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  • Writer's pictureRebecca Hastings

Scaling and Disrupting Online Marketplaces to Millions of Users, with Shirish Nadkarni



I am thrilled to be joined by the brilliant tech entrepreneur and visionary, Shirish Nadkarni! With a career spanning decades, Shirish has left an indelible mark on the tech industry, contributing to the success of iconic products like MSN, Blackberry, and Rosetta Stone.


Shirish co-founded Livemocha, a language-learning platform that rapidly garnered 15 million users across 200 countries. His wealth of experience in launching, scaling, and even exiting tech businesses is nothing short of awe-inspiring.


In this episode, we'll dive deep into Shirish's remarkable journey, uncovering the strategies and insights that propelled him to success. From overcoming the intricacies of marketplace dynamics to the art of retaining end-users and even his thoughts on the future of tech disruption, Shirish will leave you inspired and informed.


Episode Outline and Highlights


● [01:41] Shirish’s Perspective on Jumpstarting a Marketplace

● [07:54] Discussing Marketplaces Evolving into Monopolies

● [12:48] AI's Disruptive Influence on Established Marketplaces

● [15:00] The Potential Challenge to Market Monopolies by Social Networks

● [18:08] Transitioning from Founder/CEO to a Senior Employee

● [21:30] Going from Startup to Acquisition: Shirish’s Key Success Factors

● [26:10] Recognizing the Value of End-User Retention

● [28:47] The Impact of Immigration on Successful Startup Formation


How to Engage End-Users and Successfully Jumpstart a Tech Marketplace


Shirish’s astonishing career contains a series of achievements that impact millions of lives today. As I think about his career, I am fascinated by the number of products that he has been involved in which I used: Hotmail, the Blackberry, and Rosetta Stone which he sold one of his businesses. He co-founded Livemocha, a language learning platform, in 2007. They rapidly grew their users and client base to 15 million in 200 countries. I wanted to get Shirish’s insights on how they were able to gain traction in increasing their users and jumpstarting a marketplace. I was also keen to know his thoughts on jumpstarting a marketplace and how to overcome the chicken-and-egg issue of buyers and sellers.


Below are some of my takeaways:


● Focus on a specific category or geography

● Focus on the supply side of the equation first

● Local is the key to going global

● The best PR is word of mouth - so focus on your product’s value


Shirish gave examples of how this works with DoorDash, Instacart, and Livemocha.


From Startup to Acquisition - Shirish Gives His Top Tips


Shirish is the author of an amazing book, From Startup to Exit: An Insider's Guide to Launching and Scaling Your Tech Business. In our conversation, he generously shared his tips with business leaders who are aiming to scale and someday exit their businesses through selling or acquisition. He is passionate about entrepreneurship and was able to sell businesses in under four years from startup to acquisition. He said that there are two main focus areas that business leaders need to implement:


"One is establishing a company culture because as you grow rapidly, you have to hire people that are compatible with your company culture. But first, you have to establish your company culture, you have to write it down and you have to articulate that constantly as you work with the employees so that culture then gets propagated to the next set of employees and then the next set of employees and so forth"


He continued, “Second aspect, I think, is customer success and customer support. Make sure that your customers love your product, and that they continue to they don't just buy it and don't use it, they buy it and are happy with it because word of mouth can be very powerful, as we saw with Livemocha. And making sure that customers are really happy with the solution is super important.”


Shirish elaborated on these two aspects, with an emphasis on the value of retaining end-users as a primary KPI.


Market Insights and Future Disruptors


Shirish also gave his perspectives on how the current marketplace is being monopolized and what regulations can fix these actions toward consumers. He also gave fascinating opinions on subjects that are mostly relevant in the tech industry such as AI and social media platforms as disruptors. He also shared his thoughts on how immigration is positively impacting the future of technology and innovation.


About Shirish Nadkarni


Shirish Nadkarni is a serial entrepreneur with 20+ years of experience in creating consumer businesses that have scaled to tens of millions of users worldwide. He was the co-founder of Livemocha, the world’s largest language-learning site with 15+ million registered members. Livemocha pioneered the concept of social language learning and was later acquired by RosettaStone. Prior to Livemocha, Shirish was the founder of TeamOn Systems, a mobile wireless e-mail pioneer that was acquired by Research in Motion in 2002. The TeamOn technology served as the core foundation for Blackberry Internet E-mail, which had over 50 million users at its peak.


Major accomplishments include:


  • Co-Founder of Livemocha, the world's largest language learning site with over 15 million registered members. Livemocha was selected as Time Magazine Top 50 sites in 2010 and won the prestigious English Speaking Union award presented by Prince Philip, Duke of Edinburgh. Livemocha was acquired by RosettaStone.

  • Founder of TeamOn Systems, an innovative developer of wireless e-mail technologies. Successfully negotiated acquisition by Research In Motion. The TeamOn technology was the foundation for BlackBerry Internet E-mail which serviced over 50 million mobile users.

  • Contributed to RIM’s early growth in the wireless device market through a partnership with T-Mobile USA. Launched RIM's first smartphone device (7100) with a phone form factor.

  • Established MSN as an industry-leading Web portal. Responsible for Microsoft’s entry into two of the largest application categories on the Internet (E-mail and Search). Successfully negotiated the acquisition of Hotmail and partnership with Inktomi Corporation.

  • Re-established Microsoft as an undisputed market share leader in Windows development tools.

  • Responsible for Microsoft’s early entry and leadership in the PC-based e-mail market.



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