Episode description

Accelerator, Incubator, Venture Capital, Venture Studio? There are a lot of ways to get a new startup off the ground. Ben Yoskovitz, founding partner at Highline Beta, joins Barry O'Reilly on this episode of the Unlearn Podcast to talk about exactly that, and Ben shares insights into the world of venture studios, discussing his journey from founding Year One Labs, a venture studio before there were venture studios, to establishing Highline Beta. Ben's expertise in creating and scaling startups provides a unique perspective on the dynamics of venture studios and the strategies for success in the startup ecosystem. 

You always learn the most from failure, and in sharing the difficulties he had with Standout Jobs in the late 2000’s, Ben highlights the importance of building things that people actually want. By applying Lean Startup principles and working with some incredible entrepreneurs, what he was really doing was learning how to build products and companies more effectively.  Failure after failure isn’t fun, but being willing to share what you learn can help you create something incredible. “Founders do need to hear from other founders. you know, sometimes you need a shoulder to lean on,” Ben says, “and that might not be a blog post, or a podcast, that might be actually talking to another human.”

How do you make an entrepreneur panic? Tell them they’re locked into a single idea for 25 years. Barry notes that “this idea of pursuing multiple ideas in different domains, but doing it in parallel…” lets the multi-passionate and the multi-skilled create value. Ben talks about the difficulty in working with corporate partners and investors when building startups, because they’re not speaking the same language, and the same challenges keep happening again and again - this was the impetus to find a better way to create new companies. The same challenges kept happening at the same inflection points, which means it can be systematized.

Ben talks about the challenges and strategies involved in scaling a venture studio, emphasizing the need for effective people management and business model refinement. He reflects on his own experiences and acknowledges the importance of recognizing strengths and weaknesses in leadership roles. Ben discusses the evolution of Highline Beta and the considerations involved in scaling the business, including generating revenue, hiring the right talent, and defining the future direction of the studio. "I think studios are meant to create shortcuts for founders. Not in a bad way, but give me the shortcut tools to validate faster, get to market faster, raise capital faster, recruit a team faster." This can make all the difference for a new startup.

Ben and Barry discuss the trend of specialization in venture studios, with Ben highlighting the emergence of more specialized studios focusing on specific industries or markets. He emphasizes the potential benefits of vertical venture studios, where the playbooks are standardized and refined for targeted sectors. Ben envisions a future where studios become experts in niche areas, leveraging their experience to create value and drive better outcomes for startups. The conversation explores...