#96 From Startups to Streaming: Kevin Weatherman’s Playbook for AI-Driven Growth

In this special episode, Tye DeGrange, CEO of Round Barn Labs and host of Always Be Testing, reflects on his journey in marketing and the timeless principles he calls the Cowboy Code. Drawing from his upbringing on a California ranch and decades of experience leading growth at eBay, StubHub, and beyond, Tye explores what B2B marketers can learn from consumer brands.He highlights why trust and authenticity are more critical than ever in today’s trust-deficit world, and how partner and affiliate marketing can help bridge the gap. From lessons in finishing what you start, keeping promises, and “talking less but saying more,” Tye makes the case that B2B has its moment now—to embrace authenticity, invest in brand, and build lasting trust with buyers.

In this episode of the Always Be Testing podcast, Peter Denton—a seasoned growth and marketing leader with a 25+ year career in startups, product experimentation, and marketing innovation—shares a wealth of insights from his journey through the dot-com boom to leading growth at XMTP and previously Pioneer Square Labs.Peter discusses how to de-risk startups before launch, leverage APIs and data for faster insights, and adapt to changing marketing landscapes driven by AI, privacy, and emerging tech like blockchain and quantum security. From the rise of agents and protocols to the future of messaging platforms, Peter offers a masterclass on building, testing, and scaling products in today’s fast-moving world.

In this episode of Always Be Testing, host Tye DeGrange sits down with Erica Yoon, Director of Marketing at BuildOps, a vertical SaaS platform designed for commercial contractors. With prior experience at companies like Reddit, Erica brings a rich perspective on scaling marketing strategies that go beyond demand generation.

We’re joined by Lucas Beland, Co-Founder & CEO of Goloot, an innovative content platform helping Consumer and B2B brands secure content placements on a performance basis. In this episode, we dive into the evolving world of content and influencer marketing, exploring why it’s time to move past vanity metrics and focus on real business outcomes like customer acquisition cost, ROAS, and lifetime value rather than likes or impressions. We also discuss why authenticity wins—how raw, relatable, and creator-led content resonates more deeply with audiences than overproduced ads, ultimately driving stronger engagement and higher sales.

In this episode of Always Be Testing, host Tye DeGrange sits down with Kevin Weatherman, co-founder of Upscale AI, a performance streaming platform using AI to power connected TV ads for DTC brands. With a rich background that includes being the first business hire at multiple startups, angel investing, and co-founding a global run club, Kevin shares his journey from selling limo rides to Google employees to scaling AI-driven advertising solutions. Their conversation covers Kevin’s approach to identifying market trends, the evolution of A/B testing, connected TV measurement strategies, AI in creative production, the intersection of brand and performance marketing, influencer and affiliate strategies, hiring in the AI era, and personal insights from his journey to sobriety.

Sydney Sloan – CMO of G2, a leading software marketplace for businesses to discover, review, and manage technology solutions. She has extensive experience in customer marketing, community building, and scaling B2B SaaS companies. Formerly at Adobe, SalesLoft, and other high-growth companies, she’s recognized as a champion of customer advocacy.

In this episode, Ben Edelman shares insights from his years studying the intersection of economics, digital marketing, and consumer protection. He and the host dive deep into the evolution of affiliate marketing, the early days of web advertising, and how regulation and business incentives have shaped online behavior—both good and bad. Ben also reflects on ad fraud, deceptive affiliate practices, legal enforcement challenges, and how platforms and advertisers can improve accountability in the digital space.

Bryant Garvin, a 20-year veteran of the digital marketing world, announced his new position as Operator in Residence at Triple Whale. This role leverages Triple Whale's massive data set (35,000+ stores, $55B+ GMP annually) to build better products for marketers and e-commerce operators. Garvin discussed his evolved perspective on attribution, emphasizing Triple Whale's holistic approach using AI and data integration beyond simple dashboards. He highlighted the power of MOBI, Triple Whale's platform, in providing data-driven insights for strategic planning, such as Prime Day optimization. The conversation also touched upon the importance of humanizing data, considering the broader context of marketing beyond immediate clicks, and the crucial role of product quality in marketing success. Garvin shared successful marketing strategies from his past, including adding value instead of discounting and leveraging Kickstarter for product launches. He championed YouTube as an underutilized e-commerce channel and cautioned against relying solely on quick wins, advocating for long-term brand building. Finally, he emphasized the importance of authenticity and human connection in marketing, even in the age of AI, and shared a personal anecdote about his childhood dream of becoming a paleontologist.

Sales expert Sam McKenna, Founder of Sam Sales, shares her journey from solo consultant to a thriving 20-person team with 250+ clients. The podcast discusses her unique sales strategies, including the "Expand the Sandbox" method for LinkedIn prospecting, which landed her a deal with Equifax. Key takeaways include the importance of building genuine rapport with clients (even discussing breakfast!), prioritizing consistent outreach, and investing in employee growth. McKenna emphasizes the critical need for sales leadership training and highlights the detrimental effects of slow responses in communication, advocating for a "give a shit" (GAS) approach that prioritizes human connection over automation. She also shares a surprising personal anecdote about her father's grave and recommends the book "Unreasonable Hospitality." The conversation underscores the transferable nature of sales skills across various business functions and the power of human interaction in building lasting relationships.

This Always Be Testing podcast features James Little, a UK affiliate marketing legend and key figure at TopCashback. The episode covers TopCashback's 20-year history, its unique 100% cashback model, and its global success without venture capital. Little discusses the challenges and rewards of operating in various markets, the importance of clear customer education around cashback, and the evolving relationship between cashback sites and brands. He highlights the crucial role of accurate tracking and the positive impact of AWIN's move towards server-to-server tracking. The conversation also touches upon the impact of AI on affiliate marketing, the importance of mental health awareness, and Little's personal experiences.