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The Ross Simmonds Show

Ross Simmonds

Welcome to The Ross Simmonds Show. A show exploring the different sides of entrepreneurship, how Ross is growing his global marketing agency, building software, raising a family, and attempting to do so much more. On this show, Ross explores what goes into executing with excellence, embracing innovation, marketing at a high level and doing it all with intent of the playing the long game.

This show is a proud member of the HubSpot Podcast Network.

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  • 20 episodes
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  • Avg 34 min
  • English

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  • Monday · 12 min

    RSS 67: AI SEO Strategy: 5 Ways to Increase LLM Visibility and Drive Better Buyers

    In this episode of The Ross Simmonds Show, Ross breaks down how search behavior has evolved beyond Google and why brands need a broader visibility strategy in the age of ChatGPT, Perplexity, Grok, and other LLMs. He shares five practical strategies to help marketers, creators, and business owners strengthen AI visibility, influence buyer discovery, and build a smarter content distribution engine for long-term growth. Key Takeaways and Insights: 1. Increase your brand’s surface area - Visibility now depends on how often your brand appears across the sources LLMs use to generate answers. - Google and AI tools increasingly answer questions without sending users to your site. - Expanding brand mentions across blogs, videos, forums, and other platforms increases your chances of being cited. 2. Your Website Is No Longer the Only Asset That Matters - User-generated content, affiliate sites, and review platforms now play a major role in shaping buyer decisions. - Third-party trust signals can influence LLM responses even when direct traffic is declining. - Positive brand sentiment on platforms like G2, Capterra, TrustRadius, and Yelp can improve AI visibility. 3. Every LLM Sources Information Differently - Claude, Perplexity, ChatGPT, and Grok do not pull from the web in the same way. - Broad industry assumptions are less useful than prompt-specific research in your niche. - Marketers need to track which sources appear for their own target queries before building strategy 4. Reddit Requires Real Community Participation - Spamming Reddit or trying to manipulate conversations is a fast way to get banned. - Authentic engagement and value-first participation are far more effective than artificial promotion. - Building trust through genuine contribution can create a sustainable Reddit presence over time. 5. Reverse Engineer What LLMs Already Reward - Use keyword research as a proxy to estimate which queries may also appear in LLM usage. - Track prompts to see what content formats and sources are being cited. - If LLMs favor listicles, comparison pages, landing pages, YouTube videos, or Reddit threads, build for those patterns. 6. Build an AI Visibility Strategy That Drives Pipeline - The goal is not just awareness, but measurable business impact. - Teams should align SEO, content distribution, and prompt tracking into one structured visibility strategy. - Brands that play the long game will be better positioned to earn trust, citations, and conversions. — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds

  • August 17 · 52 min

    RSS 66: AI Visibility for Modern Marketers: Malte Landwehr on How to Measure LLM Search and Win More Brand Mentions

    In this episode of The Ross Simmonds Show, Ross sits down with Malte Landwehr, CMO of Peec.ai, to unpack what AI visibility really means for modern marketers and how it differs from traditional SEO. They break down how brands can measure LLM visibility, identify the right prompts to track, prioritize the channels that influence AI answers, and build a smarter cross-functional strategy to win recommendations in tools like ChatGPT, Perplexity, Gemini, and more. Key Takeaways and Insights: 1. AI Visibility vs Traditional SEO - Traditional SEO was built around earning clicks and website traffic, while AI search is increasingly about getting your brand recommended inside the answer. - In AI-driven search experiences, users may never visit your site, which changes how marketers think about attribution, brand experience, and customer journeys. - Malte explains why this shift impacts not just SEO teams, but also content, brand, support, PR, affiliate, and product documentation teams. 2. How to Measure AI Search Performance - Malte outlines four core ways to measure AI visibility: self-reported attribution, web analytics, log file analysis, and prompt tracking. - Self-reported attribution is a strong starting point for teams trying to validate whether LLMs are already influencing pipeline and revenue. - Prompt tracking stands out as the most actionable measurement method because it helps marketers spot content gaps, benchmark competitors, and prioritize next steps. 3. Prompt Tracking and Strategy That Actually Works - The best prompt strategies start with topics, intent, personas, and funnel stage rather than obsessing over exact wording. - Real-world testing shows that people use many different prompts, but LLMs often return similar brand recommendations when the underlying intent is the same. - Malte warns marketers not to overreact to tiny data sets or short-term fluctuations, and instead evaluate performance directionally across prompt sets over time. 4. The New Playbook for AI-Era Content Distribution - LLMs pull from a wide range of sources, including help centers, FAQs, social content, news sites, directories, review platforms, and community discussions. - Brands need consistent positioning across all managed and owned surfaces so AI systems can clearly understand and describe what the company does. - Smart teams use source-level visibility data to decide where to invest, whether that means digital PR, creator partnerships, editorial placements, review platforms, or competitor-inspired content. 5. Agentic Commerce and the Future of Marketing Workflows - Malte shares why agentic commerce will likely arrive faster in B2B procurement and operational workflows than in emotional consumer purchases. - He also explains how AI tools and MCP integrations are changing the software experience, allowing marketers to work through AI interfaces instead of traditional dashboards. - For early-career marketers, his advice is clear: become AI-native, use AI first to solve problems, and build the habit of testing, iterating, and learning fast. Resources & Tools: 🔗 Peec.ai — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds — Connect with Malte — ╰ Instagram: @malte.landwehr.official ╰ Twitter / X: @MalteLandwehr ╰ LinkedIn: linkedin.com/in/landwehr/

  • August 10 · 51 min

    RSS 65: Human-First Marketing: Jay Schwedelson on Building Reach With LinkedIn and Virtual Events

    In this episode of The Ross Simmonds Show, Ross chats with Jay Schwedelson as he shares a masterclass on personal branding, LinkedIn growth, virtual events, AI workflows, and building audience-first media that drives real business results. If you want practical strategies to amplify your content, humanize your brand, and create marketing that people actually remember, this conversation is packed with proven insights you can put to work immediately. Key Takeaways and Insights: 1. LinkedIn Growth and Personal Brand Strategy - Jay shares how he grew from a few hundred LinkedIn connections to more than 80,000 by posting consistently and focusing on one platform. He emphasizes that different types of content perform better on different days, with educational posts early in the week and lighter, more motivational content later on. One of the strongest takeaways: personal branding works best when it feels real, human, and native to the platform. 2. Why Lo-Fi Content Beats Overproduced Content - Jay makes the case for low-production, authentic content that shows personality instead of polish. He explains why behind-the-scenes videos, imperfect moments, and conversational posts outperform scripted, overly branded content in the age of AI-generated sameness. For marketers and creators, the big opportunity is clear: lean into humanity to build trust and attention. 3. How to Build Memorable Events People Actually Attend - Jay reveals the strategies behind his high-performing virtual events, including “earned on-demand” access and short session formats. - He shares why fun, unexpected moments like contests, celebrity appearances, and unconventional programming create stronger audience engagement. - His framework is simple but powerful: treat events as a marketing channel, not just a cost center. 4. AI, Claude, and Agentic Workflows for Marketers - Jay walks through how he uses Claude to organize audience data, identify ideal prospects, and generate highly tailored campaign proposals. - He also discusses how agentic AI could soon help marketers run and optimize campaigns with far less manual work. - His advice is direct: use AI for efficiency, but don’t let it erase originality or human perspective. 5. Leadership, Burnout, and Long-Term Success - Jay opens up about burnout, the power of saying no, and the mindset shift that helped him regain clarity. - He shares his daily “I don’t have to, I get to” reframe as a practical gratitude tool for staying grounded. - The broader message: consistency, delegation, and self-awareness are critical for sustainable growth in business and content creation. 6. Speaking, Failure, and the Philosophy Behind the Book - Jay explains the meaning behind his book title, Stupider People Have Done It, and how that idea helped him move past imposter syndrome. - He offers practical public speaking advice, including why memorized presentations fail and why relatability wins every time. - He also encourages marketers to fail faster, test ideas honestly, and stop waiting for perfect before taking action. Resources & Tools: 🔗 Stupider People Have Done It by Jay Schwedelson 🔗 JaySchwedelson.com — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds — Connect with Jay — ╰ Instagram: @​​jayschwedelson ╰ LinkedIn: linkedin.com/in/schwedelson/

  • July 31 · 1 hr 4 min

    RSS 64: How to Win AI Search: YouTube, Reddit, and the New Rules of LLM Visibility

    In this episode of The Ross Simmonds Show, Ross joins Nick in The Nick Standlea Show to break down how search is changing as Google AI Overviews, ChatGPT, Gemini, Perplexity, and other LLMs reshape how people discover brands. They unpack what marketers, creators, and business owners need to do now to improve AI visibility, build authority across platforms like YouTube and Reddit, and create content that gets found, cited, and trusted. Key Takeaways and Insights: 1. How LLMs actually build answers - Ross explains “query fan-out,” where AI tools rephrase a user’s prompt into many variations and scan multiple sources at once. - Platforms like Reddit, YouTube, Quora, Yelp, and Google results all help shape the final response. - The brands mentioned most often—and with the strongest supporting signals—are more likely to appear in AI-generated answers. 2. The coffee shop framework for local AI visibility - Local businesses should align site pages and language with the exact questions customers ask. - Review signals from Yelp, TripAdvisor, and other directories strengthen trust and authority. - Encouraging real customer conversations on Reddit and other platforms can influence how AI tools perceive your brand. 3. Why YouTube is a major AI search advantage - Google has a built-in incentive to surface YouTube content because it owns the platform and monetizes attention there. - YouTube remains one of the most powerful search engines in the world and a rich source of human-led content. - Video stands out in an AI-heavy world because it delivers a stronger sense of trust, personality, and connection. 4. Gemini, personalization, and the future of search - Google may have a long-term advantage because Gemini can connect with products like Gmail, Calendar, Chrome, and more. - Search experiences are becoming more personalized, which makes traditional ranking analysis harder. - Marketers need to prepare for a world where different users may get very different answers to the same prompt. 5. How nonprofits and mission-driven brands should adapt - Start by mapping website content to the real questions your audience asks before they know your brand exists. - Build long-form, useful resources that directly address audience pain points and decision-making moments. - Combine LLM optimization with human-centered storytelling to connect both logically and emotionally. 6. The four E’s of content that builds trust - Ross highlights four content goals: educational, engaging, entertaining, and empowering. - Strong brands don’t just publish information—they create content people want to remember and share. - Human connection still matters, especially when AI-generated content is becoming more common. 7. Old-school customer research is the new edge The deepest marketing insights still come from direct conversations with real customers. Interview transcripts, sentiment analysis, and qualitative feedback can be turned into sharper messaging with AI. The brands that win will combine human insight with AI execution, not replace one with the other. Resources & Tools: 🔗 The Nick Standlea Show — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds — Connect with Nick — ╰ Instagram: @nickstandlea ╰ LinkedIn: linkedin.com/in/nick-standlea-43732573/ ╰ YouTube: The Nick Standlea Show

  • July 25 · 17 min

    RSS 63: How I'm Running Two Companies In 2026

    In this episode of The Ross Simmonds Show, Ross takes listeners behind the curtain on how he leads both Foundation, an established enterprise agency, and Distribution.ai, an early-stage SaaS company. He breaks down the mindset, systems, team structure, AI workflows, and leadership principles that make it possible to scale one business while building another from the ground up. Key Takeaways and Insights: 1. Obsessing Over Customer Value - Both companies are anchored in consistently delivering value to clients and customers. - Ross emphasizes solving real customer problems instead of chasing activity for activity’s sake. - Incremental improvement compounds when teams stay focused on outcomes. - Long-term growth comes from building systems that keep customer value at the center. 2. Surrounding Yourself With Doers - Ross credits much of his ability to run two companies to having strong teams in place. - At Foundation, his role is to attract the right people and clients, articulate the vision, and empower the team. - At Distribution.ai, he stays closer to product roadmaps, sales, SEO, and customer discovery. - Hiring people who can do what you cannot do is one of the biggest unlocks for founders and operators. 3. Using RACI to Create Role Clarity - RACI stands for Responsible, Accountable, Consulted, and Informed. - This framework helps teams understand who owns each decision and responsibility. - Clear ownership reduces confusion, speeds up execution, and protects founder focus. - For growing teams, structured decision-making is essential to scaling without chaos. 4. AI as a Leadership Operating System - Ross explains how Claude helps reduce cognitive load and improve executive efficiency. - AI connects to tools like Fathom, Slack, email, and calendar to surface priorities and requests. - Feedback loops help identify tasks that should be delegated or transferred to the team. - When paired with great talent, AI systems help leaders move faster and think sharper. 5. Recruitment Never Stops - Ross believes founders should always be thinking about who can help level up the team. - Great hires create new capabilities the founder or existing team may not have. - Consistent content and storytelling can attract aligned talent into the organization. - A strong referral culture compounds when employees are excited to bring in people they trust. 6. Ownership Beats Activity - Busy calendars and constant output do not automatically equal meaningful progress. - True ownership means knowing the metric that matters and taking responsibility for the outcome. - Ross looks for people who are growth-minded, accountable, and aligned with company values. - Values should not live in documents or posters; they should show up in how people work every day. — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds

  • July 17 · 21 min

    RSS 62: The Curiosity Filter: Why I Hire for Search History, Not Resumes

    In this episode of The Ross Simmonds Show, Ross shares why curiosity, execution, and continuous learning are becoming more valuable than traditional credentials in marketing, tech, and business. He breaks down how hiring managers, marketers, content creators, and business leaders can identify curious talent, build stronger teams, and stay relevant as AI, search, content distribution, and audience behavior continue to evolve. Key Takeaways and Insights: 1. Curiosity as a Career Advantage - Ross shares how growing up outside major tech hubs pushed him to use the internet as his mentor. - Curiosity helped him build a self-directed education across SEO, social media, content, SaaS, Reddit, LinkedIn, Quora, and startups. - The lesson: your location, background, or lack of connections does not limit your ability to learn and grow. 2. The Hiring Trap: Stacked Resume, Weak Execution - Ross warns leaders not to confuse impressive logos and credentials with real-world capability. - Some candidates know how to follow a playbook but struggle when asked to create or adapt one. - Hiring should focus on how people think, learn, ask questions, and solve problems—not just what appears on paper. 3. How to Identify Curious Marketers - Ask candidates what they are reading, what they are learning, and how they stay sharp in their craft. - Look for people actively tinkering with new tools, especially in the age of AI. - Curious marketers bring questions, data, and insights into conversations instead of relying on old playbooks. 4. Insight-Driven Marketing Decisions - Great marketers do not recommend SEO, CMS changes, or content strategies simply because they prefer them. - They gather data, ask about pipeline goals, conversion rates, customer lifetime value, and channel performance. - Curiosity turns marketing from guesswork into a structured, strategic process. 5. Where Curious People Spend Their Time - Curious professionals go where learning is happening: communities, subreddits, Discord servers, Slack groups, LinkedIn threads, and comment sections. - They engage in discussions, debate ideas, and test what they learn. - They do not just consume marketing tips—they apply them. 6. The Signals of a High-Curiosity Team Member - They research before making recommendations. - They reverse engineer why something worked instead of blindly repeating tactics. - They invest in courses, tools, and resources because they want to become better, not just get promoted. - They challenge leaders with data-backed thinking and fresh perspectives. 7. Why Curiosity Matters in the AI Era - AI is reshaping search, content distribution, GEO, AEO, and how buyers discover brands. - Channels that worked three years ago may not be enough today. - Marketers who stay curious will adapt faster as LLMs, Reddit, YouTube, short-form video, and emerging platforms shift the landscape. 8. Building a Learning Advantage - One to two extra hours of intentional learning per week can put you ahead of people doing none. - Those who invest more deeply in their skills create a larger competitive gap. - Continuous learning builds the taste, strategy, distribution skill, and human understanding needed to stay valuable. 9. Hiring for Curiosity and Growth - Leaders should ask candidates about newsletters, podcasts, tools, personal projects, and ideas they cannot stop thinking about. - Experience with tools like Claude, Perplexity, and ChatGPT can signal active experimentation. - Building a culture of curiosity helps teams stay adaptive, strategic, and ready for what comes next. — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds

  • July 10 · 51 min

    RSS 61: Emotional Targeting: Talia Wolf on Getting From Heart to Cart

    In this episode of The Ross Simmonds Show, Ross sits down with Talia Wolf, founder of GetUplift and author of Emotional Targeting, to unpack why customer emotion is now central to CRO, SEO, content marketing, and brand trust. They explore how marketers can move beyond surface-level analytics, use AI responsibly, uncover real customer motivations, and build messaging that converts by resonating with the right audience everywhere they show up online. Key Takeaways and Insights: 1. Why CRO Starts with the “Why,” Not Just the “Where” - Talia explains why tools like GA4 and Mixpanel can show where conversion problems happen, but not why people fail to convert. - The key to better leads and sales is understanding what information is missing, what feels risky, and what stops customers from taking action. - Strong conversion strategy starts with customer research, not random funnel tweaks or generic best practices. 2. Using AI Without Losing the Customer - AI can support gap analysis, data synthesis, and ideation, but it should not replace direct customer research. - Talia recommends gathering real inputs from surveys, interviews, Reddit threads, Facebook groups, sales calls, and chat transcripts before using AI. - Once you have authentic customer language, AI can become a strategic thinking partner rather than a shortcut to generic copy. 3. Emotional Targeting in B2B Marketing - Talia argues that B2B buying is often more emotional than B2C because professional decisions carry career, reputation, and budget risks. - Two major emotional clusters drive B2B decisions: social image and self-image. - Marketers should connect features to emotional value, such as helping buyers feel confident, trusted, respected, or prepared to impress leadership. 4. Trust, SEO, and CRO Are Converging - Ross and Talia discuss why SEO and CRO can no longer operate in silos. - Modern buyers research brands across Reddit, LinkedIn, YouTube, communities, AI tools, and search results before converting. - The new opportunity is to optimize everywhere by creating consistent, emotionally resonant messaging across owned and non-owned channels. 5. Better Messaging Comes from Better Listening - Talia shares how her team identifies misunderstandings, objections, and friction points through customer conversations and community research. - Real-world examples show how addressing skepticism directly can outperform polished but vague marketing claims. - The best marketers resist the pressure to produce more and instead invest in customer insight, sharper positioning, and continuous testing. Resources & Tools: 🔗 ⁠GetUpLift ⁠ 🔗 ⁠Taliawolf.com⁠ 🔗 ⁠Heart Before Cart⁠ 🔗 ⁠Emotional Targeting Tools⁠ — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: ⁠ @RossSimmondsTV⁠ ╰ Instagram: ⁠@thecoolestcool ⁠ ╰ Twitter / X: ⁠@thecoolestcool ⁠ ╰ LinkedIn: ⁠linkedin.com/in/rosssimmonds⁠ — Connect with Talia Wolf— ╰ Instagram: ⁠@taliagw⁠ ╰ LinkedIn: ⁠linkedin.com/in/taliagw/⁠

  • July 3 · 58 min

    RSS 60: The Marketing Engineer: Nick Lafferty on Building AI Systems for Profound

    In this episode of The Ross Simmonds Show, Ross sits down with Nick Lafferty, Founding Marketing Engineer at Profound, to unpack the fast-moving world of AI visibility, AEO, GEO, and AI search. They explore how brands can earn citations across ChatGPT, Claude, Perplexity, Grok, and Google AI, why visibility is no longer just an SEO problem, and how marketers can build systems that help their teams move faster. Key Takeaways and Insights: 1. Building Marketing Taste Before Automating with AI - Nick explains why AI does not have taste on its own and why marketers need judgment, experience, and creative instincts before automating workflows. - Great marketing taste comes from studying campaigns, consuming strong creative work, testing in public, and learning from feedback. - Creating content consistently, whether through LinkedIn posts, newsletters, blogs, or videos, helps marketers sharpen their voice and understand what resonates. 2. The Rise of the Marketing Engineer - A marketing engineer is part builder, part artist: someone who understands marketing strategy and can build AI-powered systems to solve business problems. - Nick shares how he automated manual unsubscribe syncing across multiple email tools at Profound, saving time for the marketing operations team. - The strongest marketing engineers are AI-native, deeply curious, and focused on redesigning workflows with AI at the center instead of simply automating outdated processes. 3. AI Visibility, AEO, GEO, and the New Search Landscape - Nick challenges the idea that AI visibility is only a content or website problem, noting that most AI citations come from third-party sources. - Profound research shows only about 5–10% of citations come from a brand’s own domain, while the majority come from places like Reddit, YouTube, review sites, press releases, documentation, and partner ecosystems. - Enterprise brands need cross-functional alignment across SEO, PR, social, product marketing, affiliates, and content to compete in AI search. 4. Making the Case for AI Visibility Internally - Nick recommends marketers look for declining organic traffic, rising impressions with fewer clicks, inaccurate AI answers, and poor competitive comparisons as signs of an AI visibility problem. - The Profound team uses the concept “make the invisible visible” to surface hidden risks and opportunities. - Marketers should bring screenshots, prompt examples, traffic trends, and suggested solutions to leadership to win buy-in. 5. Measuring AI Visibility and Proving ROI - Nick advocates for using a required “How did you hear about us?” field to capture self-reported attribution from sources like ChatGPT, Claude, Gemini, and Perplexity. - Profound tracks AI bot traffic, server logs, citation trends, competitive benchmarks, and visibility changes over time. - The conversation highlights why measurement needs to evolve as buyers increasingly discover brands through AI-generated answers. 6. Personas, Memory, and Personalized AI Search Results - Profound’s personas feature helps brands understand how different buyer types may see different AI answers. - Teams can analyze visibility across personas such as SEO managers, CMOs, affiliate managers, PR leaders, and demand generation teams. - Personas help marketers approximate how memory and personalization may shape AI search results for different audiences. 7. Reddit, Listicles, and Off-Site Citation Strategy - Nick explains why Reddit requires a contribution-first mindset and compares it to joining a dinner party where listening matters before speaking. - Listicles may still work in some industries, especially affiliate-heavy categories, but many marketers are over-investing in them as a short-term tactic. - The bigger opportunity is building adaptable systems that can respond to changing citation patterns across AI search platforms. Resources & Tools: 🔗 Profound 🔗 Every 🔗 HubSpot 🔗 Customer.io — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds — 👋🏾 Let's stay connected — ╰ Twitter / X: @nicklafferty ╰ LinkedIn: linkedin.com/in/nicklafferty/

  • June 27 · 57 min

    RSS 59: AI Scales What You've Already Got: Matt Symes on Rewiring How You Operate

    In this episode of The Ross Simmonds Show, Ross sits down with Matt Symes, founder of Symplicity, to unpack why AI transformation fails when companies focus on tools, data, or privacy before fixing broken workflows. Matt shares a practical, workflow-first approach to using AI for sales, marketing, leadership, and business growth while helping founders avoid scaling chaos faster. Key Takeaways and Insights: 1. Why AI Won’t Fix a Broken Business - Matt explains why the “data problem” is often a stall tactic, not the real blocker to AI ROI. - Companies need to start with outcomes and workflows before buying AI tools or hiring AI leaders. - AI scales what already exists so broken systems become faster, messier, and more expensive if left unaddressed. 2. Workflow-First AI Transformation - The best first AI use case is a repetitive, time-consuming workflow that matters but does not create much strategic value. - Matt shares how an AI-powered dossier workflow replaced 10–15 hours of weekly admin work with an automated research process. - Leaders should identify the biggest business constraint—sales, marketing, delivery, or operations and use AI to improve that specific workflow. 3. Using AI to Improve Sales Conversion - Ross and Matt break down how AI can reduce sales cycle time and touchpoints. - Matt shares a real-world example of using open source intelligence and ChatGPT to prepare for a sales conversation, identify likely business problems, and close a deal in three touches. - The key lesson: AI can improve trust, relevance, and conversion when integrated directly into the sales process. 4. Strategy Before Speed - Matt emphasizes that every business must clearly define the problem it solves, who it solves it for, and the value of solving it. - The V8 example shows why businesses can lose growth opportunities when they define themselves by product category instead of customer problem. - Before making anything faster with AI, leaders must clarify their value proposition and target customer. 5. Why CEOs Should Lead AI Adoption - Matt argues that hiring a “Head of AI” too early can be a mistake if the CEO is not actively leading the mindset and workflow transformation. - AI should be treated as a teammate in value creation, not just another technology tool. - Leaders should delegate workflow ownership while staying accountable for the overall AI transformation strategy. 6. Agentic AI Use Cases for Leaders - Matt shares how he uses AI agents to monitor trusted sources, scan newsletters, and update keynote decks with timely research. - He explains how AI can support CEO responsibilities like business performance tracking, leadership coaching, 360 reviews, and scenario planning. - The conversation highlights why leaders should use AI to practice, prepare, and make better decisions, not just automate tasks. 7. Escaping the Founder’s Trap - Matt defines the founder’s trap as building a business that cannot operate without the founder playing a critical role. - He explains how founders can design businesses around their best life instead of becoming trapped by their own company. - Symplicity and Levership help companies build strategic cadence, improve workflows, and scale with more structure. Resources & Tools: 🔗 Symplicity 🔗Perplexity Computer 🔗 NotebookLM 🔗 OpenClaw 🔗 Claude Code 🔗 Claude Cowork — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds — Connect with Matt — ╰ LinkedIn: linkedin.com/in/matt-symes-8328a765/

  • June 19 · 46 min

    RSS 58: All In on Claude: Travis Tallent on Building AI Systems That Actually Scale

    In this episode of The Ross Simmonds Show, Ross sits down with Travis Tallent of DayNova to unpack how organizations can use AI tools like Claude, Claude Code, Claude Chat, and Claude Co-Work to save time, improve workflows, and amplify business growth. Travis shares practical AI agent examples for marketing, sales, operations, finance, and account management, while emphasizing a strategic approach: automate the right work, keep humans in the loop, and reinvest saved time into higher-value output. Key Takeaways and Insights: 1. Using Claude to Build Smarter AI Workflows - Travis explains why Claude is his most-used AI tool and how he uses it for deep research, competitive analysis, proposals, and decision support. - Claude Code helps build and deploy proposal workflows, while Claude Chat acts as a strategic sparring partner. - Claude Co-Work can support daily briefs, research, project prioritization, and competitive monitoring. - The key is building strong skills with brand context, tone, design rules, and clear instructions so outputs feel useful and aligned. 2. The DayNova Framework for AI Transformation - Travis introduces the DayNova framework: Narrow, Orchestrate, Validate, and Amplify. - “Narrow” means identifying which tasks are actually worth automating instead of wasting time on low-impact workflows. - “Orchestrate” focuses on shared knowledge bases, governance, brand assets, and culture skills so teams use AI consistently. - “Validate” keeps humans in the driver’s seat, while “Amplify” reinvests productivity gains into growth, innovation, and domain expertise. 3. Helping Teams Adopt AI Without Fear - Travis explains why AI adoption is not just a software rollout; it is a change management challenge. - Leaders need to acknowledge uncertainty, build psychological safety, and help teams turn anxiety into agency. - AI should be positioned as a tool to change how work gets done, not as something that replaces people’s identity or value. - Successful adoption requires trust, team-specific training, and clear communication about how saved time will be reinvested. 4. AI Agents for Every Business Function - Marketing teams can build conversational agents connected to performance data, rankings, sales trends, and campaign insights. - Operations teams can create internal knowledge bases for policies, brand guidelines, culture, travel rules, and process documentation. - Account management teams can automate meeting notes, project management updates, and client communication scoring - Finance teams can use AI for PO reconciliation, forecasting, payroll workflows, contractor payments, and month-end close support. 5. AI for Sales, Revenue, and Relationship Building - Sales teams can use AI to summarize RFPs, analyze prospects, prepare for calls, and build automated sales coaching systems. - AI-powered prospect research helps teams enter conversations with stronger context and more relevant talking points. - Travis and Ross discuss how AI can strengthen both business and personal relationships through better follow-up and context tracking. - The highest-value human work shifts toward innovation, strategy, relationship-building, and big ideas that previously lacked enough time. Resources & Tools: 🔗 DayNova 🔗 Claude 🔗 Ahrefs — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds — 👋🏾 Connect with Travis — ╰ Instagram: @tallentspeaks ╰ Twitter / X: @tallentspeaks ╰ LinkedIn: linkedin.com/in/travistallent

  • June 12 · 31 min

    RSS 57: 20 Proven Customer Acquisition Tactics to Land Your First Clients

    In this episode of The Ross Simmonds Show, Ross breaks down why founders often over-focus on perfecting the product while underinvesting in the most important part of business: getting customers to buy. He shares 20 practical customer acquisition tactics covering owned channels, outreach, community building, audience engagement, strategic partnerships, personal branding, and frictionless buying experiences. Key Takeaways and Insights: 1. Shift Your Mindset Around Sales - Stop treating every “no” as personal rejection and start seeing it as progress toward a “yes.” - Customer acquisition requires courage, repetition, and strategic thinking—not a massive budget. - Founders need to understand customer nuance, buying behavior, and how to create urgency around their offer. 2. Own Your Audience with Email - Build and maintain an email list so you can communicate directly with prospects and customers. - Make every email valuable enough to inspire, educate, entertain, or give subscribers a competitive edge. - Avoid using email only for product updates or blog announcements; turn it into a trusted resource. 3. Build a High-Value Resource Hub - Create a website section filled with useful tools, guides, quizzes, calculators, and interactive content. - Use gated resources and community features to capture leads and build deeper audience engagement. - Watch for social referral traffic as a signal that your content is valuable enough to share. 4. Create Communities Around Your Market - Build private Slack, Discord, Facebook, or Reddit communities where your ideal customers can gather. - Use these spaces to collect feedback, test ideas, host sessions, and create word-of-mouth momentum. - Stay close to your most engaged community members—they may become your strongest customers. 5. Master Personalized Outreach - Cold email still works when it is researched, relevant, and written for one specific person. - Use LinkedIn, company updates, investor reports, and business context to make outreach feel human. - Ask for feedback or a short conversation instead of immediately pushing for a demo or sale. 6. Leverage Your Existing Network - Reach out to past colleagues, classmates, and professional connections who may now be in relevant roles. - Ask for specific warm introductions and make it easy by writing the intro message for them. - Schedule no-pitch coffee chats to build awareness, gather market research, and create future evangelists. 7. Show Up Where Your Audience Already Spends Time - Participate in Reddit, Medium, Hacker News, Quora, Facebook groups, Slack communities, and X with value-first engagement. - Study the culture of each platform before posting so your contributions fit naturally. - Use podcasts, influencers, guest posts, webinars, and co-marketing to access already-established audiences. 8. Use Strategic Partnerships to Generate Leads - Build referral partnerships with complementary businesses that already serve your ideal customers. - Offer commissions, kickbacks, or revenue share to incentivize partners to send qualified leads. - Create co-branded content or guest content to borrow trust and reach from established audiences. — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds

  • June 5 · 23 min

    RSS 56: Why Smart Founders Step Away: The Data-Driven Case for Rest, Family, and Better Performance

    In this episode of The Ross Simmonds Show, Ross breaks down why stepping away from the grind isn’t falling behind but a strategic advantage. Backed by research and real-life perspective, he shows how rest, presence, and intentional time off can actually fuel better performance, creativity, and long-term success. This is a must-listen for founders, marketers, and creators playing the long game. Key Takeaways and Insights: 1. The Founder’s Dilemma: Grind vs. Presence - Internal conflict between business demands and personal life - Why many founders feel guilty stepping away - The long-term cost of always being “on” - Reframing rest as a strategic decision 2. The Hidden Cost of Hustle Culture - 72% of entrepreneurs report mental health challenges - Overworking increases risk of stroke and heart disease - Long hours may correlate with success—but also burnout - Why “more work” isn’t always the smartest path forward 3. The Science of Creative Breakthroughs - The “incubation effect” and how ideas form during rest - Why low-effort activities unlock better thinking - Real-world examples of breakthroughs away from the desk - How to structure downtime for maximum creative output 4. Why Time Off Drives Better Results - People who take vacations are more likely to earn raises - Rest improves decision-making and cognitive performance - The ROI of unplugging from work - How to think about rest as an investment, not a reward 5. Relationships Are the Ultimate Growth Strategy - 85-year Harvard study on happiness and longevity - Strong relationships outperform traditional health metrics - Loneliness as a hidden risk factor for founders - Why connection is a key part of sustainable success 6. Escaping the Founder Identity Trap - Why tying identity solely to business is dangerous - Stories of founders feeling lost after exit - The importance of building a multi-dimensional identity - How diversifying your identity strengthens resilience — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds

  • May 29 · 55 min

    RSS 55: Reddit, AI & Distribution: The B2B Playbook Most Brands Are Ignoring

    Reddit is influencing more B2B buying decisions than most marketers realize. In this episode, Jon Clark from Page 2 Podcast sits down with Ross to explore how Reddit has become a powerful force in search, why AI is transforming content distribution, and what it takes to build a marketing engine that drives real reach and results. Ross shares practical insights on SEO, content strategy, brand visibility in the age of LLMs, and why the future belongs to teams that invest as heavily in distribution as they do in creation. This conversation is packed with actionable lessons for marketers looking to stay ahead of the next wave of digital growth. Key Takeaways and Insights: 1. Building an AI-Powered Content Engine - Automating idea capture with transcriptions, cloud tools, and AI prompts. - Using spreadsheets + APIs + AI to create a personal “life operating system.” - AI accelerates execution but strategy and human oversight remain critical. - If you’re not 15–20% faster than last year, you’re underutilizing AI. 2. Reddit’s Takeover of Bottom-of-Funnel Search - Reddit now dominates long-tail, high-intent B2B queries. - “Best CRM for real estate small business” style queries are ranking. - Traditional SEO tools showed “zero volume”—but users asked Reddit anyway. - LLMs amplify this effect by generating personalized, long-tail queries. 3. How LLM Memory Changes Search Strategy - AI tools remember context (industry, revenue, location, preferences). - This creates ultra-specific queries behind the scenes. - Reddit wins because it has depth across long-tail discussions. - Strategy shift: Influence conversations where LLMs source answers. 4. The 3 Reddit Accounts Every Brand Needs - ✅ Brand Subreddit (protect your namespace immediately). - ✅ Brand Account (gratitude + reputation management only). - ✅ Personified Account (human engagement + trust building). 5. Organic + Paid Reddit = Scalable Growth - Reddit ads work best when inspired by top-performing organic posts. - Redditors reject polished corporate ads—match the culture. - Use conversational tone and authentic creative. - Lowest CPL often comes from culturally aligned campaigns. 6. Create Once, Distribute Forever (In the AI Era) - Shift from “create, create, create” to “distribute and optimize.” - Search is now multi-platform: Google, YouTube, Reddit, LLMs. - Distribution has moved from “vitamin” to “painkiller.” - Modern SEO = marketing across ecosystems. Resources & Tools: 🔗 Page 2 Podcast 🔗 Create Once. Distribute Forever — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds

  • May 23 · 25 min

    RSS 54: Build a Distribution System That Actually Drives Growth

    Too many marketers hit publish and hope for the best. In this episode, Ross breaks down why hope is not a distribution strategy and what to do instead. You’ll learn how to build a deliberate, repeatable content distribution system that amplifies reach, compounds results, and drives measurable business growth in the AI era. Key Takeaways and Insights: 1. Hope Is Not a Distribution Strategy - Publishing and “hoping” for shares, rankings, or virality is not a growth plan. - Great content alone doesn’t guarantee reach or impact. - Distribution is the difference between obscurity and authority. 2. Why Great Content Still Loses - Average content often wins because it’s distributed strategically. - Algorithms reward engagement velocity, reach, and timing not just quality. - Distribution turns good content into great content. 3. AI, LLMs & the New Search Reality - AI-powered search is reducing traditional click-through traffic. - Optimizing for rankings alone is no longer enough. - LLMs pull from platforms like Reddit, LinkedIn, and licensed content sources. - Smart distribution increases your visibility across AI-driven experiences. 4. The Five Biggest Distribution Mistakes - Publishing once and disappearing. - Relying exclusively on one channel. - Assuming organic reach is guaranteed. - Failing to repurpose content across formats. - Not tracking performance or outcomes. 5. Create Once, Distribute Forever - Turn one blog post into carousels, threads, emails, videos, and podcasts. - Break pillar assets into micro-content for every channel. - Reshare and repackage content over time don’t let it die after launch week. - Repurposing multiplies ROI without multiplying effort. 6. Build a Real Distribution Strategy (Step-by-Step) - Conduct content-market fit research: understand pains, desires, and behaviors. - Analyze channel-user fit: where your audience actually spends time. - Study attention leaders (even outside your niche) to reverse-engineer engagement. - Create a pillar asset, repurpose aggressively, distribute across owned, earned, paid, and shared channels. - Rinse, repeat, and optimize using data. Resources & Tools: 🔗 Distribution.ai 🔗 Create Once, Distribute Forever 🔗 HubSpot 🔗 Ahrefs 🔗 Google Analytics 4 🔗 SparkToro — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds

  • May 15 · 14 min

    RSS 53: The Future CMO: Why You Must Become a Media Operator in the Age of AI

    In this episode of The Ross Simmonds Show, Ross makes a bold prediction: the next great CMO will be a media operator with a marketing budget. As AI and LLMs reshape how buyers discover and decide, traditional attribution, funnels, and SEO playbooks are breaking down. If you want to win in an AI-first world, it’s time to shift from campaign thinking to category ownership. Key Takeaways and Insights: 1. The Future CMO = Media Operator - The next generation of CMOs won’t just build campaigns—they’ll own media ecosystems. - Success shifts from “creating great ads” to controlling the narrative across a category. - Media ownership (owned + partnered) becomes a strategic advantage. 2. AI Is Rewriting Buyer Behavior - LLMs like ChatGPT, Gemini, and Claude are influencing buying decisions directly. - Consumers are getting answers without visiting your website. - The opportunity isn’t to interrupt attention—it’s to shape what AI recommends. 3. The Power of LLM Memory - AI personalizes answers based on stored user context (company size, budget, role). - Each platform (Gemini, ChatGPT, Claude) has different memory advantages. - Tracking only head terms is a mistake—long-tail, bottom-of-funnel queries matter more. 4. From Presence to Scale - Old model: “How much content did we publish?” - New model: “How often are we referenced across the web?” - Visibility in conversations—onsite and offsite—is the new KPI. 5. Category Ownership Through Media Acquisition - Buy and build media assets within your niche. - Create high-value, proprietary, non-commodity content. - Distribute aggressively to influence what LLMs cite and recommend. — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds

  • May 7 · 21 min

    RSS 52: Why 44.8% of B2B Content Fails to Earn Backlinks And the 3 Formats That Actually Work

    In this episode of The Ross Simmonds Show, Ross breaks down findings from the B2B Backlink Intelligence Report, an analysis of 12,154 pages across 24 B2B brands and 11 verticals, to reveal why 44.8 percent of thought leadership content fails to earn meaningful backlinks. He exposes the 9.5-point performance gap hiding inside most B2B content strategies and shares the three underutilized formats that consistently generate authority, links, and compounding growth. Key Takeaways and Insights: 1. The 44.8% Failure Rate of Thought Leadership - Thought leadership accounts for 37 percent of B2B content but earns only 27 percent of backlinks. A 9.5-point performance gap signals massive resource misallocation across the industry. - Most teams never audit whether their executive POV content actually earns links. The data exposes a problem most marketing leaders are actively ignoring. 2. Inside the B2B Backlink Intelligence Report - The study analyzed 12,154 pages across 24 B2B brands and 11 verticals using two core questions: what format is it and how many referring domains does it earn? - The most published format turned out to be the worst performer on a per-page basis. Data replaces opinion. The receipts are in. 3. Why Thought Leadership Underperforms - Thought leadership sounds strategic but internal applause, Slack praise, and LinkedIn likes create a false sense of traction. Teams rarely check backlinks, citations, or amplification metrics. - Most brands overestimate how much the market cares about executive opinions. Journalists and analysts want citable data, clear definitions, and practical insights. Not hot takes. 4. When Thought Leadership Actually Works - It performs best when the brand is already famous. Authority compounds authority and mid-market brands rarely break through on opinion alone. - Unique data paired with a strong perspective outperforms pure POV every time. The question is not whether thought leadership works. It is whether it will work for you. 5. The Link Magnet Trifecta - Three formats consistently outperform thought leadership with higher efficiency rates, lower fail rates, and compounding backlink growth over time. - Most B2B teams are dramatically under-allocating to these formats while continuing to invest in the one with the worst returns. 6. Stats and Data Roundups: 4.25x Efficiency - Stats pages carry a fail rate of just 5.3 percent and a breakout rate of 42 percent to 1,000-plus referring domains. Journalists constantly search for consolidated, up-to-date statistics. - One well-maintained stats page can outperform a year of blog posts. Keep it fresh. Rankings and relevance drive long-term link velocity. 7. Glossary and Definition Pages - Writers link to the clearest definition available. Definitions age better than predictions or trend pieces, making these pages durable link assets. - Own the terminology in your category and you own the citations. This format remains powerful for links even as organic traffic patterns shift. 8. How-To Content Independent of Your Product - The highest-performing how-to content solves tasks even if your product did not exist. Avoid product documentation disguised as SEO content. - Utility-driven tutorials earn links because they help the broader ecosystem. Top performers covered tools and topics like Google Drive, HTML, Fiverr, and Alibaba. 9. Backlinks Still Matter in the AI Era - Google still runs on links even in AI mode. Authority signals matter more now, not less. Backlinks are infrastructure for search visibility across both traditional and generative engines. - The compounding effect rewards long-term operators. Every link earned today is a signal that shapes AI visibility tomorrow. 10. Think Like an Investor, Not an Artist - Backlinks compound after publication. Audit your content strategy before publishing another thought leadership piece and reallocate toward formats with asymmetric upside. - Invest more. Guess less. The brands that treat content like a portfolio will outperform the ones treating it like a creative outlet. Resources & Tools: 🔗 B2B Backlink Intelligence Report — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds

  • May 1 · 19 min

    RSS 51: LLM Visibility Playbook. 5 Proven Moves to Win in the AI Search Era

    In this episode of The Ross Simmonds Show, Ross breaks down why showing up in LLMs like ChatGPT, Claude, and Perplexity is the biggest marketing shift of our time and why treating it like SEO 2.0 is a losing strategy. He walks through five practical plays to build citation authority, dominate AI visibility, and engineer the kind of distribution leverage that compounds long after you press publish. Key Takeaways and Insights: 1. The Shift from SEO to GEO - In 2018, Reddit was dismissed. In 2026, it powers over 60 percent of bottom-funnel LLM citations. Google, OpenAI, and Anthropic are actively licensing and training on Reddit data. - Most teams are still optimizing for keywords and backlinks. GEO rewards authority, citations, and entity strength. The game has changed and the old playbook will not save you. 2. Play 1: Build a Citation Stack with Original Research - LLMs prioritize strong signals. Non-commodity content, original data, research, and clear POV outperforms generic blog posts every time. - Make every stat screenshot-friendly and quotable. Pitch your research to publications already cited in LLMs to compound authority and become the source models reference. 3. Play 2: Plant Flags in Communities - Reddit is one of the most cited sources in major LLMs. Identify three communities where your audience actually spends time and show up there consistently. - Use the Sherlock Homeboy Method: revive proven topics with a modern angle. Contribute value without pitching. Build reps. Create a moat competitors cannot climb. 4. Play 3: Engineer Your Entity Graph - LLMs see entities, not webpages. Companies, people, and products are all connected. Guest posts, podcast appearances, and transcripts strengthen your entity signal. - Consistent handles, bios, and positioning across platforms increase recognition. Say the same thing clearly thousands of times. Strategic repetition builds authority. 5. Play 4: Structure Content for Extraction - LLMs extract facts and quote passages. They ignore fluff. Use inverted pyramid writing: answer first, explain second. - Clear H1, H2, and H3 hierarchies improve both human and machine comprehension. Schema, lists, tables, and internal linking help models understand and cite your content. 6. Play 5: Distribution Is the Final Moat - One asset. Fifty distributions. Multiple citation paths. Most brands post once and disappear. Winners distribute relentlessly. - Every surface, LinkedIn, Reddit, YouTube, Substack, and podcasts, becomes training data. Distribution compounds trust with both humans and machines. 7. The Future: AI Agents Will Change Buying Forever - By 2038, AI assistants will mediate most purchasing decisions. Buyers will not browse. They will delegate. - The content LLMs train on today will shape tomorrow's recommendations. If you are not building your moat now, you will be rebuilding from scratch later. 8. The Long-Term Advantage Goes to Those Who Invest in Themselves - The skills that worked in 2018 will not carry you to 2038. Read. Study. Experiment. Adapt. - Earned momentum compounds through disciplined execution. Play the long game. Resources & Tools: 🔗 ChatGPT 🔗 Claude 🔗 Perplexity 🔗 Reddit 🔗 Google 🔗 OpenAI 🔗 Anthropic 🔗 LinkedIn 🔗 YouTube 🔗 Substack — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds

  • April 24 · 19 min

    RSS 50: The Bold Thesis "Distribution Is the Last Moat Standing"

    In this episode of The Ross Simmonds Show, Ross breaks down why OpenAI and HubSpot's media acquisitions this quarter aren't about content quality. They're about owning distribution. He connects the dots on what this land grab means for every B2B marketer and how to apply the same strategy without a billion-dollar balance sheet. Key Takeaways and Insights: 1. Media Acquisition Is the New Moat - OpenAI and HubSpot made bold media acquisitions in the same quarter. This isn't about content quality. It's about owning the rooms where buying decisions happen. - Distribution is leverage. And leverage compounds. The brands that win will own the audience, not just the message. 2. The Land Grab Has Already Started - Penn bought Barstool. HubSpot acquired The Hustle and Starter Story. Robinhood built a media empire. Plaid acquired fintech media to own operator attention. - The cadence of these deals is accelerating. This is not a trend. It's a land grab and most B2B teams haven't noticed. 3. Super Bowl Ads vs. Owned Attention - $27M buys six Super Bowl ads that disappear in 30 seconds. The same capital can buy a media asset with daily access to your exact ICP. - Most teams rent attention. The best operators own it. Predictable pipeline starts with predictable distribution. 4. Google's AI Shift Changes the Game - AI Overviews are reducing clicks to traditional search results while Google embeds YouTube directly into the SERP. - Media value is no longer just blog rankings. It's multimedia presence. Visibility now requires platform-native authority. 5. You Cannot Game LLM Visibility - Traditional SEO could be manipulated with backlinks and paid boosts. AI visibility requires real brand equity and positive sentiment. - LLMs train on authority signals across media properties. If you want to show up in AI answers, you must be worth citing. 6. Brand Equity Beats Editorial Independence - Acquired media serves stakeholders. Narrative shapes culture and buying media shapes narrative. - Read content with context. Ownership matters. Content influence increasingly flows through owned channels. 7. The 4 Distribution Questions Every Marketer Should Ask - Which newsletter has the audience you wish you had? Which creator has your buyers' trust? What shows does your ICP consume weekly? What niche media opportunity is still wide open? - Use LLMs and audience intelligence tools to find answers faster. The operators asking these questions now are building moats everyone else will pay to access later. 8. How to Build a Media Engine Without Buying One - Start one channel and let patience compound. Sponsor niche newsletters instead of chasing giants. Partner with trusted creators via revenue share, salary, or equity. - In the AI era, content is cheap. Reputation and distribution are scarce. Build accordingly. 9. Three Predictions for the Next Decade - By 2035, every unicorn B2B company will own a media property. Newsletter and YouTube network valuations will triple as LLM visibility becomes priced in. - Agencies will survive by brokering, building, or optimizing media ecosystems, not just producing content. 10. Distribution Is the Last Moat Standing - AI commoditized content creation. The advantage shifts to those who control reach. A true content moat goes beyond your domain. - Visibility is engineered, not hoped for. The window to build that moat cheaply is closing fast. Resources & Tools: 🔗 OpenAI 🔗 HubSpot 🔗 The Hustle 🔗 Starter Story 🔗 Robinhood 🔗 Plaid 🔗 Barstool Sports 🔗 Google 🔗 YouTube — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds

  • April 17 · 19 min

    RSS 49: Reddit Is Beating You in B2B Search And the Data Proves It

    In this episode of The Ross Simmonds Show, Ross drops new research across 8,566 high-priority B2B SaaS keywords that reveals how Reddit is quietly dominating bottom-of-funnel search, including the most expensive CPC terms in your Google Ads account. He breaks down what the data actually means for your pipeline and the exact playbook operators need to respond before the gap widens further. Key Takeaways and Insights: 1. How Reddit Changed the SEO Game -Google elevated user-generated content after seeing demand for people-first answers, and Reddit threads now outrank product and category pages across B2B SaaS. -Traditional SEO playbooks built on volume and backlinks are losing ground. The shift is not theoretical. It is happening in your highest-value queries right now. 2. The Scoreboard: Reddit's Share of the Top 3 -Reddit commands 40 to 45 percent of top-three rankings across most B2B SaaS verticals. In three of four industries analyzed, Reddit consistently beat all competitors. -Even established review sites are losing ground to subreddit threads. The brands still ignoring this are handing over pipeline. 3. Myth: Reddit Only Wins on Review Terms -Reddit wins 94 percent of the time for "best software" queries, but 77 percent of Reddit's wins come from non-review, demand-gen keywords. -Reddit is not just stealing review traffic. It is influencing pipeline at every stage of the buyer journey. 4. The CPC Paradox -At $15 to $20 CPC, Reddit wins 45 percent of the time. At $50-plus CPC, that number hits 67 percent. -You are paying $50 per click while a two-year-old Reddit thread captures the organic click above you. 5. Authority Alone Does Not Win Anymore -High domain authority no longer guarantees rankings. Brands that win build long-tail infrastructure aligned to real customer queries. -Long-tail blog content consistently outperforms thin category pages. The edge goes to operators who build depth, not just links. 6. Subreddits Are the Real Competitors -It is not Reddit as a monolith. It is specific communities. The CRM subreddit showed a 49 percent win rate. r/EmailMarketing hit 68 percent. r/SmallBusiness drove nearly 141K monthly searches across tracked queries. -One subreddit can dominate an entire B2B category. These are your real competitors. 7. Long-Tail Is Where Reddit Dominates -For keywords with six or more words, Reddit's win rate hits 87 percent. Years of user questions created a library of hyper-specific content that is nearly impossible to replicate overnight. -That long-tail depth fuels both Google rankings and LLM citations. If you are not building long-tail assets, you are invisible in AI search. 8. Reddit Now Shapes LLM Visibility -B2B buyers use peers, communities, and LLMs to validate decisions, and LLMs are citing Reddit more than ever. -If you are absent from key subreddits, you likely do not exist in AI-generated answers either. Reddit presence influences both the SERP and the model. 9. The Operator Playbook for Winning on Reddit -Run a keyword gap analysis against reddit.com. Identify three to five subreddits consistently outranking you. Engage with value, not pitches. Earn credibility first. -Invest in high-quality educational content and measure sentiment and LLM visibility as part of your growth system. This is how you build presence that compounds. Resources & Tools: 🔗 Reddit 🔗 Google — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: https://x.com/TheCoolestCool ╰ LinkedIn: linkedin.com/in/rosssimmonds

  • April 10 · 24 min

    RSS 48: The Fractional CMO Playbook: From Underdog to $270K

    In this episode of The Ross Simmonds Show, Ross breaks down how he built a quarter-million-dollar solo consulting business before 30 and how he would engineer that same growth today as a fractional CMO in the AI era. From personal brand foundations to referral flywheels to public speaking as a client acquisition engine, this is a tactical, no-excuses blueprint for building authority and pipeline as a one-person growth operation. Key Takeaways and Insights: 1.From Basement to $270K: The Origin Story -Ross built a quarter-million-dollar solo business before 30 with no elite network and no big-city advantage. Just reps, value creation, and commitment to the long game. -Underdogs win when they stop waiting for permission and start stacking consistent execution. 2.What a Fractional CMO Actually Does -A fractional CMO provides strategic marketing leadership across brand, messaging, content, search, and growth without the full-time cost. Multiple companies. Real equity upside. -It is one of the highest-leverage positions in the market right now for marketers who own outcomes, not just tasks. 3.Personal Brand Is the Foundation -If someone Googles you today, what shows up? Buy your domain. Control your narrative. Publish content aligned to your niche and your ideal client profile. -Your name is an asset. Treat it like one or someone else will define it for you. 4.Consistency Beats Excuses in the AI Era -AI removes friction. It does not replace strategy. If you have no clients and you are not posting daily, that is the problem. -Visibility is engineered through repurposing content across LinkedIn, X, Threads, YouTube, and podcasts. Not hoped for. 5.Build Leverage with Talent and AI -Combine AI systems with high-level human talent. Use tools like Claude, ChatGPT, Fathom, and Superhuman to increase capacity without adding headcount. -Hire globally. Skill beats geography. Layer systems and people and you get agency-level output from a solo operation. 6.Diversify Revenue Without Destroying Focus -Courses, speaking, e-commerce, consulting — multiple income streams are real. But side quests can build skills or kill focus depending on how you sequence them. -Depth compounds faster than scattered effort. Focus accelerates revenue growth. 7.Referral Flywheels as Passive Leverage -Do great work, earn inbound referrals, and build a referral program that earns without direct delivery. Partner with agencies and specialists to expand capability without expanding overhead. -Compounding trust beats cold outreach every time. 8.Public Speaking as a Client Acquisition Engine -Speaking landed Ross publicly traded clients. Reps build confidence. Confidence builds pipeline. Add value on stage and the rest follows. -Most people fear judgment. The reality: few remember you after two hours. Get on stage anyway. 9.Ignore Hype Cycles. Play the Long Game. -"SEO is dead" is a recurring headline. It has been wrong every time. Trends rotate. Fundamentals compound. -Decades of focused reps create unfair advantage. AI matters. Shiny objects do not. 10.Focus Is a Competitive Advantage -Stop doom-scrolling. Start building. Do not argue with trolls. Create instead. -Protect your mindset like you protect revenue. The long game rewards discipline above everything else. Resources & Tools: 🔗 Claude 🔗 ChatGPT 🔗 Fathom 🔗 Superhuman — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds

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