Bob O'Brien

Rachael Barclay (00:00) welcome to the next episode of Vantage Voices. I am Rachael Barclay, founder of Vantage, and I have with me today Bob O'Brien. Welcome, Bob. Rachael? Bob OBrien (00:10) Hey, how you doing, Rachael? Rachael Barclay (00:12) I'm doing well now that you're here. Bob OBrien (00:14) Excellent. Rachael Barclay (00:15) as you know, but maybe those who are not or watching do not know. the Vantage Voices episode is how we get to know you better. and it is one of the ways, there are several, that Vantage connects you and surfaces connections and introductions that you may not just think of normally. so we will put this in your member profile. It will go out on all streaming platforms and I'm ready if you're ready. Bob OBrien (00:38) Yeah, absolutely. Let's jump into it. See what we can get done. Yeah. Rachael Barclay (00:42) So in one sentence, Bob OBrien (00:44) What do you Rachael Barclay (00:44) who do you help and what changes for them when you do? Bob OBrien (00:47) I yeah, I I spent a long time in the tech industry and so I I help companies get ready for big changes, like pivoting to a new market, outgrowing how they've run things or even AI. So I help leaders just build what's coming before they have to react to it. Rachael Barclay (00:47) yeah, react to it. Hmm. Anticipatory. Founders have a hard time with sometimes with looking that far ahead, I I think. I can I will say that. I do. Bob OBrien (01:13) Well, yeah. And we and we know that, you know, after a while that you know, you just start to notice some patterns and that that's really why I started Third Wave, right? Was just to help leaders like you, like others, just see the change early and and get something in place before it happens. Yeah. Rachael Barclay (01:28) Yeah. So you you sit beside founders instead of in front of them. What does an advisor see that often the founder cannot? Bob OBrien (01:37) Yeah, you know, most advisors, and you know, there's a ton of us out there, but most advisors will tell founders they have blind spots, right? To look around things like hiring and cash and other areas to focus on. And and those are all true, right? what I tend to see comes down to four things. the plan. Most founders build a one year plan to survive, not a five year plan to win. Now you do that five years in a row and you've basically built you know, five one year plans that looks like a house that you walk through the bathroom to get to the kitchen from the living room. you know, every room needs to sort of make sense and and in that scenario the house just doesn't work. the second is really round team. You know, founders are really passionate, but they're strong, opinionated people that can crowd out everyone else's opinions. And so pretty soon your smartest people are just taking orders. The third is data. Rachael Barclay (02:31) just taking orders. data. of Bob OBrien (02:35) an area that I have a lot of passion around. Most founders just don't see their data as an asset. Most of them just don't really understand how to defend the valuation of it. They really undervalue it. So data becomes a big area for focus for a lot of founders, especially in the AI world. And then lastly, it's just the buyer. You know, I've sat on both sides of the table. founders think big companies want their product, big companies are asking how you fit in what they already have. And You know, at the end of the day, just trying to figure out making sure that founders understand what that buyer really wants and and delivering on it. Rachael Barclay (03:09) I love that. And so you just to go deeper into that, you've watched a lot of companies from the inside. Can you go a little bit into your of your career and I know this is sort of a loaded question, but I'm that's I'm a loaded person. Bob OBrien (03:24) Ha ha ha. Rachael Barclay (03:25) actually what it's made you be dramatic, but what do you think kills companies like you know, in Bob OBrien (03:32) Yeah. Rachael Barclay (03:32) of them? Is there is there a pattern throughout? And and then the third part of the loaded question is is it ever the thing that they think that it is? Well Bob OBrien (03:41) Yeah. Well, you know, I've I've been doing I've been doing this a long time. I've I've kind of done every generation Rachael Barclay (03:52) cloud. AWS, quick. changes. Bob OBrien (03:48) of computing you could think of from mainframes to client server to mobile to cloud. I've done it across big companies and small, you know, Microsoft, AWS. and you really start to see patterns start to emerge. And again, you know, we've talked about this. That's why I started Third Wave. it's really to help, you know, leaders see those those patterns and those changes. But to be clear, you know, it's almost never what a founder thinks. You know, founders expect it to be money or our competitor is the reason why, you know, reason why they you know, they they they fail or why they struggle. The there's really three things that I've come across, at least in my experience. One is falling in love with their product. You know, there's this old saying, you've heard me say it before, we've talked about it, you know, first-time founders focus on product. Rachael Barclay (04:30) product. Bob OBrien (04:36) Second time founders focus on distribution. The first time you're a founder, you pour everything you have into your product, making it beautiful and perfect. The second time you've learned the hard way that you know the beautiful product can only find a buyer if it can get delivered. And so really finding that distribution becomes important. So, you know, making sure that you're really pragmatic about your product and and not getting so in love with your product that you forget you still gotta distribute it. the second is really missing the product that you're actually building. You know, if if you picture, you know, think of a founder who builds this beautiful cooking app. You know, she thinks she's selling recipes and videos, but what the real people really want is everything featured in those videos. So the ingredients, the pans, the trip to the cooking store with the chef. She thinks she's running a cooking app. What she's really running is a store that has an app as the front end window. So those are two really different businesses and how you plan and staff and raise money are very different for each. Rachael Barclay (05:29) window. each. Mm. And Bob OBrien (05:36) And the third one is really holding on too long. Rachael Barclay (05:37) a Bob OBrien (05:38) you know, I've seen this in startups, I've seen it in big companies. they just you know, they they've they've had to hold on to something for a long time just because either they they're stuck in a strategy, they don't see it differently. You know, I've I've had to make the call on things like that in my own career. I've shut down failing products that used a consumer strategy to sell a business product. I've rebuilt a product from the foundation that could actually scale because foundation was on just wouldn't scale, but it meant shutting down an entire team and finding new work for them. You know, oftentimes in these situations, you know, brute force is feels like progress, but it really isn't. And a lot of founders are just busy, they're passionate, they're doing what worked until it doesn't. And then they find themselves without a plan. And it's really, you know, ironically, it's the classic emperor's new clothes problem. Everybody can see it, but nobody wants to say it. Rachael Barclay (06:10) for isn't. doesn't. wants to Bob OBrien (06:33) So I tell first-time founders, you bring the vision and I'll bring the blueprint. Rachael Barclay (06:37) the blue back. Mmm, I love that. So you so a little bit more into the work that it is that you do, which is far more than I'm going to list right here, Bob OBrien (06:47) Mm-hmm. Rachael Barclay (06:47) with what we're doing together, but you do the work that nobody puts on a slide, you know, the the maybe the unglamorous stuff, but the stuff you wish you you you find out later that you should have done. so things like the NDAs, the not compete law, the privacy rules, nobody reads until it's a problem. What is the boring thing that costs founders the most? Bob OBrien (07:06) You know, it's it's Rachael, it's always the details. You know, most founders just find details boring. You know, they're in love with their product, they put a lot of passion into it, and if they're not part of the product they love, they just feel like everything else is noise. You know, and everybody has a blind spot. Look, I have my own, but you know, if you think about it, engineers hate the sales process, salespeate the engineering details, numbers people hate the hype, designers love the spreadsheets, you know, or hate the spreadsheets. Rachael Barclay (07:21) noise. spreadsheets. Bob OBrien (07:36) So that's where the trouble starts. You know, in an NDA no one reads, a n a non compete no one checked, a contractor who never signed over the code, a privacy promise that limits your years, days, you know, limits your data years later. None of it feels urgent until an investor, which is usually the case, asks the hard question and you don't have a good answer. So that's part of why founders bring people like me in. I handle the part they don't find exciting and deal with all of them early. I used to have a mentor at Nordstrom, his name was Ted Jacob, and he used to say when it came to people kicking the can down the road on things like this, pay me now or pay me later, but you will pay. Rachael Barclay (08:17) will pay. That's a good quote. That's a good quote right there. So obviously I've known you for several years through Columbia Tower Club and and Six One and other all these other organizations. And luckily for me, we were able to talk about Vantage very early on. but how would somebody who maybe you know I'm not from the startup world, right? I'm from hospitality. And so not everybody's a founder who knows which things to go to and who how to find the right person. How what would you suggest a person who has an idea? Like at what stage should a should somebody like that try to find somebody like you? Well, Bob OBrien (08:55) Well, what I would say is they should they should find somebody like me just from a pure networking standpoint. And of course, you know, something like Vantage is really all about that, right? It's how we build these networks and how we get to know each other. what they're gonna find when they when they meet me is they're gonna probably find an honest outside read. I'm gonna tell what I see kindly, but I'm gonna tell what I see. and a lot of it just comes from having you know, sat on both sides of the table and startups and big companies, tech and business, buyer and seller. and so I really think that that if somebody were looking for somebody me, you're you're the kind of person who is looking to walk into a room with a big company, a partner, an investor, in and you're now looking for somebody who can give you an honest outside read. And I would say it wouldn't matter whether you're a first-time founder with you know, an initial startup or you're the CEO of an established company, a lot of times it's just really about perspective. And perspective can make all the difference in how you approach a particular problem. So I can usually help you see what's what's gonna go on in the room before you get there. A lot of it just comes from having been in this business a long time. and, you know, where that usually leads me is things like, for instance, you know, I'll get requests a lot of time for an investor introduction and I'll Rachael Barclay (10:03) get I'll Bob OBrien (10:17) you know, I'll be straight with you. I I only introduce people I've actually worked with. and even then I only do it if there's a fit because for and it's not me being picky. It's just it's what makes the intro worth something. Rachael Barclay (10:29) a fit. Right. Yeah. I mean you would just be introing all day long with the network you have. You have to have to Bob OBrien (10:34) Yeah. Rachael Barclay (10:37) safeguard that a little bit. okay, and so well now we're going to go into a little bit about more about vantage. So A big part of what is different about Vantage is that we lead with what can you bring to the community. and a lot of things, well I'll leave that part out. Clip that. I was gonna go to a negative thing. but we we leave with we lead with what can we bring first instead of what can we take because we find as many of us know but not all, if you lead with what you can give, you will always get more in return. So in your opinion, what can you give other vantage member just by being Bob? Yeah. Bob OBrien (11:17) Yeah. I I would just I'd say, you know, five five things I usually talk about, which is I already said an honest outside read from someone who speaks both tech and business, which is, believe it or not, not as common as you would think it would be. how a buyer or a partner or investor is gonna see you before you walk in. how you turn a One year survival plan into a five-year plan to win. obviously, my passion around data privacy and what your data is really worth. it's not just about protecting it. It's just like there's true value in the data. And a lot of times people just don't see it. And then lastly, you know, you said it, you know, my network, introductions to not only investors, but you know, lots of people in the industry from Rachael Barclay (11:55) see it. Yeah. Bob OBrien (12:04) every kind of walk of life, whether it's legal, it's marketing, it's sales, it's engineering. I just have the good fortune of having a a a long list of people I've had the privilege of working with and that can that can be really valuable to me. Rachael Barclay (12:18) And then now that we've gone through what you can give, what if I could walk anybody up to you the Bob OBrien (12:25) Mm-hmm. Rachael Barclay (12:25) city or otherwise, I mean we don't need to limit this to Seattle, Puget Bob OBrien (12:29) Yeah, yeah. Rachael Barclay (12:30) who is it? Meaning a stage, a role, a moment in their business, not just founders, like who's the perfect person? I want to challenge myself with who I find. Yeah. Bob OBrien (12:41) Yeah. Well, y you know, I kind of talked about it in the beginning. for for me, the the kind of person I would want to meet next is just any any leader who feels a big change coming. That change can be a pivot in their business, it can be a new market, it can be a new product, it can be dealing with, you know, this tidal wave of of things going on with AI that people are, you know, in many cases just really confused about. they don't don't need to be told it's coming, but they do need help getting ready for it. And that's kind of stuff that I like. I I love sort of that forward thinking, how do we plan for what the world looks like in five years? And then let's back into what we need to do today in order to make that reality. So a leader who can feel big change coming. It's like for me it's it's it's you know manna. the second is you know a CEO or a CO who's Rachael Barclay (13:25) reality. you Bob OBrien (13:38) you know few years who just realized that they've been running one year plants for five years and the way their house sorta works is okay, but boy, they're tired of walking through the bathroom to get to the kitchen and and they're ready to think about it differently. again, I I spent a long time in my career being sort of the redphone guy and being the guy who when they couldn't figure out how to do something said, Well give it to Bob, he'll figure it out And I I love those kinds of problems. Rachael Barclay (13:54) differently. of problems. Bob OBrien (14:06) Which kind of leads me to the third one, which is a current passion that I have is, you know, if if there was another person you'd introduce me to, it'd be a city council member Rachael Barclay (14:19) center. faster. years buildings. Bob OBrien (14:15) or a planner who was about ready to prove a big AI data center. You know, I you know, we we need computing capacity, but I've watched every generation of computing get smaller and faster. So what all does this look like in ten years? Right now, AI revenue runs far below the spending on these buildings. Rachael Barclay (14:39) ultimately? Bob OBrien (14:36) So that doesn't match up. Who's gonna pay for that ultimately? And a few jurisdictions in the country right now are asking those hard questions, but most jurisdictions, cities, counties, states, they don't have anything in place and they're not planning for it. And so we could find ourselves in the not too distant future with a lot of AI data centers that are empty because computing changed, and that looks a whole lot like a bunch of empty steel factories to me. And so that's a passion area that I have right now. Rachael Barclay (15:05) Ooh, I didn't know that. That's very interesting. That's got me thinking. Okay. and now I'll say we'll do the fun stuff, but that was all fun. Bob OBrien (15:14) Mm-hmm. Rachael Barclay (15:15) what is your go-to I usually say coffee, but what's your go-to adult beverage? Bob OBrien (15:22) Well yeah yeah. Well no. I I would say if if we were talking about coffee, my go to coffee is a is a pretty straightforward vanilla latte. If we're talking about a an alcoholic drink, it would be a really nice glass of Belveni scotch or a really, really Rachael Barclay (15:34) latte. Bob OBrien (15:50) Nice glass of sea smoke, sea smoke tin. Rachael Barclay (15:53) smoke tin. Mm. that's a good one. Yeah. what is currently what are you currently reading right now or I'm an audible gal myself because I like to be on the go and learn. what's your go to that you would recommend? Bob OBrien (16:06) a lot of stuff that I'm reading right now just is is obviously just focused around AI, the AI revolution, how how it all plays out. I worked with a lot of people at Microsoft over 20 years that were at the forefront of of what we now see as the AI revolution. I had the good fortune of meeting a lot of people who are at other companies like Google and Amazon who are in that. And so I really find the whole area fascinating, primarily just because of of the panacea, frankly, that I see around AI and people worried about, you know, what do we do next? And and that's the reason why I wrote a paper around the nine Rachael Barclay (16:42) okay, and then last but not least, what is the last thing that you were inspired by? Hmm. Bob OBrien (16:47) Hmm. Last thing I was inspired by. Rachael Barclay (16:50) It's hard one, I know. Bob OBrien (16:51) Yeah, I want to think about it for a minute. boy, that's a hard one. I you know Rachael Barclay (16:57) No. You could be inspired by yourself for your anniversary. Bob OBrien (16:59) gosh, that's a that's a hard one 'cause there's so many things that have been inspiring lately. Rachael Barclay (17:05) I feel like everything I actually picked that somebody would Bob OBrien (17:07) I I I could I I could I could honestly say vantage, but Rachael Barclay (17:14) seem too on the nose. Bob OBrien (17:16) Yeah, yeah, yeah, yeah. Yeah, no, I yeah, I but I will say vantage and and well let me say a couple things. One, I I one of the things that does inspire inspire me, although it sounds sort of you know pre-planned, it is vantage, primarily because it fits a really interesting model for me about how how Rachael has taken the concept of something And sort of turned it on its head and said, Well, we don't have to think about it the way we've always thought about it. You know, that John Maxwell is a business author, has this line where he says, If you do what you always did, you get what you always got. And if you talk to Rachael, you're gonna hear her say, like, all of these clubs are struggling, they're on the decline. So if you keep doing what you always did, which is just go after members. Rachael Barclay (18:08) numbers, Bob OBrien (18:09) you'll get what you always got, which is declining attendance. So at some point in time, you gotta think about it differently. And that's how I spent my whole career. Like I spent my whole career saying, hey, let's put mayonnaise in the can with tuna fish, right? Not not that you should do that, but the reality is we don't have to think about a business problem or a business opportunity the way that it's always been thought of. Sometimes we can just make a choice to do it differently. Rachael Barclay (18:37) the image is that Bob OBrien (18:37) And I and that's what I really like about Vantage is that you've made a choice to think about the problem in in a different way that has a a very different aspect that not only is beneficial to a member, but beneficial to a potential partner. And that's what draws me to it. is just that that innovative, sort of out-of-the-box thinking. In fact, there was a guy named Roy Gandarski who talked about the fact that when he built the the most Powerful electric airplane engine. His engineers said, Hey, well, you know, here's the constructs we have to stay within. And he said, No, that's a box. He goes, I want you to think he goes, I don't want there to be a box. And and where he pushed them to was there is no box. There is no framework you have to work within. Just purely innovate. And then once you come up with the most powerful engine, which they did, I think it was Rachael Barclay (19:16) box. box. within. in Bob OBrien (19:36) Three, four orders of magnitude more powerful, he said, now make it certifiable for the FAA. Now make it work, you know, at altitude. Now make it work over 300 miles. And and they still ended up with something that was way greater than what they could have had, which would maybe in one order of magnitude better. So what I really love about what you're doing is it's not about thinking outside the box, it's saying there is no box. Rachael Barclay (19:46) 200 box. Right. That's toughest Bob OBrien (20:06) So Rachael Barclay (20:07) sell about it. They're like, wait, why do you want to help? What's you? Bob OBrien (20:10) Yeah, yeah, yeah. Yeah. Yeah. What's in it for you? yeah, I I would say beyond that, the the things that really inspire me, I guess is part of why I I I wrote the paper about the non-immutable characteristics that humans have that I won't quickly replace. You know, things like you know leadership, judgment, decision making, right? I mean they can imitate it, but they can't actually do it. and I Rachael Barclay (20:36) do it. Bob OBrien (20:37) And I think people are really caught up in, my gosh, AI is now gonna replace me. in you know, like AI can't isn't going to replace you, isn't gonna replace you anytime soon, but it does mean that you have to do things differently than you did before. It means I have to do things differently than I did before. And that's where I think people get caught up. So the things that sort of interests me around AI is like people not losing their identity as as humans and what their value is. Rachael Barclay (20:56) Right. is world. Bob OBrien (21:07) in the world. And the second is, hey, there's some very real issues that are emerging out of AI, such as data centers, which is this huge panacea about building these data centers and the rush to build them. But nobody's really thinking about in five years or ten years from now, when computing changes. And it will, it's going to get smaller, it's going to get faster, it's going to need Less water, maybe no water, it's gonna need less physical footprint, maybe maybe as small as your phone. So when that happens and you have all of these empty buildings, now what do you do? And and we're talking about the retrofit of buildings that's in in the you know, near approaching trillions of dollars of retrofits and the AI revenue stream won't support that. So somebody's gonna pay for that. And it's not gonna be all of the AI companies, it's gonna be people like you and me. Rachael Barclay (22:00) you'll need. Yeah. of Bob OBrien (22:01) And I think I think jurisdictions really need to think hard about when that day comes, how do we how do we rehabilitate all of these buildings into something that's useful for society and not just have not just have a bunch of empty buildings. Rachael Barclay (22:18) buildings? I could have like a three hour conversation about this. Because absolutely. Bob OBrien (22:22) Well, you can see why that's my inspiration, so anyway. Yeah. Rachael Barclay (22:27) Okay, well, that brings us to the end of this episode or your episode of Vantage Voices. if you want to connect with Bob and you are a Vantage member, you can do so in the app. we have both for Android and iPhone. you can also do on the web. you'll also find ways to connect in the show notes. if you're finding this on all Spotify, Apple Podcasts, YouTube, or my email will be there and I can connect you with Bob myself. So thank you Bob for being here. And thank you for being a believer in Vantage and in me. usually Bob OBrien (22:57) a hundred percent. And the other place you can find me is usually standing right next to Rachael. Rachael Barclay (23:02) standing right next to Rachael. That's true. Yeah.