Chris Gilpin from OrderUp

Chris Gilpin is the CEO of OrderUp (acquired by Wealthsimple).

OrderUp's Point of Sale helps restaurants improve Front of House efficiency by 66% by empowering guests to order and pay from their phones.

Chris also Co-Founded Turnstyle Solutions (acquired by Yelp) and Ascendent a reinsurance business focused on bitcoin.

Takeaways

Working at Apple and chatting with Steve Jobs.

The hacky way they got restaurants to use Turnstyle.

The acquisition of Turnstyle by Yelp and learnings.

Chris's interest in Bitcoin led to the creation of Ascendant Capital, a reinsurance company that provides managed exposure to the Bitcoin space.

Launching OrderUp during the pandemic and being acquired by Wealthsimple.

Chris's thoughts on the Toronto tech scene.

Insights into loyalty marketing.

How to evaluate ideas and a process to turn them into a business.

The importance of meditation in Chris's life.

Chapters

00:00 Chris's time at Western and decision to pursue dual degrees

01:13 Chris's experience working at Apple

06:09 Starting TurnStyle and the motivation behind it

09:29 Scaling TurnStyle and the challenges faced

12:00 The acquisition of TurnStyle by Yelp

14:08 Chris's interest in Bitcoin and the creation of Ascendant Capital

23:48 Creation of OrderUp and interest in the POS and online ordering space

24:11 Passion for Supporting Restaurant Operators

25:08 The Seamless Integration of WeChat in Restaurants

25:37 Pivoting to Online Ordering and Payment

26:07 Challenges with Integrating with Point of Sale Systems

27:04 Becoming a Point of Sale System

27:54 The Wealthsimple Acquisition

29:28 The Toronto Tech Scene

30:27 Funding Challenges in Canada

31:19 Future Potential in Loyalty Marketing

32:03 Bridging the Gap Between Online Advertising and Offline Transactions

36:05 Chris' Process for Starting New Ventures

39:32 Chris' Focus and Future Plans

40:44 Favorite Books: 'The Bitcoin Standard' and 'How to Create a Mind'

42:33 Dealing with Hard Times: Importance of Having a Co-founder and Meditation

45:27 Encouragement to Learn About Money and Rethink the Monetary System