Greg Helbeck
Greg Helbeck has been a guest on Collecting Keys, the real estate investing podcast hosted by Mike DeHaan, Dan Austin and Dylan Koch, 4 times.
Why Your Real Estate Business is Always Out of Cash w/ Greg Helbeck
Greg Helbeck joins Mike, Dan and Dylan to discuss why so many active flippers and wholesalers stay broke despite doing dozens of deals a year. They cover marketing cost per deal versus overhead, why rentals bought at a discount (not business enterprise value) are what actually builds net worth, and the contractor and comping mistakes that quietly eat profits.
Key takeaways
- Single-member LLCs don't create tax advantages — asset protection and taxes are separate, and most complex entity structures sold online are unnecessary; an operating agreement and certificate of good standing is usually all a title company wants.
- Know your cost per deal against overhead: if marketing costs ~$5K per deal and assignments only net $15–20K, a $20K/month marketing spend needs roughly four deals a month to stay profitable.
- The investors who make the most are often doing 30–50 deals a year with low overhead and good capitalization, not 60–100 transactions; big-volume shops frequently scale back down.
- As lenders, Mike and Dan see most borrowers with $40K–$60K in the bank — sometimes $17K — even after flipping 50 houses, because they roll every deal into the next to cover the last one.
Veteran Wholesaler Calls Out Shady Tactics and Fake Gurus
Greg Helbeck returns to talk through how wholesaling has changed since 2015 and why shady tactics — especially late-stage price drops on sellers days before closing — are inviting regulation and wrecking the industry's reputation. The group covers how to beat national wholesalers without overpaying, what Washington's new 2026 wholesaling rules require, and how Greg is staying competitive by actually closing deals, putting up real earnest money, and being transparent when he intends to wholesale.
Key takeaways
- The scummiest common tactic right now is ordering a "reinspection" 5-7 days before closing and renegotiating the seller down when they're packed and can't walk — Mike and Dan describe a live example where a wholesaler dropped a seller $20K on a deal that was already sold and funded, turning a $10K fee into $30K.
- National wholesalers, not local investors, are the biggest competitive threat — they win contracts by a few hundred dollars, put down $50 earnest money, and then can't perform because they don't know the market.
- You beat them by consulting instead of selling: ask the seller what the other buyer's earnest money deposit is, then offer a meaningfully larger deposit and explain why local knowledge matters (Greg's example: lot values varying wildly along the same street in Seattle).
- Transparent wholesaling works. Greg tells sellers up front he may not be the end buyer but can connect them to one, still puts down real earnest money, and says sellers are fine with it.
What the Big Beautiful Bill Means for Real Estate Investors w/ Greg Helbeck
Greg Helbeck joins Mike, Dan and Dylan to walk through the real estate tax provisions in the "Big Beautiful Bill" — 100% bonus depreciation, Section 179, opportunity zones and the 20% pass-through deduction on net rental income — and why depreciation recapture means the savings are smaller than most people think. The conversation then shifts to why Greg flips in blue states but has lost $55,000 in cash across 11 rentals this year, plus how he used ChatGPT to rewrite his assignment agreement so a flaky end buyer can't blow up a deal.
Key takeaways
- Bonus depreciation reduces your taxable income, not your tax bill dollar-for-dollar — and recapture at 25% on sale means you still owe some of it back unless you 1031 or never sell.
- Passive investors can't use depreciation against active W-2 income unless someone in the household qualifies as a real estate professional; never invest as an LP where the tax benefit is the only upside.
- Greg flips in blue states (New York, Washington, San Diego) and has made money every year, but says blue-state rentals are brutal — evictions can take seven months versus three to four in Eastern Washington and 45 days in Hamilton County, Ohio.
- Expensive markets support bigger spreads: New York assignments run $30K–$50K with cost per deal at $8K–$10K, versus much thinner spreads in cheap Midwest markets.
10 Years of Wholesaling: Greg Helbeck on What You Should Be Doing Differently in 2025
Greg Helbeck, a wholesaler and flipper of ten years operating in New York's Hudson Valley and the Seattle area, joins Mike, Dan and Dylan to explain how he's changed his lead generation for 2025: direct mail as the primary channel, cold calling the same mail data as an inexpensive insurance policy, PPC being rebuilt, and referrals/wholesaler deals as free lead flow. The group also digs into why single-exit wholesalers in one market struggle, how bad actors (memos on title, last-minute renegotiations) are pushing wholesaling toward regulation, and how underwriting and contractor relationships separate operators who last from those who don't.
Key takeaways
- There is no "secret list" — Greg says he has bought Audantic, PropStream-type and other predictive lists and found deals overlapped with plain absentee lists; the only list that works is the "consistency list."
- Cold calling should be a supplement, not the primary channel. Greg calls the same data he mails for about $1,500/month with one caller — one cold-call deal will net over $100K — but it eats team time on "smokescreen" leads, so he's shifting budget back to PPC and mail.
- Free lead sources matter: referrals and deals bought from other wholesalers lower his blended cost per deal (around $10K) because those leads cost nothing.
- Being a wholesaler-only operator in a single market is much harder now. Multiple exits (wholesale, novate, close and flip) plus a couple of surrounding markets increase your odds — and expensive metros hold "invisible deals" where the 70% rule doesn't apply.