The Marketing B-Sides

When consumers outsource web browsing to AI agents, your website is no longer being read primarily by humans. Chris Andrew, founder of Scrunch and now VP at Sitecore, sits down with Tom to break down how the customer journey has permanently shifted toward machine-first discovery and generative engine optimization. Chris shares the story of founding Scrunch in 2023, scaling it rapidly, and navigating its acquisition by Sitecore. He addresses the 91% of marketers who claim to have an AI strategy, explaining why only 41% are actually measuring impact and taking action. We discuss why SEO was never dead, how the web is splitting into a non-visual CMS layer for AI crawlers and a personalized visual layer for humans, and how enterprise platforms are adapting to an era where AI agents make the buying decisions. Outside of MarTech, Chris shares his unconventional passion for hospitality, including how he became a certified Neapolitan pizza chef in Naples, built a winery in Oregon, and used Kim Gordon's philosophy on self-belief to break free from the safety of a W2 paycheck.

If you have spent any time scrolling social media while trying to survive corporate America, chances are you have run across Mark Cross. Known to over 100,000 followers as SVP of Global Brands and now the founder of social growth agency Dorojo, Mark has built a massive audience by holding up a hilarious, deeply empathetic mirror to the absurdity of modern work. Mark sits down with Tom for an extended conversation about leaving behind a ten-year career in tech and nonprofit fundraising to step into creator life full-time. He dismantles the myth that working for yourself is stress-free, sharing the anxiety of building benefits and pipeline from scratch. They dive into why corporate gallows humor resonates so deeply across Slack, why the bar for decent management is currently in hell (hint: let your employees go to the dentist), and why he turned down talent agencies that wanted creative control over his content. The conversation breaks down actionable growth mechanics, including how Mark gained more followers in four months on Instagram than in four years on TikTok, the power of verified comment strategies, and using the principles of The Mom Test for real business validation. Mark also reflects on doing stand-up comedy in Charleston, lessons from legendary mentors, and the pivotal animal shelter fundraiser that proved work can actually feel good when you care about the outcome.

Homefield Apparel CEO and co-founder Connor Hitchcock sits down with Tom Hootman right as college football season kicks into high gear. From packing orders by hand in 2017 to building a powerhouse vintage collegiate brand licensed with over 150 universities, Connor shares the authentic story behind Homefield's meteoric rise. We dive into what happens when an underdog brand's favorite team starts dominating, how Homefield navigates its brand voice without alienating national college football fans, and why digging through dusty university archives creates apparel people genuinely love. Connor breaks down his original grassroots marketing playbook, explaining how reaching out to niche college football bloggers, DMing 30 super-fans per school, and sending free shirts with zero strings attached built an untouchable foundation of brand equity. Connor also shares hard-learned lessons about paid media limitations, explaining why performance ads are a maintenance tool rather than a core growth driver for Homefield. We talk about modern uniform trends, physical retail expansion with their Kirkwood store, and why Homefield strictly bans AI from their creative process to protect human storytelling.

Most marketers spend their entire careers in one lane. Marc Bitanga, founder at Persuasive and former Director of Growth at Hootsuite, has hit for the cycle. Having worked in-house during massive hypergrowth, ran his own agency, freelanced, and served as a fractional executive, Marc brings a rare, 360 degree perspective to what it actually takes to survive and grow in B2B marketing. Marc sits down with Tom to pull back the curtain on the side hustle. He shares what it was like managing a million dollars in ad spend on evenings and weekends while working fifty hours a week, and the stark reality check that comes when you swap a steady paycheck for what he calls the diamond crushing pressure of making payroll. They unpack why standard SaaS marketing playbooks fail miserably when applied to agency lead generation, including the hard lesson learned from sending fifty custom, painstaking audits that yielded exactly one reply. The conversation dives deep into the mechanics of professional services: why trust transfer beats cold outreach every time, how using close the file emails helps maintain pipeline sanity, and why taking on a bad fit client guarantees you will only get referred to more bad fit clients. Marc also breaks down his three non-negotiable red flags for vetting prospects, and explains why you do not need a massive social media presence or viral personal brand to build a wildly successful business.

When you produce between 1,500 and 2,000 podcast episodes every month, you learn pretty quickly what works and what is complete noise. Rachel Elsts Downey, founder and CEO of B2B media superpower Share Your Genius, sits down with Tom to deliver a blunt masterclass on audio strategy, leadership, and breaking free from ego driven business decisions. Rachel cuts through toxic positivity to explain why founders must operate on facts over feelings. She breaks down the critical distinction between metrics of performance (like downloads and consumption rates) and metrics of success (like brand trust and pipeline velocity). We discuss the biggest mistakes brands make when launching a podcast, why the guest experience is an untapped goldmine, and how to maximize your leadership's mic time without treating conversations like a churn-and-burn assembly line. Beyond the mics, Rachel shares her personal journey from law school to media founder, why comparison is the ultimate thief of joy, and the hard earned lesson that you do not have to prove anything to anybody.