This document summarizes John Landry's 15 years of experience as an angel investor, highlighting lessons learned about evaluating investment opportunities and ensuring team success. Some key criteria for investment include evaluating whether an idea is addressing a major technological shift, if the product or service fills a scarce niche, and if the founding team has complementary skills. Landry also reflects on factors like the importance of the founding team starting together, maintaining momentum over 1-4 years, and selling investments within 3 years for best returns, rather than holding investments longer without sufficient growth. The document aims to share best practices for angel investors to identify promising startups and increase chances of successful exits.

1. Fifteen Great Years of Angel Investing … and some not as great! What to look for.. What to look out for! Angel Bootcamp – June 2010 John Landry Lead Dog Ventures LLC john@johnlandry.com

2. Let’s talk about Me.. Only for context please! Finance and Male Model Era: 1965 Babson BSBA ’69 > National Shawmut Bank 1974 Technology Era: Chairman and/or Chief Technology Officer Rut 1974 McCormack and Dodge > Dun & Bradstreet 1985 1985 Distribution Management Systems > Cullinet 1987 1987 Cullinet > Computer Associates 1989 1989 Agility Systems > Dun & Bradstreet 1990 1990 Lotus Development > IBM (Lou’s Boy) 2000 1995 Lead Dog Ventures > ???? 1997 Narrative Communications > Excite / AtHome 1999 1999 AnyDay.com > Palm 2001… Lead Dog Ventures formed! 2001 Adjoin Solutions > Computer Associates 2003 2001 AdessoSystems > Don’t Ask 2005 Infostoria > Fatwire 2007 9X Acquired, 36 Boards of Directors, 33 Current LDV Investments Recent Wins: DoubleTake, LogMeIn, Interwise, Maven Recent Investments: BlueLeaf, Daily Grommet, Koko, oneForty, Sonian

3. Criteria #1: Is it Massively Directionally Correct? What’s the Next Big Thing?.. ..it’s probably already here and it’s what you’re most skeptical about! Biggest Opportunity: Software Platform Shifts Disruptive Change vs Sustaining Change Batch to On-Line Transaction Processing PC / Client-Server / Graphical User Interface Web 1.0 > Web 2.0 NOW! CLOMOSO!.. Cloud / Mobile / Social The Perils and Profits of the Stack The Lesson: It’s not just an extension of the past.. It’s completely different! And most likely the leaders of the past won’t be the leaders of the future … and that spells opportunity! Lead Dog Examples: Sonian, Apperian, Daily Grommet.. And Animoto? …but it’s getting harder! Landry’s Theory of Scarcity

4. Criteria #2: If there’s demand, is there scarcity?… if there’s no scarcity there will be no value! The link between future value and scarcity is indisputable..The product, service, IP and the team’s talent must by in demand and scarce

5. Criteria #3 – The Team and Structure … Great People who complement each other! CEO.. The Chief Executive … Gerstner! VP uh.. The Distribution Model Business is defined by Distribution.. Who’s got the scarce idea? Obsessive about monetization.. Yes! Monetization! CTO.. The Vision Guy / Gal… Understand business goals, product management, marketing No nonsense tech credentials Outside Speaker Judge Judy Manager VP Technology.. Genius with all the warts… Back of the envelope design to working machine code.. Today! Non-stop dedication and imagination VP Engineering/Development.. Trains leave on time.. Project, management and hiring skills key Respects the genius… and vice versa. FO.. The Finance Dude Business Head, Budgets, Board Reporting

6. So What? Lessons at 60,000 feet! What Worked Better What Worked Worser Team complementary skills start together development <> innovation visionary driven original BOD / investors Time 1-4 years momentum & morale feature bias fresh stuff Outcomes Sell (50% of 30MM in 3 years) Team overlapping skills brought together later development = innovation manager driven new BOD / investors Time over 4 years (except M&D) no-mentum and no-rale schedule bias bit rot? Outcomes Hold (10% of $300M in 7 years) Cramer: Sell! Sell! Sell!