Jul 18, 2022 · 1h 13m · news
Des Traynor: How I Founded Intercom; Product Marketing Tips; Feature Creep | 20VC #907 · 20VC with Harry Stebbings
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In this episode of 20VC, Intercom co-founder Des Traynor joins host Harry Stebbings to share crucial lessons on product-led growth, tactical software development, and the realities of angel investing. Traynor breaks down the operational frameworks required to build, scale, and sunset features while highlighting how active startup operators can leverage their experience to become exceptional investors and leaders.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 15.9% of the talking time here. How this is scored →
Harry as informed peer 4.3 Guest teaching 6.4 Guest disagreement 2.4 Harry pushing back 3.4
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 4:05 Des rejects the Google threat premise
Des forcefully rejects Stebbings' premise that Google can resource any idea and crush startups, pointing out Slack, Figma, and Superhuman as clear proof of Google's focus limits.
Hardest push from Harry ▶ 4:00 Stebbings pushes back on Google's competitive advantageStebbings refuses to accept Des's claim that being first doesn't matter, arguing directly that Google can put its mind to any idea and resource it better.
Biggest teaching moment ▶ 43:19 Des breaks down the four enterprise readiness pillarsDes clearly educates the host on the behind-the-scenes realities of moving upmarket, mapping out adoptability, scalability, justifiability, and interoperability.
Harry holds his own ▶ 41:24 Stebbings frames the Marc Andreessen vs Dharmesh Shah debateStebbings demonstrates strong venture expertise by contrasting Marc Andreessen's famous 'raise prices' stance against Dharmesh Shah's view on underpricing goodwill.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| The Founding Story of Intercom | 5 | 5 | 3 | 5 | Stebbings frames the debate around founder vs idea quality using an Elizabeth Yin quote and challenges Des on whether Google can out-resource any idea. Des responds by explaining why big tech focus limitations prevent them from dominating every niche. | |
| Differentiating Early and Tactical Product Development | 4 | 6 | 2 | 3 | Stebbings probes on market sizing and CAC/LTV metrics for early startups. Des provides tactical frameworks on acid-testing differentiators first and evaluating problem frequency rather than relying on market size estimates. | |
| Why Operators Make Great Angel Investors | 3 | 6 | 1 | 2 | Stebbings asks why active operators make better angel investors. Des explains how viewing other companies gives critical perspective on Intercom's own positioning and praises Miro's focused execution over hype. | |
| Deciding to Launch a Second Product | 4 | 7 | 2 | 4 | Stebbings asks how to determine whether to launch a second product and presses on the difference between a feature and a standalone product. Des details criteria around resourcing without cannibalization and customer expectation. | |
| Knowing When to Kill a Product or Feature | 5 | 7 | 2 | 3 | Stebbings highlights the abysmal state of product marketing with a 10-word billboard challenge. Des breaks down the fundamental divergence between buyer metrics and user utility. | |
| Feature Creep, Simplicity, and Pricing Strategies | 6 | 6 | 4 | 5 | Stebbings sets up a debate between Marc Andreessen's raise prices stance and Dharmesh Shah's underpricing goodwill view. Des dismisses Andreessen's advice as overly blunt and advocates aligning price with value. | |
| What Changes When a Product Moves Upmarket | 2 | 8 | 1 | 1 | Stebbings asks what changes when moving upmarket. Des educates on the four non-negotiable enterprise pillars: adoptability, scalability, justifiability, and interoperability. | |
| Boring Ideas, Allergy to BS, and Radical Candor | 4 | 6 | 3 | 3 | Stebbings asks about Des's reputed allergy to BS and how he manages radical candor. Des offers a sharp critique of startups that turn basic Google Docs or spreadsheets into SaaS apps. | |
| Investment Misses and the Operational Challenge | 7 | 6 | 4 | 6 | Stebbings asserts strong opinions on angel check size discipline, employee expectations, and calls the only hire A-players mantra bullshit. Des counters by explaining why teams need a mix of career stages and trajectories. | |
| Hiring the Right Leader for the Business Stage | 3 | 7 | 2 | 2 | Stebbings asks about hiring executive leaders. Des explains how leadership selection must balance the previous leader's DNA and fit specific business stages. |
Statements from this episode (30)
Des Traynor prioritizes founder quality over idea quality in early-stage investments
“But if I had, if you're telling me I can only have one, I'll definitely pick the quality founder over the quality idea.”
Des Traynor: True defensibility does not exist on day one for startups
“Like, real defensibility, no, it does not exist.”
Des Traynor: Startups must test core differentiators before building standard infrastructure
“My advice in those cases is work on your differentiators first. So in the case of say an email client, oh, we have a new take on email. I would say, right here, here's what I believe. I believe you're a competent engineer. I believe you can work out SMTP and I…”
Des Traynor: Seed investments only require a $1 billion target market
“I only need the market probably to be like around a billion of like total revenue spent. For like, for this seed check to turn into a valuable series A or whatever. It doesn't need to be a monster.”
Des Traynor: CAC and LTV metrics do not matter for early-stage startups
“I think all these numbers matter, but they matter at scale. They just don't matter early on.”
Traynor: Intercom does not need to raise further venture capital
“Intercom is like a series, what's that, like D or whatever company. We don't need to raise, so hence it's not E or F or whatever”
Traynor: Angel portfolio companies have surpassed Intercom's valuation multiple times over
“I've invested in companies that have like gone on to surpass the valuation of Intercom many times over, and the founders have turned into absolute monster CEOs and monster COOs along the way.”
Des Traynor: Miro succeeded through extreme execution and fending off FigJam
“They have just been an execution machine. For a really specific problem, and they kind of stood up against an external, what could have been a threat in FigJam, and they've done really well through that as well.”
Des Traynor: High valuations tempt founders into grand statements over execution
“Because when you start telling, if you have to do, if you just sit down with a journalist and say, well, you're now worth whatever billion dollars they're worth. You feel obliged to say all this new shit, right? Like you feel obliged to say, well, we're actual…”
Traynor: Second Products Must Create Multiplicative Advantages with Core Offerings
“Is there value in doing both of these things under the same company? Like, and this is a question of like brand architecture in a sense, right? Cause if you really, if you think, Hey, I can find a second team and they're going to go and do this other thing. Wh…”
Des Traynor: Scaleups cannot launch bare-bones MVPs without damaging their brand
“If intercom launches a surveys tool, which we did in March, we can't be like limping in with an MVP that doesn't work. It would actually be brand damaging. We need to like, it needs to have all of the traits of intercom.”
Traynor: Dedicated Competitors Signal a Feature Should Be a Standalone Product
“How are they currently solving the problem that this feature slash product solves? And if the answer is they're doing it in Excel or whatever, then yeah, you could probably argue you pull it in as a feature. If they actually have another platform where they li…”
Traynor: Product features lacking organic momentum are failing
“If it doesn't have its own momentum as a feature or product, and if you find yourself just constantly trying to push a nudge and you can't get customers to stick to it, that's generally a sign that as a feature or product, it's like, it's not working.”
Traynor: Sunsetting features requires complete code removal and 12-month notice
“You end of life, which means you stop taking on new customers. You tell all the current customers, Hey, I know you depend on this thing. It's going to fade away over 12 months. Here's our suggested like a migration path off to some other way to get it done. If…”
Des Traynor: B2B Buyers Only Care About Making or Saving Money
“This is going to sound quite reductive and it kind of is, but I have two numbers to worry about Harry. Are you going to make me money or save me money? And if so, how, and why should I believe you? And that's what the buyer wants to know. Cause they're just tr…”
Des Traynor: Follow-the-Money Forces Horizontal Software Into Enterprise B2B
“Inevitably, like, the problem with most of those use cases is, once you start to follow the money, you end up back in B to B SaaS land, right? Like, or at least B to B land anyway, right? There's not a lot of money selling software to wedding planners. There's…”
Des Traynor: Horizontal Software Products Must Pick Specific Marketing Lanes
“All of your desperate attempts to horizontalize yourself When it comes to marketing, you still need to pick a lane and say, here's what we are. Even if you're just saying it for one person, you still need to say it. Like you can't be everything to everyone. Ca…”
Des Traynor: Startups With Horizontal Runway Should Delay Moving Upmarket
“If you think you just have loads of run room horizontally in the market, so you can just keep getting more and more customers like the ones you already have. And I mean, exactly like them then I, and you don't have to change your product to do that. Then I thi…”
Des Traynor: Evaluate features by total cost of ownership, not build effort
“Every complex new feature we build has to get marketed by a marketer and has to get sold by a salesperson and supported by a support person. So you have to think about the total cost of ownership of that feature, not just how hard was it to build.”
Des Traynor: Marc Andreessen's 'just raise prices' mantra is silly
“The idea of like just raise prices is silly. I think align price to value is the thing you have to do.”
Des Traynor: Enterprise readiness depends on backend capabilities, not visible features
“When people say, are you enterprise ready? What they actually mean is all of that stuff. And people forget to market it. People forget to like showcase that in the right places because it's not visible.”
Des Traynor: No consumer has the 'all data in one place' problem
“The ones that I get most bored by anything that smacks of all your data in one place, I just really don't care about. And especially if it's consumer, like just in general, it's such a, like, no one actually has that problem.”
Des Traynor: Turning glorified Google Docs into SaaS apps is never viable
“Turning spreadsheets into SaaS apps has been a good idea forever. Turning glorified Google Docs into SaaS apps, I think, has never been a good idea.”
Des Traynor passed on SpaceX due to $100k minimum check size
“There was a chance to invest in SpaceX, but, like, I didn't have a hundred grand, and that was the smallest check. And I, I'm just like, hey, like, I probably should have borrowed that money, but, like, I didn't have it.”
Des Traynor caps standard angel checks at $25K unless deeply impressed
“My check sizes might be like somewhere in like the 25 K region, unless I absolutely love the product, love the space, and I've just been blown away. In which case, I'll push for more, and I'll take what I can get.”
Des Traynor skips due diligence, requiring lead investors to perform it
“I definitely don't do a due diligence at all, but like, but at the same time, I always caveat my check and say like, I'm only doing this if there's a lead investor who is actually going to do due diligence”
Des Traynor: Resume brand names rarely guarantee candidate high performance
“Probably earlier in my career, just being blinded by the logo, I think was probably the biggest thing. Like, such and such a person worked at such and such a company... But that's probably the single biggest thing is like assuming that because somebody worked …”
Des Traynor: Functional teams require varied skill levels, not just A-players
“The ingredients of a team is not like just a load of people all walking around telling each other the best. Like you actually need a mix and people come to companies to learn. And by definition, that means they're not the best. They believe they can get better…”
Des Traynor: Executive hires should be made for four- to five-year stints
“It's very rare you're hiring for the rest of your life and their career. You're hiring for like chugs, you're hiring for like contracts of a season, like of like four or five years stints or whatever is generally this sort of norm.”
Des Traynor: Tech media is starved of optimistic, pro-tech coverage
“I think like what I'd love to change is that I would love there to be one technology publication that has two traits. One it's run by people who like technology, like as in, they believe it generally can be a cause for good in the world. And two, it is optimis…”
Shorts cut from this episode
▶ Des Traynor: This startup taught me so much · 20VC with Harr (@15:02)
▶ FOUNDERS: Do not make this common mistake · 20VC with Harry (@17:09)
▶ Two Product Marketing Tips - Part 2/2 · 20VC with Harry Steb (@29:47)
▶ Two Product Marketing Tips - Part 2/2 · 20VC with Harry Steb (@28:37)
▶ Founder vs. Idea: Which is more important? · 20VC with Harr (@2:43)