Public evidence record
Published podcast speaker
Books, apps, and tools
book / uses
“We read a bunch of Ben Thompson and we read Good Strategy/Bad Strategy, and we're like, we're going to turn this company around using strategy. So we wrote this detailed memo full of his data science and my crazy ideas on how we can actually turn the company around by adding monthly space and competing more at the margins with companies like WeWork and Knotel.”
app / likes
“What I love Not Boring to be a big and lasting thing that builds actual products and does things that outlive me, 100% I would love that.”
Claim ledger
49 transcript-backed records
01 / belief
“I think one of the most important things about 2020 and 2021 for a lot of people was learning about themselves.”
02 / belief
“If any of you want a piece of the Twitter take private, $43 or $44 million minimum check. I think actually they are taking relatively small checks from what I've seen.”
03 / prediction
“Then I think with somebody like Elon, it's either going to go horribly, horribly, horribly wrong or it's going to go really, really, really well.”
04 / evaluation
“I've written about the company, but this is a point that I am taking from Twitter, which is that somebody said it is the worst UI/UX customer experience in the biggest market out there and they have the best solution with iBuying.”
05 / recommendation
“What I love Not Boring to be a big and lasting thing that builds actual products and does things that outlive me, 100% I would love that.”
06 / commitment
“I think what I will hopefully continue to do well at is looking into the very near future, never being the earliest person on something, but being the person who can say, all right, this is actually probably worth taking a look at now, and here's actually why it's not as wild as it seems, or why this is wild as it seems but it just might work.”
07 / belief
“I think that all helps because, we'll get to Breather, that was my first year’s experience.”
08 / belief
“I think 8 out of 10 DAOs might totally fail because they have that leadership issue or who is the final decision maker issue.”
09 / belief
“I think that is the obvious one and the one that I don't have a solution to because I've said on the other side that if I have other people writing, maybe people don't want to come to Not Boring to read X, Y, and Z other person.”
10 / belief
“Someone I think signed up with Satya Nadella's email address, but it certainly wasn't him, and that email address has never opened an email.”
11 / belief
“When you think about the future, tech, and AI is stealing everyone's job, maybe that happens at some point in the future. But I think the really great thing is people are pulling resources in the right place and then you can access them at the time they make sense.”
12 / belief
“I have a few pieces coming up. So I think, chances are, we're going to just cross a million dollars in 2021.”
13 / commitment
“The kind of things that maybe before you would have gotten out of a partnership at a firm and certainly right now you get out of a partnership at a firm. It's not as formal, and I will still make more mistakes than probably a firm will make, at least on saying yes to things that maybe I shouldn't say yes to.”
14 / belief
“I'm not solely alone here, but I also can't be like, all right, Dan and Puja, you write the next Not Boring while I think about building this organization.”
15 / belief
“Definitely, I think probably because of Not Boring Club I shied away from trying to be a community manager again.”
16 / belief
“I didn't have a future job lined up, but I was interviewing, trading, and making a bunch of dumb decisions that I think would make me a better investor later on.”
17 / belief
“I've always been honest that I'm going to follow whatever I think is the most interesting. It makes my schedule miserable because I pick each week what I want to write about based on what I think the most interesting thing happening is.”
18 / belief
“I think for Acquired, for Not Boring, for good content businesses, this is why I don't want to scale it and have to write a brand guideline or the style guide.”
19 / belief
“I had a 150-person team that I think I got along really well with. So I think the sabbatical is also useful in being like, look, Packy is away in Japan right now, the company hasn't fallen apart, and your life is not miserable.”
20 / evaluation
“Even figuring out how to price the round, figuring out what should go into the term sheet, spending time negotiating that, and then being on a board, God forbid. It actually just doesn't work with my strategy because it is a house of cards already, where you move one thing and the whole thing breaks.”
21 / belief
“Exactly, and I think part of that is probably what became Uber Eats. Ultimately, these people are moving around the city on their bikes.”
22 / belief
“Our ideas in our podcast, I think, are a testament to the fact that I get things wrong all the time.”
23 / belief
“Not Boring is still, I think, even if there's a two-year bear market, we come out the other side, reload, continue to grow, things continue to get better, and all of that.”
24 / belief
“I learned later that it came down to me and somebody who ended up working for the company later who's way more talented and smarter than I am.”
25 / evaluation
“We traded pretty actively and made some of the dumbest trades in the history of the world. I think I bought Tesla during that summer at $29 and sold it.”
26 / commitment
“We read a bunch of Ben Thompson and we read Good Strategy/Bad Strategy, and we're like, we're going to turn this company around using strategy. So we wrote this detailed memo full of his data science and my crazy ideas on how we can actually turn the company around by adding monthly space and competing more at the margins with companies like WeWork and Knotel.”
27 / preference
“What's really interesting is there are actually companies that I’ll say no to that I would invest in, that I think are great businesses, and I think to have something interesting strategically, but just maybe isn't interesting enough to the audience where actually, it would still perform.”
28 / commitment
“I will give you the timeline of how this round game came together. I will give you exactly how we think about cap table construction.”
29 / recommendation
“I think really, the advisor there is like, working with some of the companies and their portfolio to think about how they tell their story, writing pieces like I wrote with Chris in The Economist, they'll introduce me to companies that they have invested in and are excited about.”
30 / preference
“I did cross country and track in high school too. That was kind of a similar vibe where for most people that's punishment making them run many miles, and I love that.”
31 / evaluation
“It was that I lied all semester and said that I was doing really well in the class. So I thought that was the best parenting lesson that I could have ever received because it was a really good lesson both in honesty and in work ethic.”
32 / recommendation
“Please, for the love of God, don't sign a lease before you actually try to build a community because it sounds like the other stuff is hard, but what's really hard is actually building a community around this kind of stuff.”
33 / recommendation
“I wrote a bunch and you can see these essays too, trying to justify how this could be a venture scale thing if you added a bunch of stuff on top and started community first.”
34 / belief
“I think the acquisition is interesting because, as you guys pointed out, it gives Slack this massive professional Salesforce to go push their product into all the [...”
35 / belief
“I think shared channels have become a part of Slack Connect and that's what Slack Connect is.”
36 / belief
“I think the F for me is trying to integrate Slack and Salesforce the products and failing and turning Slack more into Salesforce than Salesforce more into Slack.”
37 / belief
“Slack, as we'll discuss I’m sure, just reported earnings and the numbers look good, yet again. It's one of these companies that has been underappreciated but I think over time is going to build into a juggernaut.”
38 / belief
“Next year, this is a billion-dollar run rate company with 86% gross margins that just became free cash flow positive and grew from $10 million (I think) to $36 million in free cash flow this quarter.”
39 / uncertainty
“I don't know how you do that if you're Slack and how you communicate that to the enterprises that people are getting all these alerts.”
40 / belief
“I'm sick of this. The real reason that kind of suffers is that I think that Teams’ bear case.”
41 / belief
“To Slack's great benefit, you're just counting this tiny, tiny, tiny discount rate and yet it's not being reflected in the stock price if they're not taking that long-term view that I think you can't be any better than a C for me, unfortunately.”
42 / belief
“I think that's right, but I do think for this next generation, companies like Huddle are going to come out and combine the best of Discord with all of the below-the-surface-level features of Slack.”
43 / belief
“I think mine is somewhere similar and it just revolves a little bit more around Slack Connect really being what they think it's going to be and not just creating the social network at the horizontal layer but also making being the target in Salesforce a better experience, humanizing the whole sales process a little bit versus getting hit with some awful drip campaign.”
44 / evaluation
“He went on The Twenty Minute VC with Harry Stebbings and talked about being this connective tissue between different apps and what the next level of integration looks like for Slack. That would've been an amazing way to do this (I think) to be able to just embed Slack in different apps because, to your point, everything that they've done that seems really simple that makes chat seem really simple is really, really hard.”
45 / evaluation
“Slack just reported their numbers and they grew (I think) from 380,000 Slack Connect endpoints to 520,000 Slack Connect endpoints in the last quarter alone. This has been a huge area and focus for the business (maybe in retrospect) running up for a Salesforce acquisition because this certainly does make them a lot more attractive as—like Ben Thompson called it—The Work Social Network.”
46 / evaluation
“To me, that's the big risk because there's one collaboration software that people interact with directly, and then to the next generation of Slacks that are built more for this world where we all have to be collaborating with whatever that software is as the central hub, versus as something that we chat with each other on in the office.”
47 / preference
“I think more than anything, it's a way for people to try before you buy the Slack product, because your innovative partner has told you that they want you to use that product.”
48 / evaluation
“I would say that Microsoft Teams has about 10 times the number of users as Slack crossed (maybe) 100 million user range recently, whereas Slack’s in that 12 million range and haven't really reported numbers recently on that.”
49 / prediction
“To hear Stuart talk about it, that's because if Slack threatens email, then Outlook is threatened, and then the whole Microsoft Suite is threatened.”