The Ross Simmonds Show

Ross Simmonds
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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. RSS 17: Redefining Modern Leadership and HR with Craig Samson

    20 HR AGO

    RSS 17: Redefining Modern Leadership and HR with Craig Samson

    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/

    43 min
  2. RSS 16: The Death of Work-Life Balance: My Journey

    29 AUG

    RSS 16: The Death of Work-Life Balance: My Journey

    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

    28 min
  3. RSS 15: Scaling Influence: From Creator to Industry Leader

    23 AUG

    RSS 15: Scaling Influence: From Creator to Industry Leader

    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

    23 min
  4. RSS 14: Building Brands, Building Balance: Brayden Young on Disrupting B2B with Real Conversations

    15 AUG

    RSS 14: Building Brands, Building Balance: Brayden Young on Disrupting B2B with Real Conversations

    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/

    52 min
  5. RSS 13: ChatGPT 5 Just Changed the Game -- NOT A NORMAL EPISODE

    8 AUG

    RSS 13: ChatGPT 5 Just Changed the Game -- NOT A NORMAL EPISODE

    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

    9 min
  6. RSS 12: The Myth of Passive Income

    1 AUG

    RSS 12: The Myth of Passive Income

    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

    23 min
  7. RSS 11: Be the First to Reach Out: How It Changed EVERYTHING For Me

    26 JUL

    RSS 11: Be the First to Reach Out: How It Changed EVERYTHING For Me

    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

    30 min
  8. RSS 10: How to Get Your Content Seen by the Right People

    20 JUL

    RSS 10: How to Get Your Content Seen by the Right People

    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

    1h 10m
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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 - 2025
  • Episodes
    135
  • Rating
    Clean
  • Copyright
    © Foundation Inc.
  • Show Website
    The Ross Simmonds Show

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