Should brands adopt a clear, even polarizing point of view rather than play it safe to appeal broadly?

Harry Stebbings · May 11, 2022

Much product marketing is bland and neutral and means nothing; effective product marketing must be bold, almost arrogant, saying something concrete like 'a thousand songs in your pocket' rather than 'a great musical device'

'A thousand songs in your pocket' lands because it is specific and bold, whereas 'a great musical device' means nothing

23:22 20 Product: iPhone Creator, Tony Fadell on Marketing Lessons Learned from Steve Jobs, What is Truly Great Product Marketing, How The Best Product Teams Do Post-Mortems and Product Reviews & Is Product Art or Science, Data or Gut?

Tony Fadell · May 11, 2022

Putting some customers off is just differentiation: a product should be aimed at a specific target audience and be great for them rather than bland for everyone

Nobody is excited by messaging aimed at a swath of people; customers want to hear what the product means specifically for them — iPhones and Macs are not for everyone either

24:31 20 Product: iPhone Creator, Tony Fadell on Marketing Lessons Learned from Steve Jobs, What is Truly Great Product Marketing, How The Best Product Teams Do Post-Mortems and Product Reviews & Is Product Art or Science, Data or Gut?

Kieran Flanagan · Aug 10, 2022

Brands that refuse to hold points of view and fail to plug into today's culture will struggle, and meme/gif creators and independent creators will become far more important to companies

Brands sit in the middle because it's safe and comfortable, but everything is moving to pop culture — even historically boring categories like financial services became huge pop-culture content spaces

Scope: companies will need to build environments creators want to work in

24:57 20 Growth: Why You Need a Growth Hire Pre Product-Market-Fit? Why Every Company Will Be a Media Company and How To Do It | Communities; What Really Are They? How To Build Them? What Makes The Best? Why Do Many Not Work? | Kieran Flanagan, SVP Marketing @

Kieran Flanagan · Aug 10, 2022 · hedged

Elon Musk is one of the best examples of a brand doing edgy things without alienating his tribe — the edginess makes his followers embrace him more

His fans are fanatical about everything he does

Scope: setting aside other things he's done

28:39 20 Growth: Why You Need a Growth Hire Pre Product-Market-Fit? Why Every Company Will Be a Media Company and How To Do It | Communities; What Really Are They? How To Build Them? What Makes The Best? Why Do Many Not Work? | Kieran Flanagan, SVP Marketing @

Kieran Flanagan · Aug 10, 2022

Musk has more reach than any traditional media organisation because he plugs into culture and can instil emotion at mass scale — which is exactly what brands should aim for

Brands are trying to create emotional connection with their audience; you want it positive for the people you're reaching, and negative reaction is not by itself a reason to stop

Scope: don't get swayed by the negative

29:07 20 Growth: Why You Need a Growth Hire Pre Product-Market-Fit? Why Every Company Will Be a Media Company and How To Do It | Communities; What Really Are They? How To Build Them? What Makes The Best? Why Do Many Not Work? | Kieran Flanagan, SVP Marketing @

Harry Stebbings · Mar 8, 2023

Shopify's website messaging ('the global commerce platform... sell online, offline and everywhere in between') is bland and should instead be an emotive, empowerment-led message about funding merchants' lives and dreams

The current copy describes the category rather than the emotional payoff of what the software does for a merchant's life

32:44 20Product: Shopify's VP Product on Why the Founder is Always the Head of Product, What Makes Truly Special Product Managers, Why The Majority of Product Managers Need to Change, Why Top-Down Decision-Making in Product is Good & How Shopify Will Be Bigger

Keith Rabois · Nov 27, 2023

Founders should be unapologetic about what they stand for because it creates the right downstream effects

Being unapologetic produces the right effects downstream in the company

51:35 20VC: Keith Rabois and Mike Shebat on Creating an Olympian Mindset to Work Ethic, Why First-Time Founders are Better Than Serial Entrepreneurs, Why Remote Work Does Not Work, Why the Best Founders Always Start in their Teens & Why Companies are Cults?

Cem Kansu · Jun 20, 2025

Notifications work by breaking pattern — emoji and an unhinged, personal brand voice outperform sanitized corporate copy

Users get 85 other apps' notifications a day and everything blends in; a message that reads like Duo personally texting you triggers a response, whereas 'Practice now' doesn't go far

Scope: emoji explanation offered as his own read of why it works

59:06 20Product: How Duolingo Build Product 10x Faster with AI | Duolingo's Biggest Lessons on Paywalls, Push Notifications and In-App Purchases | Why Small Teams are the Future of Product | Why PMs Will Become Extinct with Cem Kansu, CPO @ Duolingo

Peter Rahal · Aug 8, 2025

Having a very clear positioning is essential, and the best brands are semi-polarizing

A niche origin helps reinforce a clear, polarizing point of view

Scope: niche origin 'probably' helps reinforce the positioning

8:31 20VC: The $BN Greenoaks Backed Protein Bar | Hitting $100M Revenues in David's First Year: Lessons & Mistakes | $0 to $600M: The Untold RXBAR Story | Product-Market-Fit, Pricing, Branding: What Every Founder Gets Wrong Today with Peter Rahal

Peter Rahal · Aug 8, 2025

RXBAR was not opinionated enough in its early days — it played it too safe on brand

Despite being a risk-taker generally, he wasn't willing to take brand risk because he just wanted people to like the product and the risk-reward wasn't there

Scope: they did have 'no BS' on the package; stated in contrast to David, which has a much stronger point of view

8:51 20VC: The $BN Greenoaks Backed Protein Bar | Hitting $100M Revenues in David's First Year: Lessons & Mistakes | $0 to $600M: The Untold RXBAR Story | Product-Market-Fit, Pricing, Branding: What Every Founder Gets Wrong Today with Peter Rahal

Peter Rahal · Aug 8, 2025

Most brands are bad because they never define a personality or point of view — they sit in the middle of the fairway and are indistinguishable

By the human-personality analogy, if they were at a party you wouldn't know they were there, wouldn't want to talk to them, and would have no idea what their point of view is

16:07 20VC: The $BN Greenoaks Backed Protein Bar | Hitting $100M Revenues in David's First Year: Lessons & Mistakes | $0 to $600M: The Untold RXBAR Story | Product-Market-Fit, Pricing, Branding: What Every Founder Gets Wrong Today with Peter Rahal

Harry Stebbings · Aug 18, 2025

Great brands are opinionated — people either love them or hate them — and not enough people are opinionated

6:33 20VC: Lovable CEO Anton Osika on $120M in ARR in 7 Months | The Honest Truth About Defensibility and Unit Economics for AI Startups | The State of Foundation Models: Long Grok, Short OpenAI, Why | Replit vs Lovable vs Bolt: What Happens

Tony Fadell · May 11, 2022

Teams market timidly because they are insecure about the product or the team and haven't actually sold themselves on it

If you don't believe it, why should anybody else — after putting years of your team's life into something, boldness should be natural; timidity signals you worked on it rather than believed in it

23:47 20 Product: iPhone Creator, Tony Fadell on Marketing Lessons Learned from Steve Jobs, What is Truly Great Product Marketing, How The Best Product Teams Do Post-Mortems and Product Reviews & Is Product Art or Science, Data or Gut?

Harry Stebbings · May 11, 2022

Bland marketing comes from a lack of confidence — a fear of putting off some customer segment by being too bold

24:26 20 Product: iPhone Creator, Tony Fadell on Marketing Lessons Learned from Steve Jobs, What is Truly Great Product Marketing, How The Best Product Teams Do Post-Mortems and Product Reviews & Is Product Art or Science, Data or Gut?

Harry Stebbings · Jun 13, 2022

The current state of product marketing is abysmal — bland, emotionally neutral and interchangeable

Everything he looks at is the same case studies and logos and nothing makes him feel anything or excites him

47:26 20VC: Hubspot Co-Founder Dharmesh Shah on The 3 Risks All Startups Face, Angel Investing Rules; No Founder Meetings and No Due Diligence, SMB vs Enterprise; Lessons on Pricing, Distribution and Why You Should Resist Going Enterprise

Harry Stebbings · Aug 10, 2022 · hedged

It is very hard to keep a brand edgy at scale once you're a public company juggling corporate and investor brands

Scale brings many different brand audiences you have to satisfy

Scope: public companies specifically

26:57 20 Growth: Why You Need a Growth Hire Pre Product-Market-Fit? Why Every Company Will Be a Media Company and How To Do It | Communities; What Really Are They? How To Build Them? What Makes The Best? Why Do Many Not Work? | Kieran Flanagan, SVP Marketing @

Glen Coates · Mar 8, 2023

Software product marketing is insanely difficult, and blandness inevitably seeps in at scale because the message has to resonate across all countries, business sizes, industries and channels

Shopify's mission audience used to be effectively small North American fashion businesses; now it is genuinely everyone, so a single message must speak to everyone and gets diluted

Scope: not offered as an excuse

33:39 20Product: Shopify's VP Product on Why the Founder is Always the Head of Product, What Makes Truly Special Product Managers, Why The Majority of Product Managers Need to Change, Why Top-Down Decision-Making in Product is Good & How Shopify Will Be Bigger

Harry Stebbings · Aug 10, 2022

Most product marketing and messaging is bland and neutral, and companies should hire people who specialise in memes and gifs for product messaging because they understand what resonates

Meme and gif specialists know what actually resonates with audiences, unlike neutral corporate messaging that speaks to no one

24:33 Hire meme and gif specialists for product messaging since they understand cultural resonance

Peter Rahal · Aug 8, 2025

Four Loko is a great branding case study because its position and customer are unmistakably clear, even if that clarity caps it from becoming ubiquitous beyond its core college market

Everything they do is absurd and outrageous, so seeing someone drink it tells you exactly what kind of night they're having; the demographic is completely clear

16:54 Polarizing clarity caps mass market ubiquity but strengthens identity

Harry Stebbings · Mar 8, 2023

An emotive, non-enterprise website message costs Shopify nothing with large brands, because big customers like Supreme or MrBeast arrive through top-down enterprise deals rather than self-serve signup

Large brands sign via boardroom enterprise processes, so site copy only needs to convert the long tail, which you can then grow with

34:35 Enterprise deal motion insulates bold messaging from large brand risk

Glen Coates · Mar 8, 2023

The customers actually alienated by a bold, emotive message are not modern brands like Supreme or MrBeast but legacy risk-averse retailers, who would read it as unsafe and go to Salesforce instead

Legacy retail buyers optimise for perceived safety and vendor legitimacy rather than founder-voice authenticity

35:24 Legacy risk averse retailers not modern brands are alienated by bold messaging