267. Advice from a Unicorn Founder Turned VC, the Future of the VC Landscape for Founders & VCs, and the Founder Love Metric (Tim Guleri)

Tim Guleri of Sierra Ventures joins Nick to discuss Advice from a Unicorn Founder Turned VC, the Future of the VC Landscape for Founders & VCs, and the Founder Love Metric. In this episode, we cover:

• Walk us through your background and path to VC
• What’s the thesis at Sierra Ventures?
• What's been your biggest influence on the firm's ethos?
• You've had two incredible outcomes as a founder... first question is do you think the process of building a company today is materially different than it was when you did it... if so how?
• We've talked a lot on the show, over the past 8 months about the effects of COVID on venture... what have been you main observations on how VCs are adjusting to investing during COVID?
• What do you think the new normal for startups looks like post-covid?
• How do you advise a founder that's in a hot space, doesn't need capital, but has inbound interest and large investment offers, maybe at inflated valuations, from tier 1 coastal investors?
• How do you handle situations where the product is just not a great fit for the market and the momentum is not building the way it should?
• You've been through the exit process this yourself and, I'd imagine, even w/ great outcomes those are some of the hardest decision one faces as a CEO... Do you have a framework or an approach to assessing whether an exit offer is strong and should be taken or whether the founder should hold out for a bigger outcome.
• There are a lot of factors that play into having to wind down a company...  are there any that standout that signal to you that it's no longer working and we need to face to reality?
• You mentioned something interesting recently pertaining to your relationship with founders and that’s that you track a metric that you dub “Founder Love”. Can you explain how you gauge and measure this?
• What do you think the venture industry looks like in 5-10 year