How Startups Win: Shefqet Avdullau on Angel Investing - S3 Ep1

Welcome back to Professional Perspectives. I'm Aurov here with my co-host, Pranit. Today, we're kicking off Season 3 with a powerful episode about the world of angel investing and startup growth. That's right, our guest is Chef Ket Avdulao, an angel investor, board advisor, mentor, and connector. In just 4 years, he's made 15 investments with 2 successful exits already. Before that, he built his career as a software engineer, then scaled and exited his own ventures. Now, he brings that first-hand founder experience to the companies he backs. Mr. Avdulao's investment thesis focuses on innovative and disruptive technologies, especially in fintech, adtech, and health tech at later stages. He prioritizes founders who are experienced and resilient, and he's passionate about helping entrepreneurs not just secure funding, but also navigate the real challenges of scaling. We're excited to dive into his journey, from engineer, to founder, to investor, and learn what makes a great founder, a compelling startup, and a lasting partnership. Mr. Avdulao, welcome to Professional Perspectives. Hi, hi guys. Thank you for having me. Two things I just wanted to touch on on that intro. Thank you for that. The first one is, I've completed 16 investments to date. I just announced one very recently yesterday, so you probably didn't have that. And the other thing, I'm stage agnostic, apart from, so on fintech, adtech, I'm stage agnostic, whereas for health tech, I just focus on late stage in series A and later. Because of the timeframe to exit, generally, health tech, madtech, biotech kind of ventures take about 10 to 12 years to exit, whereas the average for other sectors is aimed to be at five to seven years for an exit. So yeah, those are two points I wanted to touch on, but absolutely thank you for having me. Of course. Yeah, thank you, Mr. Avdulao, and congratulations on your new investment, making it the 16 investments. So to start with what you said, for our listeners, could you describe what stage agnostic is and why an investor might go down that path instead of just investing in the later stage? So it's investing at any stage. So when I got into angel investing, I was lucky to have a mentor who was doing private equity investments for about 33 years at a time. And he kind of helped me build this strategy to kind of preserve my capital. And stage agnostic means investing at any stage, no matter what stage. And the reason why I am stage agnostic is, although I do keep most of my investments in early stages, precedence seed, which are otherwise called as angel rounds, I also do make some investments in later stages, like for health tech and others in like series A or later on B and C, or even pre-IPO, because even if all my investments fail in those early stages, I still will have some of my capital preserved and probably some of the returns brought from those later stage investments. That's why I'm stage agnostic at this point. So it looks like there was actually a lot of development within obviously between your first investment to your most recent one. And your experience, what separates like a second time founder from a first time founder in terms of both approach and success rate? It's interesting. I mean, I would say the first time founders bring the fire, but the second time founders would bring the map. That's how I would describe it. So the first timers would run on this role passion, which is very, very incredibly powerful, but it can also lead them right off a cliff, whereas the second timers, they come with a playbook. They know where the traps are. I do invest in both though, but I go in knowing that a second timers journey will probably have fewer self-inflicted owns. Awesome. Yeah. And I feel like definitely there's a lot of wisdom as you get more experience in your startups compared to someone who just started in a figuring out the process. But to get started on your own journey and your early start in the career, what inspired your transition or start in angel investing? For me, it really just came down to leverage. So I got to a point where I realized I could either go on, build one more company myself or I could help others build 50, 100, 200 companies. So angel investing is just a way to scale my impact basically. So moving from writing code to writing checks that empower the best founders to build the future. It feels like the most direct way to have a hand in creating what's next than just doing just one company. Yeah, that actually makes a lot of sense. And in your transition, how would you say that your entrepreneurial journey, like founding and exiting companies, shaped the way you advise and mentor these startups? Well, it means my advice is not theoretical. So it's built on scar tissue. I mean, I've nearly missed payroll and I've had to private failing products. So when I advise a founder, I'm not giving them some text book theory. I'm giving them a playbook of my mistakes so they can hopefully avoid them. It's all just pattern recognition from someone who's actually been in the trenches. Yeah, I feel like advice can always be helpful, especially in a really sketchy and hard field to navigate through. On your LinkedIn, I was seeing that under your bio, you had something called your investment thesis. And in your investment thesis, you talk about your strategy and how you navigate in each sector. Could you quickly walk us through your investment thesis? Right. So I mean, sector-wise, I mentioned earlier, I invest in fintech, adtech, and health tech. So those are the sectors where I focus. And stage, I said I'm stage agnostic, geography-wise. I invest US and UK because of the common law and all the... I basically have worked in this market before as a software engineer and have dealt with those markets. So I know a good deal of the legal environment and the taxation system. So that's why I focus in those two countries, geography-wise. I prefer second-time founders and more, like I mentioned earlier, they will have learned the lessons. That's why I prefer them. But I also invest in first-timers as well. Yeah, that's a bit... And I try to stay away from crypto, web-three blockchain-related stuff unless they're at a unicorn stage or later on where they have kind of proven themselves. So yeah, that's roughly my thesis. Yeah, and to get into, let's say, just to specific, what do you look for first when you meet a founder or when you're first evaluating a pitch? What's kind of the first thing you look for? I mean, the first thing for me is always founder market fit. I'm trying to answer the question, why is this founder uniquely equipped to win this specific market? So I look for what I would call a targeted obsession. It's not just having a general passion. It's a deep... We'll almost feel like an unfair advantage that they have because they understand the problem better than anyone else on the planet. So that's what I look for. Yeah, and I definitely feel like that experience can help in success. But talking about success, for you personally, you've had 16 investments and two exits in just the past four years. What lessons have you learned from both the successes and the challenges? That's a good question. I mean, I think the biggest lesson that I have learned is that the market is undefeated. So a great team in a bad market will almost always lose, whereas a good team in a great market though can win big. So the second thing I've learned is that your initial plan is always wrong. Things will come on the way. So the winners are just the ones who adopt the fastest. So my exits came from founders who were ruthless about listening to the market and acting on that without hesitation. So yeah, those would be my successes and challenges. Yeah, and it seems like a big part of this is, of course, like market changing and adapting to these trends. How would you say you personally view the angel investing landscape evolving over the next five to 10 years? If I'm looking ahead, I think the hobbyist angel is going extinct though founders just have too many options to take money from someone who can add operational value. So the future, I believe, belongs to the operator angel, someone who has actually built and scaled companies and can provide a playbook, not just a check. Capital is a commodity in my eyes. So real expertise is the differentiator. Awesome. And it's a really good insight for how capital is important and also how about the angel investor field is going because I wouldn't have thought so to answer kind of what people like I just said, like a misconception, what would you say is the biggest misconception founders have about angel investors? I would say the biggest one would be reversed to what I just said earlier, like the opposite of what I just said earlier is that we're just dumb money or stepping stone to VCs. But the past angels are operators and they can provide more hands-on value in the first 12 months than a VC will in the entire life of the company. We are really the co-pilots for the most critical stage of the flight, I would say. So yeah, I think that that would be one of the misconceptions. Yeah, and as you said, like now, like the angels are getting more power and these startups are often pivoting. So how would you say you evaluate whether a pivot would strengthen or weaken a business capital? Interesting. So I mean, when I see a private pivot, I'm trying to figure out if they're running from failure or running towards an opportunity. So a pivot driven by customer discovery and not panic is what I want to see basically. So a smart pivot is not a sign of weakness. It shows the founder is more committed to solving the real problem than there are to their original idea. Yeah, and also, this is another thing I was actually confused about. So if you're a founder, pitching to angels, so the other ways, like from their perspective, what would you say is a really important quality that they should demonstrate in a meeting that kind of makes you believe in them? I mean, coachability and I guess this will be like an added on to what I said earlier. When you pivot, you have to not be obsessed with your original idea. And so if you're coachable, you will go edit with the idea that, you know, I think things are like this. I mean, the problem is this way, but I have to test it out compared to, you know, just straight out saying that I know the problem is this way and the customer is expected this way and whatever. So you have to be absolutely coachable and open to listening to the market. Yeah, that's one thing that they definitely should have. Yeah, I think that's actually really good advice for not just founders talking to angel investors, but just in general as well. And touching on your past experiences, can you share a story of a startup you backed that taught you like a surprising lesson or that showed you something unexpected? Yeah, I mean, it's been a short history so far in investing, but I have a good example say so the founder who delivered my second exit, you know, they had a very low energy laid back kind of pitch initially, I misread that as a lack of passion. But as we talked, it became clear his calm demeanor came from from like a deep confidence confidence in what he was building. So he knew his base inside out. It was a great lesson for me, you know, a flashy pitch doesn't always correlate with execution. So his quiet competencies is what ultimately led to these fantastic outcomes. So that was, you know, a surprising lesson for me. Yeah, I think that's actually really good advice too for people who are just starting out in like venture capitalism or an angel investing about how flashy it is, isn't really correlate for students or young professionals listening? How can they start getting exposure to startups and the venture ecosystem? That's a great question. I mean, my advice is always to get in the building, you know, the fastest way to learn is to join an early stage startup. And I guarantee you, I absolutely guarantee you will get, you know, more experience in two years than then you'll get in 10 at a big corporation. And you know, don't just when you approach them, don't don't don't just don't just ask, you know, to pick someone's brain, you know, find a startup you really admire and then offer it to do a specific useful project for free. You know, that way you add value before you ask for anything and you will most definitely get, you know, you get your questions answered and you will get the lessons that you need to, you know, to help get that absolute advantage on your path. That's actually really interesting advice. And along with that, what some more advice that you'd give to someone actually looking to become an investor for themselves. Okay, so I mean, if someone's starting out, my advice is this first, don't write a check for at least six months. So you know, join an angel network or a syndicate, you know, just be a student, read I would say about 3050 100 investment, you know, memos or, or pitches, you know, listen to the pitches or whatever you're going to get in a syndicate or in an angel network. And second, you know, only invest in domains you understand very deeply. So that's your only real edge. And third, you have to consider the money absolutely gone the moment you invest it. So if you can stomach a total loss, don't don't play the game. Yeah, that's what I would say. Well I feel like that is actually really good advice talking about how you might lose all the money. I feel like a lot of people when they think about angel investing, they think about investing a small amount and gaining back like a big amount. So it's really good advice to like know that you are possibly going to lose money to talk more about your personal side of angel investing and about like the connecting and the people aspect of it. I wanted to read a recommendation and the recommendation from Dragan Yovanovic on September 26, 2025. So pretty recently said in the school world, there are fewer and fewer truly good people that have become a really rarity. When you meet someone like chef get of the law, you will soon realize that such people are a real rarity and that you have found a real gem among people. What would you say is important in building your character and reputation in people and being able to be a person that someone can look back to and write such a good recommendation about. Thank you for that, I mean, be real, be genuine, be open to help and I do make my, you know, in last four years is all I'm doing and basically I'm practically retired. So at this point, I try to provide valuable, provide value in anything I'm doing even in posts or DMs or the community I run for the founders. So and it's all for free because that's not how I make my money, I make my money by investing. So I try to provide value anywhere I can to, you know, at least make the path even a little bit easier for the founders. So that's what I would say, you know, be real, provide value. Yeah, and touching I guess on this value, when you do partner with the startup, how involved are you like beyond just the initial investment? I'm a hands-on, you know, I'm an active kind of investor. So I do, like I said earlier, I do, I do provide my previous experience as well, my network. So it's not, it's not only the money that I give. So I'm always, I'm an operator, not a spectator. So my check comes with my time and I open my network, you know, help them and act as a strategic sparring partner, I would say. So I'm always telling my founders, you know, use me. So for me, the real work from my perspective begins really after the wire transfer basically. So yeah, and also I just wanted to talk about, oh, sorry, okay. I just wanted to touch back about your 16th investment and you just posted about LinkedIn to announce reading your post. And I wanted to ask you about how your personal motives are not really motives, but personal experience might back your decision. So to read a quick part of the post, it was like, this one is personal. Both of my grandmothers have suffered from diabetes. I just backed a company, Delfistim, that's developing a potential cure, one that could reverse the disease, not just manic symptoms, they're reprogramming a patient's own cells into insulin producing ones, and you talk later about why you invested in it. So would you say, why did you invest in this company and kind of like, why did your personal experiences shape it? When they pitched to me, it absolutely, you know, felt like something that would have been so helpful at a point in life where both of my grandmothers were diagnosed with diabetes basically and discovered that they had diabetes. And if this was available, my hope would be that it would have helped them a ton avoid all those issues that come with diabetes. So that's part of the personal side, but also looking at the overall impact that these, you know, these cure or this kind of what they're trying to bring to the market is going to have, that's what pushed me basically. So it was basically what made me decide to invest in this company with the founders, you know, that they're dedicated and relentless. The mission, which is, you know, it's the potential to reverse the disease and not just trade it, but the real deciding factor is, you know, it's the impact, you know, it could reshape the global health forever if they managed to do what they're trying to do. So, and I looked at it and I said, you know, even if I'm going to invest this amount, and even if I lose it, you know, I don't really mind because the question I asked myself is what if it works, you know, how many people will benefit from it? It's actually really inspiring to hear how you actually value the impact these startups that you invest in have. But obviously you can't really view all the startups are looking to every single one. So how would you say you stay up to date on disruptive technologies or market trends that these startups have to go through? It's, you know, some investors do stay, you know, updated through news and stuff. But honestly, you know, the way I do it is I stay in the deal flow, you know. My best intelligence doesn't come from reading news articles. You know, it comes from talking to the founders who are out there, you know, actively building for the future. So they see the market shifts, you know, months or even years before the press does. So for me, every pitch is actually an education I would say. So yeah, that's how I keep myself, you know, up to date. Yeah. And I was wondering about, like, kind of not really long when timing, I would you say timing affects whether a company succeeds or fails? I would say it's everything. I mean, people underestimate this. You know, timing isn't just a factor, it's the entire playing field. Great idea at the wrong time is a failed company, period. I mean, so the question I always come back to is why now? There has to be some kind of, you know, tectonic shift, some technological, cultural or regulatory that opens the window for this company to exist at this exact moment. Yeah, that's what I would say for timing, absolutely. So it sounds like timing actually is like almost the key thing with a startup, but you also do mention another important thing is that you don't invest in crypto or Web 3 unless the company is near unicorn. Why do you take that stance? It's, you know, most of the, look, my view on this is straightforward, you know. I don't invest in science projects. My thesis is all about, you know, backing companies with clear business models that will solve real world problems today. So to me, a lot of Web 3, you know, still feels like a solution in search of a problem. So in that, in that, you know, sphere, I invest in businesses not in belief systems. So I'm happy, you know, to get involved in when there are real customers and real revenue in Web 3 companies, but earlier than that, you know, I'm not going to, you know, take that path with them because I don't see it. Yeah, and I was like, you talked about this earlier about how you had a client who was very calm and their demeanor was kind of laid back and it's good that you didn't take it as a misconception for them being maybe not too passionate about their thing, about their company. Would you, could you give us another story of a startup you bagged that taught you another surprising lesson for other listeners? Yeah, I mean, I guess the positive one, I guess I'm going to give one on the negative. So when I invested early on, like in my beginning, because I didn't know much, I gave my ideas to the founder and, you know, I hoped that they would execute on them. And that's, that's why I made the investment because, you know, I saw that by making by implementing what I was suggesting, they would open up great revenue streams, but they just, you know, didn't go that way. So I guess that that's one of the other surprises that I got from that investment. It's, I mean, the investment is still very much alive and it's doing okay. But probably if they, if they listen to my advice, they might have opened up lots more revenue and would have made, you know, the path might have been a little bit more easier. We will see where things blend, but and probably they will implement them down the road in the roadmap. But yeah, I guess I would say the surprise here was that, you know, founders will not always listen to you. And so yeah, there will be those cases as well, I guess. It's actually another interesting, you know, viewpoint on this whole market or this whole like concept. Can you give us, obviously each company has is different, but can you give us like a general idea of your exit strategy? I mean, I'm always trying, especially if it's, you know, late seed or or or bridge or series in later. I'm always trying to, you know, look at those exit potentials, which path they're going to go for an exit. So it's not actually a kind of strategy that I implement because it's the companies which will implement it at the end of the day. But I try to estimate basically on my end, you know, how long it will take me to reach the exit point with this, this company and partnering and, and, you know, what the paths look like. So that I guess would be part of, you know, how, how I plan, you know, on all that and look at the potential strategy for for exits. Yeah, and before we start wrapping up, I had a question about the two different ecosystems and you talked about investing in the UK and in the US. How did startup ecosystems differ between the two areas? So US is a huge market overall, so that there is absolutely crazy demand, whereas UK is smaller market and less demand. So in essence, the way I view them is like UK is kind of a miniature of the US market at this point. They, they, they are building some, some good companies, but still the overall access to capital, which US provides is, is absolutely, you know, top of the world and nobody can come second. I mean, there are going to be so many places of that and then you're going to have a second. The access to market in US and the market size is, is absolutely amazing, fantastic. But UK is, is trying to, you know, pick up their pace. We will see how, you know, how they will manage, but absolutely they will, I guess, none in the world for, you know, for decades and probably centuries is going to reach the US market unless something absolutely, you know, unforeseen happens in the US market. But the way I see things, it's yeah, the US market is going to be the leader though. Yeah, it's really important to understand the difference between the markets in which you're investing in. And finally, just wrapping it up, we asked a question to all of our guests, actually, what's one piece of advice you'd give to your younger self about both angel investing and your transition from being an entrepreneur into this field. One advice I would give to myself is, is do what, what you love because, you know, you don't have to work for it, and especially if it's coupled with money. I mean, for me, in this instance, where I'm at right now, I said earlier that I'm practically retired, but I keep on having lots and lots of meetings with founders and, and, and to some people when I say this, that I have, you know, probably seven, eight meetings a day with founders, they come to me and say, you know, you, you're, you are working more than somebody was actually working. And I say, yes, but I, I don't see it as work because it's something I love, and I can't stop at any time doing it, but I keep on doing it because I love it. So, you know, I love providing value for the founders and I love helping them, you know, standing that hand to, to bring them up, um, yeah, to what you love would always be my advice to my younger self and, and to myself, man. Awesome. I feel like that advice is really true, and it also shows your passion, which I could clearly see from before, your passion in angel investing, but also the passion in your startups, your clients. Mr. Abdullah, thank you so much for sharing your insights and your journey. It's so inspiring to hear how you bring both experience and empathy into your work with founders. Absolutely. Your perspective grounded in having both companies yourself gives such valuable lessons for anyone interested in both entrepreneurship or investing. To our listeners, if you're thinking about startups, pitching, or even just how to evaluate opportunities, this episode is packed with them you can take for you. Don't forget to subscribe to Professional Perspectives, leave a review, and definitely join us next time as we keep exploring stories that inspire and guide future careers. Thanks for tuning in, and keep exploring your professional perspectives.