6 Lead Gen Strategies Behind 750+ House Flips from Ex-NFL Player Turned Real Estate Investor 

What does it take to go from the NFL to flipping 750+ houses? For some, it’s luck. For others, a trust fund. 

But for Dean Rogers? It was raw, relentless obsession. The kind that makes you trade million-dollar contracts for cold calls, door knocks, and spending hours talking with potential sellers. 

Most people dream of making it to the NFL. Dean got there, played for the San Diego Chargers, and then made an unexpected move: he walked away.

Not because he had to, but because he saw the writing on the wall — injuries, uncertainty, and a future he couldn’t control.  

So, he made the gutsiest decision of his career and stepped into an even tougher arena: real estate. And just like on the field, he didn’t just show up, he went all in. 

Since 2013, Dean has flipped and wholesaled thousands of properties, built an eight-figure rental portfolio, and scaled his business to over 100 deals a year.  

His secret? A lead generation system that doesn’t just deliver, it outperforms. With the right tools and a game plan full of smart, targeted actions, he turns every lead into a touchdown (and yes, more football puns are on the way). 

But it wasn’t always smooth sailing. His first few flips cost him six figures in losses — an expensive crash course in what not to do. Instead of folding, he adapted, refined his strategy, and built a machine that now runs like clockwork. 

He recently sat down with PropertyRadar CEO Mark Hockridge on The Local Leverage Podcast and pulled back the curtain on the six lead generation secrets that fueled his rise.

These aren’t generic tips. They’re the exact strategies that create consistent deal flow, month after month, year after year. 

Check out the full episode here:

If you’re serious about flipping, wholesaling, or scaling a real estate business, pay attention — because this is the playbook that actually wins the game (no pun intended this time). 

Now, let’s walk through each move to level up your lead generation strategy: 

• Fail Fast, Learn Faster: Turn Every Loss into a Lesson 

• Collab to Win More Deals with the "Friends With Benefits" Model 

• Master One Outbound Marketing Strategy Before Adding Another 

• Show. Don’t Tell. Turn One Win into a Hundred 

• Own Niche Seller Markets for Exclusive Deals 

• Build Local Authority Through Networking & Events 

Strategy #1: Fail Fast, Learn Faster: Turn Every Loss into a Lesson 

Every real estate investor has a horror story. The kind that makes your stomach drop, your palms sweat, and your bank account scream for mercy. 

The difference between those who make it and those who don’t? The successful ones don’t run. They recalibrate. They use failure like a wrecking ball — tearing down bad habits, weak strategies, and blind spots until only a bulletproof process remains. 

Take Dean. 

“My first few flips were a brutal education in real estate,” he told PropertyRadar. “My partner was already a seasoned investor, and he used to joke that everything he touched was gold and he couldn't make a mistake. I was new, eager, and ready to learn. But we rushed into deals we shouldn’t have.” 

The result? They each lost $100,000. 

Now, his partner could eat that loss — annoying, sure, but not catastrophic. For Dean? It was everything. 

"Let me just say, it hit me really hard," he admitted. “That loss forced me to work for free for an entire year.” 

But truth be told? There was no dramatic fallout. No chairs thrown across the room. Just two guys, staring at each other, asking: What are we going to do? 

“The best thing that came out of that loss happening early was realizing that neither of us blamed each other,” he said. “We just owned it, learned from it, and moved forward." 

And that right there? That’s the moment that separates the dabblers from the real players. Dean could’ve quit. Packed it up. Called it a lesson learned and moved on. Instead, he doubled down. He got back to work, analyzed every mistake, and rebuilt from scratch. 

….And that’s exactly how you turn setbacks into a lead-generation strength. 

Every loss in real estate teaches you something — if you’re paying attention. A bad deal forces you to slow down, figure out what went wrong, and sharpen your instincts. Over time, you start spotting warning signs before they turn into expensive mistakes.  

Maybe it’s a seller avoiding questions about liens, a property sitting on the market too long without price drops, or a deal that just feels too good to be true. These lessons help you stop guessing and start making smarter decisions. 

But failure doesn’t just help you avoid bad deals — it makes you better at closing good ones. You get better at spotting serious buyers instead of tire-kickers. You start recognizing motivated sellers — what situations push them to sell, when they’re most likely to negotiate, and how to reach them before anyone else.  

You also learn how to structure deals so they actually work, with contracts that protect you, negotiations that make sense, and financing that’s lined up ahead of time. And when people see that you’ve been through tough deals and still come out ahead, they trust you.  

Buyers want to work with you, sellers feel confident you’ll close, and other investors start sending deals your way. One hard-earned lesson turns into a better strategy, and before you know it, that painful loss is the reason you’re landing more deals than ever. 

Strategy #2: Collab to Win More Deals with the "Friends With Benefits" Model 

OK, so you’re knee-deep in a real estate deal, sweating over the numbers, second-guessing every move, when suddenly — boom. A call from a buddy. He’s got a lead. Not just any lead, but the kind that makes your pulse race. The kind that turns into a five-figure wire transfer and a celebratory steak dinner.

Welcome to the “Friends With Benefits” lead-sharing model, and no, it’s not what you’re thinking (well, kind of). The idea is simple: help first, profit second, and repeat until your pipeline is so full that closing deals becomes second nature. 

Why does this work? Because lead generation isn’t just about finding sellers — it’s about creating an ecosystem where leads flow to you. When you freely share opportunities, connections, and insights, you build trust. 

And in real estate, trust is currency. The more value you provide, the more people bring leads to you — not because they have to, but because they know you’ll do the same. 

Dean didn't wake up one day with a vision to be a real estate coach. He didn’t even see himself building a business empire. He just wanted to connect with people who shared his passion for deals. 

So, in February 2020, he held his first real estate meetup. It was a hit — nearly 100 people showed up. But just as momentum was building, the Coronavirus happened. 

Did Dean quit? Of course not. He took it online. “Got deals? Send them my way,” he said. “My team will handle the rest — analyze, negotiate, get them under contract. We’ll split the profits 50/50.” 

What happened next? A flood of deals. A network of investors who weren’t just competing but actively feeding each other leads. They were posting wins like: 

• “Closed a deal with John Smith — $10,000 wired to him!” 

• “Another one — $40,000 split.” 

• “This one? $125,000 payday. Check out this wire for $61,500!” 

And that’s when it clicked for Dean: this wasn’t just a business model — it was a lead-generation machine. The more deals he helped others close, the more leads came his way. He wasn’t chasing opportunities anymore. Opportunities were chasing him. 

No gimmicks. No gatekeeping. Just one rule: bring value, get value. Dean didn’t build just a business but a lead engine powered by relationships. 

“We branded it ‘Friends with Benefits’ — the better version, where we made money together,” Dean said. “If we did a deal, you were out of the friend zone. You got a shirt, a Yeti tumbler, and bragging rights.” 

“People started texting me, ‘Hey, I’m an XL. I’m bringing you a deal soon,’” he added. “And over the next 12 months, that energy helped add seven figures to our business.” 

And trust Dean, this didn’t stay small for long. What started as a local Meetup turned into a nationwide lead-sharing network called Deal Champs  

Deal Champs became the event to attend. Packed with investors, top-tier speakers, and big-name sponsors (shoutout to PropertyRadar). People weren’t looking to be lone wolves anymore. They wanted to be part of a real estate ecosystem that kept deals moving. 

The biggest breakthroughs happen when investors team up. That’s why Deal Champs became so successful — it wasn’t just about closing deals, but creating a system where deals came to you. Whether through partnerships, joint ventures, or simply sharing ideas, working together boosts your lead flow and speeds up your success. 

So, next time you get a lead and think about keeping it to yourself — stop. Pick up the phone. Share that lead. Because in this game, the fastest way to the top isn’t climbing solo. It’s about locking arms, keeping leads moving, and building something way bigger than you ever could on your own. 

Strategy #3: Master One Outbound Marketing Strategy Before Adding Another 

You know the drill. You’re trying to close deals. You’ve got a million channels staring you down — door-knocking, cold calling, online ads, direct mail, and email.  

So, what do you do? You jump from one to the next like you're trying to catch the next big Super Bowl win (the football references won’t stop coming, so don’t deflate those balls out of frustration just yet).  

But guess what happens? Momentum dies. You start half-assing every strategy and making zero progress. Sound familiar? 

Dean put it best when he said, “You can’t just bounce from strategy to strategy — you’ve got to commit to one and master it first. Because the differentiator between those who succeed and those who don't is focus."  

Door-knocking? Maximize its potential. Knock multiple times, follow up with direct mail, cold calls, and texts — layer it up. Once you've done all that consistently and seen results, add another channel 

Here’s the play by play to make the most out of your outbound efforts.  

Door-Knocking 

Door knocking still works if you’re consistent. Most investors overlook door-knocking because it’s uncomfortable — but that’s exactly why it works. Fewer people are doing it, which means less competition and more deals.  

The key? Stay engaged, be persistent, and treat every conversation as a learning opportunity. Dean "had several deals just this month from that one strategy,” he said 

It’s also your chance to build genuine connections in real-time. Think of it as the perfect icebreaker. You get to see the property firsthand, speak directly with homeowners, and read the room.  

But remember: don’t just knock and ask if they’re looking to sell. You need a tailored approach — talk about their neighborhood, highlight recent sales in the area, and show you're the local expert. The personal touch goes a long way. If you’re consistent with it, you'll start seeing those doors open wider. 

Cold Calling 

Cold calling often gets a bad rap, but it’s not about catching someone off guard and launching into a sales pitch. Instead, it’s about building a relationship right from the start. Think of it more as a conversation than a transaction.  

You’re not just calling to pitch — you’re calling to start a real conversation. Warm up the call by referencing property trends, discussing market conditions, or mentioning that you’ve been working with others in their neighborhood.  

The goal is engagement, not pressure. Ask questions that invite discussion, like, “How’s the market feeling in your area?” or “I’ve been working with a few homeowners nearby who are looking to upgrade — how’s your situation? 

By taking a conversational approach, you’re more likely to uncover their true needs and establish rapport, rather than overwhelming them with a hard sell. 

And once you’ve established that connection, tie in an offer that addresses a specific pain point. Whether it’s offering to help them upgrade their current home, find a better investment property, or solve a problem they’ve been facing, your value proposition becomes clearer.  

Online Ads 

Online ads give you the kind of reach that traditional marketing just can’t match. Whether you’re using Facebook, Google, or other platforms, the real power isn’t just in getting in front of people — it’s in reaching the right people.  

With detailed targeting, you can focus on specific neighborhoods, interests, and even behaviors, making sure your ads land where they matter most. But just putting an ad out there isn’t enough. 

Instead of running one ad and hoping for the best, create multiple versions with different headlines, images, and messages. Test them to see what grabs attention and what leads to action.  

This way, you’re not wasting money on ads that don’t work. The best ad strategies are flexible — constantly adjusting based on what gets results. 

But getting someone to click is only half the job. Where they land after clicking matters just as much. That’s why your ads should lead to a well-designed landing page with a clear next step, like signing up for a free consultation or downloading a helpful guide.  

The goal isn’t just to get views — it’s to turn those views into real opportunities. Done right, online ads aren’t just about reaching people. They’re about growing your business in a smart, efficient way. 

Direct Mail 

Direct mail often gets dismissed as outdated, but when done right, it’s one of the most effective ways to cut through the noise and get noticed.  

The secret? Personalization. A one-size-fits-all flyer won’t make an impact, but a well-crafted mail piece that speaks directly to the recipient’s situation will.  

This is where public records (think PropertyRadar) becomes your best friend — use details like how long they’ve owned the property, whether they’ve recently refinanced, or if the home is showing signs of distress.  

These insights allow you to craft messages that feel personal and relevant rather than just another sales pitch. 

Forget the generic “We buy houses” postcards — they’re easy to ignore. Instead, tailor your approach. If a homeowner has lived in their house for 20+ years, they might be considering downsizing.  

If they recently inherited a property, they could be overwhelmed with maintenance. Your mail piece should address these specific pain points, showing that you understand their situation and have a solution. 

And don’t just stop at the message — make your direct mail visually stand out. Handwritten-style envelopes, bold yet simple designs, and even lumpy mail (adding a small object inside to make it feel different) can increase the chances of it getting opened.  

The goal isn’t just to send mail — it’s to make sure it gets read and acted on. When you prioritize personalization over mass production, direct mail becomes a powerful, high-impact tool that gets results. 

Email 

Emails are a great way to stay on your prospects' radar without overwhelming them. But here's the thing — no one wants to read another generic email.  

The trick is to personalize it. Instead of sending the same message to everyone, break your list into groups based on where they are in the buying or selling process. Are they just starting to look for a home? Or are they ready to sell? Tailor your message to fit their needs. 

Your emails should add value, not just push for a sale. Share helpful tips, market updates, or insights that are relevant to them. This builds trust and shows you're focused on helping, not just selling.  

Also, the subject line is key. If it doesn’t grab their attention right away, they’ll move on. Make sure it’s interesting and relevant. Once they open the email, keep it short and sweet. People don’t have time to read long messages, so make your point quickly. 

You’re just one great email away from building stronger relationships and growing your business. Keep it helpful, stay consistent, and the results will follow. 

And remember what Dean says: “Finish One Course Until Successful.” Focus on mastering one strategy, and once it’s working, move on to the next.  

Strategy #4: Show. Don’t Tell. Turn One Win into a Hundred 

You closed a deal? Hell yeah! Now, don’t just let that success sit there — turn it into your next lead. Over and over…and over… again. 

Because in real estate, it’s not just about closing deals — it’s about showing people you close deals. And as Dean says, “When you stop playing it quiet and start sharing what you’ve done, watch the next opportunity land in your lap.” 

You need to get loud with your wins (think live football game kind of loud). No more sitting in the shadows hoping someone notices your hustle, show them! You’re a deal-closer, a property transformer, a professional who gets results.  

And you don’t just talk about it, you prove it. Got a screenshot of that wire transfer? Post it. Before-and-after pics of that flip you just finished? Blast them everywhere. Got a client who swore they’d never work with an investor but changed their mind after meeting you? Share their damn story.  

These aren’t just feel-good, fluff stories — they’re hard evidence that you’re the real deal. 

Why? Because that wire transfer screenshot? Proof you close deals. Those before-and-after photos? Client testimonials? Social proof of your character, professionalism, and that you can actually walk the walk — not just talk the talk.  

Let’s elaborate on what we mean here because we all love real-world examples and how to make them work for us… 

Before-and-after Photos  

Think about a property you've recently flipped. The "before" photo shows a house in need of work – peeling paint, overgrown lawn, and broken windows. The "after" photo shows that same house, now fully renovated with fresh paint, new landscaping, and a stunning interior.  

You can share these photos with a caption like, “From fixer-upper to dream home! Check out the transformation of this [Property Type] in [Location]. This could be your next project!” 

Email is a perfect way to share this transformation. You can easily attach the before-and-after photos, giving your audience a clear visual of your work.  

Pairing the photos with a catchy caption makes the email even more engaging, and personalizing the message helps grab the attention of potential clients. It’s a simple way to show off your skills and the value you bring! 

Client Testimonials  

And don’t forget about client testimonials. Maybe you worked with a seller who was initially skeptical about working with an investor due to bad past experiences, but after seeing how you handled the process, they were thrilled with the outcome.  

Get them to share their experience, either in a video or written testimonial, and post it to your website with something like, “Not every seller is ready to trust an investor — but after seeing how we handled things, [Client Name] was more than happy with the process. Here’s what they had to say!” 

This testimonial highlights your reliability, credibility, and ability to build strong, trusting relationships with clients. 

To wrap it up, each of these examples builds trust — and trust is everything in real estate. People want to work with someone who gets results, especially if they can relate to you.  

And when they see that, they’ll be sliding into your DMs, picking up the phone, or sending referrals your way. It’s a snowball effect: one deal leads to another and another. 

Keep in mind that consistency is everything. Don’t wait for the big stuff — share your wins all the TIME.  

Post that wire transfer like it’s your favorite meme. Drop those before-and-afters like they’re hot. Send updates in your emails. Put your success front and center on your website. Make sure everyone knows that you are crushing it.  

Over time, you’ll become the go-to pro in your area, and everyone — sellers, wholesalers, lenders — will want in on your next big deal. 

Strategy #5: Own Niche Seller Markets for Exclusive Deals 

When it comes to finding motivated sellers, most investors stick to the basics — buying the same old leads everyone else uses, which won’t give you any exclusivity at all.  

 For instance, Zillow takes a massive 40% commission on every lead they send your way. That’s almost half of the money you make from these clients, handed straight back to Zillow.  

And let’s be real — they’re handing out the same generic leads to everyone. Sure, they might look tempting, and each one may feel like it’s itching you closer to a sale, but in reality, it’s not. 

You're basically fishing in the same pond as everyone else, hoping for a bite. But if you want to stand out and land better deals, it’s time to think “niche seller.” Think probate, inherited properties, or homeowners facing financial problems. 

Just ask Dean – his team found success helping sellers in tricky situations that most others didn’t know how to handle. A big part of their achievements came from using PropertyRadar.  

They used PropertyRadar to set up filters that helped them find the right sellers quickly and without all the guesswork. Instead of wasting time on random properties, they focused on specific signs that indicated a seller was ready to make a deal.  

For example, they looked at foreclosure status, which is often a red flag that a seller is in financial trouble and might be more motivated to sell fast. They also paid attention to equity levels. Properties with high equity meant the seller wasn’t as weighed down by debt, making it more likely they'd be open to negotiation. This gave the team an advantage in striking better deals, often with less competition. 

Absentee owners were another group they targeted. These are property owners who don’t live in the house, whether because they moved away, inherited it, or just stopped managing it. Absentee owners are often looking to sell because they’re not actively using the property and might be struggling to keep up with it.  

By using these filters, Dean’s team worked smarter, not harder. Instead of blindly chasing every lead, they focused on sellers who were most likely to make a move, dramatically increasing their chances of finding leads and closing deals.  

The best part? You can do the same. With PropertyRadar, you can easily create your own custom lead lists based on the exact criteria you’re looking for. Whether you’re after homeowners in foreclosure, those with a lot of equity, or absentee owners who might be ready to sell, PropertyRadar helps you find these hidden opportunities quickly.  

Strategy #6: Build Local Authority Through Networking & Events 

The difference between constantly chasing deals and having them come to you boils down to one thing — authority.  

If you want a steady flow of opportunities, you need to be more than just another investor. You need to be the person people turn to when they need answers, guidance, or a deal done right. And that starts with positioning yourself as a local leader. 

One of the most effective ways to establish this credibility is by embedding yourself in your community. Hosting real estate meetups, speaking at industry events like Deal Champs, and collaborating with other professionals isn’t just about visibility — it’s about trust.  

The more people see you as a knowledgeable and reliable resource, the more they’ll reach out when they need help, want to do business, or know someone who does. It’s a simple formula: credibility brings deal flow. 

But building local authority isn’t just about showing up at events — it’s about being an active participant in the real estate ecosystem.  

The Deal Champs team, for example, is dedicated to helping professionals grow, particularly in lead generation. Their advice is simple but powerful: “Everything works, as long as you’re willing to stay consistent and put in the work.”  

Whether you’re farming neighborhoods, door-knocking, or using data-driven prospecting, the key is sticking with it. A half-hearted effort won’t get you far. 

At the core of all of this is networking. Too many investors treat networking as a secondary activity when, in reality, it’s the foundation of long-term success. It’s not just about making deals — it’s about forging relationships, exchanging ideas, and staying top of mind.  

Every interaction, whether at an event like the Deal Champs Summit, a local meetup, or even a casual conversation on social media, is a chance to grow your reach. 

Where to Start: Events That Help Build Your Network 

Not sure where to go? Here are some types of events that investors — whether brand new or experienced — should attend to start making connections and building authority: 

• Real Estate Investor Meetups – Local meetups (often found on Meetup.com or Facebook Groups) are a great way to connect with other investors, agents, and wholesalers in your area. These informal gatherings provide a space to share experiences, discuss deals, and find potential partners. 

• REIA (Real Estate Investors Association) Meetings – Many cities have REIA chapters that host monthly meetings for investors. These events often feature guest speakers, market updates, and networking opportunities with seasoned professionals. 

• Real Estate Conferences and Summits – Larger events like Deal Champs Summit, BiggerPockets Conference, Flip Hacking Live, or the Real Estate Wealth Expo bring together top investors and industry experts. These are ideal for learning high-level strategies, meeting potential business partners, and positioning yourself as a serious investor. 

• Local Chamber of Commerce Events – Networking beyond real estate can be just as valuable. Attending business events hosted by your local Chamber of Commerce helps you connect with community leaders, small business owners, and potential referral partners. 

• Property Auctions and Foreclosure Sales – Even if you’re not bidding, attending auctions gives you a chance to network with active investors, lenders, and distressed property specialists. 

• Landlord and Property Management Meetups – If you're into buy-and-hold investing, connecting with landlords and property managers can lead to off-market deals, partnerships, and referrals. 

• Builder and Contractor Networking Events – Flippers and developers can benefit from events where they meet builders, contractors, and suppliers who can provide insights and potential partnerships. 

The bottom line? "If you're not going to events like Deal Champ Summit, if you're not attending free meetups, if you're not connecting with people on social media, you're missing out,” Dean said.  

….Ready to get started? 

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