The Ledger
Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.
why aren't all 88 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 4 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable
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.”
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.”
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…”
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.”
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.”
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, …”
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…”
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.”
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,…”
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.”
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: 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…”
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: 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: 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.”
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.”
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: 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.”
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.”
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…”
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…”
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…”
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.”
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”
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?”
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.”
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: 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.”
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: JPMorgan Chase spends $1 billion annually on cybersecurity
“And JP Morgan, for example, spent a billion dollars a year in cybersecurity.”
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.”
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 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.”
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.”
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.”
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.”
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”
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…”