Guest: Dan Walreck — Founder, Go Beyond the Hustle | 28-Year Roofing Sales Rep Guest Links: Website: https://gobeyondthehustle.com“If I get your insurance to cover 85% of your roof, would you do it?” Why that question beats the old pitch.Dan Walreck has sold roofs for 28 years, once did $18.7 million in a single year across 595 homeowners, and was on three appointments the day before recording. He breaks down how homeowner psychology shifts every three to five years, and why “all you pay is your deductible” no longer works when 90% of homeowners carry big deductibles (3:24). The real difference now is technology and education (2:35). He also covers why reps should step on the gas in Q4 instead of coasting (9:20), and the $170,000 claim he won by spending 35 minutes on $100 worth of window screens (20:21).You’ll learn:The 85% talk track for homeowners with $5K to $10K deductiblesWhy knowing each insurance carrier’s guidelines (like ACV after 10 years) closes more dealsWhy Q4 and winter are when you build next spring’s pipelineWhy Owl lost a $16K job to a $32K bid, and what that says about trustThe question to ask every homeowner: are you basing your decision on price or value?Why reps leave companies because they don’t feel part of it, not because of moneyWhy a $1M rep in 2000 is a $2.5M rep todayWhy Dan hires 30 to 40 year olds over 22 year olds

Guests: Pavel — Owner, Pasco Construction & Revision European Windows Dan — Sales Manager, Pasco Construction & Revision European Windows Guest Links: Website: https://revisionwindows.comHow 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 winterThe free energy audit pitch using a $120 thermal cameraThe promo: buy ten windows, get free attic insulationWhy out-of-state storm chasers are making every roofer look badWhat to do from mid-December to mid-January (and when to get back to work)Turning Loom training videos into quizzes with ClaudeWhy not switching your CRM can be the smartest offseason callProLine vs JobNimbus: what each team actually likes about their CRM

Guest: Trent Lowenstein — Coach, Next Level Pros | Host, Trent and Friends Podcast Guest Links: Website: https://gonextlevelpros.comYou 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, referralsWhy non-demand calls no-show more, and how to make a booking stickWhy discounting hurts more than your gross profitWhy the red line commission model pushes reps to drop their priceWhy bringing up financing at the end sounds like asking the customer if they’re poorThe “subject to” wording swap that makes deferred payments sound normalWhy 80% of people who get approved for financing move forwardRehashing lost leads in winter with a no-payment promotion

Guest: Jeff Cronin — Founder, Primetime Consulting | Close Like Cronin Guest Links: Skool: Close Like Cronin | Instagram & Facebook: Jeff CroninHomeowners 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 insteadWhy every five digit price should have a three digit payment right next to itWhy waiting for "I can't afford it" before offering financing is a sales sinThe 6% dealer fee rule and why long no-interest deals can eat your marginHow to frame a 15-year loan so it sounds like flexibility, not a prison sentenceWhy one option per page beats dumping all three at onceHow 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

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 claimLive role play: how to pivot a denied claim into a retail conversationHow to handle "I could pay the deductible, I just don't want to"Why cedar shakes and insurance non-renewal letters are the current arbitrageWhy he asks every homeowner "have you done any research?" (including ChatGPT)His split: 33% self-generated, 67% company leadsWhy a strong brand makes cold door knocks feel warmWhy family owned and operated is a real differentiator, not just a headline

Guest: Noah Berglin — Co-Founder, Owl Roofing Guest Links: Website: https://owlroofing.comA 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 salesThe real split: what's working and what isn't at the one year markWhy sold and collected are different numbers, and why deposits are the scariest trap in roofingHow much cash a roofing company should carry into winterThe $30K storm response budget sitting ready for digital billboards and postcardsWhy 100 doors a week got harder when leads went upThe dad joke yard sign strategy and how to A/B test 500 signs at a timeWhy you're not competing with other roofers, you're competing for attention

Guest: Brianna Skiffington — Founder, Free Agency | Co-Founder, Space Heroes HVAC Guest Links: https://callspaceheroes.com | https://freeagency.ai | https://cxc.aiA 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" ruleWhy speed to lead beats everything and how to wire it into your CRMHow 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 marketThe voice memo to blog pipeline she runs with field techs from 800 miles awayTim's backlink reverse-engineering play: write for what AI wants to cite, not your ideal customer (35:00)

Guest: Sam Tacheny — Owner, Tacheny Exteriors Guest Links: Website: https://tachenyexteriors.comTwo 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 discoveryHow to find your real core values instead of aspirational ones on a wallWhy 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 focusWhat to watch for in PE acceleration clauses before you signThe hook, open loop, and pattern interrupt formula for contractor video (32:56)

Guest: Tom and Karen Belko — Owners, Vector Services Guest Links: Website: https://callvector.comHow 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 softwareThe follow-up dashboard and daily report that holds salespeople accountableWhy your CRM setup IS your business process, not an add-onThe difference between a high performing salesperson and a real sales leader (25:06)Why family owned beats PE-backed when you're recruitingThe yard sign and wrapped bus strategy for cities that ban billboards

Guest: Lance Bachmann — Founder & Owner, LB Capital | MN Exteriors Guest Links: Website: https://lbachmanncapital.comLance Bachmann grew up in foster care and group homes, went bankrupt in his 30s, and now runs LB Capital, a home service platform on track for $150 to $175 million in revenue with 14 roofing companies under MN Exteriors, all funded with his own money and zero private equity. In this episode, he explains why roofing in 2026 is where HVAC was 30 years ago, breaks down the LB Capital 50% partnership model and why retaining local brand equity is non-negotiable, and gets blunt about the three metrics that actually matter. It's a raw conversation about energy, marriage, haters, gratitude, and why most people overcomplicate a business that comes down to sold revenue, gross profit, and net income.You'll learn:Why roofing in 2026 is where HVAC was 30 years ago (and why PE can't find good companies)The LB Capital model: 50% equity, operational control, and full playbook accessWhy retaining local brand equity beats consolidating under one nameHow adding roofing to an HVAC and plumbing business added $15M in revenueThe three metrics that actually matter: sold revenue, gross profit, net incomeWhy 50% gross profit almost guarantees 15 to 20% net if operations are rightThe daily automated text report he gets at 6am (leads, booking rate, close rate, average ticket, rehash)Why he fired his own mother from bookkeeping over a mindset mismatchWhy he never discusses business with his wife (and why he thinks no one should)How bankruptcy happened: no financial literacy, not a bad economyWhy he owns real estate outright so he can never go bankrupt againSauna, ice bath, prayer, and cutting alcohol: the energy management routineThe Man in the Arena principle and why haters don't get attentionWhy he'll sell the platform but only to someone who keeps him leading it"We have obstacles, not problems" and the gratitude mindset behind it