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Interview with a Successful Startup Founder

Legaats: Why I Stopped Pursuing My 1st Startup Idea

Deepak Chhugani
Deepak Chhugani
March 17, 2018
Category of startup
Social Media
Country of startup
United States
Revenue of startups
Interview with a Failed Startup Founder

Legaats: Why I Stopped Pursuing My 1st Startup Idea

Deepak Chhugani
Deepak Chhugani
March 17, 2018
Category of startup
Social Media
Country of startup
United States
Cause of failure of the startup
Bad Business Model

Legaats was a web app where baby boomers and senior citizens could share their important life lessons. 5 were the causes of its failure.



Hello Deepak! What's your background, and what are you currently working on?

Hello! I’m Deepak. I grew up in Ecuador, my parents are Indian, and I was born in Kenya! I came to the US 7 years ago for college. Up until a year ago, most of my experience was in finance, but was always inclined to start my own business. I quit my last job at BofAML to take a few months off and try to start my own thing. About a year ago, I started Legaats(social platform where baby boomers share & document nuggets of wisdom to pass on to future generations). After 7 months full time, I decided to evolve the business to what now is The Lobby. The Lobby is a marketplace where job candidates buy 1-on-1 calls with employees at top investment banks to get personalized recruiting advice and the chance to earn an employee referral.


What was Legaats? Why did you build it?

Legaats was a web app where baby boomers and senior citizens could store, categorize, and interactively share all their most important life lessons in video, text, or photo format to pass on to future generations. I was inspired by my own grandfather’s autobiography, where I learned a lot about his life and found lots of wisdom I didn’t get the chance to hear from him directly. I wanted to replicate that sensation everywhere, and I felt that no dominant consumer platform had succeeded in tapping the idea of building your “digital legacy.” I really loved the idea of mentorship & wisdom-sharing, so it made sense to me at the time. I also researched and found that half of the US population would be above the age of 50 by the end of 2017, that this age group controlled 70% of disposable income in the country and that they were suffering from the widespread epidemic of social isolation. Legaats was meant to help alleviate that problem!


How did you attract your first customers? Which marketing strategies did you use?

For the initial user base, I attracted them organically through my own network. I’d tell friends about what I was working on, and they’d tell other friends who they thought might be interested. I’d grow the email list as best I could, and try to send out interviews & pieces of wisdom I’d score from top-notch executives that I knew people would want to read about. These executives were previous mentors, fathers of friends, and really random people I’d meet through warm introductions who were attracted to the concept.

Why did you stop trying taking Legaats forward?

The main reasons were: a) too slow to validate assumptions, b) no clear business model, c) lack of empathy with target users, d) not enjoying execution, and e) no unique competitive advantage. In more detail:

Too slow to validate assumptions:

In a previous version of this article, I said that our main problem was not having a tech co-founder for this specific idea. In hindsight, that was wrong. Not having a tech cofounder hindered our ability to build technology quickly & cheaply, but the reality is that we could have done dozens of cheap low-tech experiments to validate our core assumptions (i.e. do senior citizens alleviate social isolation by documenting life lessons using an online product? How easy is this behavior for a typically non-tech savvy audience?) I was too obsessed with trying to build something just to show people in the industry that I had built some sort of digital product, when in reality it would have been much smarter to validate our core idea quickly and spending as little as possible. Our current venture, The Lobby was validated through an unpaid LinkedIn status and spreadsheets, where we made hundreds of dollars without writing a single line of code and without any technical person involved.

No clear business model:

I may be wrong, but I think we’re way past the age where you can build a consumer-facing startup without a clear business model and hope to monetize once you have millions of users. I’m sure there still will be success stories in this realm, but with the dominance of FB and Google in the ad-space, it’s hard to see the trend that made companies like Yik Yak and Secret big prevailing. Legaats didn’t have a clear business model, and the only ones I could think of (such as charging for storage) were really not well thought out or validated. With the trends discussed, I think it’s now more important than ever to have a clearer picture of your business model even in the earliest days of your company.


Lack of empathy with target users:

After reading my grandfather’s autobiography, I thought everyone would want to know this kind of stuff about their own ancestors. Thus, I convinced myself that my experience was enough of a passion-driver that I’d figure out how to replicate this sensation for people everywhere.

The reality is much more subtle & nuanced. I started building a solution for an audience I fundamentally could not empathize with. I enjoyed mentorship and reading wisdom-type content from my grandfather, on Quora, and on Medium, but I did not understand what it took to actually get people of that age group to actually create it, and frequently.

How could I assume seniors solve their social isolation by using a web app? Maybe they just need their own families to visit them more? I’m sure someone will build something that alleviates this demographic’s isolation issue, but it will probably come from someone who can deploy a much higher degree of empathy with this audience than I ever could.


Not enjoying the execution:

This was the one I least expected, but probably the single most important reason I stopped working on Legaats. All the learnings above could have made me choose to pivot our model or probe into a more focused, tangible problem to solve for this audience; however, because I wasn’t enjoying the execution I decided to do something different altogether.

I was just not enjoying the most basic things about the process. I remember the first few meetings with my users who were 50+ years-old CEO’s, and I was deriving so much amazing wisdom & insight from them, it felt like a dream come true that this was my job.

However, I quickly realized that one thing was enjoying my conversations with them, and another was getting them and myself to produce this content online. This was incredibly frustrating, difficult, and inefficient.

Try explaining to 70 & 80-year olds how to write “blog-style” posts on a web app or to record videos of themselves giving advice and you’ll see what I mean.

Again I’ll say, someone might figure this out, but I came to a conclusion that it should probably not be me. I think the biggest red flag was when I realized I didn’t even feel like getting my own grandmother to use the product.


No unfair competitive advantage:

This last one was also very important to me. Up until Legaats, I had spent my entire life working on things that were extremely related to finance and business. Yet, here I was, trying to build a social digital product, where most conceivable success stories with those kinds of products started with at least one great coder on the team who put these products together for fun.

Looking back, it was pretty presumptuous of me to think I was going to figure out some strategy to hook millions of people on to a web application without even understanding the basics of building a simple website, without ever having worked with engineers, or having someone with those skills by my side.

That’s not to say it’s impossible, even for someone in my shoes — I just realized that life is short, and I’d probably prefer trying to start something where I actually have some unique insight or competitive advantage.

My new startup idea is based upon my existing network of top professionals and is essentially solving a problem that I solved for myself and that I’ve helped dozens of others solve over the years as a hobby.

In short, it’s a problem I know exists and it’s one that I understand. The execution is something I unconsciously enjoy because I’ve been doing it for so long on the side. Maybe our current solution isn’t the best way to solve it, but the fact that we got dozens of paying customers from day 1 with $0 investment is a much better start than what I was doing with Legaats.

Also, I can have empathy with my users because I’ve been on both sides of that market, and I also have what I think is a unique insight, which seems to be driving some of our initial traction. If I didn’t have this insight or my network as an advantage, I probably would’ve moved on to another idea, given what I learned with Legaats.


What were your biggest disadvantages?

Two big ones: a) inexperience on what it takes to cheaply validate startup ideas and b) not being the target user for my own product. Elaborated on above.

If you had to start over, what would you do differently?

It’s hard to answer this because this is how most of the people I respect learned the same hard lessons – by giving it a shot. However, in an ideal world, if I could go back with the knowledge I have today, this is how I would’ve gone about executing or at least validating Legaats:

I would have started a YouTube channel where I would ask 3-5 families to post videos of their grandparents reciting life lessons and videos every week. This costs $0 and I would have truly been able to emulate the user behavior which is getting people of this age group to interact with technology and document pieces of wisdom.

I would have then proceeded to collect arduous feedback on this entire process (i.e. did this make you feel better, how hard was this, etc.) and studied the challenges of getting people in this demographic to interact with technology as a solution to their emotional issues. 

To be honest, I can’t tell you more because, with my new mentality, I would have done this long enough to then figure out my next step. It would have been a much more iterative process. I’d have saved tons of money doing things this way and still learned more about my users than what I did in 7 months with Legaats. I would also have focused much more harshly on potential business models before plunging into spending any money on development or deciding to pursue the idea.

Lastly, I would have been much more ruthless on detaching myself from my idea. The more I think I can do this, the more merit whatever I choose to do will actually have.


Did Legaats’s failure help you achieve success with The Lobby? In which ways?

We haven’t yet “succeeded” in The Lobby, but the experience with Legaats definitely helped me gain some meaningful perspective on how to truly solve a real problem, and not one that sounds plausible in my head. That, as well as most of the other lessons mentioned in here.


What's your advice for someone who is just starting?

One phrase to all my fellow solo nontechnical founders:

"You don’t need a web app, a product, or too much money to validate your idea."

Everything you’re saying or thinking to convince yourself that you do is not true, and you’ll have a much less painful experience if you listen to what I’m saying. Solve a real problem, and find the cheapest way possible to figure out if people give a crap about what you’re doing and if they’re willing to pay for it. Even with the most techie concepts, you can now build a landing page for free, spend $10-$50 on FB ads, and figure out if there’s demand for the product. You can also leverage tons of other existing technology to help you get you a cheap MVP that isn’t completely low-tech (YouTube channels, email newsletters, landing pages, spreadsheets, free trials of necessary tools, etc.).


Which entrepreneur book would you recommend?

My two favorite work-related books are Zero to One by Peter Thiel and Outliers by Malcolm Gladwell. Zero to One really helped me understand that in order to do unique or extraordinary things, you have to think in a unique way. By thinking like the rest of the world, it’s easy to follow what everyone else does or says and lose the ability to think individually and objectively.

Outliers by Malcolm Gladwell reinforced a very important concept for me which is that there is no such thing as an overnight success. Every person who became successful “overnight” had countless hours of deliberate & hard work before they reached a point of visible success. This book is mostly a reminder that if I want to achieve my goals, I should focus on putting my head down and trying to get a little bit better every day, instead of trying to find shortcuts.


Where can we go to learn more?

Check out The Lobby and please send it to any friends trying to break into investment banking! We also have a YouTube channel for events we've hosted, with speakers such as the co-founder of Classpass, co-founder and CEO of Trigger, and head of growth at Velocity.

I occasionally write on Medium and answer IB-related questions on Quora.

Feel free to reach out at deepak@thelobby.io! Thanks for having me!


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