In this episode of "Social Radars," Jessica Livingston and Carolyn Levy interview Dan Siroker, a serial entrepreneur who went through Y Combinator twice. Siroker discusses his journey from working for the Obama campaign to founding Optimizely, a successful A/B testing company, and now Limitless, a personalized, wearable AI assistant.
Siroker starts by recounting his experience on the Obama campaign, where he introduced A/B testing to optimize the campaign website and increase donations. He then describes his return to Silicon Valley and the founding of his first startup, Carrot Sticks, an online math game for kids, which failed due to a lack of understanding of the target audience. This led him to Y Combinator with another idea called Spreadley, which was later pivoted into Optimizely.
He emphasizes the importance of building for yourself, as opposed to others, and the value of Y Combinator in teaching founders how to focus. He shares the story of how Optimizely got its first paying customer before writing a single line of code and highlights the role of Ashton Kutcher as an early investor.
Siroker shares a key lesson learned from his time at Optimizely: trusting your gut and sticking to your founder instincts, even when others, like board members or executives, suggest a different approach. He reflects on his experience of burning out at Optimizely and falling out of love with the company due to people issues and a culture he didn't want to be part of. He advises founders to be selfish, not selfless, and to find ways to stay engaged and excited about their company for the long term.
He then talks about his nonprofit, the Mind Emulation Foundation, which aimed to explore the possibility of emulating the human mind in a non-biological substance. This led to the idea of capturing everything you see, say, or hear, which eventually became Rewind AI, now rebranded as Limitless.
Siroker explains that Limitless is a personalized AI powered by everything you've seen, said, or heard. It leverages large language models and personal context to provide more relevant and useful responses. He highlights the importance of offering both privacy and convenience to encourage people to share their data.
He describes the Limitless pendant, a wearable device that captures conversations in a privacy-sensitive way. The pendant offers consent mode, which only captures the voice of people who have verbally opted in. He emphasizes that Limitless can help to alleviate the memory challenges that we all have as we get older and to provide an overall increase in productivity.
Siroker also shares the unique story of how he raised the series A for Rewind AI. He made his pitch deck public, resulting in thousands of offers to invest. He ultimately chose NEA, an investor with a long-term orientation and a founder-first mentality. Additionally, he talked about the unconventional strategy of meeting with associates to hone the company's pitch presentation and receive criticism from venture capitalists.
Dan concludes by sharing his tips for being a CEO and startup founder with three kids, emphasizing the importance of prioritization and focusing on the main thing. He said the main things for him are to be a great father, a great husband, and a great founder. He advises cutting out everything else to achieve those goals.