Haley Daiber on Missing the Big Picture When Implementing DevOps

Tuesday, 9 July 2019

Unusual Ventures’ Haley Daiber joins hosts Michael Neale and Karen Taggart to discuss DevOps implementations, technology architecture and venture capitalists.

women with laptops

Mic Neale: Hello, everyone. Another episode of DevOps Radio. I am Michael Neale from CloudBees. I’ve got my co-host, Karen, who is also from CloudBees, and a very special guest, Haley. I’m gonna let Karen introduce her ‘cause she’s done all the cyberstalking and found out tons of information about her. Thanks for coming over Haley and over to you, Karen.

Karen Taggart: Well, thanks, Michael. Hi, Haley. Thanks for joining us.

Haley Daiber: Thank you so much for having me. I’m so excited.

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Karen: Yay. So if you don’t mind I’m gonna do my little semi formal introduction from, I prefer to call it research, thank you, Michael, about you and such. So then it’s just like a said a more casual conversation. I have some questions, but also don’t hesitate to ask us some questions too if you have any for us. So looking at this research, so currently you are with Unusual Ventures, a senior associate at Unusual Ventures. You kind of stumbled into Venture in a way after spending years working at Ernst and Young in accounting and then created this app with your mom, which I can’t wait to talk about. Then of course like everybody does, as one does, so some accounting apps with mom to Harvard, Harvard Business School. The highlights I came across there from Harvard, I’m sure you have other ones, but the two that I wanted to make was that you were selected for Harvard’s Innovation Lab incubation program and the inaugural cohort of the HBS start-up boot camp, and probably most importantly _____ of the Whiskey Bourbon Spirit Society. Which is probably I’m guessing what led you.

Haley: Yeah. Definitely my most important accomplishment for sure.

Mic: I didn’t know you could do that sort of thing at uni. I just went there to study and no one told me you could do that. So that’s awesome.

Haley: Well, it was funny because they had all these other societies and me and a friend of mine, we love whiskey and bourbons. So we were like, “Hey, they’re doing all of these selective small groups of just tastings on the side. We wanna make it more inclusive and actually have it be a real club so we can do full events.” HBS told us that whiskey and bourbon was not a wide enough group. So it was originally a Whiskey, Bourbon, Scotch Society, but they made us broaden it up to be the spirit society as well to be inclusive of all.

Karen: Now did you allow clear spirits or was it just brown spirits? Let’s be honest here.

Haley: Clear spirits were allowed. We did some _____ tasting at some point. Yeah.

Karen: Cool. Opening it up. You’re thinking outside the box, outside the bottle. That’s good. So obviously of course that would lead you to become senior associate at Unusual Ventures. So first of all, I’d like to ask you about, let’s start with the app. So I was reading about the app, Forget Me Not, that you started with your mom and one of the descriptions that you had of it and one of the postings was, “Just like Andy from Devil Wears Prada following you around whispering in your ear.”

Haley: Yeah.

Karen: Talk to me about that. What’s meant by that? What does this app do? What’s it still doing?

Haley: So the original concept was I was going to all of these networking events for Ernst and Young. So they do all these recruiting of current students to get the new crop of wonderful accountants and every networking event I would go to it would be like them asking for my card, which I would never have on me, and then me seeing the same people at the next event and having that moment of, “Oh, crap. I know I met that person at this last event three weeks ago and I should remember their name and be able to go up and say hi,” and inevitably I would always forget. So we were initially thinking and we’re like, “Can’t believe we live in this day and age are still using paper business cards. That seems ridiculous.” The LinkedIn these days is servicing so many different stakeholders with recruiters and companies and not necessarily just the individual networker anymore. So we did a bunch of research and my mom has always been a huge inspiration to me and she’s always been an idea person. So I started talking to her about this idea. We really realized that the real problem is not that you don’t have your card on you, but that there’s no intuitive way of organizing all of your personal connections and then having them be usable for you in the moment that you need them. So, Forget Me Not was designed to essentially be a better version of LinkedIn to say when you meet someone you add each other on the app and then the kicker was when you met, or when you were recently nearby somebody that you had originally met, you would get a push notification from the app to say, “Hey, Michael is nearby. You should go up and say hi.” It would have their picture, their name, and anything else that you wanted to remember about this person and all of your connections would be organized by when you met them, where you met them. That automatically tagged and then you could also organize by all of the ways that you actually intuitively remember people. So I kept having that moment of, “I’m trying to remember that person I met three weeks ago.” Searching on LinkedIn via that method is almost impossible. So that’s the original genesis of it.

Karen: And LinkedIn doesn’t have that geo feature, right? So warning me that…

Haley: Yeah. It does now, which is funny. Nobody uses it. It has a feature now where you can say, “Find connections nearby,” but it’s so creepy and it’s not the purpose of LinkedIn anymore that it just gets lost in all the noise. So that was the feedback we often got was, “Oh, this is just a feature for LinkedIn.” I took that feedback, but at the same time you could say that for any company that’s just getting started. You’re ultimately solving a different problem and servicing a different core customer.

Karen: So when you say you started to get that feedback, who was telling you that? Was that when you were presenting to funders or stop and do a little bit about the path. How do you go from basically, “My mom has this idea, I have this idea,” to “Here’s an app.” That’s a big reach. I wouldn’t even know where to begin.

Haley: Totally. We had no idea where to begin. So it started as just a side project to our full time jobs. My mom has a technical background. She taught herself coding at… she got a degree in math and then when she was just starting out taught herself computer programming. So that was something that had always been an inspiration to me. So when we had this idea she was like, “All right. I’m technical. We can go out and make this happen. So let’s just do it. How hard can it be to build an app?” To get started we essentially said, “Okay. She can lead up the development process ‘cause she understands the technical aspects of it.” But in order to actually develop it she didn’t know Swift or Objective-C and so we basically looked around and connected with people that she knew and said, “Who do we know that has gotten an app off the ground and what did they do?” So we basically connected with this dev shop out of India that said, “We can create an app for you for $3,000.00,” and that’s how we got started. It was functional, but took a lot of iterations off of that and at that point I was so naive as to the world of start-ups and how you even get started. Raising money was a complete black box to me. So at the end of the day we, that’s where I went back and got some advice from a mentor of mine that was like, “If you’re interested in tech and start-ups you should really think about going back to school and some of the exposure and learnings that you can get around entrepreneurship from an MBA program could really be helpful.” So that was the process and I went into it thinking, “Yeah. All we need is money and then when we get the app it’ll just be a huge success.” Now knowing all that I do about the process, it was so enlightening to go to a program where they taught things like lead start-up. I realized like no, the biggest problem for this app being successful is not can I get a functional version out in the app store. It’s can I break the chicken and egg problem of being able to provide value to people and create a network when the whole value of the app would be the network itself. How do you provide value to anyone before you have a network built?

Karen: Isn’t it interesting how it always seems to be not about the technology?

Haley: Yeah. Exactly.

Karen: I’m struck by that. Just today I was struck again and again by how much of what we do in technology and making it successful and making it valuable and making it useful has to do with, first of all, people, but also relationships with people. Right away the first you thing you got to say was, “Who do you know? Who do you know and what do they know how to do?” Going back a little bit to Harvard, first of all, serious jealous and impressed. I’m a sucker for people who go to fancy schools especially a Harvard Business School because that’s not just fancy in name, that’s fancy in content. So congratulations. In other words, I’m impressed and jealous.

Haley: Thank you.

Karen: So you mentioned some of the things out the gate that you learned there in that program that were helpful for your own start-up. I imagine you probably learned quite a bit that’s helpful in your current position. You mentioned _____ start-up. You were talking about a couple of things about adding value. Are there any other lessons in terms of both technology and management and people, whatever, that came out of that program for you that have helped you with your own start-up, but also probably even more important, are helping you now in your position in working at Unusual?

Haley: Yeah. First of all, I’m from Austin. So I am like the opposite of a fancy person. To me Harvard Business School was I think the same as how you think about it, this crazy, unattainable, fancy institution. Ultimately it was a really influential mentor of mine that had been a professor of mine at the University of Texas. He taught actually his class at UT all kind of Harvard Business School case method style and all based on Clay Christensen’s theories on destruction and he ultimately got poached from the University of Texas to go teach at Harvard Business School. So he’s the only reason really that I even applied there and thought that that was something that I could do. So I thank him every day for that.

Karen: Are you gonna name drop here? Are you gonna credit him?

Haley: Yeah. Sure. His name is Rory McDonald. So if you have the pleasure of meeting him, definitely make that connection. He’s somebody that just truly cares about helping students and that is the one thing that lights up his day and that kind of genuine, really genuine desire to help people is so awesome. He’s actually the one that introduced me to John Vrionis too, the founder of Unusual. So fundamentally changed my life. So at HBS, I think one of the things that I just found so incredible was just the amount of events and opportunity you had to meet interesting people and learn about interesting topics. So every day on campus they have so many different events that all the different clubs put on, all the different organizations put on that bring in incredibly talented speakers and some of the smartest people in the world. So I spent most of my time while I was at HBS just going to all of these events and figuring out what was interesting to me and what I wanted to dive deeper on. So that just kind of ability to continue to learn and grow is something that was so cool and ultimately the class that Roy teaches at HBS is one of my favorites too. It’s called Building and Sustaining Successful Enterprises and it’s all based on Clay Christensen’s theories and that’s something that I constantly go back to and in my job today is thinking through, “How can we enable start-ups to not only think about what it takes to get to the next stage of financing, but what does it take to build an enterprise that continues to innovate and continues to be successful over the long term?” That’s something that is so hard to do and fundamentally comes back to people and culture and organizational change as you mentioned, Karen.

Karen: Yeah. If you wanna share ever with me what it takes to build a successful enterprise.

Haley: Right.

Karen: In the next five minute, no it’s probably a whole other topic for a whole other …but one of the things that interested me too when I was reading about you was one of the things, I believe maybe it was on your Twitter profile I think, where you said you described yourself as a wannabe engineer. I describe myself as a wannabe engineer as well because I had sort of an accidental technology experience and I’ve resisted computers my whole life. Literally my entire life. I went to a science-technology in high school and I fought like hell to take as few computer classes as possible. Then it was like I knew I wanted to go to law school because I wanted to make social change and that didn’t work. Then I wanted to work in nonprofits and I ended up building databases for those nonprofits. I taught eighth grade and I ended up building a website for the student. It was like, “What’s happening here?” Now I just succumbed to it and said I’m not an engineer and I’m kicking myself actually for not becoming one because that would have been probably a much better move. But that’s why I describe myself as a wannabe engineer, but I’m just wondering why do you describe yourself as a wannabe and why don’t you just describe yourself as an engineer?

Haley: Well, I guess because I’m not, not from a technical standpoint. I mentioned my mom earlier, she has been a big inspiration to me. She is an engineer. I have always been interested in technology. I don’t know, ultimately when you’re 18 and have to figure out what you wanna major in I think that is a ridiculous thing to put on an 18-year-old.

Karen: Oh, I so agree. I’m 45 and I have no idea, so hey.

Haley: Right. Same. So I don’t know why, I can’t tell you why I didn’t end up going into that as an actual major in school, but I was always interested in tech and start-ups and one of the reasons I chose Ernst and Young actually when I came out of accounting was in Austin especially, but really I think their brand overall is they audit a lot of the tax companies and are very start-up focused. They have their Ernst and Young Entrepreneur of the Year program. When I was an intern at EY one of my first clients was in the venture industry. So that was my first exposure to even what venture capital was and ultimately when I … my clients at EY were a lot within the semiconductor industry. So I was continually drawn to all of these technical fields and that’s something that every day I think through the pros and cons of not having that traditional technical background and not being a traditional engineer. So I think through, okay. When I’m learning about a lot of these newer technologies and the shift that’s happening in the software development process, on the one hand I think it can be beneficial because I have a much bigger picture view and I’m not in the weeds of how everything is happening. So I think there is value there. But when I’m sitting down and trying to learn what is the difference between…and Spark, and what about Data Faxes is one of our portfolio companies. Thinking through what is it about Cassandra that makes things seem so successful? How is Spinnaker a part of the process? I think it’s something that a lot of people in the industry talk about just in terms of terminology can be something that can end up excluding people, but it’s something where it does take me a little bit longer to get up to speed on all of these things, but I think that’s something that I love doing and love digging into technical details even without a technical background. So that’s the long-winded answer of why I wanna be an engineer is because I think it would be helpful to have more of a technical background at times.

Karen: Have you found though that sometimes because you don’t have that explicit technical background or that explicit engineering background that you’re able to see patterns or ideas in things that other people around you don’t?

Haley: Yeah. Even thinking through all of what’s happening within DevOps and what’s been happening over the past 10 years, I think it’s something that a lot of people with technical backgrounds and I know you guys have talked about this a lot on the podcast, especially with Chris recently, but it can be easy to think of everything as, “Oh, well, there’s this shift in technology. So this is how this is changing. This is part of the process.” And ultimately so much of DevOps and about all of these transformations, it really comes down to the people and organizations and changing the culture. So that’s what’s so fascinating to me is you can, these technological shifts can really create cultural change. I think it’s easy to get into, if you do have a technical background to get into the weeds of DevOps means this and this is why I need a DevOps engineer or this is why I need X framework to achieve this without really understanding what’s the big picture of what this shift means and what we’re trying to achieve.

Karen: Yeah. I work primarily on the cultural stuff and the change management stuff, the people and processes end of it. The technology comes around and it just makes these major cultural shifts and/or, talk about chicken and the egg, cultural shifts are making this major need for technology to happen.

Haley: True. Yeah. True. It’s even something when you think about microservices and Kubernetes. Everybody’s so excited about Kubernetes right now. You have people from huge organizations that are instituting these top-down mandates to say, “We’re implementing Kubernetes,” and it’s just so fascinating because at the end of the day the shift towards microservices is about organizational change to be able to deliver software faster. So it’s how can you create these smaller teams of people that can get things done. That’s just fundamentally not how I think a lot of these big organizations are ever going to operate. Maybe that’s pessimistic, but it will take a lot of time and a lot of that kind of bottoms-up approach in order to have that work on the one hand. Then, on the other hand, I think there’s simultaneously this shift towards wanting to abstract away all of these complexities and maybe that’s the approach that ends up working for a lot of the more established organizations that are trying to implement some of these practices without considering the cultural implications.

Karen: And I’m constantly reminded every day at my job of impacts that I never would have thought of. I just had one happen. It was a large organization that we’re trying to do CI/CD implementation and part of it is installing CloudBees. That’s part of what we’re doing. It’s a small part. You wouldn’t think that’s a big deal. You have to get to service the machines, the…. Fine, we have to get that and install the software. With this organization though, there’s not only a separate operations team that does configurations, there’s the ones that write the configurations, the ones that pass it on to the people who share the hardware and then on top of the people who implement. Then on top of that separate division within that department of people responsible for installing software, split that into two, installing custom versus purchase, break that down even further into installing … window … or whatever off the shelf, Window software versus Linux. In this case we have both. So we have to figure out who in the how. What does that mean for DevOps? How do I deal with that? I’m gonna discuss, since we’re diving into DevOps, switch over to that. I know you’re working with multiple companies and you are probably hearing about companies all the time. How are they grappling with some of this new speed of software delivery?

Haley: Yeah. Since we’re still a new firm most of our companies are maybe five people at this point. So it’s a little bit different. Actually, one of the companies we recently invested in is a really cool company. It’s called YourBase. They’re actually helping with the speed itself. So they’re helping with the build and test process through incremental code bills. So I’m actually spending I’d say probably more of my time with people that are focused on how to do that faster and solving some of those problems and then people that are struggling to figure out how to implement some of the policies.

Karen: It’d be fun to start with greenfield.

Haley: Yeah. The benefit of being a c-stage firm is you’re definitely starting green field. I have a question for you though. When you were talking through that process one of the things that I’ve been thinking about recently, and Michael, I know we’ve talked about before, is companies that have done one specific piece of the process so well. So like PagerDuty or I’m a big fan of LaunchDarkly and everything that they’re doing. I’m always thinking about how you think about the approach of saying, “When does it make sense to just do one thing and what types of customers are receptive to saying, okay, … I can clearly understand that’s what I need. This is a specific problem I have.” Similar with PagerDuty. They’re a big public company now and that was just waking people up in the middle of the night if they, that was a specific thing that they solved but solved really well. Both organizations I think I’m sure can paint the broader picture over time of how they start to do more things and offer more products. When you’re talking to some of these big organizations like you’re describing, do they look at those more point solutions or are they mostly looking for a comprehensive solution to being able to deliver software faster?

Karen: Michael, do you wanna jump in?

Mic: Yeah. I was just thinking about that. I think it’s a bit of both. It seems like large companies, Karen might see this a bit more, they all know between wanting more vendors in the mix and then fewer vendors. Almost time is sort of and if they’re in the stage of we want fewer vendors then they’ll naturally go for vendors that cover a spectrum of things ‘cause the lines between these things aren’t always clear. I think pedagogy is great because that’s a very discrete problem and they solved it the way I guess no one else had and that was valuable to people. So in so many other areas, it’s not that clearly defined. Then there’s the whole stuff almost like politics of how companies are arranged today, the different departments and like Karen was talking about, divisions and subdivisions and the budgets they have. That isn’t always necessarily optimal if you are starting completely greenfield with a brand new company in a brand new domain, but it kind of is what it is. So I think that drives a lot on whether you consider things … feature, but yeah. It is kind of cool to see these specialists sort of companies validate a very specific area and show how well it can be done. Like maybe Slack could be another example. We all use it heavily and chat’s been around forever. It’s a feature of the Microsoft program if you’re on it or Google, if you’re on that like we are. Still, a company that went out there said, “Well, let’s just refine this thing.” It’s obviously still valuable. It’s just not clear ‘cause the lines aren’t clear and practices change and companies change. Yeah. Don’t know.

Karen: Yeah. I think that my experience with it so far is that it just always has where the motivation comes from for the change. So I’ve seen a couple of different patterns so far. I’ve seen the one where a larger company might have one app dev team that’s renegade. And they’re the ones that decide, “You know what? No. We just don’t have time.” And they started gorilla opposite and next thing you know because they’re so successful it then grows into something else. So they’re that model versus the organizations that I’m seeing more and more of now because it is so much more mainstream where there’s this center of excellence or shared services team that does have a mandate. It has a mandate from the CIO or whatever and here it comes, go do DevOps, and those teams, in particular, tend to be looking for fewer tools because it’s a cash-strapped team, it’s a research-strapped team from a human perspective. It’s typically so far I’ve found most of the people with operations backgrounds and not necessarily development backgrounds, it’s people who are used to, I hate this phrase, but like buying and babysitting software. It’s like this is now the e-mail server. It’s like that and that’s just not what we’re talking about here. So I don’t know if that answers your question really. But then the teams that are more of the smaller apps teams, they are flying in and bringing in this little bit there, that little bit here, this little bit there and then teams that are, like companies find out and then they try to bring three of these app teams together and they all have their favorite tools. Then what I’m having fun with dealing now, of course, is when there’s a buyout and two different companies with two mature DevOps programs in two different directions. One buys the other or there’s a merger and how does that look. Get back to me in a year on that and how that’s shaking out ‘cause that’s fascinating. So it goes all back to relationships.

Haley: Yeah. Relationships between departments and organizations is something that I’ve been thinking a lot about how the shift is going to play out with ML models and thinking through all the tooling that’s happening with data scientists and machine learning engineers and the collaboration between all of those parties with the traditional software development and how that gets intertwined. One area we spent a lot of time on looking at was testing and how that becomes a bottleneck in some situations and what is the role of QA anymore and how do they work together and fit into the whole process. Then there’s the whole DevSecOps movement. It totally all comes back to organizational structure and people.

Karen: Yeah. And battles of the words and battles over where to do what and what Michael was talking about. It’s like it’s not always even clear what’s what. It’s like well, one team might say that that’s … team and say, “Well, that’s operations,” and another person say, “Well, no. That’s part of development,” and who’s fighting over what.

Haley: I love the conversation you guys had with Charity and just thinking through monitoring versus of observability. All of these words mean so many different things to different people.

Karen: Speaking of that too while we’re talking about the tooling and stuff and since you are talking with different companies and seeing different needs, what kind of gaps are seeing right now in DevOps in general in the tooling, in the communities at the practice?

Haley: Yeah. So I don’t know how this will play out, but I think one thing that I’ve been really interested in is actually the everything happening with testing and production and what that really means. I think companies like Gremlin are so cool in that they provide ways for people to start easily practicing some of these concepts and it’s almost the tooling that it can provide is it’s less about the technology and it’s more about driving that change.

Karen: Just for our listeners who don’t know Gremlin. You wanna just explain Gremlin?

Haley: Oh, yeah. So they’re a company all around this concept of chaos engineering, which started out at Netflix a while ago from this chaos monkey theory where essentially what you’re trying to do is figure out how to inject all of these thoughts into the system to where you’re seeing what potential issues will arise prior to them actually coming up. So it’s more of a prevention technique and you can run these game days to try and find the faults in your system before they happen. And it’s something that the concept is super interesting to me and I wonder and I was talking to Paul, I think Offman is his last name, who’s practicing at Under Armor and one of Gremlin’s early customers and I was asking him at what point does your organization have to,  at what point are they mature enough from a team standpoint in terms of practicing all of these different practices to even start to think about implementing something like chaos engineering? You have to have gone through the shift of, you’re definitely in the cloud. You’re definitely starting to process … and DevOp techniques. You’re definitely probably using containers and Kubernetes and all of these things and then maybe you can start to think about chaos engineering and some of these other more new and exciting trends that are happening. I think there’s definitely room for companies like that though to say, “We can help provide you with these tools to help you do it in a non-scary way to just easily get started trying some of these things out.” So that’s something that’s been interesting to me. Going back to testing, that’s something that we spent a lot of time on just in general and all of the different ways that that can come into practice. I’m interested to see how that evolves over time. I was talking to somebody this morning that has been, she has been a QA engineer for most of her career, seven-plus years. And thinking through, she’s actually a huge CloudBees fan. She started working with Jenkins and has a mandate to create a CI/CD pipeline for one of the companies she worked out. She’s obsessed with CloudBees. Thinking through, “How does that role change over time?” She talked about all the different titles that she’s had and how that’s changing. She was like, “Well, when I went to my most recent company as something that, the title became something where it was maybe I don’t need QA in my title. Maybe I’m just a software engineer or whatever it may be,” and thinking through the evolution of that function and how quality fits into the process and not just speed because at the end of the day all of the issues and everything that’s happening around group cause analysis and doing post mortems and the culture of not having blame, all of these things it’s like if you start, this is something that Christine from Honeycomb actually talked about at the testing and production meet-up. If you start to think about the testing process all the way through the software development process, starting even with design, then that’s something that really influences how everything plays out.

Karen: Speaking of scary, you talked about it can be scary to do some of this stuff, I’m gonna switch to my scary topic. I’m scared of venture capital. I’m gonna raise my hand and I’m gonna say it ‘cause I kind of, it’s because I’m ignorant of it. So I get this sort of icky feeling about it and I imagine Silicon Valley, the TV show, and Wall Street, the movie all wrapped into one. I think about it where I’m like, I know Michael you’ve worked in this space much more than I have. So maybe you’re not as scared as I am ‘cause you understand it, but for my benefit can you just help me understand a little bit like what at the very base level here, what venture capital is and how it all works.

Haley: Totally. It’s sad that it is that scary of a subject and a topic and that’s something that hopefully changes over time because for me I was the same way. The whole industry is really just a black box and it’s something that most people and most firms aren’t super open about how the process even works. How do I pitch you and what happens after that? So just base level, so the way that venture capital works is typically you raise money from your limited partners. So a lot of times those are pension funds, family endowments. It’s something that has been in the spotlight a lot lately is where the actual money comes from in venture capital. So that actually was one of the reasons that I was so excited to join Unusual is our LP’s are mostly nonprofits, children’s hospitals, HBCUs, organizations where ultimately we are super excited for our returns flowing back to those organizations and then the impact that they then make on their community. In general, that’s something that a lot of people don’t even understand about venture capital is it’s not just the venture capitalists that are a bunch of rich people that make investments. We have to fundraise too and get money from these large organizations that have a big profile. They’re putting money in venture capital and private equity and hedge funds and all these different asset classes. And so then the venture capitalist job is to say, “We can make the highest reference possible for you on that capital.” So our job is to then go out and find these start-ups that we think have the chance to become billion-dollar-plus companies and help them along the way. Venture capital as an industry has changed a lot over the past 10 years even. So when John actually started series A was, I think the average was probably $5 million and companies were kind of still finding product market fits. Some maybe had revenue on the enterprise side but very early traction. Now you see $20 million series As and companies and investors are looking for a lot more in terms of traction before they are willing to invest. So that’s something that the industry in general and something to know about venture capital, back to your original question, is there are so many different types of investors and so many different strategies that each firm has in terms of where their focus area is and what types of companies are looking for and what types of metrics and traction they wanna see before they invest. So for us, we decided to focus on very early-stage companies. So on the enterprise side typically pre-product in a lot of cases, pre-traction, and the goal is to help them get to those metrics and milestones that then they can go out and raise a large round from a really big firm.

Karen: So just for my benefit again with terms, LP versus GP? Can you help me out?

Haley: Yeah. So LP, that’s the limited partners. So all of the endowments, pension funds, universities, all of the people that basically are giving the venture capitalists money. GP is the venture capital firm itself and the people that make up that firm.

Karen: Gotcha. All right. So is it all just about the money or what else motivates people in the venture world and what else do you guys provide? Sorry. What else do you all provide? I’m trying to get that phrase out of my vocabulary.

Haley: Just say y’all. I’m from Texas.

Karen: Good. Y’all. I say y’all. I’m just trying to get rid of “you guys” from my vocabulary.

Karen: What else motivates people in the venture world and also what else do y’all provide companies besides cash?

Haley: Yeah. So it’s definitely different for every firm. So John and Jyoti, when they started Unusual it definitely wasn’t about the money for them. They had both done very well for themselves. John thought about doing I think a bunch of different things and ultimately his love is for this early stage where you’re spending time with founders. It’s so cool to just to be working with a company that is two people and see the process come together of how are you thinking about the version one of the product and what’s in it and how you’re scoping it and who your initial customers are gonna be and what does that go to market strategy look like. Every investor now it’s definitely a founder’s market. So every investor is trying to figure out ways where you can provide value that’s not just money and at Unusual we decided to do that through one, being very stage focused. So saying, “Look, there’s a lot of people that can provide a lot of different resources for you. Once you’ve hit all of these traction metrics and product milestones and you’re a big enough company.” The hardest stage of a company’s lifecycle is right at the beginning. So starting from day one figuring out how are you gonna get your first five customers and how are you gonna convince your first couple founding engineers that come on to your team. So we have built out, which this is really Jyoti’s brainchild, but built out something that we call the Get Ahead platform. It’s our in-house, we have an in-house director of recruiting, an in-house director of marketing, and in-house director of sales whose full-time jobs are helping our founders hire employees and figure out how they’re gonna get their first few customers. So everything from creating job descriptions to finding a pipeline of candidates, interview process, and then on the sales and go to market side it’s Scott Schwarzhoff, who’s our operating partner, he was most recently the VP of marketing at Okta and his full-time job is sitting down with often these technical founders that sell the marketing as a scary thing to them. So thinking through, “What do you put on your website? What does your first sales deck look like? How do you tell the story in a way that really resonates with these companies?” And Liam, who most recently joined us, he’s incredible. He was I think the top salesperson at MongoDB and led a team there. His full-time job now is essentially working with our founders and our early-stage companies to set up their sales process and think through how they’re doing outreach and how to increase conversion offend their pipeline and actually going out and getting customer meetings for them. So we’re trying to be and this is where the name Unusual came from. It wasn’t the original name, but it’s something that we kept telling founders and people in general, this is what we’re trying to do. We kept getting the feedback of, “Oh, wow. That’s really unusual.” So we decided to stick with it and it’s a great name to put on a nametag because everybody asks, “Why are you unusual?”

Karen: Why are you unusual? “Ask me why I’m unusual,” that’s what you should have like the ask me …

Haley: Right.

Karen: So if someone’s listening to this video, this podcast here and they wanna get into VC, they think, “This sounds fascinating,” how would you recommend they start?

Haley: Yeah. I think if you ask I think any venture capitalist this question everyone is probably gonna give you a different answer and it’s always gonna be how they got into VC. So I think the biggest takeaway is there is really no one path and I think at the end of the day venture capital firms are so frustrating on some level in the fact that they’re never hiring and they’re always hiring. So the way I approached it and this is, everyone can figure out the strategy that makes the most sense for them and their skill set and personality type and strength, but for me it was I’m just genuinely interested in technology and start-ups and I’m just gonna follow where those genuine interests are and keep making connections. Go to all the things and just establish those genuine relationships and at the end of the day I think a lot of it comes down to luck or fate or serendipity, or whatever you wanna call it, but you have to put yourself in a position where you’re starting to make your own luck. I think the first step is, happy to talk to anybody. The first step really is just reaching out and starting to make those connections.

Karen: So if someone did wanna, you just give me a segue, by the way, because I’m gonna go in some of the ending questions here and one of the ones we always like to ask is, if someone does wanna reach out to you, how can they find you? What’s the best way to reach out?

Haley: Yeah. LinkedIn message is always good. I’m always on LinkedIn or feel free to e-mail me. I’m open at this point. My e-mail is super easy. It’s just my first name, haley@unusual.vp. So happy to chat with anybody.

Karen: Awesome. Great. Do you have any recommendations for things that people should be reading or websites they should be following, conferences they should be going to?

Haley: So I am going to the CO Riley’s conference next week. So if anyone is going to that, happy to meet up with people there. I think that’s always a good one. I just signed up for the chaos engineering conference and I’ve heard actually and I didn’t get the go, but I heard … that these past couple days in … was awesome.

Karen: Oh, yeah. I’m following that on Twitter.

Haley: Then in terms of what’s best to read or listen to, I’m a big podcast person. So I’m always trying to mix it up between things that are technical, so like the Software Engineering Daily or some of the others or New Stack is good too or from just a general tech and start-up standpoint, I love How I Built This

Karen: Oh, I love How I Built This.

Haley: My favorite podcast.

Karen: Yeah. It’s so good.

Haley: It’s so cool to hear the diverse stories of not just the standard venture back to let me see this huge company, but how you can create incredible movements in companies through lots of different ways and means. I love that show.

Karen: And of course possibly one other conference ‘cause you’re Bay area, right?

Haley: Yes. Yeah. I live in San Francisco and we’re based in Menlo Park.

Karen: Excellent. So, of course, we have DevOps World | Jenkins World coming up in August.

Haley: Yeah. Of course.

Karen: Hopefully I’ll get to see you there. I’ll be heading out there. I’m east coast. That’s one of the fun things too about DevOps Radio right here. We’ve got west coast, east coast and then Michael is in Australia. So we like to go all the way around the globe.

Haley: Very cool.

Karen: I always like to have Michael here because I always say he’s the gentleman of the future. He always can help us see into tomorrow.

Mic: It’s Friday here.

Haley: For sure.

Karen: It’s Friday there.

Haley: Awesome. Happy Friday.

Karen: So Michael, did you have any last questions? I completely dominated this one?

Mic: No, no. This has been fascinating. So thanks so much for coming on, Haley. Yeah. I’m sure future topics could come up. There was a bunch of other notes we had we didn’t get to, but I think we’ve got plenty. This is good stuff and I’m sure people will find it interesting. This is like an insight into an industry that is a bit of a black box. It is a bit opaque, but it’s important to this whole area. So thanks very much for coming on.

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Michael Neale

Michael is a developer and manager with an interest in continuous delivery and artificial intelligence. He is a cofounder of CloudBees and has worn many hats over the years. He lives in Australia and often can be found on a plane when he isn’t on a video call.

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