Arjun Mahadevan

Arjun is the Founder & CEO at doola.com and the host of the 15-minute founder podcast. Before that, Arjun started on the Data & Analytics team at Dropbox before moving to Product Manager on the Growth team. He graduated from the University of Pennsylvania where he completed a dual degree between The Wharton School and The College of Arts and Sciences, concentrating in Statistics and majoring in Mathematics.

Outside of work, he's into health & fitness, LLCs, and Boston sports.

Co-Founder

"If you have a startup named X but you don't have X.com, you should probably change your name." - Paul Graham

I read that and thought he was WRONG. My company was StartPack.io, and I fiercely defended that domain choice.

That was a MASSIVE mistake.

The truth I learned the hard way: a marginal domain signals you're a marginal company. When we needed to project strength to investors and users, that .io domain signaled weakness. It created an unnecessary hurdle.

If you're building, watch this. It's the full, painful story of why the DOT COM is not "just nice to have".. it's foundational credibility.

https://lnkd.in/ebrE66h6

Talks about #llc, #fintech, #brandbuilding, #entrepreneurship, and #smallbusinessadvice

CEO of @doola The Business-in-a-Box™ for E-Commerce | LLC Formation | Bookkeeping | Business Taxes | Analytics Your E-Commerce back office. Simplified.

Paul Graham once said "If you have a startup named X but you don't have X.com, you should probably change your name."

As the founder of StartPack.io, I thought he was ABSOLUTELY wrong. I defended the domain choice as irrelevant.

The truth is, I was DEAD WRONG.

In the startup world, perception IS reality. A marginal domain signals a marginal company. I break down the painful, expensive story of how not having the .com signaled a lack of strength to investors and partners at a CRITICAL moment. Never treat your domain as a "nice to have", it is a core piece of your brand and credibility.

Watch the full video: https://lnkd.in/ebrE66h6

Got into the Y Combinator interview process with my first startup, Pemvee. ZERO code written.

But I got rejected..

This video is the full breakdown. Not just the rejection, but the CRITICAL lessons I learned about product-market fit and building a no-code MVP.

You do not need to be an engineer to start. Tools like Glide, Bubble, and Zapier let you validate your idea. Your lack of technical skill is not an excuse to not launch.

The best way to find a technical co-founder is to show them you have already LAUNCHED and validated something.

Watch this if you're building a startup: https://lnkd.in/emWWneUp

Fail fast. Learn faster. That is the only way.

Your VC wants you to blow up." That is the harsh reality and the thesis behind Paul Graham’s critical essay, "Default Alive or Default Dead."

Most startups die because they hit the fatal pinch, they are Default Dead. My company, doola, almost failed because we ran out of money. We were facing the fatal pinch head-on.

Having raised over 13 MILLION dollars, I can tell you the ONLY Plan A is SURVIVAL. In this video, I break down the three concrete steps we implemented from Paul Graham’s framework to pivot from Default Dead to Default Alive. This is about building an actual, resilient business that VCs *want* to fund, not one that *needs* to be funded.

Watch the full video: https://lnkd.in/ezA7DS54

Goals set the direction. Systems do the work. 🎯

Many founders focus 90% of their energy on setting massive goals. But as Arjun explains, the goals only tell you *where* you’re going (like setting the coordinates for a marathon).

The real secret to hitting those goals is the underlying system, the daily non-negotiable process, the operational rigor, and the consistent habits (like climbing the Eiffel Tower daily).

The challenge: Shift your focus from the ambitious target to the daily, reliable process that guarantees you get there. What's one system you're refining this week?

Join me live TOMORROW at 11:30am EST right here on LinkedIn.

Competence can be taught. Conviction is fuel. 

When we're hiring, we look beyond the skills checklist. Skills are crucial, but in the volatile, high-stakes startup world, you need people who fundamentally believe in the mission, not just the paycheck.

When the inevitable tough times hit, the unforeseen pivots, the tight deadlines, the unexpected setbacks, it’s conviction that keeps the team focused, resilient, and climbing.

We're building a mission-driven team here, and it makes all the difference.

Question for discussion: Who are the high-conviction players on your team, and what mission do they champion?

PS: The best way I’ve heard this described is hire for the “slope” not the “intercept”… for the math nerds out there, hope that resonates 🤓

Y Combinator's acceptance rate is 1-2%. It is harder to get into than every Ivy League school COMBINED.

The interview is 10 minutes. That is all you get to prove your company is worth hundreds of thousands of dollars. One BITE at the apple.

I am Arjun Mahadevan, CEO of doola, a YC-backed startup that has raised over $13M. I went through this process. I know the pressure.

In my new video, I break down the three essential questions you need to nail in those 10 minutes to secure the investment. I also share a critical BONUS TIP: Be CONCISE. Your time is extremely valuable. Do not waste it.

Watch the full breakdown on YouTube:

You're a Do'er, so let's cut through the bureaucracy. A common myth is you need a passport to start your LLC. That's false.

You do NOT need the passport for LLC formation. You can secure your company (Wyoming or Delaware) in less than one week. The process is fast; we automate the heck out of it.

But here's the reality check, the bottleneck you need to plan for:

The IRS EIN Timeline

You'll need a current passport to open your U.S. Business Bank Account. And you won't get that account without your EIN (Employer Identification Number).

As a non-US resident, we have to deal with the IRS faxing process for the EIN. While we’re seeing faster movement, you need to budget for the official timeline: up to 8 weeks. We don't overpromise; this is the lag time that determines your launch date.

The Strategy: Beat the Wait

Start the LLC process NOW. Get the company formed and the EIN process initiated. This parallel path minimizes the waiting game and positions you to hit the ground running the moment your passport is renewed and the EIN comes back.

We have a direct integration with Mercury to streamline the bank account application once the EIN clears.

Your mission today: Don't wait for perfection. Start the formation. Get the EIN clock ticking.

The 10-Minute Playbook That Built Airbnb, Stripe, and Dropbox.

Michael Seibel, CEO of Y Combinator, condensed the entire startup success manual into a 10-minute speech. The rules are clear, but the application is where 99% of founders fail.

In my new video, I break down those 9 rules and share the secret 10TH RULE that YC doesn't explicitly teach. This is the rule that allowed doola to from 0 to 1 to servingover 15,000 founders.

A quick hint: It's not about the code. It's about repeatedly acquiring customers, a hurdle most startups never clear.

If you are building, raising, or scaling, this 9-minute breakdown is the MOST valuable thing you can watch today.

WATCH THE FULL BREAKDOWN HERE:

The biggest mistake founders make when fundraising? Sending massive, high-friction emails. I learned this the hard way, and it stops right now.

Investors and connectors decide if an intro is worth it in under 30 seconds. You need to make it one-click easy for them to hit 'forward.'

I’m sharing the exact, word-for-word templates and frameworks—including the PC (Praise/Connection) and PPC (Pain/Partial Solution/CTA) structures—that I've personally used to raise over $13M for doola.

Learn the 1-paragraph blurb that gets you the yes.

Analysis Paralysis is a slow death for startups. 

In the early stages of a company, waiting for 100% certainty is a luxury only incumbents can afford. As founders, our job isn't to eliminate risk; it's to manage it through rapid, informed action.

The key is gathering enough information to make an informed, reversible decision, and then moving decisively. Speed and decisiveness compound faster than perfect planning ever will. Don't let the pursuit of perfection become the enemy of progress.

Question: What's one decision you made quickly this week that paid off?

If you raised capital, congratulations. 

Now realize it means NOTHING (well not 100% nothing... capital is still capital... but capital = guaranteed success).

Forget the "fundraised" status. Focus on the METRICS THAT BUILD SUSTAINABLE BUSINESSES. 

The biggest mistake founders make and the fix, right here: https://lnkd.in/eGfCUBuT

STOP WASTING TIME IN CANVA. THIS IS WHAT AI INFOGRAPHICS CAN DO.

You are looking at an AI infographic. This is not a designer drawing.

Google’s Nano Banana update is the first AI tool that is ACTUALLY good at strategic visuals. It turns a single prompt into an asset.

The goal of a founder is to BUILD, not to get stuck in DATA GATHERING AND RESEARCH. If you're spending time drawing diagrams, you're doing it wrong.

Use AI for leverage. MOVE FASTER.

HERE ARE TWO HIGH-LEVERAGE PROMPT EXAMPLES YOU NEED:

1. YOUR COMPETITOR LANDSCAPE: Generate a competitor landscape infographic for the [Insert Industry/Product] market. Show key players, their market share, core features, and competitive advantages, highlighting [Your Company] and its unique positioning.
2. YOUR BUSINESS MODEL: Create a lean startup canvas infographic for a [Insert Product/Service] with key sections for Customer Segments, Value Propositions, Channels, Revenue Streams, Cost Structure, Key Resources, and Key Activities. Use a minimalist design with clear labels and connections.

THIS IS UNREASONABLE LEVERAGE.

PS: Here is an actual example using this prompt: Generate a competitor landscape infographic for the US LLC market. Highlight doola's unique positioning as a Business-in-a-Box™ for E-Commerce

Starting a business is not about buying the right gear.

When I started doola, I didn't need the perfect desk, the noise-canceling headphones, or the 4K webcam.

I needed the IDEA. I needed the DRIVE.

Perfection is the enemy of progress… even today, 15,000 founders later, we don’t let the “perfect” setup stop us from DOING. Case in point: check out this stack of books for a monitor stand.

If you are waiting for the perfect moment or the perfect equipment, you are already losing. That IS your weakness. The best way to start is to JUST START.

The resources you need are already within you. You just have to COMMIT.

Your customers are the co-authors of your best product.

Most teams dread negative feedback, but a founder knows it's the fastest, cheapest path to Product-Market Fit. Criticism is not a setback; it's free research and the engine that drives essential iteration.

We must accept that our initial idea is just a rough draft. Instead of defending it, we need to actively seek out the critics and listen to the critique without ego. Rapid improvement is impossible without honest, sometimes uncomfortable, feedback.

Actionable Step: Who is one person you should call this week to ask for genuinely harsh feedback on your product or service?

Some of my best founder breakthroughs happened on so-called “lazy” days.

The days when I wasn’t pushing 100mph.

When I took a long walk, or just let my brain wander.

That’s when new ideas clicked.

That’s when I saw the solution that was sitting in front of me all week.

As founders, we often treat “time not on laptop” like a luxury.

In reality, it’s part of the job.

So if today feels “lazy,” remember, rest isn’t wasted time.

It’s strategy in disguise

PS: My favorite hack is journaling for an hour or going on a walk with no device. For whatever reason, things just CLICK when you doola those two things

PPS: PPS: My favorite analogy for this is sometimes you have to “climb the tree” to see if you’re heading up the right path still… before getting back to the trail and BUSHWHACKING your way up the mountain they call a startup... Journaling = "Climbing the Tree"

My 60-second Y Combinator Demo Day pitch helped us raise millions and now serve TENS OF THOUSANDS of businesses.

But watching it back, I see key mistakes I made in communicating the core problem and market size. The biggest lesson is what the data shows: 93 PERCENT OF COMMUNICATION IS NON-VERBAL. Your words matter, but HOW you say them matters MORE.

If I were pitching doola today, here are the three major changes I would make to my presentation, problem framing, and bottom-up sizing. Every founder needs to master their pitch, it is the single MOST IMPORTANT minute of your early business life.

What you say YES to defines your strategy. What you say NO to defines your culture.

This is one of the most fundamental truths in leadership.

Your strategy is the path you choose (the 'Yes' to markets, features, and pursuits). But your culture is what you allow, and that is entirely built upon your 'No.'

We must protect our 'No' just as fiercely as we champion our 'Yes.' It's the refusal to compromise on values, the unwillingness to work with difficult clients, and the decision not to cut essential corners that truly solidifies a strong, enduring culture.

What is one thing you've said 'No' to recently to protect your team's culture? Share your insights.

Insight from investor and entrepreneur Peter Thiel:

START YOUR LLC

BUILD AND SELL

REPEAT

STOP OVERTHINKING

Hire, Manage, and Retain Top Talent - Live Q&A

Join Arjun Mahadevan, doola's CEO, LIVE for a Weekly Q&A. ⚡️

No gatekeeping. No fluff. Just real, tactical advice.

When: Every Wednesday
Time: 11:30am EST
Where: Right here on our YouTube channel.

Join live to get your questions answered in real time.

Let’s build.

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