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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