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Quick Snapshot of Dillon Cass’s Real Estate Operation
Based in Hamden, Connecticut, Dillon Cass runs a high-volume, team-driven real estate wholesaling company. About 80% of his deals are wholesale real estate assignments, while the rest include flips and buy-and-hold properties. Cass initially focused on creative financing but soon pivoted to wholesaling, which better fit his local market dynamics.
Cass uses a wide range of exit strategies, including wholesale, novation, buy-and-hold, flips, seller finance, and subject-to, but wholesaling remains the primary engine of the business.
In an episode of the DealMachine REI Podcast, Dillon Cass breaks down how he scaled from engineer to 25 real estate deals a month, sharing insights on marketing, hiring, sales, and mindset. Want the full story in his own words? Watch the full interview below:
How He Closed His First Real Estate Deal
He started slow while juggling a full-time engineering job in New York City. Evenings were spent cold calling, often with outdated lists and wrong numbers. For months, he heard only rejections.
The turning point came in June of the previous year when Cass invested $15,000 into a high-powered data service. Though the first month yielded nothing, he finally got a response to a text he'd sent weeks earlier. The homeowner wanted to sell, and Cass locked up the property for $225,000 with an estimated value of $375,000.
That deal gave him proof of concept. In the following days, he locked up three more deals. By the end of August, he had over a quarter-million dollars in contracts, leading him to resign from his engineering job in November and move to Connecticut by January.
Why He Pivoted from Subject-To to Wholesaling in Connecticut
Initially trained under creative finance mentors like Pace Morby, Cass wanted to focus on subject-to and seller finance deals. But in Connecticut, where homeowners often hold $200,000+ in equity, those strategies proved rare.
"Subject-to works great in states with low-equity VA or FHA loans, but not here," Cass explained. "Wholesaling caught fire."
He still does creative deals when the fit is right, but his consistent success now comes from wholesaling distressed or off-market properties.
Real Estate Sales Strategy That Helped Dillon Close 25 Deals Monthly
Why In-Person Closings Win in Real Estate
In his first month, Cass lost deals by sending contracts over DocuSign. Sellers would shop offers or ask attorneys to review the paperwork.
"Now, I lock up every real deal in person. I don't leave without a signature."
This in-person approach, combined with strong objection handling, changed his win rate dramatically. He now teaches this method to his acquisition team.
Using Takeaways to Find Real Sellers Fast
Dillon opens calls with: "What's got you thinking about selling?" This simple question reveals urgency. If a seller asks for a top-dollar price, he performs a "takeaway":
"It sounds like listing with a realtor might be a better fit. I'm not your top offer, but I am your most certain offer."
This frames the choice, top price with risk vs. a guaranteed close, and filters out tire-kickers.
Marketing Tactics to Attract Motivated Seller Leads
Cold Calling for Off-Market Real Estate Leads
Most of his deals still come from cold calling. In the early days, he personally called for hours after work using a 3-line dialer. Now, a team of 15 cold callers handles volume.
He uses a layered data approach: foreclosures, probates, absentee owners, vacant homes, high-equity properties, POA transfers, and quick claim deeds.
Why Door Knocking Still Gets the Highest Spreads
Despite scaling, Cass still door knocks 20–25 homes every Sunday.
"I know if I hit 20 doors, I'll get a deal. If they're selling, they'll sell to me."
These deals often yield the largest spreads due to trust built in person.
How to Find Real Estate Buyers and Close Deals Fast
Dillon flipped his first deal himself. Others came from Facebook real estate groups, investor meetups, CRM buyer lists, and relationships with hard money lenders.
"I never had trouble moving a good deal," he says. "If the numbers make sense, the buyers are there."
Repeat buyers and joint ventures help him move volume without friction.
Building a Real Estate Team That Can Handle 25 Deals a Month
He scaled fast post-proof of concept. Today his team includes:
- 3 in-house acquisition managers
- 1 dispositions manager
- 1 transaction coordinator
- 15 cold callers
- 2 CRM specialists
- 1 executive assistant
Early hiring mistakes taught him that polish doesn't equal performance.
"You need someone who can qualify sellers fast and follow a structured process."
He trains his team to focus on the four sales pillars: motivation, timeline, condition, and price. He also reinforces story-driven selling, persuasion, and clear objection handling.
The Two-Half Real Estate Sales Process
He views sales in two halves:
- Qualification: Separate serious sellers from time-wasters. Ask clear questions, use takeaways, and disqualify quickly.
- In-Person Closing: Walk through the process, handle objections early, and close with confidence.
"Sales isn’t about being likable. It’s about following a proven process."
Why Real Estate Price Points Matter in Wholesaling
Dillon operates in a market where average home prices range from $400K to $500K. That means assignment fees are often 3-4 times higher than in lower-cost areas like Missouri.
"It’s the same amount of conversations per deal," he said, "but the payoffs are bigger. That makes it easier to scale and reinvest."
Smart Data Use for Finding Motivated Real Estate Sellers
While he once believed in a "magic list," experience taught him otherwise. Now he uses multiple data points and behavioral filters, from foreclosures to quitclaim deeds, to target sellers.
He’s even tracked less common patterns like power-of-attorney filings, age ranges, and lifestyle indicators like smoking habits.
"If you smoke and are over a certain age, there's a strong chance you're ready to sell."
His dream dataset? Credit scores with sudden drops, which could signal financial distress.
How Dillon Builds Long-Term Wealth Through Rental Properties
Cass doesn’t believe in small cash flow.
"If you’re only making $400 a month, you’re buying the wrong deals."
He prefers small multifamily buildings with strong margins. Recent deals include:
- A 5-unit expected to cash flow $3,000 to $4,000/month
- A subject-to home with a 2.4% interest rate and $1,200 monthly spread
His wholesaling skillset lets him acquire deep-discount rentals others miss.
Tools and Tech That Support a High-Volume Real Estate Business
He prefers manual mail options over automated sequences for precise timing. He wants to send targeted mail by hand when the moment is right.
His current systems already pull from niche public/private datasets. His next desired upgrade? Credit score drops as real-time seller indicators.
Lessons for Aspiring Real Estate Wholesalers
- Commit fully: Partial effort brings partial results.
- Use a real sales system: Learn it, train it, and teach it.
- Go in person: Signed deals happen face-to-face.
- Disqualify fast: Focus on the players.
- Layer your marketing: Cold calls, door knocking, SEO, mail, and PPC all have a place.
Final Takeaways: Scaling, Sales, and Real Estate Wholesaling Success
Dillon Cass's journey is proof that success follows commitment, data discipline, and smart sales training. He went from a frustrated engineer to a high-volume wholesaler doing 25 deals a month in just over a year.
His edge wasn’t magic lists. It was persistence, process, and people. He invested in mentors, studied sales systems, and built a team to execute.
For aspiring investors: treat every deal as a lesson, market with purpose, and meet sellers face-to-face. Real estate success isn’t about hacks, it’s about skill, follow-up, and consistent action.
Frequently Asked Questions About Real Estate Wholesaling
What is real estate wholesaling, and how does it work?
Real estate wholesaling is a strategy where investors secure a property under contract and assign it to another buyer for a profit, without renovating or owning it.
How many deals do top wholesalers close per month?
Top wholesalers like Dillon Cass often close 20–25 deals monthly, but newer investors may start with just 1–3 while building systems.
What’s the best marketing channel for finding motivated sellers?
Cold calling remains most effective, supported by mail, SEO, PPC, and door knocking for volume and speed.
Is it better to wholesale or buy rental properties?
It depends on your goals. Wholesaling generates fast income, while rentals provide long-term wealth. Many investors do both.
How do I know if a seller is motivated?
Ask, “What’s got you thinking about selling?” Look for urgency, property condition, and willingness to sell at a discount. Disqualify quickly if there’s no clear motivation.
How can I get my first real estate wholesale deal?
Start by pulling a targeted seller list (like probates or absentee owners) and begin cold calling consistently. Use a proven sales process and aim to meet serious leads in person to close on the spot.