Convince and Convert

Jay Baer didn't build Convince and Convert as a typical startup. Instead, he evolved from being an early digital marketing strategist into a content and media business owner. Since 1994, he had been advising companies on customer acquisition and retention. By the time of this interview, he'd worked with over 700 companies, including 32 Fortune 500 companies like Nike, Caterpillar, and Allstate. The spark wasn't about solving a single problem—it was about building an ecosystem of authority.

Jay started with a simple blog called "Jay's Blog." Over time, he realized his true competitive advantage: connecting marketing technology companies with their future customers through high-quality content. He transformed his personal blog into a digital magazine with contributions from multiple writers, then into a full media company. By the time of this interview, Convince and Convert's media division owned:

- The world's number one content marketing blog (4 million annual visitors) - The world's top marketing podcast - Six weekly podcasts - Webinars and live video content - 312 podcasts per year and 630 blog posts per year

Crucially, he realized that corporate sponsors would pay to be part of this audience delivery engine. For example, the newly-launched "Influencer Pros" podcast had two co-hosts (from Cision and Tap Influence) each paying $3,000 per month to host, plus additional sponsors paying similar amounts for ad placement.

The three-revenue-stream model proved remarkably effective. Speaking became the largest line, generating approximately $1.2M annually by 2015. Jay charged between $20,000-$25,000 per live event (with 50-60 events per year) and did 25-30 webinars annually. The podcast sponsorship business generated roughly $500,000+ per year across six shows, with each show needing to annualize at $80,000-$100,000 to launch. Consulting remained at approximately one-third of overall revenue.

Jay's speaking strategy was disciplined: increase fees by about 10% annually, maintain a "bad cop" negotiator on staff to handle rate discussions, and do only 3-5 free events per year for people who genuinely helped build his career (like Jason Dorsey, Joe Pulizzi, and Michael Stelzner). He learned from Scott Stratton that keynote speakers who command fees talk about one thing in five different ways, while underpaid workshop speakers cram in five different topics. He focused on depth over breadth.

For book launches, Jay employed an innovative pre-order strategy. When launching "Hug Your Haters," he sold directly through HugYourHaters.com rather than Amazon to control the fulfillment timing and maximize bestseller list placement. He sold over 10,000 copies before the official release date through a tiered bonus structure (I Love Haters socks, exclusive Facebook groups, webinars, one-on-one calls).

By 2015-2016, Convince and Convert had evolved into a sophisticated, multi-platform media and consulting company with three revenue lines of roughly equal size. Jay's personal brand as "the world's most retweeted person among digital marketers" drove all three businesses. He had diversified beyond consulting into speaking ($1.2M+), sponsorships ($500K+), and was actively launching books and ventures. He was also an active venture capitalist and angel investor in companies like Buffer and Sigstr.

At 46 years old, married with two children, Jay reflected on what he wished his 20-year-old self knew: patience. He had once quit a job impulsively and later realized his impatience was a weakness. He believed most entrepreneurs underestimate how long it takes to build real, lasting success—and that the "speaking ladder" (from free to $20K+ per event) typically took years to climb.