Jordan: "Thanks so much for doing this. We're super excited to have a little chat with you. To start, you could just tell us your name, who you are, your company. What does your company do?"

V: "My name is Vrijen, also go by V, founder of CareerSpan. We use conversational coaching to help candidates understand their deeper value, or their true strengths. And then we map that onto jobs that folks are looking to find candidates for. It's essentially a way for us to get much better quality applicant data and use that in a more effective way to match."

The Origin Story

Jordan: "Nice, cool. Thanks for laying that out. So what were the early days like? What inspired you to get this started? How long have you been doing it?"

V: "The original idea came on the 29th of November '22, which I remember specifically because it was the day ChatGPT launched. And I was on ‘the beach’ at McKinsey — for those who know, they know. And it occurred to me that you could use this technology not just to generate answers or output. You could actually have it ask questions. I spent most of that day aggressively researching everything from, what's the value of Socratic dialogue? Is there empirical stuff around what impact that has on cognition? All the way to, is this tech real or is this something a little bit closer to older technologies that we've seen?"

Mike: "So you were sitting at your desk at McKinsey, ChatGPT comes out, and you spend the whole day playing with it. Okay, cool."

V: "I was on ‘the beach,’ so I was at home. Walking into McKinsey is like walking onto the deck of the Death Star. I don't think I would have had the confidence at that point in my life to be playing with ChatGPT openly, at least at McKinsey HQ. But yeah, I think I had a really good instinct for where, if not where the tech was going, what one potential use case of the tech would be, especially since I was able to map it."

Mike: "How long was it from that day to the day you quit and started CareerSpan?"

V: "Two and a half months? Yeah, three and a half months because it was March 1st that I quit McKinsey. I had done some startup courses at my MBA program, but it really goes to show — I heard the word product-market fit maybe a thousand times in B-school. Couldn't have told you what it was."

Mike: "So you became obsessed."

V: "I did not have any visceral understanding of what it is. Very different case now, but yeah, pretty much immediately knew that there was value in that service for people. And more importantly, that there was value in collecting that data because I think I was just very early to the idea that you can match people on a qualitative basis as opposed to just where they went to school on a keyword basis."

From Coaching to Founder

Mike: "So it sounds like you took some startup classes at B-school. Had you always wanted to be a founder, or was this kind of like a distant dream?"

V: "It was an immensely distant dream. I came to the US — I'd done college in the US, wasn't the best student, which I'm sure is relatable to this audience, or at least some. McKinsey was one of the first big jumps up that I made career-wise, purely because I was actually hyper-unemployable despite being in a hot market."

Mike: "Says the guy that got into McKinsey."

V: "Because I had no tech background. I had a coaching background. I taught some standardized tests. Credit to me and my career coaching skills, I was able to parlay that into a narrative about how that experience would help McKinsey in a variety of marketing and sales situations. So, turning that into an offer. But I always knew I wasn't a really good fit for it. I just never had the confidence to even imagine myself as a startup person. But also, I just felt so strongly about the opportunity that I had to dive in."

Jordan: "Nice, so what was the timeline exactly? You said you went to business school and then you went to McKinsey — how far into McKinsey were you?"

V: "I was maybe three or four months into being at McKinsey, maybe four or five months. And then yeah, three months after that I was out. So it was pretty firm in the desire to build in that area. I don't know where that confidence came from, it was absolutely unearned. But I think it was certainly motivated by the realization that people need this. People need someone to essentially just be available to them to ask them questions about who they are. A lot of folks don't have that privilege, right? It's a privilege to have parents that have the time and the luxury and the awareness to bring that out of you at an early age. And I would argue 90% of folks don't have the ability to self-represent that way. So really the problem is — with all due respect to resume generators, they're bad technology because we don't need resume generation. We need people to understand what to say about themselves. The resume is just the conduit for communicating that signal. And so that's sort of how I try to encourage folks to look at the hiring process nowadays."

Who CareerSpan Serves

Jordan: "So who's your main audience? Is it a lot of people early in their career? People looking for career pivots? Or all of the above?"

V: "Kind of all of the above. We realized it was a particularly tricky marketplace maneuver because the tech on the applicant side is so generally applicable. Everyone — we've had former chiefs of staff at FAANG companies, we've had Hugo award-winning science fiction writers, and also HVAC technicians and public school teachers using CareerSpan. I would defy a lot of folks outside of social media networks to have quite the range of customers that we do. Meanwhile, on the employer side, what we're finding is that startups from seed to A are kind of great because, well, everyone's aware of how screwed hiring is. Once your referrals are tapped out, once your network is tapped out, scaling that as a talent strategy is very hard unless you commit your time wading through resumes. And so that's sort of the value add we bring to those companies."

Mike: "So it sounds like you work with both, but is your primary ICP the employer or the employee?"

V: "The person paying us is the employer. It is surprisingly hard to monetize unemployed people that are under emotional stress. Who would have thought?"

Mike: "Got it. Yeah."

Early Days

V: "We essentially went through — March 1st, quitting McKinsey, part of that mass exodus of folks around that time — and essentially go straight into work, raise friends and family around about $200, $250k, picked up a head of AI after a few false dawns with subpar co-founding options."

Mike: "Right, you're not technical, or you weren't technical."

V: "I was not technical, no. I'm actually a lot closer to technical now."

Mike: "So what were you building in the beginning? Or what were you doing in the very beginning?"

V: "When they say don't start a company with two non-technical co-founders, I now understand why, right? It was immensely difficult. Neither of us really had tech pedigree. It was the blind leading the blind. It was me just finding out in real time every day. So I would easily say maybe the good portion of that first year was burned. And I think that was definitely something we carried with us throughout the company. But at the same time, we were very lucky. We got a brilliant head of AI who was building multi-agent orchestration before folks were even thinking about that as a concept. I think the good thing was we were very early in building solid, reliable tech on very good first principles engineering. And luckily, because I had such a great person to learn from from a product and technical perspective, I think I had a lot of the fundamentals that — more recently as I've started to actually build and vibe code myself — those fundamentals have actually helped me go above and beyond in many ways."

Mike: "So were the early days about trying to find that technical partner? Or trying to find customers?"

V: "It was trying to find a technical partner because, I think we can all admit vibe coding does great now, but two years ago it was not there. It certainly wasn't there for someone like me. It was still spaghetti. We were in this weird situation where we had to build out something concrete, and to have it be a rather seamless conversational experience was actually quite taxing technically, especially for a team that was going through a lot of growing pains and specifically a product leader myself that was going through a lot of growing pains. But I think once we established — I think the first moment it clicked for me was in some of our early testing. We had an extremely high adoption rate with female public school teachers that were trying to transition into tech, which is a very weird, very niche thing. It's actually people that are not known for bragging about themselves, and are going from one environment where they're very used to communicating what they're skilled at to a new environment like tech or ed policy, where they had to essentially rewrite their story, rethink how they thought of themselves, and then turn that into this professional document that other people have been writing for their whole lives. And so that's when we knew, okay, there is this need that people have to self-express. They don't really know how to turn that into the actionable signal. And once we had built that out and obviously realized people want this but we're struggling to get them to pay for it, that was when we went more so to the institutional direction. We tried selling universities, tried selling career centers. I think one of the greatest pains in my life has been trying to sell to universities. I don't think I'm ever going to try that again. It was a lot of wandering around until we found a much stronger alignment both on the customer side and the employer side."

What Employers Actually Get Out of CareerSpan

Mike: "V, so much of the value seems to be the ability to help employees tell their own story. But it sounds like your core customer is the employer. What do the employers see and get out of CareerSpan?"

V: "On a really simple level, what are we all trying to do in that seed to Series A stage hiring? You have a certain amount of time you can allocate to going through the talent pipeline. We're all trying to optimize for how many promising, worthwhile candidates do we see for the least amount of effort. Now, historically, our options have been just accepting that we have to read a lot of resumes. But before AI, the resume meant something, right? It meant something because the words on the page couldn't just be generated out of nowhere with complete ease. When AI comes around, people are like, great, AI can reason, AI can read this, AI can handle this for me. Unfortunately, the problem is that AI can also generate a fake resume, or help someone figure out what to say to pass an ATS, which is a completely questionable technology in many ways. So what are you really supposed to do? And so I think for us, where we found a lot of alpha with recruiters and with employers is you actually need to know someone deeply. You need to be able to match them not just on the skills you're looking for, like Node.js, but what we really care about is: are they going to be a cultural fit? Are they going to add to the team dynamic, or is it going to be subtractive to bring them on? And the stat I'll end with is 46% of hires fail by the 18-month mark. And 90% of the reason they fail is a values, mindset, or soft skills mismatch. So what you can conclude is that we're actually very good at figuring out whether someone can do the underlying job. Most founders at our level are capable of discerning who's able to do the thing. It is whether they're able to do the thing at this company, on this team, in this position, under these constraints. And that's something that is a qualitative judgment on who someone is in a dynamic where that person is self-interested. So we respond by just throwing in more resumes, more assessments, more rounds of interviews. But all you're doing is adding more data to the pile without actually cutting the Gordian knot and saying, what are the most essential things to know about this person? Which are essentially, what are the trade-offs? Bring this person in — what are they going to add to the environment? What do I lose?"

Mike: "So we're really good at interviewing for function, but not so good at interviewing for fit. And you solved that problem."

V: "To the extent that — right. The problem is, to do that, you need to know a ton about the candidate. And that is essentially where the slog of building out a marketplace in this particular context came from: engaging with folks and persuading them that using this not only has intrinsic benefit, but will also sort of help bring jobs to you."

How CareerSpan Captures Culture Fit

Mike: "How do you find all that cultural and fit information? How do you learn that personal stuff about how a candidate is actually going to function?"

V: "There is some relatively major news on a professional front for me down the pipeline that may give context to why I have such a strong POV on this. But essentially the insights you need to know about someone from an informational perspective are just, how do they behave? How do they think? How do they interact with others? And so the ideal circumstance to figure that out is to just observe someone. We obviously can't do that. So what's the second best? Get them to tell you about it. As I said earlier, you can't really trust them. But lying is a sprint. It's not a marathon. Psychologically, when you get someone into the perspective of, I need to mull over the substance of what I have done, and you're being asked questions that are meant to induce reflection — not test you — it's just a completely different way of drawing information out of people. So video interviews are flawed technology, right? Because your best candidates are going to scoff at it and your worst candidates are going to be stressed out and going to perform poorly. What is much more productive is to decouple the process of getting to know someone from the process of evaluating them. And that's essentially our broader thesis for how matching can be solved in a talent context: we have to make hiring non-adversarial. We have to give employers a really good reason for helping candidates in this way. And that reason is you don't waste time. You can basically scan against thousands of folks on a semantic basis within a matter of an hour or two. And most importantly, in something that we have a few pilots in the works with VCs: essentially just building a talent pipeline. Alumni Ventures, a VC, told me that they had 10,000 hits on their job board during peak weeks. But the best case scenario is those folks are just crashing against a wall. Because cold applying isn't really working now, right? So it's a waste of time for the candidate. It doesn't direct them in any meaningful direction. And worst of all, for the founders that are trying to give every inbound candidate a fair shake, you're just sending more noise their way. So VCs are starting to realize, why am I paying Getro $10-15 grand a year for what is basically an ad that fills up my PortCo CRM but doesn't solve the underlying problem? Why not just build my own talent pipeline? And so that's where we're seeing traction — specifically the niche that we've honed in on is folks that want to build pipelines for the future."

The Future of Recruiting

Mike: "So V, what's the future of recruiting look like in your mind? The AI is writing the resume, the AI is reviewing and reading the resume. What ends up happening?"

V: "You know how in strategy games there's a fog of war — you can only see so far ahead? Everyone's fog of war is basically the first 100 to 300 candidates you give a shift about reading the resume, right? Because everyone that applies after that point — they're not hearing back. We know they're not hearing back. Even out of the first 300, which I'm being very charitable in implying that a busy founder will read 300 resumes with less than a 1% conversion rate, it just is more frustrating than anything else. And so I think in truth, the real question for me is: who is going to set up the infrastructure to collect human data at scale? Obviously, we would like for that to be us. But what society needs — to avoid some sort of scenario where your dream candidate could be five blocks over from you but you would never know — is this: that candidate is no longer just competing with everyone else in New York City. They're also competing with someone in Sri Lanka where the AI just chose to apply to your job. They're competing against basically everyone under the sun trying to fit through a small pipeline. And so I think once we get rid of some of these old practices and beliefs around what it takes to understand people, hopefully we'll have a more positive hiring landscape."

What’s Next & The Big Ask

Mike: "Sounds like you have big announcements coming on the horizon. Without any spoiler alerts, what could someone listening to this or reading about this do to help you? What do you guys need the most right now?"

Founder Life: Habits & Staying Sane

Mike: "V, that's a lot of the business stuff. Let's talk about the founder stuff. Being a founder is stressful. Recruiting is stressful. Helping people recruit is stressful. How do you stay sane? What are your hacks?"

V: "I would question the assumption that I have stayed sane in any capacity over the last few years. But assuming that's true at all, I was talking to one of the other members of the club and I was like, I feel so lame that all I say is I like to vibe code and hang out with my friends. But I think in many ways I, over the course of this journey, have figured out the stuff that really matters. I realized there was maybe a point in my life where I thought I need to have more hobbies. No — I'm a plenty high-agency person. There's a lot that I want to do and there's a lot I get out of life. I think it was just about really shedding any assumptions of what I have to do, or how much I have to socialize with what kind of group, and instead just focus on what's the stuff that lets me get up in the morning, kick ass, and focus on that."

Mike: "Hanging out with friends and vibe coding. What more do you need?"

V: "Yeah, basically prototyping and hanging out with my friends. That's why the dinners are so nice. I just get to sit there and hear about what other people are up to and then go back and code."

Why NYC?

Mike: "Beautiful. Why are you guys in New York City?"

V: "So much of the last week has been, for better or worse, a discussion about New York and how New York stacks up next to SF and why I choose to continue to be there. I think it was a hard decision because in many ways it would have been much better for the company for me to move to Boston or for my co-founder to move there. But I think to the extent that I could have lived anywhere, SF is exciting, it's fun, and I certainly hope to spend more time here. But I think there's something awesome about New York that is just more human, you know? With all due respect to the folks in SF, they're very creative and they're very smart, but I get a lot of that on Twitter and I'm able to ingest a lot of that and develop my own POV on it. I don't necessarily need to be surrounded by it. New York's just more human, right? You just see more slices of life. And at the end of the day, the most salient insights of CareerSpan — the stuff that I know within the industry, that I will be able to say I was first to, or pointed out far earlier than others — it has nothing to do with the tech. It's all to do with the deeper understanding of the human need, which is: we need to figure out whether this person should be on our team. How do we answer that in a way that is fair to the candidate, but also helps you achieve what you want, which is to get the best talent at the best price that is the most willing to work for you."

Mike: "New York, more human. I like it. That should be on a t-shirt."

V: "Let's try to make it happen."

Surprising Facts

Mike: "V, what would people be surprised to learn about you?"

V: "I think a lot of folks are surprised that I'm not American — and not only am I not American, I'm originally Indian, and I've lived in three or four countries at this point. But I generally present as pretty American and could have been born in Jersey or some part of the Northeast. I think I come off in many ways as super American, and the founder energy doesn't help either. But I think people are surprised to find out that I'm not originally from the soil."

Mike: "What other countries did you live in? And when did you move to the US?"

V: "India for 12 years, Bangladesh for five years, Singapore for five years, and the US for whatever is the difference."

Mike: "So is the US the longest?"

V: "The US is the longest now, yeah. Just this year, that'll be over 12 years on continental soil."

Mike: "Wow, that's amazing. And where do you call home? What do you identify as home?"

V: "When people ask me where I'm from, I always have the stammer and the pause and a lot of hedging. I think home is a nebulous concept. I'm part of that group labeled TCK — third culture kids. And I think the really cool thing is home is just where I'm getting things done and where the people I care about are. I have legitimately lived in over 20 houses and apartments over my 33 years of life. You just get more used to change, you get more used to transitions. And it sucks that all your loved ones aren't clustered in one place, but then you have loved ones everywhere. I can go to so many of the world's best cities and just have a couch to crash on and a person to drink beer with. I think that is one of the better treasures to find in life."

Biggest Lessons from the Founder Journey

Mike: "V, you've been in the US for a while now. You've been a founder for a while now, too. What's been the biggest surprise? What's been the biggest lesson during your founder journey?"

V: "The biggest surprise has been — I see now why founders are such massive egotists, which I say with love. Because the biggest learning for me, or the decisions that I regret the most in retrospect, are the ones where my gut was telling me something but I didn't trust it. I think a lot of us are haunted by the decisions we didn't make. You're like, if only I'd done that, if I had just put my foot down. And I think I had a really long time of just making decisions like that back to back."

Mike: "Do you have a specific one you remember?"

V: "The shift to hiring, right? There are definitely some other companies that raised millions off of simpler concepts as far as the data acquisition is concerned. I think my mistake was really focusing on trying to collect the largest, most dense bulk of data that we can in a way that was still really human-centric. And those were the kind of lessons where I'm like, my instincts were wrong on that. But that's stuff I've luckily baked in pretty easily over the three years. I'm pretty good at figuring out when I'm wrong. The evidence slaps me in the face pretty easily."

Mike: "Why do you think founders do that? Or maybe more specifically, why do you think you did that — where your gut told you something and you just waited, you hesitated, you didn't act on it?"

V: "I've often wondered why being a bit cutthroat produces good outcomes on some time scales but horrendous outcomes on others. It's almost as though when you're trying to make a decision that is ethical and grounded and PR-friendly and fulfills all of the needs — we're all folks that want to have it all. My instinct is I want to have it all. I don't want to upset my team. I want to manage their expectations, but I also want to get what I want. And I think I realized over time that on a certain number of decisions, it just so happens that the moment I made the decision, I was carrying the wrong cluster of variables in my head. Whether that was, I don't want to upset this person, so whatever — I ended up conceding to multiple design and product decisions that I regret because I was like, this person seems to know more than me, they feel a lot of conviction. That's wrong. I should have been the one feeling the conviction."

Mike: "Yeah, my way of summarizing your answer and how I actually feel is: the reason I hesitated on all those decisions is because I was scared. I was scared of upsetting someone. I was scared of being wrong. I was scared of public failure."

V: "Right. And actually those are two sides of the same coin, right? Why do I want everyone to be happy except me? Fear. And so I think the truth is it comes from a place of not trusting yourself, which is related to fear — or not trusting your analysis, or even just the information you have in the scenario. Which could have nothing to do with you, but could still be such a source of insecurity or concern that it throws you off your game."

Mike: “Wow, wow, V, I really feel like I learned something in this conversation. That's all of the standard questions we have, so thank you so much.”

Vrijen Attawar is the CEO and Co-Founder of Careerspan, an AI hiring solution built on qualitative insights that are both authentic and predictive. The concept originated from his decade-long experience as a career coach and building the company has made him an expert in matching problems involving human data. He’s also a brand evangelist for Zo.computer and runs masterclasses on preparing non-technical people for a post-technical era. Vrijen has been an active member of NYC Founders Club since 2025.