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