How Arjun Mahadevan Raised $1 Million in 2 Minutes

Hey y’all — surprise!

It’s me again.

Normally you wouldn’t hear from me again til Saturday, but I just had to get this great convo with Arjun Mahadevan, the founder of the YC-backed Doola (valued at $100M) who has helped over 10,000 founders start their companies, out there ASAP.

Along the way he’s built an audience of over 80,000 people across X and LinkedIn, and we cover it all — from fundraising to starting your company to building an audience.

Here’s our full convo:

Open doors to next-level growth with Vanta.

As a startup founder, finding product-market fit is your top priority.

But landing bigger customers requires SOC 2 or ISO 27001 compliance — a time-consuming process that pulls you away from building and shipping. That’s where Vanta comes in.

By automating up to 90% of the work needed for SOC 2, ISO 27001, and more, Vanta gets you compliant fast — opening doors to next-level growth opportunities.

Over 9,000 companies like Atlassian, Factory, and Chili Piper streamline compliance with Vanta’s automation and trusted network of security experts.

Get $1,000 off Vanta here.

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?

How We Can Help

Advertise in this newsletter to get in front of 75,000+ founders.