You’ve rewritten your pitch deck five times. Practiced your delivery in the mirror.

You’ve even told yourself, “Maybe it’s just bad timing.”

But deep down, you’re starting to wonder, “Is it me? Am I doing something wrong?”

Before you spiral, take a breath.

What if the problem isn’t your idea, your pitch, or even your timing?

What if you're just following the wrong playbook?

Before you blame your deck, your timing, or even yourself…

Let Arjun Mahadevan show you what’s actually going on behind the scenes.

Who’s Arjun Mahadevan?

Arjun is the Founder & CEO of Doola, a YC-backed startup that makes it incredibly easy for anyone, anywhere in the world, to launch and manage a U.S. business.

He’s raised over $13 million from heavyweights like Y Combinator, HubSpot Ventures, Nexus VP, and angel legends like Sahil Bloom and Dharmesh Shah.

But it didn’t come easy. He raised millions, but made mistake after mistake along the way.

He's now pulling back the curtain to share six hard-earned lessons—mistakes he made and how you can avoid them—that every founder needs to hear before raising a dime.

If you missed our earlier deep dive into how Arjun Mahadevan built momentum and raised $13M for his global-first startup, you can catch up here. ️ 

Now, let’s unpack the six costly mistakes he made along the way, and how you can avoid them.

1. Mistake: Underestimating the “Rule of 60”

When Arjun first started fundraising, he thought getting 10–15 “no’s” meant something was wrong.

It didn’t. It just meant he hadn’t spoken to enough investors.

What founders get wrong:

What to do instead:

Mindset Shift:

Fundraising isn’t a one-pitch wonder, it’s strategic volume with targeted clarity.

2. Mistake: Trying to Raise the Whole Round at Once

Instead of trying to raise a $1M round at a single valuation, Arjun learned to raise in pieces:

Why this works:

What founders get wrong:

Use this strategy to:

Mindset Shift:

Treat your round like a ladder. The higher you go, the more people want to climb it.

3. Mistake: Not Using a System to Manage Investor Outreach

Arjun admits he wasted time manually following up, forgetting who he talked to, and not knowing who was close to converting.

Fundraising = Sales. Period.

And you can’t run sales without a CRM.

What founders get wrong:

Solution:

Pro Tip: Use templates for investor updates and follow-up messages. Create a weekly rhythm.

Mindset Shift:

You don’t rise to the level of your goals, you fall to the level of your systems. (James Clear)

4. Mistake: Ignoring the 55 / 38 / 7 Rule of Communication

Arjun highlights that communication is overwhelmingly non-verbal:

So when you’re pitching via Zoom—sit up, smile, bring energy.

What founders get wrong:

How to fix it:

Mindset Shift:

Investors buy your conviction before they buy your company.

5. Mistake: Asking Before You’ve Built the Relationship

This one hit hard.

Arjun shared how building investor trust before needing capital made a world of difference.

What founders get wrong:

What to do instead:

When the time comes to raise, they’re not strangers—they’re warmed up.

Mindset Shift:

People invest in motion, not just ideas. Relationships compound.

6. Mistake: Obsessing Over the “Why” Behind Every No

Arjun noticed that when investors passed, they’d often say things like:

These reasons? Often excuses. Don’t overanalyze them.

What founders get wrong:

What to remember:

Mindset Shift:

Your success isn’t defined by one no. It’s defined by your ability to keep building after 50 of them.

 A Founder’s Perspective from the Other Side of $13M

If you’re preparing to raise:

Most importantly: Don’t quit after 10 convos.

You might be just 50 rejections away from your first term sheet.

Which of these mistakes are you currently making, and what will you fix today?

Let Arjun’s story be your edge in the fundraising game.