Roofing Insights Podcast

Roofing Insights Podcast

By Dmitry LipinskiyBusinessEntrepreneurship
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Roofing Insights Podcast episodes

  • Inside A Roofing PE Deal Nightmare: “I’m gonna go bankrupt.” | Dan Ward

    In this episode, Dmitry talks to Dan Ward, owner of Rumble Roofing. 

    ============================
    Sponsor of This Episode
    Roofing Business Partner:
    https://agentone.roofingbusinesspartner.com
    ============================
    Today's guest:
    Dan Ward
    Rumble Roofing: https://www.rumbleroofing.com
    ============================
    Dmitry’s coaching program: https://roofing-school.com
    Have a question? Text me: 612-558-4881
    Connect with Dmitry: https://dmitrylipinskiy.com/
    Contractors I recommend: https://directorii.com
    Best Deals on Underlayment: https://BemDirect.com
    ============================
    Insights:
    00:00 – Roofing Business Partner
    00:11 – Coming Up...
    00:55 – Introduction and setting the tone for the conversation
    02:18 – Dan Ward’s background and entry into the roofing industry
    04:46 – Early career lessons and mistakes that shaped his approach
    07:34 – What separates average roofers from top performers
    10:12 – Sales fundamentals most contractors overlook
    13:05 – Building trust with homeowners in competitive markets
    15:48 – The role of leadership in scaling a roofing company
    18:36 – Hiring, training, and developing strong teams
    21:27 – Common operational bottlenecks in growing roofing businesses
    24:19 – Managing reputation and long-term brand value
    27:11 – Market changes and how roofers must adapt
    30:06 – Advice for contractors stuck at the next growth ceiling
    33:14 – Lessons learned from failure and course correction
    36:08 – Industry myths that hurt roofing professionals
    39:02 – Final insights on discipline, consistency, and longevity
    41:32 – Roofing Insights Belt
    ============================
    Let's Connect:
    Facebook: http://bit.ly/RoofInFB
    Fb group: https://bit.ly/RI-private-FB-group
    Instagram: http://bit.ly/RoofInIG
    Twitter: http://bit.ly/RoofInTW
    LinkedIn: https://bit.ly/RI-LinkedIn
    ============================

    44 min
  • Building a Roofing Company Without Fear of Competitors | Jeffrey Linta

    In this episode, Dmitry talks to Linta Roofing owner Jeffery Linta. 

    ============================

    Today's guest
    Jeffrey Linta: 
    https://www.linkedin.com/in/jeffrey-linta-314b7328/
    Linta Roofing:
    https://lintaroofing.com
    ============================

    Dmitry’s coaching program: https://roofing-school.com
    Have a question? Text me: 612-558-4881
    Connect with Dmitry: https://dmitrylipinskiy.com/
    Contractors I recommend: https://directorii.com
    Best Deals on Underlayment: https://BemDirect.com
    ============================
    Insights
    00:00 – Coming up...
    00:36 – Opening context: today’s roofing market
    02:11 – Personal background and early lessons from the roofing industry
    04:47 – How roofing sales really work
    07:29 – Building trust fast with homeowners who are already skeptical
    10:18 – Why price shoppers are created by bad sales conversations
    13:06 – Educating vs. selling: changing the way roofers present valu
    16:02 – Common mistakes reps make during insurance conversations
    18:41 – Leadership gaps in roofing companies and their real cost
    21:27 – Training sales reps to think, not just follow scripts
    24:36 – The importance of standards, process, and accountability
    28:14 – Scaling roofing businesses without destroying culture
    31:22 – Social media, ego, and the modern roofing image problem
    34:47 – Long-term reputation vs. short-term wins
    38:19 – Advice for new roofers entering the industry
    41:52 – Mindset, discipline, and sustainable success
    46:40 – Key takeaways and final reflections
    ============================
    Let's Connect:
    Facebook: http://bit.ly/RoofInFB
    Fb group: https://bit.ly/RI-private-FB-group
    Instagram: http://bit.ly/RoofInIG
    Twitter: http://bit.ly/RoofInTW
    LinkedIn: https://bit.ly/RI-LinkedIn
    ============================

    47 min
  • The Truth About Supplements & AI in Roofing | Mauricio Gutierrez

    In this episode, Dmitry talks to Mauricio Gutierrez, CEO of Estimate Experts. 

    ============================

    Today's guests:
    Mauricio Gutierrez: https://www.linkedin.com/in/mauricio-gutierrez-321990177/es
    Estimate Experts: https://estimate-experts.com/
    ============================

    Mauricio supplementing company: https://estimate-experts.com/
    Dmitry’s coaching program: https://roofing-school.com
    Have a question? Text me: 612-558-4881
    Connect with Dmitry: https://dmitrylipinskiy.com/
    Contractors I recommend: https://directorii.com
    Best Deals on Underlayment: https://BemDirect.com
    ============================
    00:00 – Intro: Mauricio, Founder of Estimate Express from Colombia
    00:58 – Early Ambition: Dreaming Big and Moving to the USA
    02:05 – The Drive You Can't Teach: Key to Success
    03:32 – Tough Lesson: Toxic Boss in Colombia
    04:34 – Breaking Into Restoration & Insurance World
    06:02 – Discovering Xactimate: How Estimate Express Started
    07:31 – The Big Problem: Contractors Hate Paperwork
    08:46 – Roofing Shocker: The Trade Leaving Most Money on the Table
    09:41 – Why Roofers Lose Thousands on Every Claim
    11:06 – What Makes Estimate Express Different
    12:23 – Key Tools: Satellite, Clear Photos & Certified Estimators
    14:34 – Will AI Kill This Industry? (Honest Answer)
    19:09 – Real Turnaround: 2 Days for Estimates, 60-90 Days for Settlements
    20:30 – Claim Management: Fighting Supplements Without Being a PA
    33:00 – Insane Success Rate: Almost Zero Denials
    36:38 – Claim Inflation: Still Happening or More Professional Now?
    40:00 – Why They Switched to Flat Fees (No More Percentage)
    43:00 – What to Ask Before Hiring a Supplement Company
    46:00 – Full Transparency: Real-Time Portal & Weekly Reports
    48:00 – Supplements Are Fair: Adjusters Miss Items All the Time
    52:00 – #1 Mistake Contractors Make That Costs Them Big
    53:00 – One Key Lesson About Claims That Changes Everything
    54:00 – How to Get Started with Estimate Express (Fast Onboarding)
    55:00 – Wrap-Up
    ============================
    Let's Connect:
    Facebook: http://bit.ly/RoofInFB
    Fb group: https://bit.ly/RI-private-FB-group
    Instagram: http://bit.ly/RoofInIG
    Twitter: http://bit.ly/RoofInTW
    LinkedIn: https://bit.ly/RI-LinkedIn
    ============================

    57 min
  • Private Equity Is Easy to Beat” | Mark Easton

    In this episode, Dmitry talks to Mark Easton of Buccos Roofing. 

    ============================

    Book a Demo with JobNimbus: 
    https://jobnimbus.me/4mQCNO2
    Dmitry’s coaching program: https://roofing-school.com
    Have a question? Text me: 612-558-4881
    Contractors I recommend: https://directorii.com
    Best Deals on Underlayment: https://BemDirect.com
    ============================
    Today's guest:
    Mark Easton:
    https://www.facebook.com/buccosroof/
    https://www.instagram.com/buccosroofing/
    https://www.linkedin.com/company/buccos-roofing/
    ============================
    00:00 – Intro: "Success Is Not Just Money – Roofing Is a Business, Not a Trade"
    01:07 – The Aha Moment: "First Big Check – This Isn't a Trade, It's a Company"
    03:29 – Branding Bombs: "Yellow Shorts Everywhere – That's How We Stand Out"
    06:48 – "Fake It Till You Make It Actually Works – Here's Proof"
    10:15 – Clean Sites Win Jobs: "People Judge You by Your Job Site First"
    13:45 – Team Culture: "I Want My Guys to Make Money – Not Just Me"
    18:20 – "I Dress Up for Interviews – It's Respect for the Craft"
    22:15 – Hiring Truth: "I'd Rather Wait Than Hire the Wrong Guy"
    25:40 – Growth Trap: "Big Revenue Doesn't Mean Rich – Change That"
    28:10 – Faith in Business: "God Gave Me This – Now I Give Back"
    31:50 – "I Don't Want to Compete – I Want to Help Roofers Win"
    35:20 – Franchise Dream: "Build Something Bigger Than Just My Company"
    38:45 – "We Exposed the Scammers – Now Let's Build Real Value"
    42:10 – The Missing Link: "Most Franchises Don't Care About You"
    45:30 – Final Fire: "Let's Make Roofing Companies Great – Together"
    48:20 – Wrap-Up
    ============================
    Let's Connect:
    Facebook: http://bit.ly/RoofInFB
    Fb group: https://bit.ly/RI-private-FB-group
    Instagram: http://bit.ly/RoofInIG
    Twitter: http://bit.ly/RoofInTW
    LinkedIn: https://bit.ly/RI-LinkedIn
    ============================

    1 hr 9 min
  • Ex-Insurance Adjuster Reveals How Claims REALLY Get Paid | Matt Morgan

    In this episode, Dmitry talks to Matt Morgan of Chad Wilson Law Firm. 

    ============================

    Have denied claim? Consult with https://cwilsonlaw.com/ 
    Contractors I recommend: https://directorii.com
    Dmitry’s coaching program: https://roofing-school.com
    Have a question? Text me: 612-558-4881
    Connect with Dmitry: https://dmitrylipinskiy.com/
    Best Deals on Underlayment: https://BemDirect.com
    Roofing Insights T-shirts - https://roofinginsightsstore.com/
    ============================
    Insights
    00:00 – Chad T. Wilson Law Firm
    00:22 – Coming Up...
    01:02 – Introductions, Background & Setting the Stage
    04:18 – Getting Started in Roofing & Early Lessons
    09:55 – Field Experience vs. Office Decisions
    15:40 – Sales, Trust & Customer Expectations
    21:30 – Hiring, Training & Building the Right Team
    27:10 – Leadership Mistakes & Hard Business Lessons
    33:05 – Marketing, Branding & Standing Out Locally
    39:22 – Operations, Systems & Daily Accountability
    45:40 – Scaling Challenges & Growing Without Chaos
    52:18 – Industry Changes & Where Roofing Is Headed
    58:30 – Personal Growth, Mindset & Work–Life Balance
    01:05:12 – Advice for New Contractors
    01:11:20 – Final Thoughts, Takeaways & Closing Remarks
    ============================
    Let's Connect:
    Facebook: http://bit.ly/RoofInFB
    Fb group: https://bit.ly/RI-private-FB-group
    Instagram: http://bit.ly/RoofInIG
    Twitter: http://bit.ly/RoofInTW
    LinkedIn: https://bit.ly/RI-LinkedIn
    ============================

    1 hr 18 min
  • The Most Honest Roofing Interview I’ve Ever Done | Eric Oberembt

    In this episode, Dmitry talks with Eric Oberembt, owner of D&M Roofing. 

    ============================

    Podcast Sponsor: https://novatik.us/ (Text "metal" to 786-512-9248)
    Contractors I recommend: https://directorii.com
    Best Deals on Underlayment: https://BemDirect.com
    Dmitry’s coaching program: https://roofing-school.com
    Have a question? Text me: 612-558-4881
    Connect with Dmitry: https://dmitrylipinskiy.com/
    ============================
    Today's guest
    Eric Oberembt:
    https://www.linkedin.com/in/eric-oberembt-73968112/
    D&M Roofing:
    https://dandmroofing.com
    Roofers in Recovery:
    https://roofersinrecovery.org
    ============================
    Insights
    00:00 – Novatik
    01:35 – Coming Up
    02:12 – Cold Plunges, Saunas & Morning Routines
    04:08 – A Roofing Legacy: Starting a Company With $50
    06:56 – Growing Up in Roofing & Learning the Trade
    09:56 – Transitioning From the Field to Leadership
    13:46 – Marketing, Visibility & Owning Your Reputation
    16:36 – Building a Culture of Trust Inside the Company
    20:39 – Immigration, Labor Shortages & Work Visas
    25:00 – The Biggest Business Mistake as an Owner
    27:08 – Why No Business Truly Runs on Autopilot
    30:00 – Overhyped Roofing Trends & Industry Myths
    35:06 – AI, Private Equity & The Future of Roofing
    39:36 – Scaling Locations Without Losing Control
    54:16 – Loyalty, Family & Cutting Off Toxic Relationships
    01:05:07 – Authenticity, Relationships & Leadership Style
    01:11:02 – Leading Teams Across States & Final Takeaways
    ============================
    Let's Connect:
    Facebook: http://bit.ly/RoofInFB
    Fb group: https://bit.ly/RI-private-FB-group
    Instagram: http://bit.ly/RoofInIG
    Twitter: http://bit.ly/RoofInTW
    LinkedIn: https://bit.ly/RI-LinkedIn
    ============================

    1 hr 13 min
  • “Stop Praying for Storms.” Roofer Calls Out the Industry | Brent Tuggle

    In this episode, Dmitry talks with Brent Tuggle, owner of Tuggle Roofing. 
    ============================
    Book a Demo with JobNimbus: 
    https://jobnimbus.me/4mQCNO2
    ============================

    Contractors I recommend: https://directorii.com
    Best Deals on Underlayment: https://BemDirect.com
    Dmitry’s coaching program: https://roofing-school.com
    Have a question? Text me: 612-558-4881
    ============================
    Today's guest:
    Brent Tuggle: https://www.linkedin.com/in/brent-tuggle-ba6866173/
    https://www.tuggleroofing.com/
    https://www.facebook.com/TuggleRoofingllc/
    ============================
    00:00 – Coming up
    03:29 – Started Roofing at 14 with Zero Money
    06:48 – Clean Site Secret: “Fake It Till You Make It – But Clean Up First”
    10:15 – “You Can Be Big and Still Broke” – The Growth Trap
    13:45 – “I Dress Up for My Guys – It’s All for Them”
    18:20 – From “Bad Guy” to Life-Changing Thank Yous
    22:15 – Faith Flip: “God Told Me – Do It for Them, Not for You”
    28:10 – Insurance Chaos, Pricing Wars & Worker Problems
    33:27 – “I’d Rather Lose Money Than Do a Sh*tty Job”
    38:45 – Management Hell: How We Actually Run the Crews
    45:20 – The Turning Point: “Let Go of Control – That’s When You Explode”
    52:30 – “God Wants More for You Than You Want for Yourself”
    59:40 – “Struggle Built My Character – Now I Help Others”
    01:06:48 – Real Talk: Faith, Family & Roofing Life
    01:13:45 – “No Way I Could Do This Without God”
    01:21:15 – Insurance, Workers & Pricing in 2025 – Raw Truth
    01:28:10 – “When You Realize It’s Bigger Than You…”
    01:35:40 – Final Fire: “Make It Happen for Others – That’s the Cheat Code”
    01:42:15 – Wrap-Up
    ============================
    Let's Connect:
    Facebook: http://bit.ly/RoofInFB
    Fb group: https://bit.ly/RI-private-FB-group
    Instagram: http://bit.ly/RoofInIG
    Twitter: http://bit.ly/RoofInTW
    LinkedIn: https://bit.ly/RI-LinkedIn
    ============================


    1 hr 49 min
  • Is Your Chimney Slowly Poisoning Your Family? | Joel Orchel

    In this episode, Dmitry talks to Joel Orchel, founder of The Chimney Scientists. 

    ============================

    Insights: 
    00:00 – Cold Open: "Carbon Monoxide in Your Basement – The Silent Killer from Chimneys"
    00:54 – Branding Bombs: "Bright Yellow Trucks – Why We Stand Out in Philly"
    01:07 – Services Breakdown: "Rebuilding Fireplaces, Chimneys & More – What We Really Do"
    02:44 – Health Warning: "Your Chimney Could Be Poisoning Your Family – Here's How"
    04:10 – Shocking Truth: "Most Homeowners Don't Realize Their Chimney Is Breaking Down"
    05:20 – Backdraft Danger: "Small Leaks Turn into Carbon Monoxide Nightmares"
    06:48 – Passion for Prevention: "We're Not Just Fixing – We're Saving Lives"
    07:30 – Wrap-Up

    ============================
    Today's guest:
    https://www.linkedin.com/in/joeochal/
    https://chimneyscientists.com/
    https://www.instagram.com/chimneyscientists/

    ============================

    Refresh your brand with Dmitry: https://roofing-school.com
    Have a question? Text me: 612-558-4881
    Connect with Dmitry: https://dmitrylipinskiy.com/
    Contractors I recommend: https://directorii.com
    Best Deals on Underlayment: https://BemDirect.com


    8 min
  • What They Don’t Tell You About Selling to Private Equity | Jason Reisman

    In this episode, Dmitry talks to Jason Reisman of Eustis Roofing. 

    ============================

    Sponsor: https://novatik.us/
    Get $1,000 OFF your first order — just mention Dmitry.
    Text “Metal” to 786-512-9248 to get started!
    ============================
    00:00 – Intro
    01:14: - Coming up
    02:44 – Roofing Company of the Year SOLD to Private Equity
    03:29 – Why Jason Sold His $30M Empire: "I Hit Peak and Couldn't Grow Alone"
    05:20 – The Unexpected PE Boost: "My Team Got 30% Raises Overnight"
    07:45 – Brutal Truth: "If You're Not Performing, PE Fires You Fast"
    10:15 – What Jason Fixed Before Selling: Books, Team, and Systems
    13:45 – The CEO Identity Crisis: "Who Am I If I'm Not Climbing Roofs?"
    17:30 – "I Still Install Roofs... To Keep Crew Respect"
    21:15 – Instagram Trap: Flashy Posts Kill Installer Loyalty
    25:40 – How to Earn Respect from Your Crew Post-Sale
    28:10 – "Post Roof Details, Not Vacations – That's How You Build Quality"
    31:50 – The Hard Lesson: Installers See Your Social Media Too (And Judge You)
    33:27 – "Invite Crews to EVERY Event – Or Lose Your Team"
    35:05 – Final Fire: "Installers Control Your Quality – Treat Them Like Gold"
    36:48 – Dmitry & Jason Mic Drop: Make Installers Great Again
    38:20 – Wrap-Up: Jason's Message to Every Roofing Owner

    Dmitry’s coaching program: https://roofing-school.com
    Have a question? Text me: 612-558-4881
    Connect with Dmitry: https://dmitrylipinskiy.com/
    Contractors I recommend: https://directorii.com
    Best Deals on Underlayment: https://BemDirect.com
    Roofing Insights T-shirts - https://roofinginsightsstore.com/
    ============================
    Today's guest
    Jason Reisman:
    https://www.linkedin.com/in/jason-reisman-72484b16a/
    Eustis Roofing Company:
    https://eustisroofing.com/
    https://www.instagram.com/eustisroofingcompany/#
    https://www.facebook.com/EustisRoofing
    https://www.youtube.com/channel/UCRuMFZ4N4Sa5_sUuoxGtL9w
    ============================

    38 min
  • The SHOCKING Truth About Call Centers in Roofing Nobody Tells You | Peter Roth

    In this episode, Dmitry talks to Entrepreneur Peter Roth. 

    ============================

    Sponsor: https://thecatchall.com/
    ============================
    Insights
    00:00 – The Catch All
    00:39 – Coming Up
    01:14 – How Peter Roth entered the roofing call center world
    05:02 – When Scalify Call Centers started working with roofers
    09:30 – Understanding homeowner psychology on the first call
    13:55 – The scripts and openers that actually convert
    18:12 – Why most roofing companies fail at follow-up
    22:48 – Building a call center team that works
    27:30 – Handling storm leads vs. retail roofing calls
    32:44 – How to fix bad lead quality and wasted marketing dollars
    36:58 – Training callers to sound confident and not robotic
    41:15 – Insurance claims, touchpoints, and setting proper expectations
    46:40 – The systems Scalify uses to scale roofing call centers
    52:18 – Advice from Peter Roth to roofing owners trying to grow
    58:40 – The future of call centers in the roofing industry

    Dmitry’s coaching program: https://roofing-school.com
    Have a question? Text me: 612-558-4881

    Connect with Dmitry: https://dmitrylipinskiy.com/
    Contractors I recommend: https://directorii.com

    Best Deals on Underlayment: https://BemDirect.com
    Roofing Insights T-shirts - https://roofinginsightsstore.com/
    ============================
    Today's Guest
    Peter Roth:
    https://www.linkedin.com/in/realpeterroth/
    Scalify Call Centers:
    https://www.scalifyco.com/
    ============================

    1 hr 1 min

About Roofing Insights Podcast

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Frank conversations with Dmitry Lipinskiy and roofing industry leaders. 


Watch video episodes and more on our YouTube channel:…

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