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PODCAST

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.

business entrepreneurship

All Episodes

19:29

RSS 49: Reddit Is Beating You in B2B Search And the...

The Ross Simmonds Show ·

2026/04/17

In this episode of The Ross Simmonds Show, Ross drops new research across 8,566 high-priority B2B SaaS keywords that reveals how Reddit is quietly dominating bottom-of-funnel search, including the most expensive CPC terms in your Google Ads account. He breaks down what the data actually means for your pipeline and the exact playbook operators need to respond before the gap widens further.Key Takeaways and Insights: 1. How Reddit Changed the SEO Game -Google elevated user-generated content

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24:18

RSS 48: The Fractional CMO Playbook: From Underdog to...

The Ross Simmonds Show ·

2026/04/10

In this episode of The Ross Simmonds Show, Ross breaks down how he built a quarter-million-dollar solo consulting business before 30 and how he would engineer that same growth today as a fractional CMO in the AI era. From personal brand foundations to referral flywheels to public speaking as a client acquisition engine, this is a tactical, no-excuses blueprint for building authority and pipeline as a one-person growth operation.Key Takeaways and Insights: 1.From Basement to $270K: The Origin

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28:01

RSS 47: The 10-Year Shift: Why Distribution Is Your...

The Ross Simmonds Show ·

2026/04/01

In this episode of The Ross Simmonds Show, Ross makes the case that AI visibility isn't a new game — it's the result of a decade of distribution compounding in plain sight. He breaks down why CREAM is dead, why D.R.E.A.M. wins, and exactly which channels, from Reddit to YouTube to review sites, are shaping what Google AI Overviews, ChatGPT, and Perplexity actually cite.Key Takeaways and Insights: The 10-Year Head Start Most Brands Missed AI visibility didn't start with ChatGPT. It started

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59:53

RSS 46: AI Is Not Search. Here's What It Actually Is...

The Ross Simmonds Show ·

2026/03/27

In this episode of The Ross Simmonds Show, Ross sits down with Brittany Muller, AI educator and founder of Orange Labs, to unpack what marketers are getting wrong about large language models, why reverse engineering ChatGPT is a dead end, and how to build real leverage in a probabilistic world. From practical AI workflows to the ethical risks shaping the future of the industry, this is a first-principles breakdown of what actually matters next.Key Takeaways and Insights: 1. AI is not search,

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58:40

RSS 45: You Don't Need to Move: How Matt Paulson...

The Ross Simmonds Show ·

2026/03/20

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 today's world... and the inspiring ways he's poured that success back

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65:40

RSS 44: SEO Is Not What You Think Anymore (And Mike...

The Ross Simmonds Show ·

2026/03/13

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.Key Takeaways and Insights: 1. SEO vs. AEO vs. GEO: why it's not

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18:31

5 Underrated Career Moves That Separate Top...

The Ross Simmonds Show ·

2026/03/06

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 Takeaways and Insights: 1. Invest in Yourself (Without Waiting for

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25:53

RSS 42: The SaaS-pocalypse Is Real — But Not How You...

The Ross Simmonds Show ·

2026/02/27

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.Key Takeaways and Insights: 1. The $1 Trillion Wake-Up

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16:05

RSS 41: Reddit Is the New Front Page of B2B: Listen,...

The Ross Simmonds Show ·

2026/02/20

Key Takeaways and Insights:The New B2B Buyer Journey -Buyers seek personalized answers in Slack groups, Discord, WhatsApp, Reddit, and LLMs. -LLMs frequently leverage Reddit to inform their responses. -Influence now happens in communities—not just on your website. -If you’re not present where conversations happen, you’re invisible at decision time. Reddit’s Influence on LLMs & AI Search -Platforms like ChatGPT, Perplexity, Claude, and Gemini pull insights from Reddit. -Reddit Answers

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19:50

RSS 40: The Enterprise AI Stack Blueprint: How to...

The Ross Simmonds Show ·

2026/02/14

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 Enterprise AI - Most companies choose AI tools based on hype, not

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18:51

RSS 39: From Founder to CEO: Stop Doing More and...

The Ross Simmonds Show ·

2026/02/06

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 being the bottleneck, accept work done at 80%, and focus their time

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14:02

RSS 38: The Stockdale Paradox: How Founders Survive...

The Ross Simmonds Show ·

2026/01/30

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 can drain teams of hope. The winners, he argues, are the ones who

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54:38

RSS 37: Unlocking the Power of Partnership Marketing...

The Ross Simmonds Show ·

2026/01/24

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 growth. Clinton also introduces us to his new AI-powered platform,

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24:46

RSS 36: How to 10X Your Output with Claude or ChatGPT

The Ross Simmonds Show ·

2026/01/16

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 is a masterclass in using generative AI as your co-pilot for ideation,

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11:11

RSS 35: The Power of Saying No: Focus to Scale

The Ross Simmonds Show ·

2026/01/09

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 shares a practical framework for evaluating opportunities, a unique way

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78:31

RSS 34: Winning with Intention in the Age of AI with...

The Ross Simmonds Show ·

2026/01/03

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 philosophies about content, agency building, and mindset, this episode is

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12:19

RSS 33: Leaders Say They Want Ownership, But...

The Ross Simmonds Show ·

2025/12/26

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 fine line between leadership and control, examines the stages of

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9:19

RSS 32: Your Company Culture Is a Reflection of Your...

The Ross Simmonds Show ·

2025/12/20

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 and actionable advice, this episode challenges leaders to reflect on

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7:23

RSS 31: You Don’t Deserve a High‑Performing Team If...

The Ross Simmonds Show ·

2025/12/12

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, before looking outward, Ross encourages you to look in the mirror. He

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21:48

Generative Engine Optimization (GEO): Why I'm All In

The Ross Simmonds Show ·

2025/12/05

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 visibility across platforms, focusing not just on ranking, but on being

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167 results

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