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Stay Classy Management

Momentum Guest Speaker: Jeremy Ashburn @ Push Leads SEO

November 13, 2025 | Duration: 88 minutes View Recording

Momentum Guest Speaker: Jeremy Ashburn @ Push Leads SEO

November 13, 2025 | Duration: 88 minutes | View Recording

Introduction and Background

Jeremy Ashburn began the session by connecting with the Momentum mastermind group, which Mark had started approximately seven months ago for STR property managers. The group typically consists of managers handling anywhere from 2-3 properties up to 20-30 properties. Jeremy, based in Asheville, North Carolina, shared his journey into SEO that began when his area was devastated by Hurricane Helene about a year ago. The hurricane caused unprecedented flooding, with approximately 60% of local businesses destroyed—40% immediately and another 20% within the first year. Despite this setback, Jeremy received a $25,000 grant for business owners who survived Helene, investing roughly half into building AI systems that enhance his SEO services.

Jeremy’s professional background spans graphic design (graduating in the early 2000s), a year working at an ad agency, and eight to nine years as an executive recruiter working on 100% commission. In 2005, WordPress launched, enabling non-developers to build websites. Jeremy recognized that websites without Google visibility were essentially invisible, so he taught himself search engine optimization. After generating $20,000 per month in business by 2008, he transitioned full-time and launched his own company in 2012. Now in his 14th or 15th year, he manages 30-40 clients and aims to reach 45-50 by year’s end through systematic scaling.

Jeremy explained his connection to the STR industry through Julie George (an Australian STR consultant who built and sold a business managing 130+ properties) and Matt Floyd from Stay Classy in San Diego. Someone found Jeremy at the top of Google during the pandemic, leading to work with Stay Classy, which then connected him to Julie and subsequently the broader STR network. Jeremy emphasized his B&I networking group philosophy of “giver’s gain”—focusing on providing value and helping others rather than making sales pitches.

The Five-Step SEO Process

Jeremy outlined his comprehensive five-step SEO framework that works for both traditional Google search and emerging AI search engines:

Step 1: Keyword Research

The first step involves understanding what people are searching for in Google. For STR property managers, the best-performing keyword is “Airbnb Management [City], [State]”—for example, “Airbnb Management San Diego, California.” Other valuable search terms include “vacation rental management,” “vacation property management,” and “short-term rental property management.” Jeremy demonstrated using Ahrefs (a paid tool he recommends for accurate data) to show that “San Diego Airbnb Management” receives 50 searches per month, while “Airbnb Property Management San Diego” gets 100 monthly searches. Even terms with just 10 monthly searches are worthwhile if they convert to actual property management contracts. Free alternatives exist, but Jeremy prefers data from primary sources when conducting keyword research.

Step 2: Implementing Keywords on Your Website

Once you’ve identified relevant keywords, they must appear in your website content. Both traditional Google and AI search engines need to see these search terms on your pages. If “Airbnb management” or “vacation rental management” doesn’t appear anywhere on your site, you won’t rank in search results. AI systems read your entire site, so comprehensive keyword integration is essential. The content should feel natural and authentic rather than forced or spammy.

Step 3: SEO Blueprint (Meta Titles and Descriptions)

Jeremy showed his SEO blueprint—a comprehensive list of all website pages with optimized titles and descriptions for each. He emphasized that these meta titles and descriptions shouldn’t be left blank, as even AI systems review them. However, not every page needs keywords. For example, the Contact Us page should simply say “Contact Us” with a natural description like “Reach out to us” rather than forcing keywords where they don’t belong. This approach maintains authenticity and avoids appearing spammy to search engines when implementing on-page SEO elements.

Step 4: Publishing Inner Content Pages

This step has changed dramatically with the rise of AI search. Beyond front-facing blogs (which should be published at least once weekly at 1,000-2,000 words), websites now need substantial “inner pages”—content-rich pages specifically designed for AI consumption. Jeremy explained that AI systems are essentially large language models trained on internet content, so providing more relevant content helps them understand and recommend your business. He compared working with Google and AI to maintaining a romantic relationship—it’s not one grand gesture but consistent small actions over time that build the relationship. Just as different people have different love languages, search engines respond to various signals: regular blogging, inner page creation, keyword integration, and internal linking.

Step 5: External Link Building

The final step involves getting connections from other websites to yours. Jeremy warned that approximately 80% of SEO companies are scams—a realization he had seven years ago when a lawyer client was paying $1,400 monthly for SEO with no results. Investigation revealed the previous company was doing about 1% of the necessary work. He strongly advised holding any SEO provider accountable by demanding they show their work and prove actual results. Jeremy emphasized that legitimate SEO requires systematic processes, similar to how property managers need systems to handle 5-10+ clients effectively.

Case Study: Stay Classy Homes (San Diego)

Jeremy presented a detailed case study of Stay Classy Homes, a San Diego-based client he’s worked with for approximately two years. He first reviewed their website design, emphasizing several critical elements for STR property managers:

Website Design Best Practices

The Stay Classy website features a prominent video showcasing their work—Jeremy stressed that showing your work visually is essential, whether through video or high-quality photography. Without beautiful visuals, potential clients don’t understand what they’re paying for. The site includes clear calls-to-action (“Get My Free Income Projection”), featured property listings, team information, testimonials, and SEO-optimized content. Each property page functions like an Airbnb listing with exceptional photography, detailed descriptions pulled directly from Airbnb, and clear calls-to-action.

Jeremy emphasized that all website photography should be real, not AI-generated or stock images. While he loves AI, he believes viewers can subconsciously detect inauthentic imagery, undermining trust. The site includes a blog publishing at least one post weekly (occasionally using AI images for blog posts but prioritizing real photography). The About page and Services page both feature genuine team and property photography. Jeremy noted that if you get someone to the top of Google but they visit a poorly designed website that doesn’t convert visitors, it reflects badly on the SEO work—the entire customer journey matters.

Technical Platform Considerations

Stay Classy runs on Shopify (without e-commerce functionality). While Jeremy can work within Shopify’s constraints, he prefers WordPress for most clients because it offers more control, particularly for publishing inner hidden pages—content crucial for AI visibility. For website design, clients should expect to invest $2,000-$4,000. The most important requirement beyond attractive design is the ability to publish inner content pages that AI systems can discover and index.

Keyword Performance Results

Using Ahrefs, Jeremy demonstrated various search terms Stay Classy ranks for, including “Airbnb Management San Diego” (50 monthly searches), “Airbnb Property Management San Diego” (100 monthly searches), and even lower-volume terms like “Airbnb Management San Diego California” (10 monthly searches). He emphasized that even low-volume terms are worthwhile if they convert to property management contracts—the quality of leads matters more than quantity when developing a local SEO strategy.

AI Search Revolution and Prompt Optimization

Jeremy introduced the concept of “prompts” (search queries in AI systems) versus traditional keywords. He demonstrated a tool showing Stay Classy’s AI search presence has grown from 2,000 to 6,200 searches monthly—a 4,200-search increase in just one month. This growth mirrors broader trends: ChatGPT users globally went from 400 to 800 million in 10 months (February to October), and ChatGPT usage among Americans increased 375% year-over-year, from approximately 8% in 2024 to 38% currently.

Understanding AI Prompts

Jeremy showed actual AI search results where Stay Classy was recommended. For example, in a Gemini search for “Vacation Rental and Airbnb Management in San Diego,” Stay Classy Homes appeared in the recommendations multiple times. The tool tracks 36,000 “topic opportunities”—various questions people ask AI systems that relate to the business. While similar to traditional keywords, prompts are often phrased as complete questions: “How does Airbnb Property Management work in San Diego?” or “What are the best tools for managing Airbnb?” or “What are common challenges faced with running an Airbnb?” Understanding semantic search helps optimize for these conversational queries.

Free Tools for Prompt Research

When asked about free alternatives to the $200/month SEMrush tool, Jeremy recommended several options:

Jeremy demonstrated Answer the Public by entering “Airbnb management,” which generated numerous AI-model questions like “What are the best management services?”, “Can I hire someone to do cleaning and maintenance?”, “How can I find a property management company in my area?”, and “Where can I get guest screening services?” Creating content that answers these specific questions forms a crucial part of AI SEO strategy.

Internal Content Pages and AI-Specific Content

Jeremy explained one of the most significant changes in modern SEO: websites are evolving beyond just human-facing design pages to include AI-specific content pages. He demonstrated several examples from Stay Classy’s website:

Example 1: Five-Star Guest Experiences

This 1,000-word article titled “Creating Five-Star Guest Experiences: The Concierge’s Approach to Vacation Rental Management” exists as an inner page specifically for AI consumption. The content discusses what makes a five-star experience and how to set the stage for exceptional service. Crucially, the article includes internal links connecting to other relevant pages on the site—Jeremy noted that if pages aren’t connected to other pages through links, Google and AI systems essentially ignore them.

Example 2: Premium Management Guide

This longer page, approximately 3,000 words, serves as what Jeremy calls an “AI buffet”—a comprehensive guide about premium San Diego vacation rental management. The structure includes an introductory paragraph, a table of contents, and multiple 500-800 word sections addressing different aspects of the topic. Jeremy doesn’t concern himself with minor title duplication because this content is entirely designed for AI consumption. The page concludes with a call-to-action directing readers to contact Stay Classy Homes.

Content Creation Methodology

Jeremy developed a custom AI system called Incredible Roots to automate this content creation process. The system scans a client’s website to understand their voice and writing style, creates a “voice match” profile, queries ChatGPT to understand what people search for related to the business, then uses Claude (Jeremy’s preferred AI for writing) to generate 3,000-word articles that sound like the business owner wrote them. The entire output is delivered as a Google Doc within about 10 minutes, at a cost of approximately $1 per generation.

Incredible Roots: AI-Powered Content Generation

Jeremy demonstrated his Incredible Roots platform, offering participants free access to test it. The platform’s name comes from the metaphor that websites are like trees—the visible sections are what humans see, while the root system represents hidden inner pages that AI systems discover. The more “roots” (inner hidden pages) you have, the more AI systems find and recommend you.

Live Demonstration

Jeremy generated content for Jake (Lodge and Leisure) and Alan (Vista Pro Stays) during the session. The tool allows users to create “silos”—a pillar page with five sections (approximately 3,000 words) plus three supporting inner pages (also 3,000 words each). Users simply enter their website URL and a topic (like “hospitality first management”), and the system generates all content within minutes. The resulting Google Doc can be copied and published to any platform, implementing effective content clusters.

Backend Dashboard Functionality

For Jeremy’s agency use, the dashboard version automatically publishes content directly to WordPress or Shopify websites. He can select a client, specify their location (e.g., San Diego), choose the silo structure (large pillar page plus smaller supporting pages), enter a keyword or prompt, and click “start generating”—the system writes and publishes everything automatically. All content is customized for the specific client, referencing their location, brand name, and unique value propositions. This creates authentic AI-generated content rather than generic “AI slop.”

Pricing and Availability

Jeremy initially built Incredible Roots for his own agency to scale from 35 to 45-50 clients. He thought other agencies might want to use it but hasn’t found that market yet. He estimated pricing would likely be under $100 monthly to publish 5-10 content silos. For now, he’s offering free access for testing and feedback. His investment in developing the tool (with an Argentinian developer over five months) was motivated by the need for personalized AI content—most AI-generated content online is generic and inauthentic.

Claude for Manual Content Creation

For those who prefer not to use automated tools, Jeremy recommends Claude over ChatGPT for content creation. He shared a cautionary experience from a year ago when he had ChatGPT write 30 blogs for a client—the results were poor, with ChatGPT merely changing adjectives in existing articles rather than creating unique content. When he switched to Claude for the same task, it generated entirely new, well-written articles. Jeremy calls himself a “Claudester” and uses Claude exclusively for content writing, though he still uses ChatGPT for conversational tasks. Claude’s Projects feature allows users to upload all website pages, train it on their writing style and tone, then generate content that authentically sounds like the business owner wrote it.

Internal Linking Strategy

Jeremy explained that publishing content is only part of the equation—connecting pages to each other through internal links is equally critical. He uses a specialized tool that automatically builds internal connections across website pages. For Stay Classy, he’s created 118 internal connections, which he visualized using a diagram showing how Google and AI systems “see” websites: pages appear as dots, and lines between dots represent internal links.

The 50-Link Threshold

Research shows that pages with 50 internal links pointing to them are significantly more likely to be found by both AI systems and traditional Google. Jeremy demonstrated a content page with about five internal links, but noted the goal is to build toward much higher numbers. His automated tool helps achieve this at scale—he targets building 20-50 internal links per month for clients because manual creation by virtual assistants is time-consuming and expensive.

Practical Example

In the “Five-Star Guest Experiences” article, Jeremy showed links embedded naturally in the content. For instance, “pricing decisions” links to “The Ultimate Guide to Dynamic Pricing,” and “understanding vacation rental management” links to another relevant inner page. These contextual links signal to search engines that content is interconnected and comprehensive. Anyone doing SEO—whether hiring someone or doing it themselves—should be building 20-50 of these connections monthly to see meaningful results, following best practices for advanced internal linking.

External Link Building and Authority

Jeremy introduced the final critical component: getting other websites to link to yours. He showed that this is the step most SEO scammers fail to execute. Using a tracking tool, he displayed Stay Classy’s referring domains (unique .com websites linking to them) over time. The graph showed steady growth from about 370 referring domains in early 2023 until March/April of the current year, when Jeremy shifted strategy from quantity to quality.

Quality Over Quantity

Rather than continuing to build numerous low-value links, Jeremy focused on high-quality connections from authoritative websites. He demonstrated a guest blog post on another website about “Creating a Stylish Vacation Rental Space.” To the average reader, it appears as a standard 1,000-word blog article with links to Stay Classy Homes and the National Association of Realtors. However, the power comes from the source website’s authority.

Domain Rating Explained

Jeremy explained that Google doesn’t see website designs—it sees a number on a scale of 0-100 representing each website’s strength and overall reputation. The example blog was published on a website with a Domain Rating of 52, making it 52 times more powerful than a new website (which would have a rating of 0). If Jeremy simply created a blog on Blogger.com, Google would ignore it for approximately five years. But because the host website has strong authority (52/100), the link immediately provides value. A brand-new website starts at zero, so earning links from established, authoritative sites dramatically accelerates SEO success.

Link Building Process

Jeremy has a team that reaches out to authoritative websites to publish content. He typically allocates one-third to one-half of what clients pay him toward paying for these placements. While property managers could ask friends with websites to link to them, Jeremy warned about important rules: the linking website should be in a similar business category, and reciprocal linking (you link to them, they link back to you) looks suspicious to Google. The best approach is having another site publish a blog post mentioning your business naturally—”If you’re in San Diego looking for Airbnb management, check out Stay Classy”—with an embedded link.

Measuring SEO Results

Jeremy emphasized that measurable results are essential, whether you’re doing SEO yourself or hiring someone. He demonstrated several measurement tools and metrics:

Traditional Google Visibility

Using SEMrush (approximately $200/month to monitor five websites), Jeremy showed Stay Classy’s visibility increasing from 0% (when they started) to 13% currently. The tool tracks keyword rankings in different positions: 11 keywords at the #1 position (highlighted in yellow), 21 keywords on Google’s first page total, and numerous other rankings. For example, “Airbnb management companies San Diego” ranks at the top, and “vacation rental management San Diego” (with 10 monthly searches) also achieved top ranking.

Jeremy’s typical pricing is $1,550/month to move 20 terms to the top of Google—this is where he achieves the best results. His rates range higher and lower depending on market competitiveness and client needs, but he stressed that anyone spending money on SEO should insist on reports showing terms moving up in rankings. If a provider isn’t showing concrete ranking improvements, they’re likely not doing the work. This verification process protects clients from the approximately 80% of SEO providers Jeremy considers scammers.

Google Analytics Traffic Growth

Jeremy reviewed Stay Classy’s Google Analytics data, showing traffic increases over time. The “Direct” traffic category (where Google doesn’t know the traffic source) includes AI referrals—when someone searches via AI and visits your website, it appears as Direct traffic. “Organic Search” represents traditional Google traffic. Year-over-year comparison showed growth from 144 visitors to 211 visits (a 46% increase). While Stay Classy also grew through mergers (from managing 50-70 properties to 70-80), Jeremy estimates his SEO work generates at least 2-3 quality leads weekly.

Key Performance Indicators

Beyond traffic volume, Jeremy monitors whether visitors are engaging more with the website (more actions per visit), spending more time on pages, and converting at higher rates. After 15 years of full-time SEO work, he’s developed a systematic approach to evaluation. He always begins client relationships with a comprehensive assessment of where they currently rank and what work is required to reach the top of Google for their target keywords.

Current Performance Snapshot

As of the presentation date, Stay Classy had 13% visibility with 16 terms at the top of Google. While visibility fluctuates between 11-13%, the overall trend is positive. Looking at just the previous month, they moved from 5% back up to 13%. Particularly exciting was their near-top ranking for “Airbnb management” with 260 monthly searches—a highly competitive, high-value keyword that brings substantial visibility and lead generation potential.

The AI Search Revolution: Impact and Statistics

Jeremy transitioned to discussing the broader AI search revolution and its implications for SEO strategy. He presented compelling statistics demonstrating the explosive growth of AI search:

Adoption Statistics

Search Behavior Changes

The Brand Advantage

Despite declining overall click-through rates, brands with strong social media presence see 18% click-through rates—significantly higher than average. Jeremy emphasized that AI systems essentially ignore businesses without social media presence. Property managers should maintain consistent posting (at least once weekly) on multiple channels to strengthen their brand visibility to AI systems. Strong brands benefit because people use AI to discover options, then verify and check out businesses on traditional Google before making decisions. AI still hallucinates regularly, so users naturally cross-reference recommendations.

Industry-Specific Growth

Travel-related AI searches have exploded with 381% growth, directly relevant to the STR property management industry. People use AI for information gathering, completing tasks, and even personal reflection (like asking ChatGPT to help navigate interpersonal conflicts). The shift is particularly pronounced on mobile devices, where click-through rates have decreased dramatically as users get answers without visiting websites.

The Quality Conversion Paradox

While fewer people click through from AI searches overall, the visitors who do arrive via AI recommendations convert at rates 23 times higher than traditional Google visitors. Jeremy explained this makes intuitive sense—humans are social creatures who respond to trusted recommendations. When an AI engages in conversation, understands your needs, and recommends specific businesses, that recommendation carries more weight than simply seeing a business listed in traditional search results.

Reddit and Alternative Platforms

Jeremy highlighted Reddit as an increasingly important platform for AI visibility. Google signed a $60 million deal with Reddit, and AI systems frequently pull answers from Reddit discussions. He recommended establishing a presence on Reddit and answering questions related to property management in relevant subreddits. This strategy helps AI systems discover and recommend your business.

However, Jeremy also noted Reddit’s imperfections, referencing the famous incident when Google’s AI Overview recommended adding glue to pizza based on a sarcastic Reddit comment. Despite occasional quirks, Reddit content significantly influences AI recommendations, making it worthwhile for property managers to participate authentically in relevant discussions.

AI SEO Best Practices and Action Items

Jeremy concluded with practical recommendations for showing up in AI search results:

Essential AI SEO Strategies

Multiple AI Platforms

Jeremy noted that various AI systems are emerging beyond ChatGPT—including Perplexity, Gemini, and Claude. Each has unique strengths: ChatGPT is like a versatile handyman who handles many tasks but doesn’t write exceptional prose; Claude is like an English professor who excels at content creation with minimal hallucination; Gemini is like a photographer with strong video and visual capabilities. Property managers should understand these differences and use appropriate AI tools for different purposes.

Actionable Takeaways for Property Managers

When asked for the single most important action property managers could take, Jeremy provided a four-step process that anyone could implement immediately without hiring an SEO professional:

Step 1: Prompt Research with Answer the Public

Visit answerthepublic.com and create a free account (allows three searches daily). Enter terms like “Vacation Rental Management” or “Airbnb Management” to discover what questions people are asking AI systems. Screenshot and document these questions—they represent actual search behavior you should address with content. This free tool provides invaluable insight into the prompts AI systems encounter related to your business.

Step 2: Create a Claude Project with Your Website Content

Sign up for Claude (free tier available, though Jeremy recommends the $20/month paid version). Create a new project specifically for your website. Under the project’s Files section, add text content by copying and pasting all content from your homepage, service pages, about page, and other key pages. Don’t worry about formatting—just ensure all your website’s written content is uploaded. This trains Claude to understand your business, voice, and messaging.

Step 3: Add Writing Guidelines

Jeremy promised to email Jake (and would share with the group) his comprehensive “Writing Guidelines for Natural Language” prompt. This modified prompt instructs Claude to write content that sounds authentically human rather than AI-generated. The guidelines are extensive but essentially tell Claude to adopt conversational tone, natural language patterns, and authentic writing style that matches how humans actually communicate.

Step 4: Generate and Publish Content

Once Claude is trained on your website and has the writing guidelines, ask it to “describe the style and tone” of your content. After it provides this analysis, you can request: “Write a pillar page targeting this prompt: [insert question from Answer the Public]. Use headings, short paragraphs, write a 155-character meta description, and target 3,000-4,000 words.” Claude will generate comprehensive content that sounds like you wrote it. Publish this as an inner hidden page on your website and connect it to other relevant pages through internal links.

Additional Quick Wins

Investment Considerations and Ideal Client Profile

Jeremy was transparent about pricing and expectations for professional SEO services:

Pricing Reality

Jeremy’s standard rate is $1,550/month, which he describes as the level where he achieves the best results—typically moving 20 terms to the top of Google. He does offer rates both above and below this depending on market competitiveness and specific client needs. However, he firmly stated that “SEO for less than $1,000 a month is more or less a scam.” While he has some clients at $750-950/month, it’s more difficult to produce significant results at that investment level. Anyone claiming they can deliver meaningful SEO results for less than $1,000 monthly should be viewed with extreme skepticism.

Ideal Client Profile

Jeremy’s ideal client manages at least 10 properties, has consistent cash flow that can support a $1,000+ monthly investment, actively wants to grow their property portfolio, and has operational systems already in place. He emphasized that SEO makes sense only when your entire business operates smoothly—if you’re still figuring out basic operations, SEO will bring leads you can’t properly service, which wastes everyone’s time and money. Jeremy recently signed two new STR clients (one in Texas, one in Phoenix) and limits himself to just a couple of clients per market to avoid oversaturation and competing with his own clients.

Return on Investment

The fundamental question is cash flow viability: if SEO generates 2-3 quality leads weekly and even one converts to a property management contract, does that justify the monthly investment? For managers with 10+ properties and proven systems, the answer is typically yes. The work compounds over time—SEO isn’t an overnight solution but a long-term investment that builds visibility month after month.

Market Reality and Scam Awareness

Throughout the presentation, Jeremy repeatedly warned about the prevalence of SEO scams, estimating that 80% of SEO providers are fraudulent. He shared his personal discovery of this problem when a lawyer client was paying $1,400/month to another company with zero results. Upon investigation, Jeremy found they were doing approximately 1% of the necessary work—occasionally publishing a page but failing to execute the comprehensive strategy required for results.

Red Flags and Accountability

Jeremy urged property managers to demand accountability from any SEO provider: require them to show the actual work being performed, insist on measurable results with tracking reports, and verify that ranking improvements are actually occurring. If a provider can’t or won’t show concrete evidence of work and results, they’re likely taking your money without delivering value. The systematic approach Jeremy described—keyword research, content optimization, meta titles/descriptions, inner page creation, internal linking, and external link building—represents the full scope of legitimate SEO work. Anything less is insufficient.

Closing and Resources

Jeremy concluded by making the Fathom recording available to all participants, acknowledging that the presentation was like “sitting in front of a fire hose” with an overwhelming amount of information. He encouraged participants to:

Key Philosophy

Jeremy reiterated his B&I networking philosophy of providing value first rather than pushing sales. His entire presentation focused on education and actionable insights that property managers could implement themselves if they weren’t ready to hire professional help. For those who do want professional assistance, he emphasized the importance of finding the right fit where cash flow supports the investment and operational systems can handle the increased lead flow that successful SEO generates.

The session concluded with Jeremy offering continued availability for questions, referrals, and future presentations if the group found value in his insights about the rapidly evolving intersection of traditional SEO and AI-powered search.

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