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Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
In this episode, the hosts interview Dharmesh Shah, co-founder and CTO of HubSpot, a $25-30 billion company. (00:00) The conversation focuses on the early days of HubSpot and how Shah figured out a new model of marketing around blogging and SEO when the company had no money or connections. (00:33) Shah explains how he accidentally discovered the power of content marketing while writing his thesis, getting massive website traffic that outperformed well-funded companies with CMOs and marketing budgets. The discussion also covers the evolution from SEO to what Shah calls "AEO" (Answer Engine Optimization) in the age of AI and ChatGPT. (33:50)
• Main themes: The conversation centers on category creation through community building, the power of high-volume content creation, and adapting marketing strategies for the AI era where people increasingly use ChatGPT instead of Google for answers.
Co-founder and CTO of HubSpot, a $25-30 billion software company generating billions in revenue annually. Shah is a billionaire entrepreneur who started blogging while finishing his graduate thesis on software entrepreneurs and accidentally discovered inbound marketing principles. He's known for launching numerous side projects and maintains an active presence in the startup community through both major business ventures and experimental AI projects.
Co-hosts of My First Million podcast. Sam Parr is the founder of Hampton, an executive peer network, while Sean Puri is a serial entrepreneur and investor known for his pattern recognition in emerging business trends and market opportunities.
Shah emphasizes that success comes from putting in more iterations and higher volume of work rather than finding the perfect strategy. (28:06) He believes that "quality of outcomes is almost directly proportional to number of iterations" and that while others might be smarter, "you will not out grind me, you will not outwork me." In the early days of HubSpot, Shah was posting 3-5 blog articles per week on his personal blog while running a company, demonstrating this principle in action. (30:00) The key insight is that the universe has slower feedback loops initially, but consistent effort compounds over time.
Rather than starting with a product pitch, Shah created the "inbound marketing" movement first, building community around the concept before selling tools. (05:30) HubSpot deliberately didn't trademark "inbound marketing" and made their conference about the movement, not the company. They even allowed competitors to attend and speak, focusing on educating the market about this new approach to marketing. This strategy of category creation through movement building has been replicated by others like Russell Brunson with "funnel hacking" and Brian Johnson with the "don't die" longevity movement.
Shah's approach to SEO was counterintuitive - instead of trying to trick Google's algorithm, he focused on creating content that genuinely deserved to rank higher than existing results. (24:00) His advice was simple: search for your target keyword, look at what's ranking, and honestly ask if your content would be more valuable to someone searching for that term. This "white hat" approach of serving user intent rather than gaming systems has proven sustainable over decades, with some of his 19-year-old content still driving traffic and revenue today.
Shah distinguishes between "owning" versus "renting" your marketing channels. (25:27) Paid advertising is like "renting someone else's microphone" - the traffic stops the moment you stop paying, and you don't control pricing. SEO and content marketing, however, are like "building your own property on your own land" that compounds in value over time. This ownership mentality extends to building sustainable, long-term assets that appreciate rather than depreciate, giving you more control and predictable returns on your marketing investment.
As AI tools like ChatGPT capture more search traffic, Shah advocates for "AEO" (Answer Engine Optimization) as the successor to SEO. (35:01) The key differences: structure content in question-and-answer format rather than narrative prose, ensure AI bots can crawl your site, and focus on being definitively helpful since AI gives fewer options than Google's "10 blue links." Success in AEO requires creating content that AI can easily understand and cite, particularly focusing on structured data and clear, authoritative answers to common questions.