Gary Gregory, CEO and Founder of Sirius Software

I attended the Fall Kick-off for the $50K a couple of weeks ago. Gary Gregory of Sirius Software and MIT alum gave the keynote. Gary's presentation is available for download here.

Notes:

MIT in '69 was a hotbed of scientific discovery and technology development

30% of students lived in fraternities

Joining a frat (ATO) has been key to his success

It taught him how to work in a hierarchy, how to work in a team, and it beat in certain social and leadership skills

He dropped freshman Calc (18.02) 4 times but eventually passed

Got a job in NYC through a MIT connection

Whenever you get on a team, make sure you do your part. People will come back to you if you do a good job.

Being a TA taught him how to teach people complicated things

Joined a MIT spin-off called Computer Corporation of America (CCA)

Started as a Computer Scientist, then worked with customers

If you can blend technical background with an understanding of business and customers, you are at a huge advantage in the marketplace

Moved to Progress Software – basically a group of MIT people (including some frat brothers)

Make sure your expectations are aligned with investors

He left Progress and started Sirius Software. The company has done really well and he receives (and turns down) buyout offers frequently

Easy part for MIT students is the technology. Difficult part is communicating technical concepts to non-tech people

Hard parts of being a tech entrepreneur:
* Develop sufficient understanding of the problem space
* Overcoming risk aversion, be willing to fail
* Assembling the right team

Believes strongly in incremental self-funded start-ups

First two companies he made a lot of money for other people

Make sure you have at least 20% in your hands before you get investors involved.