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 30 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
Papa: VCs succeed through luck and portfolio theory, not picking genius
“The thing about venture capital is you have folks that are wrong more than half the time, yet claim their geniuses that they knew exactly the right companies to pick. It's really portfolio theory. That's their friend. They're getting lucky. It'd be much more h…”
Papa: Institutional allocators never reach out for backdoor VC references
“What surprises me is I have yet to have an allocator reach out as a backdoor reference. It's never happened. They basically take the references that the firm offers, and that's who they call.”
Papa: Improving site performance 1-2% yields a 10% sales increase
“You improve site performance a percent or two, you're going to sell 10% more, believe it or not.”
Papa Seeded Toast With $500K Expecting an Early Acqui-Hire
“I'll commit the first 500 K. If you pay me that back in the next few years, you'll get most of the equity back. Pretty aggressive terms because it was going to be an acqui-hire and I should get some return if it is. 250 K into that, they started to displace th…”
Toast laid off half its workforce eight weeks after February 2020 funding
“They just closed the financing in February. They were gearing up to double the size of the company, double the team, And by the end of March, probably eight weeks after that closed, instead we were announcing we had to let go half the company because we couldn…”
Papa: Early-stage venture will always be regional because trust requires prior relationships
“One of the reasons you're always going to have some regional nature in the earlier stages of these is if you're backing great people, it tends to be someone you already know. You're going to have more confidence. You're going to stretch more. You're going to s…”
Papa: Boston VC historically replaced founders with hired-gun CEOs to flip companies
“Historically, Boston was more conservative and they wouldn't swing for the fences. The Boston venture scene was very much, we're going to put in place a hired gun CEO. When that person's done vesting, they're going to want to flip the company and go to their n…”
Papa: Product Pricing Databases Require Three-Click Search for Monetization
“The only way you could monetize such a database is if someone could find something within three clicks. If they had to spend a lot of time looking for that pricing information, they weren't going to use it.”
Papa: Endeca's Founding Was the Birth of Modern Faceted Search
“And that was the birth of guided navigation or faceted search, which is everywhere on the internet today. You use it all the time and you don't even realize it.”
Papa: Post-2000 VCs Shifted Completely from Backing Inexperience to Seasoned Operators
“In 99, the temporal wisdom was back folks without experience because they'll see new ways of solving problems. So it became an asset to be inexperienced. Once we got through 2000, the pendulum swung all the way back hard. All investors wanted to see is that yo…”
Papa: IBM spent $20M on Endeca software it couldn't build internally
“They spent twenty million dollars on us over the years and were using us for very important internal applications that they could not power with their own software.”
Papa: SAP Invested in Endeca but Refused to Discuss Acquiring It
“One of them was SAP. They were an investor in the company, and I couldn't get their corporate development team to even talk to us.”
Papa: Acquiring Endeca Made Oracle the Dominant On-Prem E-Commerce Vendor Overnight
“They basically overnight went from competing for every deal with IBM to suddenly being the dominant on-prem e-commerce company.”
Papa: Reframing Endeca as e-commerce sooner could have rivaled Shopify
“If I had framed the world as e-commerce sooner, we probably would have had a much longer runway as an independent company. We would have at least had a chance to enter the world of Shopify, but we didn't.”
Papa: Solving hard technical problems creates intrinsic assets without needing consumer eyeballs
“I focused on harder technical problems where if we just solve the technical problem, we have a base asset versus you have to get to a bunch of eyeballs before you have an asset.”
Papa: Whiteboard startup success requires founders to reinvent themselves every six months
“But there are people that can reinvent themselves every six months, which is what you need to do if you're going to be a success in an entrepreneurial company from a whiteboard. What you have to do for that first six months is very different than the next.”
Papa: A founder unable to get former co-workers to invest is a red flag
“That is the number one thing to focus on, is to really get to know someone, get to know people that have worked with them, and I've had folks that I've put money behind that they couldn't get any of their former co-workers to invest behind them. Pretty big red…”
Toast had only two VC firms competing to invest in fall 2015
“In fact, the only two firms that were competing to back it at a reasonable valuation were my two lead investors at Indeca that fall.”
Papa: Silicon Valley refused to fund Kiva Systems' hardware before Boston backed it
“My favorite example is Kiva Systems, the robot company that Amazon bought. No one would back hardware in Silicon Valley when they were being founded. Came to Boston, found folks interested in backing what today we call hard tech.”
Papa: Founders must contextualize advice because mentors project personal experience
“The other bit of advice I always give the entrepreneur is when people give you advice, remember you're the only one that can contextualize it to your business. When people give advice, they're typically contextualizing it to what made them successful, which ma…”
Papa: 2001 saw first year-over-year decline in global IT spending
“And the world of IT spend froze in 2001. It was the first year over year decline.”
Papa: Endeca was down to under two months of cash in August 2001
“By the time we got to August, 2001, we had less than two months cash left.”
Papa: Endeca reached a $2M Q4 2001 after near-zero revenue that year
“The other thing to note here is we went from having no revenue all year, or virtually none, because we had one customer from the year before, to doing a two million dollar quarter in Q-IV, which was a very strong quarter.”
Papa: Endeca counted half of the top 100 e-commerce sites as customers
“We had half of the top 100 e-commerce sites.”
Papa: Oracle Finalized the $1.1B Endeca Deal in Six Weeks
“From first email to announcement with Oracle was six weeks, a testament to how fast Oracle can align their teams and make something happen.”
Papa: Endeca could have exited to Amazon around 2005
“There were two other moments we could have exited the business. One was around 2005 where Amazon was very attracted to what we were doing.”
Papa: 2012 silicon spinout generates over $1M weekly, tracks 2023 IPO
“And sure enough, I spun a silicon company out of a university in Europe in 2012. And they're on track to go public next year. They're now up over a million a week.”
Toast founders built second commerce app on Apple App Store
“In fact, they were the second mobile app in the Apple App Store for commerce after Amazon.”