500.co/challenge #moneyball4startups MONEYBALL STARTUPS +
IT’S NOT SPRAY AND PRAY. IT’S A PROCESS. PAUL SINGH 500 Startups @paulsingh・paul@500startups.com・angel.co/paulsingh

500.co/challenge #moneyball4startups GETTING TO KNOW
500 STARTUPS BECAUSE WE’RE KIND OF A BIG DEAL PAUL SINGH @paulsingh・paul@500startups.com・angel.co/paulsingh

500.co/challenge #moneyball4startups THE BIG OPPORTUNITY
IN EARLY STAGE TECH INVESTING: API TO VENTURE CAPITAL & FUNCTIONAL EXPERTISE (FOR FOUNDERS. FOR INVESTORS. FOR GOVERNMENT.)

500.co/challenge #moneyball4startups FOUNDERS: BUILD SOMETHING
PEOPLE WANT

500.co/challenge #moneyball4startups INVESTORS: WRITE CHECKS
AND ADD VALUE

500.co/challenge #moneyball4startups GOVERNMENT: MAKE LIFE
EASY FOR INVESTORS & FOUNDERS

500.co/challenge #moneyball4startups “ VENTURE CAPITAL
IS OPEN TO ATTACK BY DISRUPTIVE NEW BUSINESS MODELS AND TECHNOLOGY. -- NAVAL RAVIKANT (@naval)

500.co/challenge #moneyball4startups
(R)EVOLUTION IN THINKING

500.co/challenge #moneyball4startups EARLY STAGE STARTUPS
HAVE CHANGED

500.co/challenge #moneyball4startups WEB GETS BIGGER.
WORLD GETS SMALLER.

500.co/challenge #moneyball4startups CLOUD, OPEN SOURCE
AND ONLINE DISTRIBUTION DRIVING STARTUP COSTS LOWER THAN EVERBUT SCALING STILL COSTS MONEY

500.co/challenge #moneyball4startups TRACTION IS THE
NEW INTELLECTUAL PROPERTY PLATFORMS (SEARCH, SOCIAL & MOBILE) PRIMARILY DRIVING THE CHANGE. NO LONGER “GOOD ENOUGH” TO DEPEND ON TECH DIFFERENTIATION.

500.co/challenge #moneyball4startups CAPITAL INCREASINGLY COMMODITIZED
RISE OF THE ANGELS, YO!

500.co/challenge #moneyball4startups NEW REALITY: MONEY
FOLLOWS FOUNDERS

500.co/challenge #moneyball4startups SIGNALS ARE EVERYWHERE
BIG DATA + OPEN SOURCE ANALYTICS = NEW TECHNIQUES FOR VC

500.co/challenge #moneyball4startups WALL STREET BEAT
US TO IT

500.co/challenge #moneyball4startups

500.co/challenge #moneyball4startups “ UBS PROPRIETARY
SATELLITE PARKING LOT FILL RATE ANALYSIS POINTS TO AN INTERESTING CADENCE INTRA-QUARTER AND POTENTIAL UPSIDE TO OUR VIEW.

500.co/challenge #moneyball4startups 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.

500.co/challenge #moneyball4startups IT TURNS OUT,
WE CAN DO IT, TOO SURPRISE!

500.co/challenge #moneyball4startups + “GUT” +
TRUSTED MENTORS + MUCH, MUCH MORE DATA.

500.co/challenge #moneyball4startups SENTIMENT ANALYSIS WHAT
IS THE TEAM THINKING? WHAT DOES THE MARKET THINK? WHAT DO MY PEERS/MENTORS THINK?

500.co/challenge #moneyball4startups 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.

500.co/challenge #moneyball4startups 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.

500.co/challenge #moneyball4startups 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

500.co/challenge #moneyball4startups EARLY STAGE VC
IS CHANGING HAS CHANGED

500.co/challenge #moneyball4startups STATE OF THE
ART IN EARLY STAGE INVESTING IS NOT VERY SOPHISTICATED AT THE EARLIEST STAGE, YOU HAVE LIMITED DATA TO MAKE DECISIONS WITH -- BETTER TO LOOK FOR DEAL FLOW VIA TRUSTED REFERRALS, USE A CHECKLIST, DECIDE YES/NO QUICKLY AND KEEP LEGAL/FINANCE SIMPLE.

500.co/challenge #moneyball4startups MONEYBALL IT’S NOT
SPRAY AND PRAY. IT’S A PROCESS.

500.co/challenge #moneyball4startups 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)

500.co/challenge #moneyball4startups INITIAL BET DESIGNED
TO GIVE US MORE DATA FOR SUBSEQUENT BETS

500.co/challenge #moneyball4startups QUANTITATIVE PORTFOLIO APPROACH
BENEFITS: CONTROLLED RISK + OUTSIZED RETURN POTENTIAL

500.co/challenge #moneyball4startups 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

500.co/challenge #moneyball4startups MODERN PORTFOLIO THEORY:
RISK MITIGATION THROUGH DIVERSIFICATION

500.co/challenge #moneyball4startups HIGH VOLUME INVESTING
ALLOWS FOR HIGH ERROR RATE

500.co/challenge #moneyball4startups TRACK IRR &
VALUATIONS WITHIN YOUR PORTFOLIO AT LEAST YEARLY. RECOMMEND QUARTERLY.

500.co/challenge #moneyball4startups CONTROLLED RISK: OUTSIZED
RETURN POTENTIAL

500.co/challenge #moneyball4startups PORTFOLIO IRR QUICKLY
POSITIVE (WITH SMALLER EARLY EXITS AND PROMISING DEALS GETTING FUNDED)

500.co/challenge #moneyball4startups EVEN “SMALLER” EXITS
CAN MOVE THE NEEDLE DON’T FORGET: YOU CAN SELL POSITIONS TO DOWNSTREAM OR SECONDARY BUYERS TOO.

500.co/challenge #moneyball4startups LAW OF LARGE
NUMBERS FTW!

500.co/challenge #moneyball4startups INDIVIDUAL BETS ARE
SMALL MUCH EASIER TO RUN AN EXPERIMENT ON A $50K INITIAL CHECK INSTEAD OF $250K+

500.co/challenge #moneyball4startups 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.

500.co/challenge #moneyball4startups 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.

500.co/challenge #moneyball4startups 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”)

500.co/challenge #moneyball4startups DEAL TERMS SO
YOU FOUND A STARTUP YOU LOVE?

500.co/challenge #moneyball4startups
DEBT VS EQUITY

500.co/challenge #moneyball4startups CONVERTIBLE NOTES ARE
OK (REALLY!) LOWER LEGAL FEES, LESS DOCS, QUICKER TO EXECUTE. WHEN CAPPED, THEY FUNCTION SIMILAR TO PRICED ROUNDS.

500.co/challenge #moneyball4startups STANDARD DOCS ARE
YOUR FRIENDS WHEN IN DOUBT, DO NOT INNOVATE IN FINANCE OR LEGAL

500.co/challenge #moneyball4startups PRO RATA &
INFO RIGHTS ALWAYS. ALWAYS. ALWAYS. ALWAYS. ALWAYS. (GET IT?)

500.co/challenge #moneyball4startups FOCUS ON VALUATION
& MULTIPLES OWNERSHIP % MATTERS MUCH LESS. FOCUS ON REQUIRED EXIT SIZE RATHER THAN SOME MYTHICAL OWNERSHIP TARGET.

500.co/challenge #moneyball4startups IT’S HARD TO
MAKE MONEY ON VALUATIONS > $5M (PRO TIP: CONSIDER MIN. RETURN REQUIREMENTS FOR DOWNSIDE SCENARIOS)

500.co/challenge #moneyball4startups 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.

500.co/challenge #moneyball4startups
AVOID BOARD SEATS

500.co/challenge #moneyball4startups MOST BOARDS PROVIDE
MINIMAL VALUE-ADD

500.co/challenge #moneyball4startups 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).

500.co/challenge #moneyball4startups DO NOT INNOVATE
IN FINANCE OR LEGAL

500.co/challenge #moneyball4startups 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

500.co/challenge #moneyball4startups 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

500.co/challenge #moneyball4startups BE A SMART
INVESTOR FOCUS ON INFORMATION ASYMMETRY & PRICE/MULTIPLES.

500.co/challenge #moneyball4startups “ BY ITS
NATURE, THE INTERNET UNDERMINES ANYONE WHOSE STATUS DEPENDS ON PRIVILEGED ACCESS TO INFORMATION. -- MICHAEL LEWIS

500.co/challenge #moneyball4startups THE BIG OPPORTUNITY
IN EARLY STAGE TECH INVESTING: API TO VENTURE CAPITAL & FUNCTIONAL EXPERTISE (FOR FOUNDERS. FOR INVESTORS. FOR GOVERNMENT.)

500.co/challenge #moneyball4startups
500.co/challenge

500.co/challenge #moneyball4startups MONEYBALL STARTUPS +
IT’S NOT SPRAY AND PRAY. IT’S A PROCESS. PAUL SINGH 500 Startups @paulsingh・paul@500startups.com・angel.co/paulsingh