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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 →

Insight
Sim: Founders must deliver 10x value narrowly before expanding their platform vision
“You've got to be able to zoom in on the end user, zoom in on how you make their life 10 times better with your product and how you can uniquely solve that problem. So you sell the product, but then you can market the vision to us.”
Ed Sim Jan 10, 2024 ▶ 42:16 Ed Sim & Jamin Ball: Did Figma Kill M&A Markets & 3 Requirements to IPO in 2024 | E1101 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Sim: Cybersecurity will be exempt from the tech antitrust M&A freeze
“Very few, huge M and A's because of antitrust, maybe save cybersecurity, which has national security interests and those things tend to go a little bit faster.”
Ed Sim Jan 10, 2024 ▶ 46:18 Ed Sim & Jamin Ball: Did Figma Kill M&A Markets & 3 Requirements to IPO in 2024 | E1101 · 20VC with Harry Stebbings
Prediction Held up
Sim: Unicorns will acquire private startups to build platforms before IPO
“You're going to see more private to private as well. And the reason why that makes sense for a private company is because if you're a one product company, going back to the platform play, you're going to go, you're going to have to buy another product or two a…”
Ed Sim Jan 10, 2024 ▶ 48:57 Ed Sim & Jamin Ball: Did Figma Kill M&A Markets & 3 Requirements to IPO in 2024 | E1101 · 20VC with Harry Stebbings
Prediction Held up
Sim: Most 2024 tech IPOs will be down rounds from the ZIRP era
“Look, the margin majority of companies that go do go public this year will be down rounds from the prior rounds, especially if they're raised towards the Zerp era.”
Ed Sim Jan 10, 2024 ▶ 55:22 Ed Sim & Jamin Ball: Did Figma Kill M&A Markets & 3 Requirements to IPO in 2024 | E1101 · 20VC with Harry Stebbings
Prediction Partly held up
Sim: Software net dollar retention will normalize to 110% to 115%
“From there, you know, this new cohort of customers, I think that retention is going to get back to a place where it's more like one, 10. So that can be one, 31, 40, but maybe healthy numbers like one, 10, one, 15.”
Ed Sim Jan 10, 2024 ▶ 1:03:33 Ed Sim & Jamin Ball: Did Figma Kill M&A Markets & 3 Requirements to IPO in 2024 | E1101 · 20VC with Harry Stebbings
Insight
Sim: Investors should challenge founders during good times and support them during bad
“When things are going really, really well, that's when you challenge the foundries even more. And when things are shitty, that's where you kind of pick them off from the ground and maybe kind of cheer them on a little bit. So I call that my three CH is cheer, …”
Ed Sim Jan 10, 2024 ▶ 1:05:03 Ed Sim & Jamin Ball: Did Figma Kill M&A Markets & 3 Requirements to IPO in 2024 | E1101 · 20VC with Harry Stebbings
Prediction Partly held up
Sim: Microsoft's AI leadership will drive cloud market share and H2 revenue
“Because of their lead on everything AI that they're taking market share on the cloud side. So I think that that's going to drive a lot of their business. And I'm hoping that by the back half of the year, you know, you start seeing some of the revenue numbers r…”
Ed Sim Jan 10, 2024 ▶ 1:06:52 Ed Sim & Jamin Ball: Did Figma Kill M&A Markets & 3 Requirements to IPO in 2024 | E1101 · 20VC with Harry Stebbings
Insight
Sim: Enterprise AI adoption requires dedicated AI security
“I think that there's no AI in the enterprise without AI security. And I think that's a completely new category now.”
Ed Sim Jan 10, 2024 ▶ 1:09:17 Ed Sim & Jamin Ball: Did Figma Kill M&A Markets & 3 Requirements to IPO in 2024 | E1101 · 20VC with Harry Stebbings
Insight
Sim: Inception rounds split into discovery, classic, and Megatron jumbo tiers
“The point is the three rounds are, there's a discovery round, which my opinion is less than two million. So it's usually like maybe a first time founder exploring a new market. It would graduate to the next round, which would be a classic. And a classic round,…”
Ed Sim Oct 27, 2023 ▶ 0:00 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 prefers structuring Boldstart inception rounds at $3M to $4M
“I would prefer Your classic structure of three to four million dollars, to be honest with you.”
Ed Sim Oct 27, 2023 ▶ 1:47 Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E1076 · 20VC with Harry Stebbings
Insight
Sim: Repeat founders avoid pre-seed rounds to prevent extra equity dilution
“A lot of times founders who are second and third time founders don't want to even be called to have a pre-seed round because it presupposes you need a seed round. And what does that mean to you, Harry? It means that if you have a pre-seed round and you have a …”
Ed Sim Oct 27, 2023 ▶ 2:27 Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E1076 · 20VC with Harry Stebbings
Disclosure
Ed Sim: Boldstart will split $8M–$10M seed rounds for exceptional founders
“The way that we've evolved now is that sometimes I have to play ball, Harry, right? Sometimes there are some exceptional founders where, okay, you know what? I will split. An eight to ten million dollar round for that exceptional founder, depending on what tha…”
Ed Sim Oct 27, 2023 ▶ 7:03 Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E1076 · 20VC with Harry Stebbings
Assertion Partly supported
Sim: Boldstart funded Snyk through three pre-Series A capital rounds
“You know, guy from sneak, Harry, do you know how many rounds he raised before? He raised his A three rounds of capital before his A. Guess who gave him all three rounds?”
Ed Sim Oct 27, 2023 ▶ 16:16 Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E1076 · 20VC with Harry Stebbings
Assertion Partly supported
Ed Sim: Only 25% of cloud migration is complete
“We're still only 25% of the way of migration from on-prem to Cloud right now”
Ed Sim Oct 27, 2023 ▶ 20:18 Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E1076 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Ed Sim: Top Infrastructure Startups Still Raising Growth Rounds at $250M-$400M Valuations
“There's still pockets Of opportunity where people are going from one to three to four million in the infrastructure space that I see to 10 to 12 kind of on the forecast and they're still raising at two 50 to 400 now.”
Ed Sim Oct 27, 2023 ▶ 32:47 Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E1076 · 20VC with Harry Stebbings
Insight
Sim: Startups solving hard technical problems appear slow before hitting rapid growth
“Some of the hardest problems to solve will take longer and it'll look like your slowest plotting company to start with. But in the long run, to your point, these things are the ones that can actually go, you know, hit the J curve pretty quickly.”
Ed Sim Oct 27, 2023 ▶ 40:51 Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E1076 · 20VC with Harry Stebbings
Insight
Startups taking on incumbents must build baseline table-stakes features first
“No matter how, how, how big of a vision you have, you still need at least the table stakes of, you know, check box of four things that they may need before they even believe in your vision. So it takes longer.”
Ed Sim Oct 27, 2023 ▶ 43:20 Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E1076 · 20VC with Harry Stebbings
Insight
Ed Sim: Underwrite tech startups assuming 10x to 14x forward multiples
“So you've got to build your business and your investment strategy and your ownership strategy around looking at a world where we get 10 to 14 for the best companies forward next year's numbers.”
Ed Sim Oct 27, 2023 ▶ 48:24 Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E1076 · 20VC with Harry Stebbings
Assertion Supported
Pre-cloud enterprise startups required $4M to $5M Series A rounds
“A traditional way of building an enterprise startup would usually require at least four or five million dollars in an A round up, up until the point that, The newer entrepreneurs took advantage of the cloud and open source.”
Ed Sim Nov 30, 2015 ▶ 6:17 20 VC 092: The Repeatable Playbook of SaaS with Ed Sim, Founding Partner @ BoldStart Ventures
Insight
Enterprise founders achieve repeatable success easier than consumer entrepreneurs
“And in consumer, I think it's harder to be a repeat consumer entrepreneur, right? Because you typically start an app, you know, let's say, and launch that thing, and then you try to start another one, but you can't bring that same customer base over. You've go…”
Ed Sim Nov 30, 2015 ▶ 12:32 20 VC 092: The Repeatable Playbook of SaaS with Ed Sim, Founding Partner @ BoldStart Ventures
Insight
Modern SaaS scales via marketing and inside sales, not field reps
“Instead of building a huge regional direct sales force, you know, Today you may bring on a marketing person to be a lead generation machine, right? And then you have built an inside sales force to kind of, you know, follow up on those leads, and then you bring…”
Ed Sim Nov 30, 2015 ▶ 16:37 20 VC 092: The Repeatable Playbook of SaaS with Ed Sim, Founding Partner @ BoldStart Ventures
Prediction Not checkable as stated
Legacy enterprise IT will be replaced by micro-enterprise architectures
“I think the whole monolithic IT infrastructure is getting turned upside down. I like to think of the world as becoming You know, I almost call it the micro enterprise, right? Instead of kind of buying these monolithic, five million dollar, ten million dollar s…”
Ed Sim Nov 30, 2015 ▶ 20:05 20 VC 092: The Repeatable Playbook of SaaS with Ed Sim, Founding Partner @ BoldStart Ventures
Disclosure
BoldStart Ventures strictly keeps seed valuation caps below $10M
“We'll just say sub 10, and it could range from much lower to, you know, upper, up on the upper range. It depends on who the founders are, what their background is, and, you know, and how much they're raising.”
Ed Sim Nov 30, 2015 ▶ 21:37 20 VC 092: The Repeatable Playbook of SaaS with Ed Sim, Founding Partner @ BoldStart Ventures
Disclosure
Sim: Boldstart made eight net new investments in 2023 versus three in 2022
“We did eight net new investments last year, and we only did three the prior year with our largest fund yet”
Ed Sim Jan 10, 2024 ▶ 24:59 Ed Sim & Jamin Ball: Did Figma Kill M&A Markets & 3 Requirements to IPO in 2024 | E1101 · 20VC with Harry Stebbings

Show 16statements(16 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
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