Episode 417: From Nine Rejections to Two IPOs with Babu Sivadasan
What if the job you almost didn't get became the foundation for building two public companies? That's exactly what happened to Babu Sivadasan, who was rejected by nine firms before landing his first job out of college, a job he still calls the best deal he ever made.
Babu is a serial entrepreneur and engineer who co-founded stamps.com and later co-founded Envestnet, two category-defining platforms in commerce and wealth management technology. He's now the founder of Jiffy AI, applying artificial intelligence to how software gets created and deployed.
In this episode, Babu traces a 1990s patent that became stamps.com, a demo computer damaged in his suitcase before a make-or-break Postal Service pitch, and an accidental pivot into wealth management that led to Envestnet. He also shares why he believes natural language will replace traditional programming, and how that belief now drives Jiffy AI.
Whether you're weighing whether to raise capital or curious how AI is reshaping wealth management technology, this conversation offers a rare, three-decade view of how founders build through very different technology eras.
FOR MORE ON BABU SIVADASAN: https://www.jiffy.ai
FOR MORE ON COREY KUPFER: https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/
Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.
Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!
Episode Highlights with Timestamps
[02:20] - Rejected by nine firms before landing his first job
[05:17] - The 1990s patent that became stamps.com
[13:19] - A damaged demo computer and a make-or-break Postal Service pitch
[25:15] - The accidental pivot into wealth management
[32:41] - Unifying a fragmented advisor tech stack at Envestnet
[54:06] - Jiffy AI today: Series B funded, $61 million raised
Guest Bio
Babu Sivadasan is a serial entrepreneur with deep experience building and scaling public companies backed by a strong engineering foundation. He co-founded stamps.com and later co-founded Envestnet, helping shape category-defining platforms in commerce and financial services. He is now the founder of Jiffy AI, applying natural language AI technology to how software is created and deployed for the wealth management industry. Babu is also an active angel investor and mentor, supporting startups across Silicon Valley and India.
Related Episodes
Episode 328 - Richard Manders: a fellow engineer-turned-founder whose curiosity about how things work led him from an early career in automation to building and scaling multiple companies with private equity backing.
Episode 370 - Gerry Hays: explores how collapsing startup costs and artificial intelligence are reshaping who can raise capital and become a founder, a theme that runs through Babu's own move from the cloud era into the AI era.
Episode 350 - Tom Dillon: examines when founders should look beyond venture capital for funding, a question Babu faced directly in the cash-strapped early days of stamps.com.
