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.

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Follow Arjun’s journey:

🐦 X → x.com/ArjunMahadevan 

💼 LinkedIn → linkedin.com/in/mahadevanarjun 

🚀 Startup → doola.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?