A complete paid acquisition strategy, VSL funnel, ad scripts, and email sequence built specifically for your course and your story.
Jason, you have 25 years of real estate experience. You won Ernst & Young Entrepreneur of the Year. You are building a 100-unit STR portfolio in Tampa. You develop luxury beachfront homes in Redington Beach.
And your $500 course lives on a basic Teachable page with no ads, no funnel, no VSL, and no email capture.
That gap between what you have built and how your education business shows up online is one of the widest I have seen. So I built the marketing system that closes it. Everything below is specific to Scaling Short Term Rentals. Nobody else can use it.
4 deliverables built from 25+ hours of research into your business, your competitors, and your market.
We checked all three of your websites. scalingshorttermrentals.com, assetme126.com, and jasonmatthewsfl.exprealty.com.
None of them have a Facebook pixel installed. No Meta tracking. No CAPI. No Hyros. No TripleWhale. The only analytics on your Teachable site are platform defaults (Google Analytics, Heap, Sift). Those are Teachable's tracking, not yours.
Your course page has one call to action: "ENROLL TODAY." That button goes directly to Teachable checkout. No opt-in page. No lead magnet. No VSL. No email capture. No nurture sequence. Nothing between "I found this page" and "give me $500."
You were a top 60 basketball recruit. You turned down the NBA. You went to Wall Street. You survived 6 recessions. You won Ernst & Young Entrepreneur of the Year. You are building a 100-unit portfolio.
A visitor to your Teachable page sees: "Hi, I'm Jason. I am a seasoned real estate executive with over 25 years of real estate experience." That is it.
No email opt-in forms on any of your sites. No lead magnets. No free PDFs. No free video training. No newsletter signup. Every time you appear on a podcast, every time someone finds your Instagram, that person disappears if they do not buy immediately.
Why Meta (Facebook/Instagram): Your audience (aspiring STR investors, ages 25-55, interested in real estate investing, Airbnb hosting, passive income) lives on these platforms. Targeting is straightforward: interest-based (Airbnb, VRBO, short-term rental, real estate investing), lookalike audiences from your student list, and retargeting website visitors once the pixel is installed.
| Phase | Monthly Budget | Expected Results | Timeline |
|---|---|---|---|
| Testing | $1,500/month | 5-8 ad variations, 50-100 leads | Month 1-2 |
| Optimization | $3,000/month | Scale winners, 100-200 leads | Month 3-4 |
| Scale | $5,000-10,000/month | Proven ads at scale, 200-500+ leads | Month 5+ |
| Metric | Conservative | Moderate |
|---|---|---|
| Monthly ad spend | $3,000 | $5,000 |
| Cost per lead | $15-30 | $15-30 |
| Leads per month | 100-200 | 167-333 |
| VSL conversion rate | 2% | 3% |
| Course sales per month | 2-4 | 5-10 |
| Monthly course revenue | $1,000-2,000 | $2,500-5,000 |
| Coaching upsell (20%) | $400-800 | $997-1,994 |
| Total monthly revenue | $1,400-2,800 | $3,497-6,994 |
Angle: Most STR courses are taught by people who started 3 years ago. Jason has 25 years of experience, survived 6 recessions, and is actively building a 100-unit portfolio. The course is the shortcut to everything he learned the hard way.
Target audience: People interested in Airbnb hosting who are overwhelmed by information. They have watched 50 YouTube videos but have not taken action because they do not trust the 24-year-old who just bought his first property telling them how to invest.
Landing flow: Ad (talking head) → Opt-in for free guide → Email sequence → VSL → Course checkout
The opt-in captures their email with a free guide: "5 Mistakes That Kill First-Time STR Investors." The thank you page autoplays the VSL. The email sequence nurtures over 10 days. The course checkout is the existing Teachable page.
Format: Talking head with B-roll of your Redington Beach properties.
"Instead, I went to Wall Street. Then I spent 25 years in real estate. I survived the dot-com crash, 9/11, the 2008 housing collapse, the oil bust, and COVID."
"And through all of it, I kept buying properties. Today, I am building a 100-unit short-term rental portfolio on the Gulf Coast of Florida."
"This video is for the person who wants to build wealth through short-term rentals but does not know where to start. Or the person who started but hit a wall and cannot figure out why."
"I have been through all of it. Six times. And here is what I learned: the people who lose money in real estate are the ones who followed advice from someone who has never been tested."
"The strategies I teach are not theories. They are the exact systems I use to run my own STR portfolio. Every property I manage, every deal I underwrite, every team I build. It all comes from 25 years of doing this at every level."
Walk through the journey. Keep it real.
The story does the selling. You have more credibility in one paragraph than most STR educators have in their entire career.
Preview the 3 core modules. Give enough to understand the system but not enough to do it without you.
Module 1: Identify Great Properties
"Most people pick a property because it looks nice on Zillow. I will show you how to use data tools to find locations that most hosts do not know about. The same tools I use to underwrite deals for my own portfolio."
Give one specific example from your experience. "In 2022, I found a property in [area] that every other investor passed on because [reason]. We acquired it, set it up as an STR, and it generated [specific result]."
Module 2: Create a Memorable Stay
"The difference between a 4-star review and a 5-star review is the difference between 60% occupancy and 90% occupancy. I will show you exactly how to design the guest experience. Not from a YouTube video. From managing actual properties across the Gulf Coast."
Module 3: Build a Scalable Team
"I do not manage my properties myself. I have a team. Merin Vacation Rentals handles the day-to-day operations while I focus on acquiring and developing. In the course, I teach you how to build that same infrastructure so you can step away from the mundane and focus on growth."
Use your own track record as proof. You are not selling theory. You are selling the system that built everything you have:
"That includes everything: all three modules, the data tools training, my guest experience framework, the team-building system. Plus monthly 1-on-1 coaching calls with me directly. Plus access to the private Facebook group where you can connect with other investors and ask questions."
"If you are serious about building an STR portfolio, this is the fastest way to get there. You can spend the next 2 years watching YouTube videos and making expensive mistakes. Or you can learn from someone who has 25 years of experience and is actively doing this at scale."
"And if you are not sure yet, that is fine. Download the free guide first. '5 Mistakes That Kill First-Time STR Investors.' It is free. No strings attached. Start there and see if this approach makes sense for you."
Angle: You have more experience than anyone teaching this. Lead with that.
Production: Film at one of your Redington Beach properties. Natural light. Casual clothes. Walk and talk through the property while you deliver the script. Let the property be the proof.
Angle: Your origin story is unlike anyone else in the STR space.
Production: Sit-down interview style. Close crop. Direct to camera. Let the story carry it. No B-roll needed. The words are the content.
Angle: Speak to the person who has consumed all the free content but still has not started.
Production: Film at your desk or home office. Casual, direct. This script is about empathy, not showing off properties. Calm, confident energy.
Triggered when a prospect opts in for the free guide: "5 Mistakes That Kill First-Time STR Investors"
15 minutes. I will show you exactly how we would implement the funnel, the ads, and the email system for Scaling Short Term Rentals.
Book a 15-Minute Call or Reply to colin.d@crdmarketing.com