Shirish Nadkarni, Founder, Livemocha; TeamOn Systems

Shirish Nadkarni, Founder, Livemocha; TeamOn Systems

Shirish Nadkarni is a Serial Entrepreneur with proven success in creating multiple consumer businesses that have scaled to tens of millions of users worldwide. Shirish was the co-founder of Livemocha, the world’s largest language learning site with 15+ million registered members from over 200 countries.



This episode of The Brand Called You brings you lessons on entrepreneurship, investment and running a business from a well established entrepreneur who has done a lot of startups and now advises and invests in startups. We are privileged to welcome the founder of Livemocha and TeamOnSystems.

Shirish is an quintessential entrepreneur with several successful startups and exits. He is also an angel investor.

Shirish has also authored a book titled ‘From Startup to Exit: An Insider’s Guide to Launching and Scaling Your Tech Business’.

Shirish’s Successful Exit

Shirish tells us that he founded two companies, TeamOnSystems, which was an early pioneer in mobile email. In 2002, the company was acquired by BlackBerry.

In 2007, Shirish founded another company called Livemocha which pioneered the notion of social language learning where one could learn other languages from their native speakers. In 2012, this company was acquired by Rosetta Stone.

Pros and Cons of having a partner and going solo

Shirish says that most of the VCs don’t fund start-ups that do not have multiple partners unless one is a successful entrepreneur. He also tells us that in both his startups he had co-founders who helped him. He says it is very lonely at the top, so it is beneficial to have partners who can help you arrive at the right decision.

Common Mistakes that Startup Entrepreneurs Make

Shirish tells us that he has seen two main mistakes that are made by founders. They are:

  • Not doing enough research to understand the pain point the entrepreneur is trying to address.
  • Not spending enough time in making the Product Market Fit and starting spending money on marketing.

At what stage should a Startup start to scale up?

Shirish talks about two things after an entrepreneur should think of scaling up. They are:

Product Market Fit

Shirish tells us that a Startup should start to scale up as soon as it has achieved the Product Market Fit. To find out whether one has achieved it or not, one should look at his user growth, potential customers, customer retention etc.

Perfecting Sales Motion

If an enterprise has perfected its sales motion in a manner that is profitable, it should probably think of scaling up and pouring the money in.

Bootstrapping versus raising money

Shirish generally advises the entrepreneurs to bootstrap until they have customer traction. Once the enterprise has a few customers that are really enthusiastic about the product, the enterprise can go to investors and present to them that it has achieved the product market fit. Shirish adds that if one bootstraps for too long, then you run the risk that you are not growing fast enough.

What are the key metrics Shirish looks for in an Enterprise, before investing in it?

There are many factors that Shirish looks for in an enterprise before making an investment. However, the following are the key metrics he sees:

Founding Team

Shirish first looks at the founding team, it’s worth, the level of expertise they have, their understanding of the industry etc.

Product Market Fit

Has the enterprise achieved product market fit or not, do they have traction with their customers or not etc.

Customer Retention

If an enterprise is acquiring customers and retaining them well, Shirish considers it a good aspect for an affirmative decision of investing in the enterprise.

As an angel investor, how involved does Shirish get into the internal affairs and governance of the company

Shirish says that he doesn’t make an investment just for the sake of investing. Instead he invests in the companies in which he believes that he could add value. So he advises and mentors those companies from time to time, or he takes the formal advisory role and tries to spend enough time with them.

Shirish’s advice for the Product Market Fit

  • Shirish believes that if one wants to achieve the product market fit, he first needs to focus on the problem that customers are facing.
  • If the problem the entrepreneur is addressing is not among the top three problems of the customers, he immediately needs to pivot and ask the customers more about their problems and solutions needed for them.
  • After that he needs to figure out the solution and build a product according to it.
  • Then the entrepreneur can get some customers to use it for trail, get feedback and
  • then make adjustments accordingly.

Shirish’s advice to the Young Entrepreneurs starting their journey

Shirish advises the young entrepreneurs to explore the Startup world as early as possible because at that time you have more potential and lesser risk.


Shirish Nadkarni is a serial entrepreneur with proven success in creating multiple consumer businesses that have scaled to tens of millions of users worldwide. Shirish was the co-founder of Livemocha, the world’s largest language learning site with 15+ million registered members from over 200 countries. Livemocha was acquired by RosettaStone in 2013. Prior to Livemocha, Shirish was the founder of TeamOn Systems, a mobile wireless e-mail pioneer that was acquired by BlackBerry in 2002. The TeamOn technology served as the core foundation for Blackberry Internet E-mail which serviced over 50 million BlackBerry users. Shirish started his career at Microsoft where engineered the acquisition of Hotmail and launched MSN.Com which became a leading web portal in the early days of the internet. Shirish is the author of “From Startup to Exit – An Insider’s Guide to launching and scaling your Tech business”.

Shirish received his MBA from Harvard Business School and a BSE in Electrical Engineering from the University of Michigan. He serves on the board of TiE Seattle where he chairs a number of programs including the GoVertical Startup Creation Workshop, the TiE Entrepreneur Institute and the Z5 Catalyst funding initiative.

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