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/
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
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
In this episode of The Ross Simmonds Show, Ross dives into the practical, strategic use of artificial intelligence (AI) in content creation. He addresses a common fear among creators: that AI-generated material lacks originality and authenticity. Ross argues that when used correctly, AI doesn’t replace the human voice—it amplifies it. He lays out a five-step framework to integrate AI as a content copilot rather than a creator replacement, covering research, drafting, repurposing, optimization, and personalization. Real-world examples and tools are shared throughout to guide marketers and creators on how to scale their impact with AI—without sounding robotic. If you're playing the long game with your content strategy, this episode is a must-listen. Key Takeaways and Insights: 1. The Fear is Real—but Beating It Is Possible - Common creator concern: AI-generated content sounding generic - The solution: using AI as a creative partner, not a copy-paste machine 2. The AI Content Framework: 5 Key Areas - Research - AI allows you to conduct extensive research at scale - First Draft Creation - AI breaks writer’s block with structured first drafts - Repurposing Content - Repurpose blog posts into: - Social media posts - Podcasts - Newsletters - Video scripts - Optimization for SEO - AI can help you optimize content by identifying: - Keyword gaps - Better H1s/H2s - On-page SEO improvements - Tailorization & Personalization - AI enables communication at scale without sounding generic 3. Content as a Living ROI-Generating Asset - Content should be continuously updated and repurposed to earn maximum ROI - Multiply your hourly worth by time spent on content—then ensure that asset provides returns Resources & Tools: 🔗 Distribution.ai 🔗 ChatGPT 🔗 Microsoft Copilot 🔗 Replit 🔗 Loop Marketing Framework from HubSpot — 👋🏾 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 sits down with Dusty Holcomb, seasoned executive and founder of Arcqus Group, to talk about what it truly means to lead in today’s complex world. With over two decades of experience leading high-growth companies in logistics and eCommerce, Dusty shares powerful lessons on embracing vulnerability, building with intent, saying “no” to distractions, and remaining anchored in purpose. Whether you're a CEO, entrepreneur, or people leader, this conversation offers insights on self-leadership, scaling effectively, and building transformative leadership habits. Packed with real-world stories, frameworks, and actionable wisdom, this episode is a must-listen for those playing the long game. 1. Vulnerability in Leadership - How Dusty overcame surface-level transparency. - Leadership as a learned, active behavior. - Advice for leaders hesitant to open up. 2. Leading Through Chaos and Saying No - A Red Stag story: Saying no to a dream client to stay aligned with brand promise. - Anchoring every decision in first principles and mission clarity. - Use thinking time and decision frameworks to combat shiny object syndrome. 3. Challenges Facing Modern Leaders - More decisions than ever before (hello, AI). - Being “ruthlessly focused.” - Framework: “Distill it to three—and then to one.” 4. Habits, Rhythms, and Self-Leadership - Why self-care isn’t selfish. - Quarterly reviews and morning/evening routines. - Framework: Accountability through public commitment. 5. Creating Safe Spaces for Growth - How vulnerability leads to transformation in small groups. - Real stories of powerful breakthroughs and support in cohorts. 6. Three Key Lessons Dusty Would Tell His Younger Self - Trust your gut (and verify it). - You’re in the seat for a reason. - Surround yourself with good mentors and advisors. 7. On Gut Feelings and Building Confidence - Exercises to validate gut instincts. - Frame tough decisions: “What’s the worst that could happen?” 8. Breaking Imposter Syndrome - Tools for building conviction and clarity in your role. - Practice "the gap and the gain" mindset. 9 . Mentorship: How to Find and Add Value to a Mentor - Don’t chase billionaires – start with thought leadership and inner circle. - Great mentors learn from your questions. - “We often teach what we most need to learn.” 10. 3 Pain Points Most Leaders Face - Frustration vs. results gap. - “Why does everything fall on me?” - Leadership loneliness and isolation. 11. Coaching Execution Starts with Clarity & Alignment - Execution problems often stem from unclear expectations. - Solving upstream issues unlocks downstream performance. 14. The Role of CEOs: Vision and Connection - A CEO’s job is connecting purpose, vision, and plan. - Always be teaching and reinforcing the why. Resources & Tools: 🔗Arcqus Group — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds — 👋🏾 Stay connected with Dusty — ╰ Instagram: @wareagledusty ╰ Twitter / X: @wareagledusty ╰ LinkedIn: linkedin.com/in/dustyholcomb/
In this episode of The Ross Simmonds Show, Ross was interviewed by Rich Brooks to debunk the myth that content marketing ends when you press publish. Together, they explore the essential strategies behind effective content distribution, including Ross’s powerful framework: Repurpose, Remix, and Reshare. From leveraging AI tools like Distribution.ai to embracing video in B2B content strategy, this conversation is packed with actionable insights to help your content reach the audience it deserves. Key Takeaways and Insights: 1. The Real Work Starts After “Publish” - Publishing is not the final step—it’s the starting line. - Measure not by how often you publish but by how many people you reach and engage. - Most content dies in obscurity because it's never distributed effectively. 2. What is Content Distribution, Really? - The process of ensuring your content is discovered by the right audience. - Requires deep audience and channel research to deliver content in the right format at the right place. - It’s about strategy, not just amplification. 3. The Three R’s Framework: Repurpose, Remix, Reshare - Repurpose: Turn one content asset (e.g. webinar) into blog posts, newsletters, eBooks. - Remix: Reformat – video into audio, cut clips for social media. - Reshare: Continuously circulate evergreen content; don't assume one post is enough. - Modernize and refresh content similar to how Disney reboots classic stories. 4. Should You Lead with Video, Audio, or Text? - Best: Video – it’s the most repurposable and personal format, even in B2B. - Next: Audio – podcasting creates parasocial relationships and trust. - Last: Text – still valuable, but easier to fake and less engaging. - Embrace the format that aligns with your strength—but don't ignore video if you're serious about future visibility. 5. Using AI To Scale Content Distribution - AI is an accelerant: great marketers get greater, fast. - AI tools like Distribution.ai help apply your brand voice and create promotional content at scale. - Human review is still critical—AI is great, but human nuance still wins. 6. SEO Is Not Dead - "SEO is dead" is a myth. Search has evolved, not vanished. - Think beyond Google: people search on LinkedIn, Reddit, YouTube, Facebook, Instagram. - Optimize for discovery wherever your audience is searching. Resources & Tools: 🔗 Distribution.ai 🔗 Ross’s Book: “Create Once, Distribute Forever” 🔗 Agents of Change - Smart Content Distribution Strategies with Ross Simmonds — 👋🏾 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 why Reddit has emerged as the most powerful organic marketing platform heading into 2025. From transforming million-dollar buying decisions to influencing AI language models like ChatGPT and Google's AI Overviews, Reddit isn't just a content site — it's a market-shaping force. Ross unpacks exactly how and why Reddit has become a SERP-dominating player, how brands can harness its authenticity-fueled power, and introduces his signature Reddit marketing framework: R.O.S.S (Reddit Operating System of Scale). Key Takeaways and Insights: 1. The Power of a Single Reddit Thread - Deals are won or lost based on one Reddit post - Reddit is no longer just memes — it’s shaping corporate decisions 2. The Rise of Reddit in Organic Search - Reddit ranked 2nd after Wikipedia for Google search traffic in late 2024 - Outperformed YouTube in search visibility - Took over bottom-of-funnel consideration traffic from platforms like G2 and Capterra 3. Why Traditional SEO is Failing - Marketers ruined trust in content with affiliate-driven blog posts - Reddit now draws 600M+ monthly visits from Google - 1,328% YoY growth in Reddit's search visibility 4. Google's Algorithm Shift & Reddit’s Role - Reddit's authentic content aligns with Google’s user-first approach - Google’s $60M data licensing deal with Reddit (2024) - New "Forums" search tab prioritizing Reddit threads 5. Reddit vs Traditional Media & Review Sites - Reddit ranks for 5.7M+ transactional keywords - Competes with giants like Wirecutter and New York Times for product discovery - 5.1M overlapping keywords with major publishers 6. Reddit's Impact on AI Training - Reddit content now foundational for LLMs (Large Language Models) - Google, OpenAI, and others using Reddit content to train AI - AI outputs now reflect sentiment from Reddit conversations 7. How Reddit Influences AI Answers - Brand reputation on Reddit can directly influence AI-generated recommendations - Reddit as a real-time, user-driven knowledge base for AI Resources & Tools: 🔗GummySearch 🔗Brandwatch 🔗Reddit List 🔗Sparktoro — 👋🏾 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 breaks down how artificial intelligence is fundamentally changing the way consumers discover, evaluate, and choose products or services. Traditional SEO strategies and marketing funnels are no longer as effective in a world where AI platforms like ChatGPT, Claude, Gemini, and TikTok summaries serve as the first touchpoint for buyers. Ross not only highlights these seismic shifts but also provides a concrete blueprint for brands looking to thrive in an AI-influenced world: show up where the machines are listening, create confident content, and double down on what only humans can do—empathize and build trust. Key Takeaways and Insights: 1. AI Has Become the New Middleman - AI is now the layer between businesses and buyers—not your website, blog, or email campaign anymore. - Platforms like Google Search are now serving AI-generated answers directly in the SERPs. Users no longer need to click through to content. 2. The Rise of AI-Powered Discovery - Tools like ChatGPT, Claude, and Gemini are replacing traditional search. - Platforms like Reddit and TikTok are leveraging AI to deliver research-based answers and recommendations. 3. AI Discovery vs. Traditional SEO - Search is now decentralized—starting on TikTok, Reddit, Instagram, and AI tools. - “GEO” (Generative Experience Optimization) is not just another flavor of SEO—it's a new paradigm. 4. Evaluation Before Interaction - Buyers are arriving at demos already informed via AI comparisons and analysis. - Trust has already been formed—or lost—before your team speaks to the buyer. 5. AI’s Interpretation of Trust - AI evaluates trust by looking at author credibility, citations, platform presence and content quality. - Influencing LLMs (Large Language Models) is now as important as influencing people. 6. Actionable Solutions - Solution #1: Shift Your Mindset - Solution #2: Build Authoritative Content Moats - Solution #3: Align for the Pre-Sales Journey 7. The Ultimate Competitive Edge: Being Human - AI can't replicate human empathy, intuition, or emotional intelligence. - Your ability to build trust in 1:1 conversations and real-world engagement is your moat. Resources & Tools: 🔗 ChatGPT 🔗 Claude 🔗 Gemini 🔗 Reddit AI Tools 🔗 Perplexity AI — 👋🏾 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 talks with Craig Samson, founder of Gran Sasso HR Solutions, about modern leadership, people strategy, and rebuilding organizational culture. Craig shares practical frameworks for leading with vulnerability, building high-performing teams, and evolving HR from a support function into a strategic driver of business value. He also dives into the importance of self-awareness, psychological safety, and how to lead effectively in both in-person and remote-first organizations. Whether you're a founder hiring your first team, a new people leader, or an executive looking to scale a performance-driven culture, this episode is packed with actionable leadership wisdom. Key Takeaways and Insights: 1. What Makes a Great Modern Leader - Effective leaders today lead with authenticity, vulnerability, and trust. - Leadership is no longer about knowing everything—it’s about empowering others. - Letting go of traditional ego-driven expectations is key to being relatable. 2. Vulnerability in Leadership: Turning Weakness into Strength - Vulnerability builds trust—it's OK (and essential) to not have all the answers. - Invite collaboration by admitting shortcomings and asking for help. - “The more you give it away, the more you get back.” 3. Advice for Founders Building First-Time Leadership Teams - Founders should avoid hiring clones of themselves. - Surround yourself with diverse thinkers—balancing fast-moving visionaries with detail-focused operators. - Slow down to clearly communicate expectations. 4. Frameworks for Building Balanced Teams - Understand human biases: we tend to gravitate toward those who are like us. - Craig recommends the DiSC personality tool to build self-awareness and team compatibility. 5. Elevating HR to a Strategic Advantage - HR must shift from policy enforcement to business partnership. - Use data to show ROI on people investments (absenteeism, turnover, engagement). - Craig recommends anonymous employee engagement surveys to get deeper insights. 6. Transforming Culture at Scale - Craig shares a case study from his time overhauling HR at a billion-dollar retailer. - Flipped the HR model by sending teams into the field to rebuild trust and partnership with operations. - Engagement and performance increased significantly post-transformation. 7. Remote Leadership & Trust - Manage to deliverables, not screen time. - Over-communicate expectations and purpose. - Use in-person time strategically to build deep connections. Resources & Tools: 🔗 DiSC Behavioral Assessment 🔗 Gran Sasso HR — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds — Connect with Craig — ╰ Twitter / X: @craigsampson07 ╰ LinkedIn: linkedin.com/in/craig-sampson-263b3527/
In this episode of The Ross Simmonds Show, Ross dives deep into the real cost of high performance and ambition. From managing two companies and global speaking engagements to parenting with intention, Ross offers a transparent look at his life and how he approaches productivity, sacrifice, and sustainability — not through the lens of balance, but through integration. If you're someone who's chasing big things and wondering how to keep going without losing yourself, this episode is packed with insights and frameworks to help you build for the long game. Key Takeaways and Insights: 1. The Myth of Balance - High achievement rarely comes from comfort or balance. - Growth is messy, intense, and requires sacrifice. - Striving for a 1% outcome means choosing priorities with intention, not perfection. 2. Living With Intention, Not Guilt - Balance isn't about doing everything — it’s about choosing what matters most. - “Every yes is a no to something else.” Choose your “yes” intentionally. 3. Say No Strategically - Practical example: saying no to ad-hoc calls or meetings without clear agendas. - Use your calendar to reflect your life priorities — from anniversaries to golf sessions. 4. Mindset Shifts That Scale - Shift mindset from scarcity ("I don’t have time") to gratitude ("I get to do this"). - Burnout often stems from expecting trade-offs without acknowledging purpose. Resources & Tools: 🔗 Garmin Watch — 👋🏾 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 explores the journey from content creator to respected industry leader. He breaks down what it really takes to shift from getting attention online to earning recognition and influence in your niche. If you're focused on building long-term authority, leading important conversations, and creating real impact with your online presence, this episode is for you. Key Takeaways and Insights: 1. Build Depth, Not Just Reach - Authority is built with repetition, storytelling, and action—not virality. - Creators get likes, leaders drive action. - Leadership = influence, invitations, and impact. 2. Show, Don’t Just Tell - Depth is more powerful than width: Own one niche instead of dabbling in many. - Importance of specialization—become a 1%-er in your niche. 3. Create Signature (Evergreen) Assets- Build evergreen content—that’s share-worthy even when you're offline. - Influence grows when people see you apply what you preach - Move beyond short-form content that disappears in the scroll. - Recommended formats: podcasts, books, blogs, keynote decks. 4. Consistency Is the Currency of Trust - Trust comes through delivering value, not asking for attention. - Consistency > Inspiration. 5. Connect With Other Leaders - Influence multiplies with strong associations. - Want to build influence? Start by playing a long game, not chasing trends. - True influence = outcomes, not impressions. - Vulnerability & authenticity build trust. - Don’t only create content—create conversations. - Commit deeper. Go further. Build impact. Resources & Tools: 🔗Create Once, Distribute Forever 🔗Foundation Marketing 🔗Distribution.ai — 👋🏾 Let's stay connected —╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds ╰ Website: rosssimmonds.com
In 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/
In 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
In 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
In 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
In 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
In 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
In 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
In 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
In this episode of The Ross Simmonds Show, Ross dives deep into a topic that many leaders shy away from: the loneliness of leadership. He opens up about his experiences as a solo founder, the mental and emotional burden that comes with leading organizations, and how success can bring unexpected isolation. More importantly, Ross offers practical and powerful advice on how leaders can build resilience, create support systems, and avoid common traps that lead to burnout and self-doubt. If you’ve ever felt alone at the top, this is the reminder you didn’t know you needed. Key Takeaways and Insights: 1. The Quiet Weight of Foundership - Leadership is often glamorized from the outside, but behind closed doors, it can be emotionally and mentally taxing. - Founders are expected to always be “on” — delivering, solving, and showing up, even during personal lows. - “Being a founder is a gift, but it’s also one of the loneliest jobs.” 2. What Makes Leadership So Isolating - It’s not physical solitude, but the responsibility that isolates leaders. - You make decisions that shape careers — sometimes lives — and often have no one to share the burden with. 3. The Trap of Self-Containment - One of the biggest mistakes is trying to carry everything alone. - Delegating responsibility and building trust with team members can alleviate this loneliness. 4. Four Reasons Leaders Feel Isolated - 🧠 Information Asymmetry Leaders have a different view of company data, performance, and risks. Transparency can reduce the burden and build empathy. - ❤️ Emotional Labor Leaders are expected to remain steady and optimistic, even when they're struggling inside. Emotional resilience is important, but suppressing emotion leads to burnout. - Identity Tied to Business Outcomes When your self-worth becomes linked to business success, every failure feels personal. - Shrinking Circle of Trust As you succeed, your peer group shrinks — making honesty and vulnerability harder. 5. How to Fix It: Four Strategies - Build a True Inner Circle - Or start a group chat with like-minded entrepreneurs. - Find two kinds of mentors: Someone ahead of you to guide you. Someone behind you to keep you pushing forward. - Intentional Reflection - Thoughtfully Include Your Team in Pressure - Work With a Coach or Therapist 6. From Loneliness to Connection - Celebrate wins publicly to avoid harboring joy alone. - Share successes with your team, friends, and family. - “You shift from performing to living.” 8. Final Reflections: You’re Not Alone - Loneliness is common but not permanent. - You can go further with people, with honesty, and with emotional openness. - He who wears the crown must bear the weight — but not alone. Resources & Tools: 🔗 EO (Entrepreneurs' Organization) 🔗 YPO (Young Presidents' Organization) 🔗 Hampton 🔗 Ross Simmons Show Archive — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds