The Ross Simmonds Show

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.

Episodes

RSS 45: You Don't Need to Move: How Matt Paulson Built $200M+ in Wealth from His Small Town & What He'd Do Differently Now

March 20, 2026 • 58 mins
Stop scrolling through fantasies about moving to big cities... this episode will hit different. Matt Paulson joined me to break down how he created roughly $200 million in wealth through MarketBeat while based in Sioux Falls (population ~200k). We go in on the non-negotiable principles that drove his 20-year compounding success... why location independence + community roots beat the coastal grind... exactly how he'd start over in t...
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RSS 44: SEO Is Not What You Think Anymore And Mike King Explains Why

March 13, 2026 • 65 mins
In this episode of The Ross Simmonds Show, Ross sits down with Mike King, founder of iPullRank, to unpack the seismic shift from traditional SEO to AI search, AEO, and GEO, and why framing it as "just SEO" is quietly costing teams budget, influence, and growth. Together, they break down the Google leak, retrieval-augmented generation (RAG), content ecosystems, and what separates operators from spectators in the next era of search. ...
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RSS 43: 5 Underrated Career Moves That Separate Top Performers from the Pack

March 6, 2026 • 18 mins
In this episode of The Ross Simmonds Show, Ross breaks down five underrated career strategies that quietly separate high performers from everyone else. From investing in yourself without permission to thinking in decades instead of quarters, this is a tactical blueprint for anyone serious about long-term growth. If you're playing the long game in your career, this episode gives you the mindset and structure to win it. Key Takeaw...
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RSS 42: The SaaS-pocalypse Is Real — But Not How You Think

February 27, 2026 • 25 mins
In this episode of The Ross Simmonds Show, Ross breaks down the so-called “SaaSpocalypse” after $1 trillion in SaaS market cap vanished in a single week. While headlines scream that “AI will replace SaaS,” Ross argues the reality is far more nuanced. He introduces a three-part framework: Exposed, Embedded, Evolved, and outlines the strategic shifts founders and marketers must make to survive and compound in the age of AI agents. ...
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RSS 41: Reddit Is the New Front Page of B2B: Listen, Learn, Then Leap

February 20, 2026 • 16 mins
B2B buyers no longer rely solely on Google or your website for answers, they turn to private communities, Reddit, and even LLMs like ChatGPT and Perplexity. This episode of The Ross Simmons Show, breaks down why Reddit has become a critical influence layer in the modern buyer’s journey and how brands can win by combining SEO fundamentals, off-site visibility, and a disciplined Reddit strategy built on listening first. Key Takeaw...
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RSS 40: The Enterprise AI Stack Blueprint: How to Build It Right (Without Wasting Millions)

February 14, 2026 • 19 mins
Every enterprise is building an AI stack, but most are doing it wrong. In this episode, Ross breaks down a tactical, use-case-driven framework for building an AI stack that actually works. If you’re a marketer, operator, or executive looking to leverage AI strategically (without blowing your budget or ignoring compliance), this episode gives you the structure you need to win. Key Takeaways and Insights: 1. The Hard Truth About ...
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RSS 39: From Founder to CEO: Stop Doing More and Start Leading

February 6, 2026 • 18 mins
In this episode of The Ross Simmonds Show, Ross talks about the skills that create early traction don’t scale; growth requires letting go, delegating, and evolving into a CEO. Scaling isn’t just about revenue or headcount, it’s about scaling yourself. That means building trust, hiring people better than you in their domains, creating systems, rituals, and documentation, and replacing instinct with infrastructure. Founders must stop...
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RSS 38: The Stockdale Paradox: How Founders Survive Without Toxic Optimism

January 30, 2026 • 14 mins
In this episode of The Ross Simmonds Show, Ross explains why blind optimism can be one of the most dangerous traits for a founder. He introduces the Stockdale Paradox, the idea that great leaders balance unwavering belief in long-term success with full acceptance of the brutal facts in front of them. Ross shares how toxic positivity can cause founders to ignore churn, burn, and hard realities until it’s too late, while pessimism...
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RSS 37: Unlocking the Power of Partnership Marketing with Clinton Senkow

January 23, 2026 • 54 mins
In this episode of The Ross Simmonds Show, Ross sits down with long-time friend Clinton Senkow, a leading expert in partnership marketing. They explore the core principles of building successful partnerships, why most companies underutilize this growth tactic, and how AI is transforming the partnership landscape. Clinton shares actionable advice for startups and established companies looking to harness partnerships to accelerate gr...
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RSS 36: How to 10X Your Output with Claude or ChatGPT

January 16, 2026 • 24 mins
In this episode of The Ross Simmonds Show, Ross dives deep into the ways AI is reshaping how entrepreneurs, marketers, and content creators work and how you can use tools like Claude, ChatGPT, and Distribution.AI to get an edge instead of being left behind. Ross shares strategic frameworks, prompting techniques, and real-life use cases that show how AI isn't here to replace you, it's here to elevate what you do best. This episode i...
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RSS 35: The Power of Saying No: Focus to Scale

January 9, 2026 • 12 mins
In this episode of The Ross Simmonds Show, Ross dives deep into the underrated strength behind the word “no.” He unpacks why saying yes too often can lead to dilution of focus, scattered priorities, and slower growth—both for individuals and companies. Drawing from personal experiences building Foundation Marketing and working with world-class SaaS brands, Ross lays out how intentional decision-making drives scalable results. He sh...
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RSS 34: Winning with Intention in the Age of AI with Will Reynolds

January 2, 2026 • 78 mins
In this episode of The Ross Simmonds Show,  Ross sits down with Wil Reynolds—founder of Seer Interactive and an icon in the world of search—to explore how to play the long game in marketing, leadership, and entrepreneurship. Will doesn't hold back as he shares tactical insights into how AI is reshaping content creation, search, and discovery. From real-world applications of tools like PhantomBuster and Claude Code to personal philo...
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RSS 33: Leaders Say They Want Ownership, But Micromanage Everything

December 26, 2025 • 12 mins
In this episode of The Ross Simmonds Show, Ross dives into one of the most common yet damaging habits of leaders: micromanagement. While founders and leaders often express the desire for team members who “act like owners,” their own behavior can stifle that very ownership. Ross explores the concept of the "Ownership Window," offering a strategic framework for when leaders should be hands-on and when to step back. He breaks down the...
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RSS 32: Your Company Culture Is a Reflection of Your Worst Habits

December 19, 2025 • 9 mins
In this episode of The Ross Simmonds Show, Ross gets real about what culture truly is inside an organization. Spoiler alert: it’s not your values deck, your company retreats, or the catchphrases painted on your office walls. Culture is what your team experiences—and that starts with leadership. Ross unpacks how the most problematic leadership habits quietly become the blueprint of a company’s culture. Through personal insights a...
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RSS 31: You Don’t Deserve a High‑Performing Team If You’re Not a High‑Performing Leader

December 12, 2025 • 7 mins
In this episode of The Ross Simmonds Show, Ross delivers a candid message to founders, executives, and team leaders. If you're demanding high performance from your team but not modeling it yourself, the problem starts with you. Ross explores how poor leadership habits affect team culture and performance — and why success begins with self-awareness, accountability, and leading by example. If you're frustrated with team results, b...
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RSS 30: Generative Engine Optimization (GEO): Why I'm All In

December 5, 2025 • 21 mins
In this episode of The Ross Simmonds Show, Ross dives deep into one of the most fundamental marketing shifts of our time — the emergence of Generative Engine Optimization (GEO). As AI-powered discovery tools like ChatGPT, Perplexity, Google AI Overviews, Reddit Answers, TikTok Search, and more evolve, traditional SEO strategies are no longer enough. Ross unpacks how marketers need to rethink content creation, distribution, and visi...
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RSS 29: How to Use AI With Intention, Not Just Curiosity

November 28, 2025 • 18 mins
In this episode of The Ross Simmonds Show, Ross dives deep into embracing AI with clarity and direction rather than chaos and overwhelm. Rather than chasing trendy tools or piling on new software, Ross introduces the powerful AIM Framework—a proven model he’s developed to help founders, marketers, and operators use AI with intentionality. AIM stands for Accelerate, Integrate, and Multiply. Whether you're a startup founder, marke...
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RSS 28: The Personal Brand Playbook: Leverage Your Expertise

November 21, 2025 • 23 mins
In this episode of The Ross Simmonds Show, Ross dives deep into why building a personal brand is no longer optional—especially in today’s creator-driven, AI-powered world. Ross shares a tactical blueprint for building a brand that doesn’t just look good but actually drives opportunity, revenue, and trust. He breaks down a step-by-step approach on how to show up online with integrity, authenticity, and strategic precision. Whether y...
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RSS 27: Reddit Is Eating the Bottom of the Funnel

November 14, 2025 • 11 mins
In this episode of The Ross Simmonds Show, Ross breaks down why B2B marketers need to rethink their bottom-of-funnel strategies. Traditional review sites like G2, Capterra, and TrustRadius are losing ground in high-intent search queries—and Reddit is stepping up to take their place. Ross explores how Reddit outperforms review platforms in organic reach, how it’s shaping AI results, and exactly how brands can build a strategic, valu...
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RSS 26: Exploring Reddit Marketing, Digital Entrepreneurship & AI Distribution

November 7, 2025 • 32 mins
In this episode of The Ross Simmonds Show, Caleb Turner interviews Ross and they dive deep into the mindset and strategies behind building a personal brand, marketing via Reddit, leveraging AI for content distribution, and tactically navigating the future of search in an AI-driven world. Whether you're an emerging entrepreneur or a seasoned marketer, this episode offers insights for anyone looking to grow their influence and impact...
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