The Ross Simmonds Show

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.

The Ross Simmonds Show is a business podcast hosted by Ross Simmonds, with 184 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Ross Simmonds hosts The Ross Simmonds Show, a business show with 184 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  The Ross Simmonds Show

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

  Aug 17, 202653 min

  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/

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  The Ross Simmonds Show

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

  Aug 10, 202650 min

  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/

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  The Ross Simmonds Show

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

  Jul 31, 20261h 4m

  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

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  The Ross Simmonds Show

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

  Jul 24, 202617 min

  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

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  The Ross Simmonds Show

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

  Jul 17, 202622 min

  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

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