One of the key issues that employers and job seekers face today is the overcompetitiveness of the job market. Many industries are affected by the pandemic, and companies are finding ways to efficiently spend budget by hiring the right person fit for the job. At the same time, the sheer number of displaced workforce contributed more to the already cutthroat employment marketplace. Our guest in this episode, Brett Waikart, leads a company that aims to reshape how corporate recruiters hire valuable team members, making the hiring process more effective, efficient, and equitable.
Brett is MBA 2020 and Co-Founder and CEO of Skilful.ly, an employment platform that focuses on demonstrated in-demand job skills, science-backed cognitive strengths, and drive to hustle. Through this platform, skilled job seekers can access opportunities that are otherwise only accessible to university graduates.
Listen to this podcast to discover how Brett and his team started creating an equitable and efficient hiring process for recruiters and job-seeking candidates.
What is Skilful.ly and how does it provide an equitable opportunity to job seekers?
[00:00:33] Skillful.ly at its core is building a more equitable alternative to allow the employment platforms that are out there today. And we reached that equity by focusing on the demonstration of relevant job skills first and foremost.
[00:01:31] It is built around the premise that what really matters and what’s really most representative of someone’s potential in a particular job is not the match in some of those factors that have become the heuristics, that have become the metrics that those systems really based themselves off of, but rather the affirmative confirmation that you actually have the skills that are required for a particular job.
What do you consider the most important aspect of becoming a startup founder?
[00:35:10] I think what gets lost is just how meaningful it is and how important it is to find the team that you want to work with to build those relationships, to invest in them. I think that is maybe the hardest challenge, but the most rewarding pursuit in terms of the benefits that have accrued from that is to spend a lot of time and a lot of thought on how to build that team. That is the secret to your long-term success, as opposed to any idea that’s locked up between your ears.
(Transcripts may contain a few typographical errors due to audio quality during the podcast recording.)
[00:00:04] Chris Kim: Hello, and welcome to the OneHaas Alumni Podcast. I’m Chris Kim, and I’m here with our host Sean Li. Today we have Brett Waikart, Haas alum and CEO of Skillful.ly. Skillful.ly builds tools for employers to design and manage a workforce defined by skills. Brett, welcome, and glad to have you on the show.
[00:00:23] Brett Waikart: Guys, so good to be here. Thanks for having me.
[00:00:25] Chris Kim: Could you talk a bit about what Skillful.ly is and what you do to focus on as you’re in your role as the CEO of the company?
[00:00:32] Brett Waikart: Sure. Skillful.ly, at its core, is building a more equitable alternative to a lot of the employment platforms that are out there today. We reach that equity by focusing on the demonstration of relevant job skills, first and foremost. So a lot of the other platforms that are out there today, they build this monstrous base of job seekers; think of LinkedIn global audience or Indeed. The amount of job postings and on the sites, the technology is really focused on going from this large global group of candidates and then whittling it down to a much smaller group of candidates that is engageable and manageable by a human HR officer on the other side of the computer or the employer. That is what we refer to as a kind of negative logic filtering, where you’re looking for reasons to eliminate somebody from that candidate pool.
You’re looking for may be gaps in employment, or they didn’t go to the right school or have the right background, whatever it may be. There are a thousand different ways to eliminate somebody. Skillful.ly is built around the premise that what really matters and what’s really most representative of someone’s potential. And a particular job is not the match in some of those factors that have become the heuristics that have become the metrics that those systems really base themselves off of. But rather the affirmative confirmation that you actually have the skills that are required for a particular job, the deeper and deeper we’ve gone into this, the more interesting the subject becomes, but what we are able to do on a not just employer by employer, but on a role-by-role basis is to determine the specific skills that employer is looking for. Those could be job skills that could be intrinsic skills like cognitive or behavioral innate skills.
And that forms a unique archetype. A target that manager is really looking for and what we do, our technology is essentially matching software that then looks at the skillsets, the unique skill sets of every member on our platform, every job seeker, and then introduces that member to a job based on that fit based on that match in terms of the skills somebody has and then the skills and employers looking for. That’s step one for our process, we don’t filter the candidate pool beforehand by age, race, gender by school, by academic or education, or employment background. It really starts with that skill, that’s the foundational thesis. And then I think the second part of the question is what do I do as CEO there, just try to stay out of the way of all of the brilliant people who we’ve convinced to come work on this project with us.
I think you’ve spoken to one of my co-founders Kelly Cure, who is an absolutely sensational rockstar. She runs our growth, but she really runs everything that is looking at our job seeker audience and how we grow that. Johnson, the third co-founder, the third leg of the stool, is our Head of Product and is looking at everything there in terms of the product vision and the development of the technical piece. And then I fit into really speaking to a lot of the external stakeholders. So a lot of the employers, a lot of the investors, the partners, that’s kind of the general breakdown, but I think as Sean and, you know, things become a little bit less organized, especially in a quickly growing company. So Chief Everything Officer tends to be what it really means.
[00:03:43] Chris Kim: That’s awesome to hear, Brett. Where did you grow up, and how did that, you know, your early life influence where you are today, you know, and maybe even how you lead the company?
[00:03:51] Brett Waikart: Great question. So I grew up outside of DC. I grew up in Maryland on the east coast. Very cool. I was convinced I was gonna be an east coast kid for my and entire life. I think I turned 35 in a few weeks here. And I don’t think it was until I hit my late twenties that I realized I was going to be California-bound. But in my early career, I was a finance guy. I went through business school as an undergrad, and I was convinced I was going to be on a kind of stereotypical finance track. I graduated in 2008, which is just about the worst possible year to graduate with a finance degree. Just like a few minor news items there that, if you were planning to go onto a path, I had an offer online from a couple of the bigger investment banks, and they got rescinded as soon as the Lehmann news came out, and everyone started a years-long job freeze, and the finance industry became a different place.
So that really gave me a front-row seat one to the way that a lot of the finance industry looks at employment and looks at human capital, kind of looking at it from that side. I was in finance for seven or eight years long enough to start building and growing, and hiring teams of my own. And I think that really served to look from the inside to recognize where there were things that were broken, but that was just accepted as like, hey, this is the way things are. I helped co-found a charity, Portfolios with Purpose, shortly thereafter. It was back in 2013 when I stepped in and helped lead that organization. And that path that step off of the finance track was probably my first experience in understanding that you could pick a problem, you could find something that was just structurally wrong and start to propose a solution and get people behind it and get momentum and resources and energy behind whatever solution that may be.
And we can unpack all of that. But I think that was probably the first little pivot step that took me off of the lifelong finance career trajectory, very New York-focused to looking for something more. And, you know, we’ll skip over a couple of stepping stones along the way. I ended up in Cal; I came out to San Francisco with Berkeley, with Haas in the back of my mind, although not sure I was going to do it. And then, through all of that process over the years, Haas was really kind of an incubator. It was really an awesome opportunity to think up what Skillful.ly could turn into and what we were trying to do in the world. I’ve always thought it’s one of the most fun things to be able to kind of look over your shoulder and try to connect the dots to try to see how one thing has led to another. And yeah, I’m still always amazed and miffed about how I ended up here, but so grateful for it.
[00:06:23] Sean Li: And you nailed the mission and the purpose of this podcast, where it is just collecting people’s stories and trying to connect the dots and trying to find recurring themes, and then connecting people based on these themes, right? That ultimately derives the passions in our lives.
[00:06:40] Chris Kim: Hey, Brett, you talked about your transition moving out of finance. I’ve seemed to become good at asking this question. You invested the time and energy in college to study finance, and then you went into finance for a number of years. What got you to come off of that track and kind of pivot in a totally different direction, almost like the same thing you were saying, like an east coaster for life, and then somehow ended up on the west coast, the long term here?
[00:07:04] Brett Waikart: Chris, that’s an excellent question to get to the heart of the matter. The long and short of it is there was a real health scare with someone in my family, one of my parents, and I left New York at the time to come down and support and to just to kind of be present and be there. And it was this kind of an inflection point where it was my father, and he was diagnosed with a type of cancer that was just more aggressive than anybody was expecting. And he’s fine now, and he’s bounced back, and technically it’s in remission, and he’s playing golf just like you would never imagine anything ever happened. But I remember at the time; it was like the universe grabbed me by the shoulders and just shook me really stinking hard. It was one of these moments that kind of brought into focus. The fact that I wasn’t really getting everything out of my job. Now we’re talking about beyond the compensation, beyond the pay, how you’re filling your own cup. I wasn’t getting out of it, what I wanted for the rest of my career. And that whole process was really interesting to kind of look back on or is really interesting to look back on. But I remember it surfacing this feeling of kind of like this deep inner dissatisfaction is maybe the best way to put it and coming back out of that, it served as the opportunity to kind of rethink things, to look around, to look at the folks that were on my path, maybe five or ten years ahead of me. And for me to say, I don’t like your point; I’ve invested time, money, effort. It was hard getting a career started in finance starting in 2008.
That’s not a fun time to try to grind out a career there. It was also just this, like looking down the road and trying to project myself into the same role, the same kind of trajectory, ten years, hence. And it was just something that I didn’t; I couldn’t live with. The Portfolios With Purpose, the charity that I helped to co-found and then run, was really just the first step towards something that felt and not to get too, maybe fluffy with this, but like a step towards something that emotionally resounded in a way that the career had it. I actually had a mentor at the time who I was talking to about this. And he gave me incredible advice that I wasn’t expecting at the time. But he spoke about, think about your own internal, emotional Richter Scale, what actually leaves a mark.
When you think about it, what was the interaction or the experience that made you feel most yourself but just made you feel the most? And it had nothing whatsoever when I thought back on it, to what I was doing for my job, for the work, for the path I was on. And it really led to leaning into and making a more central part of my life, the work that we were doing at the charity at that time. And that was purely one step of course correction. It was by no means the end objective. I think everyone’s still searching for whatever that end goal might be. And maybe that’s kind of the point of all of this, but that was the transition. It was that kind of moment. That health scare triggered a way of thinking that I think wouldn’t have happened to me naturally or wouldn’t have happened on its own.
And then that just led to branching off in terms of the path I was walking down and led to a whole series of things that brought me out here to California. Chris, that really is the central question, you know, that kind of jumping-off point and how that led us or led me to where I am right now. I love sharing that story. And Sean, to your point, the fun of your job, I love hearing kind of the counterpoints and the reciprocals in other people’s lives, but I think it’s what matters that idea of the emotional Richter Scale is always stuck with me.
[00:10:35] Sean Li: How did you get into what you’re doing now?
[00:10:38] Brett Waikart: Let me give you a very brief tour of what the charity did because it led directly to what I’m doing now. So Portfolios With Purpose started off as out of the desire to raise more money for some of the charities that were just near and dear to our hearts. And it started as a simple game. It started as essentially fantasy sports stock picking. And so, instead of picking a team of football players with a bunch of your friends, you picked a charity that you were going to represent, and you picked a bunch of stocks for your portfolio. And we wrote a little bit of software that just kept track of you versus everyone else on the leaderboard. And it was fun. There were 50 people the first year; it was never; I don’t think we ever had the ambitions or to grow the way it did, but the next year, our colleagues, the folks that we worked with, and our friends all heard about it.
And a couple of our bosses heard about this too. Some of the folks who run some of the biggest hedge funds in the world and some of the executives at big banks joined in that second year of the contest. And I remember, I think this is probably out on CNBC, somewhere it’s out on the internet, I’m sure. Still, we got a call from one of the producers at CNBC in that second year saying, “Hey, we’ve heard that you’re running this super-secret stock-picking contest with all of these crazy personalities. Is that true? And would you want to come on and talk about it?” And listen, from our perspective, this thing had barely come together, and this person had been told a fish story of exactly just how big and how the secret of an organization we were when we say, sure, yeah, let’s go talk about it.
This would be great. And so we skip over to New Jersey, where the studios are. One of my co-founders stepped on the show, and they put the website and our name at the bottom of the chyron on CNBC. And I mean, Sean, listen, our website was stuck together with duct tape and bubble gum at the time, I think like a stiff breeze, would’ve knocked it over much less a CNBC viewership midday. And so, predictably, the website gets overrun. It’s an absolute mess of a chaotic pile of broken websites. And we realized, oh, this is going to be a thing. And that next year, we grew to a couple of thousand members and now 5,000 and then 10,000, it’s grown and grown and grown. And it’s been this really fun community to grow. We’ve raised about 5 million for charity through this contest over the years. It’s been great.
We’re super proud of that in itself. But to get to your original question, what we were creating was this really fantastic community. And this community of folks who were kind of philanthropically minded, who had an interest in trading and investing. This was before the Robinhood and the Wall Street bets days, but we were still picking up exactly that momentum. And we had a huge student population that was coming to our site and playing this contest and learning how to invest in our platform where technology was capturing all of this. We had really good information on who was good in a particular job, or with this particular skill who was learning, what that learning speed was, who was most engaged. And so, about a year or two later, we got a knock on the door. First was Citi, the big investment bank and then Barclays, and then Goldman.
And we’ve spoken to everybody on the street since then, but the conversation always goes something along the lines of, “Hey, this is a great charity. We’d love to support you. We’d love to sponsor. Can we take a look at that data?” And we would have so many people that would look at us as an interesting talent funnel because we cast a very broad net. We accept all comers. This person anybody who has even the slightest interest in this skill of investing can come to Portfolios with Purpose and learn how to invest. But we would capture really interesting information on their kind of learning curve, their trajectory, and that information was exceptionally valuable and really interesting to big employers who were looking to expand the talent pools that they were hiring out of. And what they were doing is what we would now call all skills first recruitment, where they were starting, not from where somebody learned a particular skill.
That’s not asking what four walls physically or virtually you stood on inside when you learned how to invest. It’s just a question, Hey, were you good at investing? Because it’s a core, fundamental skill to these different career paths. And over the next two or three years, we would just introduce a dozen people here, a couple of dozen people there. It was very informal. But then I remember we got called into the main city boardroom by the president of Citi at the time saying, “Hey kids, this is really wonderful what you’re doing—and basically running off of an Excel spreadsheet. What do you think about doing this as an enterprise piece for all of our offices globally?” And we just sit there, and I think our budget might have been maybe like a hundred, 200 grand a year, like on a good year.
We weren’t paying ourselves. This was all for fun. So we giggle a little bit and look across the table and say, Oh, sorry. We can’t. But what we can do is exactly what we’ve done. We spun out a new company, a public benefit corporation, which is a for-profit company, but with the social mission prioritized over the financial one. And that is entirely focused around that core insight. And the idea here is to provide that prize level solution for employers like City, Slack, BlackRock, EY, Deloitte, anybody who is interested in looking at the labor pool a little bit differently, starting with skills, as opposed to starting with alma maters or GPAs or whatever they’ve used in the past. And that’s what has, so to be honest; we had that initial experience when I was still in my first year of the EW program at Haas and having that kind of a conversation; that’s definitely an eye-opener. And I kind of put my head down and as a group started to set into work thinking, well, how can we build towards this four years later, here’s Skillful.ly.
[00:16:10] Sean Li: Have you guys had to fundraise at all?
[00:16:12] Brett Waikart: We have. So we’ve raised an insider’s round. We’ll call it. We haven’t accepted institutional money. We probably will soon, but we haven’t yet. We’ve been entirely insider-funded friends and family, and it’s been an interesting road, but we’ve begged, borrowed, and stolen with a couple of hundred grand of funding where we’ve built out a product where this is a two-sided employment marketplace. That’s how we’ve structured a two-sided market, where the job seekers are the supply, the employers are the demand. What exists today is a fully built out user, UI/UX for the learner, for the job seeker. And then we work with the employers in a very kind of hand-to-hand combat type of style, where we’ll automate more of that down the road. We’re, and we raise funding when we get a better understanding of our sales mechanism and the repeatable kind of process that we wanna offer to our customers. To date, we’ve been hustling off of a relatively bootstrapped operation. So who knows, maybe ask me again next season, and maybe things will change by then.
[00:17:10] Sean Li: That is amazing. We’ve done something similar as well. I just love the idea because it’s always bothered me. I don’t know if I should be talking about this, but at least publicly, maybe we might redact this, but it’s always bothered me that finding a job or just matching skills does not exist. LinkedIn doesn’t do this. Like when they post a job, and it says like, we need X, Y, and Z, and LinkedIn knows what skills I have. Supposedly when they know my resume, they have my information. Why can’t they just say, oh, you have X and Y, here’s Z take this course? And now you can apply, right? Why is this such a black box? Why, you know, why doesn’t something exist? Just help me get that job and point me in a rush. And so what you guys are doing makes perfect sense to me.
[00:17:58] Brett Waikart: I hope we don’t redact this. This is the fun stuff.
[00:18:02] Sean Li: I don’t want to redact it. I want LinkedIn to get the idea.
[00:18:06] Brett Waikart: I hear you; there you go. If that happens, maybe we can talk about that. I guess that’s another; that’s what my father would call a champagne problem. If LinkedIn is coming after you and trying to feel your idea. But no, I, you know what it is. I think there’s room for both approaches. Cause they both accomplish very different things. The arc of technology here, the deeper we’ve gone into this subject, the more and more interesting it gets, just as almost like an anthropological experiment. So here is like a super-fast history lesson of just this particular space and the late ’90s, the rise of the digital application to a job that became common, where instead of mailing in a resume or calling into an HR person to talk about, Hey, I’m qualified for this job. You can submit an application online. And so for an average job posting, maybe a manager was getting 10, maybe 20 resumes to review applicants to engage and decide if they’re qualified.
Well, now they’re getting hundreds. If not thousands, that was the impetus for the creation of LinkedIn recruiter and Indeed, online job boards and resume networks, because then what you needed to provide that HR manager was a tool to make this sea of applications manageable, have this be something that they could skim the top off of basically saying, Hey, we’re gonna take the very best of these candidates. And then those are going to be the ones that we spend time with. And in the last 20 years, since I think LinkedIn went public in 2003, LinkedIn has done this wonderful job in a very lightweight fashion, scraping some basic layers of information about who you are as a person, who you are as a professional, and there’s the resume data. And then there’s the network data. The resume data, obviously that’s, those are all of the keywords.
Where’d you go to school? What are your jobs? What are your interests? And then the network is all; who did you know? And do you know somebody I know? Because I’m going to trust you more, and you’re probably going to be more qualified in my mind, or I’ll be more comfortable hiring you. Great for that core problem that this was trying to solve. It makes a ton of sense. That is a great way for technology to provide the benefits of scale of being able to reach this incredibly large audience and then boil it down to a smaller group that hypothetically is gonna be more targeted towards what you want than the rest. What LinkedIn does beautifully well. And what a lot of these platforms have all really mastered is the idea of what is called a weak ties network. Weak ties, just in that you only have to submit a PDF of your resume and click a couple of buttons to like this and connect to that person.
And there you go, that’s all you need. We’re structured differently in terms of our network structure. And then in terms of the user behavior that a learner has to actually practice on our site. So instead of coming in and uploading your resume, which is a self, attested version of your qualifications, it’s you saying, this is why I’m qualified for a job. What you do with Skillful.ly is you literally prove those qualifications on our site. You earn those qualifications through the time that you might otherwise spend writing a cover letter or recrafting your resume. Instead of doing that, we ask you to actually do the work, do something that is representative of the work you might do in a job that you’re going for. But that, as a result, gives the jobseeker far better information about what a job really entails.
What is in this is, do I really like this? Am I gonna hate it? Do I wanna do something different? Well, let’s get you that information before you accept a job offer and start going down, however long the road is. But then, for the employer, you get much granular, much deeper insight about what somebody is capable of, what their potential is. And what’s interesting is that LinkedIn scales incredibly quickly. And that scale is what their entire business is built around. It is on creating a network that spans the globe and that maybe it’s sometimes crude fashions can then be organized into buckets by keywords, by likes, by your behavior on the site.
[00:21:50] Sean Li: But it is very crude, though.
[00:21:52] Brett Waikart: Let’s face it. We’re all graduates of Haas, one of the best business schools in the world; we all are exceptionally well connected by virtue of that, by the privilege of being able to go to that institution as well as what came before it.
So we are the ones that benefit from that LinkedIn system. That all these tools have been built to benefit people like us that have similar backgrounds, similar track records, but we are by far the minority of the actual global workforce. And what gets fascinating, like where this really gets interesting to unpack, is when you sit with an employer and we sit with Franklin Templeton and talk out what they’re looking for in a particular analyst role or an intern role, Franklin Templeton is amazing. Cause they already have this progressive vocabulary that they’re already thinking of people in terms of skill sets, not necessarily backgrounds or resumes, but the qualifications they’re looking for are skills that are universally acceptable, whether or not you went to Haas, Cal, or you went to Brooklyn Community College, out of the CUNY system, as these skills exist in the workforce in a way that LinkedIn is not going to elevate.
They’re not gonna point you in the direction of where that skill is. They’re gonna point you in terms of these other markers that are kind of historical representatives of having a particular trait; it’s an association or affiliation at worst, it’s a lazy heuristic, a lazy shortcut. They’re gonna provide scale, but they’re gonna have that type two error where they’re going to say, Hey, listen, this person is probably qualified. Probably they look and smell like somebody you’ve hired before. This is probably going to work, but it misses the majority of the labor pool. The majority of the actual hireable talent that exists out there would be just as, if not more than more qualified than what you’re gonna get with the status quo tool. And that person’s not getting looked at there’s you’re not competing against 12 other companies because somebody went to Cal or Harvard or wherever, but these people have the skills that you need in the labor market right now, the workplace, it is like never before oriented around a rapidly shifting set of skills that make somebody good in a particular job at that moment in time.
And when the demand for skills becomes more fluid and more dynamic, that’s when you start seeing cracks in the LinkedIn model, that’s where you see an opportunity for us, for instance, to step in and provide a compliment, you know, we’re not saying we’re gonna displace these behemoths. They have a tremendous footprint, and they’re wonderful companies, but they miss something. And that little something that’s enough to unpack, that’s enough to spend time exploring.
[00:24:18] Sean Li: I think you’re being a little bit modest there. Maybe you wanna be modest, so they don’t feel threatened yet.
[00:24:24] Brett Waikart: I’m gonna wake up. My LinkedIn page is mysteriously gonna be gone. Somebody’s gonna reach in and be like this guy, can’t be looking at our paper anymore. I can’t be looking at our platform.
[00:24:32] Sean Li: I really do think fundamentally, what you guys are doing is so important because you’re absolutely right. The recruiter or an HR person is getting a 10, 20 resume. They have the time to really talk, filter, and analyze. But when you’re getting hundreds, thousands of resumes, you do that skimming process; just skim the top. And the way you skip from the top is, like you said, by these outdated methods of just looking at the top schools and whatnots, and it’s not a very equitable or fair process at all. And a lot of times, just from my own personal experience. We’re not talking about Berkeley; just because someone went to Harvard or Stanford doesn’t mean they’re gonna be a great employee or it’s the right fit. I think what you guys are doing is amazing.
[00:25:17] Brett Waikart: It really is. The more and more interesting, the deeper you go down; speaking of Harvard Business Review, I just put out a wonderful bit of research just a couple of weeks ago, but that speaks exactly to this. And one of the things they call out is that a lot of this software it’s turned into black-box algorithms that are making decisions on who to screen out and who to introduce an HR manager to. And some of the most frequently used bits of negative filter logic reasons why that is excluded from consideration. One of the biggest is that the screener will see a gap in employment in terms of between particular jobs, and that’s justification for a huge percentage of the workforce of the actual employers that a candidate will immediately get screened out just from that.
And it’s not an HR manager looking at this resume and saying, Hmm, they look like they have a skill, but there’s this gap. It’s a computer who says, okay, these two dates, don’t sandwich together, you’re out of here. And so what that then excludes is people coming back for military service mothers returning to the workforce. People who’ve taken a break to be able to care for family members who are sick. All of these things like life happen in those gaps. And that is the most unfair reason why somebody would not be seen or not considered for a job. And it’s insane if they have the skills, if they have the energy, the hustle, the know-how to prove that they’re qualified, that they can do a job, but they’re excluded for something like that. Something’s broken. And it happens all the time, everywhere, more than people will want to admit. But that’s one of the use cases for us. That’s why we have equity in our tagline because the system needs to be able to accommodate situations like that.
[00:26:59] Chris Kim: Right. Could you explain why companies might do that? And I think for folks who maybe work in HR, they have some sense of, you know, what the motivation might be there, but from an outsider’s perspective, you might just think, Hey, I wanna look at the biggest pool possible. I want to get as many people in that recruiting process so I can pick and choose. Why would a company want to just screen out people almost automatically in those situations? And why is that important for products like Skillful.ly that are doing the opposite, really looking at skills?
[00:27:27] Brett Waikart: Yeah, it’s a great question. More is more until it’s not. And this idea that more candidates for a particular job mean that you’ll have a larger audience to select the very best from, you know, there’s an upper balance on when more is more stops being the truth that like the physics of this means that there is an upper cap in terms of the number of people that an HR manager or a team can engage with. Particularly when you look at, like let’s segment, the populations of companies out there to companies that you would call a brand name versus companies that might be off-brand or somebody who doesn’t benefit from that, but let’s think of like an apple or a black rock or a bank of the area, somebody who’s like a well-recognized kind of brand. When they put something up online, they put a job description up there.
They’re not just getting hundreds of applications; they’re getting thousands. And behind that job posting is still a single hiring manager. Who’s responsible for getting somebody like a button, the seat for that particular role. And so just by the very nature of it, by the fast-paced nature of hiring by how competitive it is by how stretched thin, and honestly, oftentimes under-resourced that some of these HR teams really are like, I think certain sectors do a very good job of identifying their people as a strategic asset, but plenty of others look at HR as an administrative function. And there, there’s a finite amount of resources that go into this. And so, those types of tools that make a job more manageable have universal appeal. And if the alternative is saying that I’m either gonna use this tool, what’s the old saying nobody ever got fired for hiring IBM for a job like nobody ever got fired for using a LinkedIn recruiter.
Of course, everyone uses a LinkedIn recruiter. Why not? Of course, I’m gonna use an Indeed job posting or a handshake for the campus, whatever it may be. These tools are everywhere. They’re ubiquitous. And the assumption is that, okay, that’s a rational step for an HR manager to take, to win that down one way or the other. And sure, it may be imperfect. They may be missing some candidates, but they’re gonna get hired and are going to be able to get onto the next role. And then we’re all gonna cross our fingers that they can retain that employee here, that employee is able to do what they said they were able to do. That’s the thing that the negative outcome of a bad hire typically takes time to realize when you have to spend upfront to be able to make that hire. So the fact that there’s that mismatch in timing means that you can continually make the same mistake, the same expense item, when you’re hiring somebody who you’re not gonna be able to retain or who isn’t a good fit for a role.
You’re not being forced to come to terms with that at the moment of hire; to be honest, that’s what makes our job challenging, or our job interesting is to be able to illustrate to employers the potential that has been missed. What’s been lost in that process. In some ways, I think that we have paddled into the right wave; COVID, Black Lives Matter, the murder of George Floyd, it surfaced a lot of really difficult conversations around structural biases, around negative employment outcomes, around participation rates in the economy that were uneven demographically. And then that has been, the next logical step is to say, oh, I wanna do something about it that wasn’t there maybe four or five years ago. It is now. And Skillful.ly is perfectly positioned to raise our hand to say, Hey, you can do something here. We can help. But I think that’s the logic that is going through the head of the HR manager. It’s an impossible task to try to find that perfect hire out of a thousand or more applicants. And so, how do you do it? I think it’s kind of a constant process of trial and error.
[00:30:57] Chris Kim: Brett, I know you; you just touched a bit about how work has changed in the pandemic. What has it been like leading a company during the pandemic, and where have you felt the most, just pressure to grow or to change us? Like everything around us is just changing, and we’re still in a state of flux. I think for a lot of us, even today,
[00:31:15] Brett Waikart: Man, we were talking about this before we hit record, I think, but what an interesting time to be building a company and to be putting something out there. I wanted one to say like, Hey, we’re privileged. We’re lucky to have work, to put our heads down and focus on. We’re lucky to be able to build something to be in a position here. I think there are so many people that the pandemic took that away from them and created a ton of frustration of angst of lost potential. And so one, there’s just gratitude there to say, Hey, the pandemic, it was a fortunate circumstance that it lined up and we had the opportunity just to put our head down and build in the same instance, we’re building a company, and we’re, we as there’s three of us, co-founders at Skillful.ly, we’re all very, very close, but then there’s a team outside of that.
And the question of how do you create company culture? How do you instill the values that the three of us had when we decided to create this thing? How do you do that when you’re not all in the room with everybody else when you’re not able to all come together? So that has been a challenge for sure; from COVID, it’s been a blessing to be able to just kind of put your head down and grind and just work. I remember the first couple months of COVID; it was just like, all right, I’m gonna get up at eight. I’m gonna crack my laptop up. And then at 10:00 PM, there’s nothing else to do. I’m gonna work. And until down on my couch and then go back and forth, and you get a lot done that way. Another downside of this is I’m a social animal, just like a lot of us are.
And you know, I’m a hugger, I’m a high-fiver, I’m a boisterous yell, joke, laugh. And like you, can’t one side of conversations with my Bernadoodle Chief Human Resources officer that only goes so far. You can only really get so much out of that. Yeah. It’s been kind of an opportunity and a challenge in a lot of different ways, but what’s been fascinating for us is that I think COVID, we started building this thing. We founded this in 2019 before COVID really came to the forefront. What we had no idea was that wave we were paddling into because COVID was the great equalizer, especially if you were in school. We were talking about this before I was finishing up my EW, and we had just transitioned into zoom-only classes, but the whole world did. No matter again, if you went to Harvard BCC, any school in the world doesn’t matter, you were still in zoom classes, sitting there on your couch and your pajamas watching somebody talk to you on that screen.
And so, everyone was learning exactly the same way. It became so much harder to continue making the argument that the four walls, virtual or physical, you were learning within that mattered in a substantive way that made some type of incredibly significant difference between who is prepared or qualified for a job and who isn’t. And maybe it took a global pandemic for us to be able to make that argument effectively. But I don’t think we would’ve gotten to where we are right now without that helping to wake people up to this reality. So there’s a double-edged sword, a dozen different ways if that makes sense, but it’s been an interesting ride for sure.
[00:34:02] Chris Kim: Great. Brett, I know we’ve had a couple of folks who have founded their own startups coming out of Haas or gone on to become CEOs. What type of advice would you give to either current students or Haasies, or other folks who are listening to the conversation in terms of what is something that’s important to think about when you’re thinking about starting your own company, or becoming a founder at a startup?
[00:34:23] Brett Waikart: That’s a great question. I think if I were to look back on any of the successes as small and as early as they’ve been at Skillful.ly and anything I’ve ever led previously, the number one factor that has contributed to every single win that I would’ve not have had that win without is the people that form the team around me that are around us, that actually forms the group that you’re working together with. I think early days, Silicon Valley, and the idea of the single founder coding away in their garage, Steve Jobs and wise the act sitting there building the first Apple computer that gets over-romanticized. And I think what gets lost is just how meaningful it is and how important it is to find the team that you want to work with to build those relationships, to invest in them. I think that is maybe the hardest challenge, but the most rewarding pursuit in terms of the benefits that have accrued from that is to spend a lot of time and a lot of thought on how to build that team.
And that is really gonna be the secret to your long-term success, as opposed to any idea that’s locked up between your years. So I would say that I’m very fortunate; both my co-founders Kelly, who was a full-time MBA student, graduated last year. Johnson was a Master of Engineering student who graduated, I think, in 2019 with me. Those two are absolutely incredible and then that has just been multiplied as they’ve gone into their networks and found people that we’ve brought on board. And if you’re building a company, if you’re building something, if you have an idea for anyone listening, the only bit of advice I could give is to say, listen, think really hard about cultivating that team, because that makes the most, the most difference of anything else. The only other, the other piece for this, this has been a constant roller coaster. Like it is just one big learning curve that never quits.
I’m sure this resounds in a lot of ways, but whether it’s me, one of the other co-founders, anybody on the team, we’re doing something new that hasn’t really existed before. And so there’s not a playbook. There’s not really, uh, a set of answers or script that we can read off for this. The one thing I can recommend, I just read a lot. If I ever have the inkling of something that I’m not familiar with or something that I’m not as smart on as I think I should be, I have an unlimited Amazon Kindle budget. I mind my finances kind of tightly, but there are a few things that I’ll spend on. And for me, I’ll have probably five to six to seven books open at any given time that I’m just kind of cruising through. And that usually turns over once a month.
Sean Li: Any top books that you recommend?
Brett Waikart: Oh man, I am deep into a couple right now for sure. So I love Steve Blanks’, A Startup Owner’s Manual; that’s a classic that’s easy. Eric Ries, The Lean Startup. That’s another one. Ryan Holiday’s Growth Hacking is a wonderful book in terms of how to cultivate an audience of users or learners, a book called The Mom Test. Have you read that one? Do you have it right there? Or that was actually recommended to me by Johnson. Johnson’s also a big bookworm, but that’s been a phenomenal book that’s made it very clear just how terrible I was at customer interviews and how important it is to get better at those. Those are what’s open right now. Anything by Peter Drucker has been good. The Hard Thing About Hard Things is an old favorite. That’s another one.
[00:37:37] Sean Li: I had this on my desk all the time.
[00:37:39] Brett Waikart: Yeah, no, that’s a good one. Honestly, what’s been most rewarding, what’s made me most effective is like I remember what I was talking about at the beginning of COVID working for 14 hours with the laptop on my lap and just kind of grinding. I was not nearly as effective as I am now just because making space and time for that for reading with just like space for the absorption of ideas, to figure out, to think about how they resound to share that with other people on the team, I’ve found the importance of routine in terms of my own effectiveness with the rest of the team, to be able to show up as a whole person. But a lot of that is spent in reading, reflection, and a lot of writing. I think that was more than just a single recommendation for the listeners, but that’s what’s made the biggest difference for me.
[00:38:24] Sean Li: That’s you listed all the books that are important.
[00:38:27] Brett Waikart: I’m sure you could put together that’s the kinda must-reads, but I’m sure that they’re all on there.
[00:38:35] Sean Li: I also had to follow up on the question with your co-founders. We hear these news stories a lot about finding the right people to work with, but it’s rare for me to hear about what are the sets of skills that speak of Skillful.ly, what are the skills that you guys were looking for in each other that complement one another?
[00:38:53] Brett Waikart: That’s a great question. We think we joke about this a whole bunch. There are two components, and this is something that we think about with Skillful.ly as well, first off as co-founders, you wanna be really good at what you are doing as a co-founder as a member of that group, but you also wanna make sure that your skills are very different than the other co-founders in that group. And that’s just, you know, that’s logic. Everyone can kind of recognize that at face value. And so, we were fortunate. Johnson has his engineering background, very deep product vision, and represents the technical product side of what we’re doing. Kelly was actually a founder herself. She was a CEO previously before we joined forces under the Skillful.ly banner. And I’m so fortunate that I was able to talk her into thinking that wasn’t a terrible idea, but she was running a company that was very focused on a different segment of the user experience than I was thinking about.
We do have different skills. We relate to people differently, but she was thinking very deeply about an area of the user experience of employment than I was. It was really fortuitous. I introduced them to Kelly; I never would’ve met her through the MBA circle. We were all working together in the apartment of a mutual friend where Johnson and I were on a whiteboard in this guy’s kitchen. And she and her other friend were in the living room across like, you know, down the hall, working on her thing. And we literally overheard what each other was working on. We’re like, wait for a second, that sounds like what we’re doing.
[00:40:20] Sean Li: Who posted this mutual friend? Who’s this connector?
[00:40:24] Brett Waikart: Engineering guy, a good friend. He’s in the Bay. He’s now on the investor side, just like a member of the Haas network, but we never would’ve crossed paths otherwise. And I remember that started, I was so impressed with both Johnson and Kelly, but the way that Kelly had gone about building her business, what she was focusing on and you would ask like, what’s most important what we’re looking for, there’s this skill component, but then there’s also the mission component. Like how deeply do you care about this in terms of that emotional Richter scale, again, from beforehand that we were talking about. Both Kelly and I had a different way and path that kind of brought us to focusing on a very similar problem or different sides of the same problem. And we recognized that in each other immediately, and that kind of formed the basis of how she came into the group.
Johnson was in first, and then Kelly came in right afterward. But I think that shared belief and energy behind the mission of what we’re trying to do is what really glued the team together in a way that we’re, we always joke. We’re just so grateful we found each other, but it has made all of the difference. I think, any hardship, any speed bump, any curveball that’s been thrown our way. It’s always been something we’ve been able to manage as a group. And it’s because we took the time to make sure that those founder relationships were solid. But yeah, interesting how the world brings you together.
[00:41:41] Chris Kim: That’s an amazing story, Brett; as we wrap up rapid-fire time, I have a couple of questions, east coast or west coast?
[00:41:49] Brett Waikart: West coast for the life you’re never getting out of here, stick dynamite under me to get me back to the east coast.
[00:41:54] Chris Kim: Sounds good. Okay. For the EWs in the audience, evening or weekend class?
[00:42:01] Brett Waikart: At the risk of losing some friends, evening, for sure. I think having those were really busy weeks, but still being able to have your weekends to go surfing or camping or whatever. That was the only thing that got me through. I couldn’t imagine the folks who did the weekends are just stone, cold assassins. I don’t; there are different breeds of people that can manage that. I am so impressed, but for me, evenings, for sure.
[00:42:24] Sean Li: I’ll see, for life.
[00:42:29] Chris Kim: All right. Brett, a person or leader that you admire.
[00:42:33] Brett Waikart: Oh, man. Yeah, my father.
[00:42:36] Chris Kim: That’s awesome. And last one here. One thing that gets you excited to take on the day?
[00:42:41] Brett Waikart: I would say the prospect of surfing later that afternoon. I’m all about my hobbies. The hobbies are what keep me sane, as anybody on the team would attest to. So I need those little kinds of goodies at the end of the day to keep me focused.
[00:42:56] Chris Kim: Well, Brett, it’s been great to have you on the show and to hear about your story and everything that you guys are doing at Skillful.ly. We definitely wish you and Skillful.ly all the best in the future. And want to say, thanks again,
[00:43:07] Brett Waikart: Such a pleasure, guys. Thank you for having me. This has been a lot of fun and I hope to come back sometime in the future.
[00:43:16] Sean Li: Thanks again for tuning in to this episode of the OneHaas Podcast. If you enjoyed our show today, please remember to hit that subscribe or follow button on your favorite podcast player. We’d also really appreciate you giving us a five-star rating and review. If you’re looking for more content, please check out our website at haas.fm. That’s spelled H-A-A-S dot FM. You can subscribe to our monthly newsletter and check out some of our other Berkeley Haas podcasts. And until next time, Go Bears!