The art of scaling with purpose with Abhik Pramanik
47m 7s
In this podcast episode, host Matt Tate interviews a founder from Ashby about their entrepreneurial experiences and insights. The guest shares his journey from a dream job in visual effects to entrepreneurship, driven by a desire to build something impactful. Both discuss learning from past failures and leadership shortcomings at previous companies, emphasizing the necessity of setting a high bar and executing effectively. They detail how thorough market validation—such as interviewing over 100 recruiters—was crucial before launching Ashby, which aimed to create a 10x better recruiting software by addressing widespread customer dissatisfaction. The conversation explores how traits like passion and curiosity often make entrepreneurs "terrible employees" in traditional settings, as they take on excessive ownership. Additionally, they note how economic downturns can benefit startups by forcing companies to seek integrated, budget-friendly solutions. A recurring theme is the importance of continuously listening to customers and adapting, contrasting with legacy firms that may lose focus due to overconfidence or distraction.
I think what Benji and I really thought about is like, what are the things at previous companies that we've been at? Where did leadership fail? And what do we need to like keep running with the torch and what do we need to hand off to other people? For us, setting a high bar was just something like being Benji have to do. And on top of that, Benji has to set the vision for product. So I think this goes back to like, what are you trying to accomplish with your company? What is the strategy to be successful for us? It's execution. Hi, I'm Matt Tate, founder of Decimal and host of After the First Million Podcast. And like you, I've taken the lead. Not just to start a business, but to scale and grow it. I've hustled from zero to that first million and now I'm building for the next year. I know firsthand what the messy middle looks like. And we need more than just numbers. We need strategy. We need community. And we need real conversations about what growth takes. In our line of work, scaling beyond a million means going beyond the spreadsheet. This is where you learn how to grow. This is After the First Million. All right, welcome to today's episode of After the First Million. I am excited to introduce everybody and to have a conversation with a beak from Ashby. And I have to admit straight away, Decimal is a long time Ashby user for our own recruiting and really tracking our whole hiring process. And how they built the software compared to other softwares that I've used has just been a huge game changer for us. But a big story is really cool. And in fact, I was just laughing with them right before this that are prepped right before the call. I should have totally recorded because we really dove into some really cool stuff about running a business and thinking through things and entrepreneurship. And so before we get started, a beak, welcome to After the First Million. I really appreciate you joining. Thank you for having me, Matt. So one of the things that I always think about is, and this is not my first company, those of us that start businesses have to be a little crazy. When did you realize you were one of the crazy ones? I would say pretty early on of college, I think college was kind of my place to kind of figure out what I wanted to do. I always loved arts and CS before college. College was kind of my way to like figure out how do I know the two. And then I went into visual effects straight out of college. That was like my lifelong dream of like I wanted to work in movies and film. And I got my shots. And I was working at industrial light in magic at the time. What was really interesting was about a year and eight months in if I remember correctly, I really wanted to build an app because I was playing like flag football. And I wanted to build an app to like find other people to play flag football with. And this was like crazy idea. Like I had my dream job. And then all of a sudden I felt like I had to leave to build this idea. And I remember I was like talking to my parents. And they're like, this is what you've been like dreaming of your entire life. This work and film. And you get it. And you just want to quit to go do your own thing. And I think at that point, I realized like I really wanted to like build something big and massive and touch millions of people and like do that my way versus you know, showing something like Pixar or Island. It's funny. I always joke that I'm a terrible employee. And I wonder if part of that too is just I like having the freedom to dive in and to pull on the thread of curiosity. And it sounds like that's part of your journey too. Maybe not the terrible employee part. I'm a terrible employee. If Tracy and Ralph from Plangerid are listening to this like they I knew them very well at Plangerid. And I think I definitely got on their nerves quite a bit. Like even when I joined other companies, I don't know about you. But like I was very passionate about their mission. And like I almost put it on myself. I was like like with Plangerid, I was like we're going to change the way construction use a software. And like I just lived and breathe it every day. I remember I worked as hard at Plangerid as I work at Ashbee today. But I think the problem there is like you you're a terrible employee because you take on their worries and their concerns when duality is like you don't have the agency to like act against those. But then you go and act against those. And then they're like what are you doing? This is not your domain like stop. I think that totally makes sense. I mean and that's the way I was. Like you you take on the the passion and like you dive into like this is the mission of this company. We can do this. And this is how we should do it. And the minute you start thinking this is how we should do it. And it diverges from leadership's thoughts on this is how we should do it. But you do it anyway kind of. That's when that friction happens. And it's the beginning of the end for people like you and I. Oh yes. Funny story. I remember I was so passionate about like one direction. I'll take the company and I wrote a thesis of like here's where we need to take Plangerid. I regret writing that. I remember Kevin who was now at Ashbee. He was like a bee. You're going to meet the dog house if you send this out. And I was like don't care. I really want us to like be huge. And it was done. That's just like your the mentality of not realizing. Hey like this is not your baby. It's someone else's like they are calling the shots. Well it's funny. Then you have kids. And somebody tells you how you should raise that kid and you start to say ah this is where I went wrong in sending those that thesis or for in my case in doing other things where you're like okay you start to have empathy for the people that you maybe weren't great at working for. Oh absolutely. I mean now that you know Benji and I are at Ashbee and like we're like living and breathing this for like six years. You kind of look back and you're like I had a limited purview like it may have been enough to like have some intelligence ideas but like in Plangerid's case trace in Ralph like lived and breathed that for like several years before I was there like they knew the ins and outs of our customers more than you know I did and they had a head start like there was almost no way I could catch up to them because they were on the front lines. And so now that you start Ashbee like you kind of feel that because like you kind of have to gently tell people sometimes like hey I know you feel this way strongly but there's like a series of things we have learned over time to get to this point. And we're not always right but it is deliberate and methodical. We've thought deeply about this problem and come to this conclusion just because you're thinking deeply isn't a bad thing but don't discount the fact that we have to. How did recruiting and Ashbee become a passion project that is now an amazing company? So Benji and I worked at Plangerid together. This is my second company it's Benji's first company. I was not looking to start another company. So after my first company I shut it down. I realized I had very naive in a lot of ways. I really wanted to work at growth companies to really understand once you find product market fit what does that next phase look like and learn a lot about the problems and like how to solve those problems and be able to experiment at that scale. You just can't do that when you're like at an early stage startup. But at some point like you said we're crazy and so Benji came knocking. He was ready to start a company and he had really went through the high growth phase at Plangerid and used all the recruiting tools. He cared deeply about hiring and he was just like the tools are not great. I wanted to do basic things basic reports and I couldn't do it at the duoden spreadsheets. There's something fundamentally broken about this. And so then when we looked at the market we were like there's a lot of customer pain. There's a big market and the people are not satisfied with their solutions. And then on top of this they're compensating for all these like ancillary tools like scheduling, sourcing. This is a great place. And for Benji and I we really believe that we are great executors. And so this is like an execution play. We have to build 10x better software but we don't have to prove a market exists when we're at Plangerid. You have to basically prove that we could replace paper with software. Here software already existed. We just have built a 10x better. So all of that put together plus Benji and I having a really good working relationship. Like we we challenged each other. It wasn't just we were friends which we were outside of work. We challenged each other at work. Putting it all together it was seemed like a no-brainer. It just felt obvious at that point and the rest of the rest of the history. I think that's interesting. Like you before decimal I had a failed startup. It was like restaurant marketing tech. It was a great idea really bad business. It was one of those things that everybody conceptually was like oh this is cool. Like I really like this. And then you get into it and you're like can't really sell a lot of this. Raised a bunch of money. I ended up shutting it down and my wife looked at me and she goes hey for two years. It's all I care about. Two years. Will you go get benefits? Two years. And she's the same. She's a partner at a big law firm and she used to work for the state and got way cooler jobs than I ever have. But she was like I would just like you to be steady for two years. I lasted 13 months. 13 months? I did. And I'll never forget it because we started decimal in January of 2020. I went to a large accounting firm and they brought me in to be an entrepreneur residence. They said start a bunch of things. Help us make much money. It was fun. Like I had a blast. And that's ultimately how I went from having no background.
in accounting to running a very large bookkeeping firm. But we went to this Christmas party for the whole firm and she looked at my co-founder who I brought to help me and we walked out of that Christmas party and she goes, "You guys need to get the hell out of here." Like whatever you're doing, like build towards mid-summer, getting out, like you guys have to go. Like this is not a good place for you. It'll never let you grow this where you want to grow it and you're launching in effectively two weeks, build your exit strategy. Pandemic it. So that changed the whole thought process around everything. But it was kind of same as you. Like I wasn't ready to start anything and then all of a sudden I'm crazy and this good opportunity came and I thought it was a nice safe place to do it and then I was like, "No, it's better out." And it's been way better outside of it. I think it's fascinating how many of us take a failure and that failure makes us just that much better to then succeed in the next round. There's so much I learned in the process of starting my first company but like I think the other part of it was just like it was so depressing, shutting it down. With Ashvi, we talked to 100 recruiters. Like I say this and it sounds ridiculous but like I had a signing bonus I had to pay back. Like Benji was like you're quitting and I was like, "Do I have a signing bonus? Like I have to pay that back if I leave." And he was like, "No." And I was like, "All right, well then I have to be damn sure that this is the right idea." So we talked to 100 recruiters and like that was what it took for me to get very convinced because like if we talk to two or three it's like does that make sense? Like I want to talk to you know, mid-market companies, enterprise companies and that's what it took for you a decimal like what did it take to really make that crazy move. I'd run three companies before that and I had major pain with my bookkeeping and bill pay and like just getting it done, going through vendors, hiring people. Like it was a really painful process. And so I then started talking like you, like we talked about 100 small businesses and just people we knew or people we knew and we just networked our way around just asking questions and we easily talked to three X. Like we validated the problem about 30 in like you I'm like, "I need to go further." Like if I'm going to make this move, if I'm going to do this I need to be a thousand percent sure. And then we're in an accounting firm at the time watching how they're doing it and they're supposed to be the best. And we're just watching them do it and we're like, "This is terrible." Like you're the best like, "Oh my gosh, we can easily do 10 X." And so it's like that 10 X that you talked about. And so we validated the problem on both sides of the marketplace, the buyer and the purveyor of services. And we said, "You know what? We can do this better. We can make more money and we can create better experiences." And ultimately that's how we've built what we've done and it's been fun. And we've always talked about luck. Like there was a little bit of luck in our story as well because Benji and I had been throwing around different ideas. Benji was very competitive on recruiting and a lot of credit to him for just like standing his ground over time. I was like, "Hey, I really want to work together." Now you've got me excited about starting a company but like recruiting greenhouse lever have been around for a while. Like why? And you know, I haven't lived and breathed the problem until we started Ashbee. So I was like, "Maybe we do financial planning software." I think that was the other thing we had turned around because we had a couple of friends in the finance team at Plangerid and there she was like, "Modly." And like I think you hear a lot of startups going after this but like fundamentally we did talk to a bunch of people but I met my wife at the time, right around the time that we started Ashbee. And she's in finance at like a Fortune 15 company and they're still using Excel and she showed me and walked me through her models and like Benji and I were like, "Excel's actually really good at this." Yes, we could like try to compete with it but at the enterprise scale like Excel is just like a canvas to paint on and you have enough people that can like do it in a way that like is very specific to the company. Like the younger startups, they just kind of want a dumb tool to like model it or they would just want like an Excel template that they get from you know investors or from their incubator. And I met my wife right at that time and she was like, "Don't do this. Like do not do this. You should do the recruiting idea." That's good advice. I mean marrying her was probably a better move but like it sounds like it worked out well in a lot of areas. Yes, I mean Benji always always 100% in recruiting but like Benji also convinced me. I was a bit skeptical but again that was naive a tear on my part. I just didn't know any better because I hadn't done recruiting at the time. Like plays such a key role and I don't know about you both of us kind of started around the pandemic. And for me that meant that my business went to zero overnight like literally six weeks after we started but then all of a sudden it just took off. And then the world, businesses that were working towards being better at being fully remote and digitally capable and on the cloud and all the terms that you kind of hear were forced to do it and found how much easier it was. And I wonder if part of that like being in this kind of post pandemic world has also benefited you guys as people are using software in different ways and thinking about their recruiting and thinking about their back office and they've changed perspectives and it broke them out of the way that we always do it mentality. Yeah. I wouldn't say it's the pandemic I would say there's luck in the swings of the macroeconomic factors that we've seen over time that have really fueled us. A really good example of that was when the market crashed around 2022, 2023. So our goal is to build all in one recruiting software. That is a huge mandate like we need to replace not only the legacy HTSs but we need to replace all the scheduling tools, the sourcing tools. These are themselves venture backed companies and we need to build all of the software and we need to like convince people that the sum of all these parts is better than buying these individual pieces of software. Back in 2022, we had replaced the legacy HTS but we were like missing a couple of features and then for the scheduling and salary software, we were also like maybe 70% at most of the best in class but because recruiting budgets for shrinking, people were like I just can't like I have to compromise somewhere and so this kind of downswing in the economy and the lowering of budgets helped us because we could sell Ashv as all in one and people knew they were compromising at the time but they just kind of had to. They're like I either just get my legacy HTS and like not these great tools or I get Ashv, I get certain percentage of these great tools and it kind of all works together and so people could take bets on us and then the rest was on us. We had to take that luck and run with it. We had to actually build 100% of best in class in these other areas and we did. We're barreling towards that today and again we could have been successful a different way but it allowed us to accelerate our master plan a lot faster. You know one of the things that you're kind of tap dancing around that I think is really cool that I find with tech companies in general that service businesses and you've been around a million too, don't do as well. You guys seem and you seem in particular like you deeply thought through this problem and how to create a great experience for your customers, continually improve it and keep them as long term customers. Why do you think other people don't do that so well? I think the way I've put it is some people are just on a position to be able to do it. If you look at the recruiting space at some point people have been purchased by private equity and that is now you're trying to pull out profits from these companies and that means you're cutting support, you're basically cutting R&D. So in some of the legacy ads are just kind of hamstrung by like focusing very cheerly on unmargin and profit but it doesn't always play out that way with the private equity purchase but like in this case it did. I sometimes sometimes some people just stop listening to their customers and I don't know why at some point like a company just becomes too confident. I don't know if confidence is the right word, they just kind of lose sight of like hey just listen to your customers. I'm sure a lot of it's overconfident but do you think a lot of it's just distracted to? Distracted by what though? Well is it distracted by we heard our customers, they told us to do something, we're doing it but then not listening while doing it. Whereas like that startup mentality, you and I both started companies. The theory that you start with even in that first listening so that you talk to a bunch of recruiters right, you guys came up with a theory then you started to build. There's no way this end product is exactly what you initially thought you were going to build. Like you end up moving along as you keep listening, as you keep like learning, as you keep improving and like that's that kind of startup mentality and I do think at some point people either get distracted by
by their vision or all the trappings of running a business and they stop doing that kind of process that we all run at startups. - In our space, I think what we've seen from some of the top players is, we've heard that they have their own belief about where recruiting is going. It's almost like, hey, we're the top player. Here's our opinion of how you should do recruiting. And they kind of pushed their features in service like you said, they have their own vision of where recruiting is going and that sometimes misses the mark. You have to have a vision to start something and make it successful because otherwise, you're just kind of like building exactly what your customer says. But at some point, this is the vision. This is like, everyone's gonna follow us because we know what's best for people. And I think like one of the things that Ben and I have done is we've listened to the market. For instance, in 2021, if you asked all our customers, like where do you want Ashbeet to focus? It's like sourcing, sourcing, sourcing, sourcing. Like we have so many jobs open, non-Nuff candidates out there, you know, find all those candidates. Now if you switch to 2022, all of a sudden people are like, we need to slash headcount, we need to close all our jobs. We have a couple of jobs open, we're doing backfills. If you ask a lot of our customers, like where do you want Ashbeet to focus? It is on inbound, handling inbound volume, which is still somewhat true today, which is like we have 2000 applicants for a role. How do we sift through these people? If you built a vision in 2021 and you're like, we're gonna build sourcing for the next year, you have to be nimble. Like we were nimble, we just basically were like, shift it a lot of our focus on to handling inbound volume. And so I think the vision can sometimes work against you. - Every business and needs that North Star, like for you guys, you want to build that all in one. That's the North Star. How you get there listening, that changes, but it doesn't change that North Star. I think that's probably the nuance differences. When you pack too much into that, that's when you start to lose the listening. I really like the listening to the customer base because I feel like not enough companies figure out how to systematize that too. And it kind of becomes an OSHA moment every once in a while. Like, oh shit, I should go listen to my customers or oh shit, I gotta figure this out. And it's more than NPS scores too. It's like actually deeply understanding and listening. How have you guys kind of really systematized that? 'Cause it sounds like you've listened, you've pivoted and you've kept up with the market. And as a user, I can see all the changes or my team can't, they don't let me do anything. But how have you been able to maintain that consistency? - I want to say there's like a system I can teach and tell you and articulate to you. But I think it's really one, Benji just says close to customers. I recruit every day. Like I am my own recruiter. So part of me building empathy with recruiting. And this is also a little bit of not luck, but we are growing. And so I get to see different scales of our customers. Simply by me doing recruiting every single day. And so it used to be that I was the only person recruiting for engineering. And now I have hiring managers reporting to me who are also doing recruiting. And so now I see like how does Ash be scaled to a team? So Benji's talking to customers. I talk to customers not as much, but I literally just use the product day in and day out. And I think that is a bit of a secret sauce that we have is we can use our own software. And we're scaling. And so now I can see how our software scales to different levels of folks. And I think that I do approach recruiting with a bit of not sophistication. I try to make it as automated as possible. And so I think about what are some things I need for myself to be able to not have to spend a lot of time doing the not-nice test. And then those will be ideas that Benji and I come up with and then we're gonna ship to our customers. But sometimes we're able to anticipate some of our enterprise customers needs because we ourselves are trying to build a very sophisticated recruiting process. And then we end up just thinking of features and our customers are like, we have this problem. And we're like, oh yeah, we were thinking about this. Here's conditional activities for instance. That's an example of something we were thought of thinking about. And then one of our customers, who's 8,000 people e-commerce company, it was just like, we have this problem. We're like, yep, we have this problem too. We have an idea for it. - You know, one of the things that I've been thinking a lot about lately is really creating true partnerships between tech companies and customers. And in my case, it's accounting firms or bookkeeping firms and the companies that actually provide the technology because you come from a space and you're recruiting with a lot of legacy software. Accounting QuickBooks is the legacy software. It owns the largest market share of any other tech company. I mean, it's insane. But what it's done in my industry is created this more of a vendor user perspective, where it's not actually a true partnership. But then you're seeing this next generation of tech companies come in and say, hey, we actually want to build for you. We want to create a relationship where we're working together versus you just using and us maybe sort of listening but really doing what we want. And it's creating these new opportunities and growth and creating a different sense of community within the industry that I think is really, really cool. And it sounds like you all have really kind of built towards that as well. - Ben, I really wanted to build a great customer success team and something we invested in quite a bit, customer success support. People we brought on those teams are fantastic. They feel the pain of the customer and they're able to articulate that back to us. It's almost like their profile is almost there, like very sensitive to the needs of like other people. And we've hired a great team on that front. And that's something that like you hear from our customers is like, Beth is fantastic. I love working with Beth. Like they know them on a first name basis. They just talk about them all the time. And it's almost like they are, they're almost as like front and center as the product itself. But like that creates a true partnership. Again, like we're not just building up people tell us, but like the customer success team is able to really bring back a lot of the problems. They work with the product team to kind of like talk about, like, hey, how do we message this back to the customer? Are we gonna solve this problem if not why? And have like come back to the customer with like, we're going to build this. It's coming soon. There's just a lot of collaboration within our company to make sure that when we do communicate back to our customers, it feels like a relationship as opposed to us saying, no, yes, no, yes, no, no, no. Which I think is what most companies do is just like, say no, say yes, rather than like actually articulate the why behind it and like our motivations. We're transitioning 250 clients onto puzzle, a brand new AI native ledger and competitor to courtbooks. Still have 600 clients on QuickBooks. So it's not like it's going anywhere anytime soon. But over the last week, we've been working with them and doing a back and forth on blog posts and press releases and kind of all this stuff that goes with it. And we've been asynchronously working. And I'll have an opinion, they'll push back, they'll have an opinion. And it's been that kind of back and forth of a true partnership. And I get it with my co-founder and it sounds like you and Benji have it too, where when you guys actually push back and you have a deep conversation, neither one of you is 100% right? The other person gets you there together. And that to me is what you're talking about in the your customer success team and listening is, the customer has an idea of what they need. But sometimes they're not great at really articulating the underlying thing that they truly need. They're good at telling you the symptoms and you have to then pull out and figure out the core use case and the core really reason that also helps make the symptom better. And that type of listening is a true partnership. - Yes, and I think your customer success team and your support team have to be really in tune with the product and the customer needs. So like I went to an implementation for a customer. I went on site and it was amazing to watch like our success team work because they're in a mad rush to implement your software and they're like, this doesn't exist. We can't do this. You just can't do this in the software. I think if you didn't have a good customer success team, they would just come back to product and be like, they don't have this. Like we need to build this. Whereas Kira was there on site with me and her response was, tell me what problem you're trying to solve and then they were able to craft a solution with our existing product for it. Because our product is flexible, you should be able to solve a lot of needs that you end up with problems that you have. And when we couldn't, that was when we had a discussion. But like the thing there is like, I think there's a reaction sometimes from startups just be like, oh, we'll build it or we're just saying no. Rather than like, hey, let's think about our product and like, how could they solve this in our product? It might be a compromise, but it might like solve the problem just well enough that we buy ourselves some time. And that's the other thing I think that like, [BLANK_AUDIO]
important is thinking about what do you build now versus what do you build later. I think a lot of things we've seen are customers are like, I need this. Yes, I know you need this and we will build it. Like do we build this now or do we build this later? And I think that's something that we've been generally good at and Benji leaves product. And so I think you've been very good at like kind of anticipating we have 100 things we know we will need to build over the next five years. How do we sequence them in the right ways? Such that it gets us to the next milestone. That's like really listening to customers and feeling figuring out when to push back and when to say yes. There's another really important thing. And I talk about it, we don't build product. We do adapt and change services and solutions and what we do. Sequencing out change and not trying to do too much at one time and understanding how much your team can handle and as you grow they can handle more but how much more that I think is also a really important thing to building a successful culture in addition to a successful company. - I would agree. I mean, I think you have to be very deliberate and methodical about how you approach this. I think it's easy to say yes to everything. It's easy to say no to everything. I think really where things get ours, just like thinking about like, I have limited resources. How do I use this in the most effective way? I think back in 2021 everyone's like, let's just hire and then we'll get infinite resources. You saw the consequence of that. But I think really the most successful companies are made because they know their constraints and they work within those constraints to kind of, I think build magic. - Yeah, and I think the addition there is, they also are willing to push the boundaries, but not too far. People like you and me, we have no problem jumping out of the airplane. I do like having the parachute making kid on the way down. Those are kind of the important things. I see a lot of people start companies and it's like you really don't know what you're getting yourself into. You have the kernel of an idea like, this is great, it's awesome. You need a little bit more here. You need to really figure this out. And then as a team scales, you become astronomically more complex. And then you're dealing with more people. One of the things I'm interested in as we've grown, and I'm interested if it's similar with you all, I've learned very quickly where my deficiencies are too. And having to hire people that are better at me in a lot of different areas. And I found that to be a really big key, but also like, it was something I did very poorly at my first company and I've gotten way, way better at and this one is just being like, I really suck at this. I need to hire this person where I need to hire for this function and they need to be way better than me. How have you guys kind of filled out and grown as yourselves as co-founders, but then how has that allowed the business to grow and affected your hiring? - I think what NGNI really thought about is like, what are the things at previous companies that we've been at? Like where did leadership fail? And what do we need to keep running with the torch and what do we need to hand off to other people? And like for us, it's like setting a high bar was just something like being Benji have to do. Like what is the strategy to be successful? For us, it's execution. And so when I thought about as Ashby grew, where do I need to put myself to one, like really be opinionated in a way that benefits the company? And something that like I feel like I am somewhat qualified to do, I just think when you start a company, you're not really qualified to do a lot of things that like the scale we're at today. And to me, it was like I have worked with great engineering teams early in my career. And I want to build a fantastic engineering team because as a company that's really about building 10x software, our engineering team is one of the foundational pieces to doing that. We need to move fast, we need a ton of ownership. We need people who are just excellent at thinking of distractions. Then when I looked at my previous companies, it was like, not all of these engineering teams are well run. Like, and also I felt bored as an engineer. Like there was this process. And I was like, these are things that, if I can innovate, innovate in quotes, like if I can just be different in this area, like that gives us a competitive edge as we grow. And so that's where I decided to place myself. And then the other interior areas, like we just need to hire people who, like you said, know this better than us and who are going to be able to help us like think about this problem in ways that like leverage their experience and also their kind of like different perspectives. That's the way I think about it. - That's awesome. - How have you thought about yourself as you scale? - You know, I got lucky. When we started to really scale, I realized that I was quickly coming up on stuff I'd never done. And sizes of companies and complexities that I'd never led before. I hired a great coach. And he's really helped me to hold a mirror up to where my deficiencies are. And to do it ahead of time. Because, I mean, I'm sure you can see this when you're scaling. Sometimes the nature of your job changes every two to three months. Like astronomically changes. Like most businesses that grow, like maybe they have one massive change a year or every two years. But like when you're scaling as quickly as we have and you have, like sometimes like every three months and you're like, man, I got a totally different job right now. And so having a coach really helped me. But what I have ultimately learned is like, I do good on kind of the vision side. And I'm a really good relationship person. I'm a terrible execution guy. I'm just not good at it. My joke is I'm really good at convincing people to jump off a bridge. I can't get them to line up to do it. And so hiring a COO was a big thing for me. Where it's like, hey, I need somebody to run this business. Like day to day, like run the company, run sales, run operations. Like I need somebody that can do that better than me because I'm just not good. I'm good on that very high level. And I'm really good on the down like tactical low level. And I'm a good conversationalist and help here. But I'm not good at running those types of teams for a long period of time. And that's been a big learning for me. I was going to say I'm not opposite. I'm very much execution. And I don't know if I'm visionary. I just love building great software. And figuring out the nuts and bolts to make that great. So yeah, it's interesting. But I was going to say executive hiring seems like a very important facet of this, which is hiring great execs. And that's something I think we've done very well. Benji hired all of them. But I think we done really well on that. That becomes kind of the first tough point when you start out and it's you and your co-founder. And you guys are making all the decisions. And then at some point that room grows and you're like, now it's all of us making a decision. And maybe I think once a year, maybe once every two years, we run into a decision that it's locked and I got to make it CEO. I have to be the one that puts my thumb on the scale. But that also was a tough thing to say, hey, we now have a leadership room. We all have an equal vote. Mine may be two when I need it to be two. But that was also kind of a just dynamic change. And it changed the dynamics with my co-founder a little bit too when it was just like time to grow up as a business. It's an interesting transition. I've seen this happen at previous companies where we brought in executives and felt different. I think for us, it didn't feel that there's this moment that's been seared in my mind. I was talking with another founder. And they were like, do you hate your VP of sales yet? And I was like, what? Why would you ask this question? I was like, if I didn't like our VP of sales, they wouldn't be here. Like, bend you down the board, be make the decision to let them go. They talked about how they were kind of in a position where it was like the VP of sales that built a good relationship and had previous relationships with their board. And there's all this drama that happens at like the executive level. And I saw that at previous companies too. And I think we have had the fortune of every half year, we rent an Airbnb and we all just stay in the house together for three days and just like plan for like the next six months, one year and talk. And it's incredibly fun. Like, I love talking to everyone of our leaders and yeah, Mike at VP of sales, Kelsey in success and like marketing and gym. And we just brought on Shane to lead finance. Like, it's just so fun. Me and Veggie were like kids, but like we're all kids. Like we all want what's best for this company. We're all kind of willing to make compromises to like work together. But we're all just like sitting in the room spitballing. And it's kind of amazing. Like it's just an amazing feeling. And again, this is my first time with the company with an executive leadership team. But like at previous companies, I didn't get the feeling that like the founders and the exact teamwork really on the same wavelength. And I think that's huge. I think that's really important for the executive team to be really jelling together. That's really cool. Was you look at 2025? What's on the document? We're moving heavy into enterprise.
We have snowflake opening eyes customers getting more of those folks as customers. There's some really exciting challenges from a product perspective of serving 200-300 person recruiting teams with like interviewers that are number in like the hundreds that they have to like figure out in schedule. Part of that's building new products, something you know all of us know as founders. We're venture backed right so like at some point we need to figure out what's that next kind of product. We have to go multi-product and so going multi-product is a big focus for us which is super fun. Also very interesting it's an interesting challenge like how do you build a brand new product inside your company and that's going to be fun and just like figuring out how to do that is going to be interesting and then just making a product better there's like so much exciting technology coming out AI you know that's the hot buzz word today. I was using cursor the other day to code and I was like this is amazing. It's not going to replace me as an engineer so I'm going to replace our engineering team but like it's very clear that AI is going to make people better if you learn how to use it just like any other tool and I think that's the same for recruiting. AI is not going to place recruiters. What it is it's going to make them better it's going to remove a lot of the monotony out of their day and I'm really excited to explore that in this space. Well I think that's really cool you guys have built a great product and I like how you're building a great company too. I used to think like the products and services that we were putting out there was the baby. We all think of our company as a baby it's our kid. Yeah it's really the whole like culture it's the team it's that I feel more adherence to I mean it's I like both those feelings you get working with them to push forward to something really cool that's what I think is truly awesome. As you think about it right like when you're five people the things I produce make a material impact in the way the company kind of moves forward. At our scale now 150 plus people like coding is not going to move the needle for Ashbee and it's really about like figuring out how to design a culture where like yes an engineer can build something and it moves the needle because they're in a culture that allows them to move that needle versus be a cog in a wheel and not just to me so exciting like I want to build a company where I myself could just like be an IC and like have a ton of fun if it kind of winded it back to our earlier conversation that's like I was like a rebel at every startup I was at there was moments in time where I was just given enough freedom that rebelliousness turned into like a benefit for the company and like I want to build a culture that does that and I think there's this natural tendency as a company grows for consistency in output rather than exceptional output and so they they build in all these processes so that like the rebels kind of just feel lost in process and I think on engineering it's very clear that you can hire an engineer who thinks about product thinks about design and can build a brand new product without really much support like how do you do that at 50 person engineering team underperson and that's like a really fun challenge for me I just think about this all the time and like the product is almost like secondary to that because you're like the product will build if I build this great team yeah a great product can be there in a bad team will make it worse but a great team will always start to produce a better product yeah I mean we have product market fit to some degree and like it's really about accelerating that and you can hire a team to maintain product market fit but that doesn't make you amazing like what makes you amazing is hiring even more amazing people no I agree and I think honest guy that's the perfect way to end this I really appreciate you taking the time and having this conversation I've been taking notes I've learned a ton and I think it's awesome thank you thanks for having me and I love the conversation it's been really great to learn about like decimal like you're approaching things differently than I've seen before and it's just like the prelude to this was just it was just so fun to talk about business and strategy it's always great to find a good thread that you can just keep pulling on growth doesn't stop at the first milestone or even the first million it's really about what comes next build your firm as if you've already passed that first million and are still going in every episode I'm gonna pull out key lessons to help you grow with an after the first million mindset all right here's what stood out to me from my conversation with a beak it was a great chap but three things stood out number one your first idea doesn't have to be your last number two listening to your customers is key but knowing when to push back is also important and three building a great product or service is really important but building a great team is everything it's your foundation so when we go to your first idea doesn't have to be your last as you've seen in a beak's story and his career and even with mine you might have a winding path to get to your destination a beak started in visual effects moved into tech and now helps lead a fast growing software company the point be flexible be flexible in your services to it when you're in startup phase what you're doing today may not be exactly what you're doing later pricing may be different service components scope be willing to be flexible but also know what you're doing and then number two when we get to listening to your clients or customers they obviously have opinions and they know what they want but sometimes you know what they need and that can be a little different it's really important to align incentives and figure out the balance between what the customer and the client wants and asks for and what you know that they truly need number three finally building a great product or service is important but the team is the foundation for everything a beak in his team they help other teams grow so he knows a lot about how to build that foundation and what's important you focusing on your people focusing on yourself and focusing on what you're building as a culture is the foundation for all the great stuff that you're going to build later it was a great conversation and I can't wait to see where Ashby goes next thanks so much for listening after the first million is presented by decimal to listen to more episodes and find tips to help make running a business easier is at decimal.com/afm want to join the conversation reach out to me on linkedin and let's explore the messy middle
Podcast Summary
Key Points:
The host, Matt Tate, and guest, a founder from Ashby, discuss their entrepreneurial journeys, including past failures and lessons learned about leadership and execution.
Both emphasize the importance of deeply understanding customer pain points through extensive validation (e.g., interviewing 100+ recruiters) before starting a company.
They highlight how personal traits like passion, curiosity, and being a "terrible employee" in traditional roles often drive entrepreneurship, as well as the value of learning from past mistakes.
The conversation covers how macroeconomic factors, like budget cuts during downturns, can create opportunities for startups offering integrated, cost-effective solutions.
A key theme is the need for continuous customer listening and execution to build superior products, contrasting with legacy companies that may become overconfident or distracted.
Summary:
In this podcast episode, host Matt Tate interviews a founder from Ashby about their entrepreneurial experiences and insights. The guest shares his journey from a dream job in visual effects to entrepreneurship, driven by a desire to build something impactful. Both discuss learning from past failures and leadership shortcomings at previous companies, emphasizing the necessity of setting a high bar and executing effectively.
They detail how thorough market validation—such as interviewing over 100 recruiters—was crucial before launching Ashby, which aimed to create a 10x better recruiting software by addressing widespread customer dissatisfaction. The conversation explores how traits like passion and curiosity often make entrepreneurs "terrible employees" in traditional settings, as they take on excessive ownership. Additionally, they note how economic downturns can benefit startups by forcing companies to seek integrated, budget-friendly solutions.
A recurring theme is the importance of continuously listening to customers and adapting, contrasting with legacy firms that may lose focus due to overconfidence or distraction.
FAQs
Benji and the co-founder identified significant pain points in existing recruiting tools while working at Plangrid, recognizing a market need for a 10x better solution that integrates scheduling, sourcing, and reporting into one platform.
They conducted extensive validation by interviewing over 100 recruiters and analyzing the market, ensuring there was substantial customer dissatisfaction and a clear opportunity for an all-in-one recruiting software.
Previous startup failures provided valuable lessons in execution and market understanding, making the founders more determined and better prepared to build a successful company with a validated problem-solution fit.
Budget constraints during economic downturns led companies to seek cost-effective, all-in-one solutions, allowing Ashby to gain customers who were willing to compromise on some features for an integrated platform, accelerating their growth.
Some legacy companies, especially those acquired by private equity, may prioritize profits over innovation, cutting R&D and customer support, or they become overconfident and stop actively listening to customer feedback.
Continuously listening to customers, adapting based on feedback, and staying focused on solving real problems rather than getting distracted by the operational aspects or a fixed vision are essential to sustaining innovation.
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