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Ed Sim

Founder & Managing Partner, boldstart ventures · 3 appearances on the record.

computed by AI from the episodes · how this works → · full disclaimer →

investorfounderauthor@edsim ↗LinkedIn ↗boldstart.vc ↗

Ed Sim specializes in inception- and seed-stage investments in enterprise infrastructure, cybersecurity, SaaS, and AI, having backed companies such as Snyk, Protect AI, Kustomer, Clay, and Superhuman at formation. He previously co-founded Dawntreader Ventures and publishes the newsletter What's in AI/Infra/VC.

88statements → 44claims → 24claims resolved → 46%fully supported → 3.83/5average certainty → 2.14/5average debate potential → 4.2/5argument clarity · the sources → 23said about them ↓

11 supported 10 partly supported 3 contradicted 5 not yet assessed 15 not checkable as stated how the 44 claims stand · each chip opens the sources

22 predictions · 22 assertions · 4 opinions · 23 insights · 15 disclosures · 2 what ifs · every statement was checked. The predictions and assertions are the 44 claims: statements the public record can support or contradict. 24 are resolved, 5 are not yet assessed, and 15 name no date, number or outcome precise enough to check. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.

The record, in short

What the tape says about how Ed argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.

Their most notable supported claim

Assertion Supported
Sim: Loom sold for under $1B after a $1.5B peak 2021 valuation
“At the end of last year, I'm not in the room with Loom, but that last round valuation was at 1.5 billion dollars, right? That was led in 20, 21, and they sold for nine 99 or something, nine 50, right?”
Ed Sim Jan 10, 2024 ▶ 20:52 Ed Sim & Jamin Ball: Did Figma Kill M&A Markets & 3 Requirements to IPO in 2024 | E1101 · 20VC with Harry Stebbings

Their most notable contradicted claim

Assertion Contradicted
Ed Sim: Billion-dollar multi-stage VC funds stopped growth investing in 2022
“The spigot dried out last year, all the big multi-stage firms with a billion dollar plus funds stopped investing in growth.”
Ed Sim Oct 27, 2023 ▶ 3:26 Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E1076 · 20VC with Harry Stebbings

Expressed certainty vs assessment result

none yet certainty 1
none yet certainty 2
75% certainty 3
68% certainty 4
33% certainty 5

weighted support: a fully supported claim counts one, a partly supported claim counts half. Each filled bar is clickable and opens exactly those claims; "none yet" means nothing said at that certainty level has resolved yet

Argument clarity: do they answer the question? how? →

4.2 / 5 directness 4.4 · coherence 4.3 · precision 4.1 · compression 3.7

redirected or did not address 5 of 53 assessed questions (9%). Watch them ▸

This is a score against a rubric. It is not a rank. Every host question → answer exchange is scored with names hidden on directness, coherence, precision and compression, 1–5 each, on meaning alone: disfluencies are ignored, and only raw unedited episodes count. This is the score that measures thought. Every scored exchange, scores shown → · The rubric and its checks →

How they sound: speaking style how? →

285 words/min while actually speaking · 16.9 um and uh per 1k words · 10.9 false starts per 1k · 31.6% of pauses land inside a clause

Measured by listening to the audio itself: 19,353 words across 3 episodes of raw-level tape, transcribed verbatim with every um and uh kept, each one attributed only where the alignment onto our timed stream is unambiguous. These are measurements of speaking style. We do not rank them: across this corpus, fluency and argument quality are nearly uncorrelated (ρ≈0.2), and smooth talking does not signal clear thinking. How it's measured →

How the interview went all their pushback → series average →

Across 3 rated episodes:

host pushback ▾ 4.3/10
pushed back at the host ▾ 2/10
setup questions received 43%

Everything Ed Sim said on 20VC that made the record, most notable first. Filter by type, assessment or year in the ledger →

Assertion Partly supported
Sim: Meta's acquisition of Kustomer took 16 months due to antitrust regulations
“I sat through the customer thing. It took us 16 months from signing to sell to Meta because of antitrust regulations, right?”
Ed Sim Jan 10, 2024 ▶ 27:20 Ed Sim & Jamin Ball: Did Figma Kill M&A Markets & 3 Requirements to IPO in 2024 | E1101 · 20VC with Harry Stebbings
Disclosure
Sim: Boldstart funded Snyk three times prior to its Series A
“Guy from sneak we funded him three times before he got his A round done.”
Ed Sim Jan 10, 2024 ▶ 35:14 Ed Sim & Jamin Ball: Did Figma Kill M&A Markets & 3 Requirements to IPO in 2024 | E1101 · 20VC with Harry Stebbings
Assertion Supported
Sim: Median pre-seed company age is 1.2 years, seed is 2.7
“The median age of a company that raises a pre-seed round is 1.2 years of age now. And the median age of a company that raises a seed round is 2.7.”
Ed Sim Oct 27, 2023 ▶ 2:14 Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E1076 · 20VC with Harry Stebbings
Assertion Supported
Ed Sim: Global quarterly VC funding dropped from $200B to $73B
“If you look at the peak, I think the peak was Q four, 20, 21, that about two hundred billion dollars was invested. Most recently it was seventy three billion in the last quarter.”
Ed Sim Oct 27, 2023 ▶ 3:37 Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E1076 · 20VC with Harry Stebbings
Disclosure
Sim: Boldstart Writes $4M-$6M Follow-On Checks for High-Executing Portfolio Companies
“When I start with a three and a half, four million dollar check, I'm writing a four to six million dollar check in the next round if the company's executed.”
Ed Sim Oct 27, 2023 ▶ 15:49 Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E1076 · 20VC with Harry Stebbings
Assertion Not publicly verifiable
Ed Sim: JPMorgan Chase spends $1 billion annually on cybersecurity
“And JP Morgan, for example, spent a billion dollars a year in cybersecurity.”
Ed Sim Oct 27, 2023 ▶ 20:31 Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E1076 · 20VC with Harry Stebbings
Disclosure
Sim: 55% of Boldstart portfolio companies feature AI offerings today
“Currently in the portfolio of our companies that are running from funds four through six, 55% of our portfolio companies have an AI related offering today.”
Ed Sim Oct 27, 2023 ▶ 26:50 Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E1076 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Sim: 80% of Boldstart portfolio will offer AI within 12 months
“Within the next 12 months, okay, 80% of the portfolio will have an AI offering.”
Ed Sim Oct 27, 2023 ▶ 27:01 Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E1076 · 20VC with Harry Stebbings
Disclosure
Ed Sim raised $1M for Boldstart Fund I, making 10 seed investments
“I just took a million dollars in and made 10 investments of about a 100,000 a pop.”
Ed Sim Nov 30, 2015 ▶ 5:17 20 VC 092: The Repeatable Playbook of SaaS with Ed Sim, Founding Partner @ BoldStart Ventures
Disclosure
Boldstart Fund I pre-money valuations never exceeded $6M in 2010
“I think in fund one, I don't think we paid higher than a five, Million dollar pre-money for any of our investments. Five or six.”
Ed Sim Nov 30, 2015 ▶ 5:27 20 VC 092: The Repeatable Playbook of SaaS with Ed Sim, Founding Partner @ BoldStart Ventures
Disclosure
Boldstart Ventures sold four Fund I companies within two years of launch
“We built that portfolio up in 2010, and by 2012, we had sold, ah, I think four of our companies.”
Ed Sim Nov 30, 2015 ▶ 5:34 20 VC 092: The Repeatable Playbook of SaaS with Ed Sim, Founding Partner @ BoldStart Ventures
Assertion Partly supported
LivePerson spent $20M of its $30M raised building proprietary infrastructure
“A company like LivePerson, we probably raised, you know, over thirty million dollars in about 12 months. And 20 of that went to build our infrastructure because we wanted to build for success, and you needed to build a platform that could scale.”
Ed Sim Nov 30, 2015 ▶ 6:50 20 VC 092: The Repeatable Playbook of SaaS with Ed Sim, Founding Partner @ BoldStart Ventures
Disclosure
Five of BoldStart's last six investments were repeat entrepreneurs
“We funded, I think the last five or six companies we funded, five of them were repeat entrepreneurs who have built, you know, and scaled companies before”
Ed Sim Nov 30, 2015 ▶ 8:35 20 VC 092: The Repeatable Playbook of SaaS with Ed Sim, Founding Partner @ BoldStart Ventures
Disclosure
BoldStart receives 75% of its deal flow from its founder network
“I mean, I think we've tracked that about 75% of our flow comes from founders, whether they be founders that we funded before, you know, their VPs, The engineers that work there, or even, you know, from founders in our existing portfolio who are referring their…”
Ed Sim Nov 30, 2015 ▶ 13:35 20 VC 092: The Repeatable Playbook of SaaS with Ed Sim, Founding Partner @ BoldStart Ventures
Assertion Partly supported
Micro-VC funds grew from nearly zero in 2010 to 400 by 2015
“When I started this in 2010, I think one of the only micro VCs was Jeff Clavier, soft tech. ... Since that time, I think there's 350 or 400 now, quote unquote, micro VCs.”
Ed Sim Nov 30, 2015 ▶ 15:11 20 VC 092: The Repeatable Playbook of SaaS with Ed Sim, Founding Partner @ BoldStart Ventures
Disclosure
Sim: Boldstart launched as a $1M fund in 2010
“We remember we started out with a million dollar fund. And bold start one. This was in 2010 when seed was the first round of record.”
Ed Sim Oct 27, 2023 ▶ 18:30 Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E1076 · 20VC with Harry Stebbings

The other half of the tape: Ed Sim's own voice is left out of every number here. Other people bring the name up 23 times in 11 episodes on 20VC. every mention, with the transcript →

Who brings them up most Harry Stebbings 16Rahul Vohra 3Guy Podjarny 2Hussein Kanji 1Adam Besvinick 1

Every mention by year

tap a year for its mentions
00428320152016201720182019202020212022202320242025episodesmentions
02320152016201720182019202020212022202320242025episodes it came up in
0021.54320152016201720182019202020212022202320242025episodesmentions per episode
2025 1 mention in 1 episode
2023 4 mentions in 2 episodes 2 per episode
2022 3 mentions in 1 episode
2020 2 mentions in 1 episode
2019 7 mentions in 2 episodes 4 per episode
2016 2 mentions in 1 episode
2015 4 mentions in 3 episodes 1 per episode

Appearances (3)

EpisodeDateSpeaking time
Ed Sim & Jamin Ball: Did Figma Kill M&A Markets & 3 Requirements to IPO in 2024 | E1101 · Jan 10, 2024 26m
Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E10 Oct 27, 2023 35m
20 VC 092: The Repeatable Playbook of SaaS with Ed Sim, Founding Partner @ BoldStart Ventu Nov 30, 2015 17m
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