
The Ross Simmonds Show
Welcome to The Ross Simmonds Show. A show exploring the different sides of entrepreneurship, how Ross is growing his global marketing agency, building software, raising a family, and attempting to do so much more. On this show, Ross explores what goes into executing with excellence, embracing innovation, marketing at a high level and doing it all with intent of the playing the long game.This show is a proud member of the HubSpot Podcast Network.
Latest episodes

Jul 12, 2025 • 16min
How Marketers Can Thrive During Budget Cuts & Downturns
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:
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.
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.
Proven Tactics for Marketing with Zero Budget
Repurpose your top-performing historical content.
Example reuse: LinkedIn carousels, Reddit posts, YouTube Shorts.
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.
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.
Embrace Evergreen Content
Create assets that compound over time vs. quick hits.
Focus on material that drives long-term ROI.
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

Jul 5, 2025 • 22min
How To Get More Leverage & Do More With Less
Discover how to achieve 10x results without doubling your efforts through the power of leverage. Dive into the four core types: leverage through people by effective delegation and empowering teams; leverage through code via automation and low-code tools; and leverage through capital to make smart investments that save time. Gain actionable insights and mindset shifts that can help reclaim your time and enhance productivity, making it easier to scale your impact and drive growth.

Jun 28, 2025 • 19min
Fix These B2B Bottlenecks to Unlock Hypergrowth
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:
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.
🛠Quick fixes:
Add a self-serve option.
Implement interactive product demos.
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.
🙌 Practical Tip:
Use Loom videos and personalized templates to improve onboarding experience.
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.
Internal Team Silos
Misalignment between sales, marketing, and success leads to a broken customer journey.
Growth should be a team sport centered around shared KPIs.
Everyone should obsess over customer outcomes and revenue.
🧩 Solution:
Create a growth squad that spans multiple departments and reviews customer journeys collectively.
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

Jun 21, 2025 • 26min
The Loneliness of Leadership: Founders, You're Not Alone
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:
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.”
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.
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.
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.
How to Fix It: Four Strategies
👫 Build a True Inner Circle
Join peer groups like:
EO (Entrepreneurs' Organization)
YPO (Young Presidents' Organization)
Hampton
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
Use journaling, podcasting, or downtime to process your emotions and gain clarity.
Create space to think beyond day-to-day operations.
🌪️ Thoughtfully Include Your Team in Pressure
Transparency ≠ emotional dumping.
Share relevant challenges and strategically invite collaboration.
Avoid transferring overwhelming anxiety to junior team members.
🧠 Work With a Coach or Therapist
Coaches help with clarity and accountability.
Therapy can help unpack the deeper emotional toll of leadership.
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.”
Final Reflections: You’re Not Alone
Loneliness is common but not permanent.
“You can go further with people, with honesty, and with emotional openness.”
Wise closing quote: “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

6 snips
Jun 14, 2025 • 23min
Generative Engine Optimization & the Power of Memory
Explore the transformative world of Generative Engine Optimization (GEO) and how AI is reshaping search strategies. Discover the importance of memory and personalization in creating more effective content. Learn actionable tactics for building author entities and enhancing brand visibility. The conversation emphasizes moving from traditional SEO practices to a more context-rich, conversation-based approach, ensuring your marketing evolves alongside intelligent algorithms.

Jun 7, 2025 • 26min
Distribution Strategy 101
Learn why simply hoping for virality won't cut it in the world of content distribution. Discover the five common mistakes marketers make, from publishing once to relying on a single channel. Emphasize the importance of a multi-channel strategy to maximize audience reach. Delve into the necessity of transforming good content into impactful results through a structured distribution plan. Plus, get tips on tracking engagement and adapting your strategy based on data insights.

May 31, 2025 • 22min
The AI Hype Cycle in Marketing
In this episode of The Ross Simmonds Show, Ross cuts through the overwhelming noise around AI in marketing to reveal what’s real, what’s useful, and what’s pure hype. From AI-fueled content creation and personalization to ads, analytics, and the dangers of AI deepfakes, Ross shares his honest take on how marketers can harness AI effectively—without losing their creativity (or their jobs). Hint: AI isn’t here to replace great marketers, but it will expose mediocre ones. Whether you’re feeling FOMO about AI tools or tired from constant information overload, this episode offers grounded insights and an actionable roadmap for embracing AI in a sustainable and meaningful way.
Key Takeaways and Insights:
Understanding the Current AI Hype Cycle
AI is at the peak of inflated expectations.
Nearly every tool is rushing to add AI capabilities.
$10B spent in AI implementation efforts by consulting firms.
The opportunity is real—but so is the noise.
Content Creation: The Draft, Not the Director
Tools like ChatGPT, Jasper, Rytr, SEMrush, and HubSpot offer “okay” drafts.
Great marketers use AI for first drafts, then add emotion, creativity, and data.
AI helps compress content production time significantly.
Key quote: “The AI tool is not your creative director.”
Repurposing & Distribution at Scale
One of the best use cases for AI in content marketing.
Turn one podcast into dozens of social assets, short videos, quotes, etc.
Old content can be brought back to life using AI.
24/7 brand promotion equals scale and efficiency.
AI for Creating Visuals & Ads
Tools now allow marketers to generate images and mock ads from product photos.
Emerging use case: image creation with tools like ChatGPT’s DALL·E.
AI lowers cost and time for creative asset generation.
AI-Powered Insights from Data
AI can identify behavior trends, segment audiences, and support lead scoring.
Automate personalized communications triggered by user behavior.
In-depth AI-based customer feedback analysis is now possible.
Reminder: "Good data = good AI."
Personalization: Right Message, Right Time
AI enables highly tailored emails, landing pages, and even video messages.
Important: Avoid going too far or getting creepy with data usage.
Balance personalization with ethics and relevance.
The Fluff: SEO Snake Oil & “Turnkey” Strategies
Beware of tools promising 10,000 blog posts and instant rankings.
"Hallucination" risk with auto-generated content hurts SEO in the long run.
One-click marketing strategy generators? Hard pass.
Deepfakes & AI Influencers
Increasing use of AI-generated personas to push products deceptively.
Danger of consumers being misled by realistic but fake endorsements.
The Future of Marketing & AI
AI will not replace everyone—but will replace some.
“It’s a force multiplier for the great. A replacement for the mediocre.”
Use AI to do more, faster—but don’t skip thinking and strategy.
To thrive, marketers must master the human elements: storytelling, empathy, strategy, and creativity.
Resources & Tools:
🔗Distribution.ai
🔗Japser
🔗ChatGPT
🔗Rytr
🔗HubSpot AI
🔗SEMrush AI Writing Tools
— 👋🏾 Let's stay connected —
╰ Subscribe to my channel: @RossSimmondsTV
╰ Instagram: @thecoolestcool
╰ Twitter / X: @thecoolestcool
╰ LinkedIn: linkedin.com/in/rosssimmonds

May 24, 2025 • 18min
Google AI Mode
Explore the exciting transformation brought by Google’s AI Mode, launching a new era of personalized search experiences. Discover how traditional SEO practices are fading as users receive synthesized, AI-driven responses. Marketers are urged to focus on intent-based content strategies and enhance their omnichannel presence. Learn about the innovative 'agentic booking' feature that simplifies multi-step tasks. The podcast dives deep into evolving marketing techniques, emphasizing targeted approaches in a rapidly changing digital landscape.

May 10, 2025 • 11min
Behind the Scenes with Ross: A Big New Chapter
In this episode of Create Like The Greats, Ross Simmonds shares a personal journal-style update on his business journey and a major new strategic partnership. Ross walks listeners through the evolution of his brand Foundation Marketing, a newly formed alliance with education-sector marketing leader Carnegie, and the power of delivering value in every room you enter. This episode delivers insight into the journey from humble beginnings to significant success and highlights the long-term impact of authentic relationship-building, content creation, and value-driven partnerships.
Key Takeaways and Insights:
A Major Partnership Announcement
Ross announces the new partnership between Foundation Marketing and Carnegie
Carnegie Dartlet - Higher Education Marketing Organization
The Power of Speaking & Connection
Importance of showing up with value in every room
The origin story of how opportunities arise from consistent effort and public speaking
Ross’s Content Creation Journey
Ross’s early days blogging in his basement with little money (and lots of instant coffee)
Turning point: speaking invitation to Miami from a reader
Lesson: "You can live anywhere in the world, create content, and reach people globally"
About the Carnegie Partnership
Announcement revisited: Foundation + Carnegie collaboration to serve higher education clients
Carnegie’s strength: deep experience with higher ed digital marketing
Foundation’s traditional focus: B2B and SaaS, now expanding into higher ed
Early wins and the rewarding nature of impacting students’ journeys
How the Partnership Came to Be: Storytime
Carnegie first approached Ross via a DM inviting him to speak at their Orlando event
Ross’s mindset: treat the audience with full value even though it wasn't his target industry
Result: strong impact, positive reception, and future opportunity
Round Two: The Follow-Up Years Later
Ross’s wife encourages follow-up; he DMs Carnegie again
They invite him to speak a second time
Second session’s topic: content as a competitive edge, SEO as a moat
Deeper engagement: internal training, workshops at Carnegie
The Partnership Comes to Life
The relationship matures into a formal partnership
Foundation and Carnegie now jointly create content for higher ed institutions
Goal: drive meaningful, measurable results in the education space
Collaboration Vs. Scarcity
Business lesson: “If you want to go fast, go alone. If you want to go far, go together.”
Value of partnering with aligned people and organizations
Nuggets of wisdom from Ross’s grandmother: “There’s enough for everyone to eat”
Encouragement for listeners to seek partnerships that drive both impact and personal alignment
Resources & Tools:
🔗 Distribution.ai
🔗Carnegie and Foundation Partnership
— 👋🏾 Let's stay connected —
╰ Subscribe to my channel: @RossSimmondsTV
╰ Instagram: @thecoolestcool
╰ Twitter / X: @thecoolestcool
╰ LinkedIn: linkedin.com/in/rosssimmonds

May 3, 2025 • 17min
SEO, Reddit & the Future of Marketing
In this special episode of Create Like the Greats, Ross Simmonds sits down with SEO expert Garrett Sussman from iPullRank for a dynamic conversation recorded ahead of SEO Week. They unpack the current and future state of search, the increasing relevance of Reddit in SEO strategies, and how marketers must evolve with AI-driven search behaviors. Ross also previews his upcoming SEO Week talk on Reddit, AI, and user-generated content—and shares a tactical gem that every brand should act on today.
Key Takeaways and Insights:
SEO Week 2026 Preview
SEO Week will return to NYC in 2026 featuring top minds in SEO, content marketing, social, AI, and more.
The State of Search: Chaotic but Beautiful
Search has dramatically evolved; it's no longer just about Google.
Fragmented discovery across TikTok, Reddit, YouTube, ChatGPT, Perplexity.
Emphasis on first principles: high-quality content, user intent, and storytelling.
Marketers must now behave more like... well, marketers, not just SEOs.
Creating Content That Scales
SEO in 2024+ requires multimedia optimization:
Text + video (especially YouTube) for better SERP coverage.
Understanding where your audience starts their search journey.
Reddit threads and YouTube videos are now ranking in Google results, diversifying content visibility.
Reddit + AI + UGC: A Preview of Ross's Talk at SEO Week
Reddit is emerging as a powerful and underused SEO platform.
Ross's team is scraping and analyzing subreddits, mapping them to keywords and AI outputs.
Google & OpenAI have data licensing deals with Reddit—proof of its strategic value.
Reddit content is influencing AI-generated responses… and SEO strategies must adapt.
Tactical Insight: Own Your Subreddit
Brands should immediately create and claim their subreddit—even if not actively using it.
Prevent brand impersonation or NSFW sabotage by securing the namespace.
“It's as basic as securing your domain or Twitter handle,”
💡 Bonus Tip:If another user claimed your brand subreddit, reach out to the mod team to request control.
What's Next: The Future of Search
Rise in brand mentions could impact search visibility.
Voice search is finally finding a place—via AI assistants and wearable UIs.
Search is becoming more immersive—but Google is far from dead.
SEOs must balance short-term tactics with long-term strategic brand building.
Resources & Tools:
🔗Distribution.ai
🔗seoweek.org
🔗Create Once, Distribute Forever
— 👋🏾 Let's stay connected —
╰ Subscribe to my channel: @RossSimmondsTV
╰ Instagram: @thecoolestcool
╰ Twitter / X: @thecoolestcool
╰ LinkedIn: linkedin.com/in/rosssimmonds