Making It Safe To Break Things

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 loaded with actionable wisdom and candid perspective. Wil also opens up about what he’d do if he had to start over from scratch, the dangers of imposter syndrome, and how to use AI to interview subject matter experts in a scalable way.

Key Takeaways and Insights:

1. Respect the Audience’s Attention

- Share only what you genuinely believe will teach someone something.

- Use a simple gut-check: “Would I want to see this in my feed?”

- Don’t post to post—post to educate and create real value.

2. “Real Stuff” Builds Trust

- The most resonant content is often the painful, honest, behind-the-scenes truth.

- Being raw and human builds long-term sentiment—and turns strangers into future clients.

- The posts that work are raw: mistakes, broken processes, real lessons.

3. Distribution Beats “Perfect Content Process”

- Over-engineered content processes don’t matter if nobody distributes the output.

- Optimize for conversation + sharing, then adapt it for search after you know it hits.

4. Use Data + AI to Run Experiments (and Get Leverage)

- Tools like PhantomBuster + Claude/Claude Code can turn LinkedIn into a research + lead engine.

- Track who engages (titles, industries), then use that insight for outreach and pipeline planning.

- Blend paid + organic data to spot waste/opportunity (e.g., language intent mismatches, “people also ask” signals).

- The goal isn’t replacing people — it’s pulling real knowledge out of them faster.

5. Future-Proofing Means Adaptability

- The real edge is staying unsatisfied with the status quo and constantly testing new approaches.

- Leaders should make it safe to “break things” while learning—innovation is messy by nature.

- Wil’s focus isn’t predicting 10 years out—it’s preparing people now for automation shifts through skills, reps, and experimentation.

Resources & Tools:

🔗 PhantomBuster

🔗 Claude

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