Sideways Rain

Sideways Rain
Podcast Description
In the unpredictable storm of building businesses, Sideways Rain explores the art and science of innovation and entrepreneurship. Hosted by two industry leaders—JR Spiess, CEO of The 180 Group, and Kris McNeil, Co-Founder of WIFT—this podcast delves into the challenges, pivots, and breakthroughs of scaling ventures in both the digital and experiential worlds. From tech solutions to human connections, we tackle the chaos of business growth with stories, strategies, and insights that help you thrive no matter where the rain comes from.
Podcast Insights
Content Themes
The podcast focuses on themes such as innovation, entrepreneurship, and technology with specific episodes covering work-life balance for entrepreneurs, tech development challenges, and the role of public relations in business success. For example, an episode titled The Truth About Work-Life Balance shares candid stories of navigating personal and professional chaos, while Navigating the Chaos of Tech & Innovation discusses the unpredictable nature of software development.

In the unpredictable storm of building businesses, Sideways Rain explores the art and science of innovation and entrepreneurship. Hosted by two industry leaders—JR Spiess, CEO of The 180 Group, and Kris McNeil, Co-Founder of WIFT—this podcast delves into the challenges, pivots, and breakthroughs of scaling ventures in both the digital and experiential worlds. From tech solutions to human connections, we tackle the chaos of business growth with stories, strategies, and insights that help you thrive no matter where the rain comes from.
In Episode 14 of Sideways Rain, JR and Kris sit down with product manager Kenny Corum (formerly of Axios, now at Oura) to unpack the reality of working in product—and what it really takes to break in.
From walking away from a steady job to building trust with skeptical customers, Kenny shares the twists, pivots, and risks that shaped his journey. They dive deep into the importance of listening, honest feedback, scope creep, and how customer success skills can become the backbone of a great product career.
Whether you’re in tech, building a startup, or just figuring out your next move, this one’s for you.
Topics include:
- Why Kenny quit without another job—and what happened next
- Product management vs. customer success
- The power of listening and honest user feedback
- Dealing with ambiguity, scope creep, and tough pivots
- What makes a great PM (and why it’s not what you think)
- Lessons from building WIFT, Oura Ring, and beyond
Links:
- Email: [email protected]
- LinkedIn: https://www.linkedin.com/in/kenny-corum
- Product Podcast: https://podcasts.apple.com/us/podcast/the-product-podcast/id1219400787
- Oura: https://ouraring.com/
- Lucky Buns: https://www.luckybuns.com/location/union-market-location-lucky-buns/

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