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#m4s




MONEYBALL STARTUPS           +
        IT’S NOT SPRAY AND PRAY. IT’S A PROCESS.



                      PAUL SINGH

                      500 Startups

 @paulsingh・paul@500startups.com・resultsjunkies.com/blog
#m4s




 GETTING TO KNOW




500 STARTUPS       BECAUSE WE’RE KIND OF A BIG DEAL




                     PAUL SINGH

@paulsingh・paul@500startups.com・resultsjunkies.com/blog
#m4s




THE BIG OPPORTUNITY IN EARLY STAGE TECH INVESTING:




API TO VENTURE CAPITAL
& FUNCTIONAL EXPERTISE
(FOR FOUNDERS. FOR INVESTORS. FOR GOVERNMENT.)
#m4s




FOUNDERS:




BUILD SOMETHING
PEOPLE WANT
#m4s




INVESTORS:




WRITE CHECKS AND
ADD VALUE
#m4s




GOVERNMENT:




MAKE LIFE EASY
FOR INVESTORS &
FOUNDERS
#m4s




“ VENTURE CAPITAL IS
  OPEN TO ATTACK BY
  DISRUPTIVE NEW
  BUSINESS MODELS AND
  TECHNOLOGY.
  -- NAVAL RAVIKANT (@naval)
#m4s




(R)EVOLUTION IN THINKING
#m4s




 EARLY STAGE
  STARTUPS
HAVE CHANGED
#m4s




 CLOUD, OPEN SOURCE AND ONLINE DISTRIBUTION DRIVING




 STARTUP COSTS
LOWER THAN EVER
           BUT SCALING STILL COSTS MONEY
#m4s




 WEB GETS BIGGER.
WORLD GETS SMALLER.
#m4s




  TRACTION IS THE NEW
INTELLECTUAL PROPERTY
PLATFORMS (SEARCH, SOCIAL & MOBILE) PRIMARILY DRIVING THE CHANGE.
  NO LONGER “GOOD ENOUGH” TO DEPEND ON TECH DIFFERENTIATION.
#m4s




   CAPITAL
INCREASINGLY
COMMODITIZED
   RISE OF THE ANGELS, YO!
#m4s




 NEW REALITY:
MONEY FOLLOWS
  FOUNDERS
#m4s




      SIGNALS ARE
      EVERYWHERE
BIG DATA + OPEN SOURCE ANALYTICS = NEW TECHNIQUES FOR VC
#m4s




WALL STREET
BEAT US TO IT
#m4s
#m4s




“   UBS PROPRIETARY
    SATELLITE PARKING LOT
    FILL RATE ANALYSIS
    POINTS TO AN
    INTERESTING CADENCE
    INTRA-QUARTER AND
    POTENTIAL UPSIDE TO
    OUR VIEW.
#m4s
#m4s




“
TWICE A WEEK A SMALL
HELICOPTER CIRCLES
OVER CUSHING’S TANK
FARMS ON AN OIL
INDUSTRY SPYING
MISSION.
#m4s




    WALL STREET
    ISN’T ALONE
THESE TECHNIQUES ALREADY USED TO UNDERWRITE IN-VITRO
  FERTILIZATION LENDING, PAYDAY LOANS, SUBPRIME AUTO
  LENDING, HOME/PERSONAL/AUTO INSURANCE AND MORE.
#m4s




IT TURNS OUT,




WE CAN DO IT, TOO
                SURPRISE!
#m4s




+ “GUT” + TRUSTED MENTORS + MUCH, MUCH MORE DATA.
#m4s




        SENTIMENT
         ANALYSIS
WHAT IS THE TEAM THINKING? WHAT DOES THE MARKET THINK?
           WHAT DO MY PEERS/MENTORS THINK?
#m4s




   NEEDLE IN THE
    HAYSTACK
 REAL USE CASES: SIGNS THAT A FUNDING ROUND IS ABOUT TO
OCCUR AND/OR SIGNS THAT A PRODUCT IS ABOUT TO EXPLODE.

  VERY HARD TO DO ACCURATELY BUT PAYOFF IS BIG & FAST.
#m4s




FASTER PORTFOLIO
    TRENDS
  CURRENT SYSTEMS OF QUARTERLY/AD-HOC REPORTING IS
    BROKEN -- SELF REPORTED DATA IS OFTEN BIASED.

THE RAW DATA IS THERE, THE SYSTEMS TO COLLECT IT AND THE
         ALGORITHMS TO ANALYZE IT ARE MISSING.
#m4s




     500 CHECKLIST
Product solves a problem for a specific target customer
Capital-efficient businesses - operational @ <$1M funding
Primarily internet-based distribution - search, social, mobile, local
Simple revenue models - transactions, subscriptions or affiliate
Functional prototype before investment (or previous success)
Small but measurable usage - some customers, early revenue
Small but cross-functional team - engineer, design/UX, marketing
#m4s




EARLY STAGE VC
 IS CHANGING
 HAS CHANGED
#m4s




STATE OF THE ART IN EARLY
 STAGE INVESTING IS NOT
   VERY SOPHISTICATED
     TRUST REFERRALS. MOVE FAST. KEEP LEGAL/FINANCE SIMPLE.
BUILD RELATIONSHIPS WITH OTHER INVESTORS, SYNDICATE EVERYTHING.
#m4s




MONEYBALL
IT’S NOT SPRAY AND PRAY. IT’S A PROCESS.
#m4s




           MY PRIMARY GOAL IS TO




      BUY WINS
NOT NECESSARILY BUYING INTO THE HOTTEST DEALS.

 FOCUS ON TEAM, EXECUTION, TRACTION & DATA.
 (STICK AROUND... I’M GOING TO SHOW YOU HOW)
#m4s




INITIAL BET DESIGNED TO
 GIVE US MORE DATA FOR
    SUBSEQUENT BETS
#m4s




   QUANTITATIVE
    PORTFOLIO
    APPROACH
BENEFITS: CONTROLLED RISK + OUTSIZED RETURN POTENTIAL
#m4s


                                   Monte Carlo Simulation of Angel Investing
                  5

                                   mean              median                 std dev
                3.75
Exit Multiple




                 2.5



                1.25



                  0
                       0   2   4   6   8   10   12    14   16     18   20   22   24   26   28   30
                                                     # of Deals
#m4s
    MODERN PORTFOLIO THEORY:




RISK MITIGATION
   THROUGH
DIVERSIFICATION
#m4s




    HIGH VOLUME
 INVESTING ALLOWS
FOR HIGH ERROR RATE
#m4s




   TRACK IRR &
VALUATIONS WITHIN
 YOUR PORTFOLIO
   AT LEAST YEARLY. RECOMMEND QUARTERLY.
#m4s




CONTROLLED RISK:
OUTSIZED RETURN
   POTENTIAL
#m4s




  PORTFOLIO IRR
 QUICKLY POSITIVE
(WITH SMALLER EARLY EXITS AND PROMISING DEALS GETTING FUNDED)
#m4s




EVEN “SMALLER”
EXITS CAN MOVE
  THE NEEDLE
  DON’T FORGET: YOU CAN SELL POSITIONS TO
  DOWNSTREAM OR SECONDARY BUYERS TOO.
#m4s




INDIVIDUAL BETS
   ARE SMALL
  MUCH EASIER TO RUN AN EXPERIMENT ON A
   $50K INITIAL CHECK INSTEAD OF $250K+
#m4s




               BAD BETS
               FAIL FAST
SMALLER CHECK SIZES FORCE COMPANIES TO PROVE THEORIES FASTER.
ALLOWING INVESTORS TO QUICKLY ITERATE OUR FORECASTING/FUNDING
   MODEL. FEWER “LIVING DEAD” AND QUICKER RETURN ON RESULTS.
#m4s




       FAILURE RATES
         ARE HIGH
 DIVERSITY OF HIGH VOLUME INVESTING ALLOWS FOR HIGH ERROR RATE.
FUND IRR QUICKLY POSITIVE WITH SMALLER, EARLY EXITS AND PROMISING
                      DEALS GETTING FUNDED.

DILIGENCE HAPPENS IN THE REAR VIEW MIRROR, NOT THE CRYSTAL BALL.
#m4s




ALLOCATE FOR FOLLOW-ONS
            30% Capital - Initial Bets
                         target 10-20 deals




            70% Capital - Follow On
              filter out failures, follow-on the top 20%




    (...OR “HOW TO AVOID GETTING SQUASHED”)
#m4s




DEAL TERMS
SO YOU FOUND A STARTUP YOU LOVE?
#m4s




DEBT VS EQUITY
#m4s




CONVERTIBLE NOTES
 ARE OK (REALLY!)
 LOWER LEGAL FEES, LESS DOCS, QUICKER TO EXECUTE. WHEN
    CAPPED, THEY FUNCTION SIMILAR TO PRICED ROUNDS.
#m4s




 STANDARD DOCS
ARE YOUR FRIENDS
 WHEN IN DOUBT, DO NOT INNOVATE IN FINANCE OR LEGAL
#m4s




   PRO RATA &
   INFO RIGHTS
ALWAYS. ALWAYS. ALWAYS. ALWAYS. ALWAYS. (GET IT?)
#m4s




      FOCUS ON
     VALUATION &
      MULTIPLES
OWNERSHIP % MATTERS MUCH LESS. FOCUS ON REQUIRED EXIT
  SIZE RATHER THAN SOME MYTHICAL OWNERSHIP TARGET.
#m4s




 IT’S HARD TO MAKE
      MONEY ON
 VALUATIONS > $5M
(PRO TIP: CONSIDER MIN. RETURN REQUIREMENTS FOR DOWNSIDE SCENARIOS)
#m4s




                   YOUR PRIMARY GOAL




LET FOUNDERS GET
  BACK TO WORK
THIS IS A LONG GAME: AVOID LOSING YOUR REPUTATION OVER 1%.
     WHEN IN DOUBT, LEAN TOWARDS THE ENTREPRENEUR.
#m4s




AVOID BOARD SEATS
#m4s




 MOST BOARDS
PROVIDE MINIMAL
   VALUE-ADD
#m4s




BEST DEALS USUALLY
  REQUIRE LIMITED
  BOARD SUPPORT
 SPEND YOUR TIME SOURCING NEW DEALS. LIMIT TIME ON
  SIDEWAYS DEALS. LET THE WINNERS KEEP ON WINNING
   (AND ANSWER YOUR PHONE WHEN THEY NEED YOU).
#m4s




DO NOT INNOVATE IN
 FINANCE OR LEGAL
#m4s




     INVESTING
   IS A PROCESS
DABBLING IN INVESTING IS (AT BEST) GAMBLING. BETTER TO
 WALK AWAY OR PURSUE INVESTING NEARLY FULL TIME OR
       FIND SOMEONE TO MANAGE YOUR MONEY
#m4s




           BE AN ACTIVE
            INVESTOR
PORTFOLIO EFFECTS & THE LEAN STARTUP MOVEMENT ARE YOUR FRIENDS

YOU CAN EXPECT FAVORABLE WITH 10 DEALS BUT IT TAKES 20+ TO BE SAFE
#m4s




     BE A SMART
      INVESTOR
FOCUS ON INFORMATION ASYMMETRY & PRICE/MULTIPLES.
#m4s




“   BY ITS NATURE, THE
    INTERNET UNDERMINES
    ANYONE WHOSE STATUS
    DEPENDS ON
    PRIVILEGED ACCESS TO
    INFORMATION.
    -- MICHAEL LEWIS
#m4s




THE BIG OPPORTUNITY IN EARLY STAGE TECH INVESTING:




API TO VENTURE CAPITAL
& FUNCTIONAL EXPERTISE
(FOR FOUNDERS. FOR INVESTORS. FOR GOVERNMENT.)
#m4s




MONEYBALL STARTUPS           +
        IT’S NOT SPRAY AND PRAY. IT’S A PROCESS.



                      PAUL SINGH

                      500 Startups

 @paulsingh・paul@500startups.com・resultsjunkies.com/blog

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Moneyball: A Quantitative Approach to Angel Investing (NASSCOM Product Conclave - India - Nov 2012)

  • 1. #m4s MONEYBALL STARTUPS + IT’S NOT SPRAY AND PRAY. IT’S A PROCESS. PAUL SINGH 500 Startups @paulsingh・paul@500startups.com・resultsjunkies.com/blog
  • 2. #m4s GETTING TO KNOW 500 STARTUPS BECAUSE WE’RE KIND OF A BIG DEAL PAUL SINGH @paulsingh・paul@500startups.com・resultsjunkies.com/blog
  • 3. #m4s THE BIG OPPORTUNITY IN EARLY STAGE TECH INVESTING: API TO VENTURE CAPITAL & FUNCTIONAL EXPERTISE (FOR FOUNDERS. FOR INVESTORS. FOR GOVERNMENT.)
  • 6. #m4s GOVERNMENT: MAKE LIFE EASY FOR INVESTORS & FOUNDERS
  • 7. #m4s “ VENTURE CAPITAL IS OPEN TO ATTACK BY DISRUPTIVE NEW BUSINESS MODELS AND TECHNOLOGY. -- NAVAL RAVIKANT (@naval)
  • 9. #m4s EARLY STAGE STARTUPS HAVE CHANGED
  • 10. #m4s CLOUD, OPEN SOURCE AND ONLINE DISTRIBUTION DRIVING STARTUP COSTS LOWER THAN EVER BUT SCALING STILL COSTS MONEY
  • 11. #m4s WEB GETS BIGGER. WORLD GETS SMALLER.
  • 12. #m4s TRACTION IS THE NEW INTELLECTUAL PROPERTY PLATFORMS (SEARCH, SOCIAL & MOBILE) PRIMARILY DRIVING THE CHANGE. NO LONGER “GOOD ENOUGH” TO DEPEND ON TECH DIFFERENTIATION.
  • 13. #m4s CAPITAL INCREASINGLY COMMODITIZED RISE OF THE ANGELS, YO!
  • 14. #m4s NEW REALITY: MONEY FOLLOWS FOUNDERS
  • 15. #m4s SIGNALS ARE EVERYWHERE BIG DATA + OPEN SOURCE ANALYTICS = NEW TECHNIQUES FOR VC
  • 17. #m4s
  • 18. #m4s “ UBS PROPRIETARY SATELLITE PARKING LOT FILL RATE ANALYSIS POINTS TO AN INTERESTING CADENCE INTRA-QUARTER AND POTENTIAL UPSIDE TO OUR VIEW.
  • 19. #m4s
  • 20. #m4s “ TWICE A WEEK A SMALL HELICOPTER CIRCLES OVER CUSHING’S TANK FARMS ON AN OIL INDUSTRY SPYING MISSION.
  • 21. #m4s WALL STREET ISN’T ALONE THESE TECHNIQUES ALREADY USED TO UNDERWRITE IN-VITRO FERTILIZATION LENDING, PAYDAY LOANS, SUBPRIME AUTO LENDING, HOME/PERSONAL/AUTO INSURANCE AND MORE.
  • 22. #m4s IT TURNS OUT, WE CAN DO IT, TOO SURPRISE!
  • 23. #m4s + “GUT” + TRUSTED MENTORS + MUCH, MUCH MORE DATA.
  • 24. #m4s SENTIMENT ANALYSIS WHAT IS THE TEAM THINKING? WHAT DOES THE MARKET THINK? WHAT DO MY PEERS/MENTORS THINK?
  • 25. #m4s NEEDLE IN THE HAYSTACK REAL USE CASES: SIGNS THAT A FUNDING ROUND IS ABOUT TO OCCUR AND/OR SIGNS THAT A PRODUCT IS ABOUT TO EXPLODE. VERY HARD TO DO ACCURATELY BUT PAYOFF IS BIG & FAST.
  • 26. #m4s FASTER PORTFOLIO TRENDS CURRENT SYSTEMS OF QUARTERLY/AD-HOC REPORTING IS BROKEN -- SELF REPORTED DATA IS OFTEN BIASED. THE RAW DATA IS THERE, THE SYSTEMS TO COLLECT IT AND THE ALGORITHMS TO ANALYZE IT ARE MISSING.
  • 27. #m4s 500 CHECKLIST Product solves a problem for a specific target customer Capital-efficient businesses - operational @ <$1M funding Primarily internet-based distribution - search, social, mobile, local Simple revenue models - transactions, subscriptions or affiliate Functional prototype before investment (or previous success) Small but measurable usage - some customers, early revenue Small but cross-functional team - engineer, design/UX, marketing
  • 28. #m4s EARLY STAGE VC IS CHANGING HAS CHANGED
  • 29. #m4s STATE OF THE ART IN EARLY STAGE INVESTING IS NOT VERY SOPHISTICATED TRUST REFERRALS. MOVE FAST. KEEP LEGAL/FINANCE SIMPLE. BUILD RELATIONSHIPS WITH OTHER INVESTORS, SYNDICATE EVERYTHING.
  • 30. #m4s MONEYBALL IT’S NOT SPRAY AND PRAY. IT’S A PROCESS.
  • 31. #m4s MY PRIMARY GOAL IS TO BUY WINS NOT NECESSARILY BUYING INTO THE HOTTEST DEALS. FOCUS ON TEAM, EXECUTION, TRACTION & DATA. (STICK AROUND... I’M GOING TO SHOW YOU HOW)
  • 32. #m4s INITIAL BET DESIGNED TO GIVE US MORE DATA FOR SUBSEQUENT BETS
  • 33. #m4s QUANTITATIVE PORTFOLIO APPROACH BENEFITS: CONTROLLED RISK + OUTSIZED RETURN POTENTIAL
  • 34. #m4s Monte Carlo Simulation of Angel Investing 5 mean median std dev 3.75 Exit Multiple 2.5 1.25 0 0 2 4 6 8 10 12 14 16 18 20 22 24 26 28 30 # of Deals
  • 35. #m4s MODERN PORTFOLIO THEORY: RISK MITIGATION THROUGH DIVERSIFICATION
  • 36. #m4s HIGH VOLUME INVESTING ALLOWS FOR HIGH ERROR RATE
  • 37. #m4s TRACK IRR & VALUATIONS WITHIN YOUR PORTFOLIO AT LEAST YEARLY. RECOMMEND QUARTERLY.
  • 39. #m4s PORTFOLIO IRR QUICKLY POSITIVE (WITH SMALLER EARLY EXITS AND PROMISING DEALS GETTING FUNDED)
  • 40. #m4s EVEN “SMALLER” EXITS CAN MOVE THE NEEDLE DON’T FORGET: YOU CAN SELL POSITIONS TO DOWNSTREAM OR SECONDARY BUYERS TOO.
  • 41. #m4s INDIVIDUAL BETS ARE SMALL MUCH EASIER TO RUN AN EXPERIMENT ON A $50K INITIAL CHECK INSTEAD OF $250K+
  • 42. #m4s BAD BETS FAIL FAST SMALLER CHECK SIZES FORCE COMPANIES TO PROVE THEORIES FASTER. ALLOWING INVESTORS TO QUICKLY ITERATE OUR FORECASTING/FUNDING MODEL. FEWER “LIVING DEAD” AND QUICKER RETURN ON RESULTS.
  • 43. #m4s FAILURE RATES ARE HIGH DIVERSITY OF HIGH VOLUME INVESTING ALLOWS FOR HIGH ERROR RATE. FUND IRR QUICKLY POSITIVE WITH SMALLER, EARLY EXITS AND PROMISING DEALS GETTING FUNDED. DILIGENCE HAPPENS IN THE REAR VIEW MIRROR, NOT THE CRYSTAL BALL.
  • 44. #m4s ALLOCATE FOR FOLLOW-ONS 30% Capital - Initial Bets target 10-20 deals 70% Capital - Follow On filter out failures, follow-on the top 20% (...OR “HOW TO AVOID GETTING SQUASHED”)
  • 45. #m4s DEAL TERMS SO YOU FOUND A STARTUP YOU LOVE?
  • 47. #m4s CONVERTIBLE NOTES ARE OK (REALLY!) LOWER LEGAL FEES, LESS DOCS, QUICKER TO EXECUTE. WHEN CAPPED, THEY FUNCTION SIMILAR TO PRICED ROUNDS.
  • 48. #m4s STANDARD DOCS ARE YOUR FRIENDS WHEN IN DOUBT, DO NOT INNOVATE IN FINANCE OR LEGAL
  • 49. #m4s PRO RATA & INFO RIGHTS ALWAYS. ALWAYS. ALWAYS. ALWAYS. ALWAYS. (GET IT?)
  • 50. #m4s FOCUS ON VALUATION & MULTIPLES OWNERSHIP % MATTERS MUCH LESS. FOCUS ON REQUIRED EXIT SIZE RATHER THAN SOME MYTHICAL OWNERSHIP TARGET.
  • 51. #m4s IT’S HARD TO MAKE MONEY ON VALUATIONS > $5M (PRO TIP: CONSIDER MIN. RETURN REQUIREMENTS FOR DOWNSIDE SCENARIOS)
  • 52. #m4s YOUR PRIMARY GOAL LET FOUNDERS GET BACK TO WORK THIS IS A LONG GAME: AVOID LOSING YOUR REPUTATION OVER 1%. WHEN IN DOUBT, LEAN TOWARDS THE ENTREPRENEUR.
  • 54. #m4s MOST BOARDS PROVIDE MINIMAL VALUE-ADD
  • 55. #m4s BEST DEALS USUALLY REQUIRE LIMITED BOARD SUPPORT SPEND YOUR TIME SOURCING NEW DEALS. LIMIT TIME ON SIDEWAYS DEALS. LET THE WINNERS KEEP ON WINNING (AND ANSWER YOUR PHONE WHEN THEY NEED YOU).
  • 56. #m4s DO NOT INNOVATE IN FINANCE OR LEGAL
  • 57. #m4s INVESTING IS A PROCESS DABBLING IN INVESTING IS (AT BEST) GAMBLING. BETTER TO WALK AWAY OR PURSUE INVESTING NEARLY FULL TIME OR FIND SOMEONE TO MANAGE YOUR MONEY
  • 58. #m4s BE AN ACTIVE INVESTOR PORTFOLIO EFFECTS & THE LEAN STARTUP MOVEMENT ARE YOUR FRIENDS YOU CAN EXPECT FAVORABLE WITH 10 DEALS BUT IT TAKES 20+ TO BE SAFE
  • 59. #m4s BE A SMART INVESTOR FOCUS ON INFORMATION ASYMMETRY & PRICE/MULTIPLES.
  • 60. #m4s “ BY ITS NATURE, THE INTERNET UNDERMINES ANYONE WHOSE STATUS DEPENDS ON PRIVILEGED ACCESS TO INFORMATION. -- MICHAEL LEWIS
  • 61. #m4s THE BIG OPPORTUNITY IN EARLY STAGE TECH INVESTING: API TO VENTURE CAPITAL & FUNCTIONAL EXPERTISE (FOR FOUNDERS. FOR INVESTORS. FOR GOVERNMENT.)
  • 62. #m4s MONEYBALL STARTUPS + IT’S NOT SPRAY AND PRAY. IT’S A PROCESS. PAUL SINGH 500 Startups @paulsingh・paul@500startups.com・resultsjunkies.com/blog