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    Business

    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.

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    Copyright: © Foundation Inc.

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    Latest Episodes:
    RSS 32: Your Company Culture Is a Reflection of Your Worst Habits Dec 20, 2025
    Show notes

    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


    RSS 31: You Don’t Deserve a High‑Performing Team If You’re Not a High‑Performing Leader Dec 12, 2025
    Show notes

    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


    RSS 30: Generative Engine Optimization (GEO): Why I'm All In Dec 05, 2025
    Show notes

    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


    RSS 29: How to Use AI With Intention, Not Just Curiosity Nov 28, 2025
    Show notes

    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


    RSS 28: The Personal Brand Playbook: Leverage Your Expertise Nov 21, 2025
    Show notes

    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


    RSS 27: Reddit Is Eating the Bottom of the Funnel Nov 14, 2025
    Show notes

    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


    RSS 26: Exploring Reddit Marketing, Digital Entrepreneurship & AI Distribution Nov 07, 2025
    Show notes

    In this episode of The Ross Simmonds Show, Caleb Turner interviews Ross and they dive deep into the mindset and strategies behind building a personal brand, marketing via Reddit, leveraging AI for content distribution, and tactically navigating the future of search in an AI-driven world. Whether you're an emerging entrepreneur or a seasoned marketer, this episode offers insights for anyone looking to grow their influence and impact in today’s digital landscape.


    Key Takeaways and Insights:


    1. Entrepreneurship vs. Employment

    - Difference between entrepreneurs, business owners, and 9-to-5 employees.

    - Importance of desiring time and life control.

    - Business as art and expression: why entrepreneurship enables creative freedom.


    2. Starting Your Digital Marketing Business

    - Set up a personal website (FirstnameLastname.com).

    - Invest in brand identity: logo, photos, LinkedIn optimization.

    - Create value-aligned content: video, writing, podcasting, etc.

    - Embrace “the courage to be disliked."


    3. The Role of Mentorship in Success

    - Early mentorship from local entrepreneurs and learning the ropes through reading.

    - The power of “mentorship at scale” via online creators and writers.

    - Ross now stands shoulder-to-shoulder with his digital mentors.


    4. Reddit Marketing: A Tactical Overview

    - Reddit is now influencing AI search results and is more trusted than traditional blogs.

    - 3 Entry Strategies for Reddit Marketing:

    — Social Listening – Understand what subreddits you're already part of.

    — Value Posting – Build karma by helping others before promoting.

    — Reddit Ads – Use remarketing to re-engage users.


    5. How to ensure your brand is visible in AI search results

    - Contribute to high-authority domains.

    - Create YouTube content, answer questions on Reddit, and be cited in forums and newsletters.

    - Comprehensive digital presence is key—not just your own website.


    Resources & Tools:

    🔗 Ross Simmonds x Caleb Turner

    🔗 Distribution.ai

    🔗 Reddit Pro

    🔗 Create Once, Distribute Forever


    — 👋🏾 Let's stay connected —

    ╰ Subscribe to my channel: @RossSimmondsTV

    ╰ Instagram: @thecoolestcool

    ╰ Twitter / X: @thecoolestcool

    ╰ LinkedIn: linkedin.com/in/rosssimmonds


    — Connect with Caleb Turner —

    ╰ Subscribe to my channel: @growyourbizwithcaleb

    ╰ LinkedIn: linkedin.com/in/calebcturner/


    RSS 25: AI's Impact on Marketing, SEO, and B2B Growth Nov 01, 2025
    Show notes

    In this episode of The Ross Simmonds Show, Ross was invited by Craig Hewitt of Rogue Startups Podcast to explore how AI is transforming B2B marketing, sales operations, and digital strategy. They cover the decline of traditional SEO, the rise of Reddit as a powerful discovery platform, the evolving importance of LinkedIn and YouTube, and practical advice on AI tools, personalization, and productivity. This is a must-listen for marketers, SaaS founders, and anyone looking to future-proof their growth strategies in an AI-driven world.


    Key Takeaways and Insights:


    1. What’s working now?” in B2B and SaaS marketing

    - Personal brand content from team members on social media.

    - Micro-influencers and content creators paid on performance for lead-generating videos.


    2. Create “ridiculously valuable” and original content

    - insightful data or perspectives that AI can’t replicate.

    - AI makes distribution and repurposing easier, but not idea generation or storytelling.

    - Personalization tools like Loom or LinkedIn voice messages still work well, but are hard to scale.


    3. Content Repurposing & Platform Strategy

    - Repurposing content—doing it well beyond basic automation tools.

    - LinkedIn → best for B2B buyers and thought leadership.

    - Twitter/X → still relevant for technical audiences and startup visibility.

    - Instagram → underutilized channel with potential.

    - YouTube → huge upside for discoverability + long-form value, but tough to execute well.


    4. SEO in Decline?

    - AI has definitely reduced Google traffic—marketers must embrace multi-channel discovery. - YouTube, Instagram, Reddit, and social as the new search engines.


    5. Bonus Frameworks:

    - “Ross’s Hierarchy of Needs”: Revenue > Traffic > Channels.

    - “Distribution Framework”: Audience Attention vs Competitive Saturation = Channel Opportunity. Underhyped vs Overhyped AI Trends

    - Underhyped: Reddit - Massive influence in buyer decisions. - Google indexing Reddit heavily due to user trust.

    - Overhyped: Quora - Once valuable, now polluted and ineffective.


    Resources & Tools:

    🔗 The Reddit Marketing Code

    🔗 Distribution.ai

    🔗 Loom

    🔗 Trigify

    🔗 Clay


    — 👋🏾 Let's stay connected —

    ╰ Subscribe to my channel: @RossSimmondsTV

    ╰ Instagram: @thecoolestcool

    ╰ Twitter / X: @thecoolestcool

    ╰ LinkedIn: linkedin.com/in/rosssimmonds


    — 👋🏾 Follow Craig —

    ╰ Subscribe to Rogue Startups: roguestartups.com/subscribe

    ╰ Twitter / X: @TheCraigHewitt

    ╰ LinkedIn: linkedin.com/in/craig-hewitt-78386a66/


    RSS 24: Press Publish, Even When You’re Not Ready Oct 24, 2025
    Show notes

    In this episode of The Ross Simmonds Show, Ross dives into a hard truth that many creators, entrepreneurs, and aspiring founders need to hear: no one is thinking about you as much as you think—and that’s a good thing. Ross explores the concept of the “ego trap,” the fear of judgment, and the self-doubt that prevents people from pressing publish on the very ideas that could change their lives. With heartfelt personal stories and actionable advice, this episode is a rallying cry for creators to take messy action, press publish, and embrace the power of momentum.


    Whether you're just starting or you've been holding back on launching something important, this episode will give you the encouragement—and the permission—you need to start sharing your work with the world.


    Key Takeaways and Insights:

    1. The Ego Trap

    - You're not holding back because of lack of skills—you’re trapped by your own ego.

    - The fear of judgment is a mental trap, not a real obstacle.


    2. Why “No One Is Watching” Is Good News

    - In the beginning, being invisible is a superpower.

    - Use this phase to test ideas, experiment, and find your voice without scrutiny.


    3. The Value of Imperfect Action

    - Pressing publish—even on a rough draft—lets you start the feedback and improvement cycle.

    - Perfectionism kills progress.


    4. Focus on Creation, Not Criticism

    - People who criticize from the sidelines are rarely building anything.

    - Judgment is easy, execution is rare—be a creator, not just a consumer.

    - Don’t wait until it’s perfect. Take the risk. Hit publish. Launch the thing.

    - You won’t be remembered for what you almost did—only for what you actually shipped.


    Resources & Tools:

    🔗 Foundation Marketing

    🔗 Distribution.ai


    — 👋🏾 Let's stay connected —

    ╰ Subscribe to my channel: @RossSimmondsTV

    ╰ Instagram: @thecoolestcool

    ╰ Twitter / X: @thecoolestcool

    ╰ LinkedIn: linkedin.com/in/rosssimmonds


    RSS 23: 10 Real Ways to Get Ahead of Most People Oct 17, 2025
    Show notes

    In this episode of The Ross Simmonds Show, Ross shares ten powerful, no-fluff strategies to separate yourself from the crowd. If you’re tired of being stuck in a cycle of dreaming and talking about success without making any progress, this episode is for you.

    Ross dives deep into the habits, mindsets, and decisions that differentiate top performers from the majority. With personal stories, actionable insights, and a challenge to get moving, this episode is all about taking control, creating leverage in your life, and staying disciplined to win.


    Key Takeaways and Insights:

    1. Take Action Before You’re Ready

    - Waiting for perfect conditions leads to inaction.

    - “Feelings don’t matter. The universe doesn't care about your feelings.”

    - Start messy, learn by doing.


    2. Make Discipline Your Default

    - Motivation is fleeting, but consistency builds long-term success.

    - “Success isn’t about doing what you feel like doing... it’s doing what you have to do.”


    3. Build in Public

    - Share your goals and progress openly to build momentum and hold yourself accountable.

    - Letting people see your journey helps them invest in you—not just the outcome.


    4. Become Obsessively Useful

    - Be someone others want to work with by being helpful and solution-oriented.

    - Ask: “How can I help you?” → Builds long-lasting, valuable networks.


    5. Read More Than You Scroll

    - Social media is filled with “empty calories.”

    - Trade entertainment for intentional growth—30 pages of a book > 30 minutes of scrolling.

    - Consider books, reports, and content that challenges your thinking.


    6. Say No More Often

    - “Distraction is a dream killer.”

    - Saying no protects your energy and time for what truly matters.

    - Be selective with your commitments.


    7. Understand the Value of Leverage

    - Outsourcing non-core tasks is not a luxury—it’s a smart use of time.

    - Example: Paying for laundry outsourced an hour of work and improved productivity.

    - Build systems that run without you.


    8. Practice & Improve Writing

    - Strong communication skills (especially written) amplify your impact.

    - Set writing goals. Accept feedback. Keep refining.

    - Key for storytelling, leadership, and persuasion.


    9. Enter Strategic Rooms

    - Seek out environments that challenge you and your thinking.

    - Surround yourself with people ahead of you to learn and be inspired.


    10. Execute Faster Than You Overthink

    - Analysis paralysis kills dreams.

    - Planning alone doesn’t win—execution does.

    - Speed separates idea generators from winners.


    — 👋🏾 Let's stay connected —

    ╰ Subscribe to my channel: @RossSimmondsTV

    ╰ Instagram: @thecoolestcool

    ╰ Twitter / X: @thecoolestcool

    ╰ LinkedIn: linkedin.com/in/rosssimmonds


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