A not-so-brand spanking new podcast!
Dec. 5, 2023

Rewind.ai & Optimizely CEO & Founder, Dan Siroker, on augmenting human memory with AI, building Optimizely, AI in operations, privacy and security, hiring and building extraordinary teams, and AI's impact on STEM education

Rewind.ai & Optimizely CEO & Founder, Dan Siroker, on augmenting human memory with AI, building Optimizely, AI in operations, privacy and security, hiring and building extraordinary teams, and AI's impact on STEM education

We're thrilled to welcome Dan Sroker, co-founder and CEO of Rewind, and former CEO and co-founder of Optimizely, to Between Two COOs! This episode centers around an eye-opening conversation about the potential of AI to augment human memory, transforming every digital interaction into an AI-able, searchable database. Yes, you heard it right! We are talking about having a "superpower" that could change the way we perceive and utilize our memory.

During the discussion, we also shine a light on the future of AI in operations, how it can amplify human capabilities, and importantly, the full impact on productivity. However, we don't shy away from the hard questions either. There is a crucial conversation on privacy and security in AI, and the stark warning that those businesses not getting on board may well struggle in the future. We also navigate through the role of AI in remote work and the possibility of smaller teams punching above their weight with the help of technology.

Lastly, we touch upon the prime importance of STEM education in fostering creativity and problem-solving skills, and how it finds its place in the world of technology. We discuss the dynamics of having a COO and chief of staff, why company values matter, the importance of psychological safety in team building, and the art of conducting effective reference checks during hiring. This episode is a riveting exploration of how technology intertwines with our lives and how we can make it work for us. Tune in for an enlightening discussion!

(05:11 - 05:38) Memory and the Evolving Digital Age

(06:56 - 08:05) Tech and Memory Retrieval

(11:40 - 12:51) Chat GPT and Data Privacy Integration

(17:34 - 18:44) Leveraging AI for Company Augmentation

(22:34 - 23:47) AI for Efficiency and Exceptional Hiring

(30:31 - 31:01) Pivoting to Capture Meeting Data

(38:38 - 39:00) COO and Chief of Staff Collaboration

(43:27 - 44:27) Using Cultural Values as a Guide

(47:10 - 48:20) Accountability and Candor in Successful Teams

(55:58 - 57:01) Impressions of AI Summarization

---

(00:11) Augmenting Human Memory With AI

 

This chapter of Between Two COOs features a conversation with Dan Sroker, co-founder and CEO of Rewind, a personalized AI tool that augments human memory. Host Michael Kanag explores the inspiration behind Rewind and how it can give users a "superpower" by making all their digital interactions searchable and AI-able. They also discuss the importance of memory and how technology can enhance our natural capabilities. The conversation touches on the potential impact of relying on AI for memory recall and draws parallels to the evolution of phone numbers. Overall, this chapter explores the fascinating intersection of technology and human memory.

 

(12:51) The Future of AI in Operations

 

This chapter explores the potential impact of AI on future operations. Our guest, who has experience in scaling a company using AI, discusses how AI can be a powerful tool for leveraging human capabilities and increasing productivity. We also touch on the importance of privacy and security in AI, highlighting how companies that do not embrace it may struggle to compete in the future. The conversation concludes with a discussion on the role of AI in remote work and the potential for smaller teams to achieve more with the help of technology.

 

(18:44) Enhancing Productivity With Artificial Intelligence

 

This chapter explores the impact of AI on workplace productivity and efficiency. We discuss the release of GPT-4 and its potential to speed up tasks and increase productivity. Privacy challenges and the importance of employee awareness are also addressed. We examine how AI can bridge the gap between ambiguity and tasks, using Rewind's email summarization feature as an example. The significance of hiring exceptional senior staff and maintaining focus to achieve more with less is emphasized. Lastly, we touch on the potential impact of AI on the job market for recent graduates.

 

(27:19) The Impact of STEM on Technology

 

This chapter emphasizes the significance of STEM education in fostering creativity and problem-solving skills through technology. Our guest shares their personal journey with robotics, which led to the creation of innovative products like Optimize-A and Mac. The discussion also highlights the role of M1 and M2 chips in their company's pivot and how it enables local data privacy. Ultimately, we are reminded of the transformative potential of technology and the importance of adapting and maximizing its benefits.

 

(38:29) COOs and Chiefs of Staff

 

This chapter explores the dynamics of having a COO and chief of staff simultaneously, and how this partnership can benefit a company. We discuss the importance of screening for a good COO and chief of staff, as well as their role in creating a positive work environment. The former CEO shares his experience of achieving the number one spot for best place to work and the role of psychological safety in creating a fantastic workplace. Overall, this chapter provides valuable insights into the importance of a strong partnership between a CEO and their COO and chief of staff, and how it can contribute to the success of a company.

 

(42:23) Cultural Values in a Company

 

This chapter emphasizes the importance of defining and living up to company values. The host, who has experience at Google and now runs his own company, shares insights on creating a strong company culture by clearly defining values and behaviors that align with them. He highlights the need for these values to be a living document, constantly evolving and being used as a basis for performance management. The conversation also touches on the potential pitfalls of using values as a marketing tactic rather than a genuine reflection of the company's beliefs. Overall, this chapter highlights the role of company values in creating a positive and successful work environment.

 

(45:58) Psychological Safety in Leadership Importance

 

This chapter explores the importance of psychological safety in creating a successful and cohesive team. We discuss the guest's experience with psychological safety in their previous company and how they are implementing it in their current venture. We emphasize the need for a shared language and vernacular around psychological safety to create a sense of safety within a team. The guest also shares their regrets about not maintaining a balance of comfort and accountability in their previous company as they grew. We highlight the importance of a long-term orientation and hiring slowly to maintain a strong culture. The chapter concludes with the guest discussing their vision for their current venture and their determination to make it their life's work.

 

(52:03) Ask the Right Question and Succeed

 

This chapter explores the importance of conducting effective reference checks during the hiring process. We discuss the significance of asking the right questions and building rapport with references to obtain honest and valuable feedback on potential candidates. Additionally, we touch on the game-changing role of AI in the hiring process. The chapter concludes with a discussion on how to handle unexpected moments that may arise in the workplace.

 

 

Transcript

00:11 - Michael Koenig (Host)

Hello and welcome to Between Two COOs, where phenomenal chief operating officers come to share their knowledge, advice and, at the very end, a crazy story. I'm your host, michael Kanag, and occasionally I like to bring on a CEO to bring their perspective and also learn a bit about their industry. That in mind, our guest today is Dan Sroker, co-founder and CEO of Rewind, a personalized tool that uses AI to basically augment human memory. Dan calls it a co-pilot for your mind, and if Dan's name rings a bell, it's because he founded Optimizely and grew it to 120 million in ARR. He was also a key member of President Obama's campaign back in 2008, where he helped pioneer the use of data to optimize fundraising media the entire thing, which was a major factor in the election win. It's also when we first got to know each other, albeit briefly, dan welcome.

 

01:02

Thanks for being here, thanks for having me. So here's how I'm thinking about this. There's so much to talk about. Let's start with Rewind, dive into some AGI and then get into operations, because, after all, this is an ops podcast. Sound like a plan, sounds great, all right, wonderful. Let's talk a little bit about Rewind. Give us the nickel tour.

 

01:24 - Dan Siroker (Guest)

Yeah, so Rewind is a truly personalized AI.

 

01:26

You know there's a lot of AI solutions out there today that lets you ask any general question and you'll get the same or similar response to anyone else.

 

01:34

But the inspiration for our product came out of this realization that we can use technology to augment our human capabilities and give us superpowers.

 

01:43

For me, that happened personally about 20 years ago when I started to go deaf, and in my 20s I realized only when getting a hearing aid how much I had lost, and that ability to gain it all back in an instant really felt like gaining a superpower.

 

01:58

You have to lose a sense and gain it back again is quite magical, and that put me on a hunt for ways technology can augment human capabilities, and so lucky for us is that that intersected with this now very exciting wave of technology around AI. So we've kind of pioneered using all the data about you everything you've seen, said or heard on your Mac and now, as of yesterday, on your iPhone and making it searchable and making it AI-able if that's now a verb where you can now use AI to ask any question about anything you've seen, said or heard so simple things as writing you an email or reminding you like hey, how do I know this, michael guy? And going back and actually seeing all the times we've interacted, seeing the touchpoints of our past synthesized for you, is really does feel like gaining a superpower.

 

02:45 - Michael Koenig (Host)

And I love it because I have a horrible memory and it's getting worse, right, because that's what happens as we get older. And so when I saw what you were working on, I was like, oh, this is pretty interesting. I call my partner. We like to joke that she's my external hard drive, mine is, mine is. Yeah, yeah it was interesting.

 

03:04 - Dan Siroker (Guest)

Actually, memory I was. So I started this journey where I had a hearing loss and I started going on this research expedition on what are other human capabilities, like hearing that people don't realize is quite as bad as it is. It gets worse as you get older and the one that really stood out was memory. You know, studies show that we forget 90% of our experiences after just one week. It follows what's called the forgetting curve. And not only that, but typically your memory gets worse every year after you turn 20. So you turn 20, your memory peaks and then every year thereafter it gets worse.

 

03:36

And on top of that, most people don't realize it. So you've got this like already base level of memory. That's pretty bad. You don't know what you don't know, so you don't realize how much you're forgetting often. And then it gets worse every year and that's kind of a boiling frog dynamic where you kind of thought you had good memory and then all of a sudden you start realizing boy, I don't know how I know this person or what was my action item for that last meeting? And that's where we saw this huge opportunity to use AI to augment our natural biological, limited memory with a, you know, super intelligent memory.

 

04:02 - Michael Koenig (Host)

This is interesting because we're talking about memory augmentation. We're also talking about what happens as you get older. Every now and then, I like to take a question from the audience, and this one comes from my colleague, justin Riley, who's the CEO of Wave Low, which is one of the companies that makes up the two cast family. Justin asks and he takes a very similar approach, by the way he thinks about AI not as replacement but as augmentation. And so he asks how does rewind thread that needle of being a useful recall tool but not changing the fundamental makeup of how a human experiences memory? And I think that's the end of the quote, but I think an extension of that is if we rely so much on something else to remember things for us, does our memory just go out the door because we're no longer trying to recall?

 

04:55 - Dan Siroker (Guest)

It's a really fascinating question, one that I've thought about, and if you look at the history of this question, the analogies can actually maybe be pretty illuminating. You know, there was a time in my childhood where I had to remember the phone number of my friends, and if I wanted to actually call them, I had to remember it and I'd had to dial it in. I didn't actually have to put an area code in, which is probably crazy for kids these days why. Why you'd have to put an area code and you just put in the number and it would, the phone would ring and you know, and I knew my best five friends. I knew their phone numbers. Today I don't know anyone's phone numbers. You know, I know my wife's number, I know my own number because people ask me for that, but then everything else is in my phone.

 

05:27

And, like, am I any worse off because I don't remember my friend's phone numbers? No, like it's just a piece of technology that can augment something that otherwise I would have to memorize, and now I don't. And another example is is getting from point A to point B. You know, when I grew up, you had to know cross streets. You had to know, like, how to get from one place to another because of you know that's the way. You know just how we navigated the world. And then you know this website called map quest came along and then now takes Google maps. And you don't have to know any of that, you don't have to remember cross streets, you just put in your destination. It will dynamically decide how best to get you there through the traffic that's out in the road, and your better life is better for it.

 

06:00

So I don't think we lose anything by outsourcing parts of our mind or parts of our memory to technology. You know it's not everything. It's the parts that technology is well served to store, things like numbers, things like directions and locations. And there's so many other parts of your mind that are like that that you don't need to remember. It feels maybe nostalgic to think oh well, would I be my own self if I don't remember all of these facts about something? And I would argue that it actually creates space, it creates creativity in your mind. So you're not obsessed with what was that thing I supposed to do. You're not racking your brain Every moment. You're racking your brain trying to remember something is a moment. You're not thinking about the future or connecting the dots or being creative. So I see it very much as a pedestal in which our minds can evolve to become greater and better, not worse and limited, because we're now in some dystopian you know Wally universe, we're just sitting around in a scooter, disconnected from reality. I think it's quite the opposite.

 

06:56 - Michael Koenig (Host)

And it's interesting another area, because I was also thinking about how does tech augment my memory in general? So I have Google Home displays throughout my house. I also have two little kids and so many of the memories that I have forgotten come back to me as soon as I see a photo of my kid eating ice cream upside down on something crazy like that, and I'm like, oh wow. And the more I see these pictures, the more I remember it, and I assume the same thing is happening for my kids. Maybe they remember things in greater detail or even in greater breadth at age from age two than they would have otherwise. So I think that'll also be an interesting experiment, yeah.

 

07:44 - Dan Siroker (Guest)

In many ways our memories are encoded in a way that are very hard to retrieve linearly, but can be retrieved through recognition. You know, photos does that? Music does that for some people, smells do that for others. So people, even with advanced dementia, can recall and like, retrieve parts of their mind that many had thought were gone forever, through these kind of sensorial experiences of smells and music and dance. And so that's, I think, another way. Again we're augmenting and making us better through technology, not making us worse, because the worst thing is having in your mind. You can't retrieve it. It's like a, you know a vault with no key. But with technology you can get to those memories and cherish them.

 

08:19 - Michael Koenig (Host)

Yeah, absolutely so. We talked about rewind and a big part of it. The way it works is it's a desktop application that you install and it essentially sees everything on your desktop. It listens to your conversations, both the input and the output, and then it does this magical thing of somehow compressing it to not take up a lot of space and then integrates chat, gpt, as you described, so that you can query everything. It's all index, et cetera. There's obviously some privacy things that we need to talk about. How have you approached that?

 

08:55 - Dan Siroker (Guest)

The approach starts with the realization that there is nothing more important than the trust and privacy of our users, and we started with that. I mean this is exciting. You know we call it privacy or private by design or privacy. First we started as the as the foundation of thinking how we built this product. We could have built what we built entirely as a cloud based web app. That's my background. Optimize Lee was a SaaS web product. I know JavaScript quite well. I could have helped build that. Instead we did.

 

09:20

The crazy thing is we pivoted from what was a product we had before called scribe and online meeting bot. We pivoted from a cloud based technology that I knew intimately well to an entirely new domain of technology. I knew nothing about native Mac OS low level system. You know optimized software because of the fact that now we could offer a product entirely local, or at least all the recordings you stored locally. That was a decision we made, recognizing that the convenience and value of what we're offering was quite high, but at the same time, if you could give that and give people the assurance that no one like us like if we're compelled as a company to look at some of these recordings we can't like we're for, subpoenaed, we can't do it. There's nothing, it's on your desk, we don't have access to it, your employer doesn't have access to it, only you have access to your data. And so we thought if we could do that and give you the convenience, that's the best of both worlds. So that's where we started with was just this premise that, okay, we need to focus on privacy first approach. What we do is unique, it's new, it's for people to get comfortable with it Initially. It needs to show that we care and not just that we talk the talk, but we walk the walk. What we found is interesting. So we started with that approach and, surprisingly, a lot of people were like, oh, this is amazing, I'll use it right away.

 

10:31

And then, as soon as they get to that aha moment using our product, it's usually, you know, an example would be something that they couldn't have found any other way. Or maybe they're writing an email and they hit discard instead of send, and or they tab crash, or some information that they really needed disappeared and rewind was able to go back to it. As soon as that first moment happens, people's minds shift. Now it's all about convenience. And then people are starting to ask hey, can you synchronize this data across my phone and my Mac and can I ask questions on my Mac and my phone? And all of the things that we were so careful to avoid in the beginning.

 

11:05

When people become, you know, activated and have seen that first magical moment, then their minds have shift shifts. So now that's why we're launching we just launched iPhone. You know, soon we'll be launching the ability to, in an end to end encrypted way, synchronize data across your devices, and so we're sort of paving the path as our users are pushing us toward more and more of what they want. But it all again starts with a privacy first approach. Everything is stored locally on your machine. We don't have access to it, and I think that's sort of foundational to giving the right return on investment for users that they think about adopting a new, different kind of technology.

 

11:40 - Michael Koenig (Host)

You have integrated chat GPT in one of the videos, or maybe it was on your website. You mentioned that the information, because it is stored locally, isn't used to train any sort of models or LLM there. How does that work with chat GPT? Because everything you pop into it is used to train the model.

 

12:03 - Dan Siroker (Guest)

Actually that's incorrect. If you use the API for GPT for Open AI has been very clear that they do not train any of their models using the GPT for API. If you use the Consumer chat GPT interface on the website, they, I think, likely trained, but they're very clear. It's like black and white on their website. Anything used to their API is not used to train, and not only that, but it's only retained for 30 days. So after 30 days, anything sent to the GPT for API is deleted, and and again. Even in those 30 days, nothing, nothing is used for training.

 

12:35 - Michael Koenig (Host)

Oh, fantastic. Okay, I Mentioned privacy and security. You were recently on a, and there's a little bit of a lead in here. You were recently on this week in startups with Jason Calcanis, and he came in, by the way, pretty fiery, but you called him down at the end, which nicely done. It's no easy, pete, thank you, but he looked at and, and he described his reaction to this as terrified and intrigued, and that he was uncomfortable using it. Now, right, he also pointed out, potentially, some of the legal liabilities. You already talked about how this stuff can't be subpoenaed. One of your use cases on your site, though, is for execs, like our COO listeners. The most sensitive matters of a company come across our desktops. How do we get comfortable with? Yeah?

 

13:36 - Dan Siroker (Guest)

I think, if you zoom out and look at the broader World and imagine where we're gonna be in 10 years, the companies that succeed or fail are we, the ones that embrace AI as a way to get 10%, 20%, in some cases, two or three or ten times better. And In those situations, the people who are actually the most successful in their roles as COOs are the ones that don't just say my job in 10 years will be the same, but slightly different. It's gonna be. It's gonna be fundamentally different, like every decision I'm gonna make is gonna be informed through not just data, but AI synthesizing the data. For me, I'm gonna be able to be in five meetings at once, not just one. It's it's thinking that every minute of my day is precious and if I can use technology to augment my memory, my capabilities, to give me Superpowers, that is better for me, that's better for my company, that's better for the world. So I think it's it's in that broader landscape that you have to ask yourself okay, if in the world unless you think, ai is just hype and it's gonna go away Well, maybe some, maybe that's true.

 

14:33

I, I think, more likely a fundamentally the way we work every day will be different and the companies that can actually Credibly, like us, claim that privacy is at the core of what we do.

 

14:43

We store data in a way that is almost impossible is, by sort of the way it's foundationally designed Is the most privacy centric model. We, I think, will be your partner in, you know, surviving in that world, you know. So you either have to say it's not gonna be a big deal, the AI thing is not gonna happen, or you have to say, you know, I'm just gonna pretend like it is a big deal, I'm gonna be one of the companies that decides you know, it's not important for us, and then your company's not gonna exist. So like in that sense, like I didn't create this whole AI way, but I'm just trying to help companies write it, and if, if I can do that in a way that respects the privacy of their company, their data, my, my guess is, maybe today your, your CIO, is not gonna be that keen, but in three or four years, when they see the alternatives, which is maybe an entirely cloud-based solutions or ones in which data is used to train models, I think then it'll be pretty clear that this is the path for them.

 

15:34 - Michael Koenig (Host)

I hadn't expected to have Privacy so early on in AI. I had expected this to be something much further down the road. If you know, the we were to follow the trend of social media or search or things like this. Privacy really doesn't get added in until People are up in arms about it, and so I love that you took the privacy and security approach first in. John, my, my CISO Are we cool with this now? Can I use it? I Really want to know. I'm sure he still says no, but I hope that we can bring him along. You talked about ten years out and you started talking about how the companies that don't embrace AI now are just set to fail. Similarly, I think something can be said around remote work and productivity and learning to be able to, to work and excel, and in that field, if we think about operations and the applications of AI and I think you are very qualified to Answer this question, having scaled optimistically from nothing to 120 mil what do we think? The application beyond rewind of AI in ops?

 

16:50 - Dan Siroker (Guest)

could be, yeah, the one word I would use is leverage. In analogy I'll draw is like imagine thinking about ops in a world before computers. In a world after computers, there's a lot of people in your company doing operations who had to do wrote, manual tasks with pens and paper, and you needed an army of people to do things that with the end of computers now could be automated away. I think similarly, if not more so, ai is gonna do the same thing. It's going to be a giant lever in which any one human being at your company can do 10 or 100 times more, and to do it joyfully, not because they're working harder, because they're working smarter with technology. And so the future looks like smaller teams doing more.

 

17:31

Companies that don't embrace AI are gonna be bigger teams that are gonna be greater. You know competitive threat at greater competitive that markets will look at their company say, hey, why? Why do you have? You know every, everything you think today of what is a good PNL or balance sheet for your company in the future. When you compare your company in your industry with one that is a Competitor that is braced AI, it's gonna look fundamentally different. So expectations will rise from the public, markets, from investors, and, and it'll be.

 

17:56

It'll be silly like I look at our company today. Today, we're 18 people at rewind. Many of us use AI every day to do our jobs better. I, you know no knock on optimizer, but I feel like, as a team of 18, we're able to do more quickly than a team of 450 I had when I was running optimously, and A big part of that is AI, its technology, its leverage. And so I think, the future, if you're, if you're a COO and thinking about your company in the future, you should ask yourself not you know what is my? You know how do I get more people in my org chart? It's like, how do I make every one person in my company better, more augmented, more capable? Sure, there'll be some parts that maybe no longer exist, some teams that no longer need to exist, but for the most part, the leverage you're gonna get isn't from replacing people with AI. It's going to be augmenting your existing people and making them 10 or 100 times more productive.

 

18:42 - Michael Koenig (Host)

I completely agree with you, of course. When GPT-4 came out, basically we said to everyone in the company hey look, we don't know what this is going to be like, but you can definitely do more faster. And I have the app installed on my phone and I'm just asking myself at the end of the day, how did GPT-4? Make my life faster and how did I do more today with it?

 

19:09

I think the real big challenge for the company is twofold. The first is around privacy. We saw what happened with Samsung, how they had uploaded all this proprietary IP. So first it's making sure that everyone throughout the company and when you're a 1300 person company, that's complicated, but making sure everyone has an appreciation Okay, don't upload this or don't use your work email. The other part to it is that it's such a broad tool and it asks people to essentially be creative in figuring out how it can augment it. You guys have gone in and you've taken a much more specified approach to it and I just I love that. I don't know if that there's a question in there. Those are just more like observations and feelings.

 

20:05 - Dan Siroker (Guest)

Yeah, I'll share. I'll share one insight we had over the last few weeks which is Related, which is you know, you're right that AI today, chat, gpt, is so broad you don't even know what to ask. We have found that the most powerful and valuable features we offer are ones where we sort of bridge the gap between that Ambiguity and the task you're doing. A perfect example is today, with rewind. If you're in a meeting, a zoom meeting with a colleague or a team meeting, the first thing will pop up and say join a record. We know you're about to join a meeting. You join. That's pretty helpful.

 

20:33

At the end of the meeting you get a little prompt that says Summarize and draft email and what it will do is take everything you said, everything your colleagues said, summarize it and turn it into like a five bulleted list in a draft in In your email inbox to the attendees of the meeting knowing, because we know who's in the meeting, we know their names, and that's a perfect example of using technology sort of bridge the gap between the ambiguity. What's possible with like the actual like that is you know five things less, you know. You know, especially if you're back-to-back meetings there's no way you're gonna write a summary. This makes you look good in for your colleagues. You look like you've got a superpower, and that's the thing that I think AI is best served to do is like bridge that gap between the things you're already gonna do. But now, instead of spending 15 minutes after every meeting summarizing, sending notes, actions, have the AI do it for you.

 

21:15 - Michael Koenig (Host)

That's phenomenal, because oftentimes we'll have meetings, there'll be great ideas that come up, great action items and so often, unfortunately, things just get dropped and Talk was great but then action didn't happen. This kind of ensures that at least People remember what the meeting was about and then go the next step and integrate with a sauna. Turn them into action.

 

21:39 - Dan Siroker (Guest)

Yeah, we thought meetings are a black hole for information. It's like you go there, everyone talks. Like I said earlier, the forgetting curve tells us 90% of what's gonna happen in that meeting. It's forgotten the next weekly team meeting. And so just taking what's already said and in a very expensive setting, everyone's salary for that one hours is it's not Incons, is not, it's not insignificant and then taking that and turning the values, insights of that into actual action follow-up. That's super valuable to companies. I.

 

22:07 - Michael Koenig (Host)

You mentioned 18 people. You have built so much right. A small team doing very big things here, 450 people at Optimizely. Obviously, the tech has come a long way in enabling that. You have a phenomenally low burn rate and a lot of cash in the bank because of that. A lot of runway, a lot of ability to get out there, figure things out. How has AI and I was gonna say, oh, how have you done that?

 

22:33 - Dan Siroker (Guest)

AI we use.

 

22:34 - Michael Koenig (Host)

AI right Outside of Rewind and the feature you just talked about, though, how do you all think about applying AI to do more with less?

 

22:44 - Dan Siroker (Guest)

Yeah, I mean, it's not just AI, by the way, it's a phenomenal team Like, I think, hiring people well above. You know, if I look back, the first 18 people at Optimizely the kind of people I work with. They wouldn't have worked with me. I didn't know what I was doing. I was just like they could have worked anywhere. They would have been making three or four times as much money working, as you know, fancy, spancy individual contributor at Facebook or Google at the time. So I just think I feel fortunate that I've been able to hire truly exceptional people. And you know, the myth of the 10X engineer is certainly true and with AI, it's the 100X engineer is the one that you know can do more with less. So that's, I think, a key part is really senior folks and honestly, if I'm candid, it makes me really worried what it's like for kids graduating today. You know, in a world where you know people who have experience, who can use AI to make them even better, you know it's gonna be a tough. You know why I personally we don't hire junior engineers. We only hire, you know, senior staff level, principal level, engineers, designers, and you know it's anyway. So that's a topic for what that means for society. But yeah, I mean to do more with less comes with the great people.

 

23:48

I think another thing that I have learned the hard way is focus. You know, I always, at Optimize, used to think I was focused, but then, in hindsight, now, boy was I not. You know, and you know, Steve Jobs has this famous quote that Johnny Ive recently retold, which was that, you know, focus to him meant not doing something that, with every bone in your body, you want to do, but you decide not to do that thing that you really, really wanna do because you're focusing on something else. And that is a test. You know, and I remind myself and my team they're probably sick of me hearing it, but I say this saying that the main thing is that the main thing should stay. The main thing I say this over and over again because that is the curse of death for any organization, especially startups, is doing too much. It's indigestion, not starvation. It's saying you know, let's do Mac and iPhone and Android and Windows all on day one.

 

24:42

You know we took a very different approach. We started with Mac very, very purposefully. You know we were getting requests. We had a huge waiting list of people dying to have our product on iPhone. But we waited. We spent, you know, really a year perfecting it, learning, and then, when it came to iPhone, we could do it in three months because we learned all of these things around compression, around integration with AI and like all the things that made it possible to do it right the first time. So I think that's probably the broader lesson is great team, really experienced team, great AI and deep focus.

 

25:10 - Michael Koenig (Host)

I love that. Okay, the main thing is the main thing is the main thing three times Is that it?

 

25:15 - Dan Siroker (Guest)

The main thing is that, the main thing should stay the main.

 

25:17 - Michael Koenig (Host)

thing. Ah, should stay the main thing, and I think I first heard this.

 

25:20 - Dan Siroker (Guest)

I think HP had this as a cultural saying. I think somebody else famously quoted it, but I'd heard it from somebody who formerly worked at HP and she said this and I thought ever since and this was maybe 10 years ago I heard it and I only in the last three years as I've been working on Rewind have I really embraced that mantra.

 

25:35 - Michael Koenig (Host)

That's fantastic. Okay, I might have to take that on. Normally, my thing is, if someone's hey, this seems broken, but what do we do? How do we fix it? I just I default to four words, which is just who does what, when it's actually all quite simple. Just figure that out and it'll be smooth. The main thing is that the main thing should stay the main thing. Got it, love it. You started getting into what jobs of the future look like and I swear I didn't share my notes with you, but I actually have a question on this. Let's shift gears to be or shift back. Let's talk about kids and education. We're both dads Right now. Education there's a huge focus on STEM and in light of how quickly we're seeing the tech advances, especially for solving these structured problems, is STEM going to be as important in 20 years? And I'm asking you to look in the crystal ball here. But yeah, yeah.

 

26:39 - Dan Siroker (Guest)

I think yes, and maybe even more important, Maybe we will be standing on the shoulders of giants, so much so in 10 or 20 years that like it's just too inconceivable to be so low in the implementation details of science, in implementation digital science, I mean, like the physics, the underlying, because there's, you know, I think somebody once looked at all of the things you would need to know to make a common you know pencil and it was like huge amounts of science, like metallurgy and chemistry and all this. So like, maybe it's you know, and I look at my education, there's so many things I learned that I probably don't use every day today. So, like, learning how to learn will always be important and learning how to build will always be important. I think STEM really helps you learn how to build, how to be creative, how to use the tools that are at your disposal at any, at your disposal at any time to build something you know. Today that's maybe much more rudimentary than it'll be in 10 or 20 years, but the idea of always taking what you have around you and building something with it, I think that's gonna be fundamental. It's hard to imagine that that's not gonna be the most important thing. People have to be good at in the future.

 

27:46

I was lucky. In high school I was on the robotics team and that was like one of the things I really learned was like how to build physical things out of the things around you. We had this competition and it was all about like how do you use the constraint of the materials you have to build something great. And I similarly, you know, at Optimize-A, I viewed that very much so as like what can JavaScript let you do? That wasn't possible before with browsers getting as fast as they are. And that's what sort of inspired the first version of Optimize-A client-side A B testing.

 

28:12

That was easy for marketers to use. And similarly today with Mac, it's very similar. Like we would not exist today if not for Apple, silicon and M1 chips and M2 chips and the hardware. You know we started the product, basically realizing wow, actually this stuff is really good and fast, how can we use it to solve this problem? But before this technology existed we couldn't solve. So I think that metaskill of sort of looking around and thinking how do I use technology to solve a real problem in the world that I think STEM teaches really well and I think will be important for our kids and they're we still have a really long way to go before we have intergalactic travel.

 

28:44 - Michael Koenig (Host)

It's really not going anywhere, is it?

 

28:46 - Dan Siroker (Guest)

Yeah.

 

28:47 - Michael Koenig (Host)

You mentioned M1, m2, silicon. I was gonna. I was very interested. There was a podcast that I saw. I didn't have time to listen to it, but this is very deep into tech for you all to go. Oh my gosh, look at the M1 and M2. Like, how can we leverage that? That didn't happen overnight. Like, take us into your brain.

 

29:11 - Dan Siroker (Guest)

Yeah, and, by the way, you said something there I just want to remind you of. You said there's a podcast I didn't have time to listen to. That is the persona of the person for whom our product is perfect. Instead of listening to the podcast, ask the question what was that thing Dan said about M1, m2? Like those are the kinds of things that. Why would you spend an hour of your life listening to a podcast when you can synthesize it, get the action. Anyway, I just thought that was like a perfect example of why our product and products like ours is gonna make your life much better in the future.

 

29:34 - Michael Koenig (Host)

But yeah, I mean it's so we Sorry, would I be able to play it on 10X speed and it would get it and we'd be good?

 

29:39 - Dan Siroker (Guest)

Yeah, I mean. Or you just ask a question of it, like, if you have podcasts, you send it to Rewind and ask Rewind, hey, like what did what are the takeaways? Summarize it. Or when Dan talks about M1, what did he say? Those are the kinds of things that maybe you do now manually, like I do this too. Like I swear I saw this quote in a book and I'm like I will listen to it in audible and set a buy on Kindle and I'm command affing in the Kindle to try to find it. It's like totally broken. I should just be able to send the thing I heard to Rewind. Have Rewind. Do this synthesis for me. Tell me, hey, this is the thing you were looking for. And oh, by the way, here are the three other references to in the book and like, anyway, a bit of an aside there, but yeah, so your question is how do we get to this conclusion on M1, m2 and sort of the technology, the name of the thing? Those are it?

 

30:21

Well, it started with, you know, we I kind of alluded to it we pivoted from another idea. So when he started the company, we had built what today is called like a meeting bot. It joins Zoom meetings. It's in the cloud, captures everything that's said in the meeting, transcribes. It does sort of like summer, you know, gives you kind of a compitre chart on how long each person spoke. And that was kind of our first foray into our approach and giving human superpowers. So I thought meetings was a good place to start. But very quickly we realized there's so much more context you have outside the meeting that would make that you need to really make that successful. And we also realized that we are in this point where everyone felt weird about bots. Like having a meeting with a bot is kind of creepy, it's out in the cloud. That's really a data privacy concern. That bot is somewhere, some hard drive, somewhere. Google Cloud has the data of that.

 

31:07

And so we thought, with M1 and M2 coming out, we looked at it and the vision that I had for the company from the beginning finally became possible. Now everything that we were doing in the cloud we could do locally and if we could do it, because the technology was good enough to do the compression, we could do transcription all locally. That's what we can transcribe what you're saying, all locally. So the privacy goal now is finally realizable Like it wasn't before the technology like your computer would crawl to a stop if you tried to do what we do today before Apple Silicon. So that was really the reason we invested in it.

 

31:37

It was a big, you know, we had a big debate. We had a whole strategy doc five different strategies we're considering, of which one of them is the one we ended up pursuing, this kind of better memory strategy. In fact, three of the people on the team voted that the last choice of the five. So it was not an obvious decision to focus on you know, learning you know Apple or Apple native development and learning Swift and how to build a native app, but it was the one that was the most likely, if it were to work, to be a transformative technology and it turned out it did. So I'm glad we did. You know, that was another example of something I learned from from Optimize is being decisive and focused, and it wasn't obviously the right choice, but hindsight working pretty well.

 

32:15 - Michael Koenig (Host)

I would love to see those other four. So let me ask and only because I've been, I have scar tissue talk to me about platform risk. This is something that runs on a machine, right? We talked about this at AdNazio. Do we do worry, right? You just did the iOS app? Apple is famous for being very private when it comes to iOS. Do you worry that some of the moves that Apple might make further down the road might disrupt rewinds product? You?

 

32:54 - Dan Siroker (Guest)

know it's. It's definitely something I think about. There's four advantages we have today and I'm more worried, frankly, about Apple becoming a competitor than really pulling the rug out from it underneath us, because you know, the good news is, you know when we started this company there's one of two paths either what we're doing is a good idea or a bad idea. If it's a bad idea, it would fail. It's a good idea and so, with it being a good idea, it will attract the the, the attention of big tech, including Apple. But we today benefit from a couple of things. One, what we do is weird, and when something's weird and maybe even borderline creepy, lots of people at a big company will tell you not to do it. You know, I know for a fact that people at Apple who think that, like the future of Apple services revenue will be something like what rewind does, but for every one of those you know people fighting the fight there's a hundred people at Apple to tell you no and here's why not? And brand and privacy and concerns, and so it sort of comes down to basically the innovators dilemma. We are, and that's going to be a huge advantage for us, I hope for a few years. I think eventually Apple will do what we do.

 

33:52

But if you look at, you know something as comparable. If you look at, like the Dropbox versus iCloud, you know Apple tried to buy Dropbox. They didn't want to sell. They sort of competed and build iCloud. That was, first of all, many years after they probably should have, and in that market that is a very low switching cost. You just drag the files from one to the other.

 

34:10

We are a very different product. Everything you capture with our product is encrypted locally on your database. It is, you know, it's by design, not something that snooping eyes or you know other products can consume. So it's. The switching costs are incredibly high. So that's our huge advantage. And speed of execution. You know we release 11 times a day. I listen, I give my cell phone number to every pro subscriber. When Tim Cook starts doing that, then I know they'll take us seriously. So so, yeah, so those are our advantages today.

 

34:38

So that's more broadly around Apple as a competitor, I think from a platform perspective. You know we don't break any rules. We play all by the same rules they have in the APIs. Everything is a published API Like, if anything. They love what we do. You know one of the first things we got when we announced our product was this is so crazy. I did not expect this. We let we first announced November 1st. Within days, I was getting people emailing me with receipts of purchasing Apple new Apple laptops, because we said we're only going to work on M1 chips. And it's people saying I love what you're guys doing so much. I just went out and bought a $1900 laptop to use your product. So in that sense, we are apples. That's the reason Apple has built this great platform for developers like us to build software that drives hardware sales. So so I'm not too worried about them pulling the Roy out for us, given that they get quite a bit of revenue from from users who want our product.

 

35:24 - Michael Koenig (Host)

Yeah, and that's also like. The question that some will ask is what happens if Google does this? Well then, either they buy us or we're out of business. I don't know what to tell you, but nonetheless, this is how things develop.

 

35:36 - Dan Siroker (Guest)

Well, I mean, I think I actually think we have a credible claim to build a successful independent company. If you look at the big tech company, google, this would be make you know. There's rumors even later in Sergey, when they built Google desktop. Their vision for that long ago was something like what we do today, but, like I said, technology wasn't there yet, couldn't do it. But even Google, like they have a fundamental business model conflict. Their innovators dilemma is like as soon as, if Google offered exactly what did today, we would crush them, because all you would have to say is do you want ads targeted better because of the data that you collect and like? So they have fun and we are a subscription service. You pay us money. We don't have access to the data. Google's approach would be very different. So I think they're the least of my concerns.

 

36:11

I think Apple is the only of the big tech companies who could do this. But, again, what we do is weird and creepy. Hopefully, no one important at Apple is looking for this and you know, if, as long as they think we're weird and creepy and we can fly out of the radar, I think we can build years of a head start and you know what, honestly, one day. I love Apple. If we were to join forces with them, I'm very happy to acquire them. I have no problem. You know, I have no problem with that. I think culturally it'd be a good fit. It's going to be a while before I think that's going to work out.

 

36:39 - Michael Koenig (Host)

Yeah, no, it's. You got to have goals. You got to have goals. Let's get back into some operations a little. Now you have a chief of staff, is that correct? That's right? Yeah, yeah, and you had that it optimistically and now have it at rewind as well. Tell me a little bit about that decision. How do you like? Why a chief of staff? And then, how do you work together?

 

37:05 - Dan Siroker (Guest)

Yeah, yeah, we have a chief of staff here. I also had to say, oh, it optimizes. I've definitely had that experience. But, yeah, we work together very collaboratively. I think of her as an extension of me. So the things that I would otherwise do but but don't have time to do or she would be just as well suited, if not better, to do she, she owns. So there's a set of things in that camp A lot of the administrative stuff, thinking that we do quarterly retreats, we all go together and so thinking through how to set those up for success.

 

37:34

You know, just recently you know a topic that was very important that I wanted to spend time as a group Working through was psychological safety, talking about what that means and having a kind of conversation with that. So she did a great job of owning that, thinking through how to have that conversation. And so you know, in that sense I see it as just an extension of me as the CEO and and she's able to bring her unique skills and perspective. You know I'm much more excited about what's possible and open minded and optimistic. She's much more, you know, execution oriented and sort of traditional COO kind of mindset, which is also really good compliment. And similarly at Optimize, I had a COO who also, you know, he actually ran a huge part of the company but was fantastic as being a compliment to myself, and it was one of those things where you know one plus one equals three, where you know I could bring my unique perspective, that orientation, bring theirs, and together we get to a much better rational view of the world and a path.

 

38:26 - Michael Koenig (Host)

Interesting Tell me about. Did you have the COO and the chief of staff simultaneously?

 

38:32 - Dan Siroker (Guest)

I did yeah at Optimize. I did yeah, yeah, yeah.

 

38:35 - Michael Koenig (Host)

What was that like? How, what was that interaction? How did they work together?

 

38:40 - Dan Siroker (Guest)

Yeah, I didn't see often how the two of them worked, you know when I wasn't there, but together we as a team worked really well. I think the COO at Optimize the fantastic, one of the best executives ever hired. He actually was promoted from within. He was our CFO actually for a long period of time and then he took on customer success and managed that part of the company, became our COO, was a fantastic thought partner and was very, very much wanted and when I think, coming to the company wanted a partner in the CEO to work together to build something great, much more strategic, my chief of staff I had some fantastic chief of staffs at Optimize.

 

39:21

Many of them have gone off to be chiefs of staff to the stars like Elon Musk and the you know the console brother. So I feel really good that I'm like stepping stone on their ever progressing career of success. But you know, I know what it looks like because I can see. You know where they ended up.

 

39:36

So in those roles I think you know, one of the things that I really valued was somebody who could take a very ambiguous, ill-formed thought of mine, like I could utter a sentence without much structure and they could actually translate it into the organization, kind of what you said earlier, like who, what, when or whatever. Like you know, they could be a good at making sure that these often dumb ideas but sometimes there's some kernels of good ideas turned into the next steps. They didn't just die on the vine, but they were sort of translated into the day-to-day. They're good at holding sort of keeping processes in place to hold people accountable, making sure that the things we were talking about in one setting got translated to another. And yeah, it's a fantastic role Highly recommend. I can't imagine being a CEO without a chief of staff or eventually, probably a CEO.

 

40:22 - Michael Koenig (Host)

That's fantastic. Now, you just said you know what good looks like, clearly, so everything that you just discussed, though, is things that you learn and experience once they're in the role. How do you screen for that?

 

40:35 - Dan Siroker (Guest)

Pretty poor. I do not know, because I'm never really I'm more lucky than good. You know I've made some misfires and I, honestly, am just more lucky than good. I do not know how to screen for really good chiefs of staff or COOs. Like I said, our COO is actually promoted from within.

 

40:51

It's a really hard. It's a really hard job because a lot of it is also just that unique partnership with the CEO and like how do you that intermeshing? You know each CEO is different. What they need in this role is different. You need somebody who's different enough from you but compliments you in a way that actually together you're able to be.

 

41:07

You know, if I were a perfect CEO, I could do all the things the CEO CEO could do, but I'm not. I've got my flaws. I got my strengths, my weaknesses and I need somebody who can compliment those and you know, and mutually we respect like they're great at one part of the world and how to lead and I'm part great Another and together we can do more. And I think that's actually, if I look back at the best COOs and folks who it's them also recognizing that they're not the end all be all, like they couldn't really do the job of CEO. They know that actually, you know, what I'm best suited for on this planet is to be a great COO, partnering with a CEO, and it's not so much like oh, I could just do their job and I'm not there yet, it's like it's really true partnership, not a you know, while I'm just in some you know, some other role and one day I hope to be a CEO role.

 

41:49 - Michael Koenig (Host)

When you were at Optimize Lee and steering the helm you, you were at, I think, 450 people or so and Optimize Lee was ranked the number one best place to work by the San Francisco business times. You talk now about psychological safety. That certainly goes a long way to people feeling comfortable. How did you approach just achieving that? How did you approach building such a fantastic place to be?

 

42:17 - Dan Siroker (Guest)

It's it starts with values and not just talking the talk around values but but walking the walk. So we, early on in Optimize Lee, made a commitment to a set of values. It's spelled out an acronym Optify ownership, passion, trust, integrity, fearlessness and transparency, with a Y at the end, so Optify. And for each of those values we had a very specific set of behaviors that lived up to those values. And those behaviors were very. They weren't just obvious, you know, integrity is kind of obvious but a lot of companies like Enron, on the day of their collapse and they've walked in the lobby of Enron it was actually emblazoned into stone the word integrity. So you know there, you know it's, and that's what I mean by walking the walk. So I think we did that well. You know, I think one of the things I learned out how important it is to be to at least put it pen to paper. People talk to Google. One of the things that killed me was, you know, I interviewed like a thousand people Google, even though I was like a very low person on the total poll. We were hiring like crazy and every person I interviewed I had to assess them on how googly they were and there was no definition for googly-ness, and that was like the thing that killed me. Like I decided, if I want to start a company, at least I want to define what our culture is, so that it doesn't become a recipe for unconscious bias. It's not like, oh, they weren't a culture fit Well. Like there's no definition of what our culture is. So you know, and so that was my first goal is like define what the culture is. And then the second was how do we live those cultural values? And the way I did that was anytime I had to make important decision, I would always open a culture doc. We had a document that described it. I always went back to that as kind of the constitution. You know, I thought of it as very much like I'm a Supreme Court justice, I've got to look at the law to ask myself what's going to best live up to these values. And some of the hardest decisions I made I use as our culture, as, or the values in our culture, as the, as the, the sort of deciding factor. And then, when I made the decision, I would explain why I said the reason why I'm deciding to do this is because, as our culture talked about, fearlessness is important and much rather many decisions are two-way doors, so that was the thing that I think helped it optimise.

 

44:06

I've evolved that substantially here at rewind. I think we mistook cute and simple as a as more valuable than like, comprehensive and and and and. So in rewind we have actually 14 cultural values no fancy acronym. We have two high-level themes of impact and teamwork but and we put our culture doc up there. If you go to rewindai slash careers You'll see it's there's a culture doc link. It's the same notion, doc. We use internally as we share externally. You can see all the comments and that defines really like and and. Every quarter we do 360s and every 360. The key criteria, everything you evaluate each other on is how well does this person develop to our cultural values? And that's another factor. That like shows us we walk the walk. Like I'm held accountable to our culture by my team, I similarly I hold them accountable. So we just create cultural values as the DNA of the company and I think that's when everyone has that shared understanding. I think that creates psychological safety. Everyone has a clarity on what's expected of them. So that's how we've done anything 14.

 

45:03 - Michael Koenig (Host)

Do you foresee your values evolving similarly to Github? Right Github or no? Was it GitLab? Excuse me.

 

45:11 - Dan Siroker (Guest)

Yeah, they absolutely every new hire. I tell them our culture is a living document and you can go to again. You literally go to rewindai slash careers. You can see a culture man with there. We explain what our values are. You can see the revision history. We tweak them all the time. They're pretty well-baked today, but we ask ourselves a regular cadence. We do retrospectives every two months. We ask, we want to make sure that we're We've we've defined these values in a way that serve us. They're not meant to be lip service. They're not meant to be recruiting tactics. You know it's. We hope people come to us because our values, but only because it's a match for them, not because there's some kind of marketing gimmick, because this is also how we hold each other accountable, like we know every quarter. You'll know how am I living up to transparency? How am I living up to decisiveness? How am I living up to resourcefulness? Now, these are values that we think will make us successful and that's why we use them as the basis for performance management.

 

45:58 - Michael Koenig (Host)

And then talk to me about psychological safety, which is something that you mentioned previously. Tell us about that. Why was it something that you focused on? Why now, and how?

 

46:08 - Dan Siroker (Guest)

Yeah, I mean we, we focused on it in part because we felt there's an opportunity to have a shared language and vernacular. In many ways, just talking about it creates it, because people know, oh dancing to care about psychological safety. Maybe that's something, it's important to him. So I think if you're thinking about talking about it, do talk about it, because I think the more you talk about, the more people feel it. It's also something that, if I look back at some of my regrets about optimizely, there there's a two by two quadrant. I can try to pull it up in psychological safety and I think the two by two conderate, conderant the the axes of the two by two corner. One is Comfortable, yes, no, and the other one is like, accountable, yes, no, something like, or maybe it's something like Candid or something, and in each of those quadrants you know they describe it as a certain thing.

 

46:54

The ideal of psychological safety is like comfortable and candid and comfortable and Accountability. Like you have the balance of, you feel like you can say what you think, you don't have to worry about the repercussions of what you say and you're being held accountable to a high standard. And that high standard doesn't create a lack of psychological safety and optimizely. We started that way and then over time, as we got successful, we had, like you know, amazing series A and B.

 

47:15

Like we, we got this collective disease of Of getting you know comfortable but without accountability. We were and we were. It kind of like the way I think it was, like we all had locked arms, kind of kumbaya off a cliff, you know. I'd much rather somebody yell out there's a cliff, you know, and be willing to admit that. Then everyone feel this false sense of, of security and that's the thing I really wanted to avoid. It rewind is like, even though and especially, thinks things are going well. I feel like it's my important, my job as a leader, to remind people like it's not always gonna be up into the right, like there really moments in time where you know it's gonna be hard, like we're gonna have times when who?

 

47:50 - Michael Koenig (Host)

knows.

 

47:50 - Dan Siroker (Guest)

Apple launches exact clone of what we do and offers it for free. Like in those moments, we need to have that candor and that muscle around, kind of a wartime mentality and high accountability for one another that you lose when things are, things are good.

 

48:03 - Michael Koenig (Host)

Hmm, and it's operating as a unit when you're talking about that. You can't operate as a unit if people aren't feeling safe to be able to contribute.

 

48:12 - Dan Siroker (Guest)

Yeah, and it's, it's. It's also related to me just knowing that Everyone I expect everyone on the team, if they see something, say something like their job isn't just to be a cog in the machine. I hired incredibly experienced, highly capable people. I pay them top of market compensation, not just because of the title that they were hired, her for, but because of their smart, general, per perspective point of view, and so if an engineer sees something wrong in our marketing, they should say something. If you know, if our designer thinks that I'm making a bad decision, they should say something. You know, like that's part of the the contract I'm trying to build is that I? I know I'm not perfect. I know I have a lot of dumb ideas. I want to create an environment where I can throw those dumb ideas out there and I get the bad ones all get ripped to shred and shut down. The good ones get, you know, watered a little bit and turn into something great, and not just for me, but everyone on the team as well.

 

48:55 - Michael Koenig (Host)

Yeah, how do you maintain that you grew optimizely Right? You've talked a little bit about the lessons. You've learned what you've wanted to do differently, and this is your 18 people now, and rewind is gonna be around for a long, long time. Hopefully it will. I don't mean to throw in the hopefully, no, but as you go on, it's just so important I.

 

49:21 - Dan Siroker (Guest)

Think well first. Yeah, I mean I hope to do this is my life's work. I want to be doing rewind for decades to come and In our vision is to give human superpowers, and I think that's it's gonna be quite a while before we achieve you know the full scope of what that could mean. So I do think it starts with an, I guess with a long term orientation and from that, ironically, comes Conclusion, which is to hire slowly. You know, I've been very purposeful and like not making the mistake.

 

49:45

I made it optimizing and optimizing your raise a $28 million series a and then a $57 million series B, and then that alone would have been fine. We raised a lot of money, great, got a cash to make, but then we coupled that with a secondary mistake of then spending it. You know like it was hard for me as it's first time CEO. I hired this amazing head of marketing. They're like, oh, we should, we need a comms person, we need this person. I was like, okay, that's what you say for marketing. Great, and not having that constraint, that willingness to say no and focus and say let's try to do more with 18 and see how that goes. Then you know to do maybe less or even the same with 30 or 40, which we could have easily done by now. I think that's the that's gonna help a lot. That's how you maintain kind of the culture.

 

50:20

You don't let it go from what I saw in optimizing, which was like a high psychological safety, high accountability, to a you know Safe, but you know, but kind of you know, like I would say, low accountability culture. That's part of it, is it's growing slowly, it's it's being very perfect. So in the recruiting process I've very, very much believe in references. Now I didn't do a good job of that.

 

50:43

My first company leaning into references now like that is almost the most important part of the recruiting process is Is doing really good references, back channel references and and being willing and I've done this being willing to say no to a phenomenal candidate who checks all the boxes on Can they do the job? Are they a great engineer? Are they great? You know, but they they fail on the cultural aspects and they fail in the references. You know we're willing to say no to great people because we think that it's more important to build the right DNA in the culture up front Then it is to have a amazing tactician for the next six months or a year, but ultimately will be kind of a cancer to the culture hmm, do you have a favorite reference question?

 

51:20

I do. My favorite reference question is usually I do 15 minute references and then most of it is just build a report to get them to be honest, so that when I ask this question they actually give me an answer. So the question is near the end I'll ask hey, michael, look, we're gonna hire, we're probably gonna hire Bob. But you know, if we hire Bob and in six months you and I bump into each other and I tell you it did not work out with Bob, what is your first instinct as to why and usually with that lens, with that accountability, look, I'm gonna bump into you and you're gonna tell me and people like to predict the future, that's where I'll get the truth that I'll get something's like.

 

51:52

Well, you know what would probably happen Bob probably got disengaged. You know, bob probably got excited for the first few weeks and then maybe Bob decided he wants to go start a startup or everything. Right, okay, this person's maybe not committed, maybe they're not focused. You know you hear the things that the other ways don't come out when you ask for strengths and weaknesses and anyway, that's been so far my most successful question.

 

52:10 - Michael Koenig (Host)

Such a great question. Where'd that come from? Is this?

 

52:14 - Dan Siroker (Guest)

I don't know, I'm sure.

 

52:15 - Michael Koenig (Host)

I stole it from somebody.

 

52:16 - Dan Siroker (Guest)

I mean for a long time when I did references. You wouldn't be surprised, given my experience of optimizing. I would a be test my questions and I literally would just every time I do a reference.

 

52:24 - Michael Koenig (Host)

Of course you did and this question just.

 

52:27 - Dan Siroker (Guest)

I started to ask it I probably heard it somewhere and it just started to get things that had I not asked that question, I would have not had information. It's really hard in the back channel reference of somebody you don't know to get to be honest with you in 15 minutes Is really really hard. Like the stakes are pretty high for them. The the return for them is not very low. So this question, for whatever reason, strikes the right balance of like hey, you're gonna bump me, okay, I don't want to look like an idiot, not tell you the one thing you really should know about this person.

 

52:50 - Michael Koenig (Host)

Yeah, important distinction there. That's a back channel reference.

 

52:57 - Dan Siroker (Guest)

Question of regular references as well, and usually the other trick I do there is I never asked the candidate to introduce me to our reference. Instead, I'll ask the candidate give me a list of five references, title their email a little blurb how you know them, and then I'll reach out. Even that subtle difference alone, you got a lot more anus. Honest, if there's a direct one-on-one introduction, oftentimes the reference won't be as candid, and then usually I'll ask at the end of those references by the way, this is something my chief of staff now is taking on and she's on fantastic. She's now does these references for me and can do just as well as I can't, not better. But usually at the end of those five references we asked for, we asked them who, somebody else who might give us a unique perspective on this Candidate, and then you get to that, that first order.

 

53:34

And then usually the thing is, even if that first reference who knew that they were given, doesn't want to say anything bad, what they might do is give you the person who's gonna give you the real dirt, you know, because they won't feel as bad about that. They're like oh you know, you should talk to you. I think Dylan might have a really unique perspective on Bob. Like I'll talk to Dylan and we reach out to Dylan, dylan's like, oh, do not hire Bob here. To find, like you know, that's that's when you also get some truth, because people want to be honest, they don't want you to be saddled with, you know, a bad hire. So it's just sometimes it's not in their best interest.

 

54:02 - Michael Koenig (Host)

You see me smiling because that's my last question that I love not necessarily the last, but it's in there. I actually had someone ping me and he's hey, you're talking about 25 people. What's going on here? You're reaching out like just make sure that someone doesn't find out that I'm looking, I'm like I know I, but yeah, there's so much value in doing those. You and I'm mindful of our time here. I am. This is just a great conversation. You mentioned getting people to go at ease right in the beginning so that you can ask that question and get a true answer. So, building that rapport, what's your approach?

 

54:37 - Dan Siroker (Guest)

Usually I'll start with you Letting well I also. The approach generally is I want them to leave this experience very positive because often maybe we might be recruiting them down the line. So part of it is me selling them on our idea or vision. I don't miss the opportunity to tell our story, explain why we're doing how. It was inspired of my, my losing my hearing and the dire to create superpowers. So I don't make it as transactional, I make it more relationship. Even though it's a short meeting, I also don't want to make it too long because I don't you know they're doing them, me a favor, so so trying to strike the right balance and and yeah, generally it's around Respect, treating them in a way that I would want to be treated if I would ask, as a reference, letting them know how much we appreciate it, how meaningful this is to the two, the decision how much we value them. As an expert on this person, like you know, making them feel as important as they are because they are.

 

55:26

I truly believe, like I have been asked to do references for people and I can tell the person asking me and interviewing me on the candidate has already made up their mind or they don't care what I have to say. They're just checking a box, and when they do that, I'm so much less likely to want to give them the actual, honest answer. Because I'm like, look, why would I take a risk and tell you something that might piss off this person? Because it's true, and probably not something they want other people to know. But if you're already gonna make your mind, you're gonna hire and then like what's the point? So that's. Another part is like I try to treat the reference or the reference the person talk to you the same way I would want to be treated if I'm being asked to do a reference.

 

55:58 - Michael Koenig (Host)

We've gone way over time. I had so many questions that I wanted to talk about that. We didn't get to. It's unfortunate. Maybe we have time for my final and favorite, which is as execs, we have had those times where something comes up and it's just never thought. I'd see that that is Absolutely crazy. Do you have one that you can share with us? The best one I?

 

56:22 - Dan Siroker (Guest)

the first instinct as to the question is related to the makes it earlier, which is it's gonna sound so dumb. This AI thing is pretty freaking good, this whole AI. Like the first time I saw a summarization, like just this morning we had an executive meeting, 90 minute meeting went real along. I was running rewind on it and we summarize it into five bullet points and it was so freaking good. It reminded me of my first job at Google's, an associate product manager. My job is like to take notes straight out of college, taking notes for these senior executives.

 

56:52

You know, type it away and I couldn't have done as good as the AI did in summarizing the content, the substance, the, the objectiveness. So I am. If you have not had these moments in the last six months, this chat you PT came out where you're just not blown away by what AI can do that probably a human couldn't even do. Then you're not looking hard enough because these things are just so magical so I'll just leave it there. It's to say like if you have you not had that moment, you're in, you get your head out of the sand and and try some of these products, because the things they can do today are Just truly mind-blowing. They're changing the world.

 

57:24 - Michael Koenig (Host)

I have that moment, but another moment that I think of that is like. The moment was when I first held an iPhone in 2007, and I was outside in Colorado in an open-air market. Before that, I had this LG flip phone, which I actually have right here. Crazy enough, my daughter was playing with it. The screen is broken, but I held it and I went holy crap, I have, like Humanities, knowledge in the palm of my hand, so it was remarkable. I had that same thing, dan. It was awesome. Thank you so much.

 

57:55

I've so enjoyed this conversation. We might have to have another and rewind for that. See, I was gonna do that. I wanted to use the word rewind to recollect something multiple times, and I held off until now. Anyways, dan, where can people go to keep you and learn more about rewind, rewindai? Perfect, there you have it. Well, thank you very much for listening to between two COOs. I'm your host, michael Kanig, and a very special Thank you to Dan Sorokor for joining us today. Tune in next time for our next COO chat on between two COOs, and be sure to subscribe on Apple Podcast, spotify, blah, blah, blah, blah, blah, blah, blah, blah, blah. You have the idea. Tune in to the next episode and until then, so long, tailine 你.