He’s 28 Investing From $600 Million Fund, $4.2 Billion Under Management

Michael Gilroy

In Episode #338, Nathan interviews Michael Gilroy, a tech investor and partner with Canaan investment. Canaan’s an early-stage venture firm with $4.2 billion of capital under management. Michael moved there when he realised he wanted to engage with the companies he was investing in. Listen in to hear the ins and outs of technology investment, just how Michael secured an investment deal with Bellhops, and why we should be working less.



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Famous 5:

Time Stamped Show Notes:

  • 01:02 – Nathan’s introduction
  • 02:00 – Welcoming Michael to the show
  • 02:24 – Michael started his career working with M&A and private capital investment in Silicon Valley
  • 02:50 – He was involved in the 2012 Oracle deal
  • 03:58 – How did Michael get into technology investment?
  • 04:28 – “I had no idea what I wanted to be when I grew up”
  • 04:50 – “You genuinely have to be passionate about investment banking…you see a lot of people churn out”
  • 05:25 – Michael worked at GCA for 5 years in New York
  • 06:39 – “The great thing about venture capital is that when you invest, that’s just the start of the deal”
  • 07:35 – Canaan is an early-stage investor – meaning that they support the companies they invest in
  • 09:30 – What are the roles in a venture firm? And what’s Michael’s next step?
  • 10:29 – How can Michael move up the ranks at Canaan?
  • 11:28 – How do you bring in companies like Bellhops for investment?
  • 11:40 – “It’s all about your network…And it’s important to go deep on a couple of different verticals. You can’t do everything”
  • 13:08 – Michael’s looking to start making fintech deals
  • 13:30 – Connect with Michael on Twitter
  • 15:15 – The Famous Five

3 Key Points:

  1. Work less. Enjoy life.
  2. Making good deals and bringing value to a company is all about your network. Nurture solid relationships with the people around you.
  3. If you’re looking for early-stage investors, find a partner investor who’ll bring more than just money to the table. You’re building a long-term relationship!

Resources Mentioned:

  • Host Gator – The site Nathan uses to buy his domain names and hosting for cheapest price possible.
  • Freshbooks – The site Nathan uses to manage his invoices and accounts.
  • Leadpages  – The drag and drop tool Nathan uses to quickly create his webinar landing pages which convert at 35%+
  • Audible – Nathan uses Audible when he’s driving from Austin to San Antonio (1.5 hour drive) to listen to audio books.