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.
📚 1,800 Pitch Decks (Free) → deck-database.carrd.co
Follow Arjun’s journey:
🐦 X → x.com/ArjunMahadevan
💼 LinkedIn → linkedin.com/in/mahadevanarjun
🚀 Startup → doola.com
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📝 Newsletter → join.foundingjourney.com
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💼 LinkedIn → linkedin.com/in/michael-houck
In this conversation we discuss:
Founder Mode
- (00:00) — Intro
- (04:09) — Fundraising skills applications to life
- (05:07) — Creating a founder brand
- (06:35) — How Arjun is thinking about AI
- (12:07) — Advice to a first-time founder
- (24:31) — What Arjun took from working at Dropbox
- (26:35) — Dealing with failure as a 1st-time founder
Fundraising
- (01:13) — How to raise $1M in 2 minutes
- (14:45) — Going through OnDeck & Y Combinator
- (17:59) — doola’s value prop
- (21:03) — doola’s pivot during YC batch
Startup Strategy & Operations
- (08:01) — Why doola niched down to E-commerce
- (10:21) — Why data isn’t as actionable as we think
- (30:25) — Importance of asymmetric upside
- (44:08) — How to know when to build vs. partner with external vendors
- (46:36) — Incorporation
- (50:38) — Importance of bookkeeping
Growth
- (32:38) — The content funnel
- (35:25) — Creating content for systems
- (37:45) — Content platforms to be excited about
- (41:09) — Why any problem can be solved by talking to customers
Rapid Fire
- (53:23) — Who is one investor you’d recommend?
- (53:44) — One thing you’d change about startups?
- (54:29) — Advice for first-time founders?
- (55:33) — Something you believe that most disagree with?
