Roofing Insights Podcast

Dmitry Lipinskiy
  • 4.8 (25)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

Frank conversations with Dmitry Lipinskiy and roofing industry leaders.  Watch video episodes and more on our YouTube channel: https://bit.ly/RoofingInsights

  1. 6D AGO

    Falling From A Two-Story Roof | Jason Einsiedel

    Dmitry talks to Jason Einsiedel about his roofing career, a traumatic fall, and his hard-won recovery.  ============================ Sponsor of This Episode: Best Roofing Shoes Order Yours Here: https://shop.contrafootwear.com/?ref=DMITRYLIPINSKIY ============================ Today's guest: Bridget Como Forensic Building Science: https://www.forensicbuildingscience.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 - Introduction 01:40 - Jason’s Career in the Roofing Trade 03:44 - Taking the Leap: Starting His Own Business 04:42 - Witnessing Accidents Early in His Career 06:20 - The Day of the Accident: A Cousin's House 07:17 - The Moment of the Fall: A Slip on Plastic 08:45 - Impact and Immediate Aftermath 10:50 - The Severe Injuries 11:53 - A Grueling 6-Month Recovery Journey 13:10 - How the Accident Affected His Family 18:29 - The "Invincibility" Mentality in Roofing 21:17 - Living with the "New Normal" & Chronic Pain 28:01 - Life Lessons: Finding Perspective after Tragedy ============================

    36 min

  2. MAR 24

    Stop Chasing Revenue: Build a Profitable Roofing Company | Sean Moriarty

    In this episode, Dmitry talks to Sean Moriarty, Executive Roof Coach.  ============================ Sponsor of This Episode: Work Ninjas Expert Back Office For Roofing Companies - https://workninjas.com/ ============================ Today's guest: Bridget Como Forensic Building Science: https://www.forensicbuildingscience.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 Introduction & Studio Setup – 4 Years Later 01:15 Going Sober – The Turning Point 08:30 From Sobriety to Systems & Executive Roof Coach 09:40 Partnerships, Lawsuits & Rebuilding the Business 15:30 Commercial Roofing Reality – Systems vs Workflow 20:20 Million-Dollar Contracts & The Margin Trap 23:00 Payment Disputes, Retainage & GC Conflicts 27:30 Business, Coaching & Building a Foundation 33:00 What Makes a Real Coach? 38:00 CrossFit, Discipline & Personal Standards 39:30 Stuck at $2–3M? Systems vs More Leads 41:00 AI in Roofing – Leverage, Not Replacement 42:00 Marketing Mistakes & Why Agencies Fail 44:30 Money, Lifestyle & Owner Discipline 46:00 When Should an Owner Step Out of Production? 47:00 Customer Experience & Industry Reputation 49:50 Service & Maintenance as the Real Opportunity 52:10 Why Roofers Stay Broke 53:00 Ego vs Ignorance 54:30 Roof Rejuvenation Debate (Roof Max, GoNano) 58:00 Storm Chasers & The Future of Sales 01:00:50 Leadership, Hiring & Owning Your Role 01:02:40 $1M vs $10M Company – Mindset & Investment 01:03:30 Advice for Overwhelmed Entrepreneurs ============================

    1h 5m

  3. MAR 18

    Why Claims Get Denied, According to a Building Science Expert | Bridget Como

    In this episode, Dmitry talks to building science expert Bridget Como.  ============================ Sponsor of This Episode Take $1500 off your first GoNano order:  https://gonano.com/partners/roofing-insights ============================ Today's guest: Bridget Como Forensic Building Science: https://www.forensicbuildingscience.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 ============================

    1h 2m

  4. MAR 16

    $7.5M to $32M in 4 Years: How Trust Roofing Exploded | Robin Scherer

    In this episode, Dmitry talks to Robin Scherer, owner of Trust Roofing.  ============================ Sponsor of This Video: Book a Demo with JobNimbus:  https://jobnimbus.me/4mQCNO2 ============================ Today's Guest: Robin Scherer: https://www.linkedin.com/in/robinroofs/ Trust Roofing: https://trustroofing.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 – JobNimbus 00:07 – Coming Up... 00:43 – What really changes when scaling a roofing company 03:30 – Robin Scherer’s background in sales and business 07:30 – Building strong culture and high-performing teams 10:45 – Systems, processes, and structure for rapid growth 14:55 – Hiring, training, and mistakes made while scaling 17:30 – Consumer education and the impact of Google and AI 20:40 – Retail roofing vs. insurance work: why branding wins 23:30 – What’s harder now than when the company started 25:00 – Costly jobsite mistakes and risk management 28:15 – Warranties, claims, and customer service as marketing 31:00 – Commercial operations and field stories 34:50 – Why owners must understand real roof work 36:10 – Roofing trends: metal, stone-coated, and innovation 39:20 – Leadership growth and industry blind spots 43:00 – Insurance pitfalls and young roofer mistakes 46:00 – False promises in roofing and hard lessons learned 49:20 – Fighting insurance carriers and state-by-state differences 52:00 – Work-life balance and CEO pressure 55:30 – Final mindset advice and closing thoughts ============================ 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 ============================

    58 min

  5. FEB 9

    Roofing's Retail Takeover: "You Can't Depend On Insurance." | Kenny Baden

    In this episode, Dmitry talks to Kenny Baden about his recovery journey, consulting, content and the future of retail roofing.  ============================ Sponsor of This Episode Estimate Experts: https://estimate-experts.com ============================ Today's guest: Kenny Baden Baden Consulting: https://badenconsulting.net/about ============================ 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 – Extended intro 02:19 – Interview begins: suits, image, and first impressions 03:49 – Culture shift: suits vs casual (Patrick Bet-David, Hunter Ballou) 05:49 – Image as a brand and sales advantage 07:29 – Look good, feel good, play good 08:24 – Being in a room full of winners 10:49 – Losing everything and starting from zero 12:04 – Dressing with intention as a strategy 14:19 – Addiction, humility, and losing direction 17:04 – From college graduate to convicted felon 18:19 – What addiction really feels like 20:34 – The real turning point 22:49 – Redirecting destructive energy into success 25:29 – Consulting, content, and industry truth 27:54 – Instagram culture vs real results 29:14 – You can’t fake the work 31:29 – Mentors, networks, and real growth 33:44 – Immigration pressure and job sites 38:19 – Private equity and generational wealth 39:59 – Closing thoughts on opportunity and leadership ============================ 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 ============================

    1h 2m

  6. JAN 12

    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

  7. JAN 5

    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

  8. 12/29/2025

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

    56 min
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4.8
out of 5
25 Ratings

About

Frank conversations with Dmitry Lipinskiy and roofing industry leaders.  Watch video episodes and more on our YouTube channel: https://bit.ly/RoofingInsights

Information

  • Creator
    Dmitry Lipinskiy
  • Years Active
    2021 - 2026
  • Episodes
    107
  • Rating
    Explicit
  • Copyright
    © 2026 Roofing Insights Podcast
  • Show Website
    Roofing Insights Podcast

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