guest Links: Facebook: Ryan Fitzgerald (Las Vegas, Nevada)

This episode covers how to layer a plumbing department onto an existing HVAC company and scale it from almost nothing to over $5 million in a single year. Ryan Fitzgerald joined a company in Las Vegas that was doing $14 million in HVAC but only $400,000 in plumbing, and within his first full year built the plumbing side to $5.4 million with a team of eight technicians and four installers. He breaks down exactly how that happened: a dedicated outbound team hammering phones to fill the board, assigning calls based on each tech's strengths and weaknesses, a four-option sales process where the homeowner feels empowered to choose rather than pressured, and leveraging HVAC cross-selling to get plumbing in the door. The conversation gets into why implementing systems too early can actually hurt you, including a real example of a field manager role they tried at $5 million that created friction between installers and sales techs and had to be pulled back until $7 or $8 million. Ryan also shares how growing too fast led to warranty callbacks when his install crew got overloaded, how he trains techs to turn leak detection and water quality testing into high-ticket opportunities in the Las Vegas market through education rather than pressure selling, and why the culture shift between HVAC and plumbing went from "redheaded stepchild" to healthy competition once the plumbing guys started keeping pace on revenue. He explains his leadership approach of quarterly deep dives with each team member, leading by example by still jumping into the trenches, and why accountability has to go both ways between leaders and the team.

Guest: Brad Strawbridge — Founder, Capital City Roofing & BuilderLync

Guest Links: Website: https://builderlync.com/

This episode covers practical, real-world ways roofing companies are using AI right now to automate non-revenue tasks and free up teams to focus on selling and customer experience. Brad Strawbridge walks through how he uses Claude Co-Work to build reusable workflows that automate everything from proposal creation to dispatching sales reps, how the teach feature lets you record clicks and turn any repetitive CRM process into a saved workflow you can trigger with a forward slash command or put on a schedule. He explains how he built Capital City University, a full training curriculum for roofing using Notebook LM with manufacturer materials and RCA-approved content uploaded as knowledge sources. The conversation also covers BuilderLync, an all-in-one CRM built specifically for roofers that replaces five or six separate tools, handling everything from AI-powered cold outreach and lead nurturing to scheduling, dispatching, supplements, bookkeeping, and payment collection. Brad shares his take on why newer roofing companies have a massive advantage right now by starting AI-first instead of trying to retrofit old processes, why the best way to use AI is to give it a ridiculous amount of context before asking for answers, and his five-year outlook on where roofing is headed with the Roofing Alliance bringing the trade into universities and driving technology adoption across the industry.