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INVESTING IN EXCEPTIONAL
SOFTWARE COMPANIES
C O N F I D E N T I A L | T R A D E S E C R E T
2
A G E N D A
▸ Introduction and Background
▸ Tom Brady Case Study
▸ Data-Driven Investing in Software Companies
▸ What We Look for in Companies and Founders
▸ Investing in LeagueApps
3
C O N F I D E N T I A L | T R A D E S E C R E T
645 Ventures is a seed stage firm that applies a data-intensive, growth stage investing lens to
sourcing, due diligence, and value creation for fast-growing, early-stage companies.
645 Voyager (our proprietary software platform) complements strategic relationships with top VCs
and Cornell Tech to assist us in identifying high-potential companies that can each return our fund.
Geographic Focus: (Top 3 Venture Markets) New York, Boston, Bay Area
Sector Focus: Enterprise SaaS & Infrastructure as a Service, Nascent markets: Computer Vision,
AI, AR/VR, Marketplaces & Consumer Internet
Notable LPs: Some of the top venture capital investors in the industry, including GPs at
Andreessen Horowitz, First Round Capital, OpenView Ventures, Union Square Ventures
6 4 5 V E N T U R E S O V E R V I E W
C O N F I D E N T I A L | T R A D E S E C R E T
4
W H A T C A N T O M B R A D Y T E A C H U S A B O U T
I N V E S T I N G I N E N T R E P R E N E U R S ?
▸ Fact: Tom Brady was drafted with the
199th pick in the 2000 NFL Draft. He was
the 7th quarterback selected in that draft.
▸ Fact: Tom Brady is the only QB to win
five Super Bowls.
▸ Fact: Tom Brady is considered by many
to be the biggest steal in NFL draft
history.
▸ Question: What did NFL scouts fail to
measure about Tom Brady? What can
this failure teach us about evaluating and
investing in exceptional software
companies and teams?
D O N ’ T J U D G E A B O O K B Y I T S C O V E R
C O N F I D E N T I A L | T R A D E S E C R E T
6
T O M B R A D Y ’ S C O L L E G E P E R F O R M A N C E
COLLEGE PERFORMANCE:
▸ Despite only starting for two years, Brady finished 3rd in
Michigan history in pass attempts and completions, 4th in yards
and completion percentage, and 5th in touchdown passes.
▸ Record: 20 wins, 5 losses as a starter (won 80% of games).
▸ Won two bowl games.
▸ Nicknamed “the comeback kid” – Brady continually brought
Michigan back in close games
PERFORMANCE EVALUATION:
▸ Ability to win
▸ Precise passing ability and passing accuracy
▸ Good arm
▸ Strong performance in pressure situations
▸ Overcomes adversity
C O N F I D E N T I A L | T R A D E S E C R E T
7
T O M B R A D Y A T T H E N F L C O M B I N E
2000 NFL COMBINE:
▸ Brady performed poorly on every combine test
▸ He ran a 5.28 40 time, one of the worst times ever run by a QB
▸ His vertical leap was 24.5 inches, also terrible
NFL$Combine$Performance:$QB$Comparison:
Player 40:Dash 20:Dash 10:Dash Vertical Broad Shuttle 3:Cone
Andrew'Luck 4.67 36 10'04" 4.28 6.8
Robert'Griffin'III 4.41 39 10'
Tom'Brady 5.28 2.94 1.7 24'1/2 08'03" 4.38 7.2
Drew'Brees 4.83 2.75 1.66 32 08'09" 4.21 7.09
Aaron'Rodgers 4.71 2.75 1.65 34'1/2 09'02" 7.39
Tom$Brady$Rank Last Last Last Last Last Last 2nd$to$Last
Article: “Tom Brady May be the Worst QB in the history of the NFL,
according to NFL Combine Numbers”
C O N F I D E N T I A L | T R A D E S E C R E T
8
N F L S C O U T E V A L U A T I O N
▸ Draft Report on Brady: “Poor build. Skinny. Lacks great
physical stature and strength. Lacks mobility and ability to
avoid the rush. Lacks a really strong arm. Can’t drive the
ball downfield. Does not throw a really tight spiral. System
type player who can get exposed if forced to ad-lib. Gets
knocked down easily”
▸ Steve Mariucci (49ers Coach): “[Brady] looked like he
hadn’t ever seen a weight room. Ran a 5.2 something, one
of the slowest QBs in the combine… He had an OK arm”
▸ Tom Brady Response: “What the hell do these people
know? That sounds like Joe Montana right there”
Key Idea: The NFL Combine Measures the Wrong Things
C O N F I D E N T I A L | T R A D E S E C R E T
9
S C O U T S O V E R L O O K E D T H E I N T A N G I B L E S
▸ Tremendous Resilience: In his
freshman year in high school, Brady
was the backup QB on a team that
went 0-8. He started his career 7th on
the Michigan QB depth chart.
▸ Leadership Ability: “There is no
greater leader in intercollegiate
athletics than Tom Brady” (Michigan
Coach Lloyd Carr)
▸ Responds to Pressure: Played better
when the game was on the line
▸ Love of the Game: Always first to
practice. Always in the film room.
C O N F I D E N T I A L | T R A D E S E C R E T
10
W H A T T O M B R A D Y T E A C H E S U S A B O U T I N V E S T I N G I N
E X C E P T I O N A L S O F T W A R E C O M P A N I E S
▸ Looks can be deceiving: Beware of superficial pattern-matching;
look more deeply at what drives the entrepreneur
▸ Look for predictable performance metrics
▸ When evaluating entrepreneurial teams, place a premium on
resourcefulness, scrappiness, and ability to overcome adversity
▸ Avoid herd mentality
▸ Use analytics to determine which qualities are consistently
undervalued
▸ Measure the right things; don’t apply tests that have nothing to
do with actual performance
▸ You can’t measure heart, but you can observe how it manifests
itself
11
C O N F I D E N T I A L | T R A D E S E C R E T
T R A D I T I O N A L E A R L Y - S T A G E I N V E S T I N G L O O K S A L O T
L I K E O L D - S C H O O L S C O U T I N G
Venture capital investors “know it when they see it”
12
C O N F I D E N T I A L | T R A D E S E C R E T
W E A P P L Y A M O N E Y B A L L A P P R O A C H T O E A R L Y - S T A G E
I N V E S T I N G
13
C O N F I D E N T I A L | T R A D E S E C R E T
E V O L U T I O N O F D A T A - D R I V E N D E A L S O U R C I N G
▸ Network-driven sourcing
▸ Largely constrained by geography
▸ Limited data signals; primarily “gut feel”
investing
▸ Inability to systematically cover industries
HI STO RI CAL
CHARACTERI STI CS
▸ Outbound deal sourcing
▸ Broad startup coverage across
geographies
▸ Data signals collected manually
▸ Systematic coverage of industries
NEW CHARACTERI STI CS
▸ Outbound + network-based deal sourcing
▸ Broad startup coverage across
geographies
▸ Data signals collected via database APIs
▸ Systematic coverage of industries
EARLY STAGE GROWTH STAGE
EVOLUTION OF EARLY STAGE
C O N F I D E N T I A L | T R A D E S E C R E T
K E Y E L E M E N T S O F 6 4 5 V E N T U R E S
We define growth seed as rapidly-growing
software and Internet companies with
customer/user traction, where team, market,
and investor characteristics evidence a large
potential opportunity
▸ Target market opportunity: $1B or greater
▸ Target revenue size: $500k to $5m
▸ Target round size: $750k to $3m
UNBEATABLE
FRAMEWORK
ALGORITHMIC SCORING,
PATTERN RECOGNITION,
AUTOMATION
RELATIONSHIP-BUILDING,
CREAIVITY
INSITITUITIONAL
MEMORY, EFFICIENCY,
SCALABILITY
HUMAN
INTERACTION
SOFTWARE
+
14
We apply software at each stage of our investment process (sourcing, evaluation,
and value-add) to enable a far more scalable investment model at the growth seed
stage.
▸ We apply an outbound sourcing and
evaluation approach
▸ We are typically the first or one of the first
institutional investors in a deal, and we can
follow or invest alongside angels and angel
groups
Our in-house engineering team manages a proprietary data platform that tracks and
analyzes startup data signals, covering team, growth, market, and investor characteristics
C O N F I D E N T I A L | T R A D E S E C R E T
15
W H Y I N V E S T I N S O F T W A R E ?
Software companies can grow with limited capital, and
produce externally observable performance metrics.
The data doesn’t often lie
WHAT WE LOOK FOR:
▸ Exceptional founders with track records of success
▸ Sticky products with low customer churn
▸ Rapid revenue growth with low cash burn
▸ Strong sales economics: LTV >> CAC
▸ Large addressable market opportunity (>$1B)
C O N F I D E N T I A L | T R A D E S E C R E T
16
H O W W E E V A L U A T E S T A R T U P F O U N D E R S
WHAT WE LOOK FOR IN FOUNDERS:
▸ Objective evidence of performance
▸ Historical evidence of founder commitment and
leadership
▸ Skills that are well-tuned to the specific entrepreneurial
opportunity (“can’t see this person doing anything else”)
▸ “Love of the game”; passion for what they do
▸ Winning Attitude
WHAT WE AVOID IN FOUNDERS:
▸ “Looks the part”
▸ Lack of commitment
▸ Clear holes in the team
▸ Low ethical/moral orientation
C O N F I D E N T I A L | T R A D E S E C R E T
17
H O W W E E V A L U A T E F O U N D E R S W I T H D A T A
▸ Commitment: How long have the founders worked together?
▸ Domain expertise: What have the founders done before? What
level of domain expertise do they have?
▸ Evidence of leadership ability
▸ Previous successes
▸ Ability to Recruit: Who have the founders recruited to join their
team?
▸ Strong Culture: What is it like to walk around the company’s
office?
▸ Attention to Detail and Responsiveness
▸ No Major Holes in the Team
WE APPLY A POINTS SYSTEM TO FOUNDING TEAMS (“TEAM ALPHA”)
AND WE SCORE ALL OF THE CHARACTERISTICS LISTED ABOVE
C O N F I D E N T I A L | T R A D E S E C R E T
18
H O W W E E V A L U A T E C O M P A N Y P E R F O R M A N C E D A T A
▸ Evidence of Traction: Key customer wins, employee growth
▸ Revenue growth
▸ Performance metrics: revenue retention, payback period,
LTV/CAC ratio
▸ Quality of business model: gross margins, net margins
▸ Customer affinity for a company’s product: Net promoter
score
▸ Productivity of sales and marketing operation
▸ Size of addressable market: $1B or greater
C O N F I D E N T I A L | T R A D E S E C R E T
I D E A S F O R E N T R E P R E N E U R S T O R E M E M B E R
19

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Invest in Top Software Founders and Companies

  • 2. C O N F I D E N T I A L | T R A D E S E C R E T 2 A G E N D A ▸ Introduction and Background ▸ Tom Brady Case Study ▸ Data-Driven Investing in Software Companies ▸ What We Look for in Companies and Founders ▸ Investing in LeagueApps
  • 3. 3 C O N F I D E N T I A L | T R A D E S E C R E T 645 Ventures is a seed stage firm that applies a data-intensive, growth stage investing lens to sourcing, due diligence, and value creation for fast-growing, early-stage companies. 645 Voyager (our proprietary software platform) complements strategic relationships with top VCs and Cornell Tech to assist us in identifying high-potential companies that can each return our fund. Geographic Focus: (Top 3 Venture Markets) New York, Boston, Bay Area Sector Focus: Enterprise SaaS & Infrastructure as a Service, Nascent markets: Computer Vision, AI, AR/VR, Marketplaces & Consumer Internet Notable LPs: Some of the top venture capital investors in the industry, including GPs at Andreessen Horowitz, First Round Capital, OpenView Ventures, Union Square Ventures 6 4 5 V E N T U R E S O V E R V I E W
  • 4. C O N F I D E N T I A L | T R A D E S E C R E T 4 W H A T C A N T O M B R A D Y T E A C H U S A B O U T I N V E S T I N G I N E N T R E P R E N E U R S ? ▸ Fact: Tom Brady was drafted with the 199th pick in the 2000 NFL Draft. He was the 7th quarterback selected in that draft. ▸ Fact: Tom Brady is the only QB to win five Super Bowls. ▸ Fact: Tom Brady is considered by many to be the biggest steal in NFL draft history. ▸ Question: What did NFL scouts fail to measure about Tom Brady? What can this failure teach us about evaluating and investing in exceptional software companies and teams?
  • 5. D O N ’ T J U D G E A B O O K B Y I T S C O V E R
  • 6. C O N F I D E N T I A L | T R A D E S E C R E T 6 T O M B R A D Y ’ S C O L L E G E P E R F O R M A N C E COLLEGE PERFORMANCE: ▸ Despite only starting for two years, Brady finished 3rd in Michigan history in pass attempts and completions, 4th in yards and completion percentage, and 5th in touchdown passes. ▸ Record: 20 wins, 5 losses as a starter (won 80% of games). ▸ Won two bowl games. ▸ Nicknamed “the comeback kid” – Brady continually brought Michigan back in close games PERFORMANCE EVALUATION: ▸ Ability to win ▸ Precise passing ability and passing accuracy ▸ Good arm ▸ Strong performance in pressure situations ▸ Overcomes adversity
  • 7. C O N F I D E N T I A L | T R A D E S E C R E T 7 T O M B R A D Y A T T H E N F L C O M B I N E 2000 NFL COMBINE: ▸ Brady performed poorly on every combine test ▸ He ran a 5.28 40 time, one of the worst times ever run by a QB ▸ His vertical leap was 24.5 inches, also terrible NFL$Combine$Performance:$QB$Comparison: Player 40:Dash 20:Dash 10:Dash Vertical Broad Shuttle 3:Cone Andrew'Luck 4.67 36 10'04" 4.28 6.8 Robert'Griffin'III 4.41 39 10' Tom'Brady 5.28 2.94 1.7 24'1/2 08'03" 4.38 7.2 Drew'Brees 4.83 2.75 1.66 32 08'09" 4.21 7.09 Aaron'Rodgers 4.71 2.75 1.65 34'1/2 09'02" 7.39 Tom$Brady$Rank Last Last Last Last Last Last 2nd$to$Last Article: “Tom Brady May be the Worst QB in the history of the NFL, according to NFL Combine Numbers”
  • 8. C O N F I D E N T I A L | T R A D E S E C R E T 8 N F L S C O U T E V A L U A T I O N ▸ Draft Report on Brady: “Poor build. Skinny. Lacks great physical stature and strength. Lacks mobility and ability to avoid the rush. Lacks a really strong arm. Can’t drive the ball downfield. Does not throw a really tight spiral. System type player who can get exposed if forced to ad-lib. Gets knocked down easily” ▸ Steve Mariucci (49ers Coach): “[Brady] looked like he hadn’t ever seen a weight room. Ran a 5.2 something, one of the slowest QBs in the combine… He had an OK arm” ▸ Tom Brady Response: “What the hell do these people know? That sounds like Joe Montana right there” Key Idea: The NFL Combine Measures the Wrong Things
  • 9. C O N F I D E N T I A L | T R A D E S E C R E T 9 S C O U T S O V E R L O O K E D T H E I N T A N G I B L E S ▸ Tremendous Resilience: In his freshman year in high school, Brady was the backup QB on a team that went 0-8. He started his career 7th on the Michigan QB depth chart. ▸ Leadership Ability: “There is no greater leader in intercollegiate athletics than Tom Brady” (Michigan Coach Lloyd Carr) ▸ Responds to Pressure: Played better when the game was on the line ▸ Love of the Game: Always first to practice. Always in the film room.
  • 10. C O N F I D E N T I A L | T R A D E S E C R E T 10 W H A T T O M B R A D Y T E A C H E S U S A B O U T I N V E S T I N G I N E X C E P T I O N A L S O F T W A R E C O M P A N I E S ▸ Looks can be deceiving: Beware of superficial pattern-matching; look more deeply at what drives the entrepreneur ▸ Look for predictable performance metrics ▸ When evaluating entrepreneurial teams, place a premium on resourcefulness, scrappiness, and ability to overcome adversity ▸ Avoid herd mentality ▸ Use analytics to determine which qualities are consistently undervalued ▸ Measure the right things; don’t apply tests that have nothing to do with actual performance ▸ You can’t measure heart, but you can observe how it manifests itself
  • 11. 11 C O N F I D E N T I A L | T R A D E S E C R E T T R A D I T I O N A L E A R L Y - S T A G E I N V E S T I N G L O O K S A L O T L I K E O L D - S C H O O L S C O U T I N G Venture capital investors “know it when they see it”
  • 12. 12 C O N F I D E N T I A L | T R A D E S E C R E T W E A P P L Y A M O N E Y B A L L A P P R O A C H T O E A R L Y - S T A G E I N V E S T I N G
  • 13. 13 C O N F I D E N T I A L | T R A D E S E C R E T E V O L U T I O N O F D A T A - D R I V E N D E A L S O U R C I N G ▸ Network-driven sourcing ▸ Largely constrained by geography ▸ Limited data signals; primarily “gut feel” investing ▸ Inability to systematically cover industries HI STO RI CAL CHARACTERI STI CS ▸ Outbound deal sourcing ▸ Broad startup coverage across geographies ▸ Data signals collected manually ▸ Systematic coverage of industries NEW CHARACTERI STI CS ▸ Outbound + network-based deal sourcing ▸ Broad startup coverage across geographies ▸ Data signals collected via database APIs ▸ Systematic coverage of industries EARLY STAGE GROWTH STAGE EVOLUTION OF EARLY STAGE
  • 14. C O N F I D E N T I A L | T R A D E S E C R E T K E Y E L E M E N T S O F 6 4 5 V E N T U R E S We define growth seed as rapidly-growing software and Internet companies with customer/user traction, where team, market, and investor characteristics evidence a large potential opportunity ▸ Target market opportunity: $1B or greater ▸ Target revenue size: $500k to $5m ▸ Target round size: $750k to $3m UNBEATABLE FRAMEWORK ALGORITHMIC SCORING, PATTERN RECOGNITION, AUTOMATION RELATIONSHIP-BUILDING, CREAIVITY INSITITUITIONAL MEMORY, EFFICIENCY, SCALABILITY HUMAN INTERACTION SOFTWARE + 14 We apply software at each stage of our investment process (sourcing, evaluation, and value-add) to enable a far more scalable investment model at the growth seed stage. ▸ We apply an outbound sourcing and evaluation approach ▸ We are typically the first or one of the first institutional investors in a deal, and we can follow or invest alongside angels and angel groups Our in-house engineering team manages a proprietary data platform that tracks and analyzes startup data signals, covering team, growth, market, and investor characteristics
  • 15. C O N F I D E N T I A L | T R A D E S E C R E T 15 W H Y I N V E S T I N S O F T W A R E ? Software companies can grow with limited capital, and produce externally observable performance metrics. The data doesn’t often lie WHAT WE LOOK FOR: ▸ Exceptional founders with track records of success ▸ Sticky products with low customer churn ▸ Rapid revenue growth with low cash burn ▸ Strong sales economics: LTV >> CAC ▸ Large addressable market opportunity (>$1B)
  • 16. C O N F I D E N T I A L | T R A D E S E C R E T 16 H O W W E E V A L U A T E S T A R T U P F O U N D E R S WHAT WE LOOK FOR IN FOUNDERS: ▸ Objective evidence of performance ▸ Historical evidence of founder commitment and leadership ▸ Skills that are well-tuned to the specific entrepreneurial opportunity (“can’t see this person doing anything else”) ▸ “Love of the game”; passion for what they do ▸ Winning Attitude WHAT WE AVOID IN FOUNDERS: ▸ “Looks the part” ▸ Lack of commitment ▸ Clear holes in the team ▸ Low ethical/moral orientation
  • 17. C O N F I D E N T I A L | T R A D E S E C R E T 17 H O W W E E V A L U A T E F O U N D E R S W I T H D A T A ▸ Commitment: How long have the founders worked together? ▸ Domain expertise: What have the founders done before? What level of domain expertise do they have? ▸ Evidence of leadership ability ▸ Previous successes ▸ Ability to Recruit: Who have the founders recruited to join their team? ▸ Strong Culture: What is it like to walk around the company’s office? ▸ Attention to Detail and Responsiveness ▸ No Major Holes in the Team WE APPLY A POINTS SYSTEM TO FOUNDING TEAMS (“TEAM ALPHA”) AND WE SCORE ALL OF THE CHARACTERISTICS LISTED ABOVE
  • 18. C O N F I D E N T I A L | T R A D E S E C R E T 18 H O W W E E V A L U A T E C O M P A N Y P E R F O R M A N C E D A T A ▸ Evidence of Traction: Key customer wins, employee growth ▸ Revenue growth ▸ Performance metrics: revenue retention, payback period, LTV/CAC ratio ▸ Quality of business model: gross margins, net margins ▸ Customer affinity for a company’s product: Net promoter score ▸ Productivity of sales and marketing operation ▸ Size of addressable market: $1B or greater
  • 19. C O N F I D E N T I A L | T R A D E S E C R E T I D E A S F O R E N T R E P R E N E U R S T O R E M E M B E R 19