Transcribed by https://otter.ai
Wade Chambers
You will watch a lot of entrepreneurs get to the point of like, Oh my god, this is the coolest thing ever. If I build this, every single human on the planet and all of the extraterrestrials are going to want this.
Scott McGrew
I’m Scott McGrew. Welcome to Sand Hill Road.
Ronald Reagan
My fellow Americans
This is the 34th time I’ll speak to you from the Oval Office and the last, I’m looking at a photograph and I can tell it’s from the 1980s simply by the fact that it’s of Ronald Reagan in the Oval Office. His eyes are bright, and he’s got a snazzy tie pin and a crisp white pocket square in the pocket of a dark suit. He’s standing next to and shaking hands with a young man, I’m going to guess early 20s but I’ll find out later 19 The kid is wearing a dark suit blue tie and has stepped forward a bit towards the camera. Go look at that picture in detail and just look at the handshake. Like my knuckles are white. I’m gripping it so hard. And the thing was is like they had us it was a photo op to go in as he was leaving office. And I mean, it’s kind of a big deal to get the photo op in the Oval Office. That’s way chambers and I’ll explain how he fits into
Scott McGrew
Our interviews with venture capital in a bit. But the reason Wade is in the white house in 1988 is he works in the white house in 1988. He’s 19. And I’m starting to think, wow, you know, I’ve seen him so many times, but like, this is the leader of the free world. This is the most powerful person I know. And it was the the first time with the exception of being on the air today.
Wade Chambers
My hands were ice cold, but sweating. Oh, yes. And so I walked into the room and and they told you sort of you walk in, you look at the president, you look at the camera, shake the hand, and then you’re going to walk out the other side, and it’s like, literally all of three seconds or something along those lines.
So I walk up, I grabbed his hand, and I’m staring at him. And he starts twitching his head, right and he looked at me and then twitched away and then he looked at me
twitched away. And I’m like, What’s going on here? Like what? What? No. every other time I’ve seen the president like he was very engaged like what is going on? And then you look back at me and he twitched another time. I’m like, What? And I look over there and of course there’s a camera there you gotta get you gotta get my picture taken. And but the end it’s a nice pleasant picture and, but if you go in and you use zoom in on that handshake, it is quite clear that I am very, very nervous in that shot. But he was phenomenal. He was truly world class at what he did from the ability to connect with humans and and make them feel like they were special.
Scott McGrew
How does the young man from Missouri end up in his teen years in the White House and this situation room specifically?
Wade Chambers
Yeah, that that is a bit of a story.
Scott McGrew
I’ll come back to that story in a moment, it’s even more surprising than you think. Wade came to my attention as Chief Technical Officer at Grand Rounds, a healthcare company. But he’s been on my radar since he was at Twitter. And before that at Greylock partners, where he worked as Executive in Residence, that’s a venture capital position we’ve not talked about on this podcast before, think of Executive in Residence as the I’ve been there done that person ready to help the funds, young entrepreneurs.
Wade Chambers
There’s a bunch of younger talent that’s actually starting to create companies. And they have all of the energy all of the intellect and less of the wisdom. And so when they can actually tap into somebody who’s hit the wall hard before a few times, and can say like, How did it feel when you hit that wall? How do I avoid that wall? Then there’s something that you can you can give to them that helps them accelerate
Scott McGrew
what are the walls In your experience, what are the common denominators for young entrepreneurs who go back to their to their venture capital funding and the Executive in Residence and say, I have done x or I’ve not achieved x? And everyone says, Oh, yeah, that’s a big one.
Wade Chambers
Yeah. Well, there’s there’s a bunch of different things, believing hype. A lot of times it’s ego, a lot of times it’s blind spots, the things that you don’t know. I love the Steve Blank, four stages to an epiphany, like, go out and engage the market. Can you find somebody who’s willing to put ink on a check, and actually pay you for the thing that you’re trying to create? Can you find a second person that’s willing to do the same thing 10 people who are willing to do the same thing? And is the product stopping its rate of change? You’ve probably figured out product market fit when those things start to be the case. Instead, you will watch a lot of entrepreneurs Get to the point of like, Oh my god, this is the coolest thing ever. If I build this, every single human on the planet and all of the extraterrestrials are going to want this. And they are so stuck on the idea that they never go out and try and prove it. That’s a pretty big deal.
Scott McGrew
It is amazing. And this happens in the news industry as well because we’re pressured. You know, did you tweet something today? How many retweets did it get? In which I want to ask my bosses but nobody’s writing a check for that. That it’s, it’s it’s something you can measure. But in the end, we’re not making money off of that thing. It can be sort of that epiphany to a young entrepreneur, that Listen, if nobody’s going to pay you money for it. It really doesn’t matter that much.
Wade Chambers
Yeah, I mean, I learned as a business. I lived through that stage as well. Right. Like we’re paying for eyeballs. Yeah, and if you think back to the late 90s early 2000s, right, like, yeah, we’re losing money on every person, but we’re going to make it up in scale. It didn’t quite work out that way for everyone. But I think that there were class of companies where you kind of knew there was a way to be able to monetize it. The real question is, is could you get the volume? And then could you retain those eyeballs? And if so then like, advertising became a thing or up sells, micro payments, etc. That is the exception and largely that has been built.
Scott McGrew
One of the things you did before grand rounds and was Twitter and you have been credited for doing exactly that Twitter had eyeballs but it didn’t have money. You helped bring revenue to Twitter. That’s, that’s an enormous accomplishment.
Wade Chambers
To be fair, they already had a lot of revenue before before I came. But a lot of it was brand advertising. And tell apart, which is how I got there came in through acquisition. And we had the ability to understand a person’s intent and interest at that point in time. So outside of brand advertising, could we understand what they wanted to buy? And could we put the right product in front of them at the right time? Lot of those same ideas actually, naturally translate to Grand Rounds as well? Can we make sure that we understand what they’re going through and who’s the right position put in front of them, but back then, it was less understand our audience, the duopoly of Google and Facebook, I think every advertiser out there wants another option. They know that prices go up when there’s only two people in the market and if there’s another place that we could go, that actually bring some equilibrium to the market. And it was really exciting. To be able to give them that third option.
Scott McGrew
Also on your resume is AOL and Hewlett Packard and Yahoo. These are companies that at the time, were so important, and so exciting to work at. And in retrospect, they’re AOL, Yahoo and Hewlett Packard and my apologies to anyone who works there. Now that I sound like I am, I am saying that they are not the most important companies in the world, but they’re not the most important companies in the world. what lessons can you take out of those companies that were important, but aren’t as much any longer or do you disagree with my premise? Well,
Wade Chambers
one correction. So while I did work at a well, they acquired Netscape. That’s where I was at.
Scott McGrew
HP still used to work at AOL. I
Wade Chambers
did HP Bought ops where I didn’t work at HP. I did ran engineering for ops where and there’s Marc Andreessen, Ben Horowitz Oh,
Scott McGrew
yeah, we’re getting we know we’re gonna get to that.
Wade Chambers
But to go back, what I find is that there are a bunch of companies that sort of show the way. Right. And so while they may not have prominence today, they sort of showed the way of what the next wave was able to sort of come in and complete the promise of what was shown before. I think that you can look at that very clearly with Netscape. Netscape showed the way of Oh, a browser. Well, Microsoft said, Yeah, but it should be free. Netscape built out an awful lot of enterprise software, servers, middleware, etc. Lots of other companies afterwards was like, Oh, I know how we could monetize that even better and provide more functionality etc. Ops where same thing We actually allowed you to automate it. How do you provision servers? How do you go out and build a full stack of where this the startup that wants to become big and be able to scale overnight? How can we do that? I don’t know that there’s a direct correlation between what AWS does today. But this preceded it by a number of years and allows you to package things up and deploy it. So it kind of proved the point that there was a company that you could that could package up your software and help it scale. And so I think there’s a whole round of companies afterwards that came through and actually delivered on what they saw in the first version, the one dot O, and was able to do much, much better to
Scott McGrew
Was it an ops were at 28 that you became your first management job?
Wade Chambers
I started man Well, there is the one of those hit the wall experiences and oh my god, that was a disaster. Then I went back to being an individual contributor for a period of time and at Netscape was reproached and like, dude, you should be a manager. And I’m like, I know, I know this story. This is going to be horrible. I think I want to start
Scott McGrew
with a disaster. Give me the backstory about being a disasters manager. Oh, wow.
Wade Chambers
Okay, so I was a pretty good engineer. Like I was actually, I think, better than average. And I always sort of gravitated towards the front of projects. And I knew how to simplify things. I knew how to make things work at scale. I knew how to build distributed systems, etc. And so after a while, you start to become the project lead the technical lead. And I was definitely doing that. And at some point, the CEO is small enough company, the CEO stops by and he’s like, we, you should be a manager. And like, the CEO, is recognizing that I should be a manager like Of course, I should be doing this. And so yeah, let’s do that. And so the very next day, I’m a manager. Awesome. Okay, no. Yes. So we just kept doing things the same way. And you know, I’d get people into the room and it’s like, oh my god, in the shower this morning, I had this great idea. And here’s what we should do. And john, you should be doing this and Derek, you should be doing that. Etc, etc. And I thought everything was going smashing Lee. And then people started to quit. And I was okay, what’s going on here? Like, don’t you guys know we’re killing it. And I had one senior engineer who was very kind and took me out to lunch and was saying, like, you are probably the worst boss I’ve ever had. And I’m like, What are you talking about? And he’s like, I haven’t grown one bit, since you’ve been my manager. There is you suck all of the air out of the room. There is no forward career growth for me here. And everybody else is feeling the same way. I have this belief that like people can detect excellence and they can detect bullshit. It was very clear. He was telling the truth, and and was trying to be excellent in the way that he was doing it. And he was so spot on. Right, all of those things he was saying was incredibly to true. And honestly, no one no one had taught me what management was or what my role is or how I should be thinking about that differently. So I retreated to competence. I went back to that thing that I knew how to do very, very well and I started slinging code again, and did that for another few years.
Scott McGrew
And then Ben Horowitz tells you you can do it again. Yeah, I mean, Ben Horowitz of all people
Wade Chambers
then Ben’s gifted I mean, like that, that that dude is super smart, super humble, and very capable at what he does. And so after the the acquisition by AOL of Netscape, he took over the shopping division at at now, AOL. And what we found is like, you know, this is back in the 90s. And there’s not a lot of infrastructure and so every time AOL would turn on a new merchant, we just killed their site. And so was working with Ben to make sure that we’ve got the right search, we’ve got the right systems, etc. And I think that Ben had a chance to see me as an icy and also saw leadership chops and in that, like, I would move towards the fire. I would try and help things out. And I think that’s when Ben was like, okay, you know, there’s a lot of the right characteristics in the sky. And, you know, I think he should be a manager inside of the team. So he approached me with that. And I’m like, dude, no, I suck. I know, I suck, I really do suck and told him the story about the previous company. And he’s like, has anybody ever talked to you about what it actually means to be a manager? And he broke it down, right in a way that like, I got it, or at least I got the concepts. And he volunteered to help me practice and to help me go through the growth that was necessary for me to become a competent manager. And so like, at the point in time, I’m like, you know, oh, it’s been now you know,
Scott McGrew
Andreessen would cost to hire Ben Horowitz yet you how to be a better manager, right?
Wade Chambers
Yeah, I don’t want to pay that bill. So
Scott McGrew
what is the second time around? Just a couple that didn’t made you the better manager? You’re the CTO of Grand Rounds now. So clearly, you’re a pretty good manager. What did you do the second time around?
Wade Chambers
Well, it wasn’t about me. Right? Like, the whole point. Is your team growing? Are you capable of winning? Are you capable of understanding what the company needs and then working backwards from that? Right? A lot of first time managers like if you were to think about individuals are part of teams that build product or build results for the company, they kind of go left to right in that sequence. It’s like, oh, I’ve got some people and can I hire somebody new and Oh, they look good, etc. And what’s the minimal amount that we need as a team to to have a ship something and what’s that something would we commit to, and hopefully the company benefits from it. And I think that senior people come at it. are more professional leaders and managers think about it from right to left. What are we trying to do as a company? What do we need to achieve? What will create true competitive advantage for us? Interesting, if that’s true? What’s the desired results that we need? Like what will create a genuine business impact and create real competitive advantage? Then you can work backwards from that to say, what’s the design of the machine that has the highest likelihood of creating that business impact that that we need? What’s the separation of concerns? What’s the separation of responsibilities? What are the competencies and skill sets that we need? Excellent. Okay. Let’s make sure that the team has the ability to attract that and we have the ability to go hire, retain, grow that so now it’s all for purpose. It’s all in focus. Then really help set a lot of the cornerstones of that for me to be able to make sure that I was looking at my job correctly. My job was to win and then increase my capacity to win. And do that with teams. one of your most famous managers was Ronald Reagan. You worked for Ronald Reagan. Now everyone in the federal government worked for ronald reagan at one point, if that was long enough ago, but you worked in the same room as Ronald Reagan, that man was talented. He had that ability to make you feel like he was you were his favorite. Within seconds, like that ability to and I’m sure being an actor and everything else helped with that. But like, genuinely you felt like you had a connection with him within seconds, and he didn’t feel aloof or beyond anyone. He felt very much connected to everybody in that room, and made sure that he made time to to work the room as well. It was one of those things that Actually the you were talking earlier about the picture of me being in
Scott McGrew
Yes. I’ve seen a picture of you and Ronald Reagan. You’re what? 19?
Wade Chambers
Yeah, I’m so I’m surprised that I actually made it there. my early years. There’s nothing from my early years that would suggest that I’d be sitting here talking to you. My parents were extremely poor. My stepfather had a second grade education. You know, they weren’t conscious parents that were thinking about, like, how do we put him on the path? So like college was never a thing that I even considered like there was just no opportunity for me to do that. But I knew that I might. My father was an auto body repair man. I knew that in Southeast Missouri. If I was going to stay there, my life was not going to be so good. I knew that I needed to leave that. I had no idea what I needed to do. I just knew that that wasn’t the thing. I knew I needed to put myself in a position to win had no idea what that would be. So I joined the Air Force. And Air Force will give me structure. Air Force would allow me to do things and that’s how I got to be an administrative specialist. And that I’m thinking like, okay, every day when I’m working in my dad’s shop in Missouri, I have to go home and scrub my hands for 30 minutes to like, get all the Paint and Primer and all of those sort of things off. Wow, being at a desk in the Air Force, that will be better that is significantly better. And each time so then I went and I was at the Pentagon for three years before before the White House. And what I found is like there’s a whole bunch of people who will teach you stuff, right? Like you just got to be interested I from a young age was tearing apart radios to rewire speakers throughout my bedroom so that like I could listen to music louder. It was intended to be, and a lot of sort of things that look anything that combined sort of process art and science. And so at the Pentagon, you know, I found a person who worked in as a sis admin there and was wanting in was willing to teach me how to do like scripting, to do basic things on the computer. And I started investing in that and, and the more that I could do that I could learn other things. And so a slot came open at the White House. And it was, I had worked with enough different people and they had see me apply myself and like wanting to do more and more and I was hungry. I would be willing to work at it. That Midwestern work ethic definitely paid off along those lines. But I just continued to continuously every new opportunity run towards it. And when the spot came open at the White House, I was like, I would like To do that I want to do that was interviewed for it and got the role.
Scott McGrew
So you end up creating graphics for the Situation Room in the White House, which in the movies is incredibly dramatic. Are you making graphics of maps and bombers? And what’s what are you making graphics
Wade Chambers
of all of the above and but initially you’re going to not be so impressed. Right if you were going to create a, for example, a one pager of like something that’s going on. When I first got there, it was you would go grab an Atlas, you would look for a pastel colored map, because when you put it on the Xerox, it was not going to copy the color. So you’d basically get an outline. And then you would go into Jane’s, which was a military catalog and you go find a picture of the thing that that was in question or contributing, somehow, you’d make a copy of that you’d cut it out, you would paste it on the other thing, you would then take a post that you would type on a manual typewriter. What was going on, you would put it on there, you would draw with a ruler, an arrow or something along those lines. And then you take it back to this exact same Xerox copy and copier and now you have the thing that might go into the presidential daily briefing or be used in some other way. Well, that’s 1987. There’s this cool thing called a Macintosh that’s starting to happen, happen. And Mac two was out. And all of a sudden, you could start to have bitmap graphics. You could actually start to do word processing on the screen. You could actually scan things in and take the clip art and move them onto a page. The world vector shoreline other digital forms of mapping systems were starting to come on on, well, not online. That was much, much later. But we’re starting to be available inside of the God and National Security Council and that arena. So he started have access to things before now you could do things more and more digitally. My contribution inside of that was one two to be at the leading edge of like trying to make it more and more digital. But then also that that’s at the point in time where I was like, women were still doing a lot of this manually. What if we were just to write a program that does parts of this? And so then I started teaching myself hyper card. No one knows what hyper card is anymore except for You if you’ve been around a while, you probably remember what hyper card and turbo Pascal and all of those sort of things were. But we had a very talented set of programmers down in the White House situation support stuff. That actually helped me learn how to program be able to automate more and more of the these activities that I was doing. until the point where, you know, there was less being an administrative person and more like focusing on the graphics and building systems necessary to do that. So much so that the Deputy Director of the White House situation support staff left to start his own software company. And that’s when he reached out to me and said, like, Wade, you need to come be a programmer full time and get out of the Air Force. And at that point, time, I sort of looked up what a four star general was making, and I’m like, yeah, this is probably a better bet for me, but Scared the snot out of me. But I took the leap, it worked out.
Scott McGrew
Would the young man in Southeast Missouri believe the person you are today?
Wade Chambers
It would have been pretty hard to see that connection. I mean, all of my training at that point in time would have suggested the opposite. You know, I, I watched friends, you know, die. I had lots of people invest in like, the dumb stuff, selling drugs and doing those sorts of things. And it felt like a shrinking pie. Right. It felt like for you to get ahead, somebody else had to lose. And so like, that was my mindset, at that point in time. It’s very different here, right? It’s an expanding pie. There’s all sorts of growth. There are people who want to help you out? There’s people who want to see you succeed. There are people who are willing to invest their off hours to help you work through that. But that’s a very different place than where I started. So, I think I would have had a hard time seeing like the current version of me. I would have been excited. If I could have seen that.
Scott McGrew
Way chambers, CTO of grand rounds. Next week, Bhutto, potty investor in India. Is there a difference between an Indian American who is American and an Indian American who came from India and became an American? Are there different approaches to anything that I would not be aware of?
Unknown Speaker
You know, it’s it’s, I would say yes.
Scott McGrew
Sand Hill Road is written and produced by Me Scott McGrew produced and edited by Sean Myers and executive produced by Sarah bueno. And Stephanie a journey. For more interviews with Silicon Valley’s most influential entrepreneurs. Check me out on TV at press here. That’s Sunday mornings on NBC Bay Area, and everywhere on the world on iTunes. At it press here TV. com.
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