Nov 3, 2024 · 1h 15m · lennys-podcast
Just evil enough: Subversive marketing strategies for startups | Alistair Croll
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In this episode, author and startup adviser Alistair Croll joins Lenny Rachitsky to explore subversive marketing strategies and zero-day distribution exploits from his book, 'Just Evil Enough.' They discuss how founders can overcome modern distribution bottlenecks, achieve product-medium-market fit, and ethically leverage technical, regulatory, and cognitive loopholes to build sustainable competitive advantages.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Lenny holds 22.3% of the talking time here. How this is scored →
Lenny as informed peer 5.2 Guest teaching 6.0 Guest disagreement 2.4 Lenny pushing back 1.5
speaking balance: gold is Lenny, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 23:30 Alistair calls out Lenny's high agreeableness
Alistair contrarianly pushes Lenny on business school orthodoxies and directly challenges his agreeable nature, urging him to embrace disagreeability.
Hardest push from Lenny ▶ 19:16 Lenny challenges marketing stunts vs sustainable growthLenny pushes back against relying purely on transient viral stunts, questioning whether these tactics can generate sustainable growth engines.
Biggest teaching moment ▶ 17:03 Stanford $5 seed capital exploit lessonAlistair breaks down how the winning Stanford team bypassed the challenge constraints by monetizing their presentation time rather than building standard micro-businesses.
Lenny holds their own ▶ 52:01 Lenny invokes April Dunford on positioning vs reframingLenny cites positioning authority April Dunford to challenge Alistair's distinction between competitive positioning and market reframing.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Lenny as informed peer | Guest teaching | Guest disagreement | Lenny pushing back | Why |
|---|---|---|---|---|---|---|
| The Motivation Behind Writing Just Evil Enough | 4 | 5 | 2 | 1 | Lenny opens by asking about the inspiration behind the book and sets up the premise of unconventional startup growth. Alistair frames traditional product management as flawed for ignoring distribution and unfair advantages. The dynamic is collaborative and setting the foundational narrative. | |
| Sponsor Break: Hex Modern Data Platform | 5 | 6 | 3 | 2 | Following an ad read, Alistair breaks down historic exploits like Netflix's postal network misappropriation and Bumble's university flyer campaign. Lenny synthesizes the distinction between standard marketing playbooks and zero-day exploits. | |
| The Origin of Just Evil Enough and Solving the Cold Start Problem | 6 | 5 | 2 | 1 | Lenny and Alistair reminisce about Year One Labs and LocalMind, where Alistair coined the phrase 'just evil enough' when advising Lenny to seed synthetic questions to solve the cold start problem. Lenny shares his own experience of transitioning from being overly agreeable to pragmatic. | |
| The Core Pillars: System Awareness, Novelty, and Disagreeability | 4 | 7 | 3 | 1 | Alistair outlines the three core pillars: system awareness, novelty, and disagreeability. He shares the Stanford $5 challenge case study to demonstrate how understanding the system yields superior results over incremental effort. | |
| Structural Value Chain Exploits versus Disposable Growth Hacks | 6 | 7 | 4 | 4 | Lenny pushes back on whether these tactics are merely transient turbo-boost spikes rather than sustainable growth engines. Alistair educates on structural value chain shifts like Ikea's flat-packing and playfully challenges Lenny to embrace more disagreeable thinking. | |
| The Recon Canvas: Scanning Product, Medium, and Market | 5 | 7 | 3 | 1 | Alistair presents his Recon Canvas framework and introduces the concept of product-medium-market fit, arguing traditional product-market fit is outdated. He illustrates platform mechanics using Burger King's retro-liking stunt. | |
| Coordinated Launches, Stunts, and Introducing the 11 Tactics | 6 | 6 | 2 | 1 | Lenny shares the Runway timed-lockbox campaign as an example of medium exploitation. Alistair recounts how he hacked the launch of Lean Analytics by turning influencer pre-orders into a competitive campaign. | |
| Sponsor Break: Vanta Compliance Automation | 5 | 7 | 2 | 1 | Following the mid-roll ad, Alistair details Tactic 1 (bug into feature with Salesforce) and Tactic 2 (buyer upgrade with Mr. Clean and bridge drones). Lenny mirrors the concepts back to clarify how audience shifts avoid engineering rework. | |
| Tactics 3, 4 & 5: Exclusive Access, Ethical Bait-and-Switch, and Bundling | 5 | 6 | 2 | 1 | Alistair details access advantages, ethical bait-and-switch models like Tupperware and Energage, and combination bundling like Kraft Mac & Cheese or mattress disposal. Lenny confirms key criteria that prevent bait-and-switch from becoming fraudulent. | |
| Tactics 6 & 7: Information Arbitrage and Scaled Data Aggregation | 6 | 7 | 3 | 2 | Alistair details information arbitrage (from 16th-century optical telegraph fraud to FarmVille's inside API advantage) and scaled data aggregation (Busbud generating programmatic SEO pages). Lenny draws parallels to high-frequency trading infrastructure. | |
| Tactic 8: Strategic Reframing and Changing Competitive Axes | 7 | 6 | 3 | 3 | Alistair describes strategic reframing using Tom's of Maine toothpaste and Tesla's acceleration focus. Lenny pushes on the distinction between positioning and reframing, referencing positioning expert April Dunford's perspective. | |
| Tactics 9, 10 & 11: Regulation, Misappropriation, and Shifting the Overton Window | 5 | 7 | 2 | 1 | Alistair covers regulatory arbitrage (organ donation defaults, van parklets), misappropriation, and shifting the Overton Window (Bodyform's red liquid ads). Lenny summarizes the comprehensive list of 11 tactics. | |
| Operationalizing Disagreeability: Ideation, Testing, and Investor Pitching | 5 | 6 | 2 | 1 | Lenny asks how product teams can operationalize subversive ideation without spiraling into ineffective stunts. Alistair shares brainstorming techniques such as TRIZ, pre-mortems, construal level theory, and spiky points of view. | |
| The Shifting Economics of Software Creation and Subversive Publishing | 6 | 6 | 2 | 1 | Lenny notes how generative AI shifts competitive advantage entirely to distribution. Alistair elaborates on the inverted economics of risk in software development and explains how he restructured his own book publishing model. | |
| Ethical Guardrails: Defining When Tactics Become Too Evil | 4 | 6 | 2 | 1 | Lenny prompts Alistair to establish ethical boundary lines. Alistair gives clear guardrails against dark patterns, criminal deception, and non-consensual tactics, citing negative examples like obituary scraping and the PT Cruiser CAFE standards loophole. | |
| Lightning Round: Recommended Books, Media, Life Mottos, and Gadgets | 4 | 4 | 2 | 1 | In the lightning round, Alistair shares his recommended reading, movies, hardware hacks, and life mottos. The dialogue is lighthearted and conversational. | |
| Reflections on Year One Labs and Early Montreal Startup Hustle | 5 | 4 | 2 | 2 | Alistair and Lenny reminisce about Year One Labs hackathons in Montreal and Lenny's early product analytics prototyping. Lenny closes the episode by directing listeners to Alistair's resources. |
Statements from this episode (25)
Product managers fail by obsessing over features instead of go-to-market strategy
“The product managers are in, in many cases, missing the point. Like my sense is when you talk to a product manager, they're so consumed to the next feature and what to do. And that's the kind of concrete objective thing. I think many of them are doomed because…”
Subversive marketing means leveraging systems in ways their creators never intended
“It's not that they did something evil. It's that they did something to use a system in a way its creators didn't intend.”
Blockbuster launched streaming before Netflix, but limited broadband made it unviable
“A lot of people forget that Blockbuster had streaming first. Streaming wasn't a good play at the start of the online video industry, because The penetration of broadband in the U S was very limited.”
Discovering a zero-day marketing exploit is as important as building features
“Finding that go to market strategy, that unfair, unprecedented, we call them zero day marketing exploits is as important as building the right product feature, you know, having a seamless onboarding process and so on.”
Startups must be 'just evil enough' to provoke necessary behavioral changes
“It is so, so important to like understand the boundaries of what you can do if you are essentially disagreeing with the status quo in order to prove that your idea is better. So I've always talked about this idea of not being evil, but being just evil enough t…”
Scott Belsky seeded Behance by interviewing top designers who refused invites
“He said that for the launch of Behance, he reached out and asked all these influential designers to join his platform. And they said, no. And then he said, oh, okay, pivot. Hey, I'd like to do an interview about you for my platform. And they said, oh sure. And…”
Coinbase's worst-rated Super Bowl QR ad drove 20M hits, crashing servers
“Coinbase bought a 62nd Super Bowl app where they bounced a QR code around the screen for 60 seconds. Is it stupid? Yeah. I mean, they were ranked the worst of 64 Superbowl ads, but they got twenty million hits and their servers fell over.”
Growth hacks are superficial, but zero-day marketing exploits fundamentally subvert industries
“I'm not a big fan of growth hacks. A growth hack traditionally is sort of product agnostic. So when you move your mouse off the screen and it pops up a little window saying, Hey, why are you leaving? There was a time that was cool. Now it's just like that mous…”
Product-market fit is overrated; founders must instead pursue product-medium-market fit
“That's another hot take of mine is I think the product market fits overrated. You have to actually think about product medium market fit.”
Runway sent influencers locked bags with three-day countdowns to build hype
“They did this really clever strategy where they sent all these influencer types on Twitter, a package that it arrives and it's a bag with a lock on it. And the lock says this will open in three days. And there's a countdown that's counting down and you can't l…”
Liquid Death requires at least 50% ad disapproval before launching campaigns
“They do not go ahead with a with a campaign or an ad unless it gets 50% disapproval. That's like their North star metric.”
Mr. Clean Magic Eraser began as melamine foam for aircraft insulation
“Mr. Clean's magic eraser started out as melamine foam for aircraft insulation until the company noticed that people were wetting it and using it to clean stains off things.”
Repositioning Coradiant closed Fidelity, Salesforce, and LinkedIn in just three months
“Within three months, Fidelity, Salesforce, and LinkedIn had bought our biggest product just because I learned how to explain it to a different customer.”
Bait-and-switch is ethical only if buyers are delighted or promises kept
“Bait and switch can be evil unless the buyer is delighted with the thing you've switched them for, or you also deliver the thing you promised.”
Bundling adjacent steps in the value chain dramatically simplifies consumer offerings
“Often it's just before or just after the product that dramatically simplifies the offering for the consumer.”
Zuckerberg tipped off Mark Pincus about timeline posting, driving FarmVille's growth
“Pincus and Zuckerberg were very good friends and Zuckerberg told Pincus that apps were going to be allowed to post to users timelines. This is why FarmVille grew almost overnight.”
Reframing offers customers new evaluation dimensions rather than competing on existing ones
“Reframing isn't just about competing on existing dimensions. It's about giving the customer a different set of dimensions. And that won't happen for the whole market, but it'll happen for one of those segments.”
Positioning is placing a product on a grid; reframing is drawing it
“So we actually think that positioning is simply where you are on a grid. Reframing is drawing the grid.”
Austria's opt-out organ donation policy reaches 99.6% versus Germany's 12%
“Austria's opt out. You're gonna deliver your organs when you die, unless you explicitly say you don't want to. In Germany, you have to opt in. They're not donated unless you explicitly do so. Germany has 12% organ donors. Austria has like 99.6.”
Companies gain an advantage by targeting shifted niche Overton windows
“And there is a tremendous advantage to understanding that one part of the market is already has an Overton window. That's different from the mainstream market. And then you can appeal to that and they will respect you for it.”
Startups pitching investors without a zero-day go-to-market exploit will probably fail
“If you're talking to an investor and that you don't have a zero day, go to market exploit that creates attention and turns it into sustainable, lucrative demand. You are probably going to fail.”
Chrysler classified the PT Cruiser as a truck to bypass fuel standards
“Every car manufacturer has to meet fuel efficiency standards for its car line and its truck line. And it turns out that Chrysler's trucks were terrible on fuel. So what happens is the automakers decided they would make this terrible little car called the PT Ch…”
Dan and Chip Heath's 'Made to Stick' is the best marketing textbook
“And I gotta say the best marketing textbook ever is Dan and Chip Heath's Made to Stick.”
Brand names no longer matter for products purchased on Amazon
“Brand names don't matter anymore. And you there, it's like someone threw up on a keyboard and that's the name of the company now for half the products you buy on Amazon, because that's not how you actually choose the product.”
Anker escaped the Amazon commodity trap through packaging and product quality
“I think anchor and KER is a good example of a company that was just one of many power companies, but they did their packaging, right. And their products, right. And now they're like a well-known name. So it takes real work to escape that trap.”