Podcast When It Clicked

Behind every business success story is a moment where fate hangs in the balance. Meet the people building the businesses and products you THINK you know to discover the secret history of how it all came together—to the one moment when it all, finally, clicked.
Play Trailer
When It Clicked

Get episode alerts delivered to your device

Subscribe now

Host Meet Ilana Strauss.

"The news can make starting a business seem one-dimensional. But 'When It Clicked' pulls back the veil and tells you the whole story, stumbles and all."
Ilana Strauss is a journalist from Chicago.
Her work has appeared in The Atlantic, The Economist, National Geographic, Snap Judgement, and other outlets.

Latest Episodes Listen now to When It Clicked.

Google Docs (Writely)

Before it became Google Docs, it was Writely, software that broke new ground by enabling real-time document collaboration. We look back with its founders on why they initially turned down Google, the need to create a fake save button, and how they discovered the feature that defined the software’s success.


After countless hours spent battling with a stack of forms and a Kinko’s fax machine, Parker Conrad knew the HR process was ripe for a revamp. In this episode, we’ll hear how this three-time founder discovered an untapped market within employee management, changed the mindset around HR tech, and turned Rippling into a billion dollar company.


Today, Shopify powers more than 1.7 million merchants with enough sales to make it the second largest online retailer in the U.S. But getting here meant making some unconventional choices. In this episode, we dive deep into the company’s backstory to learn why Shopify decided to do more than build “websites with shopping carts” and how its plan to turn everyone into an entrepreneur led to its success.


Scratchpad was designed as a tool to simplify Salesforce. But for neurodiverse individuals, it’s also a lifeline. In this episode, we peel back the curtain on Scratchpad to find out how its founders tapped into its neurodiverse users, and how designing a product for the various ways people think made all the difference.


Email is a tool people love to hate—so much that many tech companies have tried to kill it for good. But Mathilde Collin saw the flaws with email as an opportunity, and set out to build a company around improving the inbox. In this episode, we delve into the founding of Front, and find out how two entrepreneurs from France built a billion dollar business on a software tool others had overlooked.

Feedback Join other listeners & let us know
what you think.

Sign up for FREE and start using ClickUp in seconds!

Please enter a valid email address