Roy Rodenstein shares his experiences as an entrepreneur and lessons learned from founding Going.com and BootstrappedLocal Marketing. Some key points include: - He started by proving the concept in one city (Boston) before scaling to other cities like New York and San Francisco. - Early marketing efforts focused on friends/family and local events to build awareness within specific geographies. - Funding was used to launch larger local marketing events and hire local staff to further grow in existing cities and expand to new ones. - Advice is given around early team building, when to hire full-time vs part-time/contractors, and fundraising strategies for different cities.

1. An Entrepreneurial Journey:Flowers Smelled, Lessons LearnedRoy RodensteinCMU Alumni Association3/3/2011

2. About Me@royrod how2startup.comCompaniesMentorInvestor/AdvisorUX researcherearly employeeacquired byco-founderacquired by

3. What’s An Entrepreneur?Stomach of steelquitting job, no pay, uncertainty/riskmassive ups and downsSelf-starterBounce back from rejectionDriven to realize a visionSkills, ability & willingness to learnNo egomenial, dirty workZen view on all feedbackGo for it!

4. Going.com & BootstrappedLocal Marketing

5. Going History in a Nutshell$500k SeedAdditional FundingCo-found Going.comAcquiredRejected by YC$3M Series AQuit Day Job20052006200720082009

6. What’s So Hard About Local?Product“Cold start” problem, per geoNeed local relevance, e.g. contentGeo BrandingVillageVoice, SF WeeklyGood luck getting Voice.com

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

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

9. 2. Bootstrap Local MarketingGrew marketing in concentric layers…1st: 100 close friends + family2nd: attended 4 house parties/night with my cofounder for 3 months3rd: created our own events, traditions4rd: cross-marketing w/local orgsYoung alumni club, salsa fans group, etc.5th: hire local stringers for 5 hrs/wk

10. 3. Scale Marketing w/Funding6th: Launch event in BostonFenway Fest: TV, subway, partner promosRed Sox said no-go afternoon before. Ouch.7th: National launch at Demo ‘068th: Hired local full-/part-time staff9th: SEM (geo-targeted)10th: Launch events in NY, SF, Chicago11th: Local PR

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

12. Early Stage Team-Building

13. How I think about early stage teamsWhat are my strengths & weaknesses?Skills: Hacking, Product, Marketing, Sales, Finance, ManagementQualities: detail oriented vs. macro view, people person, communicationBe brutally honest with yourselfWhat strengths does the company needNow?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 hard1-3 calendar months, days of real effort on spec, interviews, negotiationFiring is really hardHiring wrong person full-time is very costlyLayoffs take toll on the team and your credibilityWhen in doubt, start with low commitmentTemp-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, MarketingThese 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 finePlan out hires at least 6-12 months in advance (e.g. Excel gantt)

17. What makes a founder?Believes in the visionCommitted to the companySustained 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 likeSpooks 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 UpBostonGreat for Mobile, B2B/SaaS, E-Commerce etc.Pro: If you recruit a star, better chance to hold onto themCon: Few superangels/MicroVCs, so seed round valuations lowerSF#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 loyaltyNYCGreat for Ad Networks, Fashion, Cloud, ‘Hip’ ServicesPro: Growing angel and VC scene, though still smaller than BostonCon: Expensive to operate other than deep Brooklyn or NJ

23. Further ResourcesAngel, Incubator, VC ListsXconomy: http://www.xconomy.com/boston/resources/Jon Pierce Boston Angels List: http://twitter.com/jonpierce/boston-angelsRelevant BlogsVentureHacks: http://www.venturehacks.comMark Suster: http://www.bothsidesofthetable.comBrad Feld: http://www.feld.comChris Dixon: http://cdixon.orgFred Wilson: http://www.avc.comPaul Graham: http://www.paulgraham.com/articles.html(me): http://how2startup.comDocumentsYC Series AA Funding Docs: http://ycombinator.com/seriesaa.htmlAVC Seed Docs: http://avc.com/a_vc/2010/03/standardized-venture-funding-docs.htmlWilson Sonsini Term Sheet Generator: https://dealbuilder.wsgr.comBostonDart Boston: http://dartboston.comGreenhorn Connect: http://www.greenhornconnect.comWeb Innovators Group: http://www.webinnovatorsgroup.comTechstars: http://techstars.org/bostonMassChallenge: http://www.masschallenge.org/