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by Patrick O’Shaughnessy

This week’s guest is, Zack Kanter, the founder and CEO of the Stedi.  Zack and I decided not to talk much about his business on this podcast and opted instead to explore more generally, so a bit of an introduction to what they do may be helpful here for some extra context. Stedi is a platform for exchanging and automating 300+ types of business-to-business transactions – transactions like purchase orders, invoices, etc. It’s a modern take on an archaic protocol called EDI – electronic data interchange, something I’d never even heard of until several months ago. Learning about EDI is a bit like finding out about the Matrix – every physical object you come across, from the food you ate for breakfast to the clothes you’re wearing and consumer electronics you use – anything with a barcode on it – was likely touched by EDI, often dozens of times before making it into your hands. Stedi is the first update to this messaging later in decades.

Our conversation in this podcast is about business in general, starting with Zack’s fascination with Walmart and Amazon. I should also not that my family is a recent investor in Stedi, and I’m thankful to have learned a great deal from him over the past few months. Please enjoy our conversation.

Show Notes

1:52 – (First Question) – Interest in Walmart and Amazon

            4:02 – Sam Walton:
Made In America

4:49 – What from their success can be applied elsewhere

11:07– The idea of tempo with a business

17:17 – Ability for a business to expand laterally

24:33 – Magic of Amazon as a constitution

26:24 – The concept of the OODA loop

            26:40 – Boyd:
The Fighter Pilot Who Changed the Art of War

31:51 – Orientation within software businesses

            32:24 – The
Systems Bible: The Beginner’s Guide to Systems Large and Small

38:03 – Lessons in building software

            38:37– Certain
to Win: The Strategy of John Boyd, Applied to Business

41:51 – Setting common vision for a company

44:14 – Changing dynamic of teams and how different size
teams can accomplish different things

48:00 – How leaders should think about build vs buy

51:07 – The different types of value propositions

53:07 – Utility for companies

57:31 – Concept of network health and the best question from

1:04:04 – Massive projects are less frequent in a world
where we can do a lot quickly

            1:04:08 – Wait but Why

1:09:37 – Just in time vs just in case learning framework

1:11:55 – His favorite question

1:13:39 – Why is most commonly heard advice wrong

1:18:06 – Kindest thing anyone has done for Zack

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