We pulled lessons from Jonathan Swanson’s episode on the DealMachine REI Podcast and compared them to what other high-performing wholesalers teach, and this is what we came up with for real estate investing tips that are simple and repeatable.
Swanson’s story is a reminder that real estate rewards consistency more than cleverness. He walked away from corporate healthcare, closed his first deal for $25,000, and built a flexible life with rentals, flips, and short-term stays. His main point is clear: get off the sidelines, work your local area, and keep your marketing direct.
That is the heart of wholesale real estate. Show up, follow up, and stack reps until the phone starts ringing.
The Core Lesson: Action Beats Perfection
New investors stall for one reason more than any other. They wait for the perfect plan.
Swanson’s approach is the opposite. He believes steady action creates deal flow, cash, and confidence. His first deal back in 2004 was simple. He bought, did minimal prep, and sold to another investor. He made $25,000 without overthinking it.
Two decades later, he still wins with simple moves:
- Driving for dollars
- Simple postcards
- In-person networking
As Swanson puts it:
“Figure out something you want to do and just go do it.”
Best-Practice Consensus: Driving For Dollars Still Wins
One of your biggest “unfair advantages” as a new investor is that you can do what most people will not do. You can drive neighborhoods, spot problems, and talk to real owners.
Swanson’s driving-for-dollars approach matches what you see from other proven wholesalers who are known for results:
What The Top Producers Agree On
Across multiple high-volume operators, the best practice is the same:
- Build Your Own List, Do Not Buy A Generic List
A list made from real property conditions is harder to copy and usually has less competition. - Focus On One Tight Area
When you work the same pockets, you learn street-by-street values, rents, and buyer demand. - Follow Up More Than You Think You Should
Most deals do not come from the first call or the first postcard. They come from steady follow-up. - Keep The First Message Simple
A basic offer to help, plus a clear phone number, beats fancy wording.
Swanson does this by driving for dollars and postcards. Other top wholesalers often blend driving for dollars with outbound calling and strong buyer relationships. The method varies, but the core engine is the same: a local list you built yourself, plus consistent contact.
If you want to do this efficiently, DealMachine helps you:
- Pin properties while you drive
- Organize leads by neighborhood
- Track touchpoints and follow-up
- Keep notes on motivation, condition, and timeline
Evidence From The Field: Wins And Painful Lessons
Swanson’s path is not theory. It is a deal-by-deal process.
- First deal: bought, did minimal prep, sold to another investor, netted $25,000
- Current business: 36 rentals, plus flips and short-term rentals
- Recent off-market win: bought just under $100,000, put in over $50,000, listed at $240,000, expected net of $65,000–$70,000 after costs
He also learned the hard way that time can crush profit. A flip stuck in a flood zone dragged on and lost about $10,000 after holding costs. It required extra steps, such as a survey, dirt work, and an LOMA.
The lesson is not “avoid tough deals forever.” The lesson is “price risk correctly.” If the spread is thin, one problem can wipe you out.
Wholesaling Workflow: From Driving To Assignment Fee
This workflow is the simplest path from “I found a house” to “I got paid.”
Here’s the workflow in plain steps:
- Drive for dollars and build a local list
- Find the owner's contact info
- Outreach by mail, call, or door knock
- Answer the phone and qualify the seller
- Make the offer and get it under contract
- Open the title and confirm you can assign
- Send the deal to your buyers' list
- Close and collect the assignment fee (or double close)
Real Estate Investing Tips: A Tactical Playbook New Investors Can Use
Swanson’s advice is practical and beginner-friendly. None of it requires a license in most areas. None of it requires a huge budget.
Build A 200-Property Driving For Dollars List
Drive your target area and look for signs like:
- Overgrown grass
- Boarded windows
- Peeling paint
- Notices on doors
- Piles of trash
- Vacant feel
Start small. Two hundred properties are enough to get traction if you are consistent.
Mail That Gets Calls
Swanson found that adding a headshot helped the response. It makes you feel real, not like a faceless company.
Keep copy plain:
- “I’m interested in buying your house.”
- “I can buy as-is.”
- “We can close on your schedule.”
- “Call or text me at this number.”
Use “Close On Your Schedule”
This line reduces seller fear. Many sellers do not want fast. They want control.
This also helps you compete against “close in 7 days” marketing because you are speaking to a real human need.
Track Results By List
Swanson tracks by list using different phone numbers so he knows what is working.
A clean setup:
- One number for driving for dollars
- One number for code violations
- One number for landlord outreach
When you know which list produces calls, you can spend more time and money on the winner.
Show Up At Your Local REIA
In-person rooms still matter because money and deals move through relationships.
Your goal at each meeting:
- Meet five active buyers
- Meet two private lenders
- Meet one agent who works on investor deals
- Follow up within 48 hours
Expanded Legal Section: Disclosures In Major States
Wholesaling rules vary by state. Some states focus heavily on disclosure language, and some focus on whether you are acting like a broker.
This table is not legal advice. It is a starting point, so you ask better questions when you talk to a local real estate attorney.
|
State |
What To Disclose |
What To Watch Out For |
Practical Compliance Tip |
|
Texas |
Texas has specific notice rules around assigning a buyer’s interest. Disclosures often focus on making it clear you do not hold legal title and that you are selling/assigning a contract interest. |
Failing to give the required notice to the right parties at the right time can create problems. |
Put clear “equitable interest” disclosure language in your assignment agreement and keep a standard written notice process. |
|
Illinois |
Illinois is known for stricter limits and disclosure expectations for unlicensed activity. Written disclosure that you do not hold legal title is commonly discussed, along with limits on how often an unlicensed person can wholesale. |
Repeated transactions without a license can be treated as illegal brokerage activity depending on the facts. |
Do not “market the property” like an agent. Market your contract interest, disclose clearly, and get attorney guidance early. |
|
Florida |
Florida’s licensing law focuses on acting “for another” for compensation. Publicly advertising a property you do not own can create risk if it appears to be brokerage activity. |
Marketing the property itself as if you represent the seller can cross the line. |
Keep marketing tied to your contract rights and avoid language that implies you are listing the property for the owner. |
If you only remember one thing: be transparent about what you own. In wholesaling, you are usually selling your contract position, not the property itself.
Holding Costs: The Silent Profit Killer
Swanson’s flood-zone deal points to a common beginner mistake. People underestimate holding costs and time.
Even if you do not borrow money, you still pay to own a house. Taxes, insurance, utilities, lawn care, and time do not stop.
Simple Holding Cost Formula
- Monthly Holding Cost = Interest + Taxes + Insurance + Utilities + Lawn/Trash + HOA + Other
- Total Holding Cost = Monthly Holding Cost × Months Held
The 7-Day Plan (And How To Turn It Into A LinkedIn Challenge)
Swanson’s call to action is simple: stop waiting and stack reps. Here is the same 7-day plan, organized as a LinkedIn challenge you can run to build authority and community.
Day 1: Pick Your Farm Area
Post: “I’m choosing one neighborhood and committing to it for 30 days.”
Action: Drive the area once without stopping. Learn the streets.
Day 2: Build Your First 50-Property List
Post: “Today I’m building a list from what I see, not what I scrape.”
Action: Tag 50 properties and add notes on condition.
Day 3: Finish The 200-Property List
Post: “Volume matters. I’m going to 200.”
Action: Tag the next 150 properties.
Day 4: Send Your First 200 Touches
Post: “I sent mail to my list. No fancy copy. Just clear intent.”
Action: Mail postcards or letters and track the list source.
Day 5: Call And Follow Up
Post: “Most deals are follow-up. I’m calling everyone back.”
Action: Return every missed call and log outcomes.
Day 6: Build Your Buyers List
Post: “Deals are easy when buyers are ready.”
Action: Meet buyers at REIA, collect buy boxes, and save contacts.
Day 7: Make Offers
Post: “The only way to learn offers is to make offers.”
Action: Make two to five offers based on condition and timeline.
If you do this and stay consistent, the first check becomes a when, not an if.
FAQs
Do I Need A Lot Of Money To Start Wholesaling?
No. Many wholesalers start with a purchase agreement, a solid closing partner, and a buyer's list. The main cost is marketing and time spent following up.
What Should My First Marketing Step Be?
Start by driving for dollars to create a list based on real property conditions. Then send a simple email or call the owners and track results.
How Do I Find Real Cash Buyers And Lenders?
Show up at local investor meetups and REIA meetings. Ask who is actively buying now and what they want, then keep those contacts organized.
What Is The Biggest Mistake New Wholesalers Make?
Waiting for the perfect instead of taking steady action. The second biggest mistake is underestimating holding costs and time on deals that drag out.