The Ross Simmonds Show

Ross Simmonds
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  • Entrepreneurship
  • Updated twice weekly

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 59: AI Scales What You've Already Got: Matt Symes on Rewiring How You Operate

    13 hr ago

    RSS 59: AI Scales What You've Already Got: Matt Symes on Rewiring How You Operate

    In this episode of The Ross Simmonds Show, Ross sits down with Matt Symes, founder of Symplicity, to unpack why AI transformation fails when companies focus on tools, data, or privacy before fixing broken workflows. Matt shares a practical, workflow-first approach to using AI for sales, marketing, leadership, and business growth while helping founders avoid scaling chaos faster. Key Takeaways and Insights: 1. Why AI Won’t Fix a Broken Business - Matt explains why the “data problem” is often a stall tactic, not the real blocker to AI ROI. - Companies need to start with outcomes and workflows before buying AI tools or hiring AI leaders. - AI scales what already exists so broken systems become faster, messier, and more expensive if left unaddressed. 2. Workflow-First AI Transformation - The best first AI use case is a repetitive, time-consuming workflow that matters but does not create much strategic value. - Matt shares how an AI-powered dossier workflow replaced 10–15 hours of weekly admin work with an automated research process. - Leaders should identify the biggest business constraint—sales, marketing, delivery, or operations and use AI to improve that specific workflow. 3. Using AI to Improve Sales Conversion - Ross and Matt break down how AI can reduce sales cycle time and touchpoints. - Matt shares a real-world example of using open source intelligence and ChatGPT to prepare for a sales conversation, identify likely business problems, and close a deal in three touches. - The key lesson: AI can improve trust, relevance, and conversion when integrated directly into the sales process. 4. Strategy Before Speed - Matt emphasizes that every business must clearly define the problem it solves, who it solves it for, and the value of solving it. - The V8 example shows why businesses can lose growth opportunities when they define themselves by product category instead of customer problem. - Before making anything faster with AI, leaders must clarify their value proposition and target customer. 5. Why CEOs Should Lead AI Adoption - Matt argues that hiring a “Head of AI” too early can be a mistake if the CEO is not actively leading the mindset and workflow transformation. - AI should be treated as a teammate in value creation, not just another technology tool. - Leaders should delegate workflow ownership while staying accountable for the overall AI transformation strategy. 6. Agentic AI Use Cases for Leaders - Matt shares how he uses AI agents to monitor trusted sources, scan newsletters, and update keynote decks with timely research. - He explains how AI can support CEO responsibilities like business performance tracking, leadership coaching, 360 reviews, and scenario planning. - The conversation highlights why leaders should use AI to practice, prepare, and make better decisions, not just automate tasks. 7. Escaping the Founder’s Trap - Matt defines the founder’s trap as building a business that cannot operate without the founder playing a critical role. - He explains how founders can design businesses around their best life instead of becoming trapped by their own company. - Symplicity and Levership help companies build strategic cadence, improve workflows, and scale with more structure. Resources & Tools: 🔗 Symplicity 🔗Perplexity Computer  🔗 NotebookLM 🔗 OpenClaw  🔗 Claude Code  🔗 Claude Cowork — 👋🏾 Let's stay connected — ╰ Subscribe to my channel:  @RossSimmondsTV  ╰ Instagram:  @thecoolestcool   ╰ Twitter / X: @thecoolestcool   ╰ LinkedIn: linkedin.com/in/rosssimmonds — Connect with Matt  — ╰ LinkedIn: linkedin.com/in/matt-symes-8328a765/

    57 min
  2. RSS 58: All In on Claude: Travis Tallent on Building AI Systems That Actually Scale

    19 Jun

    RSS 58: All In on Claude: Travis Tallent on Building AI Systems That Actually Scale

    In this episode of The Ross Simmonds Show, Ross sits down with Travis Tallent of DayNova to unpack how organizations can use AI tools like Claude, Claude Code, Claude Chat, and Claude Co-Work to save time, improve workflows, and amplify business growth. Travis shares practical AI agent examples for marketing, sales, operations, finance, and account management, while emphasizing a strategic approach: automate the right work, keep humans in the loop, and reinvest saved time into higher-value output. Key Takeaways and Insights: 1. Using Claude to Build Smarter AI Workflows - Travis explains why Claude is his most-used AI tool and how he uses it for deep research, competitive analysis, proposals, and decision support. - Claude Code helps build and deploy proposal workflows, while Claude Chat acts as a strategic sparring partner. - Claude Co-Work can support daily briefs, research, project prioritization, and competitive monitoring. - The key is building strong skills with brand context, tone, design rules, and clear instructions so outputs feel useful and aligned. 2. The DayNova Framework for AI Transformation - Travis introduces the DayNova framework: Narrow, Orchestrate, Validate, and Amplify. - “Narrow” means identifying which tasks are actually worth automating instead of wasting time on low-impact workflows. - “Orchestrate” focuses on shared knowledge bases, governance, brand assets, and culture skills so teams use AI consistently. - “Validate” keeps humans in the driver’s seat, while “Amplify” reinvests productivity gains into growth, innovation, and domain expertise. 3. Helping Teams Adopt AI Without Fear - Travis explains why AI adoption is not just a software rollout; it is a change management challenge. - Leaders need to acknowledge uncertainty, build psychological safety, and help teams turn anxiety into agency. - AI should be positioned as a tool to change how work gets done, not as something that replaces people’s identity or value. - Successful adoption requires trust, team-specific training, and clear communication about how saved time will be reinvested. 4. AI Agents for Every Business Function - Marketing teams can build conversational agents connected to performance data, rankings, sales trends, and campaign insights. - Operations teams can create internal knowledge bases for policies, brand guidelines, culture, travel rules, and process documentation. - Account management teams can automate meeting notes, project management updates, and client communication scoring - Finance teams can use AI for PO reconciliation, forecasting, payroll workflows, contractor payments, and month-end close support. 5. AI for Sales, Revenue, and Relationship Building - Sales teams can use AI to summarize RFPs, analyze prospects, prepare for calls, and build automated sales coaching systems. - AI-powered prospect research helps teams enter conversations with stronger context and more relevant talking points. - Travis and Ross discuss how AI can strengthen both business and personal relationships through better follow-up and context tracking. - The highest-value human work shifts toward innovation, strategy, relationship-building, and big ideas that previously lacked enough time. Resources & Tools: 🔗 DayNova  🔗 Claude 🔗 Ahrefs — 👋🏾 Let's stay connected — ╰ Subscribe to my channel:  @RossSimmondsTV  ╰ Instagram:  @thecoolestcool   ╰ Twitter / X: @thecoolestcool   ╰ LinkedIn: linkedin.com/in/rosssimmonds — 👋🏾 Connect with Travis  — ╰ Instagram:  @tallentspeaks ╰ Twitter / X: @tallentspeaks ╰ LinkedIn: linkedin.com/in/travistallent

    46 min
  3. RSS 57: 20 Proven Customer Acquisition Tactics to Land Your First Clients

    12 Jun

    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
  4. 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
  5. 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
  6. 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
  7. 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

  8. 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
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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 - 2026
  • Episodes
    177
  • Rating
    Explicit
  • Copyright
    © Foundation Inc.
  • Show Website
    The Ross Simmonds Show

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