Starting a Wholesaling Business for $100: AI, Data and the 2026 Market
Two things came out of this conversation between Greg Helbeck, Mike DeHaan and Dylan Koch: the cost of starting a wholesaling business has collapsed, and the market is punishing operators very differently depending on where they stand. Greg shared real losses on Seattle-area flips. Dylan called this the slowest stretch he's seen in Cincinnati. Here's what they said and what it means for how you operate.
What does the late-2026 housing market actually look like?
Greg operates in two very different places: the Seattle area and upstate New York. He bought a flip in Marysville, Washington in April or May, has held it five months, and is now selling it at a roughly $25,000 loss — and it only moved after a price cut. On a Federal Way flip where he expected a solid five-figure profit, he says he'll walk away with about $9,000, which he considers lucky.
Greg's read on Washington is heavy inventory, more supply coming, and people leaving the state. If you don't have the best house at the best price, he says, you sit. New York is different in his experience: buyers moving out of New York City plus difficulty building means a good house priced fairly still sells quickly, though the days of going 15 offers deep are gone.
Mike sees a similar migration pattern in Spokane, where Seattle buyers move east. He and Dan listed a fully remodeled rental on a Thursday, got about 15 walkthroughs over the weekend, three offers, and accepted one over asking. The difference, Mike says, was price discipline — comparable homes were asking more without being remodeled. His take: location still matters most, but it has to be quality plus location now.
Dylan's Cincinnati numbers are the bluntest. He's cut a listing in a class A area twice and is still chasing a comp that sold on the same street in August 2026. Two other properties went under contract only with buyers who had to sell their own homes first; both fell out. Days on market up, inventory up. He called it the slowest he's seen since he started.
How has AI cut the cost of starting a wholesaling business?
Mike said the old startup stack for wholesaling — list pulling, skip tracing, dialers, multiple subscriptions — ran $5,000 to $6,000 before you made a single call. Greg's argument is that most of that is now replaceable. He described using Grok's agent to pull county-level data: ownership records, what's listed, what's sold.
Dylan said he'd tried the same thing with Claude for niche, county-specific data and couldn't get it to work. With Grok's agent, he had the basics running in about two hours one afternoon. Greg's explanation is that it runs its own browser and virtual machine, so it operates like a person clicking through a site. Greg noted Manus was the pioneer with that approach. Before, Dylan said, you were hiring someone on Fiverr, handing over computer access, and starting over every time a URL changed.
On data and dialing, Greg said the current version of Deal Machine includes phone numbers in the subscription and called it "chat GPT for real estate." He stressed he has no affiliation with the company. Greg put it at $200 a month, or around $50 a month if you're on a tight budget, with Grok's agent running about $15. Mike's number for getting started: roughly $100.
Greg's broader point is that data is a commodity, like gas — whoever's cheapest gets the business. Skip tracing felt revolutionary in 2018; now contact information is widely available. The edge moves to whoever executes and builds a system around it.
Why do sloppy operators make it easy to compete?
Greg told a story about buying a deal from another wholesaler in a building where he already owned units. He offered to take it sight unseen and wire $10,000 immediately. He was told two weeks to close; it took almost two months, with title problems and no updates unless he chased them. When Greg finally texted the seller about a key, the seller cursed him out — he assumed Greg was the wholesaler who'd put him through that process.
Greg's takeaway: most people in this business do it badly, so standing out is easy. If you sound reasonable on the phone, listen, actually try to solve the problem and follow up, you're ahead of most of the people calling that same seller. Mike's version is shorter: do what you say you're going to do.
All three pushed back on operators who brag about cost per contract. Dylan's position is that cost per deal is the only metric that matters, because contracts that don't close are worthless. Mike described a clip where someone said he used to expect nine of ten contracts to close and now expects two of ten — which the hosts read as locking up bad contracts, not a market problem. Mike also shared a Spokane example: a buyer he knows signed five contracts in a week on deals another wholesaler had already marketed, at $70,000 to $100,000 less than the original prices.
What's changing on the legal side of assignments?
Dylan said Ohio's new disclosure has to be timestamped before the purchase and sale agreement is signed, so you can't spring an addendum at closing. Mike described a Georgia deal his lending side funded where a Miami party assigned a contract to a local Atlanta buyer for $0 and collected a separate $25,000 consulting fee, with the paperwork specifying it was not an assignment fee and disclosing the equitable interest.
Mike's practical note: structured that way, the fee isn't part of the purchase price, so it can't be wrapped into the loan — the buyer brought it out of pocket. He said he doesn't know Georgia's specific rules. None of this is legal advice; check your own state's requirements.
The through line: the barrier to starting has never been lower, and the cost of being sloppy has never been higher. Greg closed with something a broker friend said about Washington — if you're surviving in that market right now, you're thriving. Listen to the full episode for more on market-by-market spreads.
Frequently asked questions
How much does it cost to start wholesaling in 2026?
Mike estimated around $100, down from the $5,000 to $6,000 it used to take. Greg's stack is an AI agent subscription plus a data tool with built-in phone numbers.
Is cost per contract a useful metric?
Dylan said no — he doesn't take anyone seriously who brags about it, because only cost per closed deal matters. Greg added that a cheap contract priced above market won't convert.
Are rentals still attractive right now?
Greg argued rentals look worse to many buyers given rates and price-to-rent ratios in expensive markets. Dylan countered with a Cincinnati four-unit grossing $3,600 a month, which Greg agreed is well past the 1% rule.
Educational content from the Collecting Keys podcast. Not financial, legal or tax advice.