From journalist to CMO & Co-founder, criteria of making career decisions and more | Rapti Gupta (Bugasura, HSR Founders Club)

This transcript has been lightly edited for brevity. 

Mita Mandawker (00:07):

Hello and welcome to Ctrl + Alt + Marketing. I am your host, Mita Mandawker. My guest today is Rapti Gupta, co founder and CMO of Bugasura and also the co founder for HSR Founders Club. Now, Rapti is a marketing leader with an atypical career path. I say atypical because she started her career as a journalist and later moved into startups as she tried to make the best use of the content skills that she learned during her time in journalism. And the rest is history. From managing content to becoming a CMO and co founder, she's done it all. If you're curious how someone with the love for words made it to the C suite, this is the episode to listen to. So let's dive into part one of Rapti's story. 

Rapti Gupta (00:53):

Thanks Mita for having me on the podcast. I'm also super excited for your podcast journey. I hope this becomes one of those podcasts that goes into the history of podcasting. I hope. I am really happy to be able to share my journey with you today or the podcast. I'll just give you a little bit of an overview into what I do and what my journey has been. I have about twelve years of experience in marketing and essentially twelve years of experience in my entire career. But I didn't really get into marketing right from the start. So I started off as an Internet journalist at International Business Times. And, you know, I spent about two years there. And, you know, I every day I was editing and writing 5 - 300 word articles for 300 to 500 word articles and also editing another three of them, right? 

Rapti Gupta (01:55):

So I think I got a head start on how should we be spotting the right kind of content that works, how headlines work, how content works, how editing works, how writing works, and how books should be designed, how leads should be designed, etcetera. And at that time, I had a great mentor at International Business Times, Miss Bharti. She had worked at brandequity and a whole bunch of other great publications. I was very, very thankful for being able to be her mentee at that point. So doing that for about two years, every day, writing and editing six, seven articles every day, I think it just made me super efficient in writing content. And this was around the time in Bangalore when the startups in a scene was just booming, right around 2014 ish. Around that time. 

Rapti Gupta (02:53):

And very early on, I figured out that while I really enjoy writing and while I really enjoy content in general, I did not want to pursue journalism as a full time career. Because honestly, I figured out very quickly that there's not much money to make internet journalism at that point, right? And you got to make money, right? So at that time, I joined an early stage startup. After two years of my STD, International Business Times, I joined the startup called Affimity, which was a social media startup. This was like a passion based network for people to come and consume content and share content and make friends. I was there for about two years where what I did over there was essentially populate the channels with different types of content, drive users to the platform. 

Rapti Gupta (03:50):

And that's where I learned this whole social media parts and the community parts, which I'm still very bullish about. And we'll talk more about communities later on in the podcast. But essentially, this is where I learned how to engage with your content or how to get users to engage with your content. So two years into the startup scene and one fine day our CEO comes and tells us, hey, we've run out of money and we're going to shut down. You probably have 15 days time or something, and we'll support you and all of that. But having such a setback very early on in my career, I don't remember being afraid at that time. You know, I, I somehow felt that it's okay, we find another job, it's just another job. There are, there's bigger fish to fry. 

Rapti Gupta (04:46):

I don't think I was ever very afraid about, you know, losing my job or losing my career at that point, because I still knew that, hey, I learned something on this job, and what I'm going to do next is just going to compound what I've already learned from you. So having taken that experience, you know, I started, you know, interviewing at different places. And for a very short and brief period of time, I joined this big company. I won't name the company on the podcast, but I joined this company. And, you know, there I joined as a product, a content marketer over there. So what did, what my job essentially had entailed was write email copies, write push notification copies, and write blogs. 

Rapti Gupta (05:43):

And the way we were being assessed, or our performance was being assessed was for the number of words that we are churning out on a week over week basis. And I was like, what? How? That was one of the criteria, although there was other criteria, like how much open rate was your emailers getting, how much open rate was your subject line getting? Which I thought was fair, but the number of words just did not make any sense to me. And, you know, I spent just three months there only three months, and it wasn't fun at all for me. And, you know, when I went to my manager and I told him he was not working out and this is not what I want to do, he was like, oh, man, we really wanted to work a little longer with you. 

Rapti Gupta (06:30):

We see a lot of potential in you. But, you know, somehow I knew that this is not what I was interested in and this is not what I wanted to do. Right. I wanted to use the skills that I had learned during my journalism time, during my time at Affimity and use them to bring in some sort of impact in a company. So for newbies who are watching this, you know, if you're worrying about, you know, let's say you got laid off or let's say you're still wondering what direction should your career take? I think it's very important to understand what really excites you in the beginning, and I, so that you can put in your hundred percent to it and then refine from there on, you know? So that's when I also interviewed at Instamojo, and that has been my longest career stint. 

Rapti Gupta (07:24):

I was at Instamojo for about five and a half years. And I started off as a content writer there. And initially I think there was some, you know, some sort of a, what would you say, like some sort of a hesitation or doubt on, you know, how will this content work? How do you, how do you make fintech fun, right? Like, how do you make b two b fun, right? That's something that we are still talking about. Like, it's been done. It's been done and dusted so many times, but I still see people talking about how B2B is boring. Fintech is boring, and all of that is boring, right? So I think there was a lot of hesitation and doubt. And, you know, there was just a general thing of confusion, like, how is this going to be fun? 

Rapti Gupta (08:14):

How is she going to make this part right? And, you know, what we did at that time was just, we just got like a bunch of us. Like, it was my SEO head, it was me and my growth head. The three of us, we just got into a room. And of course, our CEO was also there at that time. So the few of us, we got into a conference room and we started bouncing ideas off each other. Like, what should we do? How should we, you know, like, think about educating SMEs, about how they should run their businesses. And, you know, from there, we came on to, came into starting a newsletter, which is the SME wrap. I think it still runs. We had about. By the time I left Instamojo, were about 2.53 lakh subscribers with about 20% open rates. 

Rapti Gupta (09:08):

And essentially what the SME wrap was having a fun twist or giving a fun twist to any latest news or latest developments that the. That was happening in the business world. The biggest example, GST. Right? So when GST was coming out, and I think all of us, I know that a lot of us still don't understand GST, but for smaller businesses, it was even more difficult to wrap their heads around because it was pretty complex. And you also didn't know who qualified for what. What kind of GST should you be filing based on the type of business that you are, etcetera. Right. So what we did was we actually, you know, sort of wrote an edition where, you know, it's a conversation between Gabbar from sholay and samba. Right. Like, so a take on that. You know, like, so those kind of things. 

Rapti Gupta (10:12):

It also helped that the user was very familiar with hindi speaking and pop culture references, really worked with them. So, you know, we sent out editions like that. Another memorable addition was that every time the budget came out in February, March of the financial year, we would always do a live capture and a live stream of the budget and take out only the parts that were applicable to the. To the SME's or our user base. Right? So there was this one edition that we sent from the name of Nirmala Sitaraman. The wrong name was Nirmala Sitaraman. Yeah. And I think my CEO was also like, you know, he was Nirmala sending me a email and he's opened it and he thought was. It was the. It was the SME wrap. And he was like, what? He just had a good. Laughter. 

Rapti Gupta (11:08):

He called me and he told me, like, we should do more of this. Right? And in fact, it also kind of went a slight. Not viral, but it got a few comments or shares even on Twitter right. At that time, where people were like, this is such a great way to educate people about what's happening. And some of them are also pissed. They were like, you can't do this. This is wrong. But then, at the end of the day, everybody understood that there is this newsletter that you go to for the right kind of advice or the right kind of business advice. Right. And that's how, you know, we did a lot of experiments and content. I, in fact, even went on to build an e learning product for Instamojo, which was a lead magnet for Instamojo. It was called mojo versity. 

Rapti Gupta (11:54):

It's still live. You could still go and take three courses. If you're a small business over there, which are self paced, you could still take them. You get a certificate as well on the completion of that course. So borrowing from that example of GST, we figured out that since we are not experts at GST, and this is definitely a problem, how do we educate the masses and also build that trust for the customers to make a buying decision from Instamojo? So we decided that, hey, why don't we, you know, partner up with the biggest leader in taxation india, which was clear tax at that point, right? So we partnered up with Cleartax and we created a course of. We created a course on GST and it broke down each and everything. 

Rapti Gupta (12:40):

And, you know, I think in 1 hour, you could complete a GST course as well because it was that well crystallized by the clear tax team as well. So, you know, that became a lead magnet. That also became a very big brand and thought leadership channel for us. In fact, it also became a very big lead channel for us. Right? So a lot of people would complete courses and they would even now, if you go to LinkedIn and search for Mojo versity, you will see a whole bunch of people sharing their certificates of how they've completed courses on Mojo versity. Right? Similarly, we also work with HubSpot to bring out an email marketing course. Right? 

Rapti Gupta (13:22):

So initially, when I was talking to HubSpot about this, HubSpot was trying to break into India at that time and wanted to also cater to the SMB market india. So HubSpot was very like, we already have an academy. Why would we want to do this? We already have this. So I was like, see, we have the user base that you need, and I think that you wouldn't have to put any extra work to do this. What we can do is you have a whole bunch of articles that already talk about email marketing for small businesses and you have a bunch of checklists and all of that. We could repurpose those and do a collaborative course. So we would share all the leads that signed up to mojo versity would also be shared with, let's say, your HubSpot or your Cleartax. 

Rapti Gupta (14:09):

So whoever we're partnering with. So it was a win situation for both the companies, building a product for mojo versity as well, and then going on to do a podcast as well. During the lockdown, you know, we would just collect. We would just connect with our customers on Zoom calls and do an audio podcast with the same earphones. And they were also on their same earphones. And, you know, the job was to bring out these great stories from tier two and tier three cities. And, you know, everything was a jugaad at that time during COVID as well, because there were quite a few challenges that we had to go through. Like, I did not have. I did not have access to get a mic from somewhere as well at that time. 

Rapti Gupta (14:51):

And, yeah, because our apartment was in that hot zone quarantine where nothing could enter or go, and you would only have groceries delivered to you. Right. And budget that. So there were some issues, but work had to still go on. Right? So we had to keep doing this. So we just said, let's. Let's make use of whatever we have, whatever resources we have, and let's get this done. So, yeah, I think at Instamojo did a whole bunch of things. It was, it was the most fulfilling experience of my career. Tried my hands at everything, right? From content to branding to events to, you name it, like, even building a product. And, you know, there came a point during my time at Instamojo is that I started feeling a bit stuck. 

Rapti Gupta (15:44):

You know, I also started feeling like I've been doing this and marketing to the same user base or working in the same industry for a very long time. And five and a half years is a long time. And, you know, it was also a part of. It was also the peer pressure. 

Rapti Gupta (16:00):

Like, because a lot of them were also skipping jobs and doing really well at their jobs, right? Like, I could see that they were all moving on in 2-2-2-2 years and they were all leveling up in their skill sets as well. So at some. After five and a half years, I was like, yeah, I think now I've hit my top level of this thing. The limit, essentially. I've hit that limit where I couldn't. I think I should go and do something else. Probably explore a new market, explore a new demographic, explore something, right. Something new. So that's when I, you know, I just started looking out for my other opportunities and that's when Bugasura happened to me. Fun fact, I joined Bugasura as the head of marketing, right? Because that's the, that's a. 

Rapti Gupta (16:53):

The role that Pradeep and Avinash, where Pradeep is the CEO, Avinash is the CTO. They were looking for a marketing head. They were not looking for a co founder. So Pradeep had this long Google form, you know, it was very eccentric. Not your regular, average form. It had deeper questions like, have you ever failed in life? You know, what makes you, what keeps you up at night? Or some of those kind of philosophical questions, right? And I really had a lot of fun filling that form, and I actually took time out to fill that form as well. So I fill the form, I hit submit, and I think 15 or 20 minutes later, I get a call from Pradeep. Yeah. And, and we started chatting, and we had a two hour long conversation, and we spoke about imposter syndrome.

Rapti Gupta (17:51):

We spoke about my career, we spoke about his career. We spoke about his experiences. And, you know, somehow it felt like, hey, this was, this is the kind of person, and this is the kind of, you know, culture that I want to be at. And also, the product was very interesting to me for two reasons. Right? A, it was a developer tool. It is a developer tool. And developers happen to be the hardest people to market to, the hardest demographics to market to. Most marketers will agree this. Especially marketers who work at developer tool companies, right? And I was like, I want to do this. I want to take this challenge, and if I fail. I don't. 

Rapti Gupta (18:33):

It doesn't matter, but I want to take this challenge up and I want to see how I do it, because that's the only way I could beat my own imposter syndrome. No amount of meditation or no amount of, you know, motivational talks or no amount of podcasts, for that matter, is going to break that imposter syndrome until you go and do the work and do the hard work. Right. The hard skills are definitely necessary. Yeah. So I got hired at around October, in October 2022. And in November, I did a product hunt launch. I did not wait for. For any time to start executing.

Rapti Gupta (19:11):

Because for me, it was about, there were certain things that were set up, like who the ICP was, was set up, who the, you know, who we should be targeting, what the kind of, what were the kind of accounts, what were the kind of size of companies, etcetera, that was pretty much set. But what was missing was a feedback loop of usage and the adoption part. Right? So. And that's exactly why Pradeep and Avinash also needed a marketing head. The go to market needed to be accelerated. So I was like, your product is ready. It's not in an MVP stage or it's not in a very shaky stage. Why are we not launching it? So what happened was they had tried to do a product and launch earlier. But that didn't work out because the strategy for it was missing. 

Rapti Gupta (20:02):

So what I did was in November, I launched the product. I launched Bugasara product hunt with a proper strategy in place. And I've spoken about my product hunt strategy in multiple other podcasts and other articles. We can link them down below. Probably what happened was that we became product of the day and we got a whole ton of reviews. We even closed some revenue from the product endpoints. And I think that gave my founders, a lot of my co founders now a lot of confidence about the product itself and the fact that, hey, this can work. And I think since then, I have not looked back. We've kept on explaining, experimenting, doing some sort of experiments to understand and define the market, and also to keep building that repeatable predictability in the business. So that's something that we're still working on. 

Rapti Gupta (21:05):

That's something that we're still solving. But six months into my journey at Bugasura, I think what Pradeep and Avinash, saw was, the level of ownership that I worked on the product, and I think that was a very big motivator for them and also very big trigger for them to come and tell me that, hey, Rapti, I think we want to offer you this role. And I didn't immediately accept. I, in fact, took a couple weeks probably, to think about it. I spoke to my peers as well, who probably had similar journeys. And then I thought, yeah, let's do this. You know, like, this is also something new. I want to take this risk. I want to take this lunge and see what happens. It doesn't matter if I fail. 

Rapti Gupta (21:55):

I think one thing that has been, you know, sort of at the baseline of my entire career is that I've not been afraid. You know, I've been fearless. I've not been afraid to take those risks. And the minute that I start thinking about how I'm going to look, what is my reputation going to be? What am I going to learn? What if I lose my job? I've realized that the day I feel that way, that is the day I sort of end my career. But there is a flip side to it. The flip side is that in general, I'm a very scared person. Scared of becoming obsolete. I. The reason that I'm not scared of taking up or failing on something is because I'm not. I'm really afraid of becoming obsolete at some point. 

Rapti Gupta (22:46):

You know, like all these years of hard work and all these years of pushing through multiple things and, you know, getting things done, what have they resulted to you? Right. You want to essentially go to a point where you get some sort of insights and get some sort of learning from the point that you have reached at. Right. So I think that's what keeps me going. And I think from that particular part where I feel that I should take more risks, I took this risk as well, and that's how I became the CMO at Bugasura. And, yeah, we are still, the goal for this financial year for us is to become operationally profitable and we are moving ahead on that. Yeah, that's how my journey has been. 

Mita Mandawker (23:36):Firstly, so many wonderful things to unpack from everything that you've shared so far. But firstly, before I get into that, I would like to congratulate you. It's always so exciting to see a marketer on the cap table being a part of a founding team. And honestly, it's inspiring. Super duper inspiring. Okay. I think one of the things that I really. Okay. You've shared, like, your entire journey, and frankly, rapti, it's quite a few twists and turns and it's all come together really well. I think my favorite parts of everything that you've shared has been the kind of creativity that you brought to the table when it came to Instamojo, stint, you know, biggest stint of your career, and to actually even go and push the boundaries of creativity in a. In an industry which is traditionally very slightly fuddy duddy. 

Mita Mandawker (24:37):

And regulated, so to speak. I think the Nirmala Sitaraman one was the best one. I think I literally laughed. 

Rapti Gupta (24:47):

Yeah. And we did. But I think like that. I think that's what, I think that's what kept the entire team also very convinced about our marketing, because that worked. Right. If your internal teams are not excited about your marketing, then obviously your customers are not going to be interested because your internal teams are the ones who are building the product and they understand ICP as well. But yeah, it's definitely was one of the most creative journeys that I've had here. 

Mita Mandawker (25:23):

And I think, and once a secondary part of the whole journey that you shared and that kind of comes across when you were even talking about the companies you worked with has been the founding teams in general. They've been different as compared to a lot of setups that other marketers have experienced. Actually, I would like to understand one thing. So you've had, even when we spoke initially, you mentioned having a very distinct personal criteria in place when it came to making decisions about your career opportunities. Founder fit, market fit. Like you mentioned about the competitive landscape, is there someone like, you know, operating in a good space and the purpose.

Rapti Gupta (26:08):

Of the company itself? 

Mita Mandawker (26:09):

I think one thing that I would really like to understand, and can we get into these factors a little more in detail? Because this is a career podcast, and I think our listeners would really find it helpful, you know, to understand how to use these criteria. 

Rapti Gupta (26:24):

So I'll tell you what my criteria was and why that was my criteria as well. So early on, I think when I started working at my journalism stint, right there, I think I understood. Yeah, there I think I understood how the nook, the nitty gritties of it work, right. And I was working under a female mentor, and I realized that, you know, I needed to connect very deeply to my work to be able to give out my hundred percent. So I'm a very emotional worker. So I need to connect to the purpose. I need to connect to the greater good or the greater impact that the company can have on a single life or a single business. For me to be able to work over there, right. That was definitely one of my things because, again, very passion driven.

Rapti Gupta (27:28):

I never thought of myself as an employee. I always thought of myself as an entrepreneur, even when I was working at any other company. Are my skill sets appreciating or are they depreciating? I never wanted to be a depreciating asset. I wanted to be an appreciating asset, and I wanted my skills and my valuation and everything to go up over time. So I think that was one of the biggest reasons that I wanted to pick places where I can create impact with. 

Rapti Gupta (27:59):

So I did try my hands at the big company that I told you about, which I don't want to name, but because I didn't spend a lot of time there, I figured out that I'm not a good fit for slow moving or slow moving companies or slow moving cultures or where there's lot of red tape or there's lot of approval processes and all of that. I just rest less in nature like that. Where I wanted to do things fast, learn fast, I think that's something that I've always had. I wanted to fail fast. I wanted to learn fast. I wanted to, you know, just pick up things because for some invisible alarm clock, you know, sort of hanging in front of me where I'm like, nay mekwi, I want to do this, I want to do that, I want to pick this up. 

Rapti Gupta (28:49):

I want to see how this delights the user or how this impacts the product. Right. So that was definitely one of the reasons. And thirdly, I think the culture is very important for me. The kind of people that you spend, what, how much? 10 hours at work today. Almost 10 hours at work today. You can say that you're spending 8 hours, but when you're going to office, you know that some of the other things are getting extended. You're either in meetings or at least your brain is 10 hours in at work. So you might as well surround yourself with people who are. Who are smarter than you, who are doing better things, who understand problem statements better than you. Right? So that's something that I think was definitely a plus. 

Rapti Gupta (29:34):

And the third thing is that, is the market big enough for this product of flourish? Right. And does the market have a big ass demon to sort of fight with the David versus Goliath scene? Is there a Goliath in the market? And can you, being the David, go up or go against the goliath? So I think for Bugasura, that was definitely the scene, I think, when Pradeep came up with a vision for the product, the idea was that, you know, everybody in the world uses Jira. Most enterprises also use Jira, but not a lot of technologists actually enjoy using Jira. Is it a very enjoyable experience? No, it's an experience because it's a legacy experience. It has been handed down like a memento of or like a antique piece, you know, over generations. 

Rapti Gupta (30:39):

And people are like me as a marketer, I had to use Jira, and I was like, why the hell am I using Jira? I had a personal dislike for it as well. Right? And, you know, that's what I thought, that there is a pull in this market. So how is it that. How is it that there's this, you know, pull, or there's this pull factor which they have created and this legacy that they've created. There's got to be some magic in the user, right? Not just the product, also the user. Which is why the demography was also very interesting. See, the thing that I figured out about technology, so, like, for example, your CTOs or your engineering leaders, so they're very loyal people. You know, what they. What they generally are into is like, I want something, nonsense, that's going to solve my problem. 

Rapti Gupta (31:33):

And if that solves my problem really well, I'm not going to spend a lot of time looking at other tools if, and I'll tell you how things have changed in the market over time as well. Now, today, technologists are like, we build it by ourselves, we won't buy technology. We'll just build it by ourselves. Is it that easy? Because it's that easy today. Right. So the whole, you know, there's also this website called I fucking hate jira.com. It's just got anonymous hate for Jira. Anonymous hate for Jira. Right. You just press the button and you see why people hate Jira. That's a great starting point for us in terms of marketing. Right? Like why you should move away from Jira. 

Rapti Gupta (32:19):

But, you know, while I worked with Bugasura, I also understood that the market, sure, there is a market, but I think there's a lot of scope for us to bring in Pradeep's testing skills into the product. Can we productify Pradeep's brain? I think that, and he's already done that with Moolya as a services company, which is Bugasura's parent company right now, I think the opportunity lies in the fact that Pradeep's the way that he thinks about testing. If we can productize that, combine that with the market pull of what Jira has created with what the other incumbents like for there are other players, ClickUp, there's Monday, etcetera, which are project management tools. These all double up as bug trackers. And in most companies, product managers are doubling up their project management tools as bug trackers. 

Rapti Gupta (33:19):

But to explain the need for why you need a specific bug tracker, why you need an issue tracker, why you need a specific tool for testing and tracking and managing your bugs, I think that is the problem statement that we are trying to solve. And I think that's a very exciting space at this point. So far, it's looking really good and that's something that we are doing. So, coming back to my career choices, I think, yes, the fond of it, my own nature of what I want to do and how I want to challenge myself, and number three, if the market's big enough, I think you should. I think those were my three criteria, to pick up another tool, a new role. 

Mita Mandawker (34:07):

And that wraps up today's episode of Ctrl + Alt + Marketing. I hope you found this conversation as enlightening and enjoyable as I did. Thank you for tuning in and staying with us till the end. Your support means the world to us. Please show us your support by hitting the subscribe button and leaving a five star review and also telling your friends about control alt marketing. Your feedback helps us reach more marketers like yourself. To stay updated on the upcoming episodes and gain access to extreme exclusive bonus content. Be sure to sign up for our newsletter at the link in the show notes well send you episode updates, insider tips and more right to your inbox. We love hearing from our listeners, so if you have any thoughts, suggestions, or even just want to say hello, drop us a line at marketershelpmarketers1@gmail.com. 

Mita Mandawker (34:59):

Until next time, take care and ill see you on the next episode of Ctrl + Alt + Marketing, where Marketers Help Marketers.