Categories: Startup Stories

The Inside Scoop on, a Differentiated Matchmaking Platform for Quality Singles

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The first few years of an individual’s professional life is cherished, even more so as individuals tend to invest a lot of time for work before deciding to ‘settle’ down, find a partner and then hopefully raise a family alongside professional commitments in order to earn and make the best of what life has to offer. The free market economy is a competitive one and therefore, individuals ought to understand the socio-economic environments to which they belong to, in order to make the best decisions and make progress in their respective lives. 

India is a young country, with a median age just under 30 years. Incredibly almost half the country, which is 600-700 million, is composed of the under 25s, a massive cohort who will create new trends and add cultural dynamics to India’s already vast, diverse population. Many cultural clashes are the norm in India, from clothing styles to language to cuisine, to sexual orientations and religious beliefs, in tandem with thoughts which are labelled progressive, conservative or regressive. 

All these factors of diversity surely ought to play a huge role when an individual decides to start a family with his or her mate. 

The Inside Scoop on, a Differentiated Matchmaking Platform for Quality Singles

We are pleased to have been able to sit down, virtually, with Anil Kumar, the founder and CEO of  We asked him about his company, his professional background, how he came to found his startup, and salient aspects of life as an entrepreneur.  Here are our questions and his answers.  You can follow him on Twitter at @aktxt.

Tell us about your startup.

I founded and run 

It is a matchmaking platform for quality singles, whether they are ready for marriage or want to get to know someone as friends first.  Jodi365 is primarily a self-service online platform (on the web and, currently, Android); yet, we also provide personalized matchmaking assistance to discerning clients.

A startup, by the widely accepted definition, is a venture in its early stages, developing a novel product or service to address a problem and in the process searching for a viable, scalable, or repeatable business model.  So, it may be more appropriate to refer to my growing business, which I founded in 2009, as a scaleup instead.

What made you start your startup and what problem does it solve?

You can say that I recognized the opportunity thanks to an intimate awareness of customer pain.

As someone who was single in his 20s and into his 30s, like many busy, career-focused single professionals, I found it hard to come across potential partners in the course of daily life.  Options had emerged online, but the prevailing sites didn’t quite work for me.  It didn’t occur to me that there might be a better way, or that I could do something about it, as in working to introduce a better way.  Upon giving up on one channel or the other, I would just go about my life, as a typical consumer would.

The dots got connected in early 2009, during the home stretch of my MBA program at the Chicago Booth School of Business.  Specifically, this a-ha moment came to me: That there was a gap in the marketplace, more so for a changing India, and that a “refreshingly different” matchmaking platform catering to educated professionals would be well received.

Tell us about yourself, your previous jobs/ventures? What were you doing before this startup?

I have acquired varied professional experience over the past couple of decades, as a code developer, researcher, consulting engineer, NGO head, entrepreneur, and angel investor.  However, it may be more helpful to younger professionals to point out that the arc of my career has been far from linear.  Why, “What next and how to forge ahead?” were seldom clear.  I pushed against various doors in a desire to grow and get ahead.  Some didn’t open, some did, while some other opportunities and paths opened up in unexpected directions.

Engineering interested me enough to pursue my dream of studying at IIT-Madras.  I then chose to pursue a research career, in academia, and that led me to the US, where I earned a PhD in computational hydrodynamics.  My career aspirations evolved, in part due to my inability to cope with the stress of grad school.  (The startup struggle, I often like to point out, feels like a breeze in comparison.  Of course, that may be in part to my being older and wiser and, more importantly, accepting that failure is an option and not a bad thing – a mindset that wasn’t the case in my younger years.)

So, I moved to industry instead and spent seven years at a boutique consulting firm in Seattle, providing specialized engineering and consulting services to clients in the marine industry.  While in Seattle, the desire to contribute to greater good had me taking on volunteer and leadership roles, on the side, at NGOs that worked to raise awareness of animal rights and the health and environmental benefits of a vegan lifestyle.

I wanted to do more, something entrepreneurial, but wasn’t sure of what, when, where, how, and with whom to start something.  I saw merit in returning to school for an MBA, part-time, and enrolled in Chicago Booth’s Weekend MBA program, while still living and working full-time in Seattle.

Prior to founding FreeElective, Jodi365’s parent company, I was the lead associate at Hyde Park Angels, one of the largest angel investment networks in the US Midwest today.  My apprenticeship with HPA in its early stages ranks among the highlights of my education at Chicago Booth, for how it prepared me for my subsequent entrepreneurial journey.

Where is your startup based out of? Why do you think that is the best place for you?

I am reminded of the saying, “Home is wherever you hang your hat.”

I founded FreeElective, Jodi365’s parent company, out of my downtown Chicago studio in the spring of 2009.

It made sense, with my consciously choosing to bootstrap the business, to stretch my finite dollars further by building the platform cost-effectively out of India.  Even otherwise, being in India was critical to executing on the opportunity that motivated the founding of Jodi365: Introducing a next-generation matchmaking platform for a changing India.

So, I set up FreeElective Network, an Indian subsidiary the following year, out of Chennai, my home town.  I debated between Chennai and Bengaluru and even scouted for rentals in Bengaluru, but settled with Chennai for a combination of reasons.

As India-based, tech entrepreneur friends advised me, it would likely be easier for me to recruit entrepreneurial talent – not a given, especially a decade ago, when it was much less glamorous – in a Bengaluru; however, it would be easier to retain talent in Chennai, in part for cultural reasons.  

The decision was, of course, influenced by my immediate family’s still being based in Chennai.  I am grateful that, by choosing to be based in Chennai again, I have been able to spend more time with my elderly parents and to bond with my little nephews and nieces over the past decade.  I also don’t mind not having to endure sugary sambar, as is the norm in Bengaluru!

As a startup founder, what are you paranoid about? What keeps you awake at night?

There is no shortage of worries that keep a startup founder up at night.  Every entrepreneur has their variant of “The Struggle” that Ben Horowitz described eloquently.

I have had different specific challenges dominate at different times over the course of building and growing Jodi365.  These include:

  • finding and recruiting the right talent
  • building a product that works and scales
  • raising the necessary funds and making sure that money doesn’t run out
  • retaining talent
  • dealing with inevitable team churn and ensuring smooth transitions
  • figuring out the business model
  • marketing and monetizing the business effectively
  • dealing with user churn (an inherent challenge in matchmaking)
  • not fretting about the competition (however natural that may be), even as many others woke up to the ripe opportunity for “disrupting” the staid matrimonial industry
  • prioritizing continued product development smartly
  • keeping software glitches in check
  • guarding against hardware crashes (on the cloud and on local laptops) and the potential loss of data
  • ensuring that our software and sensitive data remain secure against hackers
  • complying with regulatory overkill and the complications that result from even unintended oversight
  • managing user expectations
  • dealing with difficult clients
  • warding off scammers and preserving the site’s reputation for quality
  • maintaining team morale and keeping them motivated, by cushioning them from some stressors and by openly sharing my challenges in dealing with some others
  • responding to crises and scampering to operate uninterrupted (e.g., during this pandemic, in times of citywide strikes and political uncertainty, and during the devastating 2015 Chennai floods and its aftermath)
  • managing one’s personal relationships and making regular deposits in one’s relationship banks
  • and being mindful, through all this, of my own emotions during the emotional roller-coaster that startup life is.

So, there isn’t any single fear; it’s more a concern that, of all the possible things that can go wrong in any given week – and there is such a thing as Murphy’s Law! – the floor may suddenly cave beneath me.

I am grateful, though, that despite all this, I am generally able to sleep soundly and to wake up with a sense of purpose, a decade-plus in.

Who are your competitors and how are you better than them?

There is no shortage of competition in the matchmaking business.  Matchmakers have been in existence for probably as long as humans have sought to enter into relationships.  This is especially true in Indian society, in which everybody and their aunt tries to play matchmaker, with varying degrees of success.  Indian Matchmaking, the hit show on Netflix reminded many of that recently.  Our competition also includes the so-called “marriage bureaus”; traditional, matrimonial sites for the marriage-minded; and newer, casual-dating apps.

Fundamentally, Jodi365 is not a typical matrimonial site.  It is not a frivolous dating app, either.  Rather, it is a thoughtful hybrid that helps quality singles find the right match, at a pace that’s right for them.  Jodi365 is primarily a self-service online platform; yet, we also provide personalized matchmaking assistance to those who value the expertise and guidance on offer from our team of relationship managers.

We do make an earnest case for how Jodi365 is differentiated from its competitors – see the “We believe” section of  Ways in which we stand out from the competition include: 

  • Our focus on the niche segment of “quality singles” – with education being a proxy, however approximate, for quality – rather than aiming to be everything for everybody.  We subject users to a detailed profile questionnaire before they can even browse matches.  The detailed information enables us to provide more relevant matches.  Just as importantly, the comprehensive questionnaire weeds out those who’re not quite serious about finding a match, and that works well for us and our user base of genuine users.
  • Our commitment to user privacy: Unlike the competition, we don’t expose users’ names, profiles, or even photos to web search engines, to random visitors (as bait), or even to any registered user.  A user’s profile and photos are displayed by default only to registered users with verified phone numbers and who also pass one’s match filters.  We also offer additional, unmatched privacy safeguards for users’ names, photos, phone numbers, and sensitive profile details.
  • Our diligent efforts to maintain a user base of only genuine profiles.  In addition to requiring that users verify their mobile phone number, we ask that users provide, for our inspection and not for display, a government-issued photo ID (passport, driver’s license, or Aadhaar card), a real-time selfie video, college/university diplomas, and employee ID.  We manually screen 100% of user profiles and call users as necessary, in striving to ensure that there are no fake profiles here.  We are also ruthless when it comes to booting users out should they not abide by our terms of service, especially our code of conduct. (Simply put, do not misrepresent yourself, and conduct yourself honorably in your interactions with other users.)
  • Our emphasis on helping to ensure true compatibility, through our matching process and the way in which we facilitate gradual, deliberate interactions.  As we like to say, Jodi365 isn’t classified ads gone online or a mere catalog of bio data.
  • Our focus on innovation, through measures such as selfie video verification of profiles and our SecureDial™ phone system.  SecureDial lets users talk to each other, phone to phone, with each other’s prior consent, but without having to reveal their phone numbers.

More than that, again, we don’t fret about the competition.  I like to draw a parallel to the auto industry.  Nobody asks a Tata, “Why are you getting into the family car segment?” or a Toyota, “Why are you introducing another model?”  Sure, auto companies need to make a case for how their car is better than a competitor’s.  However, as long as a business is able to offer a good product or service, at a compelling, competitive price, more power to them!  In a large, growing market, there’s a good chance that there will be enough takers for each good make and model.  

As the saying goes, a rising tide lifts all boats.  That applies to the growing matchmaking industry, too, thanks to rising internet penetration in the country.  Moreover, given the inherent churn in the business and the absence of true network effects, it isn’t a case of “Winner takes all,” either.  As long as we stay focused on helping our users, we’ll continue to be fine.

How hard is it to have a work-life balance as a startup founder and how do you manage it?

It is very hard, and I have had enough opportunity to ponder over what I may be doing wrong and what I could do better.  I can’t claim to have cracked the puzzle.  I’m not sure if such a thing as balance is even possible.  Then again, ReWork: Change the Way You Work, by Jason Fried and David Heinemeier Hansson, remains on my to-read pile, and I wouldn’t mind coming around to a different view on balance.

What helps, even today, is the awareness that sleep, a good diet, and regular exercise are important in staying at the top of one’s game in this long race, which also consists of frequent sprints.

A friend’s kind gift of “Why We Sleep” continues to sleep soundly on my nightstand, unread, but I am better about getting in regular exercise several times a week.  My routine consists, on average, of about 10 minutes of some favorite free-body exercises, light yoga, and intense skipping, as I’ve described on Twitter.

Have you raised funding? If yes, then we would like to know the details. If no then please tell us if you are looking to raise.

Yes, after bootstrapping for 9+ years, we’ve gone about raising a small round of funding, as part of accelerating our growth.

I am in two minds on making a big deal about it, as we close the round.  On the one hand, it is immense validation to have the backing that we have, and that does count for something in the market, whether it is to influence potential users or hires.

Yet, on the other, I don’t want to contribute to more startup porn, with the focus being not only the quality and viability of a business but instead on how big a round one raised, from whom, and how often.

I’d rather help to drive home the point that funding does not equate to success.  Borrowing the phrase from mathematics, it may be a necessary but not a sufficient condition!

What’s the biggest misconception people have about you? Why do they have that? What’s the reality?

This is a tough one.  Looking inward and introspecting is a lot harder than cranking some cold, inanimate project out, as it involves navigating around personal blind spots—unknown unknowns by definition!

The answer may depend on whom you ask, but one does come to mind.  I have long had a reputation for being stubborn.  The “determination” and “perseverance” that I do get complimented for, occasionally, are but other sides of the same coin.  So, the perception may be a function of where someone’s seat is, relative to me, at the table and what their outlook is – beside me, opposite me, expecting something of me, or even looking up to me.

However, as deserving as the reputation may be, I don’t think I have received due credit, especially in close relationships, for being flexible too.  I don’t expect a medal; I am merely reflecting on how I have mellowed, like most people do over time.  (Humbling knocks in life have helped, of course, as was learning to spell self-awareness, starting as late in life as 30.)

Sometimes our reputations precede us, I suppose.  As for what reality is, this favorite quote comes to mind: “Nothing is ever as good or as bad as it seems to be.”  Besides, I have enough other things to worry about than someone’s potential misconception about me.

…Come to think of it, another likely misconception comes to mind: Many acquaintances must think of me as a nice guy.  That may be a nice thing itself, but it’s also dangerous.

I think back to a longstanding dilemma, from my years as a young adult in college and grad school: Do I be polite or do I be honest?  I’d often choose to be polite, so as not to hurt someone’s feelings and to act—and acting is the dangerous part—as a decent person would.

In recent years, though, I’ve done a re-think on this and am biasing more towards communicating honestly, even if bluntly at times, because I think it’s better to be authentic, to be true to ourselves, than to try to be nice.

The challenge becomes this: How to practice radical candor without being an outright jerk?  (Hello, Nassim Nicholas Taleb!)  As a young team mate at work brought up recently, in an enriching conversation on team culture, “Truth without kindness is cruelty.”  (It boggles my mind that she is just a year out of college.) 

I’d encourage others also to practice kind, straight talk.  It takes some getting used to, especially when at the receiving end, so I’d also recommend practicing and using “I statements,” rather than “You statements.”  But it makes for better, authentic dialogue and relationships in the long run.

What gets you excited about this company?

Umm, for one, it’s my baby.  And we know how, even if consensus may be that a baby is outright ugly, it will still be the apple of its parent’s eye.

As for what gets me excited: I am surely biased and may well be delusional (as entrepreneurs by nature are), but the business opportunity is as appealing as when I founded Jodi365.  If anything, it is more real, as the early predictions of how large and untapped the market is have been getting validated.

I am more mindful today of how difficult it is to build a two-sided market, but that makes it all the more gratifying to behold how far we’ve come.  I consider myself fortunate to be still standing, still very much in the game, and still able to be bullish about our business prospects.

It is also very heartening when we hear, as we regularly do, about someone’s having found a match on Jodi365.

Onward and upward! 

Tell us how a day in your life looks like? Your schedule for a day right from the time you get up till you hit the bed at night.

It varies, more so in this extended Covid-19 season.  

I am usually up at 7ish a.m., after going to bed shortly after midnight.  I get online within about an hour of waking up and like to work in a productive burst, without breakfast, until a late lunch.  (It’s seldom before 2 p.m. and often as late as 4 p.m.)  

For better or worse, I am very hands-on with the various aspects of the business.  Mornings start with taking stock of what’s on the work plate for the day of different teams – tech, design, marketing, and customer service.  Indeed, much of my day goes in reviewing the work of team mates and making headway in different areas along with them.  It’s a “manager’s schedule” and not how I’d like to spend most of it.  If I could (afford to) delegate more, I would.  Change has been coming, albeit slowly. 

If there are operational or housekeeping issues, or routine phone calls to make, I strive to defer them to a post-lunch session, when my brain is dulled by a full meal and doesn’t need to be at its sharpest.

I like to carve some time out, at least a few times a week, to get on calls with our users.  It helps in understanding the challenges that singles continue to face, especially as times evolve and even as competing services come and go, after showing shiny new objects to the world.  For the same reason, as and when inspired, several times a week, I also dive into live support chat and customer emails.

Team mates, working from 12+ cities and towns across the country, wrap up their work day between 6 and 8 p.m. and I unwind for a bit after that.

If I don’t get a light morning or pre-lunch exercise in, I do that pre-dinner, which is usually late, by 10 p.m.  One benefit of this pandemic-enforced work-from-home routine is that I can break into occasional, invigorating sets of push-ups or pull-ups at odd times throughout during the day.  I also make it a point to break away from my laptop and take occasional calls outdoors, so that I can walk about while talking, more so between 11 a.m. and 3 p.m., for exposure to the midday sun.  (It is astonishing how many people don’t realize how deficient they are in Vitamin D, an essential nutrient.)

I surf the web; check my social media feeds; do some recreational reading (my Twitter feed is the primary spring board for readings online); keep up with news headlines (even though we’re better off avoiding much of what passes off as news); stock up occasionally on more Kindle books than I may ever get to read; veg out on YouTube a bit (hardly any TV, consciously); enjoy playing Blitz chess online; spend some time with family occasionally, checking on my elderly parents; and catch up with friends online or over the phone some nights.

If the brain isn’t fully fried, I get back online post dinner to attend to unfinished work.  There’s always unfinished work, but the brain isn’t always willing.  When the night shift keeps me up longer than usual and I start the day with insufficient sleep, I don’t hesitate to take a nap of between 30 and 90 minutes after lunch.

Rinse and repeat.  That’s my work week.

I look forward to Saturdays and Sundays.  Only the support team comes online and so I have fewer demands on my time.  That frees me up to keep a “Maker’s schedule,” with larger blocks of time to devote, uninterrupted, to matters and projects that need more than the smaller chunks possible on weekdays.

Rather than fret about not being productive enough, I’m still learning how to get smarter and to be more at peace with what I am able to accomplish each day.

It may not seem like a fun schedule and the risk of burn-out is real.  Yet, so are the consequences of taking one’s hands off the wheel or eyes off the road.  We make time for what matters most to us, after all, and I am grateful to have meaningful work that keeps me occupied, especially when there’s a bloodbath around us in this economy.  As a dear friend and well-wisher likes to remind me, “The pressure of work is far better than the pressure of no work.”

Tell us about your team and how did you meet each other?

For better or worse, I have been a solo founder.  How my team came together is through a patient, deliberate wooing and onboarding of people with the varied skill sets that it takes to build such a business.

It was tough in the early years.  I may have an advanced degree in scientific computing and have done my time as a coder (developing cutting-edge computational-hydrodynamics software), but I haven’t had the skill sets necessary to architect a matchmaking platform.

I used to worry about how it took a team and how potential investors especially like to talk about how they invest only in startups with at least two co-founders.  What may have seemed like a liability early on I have come to see as a strength.  It takes a lot of heart for startup teams to push a boulder uphill for as long as I have.  It would doubtless have been easier with a co-founder or two with complementary skill sets, but it’s more likely that few co-founders would have had the same levels of risk tolerance, hunger, or belief to have kept at it on such a challenging business.  (I have seen a few dozen Indian matchmaking sites and apps surface and disappear over the past decade!)  With a set product and a growing organization now, recruiting the necessary talent is far from the challenge that it once was.

My leadership experience from running an NGO helped in this regard.  Not only was it analogous, in that we were constantly operating in a fast-paced, cash-constrained environment, but also I had to motivate people constantly to step up and help to lift the load, without regard to compensation.  This sage counsel stayed with me and helped: “People like to be a part of something good.”  I focused on enabling and projecting that.

I believed that the longer that I persevered in building something that looked real (in contrast to the original slideware) and good, the easier it would become to attract good talent.  It’s precisely how it has played out.

Something else, which has been enshrined in a core company value, is worth highlighting: I wouldn’t have a business without our online platform.  I wouldn’t have that platform or product without good people to build and run it.  Put your people first and motivate them to put your customers first.  Treat your team fairly.  Help them grow.  The better they get, the better your business gets.

It’s possible.

Know a great startup story or want to share your own? Write to us at and we will get back to you. For more updates follow Bangalore Insider on Facebook and Instagram.

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Bhumikka Yaadav

Hi, I am Bhumikka Yaadav. I did my post-graduation in marketing. I hold a total of 7.5 years of experience. I currently work with BangaloreInsider. I used to work in an e-commerce company before working on my current profession. I love being associated with BangaloreInsider because I enjoy connecting and interacting with a whole bunch of talented people. And these startups keep me motivated as well.

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