Podcast
The Ross Simmonds Show
Hosted by Ross Simmonds · EN
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.
44episodes
Episodes
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RSS 35: The Power of Saying No: Focus to Scale
Jan 900:12:41Tap to summarizeIn 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
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RSS 34: Winning with Intention in the Age of AI with Will Reynolds
Jan 301:18:31Tap to summarizeIn 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/
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Building Brands, Building Balance: Brayden Young on Disrupting B2B with Real Conversations
Aug 15, 202500:52:13Tap to summarizeIn this episode of The Ross Simmonds Show, Ross sits down with Brayden Young, co-founder & CEO of Slash Experts and original co-founder of Sendoso, to break down what it takes to cut through the noise in B2B sales and marketing. Brayden reflects on his entrepreneurial journey, the evolution of go-to-market strategies for 2025 and beyond, and how AI is reshaping the landscape for marketers, founders, and sales teams. They dive into personal philosophies, balancing family with drive, using strategic gifting as a growth lever, and how connecting customers with prospects is transforming the sales cycle. If you're in the trenches of building or scaling a company, this episode is packed with invaluable lessons. Key Takeaways and Insights: 1. Human conversations > traditional sales decks: Connecting real customers with prospects accelerates trust and conversions. 2. Strategic gifting is about thoughtful timing, not splashy spend. Think: handwritten notes, trigger-based outreach, and lifecycle communications. 3. Reviews are great, but community-driven insights and live interactions are the future of software buying. 4. AI is shifting go-to-market: fewer people, more productivity. Understanding how to use AI is now table stakes. 5. Success is relative: It’s not just revenue — it’s freedom, fulfillment, and building something that lasts 6. Brayden’s Personal Frameworks “Don’t build in a silo” — Always validate with customers before building product. “Three People Rule” — The only people he calls for big advice: wife, mom, co-founder. “Suck It Up or Go for a Walk” — His motivational speeches with his wife. First-time employee comp tip: Pick a high milestone and negotiate for equity or secondaries if you hit it. Resources & Tools: 🔗 Slash Experts 🔗 Sendoso 🔗 ClickUp 🔗 Punch Financial 🔗 Quickbooks 🔗 Get Parallel — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds — 👋🏾 Connect with Braydan Young — ╰ LinkedIn: linkedin.com/in/braydanyoung/
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ChatGPT 5 Just Changed the Game -- NOT A NORMAL EPISODE
Aug 8, 202500:09:13Tap to summarizeIn this episode of The Ross Simmonds Show, Ross dives into the powerful implications of OpenAI's newly released ChatGPT-5. Far beyond a minor update, this version represents a paradigm shift in AI capabilities, from extended context retention to creating fully functional applications with a single prompt. The discussion centers around the disruptive impact of GPT-5 on knowledge work, the rising bar for professional performance, and how leveraging AI tools is becoming the new baseline for productivity and innovation. The host also shares insights into deploying AI tools within organizations and offers practical advice on how to prepare for a rapidly changing future. Key Takeaways and Insights: 1. What ChatGPT-5 Can Do - GPT-5 is not just faster or smarter—it fundamentally transforms human-AI collaboration. - Capable of complex reasoning, task execution, and creating entire games from a single input prompt. - Designed for more advanced applications, such as coding, diagnosing, designing, and more. 2. Real-World Use Cases & Case Studies - Designers creating brand kits in seconds. - Founders launch entire landing pages with GPT-5. - Students using it for interview prep. - Customer service automation through LLMs. - Developers use it for QA and debugging. 3. The New Productivity Baseline - Mediocrity is no longer sustainable in a world where AI delivers solid output instantly. - Professionals Chatmust either augment with AI or risk becoming obsolete. - Being an early adopter leads to significant competitive advantage. 4. AI Adoption Is No Longer Optional - Skipping AI in 2025 likened to ignoring the internet in 2005. - Skeptics are compared to beachgoers dismissing a tsunami as a "big wave." - AI is poised to transform white-collar work more dramatically than social media or mobile tech. Resources & Tools: 🔗ChatGPT 🔗Distribution.ai 🔗Fathom — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds
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The Myth of Passive Income
Aug 1, 202500:23:03Tap to summarizeIn this episode of The Ross Simmonds Show, Ross dives deep into the truth about passive income and reveals the five proven strategies that actually work. From selling digital products to affiliate monetization and licensing your intellectual property, Ross breaks down what separates profitable systems from scammy shortcuts. Whether you're a creator, entrepreneur, or looking for side-hustle inspiration, this is your blueprint to sustainable online income, powered by intention, strategy, and distribution, not luck. Key Takeaways and Insights: 1. What Actually Works: 5 Real Paths to Online Income - Digital Products - Affiliate Monetization with Evergreen Content - SaaS Products & Memberships - Content Licensing - Investing in Income-Producing Assets 2. The Path Forward: How To Start Building Your Streams - Solve a real problem - big or small - Build a distribution system (landing pages, email, social automation) - Start with a tiny minimum viable product (MVP) - Validate with real buyers and feedback 3. Distribution Is Everything - Don’t build in silence - Promote your work relentlessly on platforms like X (Twitter), LinkedIn Resources & Tools: 🔗 Gumroad 🔗 Podia 🔗 Kajabi 🔗 Etsy 🔗 Shopify Templates 🔗 HubSpot 🔗 Distribution.ai — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds
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Be the First to Reach Out: How It Changed EVERYTHING For Me
Jul 26, 202500:30:26Tap to summarizeIn this episode of The Ross Simmonds Show, Ross shares one deceptively simple yet life-changing principle: be the first to reach out. Whether you’re leading a team, navigating a personal relationship, seeking mentorship, building partnerships, or managing conflict, Ross demonstrates how initiating connection and communication can accelerate trust, progress, and performance. Packed with real-life examples and actionable strategies, Ross discusses how taking the first step to connect helps address miscommunication, foster alignment, and strengthen relationships that are essential for both life and business success. Key Takeaways and Insights: 1. Why Being First to Reach Out Changes Everything - The small act of going first can build trust, momentum, and connection. - Many people wait due to fear, assumption, or the hope that someone else will act. - Those who lead with action never wait for permission or perfect timing. 2. The Power of Action-Oriented Leadership - Solid leaders act. They see a problem and address it rather than avoid it. - Reach out for and give feedback proactively. It's contagious and builds a culture of communication. 3. Practical Applications - Micro Check-Ins (Positive or Challenging Situations) - Conflict Resolution: Reach First, React Less - Mentorship Starts With Initiative - Strategic Outreach for Partnerships - Internal Communication as Leadership 4. Cultural Leadership Lessons - Grandmother's Legacy: Consistent Outreach - Creating a Culture of Trust and Problem Solving - Build a High-Performance, Low-Ego Team — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds
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How to Get Your Content Seen by the Right People
Jul 20, 202501:09:45Tap to summarizeIn this episode of The Ross Simmonds Show, Ross breaks down the keys to building an influential brand through content creation, distribution, and experimentation. This conversation covers everything from overcoming imposter syndrome and mastering content distribution to riding the AI wave and scaling your creative vision. Whether you're a content creator, small business owner, or digital marketer, this conversation delivers no-fluff, highly actionable strategies to amplify your reach and scale with focus. Key Takeaways and Insights: 1. Content is King, but Distribution is the Empire- Creating great content is only the beginning; distribution is where the magic happens. - Most content fails not because it’s bad, but because nobody sees it. - Creators must go beyond publishing: share content in forums, repurpose assets, email it, and push it across platforms. 2. Build Your Brand by Being Relentlessly Valuable - Early wins come from proving value to just one or two clients and letting word of mouth do the rest. - Niche down, provide specific, hyper-relevant advice, and soon you'll be the go-to expert for that audience. - “Give value to the internet and the internet will give it back” is Ross's philosophy in a nutshell. 3 Experimentation is a Growth Engine- Ross’s mantra: Build, Ship, Learn, Decide. - Every breakthrough he’s had, from fantasy football blogs to SaaS products, started with small experiments. - As your business grows, so should the size (and risk) of your experiments. 4. Imposter Syndrome Will Kill Your Momentum - You don’t need to be the best to start; you just need to be better than your clients at the thing you're offering. - Most people fail because they talk themselves out of even trying. - Ross urges creators to let go of self-doubt and lean into bold action. 5. AI is a Game Changer, Use it or Fall Behind - Ross actively uses tools like ChatGPT, ElevenLabs, and Descript to speed up workflows, enhance creativity, and save time. - While AI brings ethical challenges (like deepfakes), its potential for creators is enormous, from scriptwriting to content remixing. - Strategic use of AI will become a competitive advantage in the coming years. Resources & Tools: 🔗 Foundation Marketing 🔗 Distribution.ai 🔗 Ross' Book: Create Once, Distribute Forever 🔗ElevenLabs 🔗 Descript — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds
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How Marketers Can Thrive During Budget Cuts & Downturns
Jul 12, 202500:16:01Tap to summarizeIn this episode of The Ross Simmonds Show, Ross tackles a crucial and timely topic: how marketers can not only survive but thrive during economic downturns. When budgets are slashed and expectations remain sky-high, too many marketers retreat. But as Ross argues, downturns are hidden opportunities for bold, creative, and strategic professionals. You’ll learn why your mindset matters, which marketing mistakes to avoid in a crisis, and most importantly, what you can do right now with limited resources to build brand equity, generate demand, and outmaneuver your competition. Key Takeaways and Insights: 1. Mindset Wins the Long Game - The best marketers stay calm and ruthlessly prioritize value. - Budget constraints can clarify what really drives results. - Insight: Constraints don’t kill creativity—they sharpen it. 2. The Three Biggest Mistakes Marketers Make in a Downturn - ❌ Cutting brand investment entirely. - ❌ Over-investing in high-cost, low-yield paid channels. - ❌ Playing it safe and copying competitors. 3. Proven Tactics for Marketing with Zero Budget - Repurpose your top-performing historical content. - Example reuse: LinkedIn carousels, Reddit posts, YouTube Shorts. 4. Earn Trust When Paid Clicks Are Too Expensive - Invest in podcast appearances, guest posts, and owned content. - Use first-party proprietary or curated data to support thought leadership. 5. Double Down on Your Current Customers - Strengthen relationships via community, VIP content, and proactive help. - Empower your customers to become brand advocates. - Insight: Word of mouth cannot be budget-cut. 6. Embrace Evergreen Content - Create assets that compound over time vs. quick hits. - Focus on material that drives long-term ROI. 7. Collaborate for Free Distribution - Build co-branded content and share audiences with aligned partners. - Example: Ross shares a story about early Snapchat takeovers (“Snap Swaps”). Resources & Tools: 🔗 Distribution.ai 🔗 Foundation Marketing 🔗 HubSpot — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds
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How To Get More Leverage & Do More With Less
Jul 5, 202500:22:27Tap to summarizeIn this episode of The Ross Simmonds Show, Ross breaks down the powerful concept of leverage, the secret behind how high-performers achieve 10x results without working 10x harder. Ross introduces the four core types of leverage (People, Capital, Code, and Content) and provides actionable insights, mindset shifts, and examples on how to use them to reclaim your time, scale your impact, and accelerate growth. Whether you're an entrepreneur, creator, marketer, or employer, this episode offers a practical framework to help you work smarter and more effectively. Key Takeaways and Insights: 1. Leverage Through People - Delegation is key, but do it like a founder, not a manager. - Transfer ownership, not just tasks. - Empower teams by sharing outcomes and allowing room for creativity. - Ask yourself: What $5/hour work are you holding onto that’s blocking your $1,000/hour work? 2. Leverage Through Code - Automation and modern software replace manual workflows. - Today, you don’t need a dev team to build tools—AI can generate scripts and automation for you. - Built internal apps and CRMs with no/low code tools. - Automate tasks through scheduling, reporting, and workflows. 3. Leverage Through Capital - Every dollar should buy back time or create compounding value. - Use capital to invest, buy access, or convert traffic into sales. - Examples: Affiliate programs Investing in dividend stocks or crypto Ad spend on proven funnels 4. Leverage Through Content - Content builds trust while you sleep. - It is a scalable, reusable asset—blog posts, podcasts, guides, videos. - "Create once, distribute forever" is the mantra. - Your content is always working—even when you’re not. Resources & Tools: 🔗Create Once, Distribute Forever 🔗ChatGPT 🔗Upwork 🔗Fiverr 🔗N8N - Workflow Automation 🔗HubSpot 🔗Lovable — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds
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Fix These B2B Bottlenecks to Unlock Hypergrowth
Jun 28, 202500:18:59Tap to summarizeIn this episode of The Ross Simmonds Show, Ross unpacks the silent bottlenecks that are stalling high-potential B2B companies, regardless of their size or success. Drawing from years of experience working with startups to publicly traded enterprises, Ross highlights the most overlooked internal barriers to growth and, more importantly, how to eliminate them. You’ll walk away with actionable advice and frameworks to optimize your messaging, sales cycle, onboarding flow, content strategy, and team alignment, all aimed at transforming friction into momentum. Key Takeaways and Insights: 1. Common B2B Bottlenecks - Misaligned Messaging Speaking to investors instead of customers is a fatal UX misstep. Use real customer language on homepages and in sales materials. Focus on emotional resonance and clarity, not buzzwords. Apply the AIDA framework: Attention, Interest, Desire, Action. - Bloated Revenue Process Long, complicated sales cycles add friction, not value. Reduce approvals and handoffs—especially for low-ticket SaaS products. Make buying intuitive: include pricing, live demos, streamlined decks. - Weak Onboarding & Lack of Quick Wins Onboarding should feel like success, not a setup chore. Deliver fast value: think checklists, 48-hour wins, and proactive outreach. High delight in the first week = low churn in the future. - Lack of Content Distribution “It's not the content industry. It’s the content marketing industry.” Great content often goes unseen due to weak promos. Break down and repurpose one asset across multiple platforms. Misalignment between sales, marketing, and success leads to a broken customer journey. Growth should be a team sport centered around shared KPIs. 2. Ross’s 3-Step Audit Framework - IMPACT – What’s costing us the most right now? - URGENCY – What needs to be fixed immediately? - EASE – What's a quick win we could implement this week? Resources & Tools: 🔗 Create Once, Distribute Forever by Ross Simmonds 🔗 Distribution.ai 🔗 HubSpot 🔗 Loom — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds
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