The Ross Simmonds Show

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/

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

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

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

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