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The Ross Simmonds Show

Ross Simmonds
The Ross Simmonds Show
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191 episodes

  • The Ross Simmonds Show

    RSS 72: Revenue Systems That Scale: Doug Davidoff on Building Predictable Growth

    28/09/2026 | 48 mins.
    In this episode of The Ross Simmonds Show, I sit down with Doug Davidoff to break down how high-growth companies build predictable revenue systems through better decisions and disciplined execution. If you want a more strategic approach to RevOps, sales leadership, go-to-market strategy, and AI in sales, this conversation gives you a practical framework you can apply in the next 90 days.

    Key Takeaways and Insights:

    1. Why "sounds good" advice stalls growth

    - Doug explains why advice that feels exciting but lacks market validation often leads teams in the wrong direction.

    - Real growth comes from testing ideas in the market, learning from customer behavior, and adjusting based on actual feedback.

    - The fastest-growing companies don't assume certainty. They build around experimentation.

    2. The revenue acceleration framework in action

    - Doug shares the core principle of hypothesis-driven growth: make a decision, test it, measure the result, and refine.

    - He makes the case that the companies that learn the fastest often build the most sustainable competitive advantage.

    - A strong revenue system is built through continuous feedback loops between strategy and execution.

    3. The three zones of execution

    - Zone 1 focuses on the next 90 days and the day-to-day performance required to run the business.

    - Zone 2, the enablement zone, is where companies operationalize change and prepare for future growth.

    - Zone 3 is the transformation zone, where leaders define the long-term vision and direction of the company.

    - Doug explains that most teams have plenty of ambition. Where they struggle is skipping the structure that connects today's work to tomorrow's outcomes.

    4. Process, discipline, and predictable growth

    - Successful organizations rely on routines and review cycles to drive results instead of counting on heroic effort.

    - Doug highlights the importance of focusing on inputs alongside outputs to create more predictable sales and revenue performance.

    - He pushes leaders to cut the noise and focus on the two or three initiatives that matter most.

    5. AI, sales systems, and staying strategic

    - Doug shares a balanced perspective on AI in revenue operations, arguing that most companies are still in the early stages.

    - AI can accelerate execution, but only when the underlying process and data are already clear.

    - The real advantage comes from using AI to support better thinking.

    6. Lessons from sports for sales and leadership

    - Drawing from his experience coaching college baseball, Doug explains how process drives performance in both sports and business.

    - Just like hitters need a repeatable swing path, sales teams need a repeatable path that increases the probability of success.

    - Great leaders stay focused on fundamentals and steady improvement over time.

    Resources & Tools:

    🔗 LiftEnablement.com - https://www.liftenablement.com/

    🔗 The RevOps Show - https://www.liftenablement.com/podcasts/revops-show

    — 👋🏾 Let's stay connected —

    ╰ Subscribe to my channel: @RossSimmondsTV

    ╰ Instagram: @thecoolestcool

    ╰ Twitter / X: @thecoolestcool

    ╰ LinkedIn: linkedin.com/in/rosssimmonds

    — Connect with Doug —

    ╰ LinkedIn: linkedin.com/in/doug-davidoff-76396b1/
  • The Ross Simmonds Show

    RSS 71: How to Become Unignorable: Katelyn Bourgoin on Owning One Idea and Building a Brand People Remember

    21/09/2026 | 53 mins.
    In this episode of The Ross Simmonds Show, I sit down with Katelyn Bourgoin to unpack what it really takes to become unignorable in today's crowded content landscape. We explore how marketers, creators, consultants, and founders can own an idea, build compound authority, and turn strategic content distribution into long-term brand equity.

    Key Takeaways and Insights:

    1. What It Means to Be UNIGNORABLE

    - Katelyn explains why great content alone is no longer enough in a saturated market.

    - The real advantage comes from owning a clear, memorable idea in the minds of your audience.

    - We break down how repetition, positioning, and trust help brands stand out over time.

    2. How to Own an Idea in Your Market

    - The conversation highlights examples like Cody Sanchez, James Clear, Simon Sinek, and Seth Godin to show how ownable ideas spread.

    - Katelyn shares the difference between catchy language and the deeper argument underneath it.

    - Learn why the strongest personal brands are built on revelatory ideas that change how people think.

    3. A Practical Framework for Thought Leadership

    - Katelyn outlines a five-part framework for shaping an ownable idea: aspiration, problem, lens, revelation, and directive.

    - She emphasizes aligning your message with what your buyers need to hear, not just what you want to say.

    - This section is especially useful for digital marketers and business owners looking for a repeatable content strategy.

    4. AI, Content Creation, and Better Judgment

    - AI can speed up drafting and ideation support, but it should not replace real learning or strategic thinking.

    - The key takeaway: use AI to amplify your process, not to shortcut the development of judgment and expertise.

    5. Building Authority Through Experience and Consistency

    - Katelyn shares why credibility matters and why doing the reps often comes before becoming a thought leader.

    - We discuss the "messenger effect" and why who says something can matter as much as what is being said.

    - The episode reinforces a strategic truth: consistent publishing compounds slowly, then pays off in a big way.

    6. Entrepreneurship, Resilience, and Finding Your Path

    - Katelyn opens up about startups, bankruptcy, burnout, and the lessons that shaped her current business model.

    - She explains why founders need to get honest about what they actually want instead of chasing someone else's version of success.

    - This part of the conversation offers encouraging guidance for anyone navigating uncertainty, reinvention, or early-stage growth.

    Resources & Tools:

    🔗Be UNIGNORABLE - https://beunignorable.com/

    — 👋🏾 Let's stay connected —

    ╰ Subscribe to my channel: @RossSimmondsTV

    ╰ Instagram: @thecoolestcool

    ╰ Twitter / X: @thecoolestcool

    ╰ LinkedIn: linkedin.com/in/rosssimmonds

    — Connect with Katelyn —

    ╰ Twitter / X: @KateBour

    ╰ LinkedIn: linkedin.com/in/katebour/
  • The Ross Simmonds Show

    RSS 70: Mastering Time: Prioritization Over Productivity

    14/09/2026 | 14 mins.
    In this episode of The Ross Simmonds Show, I challenge the common belief that productivity struggles come from not having enough time. Instead, I make the case that the real issue is weak prioritization, and I share a practical framework for using calendars, delegation, and focused decision-making to create meaningful progress.

    Key Takeaways and Insights:

    1. Every Priority Has a Price

    - Choosing one priority means consciously saying no to something else.

    - Treating every task as equally urgent leads to stalled momentum and scattered energy.

    - High-impact work often creates outsized returns, even when it takes less effort than lower-value tasks.

    2. Applying the 80/20 Rule to Your Work

    - A small percentage of your efforts often drives the majority of your results.

    - The goal is to identify the few actions with the highest return and spend more time there.

    - This mindset helps marketers, creators, and business owners stop overinvesting in tasks that do not move the needle.

    3. Your Calendar Reveals Your Commitment

    - Calendars are one of the most important tools for achieving goals.

    - If a goal is not reflected in your schedule, it is probably not a true priority.

    - Intentional calendar planning creates structure, accountability, and better follow-through.

    4. Time Blocking with Intention

    - I share how I have used calendar systems for years to protect focused work and personal commitments.

    - I recommend scheduling everything that matters, from deep work to family time.

    - Repeatable blocks like no-meeting days can help create consistency and protect your best energy.

    5. Categorize Your Time for Better ROI

    - Tracking where your time goes helps you measure whether your effort aligns with your goals.

    - Categories like sales, marketing, personal development, and family create visibility into what is actually getting your attention.

    - For leaders, this same approach can help teams improve performance and resource allocation.

    6. Stop Being the Bottleneck

    - Leaders often slow growth by making themselves the default answer for every decision.

    - I frame this as an ego issue as much as an operational one.

    - Delegation, empowerment, and trust are essential if you want your team and your business to scale.

    7. Delegate to Unlock Growth

    - I reflect on my own experience as a founder who used to approve everything.

    - Real growth happened when I gave ownership and accountability to others.

    - Training people to make strong decisions frees you to focus on the highest-value work.

    8. Better Outcomes Come from Better Decisions

    - Constant activity is not the same as meaningful progress.

    - One thoughtful, well-timed decision can create more impact than dozens of small reactive tasks.

    - Strategic leaders focus less on looking busy and more on solving the right problem.

    9. Think in Sprints Around the Biggest Problem

    - Identify the single biggest issue holding them back.

    - Focus your energy relentlessly on that one constraint instead of bouncing between distractions.

    - Breakthroughs often come from sustained attention on one important problem over a defined period.

    — 👋🏾 Let's stay connected —

    ╰ Subscribe to my channel: @RossSimmondsTV

    ╰ Instagram: @thecoolestcool

    ╰ Twitter / X: @thecoolestcool

    ╰ LinkedIn: linkedin.com/in/rosssimmonds
  • The Ross Simmonds Show

    RSS 69: B2B Marketing Growth Strategies: What Dave Gerhardt Gets Right About Content, Distribution and Brand

    07/09/2026 | 45 mins.
    In this episode of The Ross Simmonds Show, I sit down with Dave Gerhardt to unpack what it really takes to win in B2B marketing today, from building brand through content and community to creating distribution that compounds over time. We also dive into AI, events, audience trust, hiring, and the mindset shifts required to build a durable media brand in a crowded market.

    Key Takeaways and Insights:

    1. B2B Marketing Strategy in a Media-First World

    - Dave explains why marketing a media business differs from marketing a software company, especially when the product is the audience's attention.

    - We get into why more software brands are buying media companies to gain distribution, relevance, and brand equity.

    - We explore how owned media and off-platform content can strengthen visibility, including emerging benefits tied to AI search and LLM citations.

    2. The Playbook for Starting from Scratch

    - Dave shares how he would approach B2B growth if he had to rebuild without his existing audience or personal brand.

    - His framework starts with understanding the buyer deeply, then creating highly specific content for a clearly defined niche.

    - A key takeaway I pull from this: great marketers do not force channels, they go where the audience already is, whether that is LinkedIn, YouTube, or even Facebook groups.

    3. Building Exit Five Through Brand, Quality, and Focus

    - Dave breaks down the pivotal moves that helped Exit Five grow: rebranding, hiring key operators, and raising the quality bar across content and events.

    - He explains why perception matters in marketing and how a real brand creates more long-term value than a personality-led business alone.

    - This reinforces something I believe strongly: when you take the work more seriously, the market often responds in kind.

    4. AI, Human Creativity, and the Future of Marketing

    - Dave and I discuss where AI helps and where it falls short, especially in storytelling, originality, and emotional nuance.

    - Dave shares a candid lesson from writing a keynote and why relying too heavily on AI can flatten great ideas into generic output.

    - For marketers, my takeaway is clear: use AI as a tool, but keep human insight at the center of content creation.

    5. Community, Events, and Real-World Connection

    - In-person events as a competitive advantage in a digital-first world.

    - Dave explains how event curation, speaker selection, and genuine audience experiences can drive brand loyalty beyond direct ROI metrics.

    - We also discuss why analog experiences and real relationships are becoming even more valuable as digital content becomes easier to mass-produce.

    6. Lessons on Leadership, Talent, and Continuous Improvement

    - Dave reflects on hard feedback, impulsiveness, sponsor fit, and the importance of not arguing when protecting brand trust.

    - He shares how Exit Five attracts top talent through brand reputation, product quality, and operational rigor.

    - The broader lesson I take away is strategic and practical: strong businesses are built through focus, iteration, and a willingness to raise the standard over time.

    Resources & Tools:

    🔗 Exit Five - https://exitfive.com/

    🔗 Drive 2026 - https://exitfive.com/drive/

    — 👋🏾 Let's stay connected —

    ╰ Subscribe to my channel: @RossSimmondsTV

    ╰ Instagram: @thecoolestcool

    ╰ Twitter / X: @thecoolestcool

    ╰ LinkedIn: linkedin.com/in/rosssimmonds

    — Connect with Dave —

    ╰ Twitter / X: @davegerhardt

    ╰ LinkedIn: linkedin.com/in/davegerhardt
  • The Ross Simmonds Show

    RSS 68: Reddit, ChatGPT, and the Truth About AI Citations: Why Smart Marketers Shouldn’t Panic

    31/08/2026 | 18 mins.
    In this episode of The Ross Simmonds Show, I break down what Reddit’s decline in ChatGPT citations actually means for marketers, brands, and content teams. Instead of reacting to headlines, I share a more strategic view of Reddit’s role in AI search, Google visibility, community engagement, and bottom-of-funnel influence.

    Key Takeaways and Insights:

    1. The Reddit Citation Panic Explained

    - I address the wave of reactions after reports showed Reddit appearing less often in ChatGPT citations.

    - This shift is not a signal to abandon Reddit altogether.

    - The bigger lesson: marketers need context before making channel decisions.

    2. Not All LLM Prompts Are Created Equal

    - Different prompts require different types of sources, and Reddit is not ideal for every query.

    - Reddit may be useful for software, tech, and troubleshooting questions, but less appropriate for sensitive topics like health.

    - Citation changes should be evaluated based on use case, not hype.

    3. Why Marketers Need to Track Citations Themselves

    - Third party studies can be helpful, but they do not replace brand specific monitoring.

    - I encourage teams to benchmark how their own prompts, categories, and keywords perform across LLMs.

    - Ongoing tracking is essential for adapting to algorithm changes in AI search.

    4. Reddit Still Matters for Enterprise and Bottom of Funnel Queries

    - Even with fewer citations overall, Reddit remains relevant for transactional and bottom of funnel enterprise software searches.

    - For B2B marketers, that means Reddit can still influence high intent buyers.

    - Strategic prompt tracking can uncover where Reddit continues to drive value.

    5. AI Search Is Changing Constantly

    - Volatility is now part of digital marketing.

    - Citation sources can shift between Reddit, LinkedIn, YouTube, review sites, and competitors at any time.

    - The most effective marketers build systems to monitor change instead of reacting emotionally.

    6. Google Still Gives Reddit Massive Visibility

    - Reddit's value goes beyond ChatGPT because Google still heavily features Reddit in organic search, AI Overviews, and AI Mode.

    - As long as Google dominates search behavior, Reddit remains strategically important.

    - Marketers should think beyond one platform when evaluating channel performance.

    7. Reddit Is Still Where Real Buyers Ask Real Questions

    - Millions of users visit Reddit daily to research products, services, tools, and business decisions.

    - The platform remains a trusted space for niche discussions, peer recommendations, and category conversations.

    - That creates strong opportunities for brands that want to influence informed buyers.

    8. Value Wins on Reddit

    - Reddit's strong moderation and anti spam systems are a big reason the platform still matters.

    - Brands that show up only to promote themselves will struggle.

    - Brands that consistently help, educate, and participate authentically can build real credibility.

    9. A Smarter Reddit Strategy for Brands

    - Teams can study top performing posts, identify audience needs, and create content that genuinely helps the community.

    - The best Reddit strategy starts with value, not self promotion.

    - Instead of dropping Reddit because of one data point, brands should diversify their approach across SEO, community, ads, and AI visibility.

    — 👋🏾 Let's stay connected —

    ╰ Subscribe to my channel: @RossSimmondsTV

    ╰ Instagram: @thecoolestcool

    ╰ Twitter / X: @thecoolestcool

    ╰ LinkedIn: linkedin.com/in/rosssimmonds
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About 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.
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