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.

It is easy to scroll through LinkedIn and convince yourself that every executive has it completely figured out. But according to Heidi Henderson, Chief Marketing Officer at Engineered Tax Services and host of the Slash Tax podcast, real professional stability does not come from pretending to know everything. Instead, Heidi joins Tom to explain how mentorship and critical thinking give you true security in a quickly evolving AI era, sharing her own non-traditional journey from a windowless accounting office to commanding the room as a creative marketing leader.

Heidi pulls back the curtain on what it takes to build authentic trust in a highly competitive, heavily commoditized industry. We discuss why raising your hand to help, attaching yourself to seasoned experts, and showing up completely vulnerable is a career superpower. We also dive into the relentless nature of modern media, what Tom calls the infinite mail delivery route where there is no permanent finish line, and why True ROI is built on long term human relationships rather than automated quick fixes.

We take a pragmatic look at the current state of AI platforms, with Heidi sharing how using multiple tools can act like an organizer on steroids for drafting video scripts, while simultaneously forcing our own critical thinking skills to be on steroids to catch and validate blatant errors like mismatched calendar dates. This episode is a call to action for leaders to keep their analytical filters sharp, embrace their wrinkles over robot facades, and focus entirely on the real human being behind the work.

Paid social moves fast, but the traditional ways of training the people who run the accounts are broken. Akvile DeFazio, Founder of Akvertise and creator of the Social Ad Academy, joins Tom to talk about why she is channeling her energy into mentoring the next generation of advertisers. In a sea of scandalous internet gurus and copy-paste hustle bros, Akvile is building a judgment free zone where greener marketers can ask real questions without fear of costly mistakes.

Akvile shares her transition from feeling allergic to the traditional agency path to running a highly intentional, selective collective of experts. We talk about the major value shift happening in paid social, where manual button-pressing and hyper-segmented targeting are dead, leaving creative strategy and deep business context as the ultimate differentiators.

We also cover the psychological safety required to help junior talent thrive, why you should always hire entry level roles in pairs, and the blueprint behind Akvile’s remarkable six to seven year average client retention rate. Stick around until the end for an absolute masterclass of a playlist featuring A Tribe Called Quest and Method Man.

We love to treat our own brands like they are the center of the universe. But according to Dr. Mansur Khamitov, Assistant Professor of Marketing at the Indiana University Kelley School of Business, that exact bias is a major blind spot for modern executives. Mansur joins Tom to deliver a blunt reality check on corporate optimism, drawing from his research on consumer psychology and his years managing household brands at Procter and Gamble and in big pharma.

Mansur breaks down the staggering reality of the modern marketplace, where the average consumer is bombarded by up to 5,000 brand messages a day and could care less if 80 percent of those brands suddenly vanished overnight. We discuss how to break out of the C-suite echo chamber, the value of letting customers be wrong, and the mathematical reality of regression to the mean when navigating the natural highs and lows of agency life.

We also take a close look at the next generation of marketers entering the workforce. Mansur explains why Gen Z is fiercely values driven, often prioritizing an organization's core mission over a higher paycheck, and why brands need to look past automated HR algorithms to find the real grit and perseverance that defines top tier talent.

Every business student who has marched through Indiana University since 1967 knows K201, the legendary Computers in Business course. But the era of simple software shortcuts is officially over. Brant Moriarity, Director of the course at the Kelley School of Business, joins Tom to break down the massive, structural evolution of higher ed technology and analytics education.

Brant shares the reality of teaching a course to 2,300 freshmen every semester in a world completely altered by the shift to AI. We explore Kelley's new pedagogical framework called Build, Adapt, Defend. This system is designed to force entry-level students out of passive button-pushing and into live-fire problem solving. Brant also dismantles common misconceptions about Gen Z tech literacy, noting that while they are born with mobile devices in hand, basic enterprise file organization and system troubleshooting remain an active learning curve.

From navigating administrative red tape across nine separate college campuses to a hilariously diverse musical history that spans Marilyn Manson and underground West Coast hip-hop, this episode offers a direct window into how the next generation of business leaders is being trained to handle data, disruption, and data-backed human judgment.

In an industry obsessed with the "business of yes," Renia Carsillo has spent 20 years building a firm based on the power of the right fit. A former Assistant VP in banking with a degree in Iranian Politics, Renia brings a pragmatism to Realign Consulting that most agencies lack. She joins Tom to discuss her "Three Bright Lines" for vetting clients: believing in their mission, trusting their team, and ensuring they have at least a six-month financial runway to allow for foundational work.

Beyond the mechanics of agency growth, Renia dives into a staggering statistic: while 48% of new businesses are started by women, only 6% ever gross more than $250,000. We discuss the systemic and "soft" hurdles, from credit access to the lack of domestic support structures, that keep those numbers low, and Renia’s new mission to profile the women who have broken through that barrier.

We also tackle the AI hype cycle. Renia explains why she’s skeptical of anyone calling themselves an "AI Expert" and why she forbids her team from using "God Mode" commands. From her color-coded quarterly planning to the 2-day offsite strategy retreats she mandates for every client, this episode is a guide for leaders who want to stop reacting and start building.