Co-founder of Brainhub, Matt describes himself as a “serial entrepreneur”. Throughout his career, Matt has developed several startups in Germany, wearing many hats- from a marketer to an IT Engineer and customer support specialist. As a host of the Better Tech Leadership podcast, Matt talks about growing successful businesses and the challenges of being a startup founder and investor.
Jeff Winner is the Co-Founder and CEO of a stealth startup focused on AI and financial services. With a career that bridges Silicon Valley innovation and Wall Street rigor, Jeff has held leadership roles at top firms, including Goldman Sachs, Stripe, and Twitter. As the former CTO and CEO of Happy Money, he spearheaded groundbreaking financial products aimed at enhancing financial well-being. An MIT graduate in computer science and electrical engineering, Jeff brings deep expertise in fintech, security, distributed systems, and AI.
This transcription of the podcast is AI-generated and may contain errors or inaccuracies.
Matt
My name is Matt and I will be talking with Jeff Winner about navigating leadership challenges in high pressure tech environments. Good morning, Jeff. How are you doing?
Jeff Winner
I'm doing well today. How are you?
Matt
I'm doing great. I'm really looking forward to our talk. I think you have seen many organizations from the inside, from the engineering perspective, Twitter, Uber, Happy money, Stripe. So like a lot of different experiences, Goldman Sachs is another one that I had in mind. So I'm really looking forward to hear your lessons learned from those organizations. The first thing that I wanted to start because I think for me and my and our listeners, the most interesting part is the lessons from the organization that you have. You're quite a while in the tech and I'm just wondering like the first thing from the list, what are the biggest lessons learned from the Stripe?
Jeff Winner
Yeah, sure. So working at Stripe was an amazing experience. I mean I learned a ton of important lessons about building a great culture and building products and scaling organizations. But if I had to just pick one thing, it would be like the incredible value of well written documents and communication. So Stripe heavily emphasizes clearly written, accessible documents of all kinds. Emails, everything is covered by the Stripe tone. And that makes for a set of documents that create a strong history for the company and also a really deep repository to help you understand why decisions were made.
And that helps new employees to come on board quickly. And it also helps reposition employees that have been there. You know, things are moving quickly, you might forget. You can go back and review the comprehensive document and come up to speak quickly and understand if those decisions are still good because the document or maybe something you need to revisit. And it was, I've seen that touched on in other places, but Stripe just was like totally all in on it. And it also had the effect of helping. One of the things I've noticed with younger employees is they don't spend so much time learning to create well written anything.
Well written emails, well written texts or anything. And I think it really helped them build a skill that will be valuable for them as they go forward in your career.
Matt
And when I look at the other organization, I mean Twitter and Uber, for me Twitter, it sounds like a more loose atmosphere. Uber sounds like a really pushy, really hard deadlines. I might be wrong.
Jeff Winner
Stripe had Stripe and Uber. Both were very hard pushing organizations, very, very strong on deadlines and execution. And Twitter was a little bit, it's a much older organization, so it had a lot of communication channels and people used them a different way. So it wasn't nearly as consistent across the organization. They did invest heavily in a thing called Confluence, which is a system for published documentation, and they did a really nice job there. But as you sort of went out from that to less formal communication became, it became sort of less structured and less common and more difficult to find at Uber. Uber was very oriented towards presentations.
And presentations are like good, they can be informative. Many people like to consume content that's not written. But in general, presentations are a form of performance art and if you want to have someone teach you, they have to present it to you over and over again. And most people who ever had fantastic presentation skills. But it still has that drawback that if, if I wanted to go through all the historic or historical presentations, I'd have to find each author and have them presented to me rather than just taking the time to read it myself. So different styles for different things and moving between those organizations, especially coming on new and coming up to speed at the pace the strike was going, it was fantastic for me to just be able to take evenings and weekends and read through tons of documents and just get more and more context.
Matt
Is there anything from Twitter or Uber that you have learned and had like a huge impact? So now you are, you will be building a new next big thing and I'm just wondering, are there any lessons that you would apply from those organizations?
Jeff Winner
I think that at Twitter there was a really strong way that people had access and presentations all the way up to Dick, who was the CEO when I was there in order to do new business initiatives. It was really well structured and you could go in front of him and the way the arguments were presented and get a decision quickly that had the effect of sort of inviting anyone in the company to have a cool new idea. And they knew how like, like, like you can get to this place where you don't know how to present a new idea to get it done. And Twitter, how presented was pretty well structured and you could go right up your chain and it could kind of be. I, I really only saw engineering because that's where I was in. But it could be from anywhere in the organization.
And they had a way of doing that. They had. You could get a decision on what kind of investment they would make very quickly from Dick. And then at Uber the growth was very, very fast. And one of the things that they did, and it's not totally unique, but it really stood out, there was a very strong investment in developer productivity. They have one of their corporate things was let coders code. And that's all well and good, but you have to have a really great system for ensuring that the developers won't break anything and allowing people to build new stuff and push it out into a huge microservices environment.
And they made a big investment in that. And I think it made a big difference for both how quickly new engineers could contribute and how much they could contribute.
Matt
On the other hand, you work on the Goldman Sachs, so I assume this is a bit different culture. This is company which is quite long on the market and I think that all of us, we tend to demonize the corporations, but I think it's still an amazing place to learn things. Right, right. Because they are doing it for quite a long time and there's for sure a lot of lessons learned, especially thanks to the scale and the time on the market, of course. And I'm just wondering what could the organizations that we talk about, the startups, could learn from Goldman Sachs?
Jeff Winner
Yeah. So it was a big change in culture for me to go from Having done essentially 25 years of startup companies to go to Goldman Sachs, which is at that time almost 150-year-old company with a lot of history and a lot of value of the Goldman Sachs way of doing things, some of which were great, some of which were not. But one of the things that I found the most surprising and it didn't match my public perception of GS and I think it doesn't match many people's perception of GS is that they have an extremely solid foundation of teamwork and, and so everyone there knew I was on a critical project. Right. I was there to lead the team to build the Apple card and it was extremely stressful and I was brand new. I didn't know how anything works. And I found that anyone I reached out to across the whole organization just really quickly understood that priority dropped.
What they were doing provided me the help would reach out again and again to communicate with me. So a lot of frequent communication in order to make sure I was doing okay and that, that their help was effective. And I think that that can be something unless you do it consciously. And I think they do do consciously to maintain the sense of a team that you could lose that as your startup grows because it's, it's easy to be a team when there's 10 of you. It's kind of easy to be a team when there's 50, but when there's 30,000 people, not so easy. And so they had a very strong idea of keeping people informed and I would keep lots of people informed. And matrix management which I had never really done very much, but.
But did seem to work well for a new person to have a lot of managers to help me out. And so I'm not sure that any particular mechanics would be the right way to do it. But I think if you're a leader of a startup, understanding that you need to sort of constantly keep this attitude of we are a team, we're here to help each other. If you know someone's working on something important and they're struggling, you should jump in and help them. And I found that to be completely true. Yes.
Matt
I was reading recently, I think this week, a report from Goldman Sachs regarding the AI. It's a really interesting piece because it's all a lot about the micro macroeconomics and the AI and like the current drive into this direction of all organizations. So there are huge investment in AI and they are, they're making like a thesis or they are just wondering if we will see any like, if like such a future investment will show the proper return on investments because the investments are huge in organizations. So this is more of a philosophic question maybe because nobody exactly knows, but maybe how do you feel it? Like, how do you see the AI in upcoming years and those huge investment, will we see the proper returns?
Jeff Winner
Yeah, I, I think that the initial round of what people looking at AI, which is essentially thin wrappers over the chatbot itself in order to provide things like customer support and those sorts of, those sorts of areas. I mean there's integration and stuff you do, but you're not extending the capabilities in the AI very much are starting to bear fruit. They aren't giant investments, but, but they were giant, certainly giant investments by Anthropic and OpenAI to build, to build such fantastic lm. And I think we're seeing those already bear fruit both in terms of productivity of those employees and also in terms of reducing the number of those employees. I think the place that we have not seen it bear fruit and one thing I read this book, Co Intelligence and I like to keep this in mind is that you should think of the AI we're using now as the worst AI you will ever use. And so it's easy to marvel at the capabilities it has, amazing capabilities. But you have to keep in mind that it's improving rapidly and we've already seen costs come down, we see new capabilities added, people get upset that they're, you know, oh, we've only saw it improve dramatically and took six months.
Well, that is no time. Right. And so I think we will See it grow more and more into places where what it does is it grows your business or grows the economy rather than is strictly about replacing labor costs and operational efficiency. I, I would think that everyone and every form of knowledge work will be touched by AI in a pretty significant way over the next couple years. I don't think that's controversial at all. I think we will see as with any sort of organizational transformation initially probably a drop in productivity like because. Because people are learning how to do a new thing, that's to be expected.
But then over time as they get familiar with the capabilities or it's embedded better into the tools they use, which we're also starting to see that we will see huge improvements in productivity. I do think that there is going to be a significant impediment that there wasn't a requirement for a really efficient organization of your corporate information. And with AI, because it'll just happily tell people anything. Right? You have to make sure that you've constrained it properly around your corporate information. And so you're going to need to think about like you'll see these plugins and they want to see all of your email. Well at a small startup, whatever, that's fine.
Everybody at the startup can see any of my emails. Right. But at a company like GS, you definitely cannot do that. I mean there are regulatory reasons, you cannot do it. And so it's going to be interesting to think about how people think about constraining the access of the AI to information and then also how they think about constraining individuals access to the AI. I think it will be a stumbling block that unfortunately can't be solved by the AI. And it'll probably take.
By the time we solve that everywhere, the AI's capabilities will probably be like totally amazing and we'll be dying to get them in there but, but we'll have to solve the information architecture of the company companies.
Matt
And do you see already an impact on yourself on or like the leadership roles like the Director of Engineering's head of VPs of the AI?
Jeff Winner
Oh yeah, I see, you know, certain days some people are resisting it. But for myself as CEO and cto, I try to make the best use of AI that I can. And I get a huge boost for the obvious stuff that everyone would kind of think of like writing vision documents, making requirements, updating specifications, doing product designs, going from the blank page. Like a lot of times I'll go open blank page. It'll give me not awesome stuff but like it gets me started and gets me rolling and Then I can go faster myself. And I think that that's an important place to think about learning how to actually make good use, do good prompt engineering, which is not like totally straightforward and to get great results and, and play around with it and sort of get that feeling. I mean, I've been around a long time, so I remember when people didn't know how to Google things and, and I actually did a full text retrieval startup a long time ago.
So I sort of understood how to make queries that would work with the text engine. And then you sort of saw over a few years, everybody knows how to Google everything pretty effectively. You get the answer on the front first page. I kind of think that's where we are now with creating good prompts to get the result you want. I could give you an example at, at, at Bill Go, which is the company I was at before I started this new thing.
We use Microsoft products. So I got the transcription turned on and I said, oh, you can just put the transcription in the chat and you can get a summary of the meeting with action items and all that and no one could do it but me. And then finally I, I, I, I sat down with one of my, my reports who was the director of engineering.
I'm like, well, what are you doing? And he's like, oh, make a summary of this meeting. I'm like, no, that, that's not how you write the prompt. And my, I, I gave it my prompt which was three paragraphs long. And then he started to get good results. And it made me realize that hey, this isn't about putting a few terms in and having search come back. It's about learning how to use it.
Now there's a ton of note takers and summarize it summarizers now that you can plug into video conferencing. I suspect that what they're really solving for people is this prompt engineering problem to get a good result because most of them I've seen get pretty good results. And I think it will take time for folks to learn to do that or time for it to become embedded in a way where they don't need to learn to do it. One of the things that it does a great job for is generating performance reviews. I mean, if you have the data, if you don't have the data, too bad it can't help you, right? You should have gathered the data over the course of the year. It's kind of the manager's job.
But if you have the data and you can give it some direction again A two or three paragraph prompt. It can get you over the blank page and produce a pretty good result and then you can work from there.
Matt
Yeah, I fully agree with the prompt engineering. So I see it like this as a, it helped me to become a better leader. So I notice it when I, when I prepare like really good prompt. It's like delegating a task or delegating a problem to solve to, to your, to your people. Right? If you give like enough context, if you good give you like good explanation of why you're the, you are doing it. You, you give all that information, you get the better output.
It's the same with the, with the chat GPT it's, but it's hard to understand at the very beginning.
Jeff Winner
I feel it's also tempting to think of the LLMs as a person especially as you interact with them because they, they seem to have a little bit of a personality and you can even I, I, I, I, I always tell it to write. I, I like Steinbeck as an author and I always tell it to write things in the style of Steinbeck and then I'm too embarrassed to use them because it's so well written. But, but I found that you can also give it a bit of a personality to match your own personality. And I did one of these enneagram things and I told I'm an enneagram 88 Wing 9 and I and I told it just that and I said oh, help me write.
And it did a good job. And so I think that you can understand that it's not a person. Right? What it does is it takes all this context to use the prediction for what the next word can be. And as thinking about that helps you so. But it is very true. I will find myself just, I use it for everything.
I used to plan dinner parties, I used to do everything. And I will find myself conversing with it like and then I'm like oh, what am I doing? I have a task to get done here. But I think that, that if you think about it as really a computer program, it will help you underline the ability of important prompts. It probably will help you manage your people as you pointed out, because you'll get better at delegating tasks and telling them what to do. Right?
Matt
And the humanizing thing, it's really interesting. I think there will be more and more of that that will not recognize if this is written by a human or this is written by AI. So like in the music industry, what they have, they have like you know, when You, I don't know, when you record the drums and you do it like fully on the program, on the software, right?
Jeff Winner
It's too perfect.
Matt
So they have the plugin called like a humanizer, right? So they randomize like the strength, they randomize the timing and all that kind of stuff. So then you cannot see and you cannot distinguish like a human from the, from the algorithm.
Jeff Winner
So also you give a sample of your own writing. Like if you, if you go on and make a little custom GPT that's like I made one that is my meeting summarizer and I gave it, gave it like in the little fine tuning area. I gave it five or six examples of how I write them and did much better. It sounds much more like me right out of the bat. Right.
Matt
And let's talk about the controversial opinions or decision making. I'm always looking for some contrarian approaches to the engineering or leading or building the stuff on the engineering side. And I think you have like plenty of examples here. So I'm just wondering if you can share something that is maybe not so common in industry, but it works for you.
Jeff Winner
Yeah, I'm not, I know this is not common and I think that anytime I say it, and I actually wrote a little article in Forbes about it and it's definitely not universal, but I think it is critical for every engineer or really every employee at the company to be extremely well educated about the business the company is in and how that business works. How like at stripe, how the flow of funds work, helps it work for authorizing a card. And we all read this, this book, Payment Systems in the US which is, I liked it. Lots of people thought it was boring. It's, you know, but you at least came out of it and you know the history and you know why the payment systems work that way and you know how they work. You know how the funds movement work. And everybody was expected to know that.
And I thought that was fantastic because you can see places that talk about business people and technical people. And your technical people are not there to do research. They are there to move your business forward. And they are business people. They just use different skills. So why is a, why is a person who moves the business forward by writing marketing a business person and a person who moves the business forward by writing code and building code not. And so I think you need to adjust in your head this attitude that everyone at the table, as a business person, everyone is capable of understanding what the business does and what the key levers are.
And everyone brings different ways to move the business format forward. I mean, don't to say one is better than another. But I will tell you that if you build an engineering team full of people that think of themselves as business people who happen to write code to solve business problems, you will have a much better company. And I, I, I think that if you have an, have an engineer in there, unless their skills are crazy specialized, who is not interested in doing that, I would replace them because it can be this virus of oh, I just want to write the code, tell me what code to write. And it's like, no, you make a million decisions. You need to know how the business works. We want to get your creativity into solving business problems.
We want to get your perspectives on what we should do next. And so it provides them a more expansive role and for the right people, it makes it way, way more rewarding. So anyway, that's what I think is a thing that is, as I said, not controversial really, but lots of people don't do it.
Matt
But I think it's brilliant. So I had the same approach in my organization for many years, but it's really difficult to find the right people I think who have enough interest to solving. But when you find the right people, you can decentralize the decision making on each level. So I think it's brilliant. And you get like a different angles, different decisions, different views and thanks to that you create like a way more better output. And regarding your role on the engineering side, on the leadership side, what are the biggest pain points on challenges or maybe something because you are you. We are learning each year, right.
And I'm just wondering in your case, on your plate, what are your biggest challenges on the pain points that you're trying to solve right now or this year?
Jeff Winner
So, so for me right now I'm in the CEO role and I was previously in the CEO role of Happy Money as well, which is somewhat new for me. I spent many, many years as a cto. One of the things that is a challenge for me in this CEO role and I think that people don't really see it, is the huge number of short emails, short meetings and interruptions that I have every day. You can look today, I think I have nine half hour meetings and that could be. Yeah, right. It really scatters your attention and sprinkled in between that is emails that need to be answered or people will slack me and I need to answer something. And so it's really difficult to bring my full attention to each task when I have 20 more important things waiting for me.
And I Know it right. Like, I'm very good at inbox zero, but, but that just puts them in there with a star. And I know I've got them sitting there and I know, I know I have to deal with them at some place. Don't know if I have a magic bullet here. I have had a very strong mindfulness practice for over 20 years, and I will find myself leaning on that, like, if I, if I, if I find myself just like, becoming totally scattered. Like, I'm working on one thing and I'm thinking about all the others. I often take one or two minutes, just sit back, you know, like, focus my attention on my breath or something, which is kind of mindfulness I do, and try to bring myself to a place where I can focus on that one task and get it done.
That being said, it's not easy. And, and I think that it's one thing I talk to my current team about is one thing I, I talk to the team about at Happy Money is that I, I, I will try to absorb all the interrupts I can so that you don't have to, because I now I'm really well aware of what it does to your psyche to have that raining down on you. And so in addition to, like, delegating as much as I can, I don't delegate those, like, sort of little interrupted tasks that are just, I don't know, scatter your intell, Scatter your attention.
Matt
And you know what? I'm, I'm thinking like that the slack at some point should be banned. I don't know how about you, but I, I'm an inbox zero person, right? And, but I absolutely love the Async way of communication. I hate answering the calls because of this, this, the, you know, it, I, I, I hate the, the, the context, sweetie. And the same with the, the slack. So much things going on that I prefer email.
So after a few years of using the slack, I'm, I'm just, I just love to go back to the email and like, work with it. I don't, Yeah, I have a couple.
Jeff Winner
As I do there. I, I, I have my own communication norms that I like and I do take a lot of them from, from what I learned at Stripe where I ran a big team, but also Goldman. My, my team was huge, over 2,000 people. So, and the, the, the things that I do is everybody loves the slack, everybody loves the text. I'll just tell people we need to take this one to email, right? You know, like, like everybody and then an email. I love G Suite like is the best thing ever, right?
And so I, I will also take a mail thread and say hey, I'm taking this over to a doc. We're collaborating in a doc on this because, because the email is they might have the time to sit and read through the whole thread but for me I'm going to drop back into a thread and have to read a huge amount of stuff back and forth in order to catch back up because I went off and did something else in the middle of it and so I'm pretty insistent about which communication channels people use. I generally think of Slack as one and done some, one question I can just answer and I create an expectation from folks and I'm only going to look at it like a couple times a day and that if you need me urgently, send me a text message. Which very fortunately they do understand the meaning of urgently. So that doesn't happen very often.
Matt
And so because what, what got my interest, you work so many years on director leader, tech leadership, engineering side and the big organizations and now you're starting a startup after a while and I assume this, this, this is like a challenging process to make this step and it's really hard maybe to make the decision. So I'm just wondering like could you tell me about the process behind it, like why you decided to start a new thing, why you haven't decided to go, I don't know, to Morgan Stanley or you know.
Jeff Winner
Yeah, it's, it's sort of a something I, it's probably not best for like having your career development. But I love to do new things and I've been really lucky to have been born when I wasn't and be a technology leader. I've seen like so many major changes and I'm kind of getting toward the end of my career and I wanted to definitely work on something in AI, but I have really strong feelings about. I don't want to do just a chatbot. I love to do complicated back end systems. I want to provide something that solves a complex problem at leveraging the capabilities of AI. And when I came up with a good product idea I decided I would jump in and do the startup again mostly so that I could do something in AI.
I really don't want to miss. Like think about if you're, if you're within 10 years at the end of your career and a huge transformation happens again. Like if you're a technologist, you don't want to miss out on that. And I didn't want to miss out on it either. And so that's what really drove me is I wanted to not really dive in and build the base models and stuff, that, that ship has already sailed, but be a part of the embedding of AI and everything we use in a way that makes it useful. So that drew me into it. I, I have back and forth, gone between running big teams of hundreds of people to running teams of five.
A lot of times it is really different. One thing that is nice about having done it so many times is you see those transition points coming. So, like, oh, we're going to hit 50 people now. We need to switch to this style of communication in this and, and use this way for doing our meetings. Everybody can't be in every meeting anymore. Everybody's not going to know anyone. And so the bumps of scaling get a.
They're never easy. A little easier to get over. So that, that's the reason is I, I'm not going to be a technologist to miss out on AI.
Matt
And what is the hardest thing that you have done in your career? If you look back?
Jeff Winner
The hardest thing I have ever had to do is layoffs. I hate doing layoffs. I'm, I, I am a team player. I understand the need for them. I understand the business reality. We've had economic ups and downs and there's not everything you can prepare for. Sometimes you just have to live through them.
But I do a pretty rigorous job of performance management on my team, and so I always feel like I only have great folks on the team. Right. And when I have to let one of them go, it's. It's just like, never easy for me. Right. You know, it's the hardest thing. I spend nights and nights worried about it.
I think about each person. I feel bad about that, you know, and so I kind of think it's okay. Don't ever want it to become easy for me, and it's a fact of life. But every time I've had to do it, it just breaks my heart.
Matt
You know what? Like, a lot of my guests are mentioning the same thing, like layoffs. It's. I think we are just human and it's really hard to cope with that still. And sometimes, like very often, like the recent two years, right, the recession, so we don't have the impact on the economy, Right. So the economy just impacted all of their organizations. And you just have to do it.
But it's still, it's really, really hard even if you understand it. So, yeah, I totally get it.
Jeff Winner
No, I get the need. And you know what? There's hard things you have to do. And it's just I, I wouldn't want to really be around people where it was easy, you know.
Matt
And how do you see the upcoming years, like 20, 24, 2025? Do you, do you already feel that the recession is coming to the end? That you see like a more positive signs on the investment sides in the startups?
Jeff Winner
Well, we all know there's a huge amount of cash sitting on the sidelines. We all hope for interest rates to come down and I think that both of those are in the making. I doubt that we're going to have you know, like there is this sort of like 10 year cycle where we have two years of recession and eight years of good times and we need to remember that. And I'm now old enough, I've lived through lots of those cycles. It sort of works that way. It feels like we're sort of. This was, was a unique one in that the COVID Well, Covid not itself but the, the quarantining of people like really smack the economy hard and then at the same time we injected a huge amount of cash and we're just going to have to inflate our way out of that unless we dramatically improve the productivity.
I think that's going to be hard transitions for individuals. I believe that we're going to see the overall productivity impact of AI and the follow on things from AI like robotics and automation and stuff like that will be a significant force in helping the economy recover more quickly. So I, I am not thinking there's going to be a big recovery this year, but I, but I got to believe by 25 or 26 we're going to see ourselves back in one of those eight year good periods of, of solid growth, I hope as technologists powered by AI but you know, also there's just a regular business cycle.
Matt
And regarding the team setup, I'm just wondering because you have seen a lot of setups and everybody's talking about the remote hybrid in office. And in your case, what approach do you take especially with the new company because it's really hard to build the culture when you're for example, fully remote.
Jeff Winner
So I have managed fully distributed teams ever since the beginning of the pandemic. We didn't have any choice. They said everybody go home only for two weeks. But I didn't believe that and fortunately so we designed processes. I think that as long as you have enough time together that's targeted at almost specifically building human relationships, then you can make that work better. At my new Company, everybody has worked like with me, kind of for me. They reported to me, but they actually didn't work for me.
They worked for the company. And, and that has helped us to build because we already know each other. It's helped us to build communication norms. And I think that sometimes as a manager, I was like first time CEO and we went remote and I was very afraid about what was going to happen and how that was going to work. And so I put a huge amount of work into more communication, more written communication, coffee chats on Zoom company, all hands on Zoom every week. And I think that helped a lot. It was not free, but when I think about the level of productivity we got about it and the level of support it gave for people's lives, like you had small children and stuff like that.
And, and, and their, their lives are much easier. It was worth it. I'm suspecting when people fail, they, they think it's just going to be free.
It's not free. Like, like you have to invest really heavily in keeping everyone aligned. And one of the things that was really amazing at happy money and, and you know, as I said, new CEO, newly distributed company by force. Right. Rather than by choice, is that as we did surveys of the company, people were more engaged and more aligned. And not just saying they were more aligned. We asked questions about things and they actually gave the right answers.
And so I think that communication paid off. And when we asked broadly, they like, I feel like I know more about what's going on than I ever did when we were in the office. And so it was worth the 15 hours a week I worked on making sure everyone was aligned and communicated well with. But if you don't do that, it's not free. But you don't have to pay for an office, so, you know, take the extra time and make that work.
Matt
And the last question that I wanted to ask you, you already mentioned a few books, but maybe could you mention and recommend any books, podcasts, or resources that have been particularly helpful for you as a, as a leader?
Jeff Winner
So I know I'm on, I'm doing a podcast now, but I'm not a podcast person. I'm usually a books person.
I like books. There is a great book called Multipliers by Liz Wiseman who does organizational dynamics and she talks to you about one. The specific job of a manager is to improve the productivity, multiply the productivity of the people that work for them and gives you ways of thinking about that and multiplier behaviors and divider behaviors and how to watch For Red Flags. Really good book, easy to digest and also you can print the little cards out and follow that. For me in particular, the Google SRE book provides a really good look at that methodology of building very highly scalable, very reliable systems. And reading that even as a non technologist understand how that works is a great thing to do. I like the book Intangibles and Intangibles is about sports teams, but what they really dive into is how the personalities of the individuals involved affect how the team works together.
And I found it pretty easy to translate that into how I think about team dynamics. You know, not, not 100% easy but. But was definitely a good look at, at, at that. There's a more controversial book I like and is meticulously well researched. So I'm guessing everything they're saying is right. It's called the nine Lies about Work. And they take things that like you just think are true and then they do research and show you that they're not true. And so, so that, that, that's a really good thing to keep in mind because it's easy to slip into this, oh, I think this is true.
And then you're like, no, that was one of the lies. Oh, I gotta, I gotta go go do something else. As I think there is. There's one website that I go to all the time and I used to go to it every day but. And it's called, there's an AI for that. And it's, it's almost like an early version of Yahoo for the web. Like it's, it's an ontology of everything and now it's starting to have search and I stopped going every day because I couldn't keep up.
Like I couldn't even read about every new AI thing every day. But if you went there and searched, it's a, they do a pretty good job of taking the scope of what's going in the industry and they can point you at something. They don't do a lot of editorializing because the pace is too fast, but it's reasonable to look at.
Matt
I saw this website, it reminds me the product hunt in the early days. So each startup that there's, you know, each day you have a ton of new startups, right.
And it's really hard to follow. So that's a cool website. Jeff, thank you so much for a really interesting talk. I really appreciate it. I have Finger crossed for your next dance. I really hope that it will be another unicorn or even something bigger. So finger crossed here.
Jeff Winner
Alrighty. Well, thank you so much, Matt. Follow Matt on LinkedIn and subscribe to the Better Tech Leadership newsletter.
Matt
Sa.
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