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When Google’s algorithm changes caused HubSpot’s traffic to plummet 80%, most companies would have panicked.

Aja Frost saw an opportunity.

As Senior Director of Global Growth at HubSpot, Aja led the transformation that helped HubSpot not only recover—but become the most-cited CRM in generative AI results.

In this episode of FUTUREPROOF., Jeremy Goldman sits down with Aja to talk about how the rules of discovery, demand, and digital visibility are being rewritten in real time—and why Answer Engine Optimization (AEO) may be the next big discipline marketers can’t afford to ignore.

They discuss:
🔍 What happens when users trust ChatGPT more than Google
🧠 How HubSpot rebuilt its content strategy around AI answers
💬 The formula for getting cited by AI models—and what most brands get wrong
📈 Why visibility beats clicks in an LLM-driven world
🌐 The new off-site frontier: Reddit, YouTube, and the “dark funnel” of discovery
⚙️ How to measure success when your customer journey starts with a chatbot

If you work in marketing, SEO, or content—and you’ve felt the ground shifting under your feet—this episode will help you understand how to thrive in the AI search era.

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In a world where algorithms amplify outrage and newsfeeds reward noise, 1440 Media has quietly built something radical — a daily newsletter that promises “all your news, none of the bias.”

This week on FUTUREPROOF., Jeremy Goldman talks with Tim Huelskamp, CEO and cofounder of 1440, about how a 15-person team grew to reach over 4 million subscribers without chasing clicks, outrage, or political extremes.

Tim shares what he’s learned about:
- How 1440 found “white space” in a crowded media market
- Why being unbiased is both a superpower and a branding challenge
- How 1440’s ad model bucks media’s obsession with vanity metrics
- Why curiosity—not content—is the new currency for growth
- And what The Free Press sale reveals about the shifting trust economy

If you’re tired of doomscrolling and looking for what’s next in digital publishing, this conversation offers a blueprint for rebuilding trust, curiosity, and connection—one inbox at a time.

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As AI reshapes the world faster than most of us can process, we’re left with an uncomfortable question: What does it really mean to be human now?

This week on FUTUREPROOF., Jeremy sits down with Jeff Burningham — tech entrepreneur, investor, and author of The Last Book Written by a Human — to explore how we can cultivate wisdom, purpose, and empathy in an age obsessed with speed, scale, and artificial intelligence.

Jeff’s story is as surprising as it is inspiring: from Mormon missionary to real estate mogul, from political candidate to spiritual seeker. After years of building billion-dollar companies, he found himself confronting a deeper question — not how to make more, but how to matter more.

In this episode, Jeff and Jeremy discuss:

• Why becoming wiser, not just smarter, is the next competitive advantage
• How technology mirrors our consciousness — including our biases and blind spots
• Why the future of leadership depends on emotional and moral intelligence
• What it means to design an economy — and a life — centered on meaning, not metrics
• And how AI’s reflection of us can become humanity’s greatest teacher

Whether you’re a founder navigating AI disruption or a curious human trying to stay grounded in a digital age, this conversation will remind you that wisdom — not code — may be the ultimate frontier.