Dec 14, 2021 • 1HR 0M

Boldstart ventures Ed Sim on starting his career during the dot-com bubble, the opportunity as being a true day one investor, and views on today's VC market compared to past eras

Episode 64

Samir Kaji
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Venture Unlocked is the playbook for starting, operating, & scaling a successful venture capital firm. Samir Kaji, Host of Venture Unlocked has +20-years of experience assisting & advising startups and venture firms. Listen for VC fund guidance.
Episode details

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.

Our guest today is Ed Sim, founder and general partner of boldstart ventures, an NYC-based firm started in 2010 with the focus on being a day-one partner for founders. Boldstart had a modest beginning, with only a $1M fund in 2010. It has since grown to just under $500M in AUM. Some of his first check investments include Snyk, Kustomer, BigID, and Superhuman.

Ed previously co-founded and was a managing partner at Dawntreader Ventures in 1998. Dawntreader grew to $290 AUM and invested in seed and early-stage software, Internet, and digital media companies.

He began his career at JP Morgan, and early on in his career learned how to code. Ed did his undergrad at Harvard College and was a four-year letterman on the men’s lacrosse team.

Ever insightful and candid, Ed provided so many great nuggets around building a firm, navigating markets, and tell us why exactly he’s decided to stay true to the original thesis of backing entrepreneurs at early formation.

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In this episode we discuss:

01:22 Ed’s decision to become a fulltime investor

03:06 Why Ed turned down a Harvard MBA to start his first fund

04:54 The investment thesis behind boldstart and how it was informed by his time at Dawntreader.

08:21 How early days of running a new firm will test resiliency

09:57 What was their major inflection point?

13:18 How Ed gets comfortable with being the first check in, often pre-product, and ways to mitigate risk.

16:14 Patterns Ed has seen when looking at his successful investments

20:03 How he spots “non-obvious” founders and deals

27:27 How they underwrite to what can be a “fund returner”

31:35 How boldstart thinks about generating alpha in such a competitive seed market

36:08 Where he believes we are in the market cycle today, and what the years ahead may look like

43:52 The non-obvious things a venture investor needs to think about to maintain durability over the long term

47:28 What emerging managers need to think about when evaluating when to join a firm versus starting their own.

50:38 The most counterintuitive lesson Ed has learned about being a venture capitalist

53:28 The founder that helped define Ed as an investor

57:28 The investor that has been most influential to his career

Mentioned in this episode:
boldstart ventures

I’d love to know what you took away from this conversation with Ed. Follow me @SamirKaji and give me your insights and questions with the hashtag #ventureunlocked. If you’d like to be considered as a guest or have someone you’d like to hear from (GP or LP), drop me a direct message on Twitter.

Podcast Production support provided by Agent Bee Agency