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  • Writer's pictureCreative Return


Updated: May 28, 2023

Raising capital and running a Silicon Valley business are high-pressure endeavors. Jason Tan and his team have raised over $100,000,000 to build their company vision of Sift. As we hear, being human is one of the best things you can do to run a successful business.

Jason is also an alumnus of the famous Y Combinator incubator program and explains how his role as a leader is continuously evolving. He speaks candidly about his battles with depression as an entrepreneur as well as some solid lessons you can apply when financing your business.

“I think it’s just remarkable how, in professional sports, these players have five different types of coaches, and it’s expected. Yet, in business, we don’t really celebrate that type of culture and attitude as much as I think we should and need to. Having a coach for your mind is one of the most high-leverage investments anyone can make.” — @jasontan [0:29:11]

When asked about building relationships with VCs, Jason made a point about investors being curious people, and suggests leveraging this by helping feed their curiosity so they are better off for meeting you. Another coffee meeting is not what a professional investor needs.

“Investors I’ve found to be very naturally curious people, and they really enjoy learning. At a bare minimum, if you two are connecting, you can help each other learn.” — @jasontan [0:37:40]

Enjoy the show!



  • Jason introduces his company, Sift, which helps online business use trust to drive growth.

  • Jason shares a bit about his background and how he developed his entrepreneurial spirit.

  • Jason’s experience of Y Combinator: it offered a community of other founders to connect with.

  • How the program changed Jason’s pitch and view, and how he feels it has impacted him now.

  • Online fraud, prevention, and driving greater trust – Jason talks about what it is that Sift does.

  • Fraud as a cat-and-mouse game – what Sift does is provide a partner that’s one step ahead.

  • Sift helps customers use trust as a way to reimagine the friction in their user experience.

  • Sift focuses on consumer-facing digital businesses with exposure to risk at different stages of the user journey, like in e-commerce.

  • Jason talks about how the default internet experience today is “guilty until proven innocent,” and how Sift is working to change that.

  • What kind of fraud and safety concerns business executives should be aware of, day-to-day.

  • Jason’s early experience at Zillow and what he learned about the value of company culture.

  • The value of experienced leaders – they can help you see around certain corners sooner.

  • From Zillow to starting Sift – Jason talks about what drove him to start his own tech company.

  • Jason’s struggle with depression, the stigma, and why he believes it’s crucial to talk about it.

  • Jason believes that having a coach for your mind is the best investment anyone could make.

  • Jason thinks more high-profile people should be more open about mental health struggles.

  • Build investor relationships upfront, understand their interests, learn how to tell a good story.

  • When Jason came to embrace telling an effective story – storytelling should be dynamic.

  • Jason has found that investors are naturally curious people, and suggests helping them learn.

  • Bringing on VC money and the related difficulties – Jason says stand up and speak directly, but do so with compassion and respect.

  • Jason learned these skills by setting the tone, and learning to separate facts from opinions.

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