Dec 13, 2017 · 1h 9m · y-combinator
Be Wary of Solving a Small, Rare Problem - Des Traynor of Intercom · Y Combinator
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In this Y Combinator interview, Intercom co-founder Des Traynor shares actionable strategies on content marketing, scaling company culture, and product positioning, emphasizing why founders must focus on solving big, frequent problems.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →
The partners as informed peer 3.0 Guest teaching 5.1 Guest disagreement 1.6 The partners pushing back 1.0
speaking balance: gold is the partners, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 0:14 Calling engineer marketing beliefs absolute nonsense
Des forcefully dismisses the conventional engineering belief that marketing is simply pouring money into CAC/LTV positive keywords to double returns.
Hardest push from the partners ▶ 0:04 Questioning user poaching from ExceptionalCraig directly asks if Intercom simply stole all its users from the founders' previous company Exceptional upon exit.
Biggest teaching moment ▶ 0:41 Framework for evaluating small vs rare problemsDes delivers a structured breakdown explaining why startups building beautiful solutions for small, infrequent problems inevitably fail.
The partners hold their own ▶ 1:05 Connecting fintech complexity to misaligned fee incentivesCraig demonstrates strong domain analysis by showing how financial incumbents are deliberately incentivized toward complexity and citing Vanguard's disruption.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | The partners as informed peer | Guest teaching | Guest disagreement | The partners pushing back | Why |
|---|---|---|---|---|---|---|
| Meeting Co-Founders and Early Academic Background | 2 | 4 | 1 | 1 | Des Traynor shares the origin story of Intercom, his academic research background, and transitioning from Exceptional to Intercom. Craig asks straightforward foundational questions to facilitate the story. | |
| Content Marketing Strategy and Building Audience Trust | 3 | 5 | 2 | 1 | Traynor explains Intercom's philosophy of content first, marketing second, and warns against making content purely promotional. Craig agrees and validates the approach with brief observations. | |
| Founder Role Shifts and Learning Executive Marketing | 3 | 4 | 1 | 1 | Des discusses evolving from UX design to support, recruiting, and eventually executive marketing. Craig asks how founders navigate cross-functional role transitions. | |
| Mapping Strategic Buyer Journeys and Marketing Principles | 4 | 6 | 2 | 1 | Des details marketing principles and how customers look for solutions at varying levels of abstraction rather than searching for specific brands. Craig relates this to Y Combinator's own top-of-funnel marketing dynamics. | |
| Marketing Funnels, Attribution, and Problem-First Messaging | 3 | 6 | 2 | 1 | Des gives a detailed masterclass on why purely attributable paid marketing fails when brand marketing is neglected, and explains problem-first landing pages. Craig provides an audio editing problem analogy. | |
| Aligning Product Strategy, Company Mission, and Brand | 2 | 5 | 1 | 1 | Des explores why product strategy, brand, and marketing must remain tightly aligned to a core mission ('making internet business personal'). Craig prompts him on handling product portfolio growth. | |
| Scaling Culture, Onboarding, and Leadership Management | 2 | 5 | 2 | 1 | Des analyzes the challenges of scaling onboarding across multi-office teams and hiring senior executives in unfamiliar fields. Craig asks about practical onboarding approaches and executive management books. | |
| Evaluating Startup Ideas and Avoiding Small Problems | 3 | 6 | 2 | 1 | Des outlines his framework for startup problems, warning founders against small, rare problems and fake traction from low-priced high-touch services. Craig chips in on market size and high-touch traps. | |
| Brand Architecture and Unbundling Intercom's Product | 4 | 6 | 2 | 1 | Des explains brand architecture, distinguishing specific vs abstract brands and explaining why Intercom unbundled its suite into separate support and marketing offerings. Craig relates this to commoditization risks at YC. | |
| Conversion Optimization and Executive Leadership Shifts | 4 | 4 | 1 | 1 | Des reflects on conversion optimization, UI audio branding, shifting back toward product, and potential future industry problems like soccer streaming and fintech bureaucracy. Craig actively joins the ideation around financial simplification and Vanguard. |
Statements from this episode (18)
Template-based grading encourages computer science students to memorize without understanding
“The way, and this is true worldwide, I think, the way, like, people in universities would mark a piece of code is they say, all right, we'll give them three points if they have a for loop, and two points if they have an if statement, and people just learned th…”
Des Traynor wrote roughly 93 of Intercom's first 100 blog posts
“I wrote, I think I wrote 93 of the first 100 posts.”
Effective content marketing helps users solve broad problems before pitching
“The advice I'd give people is usually like, think about who your actual end target user is and think of all the problems in their life that you can help them with. And then try and help them as much as you can. And then every now and then hopefully you're, if …”
Intercom's blog is the company's dominant source of inbound traffic
“And it's one of our, you know, it is our dominant traffic source, but we, you know, that wasn't true for the first 100 posts.”
Marketing organization structures lack standard playbooks and vary across companies
“I've talked to maybe 50 different VPs of marketing at this point about how their marketing org is structured, and they're all different. Like, very, like, not just different as an, ooh, you put one person in, but like, substantively different. Like, even like,…”
Engineering-driven paid search rarely works as a deterministic growth engine
“The engineer's approach to marketing is, like, We're going to hire a marketer, and they're going to find the keywords that are CAC LTV positive. That is, the customer acquisition cost is less than the LTV, and we're going to dump all of our fifty million dolla…”
Relying strictly on attributable marketing causes overall growth to suffer
“In general, the marketing world is one where you move from like, This is really hard to attribute, and it costs a lot of money down to, like, hey, we spent seven cent and it kicked ass, right? But that whole thing is a spectrum, and you have to be willing to d…”
Companies cannot sell a solution until customers have bought the problem
“You can't sell somebody on the solution until they've bought the problem.”
Product, marketing, code, and design are renderings of one core idea
“Product and marketing and code and design are all like, they're all renderings of the same core idea.”
Startups must build what they sell and sell what they build
“Karen Peacock, who's our CEO, she always says, build what you sell, sell what you build. If you're not doing both of those things, you're in Fucking trouble, basically, right?”
Hiring one misaligned manager creates entire misaligned departments
“If you hire one person who's not on the same page, and you let them hire people, they're gonna hire more people who aren't on the same page. And next thing, you have whole wings of the company working against you in bad ways.”
Founders without marketing expertise are easily duped by smooth-talking candidates
“Marketers and salespeople are good at marketing to you and selling to you. So if you've never hired a salesperson before, don't be shocked if the first person that comes to you sells you on the role, you know?”
Startups building products to solve small, rare problems never succeed
“The next piece I would say to people is like, you have to find, you know, be really wary of solving a small, rare problem. You can solve a big problem. You can solve a rare problem. Sorry, you can solve a small problem, fine. A rare problem, fine. But small an…”
High-touch founder onboarding requires charging more than nine dollars a month
“If you're going to spend 30 minutes talking to every single customer who needs to install, and you've no bigger picture as to how you're not going to be necessary, you need to be charging more than nine dollars a month.”
Specific brand names limit expansion; ambiguous brand names hurt conversion
“It's hard to expand a brand that has a high degree of specificity. It's hard to convert a brand that has a high degree of ambiguity.”
Tailoring website onboarding by persona doubled or tripled Intercom's conversion rate
“Over the years of experimentation, we've really doubled or trebled our actual conversion rate through things like that.”
Global soccer broadcasting piracy matches pre-iTunes music industry levels
“Piracy in soccer is, I would say, at, like, the levels pre-iTunes, if you remember, in the music industry, right? Like, there are, like, there is an equivalent of Kazaz. There are many of them. And no one's doing anything to solve it.”
Founders avoid massive fintech simplification opportunities due to operational schlep work
“I think that model, and I'm not saying chatbots aren't the thing here so much as drastic simplification is the thing. The Q and A maybe suggests that a chatbot might be like charming as a way to do it, or like at least unique from a brand perspective. But I th…”