Makin Mighty: The Challenger Sessions

Send us Fan Mail What do retailers actually want from challenger brands — and what gets you ignored instantly? In this episode of Makin Mighty: The Challenger Sessions , Simon Greenwood-Haigh speaks with Chris Otto , who spent nearly 20 years at Co-op in buying roles and leading buying teams across frozen, impulse and grocery. We get into:  what “challenger” really means from a retailer perspectiv...

Send us Fan Mail AI is everywhere in sales right now — and most of what people are doing either turns into spam, or it’s so complicated nobody uses it. In this episode of Makin Mighty: The Challenger Sessions , Simon Greenwood-Haigh speaks with Craig — founder of Cheesies and a commercial operator/consultant turned AI practitioner — about how challenger brands can use AI to sell more without losin...

Send us Fan Mail Getting listed is exciting. Staying listed is the hard bit. In this episode of Makin Mighty: The Challenger Sessions , Simon Greenwood-Haigh speaks with Ja and Jag , founders of Superfoodio , about what really drives rate of sale once you’re on shelf. They share practical, founder-level tactics on: why availability is the first battle (and how brands get caught out) early retail m...

Send us Fan Mail How do you make a 200-year-old heritage brand behave like a modern challenger — without losing what made it famous? In this episode of Makin Mighty: The Challenger Sessions , Simon Greenwood-Haigh speaks with Josh Daly , who helped take Grey Poupon from being “in the wilderness” to behaving like a brand with a clear point of view. We get into: why Grey Poupon got delisted (and why...

Send us Fan Mail Early-stage founders often try to rush to “perfect” — perfect branding, perfect plans, perfect decks — before they’ve sold a single unit. In this co-hosted episode of Makin Mighty: The Challenger Sessions , Simon Greenwood-Haigh and Scott Cramner unpack what “good enough” really means for challenger brands, and why perfection is often just procrastination dressed up as strategy. W...

Send us Fan Mail Loads of challenger brands describe themselves as “premium”. But premium isn’t a word you write in a strategy doc — it’s something you deliver , end to end. In this co-hosted episode of Makin Mighty: The Challenger Sessions , Simon Greenwood-Haigh and Scott Cramner break down the difference between looking premium and being premium — and why getting this wrong is one of the fastes...

Send us Fan Mail Founders love their origin story. Buyers don’t buy it. In this co-hosted episode of Makin Mighty: The Challenger Sessions , Simon Greenwood-Haigh and Scott Cramner unpack why brand storytelling so often falls flat in retail and commercial conversations. We talk about: why relevance beats romance when you’re trying to sell why your brand is the sidekick, not the hero when storytell...

Send us Fan Mail A lot of founders blame the algorithm when their content doesn’t land. It’s a convenient scapegoat. In this co-hosted episode of Makin Mighty: The Challenger Sessions , Simon Greenwood-Haigh and Scott Cramner unpack what’s really going on: most challenger brands don’t have an algorithm problem — they’ve got a messaging problem. We get into: why “going viral” is not a strategy how...

Send us Fan Mail Getting listed is not the win...it’s permission to start proving yourself. In this episode of Makin Mighty: The Challenger Sessions , Simon Greenwood-Haigh is joined by Jasmine Wheelhouse (CEO/“Pea-EO” of Taking the Pea ) to talk honestly about the retail reality for challenger brands: getting a buyer’s attention, winning the pitch, and what it takes to stay listed once you’re on...

Send us Fan Mail Design matters. But design cannot rescue a product or business that does not deliver. In this co-hosted episode of Makin Mighty: The Challenger Sessions , Simon Greenwood-Haigh and Scott Cramner get into the uncomfortable truth founders need to hear: if you are using design to hide bigger problems, the market will find you out fast. We talk about: why great branding cannot compens...

Send us Fan Mail A lot of early-stage brands feel world-class before they’ve actually proven anything. In this co-hosted episode of Makin Mighty: The Challenger Sessions , Simon Greenwood-Haigh and Scott dig into a pattern we keep seeing: confidence that shows up before competence...and how it quietly kills momentum. We talk about where overconfidence shows up first (hint: it’s usually not where f...

Send us Fan Mail Most food and drink brands say they’ve got a tone of voice but walk down any supermarket aisle and you’d struggle to tell them apart. In this episode of Makin Mighty: The Challenger Sessions , Simon Greenwood-Haigh is joined by Kevin Karaca , founder of The House Outside , to unpack what tone of voice actually is, why so many brands play it safe, and how challenger brands can use...

Send us Fan Mail Chilled is one of the toughest places to build a food brand and most challengers don’t survive it. In this episode of Makin Mighty: The Challenger Sessions , Simon Greenwood-Haigh sits down with Gaz Booth, founder of Holy Moly, to talk honestly about what it really takes to break through in a brutal category. We get into the real story behind the brand, the early mistakes, what sc...

Send us Fan Mail In this first solo episode of Makin Mighty: The Challenger Sessions , Simon Greenwood-Haigh breaks down what a challenger brand actually is and why most brands get it wrong. It’s a short, honest look at the mindset that separates real challengers from the ones who only use the word in their pitch deck. Simon shares the core truths he’s seen across the industry, the common traps fo...