True Builders
You Can Fail, But Not Too Much with Rory O'Driscoll
Published October 12, 2023

Embark on a journey into the dynamic world of business and tech trends with Rory O’Driscoll, Partner at Scale Venture Partners

In today's rapidly-evolving business landscape, staying ahead of the curve requires more than just a crystal ball. It demands a deep understanding of the shifting tides, such as the rise of Software-as-a-Service (SaaS) and cloud computing. As CEOs and founders continue to process advice and navigate the complex world of venture funding sources, they are acutely aware of the challenges posed by current market conditions. The reality is that some CEOs fail, and some founders stumble, but the key is not to fail too much.

With 25 years of active investment experience, Rory is our guide, unraveling the complexities of predicting valuations and dissecting the evolving economy. As partner at Scale Venture Partners, he focuses on early-revenue software companies tapping into the SaaS and cloud-based enterprise computing surge. His remarkable track record, featuring successful investments in, Box, DocuSign, and others, has earned him a place on the Forbes Midas List.

In our conversation with Rory, we plunge into a spectrum of thought-provoking topics crucial for anyone intrigued by business, leadership, and technology trends. We explore the intricacies of predicting valuations and navigating the ever-changing economy, shedding light on the growing significance of SaaS and cloud computing. We emphasize the pivotal role of leaders in successfully navigating uncertainty and highlight the importance of data-driven decision-making in shaping the future of work. Drawing from his extensive experience, Rory outlines key qualities contributing to the success of founders and CEOs. We also tackle the challenges of self-awareness, offer valuable advice, and discuss strategies for recovering from failure while maintaining enthusiasm in one's work.

Notable Quotes

  • "The right advice is situational, conditional, and should recognize the risk of bias from the advice giver.” - Josh [02:00]

  • “If you're an entrepreneur and you're running your business, you've got to at least be aware of where the venture is coming from, because if you need money, you depend on a venture. But at the same time, you can't let them dominate your life because frankly, I think we are a little overbought.” - Rory [03:24]

  • “I think part of being a leader is: part of what you get paid for is literally internalizing the uncertainty, absorbing the uncertainty and keeping some of it away from the team.” - Rory [07:58]

  • “What COVID did was blow away your assumptions, the cobwebs on what could be done, and it's clear that remote can work reasonably well.” - Rory [24:04]

  • “For CEOs, you're selecting on the basis of strengths, not lack of weaknesses. In other words, I'll take a founder with some profound weaknesses if they're awesome at something, and that's something that's important to the business.” - Rory [35:33]

  • "You can feel you've got this style; you can feel you've made a lot of money for your investors, and you can be horribly wrong the next morning, and you can just wake up and feel like an idiot.” - Rory [46:50]

Our Guest

Rory O'Driscoll

Rory O'Driscoll, a Partner at Scale Venture Partners for more than a quarter-century, specializes in guiding early-revenue software firms as they embrace the realms of SaaS and cloud enterprise. Recognized on the Forbes Midas List, Rory boasts a track record of successful investments that underscores his seasoned expertise in the dynamic landscape of technology ventures.

Resources & Links

True Builders Podcast

Rory O'Driscoll