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.
Most people get into events because they love the energy. The problem is loving events and knowing how to run an event business are two completely different things.
Andrew Roby, founder of Andrew Roby Events, learned that the hard way. Coming out of the Army in 2005 after serving at the Old Guard and navigating multiple deployments that took a real toll on his mental health, he was nearly homeless when he launched his firm. He knew how to execute events with military precision. He had no idea how to run a business.
On this episode, Andrew breaks down the real gap in our industry education, why selling logistics is a losing game, how he restructured his entire operation to stop working in the business and start working on it, and what it actually means to price your value correctly.
He also gets into mental health, the discipline of disconnecting, why he thinks industry conferences are overrated, and why your social media might be talking to the wrong people entirely.
Quick hits from the episode:
- Andrew Roby Events
- Follow Andrew on LinkedIn
- Book recommendation: The Body Keeps the Score by Bessel van der Kolk
- Andrew's Hotel Guest Experience Audit
If this one hits home, send it to someone in your network. That is what we are here for.

Disclaimer
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