Header image for Episode 2019-06 of the Crommunity Podcast
  • 15
  • August

Exploring Clouds, US vs Canadian Companies, and Corporate Development with Cassio Sampaio (Crommunity Podcast)

My guest on this episode is Cassio Sampaio, a seasoned tech veteran whose career includes stints running professional services departments, product management teams, and marketing organizations, but I was particularly excited to explore his experience with corporate development—and, specifically, mergers and acquisitions.

Cassio also brings an informed international perspective. Over the years, he’s worked in Brazil, the Czech Republic, Canada, and the US—plus, he’s travelled basically everywhere.

Nowadays, he makes his home in the heart of Silicon Valley, at a company you’ve definitely heard of, but which makes it pretty clear in their employment agreement that you aren’t supposed to represent them on podcasts and things.

So let me be 100% clear, for any lawyers out there: I’m talking to Cassio the friend and former colleague in his capacity as himself and his past career, not his present position =D

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Sit back, relax, and enjoy learning about clouds, scaling, the differences between Canadian companies and US companies, and corporate development.

You can grab the mp3 here.

Here’s your handy topic-and-timing guide:

  • [3:00] Cassio’s transition from ~12 years in telecom into the exciting world of public clouds, which actually represented a return to his hosting and infrastructure roots, and some of the major differences

Telecom’s not known for moving fast and breaking things. (When things break in telecom) people get very upset, including regulators, which I think is a very important difference between new tech and old tech.

  • [4:45] A little bit about the investment and network evolution cycles in telecom, and how over-the-top services threaten the entire business model (the entire Thing-as-a-Service revolution depends on reliable telecommunications, but the telecoms themselves aren’t the ones getting paid)
  • [9:39] The cloooooooouuuuuud! Amazon (“They are a logistics company, and this is a logistics problem.”), scaling (“How do you buy, rack, stack, install, manage, 350,000 new servers coming into your data centers?”), how it’s more than just someone else’s computer, big data, AI…

Telco and cloud are about moving and storing data faster, cheaper, and better than yesterday. It’s a constant move towards efficiency and volume.

  • [18:07] Are we in an age of incremental improvement, rather than real innovation?
  • [20:43] Cassio’s time at Digital Ocean, including contrasts between Canadian and US companies, the strong risk of analysis paralysis in today’s data-heavy businesses, retrospective data, leading metrics, and creative destruction vs incremental change

The one thing that struck me (at Digital Ocean) was the willingness to bet on things, without the need to find a lot of confirmation. Maybe it’s a New York thing…? They’re a decisive bunch.

  • [28:33] The crucial role of funding/capital and the vast differences between the capital available to US companies contrasted with Canadian companies

Without the capital, you’re going to have to be bean-counting.

  • [31:33] A classic Cassio+Lee mini-rant/discussion about where successful startups really come from, and how beanbag chairs, Nerf gun fights, free food, repurposing old warehouses, and other superficial actions and gimmicks have absolutely nothing to do with it
  • [36:02] Cassio’s adventures in corporate development, what goes into finding and acquiring companies, types of deals (tuck-ins, acqui-hires, buying revenue…), the things the bankers can’t capture in their spreadsheets, what can kill a deal (jogging!), and much more (steeply progressive consumption tax!)

If you string along your acquisition target for months and months and months, you’re doing yourself a disservice if you really want to buy that company and you force them to go through a 14-month acquisition process. Trust me, they’re not going to be thinking a lot about their clients at that point.

  • [1:00:36] Rapid fire! Bieber, Neymar, Chalet Sauce, sea snails, Dostoyevsky, and Piketty

Header/Featured photo credit: Cassio Sampaio and Matt Botsford 


  1. Was great to hear these familiar yet contrasting accents conversing in one space again. Nice work!

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