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Investor Series: Yousuf Khan (Ridge Ventures) on the State of Early-Stage Software Investing

47m 14s

Investor Series: Yousuf Khan (Ridge Ventures) on the State of Early-Stage Software Investing

In this podcast, Yusuf Khan, a partner at Ridge Ventures, shares his journey from an accidental CIO to a venture capitalist, emphasizing his passion for early-stage B2B software. Ridge Ventures, investing out of its fifth fund, targets seed and Series A companies, leveraging Yusuf’s operator experience to add value through go-to-market support. Despite a challenging macroeconomic environment with valuation corrections and budget contractions, Yusuf remains optimistic, noting that downturns historically foster resilient companies and that technology remains central to business transformation. He highlights that early-stage investing is less affected by market swings, with $260 billion in venture funds raised last year. Key challenges for SaaS firms include customer qualification and retention, requiring rigorous focus on identifying ideal buyers and ensuring customer success. Yusuf advises founders to reinforce teams, build self-awareness, and prioritize fundamentals like messaging and execution. He encourages new investors to view downturns as forcing functions for building strong foundations, as stable companies endure through cycles. Overall, Yusuf’s perspective balances realism with optimism, stressing that disciplined, customer-centric strategies drive long-term success in enterprise software.

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Hello and welcome to the A-level Capital podcast, a show where we speak to entrepreneurs and venture capitalists about the stories behind scale and life lessons learned along the way. This podcast is brought to you by A-level Capital, a student-run venture capital firm at Johns Hopkins University that invests in J.H.E.E. affiliated startups. My name is Rumi Naupman, I'm an economics major at Hopkins and managing partner at A-level Capital. And my name is Nusharau, I'm also managing partner at A-level and studying cognitive science here at Hopkins. Our guest today is Yusuf Khan. Yusuf is a partner at Ridge Ventures, a venture firm that invests in seed and series A focused on B2B software. They have an impressive portfolio of companies including Fastly, Discord and Braze. Recently they were also the lead investors in a cloud data security company called Theum, and A-level actually participated in the round which is how we got connected. I hope you enjoy the conversation. Hi Yusuf, it's so great to have you on, thank you for being here. Thank you for making the time, I know you had about 17 other people that you want to speak with and that when you call me up at 2 a.m. and send me an email and say, "Everybody's dropped out, I am your go-to." So Jumai Manusha, thank you very much for making the time. No, in all seriousness, thank you for the opportunity, really excited about what you and the team are building and yeah. Osmo, we are honored to have you. I think a good place to start is just with a little bit of background on yourself. How did you make your way into Venture? What was your experience prior to Venture? Very good question. I would consider myself the unconventional VC, but I was prior to this. I was an accidental CIO, a chief information officer of several companies. So several years ago, well a couple of decades ago, let's be honest, look at this gray hair, it's madness. I started my working for a CTO at an internet startup, at a great experience of understanding how to build technology teams on the e-commerce side of things. And I kept building up my career in IT and a number of different areas from software to infrastructure, to security to network management procurement others. And I always was attached to working with early stage companies, I was just fascinated by a lot of the innovation that was happening. And over time, as I progressed in my career with multiple other CIO roles, I also started advising a number of companies at early stages, especially ones that I was super excited about from a product standpoint. One of them was Zoom, which of course went on to do really well both for investors, but also as a team and as a company, as a product offering, as transformational. It was one of the early cohort of customers and early advisor to the company. And then also a number of other companies like MoveWorks, where I was the very first customer, and companies where I was a founding advisor like productive. And so I was very entrenched in the startup ecosystem. And after I'd done my fifth CIO role, I decided that it was at that time, I really enjoyed working with startups and I wanted to do that full time. And therefore, Venture was the right place to be. You know, really building a career venture requires a couple of things. In my viewpoint, one is about relationships, second intention, and deep intellectual interests as well. And so that's why I'm really excited about what A-level capital is doing because you're doing it at the ground level with a number of founders and understanding that. And I think the successful VC firms, especially VCs, are people who have that kind of alignment. And I'd like to think I'm still early in my venture careers, but it's been fantastic to date and I'm really enjoying the transition. That's awesome. You said, tell us more about your fund about Ridge and what's your guys' investment thesis and what are a few portfolio companies that you're most excited about? Yeah, so we've been around for quite a few funds. We're now investing out of our fifth fund. We are focused on B2B software. We think that's a trillion-dollar opportunity because more businesses are buying more software than ever before. And whether you're honestly a small business, whether it's an accountancy practice of 10 people or, you know, enterprise technology company or large consumer goods company, the reality is each of your functions are likely to be able to optimize through technology. That's either going through AI or automation technology. It's going to be being able to look at more software and fast solutions. Definitively, data is right at the heart of a company's strategy. And so we believe that kind of B2B software is where the focus is. And so we're really focused on that as an investment strategy. We focus on seed and series A. B2B software companies. We will typically lead an investment, sometimes we'll participate. We work very well with founders over the course of, you know, by being thoughtful listeners. Our specialty is really about being able to take a business to the next level of their journey in terms of going to market. So everything from introducing them to early customers, which were happily put into a term sheet and hold ourselves accountable, right down to helping them with their product narrative, knowing how to sell and how to position the product, thinking about how you build a sales development or and a go-to-market organization. So these are the things that we speak to tons of founders of in an industry specifically such as B2B software. We've had some great successes over the years. We were early investors in FASSILE, which went public. We were some earliest investors in Braze, which also went public in late 2021. I'm super excited to have advised the firm early on. A few years ago before becoming a partner in the firm, you know, recently we, both of us, are both of our firms invested in Theo, which I'm super excited about, which is the cloud data security space. Investors in other companies like Lightyear, which has been doing super well in the kind of B2B Telecom procurement space. Typically, I've looked at companies where using my operator experience as a former CIO interim CIO, early stage employee of companies, what problems those companies are looking to solve for. And if I can relate to that from a customer vantage point, then I get excited and interested. That doesn't, it's just one of my thought processes that I go through. And so that's typically, you know, how we tend to operate where we can add value to a company as they go to market, what's a good fit, but specifically B2B. Given your focus on B2B software and just your general experience in the space, I think this conversation will be a great opportunity for us to kind of get a pulse and temperature check on enterprise investing today. You know, there's obviously lots of news still in the public markets, layoffs, valuation cuts, overall not incredibly positive, especially relative to 2021. You guys at Ridge, though, are investing at the very early stages, you know, seed series A. What are you all seeing? How would you describe the overall state of early stage enterprise software investing today? Sorry, are you referring to some market dynamic? I don't know what you're talking about. I've had an amazing view. You've had an amazing 2022. That's incredible. Look how happy I am. It's fantastic. No, it all honestly. Look, there has been quite a rough entumble and turbulence in the market. No one's denying that, but the reality is that the early stages, that really, while is a factor, it's not it's not over-encompassing, right? And I think what happens is it's actually a great time to build a company. Some of the best companies were built during a downturn. You know, we invest at the early stages. So the data points are not as wide as you would have at a much larger investment opportunity. So we typically work with founders at the early stages. It's a real big investment in the team in kind of the market that are operating it. And my guiding philosophy is that companies are built over time and there will be economic cycles up and down. But the reality is that we're in a much more interconnected global economy than we've ever done before. And that typically means that you'll see ups and downs, but you'll basically see improvements in different sectors over the course of you know, a few months, you know, sometimes it won't be as long lasting. At least that's my vantage point. It's not because I'm a complete optimist because a couple of years ago we have the world shut down during global pandemic. Okay? And so if you think about that, the world literally shut down restaurants, roads, shelter in place, people at home. But guess what? Technology was at the heart of transforming both people's lives as well as industries. And yes, you know, a lot of people were affected, but ultimately you saw that technology played a big part in companies in terms of growth. You saw that with cloud platforms. You saw that with the evolution and building of software. And you saw that in the investment climate, there was $260 billion raised last year in venture funds. There was about $300 billion invested just last year alone. And substantial amount of that was also, you know, comparable to that the year before during 2020. So I remain both optimistic. I think at the early stages, it definitely affects how you think about a company may be fundraising because you don't have, you know, the valuations are probably not as I would say insane in some cases. So sometimes a correction, you know, is required in certain conversations. But we because we believe in kind of a long term opportunity, we will invest at the earlier stages and see where we can be able to add value. We've seen companies do, you know, really well. Not saying it's been all rosy. There have been some companies that have been affected, of course, because they're selling into environments, which have contracted their budget or otherwise. But that's how you build a company, navigate through tough times and you better teams that can do that. I really like your perspective, you see. If I was telling you, mean, just the other day that people can be so rash and maybe even a little dramatic whenever we see any volatility and pressure in the markets. So with that, how has your investing cadence for the year changed in comparison to the year before? And have you guys at Ridge had to adjust your evaluation expectations. You know we are very disciplined. We take great pride in that. I think the reality is when we think about companies, we want to basically put in and understand where they are from a market perspective. Valuations are ultimately determined by the market. We've been able to happily say, "Yeah, we walk away from some companies that we think are overvalued. We don't think is a good investment, but not just because of valuation." As I said earlier, we've had maybe a couple of conversations where we talked about valuation. It's not a big part of the conversation to be particular. In terms of cadence, we remain super active, investing out of our fifth fund, which we raised this year. So we are active out there. We've grown the team by adding in a couple of partners and members on the investment team. Definitely the activity, of course, there are a number of companies and founders who said they don't want to raise and they're being more cautious because they want to manage their burn and that's totally fine. But it's another day in the bench business. You keep continued to basically talk to great companies and great founders. Sometimes when they're forming the company and they're thinking about it, others who we met last year and want to reconnect with us, but it's a very, very busy time. It has been a very, very busy year. When thinking about both evaluating and supporting your portfolio companies, have you seen them hit their ARR and other growth targets for the year? Ultimately, you understand that the company will be built over several years. You understand that there's a macroeconomic environment which is affected certain industries, whereby budgets may well have been affected and therefore that slows the sales cycle. But ultimately, if you've built a solution of value, if you've built a solution of impact and you've been able to go through a rigorous sales process, that sale will eventually happen versus it being completely stopped. So in a lot of cases, it's about when, not if, the thing about startups is, especially in early stage companies, irrespective of what's happening in the macroeconomic environment, they will go through their own challenges. They'll be turnover in the team at the leadership level in some way, shape and form. They will be a shift in the product thinking. They will be a shift in the market investing. So I would say outside of what's happening in the macro environment, that's just a natural part of the course. We want to be thoughtful listeners on the board versus being able to be prescriptive. We'll give guidance, we'll provide data and ultimately the objective is partnership. Our ability to partner with the team and to be able to be supportive and be helpful and of course, have a thought partnership and kind of an intellectual discussion about how to build a company. Because we've both got shared goals there. Our goals are aligned and I think that's super important for a successful VC firm and a venture investor and a board member to have with a founder. We're proud to say that we built that of the course of last decade plus. We talked about dealing with a difficult macro environment earlier. What would you say are some of the biggest challenges that are specific to SaaS companies in this climate? Have you found that customer acquisition happens to become this really big hurdle? Is it nutrition or retention? You know, I think that one of the consistent problems is customer qualification. I think that's always one of the challenges for me to be companies is to identify which customers are the right fit for them and that requires quite a bit of work. You need to identify who the right buyer is in the organization. Are they forward looking thinker? Are they reactive to the market? What does the buying cycle look like? Are they a good fit from a technical environment? So there's a lot of work that needs to go into that process. Sometimes it's based on relationships and introductions. For example, I make a ton of introductions to founders with CIOs, CTOs, CISOs and otherwise because I know their barmants and I can relate to it having been a former sea level executive at public companies. So I think customer qualification is one of the key things. I think the second which is pretty consistent, especially in this time is retention and customer success. I think the companies that will win in B2B enterprise are the ones who provide transformational customer experience. That which is focused on retaining your customer, making them wildly successful, being able to deploy out of solution and really truly partner with them to be able to make sure that they get the visible win and the fact that the outcome that the customer is expecting is aligned with what they were sold when the company was first pitched to them. That's really interesting. I mean, I feel like your tone so far has been pretty optimistic. We've seen a lot of more doomsday scenarios. Twitter can sometimes become a really dark place. So it's very cool to see your optimism. What advice in general are you giving your portfolio companies at this time? Look, I think there's a couple of key things. Well, yeah, I am optimistic. Sure. Okay. I will, I will have to admit that. But I'm also a realist, right? I mean, you have to remember the stage that you invest in is different. The company is that, you know, you get excited about, I love my job. I love the ability to be able to talk to founders about the problems they're trying to solve for. So perhaps I may have had a bit too much sugar this morning, guilty as charged. Maybe you want or two more cappuccinos shouldn't have basically been taken. But you know what, it's Monday in the venture business and that's basically what happened. But the reality is this. Look, over the course of time, one of the things I've seen in economic cycles is you've seen a downturn. I've seen a couple of downturns over time, but the level of bounce back and the cycle for bounce back has become shorter. So I remain optimistic for that purpose. The second is it's just about rigorous focus. So actually, I think last year, yeah, I would say last year there was a little bit of craziness, right? There was some of the valuations and some of the companies that were being valued at I think was grossly inflated. You know, that's not a shocker to anyone, right? You know, the advice I give now is relatively consistent to what I've given, which is really about business building. So our focus at this stage is being able to say, how do you build a business? Of course, we're aware of a macro environment, which has affected them in terms of their sales pipeline, in terms of their revenue targets, in terms of their messaging. But the core foundations of basically building business remain the same. You need to have a great message, you need to have a great team, you ultimately need to have a great part of roadmap and a good initial product of value. And then the question is, how do you execute in a in a market, which may be turbulent? And that's where the advice is very relevant in specific areas. And so I focus a lot of my time on that. You mentioned previous lessons from downturns there. You know, obviously, we're very new investors, A level is a student-run fund. I haven't really seen macro cycles. I barely remember 2008. I was like seven years old at the time. What are some of your takeaways from previous downturns? Maybe even lessons learned or advice that you could give new investors like myself? Yeah, I mean, you're not missing much. The thing is that each of those downturns were very different. 2000, you know, definitively was vastly different because that was really when the tech industry was finally taken off, especially with the evolution and the kind of impact of the internet e-commerce. And that was kind of driven there. 2008, there was a global financial crisis that just had effects across every industry rather than just tech, but that was a downturn. The biggest advice I give to founders is you really need to have a lot of rigor. One, you know, is to say make sure you reinforce your team and make sure that you understand the gaps are in your team and how you fill that. Second, build some self-awareness and understanding that there are certain things that you as a company are missing and need to resolve those. Number three, focus on customers. Number four, think about how you build a successful business, right? Think about the foundation. You know, sometimes downturns require that. Sometimes you need a bit of a shake-up to be able to say, okay, am I on the right path? And sometimes that could be a healthy thing. It's not encouraged by any matter. You don't want to have it, but you know, sometimes you need a forcing function to be able to do that. So focusing on good foundation, stable houses, which last a long time, the reason they survive is because they built on good foundation. So think of it from that advantage. When you build a good foundation, everything else will sort of take care of itself. That makes a lot of sense and I think in a very hot market, I think many companies lose track of fundamentals. So kind of getting back to the basics is not always such a bad thing. We often have this debate internally at A level. This concept of nice to have versus need to have, especially in the context of B2B software. How do you determine at Ridge whether a SaaS product is actually mission critical or, you know, just kind of a nice to have? And then especially when budgets are under so much scrutiny as they are today. The best way to do that, honestly, is to speak to customers. Look, I was an early customer of Zoom. In 2015, I guarantee it to you, most CIOs, 90% of CIOs, were not saying, I can't wait to roll out new VD computing software. That was not the priority that they had, right? But if you think about the product that Zoom had built and the company that Eric had led in terms of culture and branding and thoughtfulness and how he served customers, that was a transformational cell. And the reason that I believe Zoom was multitude, but one of them was the fact that they focused on great user experience. And it was aligned to where companies were going versus where companies are. So in video composing, I spent a decade before becoming a Zoom customer having deployed out number of video composing technologies and collaboration technologies, right from chat messaging and internal messaging such as Yammer and Skype, right down to high scale, take-pronged solutions from Tanburg and life size and others. So I've got experience and relevance to that. But I actually always understood when I started talking to Zoom was that they were building for where the company is now, where they're going. By that, basically, one of the biggest issues was the fact that you didn't have a central experience, which was unified when it comes to having video collaboration. In most other products in the market, you would have a desktop product and they would not be able to connect up to the room product. Or you would have a mobile product that was really not so good and you'd have problems. And then, the actual meeting experience was not so great. So companies when it comes to nice to have as necessary, sometimes CIOs and CTOs don't know that this is possible, right? There's education that's required at the market and Zoom did that. Zoom said, "Hey, you've got people who are on laptops and working remotely. More people in your enterprise and your company are using mobile than ever before." And of course, you've got conference rooms and shouldn't they be in the same place at the same time when they're having a meeting? It sounds insane if you think about it. Like, it sounds so obvious now, but that was not there in the market. It really wasn't in a good high quality, easy to use way. Zoom did that. And as a result of doing that, as a result of building great technology, best in class hardware, best in class software, best in class experience, you know, CIOs were like, "This is what I need to have." And they basically came around to that thinking. I was the first customer of a company called MoveWorks, was in the enterprise AI space. It automates IT support operations using a chatbot, deployed in your message systems, such as Slack or Teams, and it integrates with your service management system, like Giro Service Desk or ServiceNow. And basically, in between that, there's an intelligence layer built on NLP, and definitively being able to think at transfer learning, or doing machine learning, on understanding what the IT support issues are. I can guarantee you in 2017 when I became the first customer of MoveWorks, no CIO was saying, "I can't wait to deploy out AI for IT support." Like, it wasn't the case. And it was definitively something which was nice to have. But when you start educating the market, you discover, well, hey, on a second, I've got a 100% IT team, and 40% or 50% of the IT support issues are being dealt with manually and repetitively. Right? Surely there should be some patent matching and automation available for this. And that's what MoveWorks did. So it's not a case of nice to have or necessary. Some things are necessary. There's a lot of things that are not necessary, which may be considered nice to have. But it requires a founder to be able to position and educate the market, educate the customers about the possibilities, and then talk about the fit of that product into that company's architecture. Actually, I love that reframing. And directly on that point, what's your advice for companies who are trying to create and define new categories? Look, I think category creation is a really hard thing. The ultimate definitive go-to for that is market messaging. That requires customer education and market education. Because the problem is that a lot of people have accepted a negative standard in the industry. Things that were obvious to us, we've kind of said, that's the only way it's being done. And then you come to the realization, you're like, wow, there's a whole new thing that's actually possible. And so it takes time for people to make that leap. Sometimes it's a leap of faith, but sometimes it's being obvious. You know, the other part of this is in the consumer experience. So because technology is now overwhelmed a large part of our personal lives, we have now got this experience of being able to consume technology and get things done in our personal lives. And now we come into the workplace, and you're like, well, why is this taking so long? You know what I mean? Because that's your psyche. It's just human nature. And so as a result of that, people start coming to the conclusion, like surely this should be an onboarding experience that is similar to this other application that I joined recently. Or why doesn't this have this for our employees? And so CIOs start to think in those terms. So when you think about category creation, it's not necessarily saying, you know, why is it better? But what's missing? It's a very different sort of nuanced conversation to be told. And that requires for founders to educate the market and to be able to tell them what the possibilities are. You mentioned theom at the beginning there, which is a company that we both invested in, Ridge led the round. A level capital was lucky enough to participate. It's one that we're really excited about. I'd love to kind of use theom as a case study to understand your decision-making indiiligence process at Ridge. Helpful places start as probably just what does theom do overall overview of the company? With Theom, we had a phenomenal experience and relationship built with Navindra, yet a phenomenal engineering leader, a technology leader, a forward thinker, and somebody who was successfully built, you know, a high revenue product offering at a large company like Cisco in the past. And so I came from a space where I was a CIO of companies in the infrastructure space. So I knew of the products that he had basically built and been involved in. So I had first hand experience of like, okay, I've seen that work and I've seen that being sold and being able to have the opportunity to speak, let alone partner with someone who's basically built a high revenue, high impact product like he had done was super, super exciting for me. We built a relationship early on when he was talking about what he was building in the cloud data security space. I think what differentiates Theom and I've been a customer of a multiple products over time in different approaches. And it's a big market. The market will continue to grow. So one is if you look at the market thesis, the reality is, you know, cybersecurity budgets are only going to increase over time. Number one, number two, cybersecurity threats are also going to get more complex and very targeted over time. That's also real. The third part is you have a number of companies who are moving their workloads into large data stores by the cloud providers such as Microsoft and other data layers such as Noteflake and Databricks and others. And so what's required from a problem statement area, which something resonate with us is that, you know, and I haven't been an interim CIO of a couple of companies, you can either solve some of the security issues application and workload by workload, which is very manual, very heavy. It's not automated. It's not a holistic approach. It's not very streamlined. There's no very prioritization. And Theom used a data-driven approach for security prioritization for the most valuable asset of the company, which is the data. The architecture of the product we thought was groundbreaking. I thought the approach, the founding team of Navendra and Ravi and Supri and then the team that was being formed around them, we were super excited by and came very well referenced. We thought the product was differentiated. We believed in the market and we built a good relationship to be able to say, you know, this is a space that we want to be involved in. It also came down to relationships, you know. Navendra is exceptionally humble human being despite all of his achievements. And his objective is to build a company of long lasting value and one that he has a deep sense of pride in. You know, for me, it's a real privilege to work with somebody who has got that sort of background and who's basically built it and is ultimately going to trying to build the best product in their career. And I'd love to be able to partner with our opportunities. So that that's how we bought about the company, the diligence that we did. And yeah, look, we looked at the we looked at the co-investors. So we're super happy to partner with A-level Capital. Really excited about the platform that you're building at the stage that you're building at. You know, venture capital is really about relationships. There were a ton of funds that wanted to invest in Theo. But he was very insistent about making sure that he had a good relationship with A-level Capital and that he had made that commitment. And you know, I've only had very positive interactions with yourself. So I hope that this is one of many other companies that we're able to do together. We hope so too. That would be incredible. Yeah, we're both very excited about Theo. And it was great to be part of that round and to get to know Navendra. As you said, he was a phenomenal person. Incredibly humble, incredibly accomplished. So can't wait to see what they will be building there. You mentioned relationships. How do you think about building relationships with your portfolio companies and supporting them in their journey? I think the most important thing about relationships is you've got to listen and you've got to reflect. Ultimately, you have to remember what founders are doing is really, really hard. Just think about a lot of the founders that you'll meet over time in your career adventure as I have. Some have had very good jobs, some have had some deep personal experiences. And despite all of that, they're going to basically go after and build a company and build a product, take it to market, go from nothing, right? And then take it to, you know, hoping to be a phenomenal outcome. And that's really, really hard. And so it's very easy for, you know, people to say, well, why don't you do this and you know, do this and go to market and do this? No, my take is you've got to listen first and foremost. And then the second piece is you've got to be very focused. It's not about being found or friendly. It's about being found or focused. One of my colleagues, Zayn Rizavi, who's a principal with us, said this to me and I really resonate with me because he has been able to build a relationship with founders. And I think building a great founder experience, building good founder relationship, being thoughtful with your advice, listening, actually understanding where the company is, and then being prescriptive with your advice. It's so defined, it gives up high level stuff like, oh, you know, you should do more here. Well, what's the path? Right? And a lot of people can't do that. That's okay. They don't have that experience, or they don't have the data points to do that. But I think it's very important for people to be able to do that, especially during a downturn where people are nervous and they're worried about, you know, meeting a revenue number otherwise. So I tend to basically focus on that side. Can I make customer introductions? Can I help you give you feedback on your product? Can I think about where a right customer fit is? I tend to do that, but I also am always very conscious about giving feedback and taking feedback and I encourage both. On this topic of advice, how do you think your experience as a former CIO helps you give better advice to start up founders? I can just tell people what people want to buy. For the last 20 years, I've been involved in buying software, building software, architecting, deploying, integrating in, looking at the data. Some of it successfully, some of it not so successfully. That's okay. Lots of lessons learned. Lots of scar tissue. And as a result of that, I can relate to a customer vantage point. Hopefully, better than a lot of people. Number one, number two is I'm able to actually be able to assess what this customer sentiment may be from a market perspective, like prioritization. So not just about, hey, would I buy this product in its entirety, but hey, market-tiving-wise, does that basically relate? And that also is sometimes you're too early for a product offering. Sometimes it's not complete, and most products are not complete. Software industry in itself is imperfect by its very nature. We continue to grow, and iterate, and build, and innovate. But the reality is sometimes it's about the timing in terms of you ask yourself, why is the product needed now? You know, what need does it mean for it to be able to do that? So one of the things that I've basically provide from an operating vantage point is, is about buyer sentiment. It's also about the propensity for something to buy. But the third piece is, how teams are structured. If you think about that, you know, I've managed large teams globally. I've structured them, organized them, mentored coach led, built, hired, fired, etc. So I know what org structures look like. I know where the partnerships are. I'm able to measure that. And that just comes from experience. So I'm able to relate that to a portfolio company and tell them about their ICP, for example. And say, hey, by the way, this buyer would sponsor this initiative, or this department won't care about it, and here's why. So it's those nuanced things, which I think I'd like to provide. And hopefully, I have provided. But you're going to have to find out, and speak a bunch of founders. And hopefully, we can invest more together. It's honestly so cool to hear how your background as an operator has shaped your perspective, because that's one of the things that I really love about venture in the investing world. You know, there's no one perfect path to this space. It's really your own unique set of experiences that gives you a distinct perspective. And I think that that diversity of thought is what creates a really solid investing team. So as a former CIO, what do you think are some of the most exciting trends within the broader software space? You know, in the broader software space, ultimately, we are continuing to see a lot of drive towards automation. Definitively, there are too many tasks and activity in the enterprise, which are manual and repetitive. And they should be automated. It doesn't mean we should get away with jobs. It just basically means that people are getting tired. They can't frustrated that they have to constantly just repeat stuff. Right? It's cumbersome. It's cumbersome in our personal lives. It's not professional lives. And so we have to relate to that. And so there is a definitive drive towards much more automation. That's a broad category. You could look at things like open AI's new offering and being able to automate and be able to accelerate a whole bunch of content creation in some cases. In other cases, it's really about automation of tasks that's happening. So automation continues to be a priority area. Cybersecurity continues to be a high priority area. Irrespective of how crowded the market is, irrespective of the kind of continued growth in the number of tools and approaches, cyber security threats continue to be very, very complex, very multifaceted, and they're very targeted as well. And I think that's very, very important. I think number three is really being able to aid the customer experience and optimizing that continues to be an investment area. Really being able to think about very thought because remember customer experiences are becoming very unforgiving. You have to wait too long for something you're out. You're switching off. But like you are competing for a mind share. And so it's about the systems you have for providing good customer experience as providing the good interface to be able to do that. And that consistently requires optimization. The UX that needs to come into place. The data that's available. The product offering itself. The features. The roadmap. All of these things require constant attention and being able to try. I think one of the kind of areas which people kind of don't bypass but don't recognize how big an issue is this privacy. Privacy and compliance. This is a major, major hurdle. If you are an early stage company. If you are a later stage company. There is going to be more data enforcement and more data regulation in the time ahead. That's definitive from my standpoint. I say that pretty and fatically because I believe that data has not just been embedded in companies. I think it's overwhelmed companies and people are wanting to make data driven decisions across the sales and cross product customer experience. Otherwise you have the ingest of data sources from IOT and sensors and security and others are continued to basically explode. And this, all of this data needs to be captured, ingested, needs to be transported and processed. And then it needs to be made sense of and needs to be deployed and used effectively. And all around that layer there's regulations and compliance overhead that exists. And with all due respect, you do not have people from leading universities in the East Coast who graduated and say, "I can't wait to go into data compliance." But so reality is that those problems are going to be solved through software. That's an area where people are going to need to focus on because you don't have the team. There is probably a much bigger focus on technology that affects the workforce, the employee experience. More than before that will rate from great onboarding to just great employee experience and benefits. And the provision of extra services to be able to make sure that you're able to retain employees, think about mentorship growth. So, you know, it's a very widespread, that's what I would say. It's always encouraging to hear how much innovation there is. I'm in a room there still is for innovation. The last part of the interview is just what we call the lightning round. Short answer questions focused on career development and especially targeting students or people just starting their career and potentially interested in getting into this world of tech investing. The first one, if there's anything that you could tell your college self, what would it be? Get a better dress sense. I mean, look at me. I dress like a librarian. No offense. I mean, sweat a vest. What was I thinking? Terrible. Absolutely terrible. Other than that, it's a very good question actually. I think the one thing that comes to mind is probably understand how a business operates. Yeah, that's probably the thing that I probably discovered a little bit later. I've always very interested in business when I was in college. But being able to actually understand how a business operates, irrespective of what job you take, being able to understand how a company operates, that helps you from a career standpoint. You understand the relationships, you understand how the function, what the revenue is, but actually understanding how a company operates, I think, is key. I think the second piece of advice I would say is ask yourself, do you want to lead? Do you want to follow? There's no harm in either which one. And so that kind of self discovery is kind of important. I've probably discovered that later on that for, oh, I think I can lead. And so when I first got my first CIO role, I was like, okay, I actually hold the title, I actually hold the team, I hold the budget. I'm excited by it. Some people are not. And so, yeah, probably those two pieces of advice. Yeah, I mean, we kind of talked a lot about you as an operator. And so, maybe for people who are really early in their careers or students or just people that are interested in venture, you know, in hindsight, is it something that you recommend? Is it something that you want people to do? Go get operating experience before thinking about investing? I love this industry. I love what I do. I think it creates economic value. I think it has a positive impact in the economic cycle. And honestly, I think it allows the ability for great companies and products to come to life. And there's no shortage of examples of that. My advice for people going into venture is pretty simple. One is you really got to be invested in a long term. You've got to understand that it's a journey. And you've got to ask yourself why you want to get into it. I love seeing businesses being created and being built over time. Being able to speak to a set of founders in a cafe one day and then speaking to them two, three years later. And they're like hundreds of employees and they've got like sales kickoff and they've got a logo and swag and they're in the news. It's mind-boggling, but it's so fulfilling to basically see that. So think about the reasons you want to go into venture. You've got to love talking to founders. You generally have to love that part of the job because that is the job. And I have, pride myself, I've never laughed at any idea. I just don't. Because the reality is you just don't know. You don't know. The ability to learn is the third thing that you need to do is you have to have a thirst for learning. You have to be intellectually curious. And I'm a monumental nerd. Totally fine by that. Dress like it, act like it, study it all day long. No problem. But you have to be able to do that because the context switching that goes with the job is very real. Even if you are investing in one space, it just grows over time. There's all these different use cases and opportunities. And then the fourth thing is it's for the long term. The feedback loop for Ventures is several years. You know, you've got to get involved in the deal in a company like we have now in the field. It's going to take some time. And that's okay. But surely if you're on the journey versus being on the sidelines, I'd much rather give it a full shot and go for the win than anything else. I don't look back on it from that vantage point. So I mean, the thing is you've got to basically build relationships. Understand startups and founders. I've made myself available to early stage firms. People who are looking to go into venture. You know, I think it's a great industry to be in because I think it's a big factor in terms of how it's able to generate output in terms of companies being created, which create jobs, being able to create economic value for both founders, being able to provide innovation to customers and companies. That's very exciting for me. It takes time. You don't invest in every company in me, but you've got a job to be able to provide good returns for your LPs. You've got to be able to serve your founders. You've got to be a good partner. And I think it also tests your skills, both as an individual and what you're able to do. So I've always been interested in adventure. I love talking to founders from the very early stage even before I came into venture. I love innovation. I love technology. And I'm intellectually very curious about a lot of these areas and I go deep into them, sometimes to my own peril when I shouldn't be. But that's okay. You learn as you go along. But I encourage people and I'm happily help out anyone if anybody needs advice thinking about a career investor. I will happily basically talk to them. For people maybe not interested in venture but interested in working at startups, what are some positive signals that they should look for before signing up for a new startup? Number one is ask if the product is solving an actual problem. I think that's one of the common denominators I would say. Is it solving a business problem? Is it solving a problem that people care about? Is it a problem that is actually being solved? Is it additive or is it transformational? So that's one thing. Second is really think about the vision of the company and that comes back from the founder. Are they someone who can build a company or are they someone who've set a vision which you are excited by? Ultimately it's really about the level of excitement that you want to go towards. I say this and I'm totally conscious that it may not resonate but I think it's very important for people to go where they're most needed. And I know that's difficult to assess when you're early in your career and you think well you know who's going to really need me but you'd be very surprised at early stage companies. There's no shortage of work to do and you're going to be involved in everything. And so part of this if you're excited about the company, you're excited about the product offering, you align with the vision and you like admire the founder or the founding team or the team or the culture around it and you think you can add value than you should go for it. But what's required is for you to go through a process to be able to do it. I've seen lots of bad decisions in my honest opinion being made because people who are attracted from the economic side. I don't agree with that. I don't judge it incorrectly or otherwise. And I think the moment you think well if I get into an early stage startup and then I'll just get some stock options and I'll you know there's a lot of companies that don't too well and that's okay right. Sometimes that's that's part of an economic cycle. It's going to be good and bad but go with the right intentions and if you are deeply passionate about something I believe success follows and that's my biggest career advice that I give to anyone. Air respective career journey otherwise. If you are passionate about something, success to spawn because what happens is the inner kind of part of you of your belief system and your kind of values and your energy that just gets amplified and you don't even think twice and you just like do the best work of your career and everything else takes care of itself. So that's kind of the way I sort of think about it. So you shift to be honest. I find software and enterprise access to be really intimidating. I dedicate most of my time here at A-level tour life sciences and healthcare initiative and looking at therapeutics and diagnostic companies and I know a community of degrees to me but I'm just much more comfortable in that wheelhouse compared to some Bayland data security. So for those of us who want to learn more and familiarize ourselves with this space, what advice or what resources would you recommend? You know every industry has a language. Every industry has a vernacular. It has a way of operating a system so to speak. With that there's no shortage of resources. I think the best resources are people to be perfectly honest and I don't want to refer to them as resources but I honestly think it comes down to being able to talk to people in the industry. Founders of companies, operators in companies and enterprise B2B investors and myself. I publish my advice on LinkedIn to founders on regular basis. So there's actually no shortage of resources. I think what requires is if you're interested you take the effort to be able to move the needle forward and you connect with people accordingly. And guess what? I encourage people to reach out to people in general and people like well, what if they don't respond? Or it's okay. It's okay. It's just another day of the technology business. There's a bunch of people that will happily take your LinkedIn request or respond to email. And there's a bunch of people that won't. And that's okay. All you need is to continue to build knowledge. I honestly believe that more depth you have in the industry that better it is. So Anusha, next time I look at a biotech investment, I'm going to basically get in touch with and say listen, this is not in my realm but I spoke to these other firms and you know, I would love to get your take on it. And I'm sure you'll be like, yeah, give me five minutes, right? Anusha is truly a biotech queen. So yes, definitely send or anything that you see. I mean, I don't even know how you do what you do. I don't either. As an econ major, it baffles me but very impressive nonetheless. And then I also couldn't agree more with your point about just reaching out to people. It's so surprising to me, especially as a student, how many people answer my messages. It's something that I started doing this year and I've just been incredibly impressed. You answered me, for example, and you're on this podcast today. So good things happened. I did. Absolutely. I'd love to be able to collaborate and talk more, you know. Life is too short. Loved it. Yeah, so definitely take those shots. You don't know what happens after that. One final question and this one is especially broad. So feel free to take it any direction that you like. What is the best piece of advice that you've ever received? That's a tough one. It is a tough one. I would say the best piece of advice that I was given was go where you are most needed. I turned that around a little bit. Ultimately what it translates into is go to a place where you do the best work of your career. And you may not know that right off the bat. But sometimes it's a feeling and you have to be excited about it. I'm going to just give you the life advice that I was given for what it's worth. So this career, a professional one, but it's life advice. One of the greatest writers is Shakespeare who once wrote that if you are true to yourself, you never will have to lie to anyone. And ultimately if you are true to yourself, you will ultimately be able to provide to the community around you and the people around you who you are and it really is both liberating and being able to do that. So understand that there's a whole bunch of imperfection that exists in all of us. That's fine. Don't conflict with the truth. So the time ahead be true to yourself, but give it a fair shot. I followed that advice very closely for a very, very young age. I think that's such a great place to end the episode. Thank you so much for taking the time to speak with us today. I really enjoy the conversation. I hope others did as well. Any parting words, is there any place that you'd like people to learn more about Ridge or about your work? You know, to founders or anybody else, I'd love to talk, don't hesitate to reach out to me on LinkedIn and more than anything else, conversations like this are the forums that you're basically setting up are really important. And it shows in the fact that you're able to do a co-investment in a great B2B company based on what you've created. So you should definitely make sure that we continue to work together in time ahead. Thanks so much for listening to an episode of the A-Level Capital podcast. We had a lot of fun reporting and we hope that you enjoyed the conversation as well. If you're new to the show, go ahead and follow us on Spotify and LinkedIn. We'll be posting consistently each week. Last but not least, if you're enjoying the A-Level Capital podcast, please leave us a rating and a view wherever you listen. It really means a lot.

Podcast Summary

Key Points:

  1. Yusuf Khan is a partner at Ridge Ventures, a firm investing in seed and Series A B2B software, with notable portfolio companies including Fastly, Discord, and Braze. He transitioned from a career as a CIO and early-stage advisor (e.g., Zoom) to venture capital.
  2. Ridge Ventures focuses on B2B software, emphasizing a trillion-dollar opportunity as businesses increasingly optimize through technology. They lead investments and support founders with go-to-market strategies, customer introductions, and product positioning.
  3. Despite market turbulence (e.g., valuation cuts, layoffs), early-stage investing remains active. Yusuf views downturns as opportunities to build strong companies, noting that technology thrived during the pandemic and venture funding remained substantial ($260 billion raised, $300 billion invested last year).
  4. Key challenges for SaaS companies include customer qualification (identifying the right buyers) and retention/customer success, with a focus on delivering transformational experiences.
  5. Yusuf advises portfolio companies to maintain rigorous focus on fundamentals

Summary:

In this podcast, Yusuf Khan, a partner at Ridge Ventures, shares his journey from an accidental CIO to a venture capitalist, emphasizing his passion for early-stage B2B software. Ridge Ventures, investing out of its fifth fund, targets seed and Series A companies, leveraging Yusuf’s operator experience to add value through go-to-market support. Despite a challenging macroeconomic environment with valuation corrections and budget contractions, Yusuf remains optimistic, noting that downturns historically foster resilient companies and that technology remains central to business transformation.

He highlights that early-stage investing is less affected by market swings, with $260 billion in venture funds raised last year. Key challenges for SaaS firms include customer qualification and retention, requiring rigorous focus on identifying ideal buyers and ensuring customer success. Yusuf advises founders to reinforce teams, build self-awareness, and prioritize fundamentals like messaging and execution.

He encourages new investors to view downturns as forcing functions for building strong foundations, as stable companies endure through cycles. Overall, Yusuf’s perspective balances realism with optimism, stressing that disciplined, customer-centric strategies drive long-term success in enterprise software.

FAQs

A-level Capital is a student-run venture capital firm at Johns Hopkins University that invests in J.H.E.E. affiliated startups.

Yusuf Khan is a partner at Ridge Ventures, a venture firm investing in seed and Series A B2B software companies like Fastly, Discord, and Braze.

Ridge Ventures focuses on B2B software at seed and Series A stages, believing it's a trillion-dollar opportunity as businesses increasingly buy software for optimization. They lead investments and help founders with go-to-market strategies.

He was an accidental CIO for several companies, advised early-stage startups like Zoom, and after his fifth CIO role, moved into venture capital full-time, emphasizing relationships and intellectual curiosity.

Yusuf remains optimistic despite market turbulence, noting that early-stage investing focuses on team and market, and that downturns are good times to build companies. He highlights that $300 billion was invested last year.

Ridge remains active, investing out of their fifth fund, but is disciplined on valuations, walking away from overvalued companies. They focus on long-term opportunities and have grown their team.

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