VC Money vs Bootstrapping: How He Hit 90% Margins Without Investors

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Highlights

Kira lost his memory in a car crash at 13, and for a couple of years he couldn't hold on to anything new. After he moved to the US, he found American news doing to readers what the crash had done to him: Disorienting them. He tells Leo Young how he tested that hunch before building informed.now, from friends and family to posters around San Francisco to large anonymous surveys. Selling a single text keeps margins above 90%, which is why informed.now never needed venture money.

Top Quotes

"Your attention is your superpower. Wield it, safeguard it, and don't let it get fractured by a bunch of little meaningless distractions." (Kira Shishkin)

"There's a difference between being good at interviewing, actually knowing what to do, and actually getting things done." (Leo Young)

"Free money is very expensive. There's a myth in the world of entrepreneurship that in order to run a legitimate business, you need this external validation of an investor coming in and blessing your business with money." (Kira Shishkin)

Transcript

Leo Young: Today's guest is Kira Shishkin, CEO of informed.now, which delivers the world's news in 5 bullets a day by text, and a 4-time founder who has built in crypto, publishing, and consumer tech. At 13, he survived a car crash in Ukraine that erases memory, and everything he's built since comes back to what he's learned rebuilding it. Kira, welcome to the podcast.

Kira Shishkin: Leo, thank you so much for having me.

Leo Young: So tell us, what's been the most significant lesson that you've learned in this past year?

Kira Shishkin: Gosh. I think it's a lesson I've been learning every year, and this year in particular, which is the power of prioritizing, and just how much your life can slow down when you don't know how to prioritize properly or you don't force yourself to prioritize. I think this year's lesson has been the same, and it's been a lesson I've been trying to learn for many years. Maybe this year it will stick.

Leo Young: Yeah, you know, I had one of my teammates tell me it just feels like some days just fly by and I don't feel like I've gotten much done. But that's a crucial skill, to figure out how to spend your scarce resource, like time, money, efforts, right, to move your needle forward.

Kira Shishkin: On my team, and something I've learned from the best of the best working on my previous venture, which was an incubation in a much larger, more tenured company called Intuit, is forced prioritization, right? Even on days that don't seem as busy and you think, "I don't have to prioritize anything, I'll get to everything," it's an illusion, right? You are always scarce for time.

What we do on a team, and what I do daily, is diligently make a list of your priorities, but not stop there and actually force rank them, saying, "If I only get nothing but this done, what should be number one, number two, number three?" Then evaluate the next day: if you got done the thing that was number five or number six, but not number one, that's something you should hold yourself accountable to. The only thing that mattered is that number one item.

And that's the practice that I'm learning this year and trying to proselytize to the rest of my team and my partners and people that I'm in touch with and work with.

Leo Young: Yeah, I think that's super important too. Especially when you're at an early stage company, you're trying to compete with bigger companies. So how do you compete? You have to focus on what matters and strip everything else. But with that said, maybe you can give the audience a little bit of context on you, your journey, how you got here.

Kira Shishkin: You've framed it upfront really nicely. I'm a Ukrainian Israeli American immigrant founder, right? Generation zero. And I've built a couple of companies leading up to informed.now, but this one feels like such an alignment of honoring my own personal story of losing attention and being disoriented for years as a result of the car accident. It's also timely to what's needed right now in our culture and our society, which is news without noise, information without an agenda.

And informed.now, which has been my bread and butter, my sole focus, my first-rank priority for the last 2 years, is informed.now. We are a news research company with a mission to put the power of facts in the palm of everyday people in America, which to us in this case means news without the noise of advertisement, without the noise of bias, and without the noise of click-bait sensationalism.

Leo Young: Very interesting. And you bring up a good point that there is a lot of noise out there in news, and the evolution of news outlets, right? Before, in the 50s, people were well respected, like Will Ferrell in Anchorman, they're proper people. And now it's like there's unlimited news. There's always something scary going on. Some disease, or some foodborne illness that your mom shares on Facebook, and people are riled up over that, right? There's just a lot of noise.

Kira Shishkin: The incentives have gone awry, right? The incentives behind sharing information were once, as you're referencing, to inform people. But now it's to entertain, and to seize their attention for as long as possible so that the attention can be harvested to solicit and advertise adjacent or external services, right? Which is why when you read a news article these days, and I kind of want to flash an example to you almost,

Leo Young: Yeah.

Kira Shishkin: when you see a news article these days, most of what you're seeing on the screen is not news. It's actually the way opposite of news. It's noise content, right? So you see advertisements, clickbait, pop-ups, everything but the actual facts themselves.

Leo Young: Yeah, that is true. And I can't help but think, when you're talking about the power of prioritizing, when you strip out the noise and people focus more on what matters to them, it almost allows them to build a better life. Because right now there's this phenomenon of the monetization of attention, right? It gets in the way of things, it just brings more noise into your life that doesn't necessarily serve you.

Kira Shishkin: And I think it came with the shifted incentives, from informing people to having all these ulterior motives like advertising or maximizing engagement. A social media platform is an example of an ulterior incentive that isn't just misaligned with informing a person and leaving them alone, it's contrary to it. Because if you just give somebody what they need to know and leave them alone, they're not going to maximize their engagement on your platform, right? They're going to leave and move on with their life.

And the incentive for every social media platform, even every traditional media platform, is how can we increase readership, increase time spent, and increase our footprint on our readers' attention? I think that's unethical, right? It's not just a terrible idea, it's also unethical. It's unsustainable. And we've designed our whole project around how we reverse those incentives, where we are honoring what the reader wants and not any ulterior actor, whether advertiser, sponsor, tech platform, shareholder, or investor. What does the reader want? And that's been lost.

Leo Young: Yeah. And so bring us back to the beginning. How did you come up with this idea, and how did you evaluate the opportunity? Because I think a really important skill of an entrepreneur is identifying what is worthwhile of your investment, of time, money, attention, right?

Kira Shishkin: Gosh, I would say it goes back for a moment to that very personal thread of my story, the car accident. After the general amnesia and waking up with no memories of my life, there were a couple of years where I couldn't remember things short term. I couldn't remember long-term things like my life before it, but even things I was trying to learn in that moment. To learn anything, to understand anything, you need some short-term memory retention. I couldn't. And I couldn't really wield my focus.

It was such a disorienting state that I think that was the craziest setback and disability of my life. Forget the physical damage that I've incurred and all the other things. The damage of not being able to use your brain is the most limiting, the most crippling experience that I could have imagined.

And when I came to the US over a decade ago now, I observed that that is just the state of media here. The media here is constantly trying to disorient the reader, right? With all this extraneous, bubbling, sensationalized, click-baited, rage-baited content. And it almost triggered me. It's like, my God, I don't want anyone to have gone through that experience that I went through, but now here it is, the default experience of just opening up a news article. That put a chip on my shoulder, saying, "No, no, no, no, no. We've got to build an alternative for people that seek it."

Leo Young: Makes sense. So as far as building out the company, okay, now you have this idea. I think it makes a lot of sense. It's one that you can tell a good story on. How did you figure that it's worthwhile, that the monetization structure eventually makes sense to build this company around? Because everything kind of runs on profit, right? You have to pay for employees, all that stuff.

Kira Shishkin: And I think that is also not the final question, that everything runs on money. It's what is money being paid for? It's paid for value. It ultimately comes down to how you can be helpful to other people in a way that they will find valuable. I think that simplifies the question in many ways: Can we help people in a valuable, unique way? It simplifies the question that you're going to research into just, can you make something that's going to help people?

For me, it's sort of concentric circles, or maybe a spiral shape, like a little snail. Initially, I had to have felt it myself. I think there are entrepreneurs out there that can solve other people's problems without empathizing with them, without having experienced them themselves. I'm sure it's possible. I find it hard to do that. I need to feel the problem myself first. That's the first point on the snail spiral, and I felt it myself.

The next was, well, I have friends, I have family, I'm lucky to have friends and family. I'm going to talk to them. I'm going to say, "Hey guys, is this a good idea?" You're not literally pitching the idea, but saying, "Do you feel that reading news has become not worthwhile?" And then you get a resounding yes in the immediately accessible community, which is not enough to validate the idea, but it is an inevitable step forward toward validating it.

So then you go forward and you say, okay, I've talked to all my friends and family, now they're kind of annoyed with me for asking them too many questions, and it works, they feel the same problem. Then you go further, right? You can put up posters up in a city, which is something we did in San Francisco. You can ask friends of friends, you can go into Facebook groups and Reddit and start talking to people about the problem. "Hey, do you feel this too?" Now you're reaching much more statistically significant numbers, not just your family and friends, but people you don't know, people that don't have any motive to say these things to you. They're just in the wild.

And then ultimately you're breaking into surveys, right? How do you do larger-scale surveys that are much more anonymized, much more designed and targeted around getting a huge scale of people, 3,000, 30,000, to say the same thing? Authentically say, "I don't want to read news anymore because there are too many ads, and I wish there was a solution that had news without ads," right? That's the validating piece. We have a couple of threads: no ads, no bias, no sensationalism. But I'm just pulling on one of the examples and seeing that tested across a larger body. To me, that's the spiral that gets you from idea to conviction.

Leo Young: And what's interesting is, as far as valuable problems, I think there's a Venn diagram of what is needed, what is valued, what you're good at, et cetera. Aside from maybe just intuition to some extent, how did you figure out this is a worthwhile problem to solve, that it's demanded, to now start this company around it?

Kira Shishkin: Well, I was hoping to answer that question by painting the spiral, because as I went through these gates of sanity, they have been a resounding yes, right? There's been enough intake. What you want to avoid in this process is seeding the answer. You want to ask the person to just speak their mind and see if they get to the same conclusion on their own. When you have that at scale, going from friends and family to strangers to large-scale strangers, that's the validation that says, "Hey, this is a good idea, this is a need that's unserved."

And then, to add to that framework on the back end, you go and see if there are solutions out there trying to do something that all these people are saying needs to happen. And there weren't. To this day, there aren't. We're very much a pioneer of our category. When you see people painting the problem the same way that you see it, and you see a dearth of solutions, you're like, "Wow, there is a gap in the market." There is a thing here that people are finding valuable and nobody's doing. I think that's a wedge that you're looking for.

Leo Young: Yeah, that is interesting. And so when it comes to your company now, as far as how you build your team and right-size your team to solve the problem, I think now we have a lot of tools to give us the liberties, right? We can use AI, we can use offshore workers or something like that. What's your team like now, and how did you figure out this is the team that needs to be built?

Kira Shishkin: Well, I love that you say the word offshore workers. I think that's definitely a genre of hiring, and it's huge, especially in the tech world that I come from, at Google, at Intuit. Especially at Google, it's a huge share of people working from abroad. I do believe in that, but I think there's a slightly different mentality. A lot of people, when they say offshore workers, are mostly leaning into labor arbitrage, right? How can we get people to work for less?

For me, the framework, or the mindset, is a lot more that there is no place in the world, even San Francisco, that is the headquarters of talent, right? There are talented people in New York, there are talented people in San Francisco, there are also talented people in Nigeria. It's hard to believe because we don't associate that, but there are. It's about finding a diamond in the rough wherever the geography is.

So we hire internationally from day one, not only because I'm an international person and I've seen outstanding talent all across, but because I don't think all the people I want to hire are concentrated in a certain zip code, right? And we are a remote-first company, so we're not limited by a certain geography. The team is very international, across Asia, the Middle East, Europe, and the US, and always has that international scope to it.

We do have one core thing that is different. We hire a lot of temporary people. We run a very robust intern program year-round, right? Right now we're lucky to have 4 super talented interns, but we do that throughout the year. We structure a lot of work around people who come in and do their best, be helpful, be around, but they're students, right? So then they leave and there's a rotation. We also hire fractionally a fair amount. We hired a chief of staff fractionally recently, where we bring them in at a time when we really need somebody, but it isn't necessarily a permanent position.

With all that being said, we've stretched and shrunk as a team over the last 2 years, from 30 people down to 10 people, at different moments based on where we were in our growth stage. There are certain moments in a company where you need people. In the beginning we needed more people than we do now, and then you shrink. Being transparent with those intentions and being clear as to when you need how many people is really important. We're always looking to operate lean. We don't ever need people that don't have a clear responsibility, but that changes as you grow. It can both shrink and expand.

Leo Young: Yeah. That is interesting. And I think people sometimes forget that a business is a living, breathing thing, right? That the demands for it change over time. When you're working on the initial product, the version 1.0, it's all hands on deck. You need a lot of technical expertise. But then maybe you're doing go-to-market, so maybe it's a different kind of team that you need to get it into the hands of the people, right?

Kira Shishkin: I think there's almost a common wisdom that there's a trajectory of a company going from zero, one person, two people, almost to a thousand. But I think that's maybe an old way of thinking, of a company just linearly growing. In our case, there have been moments where it's been the opposite, where as certain operations matured, we needed fewer people, or we needed to reallocate people to different functions. In some ways, we actually started with more people than we have now, and that was intentional. In the very beginning there was a moment where we needed to bloat our team a little bit more, but the goal was not always to have 30 people.

It may change in the future, but I think especially companies these days go through these shrinking and growing cycles that don't in any way signal an unhealthiness, but just signal different needs changing all the time. There was a moment we needed more people. We don't currently.

Leo Young: Yeah. And how did you let your team know that? As you're growing and contracting, how do you set that expectation, and how do you handle the actual transition?

Kira Shishkin: It's funny, we treat everything almost like an internship, right? Whenever we hire somebody, there's always an extended work trial that is paid, and it's very much, "Hey, we're going to work together for 2 weeks and make sure this makes sense." And then if it does, we'll say, okay. These aren't all roles. Some roles are hired permanent from the start, but we have a lot of roles that are much more temporary. After that work trial, where we're testing each other out and seeing the mechanics, we'll say, "We'd love for you to join for a quarter, or for 2 quarters."

It's almost like a term. We actually hired a chief of staff for 2 terms, a winter and a spring season, and then we can reevaluate the need for that. We're in the middle of a campaign, right? We work in sprints and campaigns. Essentially you're hired for this campaign, but that campaign is going to be over eventually, and there may be opportunities to stay on permanently in other ways, but we don't want to go into that with those hopes and expectations. We're looking for people who are comfortable coming in on a fractional and more campaign basis.

But that's not all roles, to be clear. Some roles are permanent from the beginning. We have people who joined us 2 years ago and have no plans of leaving, or of us changing. But a big share of our roles are campaign based.

Leo Young: Yeah, I think that's a very interesting way to do it. The norm is, "I think I need someone, so let me go hire someone," and the most you do is maybe a trial period. But I think it's very interesting to turn it into campaigns and sprints, and say, "This is the task at hand, this is what we're bringing you on for, and we would love to continue, but businesses change and we're not sure if it's going to be there, and we just want to be mature and have that conversation up front."

Kira Shishkin: There are certain campaigns that require a certain level of skills, but then as that campaign is over, those skills are not really applied anywhere. This can be operations, product. A lot of it is growth marketing. That's the vast majority of what we focus on: how do we market and tell our story in interesting ways. So much of it is sprints.

The only real wisdom I'm sharing, if any, is that we are very transparent. We don't just assume every role is permanent. We say, "This is a campaign-based role. It can be a quarter, maybe 2 quarters, but then the campaign is over." We always try to communicate that this is a campaign-based role that isn't permanent.

Leo Young: Yeah, yeah, yeah. Very interesting. And how do you hire people? Do you use recruiters, or LinkedIn, or something? Especially for offshore.

Kira Shishkin: We do all of the above. We've worked with a lot of agencies when it comes to international. I haven't had a great experience, to be completely honest. It's hard to do. But because they don't charge up front, you get to see and learn what candidates look like in a certain area. For example, you're looking for somebody in a different time zone, right? One of the things we love is being able to have round-the-clock coverage. So we pick a geography, saying, "We'd love to have somebody who can cover the other hours of the US."

Leo Young: Interesting.

Kira Shishkin: Then we work with a bunch of agencies. Number one, we work with 2, 3, 4, 5, 6 at the same time, and get really smart at what good looks like in that market. Ultimately there's always a goal to build our own muscle. We hire through LinkedIn a lot. We have a lot of inbound through LinkedIn, so even if we don't post roles, a lot of people reach out, and we always try to take the calls, or someone on our team tries to take the calls, to just meet the person and see if there's a friendship to be had.

We love Handshake, which is the student LinkedIn. What most people don't realize is you can post jobs on Handshake, which is the student, college-focused jobs board, but mark them as applicable for alumni. Then you're essentially getting the same value as LinkedIn would, but more university vetted. We actually have a lot of talent coming from Handshake, both in terms of our interns and longer-term engagements that we appreciate.

So we work with agencies, but we don't pay up front until they bring someone we're obsessed with. We try to do a lot of agency stuff to get smart. We work on referrals. We have referral bonuses, so if somebody comes in and they're recommended by somebody else, we want to reward the recommender, and we prioritize that level of ins for sure. Handshake, LinkedIn, and a lot of it is just on-the-ground sourcing. If I'm out and about at a conference and I see somebody who has outstanding skills.

Leo Young: Yeah.

Kira Shishkin: This has actually happened to me. I was at the Stripe conference in San Francisco 2 years ago, and this girl came up and she was so passionate about some bullshit FinTech. She gave us a flyer and said, "Can I tell you about this thing?" And I was like, "Yes, tell me about this thing." We were sitting listening to her, and she was just so excited about this financial management software. It was borderline accounting stuff. And I was like, "Wait a second, before you go, can we hire you to do this?" Same thing at SaaStr, which is the next business conference coming up for our company. And we did hire her, and it was really fun.

Leo Young: Wow. Very cool. I think it's always interesting how people find talent, so to speak. It's hard, as entrepreneurs, to ask: What kind of person do I need? How do I test for it? How do I figure out who has the goods, right? Because I think there's a difference between being good at interviewing versus actually knowing what to do versus your personality and actually getting things done. So it's always interesting. Now let's say you find someone. How do you speed up the onboarding? Because I think that's another challenge too. Every company has its unique context, so how do you do that at scale? And when you're doing campaign based, it comes and goes pretty quickly.

Kira Shishkin: A bunch of technical things that we love: Looms. Huge fan of Looms, and everything should be loomed. We basically have no meetings at the company. Everything is run through Looms, because you can rewatch it, you can synthesize it, and you can watch as many times as you want. You can see the walkthrough of somebody talking to you but also showing you what they're seeing on a screen and doing it. I think that's really powerful.

And we have onboarding playbooks for each role. Every time somebody joins, we share the latest and greatest onboarding playbook, and if they take a weekend or a week to learn through it, they can get caught up very, very quickly. We have a very diligent culture: anytime you learn something new that will be valuable to a future team member, everybody contributes to the onboarding playbooks. Whether you work across operations, research, marketing, anything, if you find something that helped you, you record a Loom about it and put it in the onboarding playbook.

It's growing and learning so quickly because everybody is responsible for cultivating it. By the time the person joins and gets this playbook, it is so rich and refined. Also, we take things away if we don't think they're any good. You get a playbook that doesn't look like anything I've ever seen at a company I worked for. It's extremely thorough, a very step-by-step guide on everything, and there's a format to it that is no bullshit, high signal, low noise, things you need to know.

Leo Young: Yeah.

Kira Shishkin: And the work trial that I mentioned earlier, combined with the onboarding, combined with a learn-by-doing culture, which is very much that we'd rather have a person try and fail than wait until they feel ready and waste a month of not doing anything.

Leo Young: Makes sense. Interesting. And switching gears a little bit, I know this is your fourth venture. You've had different ventures, right? And I feel like each one teaches you maybe one or two core lessons and informs your next one. What was that like, going through the different cycles?

Kira Shishkin: Well, the first ever business was in book publishing. There were many lessons, because it was the first one, but if I take a very positive one that still applies today, it's that sometimes you can deliver a lot of value just by reorganizing information in a better way. I think informed.now is, in an airy way, walking the walk of that. It's just about reorganizing information in a clever way to deliver value.

The second business, in crypto infrastructure, taught me that working in partnership that is aligned with other people can be really beautiful. When it works, it really works, and it's fantastic. If you're able to have partners with a friendly but business-first relationship, I think it's fantastic. That business taught me a lot about working in a partnership with multiple people. It was not a solo venture.

Business number three, the incubation within Intuit, which was a two-sided marketplace, was also a redoubling of the idea that information can be valuable if reorganized. But it was also the power of marketplaces, how much value you can create by allowing people to connect in a certain way and just connecting people in the first place. So maybe I'll summarize by saying the lesson of the third business was the value of helping people connect with each other. Very few things can beat that.

That's what Uber does. DoorDash, Lyft, Amazon, marketplace businesses generally do so much for the world. We've come to take them for granted, but there is a genius in being able to orchestrate TaskRabbit, Craigslist, just helping people connect in an intentional, clear way. That's ultimate value. It's incredible. And that brings me to today.

Leo Young: Nice. And I think what you said was very interesting about the different lessons in them, especially the marketplace. That kind of leads me to think about business models. They change over time. With a lot of startups, let's say back in the early 2010s, everyone wants an app, right? Then it evolved into maybe a SaaS or a marketplace, and now SaaS is kind of dwindling a little bit because of AI, right? So what do you see as the opportunity? What's the hot business model to go into now?

Kira Shishkin: Well, I think marketplaces, right? I think that is an eternal way of adding value, which is helping people connect with each other, simply by reorganizing information in a better way. There is no genius behind TaskRabbit saying, "There are people who will help you build the couch and there are people who need a couch being built." That thing has existed on Craigslist, it exists in Facebook Marketplace. But something about making that intention very clear, and filtering, curating, and combining these two sides, people who need help with certain household tasks and people who are able to help with that, it's not even complicated. This stuff is not that complicated, right? Obviously there are a lot of details that are.

But what I'm saying is that I think the business model of building marketplaces and facilitating ways to connect people based around intention and a certain use case is going to be really powerful, and continues to be really powerful. I think about how much we take Uber for granted, how core it is to the daily experience of anybody. The Uberification of everything has been ongoing, and it's going to continue until we marketplace everything. And it's going to be easy and competitive to do that.

Leo Young: Interesting. Yeah, I think the marketplace notion of how you curate and organize and make things easier is definitely something we see at big scale and small scale, right? I think at small scale too, there are a lot of workshops popping up, like a mindfulness retreat and stuff. It's kind of like a marketplace. You're gathering people who have a like-minded way to do it. So maybe it's just society figuring out this is the way to do it.

Kira Shishkin: Just finding ways to connect people with other people, I think, continues to be the next frontier. It's not new, but it continues to be ever important.

Leo Young: Yeah, makes sense. And I did want to touch on the fact that you have a very colorful background. You've done many different things and had your hands in different experiences. When you look back you can connect the dots very well, but looking forward, in that moment, how did you know when it was time to move on, for one reason or the other? Did you think, "Well, how are people going to view me if I leave this at this time?" Was that ever a thought?

Kira Shishkin: I think the two guiding principles for my life personally, and for my life as somebody who can create value for others, come down to two questions. One: How can I help other people, and how can I be as helpful as possible to other people? That's a spectrum question, where you can have more or less. It's about optimizing how helpful I can be to the people around me. Two, which really answers the question of when it's time to leave: How quickly can I grow as a person? At a point where I feel like my growth is plateauing or slowing down in any capacity, that's when I know it's time to go find another way to help people, if I'm not growing as quickly as I used to.

I think it's inevitable when you work on anything over time that your growth curve starts plateauing. Guided by these two principles, these two questions of how can I be most helpful and how can I also grow as much as possible during it, that has been guiding for me on when I leave a thing and when I start the next thing.

Leo Young: Yeah, and I think it somewhat contradicts what people like Alex Hormozi say, right? But also, granted, his audience is a very different kind of business, whereas for you it's more tech based, right? Because he says you have to stick with what you know and become very good at it, and that usually unlocks the next level of growth, and more novelty comes then.

Kira Shishkin: I think that's very sane advice. I wasn't super familiar with the Hormozi wisdom there, but I think that makes sense. I'm always taking for granted that if you are learning at the fastest possible pace, growing at the fastest possible pace, you will become an expert within a very brief period. And there's almost a no-shit factor to sticking with what you know, because if you don't know what you're doing, it's going to be really hard to be helpful to other people. So there's almost a presupposition, a base fact, between my two principles.

Leo Young: Yeah. That makes sense. And when it comes to the company, I'm assuming that for a few of these you've raised money for it, and it's not all just bootstrapped, right?

Kira Shishkin: informed.now is purposely bootstrapped to maintain the absolute independence that we want to retain when we're trying to be pure in our incentives. Investors also have incentives that are ulterior to what the reader wants, so that's something we were very strict about from the very beginning. And because we reached profitability very quickly, we've lost the need for investors to sponsor unprofitable growth. So informed.now is homegrown to be bootstrapped. But for the previous venture, we raised upwards of 20 million dollars to run it. So it was very much a backed project.

Leo Young: And how did you decide how and when to fund, and where the money comes from? Because in my world too, all money comes with strings, right?

Kira Shishkin: I think amateur entrepreneurs don't realize that. They just think VC money is free money, and it absolutely isn't. Free money is very expensive. There is a myth in the world of entrepreneurship that in order to run a legitimate business, you need this external validation of an investor coming in and blessing your business with money. I think that's very successful propaganda on behalf of VCs, right? It's very good for their deal flow. It's very good for people who are obsessed with constantly reaching out to them.

But there's only a very specific scenario where it even makes sense to raise VC money, and that is when you need to sponsor unprofitable growth. That is not the same thing as having a shitty idea that needs sponsored unprofitable growth. It's not necessarily because your business needs it. It's probably because you have a shitty fucking business. Right. And it's very important to know the difference.

Uber is a good example, part of Uber's growth, DoorDash, these marketplace businesses where you need to land grab a market and you need to subsidize one side of the marketplace. But you have a very clear trajectory that once you do that, you're going to own the market and have monetization levers that open up to you very clearly. It makes sense in certain businesses, often marketplace businesses. But if your idea is just a bad idea and you're looking to raise money to try to force grow a bad idea unprofitably, that isn't a reason to raise venture, right? If you don't have a venture-grade business, which is the vast majority of businesses, you shouldn't raise money for it. You should think of a better business. I'm being facetious, of course.

Leo Young: Yeah. No, no, no.

Kira Shishkin: But I think there's a lot of propaganda around, "This business isn't growing profitably, therefore let's raise money."

Leo Young: I agree.

Kira Shishkin: I think you need to rethink how you make your business grow profitably. For us it was about margins. We got into profitability very quickly with informed.now because we have really intense margin spreads, right? What we're selling isn't even technology, it's a single text. So our margins are like 90% plus. With that you have a very easy, very direct way of managing your costs to get to profitability very quickly. Then you're managing growth, but you're managing profitable growth, so you don't even need to raise any money for it. You're just continuing to put money in and get growth out. It becomes much more predictable. But to your question, I would just be really wary of raising money unless you have a very good reason that you understand is a healthy reason, not "give me money because I can't grow on my own."

Leo Young: Yeah. And to that I say you have to be very careful about the incentives of the people behind the money, right? Because VCs make money by making money for their investors, so they've got to deploy it. They say, "Hey, it's good to have VC, they have their content distribution and word gets out," but that's not necessarily a one-size-fits-all solution. I think for certain people, especially if your company has such high margins, why give away ownership of the company? If anything, if you need funding, maybe it's debt, right? Debt that doesn't come with equity or something.

Kira Shishkin: I love that. I think a lot of entrepreneurs forgo the value of venture debt, and just the value of debt in a small business debt format. If you're willing to bet on your company in a way that you know this is going to work and you have a conviction, then the best way for you is to raise debt capital instead of equity capital. Why would you share the pie with somebody else if you have so much conviction that it's going to work? You don't need other people's faith. If you believe in this thing, just raise debt and put your money where your mouth is, instead of sharing equity to distribute the risk. Take on the risk if you're so confident.

Leo Young: Yeah. And how do you figure out the calculation at the back end? How do you run your calculations so that you know, okay, this is going to be profitable at some point?

Kira Shishkin: That's hard, but I don't think it's impossible. It's around having conservative base and liberal financial planning scenarios, which is mostly about predicting demand. There are many ways of building market sizing models. I don't know if we can get into the specifics of them, but it's about having scenario-based financial models based on demand, and that pertains, for example, to informed.now, with consumer-based platforms. Just spend time in the sheets, in Excel. It's not complicated stuff, especially with Claude, with AI helping you. You can coach yourself into making financial projections and demand projections, making reasonable assumptions, testing them, evaluating them, and figuring out what needs to be true for this scenario to come forward. And do you believe this thing is true or can be true?

If I'll share one high-level piece of advice, it's about building demand projections with assumptions, and then listing those assumptions: these are things that must be true for this model to realize itself, even at the base case scenario. Then look at those assumptions and ask, are these crazy things for me to believe, or are they actually pretty accessible? Are they accessible in combination with each other? And then maybe go and test. You can test an assumption by doing the same spiral research loop that will validate that this is a reasonable assumption to put in our model. Then you scenario test it. I think you can see into the future a little bit further than you would without it.

Leo Young: Yeah, for sure. That's one thing that I think a lot of people forget: break down the math as best as you can, model out the assumptions. That's why PE shops have a reputation of being bean counters, but hey, it works. They can reverse engineer a company's future and determine, "Okay, this is valuable enough to buy." And you can use that same logic for your life. Is this valuable enough for me to spend my time and attention on? Yeah. So, wrapping up, I know we're having a good conversation, but how can people reach out to you? Who are you looking to meet? Who are you looking to help? How can we help you?

Kira Shishkin: I'm always looking to meet other news minimalists, and people who are interested in signal-rich, noise-low information. informed.now does that in news. So if there are any news minimalists among us, definitely reach out. But even just anyone who thinks about how we make information signal rich and how we reshift incentives that have been plaguing media, and generally plaguing the technology sector as well, I'm always a friendly face to talk to. I'm always happy to connect. I'm really easy to reach on LinkedIn, but also across any socials online. I'm very active and available. And to check out informed.now, our name is also our website, so it's a really easy way to see the work that we do for yourself. Just go to informed.now.

Leo Young: Amazing. And what's one final message that you want to leave the listener?

Kira Shishkin: Your attention is your superpower. Use it and wield it and safeguard it, and don't let it be fractured into a bunch of little meaningless distractions. Just wield it like a sword.

Leo Young: I love it. Well, thanks for coming on, Kira.

Kira Shishkin: Leo, thank you so much for having me.