How to Find a Billion-Dollar Startup Idea

Listen or watch on Super Entrepreneurs Podcast, YouTube, Spotify, Apple Podcasts, Amazon Music, Pocket Casts, Castro, Poddtoppen, iHeartRadio, TuneIn, and Audible.

Highlights

Kira tells Shahid Durrani about the day he looked at the managing directors above him in finance and decided to get off the train. Customer obsession, a habit he built on a 5-person team at Intuit, runs through his advice: Talking to 30 people a week about an idea, shipping before a product is ready, and never telling investors you have no competition.

Top Quotes

"We think of real news as what's left behind when you strip away all its surrounding chatter and commentary." (Kira Shishkin)

"Before I got into studying the mind, I always had this underlying feeling that I was getting programmed." (Shahid Durrani)

"Founders who say 'we have no competition' raise one of the biggest red flags you could show an investor, because it signals that you're unaware of your market." (Kira Shishkin)

Transcript

Shahid Durrani: Welcome to Super Entrepreneurs Podcast. I'm your host, Shahid Durrani. Today we have with us Kira Shishkin. Kira has built 4 companies, scaled a 9 figure marketplace inside Intuit, and now runs informed.now, one of the fastest growing SMS-first news platforms. Welcome to our show, Kira.

Kira Shishkin: Wow, Shahid, thank you for welcoming me. It means a lot to be here. Thank you for that generous intro.

Shahid Durrani: No problem at all. So excited to talk to you. I love hearing what goes on within a human being to achieve what you have achieved, and to find areas where we could try to mimic it, or get ideas where others could also follow your steps and create for our fellow human beings. Because the more we innovate, the more we create, the more entrepreneurship we have out there, the better the world will be, I think.

So can you take me back to the moment when you realized, if I stayed in finance, I already know what's going to happen? What's my end? Did that realization feel like a new identity in a way? Could you share that moment with us?

Kira Shishkin: I love that you zoom into that specific moment in time, because I do think it was very memorable for me. I actually remember that specific day, and it was a very simple realization. I essentially said, okay, well, if I continue on the trajectory that I am working in, I'm going to have the life of the people that I currently look up to, right? The managing partners, the managing directors, which is what we call them in the finance world. Or even at best, perhaps, the owner of the company, or someone who is very senior in a finance career.

When I looked at them, I started to dissect their life. Would I be happy if I had their life? And frankly, I thought, well, look, actually no, I don't think I would be satisfied at all. I don't think I would be satisfied with the impact or with the freedom, because you may have financial freedom, but then you still have a lot of obligations, so to speak, that bind you in different ways and still prevent you from being free, although you have the financial freedom.

So I looked at the lives of my seniors at the time and I said, you know what, I don't look forward to this life. I'm heading in that direction right now, so I'd better get off the train if I don't like the next stop. And that for me was a realization that that's not it. I wasn't sure what it was, but I definitely knew that finance was a no for me. It's a great domain to be in when you don't know what you want. Once you start figuring that out, it's great not to overstay.

Shahid Durrani: Yeah. And you said, for not knowing what you want. Is that around the same time that you realized you wanted something bigger, or did you realize you wanted something with precision? Did you know what you actually wanted?

Kira Shishkin: I've never had a specific idea like, oh, I want to be an entrepreneur at the intersection of technology and media, thinking about world news, thinking about information overload as a problem. I never had that level of specificity. But I've always had a pulling toward entrepreneurialism, which is the instinct of observing problems and trying to articulate solutions to solve them. I feel like I've had that in me from a very young age. My very first business was actually in book publishing. To me, that has been more or less certain, and other people saw it too.

In the early stages of my career, I was doing various jobs, and a lot of my managers and bosses would tell me, "Hey, why don't you start something of your own? Why are you here?" I really appreciated that. It used to freak me out. I used to be like, "Oh my god, am I about to get fired?" But over time it gave me the confidence that they agreed my talent, my drive, and my sense of self are better expressed through entrepreneurialism, through observing problems and trying to articulate solutions.

Then informed.now, my current big focus, was an independent force that came to me and hit me out of nowhere. Throughout my life, especially my childhood, part of my personal journey was trying to reclaim focus. I was part of an accident as a kid that left me mentally experiencing disability for many years. I couldn't really concentrate. I couldn't wield my attention. At the same time, I was observing the decay of the political conversation, the cultural conversation, and the social conversation in America.

I've always blamed the news narrative for that decay, because news has become unreadable, undigestible, and very toxic. Those two observations, coupled with the entrepreneurial drive, made me think, "Wow, I want to build a solution in the space of reimagining news, because there's a real problem, both from the attention side and from the polarized content side." That pushed me to launch informed.now.

Shahid Durrani: Yeah, that's awesome. Thank you so much for sharing. With all the details, I could put myself in that time frame and sense what was happening. And that was a really good point you made about news. Before I got into studying the mind, I always had this underlying feeling that I was getting programmed. I just felt like I was guided to do certain things. I remember I used to watch Saturday Night Live when I was in my teens, and the commercials would come on. A medicine commercial would say you're literally going to die in the coming minutes if you don't do something about this, right? That started working on me.

Later, as I studied the internal world, I noticed there's so much promotion of fear to push people in a direction, toward a specific group or idea that wants you to follow, and it's usually around fear. That's how they get you, subconsciously. Can you share what you're doing differently at informed.now? You were mentioning that the news was too one-sided. How are you sharing the news that is already being publicly shared in that manner?

Kira Shishkin: I love that you pointed out the fear element, because I think it's one of the most widespread and most common tricks of the legacy news media industry. It's that and anger. Fear and anger are strong, and they're viral emotions. If you're feeling joy, it isn't as viral. When you're feeling fear, you're going to go tell your mother, your sister, your spouse, your friends, "Hey guys, I'm afraid, maybe you should also be afraid," or maybe you want to get comforted. Same with anger: "I'm angry. Be angry with me."

Other emotions, especially the more positive ones, aren't as contagious. Even laughter, when you experience it, is hard to pass on. It's very momentary, very ephemeral. It's frustrating that some of the most viral emotions are also some of the most toxic. But the legacy news industry has pushed them down on us for as long as it has existed. When you look at the front page of a newspaper, whether in physical paper copy or as a landing page online, it tends to be very provoking, agitating, galvanizing, and really pushy. "Hey, you won't believe what happened. You should be angry. They did this. They're tricking you."

It's terrible, because when you read news, you come to be informed, not influenced. And all the news that is served to us, definitely in America, is full of this intent to influence. Whether that's to influence you to have a certain reaction, a certain political opinion, or a policy opinion, or to influence you to buy something, it's a solicitation type of influence. It's ceaseless, it's structural, and it's so hard to undo in this industry.

So how do we tackle this, to honor your question more directly? We strip the news down to its core essentials. We think of news as what is left behind when you take away all the discussion and all the commentary. It's the fact base of what happened. News should answer the following questions: What happened, when did it happen, where did it happen, who did it happen to, and what is the immediate context that you need to understand? Very immediate context. And that's it. It takes a paragraph to relate these things. Sometimes it takes even less than that. That's news.

But then you open an article, maybe from CNN, maybe from Fox News, maybe from CNBC, maybe from the New York Times, and it's so long. You wonder where they got 16 paragraphs of content about this one little event. They bring in all these people: "We talked to the person outside. Here's the person outside. What do you think?" "Okay, it's really bad out here, but back over to you in the office." There's this whole kind of discussion acrobatics that inadvertently influences you to have an emotional response of agreement, disagreement, outrage, or fear, or "Oh, I agree with this, this is what I believe."

That emotional trip you go on shouldn't happen when you're reading news. That should happen when you're watching a movie, when you're being entertained. When you're reading the news, you should just get the facts, those essentials we strip down to. That's our minimalism. We call it news mindfulness, a news minimalism, a media approach.

Shahid Durrani: So you're becoming aware of what's happening without the human trigger of emotions taking it in a direction, maybe positive or negative, it doesn't matter. Taking people in a direction that others want them to go emotionally. Instead of that, we're just giving you exactly what you need as a fact to understand what's happening and then move on. Or if you need to do something about it, you do something about it, but it's just to the point.

Kira Shishkin: We're trying to honor and enable people's ability to make up their own mind. That's the power of having facts: you get to make up your own mind, and here are the ingredients to do that. The current media industry doesn't share its ingredients. As an everyday person, you don't ever get access to just the facts themselves. First of all, you only get access to news commentary, not to news itself.

Most of what Americans think of when they hear the word news is actually not news. It's news discussion. It's news commentary. It's a talking head on TV telling you some story of what's going on. It's them talking between each other. It's really like 99% discussion. And the reporting of the facts themselves is practically inaccessible to the everyday American. A lot of the rich professional elites have access to it. There are information services that are meant to inform you, but they're very expensive and come with annual commitments, and generally an everyday person can't afford these subscriptions and services. We are democratizing access to that level of presidential briefing for the everyday person, because everyday persons should have that power.

Shahid Durrani: Yeah, that's excellent. That's awesome. So you've built, in the past, 4 different companies in crypto and, like you mentioned, publishing, tech, and informed.now. Can you share the binding, invisible thread that connects them all? What is your thing that you bring to the table to make these things successful?

Kira Shishkin: There are a few things that I take very seriously, but I think the most important is what I call customer obsession. I got this term from my time at Intuit, and I think it was a perfect way to describe this approach. Instead of listening to your own gut around what you think is best for the customer, customer obsession is the art of putting the customer on the pedestal and creating a communication channel that enables you to hear them, understand what they want and what they need, and build for that. You can think of it as a research approach. You can think of it as a product strategy or a company strategy around letting the user, the customer, the client, no matter what you call them, guide you.

It's a matter of setting up a process of discovering the problem they face and getting really specific on it, so you can walk in their shoes and empathize with the problem they experience. The problem obviously varies across the different ventures I've been part of. With informed.now, it's very much the problem of "I can't read news because it takes too much time. It takes too much time for me to read all these things to find what I'm looking for, which is high-fidelity signal, what's actually going on. I don't want to read news because it's biased. I don't want to read news because it's clickbait and sensationalized, and I don't like ads in news."

These are all problems that I may have experienced myself personally, but it's not enough to experience it yourself. It needs to be checked, and you need to find resonance with a much broader community of people. You can call it user testing, you can call it need validation, but adopting the customer-obsessed approach means having as many conversations with customers as you can, hearing their problems, going through those pains, documenting them, analyzing them, and synthesizing them. That obsession with the customer's experience, with what problem they want to solve, is the running thread across every company, and I swear by it.

Shahid Durrani: Yeah, no, that's good. And now there are many platforms that you can ask for help to get a deep dive on your target audience. There are a lot of tools, especially with AI now, that people can use to gather this information. But you're right, because we're human and we can tend to just go based on emotional feelings about an idea and go all in, without studying the market to that depth, to understand where they stand and what you're offering. That's clarity on the next level, and that's only going to help you, right?

Kira Shishkin: And it's the only thing there is. There is no shortcut to understanding your customer's problem, and making up a shortcut for it is only going to waste your time. At the end of the day, everything else you do is just trying to guess the customer's need. You're going to be talking to experts, maybe hiring coaches, maybe reading books, doing all these things. All of those are proxies for actually having a direct line of communication with the user, where you can have those conversations at scale. It could be surveys, it could be conversations, it could be one-on-one interviews, where at scale you're able to understand and have open feedback loops: What is your problem? Is this solving it? How can this be better?

And it doesn't stop at the beginning. It doesn't stop when you're validating an idea. It continues, and it cannot stop as you grow the company and as it continues to evolve. You need to keep a direct pulse check on the customer at every single point, and when you start losing that, you start losing your grip on the business.

Shahid Durrani: Thank you so much for sharing that. It makes complete sense. If I have a startup idea, I can share it with you.

Kira Shishkin: Please. And you should tell your startup idea to at least 30 people per week and ask, "Do you have these problems? Are you experiencing this? Do you know anyone else who may be experiencing this problem?" Because building for one person, yourself, is not building a business. That's building a toy. You need to see if there is resonance across larger groups of people. And it's free. It doesn't cost you anything to go out in the world, get on calls, talk to your friends, talk to your family, and grow that group of people you're testing with. "Do you have trouble with this thing? Can you tell me about the last time you did your taxes? Was that difficult? What was so hard about it? Or the last time you bought a shirt, was it annoying? Was it too expensive?" Ask about those experiences with an open-ended ear.

Shahid Durrani: So, at Intuit, you helped build or hit 9 figure ARR. Can you share what actually happened in the first 90 days? Any specific actions, any strategic movement that was put in place to achieve that growth that you experienced? Not theory, but any kind of steps that you can share.

Kira Shishkin: What I just mentioned was at the core of it. I was on a team of 5 people, and we were getting on calls with the users. We were talking to them, documenting what we were learning, and trying to see patterns: What are people saying that is the same? We were trying to really test. We even flew in person to meet a couple of different target groups and had those conversations, trying to figure out whether we could fully understand, empathize with, and embody this problem. So customer obsession was a very core approach. But I've talked about it at length already, so I'll mention another thing that was important for us.

It was more of a tactical choice, and it was really about shipping, which is what we call, at least in the tech world, deploying or publishing a product. It was about publishing a product before it's ready. You can wait for weeks or months until it's perfect, at which point it's going to be too late and you might miss the momentum you were building. Or you can have something that's half-baked or clearly not ready, that looks ugly, that looks like a Frankenstein, but you ship it right away. You publish it right away, so you can start the live feedback loop right away.

I think that is really important, specifically around getting to customer insight as quickly as you can, because while the idea is in your head, it's fake. It doesn't exist. It's completely a fantasy. You need to publish it to the market, to the user. It feels uncomfortable. I'm a perfectionist, so this hurts me more than anyone. You feel uncomfortable publishing something that's not ready, that you know is a quarter of what it could be. But you have to do it, because until you publish it, you won't get real feedback and real testing. Shipping before you're ready is a necessary discipline that an early stage venture just has to adopt. You cannot be cradling your baby until it's ready. It's going to be too late, and it's not going to help your baby walk.

You need to be okay with the cringe, okay with the embarrassment, even the shame, of shipping an unready product, because the people who will give you reactions are people who say, "I wish this existed. I wish this product was good." If they care that much, it's giving you a lot of information about who the target customer is. You share a product and, for example, college girls are not reacting to it, but early career men in finance are reacting really well. They say, "Hey, this is really ugly. Can you fix this?" You're getting signals that the people who care about your product are being identified. That's just one of the many values of shipping early.

Shahid Durrani: No, excellent, excellent point. Definitely we all need to step out of the way when it comes to this type of research and not get affected by the feedback. Even if something needs to be changed, at times in a large aspect of what you thought was going to work, you could completely change with that type of research and feedback. So being open to that is very important as well. You said in the past that you were lazy but smart. Can you share what systems you built that saved you so much time that it felt wrong?

Kira Shishkin: Well, I would say you definitely want to design systems for you to become redundant. If you're designing a system that requires you to be part of it, you're not really saving yourself time. You may be reducing time a little bit, but you're not going to be able to move on from that process and hand it off. Every hire you make, every process you orchestrate, has the goal of making you redundant, because if you cannot leave this process, whether it's an editorial process, a technological process, or some sort of operations process, you're not really benefiting from it. The goal is for you to be able to step away. The goal is for the team to be able to own it.

So generally I think of every process this way: My goal is to make myself redundant and unnecessary. I don't need to approve it. I don't need to be part of it. That is critical. That's definitely the mindset you should bring. A lot of people don't think of delegation that way. They think, "Okay, you're going to help me with these things, but I'm still in charge." Well, hey, no one's challenging your bossiness. You can still be in charge, but you're not going to do yourself a favor if you are limbically attached to the operation. You need to be able to hand it off.

Another point is just my framework, and I don't think it works for everyone. It also depends on the business. I try to hire for things, and operationalize things within my team, that I already know how to do. For example, if it's a process that I'm already really good at, I want to hand that one off, because one, I know how to evaluate whether it's being done well, since I know exactly how to do it. I can train the person, I can move on to learning something new and growing somewhere else, and I can have the confidence that if something breaks, I can help the person I gave the process to, because I know how to do it.

So I love handing over processes that I'm really good at, instead of trying to hire for things I don't know how to do. Then I don't know how to train the person. I don't know how to supervise or assess quality. And if they get sick and I need to step in and help, I can't, because I have no idea how to do it. So I always focus on hiring for things I'm already proficient at, and then going to learn that new skill and adopt it myself. These are my two thoughts on creating lazy processes. First, always think of making yourself redundant, to the extent that the team can not just operate independently but also teach new members of the team how to onboard into the process. You shouldn't have to retrain the person personally; the team should be able to do that. Second, hire for things you know how to do well, because that will help you train and assess quality.

Shahid Durrani: You don't want to take the leadership role if you don't know what it's about for that aspect of what you're trying to implement. That's so important. Otherwise you're going to be asking another expert to help you with that as well, right? You also raised 30 million in the past. What do first-time founders usually get wrong when talking to investors, especially if they're non-technical?

Kira Shishkin: I would definitely say it's all about the customer obsession piece. When I look at pitches and talk to teams as an investor, but also from my experiences with much more sophisticated institutional, legacy investors, they're trying to assess how well you understand the problem. Along with that, how do you understand the market? If you're unaware of the market you exist in, that's a problem. Founders who say "we have no competition" raise one of the biggest red flags you could ever show an investor, because it signals that you're unaware of your market.

With a couple of drill down questions, and the investor doesn't even have to be an expert in the field, just asking a few follow-up questions about the customer's problem, you can quickly figure out whether the founder or the founding team understands the problem they're trying to solve. If they do, and they understand the market they exist in, that's a very strong start, because if you have the understanding, things become much more obvious.

A lot of founders get obsessed with an idea, and they may be technologically savvy, so they go and build something, but they have not tested the demand for this solution with their customer. They have not tested the demand side, and often they have not tested the supply side, meaning what solutions are already doing this well. You get both of those strains of knowledge just by talking to the target users you're looking to serve. But so many founders neglect that. That's also part of the customer obsession canon: falling in love with the user and falling in love with their problems. That's what makes you a great founder, not your ability to code an application. That is a commodity skill that is no longer unique. Anyone can now code an application. There are tools, and it's not hard. But the thing that's still irreplaceable is your insight into the problem and into the market, your understanding of it.

Shahid Durrani: Yeah. And with AI it makes things much easier to achieve. When you were doing it, you probably had to do a lot of it manually, right?

Kira Shishkin: AI would help you with the literature research. It would help you with synthesizing information.

Shahid Durrani: Even the data you get back from people, right? You can feed that in.

Kira Shishkin: Especially data, right. It will help you do a lot of research. Large language models, which are the predominant models of this AI era that we all call AI, are what we're primarily talking about, LLMs. They're excellent at regurgitating content, and they're great at analyzing written text. But the work of doing interviews, running surveys, and doing various types of tests with users is still very much a human art. There might be more tools now than ever, but you need to have your own strategy for how you validate an idea. That's not something that can be fully outsourced.

Shahid Durrani: The human presence is very important in that. Well said. Thank you, Kira. I appreciate you coming on our show today and sharing the wisdom. Hopefully we added value in the world. And if there's anything else you want to share before we end, please go ahead.

Kira Shishkin: First of all, thank you for welcoming me on the show. I hope that some of this customer obsession gospel resonates with folks, and I'm happy to share more. I'm an open book about my ventures and my experiences. My current focus is informed.now, which is both our brand name and our website. If anyone is interested in news mindfulness and media mindfulness more generally, we're always looking for feedback. We're always looking to test with our users, which is ultimately what I'm always optimizing for. So we welcome folks to give us feedback. Go to our website and see. I would love to get your reaction at informed.now.

Shahid Durrani: That's so amazing, how you shared that. And to the audience, you can see informed.now is already launched. People are already signed up for it, and he's still presenting it in the format of "test it, check it out, let me know what you think of it." Even at this stage, he's still incorporating the client base. You can sense the whole ecosystem of his world when it comes to startups.

Kira Shishkin: This is one of the biggest learnings from my time at Intuit, where we incubated the previous company that I worked on. Intuit is 40 years old as a public company. That's older than mass adoption of the computer. That's older than the iPhone. It's older than software without CDs. That company has been through every technological, internet revolution. It's a pre-internet company, and it's been around for a long time. When I talk with Intuit leaders and we work together, I ask how they are able to stay afloat and continue to lead the markets they're in. The single answer is exactly that. It's not initial, it's not temporary. It's a continuous obsession with the customer's problem and a continuous discovery.

So now we're a pretty mature product. We've been in market for a substantial amount of time, but we're still testing. We're still improving, and we're always keeping that channel open, because if that channel closes, our time is limited. If that channel of communication and understanding of the customer shuts down, it's a matter of time.

Shahid Durrani: It has to be part of it throughout the journey of the company.

Kira Shishkin: It's like the company stops breathing. It's like the blood flow stops running through the company's veins, and you cannot let that go. It's critical.

Shahid Durrani: Thank you, Kira. It was great talking to you, my friend. Keep in touch. I appreciate your time today.

Kira Shishkin: Shahid, thank you so much for having me. It has been delightful.