Roy Rodenstein CMU Boston Entrepreneurs Group 3/3/11

1. An Entrepreneurial Journey:Flowers Smelled, Lessons Learned Roy Rodenstein CMU Alumni Association 3/3/2011

2. About Me @royrod how2startup.com Companies Mentor Investor/Advisor UX researcher early employee acquired by co-founder acquired by

3. What’s An Entrepreneur? Stomach of steel quitting job, no pay, uncertainty/risk massive ups and downs Self-starter Bounce back from rejection Driven to realize a vision Skills, ability & willingness to learn No ego menial, dirty work Zen view on all feedback Go for it!

4. Going.com & BootstrappedLocal Marketing

5. Going History in a Nutshell $500k Seed Additional Funding Co-found Going.com Acquired Rejected by YC $3M Series A Quit Day Job 2005 2006 2007 2008 2009

6. What’s So Hard About Local? Product “Cold start” problem, per geo Need local relevance, e.g. content Geo Branding VillageVoice, SF Weekly Good luck getting Voice.com

7. What’s So Hard About Local? Marketing WoM is limited “Is Going available in other cities?” “Should I tell my friends in Chicago?” Traditional methods Can’t use cheap national/non-geotargeted! Impacts SEM, banners, affiliate, PR, etc. SEO Geo subdomains etc., duplicate content

8. 1. Prove It In 1 Geo, Then Scale Started in Boston, Spring ‘05 Prototyping, customer development etc. Added NY and SF after BOS reached 10k Started with stringers/part-timers

9. 2. Bootstrap Local Marketing Grew marketing in concentric layers… 1st: 100 close friends + family 2nd: attended 4 house parties/night with my cofounder for 3 months 3rd: created our own events, traditions 4rd: cross-marketing w/local orgs Young alumni club, salsa fans group, etc. 5th: hire local stringers for 5 hrs/wk

10. 3. Scale Marketing w/Funding 6th: Launch event in Boston Fenway Fest: TV, subway, partner promos Red Sox said no-go afternoon before. Ouch. 7th: National launch at Demo ‘06 8th: Hired local full-/part-time staff 9th: SEM (geo-targeted) 10th: Launch events in NY, SF, Chicago 11th: Local PR

11. Fenway Fest Subway Ad (Boston, Sept. 06)

12. Early Stage Team-Building

13. How I think about early stage teams What are my strengths & weaknesses? Skills: Hacking, Product, Marketing, Sales, Finance, Management Qualities: detail oriented vs. macro view, people person, communication Be brutally honest with yourself What strengths does the company need Now? In 6 months? In 2 years? What are sporadic vs. sustainable roles?

14. Sporadic needs “We need a new logo, so I need to hire a full-time designer ASAP!!!” Full-time hires are hard 1-3 calendar months, days of real effort on spec, interviews, negotiation Firing is really hard Hiring wrong person full-time is very costly Layoffs take toll on the team and your credibility When in doubt, start with low commitment Temp-to-hire is very common

15. Common staffing approaches

16. Sustainable needs “This area needs help now, and it still will in a year” Someone will need to lead Hacking, Product, Marketing These problems don’t “go away” Could be a founder, a sr. hire, or a jr. hire that ‘scales’ Wearing multiple hats for a while is fine Plan out hires at least 6-12 months in advance (e.g. Excel gantt)

17. What makes a founder? Believes in the vision Committed to the company Sustained fit and value “My cofounder will help a bit with emailing bloggers and users, taking a shot at drumming up some potential clients, and later we’ll figure out what else they do”

18. What a co-founder blowup looks like Spooks your investors, your team, and your cap table

19. Where to find full-time Hires Your friends Your network Craigslist Joel on Software Dice College career fairs Monster Careerbuilder Crunchboard Your friends’ networks Twitter Quora LinkedIn Facebook Blog comments Your user community Meetup groups Industry events Everywhere…

20. Fundraising Debugged

21. Fundraising Decoder Ring

22. Boston, SF, NYC: How They Stack Up Boston Great for Mobile, B2B/SaaS, E-Commerce etc. Pro: If you recruit a star, better chance to hold onto them Con: Few superangels/MicroVCs, so seed round valuations lower SF #1 by far for Consumer, Web, Gaming, etc. Pro: Can swing a dead cat and hit an angel investor; bubbl-y $$ Con: FB, Google steal all great hackers and drive prices up; no loyalty NYC Great for Ad Networks, Fashion, Cloud, ‘Hip’ Services Pro: Growing angel and VC scene, though still smaller than Boston Con: Expensive to operate other than deep Brooklyn or NJ

23. Further Resources Angel, Incubator, VC Lists Xconomy: http://www.xconomy.com/boston/resources/ Jon Pierce Boston Angels List: http://twitter.com/jonpierce/boston-angels Relevant Blogs VentureHacks: http://www.venturehacks.com Mark Suster: http://www.bothsidesofthetable.com Brad Feld: http://www.feld.com Chris Dixon: http://cdixon.org Fred Wilson: http://www.avc.com Paul Graham: http://www.paulgraham.com/articles.html (me): http://how2startup.com Documents YC Series AA Funding Docs: http://ycombinator.com/seriesaa.html AVC Seed Docs: http://avc.com/a_vc/2010/03/standardized-venture-funding-docs.html Wilson Sonsini Term Sheet Generator: https://dealbuilder.wsgr.com Boston Dart Boston: http://dartboston.com Greenhorn Connect: http://www.greenhornconnect.com Web Innovators Group: http://www.webinnovatorsgroup.com Techstars: http://techstars.org/boston MassChallenge: http://www.masschallenge.org/