Leaving Bridgewater For Solopreneurship. How David Kline Left The Largest Hedge Fund In The World To Teach The Management Playbook

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Table Of Contents

In this episode, Mike Gardon chats with David Kline. Dave is a former Chief Operating Officer of several different divisions at Bridgewater Associates, the worlds largest hedge fund with over $200M of assets under management headed by Ray Dalio, whose book Principles is a must read.

I met Dave on Twitter (@dklineii) and was fascinated by his career pivot. He successfully transitioned out of the high stress world of high finance, and is currently the owner of Skillscouter, a website that helps people find the best courses for upskilling their abilities. Dave also teaches cohort classes for growing managers. Having hired, trained and managed hundreds of high performers in the high stakes jobs of finance, Dave has seen it all, and he’s codified his management principles in what he calls the Management Accelerator.


  • David’s background
  • How working with recruiters can help you get hired quickly (David found a job in 48 hours)
  • Bridgewater - who are they, what they do, how they build teams and David’s role at Bridgewater
  • Tools and systems that Bridgewater uses, like Dot Collector
    • Dot Collector feedback is in real-time
  • How to coach people to want and accept feedback
  • How David chose to leave Bridgewater
  • David’s career pivot
  • Big takeaways that anyone can expect from David’s MGMT Accelerator
  • The big things David learned from his career change
  • David’s advice for recent graduates


Help us reach new listeners by leaving us a rating and review on Apple Podcasts! It takes less than 30 seconds and really helps our show grow, which allows us to bring on even better guests for you all! Thank you – we really appreciate it.


  • Tip From David: stay in touch with a few recruiters so you are aware of what’s going on in the industry and can change paths quickly if needed.
  • Principles by Ray Dalio - founder of Bridgewater
  • Dot Collector - tool mentioned by David
  • Learn more about David’s MGMT Accelerator
  • Follow David on Twitter, LinkedIn and his website.


Disclaimer: The transcript that follows has been generated using artificial intelligence. We strive to be as accurate as possible, but minor errors and slightly off timestamps may be present due to platform differences.

Mike Gardon (00:00):

Welcome back. You're listening to CareerCloud Radio, and this is your host Michael Gardon. I've got a great guest today, his name's Dave Kline, and he's the former chief operating officer of several different divisions of Bridgewater Associates. Bridgewater's in the news a lot, not only because it's the world's largest hedge fund with over 200 billion of assets under management, but it's also ground zero for human intellectual and organizational performance development. The founder Ray Dalio has lived his life organizing a set of principles, which he's also codified into computer code to help him make decisions. I first read principles in 2011 when it was just a PDF. Now it's one of my favorite books. It sits over my shoulder on my bookshelf, and it's on my list of most recommended books on my personal website. Back to Dave, I met Dave on Twitter and was fascinated by his career pivot.

Mike Gardon (00:49):

He was helping to run a major hedge fund and rewriting the book on organizational performance, recruiting and culture, but chose to leave this lucrative position to pursue a life as a solo entrepreneur. Dave now teaches cohort classes for growing managers, having hired, trained, and managed hundreds of high performers in high stake, job stakes jobs of finance. Dave's seen it all and he's codified his management principles into what he calls the management playbook. Dave and I get into a very interesting culture idea of idea meritocracy that Bridgewater has and how individuals can benefit from some of the tools and approaches that Bridgewater uses. We also detail Dave's big career pivot from hedge fund master of the universe to solo management education entrepreneur. I'm a sucker for a good pivot and Dave doesn't disappoint. Finally, we talk about his management accelerator. What aspiring leaders will take away from the course and why it exists. Hint something's missing in large corporate management training programs because folks from Amazon and other great companies are flocking to Dave's training. You can find out more about Dave by following him on Twitter. He's at decline II. That's at D K L I N E I I or find him on LinkedIn by searching Dave Kline. K L I N E without further ado. Here's my amazing conversation with Dave Kline. Dave, welcome to the show.

David Kline (02:20):

How are you today, Mike? Thanks for having me. I'm doing great, beautiful day here in the Northeast.

Mike Gardon (02:24):

Excellent. A beautiful day here in the Midwest as well. So I hope that's a good sign that we're gonna have a, an excellent talk. I've been wanting to talk to you for a while and I really appreciate all the time. So part of, part of my ethos is trying to get like the backstory, right? And as I was talking with you before we started, I said, I'm a guy that really, I feel like I never really had a calling. I didn't have like a plan in place necessarily for how my career was gonna go. So my first question is like, when you were in college, what did you wanna do with your life?

David Kline (02:54):

My first thought was I wanted to own my own business. And then it's funny to say with that only being true for the last 18 months and not being true for the 20 years prior. But literally when I left, it was 1999. It was just before the.com boom. And my thinking was, I'll go. I was an engineer, but I wasn't the engineer. It was electrical engineering. I wasn't the engineer like on the circuit board, like in our project groups, I was the one who presented. So I'm like, great, I'll go, I'll go consulting. I'll see a bunch of businesses. I'll pick up some skills for two or three years, and then I'll be ready to have my own business that then turned into another gig and another project. And then another company promotions and golden handcuffs get tighter. And then all of a sudden I looked up at 20 years and was like, I, that company, I was gonna start when I was 22, still hasn't been started.

David Kline (03:40):

And that probably the, if you were to ask me, like, why it's I reflected on it a lot? Like I had a pretty like scarcity mindset. We grew up relatively kinda lower middle class for most of my childhood sort of felt like we were, there were arguments about money. So like this idea of, for me, it was always like, well, could I save a little bit more? Could I have a little bit bigger cushion, a little longer runway, a little better safety net when time came to like rotate out of my next gig at Bridgewater, cuz we rotated a lot. There was a question of like, if not now, when, and that sort of started on the, the latest chapter, which I know we'll get to a little bit later,

Mike Gardon (04:15):

So correct me if I'm wrong, I'm just thinking, okay. So you had the engineering background, was that kind of born out of that mindset? Maybe like stem job's a good job. Like there's people that pay for that kind of thing?

David Kline (04:27):

Yeah, a hundred percent. Like I was actually invited into the English honors program. I was a pretty decent writer even in high school, but you know, I just sort of thought like, well I can do that on the side, but I should learn engineering. I should learn something that's gonna be valued in the future. I should do something that's hard. I certainly lived up to that barely scraping by to like knock on the door of a three oh of that degree. But then I also was a TA over in the business school for accounting and I continued to do the English stuff on the side. So there was certainly a, yeah, it was more defense and offense.

Mike Gardon (04:57):

Okay. So kind of post college and out in the real world first job or at least first major career was not really in engineering as well. Take us a little bit through your history, maybe up to Bridgewater. And I kind of want to ask some follow up questions when you get there.

David Kline (05:12):

Sure. I started at PWC back when they had a technology consulting division, which eventually I think got sold to IBM. I managed to pull down that job, despite my GPA through meeting an alumni of our fraternity, like a guy came back to recruit, he needed a place to crash. He crashed on my couch, we hit it off. He slipped me into a open interview slot on campus the next day and kind of advocated for me. And I got that gig and did that for a couple years, much like many consultants being on the road 50 weeks a year is a pretty much a grind. And so, uh, got an opportunity to work at Columbia on a project. The university did that for about nine months. That was a pretty quick gig. We could detour on why I left there, but the short version of it was I had a vacation plan with my good friends and my future wife.

David Kline (05:59):

And they told me I couldn't take it. And I told them I could. And 48 hours later, I had a job at Moody's making about 60% more than I was making at Columbia. So it was ended up being a win-win stayed there for nine years, got an MBA in the middle, which they paid for. I don't know that I would've done it, but there was no, no strings attached. And I got like a top 10 MBA from NYU and then get us to Bridgewater. The, the quick story that gives the entry to Bridgewater is a recruiter called one of my direct reports. He cleverly said, you know, I'm not really looking, but did you say the jobs in Connecticut? Cuz my boss lives in Connecticut and my phone rang that Friday and it just so happened to be, you know, summer up here. Think it's like probably June or so super hot and the train broke down three different days. So my hour commute from Connecticut down to lower Manhattan turned into like two hour commute each way. The third one breaks down, you get to the office, it's like sweaty, hot mess. And the phone rings. You're like, I don't know this number, but I kind of picked it up and you know, one thing led to another and I said, well sure let's talk nine minute commute sounds better than a two hour one. So that's the quick timeline.

Mike Gardon (07:04):

I wanna ask a follow up question cuz like you just glanced over it, but you said between PWC and Moody's, there was like 48 hours and you had a new job, like take me through that because a lot of our audiences job hunting and wondering how something like that happens as that network. How did that come about?

David Kline (07:25):

It was honestly recruiters. I call I was somewhere between ticked off and annoyed and so before I threw a stink, I sort of reached out to a couple recruiters just so I could understand what is the world like? Like it was post.com crash, right? It was 2002. So the market wasn't booming, but it was definitely bouncing back. And I had an engineering degree. I had worked at a big four consulting firm and in the process of doing that in the project, I had been attached to some pretty good software. Like I had done PeopleSoft implementations had done different analytics software. I could write SQL, not like or shattering things, but like tangible skills mm-hmm and it turns out that one of the two had an opening at Moodys that they had been struggling to fill that had kind of like that three year experience mark with someone who was technical enough to write code, but polished enough to oversee a few analysts, they rushed me.

David Kline (08:19):

They were like, can you go meet with the hiring manager tomorrow? And so met with him and he said, stick around and introduced me to his boss, met the two of the team and they're like, great. We'll have enough for you tomorrow. They sort of, it happened real fast. Wow. And it was, there was, you know, in hindsight I should have negotiated, I didn't even negotiate cuz it was so much better than what I was currently making and they solved an immediate problem for me. But yeah, again, I, I mean I have a lot of experience with recruiters on now post that time. And so I would say like, if you are, if you have tangible, valued skills in the market at a minimum, you sort of wanna stay in touch with a couple recruiters because they will have a lot of the information in Intel. But in many cases, like they get the first look at jobs, unless you had a back door into an organization where the literal team, you sort of found it before was published or posted a lot of these companies don't go through that hassle. They just sort of outsource it and let the recruiters do it.

Mike Gardon (09:07):

Interesting. Do you see the recruiters and like what's going on right now today with the job market, you know, a lot of people talk about how we're, we're essentially short jobs and there's a war for talent. Is that accelerated since that time period?

David Kline (09:21):

Oh yeah. Again, this was sort of post.com boom. So we were turning or bust, I would say, but we were turning, but we weren't, we certainly weren't out of it. And so that I idea that kind of played that forward with all the liquidity that's been flowing through the market over the last kind of couple cycles, especially the last five years. I know last stats I saw, we were probably two jobs for every one unemployed person. Now I'm sure that's some of that is tempering a little bit, but I don't think people should stare at the headlines right now of, you know, kind of high rising high risk unicorns doing 20 or 30% layoffs. Like I think that's a bit built in structurally. And even if you have giants like Amazon or other sort of slowing hiring, you still had that entire imbalance to work through. So I think it, it now more than ever, you know, you still have an opportunity to be in the driver's seat as it, as the employee versus the company.

Mike Gardon (10:08):

Interesting. All right. So, uh, like a big part of your story here is, is kind of your time at Bridgewater. Bridgewater's famous in, in circles around me, as I mentioned to you before I started my career as a prop futures trader. So I ha have a little, um, markets experience, but for our audience who maybe doesn't know Bridgewater, can you talk a little bit about what that company does hedge fund and kind of maybe like why they are sort of unique and held out at a, as a model or at least an example of how companies can build teams?

David Kline (10:39):

Yeah. So I think the, the short short version is like, this is the world's largest hedge fund it's been around for 40 plus years that sort of equates to, we were managing, you know, the number fluctuates, but call it 160 billion for the most sophisticated investors in the world. Pension funds, sovereign wealth funds, et cetera, to your point model, right? There's different types of models. There'll be funds that are algorithmic, right? They're just, they're computers that do all the trading. A lot of times they're high frequency. They're trying to just like outrun the rest of the market to produce excess returns. Bridgewater was much more like a, it's a, the macro hedge funds. So we're looking at big broad trends and then we would do that systematically, right? So we'd do very in-depth research. We'd try to re figure out like the universal principles of markets and then use that to inform our decisions that the, the people in charge of investing then make. So it's not algorithmic in that computers are doing all the work, but it is certainly systematic in that the, the lessons learned over 40 years keep getting compounded.

Mike Gardon (11:36):

Yeah. And I would say again, trying to make these multi-billion dollar decisions in highly uncertain environments, right. Always changing. I would say like money management and hedge funds are kind of always at the forefront of, of essentially trying to systematize good decisions. Mm-hmm . And then as part of that, I think what I've learned from Bridgewater and the founder, Ray Dalio and reading his books and, and all that kind of stuff is just as a part of that. It's like really systematizing human resources, people that make those decisions are aid aid, uh, computers and making decisions. I mean, in your role within that was very much developing or recruiting the people side and creating some of the management, I guess, uh, evaluation and, and processes around making the people as best as they can. Can you, can you talk a little bit about your role there?

David Kline (12:30):

Yeah. Well, let me one quick tangent, cuz you said that it's about, um, the idea of like systemizing good decisions and I think that's right. But one thing that I thought was interesting that I saw walking into Bridgewater in terms of me doing my research on whether I wanted to go work there. And it seems like it's likely playing out again is arguably the real innovation is systemizing, not making bad decisions. Like if you were to look at the chart of their returns over time in a lot of the up years in the market Bridgewater, just comparing you say, you know, to the equity index or whatever would underperform, not massively, but in those years the market might be up 12 or 15% Bridgewater might only be up six or eight, but the kind of the leap years are the years, the market tanks, right?

David Kline (13:14):

It's the 2000 and eights when everybody else is down 60% and they've CR they've looked at the system through a much longer horizon to kind of have bets in place that when that happens for very little money, they can make big returns. And so like years of that, the market down 60 they're up 40. And so that spread is massive, right? So to some degree it's not systemizing thousands of little good ideas. It's, it's really systemizing, not breaking when everyone else breaks. And that also gives you the secondary benefit of being a hedge, right. Being, not correlated to the rest of the market. Sorry, it's a bit of a detour, but it's just, um, it's an interesting phenomenon cuz you can sort of zoom out and see their total results, but realize that it's really five or six massive years that, that drive that. Yeah. And it's the years when everyone else is going the wrong way.

Mike Gardon (13:57):

Yeah. That's, that's really interesting. I mean I reading like Warren buffet and Charlie Munger, same type of thing they they're always talking about. We're just trying to not be dumb basically and wait and take the fat pitch when it comes and, and what you know, and there's so much that you can kinda, if you take that to a, from a career perspective or applying it to just your individual things that you pursue or put your, your time, um, behind the idea that like kind of minimizing decisions or just saying like that, that's something I wanna avoid kind of narrows your, your focus set and you can kind of compound that forward, um, just in your individual decisions. Which so I love the idea of like kind of listening to these really smart money managers and, and how they think about the world and what they try to do. And then I try to channel that into like how I do things just in my own personal life. I, I think that's like one of the biggest things I've learned from like reading all these books and following some of these guys. So that's,

David Kline (14:57):

Well, I think it's the perfect transition into your question in terms of my role, but also like the role of this approach, right? Like I think what's really perhaps the most profound piece is, you know, it's almost like the two parts of your brain are always battling, right? The lizard brain, which was all about fight or flight and then like the more intellectual side. And I think partly what all of these guys have done is they have through whatever means necessary either it's a tremendous discipline or in the case of Bridgewater, I think it's really through systemization they're saying like, let me somehow get out of the lizard brain and stay in the like fact data driven logical brain. Because I think a lot of us, I mean we're while watching the market swing around and like I know better and still have a lot of the same instincts, right?

David Kline (15:42):

Like, oh, it's falling. I should sell actually what it would tell you if, if you're really having a dislocation, you should probably be buying. Right. And, but it's like so hard. Cause you gotta get past that first instinctual part of your brain to get there. Versus if you just have a system that can make that decision dispassionately and give you that recommendation, then you can sort of get past that seems like Warren buffet and Charlie Munger did that through discipline. They're just like extreme exceedingly patient and disciplined. That's another path to the same place. And so, um, like I said, my roles were very much, I had, I was a COO of a couple different departments. I worked in the talent function for a while running executive recruiting. We did stuff on succession and development. If you sort of think of any company or any team as like the combination of a design, right.

David Kline (16:25):

Like process and technology and then the people to do it, that same system was sort of how Bridgewater thought of it. So you you're processing your technology, right? There's that system for trading the process was very much you either working with the clients to manage their money and connected to our strategies, or you were doing the research to figure out like how that system worked. And everyone else really was like organizing the people. Right. So even as a COO, it was everything from like how do people develop and do we have the right talent down to where do they sit and how do they collaborate? And so, um, really in all my jobs, it was very much focused on that side of the equation.

Mike Gardon (17:01):

Okay. And so I want to kind of get into a little bit of how that was done. I mean, cuz a Bridgewater is kind of famous for some interesting tools and, and it's really a lot around, I think, one learning from history and having like a lot of data points along the way so that you can kind of your traits or your, the decisions that you make or out and outcomes can be measured against historical data sets and that taking that from the investment side and applying it to people, but it sort of really starts with kind of Ray Dalio, the founders, uh, principles and his idea that he basically took over his life has, has codified principles over time, written them down, organized them in a framework and in a system for making better decisions, which he, I read as a PDF. I think I told you in like 2010 and now, you know, I've got this book on my shelf right here and it was kind of his operating system, if you will. And then it's gone from that to actually quantifiable tools for measuring performance and getting feedback that are a little bit maybe out there for most people. Can you maybe kind of go into this a little bit,

David Kline (18:14):

The history, as I understand it is race arts in his two bedroom apartment then starts making these trades. And part of what made his approach different was for every trade he made before he made it, he basically wrote down, you know, this is the trade and this is what I expect to happen. And then he'd make the trade and see what actually happened. So then he would compare that outcome to his projected outcome. And if they aligned great, he had learned something. If they didn't align, then he would try to diagnose, well, what was, what was wrong? Like why did I have that incorrect? And then he would use that understanding to kind of then make a better trade and make the same, be, you know, make a new bet and go through that same process over and over. So there was this compounding of that through time.

David Kline (18:52):

And then I think as he started to go talk about his transition or kind of his three phases of life, as he started to think about, well, how am I gonna transition out of leading Bridgewater and let the next generation of leaders do that? If you could use that same compounding to understand something as complicated as global financial markets, what he started to see is you could probably do roughly the same thing to manage people. Like at some level it might even be slightly easier, cuz it's a smaller market to understand we'd have a tendency to be slightly irrational and fickle as human beings. But that same concept of, you know, he would talk a lot about everything being another one of those. Like as much as we all feel like we're all snowflakes and deeply original and you know, whatever else, the patterns reemerge, right?

David Kline (19:33):

We all struggle with similar work things like giving feedback, different companies could be victim of groupthink. Like you, you sort of see the same things happen over and over. Some stars will have under confidence and some mediocre players will have overconfidence. And so you could over time sort of build a catalog of what are all of these sort of management moments that are gonna happen. And then what are the principles that should guide you through them so that it's not lizard brain reacting, it's that same system and compounding happening. And so the, like you said, that really started with him writing down. Like I think at the time it was a couple hundred principles. He then sort of like worked with the organization to say like what's missing. What do we add in, how do we start compounding the system that then led to, I think a couple more iterations, ultimately the book kind of maybe five years ago, which I think has more on the order of 400 of them.

David Kline (20:19):

So you could see that it evolved and grew and more people contributed to it. And then part of that was to say that, okay, that system gives you sort of the blueprint, but then you had to operationalize it right in the same way that we would build investing systems, you still needed to actually make trades. And so in the same way, we had to manage day to day on the ground. And so we took some of those most challenging moments and he started to like experiment, building little tools. One that he made public was the dot collector. Right. So it was effectively a pretty simple app where anybody at any moment could give someone feedback across 60 dimensions. So I could say like, wow, like the, the preparation for this podcast, Mike really analytical. I'd give you an eight on that. I see some really creative questions, give you a nine on that, but you missed a lot of details about how Bridgewater works.

David Kline (21:04):

So I'd give you a four on that. Mm-hmm making that up. So then it's like, okay, so now I've communicated to you. My point of view, we could transact on it. Or we couldn't like I was typical years, I'd probably get 3000 observations from different people, but those things would accumulate up into patterns like the, um, I think he's talked a lot in a couple Ted talks about like this got little baseball card. So instead of any individual like hit that a, a baseball player gets you sort of roll that up and say like on average, how often do they get hits? What's their on base percentage? How many RBIS do they have that same sort of thing would happen for us? All those observations would roll up and say, oh, Dave's pretty good at synthesizing complicated issues. And Dave's a pretty logical problem solver, Dave.

David Kline (21:45):

Yeah. So, so on detail orientation and being organized. So that really helps you when you start to think about teaming and solving problems like, oh, okay. Like this thing requires really indepth detail orientation. We're probably not gonna put Dave on that, but it's a really complicated tangled best that something needs to be like clarified like great. Let's bring him in and have him do that. And so that's sort of how you could trans you know, go from like a big system of these principles to then getting the data and then using that to actually operate instead of just sort of being, that's how it goes from being like a slogan. Like we all see those motivational posters down to the actual way we operated on the ground.

Mike Gardon (22:22):

And so just a couple things to point out for the audience. I mean, as you describe that, I think the key thing to understand about this system is that it was in real time as I understand it, correct. I mean, you could be sitting in a, in a room or I should say it was, it is cuz it's still being used. You could be sitting in a room with 10 people and on the screen you would literally see like dots and observations being logged for participants in the meeting. So this, this is one of those things where th a lot of companies may give you ratings once a year in a, in an evaluation, right before a bonus or something like that just end of the year. And that that's, that's kind of one observation. This is continuous and going on all the time, there's this transparency around it, which is uncomfortable.

Mike Gardon (23:07):

And I want to ask you a little bit about that as well. Mm-hmm but I mean, the key benefit is the, the, this happening with everybody, there's a very big incentive to be truthful and just get it out there. And then you have this sort of massive data set, and then you can compare objectively to the rest of people in the, in the company. Right. And have kind of like this base rate. So that's really important with feedback. I was just on a startup hustle podcast this morning, and we were having this conversation about, about kind of closing the loop on feedback. And I was, I was thinking about what our conversation was gonna be upcoming. And, and it's really like, I think a lot of times employees it's that comparison to a base rate that is missing for them to understand like OB oh objectively. Maybe I'm not quite as good as I think I am at this particular thing. Or I could learn X, Y, and Z to be become better.

David Kline (24:01):

If you want me, if you wanna click into the feedback, one it's super complicated and I'm personally torn on. So like I can start to deviate from what I experienced kind of my own point of view a bit, you know, if you go into, so yes, you're right. It was alwa it was real time. Like you could do it in any meeting. It was very conservative you to say it was a 10 person meeting. Cause a lot of times we prioritized as part of race transition. Like he'd like to use meetings as teaching moments. And so often you might have 50 or a hundred people invited to a meeting, all who had an iPad who could give you observations. And so occasionally you'd have some glory and get 80 people praising your creativity. Uh, and many other times they would be very quick to point out how much you might have flubbed a presentation or, uh, had a narrow point of view or been missing the big, big picture.

David Kline (24:43):

So it's real time. It's also like a Twitter feed. So you can see anyone's in the company all the time. This is where it gets some, some of the catch 22 of it. Yeah. Which, you know, again, it was like anything it's like an evolving system. So one is when you have 3000 observations, a lot of people wanna legislate every observation. So all of a sudden we get from a world of, Hey, don't worry about any particular dot, just zoom out and see the patterns, but it's still feedback. Right. And it can even feel anonymous. Right? We see this, the, the behavior in a lot of organizations, all of a sudden it starts to feel like social media. Like I'm not saying it to you, Mike, I'm writing it into an app. And for whatever reason that can sort of lower inhibitions, um, or let people be a little bit sharper than they might be.

David Kline (25:22):

And at Bridgewater that was sort of built into the culture like that was okay. We had all signed up for that, but we started to think about that in the broader world. Like that gets hard. Like not all organizations have actually signed up for that. You can get this like tax and the problem with the tax then, is it sort of like, well, if I'm gonna get legislated every time I give a piece of feedback, I'm gonna stop giving feedback. And all of a sudden the system starts to fall. So you have that piece. There's also, I guess, two other things that came to mind, one is that there's a pretty heavy bias skew in most organizations, negative versus positive. We tend to like sort of accept the things that are good as sort of like table stakes, but then hone in on like the one thing that was wrong.

David Kline (26:00):

So it can skew very negative. And most research would tell you that if you're trying to get the most out of your team at a minimum, you should be balanced. And most likely you should be skewed positive. You know, you should be taking your, your best athletes and reminding them to use their strengths, to get even stronger, not to like obsess about the places they're most weak. Like, yes, you want it to not be a liability, but I'm not gonna bring my right fielder in to pitch. I mean, I'm gonna have them work on hitting for power, which is why they're on the team or whatever that, you know, whatever the right analogy is. So you sort of get into that world too, where, you know, it, it skews negative and it gets to the last thing, which is most times feedback says a lot more about the giver than the receiver.

David Kline (26:41):

So you're bringing all of your experiences, all of your biases, all of your perspective to bear on this moment. And it, the goal of giving feedback is for the other person to get better, not for you to get something off your chest, but we're all pretty bad at actually knowing what's gonna help somebody get better. And so that's where it also can get very tangled. And I don't know that like anonymizing that into a tool actually fueled that outcome in the way you'd want. And so I think that's like, those would be pieces where even as I now like teach cohorts and we, we have an entire module on feedback, cuz this is such a big deal and so hard for people. And I think Ray was a hundred percent right. To try to like focus on this in the system because most companies are bad at it. I don't think it's fully cracked. Like it's a really hard thing to do. And I don't and simply having a tool didn't magically make it home.

Mike Gardon (27:29):

Okay. Yeah. That makes a lot of sense. I, so it's like the theory and the direction like directionally, correct. In terms of the approach and the implementation maybe, or is it's not set in stone as to, as to how that gets implemented, but the idea that we create better feedback systems and probably the timing and the, of them and the observations probably matter to some degree, um,

David Kline (27:56):

It's certainly better than the old performance management system of right. What'd you do the last two weeks? That's the only thing I can remember like this, at least you had like a record of the whole year, but again, I think there's just part of, it's sort of depended on like how much did you wanna push people to put fuel into that system? Or how much did you wanna let to be organic? You know? And it's like any tool, right? Like you, you roll out an app, is it gonna be uptaken because it's so cool or are you gonna like mandate it with compliance kind of protocols? Like, it's a pretty tricky thing to sort of like really find the balance on

Mike Gardon (28:27):

Of all the tools approaches for this. What do you think had like the most positive impact on either, you know, people's growth or the organization's decision making at a whole, however you wanna take that, I'm just like the 80 20 of it, I guess, like where, where was the most bang for the buck? You think

David Kline (28:44):

I'm like debating because I'm like on one hand, I want my answer to be the principles like that idea. At least for me going from a world of sort of, I was pretty, like I said, we have an engineering degree. I'm pretty analytical, et cetera, but this idea of sort of breaking things down into like their fundamental truths and you start to see a lot now written about like first principles thinking, right. That's how Elon, you know, did SpaceX and Tesla, et cetera. So that's like my first instinct, but one that might surprise you was we recorded all of our meetings. Like, so literally the, every room was, was set up with a recorder. You could just sort of walk in and press a button who knows it might be involved now, or you just walk in and your badge makes it start. But literally everything was recorded.

David Kline (29:23):

And this was probably the biggest Delta between what I expected and the benefit. So I, it was the one I was most like, I'm going on a reality TV show. Like this is literally being on big brother. Every single thing is recorded. It was the one I remember spending the most time debating, like, do I really wanna live like that? And then, you know, flash forward six months and I had a totally different perspective on it. Like, I, again, I'm not sure I could handle the logistics of it for a small company, but the benefits of it in terms of there was no more people talking behind each other's backs. Cause it was on tape. You know what I mean? So it was sort of like, and that, that somehow just then made you much more willing to be like, Mike, this is how I'm seeing things.

David Kline (30:01):

Let's hash it out instead of going to like a third party and winging about it. And then someone else is crying in your office and then just things I'd experienced. Other places were sort of eradicated from the system in certain ways, the idea that you could go back to the tape so many times you'd have people come into your office and like, we disagree on this thing and you're like, well, you said this and you said this and you're like, we can literally just go see what you said. Like not that hard. And it's just little things like that. So I'd say that was the one that surprised me most on the upside, based on where I was walking in the door.

Mike Gardon (30:29):

Interesting. I guess I'm trying to think of like how you take the idea of, of feedback and of, I guess resolving disputes fairly. That makes me think of what you said with the, with the recordings. So let's take it outside of Bridgewater. How do you maybe coach people to want more feedback and more truthful feedback and kind of accept that. Like I, I see the approach at Bridgewater. I'm like, that's great because we're trying to get to a truth. You gotta kind of buck up, you gotta kind of have a thick skin and you got to sort of want to go down this process of getting better and of hearing all these perspectives and maybe not emotionally getting too tied up emotionally. Like how do you maybe outside of Bridgewater, how do you coach somebody on that? Are these tools still applicable or are there just other approaches?

David Kline (31:24):

I think the, I would almost like set the, the literal apps aside. They might be right for some companies, like I think wine base just signed up for the doc collector so that, you know, that's a publicly available commercial application that might work for the right size and right. Interesting company. But I think the principles and the concepts can apply more broadly. Let's just take a couple that I think you were highlighting. So one might be, how do you get people to go from sort of fearing, receiving feedback to hungering, to receive feedback? Yeah, the reason I think it worked is, you know, first you have to build that kind of growth and like kinda learning mindset into the organization. Like you have to say like, we prioritize this and you have to show it right. You have to show that like, yep, we're gonna experiment and we're gonna make mistakes and then we're gonna learn from it and we're gonna make better experiments and make more mistakes and then learn from those.

David Kline (32:10):

And we're gonna compound and grow. Like you could literally see that everywhere in Bridgewater and not just so it wasn't just like a piece of paper telling you to do it, but then you could see people doing it. So that's showing and telling lining up. So I'd say if I was a, a founder or a small team running a small team and I wanted this to be true at first, have to like, make sure I am like showing it on a regular basis. The next way I would show it is like I would be vulnerable. I would be seeking feedback. Yes. I would be role modeling. You know, like it's mostly like, do what you want them to do first and then they'll do it. And so it's like, you need to, as the leader be the one in making that happen on a day to day basis, another thing I would be doing is, is sort of getting people.

David Kline (32:47):

So if you have this like learning culture and then you have a leader who's doing it, then I think you need to, um, you basically need to get people away from good and bad. Like this is where I find the hardest thing is people think of it as like positive feedback and negative feedback. If you listen to people like I do this a lot. When I'd interview, you kinda listen to the language they use about giving feedback or receiving feedback. And it's really charged, you know what I mean? It's like, you know, you're gonna hit people with feedback, you know, you know, punch 'em in the face. Like they crushed me with that feedback. It's like all, it's all loaded. Mm-hmm versus if you just sort of take more of like a scientist approach and it's just like, everything's generating data, hopefully the data's accurate and the accurate is gonna tell you it worked or it didn't work.

David Kline (33:29):

And if it worked, keep doing more of it and if it didn't work, change something and do something different, you know what I mean? And that almost like taking that like good, bad, like supercharged language out of your team's vocabulary and just into like true or not true, did it work or not work? That would be the other thing. And, and that just takes a lot of reps and repetition, you know, and I guess the, the last one is hire the people who are into that. Like, this is a hard thing to train. If you are one of those people who takes criticism in that way, it's one of the hardest things to loop out of. So that's why you'd see a lot of Bridgewater. People had some head military backgrounds, a lot of sports and athletes, cuz they were used to being coached like anybody who had been used to like looking back at failure and iterating on it, tended to like actually find it refreshing and people who hadn't grown up in that way. Who'd only like maybe gone through academics and gotten A's the whole time found it crushing. So I think you had pick your right people too.

Mike Gardon (34:22):

Yeah. That makes sense. Getting away from good and bad and getting towards truth, UN truth. That's I think one of the principles, I think that's in the book. So it it's an example that the, the organization, the book isn't just marketing, like it's ingrained and, and you can learn a lot from that. And I think as part of that, what you were alluding to was saying kind of treating everything as an experiment. And I think you and I had a little bit of a Twitter exchange recently on that topic. Like you're putting out a lot of stuff on Twitter and I, and I just love it around management leadership. And I do think that that is one of the, the mindsets that's missing from a lot of young employees is they're not treating it all as a process of a big, long set of roles of the dice, every single decision you make.

Mike Gardon (35:08):

Right. And looking at that in the long term. And I think when you do that, when your mind flips that switch, a lot of that emotion comes out of it. It takes a little bit of the blinders off and you can kind of say, okay, yeah, I screwed up on that big deal. Like we I've got 500,000 more decisions to make in my life and, and kind of get on with it. So I do think that's, that's like a big piece of it. So talk a little bit about Twitter. You're not at Bridgewater anymore. You've kind of done a career pivot and we love career pivots here on this show. So talk to us a little bit about what you're doing, how that decision was made to leave this amazing company, this huge well-respected company and, and kind of go to your own thing. Talk to us about that.

David Kline (35:49):

I was coming up upon, I think, 10 years, right? I'd been there about nine years. The way Bridgewater treated management is we were pretty rotational by design, right? So I had been in five departments over those 10 years. Uh, I'd been the COO of two of the bigger departments. I had run a big department that was kind of the department head. I was then working in recruiting, running executive recruiting that all sort of conspired around the same time as the pandemic. And so we went from being a company that really prized being in person like all employees were with exception of maybe a couple dozen were in Westport, Connecticut. And all of a sudden we were home, right. And we were home for much longer than we thought. And so the staff to run multiple buildings or the, the needs of kind of the, it was very clear that the world was changing in a way that the structure of the company was gonna have to change.

David Kline (36:33):

You know? And so as we restructured it, it forced some reflection for me, you know, like the next logical step was gonna be probably the COO of another big department. And was that gonna be sort of the thing you were just saying? I think of it as like collecting experiences, like in your career, you wanna collect them and they can be good and they can be bad, but both of them are gonna teach you something and prepare you. Like, even when you have failures and mistakes, you can often teach other people how to avoid them, or you can glean something important that will then help you avoid them in the future. And so was I really gonna collect any new experiences running the operations for another department at a company had been at for 10 years. And my conclusion was mostly no, that like not material enough.

David Kline (37:12):

And so we got, you know, my wife and I sort of had a real conversation. We made some interesting choices. Like we, we had done a giant renovation on a house, you know, we had always wanted to do kind of a gut renovation. We had just finished basically a five year project and thought, well, what if we sold this kind of got our money back out of it. We actually never thought we would. Cuz the housing market in Connecticut was only gonna probably stay flat or go down. But then we all know what happened in the housing market the last two years. So we sold in the June of the pandemic, we moved back to a smaller house. We sort of re you know, that got us a mortgage at much lower rate. So we like really trimmed our costs down. And we spent, we made a lot of decisions like that to sort of extend the runway.

David Kline (37:50):

And then we bought a, I left Bridgewater. We, we said like, let's give it a year. If I can find a business to buy, that'd be great. If not, then I'll, we'll reconsider whether this is the path and we'll go find something else. And so we found one in four months, um, it was an online education review site that we bought from a, a fell in Australia. And that was really meant to like, okay, now I can have cash flow. You know, it's not like a, we had a few thesis on how we'd grow at and we'd get to that in a second. But that after kicking the tires on, you know, 40 or 50 businesses, it seemed like the right one that I could operate pretty independently that would give us plenty of cash flow for a while. And that had some growth opportunities. So that, that happened. And then from there serendipity took over.

Mike Gardon (38:30):

How so

David Kline (38:32):

Well, one of the thesis on this site was there was this emerging type of course called cohort based courses. So if you've seen either Maven or Reforge or on deck, it's sort of running live cohorts of people getting trained on the same topic at the same time, they tend to be much higher price points than like a Emmy or a Skillshare or a LinkedIn learning. But they also tend to come with like the benefit of a community. Like you might be interested in online writing. You're now with 60 other online writers, all aspiring cheer each other on sharing notes. So you kind of feel like come for the class, but leave with a community mm-hmm . And so we, the part of the thesis was, well, we can start to review these sites. Like, there'll be this, no one's doing this yet. We'll do that.

David Kline (39:10):

And so in order to do that, we'll take a class. And the class I picked was saw hill Bloom's the Twitter audience building course. And part of that was because my entire business was premise on Google and Google had just changed the algorithm and my traffic went down 15%. It kind of bounced back in a couple weeks, luckily, but it was still like, whoa, whoa, whoa. Like I'm pretty concentrated. And so I went in there to build our company's Twitter hand, like our Twitter account. And I couldn't have been three minutes into the course where it's like, if you're here to build a brand Twitter account, you're wasting your time. That's really hard to do . And I was like, well, hell shit, anybody in here can build a personal Twitter account, like find your lane and write about it, et cetera. And so I started writing about a bunch of different things like online education, leadership management, and then a couple of those took off, made friends with the folks at Maven, got into their accelerator and sort of in the process of figuring out that course found this community of kind of zero to 10 year managers and leaders who weren't getting any support, who a lot of companies were thinking of it as congratulations, you've made it to the top and now you're on your own.

David Kline (40:12):

And when they asked for help, they sort of got the like management by hazing response of like, well, I figured it out. You'll figure it out too. You know, based on what I'd seen at Bridgewater through all of our efforts to like train managers and systemize, like there are some basic things you can teach people like you can teach them how to delegate. You can teach them how to give good feedback. You can teach them how to empower people to do their work and be far enough to not be micromanaging, but close enough to support. You can teach them how to size people up differently and realize that not everybody on their team is the same. And so, um, we put together a course to do that. And that's the part we, where Seren to go over. Like we've done two really successful cohorts. You know, the last one we had almost all nines and tens and people said it was worth 10 X, the value they paid tomorrow. I wrap up an cohort with on deck that where we did, we trade in 28 of their managers where I think we're about to start another one with another company next week. And so my supplemental business has become the primary business, which has been pretty, pretty wild journey. The last, you know, four months

Mike Gardon (41:08):

What's super interesting to me is the, this part about how, as I was researching, I was looking at the course and researching you a little bit. Um, you have people from Amazon and some large companies that you would think have pretty darn good management training programs, if not for the sole purpose of just attracting people, but there's something lacking. It seems like. And I mean, I, and you're in a great position to, to help with that. What do you think is lacking in most management training courses or management training programs I guess at, at companies?

David Kline (41:43):

So the two things that I've heard most consistently, cuz you're right. I, we have, it's a really big mix. Like we've had people from five continents, we've had like large, large corporations where to your point, you think they'd be super well trained and reimbursed. And then we've had my last cohort had nine founders. It's also people who, in many cases they're sort of stepping into management for the first time. Even though title wise, they might look very senior. You know, a lot of founders had a great idea. They might have a couple partners. Then they get like a seed or a series a and now they have a team of 15 and they're like, well, wait, I was the product thought person, not the leader of humans as how do I do this? But the, the two things that I've heard most consistently, so one is the majority of training comes from career trainers and, and like facilitators mm-hmm .

David Kline (42:29):

And so a lot of time the training sort of comes off of, I have this question and the response is, well, what do you think? Versus a lot of what's come back in. The comments for us is like, what I love is that you've done this for 20 years. Like you've managed teams of two and teams of 200. You've managed everyone in the same office and people in four different countries. And so that idea, if I can just sort of, at least I can trade war stories, you know, I can sort of like, this is what worked for me when I ran into that same thing or when I had this toxic employee, here's the three mistakes I made, don't do that and things of that nature. So that's one. And then the other one is there's something in a lot of organizations about like, well, what is your support structure?

David Kline (43:05):

Like, it can be very lone. They call it, you know, they say it's lonely at the top. It's also just lonely leading anything. Cause you may, for whatever reason, depending on your organization, you may not feel super comfortable or have access to your peers. You may not wanna take everything to your boss. You probably don't wanna like be chewing the ear of your team in some cases. And so to find this community of other people who are, you know, probably in non-competitive companies, similar organizations, or even very different organizations, but sort of on the same lonely journey as you are, a lot of people just said they got a tremendous value from having those like small, intimate connections of people. They can now call after the fact or people they could just, you know, we would do breakout sessions for 20 minutes and they would just we'd have three founders or, you know, three managers just riffing on a problem. And they, they said that they even, that was great. Like they didn't even need me in the room for some of that stuff. So I think those are the two things that a lot of kind of traditional corporate training doesn't give people.

Mike Gardon (43:56):

So what what's like maybe the one to three big takeaways that somebody's gonna come out of your course with,

David Kline (44:02):

I would say the one that I think surprises people is like the absolute foundational importance of being self-aware of like developing that a really keen understanding of what you are like where your strengths lie, where your mindset or your biases might help you or hurt you, you know, the skills that you might have, how you might use others to supplement them, et cetera. So just like developing that, developing that self-awareness not only helps you sort of put yourself on the field where you belong or don't belong. It also gives you a language and an appreciation for the differences of everybody else. And so we actually start the course there and it's one where pretty consistently everyone has said like of all the things on the curriculum, that one didn't seem like it was gonna be very interesting. And then at the end there, it gets one of the highest ratings where they're just like, oh, that was actually really important.

David Kline (44:50):

So that's one, I think coaching and development, like not a lot of organizations, people will often go to feedback and sort of the, like how do I give negative feedback? But instead what we're really talking about is like, how do you develop your people? Right? The, the real goal is to take someone who's a B and turn them into an a, or take an a, and like get them to be twice as impactful or strip bad work off of them. So they can like focus on where they're superpowered. And it's like, how do you do that as an individual? And how do you bring that together as a team? And how do you, what is the difference between like coaching and directing? And so I think that's usually one that people have found, um, really like lifts their teams and that they can do. And then I would say the one that everyone comes for is delegation that like setting really clear expectations with people, not just on like what the work should be like, oh, your sales quota is a, you know, $10 million, but how, you know, like what process do we use?

David Kline (45:41):

What technology, what are our corporate cultural standards? What are the behaviors we want our team to embody with customers and things of that nature. And then doing that. So that now delegation is, is just like, okay, we've agreed on this expectation. Now deviations are just us com collectively as partners comparing the difference of whatever happens to what we said was gonna happen. Um, and sort of, sort of, it moves delegation from like the old model, you know, the old Eisenhower matrix of like delegate the crap to, how do I empower you to do more on behalf of this team, because you're the best person to do it. And it's the best thing for your growth. So I think those are probably the three. I've also heard that we're one of the only trainings that do, um, we have our entire recruiting module. So apparently a lot of people keep that separate. So, and we did a lot of recruiting at Bridgewater. So I have a few reps on those.

Mike Gardon (46:29):

I know we're up kind of up against time. I do have a couple, like two more questions. I feel free to keep your answers brief if, if you need to otherwise I'm here. So I, you know, we can keep going. You made this career change. What was kind of like, what do you think the keys to making a career change like you did are, or, you know, you can take it as like maybe something that you learned from doing it.

David Kline (46:49):

Yeah. I think one I alluded to was like, for me, at least, like I needed to have a really clear understanding of my finances to know like how long was long was I could be fine for, and it was both important for me, but for my wife or my family for all of us to be on the same page. And so it, it was a pretty thorough scrub of like, what are our finances? What are our plans? A's and BS, you know, where can we cut down big expenses, et cetera. So that just having that actually gave me a lot more confidence and understanding, and then I think, well, we're 18 months into it. So take it for what it's worth. I would say like taking action, but listening for the response has been huge. So again, I talked about having a business for 10, 20 years.

David Kline (47:30):

Mm-hmm I finally took action and it was nerve-wracking and it was a little bit like a step into the breach. And then, like I said, serendipity intervened, and I think it was actually good that I didn't just like buy this business and like put blinders on and not listen to the fact that like, oh, I do need to kind of diversify my traffic and like, oh, that did open up this new concept of training and, oh wait, I actually can really like, you know, get great engagement from people on this thing and, oh, wait, that's actually now the bigger business. And so that idea of, I never would've done that if I hadn't taken action. Um, and I also probably wouldn't have done it if I hadn't taken a lot of the problem solving tools I had gotten from Bridgewater and applied them of like looking at the data, iterating and iterating through it.

Mike Gardon (48:12):

Excellent. What advice would you give to, you know, a young person, right outta college, looking at their career, looking at starting their first job, just about being, being successful.

David Kline (48:23):

I think if I were to take one of my mistakes and sort of go back and like, I would say, um, the, a job that's a seven or an eight out of happiness and fulfillment is the most dangerous one you can get into. Cause I think when you have a job, that's like a three, you know what I mean? Like you have that boss who's terrible and toxic, or the company mission doesn't align or companies go like it's such an easy choice to kind of move on and find something better. And when you're in the 10, the nine or the 10, you're like, it couldn't be better. I'm thriving. I'm collecting those experiences. I'm growing, I'm getting new challenges. I'm like psyched and the seven or eights are like, they're tricky because they're the ones where you're like, it's okay. Like, you know, I'm super privileged. I'm lucky. I've got a good job, not a great job. I would be really wary of those. Like I think you should force yourself within some reasonable timeframe, call it three to six months to force it to a nine or 10 or force it to a three or four and then choose especially early on. Like I just, if I could go back, I probably would've gotten a few more pieces of data and allowed myself to iterate faster to the place I ultimately got to.

Mike Gardon (49:28):

That's great. I love that. You're totally right. That's very tricky. You start getting comfortable, you gotta steady paycheck and you start putting up with things that maybe you wouldn't,

David Kline (49:37):

They start giving you equity. So now you're built in more long term. They gets super tricky. Fast.

Mike Gardon (49:43):

Yeah. Excellent. Well, Dave, this has been great. I found you on Twitter. I love all the stuff you're doing on Twitter and LinkedIn to my audience. If you wanna learn about leadership, if you wanna learn about management, hiring follow Dave, I'm gonna let you give out your handles and where anybody else can kind of find out more about you and your businesses.

David Kline (50:06):

Yeah, I think you've nailed the two best ones. Like I'm probably most active on Twitter. So decline II also Dave Kline on LinkedIn. And, uh, we will, we're gonna be launching the MGMT accelerator website shortly, and we'll probably have a new offering on there that will be a, a little slightly lower price point and not just a couple times a year in the, uh, accelerator. So stay tuned.

Mike Gardon (50:30):

Excellent. And we'll make sure we, you know, have links to all of that in our show notes page. And we will look forward to following you. I'm just so excited with all the stuff you put out. I love it. And just love following your journey. And I'm kind of right behind you got the site, got the Google traffic and all of that and working on more of the community based, uh, model. So I'm learn, I'm learning tons from you and I really appreciate it real, really appreciate all of your time and coming on today.

David Kline (50:58):

Thanks for having me on it's fun doing this journey together, Mike.

Mike Gardon (51:01):

All right. We'll talk to you soon.


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