At Navigate Ventures, we support the founders of B2B SaaS companies building the next generation of enterprise platforms – especially those navigating the funding gap between Series A and B. 

Through our regular Charting the Course series, we talk to founders and investors who’ve built and scaled companies – and done so many times over – to lift the lid on what it really takes to go the distance in tech. 

In this edition, our Managing Partner Ivan Nikkhoo spoke with legendary venture capitalist Tim Draper, Founder of Draper Associates, Draper University, and Co-founder of DFJ. The conversation spanned the Draper family’s legacy in venture, lessons from Tim’s most impactful investments, the power of risk-taking, and his perspective on the next wave of innovation, from bio cures and space technology to Bitcoin and AI. 

We usually start by asking VCs what drew them to venture investing. But in your case, you were born into the industry! 

Ah, but like all teenagers, I had no idea what I wanted to do! I didn’t want to do what my father and grandfather did. I wanted to be an entrepreneur. Anyway, it turned out I wanted to be an entrepreneur in so many different things that venture capital felt like the career for me. 

Tell us about your family’s legacy. 

My grandfather, General William H. Draper Jr., was the first Silicon Valley venture capitalist. He also ran the economic portion of the Marshall Plan for the reconstruction of Germany and Japan after the war. My father was a pioneer in venture capital too - he started Draper & Johnson Investment Company, then Sutter Hill Ventures, before serving as chairman of the Export–Import Bank and later as administrator of the UN Development Programme. 

He eventually became the first venture capitalist in India. He’s had an amazing career - and still goes to work - and I’ve carried on the tradition. My mission has been to spread venture capital and entrepreneurship to the rest of the world. I travel everywhere and see entrepreneurs talking about pre-money valuations from Sri Lanka to Timbuktu. 

Three of my children are now venture capitalists. My son Adam runs Boost Ventures, focused on deep tech. My daughter Jesse runs Halogen Ventures, which funds companies with women on the founding team and technologies that impact the family. My son Billy runs Path Ventures, focused on simplicity and great technology that makes people’s lives better. We drive my wife crazy at dinner because all we talk about are our deals! One of my daughters is an artist, but she somehow still gets involved. Venture capital runs deep in our family. 

You’ve made some remarkable investments over the years. Which stand out most to you? 

The one that jumps to mind is Hotmail. When we funded it, people were still licking envelopes and waiting days for delivery. Web-based email changed everything. I added the viral marketing idea, and suddenly the business spread all over the world. That innovation made it possible for everyone to communicate instantly and for free. 

Skype was another amazing one. I was on the first video Skype call ever, in Tallinn, talking to Tony Perkins in Palo Alto. It worked perfectly because they had secretly shut down 100,000 simultaneous voice calls to get enough bandwidth for the video! 

Looking ahead, I think Tesla and SpaceX will prove the most transformative. Hotmail and Skype changed communication; Tesla and SpaceX are changing how we move and explore.

How do you work out which startups have the greatest potential? 

Every investment feels like it has potential when I make it. The truth is, I don’t have certainty. I rely on instinct. I invest boldly, thinking, if this works, how great could the world be? Fear is the mind killer. If you invest fearfully, your fears will be realized. But if you invest for opportunity, you can make a fortune for everyone involved. 

What about the ones that got away? 

My real failures were missed opportunities. I brought in Google, but my partners talked me out of it. I passed on Netflix because I didn’t clock the customer acquisition model. I missed LinkedIn because I underestimated how powerful professional networking would become. And I got outbid on Facebook. Those four alone are worth trillions today! But we did back Tesla, and that’s turned out pretty well. 

You have Draper Associates and previously DFJ. Are you still involved with DFJ? 

DFJ Growth still exists, but DFJ itself became too big and too political, so I spun out and started Draper Associates. That gave everyone freedom. I’ve been able to do things that wouldn’t have fit inside DFJ, like buying Bitcoin, launching Draper University, creating Meet the Drapers, and backing Robinhood when the partnership passed on it. We’ve thrived since going our separate ways. 

How do Draper Associates and DFJ Growth differ in focus? 

Draper Associates is early stage. We’ll invest when it’s just two founders and a dog. We double down on our winners and back them again. DFJ Growth comes in much later, when companies are doing $50 million in revenue and growing at 50% or more. 

Tell us about Draper University and its origins. 

I started it because people told me entrepreneurship was innate and couldn’t be taught! I bought a hotel and turned it into a school where we turn ordinary people into entrepreneurs. We build confidence, teach them to see upside not downside, and encourage them to create their own lives and jobs. So far, 6,000 people have gone through our Hero Training, creating 2,000 companies. 35 are worth more than $100 million; five are unicorns. It’s harder to get into Draper University than Harvard or Stanford, and after 5-10 weeks, our average student creates seven jobs. 

Some students already have businesses, others just ideas, and some have neither, but they’re driven. We look for people who’ve gone deep in one area, or those with a broad understanding of how the world works. Either depth or breadth. 

You clearly have strong instincts about the entrepreneurs you back. What traits do you look for?

Some people just have this extra energy around them. Often it comes from having a mission. I like entrepreneurs who’ve been focused on a space for a while and then see something their previous company missed – all the customers were asking for this, and the company kept giving them that. 

The best founders have quiet confidence. They know they’ll get there, even if they don’t know how. They listen, but know when to stop listening and trust their instincts. 

How much time do you usually spend with them before deciding to invest? 

It could be 20 minutes, or it could take multiple meetings. Sometimes you know instantly. Other times, a few discussions can help the entrepreneur refine their thinking and point them in the right direction. 

What are the tech and innovation trends that most excite you right now? 

Firstly, pharma is moving from chemical-based treatments like chemotherapy to biological cures – using stem cells, CRISPR, mRNA, and gene editing. Big Pharma won’t like it, but bio cures are coming. 

Transportation and space are also exciting. We’re seeing innovation everywhere: hypersonic vehicles, eVTOLs, maybe San Francisco to Tokyo in two hours. 

Bitcoin’s gravitational pull is increasing. Engineers are moving their best work onto the Bitcoin blockchain, just like they did with Microsoft’s operating system. It’s becoming the global standard for currency, finance, and commerce. 

And, of course, AI is transforming every industry – including mine. We use AI in a number of ways at Draper Associates: we have a data lake generating new company ideas; we analyse founder interactions; we even use digital twins for entrepreneur coaching. AI plus robotics will redefine everything. 

And finally, your advice for young entrepreneurs just starting out? 

It comes from Nike – just do it. It’s fun, and you’ll learn more by doing than you ever will by waiting. You’ll find out quickly if this life is right for you. 

About Draper Associates 

Draper Associates is a pioneering early-stage venture capital firm founded by Tim Draper in 1985. For nearly four decades, the firm has backed visionary founders building transformative technologies that have reshaped industries and defined successive waves of innovation - from the internet and fintech to AI and frontier tech. Its portfolio includes landmark investments such as Tesla, SpaceX, Baidu, Hotmail, Coinbase, and DocuSign, among others. 

As part of the global Draper Venture Network, Draper Associates combines capital with mentorship, strategic guidance, and access to a worldwide ecosystem of investors and partners. 

The firm continues to invest in bold entrepreneurs driving technological and societal progress on a global scale. 

About Tim Draper 

Tim Draper is a third-generation venture capitalist, entrepreneur, and global advocate for innovation and entrepreneurship. He is the founder of Draper Associates, DFJ (Draper Fisher Jurvetson), and Draper University - a global human accelerator that trains and inspires entrepreneurs worldwide. Tim is also the creator of the international pitch show “Meet the Drapers,” which connects founders with investors and audiences across the globe. 

Over his career, Tim has backed dozens of category-defining companies that have shaped the modern technology landscape - spanning electric vehicles, private space exploration, digital finance, and frontier technologies. His investment legacy reflects a long-standing commitment to supporting visionary founders driving global progress. 

He holds a Bachelor’s degree in Electrical Engineering from Stanford University and an MBA from Harvard Business School. 

About Ivan Nikkhoo

Ivan Nikkhoo is the Founder and Managing Partner of Navigate Ventures, an early growth fund specializing in partnering with exceptional B2B Enterprise SaaS companies outside Silicon Valley between Series A and Growth rounds. Navigate employs a risk-mitigated strategy designed to achieve a short holding period and an accelerated path to Distributions to Paid-In Capital (DPI). A sought-after speaker, Ivan frequently shares his insights at venture capital and family office conferences globally and is a regular contributor to several leading industry publications.

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