One to Ten

Rags Gupta

Here’s a little secret: Most tech startups get to One.

They build a product, land some customers, and close funding. The harder part? Getting from One to Ten.

Tech founders struggle to progress past early adopter customers and founder-led sales—to grow from a scrappy group in which everyone just pitches in to building out an executive team and a well-functioning organization.

They struggle to go from One to Ten, from Startup to Scaleup.

To be able to scale, tech startups must achieve Product Readiness, build a Repeatable Sales Machine, and scale their Human Capital.

In One to Ten: Finding Your Way from Startup to Scaleup, B2B tech entrepreneurs will discover the tools, frameworks, and principles they need to overcome the inevitable growing pains and plot their own path to Ten and beyond.

Press & Praise

Jeremy Allaire, serial entrepreneur, Founder and CEO of Circle, Founder of Brightcove, former EIR of General Catalyst Partners, former CTO of Macromedia

Rags was instrumental in helping Brightcove go from one to one hundred. Startup founders will greatly benefit from the stories and lessons in this book.

Greg Raiz, Managing Director of Techstars

One to Ten is core reading for founders trying to accelerate their startups toward escape velocity. From sales to operations to goal setting, One to Ten is packed with gems to help founders scale.

David Chang, serial entrepreneur and investor, EIR Harvard Business School, ex-Paypal, TripAdvisor

One to Ten is incredibly spot-on, and it's a valuable "how to" guide for entrepreneurs. In addition to picking up handy tactics, you'll get a clear picture of how others have succeeded and failed at blocking and tackling growing ventures at this stage. At my own ventures, I've directly witnessed many of the same dynamics at play, so the book completely resonates with my experiences. You'll find that the chapters fly by in this well-written and engaging firsthand account. Both new founders and serial entrepreneurs will enjoy and benefit from One to Ten.

A serial entrepreneur and operator, Raghav “Rags” Gupta has worked with a number of startups and scaleups and achieved multiple exits, including being part of the founding management team at Brightcove (IPO), Chief Commercial Officer at Videoplaza (acquisition), GM EMEA at Ooyala, and COO at Humatics. He is currently President of Butlr, the breakthrough proptech startup, as well as Venture Partner at Hyperplane Venture Capital. Rags is an active angel investor, mentor, board member, and advisor working with the likes of MIT Sandbox, Harvard Launch Lab X, Dvinci, Elucidata, and Asylon, among others. Rags studied operations research at Princeton University and lives with his wife and two children outside of Boston.


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