Rebuilding Trust in News with Kira Shishkin from informed.now

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Highlights

Rohit Malhotra presses Kira on how informed.now decides what counts as a fact (upwards of 75% of its coverage comes from primary sources) and how 5 to 7 stories fit into a 150-word briefing. Kira also describes a reverse graffiti stunt that used a stencil and a pressure washer to clean its logo into a dirty Manhattan street, and admits slow hiring and partnership calls cost informed.now months.

Top Quotes

"Even more important than the pervasive bias problem is the sensationalism problem. It hurts trust and readership a lot more than Fox News having one opinion and CNN having another." (Kira Shishkin)

"At the root of all conflict is information conflict. The wars that burn our world today started that way too, and they remind us of how high the stakes really are." (Kira Shishkin)

"News is getting louder so quickly that soon every reader will have to build, buy, or rent a filter for the information they let through and the information they keep out." (Kira Shishkin)

"If you don't know your customer, you don't know what you're doing. If you know your customer really well, it doesn't matter what you're doing." (Kira Shishkin)

Transcript

Rohit Malhotra: Hi everyone, this is Rohit from Life Self Mastery, and today we're excited to have Kira Shishkin, who is the founder and CEO of informed.now, the leading news by SMS service, which imagines how Americans stay informed without the bias and noise of traditional media. He also advises portfolio founders and primary venture partners, and he founded Circuit and Kira Foundation, where he's backed ambitious builders and artists alike. Welcome to the show, Kira.

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

Rohit Malhotra: Awesome. You've had an interesting journey. I saw that you've been in the world of investment banking and the world of startups. How did you get into this world of startups, and what got you excited to build informed.now?

Kira Shishkin: As you mentioned, I had a long-winded path, from growing up in Ukraine to coming of age in Israel to coming to the US and living out my version of the American dream. I started my career in investment banking, private equity, and venture capital. But the entrepreneurial spirit within me, which I think comes from my parents, who are both entrepreneurs, bubbled up over time and got me excited about building.

informed.now is my fourth venture. Being in a state of building allows me to learn the fastest that I'm capable of learning. I'm attracted to a steep learning curve and to being able to do all the jobs when you're on a founding team. That's what brought me to building informed.now, to your question. It's a very timely venture. There's a problem in the world, and specifically in North America, that I'm very passionate about. It feels very personal to me, and that led me to start this company. Now we're in our second year, and I haven't looked back.

Rohit Malhotra: Interesting. And informed.now pitches facts over influence. So how do you personally decide what counts as a fact you can trust versus editorializing?

Kira Shishkin: I love that question, and we get it a lot, because it's probably the number one question behind our company's existence. The spirit of building informed.now is a frustration with the current media landscape. When you consume media, sometimes you notice it and sometimes you don't, but it is constantly polarizing, sensationalizing, and influencing you. A growing minority of people feel an aversion to that, and I think even calling it a minority is an understatement at this point. We're looking for a better solution, a new way to consume news without feeling influenced and without feeling drained. That is the spirit of informed.now.

The way we answer that specific curatorial question is we focus on primary sources. That really is our secret sauce. Traditional legacy media will talk about a news item without sometimes mentioning, and almost never citing, a primary source. We do the opposite. We put it first and foremost. We look across primary sources where they exist, and we read them manually ourselves to ensure that what we surface to the reader is not editorial, not opinion, and not some kind of agenda, but reporting directly from the horse's mouth. Upwards of 75% of our news research coverage comes directly from primary sources. The rest comes from reporting that is much more aggregated, in the event that a primary source is not available. That's often the case for wartime, certain breaking news, and certain cultural movements where there isn't a primary source that can inform the story.

We lean toward the primary source philosophy and methodology, and where we can't, we aggregate primary reporting. We pick our sources and aggregate in a way that seeks to eliminate any polarizing language, any opinion, and any suggestion, implicit or explicit, of how the reader should feel. We go through multiple rounds of review to ensure that when we send something out to the reader, we first of all take 100% responsibility for that content. We are not garbage in, garbage out slop. We take 100% responsibility for every word and every character in our briefs.

Secondly, we find ways to describe issues with neutral or objective words that don't give you a charge, as in this is a bad thing or this is a good thing. We go through a whole layer of review to ensure that the words are completely impartial and neutralized. We get a lot of really positive feedback from our readers. We practically get no negative feedback. There's never a point where someone tells us they feel influenced or that this is biased, and if people felt that way, they would unsubscribe. We have a really high retention of our readers.

Rohit Malhotra: Interesting. And what is the hardest part of compressing a day's news into an SMS without losing that nuance?

Kira Shishkin: Gosh, there are a lot of hard parts. I think the hardest part is deciding how much to write for each summary. The way we communicate is in a highly executive brief. It's almost bullet point like. We have a limited amount of space for every single text, and we always target about 150 words, and they're extremely concise. A single SMS usually contains from 5 to 7 news summaries, each of which is a bullet point. Deciding which details make it into the specific bullet point, and what context is valuable enough that it cannot be omitted, is always a challenge.

Rohit Malhotra: Got it. And how do you measure whether informed.now is reducing that misinformation overload versus just changing its format?

Kira Shishkin: I think that's a great question. We measure in a couple of ways, all of which come back to our reader, our customer. We're not in a place where we can save the world and be everything for everybody. We're looking to solve a very specific need for a group of people who are looking for a solution to this misinformation overload problem. A lot of what we find really reassuring is when our readers tell us, and we have a one-on-one communication with every single reader due to the SMS format, "Since I joined informed.now, I have canceled my other subscriptions because they now appear very noisy in comparison to what you guys do." Or they say, "I have never seen a service like this, because every other thing that I read is either trying to influence me to buy something external or to buy something internal within their own ecosystem."

An example is Fox News, which advertises a whole range of things well beyond their news coverage. The New York Times does the opposite. They advertise so many of their own services, the crosswords, the puzzles, the trivia, the newsletters, the prints, the humor, that it's very hard to just read the news without all the ulterior, exterior solicitation. We reduce that entirely through our mission, our philosophy, and our commitment to the reader, but also through our format. We picked SMS for its minimalism. You cannot send a thousand images, you cannot have pop-ups, and you cannot have privacy-violating, cookie-grabbing trackers. It walks the walk of news minimalism, which is really important to us, because we're not just building a company. We are building a movement, a movement for a healthier relationship with news. A movement for a generation that shouldn't have to read their parents' noisy news. We're building for that. It takes a lot of philosophical resilience and ethical commitment that is difficult to uphold. But if we wouldn't, why are we here? It's got to make sense.

Rohit Malhotra: And Kira, I also run a podcast and a newsletter. So when it comes to media, how do you go about ensuring that you're continuously growing? Are there any growth tactics you have used which have allowed you to increase your subscriber base, especially in the US and Canada?

Kira Shishkin: We've been working for a long time on our referral program, to incentivize every single reader who enjoys our work and loves what we do to be a champion for us. We want them to feel it is worthwhile to send it to their friends and refer others, so we give people referral incentives. That's a really big lever behind our growth, our referral machine. I can't think of a better way to do it, because who would be a better ambassador for our work than somebody who sees the value, is a recipient of that value, and is also sponsoring our work? We're entirely reader sponsored. We're entirely reader supported.

That's one big lever. Another is that we don't really do ads. We do a lot of nontraditional stuff. Right now in New York, I'm overseeing a campaign that my team is running around street marketing. We're showing up in places on the streets of Manhattan. One of the experiments I'll share that was really special is that we had a team take a stencil and pressure wash it onto the dirty street of New York. Another way of describing it is a reverse graffiti operation, where the street is dirty and we selectively clean just our logo with our tagline. It was not the most scalable operation, but it felt really symbolic, because in every way we were cleaning up dirt in a very dirty industry. That's exactly the clarity that we bring, and it felt like a really fitting image for our brand. That's an example of the guerrilla street marketing campaigns that we run in Manhattan.

Rohit Malhotra: Interesting. And Kira, you mentioned that you're on your fourth startup now. What's one instinct from your earlier companies that you had to unlearn before it would work for informed.now?

Kira Shishkin: Each one of my ventures had nothing to do with the previous. The first one was in book publishing, the second was in cryptocurrency infrastructure, and the third was a fintech marketplace. Now we're doing consumer news by SMS. They're very different fields. There were a lot of learnings that were transferable, and many were not.

To your question, one of the things I've had to unlearn is the fear of experimenting, the fear of doing something that isn't going to immediately have an ROI attached to it. It's making a decision that feels fuzzy, where we can't attribute a specific number to the decision. In my previous ventures, I wouldn't make that decision, and neither would my founding team. Now I've gotten more comfortable and unlearned some of that fear. We're also in the consumer world, where you have to take risks, you have to experiment, and you have to see what works, and there isn't a way to just read about it. There is no manual for early stage growth, or the channels are already saturated. So we're doing a lot of experiments, which in my previous ventures I would have been a lot more cautious around.

Rohit Malhotra: Interesting. And when you start something new, how do you decide whether it's going to be a community, a company, or a foundation? Do you specifically decide what the partnership structure would be? How do you go about thinking through...

Kira Shishkin: Thinking through what exactly?

Rohit Malhotra: The structure of the kind of work that you want to do, whether it's a company, a community, or a foundation. Since you also run the Kira Foundation and you also run a community, how do you decide that this will be a part of either a community or a company?

Kira Shishkin: It's an interesting question. I've never had doubts that I wanted the community building element of my life to be a nonprofit, a structure that doesn't monetize community. That's why to this day, Circuit is not a business project. It might change in the future. We've been around for coming on 6 years, and so far we've maintained it as a nonprofit. I never wondered if we should make it into a business. It was never on the table for me.

Kira Foundation is a brand name around the work that I do in the arts, bringing together artists, building an artistic community, and empowering emerging artists with grants and promotion, and trading and selling art from an art trading perspective. To me, those things were never a business that I wanted to run. Foundation, to me, is a casual phrase for doing mission-related work, and that was important to me.

The only company that I run right now that is a company company is informed.now, and that structure was always obvious to me. To get to a scale, to get to an impact, and to validate that our work is needed, I want to have a financial signal, a financial flare, that communicates that this is valuable to readers and readers are going to pay for it. All three projects fell into place very naturally. I never thought about whether informed.now should be a nonprofit, whether Circuit should be for-profit, or whether Kira Foundation should be something else.

Rohit Malhotra: Interesting. You mentioned that you've kept informed.now bootstrapped, but how do you think about hiring when you haven't raised a lot of funding and you're trying to hire the best talent who can help you grow the company?

Kira Shishkin: You're right. We've kept informed.now intentionally bootstrapped over all these years, and that hasn't stopped us from hiring best-in-class talent, because what matters to us is the mission. We need to see that resonance with other people. When they also feel the problem, and when they feel like we are the solution, money becomes secondary.

One of the things that has helped us a lot with hiring is that we are the only company that does what we do. There are others that do something similar, and there is a lot of indirect competition, but there isn't a lot of direct competition, in the sense that there aren't lookalike companies to ours. We're essentially the first news research company in the world. Of course, that's a statement that will be challenged, and we're okay with that. For a lot of the people that we hire, if they're on board with the mission and this is something they feel passionate about, which is obviously what we screen for, it's very hard to then go and find another company that does what we do. It's almost impossible.

Rohit Malhotra: Interesting. And Kira, you also talked about how your parents were entrepreneurs, which influenced you, but how has your background shaped the way you think about trust in institutions, in media, and in other ways?

Kira Shishkin: My background as a Ukrainian, as an Israeli, and now as an American has shown me the high stakes of misinformation overload, especially in Ukraine and Israel. It shows what can happen when there are years, if not decades, of propaganda and brainwashing, of media that doesn't have the best interest of the reader in mind but rather a political agenda, some alternative agenda, or really just a business agenda. It can skew and hurt the clarity of the population. Every real conflict that we see right now in the Middle East, in Ukraine, and in Israel is preceded by an information conflict, and information conflict is very much something that media, and especially news media, is responsible for.

Having seen that play out in Ukraine and in Israel, and then seeing it play out here when I came into the United States, I was already primed to do something about it. I've seen news media fail at really large scales, in ways that have impacted my life very personally.

Rohit Malhotra: Correct. And is there a version of the news from where you grew up that you consciously want informed.now to feel like, or feel nothing like?

Kira Shishkin: All of it, frankly. The sensationalism that has corrupted news media in Ukraine and Israel, and also globally, is probably what we are most trying to fight. Bias is definitely a sin, and it's terrible, and I think it hurts society to a great degree. Look at what it's doing to American society. The hyperpolarization that we live in today in the United States isn't an accident, and it isn't something that just coexists with news media. It is directly facilitated, and in many ways directly fabricated, by the news media of today. To me, it's tragic.

But even more important than the bias problem is the sensationalism problem. It matters a lot more than Fox News having one opinion, CNN having another, and the New York Times having another. It's not about that. I think that alone is something we can live with, and in fact we have lived with it. But the proliferation of sensationalism across every flavor of news media is, to me, the most unacceptable trend. It has been reinforced by social media, which only cares about hype and virality and does not care about accuracy, and by AI, which can produce sensationalized content at a very fast pace.

We now find ourselves in a world where even the most credible news publications resort to some of the lowest clickbait tactics on a daily basis. These are folks that I used to admire, and I'd say, wow, this is real news and the other guys are not real news. Now I look at their pages, I look at their print, I also look at print all the time, and all I see is clickbait. It's no wonder that the word of the year from Oxford Dictionaries this year is ragebait, which is very telling of the world we live in, and that's something we are fighting very hard against.

Rohit Malhotra: Interesting. And Kira, you also advise primary venture partners. What do you look for in a founder before you advise them or back them, especially in investing and advising?

Kira Shishkin: Beyond the advisory role, I've spent years in venture and a lot of time looking at companies through my own vehicle, supporting a range of entrepreneurs from the earlier stages to growth stages. To me, what matters the most is the founder's or the founding team's understanding of the customer. There's no other way to say it: If you don't know your customer, you don't know what you're doing. If you know your customer really well, it doesn't matter what you're doing. If you understand what the customer needs and wants, then even if your current product iteration isn't the right product, your ability to pivot and move around is going to be empowered. If you understand the person that you're serving, their needs, what they do, and how they think, that is really priceless.

A lot of the founders that wind up failing do not fully understand the user, the target customer that they serve. A lot of the founders that do understand their target customer wind up getting it within the first, second, third, or fourth iteration, but they get it within the same company, within the same venture.

Rohit Malhotra: Correct. And what advice would you give to portfolio founders that you don't always follow yourself but would want them to follow?

Kira Shishkin: It's a great question. There's a lot of advice that I wish I followed that I don't. Certainly doing more customer research, being closer to the customer, is always a no-brainer, and I feel like I'm never doing it enough. I have a complex that I need to do more and more of it, because it's such a big part of my vision of what makes a good venture. So spending more time with your customer, more time with the user, not worrying about whether that's scalable or not, but just doing it, is really powerful.

Another thing I'm trying to implement on my team, something I care about even at the intern level, is that I want every single person in the company to have customer interactions. If you're doing engineering, product development, research, competitive research, or finance, no matter what you're doing at the company, I want you to have some kind of exposure to our customer. If your job is purely internal, that obviously doesn't mean you're going to the front lines or you have to do sales.

What I'd love to institute, and what we're actively bringing to our team, is that every month there's either an event that everyone does, almost like a call marathon, or almost like a quota where you have to call 3 customers and just have a conversation with them. Ask them, how are you doing, how are we doing, is there anything you'd like to improve, anything you'd like to change? Engaging that feedback personally means even the finance person, the data person, and the market intelligence person who isn't in a customer-facing role has a direct pulse on who it is that we work for and who it is that we serve, and that is always our reader.

Rohit Malhotra: Right. And Kira, you mentioned that you've been on the investment side of the business. How does sitting on the investor side change how you run your company? Are there any lessons that you learned before you started your business?

Kira Shishkin: You get to see a lot of failures, a lot of things that are not the things to do, and I think it helps you selectively. There's a saying: Being smart is about being able to learn from your mistakes, and being wise is about being able to learn from the mistakes of others. I'm always trying to embody that, to the extent that I can.

When you come from the investing side and you've seen hundreds of thousands of business proposals, plans, and opportunities, and you see why you wouldn't invest in this one, why the one you invested in failed, why this one succeeded and why this one failed, you have a lot more data points to avoid decisions and directions that you'd otherwise have to learn for yourself. Frankly, we don't have enough time in the world to make all the mistakes that are out there to be made. It's about learning, to the extent that's possible, from the mistakes of others. If those 30 companies all failed doing the same thing, how can we avoid doing that thing? That lens definitely comes from the investment background, from spending a few years in venture and being exposed to a lot of case studies.

Rohit Malhotra: Got it. And if informed.now succeeds completely, what does the news industry look like in the next 10 years?

Kira Shishkin: It's a great question. With the advent and proliferation of AI into everything, I think we are years, if not months, away from being in a place where reading news without an AI filter, or without some kind of filter, is going to be impossible. I think those floodgates are already being opened. We're entering a world in media where the amount of noise, information overload, and misinformation overload is so intense and so overwhelming that it's soon going to be impossible for anybody to read news in the old, traditional way. Every reader is going to have to build, buy, rent, or somehow develop a filter for the information they let through and the information they do not let through.

In some ways, we are early to this game, because we are creating a filter for people who are seeking it, and we're doing it with our own approach. In the next couple of years, success for us looks like becoming a default alternative for a new generation of news readers. But we will also see a lot of companies similar to ours emerge to build those guards and those filters, so that people can navigate an age of misinformation overload with a lot more confidence and a lot more clarity, and not be drowned in the noise that surrounds us. It keeps getting louder.

Rohit Malhotra: Interesting. And Kira, I quickly want to do the top 3. What's your favorite business book?

Kira Shishkin: My favorite business book is a business story. It isn't a how-to book, and it isn't a book that gives a lot of advice, but in reading the story you wind up learning a lot about the way these great businessmen thought. It's a fascinating narrative. It's an early 2000s book, I want to say 2002 or 2004, and it's called Inside Intuit. It's a story collected through a range of interviews with the founders, the CEOs, and generations of leadership of Intuit, which is a publicly traded technology conglomerate on the US stock market and, frankly, one of the oldest technology companies in the world. It was built in 1983 or 1984, so it's turning 42 or 43 this year. Pretty impressive.

What you see is a great narrative of business thinking, of keeping the customer first and doing right by the customer. I definitely learned a lot about customer love and customer empathy from that book. It was great to read because I also spent a few years working at Intuit, so I could couple my reading of the book with being at the company, living it out, and seeing the story continue.

Rohit Malhotra: Interesting. We're going to put that in the show notes. If you could go back in time to when you started informed.now, what is the one thing you would have focused on or done differently?

Kira Shishkin: There are so many things that we had to get wrong, because there were no playbooks to follow. We're building something pretty unique. There aren't a lot of companies that do what we do. In fact, there are practically none. So there weren't a lot of playbooks, and there are a lot of mistakes that we had to make that we couldn't have learned from somebody else.

What would I do differently? I'd make decisions faster. There were hiring decisions and partnership decisions, and overall a range of decisions, and I think partnership and hiring were probably the biggest, where the obvious choice was available much sooner, but instead I dragged my feet and moved too slow and too indecisively. I think that has cost us months. I don't think it cost us years, but it definitely cost us some months and maybe even some quarters. If I could go back with some hindsight, I would just make faster decisions: faster hiring, faster firing, faster partnerships, faster cancellations of partnerships. I'd move a little bit quicker with conviction, rather than thinking, maybe it's going to change next month, or maybe this is just a bad month for this partnership. A lot of decisions are staring you right in the face, and you just have to have the conviction to say yes or to say no.

Rohit Malhotra: Okay, got it. Makes sense. Do you have any favorite online tools? For example, Gmail, Slack, Zoom, Claude.

Kira Shishkin: It's funny you mention that, because I am a really big fan of Google Drive and the whole Google Workspace. I think people underestimate its power because they neglect to learn all the shortcuts and all the tips and tricks that are available within it. Google Workspace can run your entire company at a huge scale. We used Google Workspace when I was at Intuit, which is a gigantic company, and we're using Google Workspace now at informed.now, a tiny startup in comparison. I think it's incredible.

One that is less obvious is Loom. I'm a really big fan of Loom by Atlassian, another technology conglomerate. It's a very simple product, and the work that they do has saved us tons of institutional knowledge that would otherwise have to be shared manually or through word of mouth. We've been able to document it through videos and screen walkthroughs. It's been really incredible how simple that is, and how effective at the same time. So Loom may be my number one as of today.

Rohit Malhotra: Interesting. Yeah, as I've been in sales and business development, Loom is also one of my favorite tools. We'll put that in the show notes. And what's the best way people can reach out to you and learn more about informed.now?

Kira Shishkin: Our name is also our website, so informed.now is a great way to learn more about our mission and to sign up. We run a completely free product. There is a premium version, and you can always become a contributing reader, but the power of facts is accessible to everybody for free, forever, and that's something we take a lot of pride in and care a lot about. You can sign up for free at informed.now. The best way to reach me is probably LinkedIn. I'm on every social media, but LinkedIn is where I spend more time.

Rohit Malhotra: Got it. We're going to pull that into the show notes. Kira, thank you so much for taking your time and speaking to us. I really enjoyed my conversation with you.

Kira Shishkin: Rohit, it's been a pleasure. Thank you for having me.