Opinion
Siroker: Rewind's 20-person team executes faster than Optimizely's 450-person team
“Today we have 20 people and rewind we had 450 and I feel like with 20 people we're able to do more and execute faster and be More tightly aligned than and ship than we ever did at Optimizely.”
Insight
Siroker: Ex-Apple founders often fail to ship due to unrealistic quality expectations
“I see a lot of companies today that are ex Apple people who've built amazing things and they go off and they spend years and years toiling away and never really ship anything. And, you know, I think they have this sense of like, it needs to be As good as the l…”
Prediction Open · timeframe Sep 2028
Siroker: Thousands of multi-billion-dollar vertical LLM application companies will emerge
“There's whole categories of companies that are going to be cat, you know, Category defining independent successful big public multi-billion dollar companies that are just applications of large language models in a specific domain for a specific user with a gre…”
Prediction Not checkable as stated
Siroker predicts 50% of work will be fundamentally changed within 10 years
“I think a lot of jobs will be gone in 10 years, but they'll likely be replaced with new ones.
I think that's probably an obvious
Conclusion.
I think on the order of probably 50% of work will go away.
It would be fundamentally changed.”
Prediction Not checkable as stated
Siroker: AGI will eventually perform half the work of human engineering teams
“Eventually, you know, I don't think it will necessarily replace engineers, but it'll certainly augment them. You'll have plenty of, you know, half the work that an engineering team does will be done by AGI, and half will be done by humans, and the human stuff …”
Disclosure
Siroker: Rewind published its unredacted investor pitch deck and video on Twitter
“That's why I announced and shared our investor deck unredacted. I didn't hide any numbers. You know, you can find it on Twitter, you know, seven minute pitch you know, millions of people have seen it.”
Assertion Supported
Siroker: Rewind stores data locally and Rewind has no access to it
“They just passively capture everything in a privacy sensitive way. It's stored locally. We don't have access to it. Only you have access to it.”
Opinion
Siroker: Meeting Bots Are Vitamins; Continuous Screen Capture Is a Painkiller
“Scribe was kind of an, and all kind of meeting bots are kind of nice to have. It's a vitamin, it's useful, you know, but like the idea that you could capture anything you've seen and never have to take notes again, that was a painkiller for some people.”
Opinion
Siroker: Google's 'Googliness' Was Poorly Defined and Occasionally Weaponized
“Google has this, Sense of Googliness that you had to assess candidates by, but it always frustrated me that there was no clear definition of what Googliness meant, what it meant to be Googly. And I actually found that it tended to, on occasion, become weaponiz…”
Opinion
Siroker: Many AI tools are flash-in-the-pan demos with zero retention
“I think a lot of AI tools today are the sort of flash in the pan, exciting, cool demo. Well, cool. Isn't it amazing that technology can do this, but then nobody sticks around.”
Insight
Siroker: Rewind AI has massive switching costs due to accumulated personal data
“The switching costs are very high. And we also have everything you've seen that are heard up until you start, since you use our rewind. So even if tomorrow, Some big tech company launches what we do. You know, we've got a lot of users who say, well, why'd I sw…”
Disclosure
Siroker: Rewind ensures it passes the 'subpoena test' by retaining zero data
“You know, for us, the test I always use is if we were subpoenaed by the government, would we hand over anything useful or meaningful? No, like we never want to be in a situation where We have data about anything you've done that then we could hand over and tha…”
Prediction Not checkable as stated
Siroker: Highly paid hourly knowledge work like legal tasks will likely disappear
“I do think things like white collar knowledge work that is high paid, lawyers being one of them, is probably a good area. I think anything where today people are paying a lot of money and people are being paid by the hour that a machine could do as better, in …”
Insight
Siroker: Public fundraising finds better long-term investor alignment than localized networks
“And that's how I view this relationship with my investor. It's something I'm going to spend the rest of my life with. I'm going to be doing this for decades. I don't want to just meet the person I, you know, find at a bar. I want to cast a wide net and potenti…”
Assertion Not checkable as stated
Siroker: Rewind turned down 20 term sheets at a $1 billion valuation
“In fact, we didn't, we had. 20 offers or more of a billion dollar valuation. We turned down.”
Insight
Siroker: Pitch junior VCs at non-target firms simply to practice your presentation
“I would hone it and use I hope I just doesn't offend anyone, but use like associates and VPs at firms that you don't want to take money on as practice. Cause you meet these people, their whole job is to meet with you and get deal flow. But like, actually, you …”
Disclosure
Siroker: Rewind is exploring custom hardware due to off-the-shelf device limitations
“We are hiring for hardware people so it's possible that down the line if we cannot, by the way, I'm very much a big fan of software. I don't know if you're if you've ever done anything hardware related, but software has many, many benefits of which I'm the big…”
Opinion
Siroker: Google culture prioritizes technical sophistication over solving customer problems
“At Google, you know, they value sophistication of the technology more than they value solving a customer problem. And so that was a cultural thing that started from the early days that served us well, served Google well for certain products like search and pro…”
Assertion Supported
Siroker: Rewind records user activity and stores all data locally
“Rewind is a truly personalized AI. So it captures everything you see, say, and hear, stores it all locally on your devices.”
Insight
Siroker: The biggest flaw of note-taking is needing foresight on future needs
“You never know what you're going to need later. That's the biggest downside to taking notes is like you need the foresight to know what is it the thing I might want later.”
Assertion Not checkable as stated
Siroker: Rewind could not exist without Apple Silicon
“And it's so, you know, co occurred with Apple Silicon becoming really powerful and enabling this before Apple Silicon, you know, rewind couldn't exist.”
Assertion Not checkable as stated
Siroker: Every Rewind engineer ships to production daily on average
“You know, we ship on average, you know, every engineer ships code production every day on average.”
Assertion Not checkable as stated
Siroker: Every new Rewind engineer ships to production within 24 hours
“Every engineer, when they start at Rewind, within 24 hours of starting, they ship to production.”
Disclosure
Siroker: Most Regrettable Founder Mistakes Were Deferring to Board or Experienced Hires
“My gut says we should do A, somebody else thinks we should do B, and it turns out poorly. There are plenty of times we said I should do A, and it turns out poorly. I don't remember any of them. The ones I remember are like these deep existential, my intuition …”