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Data-Driven Patterns for
Successful Angel Investing
Sim Simeonov
sim@fastignite.com
@simeons
Founding. Funding.
Growing. Startups.
Have fun
  & make   $$$
58
 %
 IRR
Cash-on-Cash
  3.2x
66% lose money
45% total loss
What determines investment success?
quality deal flow
  picking winners
 winning the deal
market environment
Can you pick winners?
If you can have asymmetric information
   most of the time, ignore the advice here
quality deal flow
  picking winners
 winning the deal
market environment
investment optionality

dollar cost averaging
be a player

 investment optionality
  dollar cost averaging

play a lot
Angel Investment
 Returns Analysis

Ingredients          Instructions
• Kaufmann angel     1. Clean data
  return data set
                     2. Analyze data set
• Additional data
                     3. Reverse-engineer
  from angels
                        returns probability
Tools                   distribution

• Big data kitchen   4. Do Monte Carlo
                     5. Adjust & repeat #4
                        for all interesting
                        questions
Two things you don’t
want to see made:
sausage & econometrics
The end result, however…
100%


80%

                                         >10x
60%                                      5-10x
                                         3-5x
40%                                      2-3x
                                         1-2x
20%                                      <1x


 0%
        % of    % of    % of    % of
       Angels   deals   $inv   $return
Monte Carlo results
100%


                                                        Portfolio
                   75%                                    Size Size
                                                            Portfolio
P(return > X), %




                                                             5
                                                             10
                                                             25
                   50%
                                                             50
                                                             100

                   25%



                    0%
                          0x   2x       4x      6x      8x        10x
                                    Cash-on-Cash Return
Why do a few angels get the
 lion’s share of returns?
Lucky?   Smart?
Portfolio Size
P(return > X), %


                   15%             200%
                                          5    10    25    50     100
                                                                Portfolio Size




                   10%



                   5%



                   0%
                         5x   6x          7x        8x     9x             10x

                               Cash-on-Cash Return
Answer: most likely luck
100%


                                                   Portfolio
                             200%
                                                     Size Size
                                                       Portfolio
P(return>X), %




                 75%                                    5
                                                        10
                                                        25
                                                        50
                 50%                                    100




                 25%
                        0x   1x      2x       3x             4x
                             Cash-on-Cash Return
Does the lean startup movement
   benefit angel investors?
P(failure) reduced from 60% to 50%
125%

100%

 75%

 50%

 25%

  0%
         5
               10
                      20
                              25
                                      50
                                           100
       DiffP(x > 1)        DiffP(x > 2)    DiffP(x > 3)
Answer: yes but very active angels
  get disproportionate benefits
What’s the effect of big bets?
50x vs. 1000x returns cap
80%


60%


40%


20%


 0%
       5
              10
                     20
                             25
                                     50
                                          100

      DiffP(x > 1)        DiffP(x > 2)    DiffP(x > 3)
20%

                   50x cap, 55% fail
                         vs.
10%
                  1000x cap, 60% fail

 0%
       5          10      20      25      50       100


-10%



-20%
           DiffP(x > 1)   DiffP(x > 2)   DiffP(x > 3)
Answer: big bets make the most
  sense for very active angels
Be an active angel.
Benefit from:
 - portfolio effects
 - lean startup ecosystem
 - making big bets
Be a selective angel.
Focus on:
 - information asymmetry
 - low-failure opportunities
 - price
Econometrician seeks
angel investor data for
    discrete long-term
 relationship and intense
  anything-goes analysis.
Must be clean and BS-free.
  http://sim.vc/angels
Patterns of Successful Angel Investing by Simeon Simeonov

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