Episode 255: Rob May - Founder & CTO, Dianthus

I feel like this interview was long overdue, as I’ve know Rob for a long time. I probably first met him at one of the tech events in Boston… maybe Web Innovators Group or something like that. It was during a resurgence of the tech industry in that region where a new crop of entrepreneurs were building companies and Rob’s company, Backupify, was one of the hot companies in the Boston tech scene. Backupify raised funding from top investors like First Round Capital, Avalon Ventures, General Catalyst, Lowercase Capital and top angel investors like Dharmesh Shah, Chris Sacca, and Jason Calacanis. It was a big deal because he chose to build his company in Boston instead of Silicon Valley or NYC, which helped him make a splash coming from Kentucky. Since having a successful exit with Backupify, Rob has gone on to make a major impact to not only the Boston tech scene, but to the tech industry at large as both an entrepreneur and investor. His latest company is called Dianthus, the world's only AI-first eCommerce company which is acquiring small to medium sized brands and helping them grow faster with a common AI platform that includes not just new technologies, but new AI-centric workflows, processes, and ways of working. The company just announced $11.5M in seed funding led by PJC, Underscore, and Jason Calacanis. In this episode of our podcast, we cover: * The use of AI and the areas that Rob finds the most interesting in terms of use cases. * Rob’s early professional career out of school and a look at how he got into blogging in the early days, including how it has helped him as an entrepreneur. * The story of Backupify, a backup cloud company that was started in 2008 for Salesforce and Google Apps and was acquired by Datto. * His experience as an investor - first as an angel, which includes some amazing advice on how to get started as an angel investor and then his experience as a Venture Partner at PJC. * A deep dive into the creation of his latest company, Dianthus and how they are leveraging AI as a competitive advantage. * Advice for hiring when building out your company. * And so much more. If you like the show, please remember to subscribe and review us on iTunes, Soundcloud, Spotify, Stitcher, or Google Play.