Roshan Cariappa – Being Pragmatic Will Save You From Startup Failure

Mar 16, 2021

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BIO: Roshan Cariappa has over 12 years of experience as an entrepreneur and operator at early and growth-stage startups, specializing in going from zero to one and setting up cross-functional teams. Currently, he heads Marketing at Vymo, one of the fastest-growing SaaS startups in India.

STORY: Roshan started his business in 2012, offering marketing services to startups and small businesses. He then pivoted to offering digital assets when digital marketing hit. The business was quite a success. In 2015, there was a vast consumer internet boom in India, and so Roshan thought he’d take advantage of this and pivot his business to offering tech products. He created an app to connect families. This was a huge change that worked against his company. In a few short years, the business failed.

LEARNING: Pivoting is about making small changes, not huge ones. Do not go all in; make room for risk and probability and always have a plan B.

“You can be super optimistic about your vision, but be a little pragmatic, or even slightly pessimistic about your execution.”

Roshan Cariappa

Guest profile

Roshan Cariappa has over 12 years of experience as an entrepreneur and operator at early and growth-stage startups, specializing in going from zero to one and setting up cross-functional teams.

Currently, he heads Marketing at Vymo, one of the fastest-growing SaaS startups in India, and also runs Bharatvaarta podcast (Politics, Policy, & Culture focused on India) and The Startup Operator podcast (wisdom from Indian founders, operators, and investors).

Worst investment ever

In 2012, Roshan started a business offering marketing services to startups and small businesses. The business then pivoted to building digital assets. Roshan and his team realized that digital was becoming the front and center of business, and people didn’t really have a focal point for all marketing activities. So they took advantage of this and pivoted the business.

For a couple of years, the business was doing well and making good money.

Pivoting a second time

In 2015, the team had an itch to pivot again. This time they decided that they were done with services and decided to build products. They settled on creating an app to connect families.

Going all in

At the time, there was this colossal consumer internet boom in India. There were a lot of new users on the internet, and every app business was getting funded. So there was a lot of optimism in the air. Roshan decided to go all in. He believed they could build the app successfully just as they had done with their previous offerings, the digital assets.

It was not as easy as it seems

Roshan and his team grossly underestimated the time, effort, resources, money, patience, and skills required to build a consumer app.

Roshan soon found out that App Store discovery is quite hard, and an app has to either go viral or spend a ton of money on acquisition. And once you’ve acquired these consumers, you still have to retain them and then make money out of them, which is not a trivial thing.

Having to wind up

Roshan had to wind up after a couple of years of trying to make the app a success. This was quite humiliating for him as he had to let go of people he had hired and nurtured.

The failure of the app drained all of Roshan’s self-confidence. He hit a real low point after this venture.

Lessons learned

Do not go all in make room for risk and probability

While it is good to be optimistic about the outcome of your new idea, it helps to be a little pessimistic about your execution. Before you go all in, think about risk and probability. Consider that things might fail; what will you do in that eventuality? It is always better to be prepared for such an outcome than for it to hit you by surprise.

Always have a plan B

It may sound like a cliche but always have a plan B. There is a lot of survivorship bias, especially when starting a business, so it’s going to take a lot out of you, and it’s good to have a solid plan B.

Andrew’s takeaways

Pivoting is not about making big moves but about small changes

A lot of times, when entrepreneurs want to pivot, they make big changes. But the fact is that a pivot is just a small change. Pivoting from a service to a product or a product to a service is a huge change, and you are no longer pivoting but starting a new business.

Actionable advice

Be deliberate about your choices. It is also imperative to be pragmatic about the present.

No. 1 goal for the next 12 months

Roshan’s number one goal for the next 12 months is to stay healthy and happy and keep his family happy.

Parting words

“I think we underestimate how much success can be had by not doing dumb stuff like, in my case, put everything on the line without a plan.”