StarZero All shows Try the podcast clipper →

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 →

Prediction Held up
Sim: Apple edge AI developments will not generate meaningful revenue in 2024
“My short would probably be, I mean, just what everyone's looking at now is just Apple right now. I think Apple, You know, you've got an iPhone growth issue over there at Apple, but the one thing that gets me excited about Apple is the idea of machine learning …”
Ed Sim Jan 10, 2024 ▶ 1:07:00 Ed Sim & Jamin Ball: Did Figma Kill M&A Markets & 3 Requirements to IPO in 2024 | E1101 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Sim: Boldstart's fastest-growing 2021 vintage startups are Israeli infrastructure companies
“We have over a dozen Israeli founding teams right now, and two of my fastest growing companies in fund five vintage 20, 21, which had, you know, funded inception to now from zero to about two million of ARR were both Israeli infrastructure companies.”
Ed Sim Jan 10, 2024 ▶ 1:13:30 Ed Sim & Jamin Ball: Did Figma Kill M&A Markets & 3 Requirements to IPO in 2024 | E1101 · 20VC with Harry Stebbings
Insight
Ed Sim: Incubating companies is unscalable unless it is a firm's sole focus
“And by the way, this is not incubating a company. That's not a scalable model. And that's, unless that's all you do.”
Ed Sim Oct 27, 2023 ▶ 9:12 Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E1076 · 20VC with Harry Stebbings
Disclosure
Sim: Superhuman founder locked $10M Series A in separate bank account untouched
“Then he raised pre raised a ten million dollar A round. He put it in a separate bank account and said, I'm not going to touch this thing. I'm literally just going to put it there. I don't want to see it. It's in a separate bank account. I'm only going to opera…”
Ed Sim Oct 27, 2023 ▶ 13:20 Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E1076 · 20VC with Harry Stebbings
What-if
Sim: Snyk Would Have Failed Without Continuous Internal Funding Prior to Series A
“If Guy went out trying to raise capital from someone else and I didn't have enough capital to give to him, he would have gone out of business.”
Ed Sim Oct 27, 2023 ▶ 17:15 Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E1076 · 20VC with Harry Stebbings
Assertion Contradicted
Ed Sim: Enterprise IT spending is re-accelerating
“Enterprise IT spending is re-fucking accelerating right now.”
Ed Sim Oct 27, 2023 ▶ 20:07 Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E1076 · 20VC with Harry Stebbings
Opinion
Ed Sim: Pre-seed startups raising $500K-$1M don't need a board
“If you're raising 500 K to a million, that's what I think of pre-seed, then yeah, you probably don't need a board. Yeah. Yeah. You don't need a fucking board.”
Ed Sim Oct 27, 2023 ▶ 22:21 Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E1076 · 20VC with Harry Stebbings
Insight
Ed Sim: Startups raising $3M-$4M should avoid SAFE notes for priced rounds
“If you're doing a classic round of you're raising three to four million, I like to tell the founder that, hey, you should probably not do a series of safe notes here because you never really know what you own, especially in conversion. You want to actually do …”
Ed Sim Oct 27, 2023 ▶ 22:37 Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E1076 · 20VC with Harry Stebbings
Prediction Partly held up
Ed Sim: Tech M&A volume will increase as investors seek liquidity
“I think we're going to see a lot more M and A's kind of coming ahead right now.”
Ed Sim Oct 27, 2023 ▶ 29:34 Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E1076 · 20VC with Harry Stebbings
Insight
Enterprise software markets repeat and rebuild identical tools every 10-15 years
“So that's what happens in enterprise. It's the same shit getting rebuilt every 10 or 15 years in a different way with a different pitch.”
Ed Sim Oct 27, 2023 ▶ 43:36 Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E1076 · 20VC with Harry Stebbings
Assertion Partly supported
Sim: Snyk took nearly three years to reach $1M in ARR
“It took him two and a half years to kind of get out there and get his first, you know, two and a half to three to get his first million of ARR.”
Ed Sim Oct 27, 2023 ▶ 44:10 Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E1076 · 20VC with Harry Stebbings
Prediction Partly held up
Ed Sim: Tech IPO window won't reopen until Fed cuts interest rates
“I think it's very simple. Mr. Jerome Powell signaling to the world that interest rates are under control now. And the air has been taken out of the balloon and the interest rates have to go down.”
Ed Sim Oct 27, 2023 ▶ 47:31 Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E1076 · 20VC with Harry Stebbings
Disclosure
BoldStart Ventures refuses to invest in single-founder startups
“Well, I, we never liked single co-founder, co-founded companies or single founders, number one.”
Ed Sim Nov 30, 2015 ▶ 8:20 20 VC 092: The Repeatable Playbook of SaaS with Ed Sim, Founding Partner @ BoldStart Ventures
Disclosure
BoldStart Ventures requires founders to be engineers actively building product
“And secondly, they have to be engineers. Engineers, Building product. That's really important.”
Ed Sim Nov 30, 2015 ▶ 9:03 20 VC 092: The Repeatable Playbook of SaaS with Ed Sim, Founding Partner @ BoldStart Ventures
Insight
Seed startups relying on analyst reports for market sizing are uninvestable
“If you have an analyst report to kind of show us, then it's probably not worth investing in, you know, at the seed stage.”
Ed Sim Nov 30, 2015 ▶ 14:37 20 VC 092: The Repeatable Playbook of SaaS with Ed Sim, Founding Partner @ BoldStart Ventures
Insight
Developers increasingly drive enterprise software purchasing decisions bottom-up
“I think developers are increasingly wielding more and more power in the enterprise these days, and it's one of those things where they're, you know, coding or develop, or using a new technology, they'll download it, or they'll try a free version, then they'll …”
Ed Sim Nov 30, 2015 ▶ 19:25 20 VC 092: The Repeatable Playbook of SaaS with Ed Sim, Founding Partner @ BoldStart Ventures
Assertion Supported
New York seed valuations are consistently lower than Silicon Valley
“I think that the New York valuations tend to be a little lower than the Valley.”
Ed Sim Nov 30, 2015 ▶ 21:00 20 VC 092: The Repeatable Playbook of SaaS with Ed Sim, Founding Partner @ BoldStart Ventures
Prediction Held up
AI will infiltrate every enterprise software category within five years
“I think I'm seeing a lot of kind of AI, not AI platforms, but AI being infiltrated across every segment of enterprise software. And I'm also seeing a lot of stuff where messaging is going from consumers to the enterprise as well. Messaging meaning you know, al…”
Ed Sim Nov 30, 2015 ▶ 22:22 20 VC 092: The Repeatable Playbook of SaaS with Ed Sim, Founding Partner @ BoldStart Ventures
Assertion Not checkable as stated
Sim: Third-time founders raise $10M at inception versus $1M for first-timers
“A third time founder is going to raise ten million dollars out of the gate and they may very well deserve it. Whereas a first time founder may get one.”
Ed Sim Jan 10, 2024 ▶ 2:59 Ed Sim & Jamin Ball: Did Figma Kill M&A Markets & 3 Requirements to IPO in 2024 | E1101 · 20VC with Harry Stebbings
Insight
Sim: Having 36 months of cash runway does not mean you have a business
“Just because you have 24 or 36 months of cash doesn't mean you have a business.”
Ed Sim Jan 10, 2024 ▶ 10:31 Ed Sim & Jamin Ball: Did Figma Kill M&A Markets & 3 Requirements to IPO in 2024 | E1101 · 20VC with Harry Stebbings
Insight
Sim: Early VCs need valuation discipline to succeed on $300M to $500M exits
“Cause if early guys will do well, as long as they're not paying 50 to 75 Brie for some of these inception rounds, you know, if they exit a three to 500, but you need more of those to return a fund. So it changes the dynamics of everything where ownership matte…”
Ed Sim Jan 10, 2024 ▶ 28:19 Ed Sim & Jamin Ball: Did Figma Kill M&A Markets & 3 Requirements to IPO in 2024 | E1101 · 20VC with Harry Stebbings
Insight
Sim: Two-thirds of startup bridge rounds yield positive outcomes
“I'd say probably two thirds work out more positively than negatively, but the ones that work out can be outliers.”
Ed Sim Jan 10, 2024 ▶ 35:00 Ed Sim & Jamin Ball: Did Figma Kill M&A Markets & 3 Requirements to IPO in 2024 | E1101 · 20VC with Harry Stebbings
Assertion Supported
Sim: SecurityScorecard surpassed $100M in annual recurring revenue in 2023
“Security scorecard. The market's not big enough. It's not, this is not that they did over a hundred million of error last year.”
Ed Sim Jan 10, 2024 ▶ 35:55 Ed Sim & Jamin Ball: Did Figma Kill M&A Markets & 3 Requirements to IPO in 2024 | E1101 · 20VC with Harry Stebbings
Insight
Sim: A startup's exit TAM matters far more than its initial TAM
“It's not the TAM you start with. It's a TAM you exit with.”
Ed Sim Jan 10, 2024 ▶ 41:37 Ed Sim & Jamin Ball: Did Figma Kill M&A Markets & 3 Requirements to IPO in 2024 | E1101 · 20VC with Harry Stebbings

Show 24statements(40 left)

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
Made with StarZero

Turn any episode into a week of clips.

This entire site, over 1,200 episodes transcribed, diarized, checked and made playable, runs on the StarZero media pipeline. Drop in your own episode and the podcast clipper finds the moments worth sharing, cuts them, captions them, and reframes them for every feed.

Try the podcast clipper Learn more