Transcript: Simplified.co: Co-Founder Ajay Yadav on Scaling, Building in Public & More

This episode of Startup Project is brought to you by Bear.Tax. Bear.Tax compiles all your crypto transactions and makes it easy for you to file your taxes. Check out bear.tax. That is b e a r dot t a x. Bear.Tax. Hey Ajai, welcome to the show. Thank you for having me, Atrey. So, one of the interesting things uh with the with doing a podcast is like you you have familiar people as your guests and then you can ask them questions that you would otherwise not ask uh in a regular conversation. So, I thought an interesting place to start is to talk about, you know, your journey from India to US. I think I never asked you about, you know, how your journey started before Rumi, uh your first company. So, I think that would be a good place to start, you know, how and when you came to US and, you know, what was your journey before Rumi like? Uh man, I mean, I think kind of crazy, right? I mean, every entrepreneur would would want to say, of course, failures before anything, but um, I actually did fail in uh I failed in my high school twice. That's that's setting the stage for me kind of moving to the states. Um, so senior high school, you know, 12th grade in India. So I failed twice and third time sort of my dad was like fed up and he kind of knew, I think that um, you know, it was hard to compete. I mean, I wasn't in you know, Z IIT programs, right? I think. And he was like, you know, if you if you um finally uh pass, you know, then uh hopefully you should just go out basically. And that was the stage. So I finally uh passed my senior high school by margin. Applied to bunch of schools, luckily got in and yeah, moved to the states, man. That was almost damn 16 plus years ago. Um for computer science uh undergrad program. So you moved uh as a student. Yes, I did, yes. Got it. And uh so let's talk about Rumi, your first company, right? Uh How did the, you know, idea came and uh was this in college or post college? Rumi was, um, you know, when I first moved out here, I remember 2000 6-ish. 2007 actually, I I started um tinkering with a bunch of ideas and I actually built the first uh like a dev shop, you know, from India and then building uh just websites for other people. So basically I was in the states. So here in New York, I would go around like gyms, you know, local gyms and ask him, hey, if they don't have a website, I'll build one for them. That's how I started building kind of like the website and from their website end up building like 200 projects and um build like a whole kind of company around it. Uh and then a couple of years in played with a bunch of ideas and then build an online classifieds company. So I built actually a replica or let's say was trying to copy Craigslist. But of course, a much better version like soleka.com or something in India. I did that for for a while and Rumi, I'd say was like my kind of first real uh and like venture back, venture back, typical kind of like a startup you would imagine. Yes, that was the first one. End up working on it in 2012 and it kind of came from my own pain points of, you know, finding a roommate, you know, looking at a bunch of, you know, profiles or visiting places and trying to figure out who's the right fit. And build that, um and ran that for roughly nine years. Yeah. So, one of the things I think in one of our conversations is where you mentioned, you know, the fundraising part of Rumi. Uh and obviously now you're uh doing simplified uh post Rumi. How was it different from, you know, raising funds for Rumi versus now raising for uh you know, you know, venture capital for simplified. You know, I think Atrey, I mean overall, I think everything is different, you know, when they're saying first time founders versus the repeat founders and who've done this before basically the statement is, right? You you make a lot of mistakes and I made ton of mistakes, more than I can even remember. And raising capital was one of them, you know, I think sort of like the had no idea, no connection, no network. So I pitched hundreds and hundreds of people before I got my first check. And it was always like just begging for money, always just getting out there, always pitching and the kind of the approach was it's like almost like you can how many doors uh can you like knock on, right? Like that's the approach. Like if I pitch thousand people, hopefully I'll find like 10 or 20 that believe in me and the company and they'll give me the money. So that was the approach with Rumi, very, very different than what I'm doing now with simplified. Um yeah, so it's brutal, uh time-taking. I was always raising capital. So it just always takes the space. Uh operating versus capital, it's always like operating and capital and it's just super hard. Just purely talking about the landscape, right? Like what has changed in terms of landscape according to your perspective from then to now? You know, I mean, this time raising capital for simplified has been, I wouldn't say like easier or easy, but I think it's been a different experience, you know, and I think it's because of repeat founders who've done this before, made a lot of mistakes before and built the network, right? Like we know people. And I think what we have shown people what we can do, we know if we can can we operate? So I think there's a lot of money out there for absolutely, of course, like new founders and new ideas and new start. But also there's a lot of money for repeat founders. I think and I see as a repeat founder, it's just a little bit easier than the first time because of the network you have and you can prove yourself, you can execute faster, right? You at the end of the day you can show, I can I have an idea and I can get it done. But there's definitely too much money out there and we're seeing like, you know, um all types of VCs, right? Like brand new VCs coming out. One of the biggest change I've seen is like a single GP, right? I never saw that before. Single GP funds and these indie funds coming out. A lot of the founder led funds are coming out. I mean Angeles has taken over. So there's definitely massive amounts of capital out there to be deployed into different types of companies. Yeah, uh so I think one of the things with simplified that I noticed which is which works really well when companies are raising is the separation of responsibilities. Like for example, this is my observation like you are sort of forefront uh and you can correct me if you're if I'm wrong, is that you are the forefront of certain things, especially fundraising and sort of the building in public side of simplified versus I see Katie as the CEO who is, you know, focused on the product and, you know, tech side of things. Uh, and what I've also noticed in, you know, people who raise successfully while building parallel is this clear separation of uh responsibilities and in the very early initial team, especially between the, you know, CEO, CFO, COO, uh I mean the the terms don't matter that much initially, but the responsibilities and the time management aspect of it and who's good at what, I think that separation at least for us as an investors, uh was a clear indication which is a good team versus which is a bad team. Um Yeah. Yeah, really interesting point you made out here and I think, you know, so I I was a solo founder all of my life. I mean so far three companies. Uh just built myself. Not by like choice, just by, you know, no resources basically. I had no idea. I didn't know anyone. Send up just building it myself. But being here with a co-founder, I think is hands down one of the best things uh given you have the right co-founder. You know, I've known Katie for been friends for a very long time, six, seven years at least. And when we first entered into this with the partnership, we were like, you know what, we should define our swim lanes. I think the same concept you're kind of noting to that hey, you know, you know, what we're good at and so it's like a complimentary skill, not the same exact skill. even though we have both done almost everything, right? But some things are heavier on one side than the other one and I think product naturally has been of course his background and um how he build amazing products. On for me and the same thing, I think on the other side like operating and expanding and raising and of course like uh finance, all that kind of stuff, right? I think been closer to than the other side. But um, you're right. so we're dividing those roles, but for fundraising actually what we do, we do it together actually. Because we both bring in the network together, but we definitely divide and conquer in terms of like who's taking that meeting, who's taking this meeting. The good thing is whoever we're pitching and if we're pitching from let's say you know someone, then I don't have to go in. Like I know you got this. I think that's the divide and conquer, the trust we both have and the partnership we both kind of like have built. Like go and close it. And when they need us both to be there, then we both go and kind of like close the deal, whatnot. But yes, there's very clear separation and what uh Katie is doing and leading and what am I I'm doing so we can be more very effective and just execute. The the end goal here is just to kind of keep shipping and keep executing and keep telling the story. One of the uh other interesting things about simplified and your journey has been, you were investor before, you know, becoming, you know, co-founder and CEO of simplified. So when you were sort of evaluating your next gig and what made you think that simplified is a large opportunity for you to, you know, you know be part of because committing to a new company is sort of, you know, seven to 10 year journey, right? So what was the evaluation process like, you know, uh in terms of just market size, opportunity and is it worth your next seven to 10 years of uh time? You know, um I actually wasn't planning to join any company at all, you know, I think my move was I was more actively getting into investing, you know, I've been investing as an angel for a while and I think the goal was to start something in in the in the Fintech space. I love Fintech. I think there's a lot of problems that needs to be solved in the Fintech world, you know, access to capital and I think how people get paid and whatnot. But when simplified, you know, after investing in the company in the first round, I was of course closer to it. I was definitely spending more time with Katie and what I started to realize that this was also the time when you know, people were telling more stories and consuming more content. And naturally, I think for the past couple of years, I'm really big on like kind of like sharing stories and just building a brand online and kind of sharing a journey. So sharing a journey is like telling a story and I think simplified was making it easier for anyone to tell their story by creating content and making it very, very easy to create content at scale as well. And for a very cost effective, in in a very cost effective way as well. So I think all those things kind of resonated with me like personally and in a way kind of to assess the opportunity was the Tam. And I think this is one of the things that I've learned is if you have a good idea, definitely assess are you playing the big game in a really, really, really big market. And I think content creation and marketing is a humongous market. I mean if you look at Adobe and Canva, that was my like two points like damn, Adobe's sitting at 240 billion and it can only go up. It is going up. Canva is barely getting started already at 40 billion it's only going to go up, right? Recently we've seen Miro to click up to all these amazing tools that have kind of come out either to help you create more or manage sort of like the project management stuff. So man, I just knew it. This is like the opportunity of a lifetime and I think I'm willing to spend not even one, I think two decades of my life with the right partners kind of build this company. I think the way I looked at it is if you just go into web, every second second you're on web, there's an image or a video popping up and that's where and every image or video is made by someone, somewhere using a tool. So the the Tam is potentially a percentage of web activity in the whole, right? Because it's not just about marketing anymore, it's about any knowledge worker anyways is indirectly or directly interacting with content in some way. content has become you know, purely you know, there used to be a time when marketing used to be different from a company. So marketing used to be there's a special operations of marketing which is not owned by the company itself. Now we're moving more in towards content marketing where everything has to be in a form of a story and you need tools to tell that story. So I was always imagining this Tam as a percentage of web activity because pretty much any two seconds you're on the web, you're interacting with an image that is manufactured, not by a camera, but by software. So that that's an interesting way I used to look at uh even Canva which I was a big user. Um and it it's almost obvious once you start using those tools that where is the need. Um and Canva led the way and you guys are also doing amazing job as I see the product progression over time. Yeah, definitely, man, you know, and and you know, one of the other things that that of course, you know, I've been noticing and we've been noticing is you know, if you if you really think about like especially when I look at like India and Latin America and a lot of other countries, right? Even in the US actually, you see that um, there's so many people who have never told a story, who have never created a piece of content ever before. But they are consuming and they're coming online and creating more. I think that is such a massive untapped market. But generally, I think in SMBs and businesses, we're seeing this trend of that everyone is a marketer and everyone is a creator. It's like a new way to sell stuff, new way to tell a story. It's not really selling actually, but telling a story, you know. And and even if you're selling and you're actually creating campaigns then how do you create these campaigns at the scale with your team collaborating in real time so you can do more with less. I think that's the idea of simplified, you know, so you can create more content in less time, fraction of a cost and do with your team members basically. So you you brought up Canva, right? I mean, one of the things I was uh thinking about is how do you compete now that you know, Canva is a arguably a decent sized player in the game of, you know, marketing and creating content. Are you guys focused on different geographies or different use cases? You know, how are you thinking about competition in general when you're trying to put your product and position your product? You know, such a um great question and you know, the way we kind of look at this on a daily basis is adding value. That's our focus. It's not the focus who we're competing with whatnot and I'll come back to it but I think is that okay, we've seen the sort of the and this is mostly like post- pandemic what we're seeing is people are more disconnected than connected. And I think in a virtual world and remote work and especially work in general, people are trying to build bring teams and people together so they can collaborate better. And none of these things are doing tools are doing it. I mean if you're creating a piece of content, you're using something for design, something for video, something for writing a piece of copy and then you're publishing it using some other tool, right? That's not bringing people together. Your assets are living in different places, your teams are living in different silos, tools, you're paying for too many tools, just burning too much money, almost like a SAS overload. We're like, why can't we have just one space, one place where you can come together as all of your teams, all of your different workspaces, all of your different clients in one single space and create and collaborate like never before. So I think kind of we built simplified ground up day one, there's DNA of collaboration, teams in general, you know. So that's been the DNA. I think Canva didn't start with that. I think what Canva has done is incredible and amazing, but just showing people you can do the drag and drop editing platform that can just like go and help you design anything you want to without being a professional design. We want to take it further, giving a place to replace all these apps, help you create more content, help you publish more and work with people in real time, but also a lot of automated content. Take it even further to kind of go and recommending content to people. I'm like, hey, I can't think of something. You know, simplified can help you think of a bunch of ideas and you can either publish instantly or just you can create your own actually. So I think we're kind of going beyond it now where kind of like Canva is today and we think if we do a good job in just executing and adding value, then we don't have to worry worry about the competition. We can create our own space. I think what what you uh talked about Canva is really, you know, sort of the core why I think we've succeeded because there was a point of time creating any image required, you know, complicated tooling. Uh sort of you have to learn Photoshop to do a basic image of a even if you had to have an interesting Twitter handle, uh sorry Twitter image, uh you had to go through, you know, a bunch of tools, yeah and learn and I remember doing Photoshop and thinking, I mean, this shouldn't be this hard to do a simple image editing. And I think what really Canva pioneered is this web-based drag and drop tooling and gives us also the abstraction layer at which they showed we should be doing our image editing. I think that's also very interesting because I think Photoshop will still have a place for, you know, much deeper and complicated editing for an image or a video. Um, but I think the abstraction level at which most of the individuals, marketers, content creators need uh a tool to exist. I think they've identified that abstraction level in a very uh you know, I think they identified it before anyone else identified it and made it web based. I think that's that's what really triggered and you're right. I think from there you can also think about now how you can integrate with not integrate but I think you have to sort of think end to end uh how do you solve this uh problem of you know, having 10 tools. I think any marketing team if you talk now has at least 10 tools, you know, one for creating content. so you're I think on point in terms of like the collaboration being key. Um, in a way it almost sort of feels like, you know, what Notion did uh for you know, notes. Because I think they really thought it ground up and that changed in how the abstraction level of sharing and because sharing is a big part of writing anything online, right? And that sort of was not integrated well in I think the tool I would say precursor to Notion was Evernote was successful for a time where mobile was coming in. Uh but then they sort of dropped the ball on you know, what is the real core use case our users are using, which would be sharing and why should there be a difference between a web page versus uh you know, a page in Evernote. I think that's where Notion really cracked and that opened up these thousands of use scenarios which Evernote couldn't ever achieve. But it's only possible by just three or four product features to really. Um yeah, so it's interesting when I always think about simplified as the next version of Canva, like if you improve, you take all the good things about Canva and sort of add the layer of recommendations and collaborations and uh also geographies because I think there's a aspect of focus of geographies is that misses uh that is missing today in Canva that I think also where, you know, tools like simplified can help. Yeah. No, definitely all the good things man and and and I think overall, I can think because content creation has changed, I think that when Adobe started or Canva, I think people used to do things differently, right? They taught the world to do do this way or that way. And today's world in the next decade, I think you just want to do a lot more with a lot less. And it's time and money, right? And all that stuff. So I think we have a real chance in sort of like helping people achieve those goals so they don't have to worry about these things and and they can just tell a good story basically and as fast as they can. Do you think uh Adobe will make make an acquisition in this space? Uh they should. you know. Uh I think so. I think I think recently we saw Vista Print uh made and acquire Crello, they acquired uh Canva competitor Crello. I think at some point everybody is realizing that creating content and marketing content is a need, right? You have to you just do this on a daily basis. As you said, right? You're waking up and you're consuming content. You wake up, you check your phone, every piece of thing you see has been created by someone by using some tool basically. So when you're looking at this consumption levels and creation levels, that means like all these companies who don't have access to creation, they want to get access to these companies who can actually help you create. So another thing I wanted to talk to you about is uh the sort of like build in public trend that happens and you use Twitter and LinkedIn pretty effectively in sort of uh pioneering that uh you know, building in public and telling the story of simplified and you do it quite well. So I was wondering how do you approach the whole sharing your story with simplified or even, you know, I think you also do a pretty good job of uh sort of the personal branding side of it. So I was wondering what are your tactics and strategies that you've developed over time? You know, it is it is inspired. I think I do it now a lot more, but different inspirations behind them and I think building in public you know, for every founder out there and everyone who's building something, it's always the hardest part is to figure out oh how do I get the adoption up and running, right? I mean you maybe raised capital, maybe you haven't raised money, you're building something really cool and you just want people to use it. So you get your friends and family first and then you're like, oh, who's next? And people think oh maybe let me get some organic traffic or let me actually buy the traffic, right? By paying doing some paid ads. So the approach kind of has been, okay, if you tell a story to the right people or at least just tell a story and hopefully we can find the right people. Then over time, they might be inclined towards kind of feeling like we're part of their journey or they're part of our journey and they'll end up giving us a shot, using us and spreading the word. So that's been the inspiration behind it, but the second inspiration has been um, you know, as as when you're building companies, you have a lot of stress, stress levels are high, you have a lot of things you're dealing with, lot of fires. And I do think that the one less thing that you can worry about is sort of this um dealing with issues, you know, sharing growth, numbers and whatnot. If you but put it all out there in the world and it's public, you know really worrying about how you're doing as a company. You know, you would fix stuff and you would find solutions to problems, but there's one less thing to worry about. Your employees know it, right? Your partners know it, you community knows it, your friends and family know it. If there's nothing to really hide and that gives you a lot of power because that vulnerability attracts the trust of people. And eventually they help you find these solutions that you cannot do it by yourself. I think that's the approach I've taken. It's still very early. Um, still trying to figure out what's the best way to do it. I do think sometimes maybe even do like a weekly or monthly video or something like a start video recording and just the whole journey of building the company just share with public. Hopefully when they do it, they can just take some lessons and hopefully it helps them to build their next idea or next company. I think there's a uh interesting thing with what you're doing is it fits with what your company and product does. This is this is one thing I don't like about build in public is uh I think there are certain companies you should build in private. Not every company has to be built in public. Uh, but for your company, it makes a lot of sense because you are in content creation space. I think you can crowd source ideas for your company. You can I think it is beneficial for a company like yours to do this and I think you also have the experience of what it means to tell a story. I think that why I feel like you are much better at doing when I see other founders doing it. Uh, but tactically speaking, do you approach it? Do you have a system in place where like, you know, I have to do X amount of uh you know, tweets versus pose. Do you have a tactic or a system in place? Yeah, man. Uh always definitely nailed it. I think that's the way we definitely know that that the the uh so the foundational level truth to it if we are a company helping people create content, why not recreate content and share with the world, right? Like use our own product as well. That's the idea and I think the for the tactical part, yes, it takes takes a lot of time, man. And I also get help, you know, from time to time to kind of like help me source thoughts or put it on like scheduling and planning and designing. And then kind of like it's like a you spend a weekend or something or maybe maybe like an hour or something on a on a weekday and then you kind of like plan it out basically. And the scheduler as much as you can and hopefully the cycle runs, you engage with people um and hopefully it just kind of keeps growing and keep telling the story. But yeah, it takes a lot of time actually. Let's switch gears and talk about uh you know, web 3.0 uh or what people are calling web 3.0. Because the reason I want to talk about this is because we've seen a lot of chatter about NFTs and NFTs are images which essentially are created, can be created on simplified. So are you thinking about, you know, how to and there have been a lot of founders in our last year who have pivoted their companies into different forms of web 3 ideas. Are you actively thinking about that sort of a thing or does it make sense for simplified interacting with any of the crypto technology? Uh what is your view there? Man, um interesting one. Um um personally, okay, personally I do love the space, you know, I've been a big early crypto, I think I see adopter and uh love the space. NFT I'm following it. I've been slowly testing, experimenting, buying here and there one or two to uh experiment myself and I definitely love, you know, what people are creating online and be a part of the community and whatnot. At the simplified level, I think, um, I can't tell you really what the plans are, but what I can do tell you that we do see this is a form of content creation. So we see like kind of like the uh, you know, designing something that you want to share with the world in form of an NFT, definitely is going to exist. It's definitely going to be more and more of that. So at some point we'll have to think about creating these frameworks and tools that kind of makes it easy for anyone to create a piece of art or anything and that can be of course converted into NFT with a single click of a button. So, we don't have any plans now to do it. Uh, I personally think a lot about it. I do think that simplified can play a role in a way where it can help people uh achieve these goals and share their art with the world definitely. Um, but we just don't know how, when, what and if we're going to do it, but I do see that the platform can play a role in helping people. Yeah, I think pretty much everything you could do around NFT sort of overlaps with simplified because let's say tomorrow you a content marketer for a company or a creator made a Tik Tok from simplified and it goes viral or sort of becomes, you know, uh like the first ever tweet or Tik Tok or whatever content and sort of becomes iconic in its own way, then you would want to create an NFT out of it and you could create start creating tools uh around that content. And you can sort of extend this ideology into multiple skills that all belong on simplified today. Uh so that was my motivation behind asking the question as well. Um But uh as we're, you know, almost uh towards the end of the podcast, I wanted to ask you the question of uh I think you've been a repeat entrepreneur, uh right? Before Rumi you were doing websites and then you did Rumi and now you're simplified. Why why be an entrepreneur? Why can't just do a Um, yeah. You know, they always this saying, I think there's some saying out there saying that once an entrepreneur is always an entrepreneur. I mean, I grew up in a family of entrepreneurs and I've seen my dad struggle for decades, you know, just to building his thing that he loved, failing at it miserably and then hopefully finding some success at some point in his life. Um, so been around uh grew up like this with a lot of risk and appetite for that and I think just loves solving problems. That's what it is and um, there's just always a lot of fun. I think a job, I don't think I'm a good employee to be hired. I think I'll get bored very quickly and, you know, I'm not creating adding a lot of value to the world just by being at a job. I think creating and solving problems at scale and helping hopefully a lot of people along the way is something just really enjoy. Uh, so as an entrepreneur, what do you think your core strength is uh looking back? You know, I think just getting up and getting stuff done. I think I've always realized that, you know, and you know, I've been investing for a while too. I think kind of like people skills and I've made a lot of mistakes in that as well, miserable mistakes. and I feel I keep getting better at it kind of like trying to figure out um people who can help us build things and execute fast. I think just executing man, just like you know, I've done everything from growth to product to raising capital, but I think at the end of the day, it really comes down to the ability to get something done, really get your hands dirty actually, you know. And hopefully go in and also get out as quickly as you can and then allow other people to help them grow and also do stuff. And you sort of do this multiple times and then you see this sort of like group of people that are growing and thriving and I think you just ride there with them, you know, getting your hands dirty and enjoying their journey and hopefully growing with them. So I think that's really the most fun. Uh, so we're all at the end of the podcast. Uh what is the best way for the, you know, listeners to reach out to you and, you know, find out more about simplified? Uh, I mean they can definitely go to uh simplified.co. So p l i f i d.co or they can also just find me on Twitter, you know, my um last name, y a d a v j a y, my first name on Twitter. And reach out anytime. Thanks Ajai, thanks for taking time. Thank you, man. Really appreciate it. Thank you.