- Foundevo Newsletter
- Posts
- How Arjun Mahadevan Built Doola into a $100M Rocket
How Arjun Mahadevan Built Doola into a $100M Rocket
Team CompareBizTech
April 08, 2025
Dear Founders, Builders, and Bold Dreamers,
Meet Arjun Mahadevan, the founder of Doola — a platform that enables anyone in the world to launch a U.S. business, now valued at over $100 million.
His journey is not defined by privilege or shortcuts, but by relentless focus, consistent execution, and a deep understanding of what it truly means to build something from scratch.
Arjun’s story offers powerful lessons for every startup founder navigating uncertainty:
💔 What it looks like to fail with a first startup — and still keep building
💸 How a well-crafted pitch can raise $1 million in just 2 minutes
📖 Why storytelling and building in public are no longer optional, but essential
🚀 How mastering a few high-leverage moves can unlock exponential growth
To help distill the lessons, we’ve broken down Arjun’s journey into five founder-first sections, designed to give you clarity, strategies, and actionable insights at every stage of your startup path:
🚀 Founder Framework — dive deeper into the mindset and operating system behind Doola’s $100M climb
🎯 Master the Move — explore five high-leverage strategies any founder can apply to gain traction and scale smarter
📊 Pitch Perfect — analyze Doola’s Series A pitch deck to learn how Arjun crafted a compelling story that closed capital and built conviction
📹 The Founder’s Edge — watch the interview with key timestamps to see how Arjun thinks, moves, and makes decisions in real time
📘 Inside the Playbook — access a curated vault of Arjun’s pitch decks, interviews, and strategic insights for further study
Arjun Mahadevan’s $100M Founder Framework
Imagine you're standing on stage.
There are bright lights, a 2-minute timer ticking down, and judges from HubSpot sitting in front of you, deciding whether or not to give you $1 million.
🗣️ What do you say?
🧍 How do you stand?
💫 How do you make them feel?
This is exactly where Arjun Mahadevan, founder of Doola, stood — and he walked off with a $1 million check.
❌ Not because he was the most polished speaker.
❌ Not because he had the most complex slides.
But because he understood one thing:
“People don’t buy from businesses. They buy from people.”
📌 Founder Reflection:
Are you overthinking your pitch or product… and underestimating how you make people feel when they experience your brand?
From Failed Startups to a $100M Business
Before Doola, Arjun tried (and failed at) other ideas.
A social fitness app? Didn’t work.
A video messaging tool for remote teams? Crashed — even after getting into Y Combinator.
But every failure taught him something.
🎲 He didn’t quit.
🎲 He rolled the dice again.
And with Doola, he didn’t just find a business idea. He found asymmetric upside — tiny actions that led to massive outcomes.
“Startups don’t die from running out of money. They die when the founder loses motivation.”
🧠 Founder Check-In:
Are you still motivated?
If not, are you surrounded by chimps (your tribe) or stuck in a bucket full of crabs who keep pulling you back?
How He Built a Founder Brand That Fuels the Business
You don’t need to be an influencer.
You need to be a documenter.
Arjun started small — batching tweets on weekends and repurposing them to LinkedIn. Over time, he built a following of 880,000+ people across social platforms.
The outcome?
📖 Customers found Doola through his stories.
📬 Investors sent DMs.
💼 Employees already understood the culture before joining.
“Your personal brand is not fluff. It’s distribution, trust, and hiring — rolled into one.”
📝 Think Like a Founder:
🕵️♂️ Are you hiding behind your product or building in public?
🛤️ What’s one thing you could share today about your journey?
How He Uses AI, Systems & Delegation to Scale
Most founders are stuck doing low-leverage tasks.
Arjun made a $3,000 decision: outsource everything about company formation, bookkeeping, taxes, and analytics — and built that as a service for others.
This gave founders back their time to build products, land customers, and grow — not do paperwork.
“The hardest lesson is unlearning the belief that you have to do everything yourself.”
🛠️ Founder Gut Check:
🔁 What’s one part of your startup you’re still doing just because you always have?
🕊️ What could happen if you let go of it?
From LLC to Long-Term Growth
The genius behind Doola wasn’t just helping people incorporate.
That’s a one-time transaction.
The brilliance was in asking customers:
“What are you struggling with next?”
The answer?
📚 Bookkeeping.
💰 Taxes.
📊 Analytics.
So Arjun built the back-office engine — a full suite of services wrapped in trust, community, and brand.
📊 Founder Decision:
Are you trying to scale a product… or are you solving a whole problem journey for your customer?
The Truth About Success? Just Keep Rolling.
Arjun believes success in entrepreneurship is like rolling a 100-sided dice.
At first, you may only have 1 green side — and 99 reds.
But every time you roll, you learn.
And every red eventually turns green.
“The greats have failed more times than most people have even tried.”
✨ Final Takeaway: Fortune Favors the Bold
If you’re a startup founder, solopreneur, or small business owner — here’s the truth:
💡 You don’t need the best idea.
⏰ You don’t need the perfect timing.
🚫 You don’t even need YC.
You just need to take action.
Because a bold dumbass beats a shy genius — every single time.
5 Strategies to Level Up as a Founder
Every founder hits a moment where they realize —
This isn’t just about building a product.
It’s about building yourself into the kind of person who can navigate uncertainty, lead others, and create leverage where none exists.
So how do you master your move — especially when every day feels like controlled chaos?
Here are 5 high-leverage strategies founders like Arjun Mahadevan have used to stay sharp, move fast, and build with purpose.
1️⃣ Default to Action
“Action produces information. Overthinking produces doubt.”
Start small, but start now. If you're unsure whether an idea will work, don’t stew — ship. Whether it's a cold email, a landing page, or a pricing test, the moment you act, you start learning.
📌 Micro-move: Launch something uncomfortably early. Your next big breakthrough might look like a scrappy tweet or a clunky prototype.
2️⃣ Build in Public
“If no one knows what you're building, you're leaving luck on the table.”
Share your journey online. Not to show off, but to build trust. To attract early users, collaborators, and believers. The bar is low — just 1% of people post, so showing up consistently gives you exponential visibility.
📌 Micro-move: Post once a week about what you’re learning or building. Repurpose it across LinkedIn and X.
3️⃣ Talk to Your Users — Weekly
“Most startup problems can be solved by talking to more users.”
Your product roadmap doesn’t come from your head — it lives in your customers’ frustrations, wishes, and workarounds. Doola only grew because Arjun listened deeply and acted fast.
📌 Micro-move: Schedule 3 customer discovery calls this week. Don’t sell — listen. Ask, “What’s the most frustrating part of your workflow?”
4️⃣ Automate the Back Office, Focus on the Frontline
“Your highest-leverage work lives in product, sales, and vision — not in reconciling Stripe with QuickBooks.”
Successful founders ruthlessly protect their time. Delegate taxes, bookkeeping, admin, and compliance to pros so you can focus on what moves the needle.
📌 Micro-move: Audit your week. Circle the tasks someone else could do 80% as well. Systemize or outsource them.
5️⃣ Design for Asymmetric Upside
“Some moves change everything. Focus on those.”
Write the blog post that brings in 1,000 customers. Pitch the podcast that lands your first investor. Say yes to the 2-minute pitch that turns into $1 million. Be biased toward moves that cost little — but could return massively.
📌 Micro-move: Identify one asymmetric move you can make this week — then go all in.
Doola’s Series A Pitch Deck Breakdown
This pitch deck is a clear example of how simplicity, storytelling, and structure can win over investors. It shows how Arjun Mahadevan positioned Doola’s mission, communicated traction, and framed a compelling vision for the future.
Founders can use it as a reference to craft stronger narratives, sharpen their decks, and raise with clarity and confidence.
Slide 1: Title Slide: Aspirational one-liner
Slide 2: Social Proof: Show our fundraising history
Slide 3: Problem: What is the world today / status quo?
Slide 4: Solution: What does the world look like with doola?
Slide 5-9: Vision: What is our master plan (multiple slides)?
Slide 10: Monetization: How do we make money?
Slide 11: TAM: What is the total addressable market?
Slide 12: Differentiator: What makes us different?
Slide 13: Team: Why is this team special?
Slide 14: Thank You: Outro slide with contact info
Doola’s Series A deck shows that the most effective pitches are the ones that resonate with clarity and conviction. It reflects a strong understanding of the founder journey, a focused vision, and the ability to inspire investor belief. For any founder preparing to raise, this serves as a valuable example of how to combine storytelling with real traction.
🎥Learn Directly from the Source
Why just read about a founder’s journey when you can experience it firsthand?
The Founder’s Edge section is designed to bring startup wisdom straight from the source — in this case, from Arjun Mahadevan’s powerful conversation that breaks down how he built Doola from scratch, raised $1M in 2 minutes, and scaled to a $100M+ valuation.
Watch the full video and follow along with the Founder Compass to go beyond inspiration — and gain real, tactical insight you can apply to your startup journey.
To help founders extract the most valuable lessons, we’ve created a Founder Compass — a curated set of key moments and timestamps from the full interview. These moments spotlight Arjun’s mindset, strategy, pivots, and the systems he used to win.
📍 Don’t miss: Founder Compass – Key Moments with Timestamps right below.👇
⏱️ Timestamp | 💡 Key Insight | 💬 What’s In It for Founders? |
|---|---|---|
0:00 | Arjun introduces how he helped over 10,000 startups with Doola. | Sets the tone: From zero to $100M with tactical insights. |
1:00 | How he raised $1M in 2 minutes from HubSpot. | Pitching secrets revealed — body language, tone, simple slides. |
2:30 | The "KISS" pitch method and Albert Mehrabian's 93% non-verbal rule. | Learn how to win pitches before you even speak. |
4:50 | Building a founder brand on social: “People buy from people.” | Why content ≠ fluff, it’s distribution and trust. |
6:40 | The shift from product obsession to purpose: “From negative one to zero.” | Reframe your founder journey. Start before product-market fit. |
7:50 | Why Doola niched down into e-commerce and how they picked their focus. | Learn to boil a spoon before boiling the ocean. |
10:00 | Why analytics is a daily founder habit: “You can't manage what you don't measure.” | Set up insights that are too obvious to ignore. |
11:50 | "Untouchable truths": hire slow, fire fast, niche down. | Learn what you only discover the hard way. |
12:50 | Ignore the crabs: “People will try to pull you down.” | Motivation to keep rolling despite judgment. |
14:40 | How to use customer interviews to solve any business problem. | Actionable customer development strategy. |
17:00 | Does every founder need YC or On Deck? “No. You just need action.” | Reassurance for bootstrapped or rejected founders. |
21:00 | How he knew it was time to pivot during YC. | When your product isn’t the solution users are willing to pay for. |
22:45 | The $0 lesson: Always ask customers to pay upfront. | Pre-sell before you build. Save months of dev time. |
27:00 | Arjun’s "Dice of Entrepreneurship" analogy. | Brilliant metaphor on perseverance and compounding. |
31:00 | Asymmetric upside: Examples that matter (tweets, meetups, DMs). | How to maximize return from tiny bets. |
34:00 | The "3 C’s" of content strategy: Customers, Colleagues, Capital. | Why every founder needs a personal brand. |
37:00 | Arjun’s content system: Weekend batching + repurposing. | Build a content engine without burning out. |
41:00 | Turning one-time users into long-term clients through services like bookkeeping. | Add layers of recurring revenue from founder pain points. |
44:00 | Mistake: Doola built a website builder no one used. | Learn when not to build. Product vs. platform discipline. |
47:00 | LLC vs. C-Corp + State selection for US and international founders. | Straightforward legal strategy — skip the confusion. |
49:00 | Why 30–40% of businesses churn after forming. | Real talk: It’s not just money — it’s motivation that kills most. |
50:40 | Why taxes + bookkeeping aren’t optional. | Focus on growth, outsource the grind. |
Learn from Arjun Mahadevan’s Winning Moves
Here, we’ve curated the most insightful and authentic resources from Arjun Mahadevan’s journey — including pitch decks, podcast clips, viral posts, and exclusive video breakdowns.
Whether you're launching, scaling, or pivoting, we’ve gathered everything you need to study the mindset, strategy, and systems behind Doola’s rise to a $100M+ company.
🎥 1. How Arjun Mahadevan Raised $1M in 2 Minutes (Full Interview)
A raw, honest conversation with Doola’s founder on failure, fundraising, and building a brand that sells.
🚀 2. Doola on Y Combinator: From Idea to Global Startup Infrastructure
Discover Doola’s official Y Combinator company profile — insights into their product, mission, and traction.
💡 3. How I Raised $1M in 2 Minutes – Visual Breakdown
Arjun walks through the strategy, mindset, and visuals that made his million-dollar pitch unforgettable.
📈 4. The Revenue Room: Learn Sales Psychology from First Touch
Build your revenue muscle by understanding modern sales motion, buyer psychology, and high-conversion tactics.
🎥 5. The Story Behind Doola’s $1M Pitch – HubSpot's Feature Video
HubSpot Startup’s official feature on how Doola stood out and won the $1M pitch competition.
🔗 6. Arjun’s Winning Pitch Featured by HubSpot for Startups
Learn what made Arjun’s pitch irresistible to judges — and how you can replicate the formula.
📊 7. Doola’s Series A Pitch Deck Breakdown (SlideShare)
A teardown of Doola’s investor pitch deck with notes on what works, why it works, and how to learn from it.
✅ Ready to Step Into Action?
If this story lit a spark, here’s how you can fan it into a flame:
👉 Follow us at Foundevo – where we share real stories, tactical insights, and growth ideas from founders like Arjun every week.
👉 Subscribe to our newsletter – and get startup-ready tips on building, scaling, funding, and storytelling.
👉 Share this with one founder you care about – maybe they’re waiting to roll their next green.
Join thousands of founders getting tactical insights, pitch breakdowns, and mindset shifts from startup operators who’ve scaled from 0 to $100M+. 👉 Subscribe to Foundevo and turn bold ideas into real momentum.
Reply