In this episode, Ben sits down with Casey Graham, Co-Founder and CEO of Gravy Solutions, the first-ever payment recovery solution for subscription-based businesses. Prior to launching Gravy, Casey founded the Rocket Company, which he successfully exited in 2016. During this episode, Casey opens up about how his grandfather’s suicide initially led him to the path of entrepreneurship, how his successful company exit resulted in a deep depression, and his overall perspective on company culture and leadership. He also discusses the importance of understanding your big why, separating your identity from your role at work, and much more.

In this episode, Ben sits down with Alexa Gates, Demand Generation leader at Catalyst. During their conversation, Ben and Alexa discuss the value of being direct and upfront in all communications, and why it’s essential for organizations to have a clear mission in mind from the get-go. Alexa explains how a role in demand generation can be compared to putting together the pieces of a jigsaw puzzle, and how in many ways, the function acts as the connective tissue for all marketing teams. They also discuss how we are our own biggest competition and why it’s important to check in and self-reflect regularly.

In this episode, Ben sits down with Sara Masson, the VP of Customer Success at leap tools, a company that’s on a mission to revolutionize the retail experience through AR technology. Sara recently joined the company following the birth of her daughter. During their conversation, Ben and Sara discuss a wide variety of topics including parenting, customer success, company culture and even juggling work with breastfeeding. They offer candid views on building psychological safety in the workplace, hustle culture in the startup world, and how maintaining a healthy family and social life outside of work can affect the entire company culture.

In this solo episode, Ben discusses various aspects of tech culture. He shares his perspective on recent scripted drama series that have depicted tech startup culture like Super Pumped featuring Joseph Gordon-Levitt, about the founding story of Uber, WeCrashed featuring Anne Hathaway and Jared Leto, about the founding of WeWork, and The Dropout featuring Amanda Seyfried, about Elizabeth Holmes and the story behind Theranos. Exploring the narratives surrounding these companies and their origin stories, Ben shares his perspective on what’s changed in the startup world in recent years, and the shifts he believes we’ll continue to see over the next decade in tech.

This brief episode was recorded on the day Russia invaded Ukraine, and in it, Ben shares his thoughts on compartmentalizing work and life, making the most out of the time you have, and how people can best support each other at work when things like this happen. 

In this episode, Ben broaches more hot topics in the tech landscape today. He discusses LinkedIn’s new filter option, which allows users to remove political content from their feeds, the ongoing hiring crisis in the workforce today, the Metaverse and more. Ben also emphasizes the need for clearer pathways towards building a career in tech to usher in the next generation of the workforce.

In this episode, Ben offers his take on some of the most controversial headlines in the business world today. He discusses how Peloton recently laid off 20% of its staff (2,800 people), and why people are saying the way the leadership team handled the layoffs was tone deaf. Ben also discusses how Apple classifies every employee as an “associate” after they leave the company, regardless of what their title was while they were there, and why this could affect future job prospects. Last but not least, Ben explores the results of a recent LinkedIn survey about Gen Z in the workforce. 

In this episode, host Ben Winn is back to discuss more key trends and developments happening in the SaaS community right now. He explores the impacts of inflation on wages and company-wide pay increases. Ben also discusses remote work and mental health, touching on a recent UK poll of 2,000 employees which found that only 41% were willing to raise their concerns with management.