Podcast Summary: Always Be Testing
Episode #96: From Startups to Streaming: Kevin Weatherman’s Playbook for AI-Driven Growth
Released: August 12, 2025

Introduction

In Episode #96 of the Always Be Testing podcast, host Ty DeGrange engages in an insightful conversation with Kevin Weatherman, the co-founder of Upscale AI. The episode delves deep into the intersection of startups, streaming, and AI-driven growth strategies. Kevin shares his extensive experience in performance marketing, growth experiments, and the evolving landscape of AI in advertising.

Guest Background and Journey

Kevin Weatherman brings a wealth of experience from his tenure as the first business hire at Adbrite, a company later acquired by Twitter, and his pivotal roles in various startups. He emphasizes the importance of anticipating market shifts and aligning career moves with future industry trends.

Kevin Weatherman [04:41]: "Go skate to where the puck is going. When you look at each jump that I made along my career, there was that moment in which I said, okay, three to five years from now, the world's going to look differently..."

Kevin's career trajectory exemplifies strategic foresight, having transitioned seamlessly from traditional advertising platforms to embracing AI-driven solutions in performance streaming.

Upscale AI: Revolutionizing Performance Streaming

Kevin elaborates on Upscale AI’s mission to transform connected TV (CTV) ads into a measurable performance channel. With $5.5 million raised to date, Upscale AI leverages AI to reduce creative costs and optimize ad performance for Shopify-based Direct-to-Consumer (DTC) brands.

Kevin Weatherman [02:30]: "What if we could drop the cost of creative down to zero and treat it like we do Meta, where brands are putting dozens, if not hundreds of ads into the machine learning system for streaming."

Upscale AI focuses on creating data-driven ad creatives that align with user journeys, ensuring measurable outcomes like purchases. The company has successfully scaled its operations, working with dozens of D2C brands and aiming to expand to 50-60 by year-end.

The Evolution of Testing in Marketing

Kevin underscores the critical role of testing in performance marketing, drawing from his early experiences at PubMatic where structured A/B tests were foundational.

Kevin Weatherman [07:45]: "Learning how to test is a skill that you need to learn. If you want to become a chef, you have to learn knife skills. If you want to be in performance advertising, you have to learn how to test things in general."

Over 15 years, the landscape has shifted from rudimentary A/B tests to sophisticated incrementality tests, especially in geo-targeted campaigns. Kevin highlights the transition from single tests to an "always be testing" mindset, essential for optimizing multi-touch marketing strategies.

Kevin Weatherman [12:17]: "We went from a world of like single tests to a world of always be tested."

Connected TV: Measurability and AI Integration

Addressing misconceptions about TV advertising's measurability, Kevin explains how Connected TV (CTV) has become a precise channel through AI advancements.

Kevin Weatherman [12:49]: "There are basically three levers you can pull: time of day, geo, and IP address. The fourth is syncing purchase events to logged-in users on streaming platforms."

He details how Upscale AI utilizes IP address data to link CTV views with subsequent purchases, despite challenges like IP obfuscation from platforms like iOS. This capability allows for accurate attribution and performance measurement, transforming CTV into a viable performance channel.

AI in Advertising: Current Landscape and Future Prospects

Kevin discusses the rapid advancements in AI-generated content, emphasizing the shift from human-dependent processes to AI-driven creativity.

Kevin Weatherman [16:07]: "Today, zero of our creative that are actively running have a voice actor... AI is better than humans."

He predicts that within the next year and a half, AI will enable the creation of high-quality, brand-specific television commercials without original assets, enhancing scalability and reducing costs.

Kevin Weatherman [20:24]: "In the next year and a half... there will be ads that are made that are completely devoid of original assets from the brand, that are great, high quality ads that you might not be able to tell a difference on."

Investing in the Future: Kevin’s Approach

As an angel investor, Kevin emphasizes the importance of anticipating future trends and supporting visionary founders.

Kevin Weatherman [21:18]: "Go to where the puck is going... write checks today on founders who are going to be building the future versions of this world."

He looks for founders who embody the "10x founder" traits: visionary thinking, team-building capabilities, and effective fundraising skills.

Tools and Resources for Growth

Kevin recommends Clay.com as a transformative B2B SaaS tool that automates tasks traditionally handled by sales and marketing teams, enhancing efficiency through AI integrations.

Kevin Weatherman [25:06]: "Clay's spreadsheets on steroids... automating tasks that used to take an SDR four years ago can now be done automatically."

He also suggests essential readings for aspiring entrepreneurs:

• "High Output Management" by Andrew Grove
• "The Hard Thing About Hard Things" by Ben Horowitz

These resources have been instrumental in shaping his strategic approach to business and leadership.

Rethinking Marketing Best Practices

Kevin challenges the traditional dichotomy between brand and performance marketing, advocating for an integrated approach.

Kevin Weatherman [27:33]: "The commonly misconceived notion is that in order to do brand, you can't think about performance."

He cites an example where simply mentioning the brand name multiple times in a commercial significantly boosted ad performance, illustrating the tangible benefits of blending brand and performance strategies.

AI and Hiring: Shaping the Future Workforce

Upscale AI prioritizes hiring individuals who are enthusiastic about AI, viewing it as an indispensable tool rather than a threat.

Kevin Weatherman [30:17]: "We ask in interviews, what's the last tool you used in terms of AI? How did you use it?"

He believes that proficiency in AI tools is becoming a non-negotiable skill across all roles, driving career growth and fostering innovation within the company.

Personal Insights and Closing Thoughts

Kevin shares a personal milestone, revealing his sobriety journey and its profound impact on his life and career.

Kevin Weatherman [39:05]: "At 28 years old... I don't want to drink anymore... I committed myself to sobriety."

He highlights the supportive changes in society and the availability of alternatives like Athletic Brew, making his journey both manageable and fulfilling.

Kevin concludes by inviting listeners to join his global running club, Pitch and Run, underscoring the importance of community and personal well-being alongside professional endeavors.

Kevin Weatherman [41:32]: "If you're in New York, come run with me... Follow me. I'm a big marathoner."

Conclusion

Episode #96 of Always Be Testing offers a comprehensive exploration of AI-driven growth in the advertising landscape, enriched by Kevin Weatherman’s firsthand experiences and forward-thinking strategies. Listeners gain valuable insights into performance streaming, the evolving role of AI in marketing, effective testing methodologies, and the importance of integrating brand and performance marketing. Kevin's personal anecdotes and recommendations provide both inspiration and practical guidance for entrepreneurs and marketers aiming to navigate and excel in the dynamic world of digital advertising.

Connect with Kevin Weatherman:

• LinkedIn: Kevin Weatherman
• Socials: @KevinRunsNYC
• Join Pitch and Run: Available in 15+ cities globally, including New York, London, and Dublin.

Thank you for tuning into Always Be Testing! Stay informed, stay curious, and keep experimenting.