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Starting A Tech Business. Again. And Again. And Again. (with Michael Drogalis)
1k Plays1 year ago
Ever wanted to start a tech business? Michael Drogalis has done it successfully in the past, and now he’s trying again (and again and…) as he makes a very public attempt to start 4 new tech businesses in the next 4 quarters.
He’d sound completely mad, except he’s got form: His last Kafka-based company got bought out by a tech giant, giving him enough of a safety net to try something new. And for his new approach, he’s doing the exact opposite of ‘stealth mode’. He’s publishing every step of his 4-by-4 challenge, wins and losses, for all to see. It's entrepreneurship for the Reality TV era. 😁
In an unusually vulnerable episode of Developer Voices, we talk about everything from solo software development and marketing strategies, to the inner struggle of starting out on your own, with no guarantees that the world will care. And this time with everyone watching.
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Kris on Twitter: https://twitter.com/krisajenkins
Kris on LinkedIn: https://www.linkedin.com/in/krisjenkins/
Follow Michael’s journey: https://michaeldrogalis.substack.com/
Michael on LinkedIn: https://www.linkedin.com/in/michael-drogalis-01029924/
Michael on Twitter: https://twitter.com/MichaelDrogalis
Steal Like An Artist by Austin Kleon: https://austinkleon.com/steal/
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Transcript
The Entrepreneurial Drive of Programmers
00:00:00
Speaker
Have you ever wanted to take your technical skills and start a business? I think it's actually a fairly common desire among a lot of programmers, because when you think about it, we have a lot of skills that lend themselves to building businesses. We like to build things. We're experienced in going from idea to actual working thing. We have a love of solving problems.
00:00:24
Speaker
Puzzles sure, but also especially problems that make a real difference to people, that delight people when we've finally solved what's been bugging them. And we know as well as any sector, how do you create a repeatable system that delivers something valuable over and over and scales up? We've got a lot of skills that lend themselves to businesses.
00:00:47
Speaker
But there's one area I think traditionally we're fairly lacking as programmers, and that's the sales and marketing side. I think Kevin Costner has something to answer for here. We were told, if you build it, they will come. But anyone who's tried knows that's simply not the case. No matter how great a product you build, you've still got to build the bridge from your product to the outside world and back. If you just build it, they won't come, they won't even hear you.
Michael Dragalas: From Business Sale to New Ventures
00:01:16
Speaker
So, if you want to go from working the feature factory to captaining your own ship, you've got to learn the other side. And that's this week's topic. Coming from a very much technical mindset, we're going to talk about how you bridge that gap to the outside world.
00:01:32
Speaker
And my guest for this has very good form. I'm joined by Michael Dragalas. He's already sold one technical business and he's now embarking on his next and he's got a novel idea for it. Instead of rolling the dice once, he's going to attempt to start four tech businesses in the next four quarters and publish every step of the journey, put himself under the spotlight and show people how it goes.
00:01:56
Speaker
Given that he's keen to bear all, and this is a question that will face quite a few of us in our careers, I thought I'd bring him in to discuss the practical steps of turning an idea into a solution people actually want. The external stuff of sales and marketing and price discovery and all that
00:02:14
Speaker
And also that more difficult sometimes, the inner game of understanding and empathizing with your customers. Making good decisions, but not making decisions so perfect that you paralyze yourself and never do anything.
Translating Technical Ideas to Market Solutions
00:02:28
Speaker
Not making a decision and then second-guessing yourself next week. All that external and internal game stuff that's just outside the realm of software.
00:02:38
Speaker
So, a meaty topic, let's get stuck in. I'm your host, Chris Jenkins. This is Developer Voices, and today's voice is Michael Dragalis. Joining me today is Michael Dragalis. Michael, how are you doing? Hey, thanks for having me. Doing great.
00:03:07
Speaker
Good. You're on an exciting adventure these days. I am, I am. I've recently left Confluent and I'm kind of embarking on a journey just to see what I can do as an entrepreneurial software engineer.
Lessons from Confluent
00:03:21
Speaker
What can I build? What am I good at? What am I not good at? And it's been an exciting journey so far, about three weeks in.
00:03:28
Speaker
We're going to get into this, but if we're going to talk about tech people giving up their day job to go and start their own business, we should really note that you have passed form on this. This is not your first rodeo, as they say over there. Give us your backstory, because you've sold a business before.
00:03:46
Speaker
Yeah, my story starts maybe 10, 11 years ago, I left college as a software engineer. And at the time, open source was really culturally big. And I knew that
Starting Four Tech Companies in a Year
00:03:57
Speaker
I wanted to be a part of that I wanted to have some ownership in something. And so I had started an open source company, or rather, I started an open source project. And that was kind of moderately successful.
00:04:07
Speaker
I ended up founding a business on top of that, which I eventually sold to Confluent and I spent the last five years at Confluent. So now that I've exited Confluent, I'm pretty keen to try it again and sort of see how much of that was skill and how much of that is luck and try to tilt as much of that to the skill bucket as I can. Yeah, but presumably when you sold that company, you made enough money to take a risk, not so much money that you decided to never work again in your life.
00:04:36
Speaker
So you've got a bit of a safety net going into this, I guess. But the thing I find interesting is with that comfort, you then moved to Confluent for like five years. You didn't say, oh, I'm going to immediately jump out and do thing number two. What was behind that decision? Why did you stay there for five years? And then what was the trigger that actually made you say, I want to roll the dice one more time?
00:05:01
Speaker
That was the plan, actually. When I joined, I was like, okay, I'll spend two years at Confluent. I'm a flight nurse. I'm going to go do the next thing. I'm going to relax. None of that came into fruition. It ended up being a pleasant experience. I learned a lot. I think it was a good place for me to watch what happens after you get out of day one and day two of a company and watch how you go from
00:05:24
Speaker
200 people to several thousand people. And so I learned a lot through that experience. It ended up also being a good place for me to be at a transition phase in life. I had two children during that time, and it helps to have less work chaos than you would doing an early stage company. And so it ended up being the right set of people to be around, the right set of lessons to learn.
00:05:48
Speaker
Now, five years later, I never lost that itch, but it just ended up being the right alignment of stars to try it again now. Why? What was the trigger?
00:06:04
Speaker
As Confluent got bigger, I learned a little bit about myself. What are the things that I liked and what are the things that I didn't like? I realized that I really prioritize working in a small setting, shipping fast, making quick decisions. Large companies can do incredible things that small companies can never do. But I realized what was the thing that I wanted at the end of the day. I really wanted to try something with quick iteration, quick decision making.
00:06:30
Speaker
And that's kind of what led me back to just trying this on my own. It's sort of like, can I tip the balance point of benefit and benefit and cost? Yeah, yeah. I think a lot of programmers can understand that wanting to get back to just building and shipping software quickly and working on your own thing and the freedom of it. Yeah, yeah, absolutely.
00:06:53
Speaker
Another thing I find unusual is you jumped ship and you didn't have a specific idea in mind. You had what some
First Startup: Shadow Traffic
00:07:02
Speaker
will say is a crazy plan for what you were going to do as soon as you left, and I'm going to let you outline what your plan is for the first year.
00:07:11
Speaker
Yeah, I'll tell it through a quick story. Basically, my plan while I was at Confluent was to spend my time deciding what's going to be the next company that I build. I would probably do a venture-backed company like I had attempted to do before and try to take it further than I did the last time. And so I spent years being like, alright, what's the problem that I'm going to solve? What's the billion dollar market? And I got pretty far down several different paths. And as I got closer and closer to doing it, I realized
00:07:37
Speaker
I felt a state of anxiety about choosing one problem and saying, I'm going to try to take the next 10 years to go and crush it and just spend my life on this. Something about that just didn't sit well with me. And actually, I still don't know why. But I sort of respected that. And I paused and I said, all right, that's not going to be the plan. I'm going to try something else. And I sort of concocted something rather different. Instead of doing one big company, I formulated the plan
00:08:04
Speaker
you know what would be like to do many little companies and so i i sort of put together something that i call for startups and four quarters which is basically what it sounds like you know for next year each quarter i'm gonna attempt to launch a little company a little startup with its own product and to see if i can make that succeed and i think this this ended up sort of.
00:08:25
Speaker
feeling more balanced to me. It gave me the freedom to try different products, to try different domains, to not feel bad about throwing things out that weren't working. And so far, it's been a pretty successful framework for me. It's not easy, but I think it gives me a bit better internal alignment. It feels like I'm doing the right thing with myself at this time.
00:08:50
Speaker
I mean, that's such a thing to go out on your own that you have to feel somewhere deep inside that you're doing the right thing, right? And you're well suited for it. I know that if I did that, with the best will in the world, I'd probably spend the first three months trying to decide what problem to solve in those three months.
00:09:11
Speaker
How do you, how do you say, well, maybe this isn't the billion dollar company, but this is good enough for now? How do you, how do you crystallize a problem? So I think that's the key is I don't want the billion dollar company. I actually be much happier making less money, but doing something that I'm happy with and saying that this is enough. And it's pretty counter-cultural to all of Silicon Valley to say, I'm actually going to aim lower. But that's, that's what my goal is right now.
00:09:36
Speaker
So I think that's part of it. And then I think the other part of it is saying, I've signed up in a public commitment. I've gone on LinkedIn. I've gone on Twitter. I've told all my friends and my family, I'm going to ship something in 90 days. It's the Sun Tzu death ground strategy. I've taken my ships and I've burned them and put my back to the sea or whatever. I don't want to look bad if I ended up not shipping in 90 days. I feel it's important to try to honor that commitment.
00:10:02
Speaker
Even if it's there's no serious consequences to me backing out of it i think it's internally important so it's a motivator for me to just pick a problem i think is interesting.
00:10:14
Speaker
admit that I actually don't know the market size and just say, I'm going to try and invest in 90 days and it's going to be what it's going to be. Maybe there's going to be some
Importance of Experimentation and Public Commitments
00:10:20
Speaker
traction. Maybe there's not, but it gives me the license to attempt, fail possibly and move on or succeed and just see what's there and kind of open the box and find out what's inside. Okay. Well, you best tell us what your first idea is and then we can chew through that. So what's, what's business number one?
00:10:43
Speaker
I've got a list of maybe 10 ideas. Some of them are more big than others. But I thought, okay, this is going to be a pretty challenging year. What should I do? I want to explore all kinds of different domains. I might as well not delude myself and make it harder than it already is. So I thought I'd start with what I know. My entire career has been in data infrastructure. Why don't I do something that's adjacent to that?
00:11:03
Speaker
So I've spent many years working in event streaming systems, real time systems, and I've sort of noticed that just sort of getting these systems running from scratch is pretty hard. What I've observed is something that I call the $10,000 demo problem, which is that anytime anyone wants to build
00:11:20
Speaker
Any kind of a real-time demo, it easily costs $10,000 in people's time. And the cost is actually not configuring your software. It's injecting the right data into your system to elicit the behavior you want. You need data that looks realistic, that is relationally joined across many data sets. You need it produced into your system at an appropriate cadence. And there was just nothing else out there that did this. I've seen teams construct these over and over.
00:11:46
Speaker
Internally, what I notice is that every company ends up building a little data simulation tool to try to power their system. And they do it for every project, every conference that comes up. All right, let's build the demo. It just gets done from scratch over and over. And so that's the problem that I want to solve in my first quarter. I'm building a product that I call shadow traffic to basically solve this.
00:12:05
Speaker
A container that you can download, it has a declarative API to say, I want my data to look like this. It should be produced at this distribution rate. It has relationships that join in this way. And so it sort of solves that problem of figuring out how do I go from nothing to actually building a system that's based on event data in a pretty quick way. OK. I think we can all understand that problem and the need to solve it.
00:12:34
Speaker
So you say you're not aiming for the big billion dollar problem. You're not doing a lot of market research up front. What, what made you say, okay, if my 10, this is the first one to tackle, was it like the burning personal need or the feeling that it might be the one that captures people imagination or yeah, I'd be lying if I said that I knew it's kind of just intuition based on, you know, my years of experience. I think a lot of this is just an admission to not knowing. Like I've realized, um,
00:13:02
Speaker
even the best people in business are wrong a lot of the time. But the way that you end up being right is you rapidly experiment and you learn. You just say, I don't know, but how can I figure out the answer as fast as possible?
Balancing Automation, Marketing, and Development
00:13:14
Speaker
90 days while it's a decent chunk of time, it's certainly a lot less time than two or three or four years you can spend trying to build a startup all on its own. And so I think a lot of the philosophy that I'm trying to take is to figure out how can I take
00:13:30
Speaker
anything that I want to do and turn it into as rapid of an experiment as possible and not feel bad about the results. If it doesn't work out, that's fine. I've got 15 other things stored up in the queue I'm ready to try again and eventually one of them is going to be a winner. Okay, if you throw enough doubt, you'll hit the doubt board. Yeah, essentially. One of my friends Stanislav said, I expect failure in the short term, but I expect success in the long term because I'm just not going to stop. And I think that's exactly the right mindset.
00:14:00
Speaker
Yeah, yeah, that's something nice to hold on to when the storms are going. Yeah, idea. Okay, so how do you break down 90 days? Because you've got a lot to do, you've got a certain amount of marketing, some business, a lot of software to write, and it's just you, right?
00:14:18
Speaker
Yeah, just me as a solo entrepreneur. I don't really have the benefit of having done a full quarter of this to say what works yet. But I would say so far, the key has been to have a high degree of automation. And I don't necessarily mean that in the software sense. So that is certainly a factor. And you can think about it this way. Every day that I wake up,
00:14:39
Speaker
I have to make a bunch of different decisions and the less decisions that i have to make with effort the better and so what are those decisions do i work on this or do i work on that do i work on the risk your thing or the safer thing do i do marketing today or do i do product work today i've kind of automated my.
00:14:59
Speaker
routine enough to make very few of those decisions. Or at least when I make those decisions, the decision is automatic. It doesn't take any energy from me. And so I've got myself in a cadence where the first three days of the month, I'm working on marketing. Every other day, I'm working on product. I've kind of automated the marketing from that sense. My marketing may or may not be good during the month, but I've sort of committed to this is what I'm doing. Similarly with planning, as I build the product, I've got a roadmap.
00:15:27
Speaker
I'm dynamically deciding what's in and out of scope, but I have a policy of like, this is the minimum bar I need to hit to ship. Everything else can wait. And it's required the discipline to keep coming back to that and say, I'm not going to look at every decision and spend
00:15:45
Speaker
five minutes ten minutes an hour deciding what to do i'm just gonna go based on what's on the plan and it's gonna turn out the way it is i can always adjust my policy later but this is what i'm doing right now and so far that's been the key to staying saying i'm not working heroic hours i'm working forty hours a week i have a family but it's been having that discipline plan and automation in place that's let me be effective so far okay so you're treating yourself like an employee almost of some higher plan.
00:16:13
Speaker
Yeah, I think you kind of have to. When I was younger, I could succeed by basically brute forcing any problem. I could take as long as I want. I can try all the options. I can kind of come in and out of whether I'm working on it. Right now, I don't have that much time.
00:16:29
Speaker
It really really depends on having a plan to execute and there's something comforting about that too like in the past i may have felt that something else i feel bad and, you know this time around i have a real plan and the plan may fail and that's gonna feel kind of crappy but at least i have no well-reasoned plan and that actually is comforting on its own i think that's probably a, something to lean on is the storms rolling.
00:16:54
Speaker
Yeah. That kind of hints at something larger. Is there anything from your previous business that you regret doing? Like, if I ever do this again, I'm not going to do that. I'm going to do this. I think we could spend the next six hours talking about things like that.
00:17:12
Speaker
Yeah, what are the big things that come to mind? I mean, certainly, I committed the biggest error you can make as a first-time entrepreneur, which is having no marketing and no go-to-market plan, believing that if you build a product, the customers are just going to come if it's good enough. And unfortunately, to say it is not true. You can build the greatest product in the world. The greatest product does not always win. It's the product that has the most sensible story, has the best go-to-market
00:17:40
Speaker
has the best usability. There are so many other things besides building the best set of features that makes products succeed. And so I didn't do any of that in my first company. We just thought we'd just build a product and we'd tell a couple people about it and then it would go viral from there.
00:17:56
Speaker
And I think that's the cardinal sin that every technical founder makes because people like us, you've done a company before, you know what it's like, you have a great engineering idea, and you expect the rest of it to take care of itself because that's not really part of your initial skill set. And so it's easy to punt that problem up the road.
00:18:20
Speaker
Yeah. Yeah. It's the same. You can see exactly the same structure of problem from the like stereotypical other side of the fence where someone has a great idea and a great business plan and they think actually building it will be trivial. I'll get some, I'll get some students do it in a weekend or something. Yeah. And then I'll be the head of the new Facebook. Yeah. So yeah. And I think that's kind of like, um,
00:18:44
Speaker
To me, the best possible outcome of this is developing a balanced skill set where you fall into neither of those traps. You're able to build the ideas that you want, but you also have a balanced perspective where you know all the other challenges to getting your product to market and the things that
Developing Marketing Skills as an Introvert
00:18:58
Speaker
you don't have to do. You actually don't have to implement every feature. You should spend more of your time coming up with a better story, better pricing model, a better way to connect with your customers. And I think the people who have those skills, I just admire them so much because they have such stability in what they're doing.
00:19:13
Speaker
Yeah. If only it were easier to figure out the path, it would be wonderful if we could just, as developers, spend most of our time solving problems in a way that the market responded to so we would make enough money to carry on solving problems that interested us. That's right. Yeah.
00:19:33
Speaker
It reminds me of, and I'm gonna, I wonder if the book I'm thinking of is up on my bookshelf. No, it's not. Oh, yes, it is. Hang on. God, what's his name? Austin, Austin, Cleon, Austin Cleon, who wrote Steel Like an Artist.
00:19:52
Speaker
Right. He, one of his ideas, and I think his second book was, if you want to actually be an artist, then you're just going to have to accept the fact that you're going to spend half of your time doing art and half of the time marketing your art, talking about it, right, reaching out, making it happen in the world, as well as living in your cave. Do you think that holds true for tech as well? Like, if you want to spend half your time, if you want to be a programmer,
00:20:18
Speaker
entrepreneurial programmer, you're going to have to spend half your time putting the code away and talking to people. I'm not sure what the right balance is, but I think the idea is right. You're going to go through different phases where it makes sense to kind of get heads down and build once you have a good idea of what you're doing. And at other times, you spend a lot of your time just talking to people. I think the trick is to develop
00:20:38
Speaker
the sensory feedback of when you're out of balance. Last week, I realized I haven't talked to potential customers in a while. This is a problem I have to get on it. But yeah, I think it's absolutely crucial almost no matter what you're doing to just make sure that you're out there and you're talking to people. Otherwise, you're going to commit the error of building something that nobody wants.
00:21:02
Speaker
I think it's something that people don't want to hear when they're just getting into a career of making things because I mean, often it ends up being people who are I'm a bit more like insular. I'd rather just sort of like have a quiet setting to work on my thing and I didn't think that was supposed to be part of the job. But if you sort of want to take charge of your own product and say this is the thing I want to build, I want to get it out into the world. It's just an essential part of it. It's an area of skill that has to be developed and it can't be ignored.
00:21:31
Speaker
Okay, so how do you develop it? Give me some guidance as a geek.
00:21:36
Speaker
Trial and error, I mean, it's pretty painful at first. And I can't say that I'm, you know, still great at it, but I kind of rewind what's in my mind. I was, you know, could be only described as a software engineer and maybe 2014 or even 2015. I had an idea and I really wanted to get it out there. And so I think a lot of the skill just comes from trial and error and storytelling. You have to be able to hold a conversation with people and see if they're interested. If you can't at least do that, you know, it's sort of a warning sign about whether you're really onto something big or not.
00:22:06
Speaker
I think getting yourself out there and exposed with enough volume of those conversations is important just to get comfortable with it. And then I think the other part of it is to get more skilled in doing it in a variety of mediums. So there's kind of the elevator pitch. Can you tell people in 60 seconds about what you're doing? Can you not use the terms that you know about that they don't know about? That's a whole other thing.
00:22:28
Speaker
Can you design a website that packages up your pitch so that you don't have to rely on doing it over and over so that you can basically pitch in your sleep. Can you put together the pitch deck for people who want to see in the room walk me through the five minute ultra policy presentation.
00:22:43
Speaker
And you learn skills there. The secret to giving a really good pitch is to anticipate the next question that people have in their minds and to answer those questions one in a row. And it makes people feel good because you sort of feel like you're connected with that person, like you're speaking the same language. And so I think if I was going to wrap up all this, it's sort of volume, just doing a lot of it, and then also doing it across all different kinds of situations. There's a lot more than what I described, but I think those are kind of the basics.
00:23:13
Speaker
Yeah. Yeah. It's painful, though, when you're probably naturally an introvert, right? Yeah, certainly. People in our industry tend that way. Yeah. I mean, any kind of new skill is painful to develop. It's probably more so when it sort of moves against your inclinations and is your personality. But I think the more you succeed with it, you sort of realize what's the reward out there. The reward is you take full charge of your own creative vision. It's not that you just wrote the code,
00:23:42
Speaker
You now control how do we talk about it how do we think about how do you price it to me that that's kind of the ultimate power so just be in control of what's. What's the essence of what you're building it's not necessary the case that you need to take this career path and to do what i'm doing which is say you can do a small company to do it all you can have that kind of power to larger company where you got the vision for.
00:24:04
Speaker
How do you want it to look? How do you want it to feel? I feel like those are the people who are, to me, the most exciting to work with. They just sort of are able to pierce through every layer of building the product from the sales, the marketing, the engineering. And you have these really rich discussions with them. And I feel those produce the best products in the end if you can work with people who have that ability. Yeah, yeah. They're rare, but they're fun to work with when you meet them. So how do you...
00:24:30
Speaker
Take me through that with, what's the name of the product again? I noticed solving the $10,000 demo problem. What are we calling it? Yeah, shadow traffic. And actually, what you just said is a great example. I've sort of wrapped up what I'm working on in a story. You remember the story. You remember the problem. And that's mostly what matters. I mean, if you have the problem, you're eventually going to come back to me. It doesn't really matter what the name of the product is, but the problem was memorable. And I think that's actually right there is a good example of, you know,
00:25:01
Speaker
wrapping things up in that particular way. Yeah. Yeah. I feel like you've, uh, you've injured me somehow. You've done some judo, make Jedi mind trick. That's what I'm clawing at. Yeah. But yeah, the product name is shadow traffic. I tried to come up with something that was sort of a visual representation of what I'm trying to do, which is to help people take what looks like realistic data and apply it to their own safe setting, staging environments, testing, that kind of thing. Okay.
00:25:31
Speaker
I faced this problem before when I'm trying to start something up, which is, there's the chicken and egg problem, right? You can't sell the thing to people until you've built it, but you can't really build it until you've got someone to sell it to, because you need that kind of market feedback.
00:25:51
Speaker
I've tried what you've suggested, which is building a website which kind of makes it look real, but it's always kind of hollow unless you've got a product. How are you clawing your way between that left leg, right leg, chicken and egg evolution thing to actually get to, I assume you're trying to get the first customer. I assume that's goal A, right? Yeah. Yeah. Yeah. I think the, um, the key is to figure out what, what is the,
00:26:20
Speaker
What is the essence of what you're building what's the most important part it does feel hollow when when you're really good at products like you are and you can you can vision these ten or these fifteen things when they all come together something great happens and that's true in your head but the trick is to sort of unwind and say what's what's the one or the two things that are really really important and find a way to put that on display for me with shadow traffic.
00:26:43
Speaker
The key is the declarative API. I've come up with an API that is shaped like your data. The overhead of interacting with shadow traffic is actually really small. You take your data, you copy it, you paste it, and then you change some little values in the end. It actually ends up being very similar to what your data looks like. That's the key to it. I tried to make a landing page that really emphasizes that, that shows that on full display. To me, I have to take a little bit of a leap of faith and say,
00:27:13
Speaker
That one unique feature is what's going to get people excited, and it's going to allow me to go build the next 10 or 15 features on top of that that I think are also important. And so I try to stay motivated by figuring out what's the new thing that's happening here that nobody else has, and just focus on that. A key to this is empathy, right? You've got to imagine the world from your customer's point of view, and there's no way around that.
00:27:41
Speaker
Exactly. That's right. You're doing design by wishful thinking, actually. You're imagining how it would look and planning to implement that. Do you worry that you're going to make a public promise that the API will look like this and then two weeks in find out that actually that's really hard and you can't deliver it?
00:28:02
Speaker
Yeah, not so much. I think this comes down to the build in public philosophy. So there's two ways you can build products. You can do the traditional way, which is to say, I have an idea. I'm not going to tell anybody about it because I'm very worried people are going to steal it.
Building in Public: Engaging with Audience Feedback
00:28:15
Speaker
I don't want to make any public commitments. Otherwise, people will come and be mad at me. And then you spend six months or a year or two years building it. And then hopefully, that's the thing that customers want.
00:28:25
Speaker
More times than not, that takes way more risk than the rewards you get. The risk is it's actually not the thing that customers want. People wouldn't have been mad if you put mockups in front of them in the first place. And it just ends up being harder. The diametric opposite of this is built in public, which is to say, nope, I'm not worried. Anybody's going to steal my idea. Maybe somebody does, but I've got a bunch of other ideas in the queue. That's fine. And you just talk about it incessantly. You tell people, this is what I'm thinking. What do you think? Give me feedback.
00:28:51
Speaker
And so I'm three weeks into my first quarter of building four startups in four quarters right now. And what have I done? I built a landing page and I built a prototype of the first product. I've actually already gone out there over the last week and asked for feedback from as many people as I can, showing my basic sketch of the API. And what did it cost me? I got tons of feedback. I spent a week sketching that API. I got some feedback that I need to change this, this, and this. I'm going to go do that. And I'm certainly not going to go
00:29:19
Speaker
Try to sell anything fake that like i don't believe that i can do and i haven't done yet but i am gonna constantly try to bridge that gap and say this is what's in my head.
00:29:29
Speaker
What do you think? And then get that feedback and sort of close, close the interface to the product over time. What's it going to look like? What's it going to feel like? And I feel like this, this is actually way more balanced. I'm just, I'm no longer worried that anybody's going to steal my ideas. People either think my ideas are dumb, which are fine, or they've got their own ideas, which they're actually much more motivated to go do. And, um, yeah, this has kind of been better for me in the long run, I think. You sound like you're actually enjoying marketing.
00:29:59
Speaker
Maybe. If I look at my overall skill set, it's the weakest thing. But I do think it is the gatekeeper to succeeding. You have to try really hard at the thing that you know you maybe suck at. But if you can get good at it, it's the key that's going to unlock everything for you. So yeah, I'm leaning into it. I don't think I'm very good at it right now. But I completely believe that if I can build traction with marketing, it's a key ingredient to success.
00:30:27
Speaker
Yeah. Something I realized years ago was that to make a successful business, sometimes you think, naive programming, you think the way to build a successful business is to have a fantastic product or a fantastic idea. Actually, it's more like building a table. If you've got four reasonably stable legs,
00:30:52
Speaker
You can build a table but you need all of those legs right so you need the product you need the marketing store you need a pricing structure you need. You can't miss out any pieces but i don't have to be absolutely the best in the world.
00:31:06
Speaker
That's totally right. I think the other way that's comforting for people like you and me to look at it is it's all building. We sort of think of engineering as the building. I write the code. I compile it. I've got that feedback. We've been making something. But marketing and sales are actually making things too. Just to give you a quick example, with marketing, I built the website. I've built the funnel. I've built the messaging. It's all
00:31:27
Speaker
being designed very carefully. It's not like I'm sitting in a room throwing darts and saying, I wonder what kind of business marketing words I can use synergy and stuff. I'm actually selecting words out of a thesaurus that I think are really good. It's very, very
00:31:42
Speaker
reasoned and detailed. And it's the same with sales. How do you construct a pitch that's going to lead people through that cycle of, I wonder about X. The answer is Y. I wonder about A. The answer is B. It's building all the way through. And I think if you can think of it that way, you can have a lot more fun because every day I wake up and I build something, no matter what the domain happens to be. That's a nice way of thinking about it for those of us who are in engineering persuasion, fundamentally. Yeah.
00:32:11
Speaker
Do you, um, it sounds like you've done a fair bit to de-risk this process. And one of the things you seem to be doing in de-risking it is by having this four startups in four quarters thing, you're probably building an audience which will carry through even to, if the first three ideas fail, you're carrying in a natural audience across to the fourth one. Is that a happy coincidence or a deliberate plan?
00:32:41
Speaker
Yeah, that's deliberate. And I think it's something if you look around, all your favorite people who are successful in business have built audiences for themselves. I'm not trying to do it in a greedy way where I'm courting attention at all costs. I'm trying to make it win-win, where the win for me is I have an audience, but the win for anyone who follows me is you'll get a transparent log of how am I running my businesses, you get to look at my successes and failures and learn from me. And I think that's absolutely crucial.
00:33:06
Speaker
I like to think about building an audience and making products succeed as communicating with a graph. Just picture a graph in your mind. There's all these nodes that connect. If you want to take a product to market, you have to go to each of those nodes and say, Hey, do you like my product? Do you want to buy it?
00:33:22
Speaker
The more tightly connected those nodes are the faster it is if you can just go to one big node which is like your personal network boom you're you're able to move pretty fast but if you're you're loosely connected to all these people how much longer is it gonna take to go to every person and introduce your product can you have the problem see if they're willing to try it just take significantly longer and so.
00:33:41
Speaker
Yeah, I think there's real skill on this idea of audience building, and particularly for the people who can make it win-win, not just sort of a one-way. Everyone listened to my ideas, but to sort of build a little bit of a community around what you're doing. Yeah, yeah. I would find your approach very scary, but I can certainly see the logic to it. Why do you think it would be scary for you?
00:34:06
Speaker
So I know some people who are deeply motivated by public commitments, right?
00:34:13
Speaker
I'm thinking of a particular friend of mine who anytime he wants to do anything, first thing he does is declare it to the world that he's going to do it. That works for him. It really doesn't work for me. I find that it just either I succeed or I fail as I was going to either way, but if I promised it and I fail, it just hurts. And all of my motivation is intrinsic. The things I want to do, it comes from just this burning need to do it. Yeah.
00:34:42
Speaker
I think there's a lot of power in having lived enough years and just having enough experience where you sort of know what you need to succeed. The route I'm taking of public commitment
00:34:57
Speaker
doesn't work for you. Totally fine. If you know it works for you, that's great. You need to spend zero extra time figuring out how to motivate
Understanding Motivation in Entrepreneurship
00:35:04
Speaker
yourself. And I think that that's really important because someday the pressure is going to be on the line, and you want to be able to select the tools that are best going to equip you to get to the finish line. And I think the more you know about yourself in advance, the more likely you are to succeed.
00:35:18
Speaker
Yeah, one of the best things I ever learned about management was that there's no secret to motivating people because every person has a different way of being motivated. I always remember I worked with this guy who. He in his spare time he was training for the Olympics.
00:35:38
Speaker
And he wasn't doing that well in the day job, right? And we were trying everything to try and get, cause we knew he had talent, but it wasn't really working out. And eventually one day I realized that, I mean, this is, I'm going to sound like I'm manipulating people psychologically. I just, I figured out what made him tick. Any, any work he would do, I'd say that's great, but I need you to basically, I need you to give me five more drop and give me five more. You've done a good job, but you need to push it harder. And that was exactly what motivated him.
00:36:06
Speaker
He was the kind of person who needed a coach that said, run an extra mile. And then he did his best work. It's like, that's not how I motivate myself, but figuring out the different ways people motivate themselves is like, yeah. And then you realize you can apply that same rule to yourself and suddenly you can unlock something in yourself.
00:36:26
Speaker
It's funny you bring that up. I just finished a book called The Talent Code that talks about why are people good at different things and what's the process to getting there. And there was an entire set of chapters about coaching. And it was exactly what you said, the best coaches in the world. You imagine these people in the movies who are giving motivational speeches in the locker room.
00:36:42
Speaker
In this author's view, it's mostly not at all like that in the real world with the most successful teams. The best coaches are the ones who are adapting to every player and giving different kinds of feedback, using different kinds of motivation. And more often than not, it's a quieter thing. It's sort of like, what do you need?
00:36:59
Speaker
How can I communicate with you in a way that makes sense? And it's usually not by barking at someone, it's sort of by figuring out, in that case, I need you to push a little bit further. In other cases, you need to be a little bit gentler and say, hey, you don't have to put so much pressure on yourself.
00:37:14
Speaker
And I think, yeah, this is the hard part about business. There's not really coaches. I mean, there's executive coaches out there. I'm a little skeptical of them. But a lot of this is trying to find your own way through a very almost every time you've got a unique set of problems. And this is what makes it so fun. You wake up every day in a business, you've got a set of challenges that probably nobody else has exactly faced. And you need to figure out how to wind your way through the maze. And so there's value in doing what you say, which is kind of learning to be your own coach, learning what makes you tick.
Decision-Making and Managing Growth
00:37:44
Speaker
And the people who can figure that out, I think those are the ones that are most likely to succeed when pressure's on the line.
00:37:51
Speaker
Yeah, you reminded me of something else that I quite liked. Hucking back to your idea of building things, something else I quite liked about the kind of mid phase of building a business, which you end up, as well as building these software systems, you realize there are processes, human interaction systems, ways of dealing with particular needs of customers. You end up building soft systems with the same architectural principles you'd use for building software systems, right?
00:38:21
Speaker
And that's a lot of fun. And I shall envy you when you get to that stage.
00:38:26
Speaker
Yeah, I used to actually not like people management very much. And I still wouldn't choose it for myself. But a friend did kind of describe it to me in a way that made sense. He said, it's sort of like building an API. You have this many teams. Okay, what's the contract between them? What's the purpose of these subsystems? And then what's the output of each subsystem? And how are they going to talk to each other? The more you can kind of define that in a way that you could write on paper and say, you can explain it to somebody in 60 seconds.
00:38:52
Speaker
That's good people management. I really respect that. That actually changes my perspective from being, okay, I'm going to lord over people and say, you do this and you do this. No, it's, it's a, it's a design and the ones that, that work really well. They're the most consciously, uh, consciously crafted. Yeah. Yeah. It's, um, I find system architecture very satisfying and the fact that you can craft systems in completely different domains and it's still the same principles. Yeah. That is satisfying.
00:39:22
Speaker
Let me take another thread through this, because I think you're planning to build four businesses, and here's another thing I would find very difficult. Okay, so let's say you're at the end of quarter two, your second business is an obvious failure, you drop that. End of quarter three is an obvious success. Okay, cool, then that's the one you run with.
00:39:45
Speaker
What if you get to the end of a quarter and it's kind of ticking along and it's doing okay and maybe if you put another couple of years in it will grow something sustainable. How do you choose whether to put all your chips in or kill it?
00:40:00
Speaker
I think I'll have to get back to you on that. I consider it a pretty maybe fortunate outcome if I was at least able to get to that level of traction where I was like, maybe in three months of effort, maybe there's something here. That's actually a great outcome. I think the exercise I'm going to have to go through is to figure out, okay, how much faith do I have in that idea based on just my intuition of the situation? And then how
00:40:25
Speaker
Small can i size my neck to bed it's not like i have to make each of these startup that's equally size i have some pretty small ideas that are sort of consumer oriented and i can do rather quickly and maybe six weeks for example inside i'm just gonna have to go to that motion.
00:40:40
Speaker
But I do think in the end, I'm either going to end up with a small set of multiple businesses that each do just a little bit of revenue and I'm kind of happy with, or I'm going to find the one that I want to go all in on and maybe still keep it small but decide that this is my area of focus.
00:40:57
Speaker
Um, I mean, this is probably the theme of this podcast. It's an admission of not knowing. I mean, I've got a bunch of things I like. I don't know what the market wants. I don't know what's going to work in that particular moment. I'm just going to try and then whatever kind of feels right to me at the time, um, based on, on my intuition and my judgment, I'm going to go with it. And just knowing I don't have to stop at four and four. I can, I can do five, six, and seven if none of those workout too. And, um, I'm, I'm eventually going to succeed at this. I'm pretty, pretty determined. How do you, um,
00:41:28
Speaker
How do you deal with, I mean, okay, so you can, you can say, I don't know for sure, but I know today. But how do you deal with the fact that you you're sure it's the right thing to do for today and next week you wake up and you're unsure and the week after that you're sure again and human emotions, they're very fickle, they flow in and out like the tide. And how do you take the average of how you're feeling?
00:41:54
Speaker
One thing I was hoping to do a little bit better than the last time I did this was to get off the roller coaster. Everybody talked about the startup roller coaster. One day, you feel incredible. You've got a new lead for customers. It seemed like you're going to close a deal. The next day or the next week, something terrible has happened. A critical employee has quit. The customer lead fell through. It's just awful.
00:42:14
Speaker
I was sort of hoping I'd be able to get off that roller coaster this time. So far, I really haven't actually sort of feel the swings in my emotion. But I do feel like a key to succeeding at this over time is to neutralize that and say it's not it's not gonna have no emotion, but I'll have seen enough situations where I I have a customer lead. I know there's still probably like a 15% chance that I'm going to close them as a customer.
00:42:35
Speaker
if they end up walking away, that's 85% of the time. I just know that that's going to be the case. And so I think it's going to be a combination of just doing this enough to let the volume stabilize me. And then the other is just a mantra that I have is just ride the road in front of you. There's a lot of miles up the road that I still have to go through.
00:42:59
Speaker
I'm just focused on today. And I think it's the only sane way to deal with it. I'm selectively blocking out the long term and saying, I've got this situation that I need to do. If I do it really well, that's great. And if I do it really well tomorrow, that's great.
00:43:13
Speaker
a month or two months or three months where every day I just do great at what I'm doing, I'm going to have better long-term results because of that. Big long-term successes are just lots of little short-term successes chained together. Every day, I feel a little bit overwhelmed and just say to myself, just ride the road in front of you.
00:43:30
Speaker
The marketing thing that's not working well, I'll deal with that next week. The customer email that I need to respond to another day, right now I need to solve this problem of this bug in the software and just kind of having that selective vision, I would say. Yeah. It's funny. It reminds me, again, it's like something we're very used to as programmers, which is some days as a programmer, you feel like a genius and some days you feel like a moron and you just keep writing the software until it works, right? You keep plugging with it.
00:44:00
Speaker
Yeah, I think some of that is overcoming beliefs that are not true. I mean, like, why? Why do you feel like a moron on some days? Well, maybe you did a typo that is incredibly obvious when you wake up the next morning. But it's some it's some part of your subconscious, you kind of believe, hey, at my level of seniority, I should never do that.
00:44:19
Speaker
when clearly that's not the case. Everybody does that. And so some of this is defeating those subconscious beliefs that just frankly aren't true. Unfortunately, I think it's a bit like pulling dandelions in a garden where you pull them out one day and more show up the next. But the more you kind of till the weeds back, the clearer of a mind that you can have.
00:44:41
Speaker
In a way, you're talking about depressuring things for yourself mentally. And that makes me wonder if someone came along with a VC fund and said, Michael, I think you're a genius. Here's a million dollars. Now that comes with the mainstream that it's higher pressure. Would you take it?
00:45:03
Speaker
No, definitely not. And I think it comes back to knowing what are your goals for yourself. So for me, I don't want to have that external commitment, even if the reward may be higher.
00:45:15
Speaker
I just can't say that I'm all that interested in it. I'm actually not sure at this stage, the kind of person that I am, whether the pressure would really be higher. I've managed to put a fair amount of pressure on myself to succeed with the public commitment thing. Knowing what your goals are and what you respond to. In this moment, my goals are to run a small lifestyle business. The pressure that I work well with is to have public commitments.
00:45:42
Speaker
You know, I use the word deep pressure, but I think it's sort of like, how do you set yourself up in the right situation with the right motivation? And when you kind of get that into balance between the right, I'm working on something fun that I love, and I'm also properly motivated by it. That's this sweet spot where, you know, it's allowing me to sit down for eight hours a day during the week and just totally focus on what I'm doing, and not second guess it for the most part.
Role of Family Support
00:46:06
Speaker
Yeah, okay. So not avoiding pressure, but aligning it to what suits you. I can see that. This also plays into, I mean, talking about pressures and motivations. Let's talk about your, your support system here. Specifically, how does your wife feel about this? You've just quit the job when you've got two small children. And as far as she can tell, you're in the shed noodling on marketing plans.
00:46:35
Speaker
Yeah, I think these things are a household effort. So when I was doing my first company, I hadn't yet met my wife. But it was kind of fortunate in that I got to spend a whole bunch of time when I was younger, just as I said, brute forcing the problem, I had as much time as I really needed. And at the time when I met my wife, I was sort of at the end of my company, she had met me as someone who was like clearly an entrepreneur like this, this is what I want to do with myself. This is what I love. I get up and I try to
00:46:59
Speaker
make things and show them to people and see if I can be funny. And so when I went to work at Confluent, she kind of understood that that was going to be a phase of life for me and that I was eventually going to get back to it. And so I think you really do have to have the people in your life who are going to root you on with this. I mean, I talk about waking up and being focused, but I do have many moments of self-doubt. And I think without the people around me who are going to help get me back up,
00:47:24
Speaker
Even companies that are composed of one person, they're not really one people. They're you and then they're all the people who are rooting you on and keeping you going. I'll give you an example from my last company. We had just a catastrophic moment when our initial product just didn't work. We were basically running out of money. We didn't know what we were going to do. I was just on the floor. I didn't know what to do.
00:47:45
Speaker
Our corporate lawyer of all people basically picked me back up and helped talk me through how am I going to make this work? How am I going to turn this around? And it was a key moment for me. And I think without those kinds of people in your life, you just really need them to help you when you're down because it's going to happen. You're going to have the feelings where it's just like, I'm in the darkest possible place and you need a mixture of your own drive to get out of it. And then people to also help you along the way because it's never just you.
Sharing Successes and Failures Transparently
00:48:13
Speaker
Yeah.
00:48:14
Speaker
If you hit that point again, are you going to stick with this commitment of publicly talking about that as well in your marketing? I think so. I've gotten enough messages from people
00:48:28
Speaker
have been thankful to see a little bit what's on the inside of my head as I start this. And I'm trying to balance what's going well. Well, I'm starting to build a little bit of traction in my product. What's going not well? I have moments of self-doubt all the time. And people like hearing that balance perspective. If I just get to the end of this and I'm like, I cannot do it anymore, I can promise I'm not going to go out.
00:48:52
Speaker
quietly. I'll talk about it because I just think there's so much value that can be created by walking people through your mindset of like, okay, I failed at this. Why? What are the consequences? What can I do now? And I hope not to have to do that, but it'll be painful if I do. But yeah, I guess it's just kind of my way of maybe giving back to all the people who helped me. It's sort of a scalable way to help other people to say, here's my journey. Here's why I ended up
00:49:20
Speaker
Make of it what you will. Maybe you can use some of this for yourself. Maybe not. Yeah. It seems like a very non-silicon valley way to behave, though. Where you were just supposed to talk up your success. Yeah. With all the love in the world, Silicon Valley, I think sometimes the priorities are a little bit skewed. Let's say that. Yeah. I mean, as an example of that, I noticed kind of everything that's
00:49:47
Speaker
celebrated in our world. A lot of it is fundraising. How much money did you raise? And this was certainly true before the bubble. I mean, so many companies raised just insane amounts of money. And that was the thing that was celebrated, much less what product did you build and what traction did you get? And I was kind of sick of all that. I mean, people can do what they want, but what am I going to focus on myself?
00:50:08
Speaker
I really want to build businesses that I know succeeded because of my own skill. That's the thing that I care about. And so I'm trying to build that culture around me that set of people who values that kind of success.
Future Updates and Community Engagement
00:50:21
Speaker
Yeah. Do you hope, though, to breach the point where you're hiring people and this becomes a larger concern?
00:50:29
Speaker
Maybe, I think at least for the next year, I'm pretty eager to try to just take a solo run and say, how can I take this automation thing to the highest possible level? How can I, as an individual, put my skills on display of building?
00:50:44
Speaker
marketing selling storytelling writing i'm kind of like the person wants to do the cat and i want to do all the events and yeah maybe i'm not gonna have as big as a paycheck as i could if i was gonna like found a larger company but at least for a year to i really wanted to try to see if i can make all my skills shine.
00:51:01
Speaker
I know I've got weak points, but in the worst case, this next year is going to be education free. I'm paying for my tuition. I'm failing at this and that, but I'm going to get better at it. And the worst that's going to happen is I'm going to patch over those rough areas and I'm going to come out of it a lot stronger for my next thing. Yeah. Yeah. And, um, and we get to watch along for the ride, which is interesting. I have to make you promise to come back at the end of one of these experiments and do a retrospective.
00:51:29
Speaker
Let's do it. I'll give you the whole thing. If people want to follow along, I'm writing once a week on a sub stack. I just write a little short column. What did I do this week? What worked well? What didn't? But yeah, I think it would be a lot of fun to come and give the maybe the verbal full length overview of what happens. I've already got a bit of a story so far about shadow traffic. How has building public helped me?
00:51:52
Speaker
How is my marketing working and not working i think it'll be really fun to kind of unpack all of it all after after twelve weeks. Yeah especially seeing that from a program as mindset i think certainly i can relate to more easily than someone who's got background in marketing writing out the technical experience.
00:52:14
Speaker
Yeah, absolutely. Yeah, cool. Well, we will definitely get you back. And in the meantime, we'll put a link to your sub stack in the show notes so people can find you. Michael Dragalis, thank you very much for joining us and best of luck. Thanks for having me. It's been a lot of fun.
00:52:29
Speaker
Thank you, Michael. And best of luck. I really hope you land safely. And I mean that. I'm looking at you like... I'm looking at you like a man who wants to do a parachute jump, but wants you to jump first. If you land safely, I might jump along too. If you are feeling similar, then you might want to follow along with his journey. There's a link to his sub-stack in the show notes. You can read along or you can subscribe to his mailing list and you'll get regular updates.
00:52:58
Speaker
There's also a link in the show notes to a couple of the books we discussed. The Austin Kleon books I mentioned, they're a light, a really inspiring read for, well, business, art, any creative project I'd thoroughly recommend.
00:53:12
Speaker
And before you go and do all that, if you found this episode useful, please take a moment to like it, share it, rate it, subscribe to it, click that notification. You know how all this goes. We're going to be back next week and I hope you join us. So until then, I've been your host, Chris Jenkins. This has been Developer Voices with Michael Dragalas. Thanks for listening.