In this special live episode of Big Shot, recorded at StartupFest, we are excited to welcome Heather Reisman, the trailblazing entrepreneur behind Indigo Books & Music. Heather's remarkable journey began as a single mother learning to code to support her children.

Fueled by grit, a bit of luck, and a talent for connecting with extraordinary people, Heather built Indigo into Canada’s largest bookseller. However, Heather's ambitions extend beyond her role as founder and CEO. She is also a devoted wife, mother, grandmother, and philanthropist, having contributed $100 million to the University of Toronto and supported various causes through her foundation, HSEG, which aids the education of lone soldiers after their service in the IDF. In today’s conversation, we talk about: 

• Heather’s childhood and how her working mother influenced her


• The importance of curiosity and how this value has served Heather in entrepreneurship


• Heather’s first startup, Paradigm


• Heather’s work at Cott and how she broke out of a mental funk after leaving


• Raising $25 million and founding Indigo


• Founding Kobo eReaders and selling to Rakuten for $315 million


• Heather’s life beyond work and plans for increasing Canada’s literacy

—

In This Episode We Cover:

(05:08 ) Welcome Heather Reisman

(05:35 ) What it was like growing up in the Reisman household

(10:26 ) Heather’s experience working at her mother’s retail store

(11:15 ) Heather’s early passion for books

(12:44 ) Why Curiosity is the key to everything

(14:00 ) Heather’s coding journey as a single mom

(16:00 ) Why Heather quit her job after an undeserved demotion 

(17:00 ) Heather’s time working at a consulting firm

(19:00 ) Co-founding Paradigm 

(19:56 ) Heather’s thoughts on change and why she left consulting

(24:29 ) Why Heather left Cott 

(26:55 ) Heather’s depression and the book that kickstarted the next chapter of her life

(20:24 ) The Borders deal that never worked out

(33:00 ) Raising $25 million and founding Indigo 

(37:19 ) The story of acquiring Chapters 

(39:45 ) Integrating Chapters

(42:13 ) How the ‘New Coke” failure inspired Heather to keep Chapters and Indigo separate 

(43:20 ) Why Heather founded an e-reader company called Kobo

(48:47 ) Selling Kobo to Rakuten for $315 million 

(50:19 ) The power of Heather’s Picks

(52:13 ) Taking Indigo private

(53:00 ) Heather’s literacy goals and the importance of curation

(57:00 ) How Heather balances work and family life

Where To Find Heather Reisman:

X: https://x.com/heatherreisman

Instagram: https://www.instagram.com/heatherreisman

Facebook: https://www.facebook.com/hreisman

LinkedIn: https://www.linkedin.com/in/heather-reisman-3bab2319

TikTok: https://www.tiktok.com/discover/heather-reisman-indigo

Where To Find Big Shot: 

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.bigshot.show/⁠⁠⁠⁠⁠

YouTube: ⁠⁠⁠⁠⁠⁠https://www.youtube.com/@bigshotpodcast⁠⁠⁠⁠⁠⁠  

TikTok: ⁠⁠⁠⁠⁠https://www.tiktok.com/@bigshotshow⁠⁠⁠⁠⁠

Instagram: ⁠⁠⁠⁠⁠⁠https://www.instagram.com/bigshotshow/⁠⁠⁠⁠⁠⁠  

Harley Finkelstein: ⁠⁠⁠⁠⁠⁠https://twitter.com/harleyf⁠⁠⁠⁠⁠⁠ 

David Segal: ⁠⁠⁠⁠⁠⁠https://twitter.com/tea_maverick⁠⁠⁠⁠⁠⁠

Production and Marketing: ⁠⁠⁠⁠⁠⁠⁠https://penname.co⁠