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.

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why aren't all 23 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 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

Insight
Seibert: Founders attempting a pivot need 12 months of cash runway
“You need at least a year of cash left, because if you don't have a year of cash, you're not going to have time to see this pivot through. And so it's really like founder grit and enough cash. If those aren't there, return your capital.”
Jeff Seibert Nov 22, 2023 ▶ 14:20 Jeff Seibert: Why OpenAI Will Become an Infrastructure Play | E1085 · 20VC with Harry Stebbings
Insight
Seibert: Great founders build true alignment rather than 'disagree and commit'
“I will not disagree and commit. I think this is the hallmark of great founders is you need to be able to convince your team and have the trust of your team to go all in on a new direction.”
Jeff Seibert Nov 22, 2023 ▶ 16:46 Jeff Seibert: Why OpenAI Will Become an Infrastructure Play | E1085 · 20VC with Harry Stebbings
Insight
Seibert: Horizontal AI wrappers OpenAI will solve are bad investments
“If you're working on a use case that's pretty horizontal, that like OpenAI is going to need to solve within five years in order to scale. That's not a great investment, and that's not a good use of your time as a founder.”
Jeff Seibert Nov 22, 2023 ▶ 28:21 Jeff Seibert: Why OpenAI Will Become an Infrastructure Play | E1085 · 20VC with Harry Stebbings
Insight
Seibert: Emotional attachment to a problem is a founder superpower
“I think it's so much easier to build something that you personally feel than have to sort of try to interpret other people's thoughts and beliefs about it. So no, I would not be worried about getting too emotionally involved. I think that's a superpower.”
Jeff Seibert Nov 22, 2023 ▶ 3:48 Jeff Seibert: Why OpenAI Will Become an Infrastructure Play | E1085 · 20VC with Harry Stebbings
Insight
Seibert: Imposing a paranoid founder mindset on teams is demotivating
“If you have that mentality with the team, it's very demotivating, right? It's like, what are we trying to go to? Like, when are we going to get somewhere? And so it's really important to celebrate small wins.”
Jeff Seibert Nov 22, 2023 ▶ 10:14 Jeff Seibert: Why OpenAI Will Become an Infrastructure Play | E1085 · 20VC with Harry Stebbings
Insight
Seibert: LLM fine-tuning requires surprisingly little data if high quality
“While it creates, it takes so much time, data, energy, money to train an LLM, fine tuning it can actually be done relatively straightforwardly with a surprisingly small amount of data, as long as your data is very high quality and focused.”
Jeff Seibert Nov 22, 2023 ▶ 23:56 Jeff Seibert: Why OpenAI Will Become an Infrastructure Play | E1085 · 20VC with Harry Stebbings
Insight
Seibert: Products built in 2-4 weeks scripting GPT are thin wrappers
“If your primary product value is, is scripting GPT, that's a thin wrapper. If you've built it in two to four weeks, that's a thin wrapper.”
Jeff Seibert Nov 22, 2023 ▶ 26:21 Jeff Seibert: Why OpenAI Will Become an Infrastructure Play | E1085 · 20VC with Harry Stebbings
Insight
Seibert: Down markets enable higher startup talent density than bull markets
“I actually love sort of down markets because I think in the very hot markets, it's too easy to raise capital and you peel off all the sort of like fantastic second engineers or product managers or designers or whoever they might be, and they go get funding and…”
Jeff Seibert Nov 22, 2023 ▶ 51:32 Jeff Seibert: Why OpenAI Will Become an Infrastructure Play | E1085 · 20VC with Harry Stebbings
Insight
Seibert: Customer obsession drives founder success over technical skill
“I'd say looking at my portfolio, it's not even necessarily the most techie founders that are successful, but the most sort of customer obsessed and just like really deeply personally understand the market and really want to solve it. And usually have some patt…”
Jeff Seibert Nov 22, 2023 ▶ 53:15 Jeff Seibert: Why OpenAI Will Become an Infrastructure Play | E1085 · 20VC with Harry Stebbings
Insight
Seibert: Product managers focus on competitors when lacking product vision
“I think a lot of product managers get too distracted watching the competition. And they don't have a vision for their own product.”
Jeff Seibert Nov 22, 2023 ▶ 58:35 Jeff Seibert: Why OpenAI Will Become an Infrastructure Play | E1085 · 20VC with Harry Stebbings
Insight
Paired Buddy Systems Remove the Need for Scheduled Meetings at Digits
“The way this works is we do what's called a buddy system, so every project every week is tackled by two people, some two to four people, but usually two people, and the reason is it's because you're remote, right? Instead of sort of working by yourself in your…”
Jeff Seibert May 1, 2020 ▶ 15:03 20VC: Framework For Hiring The Best Talent 100% Remotely, Raising $32M From Benchmark and GV Pre-Launch and How To Think Through Capital Efficiency and Runway Today with Jeff Seibert and Wayne Chang, Co-Founders @ Digits
Insight
Seibert: Founders must dampen startup volatility to keep teams productive
“And I think in retrospect, it's your job as the founder to really dampen this roller coaster for your team so that they can remain productive and give your team a really set direction that they feel comfortable and confident executing on.”
Jeff Seibert Jan 29, 2016 ▶ 11:36 20 VC FF 032: Jeff Seibert on Lessons From Being Acquired By Twitter & Box and Now Leading Twitter's Consumer Product
Insight
Seibert: Acquisitions are about mission acceleration, not cashing out
“My belief on acquisitions and IPOs for that matter, exits of any kind is that they are not about exiting. The entire point is to become more successful at your mission.”
Jeff Seibert Jan 29, 2016 ▶ 12:30 20 VC FF 032: Jeff Seibert on Lessons From Being Acquired By Twitter & Box and Now Leading Twitter's Consumer Product
Insight
Seibert: Designing software features for the average user is a mistake
“So the product managers who were super data-driven started designing and building features for the average user, because that's what the data told them. And they actually believed that there was something such as an average Twitter user. It's such a huge mista…”
Jeff Seibert Nov 22, 2023 ▶ 2:31 Jeff Seibert: Why OpenAI Will Become an Infrastructure Play | E1085 · 20VC with Harry Stebbings
Insight
Seibert: Startup CEOs face severe feedback isolation from internal employees
“I think there's a ton of challenges, and it's even worse for CEOs, because who in your company is going to give you really crisp, blunt feedback on what you did right and wrong?”
Jeff Seibert Nov 22, 2023 ▶ 6:36 Jeff Seibert: Why OpenAI Will Become an Infrastructure Play | E1085 · 20VC with Harry Stebbings
Insight
Seibert: Investors are too removed to critique CEO meeting behavior
“And your investors aren't involved enough in the day to day to really know. So they can give strategy advice, but they don't know how you're behaving in meetings.”
Jeff Seibert Nov 22, 2023 ▶ 6:45 Jeff Seibert: Why OpenAI Will Become an Infrastructure Play | E1085 · 20VC with Harry Stebbings
Insight
Fenton: Accounting startups win just by making the product somewhat enjoyable
“When Uber was going against the taxi industry, the NPS scores on taxis was so bad, right? Like even if Uber was mediocre, it would still be way better. And he said accounting gave him the exact same vibes. Like the status quo is just so bad that if you can mak…”
Jeff Seibert Nov 22, 2023 ▶ 18:54 Jeff Seibert: Why OpenAI Will Become an Infrastructure Play | E1085 · 20VC with Harry Stebbings
Insight
Seibert: Angel investors should keep check sizes identical across deals
“So my advice would be just like, be very disciplined. It's like do a bunch of deals because you need a portfolio and put the same amount in every time and average it out.”
Jeff Seibert Nov 22, 2023 ▶ 46:03 Jeff Seibert: Why OpenAI Will Become an Infrastructure Play | E1085 · 20VC with Harry Stebbings
Insight
Seibert: Enterprise software traction is more sustainable than consumer traction
“On the consumer side, I'd say real traction on enterprise software. Potentially more sustainable.”
Jeff Seibert Nov 22, 2023 ▶ 47:02 Jeff Seibert: Why OpenAI Will Become an Infrastructure Play | E1085 · 20VC with Harry Stebbings
Insight
Seibert: Startup leaders must answer team questions within 24 hours
“So when your team comes to you with a question, you need a decisive answer within 24 hours. And if you're slower than that, you're not moving fast enough.”
Jeff Seibert Nov 22, 2023 ▶ 58:47 Jeff Seibert: Why OpenAI Will Become an Infrastructure Play | E1085 · 20VC with Harry Stebbings
Insight
Formulaic Resume Questions Easily Reveal Candidate Career Patterns
“And it's just because it's formulaic, And you're asking the same questions for each job role. You can very easily see patterns over a person's career.”
Jeff Seibert May 1, 2020 ▶ 17:37 20VC: Framework For Hiring The Best Talent 100% Remotely, Raising $32M From Benchmark and GV Pre-Launch and How To Think Through Capital Efficiency and Runway Today with Jeff Seibert and Wayne Chang, Co-Founders @ Digits
Insight
A VC's Greatest Value-Add Is Keeping Founders Focused on Forward-Looking Strategy
“What I think is most helpful is when your investors are always looking forward because they're not caught up in the day to day. And many founders get so caught up in the day to day, their context switching, their racing between fires, that they sort of lose tr…”
Jeff Seibert May 1, 2020 ▶ 32:03 20VC: Framework For Hiring The Best Talent 100% Remotely, Raising $32M From Benchmark and GV Pre-Launch and How To Think Through Capital Efficiency and Runway Today with Jeff Seibert and Wayne Chang, Co-Founders @ Digits
Insight
Seibert: Entrepreneurs shouldn't wait for a mind-blowing, perfect idea
“And I think that was the first big lesson I learned is not to sort of hold out for this perfect concept that's going to blow the world away. Very, very few businesses start out as this like mind blowing idea that no one's ever thought of.”
Jeff Seibert Jan 29, 2016 ▶ 4:29 20 VC FF 032: Jeff Seibert on Lessons From Being Acquired By Twitter & Box and Now Leading Twitter's Consumer Product
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