The Ross Simmonds Show

Ross Simmonds
  • 0.0 (0)
  • 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. RSS 34: Winning with Intention in the Age of AI with Will Reynolds

    1 DAY AGO

    RSS 34: Winning with Intention in the Age of AI with Will Reynolds

    In this episode of The Ross Simmonds Show,  Ross sits down with Wil Reynolds—founder of Seer Interactive and an icon in the world of search—to explore how to play the long game in marketing, leadership, and entrepreneurship. Will doesn't hold back as he shares tactical insights into how AI is reshaping content creation, search, and discovery. From real-world applications of tools like PhantomBuster and Claude Code to personal philosophies about content, agency building, and mindset, this episode is loaded with actionable wisdom and candid perspective. Wil also opens up about what he’d do if he had to start over from scratch, the dangers of imposter syndrome, and how to use AI to interview subject matter experts in a scalable way. Key Takeaways and Insights: 1. Respect the Audience’s Attention - Share only what you genuinely believe will teach someone something. - Use a simple gut-check: “Would I want to see this in my feed?” - Don’t post to post—post to educate and create real value. 2. “Real Stuff” Builds Trust - The most resonant content is often the painful, honest, behind-the-scenes truth. - Being raw and human builds long-term sentiment—and turns strangers into future clients. - The posts that work are raw: mistakes, broken processes, real lessons. 3. Distribution Beats “Perfect Content Process” - Over-engineered content processes don’t matter if nobody distributes the output. - Optimize for conversation + sharing, then adapt it for search after you know it hits. 4. Use Data + AI to Run Experiments (and Get Leverage) - Tools like PhantomBuster + Claude/Claude Code can turn LinkedIn into a research + lead engine. - Track who engages (titles, industries), then use that insight for outreach and pipeline planning. - Blend paid + organic data to spot waste/opportunity (e.g., language intent mismatches, “people also ask” signals). - The goal isn’t replacing people — it’s pulling real knowledge out of them faster. 5. Future-Proofing Means Adaptability - The real edge is staying unsatisfied with the status quo and constantly testing new approaches. - Leaders should make it safe to “break things” while learning—innovation is messy by nature. - Wil’s focus isn’t predicting 10 years out—it’s preparing people now for automation shifts through skills, reps, and experimentation. Resources & Tools: 🔗 PhantomBuster 🔗 Claude — 👋🏾 Let's stay connected — ╰ Subscribe to my channel:  @RossSimmondsTV  ╰ Instagram:  @thecoolestcool   ╰ Twitter / X: @thecoolestcool   ╰ LinkedIn: linkedin.com/in/rosssimmonds — 👋🏾 Connect with Wil  — ╰ Twitter / X: @wilreynolds ╰ LinkedIn: linkedin.com/in/wilreynolds/

    1h 19m
  2. RSS 33: Leaders Say They Want Ownership, But Micromanage Everything

    26/12/2025

    RSS 33: Leaders Say They Want Ownership, But Micromanage Everything

    In this episode of The Ross Simmonds Show, Ross dives into one of the most common yet damaging habits of leaders: micromanagement. While founders and leaders often express the desire for team members who “act like owners,” their own behavior can stifle that very ownership. Ross explores the concept of the "Ownership Window," offering a strategic framework for when leaders should be hands-on and when to step back. He breaks down the fine line between leadership and control, examines the stages of team empowerment, and provides actionable insights for creating a company culture rooted in autonomy, accountability, and trust. Key Takeaways and Insights: 1. The Ownership Paradox - Leaders say they want ownership but often undermine it with controlling behaviors. - A lack of delegation leads to decision bottlenecks and ruins team morale. 2. The Downside of Micromanagement - Suck energy out of teams. - Kill trust, decision-making, and momentum. - Be mistaken for productivity from the leader’s perspective. 3. The “Ownership Window” Framework - New Hire or New System (High Support Needed): Provide clarity, oversight, and a tight feedback loop. Avoid guesswork by implementing SOPs, training, and checkpoints. - New Initiative (Strategic Oversight Needed): Leaders act more as advisors than operators. Maintain checkpoints without hovering. - Proven Leader (High Trust & Autonomy): Align on outcomes, then step back. Focus on results, not the method of execution. 4. Coaching vs. Controlling - Coaching is intentional and supportive. - Controlling is reactive and born out of ego or fear. - Leadership requires adjusting engagement based on team maturity and context. 5. Redefining Ownership in Leadership - Clear expectations of what great looks like. - Accountability for outcomes, not just tasks. - Autonomy to decide how work gets done. — 👋🏾 Let's stay connected — ╰ Subscribe to my channel:  @RossSimmondsTV  ╰ Instagram:  @thecoolestcool   ╰ Twitter / X: @thecoolestcool   ╰ LinkedIn: linkedin.com/in/rosssimmonds

    12 min
  3. RSS 32: Your Company Culture Is a Reflection of Your Worst Habits

    20/12/2025

    RSS 32: Your Company Culture Is a Reflection of Your Worst Habits

    In this episode of The Ross Simmonds Show, Ross gets real about what culture truly is inside an organization. Spoiler alert: it’s not your values deck, your company retreats, or the catchphrases painted on your office walls. Culture is what your team experiences—and that starts with leadership. Ross unpacks how the most problematic leadership habits quietly become the blueprint of a company’s culture. Through personal insights and actionable advice, this episode challenges leaders to reflect on their behaviors, confront their blind spots, and align their habits with the culture they aspire to create. Key Takeaways and Insights: 1. Culture Is Practiced, Not Preached - Culture isn’t your onboarding slide deck or a nicely printed poster—it's what your company does every single day. - If you claim a value (e.g. empathy, growth, candor), but your actions contradict it, then it’s not part of your real culture. 2. Leadership Habits Define Team Norms - “Your culture is a reflection of your worst leadership habits.” - Leaders unintentionally shape culture through the behaviors and patterns they tolerate or exhibit. 3. The Toxic Impact of Avoidance - Avoiding hard conversations or decision-making can silently simmer into dysfunction. - Leaders need to have the courage to confront their personal weaknesses to positively affect culture. 4. Build Muscle Memory for Better Leadership - If giving feedback or staying focused is hard, start building systems and routines that reinforce those behaviors. - Example: “Pursue the awkward” moments to grow stronger in them. 5. Self-Awareness Is Crucial - Ask critical questions as a leader: Am I consistent? Do I finish what I start? Am I a source of clarity or chaos? - Teams watch leaders’ actions more than they listen to their words. Walk matters more than talk. 6. Cultivate Culture by Fixing Yourself First - Introspective leadership is the foundation of thriving workplace culture. - Practical step: Make a list of personal habits that are out of alignment with your company’s stated values and strategize ways to improve. 7. Leadership Isn’t About Titles - You don’t need to be a CEO or founder to lead with intentionality. - Cultural influence can come from any level within an organization—or your life. — 👋🏾 Let's stay connected — ╰ Subscribe to my channel:  @RossSimmondsTV  ╰ Instagram:  @thecoolestcool   ╰ Twitter / X: @thecoolestcool   ╰ LinkedIn: linkedin.com/in/rosssimmonds

    9 min
  4. RSS 31: You Don’t Deserve a High‑Performing Team If You’re Not a High‑Performing Leader

    12/12/2025

    RSS 31: You Don’t Deserve a High‑Performing Team If You’re Not a High‑Performing Leader

    In this episode of The Ross Simmonds Show, Ross delivers a candid message to founders, executives, and team leaders. If you're demanding high performance from your team but not modeling it yourself, the problem starts with you. Ross explores how poor leadership habits affect team culture and performance — and why success begins with self-awareness, accountability, and leading by example. If you're frustrated with team results, before looking outward, Ross encourages you to look in the mirror. He shares lessons from his own leadership journey and offers practical questions to help you evaluate your leadership habits. Key Takeaways and Insights: 1. Leaders must model what they expect. - You can't demand elite output while operating with average habits. - Culture is a reflection of leadership. If your organization is underperforming, the root may be your own inconsistencies. - High performance trickles down. Your team won't surpass the standard you set — raise the standard, and the team will follow. - Introspection before criticism. Ask yourself hard questions about your leadership style and consistency. - Show your team what preparation looks like. Demonstrate how you lead meetings, deliver presentations, and display urgency. 2. Growth requires investment. - Leaders must continually invest in themselves to lead their teams effectively. - Excellence spreads when it's consistently displayed through actions, not just words. — 👋🏾 Let's stay connected — ╰ Subscribe to my channel:  @RossSimmondsTV  ╰ Instagram:  @thecoolestcool   ╰ Twitter / X: @thecoolestcool   ╰ LinkedIn: linkedin.com/in/rosssimmonds

    7 min
  5. RSS 30: Generative Engine Optimization (GEO): Why I'm All In

    05/12/2025

    RSS 30: Generative Engine Optimization (GEO): Why I'm All In

    In this episode of The Ross Simmonds Show, Ross dives deep into one of the most fundamental marketing shifts of our time — the emergence of Generative Engine Optimization (GEO). As AI-powered discovery tools like ChatGPT, Perplexity, Google AI Overviews, Reddit Answers, TikTok Search, and more evolve, traditional SEO strategies are no longer enough. Ross unpacks how marketers need to rethink content creation, distribution, and visibility across platforms, focusing not just on ranking, but on being cited, trusted, and remembered. Whether you’re an SEO pro, a content marketer, or someone navigating the changing digital landscape, this episode offers a powerful perspective on where discovery is heading and how you can position your brand for success. Key Takeaways and Insights: 1. The Shift from Traditional SEO to GEO - The discovery journey is changing — not all search begins (or ends) on Google. - GEO (Generative Engine Optimization) is not just about keywords and backlinks, but about engaging with AI-powered platforms like ChatGPT, Claude, Perplexity, You.com, Reddit, TikTok, YouTube, and more. - Terminology wars (AISEO, AEO, GEO) are less important than understanding the strategic implications of the shift. 2. Where AI Discovery is Happening - AI overviews and LLMs (large language models) pull data from varied sources, not just webpages — Reddit, YouTube, TikTok, and UGC are key. - Clicking is becoming less important as AI agents deliver answers before users even leave the platform. 3. YouTube’s Role in GEO - YouTube isn't just social media — it’s the second-biggest search engine and a major citation source for LLMs. - Talking head videos, product comparisons, and keyword-aligned titles matter more than ever. - A poor YouTube strategy (short, shallow clips) means your audience never finds you. 4. Listicles, PR, and Affiliate Strategy in the AI Age - AI often weighs citations based on list ranking — being #8 consistently limits visibility. - Your affiliate and digital PR strategies must now consider how high you appear on listicles that AI sources from. - Move beyond backlinks to placements, citations, and brand mentions across high-impact domains. 5. Tailoring Content for Audience-Specific Queries - LLMs recognize nuances: “best for beginners” vs. “best for enterprise” matters. - Brands should create multiple landing pages tailored to different personas (as long as it’s high quality and not duplicated). 6. The Difference Between SEO and GEO - GEO includes SEO, but it’s broader — it encompasses TikTok search, Instagram Reels, Reddit, and any platform with discovery. - GEO is about visibility in AI-powered interfaces, not just search rankings. 7. The Predictive Future of Discovery - Personalized AI results are here: Google’s AI Overviews may use Gmail, Calendar, Chrome history to shape responses. - The future consumer journey might completely bypass websites and search engines. Resources & Tools: 🔗 AirOps 🔗 Google AI Overviews — 👋🏾 Let's stay connected — ╰ Subscribe to my channel:  @RossSimmondsTV  ╰ Instagram:  @thecoolestcool   ╰ Twitter / X: @thecoolestcool   ╰ LinkedIn: linkedin.com/in/rosssimmonds

    22 min
  6. RSS 29: How to Use AI With Intention, Not Just Curiosity

    28/11/2025

    RSS 29: How to Use AI With Intention, Not Just Curiosity

    In this episode of The Ross Simmonds Show, Ross dives deep into embracing AI with clarity and direction rather than chaos and overwhelm. Rather than chasing trendy tools or piling on new software, Ross introduces the powerful AIM Framework—a proven model he’s developed to help founders, marketers, and operators use AI with intentionality. AIM stands for Accelerate, Integrate, and Multiply. Whether you're a startup founder, marketer, or operator, this episode will help you cut through the AI noise, re-center your focus, and make AI a meaningful part of your business operations—without burning out or overengineering.   Key Takeaways and Insights: 1. The AI Trap vs. The AI Advantage - Most people and teams are experimenting with AI but lack a clear direction - Too many tools, not enough strategy—resulting in overwhelm and inefficiency - AI should be used as leverage, not decoration 2. The AIM Framework Overview - Accelerate — Ask: What’s slowing you down that AI can speed up? — Time-saving use cases: email follow-ups, brainstorm facilitation, web research, document summarization —  Pro Tip: Use AI not just to cut corners, but to build momentum - Integrate — Ask: Where does process friction slow down workflow and can AI resolve it? — Look for bottlenecks across marketing, sales, operations, and finance — Real-world scenarios: auto-updating sales decks, syncing spreadsheets, draft consistency, SOP standardization — Daily mantra: “Where is there friction, and can AI remove it?” - Multiply — Ask: What’s already working well, and how can AI do more of that? — Repurpose top-performing assets using tools like Distribution.ai — Perform customer insights, expand reach, clone high performers — AI is best when compounding what already brings value Resources & Tools: 🔗Distribution.ai 🔗HubSpot Breeze 🔗Rewind 🔗Midjourney 🔗ChatGPT 🔗Claude 🔗Perplexity — 👋🏾 Let's stay connected — ╰ Subscribe to my channel:  @RossSimmondsTV  ╰ Instagram:  @thecoolestcool   ╰ Twitter / X: @thecoolestcool   ╰ LinkedIn: linkedin.com/in/rosssimmonds

    19 min
  7. RSS 28: The Personal Brand Playbook: Leverage Your Expertise

    21/11/2025

    RSS 28: The Personal Brand Playbook: Leverage Your Expertise

    In this episode of The Ross Simmonds Show, Ross dives deep into why building a personal brand is no longer optional—especially in today’s creator-driven, AI-powered world. Ross shares a tactical blueprint for building a brand that doesn’t just look good but actually drives opportunity, revenue, and trust. He breaks down a step-by-step approach on how to show up online with integrity, authenticity, and strategic precision. Whether you're a founder, creator, marketer, or professional looking to gain an edge in your industry, this episode maps out how to start planting your flag and letting your content work for you. Key Takeaways and Insights: Why Personal Branding is Essential Today - Personal branding gives you leverage in a crowded digital world. - People buy from people—visibility leads to opportunity. - Even reality TV is being replaced by the transparency of creators. Platforms like Patreon, Passes.com, and others show this shift. Step 1: Pick Your Lane - Choose one expertise you want to be known for and commit to it for 12 months. - Don’t spread yourself thin across multiple niches. - Think in terms of outcomes for your dream client or audience. Step 2: Pick One Platform to Master - Focus on one channel before expanding. - LinkedIn: B2B professionals - X/Twitter: Tech and startup pros - YouTube: Universal, gold for all creators - Instagram & TikTok: Consumers, food, fashion, lifestyle - Reddit & Substack: Targeted niches and long-form content Step 3: Show, Don’t Just Tell - Credibility is proven through your work and success, not just your job title. - Document your wins, share client transformations, and post case studies. Step 4: Teach—Even If No One’s Watching - Share your lessons learned, POVs, book summaries, insights—even as a beginner. - “You only need to be one step ahead of someone to teach them.” - Consistency matters more than virality. Step 5: Distribute Everything Thoughtfully - Just creating isn’t enough—you need to circulate content.  - Convert content between platforms: — Repurpose tweets as LinkedIn posts –- Turn blog posts into carousels — Podcast clips into Reels/Shorts Step 6: Build Systems That Scale You - Personal brand works while you sleep when you have systems and assets: - Evergreen blog content - Auto-scheduled posts - Courses, guides, eBooks - Repurposing and re-sharing your best content Resources & Tools: 🔗 Distribution.ai  🔗 HubSpot — 👋🏾 Let's stay connected — ╰ Subscribe to my channel:  @RossSimmondsTV  ╰ Instagram:  @thecoolestcool   ╰ Twitter / X: @thecoolestcool   ╰ LinkedIn: linkedin.com/in/rosssimmonds

    23 min
  8. RSS 27: Reddit Is Eating the Bottom of the Funnel

    14/11/2025

    RSS 27: Reddit Is Eating the Bottom of the Funnel

    In this episode of The Ross Simmonds Show, Ross breaks down why B2B marketers need to rethink their bottom-of-funnel strategies. Traditional review sites like G2, Capterra, and TrustRadius are losing ground in high-intent search queries—and Reddit is stepping up to take their place. Ross explores how Reddit outperforms review platforms in organic reach, how it’s shaping AI results, and exactly how brands can build a strategic, valuable presence on the platform. If you’re still spending five figures a quarter on legacy review listings, this episode is your wake-up call to adapt or fall behind. Key Takeaways and Insights: 1.  The Changing Buyer Landscape - The death of traditional review sites: G2, Capterra, and others are losing organic influence. - Buyer behavior has evolved: Reddit is becoming the go-to source for real, unfiltered reviews. 2. Reddit Is Now Dominating High-Intent Search - Keywords like “best X software” are now leading to Reddit threads. - Reddit is outperforming review sites on SERPs and AI-generated insights. 3. How AI Tools Are Using Reddit for Context - LLMs like ChatGPT, Gemini, Claude, and Perplexity reference Reddit threads for information. - Partnerships with Reddit make it a key AI content source. 4. Why Reddit Comments Are More Trustworthy - Real debates and discussions offer depth that polished reviews lack. - Even negative experiences can influence AI answers and user perception. 5. The New B2B Buyer Journey - Traditional buyer path (→ G2 → demo) is being replaced by Reddit-informed decisions.Example: Users choose tools based on multi-comment threads and user anecdotes. 6. The 3-Step Strategy for Brands to Navigate Reddit - Create a Brand Subreddit (or claim existing ones via moderators). - Establish an Official Reddit Account (use Reddit Pro). - Build a Branded Persona who engages in other subreddits as a real user. 7. Tactical Tips for Reddit Marketing - Repurpose content: Post blog entries in the subreddit with keyword-rich, helpful commentary. - Host conversations: Ask customers for Reddit reviews.  - Build a safe space with consistent value. 8. Balancing Risk & Authenticity - Reddit is not just SEO; it's a community with a low tolerance for corporate spin. - A well-managed presence drives pipeline—but failure to engage authentically can backfire. Resources & Tools: 🔗Product-Led SEO by Eli Schwartz 🔗Reddit Pro — 👋🏾 Let's stay connected — ╰ Subscribe to my channel:  @RossSimmondsTV  ╰ Instagram:  @thecoolestcool   ╰ Twitter / X: @thecoolestcool   ╰ LinkedIn: linkedin.com/in/rosssimmonds

    12 min
See All (152)

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
    152
  • Rating
    Explicit
  • Copyright
    © Foundation Inc.
  • Show Website
    The Ross Simmonds Show

You Might Also Like