Ask Frank

William Chomley

Real talk for America's small businesses to help them grow Ask Frank is the weekly 15-minute show for small businesses where every Tuesday: one owner question, one expert in the field, clear steps. From breaking $1M to scaling past $10M to exiting on your terms. We do the playbook from one truck to ten, smart debt as a wealth lever, stacking assets, and the exit. Got a burning question? Submit at talktofrank.ai and hear it on the show. Hosted by Will Chomley, founder of Frank — 🌐 talktofrank.ai 📬 Substack: substack.com/@talktofrankai 📸 Instagram: instagram.com/talktofrank.ai 🎵 TikTok: tiktok.com/@talktofranktoday 📘 Facebook: facebook.com/people/Frank-Talk-to-Frank/61583722127699

  1. Aug 5

    Trades are the new golf. Everyone wants in. Dillion Caraway on whose getting funded

    Dillon Caraway is a Senior Loan Officer at Live Oak Bank on the service contractor vertical — HVAC, plumbing, electrical, roofing, garage door. He funds trades operators across America, and he sits on one of the sharpest windows into what's actually happening in the industry right now. In this episode Dillon answers: What's actually getting funded in 2026 — the acquisition boom, the real estate plays, the working capital deals, and where PE consolidation is showing up in the tradesWhy your local bank keeps saying no: the difference between collateral-based lending (what most banks do) and cash-flow-based lending (what Live Oak specialises in) — and why that matters when you're trying to buy a competitorThe real estate purchase math: when owning the building beats leasing, and the specific scenario where it doesn't (your rent triples, and it kills your cash flow)What Live Oak actually delivers as a preferred SBA lender: 6–8 weeks start to finish, in-house approvals, and 60–90 days faster than the SBA horror storiesThe buyer profile that gets funded for an acquisition: industry experience, licensing, 680+ credit, 10% equity injection — and when Live Oak will let you split the 10% as 5% cash + 5% seller financingThe biggest mistake Dillon sees buyers make: ignoring red flags like customer concentration risk, project-based revenue mix, and employee turnoverPlus: the "silver tsunami" of owner transitions coming for the trades industry over the next 5–10 years, and why Dillon thinks change-of-ownership deals are the single biggest opportunity for the $1–5M operator right now. Got a business question you want answered on Ask Frank? Submit it at talktofrank.ai/askfrank — every episode is built around a real operator's question. 🌐 Website: talktofrank.ai 📬 Substack: substack.com/@talktofrankai 📸 Instagram: instagram.com/talktofrank.ai 🎵 TikTok: tiktok.com/@talktofranktoday 📘 Facebook: facebook.com/profile.php?id=61583722127699 ▶️ YouTube: Ask Frank — @talktofrankai 🟢 Spotify: open.spotify.com/show/1aSkX5ccK1U15oU4gte1Ug

  2. Jul 21

    He started with a $20 lawn. He ended with a $10M exit. Then he sold it—and started coding.

    At 15, Bryan Clayton mowed the neighbour's lawn to buy the $100 soccer cleats his dad wouldn't. Fifteen years later, that mower was Peachtree Landscape Group — 150 employees, eight figures in revenue, and a full acquisition by a national roll-up. Then he did the harder thing: he started over. Today Bryan is the co-founder and CEO of GreenPal, the "Uber for lawn care" — nationwide across the US, 42,000 lawn care operators on the supply side, and 300,000+ homeowners using it every week. He's aiming for a million. In this episode Bryan tells the story of: The 15-year journey from a single mower to $10M — and the specific "levels" (his words) that almost stopped him at $1M, at $2M, at $5MThe moment he realised he wasn't in the landscape business — he was in the sales business — and the 2-year rebuild that unlocked the exitThe hardest lesson of a lifestyle-vs-acquirable business: "acquirers only care about how much profit drops to the bottom line, and the systems behind it. That's it."Why he walked away from the "just invest and live the good life" post-exit plan — and what actually pulled him back inThe GreenPal cold-start playbook: how they cracked the two-sided marketplace one city at a time, hand-cranking the first dozen markets before the network took overThe power law that runs the business now: 20 of their 300 cities drive 90% of the volume — and how they're using that data to unlock the rest Got a question for the show? Submit at talktofrank.ai. 🌐 Website: talktofrank.ai 📬 Substack: substack.com/@talktofrankai 📸 Instagram: instagram.com/talktofrank.ai 🎵 TikTok: tiktok.com/@talktofranktoday 📘 Facebook: facebook.com/profile.php?id=61583722127699 ▶️ YouTube: Ask Frank — @talktofrankai 🟢 Spotify: open.spotify.com/show/1aSkX5ccK1U15oU4gte1Ug

  3. Jul 14

    Britt Wood (NALP) on the numbers that put a landscape operator in the top 20%

    A $1M landscaper in Charlotte with four trucks wants to know: am I in the top 20% — and if not, what changes? Britt Wood, CEO of NALP, gives him the actual numbers. Britt Wood runs the National Association of Landscape Professionals, the trade body representing the entire US landscape industry — from solo operators to billion-dollar roll-ups. Before NALP, he spent his career leading trade associations across retail, food service distribution, and civil engineering. In this episode Britt answers: The benchmarks that actually matter: $156K revenue per employee (not per truck), 50%+ gross margin, 90% customer retention — the numbers separating high performers from the packThe right mix of design-build vs. maintenance — where the profit is vs. where the recurring revenue lives — and why the balance matters more heading into 2027The geographies growing fastest: Carolinas, Georgia, Florida, Tennessee in the Southeast — plus Arizona, Utah, Nevada out west — and what that means for a landscaper's next expansion moveHow to actually break into commercial and municipal work: advocacy, community involvement, and why the operators who show up locally are the ones who win the big contractsThe single biggest lever for a $1-3M operator right now: employee retention — and why NALP's free technician and business-manager training is designed to help the smallest operators build itPlus: the ITR economic forecast (a $40K report NALP members get for free), the 2027 softening + 2028 rebound outlook, and why NALP costs under $1,000/year for operators under $2M in revenue. Got a question for the show? Submit at talktofrank.ai. 🌐 Website: talktofrank.ai 📬 Substack: substack.com/@talktofrankai 📸 Instagram: instagram.com/talktofrank.ai 🎵 TikTok: tiktok.com/@talktofranktoday 📘 Facebook: facebook.com/profile.php?id=61583722127699 ▶️ YouTube: Ask Frank — @talktofrankai 🟢 Spotify: open.spotify.com/show/1aSkX5ccK1U15oU4gte1Ug

  4. Jul 7

    Matt Michel on what 100 confidential exits taught him about selling a company

    Matt Michel spent 20 years as the president of Service Nation, supporting tens of thousands of small service businesses across HVAC, plumbing, electrical, and home services — before selling the company through two successful exits. He then teamed up with M&A advisor Brandon Jacob to write The Business Exit Roller Coaster, a book built on 100 in-depth, confidential interviews with former business owners about the most important financial decision of their lives. Nobody in America has heard more owners tell the truth about what actually happens in an exit than Matt and Brandon. In this episode, Matt walks through what 100 confidential conversations revealed about the emotional AND financial rollercoaster of selling a service business: Why signing the LOI is only "half-time" — all of the gain of imagining the money, none of the pain of due diligence yet to come — and why the second half is where most deals quietly dieThe proactive vs reactive divide — owners who spent a year preparing outperformed the ones forced to sell by life events, and by how muchThe "money-whipped" trap — the private-equity knock-on-the-door offer that anchors you to a number that leaves 30–50% of your actual value on the tableThe rollover-equity trap — the "second bite of the apple" pitch that's usually sold as 3–5x cash-on-cash in 2–3 years, and the operator Matt interviewed who rolled eight figures forward and got nothing backThe number check that stopped Matt's friend Chris from selling for $4M — and why doing this math BEFORE you take the meeting saves owners more money than any negotiation tactic Plus: the "golf pro vs. amateur" analogy that explains why every service business owner needs an M&A advisor (and why skimping on the caddy tip is the mistake that costs the most); the identity crisis that hits every extroverted, Type-A owner post-sale (Matt calls it the tombstone-business-card moment); the two owner stories he still thinks about — including the one with $20M in personal guarantees who described the relief of the sale as a physical weight lifting — and the single question Matt asked every one of the 100 owners: "Would you take the business back and return the money today?" Not one of them said yes. If you're a service business owner planning an exit in the next two to five years — or you just want the unvarnished truth about what actually happens between the LOI and the life after — this is the episode that pulls the curtain back on the ride nobody warns you about. Got a question for the show? Submit at talktofrank.ai. 🌐 Website: talktofrank.ai 📬 Substack: substack.com/@talktofrankai 📸 Instagram: instagram.com/talktofrank.ai 🎵 TikTok: tiktok.com/@talktofranktoday 📘 Facebook: facebook.com/profile.php?id=61583722127699 ▶️ YouTube: Ask Frank — @talktofrankai 🟢 Spotify: open.spotify.com/show/1aSkX5ccK1U15oU4gte1Ug

  5. Jun 30

    How to buy the business down the street, without blowing up your own business

    Matt Manavi is the CEO and Co-Founder of Transworld Business Advisors' Southern California operation — the largest Transworld franchisee in California, with twelve brokers serving Main Street businesses from sub-$2M up to $70M lower-middle-market. Transworld globally is the largest business brokerage and M&A advisory firm in the world. Matt has seen every flavour of trades acquisition that walks through the California door. In this episode, Matt walks through the playbook every $1–3M trades operator should run before they make an offer on the shop down the street: When buying out a competitor actually beats growing organically — and the strategic question (residential vs commercial, geographic vs service-line) you have to answer BEFORE you look at a single numberThe valuation reality check — why "I'll get two to three times revenue" is one of the most common (and wrong) things sellers tell themselves, and what businesses actually trade at (a multiple of SDE or adjusted EBITDA — not revenue)The seller-note move that adds 10% to every deal — IBBA data shows businesses where the seller carries a note sell ten percent higher than those that don't. Matt explains the standby terms the SBA actually requires, and how to negotiate interest-only for the first two yearsThe new SBA rule that's quietly killing small business acquisitions — if the seller participates in the buyer's 10% down payment, the SBA now records a FULL TEN-YEAR standby. Most sellers walk. Most deals die at the table because of itThe licensing crackdown nobody warned you about — the SBA used to let you buy an HVAC or plumbing business if you "leased" a license from someone with industry experience. Not anymore. If you don't have direct experience in the industry, SBA won't lend on the deal Got a question for the show? Submit at talktofrank.ai.🌐 Website: talktofrank.ai 📬 Substack: substack.com/@talktofrankai 📸 Instagram: instagram.com/talktofrank.ai 🎵 TikTok: tiktok.com/@talktofranktoday 📘 Facebook: facebook.com/profile.php?id=61583722127699 ▶️ YouTube: Ask Frank — @talktofrankai 🟢 Spotify: open.spotify.com/show/1aSkX5ccK1U15oU4gte1Ug

  6. Jun 23

    Jon Hyman on the $10K-per-tech 1099 shortcut that costs $100K to fix

    Jon Hyman is the Practice Chair for Employment and Labor at Wickens Herzer Panza in Cleveland, author of the Ohio Employer Law Blog — one of the most read employment-law blogs in the country — and co-founder of his firm's Craft Beer Practice. He has spent his career advising owner-operators on the worker-classification rules they don't realise apply to them until the IRS, the Department of Labor, or their state comes calling. In this episode, Jon walks through the W-2-to-1099 trap that costs trades operators an average of ten times what they thought they were saving — and the protocol for fixing it before the back-taxes show up: Why what you CALL someone doesn't define the relationship — the relationship defines the relationship, and the 1099 form on its own protects you exactly zeroThe three-framework problem nobody warns trades operators about — the IRS test, the Department of Labor test (which changed twice in two years and is in flux again right now), and the state test (Ohio is 20 factors; California is the ABC test that makes most trades 1099s flat-out illegal)The California ABC test killer — Factor B says the worker has to perform work outside the usual course of the business. A plumber at a plumbing company can never pass that test, and four other states (Massachusetts, New Jersey, Illinois and others) use the same ruleWhat's actually at stake when the IRS shows up — six years of back taxes, three years of unpaid overtime, the Affordable Care Act look-back, and personal liability that follows the director, not just the businessThe 90-day fix protocol — pull every 1099 from the last seven years, run each one through every applicable test, traffic-light them green / yellow / red, reclassify the reds immediately, and self-disclose before the government finds you (you'll get significantly more grace) Got a question for the show? Submit at talktofrank.ai. 🌐 Website: talktofrank.ai 📬 Substack: substack.com/@talktofrankai 📸 Instagram: instagram.com/talktofrank.ai 🎵 TikTok: tiktok.com/@talktofranktoday 📘 Facebook: facebook.com/profile.php?id=61583722127699 ▶️ YouTube: Ask Frank — @talktofrankai 🟢 Spotify: open.spotify.com/show/1aSkX5ccK1U15oU4gte1Ug

  7. Jun 16

    Patrick Lange on why 80% of HVAC businesses listed for sale never actually sell

    Patrick Lange is the founder of Business Modification Group, one of the most active HVAC and plumbing business brokers in the country. He started as a financial planner, bought a pool service company in his midlife-crisis years, scaled it to 300 pools a week, sold it, became a broker the long way around, and now specialises in selling only heating-and-air and plumbing companies. 167 deals later, nobody in America knows more about why $1–5M trades businesses sell — or quietly don't. In this episode, Patrick walks through what he's actually seeing across hundreds of HVAC sales, what the deal-dies-on-the-desk pattern looks like, and what every operator twelve to twenty-four months out from selling should be doing today: What 167 HVAC sales taught Patrick about why $1–2M businesses sell for less than buyers expect to pay — and why $10M businesses sell for multiples that look like science fictionThe IBBA's brutal stat: only 20% of listed businesses actually sell. Patrick names the three things that take down the other 80% — and the one that's preventable"If your name's on every Google review, you don't have a business — you have a well-paying job." The difference between selling a business and selling yourself, and why the latter rarely closes for what the owner wantsThe June SBA rule change that quietly shut down two-thirds of Patrick's deal flow — what changed, what it means for any HVAC owner planning an SBA-financed sale, and what's working now insteadThe 12–24 month pre-sale checklist — what to do TODAY to pay yourself the difference between the deal you want and the deal that quietly dies on the broker's deskPlus: the actual buyer pool in 2026 — PE consolidators, second-gen kids whose parents sold to PE and want their own business, bankers who heard "buy boring businesses," and Harvard lawyers fleeing the firm — and what each of them is actually paying for; why Patrick treats every sale like a "marriage not a divorce"; the customer-concentration trap that turns four "great" customers into a deal-killer; and the one thing Patrick would tell every HVAC owner planning to sell in the next two years to do TODAY — even if their CPA grumbles about it. If you're an HVAC, plumbing, or service operator planning to sell in the next two to five years — or you just want to know what makes one $2M business worth $4M and the one next door worth $1M — this is the episode that gets the deal off the desk and across the closing table. Got a question for the show? Submit at talktofrank.ai. 🌐 Website: talktofrank.ai 📬 Substack: substack.com/@talktofrankai 📸 Instagram: instagram.com/talktofrank.ai 🎵 TikTok: tiktok.com/@talktofranktoday 📘 Facebook: facebook.com/profile.php?id=61583722127699 ▶️ YouTube: Ask Frank — @talktofrankai 🟢 Spotify: open.spotify.com/show/1aSkX5ccK1U15oU4gte1Ug

  8. Jun 9

    Sturdy McKee on the All Blacks playbook that took him from 70-hour weeks to 6

    Sturdy McKee is the creator of the Six Hour CEO framework and one of the most respected owner-operator coaches in America. A physical therapist by training, he built and ran a six-location, forty-eight-person, $4M+ practice, in six to eight hours a week. He spent over a decade in Entrepreneurs' Organization learning from peers, and turned what he learned into a framework now taught to trades operators, contractors and service business owners across the country. In this episode, Sturdy walks through the moves that take a trades operator from "I am the operating system" to running their business like the coach of a winning team, including a detour into the New Zealand All Blacks that neither of us saw coming: Why "you can't delegate invisible work" and the dumbest, simplest tool (a whiteboard or a Google Sheet) that gets a business out of an owner's head and onto paper for the first timeThe 8-to-10-person rule why this is the natural team size one person can manage, and the multiplier structure that kicks in past itThe mindset shift from "hardest working player on the field" to "coach" the identity trap that keeps most $1–3M operators stuck on the wrong side of itThe Six Hour CEO core operating loop process, plays, scorecard, weekly meeting and why "boring is good" when it comes to weekly cadenceThe All Blacks moment Sturdy, an American PT, unprompted, rattles off the All Blacks' 78% win record since 1906, their cultural value "leave the jersey in a better place," and the stewardship lesson that lands the entire Six Hour CEO philosophy in one analogy nobody saw coming Plus: why Sturdy made profit faster the moment he went OUTSIDE his profession for business learning, the dirty little secret that 80–90% of every business (regardless of industry) is the same set of problems, the five critical "plays" every business needs documented — and the one move Sturdy would force every drowning operator to make in the first ninety days, before talking about vision, goals or anything else. If you're a trades or service operator running your business out of your head and your phone — or you just want a coach's playbook for getting your evenings back — this is the episode that gets the operating system out of you and onto paper. Got a question for the show? Submit at talktofrank.ai. 🌐 Website: talktofrank.ai 📬 Substack: substack.com/@talktofrankai 📸 Instagram: instagram.com/talktofrank.ai 🎵 TikTok: tiktok.com/@talktofranktoday 📘 Facebook: facebook.com/profile.php?id=61583722127699 ▶️ YouTube: Ask Frank — @talktofrankai 🟢 Spotify: open.spotify.com/show/1aSkX5ccK1U15oU4gte1Ug

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About

Real talk for America's small businesses to help them grow Ask Frank is the weekly 15-minute show for small businesses where every Tuesday: one owner question, one expert in the field, clear steps. From breaking $1M to scaling past $10M to exiting on your terms. We do the playbook from one truck to ten, smart debt as a wealth lever, stacking assets, and the exit. Got a burning question? Submit at talktofrank.ai and hear it on the show. Hosted by Will Chomley, founder of Frank — 🌐 talktofrank.ai 📬 Substack: substack.com/@talktofrankai 📸 Instagram: instagram.com/talktofrank.ai 🎵 TikTok: tiktok.com/@talktofranktoday 📘 Facebook: facebook.com/people/Frank-Talk-to-Frank/61583722127699

Information

  • Creator
    William Chomley
  • Years Active
    2026
  • Episodes
    13
  • Rating
    Clean
  • Copyright
    © 2026 William Chomley