The Ross Simmonds Show

Ross Simmonds
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  • Entrepreneurship
  • Updated twice weekly

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.

  1. 4 days ago

    RSS 68: Reddit, ChatGPT, and the Truth About AI Citations: Why Smart Marketers Shouldn’t Panic

    In this episode of The Ross Simmonds Show, I break down what Reddit’s decline in ChatGPT citations actually means for marketers, brands, and content teams. Instead of reacting to headlines, I share a more strategic view of Reddit’s role in AI search, Google visibility, community engagement, and bottom-of-funnel influence. Key Takeaways and Insights: 1. The Reddit Citation Panic Explained - I address the wave of reactions after reports showed Reddit appearing less often in ChatGPT citations. - This shift is not a signal to abandon Reddit altogether. - The bigger lesson: marketers need context before making channel decisions. 2. Not All LLM Prompts Are Created Equal - Different prompts require different types of sources, and Reddit is not ideal for every query. - Reddit may be useful for software, tech, and troubleshooting questions, but less appropriate for sensitive topics like health. - Citation changes should be evaluated based on use case, not hype. 3. Why Marketers Need to Track Citations Themselves - Third party studies can be helpful, but they do not replace brand specific monitoring. - I encourage teams to benchmark how their own prompts, categories, and keywords perform across LLMs. - Ongoing tracking is essential for adapting to algorithm changes in AI search. 4. Reddit Still Matters for Enterprise and Bottom of Funnel Queries - Even with fewer citations overall, Reddit remains relevant for transactional and bottom of funnel enterprise software searches. - For B2B marketers, that means Reddit can still influence high intent buyers. - Strategic prompt tracking can uncover where Reddit continues to drive value. 5. AI Search Is Changing Constantly - Volatility is now part of digital marketing. - Citation sources can shift between Reddit, LinkedIn, YouTube, review sites, and competitors at any time. - The most effective marketers build systems to monitor change instead of reacting emotionally. 6. Google Still Gives Reddit Massive Visibility - Reddit's value goes beyond ChatGPT because Google still heavily features Reddit in organic search, AI Overviews, and AI Mode. - As long as Google dominates search behavior, Reddit remains strategically important. - Marketers should think beyond one platform when evaluating channel performance. 7. Reddit Is Still Where Real Buyers Ask Real Questions - Millions of users visit Reddit daily to research products, services, tools, and business decisions. - The platform remains a trusted space for niche discussions, peer recommendations, and category conversations. - That creates strong opportunities for brands that want to influence informed buyers. 8. Value Wins on Reddit - Reddit's strong moderation and anti spam systems are a big reason the platform still matters. - Brands that show up only to promote themselves will struggle. - Brands that consistently help, educate, and participate authentically can build real credibility. 9. A Smarter Reddit Strategy for Brands - Teams can study top performing posts, identify audience needs, and create content that genuinely helps the community. - The best Reddit strategy starts with value, not self promotion. - Instead of dropping Reddit because of one data point, brands should diversify their approach across SEO, community, ads, and AI visibility. — 👋🏾 Let's stay connected — ╰ Subscribe to my channel:  @RossSimmondsTV  ╰ Instagram:  @thecoolestcool   ╰ Twitter / X: @thecoolestcool   ╰ LinkedIn: linkedin.com/in/rosssimmonds

    RSS 68: Reddit, ChatGPT, and the Truth About AI Citations: Why Smart Marketers Shouldn’t Panic

  2. 24 Aug

    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

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

  3. 17 Aug

    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/

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

  4. 10 Aug

    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/

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

  5. 31 Jul

    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

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

  6. 25 Jul

    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

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

  7. 17 Jul

    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

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

  8. 10 Jul

    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/⁠

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

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.

Information

  • Creator
    Ross Simmonds
  • Years Active
    2022 - 2026
  • Episodes
    186
  • Rating
    Explicit
  • Copyright
    © Foundation Inc.
  • Show Website
    The Ross Simmonds Show

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