• What Do Northern Roofers Do During the Winter?
    Oct 21 2026

    Guests: Pavel — Owner, Pasco Construction & Revision European Windows
    Dan — Sales Manager, Pasco Construction & Revision European Windows

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

    How do roofers stay busy in a northern winter? A company that’s survived 17 of them breaks it down.

    It’s Owl Roofing’s first winter, and Tim and Noah are honest about the anxiety: payroll, trucks, rent, and no roofs going on. So they visit Pavel and Dan at their Coon Rapids facility, a company that started with siding in 2008 and now manufactures its own European windows. Windows turned out to be the best winter product they sell (1:03), driven by a free thermal camera energy audit (18:34). The conversation also covers why Minnesota homeowners are getting fed up with door knockers (7:12), how to use the off season to build SOPs and training (10:23), and why sometimes the best decision is to not change anything (11:38).

    You’ll learn:

    • Why windows sell better than anything else in the winter
    • The free energy audit pitch using a $120 thermal camera
    • The promo: buy ten windows, get free attic insulation
    • Why out-of-state storm chasers are making every roofer look bad
    • What to do from mid-December to mid-January (and when to get back to work)
    • Turning Loom training videos into quizzes with Claude
    • Why not switching your CRM can be the smartest offseason call
    • ProLine vs JobNimbus: what each team actually likes about their CRM
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    26 min
  • The Hidden Lead Leak Could Double Your Net Profit (w/ Trent Lowenstein of Next Level Pros)
    Oct 13 2026

    Guest: Trent Lowenstein — Coach, Next Level Pros | Host, Trent and Friends Podcast
    Guest Links: Website: https://gonextlevelpros.com

    You might be one or two jobs away from doubling your net profit. The leak is between booked and sat.

    Trent Lowenstein from Next Level Pros joins Tim to diagnose Owl Roofing live, using what he calls “God mode”: looking at your business like the architect of the game instead of player one (0:47). He walks through why a 10% bump in sit rate can turn a 7% net company into a 20% net company once your fixed overhead is covered (3:21), why your operations manager should never be your CSR (11:10), and how to budget around a dead winter instead of dividing your goal by 12 (11:58). Then it gets uncomfortable: a live financing role play with the Owl team that proves exactly the problem being discussed (25:27).

    You’ll learn:

    • The flywheel metrics: booking rate, stickiness, close rate, average ticket, install efficiency, referrals
    • Why non-demand calls no-show more, and how to make a booking stick
    • Why discounting hurts more than your gross profit
    • Why the red line commission model pushes reps to drop their price
    • Why bringing up financing at the end sounds like asking the customer if they’re poor
    • The “subject to” wording swap that makes deferred payments sound normal
    • Why 80% of people who get approved for financing move forward
    • Rehashing lost leads in winter with a no-payment promotion
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    42 min
  • How to Offer Financing Without Making It Awkward
    Oct 6 2026

    Guest: Jeff Cronin — Founder, Primetime Consulting | Close Like Cronin
    Guest Links: Skool: Close Like Cronin | Instagram & Facebook: Jeff Cronin

    Homeowners aren't picking your competitor because they like them more. They're picking whoever offered financing.

    Jeff Cronin trains plumbing, HVAC, and home service sales teams across the country, and spent years at the top of the board in the field before that. He breaks down the deadly mistakes contractors make with financing, starting with the most common one: not offering it at all (9:54). Tim shares how Owl Roofing lost deals in its first summer to competitors who simply offered payments (10:30). Jeff also explains how to diagnose where revenue leaks between leads and collected money (33:59), and why chasing unicorn salespeople usually backfires (41:37).

    You'll learn:

    • Why "afford" is the word that kills the deal, and what to say instead
    • Why every five digit price should have a three digit payment right next to it
    • Why waiting for "I can't afford it" before offering financing is a sales sin
    • The 6% dealer fee rule and why long no-interest deals can eat your margin
    • How to frame a 15-year loan so it sounds like flexibility, not a prison sentence
    • Why one option per page beats dumping all three at once
    • How to tell if you have a close rate problem or an average ticket problem
    • "Pass the mic": the two words to say when you don't know what to say
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    56 min
  • Nayt Pingry on Selling $1M in first 3 Mo at Owl Roofing
    Sep 29 2026

    Guest: Nayt Pingry — Sales, Owl Roofing
    Guest Links: Website: https://owlroofing.com

    $1 million in roofing sales in three months, 80% retail, in a market where everyone is still chasing insurance.

    Nayt Pingry started as a graphic designer on the back end of roofing companies, worked his way up to sales director, then gave up management to sell full time at Owl Roofing. He started July 1st and crossed $1 million in about three months. He breaks down how he flips a denied or high-deductible insurance claim into a retail sale (7:43), why cedar shake homes are the easiest retail opportunity right now (3:01), and why homeowners are buying more practically than emotionally (18:01). Plus an honest look at the growing pains inside a company doing 20 roofs a week in year one (9:56).

    You'll learn:

    • The three questions he has homeowners ask their insurance company before filing a claim
    • Live role play: how to pivot a denied claim into a retail conversation
    • How to handle "I could pay the deductible, I just don't want to"
    • Why cedar shakes and insurance non-renewal letters are the current arbitrage
    • Why he asks every homeowner "have you done any research?" (including ChatGPT)
    • His split: 33% self-generated, 67% company leads
    • Why a strong brand makes cold door knocks feel warm
    • Why family owned and operated is a real differentiator, not just a headline
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    35 min
  • We Started a Roofing Company in a Down Market… Here’s What Happened
    Sep 22 2026

    Guest: Noah Berglin — Co-Founder, Owl Roofing
    Guest Links: Website: https://owlroofing.com

    A year ago he said don't join the roofing industry. Now he runs a roofing company. Real numbers, no spin.

    Noah Berglin came on this podcast a year ago and vented about how rough it was to be a roofing sales rep in the Twin Cities. That episode kicked off him leaving his company and co-founding Owl Roofing. This is the honest one-year check-in: $4 million sold, $5 million collected, aiming for $7 to $10 million, with roughly 50/50 retail and insurance work. He explains why the insurance model is quietly converting to retail whether contractors like it or not (3:42), why door knocking underperformed expectations (17:18), and why he thinks financing is the actual future of roofing (27:46).

    You'll learn:

    • Why actual cash value and roof payment schedules are turning insurance jobs into retail sales
    • The real split: what's working and what isn't at the one year mark
    • Why sold and collected are different numbers, and why deposits are the scariest trap in roofing
    • How much cash a roofing company should carry into winter
    • The $30K storm response budget sitting ready for digital billboards and postcards
    • Why 100 doors a week got harder when leads went up
    • The dad joke yard sign strategy and how to A/B test 500 signs at a time
    • Why you're not competing with other roofers, you're competing for attention
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    34 min
  • She Started an HVAC Company to Prove Her Marketing Works
    Sep 15 2026

    Guest: Brianna Skiffington — Founder, Free Agency | Co-Founder, Space Heroes HVAC
    Guest Links: https://callspaceheroes.com | https://freeagency.ai | https://cxc.ai

    A fractional CMO who spent 10 years marketing the trades just started her own HVAC company. Goal: $10M next year.

    Brianna Skiffington runs Free Agency, publishes Moneyball Marketing, and just launched Space Heroes HVAC in Huntsville, Alabama, remotely. She built the website with Claude in three days, is budgeting 25 to 30% on marketing through 2030, and is finally testing everything she's been telling clients to do for a decade (44:59). The conversation also gets into lead aggregators most roofers dismiss (14:38), the satellite GBP playbook after running 50 of them (40:00), and why marketers should stop pitching against each other.

    You'll learn:

    • The lead aggregators everyone says suck that actually work (Thumbtack, HomeAdvisor, Yelp, Modernize)
    • The car insurance story behind her "call three times in one minute" rule
    • Why speed to lead beats everything and how to wire it into your CRM
    • How to open a satellite GBP the right way (citations first, internet bill, Chrome hack)
    • Why you check the top 3 reviewed companies before betting on LSAs in a new market
    • The voice memo to blog pipeline she runs with field techs from 800 miles away
    • Tim's backlink reverse-engineering play: write for what AI wants to cite, not your ideal customer (35:00)
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    55 min
  • 3 Things Keeping Your Roofing Sales Team Stuck
    Sep 8 2026

    Guest: Sam Tacheny — Owner, Tacheny Exteriors
    Guest Links: Website: https://tachenyexteriors.com

    Two Twin Cities roofing competitors sit down and share everything. Culture, sales systems, PE horror stories.

    Sam Tacheny runs Tacheny Exteriors in the Twin Cities and reached out to talk shop instead of treating the competition like the enemy. The conversation gets into why private equity is flooding the roofing market and what happens when it goes wrong (14:36), the Roscoe bankruptcy that left homeowners with unfinished work, why family owned businesses should act like enterprise companies anyway, and Sam's three recommendations for building a sales team without wrecking it (21:22).

    You'll learn:

    • Why most price objections are actually a lack of discovery
    • How to find your real core values instead of aspirational ones on a wall
    • Why you need one documented selling system, not "here's some videos, good luck"
    • Why the insurance game is getting harder and retail should be your focus
    • What to watch for in PE acceleration clauses before you sign
    • The hook, open loop, and pattern interrupt formula for contractor video (32:56)
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    40 min
  • Why Most Home Service Companies Get Stuck at $3M
    Sep 1 2026

    Guest: Tom and Karen Belko — Owners, Vector Services
    Guest Links: Website: https://callvector.com

    How this HVAC and plumbing company went from $3M to over $10M in two years. Three moves did it.

    Tom and Karen run Vector Services in the Twin Cities doing HVAC, plumbing, electrical, and drains. In 2023 they were nine employees running white vans out of their houses. Now they're pushing $12.5 million and hiring a sales director. They break down the three moves that got them there: going deep on Service Titan instead of treating a CRM like a bolt-on (2:38), the Kick Charge rebrand with Dan Antonelli that put their wraps all over the metro (18:44), and hiring people smarter than them and actually getting out of the way (19:54).

    You'll learn:

    • How to get technicians to actually adopt new software
    • The follow-up dashboard and daily report that holds salespeople accountable
    • Why your CRM setup IS your business process, not an add-on
    • The difference between a high performing salesperson and a real sales leader (25:06)
    • Why family owned beats PE-backed when you're recruiting
    • The yard sign and wrapped bus strategy for cities that ban billboards
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    46 min