Motivations in Entrepreneurship: Scar Tissue vs. Mission-Driven Ambitions

“VC is more about the ground game than the air game.” – Nakul Mandan

“Entrepreneurs think it’s going to be like the Michael Keaton version, and the good ones, they actually have to work through the Christopher Nolan version of Batman.” – Ben Choi

Nakul Mandan is the founder of Audacious Ventures. Audacious is a seed stage venture firm managing ~$250M. Audacious' foundational belief is that ultimately startup success comes down to two key ingredients: Large markets and A+ teams. Accordingly, the Audacious team focuses on two jobs: 1/ Invest in force of nature founders; 2/ Help them recruit an A+ team. Then they get out of the way. Prior to founding Audacious, Nakul was a GP at Lightspeed.

Some of the companies Nakul has backed over the last decade include: Gainsight, People.ai, WorkOS, Multiverse, Marketo, 6Sense, BuildingConnected, Vartana, Tezi and Maxima, amongst others.

You can find Nakul on his socials here: X / Twitter: https://x.com/nakul LinkedIn: https://www.linkedin.com/in/nakulmandan/ Personal Website: https://www.nakulmandan.com/

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Ben Choi manages over $3B investments with many of the world’s premier venture capital firms as well as directly in early stage startups. He brings to Next Legacy a distinguished track record spanning over two decades founding and investing in early-stage technology businesses. Ben’s love for technology products formed the basis for his successful venture track record, including early stage investments in Marketo (acquired for $4.75B) and CourseHero (last valued at $3.6B). He previously ran product for Adobe’s Creative Cloud offerings and founded CoffeeTable, where he raised venture capital financing, built a team, and ultimately sold the company.

Ben is an engaged member of the Society of Kauffman Fellows and has been named to the Board of Directors for the San Francisco Chinese Culture Center and Children’s Health Council. Ben studied Computer Science at Harvard University before Mark Zuckerberg made it cool and received his MBA from Columbia Business School. Born in Peoria, raised in San Francisco, and educated in Cambridge, Ben now lives in Palo Alto with his wife, Lydia, and three very active sons.

You can find Ben on his socials here: X / Twitter: https://x.com/benjichoi LinkedIn: https://www.linkedin.com/in/bchoi/

And huge thanks to this episode's sponsor, Alchemist Accelerator: https://alchemistaccelerator.com/superclusters

OUTLINE:

[00:00] Intro

[04:14] Why is Nakul fascinated by Batman?

[06:41] Does entrepreneurial motivation often come from inspiration or frustration?

[10:33] Nakul's childhood and early upbringing

[14:37] How Nakul grew from introvert to extrovert

[16:19] Did Ben see the ambition in Nakul from the day they first met?

[18:19] How did Ben's parents' work in Chinatown influence Ben as a teenager?

[22:47] How did Ben and Nakul meet?

[28:50] Would Nakul have raised in 2020 if he knew how hard it would be?

[33:49] Why did Next Legacy not invest in Fund I, but in Fund II?

[37:49] How did Nakul react to the pass on Fund I?

[39:56] The kinds of people at Next Legacy's dinners

[43:49] Why Audacious kept a low profile in 2021

[49:01] Why Audacious deployed Fund I over 4 years, instead of 3

[51:46] Balancing the paradox of one of Audacious' cultural values

[55:14] The difference between pitching individuals and institutions

[1:00:42] What is it like to be married to an interior designer?

[1:02:40] Nakul's favorite coffee shop, bar, and restaurant

[1:05:56] What makes a sock special to Ben?

[1:07:17] Why does Ben still like venture?

[1:08:10] Why does Nakul still like venture?

[1:11:36] Thank you to Alchemist Accelerator for sponsoring!

[1:12:37] If you enjoyed this holiday episode, and want more like this, do let me know!

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