Video details

From Engineer to CEO: How to Start a Tech Company


Taavi Rehemägi

Interview with Taavi Rehemägi, co-founder and CEO of Dashbird. He tells the story of founding Dashbird, and what it took for him to go from software engineer to CEO. Learn how he built his network and found success in a completely different role!
In this interview we're covering:
-How they came up with the idea of Dashbird -Challenges of going from engineer to CEO -Essential skills for a CEO -How his engineer background made him a better CEO -How he improved the skills necessary to be a CEO -Networking tips
Excerpt from the interview:
"A CEO has to continuously learn just like a software engineer. My background in engineering helped me with the following:
-Iterating different solutions -Setting expectations toward solutions -Learning from past activities -Tracking variables
The first years of a new tech company are about learning what strategy is viable on your market. Your best bet is using data and making logical decisions. Engineers are good at this."


Karolina Tóth: Hi there, everyone. I am Karolina Tóth, and this is the Level-up Engineering podcast. I am happy to have Taavi Rehemagi with me today. But, before we start, I would like to just give you a little disclaimer, I've been really intrigued by the idea of video content. And so now, if you're listening to us on your favorite podcast platform, you can check us out on YouTube as well and see us in a video, which is kind of exciting. So, for us to keep going with this video format, we would love to hear from you. And if you don't like it, then we will not do it anymore. So, with that said, without further ado, let me welcome our guest today, Tavi Ragamagi. Heis CEO and co founder of Dashbird. And he will tell us a bit more about the company. But, today's topic is from tech lead to CEO, and we have him with the background of having started coding at the age of 14 and and having started his company just now. So, stick with us if you are an aspiring CEO, and you are right now working as a developer. Welcome, and please tell us a bit about yourself. Taavi Rehemagi: Hey, Karina, thank you for having me. It's really exciting to be here. And definitely the first first video guest is also interesting. So, let's see how that goes. So, a bit about my own background. As I said, as you said, I've been a developer for most of my life before and worked at all sorts of different technical roles in different startups, been in tech for over 10 years now with different products, and worked with different engineers with different technologies. And three years ago, and or like, since the past three years, I've been the co founder and CEO of Dashbird. We started Dashbird in so we are in 2018. And it's been a journey, we've come quite a long way since when we started, we raised venture capital, we've built a world class team, we've launched products, acquired customers, done a lot of the early stage activities that a startup goes through, and it's been quite a ride. I'm happy to talk about my experience and, and then also about the company. Dashbird is also a tool for developers. So, I think this is what makes me kind of qualified to be its CEO, or that's how we kind of came up to it as well. So, Dashbird is a monitoring and insights overview platform for distributed cloud applications. We work with companies who are hosting their applications on top of serverless infrastructures in AWS. And we provide visibility and understanding into how the application is operating. All of the failures are being reported by Dashbird, and we help companies to operate and fix and maintain and improve their applications. It's kind of like Data Dog, but for servers. Yeah. Karolina Tóth: Awesome, thank you. Thank you so much for the clarification. And with that said, you mentioned that you are qualified to to be an expert in this area. But, please tell us a bit about how your current role as CEO is different from a software engineering role. Taavi Rehemagi: Yeah, sure. So, it's obviously it's completely different. So, it's a completely different world. And I also was thinking before we had, you know, before this COVID right now that nobody's ever really qualified to be the CEO for the first time, I think I've noticed this, you know, among other founders is like, doesn't matter if you come from sales or or product management or whatever other discipline, like becoming a CEO and doing stuff across the board across like, from, you know, acquiring customers go to market strategy to product to fundraising like unless you you've actually done those things, like everybody starting from pretty much the same, same place. And it's, you know, the transition, I think, for me was a bit gradual, but also the first into cold water a little bit. So, when we started obviously, the first kind of six months was mainly just building the product and thinking about how the production work and things like that. But, after that I transitioned into more like a full time CEO role, which meant raising money, which was this whole kind of a journey that I did for the first time in my life. After that, you know, building the team iterating on the product strategy and forming the code to market activities early on in the company. And then over time, I think my role has been basically working on each one of those Areas again and again and iterating. So, it's been in product, hiring, fundraising, go to market, sales, talking to customers, being at webinars, podcasts as we are right now. Karolina Tóth: So, your role, I am assuming is, is a lot more versatile in the sense that you, when you code, you also can use a lot of different aspects of coding and, and libraries and different languages or different databases, whatever. But, now you have to kind of use different aspects of your personality, if that makes sense, like, building a business kind of wants you to just do different things. Taavi Rehemagi: Yeah, I think it's kind of basically being a generalist. So, having an opinion on, like, I don't even have as much opinions anymore around the development side, like I trust engineers to do what they do best. And I don't, you know, go into their meetings and say, like, Hey, we need to do this in that way, or something like this. But, it's basically having an opinion and kind of working on different disciplines. I think, over time this has transitioned more to be like around product strategy, and kind of how to win in any market, what do the customers really care about? Where's the kind of the biggest pain points? And then also around how do you actually take a product to market and so I think over time, those kinds of focus areas are also shifting as well. So, they start out being really product focused overtime, moving into the business side, and it's a lot about people like 80% is just about managing or, or talking to people, having different conversations. Karolina Tóth: Yeah, that's, that's amazing. Especially when you think about the general perception of who a developer is now, you may just have to talk to people. So, with that said, let me dig into a little bit about your story, what made you What made you want to start Dashbird? How did the idea came around? Taavi Rehemagi: Yeah, so the roots of Dashbird are actually, we were working on this other company or not as founders, but as, as team members in the engineering organization. And we happen to be building a serverless, which serverless is a really new kind of technology trend. It got started really in 2017, 2016. And at that time already, we were like building quite the meaningful application on serverless. And that enabled us to kind of see the future a little bit, we were ahead of the curve, not a lot of people were building stuff on it at that time, which, you know, we saw that this is going this is here to stay like serverless is a meaningful trend in cloud computing, there's a market that's emerging here and the community, but also enabled us to see the challenges that other organizations are going to face down the line. So, you know, being a couple of years ahead of time, we were seeing like, hey, like two years from now, there's going to be a lot of organizations facing the same challenges. Let's let's try to build something that would solve some of the challenges and what we would ourselves use and and it was, like, you know, started out as just something, can we build it? Could this work? Can we use it for ourselves? And then, after doing that, we kind of tried to put it out there, and it kind of started gaining traction, people started using it, there was like really positive feedback and kind of organic interest towards the product early on, which then, like, grew quite organically, and it was obvious that there is something there. Obviously, the, the strategy and the complexity of that product early on is nothing compared to what it is now. And like we've gone through, like 10s of iterations or hundreds of different, like changes to form it into, like a more mature company. Karolina Tóth: Right. So, am I correctly hearing that it wasn't really you wanting to become a CEO, per se, it was just kind of an emergent quality of you creating a product that you thought was needed. Taavi Rehemagi: So, as a group of founders, like, I think there was an ambition to to do a company, to do a startup, I think that was there. But, it wasn't like we need to do it that at any cost. It was like we knew that we want to do it at some point in our lives. And you're like looking for a right opportunity and then Dashbird kind of came along. And like the decision to be the CEO wasn't like, I have this ambition. It was kind of that we settled into, like the other co founder was was working on the tech side more and kind of organically went into that. Yeah, I think I didn't even acknowledge it as much in the beginning. Karolina Tóth: It kind of happened. So, would you say that you were kind of like an open person as a developer as well? Like would you say that you were more comfortable speaking and standing up in front of crowds than your fellow developers? Taavi Rehemagi: I think a little bit yes, I think that's always been one of my qualities in a way. But, I don't know if that matters as a quality for SEO, I guess, maybe a little bit because you need to be able to go out into the world and talk to customers and to VCs and to convince people to join your startup in terms of funding or customer or employee. So, I think that's really important. Karolina Tóth: So, what are some of the essential skills that you need as a CEO? Taavi Rehemagi: I think every kind of early stage startup needs a founder who would go out into the world and get people excited about it. I think that it's also in YC, what they say is your startup needs one evangelical founder, who is able to go out into the world and basically sell it, but you don't you, you still need a CTO who's really strong like and like the other like the go to market people, like they are just as important. So, like, it alone is just is not enough. But, you need different disciplines. But, they say that it's hard to succeed, succeed wildly, or like, really big without this kind of founder. So, I think that's the main role of a CEO. Karolina Tóth: So, would you say that you and the CTO really come together and, and help each other out in different aspects of the company? Taavi Rehemagi: Yeah, I think we definitely have a really good chemistry with, with the management team right now. And I think that the skills are definitely complimentary and the interests are also complimentary. So, we work on the product together. And I think I do like the, everything with the investors and customers. And like Mark focuses more on the on the product and engineering. So, definitely a good fit. Karolina Tóth: So, what would you say is your most exciting part, to the role of CEO? What what is it that was added to your life by becoming the CEO? Taavi Rehemagi: I think it's two main things is watching other people succeed basically, in your team, or like as customers, like when you when we build the engineering team that's releasing really good products month in the month out and succeeding or like people in the marketing team. And I think that, you know, seeing that kind of feeling a little bit responsible is, is quite amazing. And I think the other thing is looking at putting together different functions into a company that's kind of running like an orchestra or something like, you take like individual pieces of off teams and like areas, and then that forms beautifully to into a company, which is really nice to see on a kind of on like, the third person view in a way. That's interesting. Karolina Tóth: Thank you. With that said, do you have and excuse me if this is too personal, but like do you have a longing for the developers work like, like what you did as an IC, for example? Do you Do you feel like you want to go back or do you ever go back? Taavi Rehemagi: On the weekends, when I have time I just play around and like, do random coding sessions, sometimes. I'm not the event on Dashbird system, like projects, but like, just stay around, like doing challenges. I don't think I would want to go back full time. I think that it's like a really challenging role. But, it's also like really interesting. I think I'm exposed to a lot of interesting people and like things to do. And I'm, I'm enjoying it. And I think it's becoming easier over time. So, I think the first one and a half years, I was like, I would have gone back. I think now we are getting used to it and it's becoming more more interesting, more or like it was interesting, but [inaudible 14:40] Karolina Tóth: Now it's becoming perhaps a bit more like your comfort zone and and you're feeling more comfortable? Taavi Rehemagi: Yeah, you're starting to understand what you need to do. Karolina Tóth: Nice. So, are there any mistakes that you're willing to share with our listeners that you made along the way when you were transitioning into this position? And is there something that you would like to do differently? Taavi Rehemagi: I think there's been a ton of mistakes, I think, also the perspective of like you, like, usually the perspective of people is, when you're making mistakes is you're only remember the mistakes and kind of looking back at the three years, like, all I can see is mistakes right now. Obviously, there has been a lot of success as well. And like, for every bad decision, there's like, maybe 10 good decisions. You know, obviously, doing an early stage startup is not as glamorous as it might look like. And you end up making mistakes and struggling. I think the biggest mistakes were done very early on with maybe like sales or, or marketing strategies that we're we didn't know what we were doing exactly. And, and kind of losing losing momentum in some places, or, or making like strategically wrong decisions in some cases. And yeah, I think that we've always been good with engineering. So, because that's what we know, we know how to hire engineers, we know what the customer wants. In a large part, I think growing into what works in sales, and what works in marketing has been the most difficult, but also, the mistakes that I've made, don't seem like obvious mistakes at the time, like, you don't know enough information at the time you're doing those mistakes to prevent them really, as well. So, now we experienced I can see them. But, you're gonna get scars, when you're doing it in early stage startup, definitely. Karolina Tóth: Okay, but it seems like you learn from them in hindsight, right? Taavi Rehemagi: Yeah, I think, yes, but there's always new mistakes to make. Karolina Tóth: Nice. Taavi Rehemagi: [inaudible 16:57] Karolina Tóth: A bright future ahead of us. So, you, you mentioned quite a few things, let me do a little summary of what we have seen. Because I've I've heard from you that it's important to complement each other within the team, right? So, you and the co founder have to find the niche in which you have to participate to make the company the best it can be. And then I feel like you really mentioned without saying it, that you have to keep an open mind to, to all parts of the business kind of as a as a CEO. It sounds like you you learned a lot about product strategy and and marketing, as you mentioned, and just like how to run it all and all the while keeping a close pair of eyes on on the product, right Taavi Rehemagi: Yeah, I think you hit the nail there, actually. So, I think in the space we are operating, like just in my experience and and kind of the reality of most markets today is that you need to have a really smart strategy and kind of you need to hit the niche and some sort of a way or a vertical or something that other people don't see. And you need to be the best and kind of nail every discipline from like product strategy to pricing to go to market to be able to escape kind of the Death Valley of what like early stage startups go through, and to kind of go to the next stages like to go to next stages of the company each of those kind of disciplines or parts of the of the company need to work together really well. So, you, you need to constantly iterate on like until it's basically perfect. Because I think, you know, not having done a company 10 years ago, it seemed to me at that point that markets were less competitive. And like, you could get away with like, some inefficiencies maybe in the in the strategy or in the, in the products. But, now it's like, if you're in that stage where the company is like weak, and it's fighting for its life, you need to keep in mind every aspect of the business. I think later it will get easier as it gets stronger and you're able to attract talent into each one of those like areas. Karolina Tóth: So, if you can dig a little deeper in in how the company looks like right now do you have like, specific departments and and people responsible for those departments only? Taavi Rehemagi: Yeah, so I think we have quite a cool structure for a company of our stage. So, we do have, like the product functionalities is divided by by some people, mainly the CTO and me are working on the product. We have engineers, we have an architect's role. Then going into the go to market side, we have head of marketing, we have marketing specialists. We have, you know, I'm an account executive. So, all of the disciplines and like an SDR as well, or customer success. So, we kind of have the all of the functions figured out. And then we're kind of iterating each one of those areas of the business, basically, on a weekly basis trying to figure out what works, what doesn't. Karolina Tóth: Awesome. Thank you. You mentioned iteration quite a few times. And I think it's familiar to all of us working working in IT. But, I want to ask you, if you can pinpoint specifics about your skills as an engineer that you took with you, and used in your role as a CEO. Taavi Rehemagi: I think there probably are some, I think what enables you to like iteration and learning from past activities is tracking all of the things you do enter results and forming, you know, what, if you do something, what do you expect to change? Or what do you expect the result to be? And then kind of week after week, or month after month, reviewing those, those activities and those results and continuously learning. So, I think, in the first couple of years as a company that the main thing you're actually doing is learning about what kind of works and I mean, a strategy that is viable in this space. So, it's all about the data and kind of making logical decisions. So, programmers are good on that. Karolina Tóth: Yeah. Yeah. So, a lot of like what engineers do. You also mentioned the importance of strategy. And even though I'm not even an engineer, I feel like strategies is a word that's used a lot. But, maybe it's not as crystal clear to everyone. And I am wondering if and when, and what kind of outside perspective or outside help you guys pursued while you were launching the company as, as a couple of engineers, basically. Taavi Rehemagi: So, the biggest by far has been talking to other founders, especially in your own space, that are ahead of you in terms of the size and maturity of the company. And in our case, we were fortunate enough to talk with like Unicorn founders, or like, even founders of some public companies in our space, kind of a 360 view of the space. So, they once you go and talk to them about your ideas and kind of what you're doing they can easily point out flaws in your thinking and kind of give you a perspective of what they see. And having enough of your being tested and reviewed by other people, enables you to see the blind spots and things that they aren't seeing, because like big companies think a bit differently than than, like early stage startups. And [inaudible 23:16] like to come back to the strategy being a broad term, it is definitely and like, I think what what I mean by that is identifying the things that like, early on, you're searching for a niche. And in that niche, you need to understand what's the one value proposition that every user in that niche needs? Like what's the most common problem? What's the problem that people are willing to pay for? What's the problem that as a startup you can actually do? So some products are just too like, R&D heavy to do as a startup. So you need to find a way and like, who are you going to sell it to? Is it big enterprises, is its smaller companies? What's this? Where are most of the market at? Like, are they bigger companies? And how do you reach them? So the the combination of all of those questions makes up strategy. Karolina Tóth: So, now that we are at the nitty gritty, I am, I'm picturing myself, if I am a developer, and I'm listening to you. And you are talking to me about reaching out to other people, or talking to to founders. How did you reach out? Do you have like, did you have a lot of friends or have a network in this kind of area before? Or did you have some sort of offer strategy to reach out to existing founders? What do you suggest to our listeners? Taavi Rehemagi: So we started completely from scratch without any network of any kind, basically, but we got lucky in terms of the we had customers in the first year of of starting, and that allowed us some credibility to attract that target network and then those angel investors introduced us to some VC funds. And from there on, like, the guy who advised me early on was like every meeting, you go into, ask five intros to next people like ask like, make them introduce five people to you. And then if you do that for months, then the network grows exponentially, and they, like people who have been in the space, have a large network, and they know who you should be talking to at any given time. So, it's important to get in front of people who have the network, you know, considered, okay, that guy should, should like speak to him or her, being aggressive with networking, basically. Karolina Tóth: Awesome. Would you call that aggressive or would you just call it reaching out and hoping for the best? Taavi Rehemagi: Not aggressive, like with communications by just like, doing it a lot, and like, in your intentions, that, you know, you want to talk with somebody and, and the fund managers and, and like angel investors don't have a lot of time. So, if you like, kind of beat around the bush, then they might, you know, it's easier to just go out and ask what you want, and sometimes they give it to you. Karolina Tóth: Right, thank you. So, there are a couple other key takeaways in there, I feel like clear communications is definitely one of them. And then you talked about really reaching out for for knowledge from knowledgeable people and and hiring for for fit for the company's tasks that that people have to do. So, look for a marketer for for your marketing after a certain size of the company, or after a certain kind of step that you have taken. And then I I also hear that it's a lot of work, it sounds like you have had to become this jack of all trades, in a sense, is that right? Taavi Rehemagi: Yes, but it's in a really specific vertical. So, maybe I'm a jack of all trades in cloud monitoring space. So, I know it inside and out. And I know how products work, what customers want, and you know how to go to market in this particular space. Maybe it transcends a bit into other types of companies. But, you need to know your area, like, really well. Karolina Tóth: Awesome. Thank you. Thank you for that clarification, because I think it makes it sound a lot less daunting than what what I said sounded. So, thanks for that. We are at the end of the questions that I have prepared. But But I would like to ask you, is there something else or anything else that you would like to add? Taavi Rehemagi: Yeah, I think my takeaway is that I think with a lot of hard steps in the right way, like you're afraid to take it at first and it's very difficult, but even if like things don't go as planned, you're not gonna wish you didn't do it most of the time. So, I encourage people to to go out and try and like if I can do it, then anyone can do it. So, it's definitely worth it even if like you don't end up as a founder of a Unicorn company, like the life experience and the perspective it gives you is, is well worth it. So, anyone who's interested in it, you need to have interest, obviously, but definitely try. And if you want, I can maybe help. Karolina Tóth: All right, there are some other networking connections to be made there. What are some of your plans that that are in the future, if you care to share? Taavi Rehemagi: So, I think Dashbird is in a really good position at the moment in terms of I feel good about the market and the product and the team. So, I think in the next one and two years it will be it might be completely a different company in terms of size and scale. And it looks like we're in the right place at the right time. So, I'm looking forward to kind of reaching the next level in terms of people involved getting more senior roles and scaling the company. So, I think that you know, that's the only plan always as a startup founder is to scale and to grow, obviously. Looking forward to that specific next stage. Karolina Tóth: Awesome and we are looking forward to seeing that happen. [29:55]