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April 2, 2025 β€’ 58 mins

Arjun built a $100M startup by helping other founders incorporate and start their own. Along the way he went through Y Combinator and built an audience of over 80,000 people on X and LinkedIn.


πŸ“š 1,800 Pitch Decks (Free) β†’Β deck-database.carrd.co


Follow Arjun’s journey:

🐦 X β†’Β x.com/ArjunMahadevanΒ 

πŸ’Ό LinkedIn β†’Β linkedin.com/in/mahadevanarjunΒ 

πŸš€ Startup β†’Β doola.com


Follow us:

πŸ”” Subscribe β†’youtube.com/@callmehouck?sub_confirmation=1Β 

πŸ“ Newsletter β†’Β join.foundingjourney.comΒ 

πŸ“ˆ Founder Membership β†’Β upgrade.foundingjourney.comΒ 

πŸ’Ό LinkedIn β†’Β linkedin.com/in/michael-houck


In this conversation we discuss:


Founder Mode

  • (00:00) β€” Intro
  • (04:09) β€” Fundraising skills applications to life
  • (05:07) β€” Creating a founder brand
  • (06:35) β€” How Arjun is thinking about AI
  • (12:07) β€” Advice to a first-time founder
  • (24:31) β€” What Arjun took from working at Dropbox
  • (26:35) β€” Dealing with failure as a 1st-time founder


Fundraising

  • (01:13) β€” How to raise $1M in 2 minutes
  • (14:45) β€” Going through OnDeck & Y Combinator
  • (17:59) β€” doola’s value prop
  • (21:03) β€” doola’s pivot during YC batch


Startup Strategy & Operations

  • (08:01) β€” Why doola niched down to E-commerce
  • (10:21) β€” Why data isn’t as actionable as we think
  • (30:25) β€” Importance of asymmetric upside
  • (44:08) β€” How to know when to build vs. partner with external vendors
  • (46:36) β€” Incorporation
  • (50:38) β€” Importance of bookkeeping


Growth

  • (32:38) β€” The content funnel
  • (35:25) β€” Creating content for systems
  • (37:45) β€” Content platforms to be excited about
  • (41:09) β€” Why any problem can be solved by talking to customers


Rapid Fire

  • (53:23) β€” Who is one investor you’d recommend?
  • (53:44) β€” One thing you’d change about startups?
  • (54:29) β€” Advice for first-time founders?
  • (55:33) β€” Something you believe that most disagree with?
Mark as Played

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