AI-Enabled Entrepreneurship Trend

Nikhil Basu Trivedi and Mike Smith are the Co-founders of Footwork where they invest up to $15 million in Seed and Series A rounds. This is the first time they've ever sat down to record a conversation together on video.

We talk about starting the firm in 2020, their secret sauce for working with founders, lessons investing in Canva’s Seed round, scaling Stitch Fix from $0 to $1B revenue in five years with $17m in capital, why AI will enable a new wave of entrepreneurship, and how public company boards are discussing AI today.

Thank you to Tony Staehelin, Andrew Riesen, and Hunter Walk for helping brainstorming topics for the conversation.

Thank you to Flex for supporting this episode.

Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz

Timestamps:

(0:24) Starting Footwork from a tweet in 2021

(3:11) Difference between startup and public company boards

(4:52) 20-40% of board meetings are now about AI

(7:48) How Footwork’s investing in AI today

(10:37) AI will enable millions of new entrepreneurs

(15:04) 37 questions to ask when starting a VC firm

(17:40) Importance of differences

(23:08) The pace of VC is faster than operating

(26:26) Footwork’s secret sauce (2x board seats, 1-pager)

(31:59) Investors should talk to and help employees

(37:05) Building an equal-carry partnership

(39:33) How Footwork makes decisions

(43:21) Navigating short-termism and politics in VC firms

(51:18) “You’re only as good as your next investment”

(53:30) Characteristics of great founders

(58:13) Canva’s Seed pitch in 2014

(1:02:54) Joining Stitch Fix as 4th employee

(1:06:40) Scaling Stitch Fix $0 to $1B revenue in five years with $17m in capital

(1:16:48) Raising from Bill Gurley after a failed Series A

(1:19:40) Footwork’s office near YC

(1:22:10) Opportunities in consumer health

(1:25:20) Using flash mobs to win deals

(1:26:15) Dad life

Referenced

Footwork: https://www.footwork.vc/

Anything: https://www.anything.com/

Table22: https://www.table22.com/

Canva: https://www.canva.com/

Stitch Fix: https://www.stitchfix.com/

Honeydew: https://www.honeydew.com/

Follow Mike

Twitter: https://x.com/msmith492

LinkedIn: https://www.linkedin.com/in/michaelcsmith1

Follow Nikhil

Twitter: https://x.com/nbt

LinkedIn: https://www.linkedin.com/in/nikhilbt

Substack: https://nbt.substack.com/

Follow Turner

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LinkedIn: https://www.linkedin.com/in/turnernovak

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