Jason Lemkin y por qué prefiere ser CEO que VC (ENG) - Podcast #60 — vídeo y transcripción

[00:01] [Music]
[00:16] 
[00:16] Bienvenue  Monsieur  Mademoiselle  put  a
[00:19] 
[00:19] unique  manner  estamos  con  George  Romero
[00:22] 
[00:22] the  pictorial  you  serve  an  opera
[00:25] 
[00:25] Hellenic  eat  any  model  I  swear  they
[00:27] 
[00:27] start  going  Jason  Lemkin  and  if  I  wear
[00:31] 
[00:31] chimera  al  English  ballet  porque  with  a
[00:33] 
[00:33] little  on  English  how  are  you  Jason
[00:36] 
[00:36] I  am  terrific  thanks  for  having  me  on
[00:37] 
[00:37] the  podcast  thank  you  very  much  for
[00:39] 
[00:39] being  here  I  we  know  that  you're  super
[00:41] 
[00:41] tired  you've  been  in  a  whole  event  today
[00:43] 
[00:43] yes  and  yesterday  and  and  it's  been  a
[00:46] 
[00:46] hard  week  it's  been  a  great  week  it's
[00:48] 
[00:48] been  sort  of  terrific  to  be  in  Barcelona
[00:50] 
[00:50] I've  met  a  lot  of  great  people  we  did  a
[00:52] 
[00:52] great  event  it  factorials  headquarters
[00:54] 
[00:54] we  did  a  great  meet  up  with  about  a
[00:55] 
[00:55] hundred  founders  and  entrepreneurs  so
[00:57] 
[00:57] yeah  a  little  tired  but  super  excited  to
[00:59] 
[00:59] be  here  yeah  so  it  could  be  very
[01:02] 
[01:02] interesting  for  us  to  know  your  story  so
[01:05] 
[01:05] it  would  be  very  interesting  to  know
[01:06] 
[01:06] where  you  come  from  and  where  you
[01:09] 
[01:09] started  and  what  was  the  first  things
[01:12] 
[01:12] you  did  in  the  business  world  ah  boy  all
[01:16] 
[01:16] I  go  back  so  far  in  time  but  most  of  my
[01:19] 
[01:19] career  since  being  13  was  in  startups  in
[01:23] 
[01:23] some  fashion  and  I  co-founded  two
[01:26] 
[01:26] startups  the  first  one  was  seven  -  the
[01:29] 
[01:29] enterprise  but  not  software  technology
[01:31] 
[01:32] company  was  very  hard  sold  it  for  50
[01:35] 
[01:35] million  after  twelve  and  a  half  months
[01:36] 
[01:36] thought  it  would  all  be  easy  started  a
[01:39] 
[01:39] company  called  echo  sign  thought  we  do
[01:41] 
[01:41] two  million  in  revenue  our  first  year
[01:43] 
[01:43] went  from  zero  to  two  hundred  thousand
[01:45] 
[01:45] in  the  first  year  and  everyone  thought
[01:47] 
[01:47] it  was  a  failure
[01:48] 
[01:48] one  co-founder  quit  another  co-founder
[01:50] 
[01:50] fired  the  other  co-founder  a  lot  of
[01:52] 
[01:52] drama  but  I  learned  about  software  as  a
[01:55] 
[01:55] service  I  learned  how  to  sell  software  I
[01:57] 
[01:57] learned  how  to  build  enterprise  software
[01:59] 
[01:59] five  years  later  we  had  a  nine  figure
[02:01] 
[02:01] exit  to  Adobe  and  I  was  briefly  a  senior
[02:04] 
[02:04] vice-president  Adobe  in  charge  of  all
[02:06] 
[02:06] the  web  business  services  after  selling
[02:08] 
[02:08] echo  sign  and  then  and  then  I  learned
[02:12] 
[02:12] something  very  profound  for  software
[02:14] 
[02:14] I  sold  my  second  company  right  when  we
[02:17] 
[02:17] were  doing  a  million  a  month  there  were
[02:18] 
[02:18] 12  million  a  year  and  a  million  a  month
[02:20] 
[02:20] and  I  didn't  know  what  would  happen  and
[02:22] 
[02:22] I  learned  that
[02:24] 
[02:24] in  recurring  revenue  businesses  and
[02:26] 
[02:26] software  businesses  when  you  hit  about
[02:28] 
[02:28] ten  million  a  year  or  a  million  a  month
[02:30] 
[02:30] if  the  customers  are  happy  you  can't
[02:33] 
[02:33] kill  them
[02:33] 
[02:33] like  they  keep  going  even  if  you  sell  to
[02:36] 
[02:36] a  company  that  doesn't  pay  it  any
[02:37] 
[02:37] attention  as  long  as  you  nurture  it  as
[02:40] 
[02:40] long  as  you  invest  in  it  if  you  have
[02:41] 
[02:41] happy  customers  and  high  revenue
[02:43] 
[02:43] retention  that  compounds  and  even  being
[02:46] 
[02:46] a  very  small  part  of  Adobe  today  that's
[02:48] 
[02:48] not  core  that  business  is  doing  140
[02:50] 
[02:50] million  so  even  with  a  little  bit  of
[02:53] 
[02:53] neglect  from  12  million  in  2011  to  140
[02:57] 
[02:57] million  today  and  we  had  a  great  run  and
[03:00] 
[03:00] I  was  the  largest  shareholder  I  can't
[03:02] 
[03:02] complain  financially  but  I  was  sort  of
[03:04] 
[03:04] in  some  ways  haunted  by  what  if  I  had  to
[03:06] 
[03:06] sold  what  I  didn't  know  I  didn't  know
[03:08] 
[03:08] that  10  million  with  a  hundred  and
[03:10] 
[03:10] twenty  percent  revenue  retention  and
[03:12] 
[03:12] fifty  MPs  was  great  no  one  told  me  I  had
[03:14] 
[03:14] no  mentors  I  had  no  advisers  I  had  no
[03:16] 
[03:16] blog  to  read  no  Quora  answers  no  one
[03:19] 
[03:19] told  me  I  was  doing  this  i  Ted  to
[03:21] 
[03:21] investors  but  SAS  was  new  and  nobody
[03:23] 
[03:23] knew  I  was  being  compared  to  Salesforce
[03:25] 
[03:25] and  Viva  Microsystems
[03:28] 
[03:28] and  in  my  back  I  didn't  wasn't  an
[03:30] 
[03:30] accelerator  but  I  was  an  adventure  fund
[03:32] 
[03:32] and  then  that  fund  my  cohorts  in  that
[03:34] 
[03:34] class  were  Viva  which  is  sixteen  billion
[03:36] 
[03:36] Yammer  with  David  Sachs  box  with  Aaron
[03:40] 
[03:40] Levy  I'm  intact  which  was  just  sold  to
[03:44] 
[03:44] Sage  and  UK  for  nine  hundred  million  so
[03:46] 
[03:46] I  had  a  pretty  good  class  and  no  one
[03:48] 
[03:48] ever  told  me  I  did  okay  and  I  wish
[03:51] 
[03:51] someone  had  so  no  one's  fault  but  a
[03:54] 
[03:54] learning  so  after  recovering  from
[03:56] 
[03:56] selling  I  decided  hey  I  was  the  first
[03:58] 
[03:58] one  from  that  batch  to  sell  their
[04:00] 
[04:00] company  so  I  would  share  my  mistakes
[04:01] 
[04:01] like  I  didn't  have  anything  to  hide  I
[04:03] 
[04:03] didn't  have  to  pretend  I  was  doing
[04:05] 
[04:05] better  than  I  was  I  didn't  have  to
[04:06] 
[04:06] pretend  I  knew  anything  I  did  it  and  I
[04:09] 
[04:09] just  started  sharing  my  mistakes  through
[04:10] 
[04:10] a  blog  and  some  answers  encore  and  I
[04:12] 
[04:12] didn't  know  if  anyone  would  read  it  but
[04:14] 
[04:14] I  was  kind  of  depressed  after  selling  my
[04:15] 
[04:15] company  so  I  went  back  to  the  same
[04:18] 
[04:18] street  our  office  was  on  in  downtown
[04:19] 
[04:19] Palo  Alto  I  rented  my  own  office  across
[04:21] 
[04:21] the  street  from  my  old  office  to  feel
[04:23] 
[04:23] comfy  and  warm  from  having  sold  and  I
[04:25] 
[04:25] started  writing  this  blog  and  I  was  so
[04:27] 
[04:27] tired  I  couldn't  even  take  a  meeting
[04:29] 
[04:29] like  with  any  founders  but  I  wrote  this
[04:30] 
[04:30] blog  and  the  first  piece  I  wrote  was  how
[04:33] 
[04:33] everybody  lies  about  the  revenue  and
[04:35] 
[04:35] exaggerated  and  I  wrote  it  and  the
[04:37] 
[04:37] like  I  ever  got  in  social  media  with
[04:39] 
[04:39] some  aaron  levy  the  CEO  of  a  box  so  I
[04:41] 
[04:41] knew  there  was  someone  else  like  me
[04:42] 
[04:42] someone  else  was  interested  in  these
[04:44] 
[04:44] weird  topics  like  how  to  hire  a  VP  of
[04:46] 
[04:46] Sales  how  to  do  customer  success  how  to
[04:48] 
[04:48] build  a  sales  comp  plan  and  I  went  on  to
[04:51] 
[04:51] write  3,000  pieces  of  content  that  are
[04:53] 
[04:53] all  about  scaling  revenue  and  it  was
[04:55] 
[04:55] very  novel  at  the  time  and  then  two
[04:58] 
[04:58] things  happened  when  I  wrote  more  and  we
[05:00] 
[05:00] went  from  five  readers  to  three  million
[05:02] 
[05:02] views  a  month  a  hundred  thousand  on  our
[05:05] 
[05:05] podcast  three  million  on  our  media  and
[05:08] 
[05:08] then  I  started  investing  accidentally  I
[05:11] 
[05:11] didn't  intend  to  but  I  started  investing
[05:14] 
[05:14] in  euro  to  US  companies  my  first  three
[05:16] 
[05:16] investments  as  a  VC  were  pipedrive  from
[05:19] 
[05:19] Estonia  to  the  US  the  second  one  was
[05:21] 
[05:21] algo  Lea  France  to  the  US  and  the  third
[05:23] 
[05:23] one  was  talked  as  Portugal  us  before  we
[05:27] 
[05:27] got  the  investment  time  so  going  back  to
[05:30] 
[05:30] the  echoes  time  yes  sir  if  you  could  go
[05:33] 
[05:33] back  now  you  would  not  sell  the  company
[05:35] 
[05:35] with  where  the  cloud  is  in  2018  know
[05:39] 
[05:39] everyone  I  was  just  on  a  panel  with  the
[05:42] 
[05:42] company  called  smartsheet  smartsheet  IPO
[05:43] 
[05:43] this  year  2.5  million  beat  against  them
[05:45] 
[05:45] we  started  at  the  same  time  and  he's
[05:48] 
[05:48] like  of  course  in  2011  you  got  a  great
[05:49] 
[05:49] deal  but  now  it's  a  2.5  dollar  company
[05:52] 
[05:52] and  what  I  there's  this  annoying  VC  term
[05:55] 
[05:55] of  power  laws  you  you  read  andreessen
[05:57] 
[05:57] horowitz  and  they  and  this  term  it  first
[06:00] 
[06:00] annoyed  me  whatsapp  out  what's  up  what's
[06:01] 
[06:01] that  like  a  kind  of  annoying  VC  talking
[06:03] 
[06:03] about  power  laws  but  it's  especially
[06:05] 
[06:05] true  in  SAS  businesses  because  you  get
[06:08] 
[06:08] to  ten  and  if  that  business  compounds  to
[06:10] 
[06:10] 20  and  that  20  compounds  to  40  and  your
[06:12] 
[06:12] job  doesn't  get  any  easier  it's  just  as
[06:14] 
[06:14] hard  being  a  CEO  at  five  ten  as  five  as
[06:18] 
[06:18] 20  and  your  job  never  gets  easier  but
[06:20] 
[06:20] the  revenue  gets  easier  it  does  it
[06:22] 
[06:22] starts  to  occur  it  starts  to  build  on
[06:24] 
[06:24] itself  and  you  look  at  these  leaders
[06:27] 
[06:27] today  it's  crazy  but  all  these  the
[06:29] 
[06:29] Zendesk  HubSpot  New  Relic  all  these
[06:32] 
[06:32] companies  they're  guiding  they're
[06:33] 
[06:33] telling  Wall  Street  when  they'll  be  at  a
[06:35] 
[06:35] billion  in  revenue  a  billion  in  revenue
[06:38] 
[06:38] and  if  my  little  company  as  its  small
[06:42] 
[06:42] division  could  do  140  today  look  I  think
[06:46] 
[06:46] we  could  have  done  200  as  a  standalone
[06:48] 
[06:48] company
[06:49] 
[06:49] and  I  had  a  nice  exit  but  I'll  tell  you
[06:51] 
[06:51] I'd  rather  be  CEO  of  a  three  billion
[06:52] 
[06:52] dollar  company  David  IP  owed  this  year
[06:55] 
[06:55] then  as  much  as  I  love  faster  and
[06:57] 
[06:57] writing  content  and  doing  events  and
[06:59] 
[06:59] investing  I'd  rather  be  the  CEO  of  a
[07:01] 
[07:01] three  billion  dollar  company  especially
[07:03] 
[07:03] with  the  team  I  love  my  team  and  one  of
[07:06] 
[07:06] the  special  things  have  started  Bullard
[07:07] 
[07:07] a  team  of  the  exit  we  only  had  sixty  we
[07:10] 
[07:10] were  profitable
[07:11] 
[07:11] we  were  we  were  twelve  million  with
[07:13] 
[07:13] sixty  people  and  we  went  profitable  cash
[07:16] 
[07:16] flow  but  we  were  certainly  cashflow
[07:17] 
[07:17] positive  I  don't  know  clear  technical
[07:21] 
[07:21] there  are  a  number  of  reasons  some  which
[07:24] 
[07:24] are  specific  to  the  market  but  I  guess
[07:27] 
[07:27] the  real  most  important  reason  and  it
[07:29] 
[07:29] was  my  failing  as  a  CEO  is  the  team  got
[07:31] 
[07:31] tired  so  we  I  had  I  didn't  allow  anyone
[07:34] 
[07:34] to  quit  I  had  a  rule  of  no  voluntary
[07:36] 
[07:36] turnover  no  one  was  allowed  to  leave
[07:38] 
[07:38] many  people  almost  left  I  grabbed  two
[07:41] 
[07:41] engineers  in  the  parking  lot  leaving  but
[07:43] 
[07:43] no  one  quit  no  we  had  to  like  we  have  to
[07:45] 
[07:45] write  a  few  people  don't  do  it  you  can't
[07:47] 
[07:47] go  I  need  you  it's  not  what  do  you  need
[07:50] 
[07:50] a  raise  a  promotion  you  want  you  want  a
[07:54] 
[07:54] vacation  I  mean  with  it  no  one  would  use
[07:57] 
[07:57] dit  but  I  said  what  mistake  did  I  make  I
[07:59] 
[07:59] will  if  I  can  fix  it  I  will  fix  it  today
[08:01] 
[08:01] what  I  want  you  I  love  you  you're
[08:03] 
[08:03] amazing  like  it's  just  getting  good  like
[08:06] 
[08:06] and  nobody  quit  many  almost  quit  but
[08:09] 
[08:09] nobody  quit  I  had  to  pronoun  promote  my
[08:10] 
[08:10] best  engineer  to  a  director  of
[08:12] 
[08:12] engineering  I  had  to  make  a  few  other
[08:14] 
[08:14] changes  it  was  easier  on  the  revenue
[08:16] 
[08:16] side  than  the  engineers  or  even  quirkier
[08:18] 
[08:18] than  sales  people  but  I  couldn't  afford
[08:21] 
[08:21] to  lose  anyone  great  like  the  product
[08:23] 
[08:23] was  too  complicated  too  many  workflows
[08:25] 
[08:25] and  I  just  couldn't  let  couldn't  let
[08:27] 
[08:27] anybody  go  I  just  literally  even  my  CTO
[08:29] 
[08:29] and  my  co-founder  almost  quit  like  five
[08:31] 
[08:31] times  but  I  didn't  allow  him  to  go  I
[08:33] 
[08:33] said  you  just  you're  not  okay  and
[08:34] 
[08:34] eventually  even  with  my  CTO  after  five
[08:36] 
[08:36] years  he  transitioned  to  an  individual
[08:39] 
[08:39] contributor  he  didn't  have  any  more
[08:40] 
[08:40] reports  and  he  got  to  pick  his  projects
[08:43] 
[08:43] I  didn't  make  him  own  anything  anymore  I
[08:44] 
[08:44] let  him  pick  his  passion  projects  but
[08:46] 
[08:46] then  when  I  had  a  really  hard  problem  he
[08:49] 
[08:49] had  to  solve  it  I  went  and  grabbed  him
[08:50] 
[08:50] and  I  even  gave  him  a  desk  in  a  loft  he
[08:52] 
[08:52] didn't  even  have  to  interact  with
[08:53] 
[08:53] anybody  if  he  didn't  want  it  with  this
[08:54] 
[08:54] dog  he  had  his  dog  and  work  whatever  at
[08:57] 
[08:57] but  he  was  so  it  was  worth  a  hundred
[08:58] 
[08:58] engineers  so  I  could  I  didn't  let  him  go
[09:01] 
[09:01] and  in  fact  he's  one  of  the  top  senior
[09:03] 
[09:03] scientists  at  Adobe  so  he's  actually
[09:04] 
[09:04] been  working  on  this  same  product  for
[09:06] 
[09:06] thirteen  years  and  they  won't  let  him  go
[09:08] 
[09:08] he's  so  valuable  he  moved  to  Lake  Tahoe
[09:10] 
[09:10] in  California  he  doesn't  even  go  to  the
[09:12] 
[09:12] office  but  he's  so  valuable  that  they
[09:15] 
[09:15] they  came  to  the  same  conclusion  but  I
[09:16] 
[09:16] wouldn't  let  anybody  go  but  the
[09:18] 
[09:18] corollary  was  and  and  that's  just  that
[09:20] 
[09:20] that's  not  the  whole  story  but  but  the
[09:22] 
[09:22] reality  is  I  let  people  get  tired  I
[09:24] 
[09:24] recruited  a  great  VP  of  Sales  a  great  VP
[09:26] 
[09:26] of  product  a  great  vp  of  marketing  a
[09:28] 
[09:28] great  VP  of  customer  success  I  failed  to
[09:31] 
[09:31] recruit  a  great  VP  of  engineering  in
[09:32] 
[09:32] time  and  that  burnt  out  my  CTO  and  my
[09:34] 
[09:34] and  my  engineering  team  and  I  was  at  a
[09:38] 
[09:38] phase  transition  where  I  had  to  probably
[09:41] 
[09:41] level  the  team  up  like  I  had  great  VPS
[09:43] 
[09:43] but  they  weren't  all  gonna  be  the  VPS  to
[09:45] 
[09:45] go  from  12  to  250  million  they  weren't
[09:48] 
[09:48] right  and  I  didn't  want  to  top  people
[09:50] 
[09:50] and  I  didn't  want  to  I'm  a  slow
[09:51] 
[09:51] recruiter  and  this  is  why  I  talk  a  lot
[09:53] 
[09:53] about  forcing  yourself  to  spend  20%  of
[09:55] 
[09:55] your  time  recruiting  because  I  did  and  I
[09:57] 
[09:57] spent  10  percent  of  my  time  recruiting
[09:58] 
[09:58] and  so  I  balanced  that  with  no  attrition
[10:01] 
[10:01] because  if  nobody  left  in  theory  you
[10:03] 
[10:03] could  have  less  attrition  but  but  what  I
[10:06] 
[10:06] needed  to  do  was  what  I  learned  is  every
[10:08] 
[10:08] every  team  after  four  years  gets  tired
[10:11] 
[10:11] I've  never  found  a  team  in  SAS  that
[10:14] 
[10:14] doesn't  get  because  it  never  gets  easier
[10:15] 
[10:15] and  so  you  get  tired  and  then  people
[10:17] 
[10:17] quit  after  five  years  even  the  best
[10:19] 
[10:19] people  and  what  you  have  to  do  as  a
[10:20] 
[10:20] founder  as  the  CEO  is  you  have  to  reboot
[10:23] 
[10:23] your  company  every  five  years  and  I've
[10:25] 
[10:25] gone  on  to  interview  the  best  that  Jeff
[10:26] 
[10:26] lost  in  some  Twilio  is  the  looser  news
[10:28] 
[10:28] from  New  Relic  and  I  asked  him  this
[10:30] 
[10:30] question  how  often  would  you  Peter
[10:32] 
[10:32] Gaston  from  Viva  they  all  reboot  their
[10:34] 
[10:34] company  every  five  years  they  rebooted
[10:36] 
[10:36] it  doesn't  mean  the  team  turns  over  per
[10:38] 
[10:38] se  but  you  throw  everything  all  your
[10:40] 
[10:40] assumptions  out  it's  like  a  tour  of  duty
[10:42] 
[10:42] I  mean  it  wasn't  in  the  military  but  you
[10:43] 
[10:43] have  to  sign  up  for  a  second  tour  of
[10:45] 
[10:45] duty  every  five  years  to  do  it  and
[10:48] 
[10:48] easily  done  if  I'd  known  I  wouldn't  have
[10:51] 
[10:51] sold  I'm  still  a  student  of  all  of  this
[10:53] 
[10:53] you  find  new  goals  you  find  new  goals
[10:56] 
[10:56] first  of  all  the  most  important  thing  is
[10:58] 
[10:58] to  bring  in  the  next  level  of  management
[11:00] 
[11:00] you  need  a  CEO  you  need  people  here  but
[11:03] 
[11:03] everybody  today  wants  a  higher  CEO  at  a
[11:05] 
[11:05] million  or  1/2  million  no  you  need  it  at
[11:07] 
[11:07] 10  or  20  okay  we  need  someone  so  that
[11:09] 
[11:09] you  can  you  can  de-stress  your  job  that
[11:12] 
[11:12] someone  can  do  internal  and  external
[11:13] 
[11:13] so  that's  the  one  that  we've  all  learned
[11:15] 
[11:15] that  I  didn't  know  at  the  time  we  had  to
[11:17] 
[11:17] do  but  but  with  companies  I've  worked
[11:18] 
[11:18] with  I've  introduced  them  I  gave  talk
[11:21] 
[11:21] desk  at  CEO  Oh  a  bunch  of  other
[11:22] 
[11:22] companies  so  I  should  have  done  that  and
[11:26] 
[11:26] I  that's  probably  the  main  one  and  I
[11:30] 
[11:30] probably  needed  to  find  ways  to  push
[11:32] 
[11:32] some  of  my  team  out  of  their  comfort
[11:34] 
[11:34] zone  if  you  get  if  people  can  get  too
[11:36] 
[11:36] comfortable  we  were  we  were  profitable
[11:38] 
[11:38] we  were  doubling  but  there  are  things  we
[11:40] 
[11:40] weren't  doing  we  didn't  even  have  an
[11:42] 
[11:42] outbound  team  we  were  we  had  we  had  I
[11:43] 
[11:43] didn't  know  this  was  good  we  did  we  did
[11:45] 
[11:45] ten  million  all  inbound  we  never  did  a
[11:47] 
[11:47] single  outbound  call  we  didn't  have  an
[11:48] 
[11:48] SDR  on  our  team  I  should  have  pushed  the
[11:51] 
[11:51] team  my  marketing  team  we  didn't  do  any
[11:53] 
[11:53] corporate  marketing  no  brand  marketing
[11:55] 
[11:55] we  only  did  demand  Jen  we  did  nothing
[11:57] 
[11:57] and  we  should  have  done  more  events
[12:00] 
[12:00] there's  a  million  things  I  should  have
[12:01] 
[12:01] done  with  the  engineering  team  I  should
[12:02] 
[12:02] have  split  the  engineering  team  up  into
[12:04] 
[12:04] multiple  teams  I  I  the  best  VP  of
[12:07] 
[12:07] engineering  I  knew  at  10  million  I
[12:09] 
[12:09] offered  him  half  my  stock  I  offered  him
[12:12] 
[12:12] half  a  million  a  year  in  cash  and  half
[12:14] 
[12:14] my  stock  and  he  didn't  take  it  and  I
[12:17] 
[12:17] tried  three  times  but  I  know  him  well
[12:19] 
[12:19] and  actually  I  helped  him  get  into  the
[12:22] 
[12:22] last  Y  Combinator  class  and  now  he's  CEO
[12:23] 
[12:23] his  own  company  and  I  got  him  his  last
[12:25] 
[12:25] job  but  now  when  I  look  back  on  this
[12:27] 
[12:27] with  calm  eyes  I  should  have  asked  him
[12:29] 
[12:29] four  times  the  bet  and  now  I  know  I  do
[12:32] 
[12:32] know  in  my  heart  if  I'd  asked  him  four
[12:35] 
[12:35] times  with  half  my  shares  if  not  sold  he
[12:37] 
[12:37] would  I  wouldn't  have  sold  because  I
[12:39] 
[12:39] would  have  solved  my  engineering
[12:40] 
[12:40] problems  which  are  unsolvable  the  team
[12:42] 
[12:42] per  I  had  the  best  I  had  great  talent
[12:43] 
[12:43] but  the  organizational  problems  were  too
[12:46] 
[12:46] overwhelming  and  I  hired  I  got  tired  and
[12:48] 
[12:48] I  hired  a  bad  VP  of  engineering  and  the
[12:50] 
[12:50] team  revolted  and  I  just  I  should  have
[12:52] 
[12:52] been  a  better  CEO  and  solved  the  problem
[12:55] 
[12:55] but  selling  even  though  I  didn't  need  to
[12:57] 
[12:57] it  solved  a  bunch  of  problems  for  me  in
[12:59] 
[12:59] the  short  term  that  I  felt  like  was  fine
[13:01] 
[13:01] I  was  well-paid  I  bought  I  bought  my  I
[13:04] 
[13:04] bought  my  know  my  wife  did  very  well  as
[13:06] 
[13:06] an  entrepreneur  self  but  we  bought  a
[13:07] 
[13:07] bigger  house  we  bought  more  cars  and  it
[13:10] 
[13:10] seemed  okay  at  the  time  but  I  didn't
[13:12] 
[13:12] know  it  would  compound  but  I  should  have
[13:14] 
[13:14] but  the  last  thing  for  recruiting  and
[13:16] 
[13:16] Jordi  knows  this  you've  got  to  be
[13:18] 
[13:18] tenacious  so  I  should  have  asked  him
[13:20] 
[13:20] four  times  I  asked  him  and  I  just  should
[13:22] 
[13:22] have  been  a  nudge  and  you  would  have
[13:24] 
[13:24] joined  me
[13:24] 
[13:24] definitely  something  good  I  mean  yes  we
[13:28] 
[13:28] managed  to  raise  a  company  to  make  it
[13:30] 
[13:30] very  big  yes  but  today  is  different  you
[13:33] 
[13:33] can  do  the  cloud  is  so  big  look  at  a  WS
[13:36] 
[13:36] look  at  Amazon  the  explosion  of  Amazon
[13:39] 
[13:39] like  the  clout  and  we  can  talk  about  why
[13:41] 
[13:41] just  since  2015  the  cloud  has  grown  5x
[13:45] 
[13:45] like  this  is  a  generational  thing  that
[13:47] 
[13:47] if  you  haven't  been  around  for  a  while
[13:50] 
[13:50] if  you're  listening  I  don't  even  say  now
[13:52] 
[13:52] but  it  is  easy  to  say  now  but  if  you
[13:56] 
[13:56] have  to  talk  about  what  do  you  do  good
[13:58] 
[13:58] yes  what  were  your  keys  for  your
[14:00] 
[14:00] business  to  grow  from  from  scratch  to
[14:02] 
[14:02] where  you  grow  what  was  the  success  yeah
[14:05] 
[14:05] where  the  sales  where  the  weather  the
[14:07] 
[14:07] brother  the  the  the  most  important
[14:10] 
[14:10] lesson  I  think  from  the  from  I  talked
[14:13] 
[14:13] about  things  I  didn't  do  like  build  the
[14:14] 
[14:14] outbound  team  and  do  other  things  but
[14:15] 
[14:15] the  most  important  thing  I  did  do  was
[14:18] 
[14:18] triple  down  on  what  we  were  good  at  so
[14:20] 
[14:20] look  we  didn't  do  outbound  but  we  built
[14:22] 
[14:22] one  of  the  best  inbound  teams  the
[14:23] 
[14:23] industry  our  team  has  gone  on  to  run
[14:25] 
[14:25] sales  at  zenefits  at  Brax  at  show  pad  at
[14:29] 
[14:29] all  these  companies  they  just  spawned  at
[14:31] 
[14:31] many  other  leaders  our  sales  team  went
[14:34] 
[14:34] on  to  run  Joe  Gunton  what's  that  SEO
[14:36] 
[14:36] technical  SEO  Gorda  that  leads  come  from
[14:39] 
[14:39] no  what  did  they  do  write  sales  they
[14:41] 
[14:41] closed  the  mountain  behind  the  end
[14:43] 
[14:43] imagine  well  with  the  key  there  what  I
[14:47] 
[14:47] was  good  at  is  what  I'm  still  good  at
[14:48] 
[14:49] today  so  my  skills  on  creating
[14:51] 
[14:51] excitement  you  generate  the  throne  of
[14:52] 
[14:52] content  today  I  didn't  generate  content
[14:54] 
[14:54] in  the  day  but  what  I  did  back  in  the
[14:55] 
[14:55] day  is  I  spoke  everywhere  I  was  on
[14:58] 
[14:58] TechCrunch  all  the  time  I  was  at  every
[15:01] 
[15:01] event  every  partner  I  was  there  right
[15:03] 
[15:03] and  they  wanted  a  partner  I  was  there
[15:05] 
[15:05] yes  er  I  created  every  every  place  I
[15:08] 
[15:08] could  go  in  on  the  web  in  print  and  an
[15:11] 
[15:11] event  I  was  there  and  so  that's  what  I
[15:13] 
[15:13] and  then  I  did  a  second  thing  I  I  had
[15:16] 
[15:16] confidence  that  our  product  would  be
[15:19] 
[15:19] viral  and  we  had  a  low  viral  coefficient
[15:21] 
[15:21] but  I  was  a  buyer  because  I  send  a
[15:24] 
[15:24] contract  to  you  and  you  sign  it  and
[15:26] 
[15:26] eventually  you  would  sign  up  for  a
[15:27] 
[15:27] cosigner  DocuSign  because  you'd  never
[15:29] 
[15:29] use  the  product  before  and  the  ones  that
[15:31] 
[15:31] had  the  most  impressions  got  the  market
[15:33] 
[15:33] now  DocuSign  invested  very  aggressively
[15:35] 
[15:35] in  sales  and  marketing  I  did  nothing  but
[15:37] 
[15:37] we  add  milli
[15:38] 
[15:38] and  millions  of  people  using  our  product
[15:40] 
[15:40] every  month  and  the  fur  ality  was  slow
[15:42] 
[15:42] the  viral  but  but  and  so  in  the  first
[15:45] 
[15:45] year  it  sucked  in  the  first  year  they
[15:46] 
[15:46] didn't  we  had  six  users  six  users  did
[15:49] 
[15:49] not  get  you  six  million  six  users  get
[15:50] 
[15:50] you  one  more
[15:52] 
[15:52] but  around  year  three  just  word  of  mouth
[15:56] 
[15:56] and  morality  was  enough  to  grow  eighty
[15:58] 
[15:58] percent  when  we  hit  four  million  we
[16:00] 
[16:00] could  go  I  did  I  did  math  at  four
[16:02] 
[16:02] million  is  the  first  time  it  in  the  math
[16:03] 
[16:03] I  said  it  four  million  in  one  year  we
[16:05] 
[16:05] could  go  to  seven  with  no  expense  that
[16:07] 
[16:07] that  was  word  of  mouth  and  verrat  what
[16:09] 
[16:09] we  call  word  of  mouth  umbrella  I  go  to
[16:11] 
[16:11] seven  and  the  art  was  going  more  than
[16:12] 
[16:12] seven  right  so  that  year  we  went  four  to
[16:14] 
[16:14] eight  something  which  was  good  but  we
[16:18] 
[16:18] could  have  done  more  if  we  invested  more
[16:20] 
[16:20] but  so  I  was  good  at  excitement  and  then
[16:22] 
[16:22] I  was  I  was  super  like  religious  about
[16:26] 
[16:26] ease  of  use  for  the  product  and  we  would
[16:28] 
[16:28] win  deals  for  ease  of  use  so  that  helped
[16:30] 
[16:30] in  sales  but  it  also  helped  in  this
[16:32] 
[16:32] viral  marketing  because  our  product  was
[16:34] 
[16:34] the  easiest  to  use  product  at  the  time
[16:36] 
[16:36] by  far  that  helps  virally  you're  going
[16:38] 
[16:38] to  convert  to  the  product  that's  easier
[16:39] 
[16:39] to  use  and  and  and  and  these  products
[16:44] 
[16:44] both  echoes  on  and  DocuSign  over  time
[16:46] 
[16:46] you  have  convergent  evolution  and  the
[16:47] 
[16:47] products  are  very  similar  day  adobe  sign
[16:48] 
[16:48] but  back  then  they  were  very  different
[16:50] 
[16:50] and  DocuSign  was  a  very  powerful  product
[16:53] 
[16:53] very  sophisticated  i'm  with  great  work
[16:55] 
[16:55] clothes  ours  was  rudimentary  and  we
[16:57] 
[16:57] barely  pull  off  the  work  clothes  so  we
[16:59] 
[16:59] have  to  change  place  and  but  but  we  keep
[17:02] 
[17:02] on  from  the  same  point  so  anyhow  so  we
[17:07] 
[17:07] went  from  0  to  12  million  burning
[17:10] 
[17:10] probably  5  million  dollars  so  even  by
[17:14] 
[17:14] today's  standards  that's  pretty  good  for
[17:15] 
[17:15] a  venture  back  there  certainly  in  the
[17:17] 
[17:17] MailChimp's  to  the  world  that  burn
[17:18] 
[17:18] nothing  but  it  was  pretty  efficient  so
[17:19] 
[17:19] the  question  is  what  i'll  tell  you  what
[17:21] 
[17:21] we  did  right  and  then  what  i  could  have
[17:22] 
[17:22] been  more  that  the  number  one  learning
[17:24] 
[17:24] from  what  we  did  right  which  is  the
[17:25] 
[17:25] advice  it  i  give  to  all  founders  when
[17:28] 
[17:28] they're  not  sure  what  to  do  which  is
[17:30] 
[17:30] double  down  on  what  works  and  it's  very
[17:32] 
[17:32] frustrating  as  everyone  wants  to  grow
[17:34] 
[17:34] faster  i  have  yet  to  meet  a  founder  that
[17:36] 
[17:36] wanted  to  grow  more  slowly  right  no  one
[17:38] 
[17:38] wants  to  grow  slower  they  want  to  grow
[17:40] 
[17:40] faster  but  and  in  time  sometimes  moves
[17:43] 
[17:43] very  slowly  as  a  founder  likes  it  can  be
[17:45] 
[17:45] it  can  feel  like  it's  going  to  take  a
[17:47] 
[17:47] year  to  get  anywhere  a  quarter  to  do  a
[17:49] 
[17:49] release  but  when  you  don't  know  what  to
[17:51] 
[17:51] do
[17:52] 
[17:52] do  what  works  well  because  it's  better
[17:54] 
[17:54] to  grow  80%  this  year  and  and  have  some
[17:57] 
[17:57] success  then  -  then  to  not  know  what  to
[18:00] 
[18:00] do  burn  all  your  cash  and  grow  81
[18:01] 
[18:01] percent  it's  not  worth  it  and  people
[18:03] 
[18:03] flail  around  they  try  things  that  don't
[18:05] 
[18:05] work  but  usually  even  by  half  a  million
[18:07] 
[18:07] in  revenue  you  have  a  couple  things  that
[18:09] 
[18:09] work  or  how'd  you  get  there  you're  good
[18:11] 
[18:11] at  outbound  you're  good  at  inbound
[18:12] 
[18:12] you're  good  at  hustling  you're  good  at
[18:14] 
[18:14] content  marketing  you're  good  at  at
[18:16] 
[18:16] Facebook  Ads  you're  good  at  something
[18:17] 
[18:17] and  double  down  on  what  works  the  way
[18:20] 
[18:20] you  get  from  1  to  10  most  efficiently  is
[18:23] 
[18:23] by  spending  80  percent  of  your  time  on
[18:25] 
[18:25] what  already  work  just  getting  a  little
[18:26] 
[18:26] bit  better  at  it  so  so  let  me  let  me
[18:28] 
[18:28] stop  you  there  because  you  have  a  lot  of
[18:29] 
[18:29] great  content  about  how  to  go  from  1  to
[18:31] 
[18:31] 10
[18:32] 
[18:32] yes  but  I'm  sure  a  lot  of  our  audience
[18:33] 
[18:33] is  struggling  to  get  to  1  get  into  1  yes
[18:36] 
[18:36] so  how  do  you  go  from  100k  to  1  million
[18:39] 
[18:39] like  what  do  you  think  is  the  the  well
[18:42] 
[18:42] there's  one  most  important  thing  right
[18:43] 
[18:43] the  most  important  thing  from  getting  to
[18:45] 
[18:45] a  hundred  to  a  million  is  to  make  sure
[18:48] 
[18:48] you  have  enough  time  so  cash  maybe  it's
[18:52] 
[18:52] not  just  cash  it's  the  team  the  team
[18:54] 
[18:54] will  get  tiring  the  team  will  quit  if
[18:56] 
[18:56] you  get  to  a  hundred  thousand  in  revenue
[18:59] 
[18:59] okay
[19:01] 
[19:01] so  zero  to  a  hundred  KS  can  Dov  figure
[19:04] 
[19:04] out  do  whatever  ya  hustle  it's  all  okay
[19:09] 
[19:09] there's  something  but  actually  you  want
[19:12] 
[19:12] to  go  to  1  million  yes  and  now  a  hundred
[19:14] 
[19:14] I  don't  know  what  exactly  it  costs  in
[19:16] 
[19:16] Barcelona  but  I'll  tell  you  a  hundred
[19:18] 
[19:18] thousand  a  year  is  8k  a  month  and  that's
[19:20] 
[19:20] that's  not  a  lot  of  Engineers  in  San
[19:22] 
[19:22] Francisco  you  could  get  like  eight
[19:23] 
[19:23] engineers  in  San  Francisco  no  I  mean
[19:26] 
[19:26] it's  nothing  right  so  in  one  ways  it's
[19:28] 
[19:28] it's  it's  miraculous  you  have  a  hundred
[19:30] 
[19:30] customers  50  so  you  have  something
[19:32] 
[19:32] amazing  but  it's  not  enough  so  it's  very
[19:34] 
[19:34] frustrating  and  it  usually  takes  a  long
[19:36] 
[19:36] time  it  could  take  a  year  but  it's
[19:38] 
[19:38] promising  right  there  kind  of  feel  like
[19:39] 
[19:39] it's  promising  as  an  outsider  but  as  an
[19:41] 
[19:41] insider  it's  not  always  promising  it  can
[19:43] 
[19:43] be  frustrating  right  and  so  yes  you  and
[19:48] 
[19:48] I  Jordi  we  can  tell  people  push  on  like
[19:50] 
[19:50] you  did  something  amazing  you  a  hundred
[19:52] 
[19:52] thousand  in  revenue  but  last  thing  the
[19:54] 
[19:54] world  needs  is  another  software  product
[19:55] 
[19:55] there's  five  hundred  thousand  pieces  of
[19:57] 
[19:57] software  no  one's  asking  for  five
[19:59] 
[19:59] hundred  thousand  and  one  no  one  says  I
[20:01] 
[20:01] need  another  another  marketing
[20:03] 
[20:03] automation  solution  another  HR  solution
[20:05] 
[20:05] and
[20:05] 
[20:05] no  and  saying  I  need  another  ticketing
[20:08] 
[20:08] solution
[20:09] 
[20:09] no  one  has  woken  up  in  this  morning  and
[20:11] 
[20:11] said  I  need  one  more  CRM  I  can  go  and  no
[20:13] 
[20:13] one  no  one  said  that  so  if  you  got  to
[20:15] 
[20:15] 100,000  won  that's  a  great  you  did
[20:17] 
[20:17] something  amazing  you  you  you  you
[20:19] 
[20:19] birthed  something  in  the  world  that
[20:20] 
[20:20] someone  actually  wants  to  buy  for  real
[20:22] 
[20:22] they're  not  just  your  friends  in  your
[20:24] 
[20:24] old  boss  so  it's  amazing  but  it's  not
[20:25] 
[20:25] enough  yeah
[20:26] 
[20:26] so  you  can  either  you  can  either  and  so
[20:30] 
[20:30] what  you  have  to  do  there's  a  lot  of
[20:33] 
[20:33] things  you  can  try  which  we  can  chat
[20:34] 
[20:34] about  but  you  have  to  make  time  because
[20:37] 
[20:37] at  about  a  hundred  thousand  you  can
[20:39] 
[20:39] start  just  build  a  spreadsheet  what  am  i
[20:41] 
[20:41] growing  each  month  five  percent  okay  and
[20:43] 
[20:43] you  can  just  roll  it  forward  and  start
[20:45] 
[20:45] and  build  build  a  dispassionate
[20:48] 
[20:48] spreadsheet  that  says  and  I  call  this  I
[20:51] 
[20:51] brought  a  blog  post  called  an  L  for  M
[20:53] 
[20:53] model  the  last  four  months  and  at  about
[20:55] 
[20:55] a  hundred  thousand  do  this  now  don't
[20:57] 
[20:57] always  share  it  with  your  team  because
[20:59] 
[20:59] they  might  not  like  to  see  it  but  take
[21:00] 
[21:00] the  average  of  your  last  four  month
[21:02] 
[21:02] growth  rates  and  just  roll  it  forward
[21:04] 
[21:04] and  I  find  it  shockingly  predictive  if
[21:06] 
[21:06] you've  grown  11%  the  last  four  months
[21:09] 
[21:09] you  will  probably  like  eventually  it  may
[21:11] 
[21:11] decline  or  think  but  it's  pretty
[21:13] 
[21:13] predictive  for  the  next  six  to  nine
[21:14] 
[21:14] months  and  the  crisi  cos  all  the  time
[21:17] 
[21:17] not  liking  it  they  get  mad  and  they
[21:18] 
[21:18] predict  other  rates  and  they  never  hit
[21:19] 
[21:20] it  they  always  hit  the  L  for  M  so  and  as
[21:22] 
[21:22] an  investor  now  when  I  go  to  a  board
[21:23] 
[21:23] meeting  and  I  see  a  projection  I  just
[21:25] 
[21:25] just  skip  to  the  next  slide  and  I  build
[21:27] 
[21:27] the  L  flora  model  I  just  say  okay  this
[21:29] 
[21:29] is  you  ended  last  year  at  six  million
[21:31] 
[21:31] growing  eight  percent  a  month  I  know
[21:33] 
[21:33] exactly  where  you'll  be  next  year  I  just
[21:34] 
[21:34] get  all  no  no  but  but  the  prediction  or
[21:39] 
[21:39] the  last  four  months  doesn't  the  last
[21:40] 
[21:41] four  months  the  resolution  gets  better
[21:42] 
[21:42] over  time  in  the  early  days  the  numbers
[21:44] 
[21:44] are  so  small  the  L  forum  doesn't  work
[21:46] 
[21:46] after  a  couple  million  it  gets  super
[21:49] 
[21:49] predictive  but  anyhow  try  this  at  100k
[21:52] 
[21:52] and  if  it's  gonna  take  you  ten  years  to
[21:54] 
[21:54] get  to  a  million  but  maybe  you  should
[21:58] 
[21:58] quit  but  probably  you're  gonna  find  a
[22:00] 
[22:00] depressing  answer  probably  you're  gonna
[22:03] 
[22:03] find  it's  gonna  take  18  to  24  months
[22:05] 
[22:05] okay  and  that's  hard  where  you're  going
[22:08] 
[22:08] to  get  the  money  how  you  gonna  keep  the
[22:10] 
[22:10] team  together  how  you  gonna  pay  your
[22:11] 
[22:11] rent
[22:12] 
[22:12] and  you  have  to  find  a  way  as  CEO
[22:14] 
[22:14] because  you  will  fall  if  you  have  a
[22:15] 
[22:15] hundred  customers  of  course  you'll  get
[22:17] 
[22:17] two  hundred  it's  just  a  question  of  how
[22:19] 
[22:19] long
[22:19] 
[22:19] there  was  a  hundred  percent  unless  they
[22:21] 
[22:21] all  churn  unless  they  hate  you  even  then
[22:23] 
[22:23] you'll  get  two  to  two  hundred
[22:24] 
[22:24] they'll  just  all  churn  and  chili  yeah
[22:25] 
[22:25] but  if  you  figured  out  if  you  crack  the
[22:27] 
[22:27] code  for  a  hundred  you  will  get  to  two
[22:28] 
[22:28] hundred  and  in  fact  you  you  will  almost
[22:31] 
[22:31] certainly  get  to  a  thousand  given  enough
[22:33] 
[22:33] time  and  that's  how  you'll  hit  that's
[22:34] 
[22:34] how  you'll  go  from  if  you  have  a  hundred
[22:35] 
[22:35] customers  at  100k  you're  gonna  need  a
[22:37] 
[22:37] thousand  to  get  two  million  if  pricing
[22:39] 
[22:39] doesn't  change  so  the  question  is  this
[22:42] 
[22:42] is  your  job  as  founders  or  CEO  can  you
[22:44] 
[22:44] carry  the  company  there  and  I  went
[22:46] 
[22:46] through  this  myself  what  did  I  do  when  I
[22:48] 
[22:48] realized  this  when  I  built  this  model
[22:49] 
[22:49] well  first  of  all  I  stopped  taking  a
[22:52] 
[22:52] salary  second  of  all  I  put  half  the
[22:54] 
[22:54] money  I  made  in  my  first  startup  back
[22:56] 
[22:56] into  the  company  I  made  and  then  I
[22:59] 
[22:59] quietly  cut  some  expenses  that  didn't
[23:01] 
[23:01] touch  anybody  salary  and  anybody  knew  so
[23:03] 
[23:03] that's  what  I  did
[23:04] 
[23:04] why  not  raise  you  money  I  at  that  point
[23:07] 
[23:07] I  couldn't  raise  money  I  didn't  have  the
[23:08] 
[23:08] growth  anymore  I  was  I  was  between  hot
[23:10] 
[23:10] and  hot
[23:10] 
[23:10] I  went  from  hot  to  cold  the  hot  so  I  was
[23:13] 
[23:13] super  hot  because  I'd  sold  my  first
[23:15] 
[23:15] company  for  50  million  in  12  months  it
[23:17] 
[23:17] wasn't  a  billion  but  it  was  50  million
[23:18] 
[23:18] twelve  months  so  all  those  investors
[23:20] 
[23:20] offered  to  fund  me  again  so  I  raised  I
[23:23] 
[23:23] raised  a  couple  million  dollars  and  then
[23:25] 
[23:25] I  spent  all  of  it  and  we  got  up  to  you
[23:28] 
[23:28] know  might  one  of  my  co-founders  quit
[23:29] 
[23:29] and  we  were  at  300k  in  revenue  not  not
[23:31] 
[23:31] that  far  from  the  discussion
[23:32] 
[23:32] yeah  erinite  six  months  of  cash  left  so
[23:35] 
[23:35] I'm  like  what  am  I  gonna  do  like  it's
[23:37] 
[23:37] not  nothing
[23:37] 
[23:37] but  it's  not  enough  so  I  said  I  made
[23:42] 
[23:42] this  l4m  model  and  I  said  if  I  can  get
[23:44] 
[23:44] to  a  million  in  revenue  growing  10%  a
[23:45] 
[23:45] month  I  can  raise  more  money  which  is
[23:47] 
[23:47] exactly  what  happened  I  got  to  a  million
[23:48] 
[23:48] and  then  Excel  emergence  and  dfj  all
[23:52] 
[23:52] gave  me  intermission  in  a  week  okay  but
[23:54] 
[23:54] no  one  gave  me  a  term  sheet  what  300
[23:55] 
[23:55] can't  grant  300  growing  4%  a  month  okay
[23:58] 
[23:58] no  one  no  one  gave  me  no  big  team  sheeps
[24:00] 
[24:00] were  coming  in  at  that  point  so  I  said  I
[24:02] 
[24:02] did  the  math  and  I  said  I  need  eight
[24:03] 
[24:03] months  like  cuz  I  had  I  had  about  six
[24:06] 
[24:06] months  left  but  it  wasn't  good  I  did  the
[24:08] 
[24:08] math  it  wasn't  gonna  get  me  to  a  million
[24:09] 
[24:09] in  ten  percent  I  needed  eight  months  so
[24:11] 
[24:11] what  do  you  do  well  my  salary  in  the
[24:12] 
[24:12] u.s.  back  then  was  130  so  hey  like
[24:15] 
[24:15] taking  giving  that  back  is  a  little  bit
[24:17] 
[24:17] right  I  put  a  couple  hundred  thousand
[24:19] 
[24:19] more  in  and  then  I  did  raise  a  tiny  bit
[24:22] 
[24:22] more  money  and  did  a  few  other  things
[24:23] 
[24:23] and  I  think  I  probably  each  out  this  may
[24:25] 
[24:25] sound  like  a  lot  of  money  to  people  here
[24:27] 
[24:27] but  I'd  raised  two  and  I  needed  six
[24:29] 
[24:29] hundred  more  so  that's  only  thirty
[24:31] 
[24:31] percent  more  and  it  was  hard  to  get  it
[24:33] 
[24:33] that  got  me  the  eight  months  that  I
[24:35] 
[24:35] needed  and  then  that  we  got  over  the
[24:37] 
[24:37] hump  and  people  wanted  to  quit  but  I
[24:39] 
[24:39] told  him  they  weren't  allowed  to  quit
[24:40] 
[24:40] and  then  as  we  got  to  about  a  million  it
[24:44] 
[24:44] got  easier  you  know  it  wasn't  easier  for
[24:46] 
[24:46] me  as  CEO  but  for  my  little  tiny  sales
[24:48] 
[24:48] team  like  the  good  logo  started  to  come
[24:50] 
[24:50] in  and  my  sales  guy  bought  everyone
[24:51] 
[24:51] Christmas  dinner  and  like  it  was  it  was
[24:54] 
[24:54] different  and  the  engineers  started  to
[24:57] 
[24:57] actually  build  features  customers  wanted
[24:58] 
[24:58] and  everyone  got  their  wind  and  it
[25:02] 
[25:02] doesn't  sound  like  a  lot  of  money  today
[25:03] 
[25:03] but  I  raised  the  eight  million  dollars
[25:04] 
[25:04] in  the  a  and  got  but  I  had  to  I  had  to
[25:06] 
[25:06] buy  that  time  and  it  was  it  was  too  long
[25:08] 
[25:08] right  I  had  to  drag  the  team  and  I  don't
[25:11] 
[25:11] know  if  that's  a  depressing  or  an
[25:12] 
[25:12] inspiring  story  for  people  but  that's
[25:14] 
[25:14] from  a  hundred  you  have  to  drag  the  team
[25:16] 
[25:16] up  the  hill  and  it's  hard  because  you
[25:18] 
[25:18] can't  lose  any  soldiers  if  you  lose  one
[25:20] 
[25:20] great  engineer  and  the  early  days  you're
[25:21] 
[25:21] dead  that  might  be  the  only  engineer
[25:23] 
[25:23] that  knows  how  to  do  part  of  your
[25:24] 
[25:24] product  right  if  you  have  only  one  sales
[25:27] 
[25:27] rep  and  she's  great  and  she  quits
[25:28] 
[25:29] your  dad  you're  not  literally  dead  but
[25:31] 
[25:31] you're  dead  you  lose  you  literally  can't
[25:32] 
[25:32] lose  any  one  good  even  up  to  employee
[25:35] 
[25:35] fifty  if  you  lose  somebody  good  it's
[25:37] 
[25:37] like  death  you  have  until  you  have
[25:38] 
[25:38] redundancy  until  you  have  fat  on  the
[25:40] 
[25:40] system  it's  like  death  so  you  have  to
[25:42] 
[25:42] figure  out  how  am  I  gonna  keep  the  team
[25:43] 
[25:43] together  like  what  is  it  gonna  take  but
[25:47] 
[25:47] the  only  the  one  of  ice  I  can  give  you
[25:49] 
[25:49] is  people  that  are  single-digit
[25:51] 
[25:51] employees  are  romantics  no  one  no  one
[25:54] 
[25:54] joins  a  single-digit  employee  because
[25:55] 
[25:55] they're  rational  it  doesn't  make  any
[25:57] 
[25:57] sense  so  they're  romantic  so  your  job  is
[25:59] 
[25:59] to  inspire  the  romantics  in  the  tough
[26:01] 
[26:01] times  and  let  them  see  the  journey
[26:02] 
[26:02] immediately  do  be  very  good  I  don't  know
[26:05] 
[26:05] if  I  don't  think  ideally  good  but  I  did
[26:07] 
[26:07] it  good  enough  I  did  it  good  enough  to
[26:08] 
[26:08] but  I  agree  the  team  did  mock  me  a
[26:10] 
[26:10] little  bit  they  made  a  little  bit  of  fun
[26:12] 
[26:12] of  me  but  they  stayed  when  I  look  back
[26:14] 
[26:14] to  the  first  employees  of  our  like
[26:16] 
[26:16] previous  companies  like  why  in  hell  did
[26:19] 
[26:19] they  join  yes  there  is  no  rational
[26:21] 
[26:21] argument  to  judge  a  romantic  three  of  us
[26:23] 
[26:23] back  there  like  in  this  crappy  table  we
[26:25] 
[26:25] had  and  so  on  some  [ __ ]  was  the  same  for
[26:26] 
[26:26] X  it's  a  very  interesting  time  at  the
[26:28] 
[26:28] same  time  you're  trying  to  do  something
[26:29] 
[26:29] but  it's  not  a  rational  kind  of  argument
[26:31] 
[26:31] to  join  but  what  about  the  market  did
[26:34] 
[26:34] you  follow  the  market  that  moment  whose
[26:36] 
[26:36] stock  market  or  the  market  was  competing
[26:39] 
[26:39] with  you  it  was  so  small  it  was  it  was
[26:42] 
[26:42] less  than  a  million  dollar  market  when
[26:44] 
[26:44] we  started  you  said  something  very
[26:45] 
[26:45] interesting  yes  they  wrote
[26:46] 
[26:46] right  yeah  so  you  invested  in  Mongolia
[26:48] 
[26:48] and  that  the  time  of  our  Galia  was  like
[26:50] 
[26:50] just  two  million  two  million  dollars
[26:53] 
[26:53] yeah  II  signatures  was  1  million  when  we
[26:55] 
[26:55] started  the  Tam  was  1  million  but  you
[26:57] 
[26:57] feel  be  able  to  be  business  it  was  worth
[26:59] 
[26:59] a  lot  more  than  that  yeah  they  said  the
[27:01] 
[27:01] space  now  is  that  not  the  Tam  the  actual
[27:03] 
[27:03] revenue  and  the  space  is  a  little  over  a
[27:04] 
[27:04] billion  it  was  1  million  the  actual
[27:07] 
[27:07] market  was  1  million  in  2006  and  this  is
[27:09] 
[27:09] paralyzing  accounting  and  the  Act  not
[27:11] 
[27:11] the  time  the  actual  market  today  there
[27:13] 
[27:13] was  1  billion  of  revenue  in  a  space  that
[27:15] 
[27:15] between  us  DocuSign  and  a  few  other  guys
[27:18] 
[27:18] altogether  we  had  1  million  in  revenue
[27:20] 
[27:20] in  jail  takes  all  the  entire  industry
[27:21] 
[27:21] had  1  million  so  what  was  the  Tam  I  mean
[27:23] 
[27:23] the  Tam  might  be  high  on  a  spreadsheet
[27:25] 
[27:25] but  that  the  an  on  the  actual  market  was
[27:29] 
[27:29] 1  million  dollars  it  was  lower  that's
[27:31] 
[27:31] the  now  go  Lea  right  it  was  tiny
[27:33] 
[27:33] what  about  look  you  saying  but  the  but
[27:34] 
[27:35] the  theoretical  market  was  large  what
[27:36] 
[27:36] what  if  every  knowledge  worker  uses  your
[27:37] 
[27:38] product  right  what  about  what  if  every
[27:39] 
[27:39] what  if  every  small  business  in  Spain
[27:41] 
[27:41] uses  factorial  the  markets  huge  and  and
[27:43] 
[27:44] that's  our  founders  job  is  to  imagine
[27:46] 
[27:46] those  markets  without  being  delusional
[27:48] 
[27:48] like  being  a  being  visionary  but  not
[27:50] 
[27:50] because  delusional  if  you're  too
[27:52] 
[27:52] delusional  you'll  drive  the  truck  right
[27:53] 
[27:53] into  the  wall  right  that's  air  we're
[27:56] 
[27:56] misunderstanding  drone  software  and
[27:58] 
[27:58] burning  through  200  million  dollars  and
[27:59] 
[27:59] going  under  with  an  amazing  a  CEO  and
[28:02] 
[28:02] investors  but  a  delusional  view  of  where
[28:03] 
[28:03] drone  software  would  be  right  that  this
[28:05] 
[28:05] a  recent  example  in  business  suffer  so
[28:08] 
[28:08] you  can't  cross  that  line  but  you  have
[28:10] 
[28:10] to  see  that  a  million  can  be  a  billion
[28:12] 
[28:12] and  that's  hard  for  99%  of  the  world  to
[28:14] 
[28:14] see  but  your  single  digit  employees  will
[28:17] 
[28:17] do  it  we  had  a  meeting  and  I  remember
[28:19] 
[28:19] with  our  initial  engineering  team  that
[28:21] 
[28:21] first  Christmas  it  was  tough  we  were
[28:22] 
[28:22] doing  a  hundred  and  something  in  revenue
[28:23] 
[28:23] I  got  everybody  presents  and  my  CTO  was
[28:26] 
[28:26] very  skeptical  we'd  ever  made  it  but  our
[28:28] 
[28:28] top  engineer  at  the  time  he  started  to
[28:30] 
[28:30] pool  at  this  dinner  the  first  year  and
[28:31] 
[28:31] he's  like  how  many  employees  will  we
[28:33] 
[28:33] have  in  2016  in  10  years  and  he  got  out
[28:36] 
[28:36] is  his  phone  which  this  was  pre  iPhone
[28:38] 
[28:38] so  it  was  like  some  Blackberry  or  trio
[28:40] 
[28:40] or  something  and  he  looked  up  Adobe  had
[28:43] 
[28:43] 8,000  employees  and  so  he  said  we'll
[28:44] 
[28:44] have  10,000  we  will  be  bigger  than  Adobe
[28:47] 
[28:47] and  that's  that  didn't  exactly  happen
[28:49] 
[28:49] that  way  there's  some  irony  that  we
[28:51] 
[28:51] acquired  Adobe  what's  that  he  said  Dobby
[28:54] 
[28:54] no  we  will  be  10,000  it  echoes  I  know
[28:56] 
[28:56] but  he  mentioned  Adobe  yeah  he  said
[28:57] 
[28:57] we're  gonna  do  better  than  them  okay  so
[28:59] 
[28:59] my  point  is
[29:00] 
[29:00] a  romantic  but  he  that  was  his  thing  and
[29:02] 
[29:02] indeed  he  think  goes  a  hundred  percent
[29:03] 
[29:03] chance  no  but  he  that  was  his  romantic
[29:06] 
[29:06] side  so  those  are  the  people  you  want  to
[29:08] 
[29:08] keep  together  so  by  the  time  you  thought
[29:10] 
[29:10] look  you  saying  pretty  well  although
[29:15] 
[29:15] they  had  been  through  four  CEOs  so  I
[29:18] 
[29:18] learned  a  lot  about  when  you  can  rotate
[29:20] 
[29:20] in  and  out  management  teams  when  people
[29:22] 
[29:22] become  fungible  so  they  were  very
[29:24] 
[29:24] aggressive  competitor  and  a  very  good
[29:26] 
[29:26] company  and  Keith  crock  who  was  the  CEO
[29:29] 
[29:29] that  eventually  took  them  from  twenty
[29:31] 
[29:31] five  to  three  hundred  million  revenue  so
[29:33] 
[29:33] was  great  and  he  had  founded  Arriba  and
[29:36] 
[29:36] had  a  lot  of  experience  in  enterprise
[29:37] 
[29:37] software  but  before  that  they  went
[29:39] 
[29:39] through  four  CEOs  and  I  struggled  to
[29:41] 
[29:41] know  what  to  make  of  that  as  a
[29:43] 
[29:43] competitor  because  they  were  good  they
[29:44] 
[29:44] were  they  had  more  experience  than  me
[29:46] 
[29:46] but  fours  a  lot  of  CEOs  yeah  Keith  was
[29:48] 
[29:48] the  fifth  and  now  they're  on  the  sixth
[29:50] 
[29:50] so  the  Zen  learning  is  there's  different
[29:52] 
[29:52] ways  to  scale  the  mountain  right  and
[29:55] 
[29:55] they  had  actually  they  they  nominally
[29:58] 
[29:58] were  founded  in  2004  but  they're
[29:59] 
[29:59] actually  founded  in  2000  so  that's
[30:01] 
[30:01] eighteen  years  to  an  IPO  they  had  a
[30:03] 
[30:03] predecessor  company  called  doc  you  touch
[30:04] 
[30:04] so  eighteen  years  to  IPO  right  and  the
[30:08] 
[30:08] one  founder  left  was  diluted  to  less
[30:10] 
[30:10] than  one  percent  so  getting  to  well  you
[30:12] 
[30:12] know  18  years  of  dilution  is  less  than
[30:14] 
[30:14] one  percent  but  one  percent  of  six
[30:16] 
[30:16] billion  isn't  terrible  is  it  no  it's  not
[30:19] 
[30:19] terrible  but  it's  a  lot  of  risk  in  a  lot
[30:21] 
[30:21] of  time  and  so  they're  they're  very
[30:23] 
[30:23] interesting  paths  and  journeys  not  taken
[30:25] 
[30:25] they  they  ran  out  of  money  DocuSign  was
[30:27] 
[30:27] bailed  out  by  Salesforce  when  they  ran
[30:29] 
[30:29] out  of  money  much  to  my  chagrin  as  a
[30:30] 
[30:30] Salesforce  partner  but  the  investors  in
[30:32] 
[30:32] back  in  the  early  days  when  SAS  wasn't
[30:34] 
[30:34] hot  in  like  to  maybe  2010  they  ran  out
[30:37] 
[30:37] of  money  and  the  abhi  C's  wouldn't  put
[30:38] 
[30:38] any  more  money  in  and  Salesforce  came  in
[30:40] 
[30:40] and  gave  them  the  the  two  million
[30:42] 
[30:42] dollars  to  get  them  over  the  hump  for
[30:43] 
[30:43] the  next  round  so  lots  of  different
[30:45] 
[30:45] times  was  a  better  back  then  to  be
[30:46] 
[30:46] cashflow  positive  or  to  be  out  of  money
[30:48] 
[30:48] like  at  the  time  it  seemed  like  we  were
[30:50] 
[30:50] on  a  better  course  right  but  if  you  look
[30:52] 
[30:52] at  where  the  cloud  went  today  maybe
[30:54] 
[30:54] maybe  it  was  too  conservative  I  mean
[30:56] 
[30:56] it's  it's  it's  easy  with  hindsight  to
[30:59] 
[30:59] know  the  answers  but  they're  interesting
[31:00] 
[31:00] interesting  case  studies  so  Jason  after
[31:03] 
[31:03] that  you  you  became  an  investor  and
[31:05] 
[31:05] you're  clearly  an  enterpreneur  first  yes
[31:07] 
[31:07] you've  lived  on  your  own
[31:09] 
[31:09] a  person  with  an  interpreter  is  and  have
[31:12] 
[31:12] to  grow  a  company  so  you  kept  being  an
[31:14] 
[31:14] entrepreneur  first  yes  kind  of  investor
[31:16] 
[31:16] but  then  you  decided  to  start  investing
[31:18] 
[31:18] and  start  communicating  your  experience
[31:21] 
[31:21] yes  and  that's  where  you  are  today  yes
[31:24] 
[31:24] in  fact  I  accidentally  started  investing
[31:27] 
[31:27] and  this  community  called  faster  sort  of
[31:31] 
[31:31] accidentally  became  a  side  business
[31:32] 
[31:32] which  isn't  really  a  side  business
[31:34] 
[31:34] anymore  that  will  do  20  million  next
[31:35] 
[31:35] year  so  I'm  running  a  90  million  dollar
[31:38] 
[31:38] a  set  of  investment  funds  and  at  the
[31:39] 
[31:39] same  time  attempting  to  run  a  20  million
[31:42] 
[31:42] dollar  business  with  only  14  employees
[31:44] 
[31:44] so  and  so  I'm  making  all  the  same
[31:47] 
[31:47] mistakes  as  before  just  all  over  again
[31:49] 
[31:49] so  hopefully  it  makes  me  even  better  at
[31:52] 
[31:52] advice  as  I  continue  to  repeat  the  past
[31:54] 
[31:54] and  make  similar  mistakes  just  just
[31:56] 
[31:56] worse  you  didn't  consider  starting
[31:58] 
[31:58] another  company  like  a  cosign  like  I  did
[32:01] 
[32:01] not  have  a  company  I  did  not  I  actually
[32:05] 
[32:05] what's  that  it  is  I  knew  I  was  done
[32:08] 
[32:08] building  software  I  loved  I  love  parts
[32:11] 
[32:11] of  building  software  I  loved  building
[32:13] 
[32:13] the  wireframes  I  loved  planning  out
[32:15] 
[32:15] features  and  talking  about  it  I  even
[32:17] 
[32:17] like  the  terrible  parts  of  figuring  out
[32:20] 
[32:20] technical  debt  and  other  things  but  but
[32:24] 
[32:24] the  I  just  did  not  want  to  manage  and
[32:27] 
[32:27] build  another  engineering  team  again  it
[32:29] 
[32:29] wasn't  where  my  passion  was  I  have  a
[32:31] 
[32:31] product  guy  I'm  not  a  sales  guy  but  I
[32:34] 
[32:34] like  the  science  guy  no  I'm  not  a  sale
[32:36] 
[32:36] I'm  not  abhorrent  but  I  like  the  science
[32:38] 
[32:38] in  sales  you  have  one  of  the  most  famous
[32:40] 
[32:40] sales  books  for  b2b  fast  companies  and  I
[32:43] 
[32:43] have  lots  of  content  on  sales  but  it's
[32:45] 
[32:45] because  I'm  a  student  of  sales  I  don't
[32:46] 
[32:46] consider  myself  a  good  sales  person  but
[32:48] 
[32:48] I  learned  you  know  I  don't  I'm  not  a
[32:50] 
[32:50] good  sales  person  but  I  learned  to  have
[32:52] 
[32:52] when  I  hired  my  my  second  VP  of  Sales
[32:55] 
[32:55] Brendan  who  was  the  first  repeals  of
[32:56] 
[32:56] LinkedIn  that  was  the  first  time  I'd
[32:58] 
[32:58] ever  worked  with  the  great  VP  of  Sales
[33:00] 
[33:00] and  what  I  learned  is  an  incredible
[33:02] 
[33:02] respect  in  sort  of  love  affair  with  the
[33:04] 
[33:04] art  of  sales  and  so  I'm  not  good  at  it
[33:06] 
[33:06] I'm  good  at  top  of  the  funnel  marketing
[33:09] 
[33:09] that's  what  I'm  good  at  creating  an
[33:10] 
[33:10] excitement  and  demand  I'm  not  I'm  a  Tara
[33:11] 
[33:11] was  a  terrible  at  sales  and  I'm  still
[33:13] 
[33:13] terrible  at  it  but  I  but  I  fell  in  love
[33:16] 
[33:16] with  people  that  are  good  at  it  now  I'm
[33:18] 
[33:18] a  terrible  closer  I'm  horrible
[33:21] 
[33:21] but  I  but  I  enjoyed  the  science  of  sales
[33:24] 
[33:24] more  than  the  science  of  building
[33:26] 
[33:26] software  engineering  and  there's  a  bunch
[33:28] 
[33:28] of  reasons  why  but  I  said  I'm  not  done
[33:30] 
[33:30] in  life  but  I  am  done  spending  another  X
[33:34] 
[33:34] years  on  the  technical  side  of  building
[33:37] 
[33:37] the  product  I  would  only  do  it  if  I  had
[33:39] 
[33:39] a  co-founder  that  would  literally  do
[33:41] 
[33:41] everything  and  I  had  this  in  my  first
[33:43] 
[33:43] startup  know  and  I  first  started  out  I
[33:45] 
[33:45] found  her  like  you  do  Co  found  these
[33:47] 
[33:47] come  yeah  my  first  startup  with  it  was
[33:49] 
[33:49] actually  wonderful  I  my  co-founder  she
[33:51] 
[33:51] was  amazing
[33:52] 
[33:52] she  was  my  I  guess  she  was  our  CTO  and
[33:55] 
[33:55] head  of  technology  and  she  literally  was
[33:58] 
[33:58] a  magician  she  managed  all  of  our
[34:00] 
[34:00] engineers  all  of  our  issues  I  handled
[34:03] 
[34:03] customers  and  such  as  we  had  sales  even
[34:06] 
[34:06] though  I  was  bad  at  it  and  she  was  just
[34:08] 
[34:08] magical  a  magical  manager  a  magical
[34:11] 
[34:11] engineer  a  magical  everything  and  I  got
[34:13] 
[34:13] spoiled  I  thought  that's  the  way  the
[34:15] 
[34:15] world  works  like  I  could  be  evolved  a
[34:16] 
[34:16] little  bit  of  product  strategy  create
[34:18] 
[34:18] and  then  just  a  magic  leader  would  solve
[34:20] 
[34:20] literally  all  my  problems  I  helped  with
[34:22] 
[34:22] recruiting  but  she's  incredible  she  was
[34:24] 
[34:24] an  incredible  scientist  and  engineer  and
[34:26] 
[34:26] then  when  I  went  to  co-sign  I  thought  it
[34:28] 
[34:28] would  be  the  same  and  it  was  constant
[34:30] 
[34:30] conflict  constant  arguments  constant
[34:32] 
[34:32] back  I  just  can't  take  the  battles  like
[34:34] 
[34:34] I  like  a  little  bit  of  I  don't  even  like
[34:36] 
[34:36] an  engaged  conversation  I  just  like  to
[34:38] 
[34:38] have  fun  I  like  teamwork  and  and  just
[34:40] 
[34:40] this  friction  I  had  never  seen  before
[34:42] 
[34:42] and  I  thought  my  co-founder  could  manage
[34:45] 
[34:45] all  the  engineering  team  but  they  were
[34:46] 
[34:46] at  their  each  other's  throats  and  so  I
[34:48] 
[34:48] have  a  question  for  you  yes  and  you  said
[34:49] 
[34:49] your  terrible  days  be  terrible  itself
[34:54] 
[34:54] but  you  still  managed  to  be  like  a
[34:56] 
[34:56] decent  sales  organization  that's
[34:58] 
[34:58] different  and  you  created  like  massive
[35:01] 
[35:01] sales  training  inspiration  content  in
[35:03] 
[35:03] the  network  yes  so  like  for  CEO  who
[35:06] 
[35:06] doesn't  consider  him  or  herself  like
[35:08] 
[35:08] great  sales  person  how  do  you  recommend
[35:10] 
[35:10] themselves  to  go  about  leading  a  sales
[35:11] 
[35:11] organization  well  I'm  a  good  example
[35:13] 
[35:13] that  you  can  do  it  how  about  it
[35:16] 
[35:16] first  of  all  get  out  of  the  damn  office
[35:18] 
[35:18] and  go  close  something  try-try  here's
[35:22] 
[35:22] the  thing  that  you  as  a  CEO  may  think
[35:28] 
[35:28] that  you're  not  good  at  sales  and  you're
[35:29] 
[35:29] probably  not  good  at  sales  but  you  have
[35:30] 
[35:30] a  superpower  the  superpower  is  your  CEO
[35:33] 
[35:33] and  you  may  think
[35:35] 
[35:35] you're  the  CEO  of  a  five-person  company
[35:36] 
[35:36] that  that's  nothing  that's  not  even  like
[35:38] 
[35:38] being  a  senior  manager  at  a  big  tech
[35:40] 
[35:40] company  but  you're  wrong
[35:41] 
[35:41] customers  love  to  talk  to  the  CEO  they
[35:44] 
[35:44] love  it
[35:45] 
[35:45] an  average  manager  an  average  human
[35:47] 
[35:47] being  at  some  company  never  gets  to  meet
[35:49] 
[35:49] a  CEO  and  they  certainly  never  have  a
[35:52] 
[35:52] CEO  come  to  their  office  and  they
[35:53] 
[35:53] certainly  have  another  CEO  ask  how  they
[35:55] 
[35:55] can  help  it's  never  happened  and  you
[35:57] 
[35:57] know  what  they  don't  really  care  you're
[35:59] 
[35:59] a  CEO  of  a  five-person  company  put  it  on
[36:00] 
[36:00] your  business  card  put  it  on  your
[36:02] 
[36:02] LinkedIn  put  it  on  your  email  and  those
[36:04] 
[36:04] three  letters  will  empower  you  in  a  way
[36:07] 
[36:07] that  you  can't  you  can't  imagine  you  of
[36:09] 
[36:09] course  of  course  you  should  have
[36:11] 
[36:11] impostor  syndrome  and  that's  why  every
[36:13] 
[36:13] founder  can  at  least  be  and  I  say  I'm
[36:15] 
[36:15] bad  at  sales  but  the  truth  is  what  it
[36:17] 
[36:17] really  means  is  I'm  a  mediocre  closer
[36:18] 
[36:18] and  a  mediocre  opener  I'm  okay  for
[36:21] 
[36:21] dimension  but  like  most  CEOs  I'm
[36:23] 
[36:23] incredible  at  the  middle  like  cusp  like
[36:25] 
[36:25] I  could  figure  out  all  the  issues  of  a
[36:27] 
[36:27] sale  and  at  a  minimum  I  could  get  a  deal
[36:30] 
[36:30] all  the  way  down  the  pipeline
[36:31] 
[36:31] I  just  wasn't  always  great  at  creating
[36:33] 
[36:33] the  urgency  at  the  end  playing  the  games
[36:35] 
[36:35] at  the  end  saying  can  I  please  have  the
[36:37] 
[36:37] deal  on  December  31st  doing  the
[36:38] 
[36:38] discounting  just  the  art  of  sales  I  just
[36:41] 
[36:41] I  don't  have  the  passion  for  it  I  just
[36:43] 
[36:43] say  please  buy  but  but  as  CEOs  were  all
[36:46] 
[36:46] great  Midler's  we  all  know  but  when  you
[36:48] 
[36:48] know  what  happens  if  you  pair  the  CEO
[36:50] 
[36:50] with  a  good  sales  person  then  magic
[36:52] 
[36:52] happens  yeah  because  because  you  have  a
[36:54] 
[36:54] great  closer  a  great  midler  and
[36:57] 
[36:57] sometimes  a  great  opener  but  even  with
[36:58] 
[36:58] the  mediocre  opener  a  midler  and  a
[37:00] 
[37:00] closer  magic  happens  so  so  what  also  so
[37:04] 
[37:04] become  have  confidence  as  a  CEO  you'll
[37:07] 
[37:07] at  least  be  a  good  midler  the  more
[37:08] 
[37:08] customers  you  talk  to  you  will  get  by  a
[37:11] 
[37:11] hundred  customers  even  ten  customers
[37:12] 
[37:12] you'll  see  you'll  get  pretty  good  and
[37:15] 
[37:15] then  find  someone  in  sales  that  you  love
[37:18] 
[37:18] here's  the  hack  and  the  trick  to
[37:20] 
[37:20] becoming  a  good  sales  leader  you  don't
[37:21] 
[37:21] have  to  become  a  great  sales  are  in  the
[37:23] 
[37:23] beginning  what  you  have  to  become  as
[37:25] 
[37:25] this  Middler  as  this  as  this  evangelist
[37:27] 
[37:27] for  your  product  as  the  Guru  for  your
[37:29] 
[37:29] product  you  have  to  find  a  sales  rep
[37:31] 
[37:31] that  you  just  totally  believe  in  that
[37:33] 
[37:33] you  say  of  all  and  you're  not  you  maybe
[37:35] 
[37:35] you've  never  even  done  sales  before  but
[37:37] 
[37:37] meet  try  to  meet  20  sales  reps  out  there
[37:39] 
[37:39] wherever  they  come  from  and  don't  hire
[37:41] 
[37:41] the  one  that  had  the  great  experience
[37:42] 
[37:42] don't  hire  the  one  from  the  great
[37:44] 
[37:44] company  hire  the  one  that  you  would  buy
[37:46] 
[37:46] from  literally  that  you
[37:48] 
[37:48] by  from  not  that  you  think  a  customer  in
[37:50] 
[37:50] flight  that  you  would  buy  from  because
[37:51] 
[37:51] then  your  superpowers  of  Middler  will
[37:54] 
[37:54] transfer  right  over  them  and  my  magician
[37:56] 
[37:56] that  I  hired  this  one  he  actually  lived
[37:58] 
[37:58] in  his  brothers  garage  he  didn't  even
[38:00] 
[38:00] have  his  own  house  at  the  time  he  was
[38:03] 
[38:03] crazy  but  he  was  a  thespian  he  was  a
[38:05] 
[38:05] theater  major  both  his  parents  were
[38:07] 
[38:07] doctors  he  was  super  smart  and  he  loved
[38:09] 
[38:09] our  product  he  loved  our  product  and  I
[38:12] 
[38:12] believed  in  him  and  I  knew  I  could  give
[38:14] 
[38:14] him  a  lead  and  he  could  close  it  better
[38:17] 
[38:17] than  I  could  was  he  did  he  have  a
[38:18] 
[38:18] traditional  he  had  a  SAS  background  but
[38:19] 
[38:19] it  was  a  very  non-traditional  circle
[38:22] 
[38:22] he  was  mid-pack  at  best  and  he  was
[38:25] 
[38:25] probably  too  smart  to  be  sales  rep
[38:27] 
[38:27] number  50  he  was  -  he  would  overanalyze
[38:29] 
[38:29] everything  you  want  to  understand  the
[38:31] 
[38:31] customers  problems  he  would  like  spend
[38:33] 
[38:33] 10  hours  understanding  their  problems
[38:35] 
[38:35] like  it  was  too  many  the  customers  loved
[38:36] 
[38:36] them  but  maybe  40  minutes  was  enough  for
[38:39] 
[38:39] their  problems  at  10  hours  was  was  but
[38:41] 
[38:41] it  was  a  perfect  match  in  the  early  days
[38:43] 
[38:43] and  we  and  he  was  the  wingman
[38:45] 
[38:45] so  I  guarantee  you  as  a  CEO  you  can  find
[38:47] 
[38:47] that  person  you  can  find  a  sales  person
[38:49] 
[38:49] that  you  would  buy  from  and  don't  not
[38:51] 
[38:51] hire  that  person  and  then  when  you'll
[38:52] 
[38:52] have  to  then  you're  ready  for  a  head  of
[38:55] 
[38:55] sales  and  you're  ready  to  learn  the
[38:56] 
[38:56] science  so  break  these  things  up  into
[38:58] 
[38:58] steps  don't  get  overwhelmed  and  hire  two
[39:01] 
[39:01] salespeople  you'd  buy  from  and  you  will
[39:02] 
[39:02] become  an  expert  too  you'll  become  just
[39:03] 
[39:03] as  eligible  as  me  by  10  million  revenue
[39:06] 
[39:06] Jason  one  last  question  if  you  compare
[39:08] 
[39:08] your  life  as  an  entrepreneur  and  your
[39:11] 
[39:11] life  with  an  investor  yes  what  do  you
[39:13] 
[39:14] enjoy  more  and  what  does  it  work  more
[39:16] 
[39:16] financially  wow  there's  a  lot  of  loaded
[39:19] 
[39:19] questions  in  that  there  is  an  investing
[39:29] 
[39:29] there  is  a  lot  of  latent  stress  there's
[39:33] 
[39:33] a  latent  stress  to  find  another  good
[39:34] 
[39:34] deal  there's  never  enough  to  know  what
[39:36] 
[39:36] there's  never  enough  good  startups  there
[39:37] 
[39:37] are  never  enough  good  companies  to
[39:39] 
[39:39] invest  in  there  are  plenty  of  almost
[39:40] 
[39:40] good  enough  companies  there  are  200
[39:42] 
[39:42] companies  I  could  invest  in  every  year
[39:44] 
[39:44] that  are  pretty  good  but  will  never  be  a
[39:46] 
[39:46] unicorn  so  it  is  very  stressful  too  I
[39:49] 
[39:49] have  of  all  the  companies  I've  had  an  OP
[39:51] 
[39:51] that  wanted  me  to  invest  where  the
[39:53] 
[39:53] timing  was  right  that  I  knew  was  great  I
[39:55] 
[39:55] offered  to  invest  in  a  hundred  percent  I
[39:57] 
[39:57] didn't  turn  away  any  amazing  ones  I
[39:58] 
[39:58] never  said  you  an  amazing  startup  you're
[40:01] 
[40:01] amazing  but  note
[40:02] 
[40:02] like  the  Roquemore  just  a  timing
[40:06] 
[40:06] mismatch  I've  never  met  and  I'll  go  Leah
[40:09] 
[40:09] talk  to  ask  a  pipedrive  or  whatever  at
[40:11] 
[40:11] the  right  moment  in  time  where  I  just
[40:14] 
[40:14] said  now  now  like  there's  a  better  one
[40:16] 
[40:16] like  forget  I'm  gonna  do  intercom
[40:18] 
[40:18] intercom  better  than  talk  I  never  had
[40:20] 
[40:20] that
[40:20] 
[40:20] I  guess  the  Sequoia  and  Excel  out  of
[40:22] 
[40:22] that  but  I've  done  pretty  good  I'm  at  15
[40:24] 
[40:24] X  which  is  hard  to  do  what  I  still  never
[40:26] 
[40:26] had  assert  my  point  is  even  at  15  X  I
[40:28] 
[40:28] never  had  a  surplus  of  good  investment
[40:30] 
[40:30] candidates  right  just  like  you're  never
[40:31] 
[40:31] gonna  have  a  surplus  of  amazing  VP's
[40:33] 
[40:33] you'll  have  an  infinite  number  of  pretty
[40:35] 
[40:35] good  VPS  but  when  you  meet  that  amazing
[40:37] 
[40:37] VP  it  doesn't  happen  every  week  and  you
[40:39] 
[40:39] should  hire  her  instantly  even  if  you're
[40:41] 
[40:41] not  ready  hire  her  tomorrow  when  you
[40:43] 
[40:43] meet  the  magical  VP  of  Marketing  it's
[40:45] 
[40:45] the  same  with  an  investment  so  more  than
[40:47] 
[40:47] you  asked  for  there  is  this  latent
[40:49] 
[40:49] stress  but  it  is  nothing  like  being  a
[40:51] 
[40:51] CEO  that  stress  of  how  the  hell  am  I
[40:54] 
[40:54] going  to  go  from  100k  to  a  million  we
[40:55] 
[40:55] talked  about  earlier  with  not  enough
[40:56] 
[40:56] cash  the  stress  there  is  so  high  it  is
[41:00] 
[41:00] so  high  the  stress  of  working  so  hard  to
[41:03] 
[41:03] have  great  customers  and  your  website
[41:04] 
[41:04] going  down  for  an  hour
[41:05] 
[41:05] that's  stress  I'm  still  not  over  it  I'm
[41:08] 
[41:08] still  not  over  the  these  stresses  they
[41:10] 
[41:10] haunt  me  to  this  day  and  and  so  anyone
[41:15] 
[41:15] that  it  thinks  that  investing  is  as  hard
[41:17] 
[41:17] as  being  a  CEO  is  insane  and  anyone  that
[41:20] 
[41:20] thinks  it's  as  rewarding  has  never  been
[41:22] 
[41:22] a  CEO  there's  never  been  the  highest
[41:25] 
[41:25] high  I've  had  investing  has  not  even
[41:27] 
[41:27] been  close  to  my  hundreth  high  as  the
[41:29] 
[41:29] CEO  damn  I've  only  been  investing  for
[41:31] 
[41:31] five  years  what's  my  biggest  high  I
[41:33] 
[41:33] don't  know  I  like  I  haven't  and  we  can
[41:35] 
[41:35] talk  about  economics  but  the  first
[41:36] 
[41:36] unicorn  I  did  was  talk  dissed  I  was  the
[41:39] 
[41:39] first  seed  investor  in  2014  and  to  a
[41:41] 
[41:41] billion  dollars  a  month  ago  so  that's  40
[41:45] 
[41:45] X  in  in  four  years  and  that's  pretty
[41:49] 
[41:49] good  like  and  that's  a  fun  fun  ride  and
[41:52] 
[41:52] that  that's  as  good  as  it  gets  as  an
[41:54] 
[41:54] investor  other  than  like  being  paid  a
[41:56] 
[41:56] lot  of  money  but  it's  nothing  even
[41:58] 
[41:58] compared  to  some  just  team  celebrations
[42:00] 
[42:00] we  had  a  tech  o  sign  just  some  of  the
[42:02] 
[42:02] great  wins  are  our  first  million  dollar
[42:04] 
[42:04] bookings  month  100k  closing  Facebook  and
[42:07] 
[42:07] Google  these  iconic  brands  the
[42:08] 
[42:08] celebrations  we  had  our  Corp  our  first
[42:10] 
[42:10] retreat  our  two  first  team  retreat  that
[42:13] 
[42:13] people  still  talk  about  eight  years
[42:14] 
[42:14] later  the
[42:15] 
[42:15] that  all  of  those  memories  are  better
[42:17] 
[42:17] than  any  memory  I  will  ever  have  with
[42:19] 
[42:19] investing  what  you  do  get  from  invest  in
[42:22] 
[42:22] is  relationships  they're  the  CEOs  I  love
[42:24] 
[42:24] the  CEOs  of  the  algo  Lea's  of  the  talk
[42:26] 
[42:26] desks  of  the  rainforest  QAS  of  the  auto
[42:29] 
[42:29] miles  the  mix  maxes  some  of  these  you've
[42:31] 
[42:31] heard  of  some  of  you  have  in  the  beauty
[42:33] 
[42:33] to  investing  is  I  get  to  meet  these
[42:35] 
[42:35] amazing  CEOs  even  folks  like  Jordy  that
[42:38] 
[42:38] I'm  not  an  investor  in  these  are  the
[42:39] 
[42:39] these  are  the  best  parts  of  investing
[42:41] 
[42:41] these  are  the  relations  these  are
[42:42] 
[42:42] relationships  viewers  they  promise  to
[42:44] 
[42:44] you  right  yeah  these  are  the  these  are
[42:46] 
[42:46] the  relationships  I  wouldn't  otherwise
[42:47] 
[42:47] have  other  than  investing  even  as  a  CEO
[42:49] 
[42:49] you  don't  get  to  build  these
[42:50] 
[42:50] relationships  right  and  coming  here  we
[42:52] 
[42:53] are  at  Barcelona
[42:53] 
[42:53] and  seeing  Nicholas  the  CEO  of  Algol  AI
[42:55] 
[42:55] invested  at  15k  a  month  in  revenue  and
[42:58] 
[42:58] they'll  be  a  unicorn  soon  it's  wonderful
[43:00] 
[43:00] to  see  him  it's  really  great  to  be  a
[43:02] 
[43:02] tiny  part  of  this  journey  but  none  of
[43:05] 
[43:05] it's  as  good  as  the  highs  of  CEO  so  and
[43:09] 
[43:09] then  economics  being  a  crappy  VC  no
[43:14] 
[43:14] being  a  crappy  VC  is  bad  and  being  a
[43:16] 
[43:16] crappy  CEO  is  even  worse  being  a
[43:19] 
[43:19] mediocre  VC  is  much  better  than  a
[43:21] 
[43:21] mediocre  CEO  mediocre  CEO  you'll  never
[43:24] 
[43:24] make  any  money  the  salary  is  terrible
[43:26] 
[43:26] and  you  will  make  much  more  money  as  a
[43:28] 
[43:28] VC  with  less  stress
[43:29] 
[43:29] okay  um  is  a  better  being  mediocre  and
[43:32] 
[43:32] I'm  mediocre  is  probably  wrong  being
[43:34] 
[43:34] like  top  forty  percent  but  being  a  great
[43:37] 
[43:37] CEO  is  much  better  economically  -
[43:39] 
[43:39] because  I'd  much  rather  be  be  be  owned
[43:43] 
[43:43] 30%  of  Atlassian  as  the  cofounders  do  of
[43:46] 
[43:46] that  that's  six  billion  dollars  you  know
[43:48] 
[43:48] you  know  who's  made  six  billion  dollars
[43:50] 
[43:50] investing  like  one  or  two  people  and  and
[43:53] 
[43:53] you  can't  even  do  it  investing  you  have
[43:55] 
[43:55] to  do  it  post  investing  you  have  to
[43:57] 
[43:57] invest  in  Atlassian  and  then  all  the
[43:59] 
[43:59] shares  get  distributed  and  then  you  hold
[44:01] 
[44:01] them  for  a  few  more  years  but  as  an
[44:02] 
[44:02] investor  per  se  you  could  never  you
[44:04] 
[44:04] could  never  make  that  money  if  you  this
[44:06] 
[44:06] sounds  I  mean  if  it's  cathartic  let's
[44:08] 
[44:08] say  you  have  a  hundred  million  dollar
[44:09] 
[44:09] fund  top  quartile  is  doubling  that  money
[44:13] 
[44:13] so  you  turn  a  hundred  into  two  hundred
[44:14] 
[44:14] okay  that's  pretty  great  so  that's  a
[44:16] 
[44:16] hundred  and  profits  twenty  percent  go  to
[44:18] 
[44:18] the  partners  so  that's  twenty  million
[44:20] 
[44:20] but  it's  over  ten  years  so  it's  actually
[44:23] 
[44:23] two  million  a  year  let's  say  you  have
[44:25] 
[44:25] four  partners  that's  two  million  divided
[44:28] 
[44:28] by  four  that's  five  hundred  thousand
[44:29] 
[44:29] dollars  a  year  now  that  sounds  like  a
[44:30] 
[44:30] lot  of  money  on  this  on  this  but  it's
[44:33] 
[44:33] not  billionaire  money  is  it  and  that's
[44:36] 
[44:36] top  quartile  top  25%  performance  and  a
[44:38] 
[44:38] hundred  million  dollar  font  now  you  get
[44:41] 
[44:41] three  of  those  funds  and  that  500k
[44:43] 
[44:43] becomes  one  point  five  million  which
[44:44] 
[44:44] sounds  like  a  lot  of  money  but  you  just
[44:46] 
[44:46] want  to  know  economics  would  you  rather
[44:48] 
[44:48] sit  in  some  office  that  would  like
[44:50] 
[44:50] that's  quiet  all  day  long  bickering  with
[44:53] 
[44:53] your  partners  and  make  half  a  million
[44:54] 
[44:54] maybe  or  would  you  rather  have  a  chance
[44:57] 
[44:57] to  make  tons  more  and  run  your  own
[44:58] 
[44:58] company  which  path  with  paths  do  you
[45:00] 
[45:00] want  to  go  on  and  not  everyone  can  be
[45:08] 
[45:08] seized  and  most  VCS  can't  be  founders
[45:10] 
[45:10] they  fail  they  may  be  they  fail  as
[45:11] 
[45:11] founders  so  it's  it's  a  fake  choice  but
[45:13] 
[45:13] if  it's  cathartic  for  you  not  only  is
[45:17] 
[45:17] the  highs  are  higher  and  the  lows  are
[45:18] 
[45:18] lower  as  the  CEO  and  the  economics  are
[45:21] 
[45:21] the  same  the  economics  are  much  better
[45:22] 
[45:22] as  a  CEO  a  founder  if  you  crush  it  but
[45:26] 
[45:26] they're  they're  worse  if  you  fail  like
[45:27] 
[45:27] you  fail  as  a  CEO  you  make  I  don't  know
[45:30] 
[45:30] what  you  make  ins  in  Spain  what's  that
[45:32] 
[45:32] probably  negative  negative  maybe  you
[45:34] 
[45:34] make  40,000  euros  on  average  a  year  and
[45:36] 
[45:36] then  you're  out  of  a  job  yeah  and  then
[45:39] 
[45:39] you're  an  unemployed  failed  CEO  who
[45:41] 
[45:41] wants  to  hire  that  person  like  you  know
[45:42] 
[45:42] what  it's  hard  it's  hard  to  get  a  job  as
[45:45] 
[45:45] a  failed  CEO  if  you  fail  in  a  year  I'll
[45:48] 
[45:48] tell  you  in  all  seriousness  if  you  fail
[45:49] 
[45:49] in  a  year  people  will  hire  you  they'll
[45:51] 
[45:51] hire  you  as  a  VP  it's  great  actually
[45:53] 
[45:53] failed  CEO  in  one  year  even  a  year  and  a
[45:55] 
[45:55] half  like  that's  you  can  actually  get  a
[45:57] 
[45:57] good  job  all  the  time  in  fact  a  lot  of
[45:59] 
[45:59] the  tech  companies  in  the  u.s.  love  to
[46:00] 
[46:00] hire  these  people
[46:01] 
[46:01] the  uber  is  the  Airbnb  ease  they
[46:03] 
[46:03] actually  specifically  look  for  folks
[46:05] 
[46:05] that  got  somewhere  but  didn't  go  far
[46:06] 
[46:06] enough  and  they  make  them  divisional
[46:08] 
[46:08] general  managers  because  it's  a  great
[46:09] 
[46:09] training  ground  to  be  a  GM  but  let's  say
[46:11] 
[46:11] you're  a  CEO  for  four  years  and  failed
[46:13] 
[46:13] everyone  I've  met  there  to  burnout
[46:15] 
[46:15] there's  too  much  scar  tissue  I  meet  them
[46:17] 
[46:17] they  want  to  do  sales  with  me  they  want
[46:18] 
[46:19] to  do  this  but  they  can't  like  it's  it's
[46:21] 
[46:21] warped  your  brain  right  so  the  lows  are
[46:23] 
[46:23] lower  and  the  highs  are  higher  and  so
[46:26] 
[46:26] you're  crazy  to  be  a  founder  you're  just
[46:29] 
[46:29] crazy  to  do  it  so  only  do  it  if  you  if
[46:31] 
[46:31] you  truly  want  to  do  it  don't  do  it  for
[46:33] 
[46:33] the  glory  don't  do  it  because  it  sounds
[46:35] 
[46:35] cool  it's  just  too  hard  don't  be  a  want
[46:37] 
[46:37] to  preneur
[46:39] 
[46:39] but  if  you  do  it  it's  it's  better  than
[46:41] 
[46:41] anything  else  in  technology  we
[46:43] 
[46:43] definitely  know  what  you're  talking
[46:44] 
[46:44] about
[46:44] 
[46:44] yeah  yeah  the  old  similar  yeah  you  had
[46:47] 
[46:47] some  of  it  yeah
[46:48] 
[46:48] and  Jason  thank  you  very  much  for  your
[46:50] 
[46:50] opinion  yeah  thanks  for  all  the  time
[46:51] 
[46:51] thanks  for  having  me  very  interesting
[46:53] 
[46:53] thanks  mo  for  being  a  hero  man
[46:55] 
[46:55] yes  cold  very  good  I  like  the  dark  it
[46:58] 
[46:58] gets  rid  of  the  wrinkles  adds  to  the
[47:00] 
[47:00] hair  excuse  the  background  noise  we're
[47:05] 
[47:05] in  siege  is  that  the  point  man  capital
[47:07] 
[47:07] founders  meetup  so  yes  with  the  best  of
[47:09] 
[47:09] the  best
[47:10] 
[47:10] yeah  the  best  of  the  very  good  all  right
[47:13] 
[47:13] muchas  gracias  hasta  luego
[47:19] 
[47:19] [Music]