Scrappy But Successful Podcast with Gus Byleveld

Recorded 4 October 2026.

Gus Byleveld is the founder of The Wondering and a former CEO and revenue operator with 25+ years of experience building and leading B2B tech companies. He started out as an architect in Cape Town, South Africa, moved into technology sales, worked through a run of startups, and today helps CEOs of growth-stage tech companies figure out why growth is harder than it should be before they decide what to change.

In this episode, Jack and Gus dig into why a sales process should be built from the buyer journey, how AI is changing the way buyers size up sellers, and why the real gap in modern selling is trust. Gus shares the discovery question he swears by, why marketing, BDR, and customer success teams need one shared goal, and why activity is not quality. And the big question: is Gus more scrappy or more sophisticated? Jack’s verdict: a dash of scrappiness, backed by some seriously sophisticated thinking.

Chapters:

0:00 Scrappy or sophisticated? Meet Gus Byleveld
2:53 From Cape Town architect to tech sales
8:02 The Wondering and why buyer journey beats sales process
14:40 Leaving corporate for a mobile trading card startup
19:18 Two schools of thought on AI, then and now
24:25 The trust gap in modern selling
27:23 The discovery question: what does your world look like when I solve this?
34:29 One shared goal for marketing, BDRs, and customer success
38:16 What makes you uniquely qualified? The question AI can’t outsource
43:03 Get out of the building, and where to find Gus

Connect with Gus:

LinkedIn: https://www.linkedin.com/in/gusbyleveld/
The Wondering: https://thewondering.net/

Connect with Jack:

LinkedIn: https://www.linkedin.com/in/jack-tompkins/
Consulting: https://www.pineapplecf.com
AI Analyst Product: https://www.pineappleanalyst.ai/
YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng