
Starting & Selling Playground XYZ to GumGum. Rob Hall (Parallel) Media Tech Talk #41
Media Tech TalkShow Notes
Media Tech Talk #041 - Rob Hall (Parallel) Part 1
What does it take to build an ad tech company from nothing, sell it, and then come straight back to do it all again? Rob Hall has done exactly that. He co-founded Playground XYZ in 2015 on a bold bet that real, measurable human attention could be put on a scoreboard for advertisers, at a time when almost nobody believed it was possible. GumGum went on to acquire the business, Rob stayed on to lead its global data function, and then he did something most founders don't: he stopped, took a year off and travelled. Now he is back as founder and CEO of Parallel.
In Part 1, Daevid and Rob go back to the beginning: cold calling out of the Yellow Pages selling gym and pub ads, the phone trick that cracked one of the biggest accounts in the country, and why that early grind built the resilience and solution selling instincts that carried into every venture since. Rob opens up on leaving a stable managing director role to start Playground XYZ with his co-founders, the moment COVID brought the business closer to the wire than ever, and the values-driven call the team made when the obvious answer was to cut jobs.
From there the conversation turns to the exit. Rob explains why they chose to sell while the business was still accelerating, the market forces that made the timing right, how an exploratory look around quietly turned into a process, and why, despite a deal he is proud of, it remains the hardest decision he has ever made.
Part 2 picks up with Parallel and the big question: can an AI digital twin of a customer really tell a brand what a real customer will do, before a single dollar is spent?
Chapters: (00:00) Cold open: build it, sell it, do it all again (01:22) Welcome Rob Hall, calling in from London (02:21) Starting from zero: the early sales grind (04:34) The cold call that cracked a big account (05:46) Resilience, adaptability and selling a new category (06:59) Solutions over analysis paralysis (08:06) 2015: betting a stable career on attention (09:45) What nearly broke Playground XYZ (11:10) One in, all in: a values test under pressure (12:49) Staying hungry: the challenger mindset (15:06) Why sell to GumGum while still accelerating (17:33) Consolidation and competing with the giants (18:34) The hardest decision a founder makes (19:06) Keeping publisher trust through the transition (19:41) How the deal actually came together (20:37) When exploring quietly becomes a process (21:26) Coming up in Part 2: Parallel and AI digital twins
💬 Guest: Rob Hall, Founder & CEO – Parallel https://www.linkedin.com/in/hallrob/ | https://helloparallel.com/
🎧 Host: Daevid Richards – https://www.linkedin.com/in/daevidrichards/
Media Tech Talk explores ad tech, digital media, AI in advertising, programmatic monetisation, audience engagement, and the technologies shaping the future of publishing.
🏷️ #MediaTechTalk #Parallel #PlaygroundXYZ #GumGum #AttentionMeasurement #DigitalTwins #AdTech #Founders #Startups #MergersAndAcquisitions #Leadership #DigitalAdvertising #Podcast
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