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Episode Description:
In this episode of Made It, Connor Tomkies sits down with Arjun Mahadevan, founder and CEO of Doola, to unpack the journey from idea to company formation—and everything in between. Arjun shares how Doola has helped over 10,000 founders get started, the mindset shift required to go from -1 to 0, and why the first sale matters more than forming an LLC. They dive deep into AI adoption, building a content flywheel, the future of global entrepreneurship, and why media may be the most scalable moat of all. This is a crash course in thinking big, starting lean, and scaling smart.
In this episode of Made It, Connor Tomkies sits down with Arjun Mahadevan, founder and CEO of Doola, to unpack the journey from idea to company formation—and everything in between. Arjun shares how Doola has helped over 10,000 founders get started, the mindset shift required to go from -1 to 0, and why the first sale matters more than forming an LLC. They dive deep into AI adoption, building a content flywheel, the future of global entrepreneurship, and why media may be the most scalable moat of all. This is a crash course in thinking big, starting lean, and scaling smart.
Chapters:
[00:00:00] Starting Line Is Negative One
[00:01:30] Confidence Through Incorporation
[00:02:15] First Sale Over Perfection
[00:03:30] How Doola Got Its First Customer
[00:04:30] Talk First, Build Later
[00:05:30] Rise in Business Formation
[00:06:00] A Billion Founders Vision
[00:07:00] Global Reach Through Content
[00:08:15] Entrepreneurial Mindsets in Youth
[00:09:30] Education Is Trajectory-Changing
[00:10:30] Rise of Vibe Coding
[00:11:45] Embedding AI in Workflows
[00:13:00] IRL Beats Cold Outreach
[00:14:15] Software as the New Lead Magnet
[00:15:30] Future of Freemium Services
[00:16:30] Roadmap: Business in a Box
[00:17:30] High-Touch Services at Scale
[00:18:00] Long-Term Vision for Doola
[00:19:00] International Payroll Opportunity
[00:20:15] Scaling Through Partnerships
[00:21:30] Becoming Valuable to Partners
[00:22:30] Winning With Asymmetric Channels
[00:23:15] When Your Content Sells for You
[00:24:45] Moment Doola Was Born
[00:26:00] First Real Pain Point
[00:27:00] One Experiment Away
[00:28:30] Biggest Miss: Website Builder
[00:29:45] Opportunity Cost Is the Killer
[00:30:15] If Arjun Built Something Else
[00:31:30] Media Is the Scalable Moat
[00:32:15] Business Influencers to Follow
[00:33:45] Document, Don’t Influence
[00:35:00] Building Across Platforms
[00:36:00] Structuring Content Days
[00:37:30] Feedback in the Creative Process
[00:38:30] Wish I Filmed From Day One
[00:39:45] Marketing Tech Moves Fast
[00:40:15] Where to Find Arjun
Arjun's Stuff:
Website: https://www.doola.com/
X: https://x.com/ArjunMahadevan
LinkedIn: https://www.linkedin.com/in/mahadevanarjun/
My Stuff:
Podcast: https://www.madeitpod.com/
Website: https://www.connortomkies.com/
X: https://twitter.com/ConnorTomkies
LinkedIn: https://www.linkedin.com/in/connortomkies/
[00:00:00] Starting Line Is Negative One
[00:01:30] Confidence Through Incorporation
[00:02:15] First Sale Over Perfection
[00:03:30] How Doola Got Its First Customer
[00:04:30] Talk First, Build Later
[00:05:30] Rise in Business Formation
[00:06:00] A Billion Founders Vision
[00:07:00] Global Reach Through Content
[00:08:15] Entrepreneurial Mindsets in Youth
[00:09:30] Education Is Trajectory-Changing
[00:10:30] Rise of Vibe Coding
[00:11:45] Embedding AI in Workflows
[00:13:00] IRL Beats Cold Outreach
[00:14:15] Software as the New Lead Magnet
[00:15:30] Future of Freemium Services
[00:16:30] Roadmap: Business in a Box
[00:17:30] High-Touch Services at Scale
[00:18:00] Long-Term Vision for Doola
[00:19:00] International Payroll Opportunity
[00:20:15] Scaling Through Partnerships
[00:21:30] Becoming Valuable to Partners
[00:22:30] Winning With Asymmetric Channels
[00:23:15] When Your Content Sells for You
[00:24:45] Moment Doola Was Born
[00:26:00] First Real Pain Point
[00:27:00] One Experiment Away
[00:28:30] Biggest Miss: Website Builder
[00:29:45] Opportunity Cost Is the Killer
[00:30:15] If Arjun Built Something Else
[00:31:30] Media Is the Scalable Moat
[00:32:15] Business Influencers to Follow
[00:33:45] Document, Don’t Influence
[00:35:00] Building Across Platforms
[00:36:00] Structuring Content Days
[00:37:30] Feedback in the Creative Process
[00:38:30] Wish I Filmed From Day One
[00:39:45] Marketing Tech Moves Fast
[00:40:15] Where to Find Arjun
Arjun's Stuff:
Website: https://www.doola.com/
X: https://x.com/ArjunMahadevan
LinkedIn: https://www.linkedin.com/in/mahadevanarjun/
My Stuff:
Podcast: https://www.madeitpod.com/
Website: https://www.connortomkies.com/
X: https://twitter.com/ConnorTomkies
LinkedIn: https://www.linkedin.com/in/connortomkies/
Creators and Guests
What is Made It with Connor Tomkies?
"Made It" is a podcast hosted by Connor Tomkies that delves into the journeys of successful entrepreneurs who have not only built and exited their companies, but who are writing the next chapter of their journeys. The show focuses on the unique challenges and lessons learned while moving beyond the exit, offering insights and strategies for listeners aiming to grow their own businesses. Through engaging conversations with various guests, the podcast provides a blend of motivational stories, practical advice, and insider tips on entrepreneurship, business growth, and personal development.