The Ross Simmonds Show

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/

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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.

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In this episode of The Ross Simmonds Show, Ross breaks down how search behavior has evolved beyond Google and why brands need a broader visibility strategy in the age of ChatGPT, Perplexity, Grok, and other LLMs. He shares five practical strategies to help marketers, creators, and business owners strengthen AI visibility, influence buyer discovery, and build a smarter content distribution engine for long-term growth.

Key Takeaways and Insights:

1. Increase your brand’s surface area

- Visibility now depends on how often your brand appears across the sources LLMs use to generate answers.

- Google and AI tools increasingly answer questions without sending users to your site.

- Expanding brand mentions across blogs, videos, forums, and other platforms increases your chances of being cited.

2. Your Website Is No Longer the Only Asset That Matters

- User-generated content, affiliate sites, and review platforms now play a major role in shaping buyer decisions.

- Third-party trust signals can influence LLM responses even when direct traffic is declining.

- Positive brand sentiment on platforms like G2, Capterra, TrustRadius, and Yelp can improve AI visibility.

3. Every LLM Sources Information Differently

- Claude, Perplexity, ChatGPT, and Grok do not pull from the web in the same way.

- Broad industry assumptions are less useful than prompt-specific research in your niche.

- Marketers need to track which sources appear for their own target queries before building strategy

4. Reddit Requires Real Community Participation

- Spamming Reddit or trying to manipulate conversations is a fast way to get banned.

- Authentic engagement and value-first participation are far more effective than artificial promotion.

- Building trust through genuine contribution can create a sustainable Reddit presence over time.

5. Reverse Engineer What LLMs Already Reward

- Use keyword research as a proxy to estimate which queries may also appear in LLM usage.

- Track prompts to see what content formats and sources are being cited.

- If LLMs favor listicles, comparison pages, landing pages, YouTube videos, or Reddit threads, build for those patterns.

6. Build an AI Visibility Strategy That Drives Pipeline

- The goal is not just awareness, but measurable business impact.

- Teams should align SEO, content distribution, and prompt tracking into one structured visibility strategy.

- Brands that play the long game will be better positioned to earn trust, citations, and conversions.

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In this episode of The Ross Simmonds Show, Ross sits down with Malte Landwehr, CMO of Peec.ai, to unpack what AI visibility really means for modern marketers and how it differs from traditional SEO. They break down how brands can measure LLM visibility, identify the right prompts to track, prioritize the channels that influence AI answers, and build a smarter cross-functional strategy to win recommendations in tools like ChatGPT, Perplexity, Gemini, and more.

Key Takeaways and Insights:

1. AI Visibility vs Traditional SEO

- Traditional SEO was built around earning clicks and website traffic, while AI search is increasingly about getting your brand recommended inside the answer.

- In AI-driven search experiences, users may never visit your site, which changes how marketers think about attribution, brand experience, and customer journeys.

- Malte explains why this shift impacts not just SEO teams, but also content, brand, support, PR, affiliate, and product documentation teams.

2. How to Measure AI Search Performance

- Malte outlines four core ways to measure AI visibility: self-reported attribution, web analytics, log file analysis, and prompt tracking.

- Self-reported attribution is a strong starting point for teams trying to validate whether LLMs are already influencing pipeline and revenue.

- Prompt tracking stands out as the most actionable measurement method because it helps marketers spot content gaps, benchmark competitors, and prioritize next steps.

3. Prompt Tracking and Strategy That Actually Works

- The best prompt strategies start with topics, intent, personas, and funnel stage rather than obsessing over exact wording.

- Real-world testing shows that people use many different prompts, but LLMs often return similar brand recommendations when the underlying intent is the same.

- Malte warns marketers not to overreact to tiny data sets or short-term fluctuations, and instead evaluate performance directionally across prompt sets over time.

4. The New Playbook for AI-Era Content Distribution

- LLMs pull from a wide range of sources, including help centers, FAQs, social content, news sites, directories, review platforms, and community discussions.

- Brands need consistent positioning across all managed and owned surfaces so AI systems can clearly understand and describe what the company does.

- Smart teams use source-level visibility data to decide where to invest, whether that means digital PR, creator partnerships, editorial placements, review platforms, or competitor-inspired content.

5. Agentic Commerce and the Future of Marketing Workflows

- Malte shares why agentic commerce will likely arrive faster in B2B procurement and operational workflows than in emotional consumer purchases.

- He also explains how AI tools and MCP integrations are changing the software experience, allowing marketers to work through AI interfaces instead of traditional dashboards.

- For early-career marketers, his advice is clear: become AI-native, use AI first to solve problems, and build the habit of testing, iterating, and learning fast.

Resources & Tools:

🔗 Peec.ai

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╰ Instagram: @malte.landwehr.official

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╰ LinkedIn: linkedin.com/in/landwehr/

In this episode of The Ross Simmonds Show, Ross chats with Jay Schwedelson as he shares a masterclass on personal branding, LinkedIn growth, virtual events, AI workflows, and building audience-first media that drives real business results. If you want practical strategies to amplify your content, humanize your brand, and create marketing that people actually remember, this conversation is packed with proven insights you can put to work immediately.

Key Takeaways and Insights:

1. LinkedIn Growth and Personal Brand Strategy

- Jay shares how he grew from a few hundred LinkedIn connections to more than 80,000 by posting consistently and focusing on one platform.

He emphasizes that different types of content perform better on different days, with educational posts early in the week and lighter, more motivational content later on.

One of the strongest takeaways: personal branding works best when it feels real, human, and native to the platform.

2. Why Lo-Fi Content Beats Overproduced Content

- Jay makes the case for low-production, authentic content that shows personality instead of polish.

He explains why behind-the-scenes videos, imperfect moments, and conversational posts outperform scripted, overly branded content in the age of AI-generated sameness.

For marketers and creators, the big opportunity is clear: lean into humanity to build trust and attention.

3. How to Build Memorable Events People Actually Attend

- Jay reveals the strategies behind his high-performing virtual events, including “earned on-demand” access and short session formats.

- He shares why fun, unexpected moments like contests, celebrity appearances, and unconventional programming create stronger audience engagement.

- His framework is simple but powerful: treat events as a marketing channel, not just a cost center.

4. AI, Claude, and Agentic Workflows for Marketers

- Jay walks through how he uses Claude to organize audience data, identify ideal prospects, and generate highly tailored campaign proposals.

- He also discusses how agentic AI could soon help marketers run and optimize campaigns with far less manual work.

- His advice is direct: use AI for efficiency, but don’t let it erase originality or human perspective.

5. Leadership, Burnout, and Long-Term Success

- Jay opens up about burnout, the power of saying no, and the mindset shift that helped him regain clarity.

- He shares his daily “I don’t have to, I get to” reframe as a practical gratitude tool for staying grounded.

- The broader message: consistency, delegation, and self-awareness are critical for sustainable growth in business and content creation.

6. Speaking, Failure, and the Philosophy Behind the Book

- Jay explains the meaning behind his book title, Stupider People Have Done It, and how that idea helped him move past imposter syndrome.

- He offers practical public speaking advice, including why memorized presentations fail and why relatability wins every time.

- He also encourages marketers to fail faster, test ideas honestly, and stop waiting for perfect before taking action.

Resources & Tools:

🔗 Stupider People Have Done It by Jay Schwedelson

🔗 JaySchwedelson.com

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╰ Instagram: @​​jayschwedelson

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