The Ross Simmonds Show

Ross Simmonds
  • 5.0 (1)
  • 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. 5 HR AGO

    RSS 41: Reddit Is the New Front Page of B2B: Listen, Learn, Then Leap

    Key Takeaways and Insights: The New B2B Buyer Journey -Buyers seek personalized answers in Slack groups, Discord, WhatsApp, Reddit, and LLMs. -LLMs frequently leverage Reddit to inform their responses. -Influence now happens in communities—not just on your website. -If you’re not present where conversations happen, you’re invisible at decision time. Reddit’s Influence on LLMs & AI Search -Platforms like ChatGPT, Perplexity, Claude, and Gemini pull insights from Reddit. -Reddit Answers (Reddit’s native AI tool) is growing rapidly. -Showing up on Reddit increases your likelihood of influencing AI-generated responses. -Reddit is now an upstream distribution channel for AI visibility. The Three Buckets of Modern Organic Growth -Onsite optimization: technical SEO, structure, and speed. -Offsite influence: reviews, mentions, and third-party validation. -Word-of-mouth engines: content and product experiences that spark conversation. -Sustainable growth requires alignment across all three. SEO Fundamentals Still Win -Clean site architecture and clear navigation matter. -Optimize for real search queries—not internal jargon. -Remove redundant branding from meta titles. -Prioritize site speed, mobile-first performance, and backlinks. Offsite Optimization Beyond Backlinks -Be included in “best tools” lists and review content. -Win in comparison threads and niche discussions on Reddit. -Influence buying decisions where prospects evaluate options. -Visibility off your domain often matters more than traffic to it. Word of Mouth as a Growth Flywheel -Word of mouth was ranked the #1 buying factor in a Winter study. -Engineer moments that inspire customers to talk. -Reviews, tweets, blog posts, and Reddit threads compound over time. -Build systems that generate advocacy—don’t leave it to chance. Listen, Learn, Leap: The Reddit Framework -Listen: Audit what customers are saying about you. -Learn: Identify content trends and cultural norms in subreddits. -Leap: Create native content that aligns with community expectations. -Treat Reddit as a long-term investment, not a campaign channel. Finding Content-Market Fit on Reddit -Sort subreddit posts by “Top” to uncover engagement patterns. -Reverse engineer themes that drive upvotes and comments. -Look for repeated formats: transparent case studies, financial breakdowns, how-tos. -Validate resonance before scaling your posting cadence. Niche Down to Win -Large subreddits are competitive—start in focused communities. -Every B2B niche likely has an active subreddit. -Example: Reverse engineering content for r/MSPs led to strong traction. -Precision beats volume in early-stage Reddit growth. Create for Reddit Culture -Blend educational, engaging, entertaining, and empowering content. -Publish consistently once you understand audience expectations. -Repetition works—humans gravitate toward familiar story structures. -If you’ve truly listened, your audience won’t fatigue. Resources & Tools: 🔗 Reddit.com 🔗 ⁠⁠R/smallbusiness 🔗⁠ R/entrepreneur 🔗⁠ Claude — 👋🏾 Let's stay connected — ╰ Subscribe to my channel:  @RossSimmondsTV  ╰ Instagram:  @thecoolestcool   ╰ Twitter / X: @thecoolestcool   ╰ LinkedIn: linkedin.com/in/rosssimmonds

    16 min
  2. RSS 40: The Enterprise AI Stack Blueprint: How to Build It Right (Without Wasting Millions)

    6 DAYS AGO

    RSS 40: The Enterprise AI Stack Blueprint: How to Build It Right (Without Wasting Millions)

    Every enterprise is building an AI stack, but most are doing it wrong. In this episode, Ross breaks down a tactical, use-case-driven framework for building an AI stack that actually works. If you’re a marketer, operator, or executive looking to leverage AI strategically (without blowing your budget or ignoring compliance), this episode gives you the structure you need to win. Key Takeaways and Insights: 1. The Hard Truth About Enterprise AI - Most companies choose AI tools based on hype, not strategy. - Vendor pitches and social buzz are driving long-term contracts. - Locking into the wrong platform can create scaling and security nightmares. - The AI landscape changes weekly, three-year commitments require serious thought. 2. There Is No “Best” AI Tool - The right question isn’t “What’s best?” but “What’s best for this use case?” - Different teams (marketing, engineering, finance) need different tools. - Constraints, industry, and goals should guide tool selection. - Build a stack…Don’t look for a silver bullet. 3.  The 5-Layer AI Stack Framework - Layer 1: Writing & Communication Tools - Layer 2: Research & Analysis - Layer 3: Code & Technical Execution - Layer 4: Automations & Workflow Integration - Layer 5: Security & Compliance 4. Training, Ownership & Continuous Improvement - AI adoption fails without real, ongoing training. - Appoint an AI stack owner responsible for optimization and updates. - Create internal systems (e.g., Slack channels) to share prompts and workflows. - Capture institutional knowledge so it doesn’t leave with one employee. 5. Start Small, But Start Strategic - Don’t wait for “the perfect moment.” AI is already reshaping competition. - Experiment but build security and compliance from day one. - Budget realistically for training, tools, and maintenance. - Strategic AI adoption is a long-term competitive advantage. Resources & Tools: 🔗 Distribution.ai 🔗 Superhuman 🔗 Claude 🔗 Gemini 🔗 Clay — 👋🏾 Let's stay connected — ╰ Subscribe to my channel:  @RossSimmondsTV  ╰ Instagram:  @thecoolestcool   ╰ Twitter / X: @thecoolestcool   ╰ LinkedIn: linkedin.com/in/rosssimmonds

    20 min
  3. RSS 39: From Founder to CEO: Stop Doing More and Start Leading

    6 FEB

    RSS 39: From Founder to CEO: Stop Doing More and Start Leading

    In this episode of The Ross Simmonds Show, Ross talks about the skills that create early traction don’t scale; growth requires letting go, delegating, and evolving into a CEO. Scaling isn’t just about revenue or headcount, it’s about scaling yourself. That means building trust, hiring people better than you in their domains, creating systems, rituals, and documentation, and replacing instinct with infrastructure. Founders must stop being the bottleneck, accept work done at 80%, and focus their time on strategy, hiring, and long-term direction. Great leaders build leaders, not dependency. Trust is built through clarity, not micromanagement. As companies grow, founders must repeatedly evolve, face discomfort, make hard decisions quickly, and shed the “hustler” identity. You don’t scale by doing more, you scale by becoming a leader who empowers others to do more. Key Takeaways and Insights: From Founder Hustle to CEO Leadership - Why the skills that got you started won’t scale your business - The critical mindset shift from “doing everything” to leading through others - How chaos management evolves as your company grows Scaling Isn’t Just About Revenue. It’s About You.  - Why personal growth is the real bottleneck in scaling - Letting go of control to unlock the next phase of growth - Becoming a multiplier instead of a bottleneck The 3 Core Levers of Scaling: Trust, Team, and Time - A simple framework to guide CEO-level decision-making - How these levers reduce stress and improve performance How to Build Trust Without Micromanaging - Why clarity beats control every time - Setting boundaries, defining success, and giving real autonomy - Eliminating founder anxiety through better communication Hiring People Smarter Than You (And Why It Matters) - Embracing discomfort as a sign of leadership maturity - Spotting talent that raises the standard across the company Protecting Your Time as a High-Leverage Asset - Where your time creates the most long-term impact - Shifting from tactical reviews to strategic thinking Evolving Through Every Stage of Growth - Why each revenue milestone requires a new version of you - Navigating the discomfort of leadership evolution - Letting go of the “hustler” identity to scale sustainably — 👋🏾 Let's stay connected — ╰ Subscribe to my channel:  @RossSimmondsTV  ╰ Instagram:  @thecoolestcool   ╰ Twitter / X: @thecoolestcool   ╰ LinkedIn: linkedin.com/in/rosssimmonds

    19 min
  4. RSS 38: The Stockdale Paradox: How Founders Survive Without Toxic Optimism

    30 JAN

    RSS 38: The Stockdale Paradox: How Founders Survive Without Toxic Optimism

    In this episode of The Ross Simmonds Show, Ross explains why blind optimism can be one of the most dangerous traits for a founder. He introduces the Stockdale Paradox, the idea that great leaders balance unwavering belief in long-term success with full acceptance of the brutal facts in front of them. Ross shares how toxic positivity can cause founders to ignore churn, burn, and hard realities until it’s too late, while pessimism can drain teams of hope. The winners, he argues, are the ones who stay honest about where they are while still holding strong conviction that they will figure it out. This episode is a reminder that two things can be true at once: things are hard, and you can still win. Key Takeaways and Insights: 1. The Hidden Danger of Blind Optimism - Why “always stay positive” can quietly derail founders and leaders - How blind optimism kills more startups than bad markets - The difference between hope and denial 2. The Stockdale Paradox Explained - The mindset that helped Admiral James Stockdale survive seven years as a POW - Why unwavering faith and brutal honesty must coexist - How this paradox applies directly to startups and leadership 3. Toxic Optimism in Founders & Teams - Common signs of toxic optimism in startups - How ignoring churn, burn, and market shifts destroys trust - Why false confidence shortens your runway 4. The Other Extreme: Doomsday Leadership - What happens when founders lose belief in the future - How fear-driven decisions stall growth and innovation - Why teams disengage when leaders lack conviction 5. Holding Two Truths at the Same Time - How winning leaders balance realism with belief - Practical examples of confronting bad metrics while staying confident - Why this duality fuels resilience and momentum 6. Communicating Hard Truths Without Killing Morale - How great leaders share bad news transparently - Why honesty builds trust more than spin - Framing reality while reinforcing belief in the team — 👋🏾 Let's stay connected — ╰ Subscribe to my channel:  @RossSimmondsTV  ╰ Instagram:  @thecoolestcool   ╰ Twitter / X: @thecoolestcool   ╰ LinkedIn: linkedin.com/in/rosssimmonds

    14 min
  5. RSS 37: Unlocking the Power of Partnership Marketing with Clinton Senkow

    24 JAN

    RSS 37: Unlocking the Power of Partnership Marketing with Clinton Senkow

    In this episode of The Ross Simmonds Show, Ross sits down with long-time friend Clinton Senkow, a leading expert in partnership marketing. They explore the core principles of building successful partnerships, why most companies underutilize this growth tactic, and how AI is transforming the partnership landscape. Clinton shares actionable advice for startups and established companies looking to harness partnerships to accelerate growth. Clinton also introduces us to his new AI-powered platform, Partnerss.co, designed to help businesses find ideal partners in minutes, not months. Key Takeaways and Insights: 1. What is Partnership Marketing? - Leveraging another company’s audience, platform, or user base to promote your product or service - Forms of partnerships include co-marketing, co-selling, affiliate programs, and tech integrations - True partnership success comes from win-win collaborations 2. The Growth Opportunity - Partnerships can provide exponential growth versus single-channel approaches like sales or ads - Ideal for companies with product-market fit looking to scale efficiently - Helps unlock brand trust fast through warm introductions. 3. Tech Meets Strategy: AI + Partnerships - Clinton introduces Partnerss.co, his AI-powered discovery platform - Uses synergy scores and business intelligence to match companies with ideal partners - Built for speed, identifies & evaluates high-fit partner opportunities in minutes 4. When Should You Start Thinking About Partnerships? - When your company has product-market fit and understands its ideal customer - Partnerships are effective post-traction not necessarily dependent on team size 5. Realistic Partnership KPIs - Focus on conversations and strategic alignment—not just volume - Metrics include # of active partnerships, partner-influenced revenue, retention, and co-marketing reach 6. Framework to Identify Ideal Partners - Ask: “What is my customer doing before and after they use my product?” - Explore complements (not competitors) servicing the same ICP - Analyze potential for mutual value creation & platform integrations 7. Roles & Responsibilities in Partnerships - Affiliate, integration, co-sell, and co-marketing roles often require specialized skill sets - In earlier-stage companies, one partnerships lead may wear multiple hats - Successful partnerships professionals are strong networkers, communicators, and relationship builders Resources & Tools: 🔗 Partnerss.co 🔗 PartnerStack 🔗 Partnerize  — 👋🏾 Let's stay connected — ╰ Subscribe to my channel:  @RossSimmondsTV  ╰ Instagram:  @thecoolestcool   ╰ Twitter / X: @thecoolestcool   ╰ LinkedIn: linkedin.com/in/rosssimmonds — Connect with Clinton  — ╰ Instagram: @clintonsenkow ╰ Twitter / X: @ClintonSenkow ╰ LinkedIn: linkedin.com/in/clintonsenkow/

    55 min
  6. RSS 36: How to 10X Your Output with Claude or ChatGPT

    16 JAN

    RSS 36: How to 10X Your Output with Claude or ChatGPT

    In this episode of The Ross Simmonds Show, Ross dives deep into the ways AI is reshaping how entrepreneurs, marketers, and content creators work and how you can use tools like Claude, ChatGPT, and Distribution.AI to get an edge instead of being left behind. Ross shares strategic frameworks, prompting techniques, and real-life use cases that show how AI isn't here to replace you, it's here to elevate what you do best. This episode is a masterclass in using generative AI as your co-pilot for ideation, execution, and growth. Key Takeaways and Insights: 1. AI is Not a Threat - High-performing marketers treat AI as a strategic partner, not a shortcut or replacement. - The real differentiator is how you work with AI—systems, iteration, and judgment matter more than tools. - Winners focus on long-term leverage, not short-term panic. 2. Why Claude Stands Out for Marketers- Claude consistently delivers stronger brand-aligned writing for positioning, messaging, and copy. - Less “robotic” output makes it useful for customer-facing content. - Tool choice matters less than mindset 3. Repurposing Content at Scale - AI can extract quotes, threads, newsletters, and posts from long-form content. - Tools like Distribution.ai automate cross-channel repurposing and scheduling. - Claude remains a strong budget-friendly alternative for manual workflows. 4. The Four-Phase AI Workflow: Discover → Framework → Build → Polish - Break complex projects into structured phases instead of one-shot prompts. - Improves quality, alignment, and creative control. - Applicable to blogs, ebooks, GTM plans, and proposals. 5. AI Amplifies Strategy, It Doesn’t Replace It - AI handles speed and execution; humans provide judgment, taste, and insight. Marketers who avoid AI risk falling behind peers who use it strategically. Resources & Tools: 🔗Distribution.ai 🔗Claude 🔗ChatGPT — 👋🏾 Let's stay connected — ╰ Subscribe to my channel:  @RossSimmondsTV  ╰ Instagram:  @thecoolestcool   ╰ Twitter / X: @thecoolestcool   ╰ LinkedIn: linkedin.com/in/rosssimmonds

    25 min
  7. RSS 35: The Power of Saying No: Focus to Scale

    9 JAN

    RSS 35: The Power of Saying No: Focus to Scale

    In this episode of The Ross Simmonds Show, Ross dives deep into the underrated strength behind the word “no.” He unpacks why saying yes too often can lead to dilution of focus, scattered priorities, and slower growth—both for individuals and companies. Drawing from personal experiences building Foundation Marketing and working with world-class SaaS brands, Ross lays out how intentional decision-making drives scalable results. He shares a practical framework for evaluating opportunities, a unique way of using AI to filter distractions, and actionable tips for saying “no” without burning bridges.  Key Takeaways and Insights: 1. Saying yes to everything pulls you away from what matters - Every yes is also a no to something else: focus, deep work, or rest. - The more scattered your “yes” is, the harder it becomes to scale. 2. Focus beats doing more - The most successful companies don’t win by doing more — they win by doing less with intention. - Real growth comes from allocating time to the highest-value work. 3. Clarity makes saying no easier - Filter decisions with three questions: Is this aligned with my priorities right now? Does this scale or compound? Would I still do this if no one ever knew about it? - If it doesn’t help hit current goals, the answer is no. 4. Not every opportunity is worth your time - A full calendar doesn’t mean progress — it can mean distraction. - One-off wins that don’t compound cost more than they give back. 5. You can say no without burning bridges - Thank people for the opportunity and be clear about your priorities. - Saying no isn’t selfish — it’s being intentional and protecting what matters. Resources & Tools: 🔗 Vivid Vision Concept (by Cameron Herold) — 👋🏾 Let's stay connected — ╰ Subscribe to my channel:  @RossSimmondsTV  ╰ Instagram:  @thecoolestcool   ╰ Twitter / X: @thecoolestcool   ╰ LinkedIn: linkedin.com/in/rosssimmonds

    13 min
  8. RSS 34: Winning with Intention in the Age of AI with Will Reynolds

    3 JAN

    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
See All (159)

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
    159
  • Rating
    Explicit
  • Copyright
    © Foundation Inc.
  • Show Website
    The Ross Simmonds Show

You Might Also Like