Knuckle Up with Nakul

About Knuckle Up with Nakul

Knuckle Up is about the HOW of building iconic companies. Recruiting, culture, intensity, the inner game of being a founder CEO. The stuff that actually separates great companies from good ones. Hosted by Nakul Mandan (GP, Audacious Ventures), each episode goes deep with founders who’ve done it at the highest level. Not highlight reels. Operating playbooks, straight from the best of the best. knuckleuphq.substack.com (https://knuckleuphq.substack.com?utm_medium=podcast)

Publisher

Nakul Mandan

Category

business · technology

Language

en

Explicit

No

First episode

14 Apr 2026

Latest episode

13 Oct 2026

Latest episodes

4 of 15 episodes have a transcript.

1. 

   13 Oct 2026TRANSCRIPT

   How Railway says no to 90% of ideas and keeps winning | Jake Cooper (Founder, CEO)

   Nakul Mandan interviews Jake Cooper, Founder and CEO of Railway, about his disciplined approach to innovation and growth by saying no to 90% of ideas.

2. 

   22 Sept 2026TRANSCRIPT

   How Juicebox is building for the AI talent war | David Paffenholz (CEO)

   Host Nakul Mandan interviews Juicebox CEO David Paffenholz about building an AI-native recruiting platform and fostering employee retention through impact and equity.

3. 

   9 Sept 2026TRANSCRIPT

   $7B AI founder: "AI is not capable of replacing you right now"

   Nakul Mandan interviews Arvind Jain, founder and CEO of Glean, discussing AI's impact on enterprise workforces and the future of AI-native companies.

4. 

   25 Aug 2026TRANSCRIPT

   Inside Vercel's AI-era playbook: "Recursive Founder Mode"

   Nakul Mandan interviews Guillermo Rauch, founder and CEO of Vercel, about his "Recursive Founder Mode" playbook for scaling companies in the AI era.

5. 

   4 Aug 2026

   How a first-time CEO is taking on Google: No process, no NPC hires, and extreme shipping velocity

   Host Nakul Mandan interviews Will Bryk, CEO of Exa, about building a revolutionary search engine for AI agents with extreme shipping velocity and a unique hiring philosophy.

6. 

   21 Jul 2026

   0 → $1b in a year: The remarkable story of Handshake's refounding

   Host Nakul Mandan interviews Garrett Lord, CEO of Handshake, about rapidly scaling Handshake AI from zero to one billion dollars in revenue.

7. 

   7 Jul 2026

   The new marketing playbook: “Marketing Engineers” and agents as the audience

   Host Nakul Mandan interviews James Cadwallader, CEO of Profound, about the evolving marketing landscape and the rise of AI agents as the new audience.

8. 

   23 Jun 2026

   Building a $5b company without 996

   Most founders get more stressed as the company gets bigger. Immad Akhund has spent years engineering the opposite. “I’ve tried to make it so that the pressure kind of goes down as success goes up, which I think is relatively rare,” he says. “If you’re more successful, why are you more stressed about it?” This may be surprising coming from someone running one of the most loved fintechs of this generation. But Immad has reached this point through a deliberate operating philosophy that he shares in this discussion. Mercury serves around 300,000 customers, runs at a $650 million annualized run rate, and has been profitable for four years straight. One in three US startups banks with it, and in April 2026 the company won conditional approval to establish Mercury Bank, N.A. Immad has done all of it on his own terms: anti-996, still remote-first while Silicon Valley snapped back to fully in person, and hiring for curiosity and humility. The throughline is that he optimized early to be a founder for life, not for a sprint. In this conversation, Immad walks me through how that philosophy actually runs a 1,200-person company. Why 996 may not make you more productive. What Mercury’s famous curiosity interview is really testing. Why he killed one-on-ones after listening to Jensen Huang. How AI has turned the disruption of banking further in Mercury’s favor. And why, three startups in, the thing he would tell his younger self is to build something he would actually love to exist. Listen on YouTube (https://www.youtube.com/@KnuckleUpHQ), Spotify (https://open.spotify.com/show/5KorHDryscDzLwPkWEgAH1), and Apple Podcasts (https://podcasts.apple.com/us/podcast/knuckle-up-with-nakul/id1893213920) Immad Akhund is the co-founder and CEO of Mercury, the fintech banking platform founded in 2017 that serves around 300,000 businesses and runs at a $650 million annualized run rate. In April 2026, Mercury received conditional approval from the Office of the Comptroller of the Currency to establish Mercury Bank, N.A., and the company subsequently raised $200 million at a $5.2 billion valuation. Before Mercury, Akhund co-founded Heyzap, a mobile developer platform that went through Y Combinator and sold for $45 million in 2016, and earlier co-founded Clickpass. He has served as a part-time partner at Y Combinator and is a prolific angel investor backing more than 350 startups, including Airtable, Substack, and Deel. He was born in Pakistan and raised in the UK before moving to the United States. In this conversation with Immad Akhund: 00:00 Who is Immad Akhund? 01:53 Is culture just the founder’s personality externalized? 07:53 Is 996 actually less productive? 13:14 Why is Mercury still remote-first when Silicon Valley went back? 15:52 How did Immad hire Mercury’s first ten people? 20:33 What is Mercury’s famous “curiosity interview”? 25:06 How do you hold the hiring bar at 1,200 people? 28:48 What does Immad’s day-to-day look like? 34:10 How do you know when an exec is no longer right for the job? 37:32 Why does Mercury run on small, autonomous product teams? 40:27 What breaks when a company runs purely on metrics? 47:03 How is AI changing Mercury? 54:09 What does becoming a chartered bank actually change? 56:19 How did the SVB collapse end up helping Mercury? 1:03:40 What does psyche management look like 20 years in? 1:11:19 What does it mean to be at the founder “bonus levels”? 1:15:21 Quickfire: overrated traits, AI blind spots, and being proven wrong 1:17:52 What would Immad tell his 25-year-old self? Where to find Immad: * Mercury (https://mercury.com/) * X (https://x.com/immad) * LinkedIn (https://www.linkedin.com/in/iakhund/) Where to find Nakul: * X (https://x.com/nakul) * LinkedIn (https://www.linkedin.com/in/nakulmandan/) Where to find Audacious Ventures: * Website (https://www.audacious.co/) * LinkedIn (https://www.linkedin.com/company/audaciousventures/) Immad’s sharpest lines from this conversation: On pressure and success: “I’ve tried to make it so that the pressure kind of goes down as success goes up, which I think is actually relatively rare. If you’re more successful, why are you more stressed about it?” On the math of a 996 day: “The extra two hours, was that really 20% more productive? I will be shocked if it was 20% more productive. It’s maybe 5% more productive.” On where culture actually comes from: “It does start with founder personalities, but then you try to structure that, try to encourage that internally, then you hire against it. Then it becomes a self-perpetuating thing, and it also shows up in the product and how you talk to customers.” On why he killed one-on-ones: “I’ve never found one-on-ones help. One-on-ones is just an avenue for them to try to sell themselves. You need to create avenues where you have visibility into what that team is doing.” On holding execs accountable: “I don’t think execs can have excuses. I think that’s the job, to deliver on that.” On why AI favors Mercury: “I highly doubt Bank of America has an MCP. We are extremely well situated for that because we are a technology company, and that’s just what we do.” On reinvention: “I love change. I live for change. Change is the main thing I want in life.” On his advice to his 25-year-old self: “Build something that you would really love for it to exist, rather than being too spreadsheet about it.” Full Transcript: Immad Akhund on Knuckle Up Immad Akhund: 9-9 is 12 hours. The extra two hours, was that really 20% more productive? I will be shocked if it was 20% more productive. If you have five employees and you hire a sixth employee, that’s 20% more productive. You’re probably a little less creative if you’re not doing anything else in your life. I have my best ideas when I’m on a flight or driving somewhere. Sometimes these decisions or these ideas are actually worth 10x more than an extra few hours of work. I started as entrepreneur. I loved it, but I just wanted to survive. We got to a billion dollar valuation in 2021. At that point, which is like, I would say I really got into the bonus levels on this game where I was like, “I don’t even know what my next goal is.” I’ve tried to make it so the pressure goes down as success goes up, which is I think actually relatively rare. If you’re more successful, why are you more stressed about it? Nakul Mandan: Immad Akhund has built one of the most loved FinTechs of this generation. Mercury serves 300,000 customers and is at a $650 million annualized run rate. One in three US startups banks with them. The company has been profitable for four straight years, and as of last month, they have conditional approval to become Mercury Bank. But what’s interesting is that Immad has accomplished all of this on his own terms. He’s anti-996. He’s still remote first at a time when Silicon Valley has bounced back to fully in-person. He hires for traits most growth-stage companies don’t even look for. He said, “It’s dangerous when everything has to be driven by metrics.” And he said openly that he’s optimized early on to be a founder for life and not for a sprint. Today we talked to Immad about how he runs Mercury, the operating philosophy that got him here and whether that philosophy holds up as Mercury becomes a bank and AI-shaped company and a business serving companies well beyond the tech ecosystem. Knuckle up. Immad, welcome to the show. Immad Akhund: Ah, thanks for having me. Nakul Mandan: Yeah. So I want to start with something you’ve said that actually cuts through a lot of the culture theater in Silicon Valley. You’ve said that the culture is about the founder’s personality, not about some values doc, not about some rituals. The founder’s personality externalized. And I was wondering as I was preparing for this, that works for 10 people, 100 people company, maybe even stretch it to a 500 people company, but at the scale at which Mercury is today, 1000-plus people, does it still work? Immad Akhund: Oh, yeah. 100%. I mean, I think I often talk to people who talk about culture, but I think they don’t know what it means, and I think it’s like an ill-defined word and I’m an engineer, so I hate ill-defined words. So I really struggled with it for a long time. I was like, “Is it like having beers in the fridge and going, ‘That’s what it was,’ or is it like what programming language you choose, et cetera?” So I think there are probably some people mean culture and they mean something else. I think the easiest way to define culture that is very definitive and means something and you can measure it and all that is what are the personalities of the people you hire, what are the personalities that you encourage, what are the types of traits you encourage, kind of thing. You kind of have to decide that very early on because what happened in my previous company is I didn’t really understand that. So we had a bunch of salespeople that kind of ended up dominating the culture because they were the loudest voice in the room and we didn’t really have a counterculture to fix that. So it was fine, but it wasn’t like the type of company I wanted to build with Mercury. So we sat down and I think there was only four people and we’re like, “Okay, what are the personalities that we really cared about?” And for us it was kind of product-minded, humble, helpful people that were kind of curious and at that time we didn’t like meetings so we were like no process, go build things kind of people. And so we wrote that down and we tried to measure against it. We had interviews like every engineer, everyone we did product interviews with, and we would try to test people for, okay, are they high ego? So there’s a bunch of things that followed from that and we have a bunch of things within the company that encouraged that behavior. We pick one thing, like we have a channel called Grateful and people at the company, like every day there’s multiple posts where people are like, “Oh, I’m really grateful to X and Y because they helped launch this project or whatever it is.” A lot of that behavior is organic. I didn’t make that channel, it just came across. But I think it’s important and I also think different personalities can work. I always think of Uber as an example of a very competitive, high eco kind of culture, at least in the Travis days. Obviously they built a very successful company doing that. It doesn’t work for my personality. I also think it doesn’t work for the product we’re building. Yeah, maybe it could work, but I think Mercury is a very customer-centric kind of product where we’re very transparent and open with our customers and we try to be. That authenticity is part of the reason I think Mercury is successful. It does start with founder personalities, but then you try to structure that, try to encourage that internally, then you hire against it, then it becomes like a self-perpetuating thing and it also shows up in the product and how you talk to customers. Nakul Mandan: Does it potentially lead to also though having a lot of the same personality in the... Can a different personality come in into the company? Immad Akhund: Well, you need a little bit of just different energy sometimes, but it can sometimes ruin things. Sometimes you let someone who is a bad fit come as a leader. I mean, I think it’s especially an issue with exec level. I think at IC level, you can have a lot more variance and I don’t think it spoils things too much. But at a leadership level, if you have someone and then they hire people against them and for whatever reason that clashes with the rest of the company and then you can have a team that’s in a silo that... It can lead to a lot of bad things, and we are very careful at the exec level where we take a lot longer hiring and we try to test against our culture fit quite a bit. But it’s not like... You never have 100% conformity and you don’t necessarily want that either. You need enough of it that you are really being true to that culture and not letting it deteriorate. Nakul Mandan: What about the other side of it, which is the founder also evolves in the journey. Mercury has come such a long way. The Immad that started Mercury versus the Immad who is today. So has the culture evolved with your personality? Immad Akhund: We end up assessing it probably once a year and changing it once a year. Nakul Mandan: So it is a living doc. Immad Akhund: It is a living doc. Change is difficult to some extent because you don’t want to be drastically, “Now we believe in something completely different and opposite.” So what we tend to do is evaluate it from like, okay, the set of cultural things we have, are they serving us? Yeah, take that. We literally used to have one, like no meetings. I can’t remember the exact phrasing, but sometimes the fastest way to get to a decision is a meeting. Nakul Mandan: Oh, was it no weekly meeting? Immad Akhund: No, it was a very anti-meetings-like phrase. It was like, “We don’t like meetings.” And it was fine. When there’s 10 people and you’re all in a room, it doesn’t matter. But it wasn’t serving us and we got rid of that. And so there’s some that you remove and then there’s some that you’re like, “Hey, we really want to encourage this behavior.” You have to also try to shift culture by creating something. So I think one of the more recent one was we were like, “Focus on outcomes,” and then we created a bunch of things to... We try to create a bunch of rituals around the culture as well. So it’s like we’re focused on outcomes. So what are the outcomes we focus on? How do we drive that? How do we encourage it and celebrate when people are doing the right thing? How do we put in the performance management process so someone’s going to get promotion? Part of it is like, okay, maybe they did all the right things, but the outcomes didn’t happen and how do we measure all of that? So it has to be something that shifts over time. I think to some extent my personality changes over time, but not that much. I mean, I guess I started Mercury 80 years ago when I was 33. There hasn’t been drastic changes in personality. I mean, I learn a lot, but yeah, the core stuff is still the core. Nakul Mandan: In Silicon Valley these days, there’s a lot of talk about 996 constantly. It’s gone towards fully about intense cultures and you’re on the other side. You’ve built a $650 million revenue business. Obviously you have scaled in a way that very, very few people in history have scaled businesses. Can you talk about what does the 996 culture get wrong? What’s your though about this? Immad Akhund: From day zero we’ve had... We work hard, but it’s normally five days a week, whatever, 9:00 to 6:00 or something like that. We don’t have a religion around it. I have a family. I already had two kids before I started Mercury, now I have three, and I really see entrepreneurship as a long-term thing. I’ve done it for the last 20 years. I want to keep doing it for another 20 years. So I really want to do it in a way that it fits into my life. I used to be a 996 person, not because I was like, “Oh, I like 996.” It was just like I didn’t have kids, I wasn’t married. I woke up in the morning and I started... I was more than 996. I woke up at 9:00 and then I just worked till midnight being like, “Maybe you go out for dinner, maybe you don’t, and then who cares if it’s the weekend because you’re not doing anything.” That’s basically how I ran the first few years of my startup life. I think to some extent there’s been a shift with AI where being young is no longer a problem in the sense that with B2B SaaS, if you were young and you don’t have the experience to see B2B problems, it was hard to build a B2B SaaS company, which is the previous wave in the startup world. Now with AI, everything you’ve learned is probably wrong and you have to kind of reinvent it. Nakul Mandan: It’s liability problems. Immad Akhund: Yeah, it’s maybe even a liability. And also there’s just a lot of people out there that just want to play with the technology that are young, that... I started startups when I was 22. It’s the best time to do a startup. You have no obligations, you just need enough money to survive with the least amount of lifestyle cost. Yeah, there’s a big wave of young people. So I think that’s part of the shift that they don’t care. And I found personally when I was young and I was sitting on my computer all day, the reality is I wasn’t productive all day. I was on Twitter and I’m a pretty good programmer and that’s what I used to do in my early startup days, but there’s just only so much really productive in the zone programming you can do per day and the rest of the time you’re kind of pretending, sitting on a computer. So yeah, I think if you’re productive, like 9:00 to 6:00 and you’re just cranking away, I think you can be just as productive. Nakul Mandan: But your point is also that 996 is not good for the marathon of startups. Immad Akhund: Yeah, I don’t think it’s sustainable. I mean, I’d love... I’m sure there’s exceptions. But is it fun? I mean, is it fun not having a life? That’s the reality. I want to have fun. It’s like life’s too short to not have fun while we do things. I have fun building startups. It’s not a prison for me. Wow. I’m just going to... And maybe it’s fun for some people to just... I know people that it is probably fun for them to do just that and only that, but I like having friends and like spending time with my family. Nakul Mandan: If I steel man their argument a little bit, one could say, “Hey, the first few years of a startup, it’s so existential. If you don’t put everything into those first three years, especially... 996 is just a phrase, but all in all the time, then the longevity will not even matter,” versus optimizing for, “Hey, I’m going to be an entrepreneur for 20 years, maybe even longer,” which is what you’ve said. Would that argument hold, would that be a fair critique of, hey, the first three years, man? Immad Akhund: Yeah, I guess it’s okay. I mean, here’s my counterargument to it. I genuinely want to know... Let’s just take one day in this person’s life. 9-9 is 12 hours. The extra two hours from 10 hours to 12 hours, was that really 20% more productive? And I will be shocked if it was 20% more productive. It’s maybe 5% more productive. I think it’s just a reality of this. You just can’t be that much more productive. There’s only so much productive time you can have in a day. Okay, so maybe you’re getting five... I guess you’re throwing a Saturday in there. So let’s say you get 10% more productive. If you have five employees and you hire a sixth employee, that’s 20% more productive. I’m not sure, they’re working themselves to the bone. I think you’re probably a little less creative if you’re not doing anything else in your life. Even when I’m in the weekends and I’m not working, I’m thinking about Mercury. It’s processing. I have my best ideas when I’m on a flight or driving somewhere and I’m like, “Oh, why don’t we think about...” You’re grinding away, but actually sometimes these decisions or these ideas are actually worth 10x more than an extra few hours of work. That’s how a different fork can change everything. So that would be my counter to it, but at the same time, I think it’s fine. If people want to do it, I am supportive. I think it’s reasonable to say if you’re young, maybe that extra 10% is the difference and you don’t have the money to go hire an extra person. I think there’s lots of reasons why it’s completely reasonable and I’m not here dictating on what people should do. I don’t think it’s just obvious that that’s the only way to do it. Nakul Mandan: The other aspect where I think you guys are slightly different is you still are a remote-first culture and Silicon Valley dabbled with remote-first. Actually during COVID years, it was like, “Hey, talent is everywhere. Opportunity is not. Let’s get that talent.” But it bounced back pretty aggressively towards everyone in-person. What do you think of that dichotomy around remote-first versus everyone in-person? Because I do think you guys are somewhat different in this in 2026. Immad Akhund: I think when you are small and pre-product market fit, I would still recommend being in-person, and we were in-person until we were about 30 people and COVID hit. So from end of 2017 to 2020, we were in-person. I think later on there’s a lot of advantages that come from being remote and the actual in-person advantages kind of die down. We have 1,200 people. You can’t even fit them in one floor. So multiple floors. Probably most companies our scale even that in-person would have separate offices, et cetera. The really big advantage I find is talent. Often I’m hiring an exec and I’m like, “Oh, wouldn’t it be nice if this person was in San Francisco and I could see them often?” But I find someone amazing in New Jersey and I’m like, “Okay, am I going to get this amazing person? Is this amazing person going to uproot their whole life to come to SF? Probably not.” And it ends up being a differentiator. If there’s other companies that will not hire that person because they’re in New Jersey and they’re not there, then I can. So I think the talent is definitely better and is definitely differentiated. I do think there’s some downside, but it just requires more work. We create at the minimum three opportunities for people to meet in person every year. So we have an all hands where we bring the whole company together and each team gets two, and then on the leadership team, there’s probably five or six times we meet in person and we try to make those very intense in-person moments. So when you’re in office, you can go days not talking to people, or whatever, whereas when we get together, it’s like you’re doing social events together, you’re working together and you do need that in-person touchpoint to create these kind of bonds and create connections and create ideas. So yeah, I think the other pro on remote is, I think it is a little cheaper, especially in San Francisco. The cost of living’s really high, the expectations are very high. You’re competing against every whatever, and by now Anthropic, OpenAI, whatever it is. Yeah, I think on the talent side, it’s just a lot better, but it does require a lot of deliberate effort. Nakul Mandan: Yeah, on collaboration. I want to go towards your philosophy on recruiting and teams, but let’s go to the beginning. How did you hire your first 10 to 20 people? Immad Akhund: I think the super early stuff is really hard to hire. I remember after... So we raised a round from Andreessen Horowitz. So we were six million at a 23 million valuation, which- Nakul Mandan: At that time it was just you, or? Immad Akhund: It was me and my two co-founders who I’d met at my previous company. Yeah, this is 2017. So that was a unusually large and successful seed fund, especially since we were super early. We hadn’t ran much code and there was no traction or anything. And then I went to my friends that worked at Facebook and Google and all this stuff and there was nothing I could do to convince them to move. Because the problem is if you work at these big companies... If I was a seed stage startup now and I was trying to hire from Mercury, it would just be very hard because Mercury, the stock is relatively liquid and worth a lot and they pay a lot of money, whereas even if you raise $5 million or whatever, it’s very hard to sell them. So I found the two main things we could do was like, A, go to people I knew. So actually five of the initial eight people, which is what we mostly built the initial product with, worked with me at my previous company and all of them still work at Mercury. And then the other thing is young talent, people who aren’t proven. It’s just much easier to even go to Stanford or even a smaller college or whatever and you hire someone straight from college. Those people aren’t necessarily getting a chance at these kind of mega companies, but there’s some great talent there and you just have to be really thoughtful by identifying it. There’s also another set of people are just very into small companies and those people tend to be pretty good as well. Nakul Mandan: How much of your first year did you spend on recruiting? Immad Akhund: One thing I always tell entrepreneurs is like, if you want to recruit, the only way to do it is if you make your number one priority, especially as a small company. No one else is going to do it for you. Nakul Mandan: Is there any other way? When you say if you want to recruit, every founder has to recruit. It has to be that way, right? Immad Akhund: I like phases when I’m early on. So we raised that six million, I recruited up to a team of eight and then I stopped, and then we executed for a year and a half. I think we hired one other person then, but until we launched, we didn’t hire anyone else. Nakul Mandan: So for those phases, it’s the number one priority for you. Immad Akhund: Yeah. It doesn’t mean you don’t do anything else, but I find recruiting a little boring, to be honest. It’s like programming or sales is a little more fun, whereas recruiting is a bit of a grind for me, but it’s necessary. And I’m always like, if I spend one moment of my time not recruiting... To go back to that previous thing where I said if you go from five people to six people, you become 20% more productive. Especially when you’re a small team, it’s very hard to beat the productivity you’ll get from another good person. Why spend time doing something myself when I could hire that incremental person? Obviously at some point you shouldn’t hire, which we could talk about when to stop. But yeah, you wake up in the morning, you’re like, “Okay, recruiting’s my number one priority. So what’s there to do?” Job postings, trying to get referrals, emailing people that you know. It’s a grind. You just got to wake up every morning, and hitting up people on LinkedIn, whatever it is, you just have to do it. Nakul Mandan: But during that phase, when you say it’s your number one priority, how much approximately your time is spending? 50%, 30%? Immad Akhund: About 50%. Nakul Mandan: Above 50%. Immad Akhund: Yeah. I mean, if you include interviews, if you go multiple roles, it’s very time-consuming. Nakul Mandan: For the first 10, 20 people, were you looking for something specific in terms of one or two traits that really mattered that might matter slightly less today, but those 20 hires, was there something like that? Immad Akhund: I wouldn’t say it’s like the things that I don’t look for now. And often people kind of glorify those early people at startups a little bit. I actually think we get better people now than we did early because people know Mercury and we can hire really amazing people, whereas it was hard hiring great people early on. Yeah. I mean, I think there’s some attributes that are really essential when you’re early, but I would say they’re still essential now. You want people that have really strong ownership mindset. I’m always like, “Hey, it’s not like I’m not going to tell you what to do. You come here, you figure it out and you get it done kind of thing.” So you want people that have that kind of ownership mindset. I still want those people. I don’t want people who are waiting to be told what to do. And then you want people that are very product-minded, that really care, and again, we still want that. I think one thing that does happen over time is you end up having more specialists. If you want to hire someone in AML investigations, that’s pretty specialist and we go hire people with a lot of experience to do that. Early on, you want much more generalists that can slot into different things very easily. Nakul Mandan: Mercury famously has this curiosity interview. You give somebody an hour to present a non-work topic to their team or the team they would be joining. What are you testing there? Immad Akhund: So I came up with this idea and it’s probably been 12 years or something since I came up with it, but basically I’m an engineer and then I had to hire a sales team at my previous company and I was like, “These salespeople are just so good at talking.” You come up with any fricking interview questions for salespeople and you’re like, “How would you run a pipeline?” And they have these really beautiful answers to these things. So with engineering, I was like, “Okay, you just give them a coding challenge. That’s how you test if someone’s good at engineering.” So I was like, “What is the coding challenge equivalent for sales?” And then I came up with this answer that I was like, “Hey, present me a topic of your choice, spend 45 minutes preparing a presentation and you do it and we’ll talk about it.” And it was an amazing filter for salespeople. I’d have these conversations with them, they were amazing. I’d be like, “Oh, this is the best salesperson I’ve ever spoken to,” and they’d come in on these presentation things and they could not talk about anything interesting. And if you ask them questions, they wouldn’t have thoughtful responses. And it turned out to be an amazing filter for salespeople. So since then I basically kept... I was like, “Okay, it works for salespeople. Why don’t we do it for basically every role?” So we don’t do it for engineers generally. Things that have a coding challenge or designers where you can really test a work sample and see what it’s like, I think it’s less useful, and honestly, the times I’ve done it with engineers, they’re just too good at it anyway, because engineers always have some quirky thing that they know way too well. But for most other levels and roles... We do it a lot for exec hiring. It’s amazing filter for that as well. Nakul Mandan: But what are you getting there? Is it that this person is multidimensional or that there’s standard interview topics they know how to ace? Immad Akhund: So there’s a bunch of elements and we have a whole grading score for it. So it’s not that you just sit back and listen to them. It’s a much more conversational kind of thing. There is a basic thing, like are they interested in some interesting things and have they gone deep on those subjects? And most good people who are going to do a good job and at least my experience with people who are great in their job, they have weird things that they’re really interested in and they know a lot about. That’s almost universal. I mean, obviously we’re biased with Mercury, but you probably have some weird thing that you know way too much about. I think it shows you’re curious, you’re interested, you want to learn things, and it’s the types of thing. In a startup, you need people who are curious, they want to learn things because there’s always going to be something new and there’s always going to be something. So that is a strong filter. There’s also like, how do they react to... We try to intrigue them and push back and some people get real defensive about it. We want to have a culture where it’s like back and forth and we challenge you on ideas and say like... And then there’s this kind of general product. If you think about the abstract of what is product thinking and product thinking is this being able to see a problem, come up with answers and solutions to it. So we have some classic questions that we do as counters. So we’d be like... If you’re really interested in, I don’t know, pickleball, we’ll be like, “Hey, let’s say you’re in charge of making pickleball really popular in America, what would you do?” And it’s not quite build a product, but it’s kind of product thinking. And some people are just like, “Oh, yeah. I’d go do this and that in schools.” They have five or six things that come up with quickly. Other people just completely struggle and go blank on that kind of stuff and I guess we want the people that are good at it. So we actually literally look at it in terms of every single cultural value we have and how do we have one question that tests against all of that? It’s actually one of the best ways to tell ego as well. People who are high ego, they cannot handle pushback or any sort of challenge to an idea, whereas people are humble or much more like, “Oh, yeah. That’s really interesting,” and they enjoy that kind of pushback. Nakul Mandan: Has there ever been an exception made in the sense that somebody who was acing their sales scores, whatever, the interview, their past background, on the curiosity interview, they did okay, maybe not bombed it because- Immad Akhund: Not for sales. I would never make an exception for sales. This is your core job. The presentation interview is 100% correlated with a sales job. We have made exceptions for some other things. I don’t love making an exception ever really, but sometimes it’s like a very specialist skillset and this person’s got a ton of background on it, and yeah, maybe they’re not a customer-facing role and they don’t have to be that product-facing and we’ve made exceptions. I don’t love it. I personally would never make an exception, but I know some people in the team to have. Nakul Mandan: How are you ensuring that as the company has grown to 1200 people that the recruiting bar is still high? Because the first, I don’t know... Till what time were you meeting almost every person? Immad Akhund: Yeah, I think around 180 I met everyone, and then since then you basically have to take the things that you did and try to productionize them. I mean, I don’t want to keep talking about this presentation interview, but we set up a training course so other people can conduct the interview and we see how they do it and we score them on their ability to score the interview and then we take the different things we’re measuring and we turn that into a rubric that we judge in that interview process. So across all the interviews, we try to hold a bar in that sense. And then there’s also performance managing on the other side. I think no interview process is perfect. You’re trying to make a judgment after a few hours. So you just have to hold a bar on the other side as well and say, “Okay, they came in, how are they doing?” Nakul Mandan: Do you guys do a lot of back channel references? Is that a critical part of your process or not? Immad Akhund: Definitely for leaders and execs and things like that. Sometimes we end up doing it for lower level things. I don’t find them super useful outside execs, but yeah, I don’t think it’s necessarily critical. Nakul Mandan: Have any of your beliefs on recruiting and team building or even how teams are run evolved as Mercury’s scales goes up? You’ve been an entrepreneur for a long time, but this is- Immad Akhund: Oh, yeah. By far. My previous company was 20 when we sold. One thing that was a complete game changer to me, which maybe it’s obvious to everyone, but it definitely wasn’t to me, is after we raised the series A... Our series A was like 20 million raised. Someone, Josh from Gusto, he said, “Hey, maybe you should get a recruiter,” because I was asking him for tips on hiring now that we had like... I was like, “Oh, a recruiter.” And I’d kind of had experiences with external contingency recruiters, which I basically never had a good experience with. So then we ended up hiring an internal recruiter and that was completely game-changing because we went from me and someone else in the team trying to directly find people from my network, et cetera, to someone who’s just dedicated 100% of the time to finding the best talent. Complete game changer. Now we have a pretty big recruiting team of, I think it’s 15-ish. Having a great recruiting team... And actually one thing we ended up doing is that first recruiter became our VP of recruiting, but she was really strong at sussing out culture. So often... And maybe I shouldn’t say this on camera, but often people are kind of rude or dismissive of recruiters because I guess they’re used to not taking them seriously, but that’s the first touchpoint of the company. And if someone’s rude or dismissive or whatever to the recruiter, that’s a super bad sign. I guess in general, people tend to be very honest with recruiters and who they really are, whereas they’re sometimes retaining. So it actually ends up being a really strong cultural filter for us. But yeah, having an internal recruiter is a complete game changer. I often talk to people who are series A, sometimes in series B companies and they still haven’t thought of this and always told them this. So if you’re working at all with external contingency recruiters and you’re hiring two people a month or something like that, it’s a no-brainer. You’re going to save money and it’s going to be better hires. Nakul Mandan: It does seem to work better when the recruiter is treated even internally as a true partner by the VP of [inaudible 00:28:29], VP of sales and often it can be- Immad Akhund: There is literally no role at the company that works better if you don’t treat them as a true internal partner, whether it’s compliance or sales or recruiting or whatever. I think one of the biggest mistakes people make at companies is not... If you’re going to have a role, you should make them a core part of what makes you successful, otherwise you’re wasting an opportunity. Nakul Mandan: Let’s walk through what does your week look like at today’s scale, week as a CEO. So what’s your Monday like and how much time are you spending on product, sales, marketing today through the week? Immad Akhund: Well, one thing I should plug is I got rid of one-on-ones. I actually listened a year and a half or so ago to Jensen Huang and he runs this company super funny, but he’s got like 60 direct reports he said. But one of the things he said is he got rid of one-on-ones. And up until that point, I was running one-on-ones with everyone that reports to me and a few other people and I was like, “Wow. I don’t find those meetings overly useful.” And then I talked to a bunch of other CEOs and they’d also got rid of one-on-ones, not universally, but it was actually much more common than I thought. So if you have mostly leaders and execs reporting to you, I think you should probably get rid of one-on-ones. So that’s something I’ll go out there and say. But that’s freed up a lot of my time and I actually ended up then increasing the number of direct reports I had because one-on-ones are just like... They take up a lot of time. Imagine if you have 10 reports and you’re doing weekly one-on-ones, that’s one day wiped out, but they also take a lot of headspace as well. So anyway, I replaced all one-on-ones with group team meeting things with execs. So I have a series of things that we have a weekly all-exec meeting, then I have a biweekly, I think, GTM meeting, EPD execs, and then compliance and risk, legal, and then GNA. So exec meetings are on set of things we do and we try to get these into not status updates. I can’t stand status updates. It’s all like let’s go into meeting discussion topics around whatever’s the most important aspect of that team. So that’s a reasonable chunk of my meeting. On Fridays we do what I call exec workshop where it’s three hours long or something. It’s kind of like an office hours where I will either go to a team and say like, “Hey, I want you to come in and talk about what you’re working on for 30 minutes,” or a team will come to us and there’s a channel, Slack channel for it, where they’ll say, “There’s a new product launching, we want to show you what we’re working on, et cetera.” And all the execs are there, but it’s often a venue for me to see what’s happening and opine on it and for teams to get decisions made at the exec level. Then a lot of the rest of it is I’m still recruiting, especially if it’s execs, there’s a lot of... Like this morning, I mean, today I think I’ve done three interviews so far. So yeah, recruiting is a big part of the rest of it. Nakul Mandan: How much of your attention is still on product and product innovation for Mercury? Immad Akhund: Yeah, in that exec product workshop, there’s a ton of it. And then we do a ton asynchronously. So I instituted this two channels I can’t remember how long ago, two, three years ago, but we call it the pre-shipped channel and the shipped channel. And basically anything that’s often design-ready, like initial designs or sometimes it’s just like spec mode, goes to the pre-ship channel. Everyone’s part of it, but it gives me a... Yeah, I can see what everyone’s working on basically. And then the shipped channel is when it goes to production. So these channels are super busy because they’re shipping things all the time and that lets me quite quickly see, and then if I’m interested in something or have questions, I’ll either tell them to come to the exec workshop or I’ll just reach out to them. That’s my main direct involvement with product. The other place where often comes up is if you’re launching something big, I’ll go test product out and give feedback. And then the other big thing is if there is new things we are working on... I have a lot of ideas. So often, but not always, often the ideas for a new product and we’ve in the last, I guess three, four years, we’ve gone very multi-product. So we’ve got the core banking, but we also have credit cards and invoicing and bill pay, and we also just acquired a payroll company and there’s a couple of other things that we’re working on. But those ideas often come from me and then there’s a kind of process of me pitching them and seeing if an existing team can do it or instantiating a new team and then hiring against it, et cetera, that is also often top-down. Nakul Mandan: But do you think of your week as in different phases, I’m guessing similarly like, “Hey, I’m attacking this massive problem that I need to solve,” or it kind of is a steady marketing product, sales, recruiting dial? Immad Akhund: Definitely there’s always some big problem and I end up devoting quite a lot of time to it. So at the start of this year, I kind of took over as a CTO. We’re doing a CTO search. If anyone goods out there, ping me. But as taking over for CTO, I ended up reorging the team a little bit and going in there and saying like, “Okay, what are the big problems? What can I make some quick wins with?” And so that was very time-consuming. I’d say still pretty time-consuming. I’m very involved in the engineering day-to-day stuff in a way that I wasn’t before I took over. But this ends up happening every year that there’s some department where I take over because someone leaves or they’re not working out or we need to do a change. So I end up learning about all sorts of things in doing this. I think a big part of how I see my role, there’s the steady state stuff, but then there’s the chief problem solver/chief opportunity finder kind of thing and then you go very deep on that. Nakul Mandan: Actually, one topic I’d love to get your take on is how do you know an exec is no longer the right exec? So beyond the initial culture for it where somebody came in, didn’t work out, put that aside, somebody was great for two, three years, but they might not be good for the next two, three years. What are the early signals somebody’s plateaued for the next two, three years? Immad Akhund: I’d say honestly, it becomes pretty obvious by the time you make that decision and you’re normally like, “Wow. I should have decided a while ago.” Here’s some factors. Do they hire a really strong bench underneath them? I find that the best execs, you look one layer below them and you’re like, “Wow. These people could do your job.” I think that not everyone, but they normally have two people that at least or maybe three people that you’re like, “Wow. These are amazing leaders of the company.” Obviously you can’t expect that day zero from an exec, but an exec that’s done a really good job is both hired/facilitated really strong talent just below them. Number two, I think the higher up a company you go in the chain, the less excuses you can have. Me as a CEO, I have no excuse. If something’s going wrong, it’s my fault. But I think it’s the same, one level lower. To go back to the, are you driving impact? I don’t care how good your reports are. You could do these amazing presentations. I don’t care. And generally every exec has very strong things that they’re aiming for, whether it’s launching products or driving sales or whatever the metrics are that you would judge that exec on. And yeah, I don’t think execs can have excuses. I think that’s like the job is to deliver on that. So I’d say those, two talent and delivery, are probably the two most important kind of measures where people start failing. And talent is often one where you can see people not scaling. They don’t think ahead, they don’t think what is needed, but same with outcomes. They’re not necessarily driving what’s a 10x outcome. The shape of almost every org needs to be different, 10x bigger. Nakul Mandan: If you’re not doing one-on-ones, is there a risk of not catching that plateauing of that exec early on enough? Immad Akhund: I mean, I’ve never found one-on-ones help. One-on-ones is just an avenue for them to try to sell themselves. You need to create avenues where you have visibility into what that team is doing. So I guess I didn’t talk about this, but most of our teams do a quarterly review kind of thing where they write a... We do docs, we don’t do any presidency. Write a doc about what’s your team doing well, the deliveries, what are you going to do next time, do some deep dives kind of stuff. So you get a sense from that. I mean, if it’s a core thing, like it’s product or sales or whatever, you’re seeing the metrics all the time. Are we delivering? Are we behind on deadlines? Are we driving enough sales? Yeah, I find that it’s my job to have that visibility, but not doing one-on-ones does not mean I’m not interacting with them all the time. Whatever the role is, there are tons of meetings that I’m part of where I’m seeing them perform, whether it’s the exec meetings or whether it’s the group meetings or whether it’s product meetings. There’s just so many places I see, especially the people that report to me, I see them. All of them, I’ll see at least once a week, if not multiple times. So yeah, it’s up to me to understand what they’re doing and see if they’re delivering on it. Yeah, I’ve never found one-on-ones with the way to do it anyway. Nakul Mandan: And then one of your operating principles is that I think the fastest or the most functional team is a 10% team. So you guys have kind of recreated that with an eight person product team, one PM, one designer, six engineers or something like that. Immad Akhund: Yeah. Nakul Mandan: How many such teams actually exist at Mercury today? Immad Akhund: Yeah. To some extent, maybe this is changing with AI, but this comes from my startup routes. I’ve always thought, wow, startups just seem way more efficient than a big company. And if you look at it... Mercury has 400 engineers, so in theory, we should produce 40 times more than a seed-stage startup. Obviously we have to maintain a base and blah, blah, blah. So then you have to go like, “What is it that makes these small teams more efficient?” I think there’s small teams that have, I call them autonomous product teams, they have to have a overall remit where they can independently work where you’re like, “Hey, you own this thing. This is your KPI that you own. This is your product surface area. Go talk to customers, go figure out your roadmap.” And maybe there’ll be some top-down, but that team is kind of driving it and owning it and feeling the responsibility for it. I think that is an ideal team. We have so many of these at this point. Let’s see, one, two times... At least 15. Nakul Mandan: And are these truly autonomous teams now? Where do they need your approval on product decisions? Immad Akhund: My approval, very little. The bit where they’re not autonomous is when they need to work with each other and to do big things. We have one team that’s on our Mercury personal product, which is our personal banker product. But yeah, the reality is sometimes they need to work with our risk disputes team or they need to work with our cards team and then there’s some collaboration and for some teams they can really be independent. We have a invoicing team and they’re failing, but even then they have to work with a mobile team. But anyway. There are overlaps and that’s where they can’t be fully autonomous, but they all have a real ownership or on a end result that they’re driving at. And a lot of their roadmap is set internally. There’s bits where at the end of last year we did go and say like, “Hey, these are the big, big things we want to launch in 2026,” and in November last year, we set out a six item product calendar for this year, which we’re still working on. So for those teams, we were really a little more top-down and we were like, “Okay, this is a big initiative. What does it take to get this successful?” But even then somewhat the top-down is like, “We are going to launch this.” We just launched an insights product, which helps you give insights on your... But how exactly it works, what are all the features is fairly up to the team to kind of... Nakul Mandan: Are they all reporting into a head of product or? Immad Akhund: Yeah. So we have two VPs of product. One is banking and risk, and the other is experiences, and they report to my co-founder who’s kind of head of product and design. Nakul Mandan: You also said something around it’s dangerous if companies decisions are only made on metrics, and I think as an extension, I think you were talking about taste versus metrics. Correct me if I’m wrong on that, but how does that play out in your mind? Why did you say that? And then I would love to dive deeper into that once... Immad Akhund: So I think there’s some teams that are very metrics-driven and have to be. So a lot of our growth teams, you’re trying to drive conversion from sign up to application. And that’s a complicated process because we’re a bank, but there’s so many steps in that you can optimize and mostly you should be driven by metrics when you’re optimizing them. I think if that’s all you do, you’re going to end up with these kind of local maximas of like, “Oh, yeah. We optimized that and we increased conversion rate on that.” And I see some companies do that. I think to some extent Facebook, the app, Facebook lost their heart because they become so metrics-driven that they’d never actually thought about the customer. I do think the other set of things are like it’s just harder to measure metrics on a lot of improvements to customer experience. So we collect W9s. So if you want to pay a contractor, you’re supposed to collect tax information. And yeah, what are the metric we were optimizing for that? I mean, customers like it. It makes a huge difference to people’s lives because they’d have to collect these over email and type them in. It’s definitely better, but I just don’t know what metric you would drive for that. I mean, obviously you want to launch that feature and people use it, but there’s no overall company-level metric. I mean, eventually it’ll drive retention and maybe customers will tell each other about it and then there’ll be more. It’s not even about taste. I think building an amazing product that helps people, there’s just not that much that’s just pure let’s crank the wheel on optimizing metrics. So that’s my main point. At the end of the day, the company needs to drive EBITDA. We need to drive profit and that’s the only metric that really matters, but how you get there is a kind of... Nakul Mandan: Yeah, it kind of speaks to you and Mercury are both very product-led. I mean, Mercury is an extension of you. So you’re saying product, it has to be product-led, not growths-led. Immad Akhund: Yeah. It’s like, how do we help customers? How do we solve their pains? A lot of that I don’t think is a metric that you’re driving. Nakul Mandan: But then again, as you’ve scaled to such a point, how have you thought about your product taste and product intuition scaling with the company? Because now it’s like Mercury started with a beloved product. Obviously it was beloved. That’s why it got product market fit. Now you’re so many products and you’re expanding that portfolio. Immad Akhund: I mean, firstly, it’s not my product taste most of the time. I think if it comes to me and I’m the reason we... Obviously sometimes it is mine. Sometimes I see things that someone thought about at Mercury. I’m like, “Wow. I didn’t even think we could do that,” or, “That was a great idea.” And we encourage a very close collaboration between engineering, PM and design to come up with products and talk to customers. There’s no way that’s going to come from me. I’m not in the weeds on a very... Sometimes I am, but most of the time the designer working on the product has thought about it way more than I have. So the main thing I do is when that slips up, I’m going to complain a lot, not like in a, “Oh, this team sucks.” But I’ll go, and not always, but I try to go pretty deep into products we ship. Obviously I’m the user on Mercury, but I have my own fund on Mercury, my wife’s business on Mercury. So I just test these things out and I’m like, “Okay, is this good or not?” And then I give that feedback to the team. So in that sense, I think actually complaining is a pretty good skillset for... You have to try to put yourself in a mindset of like, I don’t know anything about Mercury, but what are all the things that just would bug me, if I turned up at this product, I’d be so annoyed that I have to click this button or this thing doesn’t make any sense? So I try to be this kind of mindset of I don’t want to think too much. I just want to have an amazing experience. And when it doesn’t feel like that, I can manifest that user, have a lot of sympathy for what that user would be. That I think is an important skill to have. But yeah, the product thinking and delivering a great product, you can’t be doing that top-down. The team has to be driving that. Nakul Mandan: A similar question on scale. How do you ensure it remains a very performance-driven organization at this scale? It’s just the quarterly reviews or trusting the [inaudible 00:44:56]? Immad Akhund: I guess it depends what you mean by performance-driven. What do you mean by performance-driven? Because there’s a lot of elements to that, right? There’s like, are you driving revenue? Are you launching products and things like that? Nakul Mandan: I think it’s different for different teams. My question was more oriented towards... So obviously for some metric-driven teams like growth, marketing, sales, it’s much more metric-driven, but on product, on design, customer support, there’s an intentionality and obsession with the outcome or impact. How are you ensuring that that’s just percolating through the organization even as the company scales? Because stasis sets in with scale over time or apathy. Immad Akhund: Yeah, that’s a good point. I think every team and concept at Mercury deserves its own kind of thought on how you do it. If you think about, let’s say customer support, you can be putting metrics-driven there. You’re like, “Okay, what is the customer satisfaction? How many tickets are being processed? Are we reducing our meantime to get it to a ticket?” At the engineering, you also have metrics. It’s like per request per week, or are you shipping on time to the calendar that you had set kind of thing. So I think there’s the metrics side of it. I think second part of it is culture. Do people love what they’re doing? Are they enjoying... When you’re small, again, people do things because they do things. It’s not like there’s an external, you have to perform in order... I think if people are liking what they’re doing, they’re liking the team, they understand why they’re doing it and how they’re helping customers. People want to ship things and they want to do things, I think at least the types of people we try to hire. And then you do no matter what, have to have a bar where you’re willing to fire people that are not performing. I think if you don’t hold that over time A player team gets a few B or C players and then they’re like, “Okay, these people aren’t working,” or they keep having to fill in for them and that can deteriorate the culture of the team. So you have to have that bar and you have to continuously be enforcing it. Nakul Mandan: Let’s talk about how AI is changing how Mercury is run. First of all, actually, how much of your own cadence has changed with AI? How deeply embedded is AI in your decision making or visibility into the organization? Immad Akhund: I use it a lot just for structuring my thoughts, thinking through problems, definitely seeing what everyone’s up to, and then I try to get... I wrote some code actually, did some Claude Code stuff. I mean, I’ve done some personal projects, but I wrote some production code, which I hadn’t done since 2021 actually, so that was kind of fun. But at the CEO level, it’s not necessarily been as drastic as other places. I mean, I have a literal Claude Coworker thing that helps me prepare for meetings and things like that, but I wouldn’t say it’s been complete game changer. Obviously engineering team, it’s been a complete game changer, especially for new product development. I think existing, maybe some of our core banking core and payment stuff, it helps, but it’s not been like 10x. But yeah, if you’re doing something completely new greenfield, it’s amazing. We’ve done a bunch of stuff to help encourage that. We have an AI enablement team that is working on tooling for the engineers, but also for the broader organization. So super useful there. And then on the rest of the teams, we encourage a lot of usage and then... Yeah. So whether it’s our finance team or our legal team... Our legal team’s actually the biggest users of AI. We did a vote recently. It’s like 80% of them say that it’s saved them 20 hours a week or something like that. It’s been an insane use. Nakul Mandan: Have you guys adopted things like Decagon on customer support or some of these things? Immad Akhund: Yeah. So on the customer support side, it’s been really good. About 35% of our tickets are responded straight away. We’re using Fin right now. Over time, we’re probably going to bring it completely in-house just because the next level of tickets, if we want to get it to 70%, you kind of have to go integrate into internal systems and at that point it might as well be internal. Yeah, super useful there. And then we’re launching a bunch of AI-related features where we launched a... So on part of it is connecting into AI. So we have a Mercury MCP and a Mercury CLI. So if you’re using Claud Code or Coworker or Codex or whatever it is, you can plug into Mercury and have workflows done. Nakul Mandan: As a customer? Immad Akhund: As a customer. The usage of that is going crazy. There’s lots of interesting things people are doing with it. You can analyze your finances or you can see all the pending payment requests and tie them into some of the workflow. You can generate invoices. It’s like all the things you can do in Mercury and we keep adding more and more of those features into it. So that’s been big. The second thing is we are adding more AI features directly into Mercury. So we launched this Mercury Insights thing where you can talk to your transactions, summarize them for you like, “Why did my AWS bill change in the last month?” Or whatever it is. There’s lots of kind of questions you can ask around that data. And the more of Mercury you use, the better those answers can be. If you use us for credit card and banking and invoicing, you can ask a lot more. And then we’re actually launching another thing later this year, it’s called Mercury Command, where it’ll basically let you do a bunch of the workflows that you can do within Mercury directly from AI. Instead of having to learn all the commands or string together different actions, you can just be like, “Hey, I need to pay my landlord 5K for the month,” and they’ll try to figure out what you mean and pop up something. Every action still needs affirmative action. We don’t let the AI do the action, but we can basically automate a ton of your workflows directly from Mercury. Nakul Mandan: Have you seen your sales and marketing orgs also embrace AI very aggressively or not yet? Immad Akhund: Yes, but we went through this first phase and I think it’s probably got a lot better where we went and adopted some AI SDRs and it kind of sucked. And actually I think it probably still sucks. At least the AI STRs flood the field. So then the signal-to-noise ratio is way off. So you have to be different in order to stand out. But what we have found is enabling the salespeople with the right thing to say is a really powerful thing. It’s like, who should I speak to? Someone just raised some money. It’s like as you’re sending the email, it’s like, “Oh, yeah. Congrats on the one million raised,” dot-dot-dot, or they just hired the first finance person. That’s a great point for them when they’re considering new finance deals. So we find at least right now, and I think it’ll change over time as AI and the sales team has been more useful as an enabler to internal people rather than a replacement. But yeah, we are hiring pretty aggressively on the sales side. So it’s definitely not freed up any headcount. Nakul Mandan: Has your recruiting criteria across various business functions changed towards testing for AI fluency or nativeness or not yet? Immad Akhund: Definitely on the engineering side, I think it’s almost a given that you need to be very fluent with it, and at this point, if you’re not, it’ll be surprising. I wouldn’t say it’s changed too much outside the EPD function, the engineering product design. I guess data also has become a much more AI field. So I’d say case by case on the other ones. I don’t know if the finance person needs to. Nakul Mandan: And you touched on some of the product things that are coming out, but how has AI changed taking a step back Mercury’s long-term vision? Immad Akhund: I think the interesting thing about Mercury, and maybe this is true for other startups as well, I feel like if you’re on the right side of where history’s going, then almost everything helps you. At least that’s what I’ve noticed with Mercury, which for us, the right side is banking is going to be disrupted by FinTech and technology companies are going to really be the source of that disruption. Some of the stuff is obvious. Banking is going to be online and digital. It’s going to be mobile apps and websites rather than bank branches. And one of the original thesis for Mercury was always like banking can do a lot more. It’s not just the bank account, it’s going to be the whole financial suite. So everything that’s happened... When COVID happened, that was a big boon for us because bank branches were closed and you had to come. AI is another one where it’s now the way you interact with banking and the tools you expect from banking and all the places you can use it in the back office is completely shifted. Nakul Mandan: Yeah, I highly doubt Bank of America as an MCP. Immad Akhund: Yeah. We are extremely well-situated for that because we are a technology company and that’s just what we do, whereas what would be a threat to anyone else is a big boon for us because now it’s like our differentiator is now even further. It was already great, but now if you want to be able to connect it to your MCP, there’s just no one else that’s going to do that for you. Yeah, that’s my high level take on it. Yeah, I think it means that the things that we do have changed and a lot of our focus has changed around it, but at the same time, it’s mostly accelerated the overall vision, which is still like, how do we deliver great products to our customers? How do we speed up their life and make it easier? How do we give them great insights? All of these things were in my seeds pitch. This is how I always describe Mercury. It’s just like, now we’re going to do it with AI as part of that pitch. Nakul Mandan: You also recently got the approval to establish Mercury Bank, but your interface has always been a banking interface. So does that change much for the customer or is this more about the backend operations and maybe some downstream products you can unleash because of that, but the banking interface or the Mercury interface remains the same? Immad Akhund: So the interface will be the same. It will enable a few extra features. So we’ll have Zelle support, which isn’t something we have right now. We’ll have a lot more lending products that we can offer our customers, which to this day we have a couple, but we really minimize lending. So that’s one thing. There’ll be lots of smaller changes that maybe people won’t even notice, but we will have quicker money movement. It’s just like if you control every step of it and we are trying to... When we do the Mercury bank integrations, we are going directly to the Fed and because we control every step of it, give you the biggest cutoff windows and we could just guarantee a lot more and those things will... We care about those little things even if customers sometimes don’t notice. Economically it’ll also be better for us. But I think overall it’s also what makes sense for the long term for us, which is right now if you go to mercury.com, there’s a lot of disclaimers on there because we can’t call ourselves a bank and we have to make it very clear to our customers where they’re actually banking. And that doesn’t always engender the most trust from our customers. If you don’t know about Mercury and you show up there, you’re like, “What is this? I’m not getting a bank here.” It creates confusion. I genuinely think if Mercury was a bank in a chartered sense, I don’t know why someone would not use Mercury. Yeah, at this point I can say, okay, some people used to have some reservations about using a FinTech that has this pass through bank relationship, but yeah, I think it’ll go a long way for trust. And trust has always been the biggest thing to get over with Mercury because I think our product’s always been the best, but do you trust this tiny startup? That’s what we used to be. Now we’re a big startup. But it’s a big trust thing. A bank account is not a low-trust service. That’s like something that’s going to store your money and you have to really trust it. Nakul Mandan: On that note, did the SVB crisis have a big impact on you guys? Because trust at that time was fleeing towards the big banks and a lot of people were moving because who’s too big to fail, better to park your money there? Did that month or so... Immad Akhund: It was actually net very beneficial to us. We gained two billion in deposits in that two week period and then after that point, our... Our graph went from... It was a step function change, but every month after that, we were acquiring 80% more customers and it grew at a higher gradient. And I think the reason that worked is we tried to say why we were different. We extended our FDIC insurance to five million within that week and we tried to say like, “Okay, don’t take my word for it, your money is in these kind of safe places.” And I think that people really appreciated that. Obviously they were our main competitors, so they were still around, but people stopped choosing them as their primary, so they went to us. I think in general, there was definitely some people that their lesson was like, “Now we need to go to a too big to fail bank.” But then there was other sort of people like, “Hey, actually startups can be much more transparent about where the money is and keep it safe and it’s not necessarily...” SVB was supposed to be the too big to fail bank versus Mercury anyway. So I think it ended up being a net confidence boost to us, but that was a big part of it. We had to really deliver on showing why we could be trusted at that moment. Nakul Mandan: Would being a bank challenge some of the cultural norms from being a product-led company to, I’m presuming, but correct me if I’m wrong, on more compliance requirements, more back office buttoned-up aspects of the organization? Immad Akhund: So I think one of the reasons we applied for being a bank is the reality is at the scale we’re at, we are not exempt from regulations, we are regulated by proxy. If we have a new product launch, we have to go run it by our partner banks and we have to run every marketing update by compliance. So all these things are already true. Actually though, it’s almost worse because our programs instead of being dictated by us are dictated by third-parties. So I mean, that’s the reality of any at scale FinTech that you are regulated. So that’s one thing. Number two, our aim, and maybe this is naive of me, but naivety is the reason why we do anything is there’s just not that many FinTechs at scale that become banks. Maybe two or something. So I think there’s a way to do it differently and I think I would be disappointed if we come back five years from now and I did everything that a bank does exactly how a bank does. We are not innovating and we’re not product-led and we’re not customer-centric and all of these things that... The reason we exist is because to some extent the banks failed at doing what we felt needed to be done. So yeah, I want to build a new type of institution and that’s the opportunity. The contrarian thing is how do we become a regulated bank while building a product-led high velocity kind of company? And if we can achieve that, I think that’s a huge TAM opportunity and that’s what’s fun about it. Nakul Mandan: So the other part that is changing about Mercury is that you started with the startup as a customer, but then last year, 73% of your business came from outside of Silicon Valley or outside of the startup ecosystem. Is that leading to change in how you’re thinking about product at all or you think it’s a natural extension for you? Immad Akhund: No, there’s a bunch of changes, some non-obvious ones. For a long time, all of our onboarding was very startup-centric. I mean, a lot of it still is, but we’ll ask you, who’s your VCs? And we’ll ask for your LinkedIn and all this kind of stuff. It ended up being like we weren’t always collecting the right information and being able to onboard a normal SMB. So we did a bunch of changes actually start off last year. We were like, “Okay. Yes, it should work great for startups, but let’s also collect the right information and get other types of businesses onboarded quickly.” Then we also ended up making changes to our corporate credit card product where previously if you’re a startup and you’ve raised a million dollars, you get a really nice credit limit. But if you’re a small business and you have 30K, you’ll not get access to the card. So we made a new underwriting process where even smaller cash balancers will get a card, they just have to pay it back daily. So lots of these little nuances. The product is horizontal. It’s like every business can use a banking service. That bits exist, but all the little bits that make it perfect for startups don’t always work for another type of business. So especially a cash-constrained business, which most businesses out there are. So the bunch of product changes and then there’s a bunch of go to-market kind of changes. So on the website for a long time, it just said banking for startups. So if you showed up and you’re like... Even an eCommerce company, you might be like, “Okay. Well, this isn’t really for me.” So how we talk about the product, where we market the product, the sales team, the partnership team, a lot of these things, again, it was more addition thing. We still want to do all the things we do in the startup space and our startup market share has still grown in the last year and a bit, but we also want to go nail these other spaces. And the other spaces are huge. Our growth started accelerating. So last year we grew 50%. We’re probably going to grow more than 50% this year on customer account, and that’s just because the startup space, I mean, it’s big in terms of dollars, but it’s like in terms of number of customers, it’s not as big as the small business or SMB space. Nakul Mandan: You’ve mentioned you want Mercury to keep flourishing beyond you. What does Mercury need to become in the years to come or the decades ahead, which it is not today for that dream to come true? Immad Akhund: I mean, hopefully it’s already at the phase where if I disappeared, there’s good bones there and it would keep going. I think the thing that a founding CEO can do is more disruptive things. We are going into payroll. That’s not an obvious thing for a banking service to do. I think this kind of reinvention where you’re willing to do new things and push yourself. Mercury Personal, us expanding from business to personal, I had a lot of pushback internally and I think most people now like it internally, but it was just not an obvious thing to do, and I just was like, “Hey, we’ll do it better. It’s worth it, and these are my reasons.” But organizations are probably for reasonable reasons, don’t like change and don’t like new things as much as founders. I love change. I live for change. Change is the main thing I want in life. I don’t know what the answer is there. I think obviously other people have done a CEO transition where they’ve been instrument CEOs that also like that change, they’re entrepreneurial, and that would be my hope. But I’m only like 42. I’m losing count ever... So yeah, there’s still a lot to do at Mercury, so I guess we should plan for it, but right now I’m happy to run it. Nakul Mandan: So let’s talk about the inner game. You’ve been a three-time founder. How is Immad today different than when you were on your first or second startup in terms of psyche management, how you approach founder life? Immad Akhund: That’s a good question. I think the biggest thing that you get over time is having confidence in yourself and your ideas. And when you first do a startup, at least I was very susceptible to other people’s ideas. I was like, “Oh, maybe this is the way you do a startup. Maybe that’s the way you do a startup.” And over time, A, you learn better ideas, but you also get confidence in your ideas and you’re like, “Maybe I’ll talk to Jensen Huang,” and go like, “Oh, yeah. This is a good point. One-on-ones don’t work.” But there’s a lot of other things he said where you have to have your own opinions and apply them. And I think that’s getting confidence in your own opinions, knowing who you are and going like, “Oh, this is the types of people I want to work for, this are the types of products I want to build.” That takes a long time. I would say by the time I started Mercury, I was 33 and I was probably in a better place to have most of that stuff set. Every year I’m learning something new, but it doesn’t tend to be these core dynamics of who I am and who you are does definitely influence in what type of business you build. Psyche management, it goes back to some of that 996 conversation. It was definitely like I had to learn what is a steady state for me. Something that I relearn over time is I can’t spend too much time only doing things I don’t enjoy. And there’s some elements of being a CEO where you just have to go recruit or go solve a problem and it’s not that much fun, whereas I like engineering and product and talking to customers and if I don’t give myself enough space to do that, I can definitely feel burnt out. So a lot of the psyche management goes back to burnout management. It’s like, okay, what is the steady state for you to do this for a long time and have that energy that you’re bringing to the company? And I definitely talk to some people who... Actually a lot of founders get burnt out. Yeah, that’s not healthy for them or their startup actually. I think having that management of your own state and knowing what your needs are is important. There’s a bunch of elements to that. But yeah, the core of it is sleep well, meditate and exercise and I guess have a good family life. Nakul Mandan: Are there founder CEOs that you talk to when you’re stuck on an operating matter or a leadership matter that you go to repeatedly? Immad Akhund: It depends on what the matter is, and the tricky part of running a company at scale is you don’t have that many peers that you can talk to. So we’ve had some really useful investors at Mercury, like Zach from Plaid as an investor and Qasar from Applied is an investor. So that helps. And often if I have like, “I’m hiring a CFO, what should I look for?” That kind of question, it’s really useful. And then there’s a few communities that I’m involved with. So the one I joined a year and a half ago, it’s a YPO, but that’s really useful. It’s like a very high-performance CEOs in this group. We get together once a month and everyone’s very honest and authentic in that group. So that’s a useful place for me to get... Often I find with advice is it’s mostly a good avenue for you to talk honestly about so that you kind of... Obviously there’s specific advice you get, but you also self-discover advice when you have an avenue for talking about it. Nakul Mandan: Has there been an instance recently and maybe the one-on-one Jensen thing where another CEO has been able to change your opinion or how you run the company? Immad Akhund: Yeah, there was a recent element where we are applying for this bank charter and I was trying to communicate to the compliance team around how do we want to do compliance in a regulated world, and I was getting stuck into very specific like, oh, how do we do data governance, and getting really in the weeds about it, and someone gave me this advice, I won’t say who, but really useful advice to go like, “Hey, maybe instead of being in the weeds and trying to solve each problem one by one, maybe you need to write something about what is the culture of how we approach problems in compliance.” So I wrote a doc on this is the culture of compliance, and I went really deep into when should we think actively versus when we should just copy what are the expectations from other bank compliance things. Maybe it sounds simple, but just that advice and writing that culture doc led on to a bunch of things that were super useful and really changed the way compliance worked at Mercury and really helped. But those little things, it was a blind spot for me. Afterwards, I was like, “Oh, yeah. Of course. I shouldn’t be going deep on every problem. I should be trying to solve the root of what is the culture around how we solve problems in compliance.” But sometimes you just need someone to give you that. Nakul Mandan: Is there a part of being a CEO that has become harder with scale? Immad Akhund: There’s different levels where you just have to change the way you do things. One thing that bugs me is I’m a very direct and honest person and sometimes people take you too seriously. Nakul Mandan: Every word that you say- Immad Akhund: Yeah, exactly. Once I did this, I went into a Slack channel or something and I was like, “Oh, yeah. What’s happening with this project?” And I genuinely just wanted to know what’s happening with the project. The whole team was freaking out on the backend going like, “Oh my God. Immad’s saying this project’s late, and Immad’s annoyed about it.” So now when I have to say things, I have to really disclaim them. I have to say like, “Hey, guys. I am not saying there’s any problem, but I’m just interested, and if there’s an update, I haven’t heard about it.” Just a reasonable number of disclaimers, which I’m getting it better at, but it’s not my natural mode of operation. So yeah, that’s a small thing that bugs me. There’s definitely two or three phases as a CEO and you just have to operate differently. There’s the initial phase you’re still an IC, right? Less than 30 people, you’re probably just getting stuff done as a CEO, and then you have to move to a phase where you’re mostly managing managers and that’s a different phase that’s maybe from 20, 30 people, and then eventually you get to this phase around probably around 200 where you’re mostly managing execs. And most people would say that type of size and it varies a little bit, but those three jobs as a CEO are three different jobs. They’re not the same job at all, but none of them are inherently hard or inherently easy, but you have to... I think the bit that other people sometimes struggle with, they’re like, “Oh, they really like being an IC CEO.” Whereas I’ve always been like, “I want to build the biggest company CEO because I just think that’s fun. I want to have the biggest challenge and the biggest impact.” So I’m willing to really learn and try to be the best CEO of all three of those phases. Maybe there’s a fourth phase I haven’t got there yet and all the 10,000 employees CEOs are like, “Yeah, you’re just a strategic resource allocator or something like that.” Or maybe all companies will be small companies in the future. But yeah, it’s definitely a different job at those things, but I think a big part of being as good CEO is learning to do those jobs but also enjoy the jobs and also construct them in a way that you can enjoy them, because I don’t know, I feel like if you don’t enjoy what you do, you’re not going to do a good job with it. Nakul Mandan: I also heard you say in the podcast, I think it was a recent podcast where you talked about you’re at the bonus levels as a founder now. You’ve accomplished much more than what you set out to do. Can you talk about how the scarcity era Immad versus the bonus era Immad makes decisions differently, if at all, or plays the game differently? Immad Akhund: For a long time... I have a relatively poor background. My parents were on welfare and we moved to the UK with very little. So for a long time, I started as entrepreneur, I loved it, but I didn’t have some grand ambition. I just wanted to survive. There was definitely a phase where it was just survival and I was fine with any exit, and when we sold our last company for 45 million, and that was my first 10 years of entrepreneurship, so it was a long time. I finally got to a level where I was like, “Okay, I’m happy.” And then it was a kind of existential thing. I was like, “Okay, what do I really want to do?” And I considered being an investor. I eventually decided I really love doing a startup and I wanted to go for something really big. So I do think the mentality shift allowed me to go for something much bigger that I was willing to, especially in 2017, doing a new bank was not a thing you did. I started the company and I was like, “Maybe this will take three years before I raise anything else or get to product market fit.” And I was really committed. I was like, “I’m going to spend three years doing it if that’s what’s necessary,” kind of thing. There’s no way you could take that three-year big swing if you have a much more scarcity mindset. So that was definitely a mindset shift for me. I’m trying to think of what else. I’d say then for a long time I had this other goal in my head, which is build a unicorn. Again, early on in the startup thing, everyone’s like, “Wow. Build a unicorn, get to a hundred million in revenue,” et cetera. And we got to a billion dollar valuation in 2021. So there was definitely at that point, which is I would say I really got into the bonus levels this game. I was like, “I don’t even know what my next goal is,” at least in terms of the money side of things. At that point, I would say I shifted a little bit to thinking, okay, how do I just build something that customers really love that can be as big as possible and really just disrupt banking? And so it’s a little bit more vague as a goal. Getting the first exit or the first unicorn valuation, et cetera, was a more definitive thing. Now it’s more open-ended. But yeah, I think each of those phases, you end up having more long-term goals and in some ways more long-term prep. I think this helps a little bit with your previous question around stress management. I think if you are always grateful for what you’ve achieved and you do think about it as like, “Oh, this is the bonus level,” otherwise you can be like... In some ways there’s just so much more to think about today and there’s more to stress about. I’ve tried to make it so the pressure goes down as success goes up, which is I think actually relatively rare. Nakul Mandan: I think it’s very rare, yeah. Immad Akhund: But it should be like that, right? If you’re more successful, why are you more stressed about it? Nakul Mandan: Is there something you’re still trying to prove to yourself though? Immad Akhund: I mean, there’s always someone... Elon Musk is out there. He’s running five billion-plus dollar companies, right? There’s always something if you’re somewhat competitive and there’s always... But I think there’s unhealthy, “I am not successful until I’ve squished everyone,” or something. So there’s unhealthy competition and I think I’m relatively healthy about it that there’s people out there that I think have done amazing things and maybe I can try to achieve some part of that. But yeah, it’s not something that I stress about that I need to beat other people or something. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit knuckleuphq.substack.com (https://knuckleuphq.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

9. 

   9 Jun 2026

   Startup lessons Silicon Valley won’t teach you | Cameron McCord (Co-founder of Nominal)

   Nakul Mandan interviews Cameron McCord, co-founder of Nominal, about leadership lessons from the Navy and scaling a billion-dollar hardware testing company.

10. 

    27 May 2026

    Business used to be go karting. Now it's Formula 1.

    Nakul Mandan interviews Notion co-founder Akshay Kothari about reinventing a product for the AI era and scaling a business from go-karts to Formula 1.

11. 

    19 May 2026

    Behind the curtain of a $4.5b AI-native powerhouse

    Host Nakul Mandan interviews Ashwin Sreenivas, co-founder and CTO of Decagon, about building an AI-native powerhouse and operationalizing speed.

12. 

    7 May 2026

    $50M ARR With 3 sales reps, no CRO, and one PM | Michael Grinich (CEO, WorkOS)

    Nakul Mandan interviews Michael Grinich, CEO of WorkOS, about scaling an enterprise infrastructure business with a lean sales team and a unique leadership philosophy.

13. 

    30 Apr 2026

    Nobody knows anything, product market fit is dead, and there's only one moat | Bipul Sinha

    Nakul approaches Bipul Sinha, CEO of Rubrik, to explore his unique mental models for navigating uncertainty and building a $10 billion company.

14. 

    23 Apr 2026

    Battle-tested playbooks for recuriting, reading the market, and adapting to AI

    Qasar Younis grew up on a farm in Pakistan, moved to Detroit as a kid, and worked at General Motors before landing at Google and becoming COO of Y Combinator. He then founded Applied Intuition, today a $15 billion company building AI for the physical world. In an industry where most people look up to tech founders, Qasar looks up to Sam Walton and Warren Buffett. Qasar is an N of 1 founder, and in this conversation, he shares his contrarian approach to company building. We discuss: * What truly makes a founder * The “two exceptional indicators” recruiting bar * Why Qasar’s first 10 hires lived in a house together * A simple framework for monthly performance reviews * The “golden age of small companies” * How to operate with speed and intentionality Referenced: * Andrej Karpathy (https://karpathy.ai/) * Applied Intuition (https://www.appliedintuition.com/) * Immad Akhund (https://www.linkedin.com/in/iakhund/) * Kickstarter (https://www.kickstarter.com/) * Peter Ludwig (https://www.linkedin.com/in/peterwludwig/) * 18 Mistakes That Kill Startups (http://www.paulgraham.com/startupmistakes.html) Where to find Qasar: * Website (https://qy.co/) * Twitter / X (https://x.com/qasar) * LinkedIn (https://www.linkedin.com/in/qasar/) * Applied Intuition (https://www.appliedintuition.com/) Where to find Nakul: * Twitter / X (https://x.com/nakul) * LinkedIn (https://www.linkedin.com/in/nakulmandan/) Where to find Audacious Ventures: * Website (https://www.audacious.co/) * Twitter / X (https://x.com/AudaciousHQ) * LinkedIn (https://www.linkedin.com/company/audaciousventures/) Timestamps: 00:00 Intro 01:19 What really makes someone a founder 05:26 The company that almost became Kickstarter 08:12 The most common misread on feedback 13:40 Why most founders don’t end up with the best team 19:45 How to pick a co-founder 23:38 Your first 10 hires are really your first 100 28:21 The case for hiring slow and firing slow 33:22 Red, yellow, green: how Applied gives monthly feedback 35:00 The role that knows what’s actually going on in a company 40:01 How to operate with speed and intentionality 42:41 The three things Qasar spends time on 45:57 How Applied is driving AI adoption 52:06 The type of engineer Applied is now looking for 1:01:19 Why this could be the golden age of small companies 1:09:13 Quickfire: red flags, overrated advice, and superpowers 1:12:32 Qasar’s advice to his 25-year-old self This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.knuckleup.co (https://www.knuckleup.co?utm_medium=podcast&utm_campaign=CTA_1)

15. 

    14 Apr 2026

    Frank Slootman on what most CEOs get wrong

    Frank Slootman is the only CEO in history to take three enterprise companies public: Data Domain, ServiceNow, and Snowflake. At their peak, the companies he led were worth over $200 billion combined. His playbook for building high-performance organizations, captured in his book “Amp It Up”, has become required reading for CEOs. In this conversation, Frank opens up about the fear of failure that shaped his early career, why most CEOs tolerate mediocrity for far too long, and the moment he realized Snowflake needed a different kind of leader and chose to step aside. We discuss: • Why being a CEO is a confrontational job • The “drivers vs. passengers” framework • Why references matter more than interviews • Why culture isn’t about making people feel good • How Frank faces his demons “for breakfast” • How Data Domain survived year one on $3M and a product nobody believed in • Why AI is a dislocation on the scale of the Industrial Revolution Referenced: • Amp It Up (https://www.amazon.com/AMP-Unlocking-Hypergrowth-Expectations-Intensity/dp/1119836115) • Data Domain (https://en.wikipedia.org/wiki/Dell_EMC_Data_Domain#Data_Domain_Corporation) • Elon Musk (https://x.com/elonmusk) • Google (https://www.google.com/) • Intel (https://www.intel.com/) • Peter Thiel (https://x.com/peterthiel) • Scott McNealy (https://x.com/scottmcnealy) • ServiceNow (https://www.servicenow.com/) • Snowflake (https://www.snowflake.com/) • Sridhar Ramaswamy (https://www.linkedin.com/in/sridhar-ramaswamy/) • Steve Jobs (https://en.wikipedia.org/wiki/Steve_Jobs) Where to find Frank: • LinkedIn (https://www.linkedin.com/in/frankslootman/) Where to find Nakul: • Twitter / X (https://x.com/nakul) • LinkedIn (https://www.linkedin.com/in/nakulmandan/) Where to find Audacious Ventures: • Website (https://www.audacious.co/) • Twitter / X (https://x.com/AudaciousHQ) • LinkedIn (https://www.linkedin.com/company/audaciousventures/) Timestamps: 00:49 Introduction 01:21 Why being a CEO is a confrontational job 03:51 Great people are hungry for hard feedback 08:19 Psychographic profiling: how Frank builds compatible teams 09:52 Drivers vs passengers: how to tell the difference 12:39 Why back-channel references beat interviews every time 16:19 “When there’s doubt, there’s no doubt” 20:42 Inside Frank’s Tuesday operating cadence 22:27 The “go direct” rule that breaks org chart politics 26:19 Why bigger goals force better plans 31:27 Standards are the real culture 38:17 The email Frank wrote every Monday for years 41:35 Advice for navigating today’s volatility 47:25 Facing demons for breakfast at Data Domain 54:19 Why Frank fired himself as Snowflake CEO 1:05:19 Coming to Silicon Valley “10 years late” 1:07:59 Why AI is an industrial-revolution-scale shift 1:10:01 Frank’s advice to his 25-year-old self This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.knuckleup.co (https://www.knuckleup.co?utm_medium=podcast&utm_campaign=CTA_1)

Inside a recent episode

How Railway says no to 90% of ideas and keeps winning | Jake Cooper (Founder, CEO)

Published 13 Oct 2026 · Transcript excerpt

[…] Did the product get better or did it just compound to a point? And I see this with some of our even other companies where some companies or products, they just need two, three years of compounding both product and messaging. And suddenly they're ready to explode. They didn't change anything. It was just compounding. Yeah, I would say it's definitely more iterative. than it is like some sort of like thing that I could give to people. It's like advice of like, oh, just do this and your chart will like go vertical, right? Like the just do this advice is like show up every week, tackle the biggest problem for the company that you're getting after and then figure out some way to finish your week by moving that like brick forward and just do that for 52 weeks a year. […]

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