Billion Dollar Unicorns: Strategies From 5 Entrepreneurs

You have already read my recent piece, Bootstrap First, Raise Money Later, as one of the tried and true approaches to building Unicorn companies. In this piece, I want to share with you some other strategies worth looking at as well, as part of our Billion Dollar Unicorns exploration. Each of these has a video conversation from one of our recent 1M/1M roundtables. You only need to listen to the first 30 minutes of each session.

Roll-Ups

Aaron Skonnard, founder and CEO of Pluralsight, one of the very few EdTech ventures out there that are scaling at Unicorn levels, discussed his journey over the last decade. Aaron bootstrapped Pluralsight to $12 million in revenue before raising a $27.5 million Series A at almost a $100 million valuation. From there on, the company has gone on to follow a roll-up strategy with additional funding and is currently valued at close to $1 billion.

Open Source & Freemium

Ross Mason, founder of Mulesoft, has built a terrific commercial Open Source company that is scaling at Unicorn rates, with freemium conversion rates in the 5-6% range. Ross discusses how he got the company off the ground, and built a product strategy that makes such high conversion rates possible. You can also read my Entrepreneur Journeys interview with Ross. We first encountered Mulesoft back in 2008, and covered them in March 2009. The company also bootstrapped first, raised money later.

Fiscal Discipline

Vineet Jain, founder and CEO of Egnyte, is running a potential Unicorn company in the same space as the much-hyped Box – Cloud Storage and File Sharing. In this discussion, we did a deep-dive on the space and how it is likely to evolve over time, including expanding into data management. Egnyte’s strategy is very different from that of Box, and potentially more sustainable, in my opinion. The company also bootstrapped first, then raised money.

Bootstrapping with a Paycheck

Girish Navani, CEO of eClinicalWorks, has bootstrapped a billion dollar Unicorn with a paycheck. Girish didn’t quit his job for two years, while he tested and validated his original product and customer base. Today, 16 years later, he has built a $300 million revenue company that is still 100% bootstrapped, private, and has no desire to sell out or go for an IPO.

Emphasis on IP

Chris Gladwin, CEO of Cleversafe, has built a highly valuable company using a unique and impressive IP strategy in the enterprise storage space. He has NOT bootstrapped, but rather used a ‘fat startup’ strategy. We discussed fat startups, valuation of patent portfolios, and more in this video.

More investigation and analysis of Unicorn companies can be found in my latest Entrepreneur Journeys book, Billion Dollar Unicorns. Unicorns will also be discussed with some special guests during our 1M/1M Roundtable programs over the next few weeks. To be a part of the conversation, please register here. The term Unicorn was coined in a TechCrunch article by Aileen Lee of Cowboy Ventures.

This segment is a part in the series : Billion Dollar Unicorns