The Ross Simmonds Show

Ross Simmonds

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 57: 20 Proven Customer Acquisition Tactics to Land Your First Clients

    6 days ago

    RSS 57: 20 Proven Customer Acquisition Tactics to Land Your First Clients

    In this episode of The Ross Simmonds Show, Ross breaks down why founders often over-focus on perfecting the product while underinvesting in the most important part of business: getting customers to buy. He shares 20 practical customer acquisition tactics covering owned channels, outreach, community building, audience engagement, strategic partnerships, personal branding, and frictionless buying experiences. Key Takeaways and Insights: 1. Shift Your Mindset Around Sales - Stop treating every “no” as personal rejection and start seeing it as progress toward a “yes.” - Customer acquisition requires courage, repetition, and strategic thinking—not a massive budget. - Founders need to understand customer nuance, buying behavior, and how to create urgency around their offer. 2. Own Your Audience with Email - Build and maintain an email list so you can communicate directly with prospects and customers. - Make every email valuable enough to inspire, educate, entertain, or give subscribers a competitive edge. - Avoid using email only for product updates or blog announcements; turn it into a trusted resource. 3. Build a High-Value Resource Hub - Create a website section filled with useful tools, guides, quizzes, calculators, and interactive content. - Use gated resources and community features to capture leads and build deeper audience engagement. - Watch for social referral traffic as a signal that your content is valuable enough to share. 4. Create Communities Around Your Market - Build private Slack, Discord, Facebook, or Reddit communities where your ideal customers can gather. - Use these spaces to collect feedback, test ideas, host sessions, and create word-of-mouth momentum. - Stay close to your most engaged community members—they may become your strongest customers. 5. Master Personalized Outreach - Cold email still works when it is researched, relevant, and written for one specific person. - Use LinkedIn, company updates, investor reports, and business context to make outreach feel human. - Ask for feedback or a short conversation instead of immediately pushing for a demo or sale. 6. Leverage Your Existing Network - Reach out to past colleagues, classmates, and professional connections who may now be in relevant roles. - Ask for specific warm introductions and make it easy by writing the intro message for them. - Schedule no-pitch coffee chats to build awareness, gather market research, and create future evangelists. 7. Show Up Where Your Audience Already Spends Time - Participate in Reddit, Medium, Hacker News, Quora, Facebook groups, Slack communities, and X with value-first engagement. - Study the culture of each platform before posting so your contributions fit naturally. - Use podcasts, influencers, guest posts, webinars, and co-marketing to access already-established audiences. 8. Use Strategic Partnerships to Generate Leads - Build referral partnerships with complementary businesses that already serve your ideal customers. - Offer commissions, kickbacks, or revenue share to incentivize partners to send qualified leads. - Create co-branded content or guest content to borrow trust and reach from established audiences. — 👋🏾 Let's stay connected — ╰ Subscribe to my channel:  @RossSimmondsTV  ╰ Instagram:  @thecoolestcool   ╰ Twitter / X: @thecoolestcool   ╰ LinkedIn: linkedin.com/in/rosssimmonds

    32 min
  2. RSS 56: Why Smart Founders Step Away: The Data-Driven Case for Rest, Family, and Better Performance

    5 Jun

    RSS 56: Why Smart Founders Step Away: The Data-Driven Case for Rest, Family, and Better Performance

    In this episode of The Ross Simmonds Show, Ross breaks down why stepping away from the grind isn’t falling behind but a strategic advantage. Backed by research and real-life perspective, he shows how rest, presence, and intentional time off can actually fuel better performance, creativity, and long-term success. This is a must-listen for founders, marketers, and creators playing the long game. Key Takeaways and Insights: 1.  The Founder’s Dilemma: Grind vs. Presence - Internal conflict between business demands and personal life - Why many founders feel guilty stepping away - The long-term cost of always being “on” - Reframing rest as a strategic decision 2. The Hidden Cost of Hustle Culture - 72% of entrepreneurs report mental health challenges - Overworking increases risk of stroke and heart disease - Long hours may correlate with success—but also burnout - Why “more work” isn’t always the smartest path forward 3. The Science of Creative Breakthroughs - The “incubation effect” and how ideas form during rest - Why low-effort activities unlock better thinking - Real-world examples of breakthroughs away from the desk - How to structure downtime for maximum creative output 4. Why Time Off Drives Better Results - People who take vacations are more likely to earn raises - Rest improves decision-making and cognitive performance - The ROI of unplugging from work - How to think about rest as an investment, not a reward 5. Relationships Are the Ultimate Growth Strategy - 85-year Harvard study on happiness and longevity - Strong relationships outperform traditional health metrics - Loneliness as a hidden risk factor for founders - Why connection is a key part of sustainable success 6. Escaping the Founder Identity Trap - Why tying identity solely to business is dangerous - Stories of founders feeling lost after exit - The importance of building a multi-dimensional identity - How diversifying your identity strengthens resilience — 👋🏾 Let's stay connected — ╰ Subscribe to my channel:  @RossSimmondsTV  ╰ Instagram:  @thecoolestcool   ╰ Twitter / X: @thecoolestcool   ╰ LinkedIn: linkedin.com/in/rosssimmonds

    23 min
  3. RSS 55: Reddit, AI & Distribution: The B2B Playbook Most Brands Are Ignoring

    29 May

    RSS 55: Reddit, AI & Distribution: The B2B Playbook Most Brands Are Ignoring

    Reddit is influencing more B2B buying decisions than most marketers realize. In this episode, Jon Clark from Page 2 Podcast sits down with Ross to explore how Reddit has become a powerful force in search, why AI is transforming content distribution, and what it takes to build a marketing engine that drives real reach and results. Ross shares practical insights on SEO, content strategy, brand visibility in the age of LLMs, and why the future belongs to teams that invest as heavily in distribution as they do in creation. This conversation is packed with actionable lessons for marketers looking to stay ahead of the next wave of digital growth. Key Takeaways and Insights: 1. Building an AI-Powered Content Engine - Automating idea capture with transcriptions, cloud tools, and AI prompts. - Using spreadsheets + APIs + AI to create a personal “life operating system.” - AI accelerates execution but strategy and human oversight remain critical. - If you’re not 15–20% faster than last year, you’re underutilizing AI. 2.  Reddit’s Takeover of Bottom-of-Funnel Search - Reddit now dominates long-tail, high-intent B2B queries. - “Best CRM for real estate small business” style queries are ranking. - Traditional SEO tools showed “zero volume”—but users asked Reddit anyway. - LLMs amplify this effect by generating personalized, long-tail queries. 3. How LLM Memory Changes Search Strategy - AI tools remember context (industry, revenue, location, preferences). - This creates ultra-specific queries behind the scenes. - Reddit wins because it has depth across long-tail discussions. - Strategy shift: Influence conversations where LLMs source answers. 4. The 3 Reddit Accounts Every Brand Needs - ✅ Brand Subreddit (protect your namespace immediately). - ✅ Brand Account (gratitude + reputation management only). - ✅ Personified Account (human engagement + trust building). 5. Organic + Paid Reddit = Scalable Growth - Reddit ads work best when inspired by top-performing organic posts. - Redditors reject polished corporate ads—match the culture. - Use conversational tone and authentic creative. - Lowest CPL often comes from culturally aligned campaigns. 6. Create Once, Distribute Forever (In the AI Era) - Shift from “create, create, create” to “distribute and optimize.” - Search is now multi-platform: Google, YouTube, Reddit, LLMs. - Distribution has moved from “vitamin” to “painkiller.” - Modern SEO = marketing across ecosystems. Resources & Tools: 🔗 Page 2 Podcast  🔗 Create Once. Distribute Forever  — 👋🏾 Let's stay connected — ╰ Subscribe to my channel:  @RossSimmondsTV  ╰ Instagram:  @thecoolestcool   ╰ Twitter / X: @thecoolestcool   ╰ LinkedIn: linkedin.com/in/rosssimmonds

    56 min
  4. RSS 54: Build a Distribution System That Actually Drives Growth

    23 May

    RSS 54: Build a Distribution System That Actually Drives Growth

    Too many marketers hit publish and hope for the best. In this episode, Ross breaks down why hope is not a distribution strategy and what to do instead. You’ll learn how to build a deliberate, repeatable content distribution system that amplifies reach, compounds results, and drives measurable business growth in the AI era. Key Takeaways and Insights: 1. Hope Is Not a Distribution Strategy - Publishing and “hoping” for shares, rankings, or virality is not a growth plan. - Great content alone doesn’t guarantee reach or impact. - Distribution is the difference between obscurity and authority. 2. Why Great Content Still Loses - Average content often wins because it’s distributed strategically. - Algorithms reward engagement velocity, reach, and timing not just quality. - Distribution turns good content into great content. 3. AI, LLMs & the New Search Reality - AI-powered search is reducing traditional click-through traffic. - Optimizing for rankings alone is no longer enough. - LLMs pull from platforms like Reddit, LinkedIn, and licensed content sources. - Smart distribution increases your visibility across AI-driven experiences. 4. The Five Biggest Distribution Mistakes - Publishing once and disappearing. - Relying exclusively on one channel. - Assuming organic reach is guaranteed. - Failing to repurpose content across formats. - Not tracking performance or outcomes. 5. Create Once, Distribute Forever - Turn one blog post into carousels, threads, emails, videos, and podcasts. - Break pillar assets into micro-content for every channel. - Reshare and repackage content over time don’t let it die after launch week. - Repurposing multiplies ROI without multiplying effort. 6. Build a Real Distribution Strategy (Step-by-Step) - Conduct content-market fit research: understand pains, desires, and behaviors. - Analyze channel-user fit: where your audience actually spends time. - Study attention leaders (even outside your niche) to reverse-engineer engagement. - Create a pillar asset, repurpose aggressively, distribute across owned, earned, paid, and shared channels. - Rinse, repeat, and optimize using data. Resources & Tools: 🔗 Distribution.ai 🔗 Create Once, Distribute Forever 🔗 HubSpot 🔗 Ahrefs 🔗 Google Analytics 4 🔗 SparkToro — 👋🏾 Let's stay connected — ╰ Subscribe to my channel:  @RossSimmondsTV  ╰ Instagram:  @thecoolestcool   ╰ Twitter / X: @thecoolestcool   ╰ LinkedIn: linkedin.com/in/rosssimmonds

    26 min
  5. RSS 53: The Future CMO: Why You Must Become a Media Operator in the Age of AI

    15 May

    RSS 53: The Future CMO: Why You Must Become a Media Operator in the Age of AI

    In this episode of The Ross Simmonds Show, Ross makes a bold prediction: the next great CMO will be a media operator with a marketing budget. As AI and LLMs reshape how buyers discover and decide, traditional attribution, funnels, and SEO playbooks are breaking down. If you want to win in an AI-first world, it’s time to shift from campaign thinking to category ownership. Key Takeaways and Insights: 1. The Future CMO = Media Operator - The next generation of CMOs won’t just build campaigns—they’ll own media ecosystems. - Success shifts from “creating great ads” to controlling the narrative across a category. - Media ownership (owned + partnered) becomes a strategic advantage. 2. AI Is Rewriting Buyer Behavior - LLMs like ChatGPT, Gemini, and Claude are influencing buying decisions directly. - Consumers are getting answers without visiting your website. - The opportunity isn’t to interrupt attention—it’s to shape what AI recommends. 3. The Power of LLM Memory - AI personalizes answers based on stored user context (company size, budget, role). - Each platform (Gemini, ChatGPT, Claude) has different memory advantages. - Tracking only head terms is a mistake—long-tail, bottom-of-funnel queries matter more. 4. From Presence to Scale - Old model: “How much content did we publish?” - New model: “How often are we referenced across the web?” - Visibility in conversations—onsite and offsite—is the new KPI. 5. Category Ownership Through Media Acquisition - Buy and build media assets within your niche. - Create high-value, proprietary, non-commodity content. - Distribute aggressively to influence what LLMs cite and recommend. — 👋🏾 Let's stay connected — ╰ Subscribe to my channel:  @RossSimmondsTV  ╰ Instagram:  @thecoolestcool   ╰ Twitter / X: @thecoolestcool   ╰ LinkedIn: linkedin.com/in/rosssimmonds

    15 min
  6. 7 May

    RSS 52: Why 44.8% of B2B Content Fails to Earn Backlinks And the 3 Formats That Actually Work

    In this episode of The Ross Simmonds Show, Ross breaks down findings from the B2B Backlink Intelligence Report, an analysis of 12,154 pages across 24 B2B brands and 11 verticals, to reveal why 44.8 percent of thought leadership content fails to earn meaningful backlinks. He exposes the 9.5-point performance gap hiding inside most B2B content strategies and shares the three underutilized formats that consistently generate authority, links, and compounding growth. Key Takeaways and Insights: 1. The 44.8% Failure Rate of Thought Leadership - Thought leadership accounts for 37 percent of B2B content but earns only 27 percent of backlinks. A 9.5-point performance gap signals massive resource misallocation across the industry. - Most teams never audit whether their executive POV content actually earns links. The data exposes a problem most marketing leaders are actively ignoring. 2. Inside the B2B Backlink Intelligence Report - The study analyzed 12,154 pages across 24 B2B brands and 11 verticals using two core questions: what format is it and how many referring domains does it earn? - The most published format turned out to be the worst performer on a per-page basis. Data replaces opinion. The receipts are in. 3. Why Thought Leadership Underperforms - Thought leadership sounds strategic but internal applause, Slack praise, and LinkedIn likes create a false sense of traction. Teams rarely check backlinks, citations, or amplification metrics. - Most brands overestimate how much the market cares about executive opinions. Journalists and analysts want citable data, clear definitions, and practical insights. Not hot takes. 4. When Thought Leadership Actually Works - It performs best when the brand is already famous. Authority compounds authority and mid-market brands rarely break through on opinion alone. - Unique data paired with a strong perspective outperforms pure POV every time. The question is not whether thought leadership works. It is whether it will work for you. 5. The Link Magnet Trifecta - Three formats consistently outperform thought leadership with higher efficiency rates, lower fail rates, and compounding backlink growth over time. - Most B2B teams are dramatically under-allocating to these formats while continuing to invest in the one with the worst returns. 6. Stats and Data Roundups: 4.25x Efficiency - Stats pages carry a fail rate of just 5.3 percent and a breakout rate of 42 percent to 1,000-plus referring domains. Journalists constantly search for consolidated, up-to-date statistics. - One well-maintained stats page can outperform a year of blog posts. Keep it fresh. Rankings and relevance drive long-term link velocity. 7. Glossary and Definition Pages - Writers link to the clearest definition available. Definitions age better than predictions or trend pieces, making these pages durable link assets. - Own the terminology in your category and you own the citations. This format remains powerful for links even as organic traffic patterns shift. 8. How-To Content Independent of Your Product - The highest-performing how-to content solves tasks even if your product did not exist. Avoid product documentation disguised as SEO content. - Utility-driven tutorials earn links because they help the broader ecosystem. Top performers covered tools and topics like Google Drive, HTML, Fiverr, and Alibaba. 9. Backlinks Still Matter in the AI Era - Google still runs on links even in AI mode. Authority signals matter more now, not less. Backlinks are infrastructure for search visibility across both traditional and generative engines. - The compounding effect rewards long-term operators. Every link earned today is a signal that shapes AI visibility tomorrow. 10. Think Like an Investor, Not an Artist - Backlinks compound after publication. Audit your content strategy before publishing another thought leadership piece and reallocate toward formats with asymmetric upside. - Invest more. Guess less. The brands that treat content like a portfolio will outperform the ones treating it like a creative outlet. Resources & Tools: 🔗 B2B Backlink Intelligence Report — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds

    21 min
  7. 1 May

    RSS 51: LLM Visibility Playbook. 5 Proven Moves to Win in the AI Search Era

    In this episode of The Ross Simmonds Show, Ross breaks down why showing up in LLMs like ChatGPT, Claude, and Perplexity is the biggest marketing shift of our time and why treating it like SEO 2.0 is a losing strategy. He walks through five practical plays to build citation authority, dominate AI visibility, and engineer the kind of distribution leverage that compounds long after you press publish. Key Takeaways and Insights: 1. The Shift from SEO to GEO - In 2018, Reddit was dismissed. In 2026, it powers over 60 percent of bottom-funnel LLM citations. Google, OpenAI, and Anthropic are actively licensing and training on Reddit data. - Most teams are still optimizing for keywords and backlinks. GEO rewards authority, citations, and entity strength. The game has changed and the old playbook will not save you. 2. Play 1: Build a Citation Stack with Original Research - LLMs prioritize strong signals. Non-commodity content, original data, research, and clear POV outperforms generic blog posts every time. - Make every stat screenshot-friendly and quotable. Pitch your research to publications already cited in LLMs to compound authority and become the source models reference. 3. Play 2: Plant Flags in Communities - Reddit is one of the most cited sources in major LLMs. Identify three communities where your audience actually spends time and show up there consistently. - Use the Sherlock Homeboy Method: revive proven topics with a modern angle. Contribute value without pitching. Build reps. Create a moat competitors cannot climb. 4. Play 3: Engineer Your Entity Graph - LLMs see entities, not webpages. Companies, people, and products are all connected. Guest posts, podcast appearances, and transcripts strengthen your entity signal. - Consistent handles, bios, and positioning across platforms increase recognition. Say the same thing clearly thousands of times. Strategic repetition builds authority. 5. Play 4: Structure Content for Extraction - LLMs extract facts and quote passages. They ignore fluff. Use inverted pyramid writing: answer first, explain second. - Clear H1, H2, and H3 hierarchies improve both human and machine comprehension. Schema, lists, tables, and internal linking help models understand and cite your content. 6. Play 5: Distribution Is the Final Moat - One asset. Fifty distributions. Multiple citation paths. Most brands post once and disappear. Winners distribute relentlessly. - Every surface, LinkedIn, Reddit, YouTube, Substack, and podcasts, becomes training data. Distribution compounds trust with both humans and machines. 7. The Future: AI Agents Will Change Buying Forever - By 2038, AI assistants will mediate most purchasing decisions. Buyers will not browse. They will delegate. - The content LLMs train on today will shape tomorrow's recommendations. If you are not building your moat now, you will be rebuilding from scratch later. 8. The Long-Term Advantage Goes to Those Who Invest in Themselves - The skills that worked in 2018 will not carry you to 2038. Read. Study. Experiment. Adapt. - Earned momentum compounds through disciplined execution. Play the long game. Resources & Tools: 🔗 ChatGPT 🔗 Claude 🔗 Perplexity 🔗 Reddit 🔗 Google 🔗 OpenAI 🔗 Anthropic 🔗 LinkedIn 🔗 YouTube 🔗 Substack — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds

    19 min
  8. 24 Apr

    RSS 50: The Bold Thesis "Distribution Is the Last Moat Standing"

    In this episode of The Ross Simmonds Show, Ross breaks down why OpenAI and HubSpot's media acquisitions this quarter aren't about content quality. They're about owning distribution. He connects the dots on what this land grab means for every B2B marketer and how to apply the same strategy without a billion-dollar balance sheet. Key Takeaways and Insights: 1. Media Acquisition Is the New Moat - OpenAI and HubSpot made bold media acquisitions in the same quarter. This isn't about content quality. It's about owning the rooms where buying decisions happen. - Distribution is leverage. And leverage compounds. The brands that win will own the audience, not just the message. 2. The Land Grab Has Already Started - Penn bought Barstool. HubSpot acquired The Hustle and Starter Story. Robinhood built a media empire. Plaid acquired fintech media to own operator attention. - The cadence of these deals is accelerating. This is not a trend. It's a land grab and most B2B teams haven't noticed. 3. Super Bowl Ads vs. Owned Attention - $27M buys six Super Bowl ads that disappear in 30 seconds. The same capital can buy a media asset with daily access to your exact ICP. - Most teams rent attention. The best operators own it. Predictable pipeline starts with predictable distribution. 4. Google's AI Shift Changes the Game - AI Overviews are reducing clicks to traditional search results while Google embeds YouTube directly into the SERP. - Media value is no longer just blog rankings. It's multimedia presence. Visibility now requires platform-native authority. 5. You Cannot Game LLM Visibility - Traditional SEO could be manipulated with backlinks and paid boosts. AI visibility requires real brand equity and positive sentiment. - LLMs train on authority signals across media properties. If you want to show up in AI answers, you must be worth citing. 6. Brand Equity Beats Editorial Independence - Acquired media serves stakeholders. Narrative shapes culture and buying media shapes narrative. - Read content with context. Ownership matters. Content influence increasingly flows through owned channels. 7. The 4 Distribution Questions Every Marketer Should Ask - Which newsletter has the audience you wish you had? Which creator has your buyers' trust? What shows does your ICP consume weekly? What niche media opportunity is still wide open? - Use LLMs and audience intelligence tools to find answers faster. The operators asking these questions now are building moats everyone else will pay to access later. 8. How to Build a Media Engine Without Buying One - Start one channel and let patience compound. Sponsor niche newsletters instead of chasing giants. Partner with trusted creators via revenue share, salary, or equity. - In the AI era, content is cheap. Reputation and distribution are scarce. Build accordingly. 9. Three Predictions for the Next Decade - By 2035, every unicorn B2B company will own a media property. Newsletter and YouTube network valuations will triple as LLM visibility becomes priced in. - Agencies will survive by brokering, building, or optimizing media ecosystems, not just producing content. 10. Distribution Is the Last Moat Standing - AI commoditized content creation. The advantage shifts to those who control reach. A true content moat goes beyond your domain. - Visibility is engineered, not hoped for. The window to build that moat cheaply is closing fast. Resources & Tools: 🔗 OpenAI 🔗 HubSpot 🔗 The Hustle 🔗 Starter Story 🔗 Robinhood 🔗 Plaid 🔗 Barstool Sports 🔗 Google  🔗 YouTube — 👋🏾 Let's stay connected — ╰ Subscribe to my channel: @RossSimmondsTV ╰ Instagram: @thecoolestcool ╰ Twitter / X: @thecoolestcool ╰ LinkedIn: linkedin.com/in/rosssimmonds

    20 min

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.

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