Overview
Memo was a messaging application founded in 2019 by Peter Saxton and Richard Shepherd in Exeter, UK. The company entered Y Combinator's Summer 2020 batch with a pitch to replace email and Slack with a calmer, richer form of asynchronous communication — one that let users comment on individual words, sentences, or paragraphs, and share links, videos, and galleries in a more structured format than a chat thread. It operated under the domain sendmemo.app and raised approximately $150,000 from YC as its sole institutional funding round.[1][13]
Memo failed because it attempted to displace deeply entrenched communication incumbents with incremental UX improvements, while lacking the distribution strategy, network density, or runway to make those improvements matter. The product's core value — "feel-good communication" — was real as a user frustration but insufficient as a switching argument for teams already embedded in Slack or email workflows.
The company is listed as permanently closed on Crunchbase, and the sendmemo.app domain now resolves to a parking page.[15][4] No acquisition, acqui-hire, or public shutdown announcement was made. Peter Saxton subsequently founded DID.app, a passwordless authentication product, and later pivoted further to building EYG, a new programming language — a trajectory that suggests a clean break from the communication space rather than a continued belief in the original thesis.[10][11]
Founding Story
Peter Saxton and Richard Shepherd founded Memo in 2019 in Exeter, a mid-sized city in southwest England with a modest but growing tech community. The two founders brought complementary technical backgrounds: Saxton described himself as an experienced developer with expertise in API design, web application UI, and infrastructure reliability, with an academic background in Quantum Optics and, per Crunchbase, prior executive experience at Bango, a mobile commerce company.[9][21] Shepherd described himself as a "UK based founder and full-stack web developer with sales experience running my creative agency in the south west of England."[8]
How the two met is not documented in any public source. What is documented is the shared frustration that animated the product: the belief that existing communication tools — email in particular, but also Slack — had become hostile to focused, meaningful work. The YC listing frames this directly: "Forget laborious old email and hyperactive Slack. We built Memo as the feel-good alternative that will make you love communication again."[6] Shepherd's portfolio site confirms the collaborative origin: "Peter and I developed Memo together during our time at YCombinator. Memo re-evaluated how online communication could work."[18]
The founding insight was not technically novel — the "communication overload" problem had been articulated by dozens of prior startups — but Saxton and Shepherd believed the execution gap was real. Existing tools had been designed for speed and volume, not depth and clarity. Their answer was a messaging layer that borrowed from document annotation: the ability to comment on any word, sentence, or paragraph within a message, combined with rich media embedding and a visual design intended to feel calmer than a Slack channel.[19]
The company applied to and was accepted into Y Combinator's S20 batch, which was announced as fully remote on April 20, 2020, due to the COVID-19 pandemic.[20] This was an unusual cohort environment: the peer network, in-person mentorship, and serendipitous introductions that typically define the YC experience were compressed into video calls. Whether this materially affected Memo's trajectory is speculative, but the remote format almost certainly reduced the density of investor relationships that founders typically build during the program.
One data anomaly worth noting: Tracxn tracks Memo under the alias "Plum Mail," associated with the legal entity MEMO LTD, and describes it as a provider of "email services."[16] Whether "Plum Mail" represents an early product name, a pre-YC iteration, or simply a data error in Tracxn's system is unknown. No public record confirms a formal pivot or rebrand.
Timeline
- 2019 — Memo founded by Peter Saxton and Richard Shepherd in Exeter, UK.[1]
- April 20, 2020 — Y Combinator officially shifts the S20 batch to a fully remote format due to COVID-19.[20]
- 2020 — Memo accepted into YC S20 batch.[1]
- August 2020 — Memo listed on BetaList as an async communication tool with paragraph-level commenting.[19]
- August 22–25, 2020 — Memo raises seed round from Y Combinator; amount recorded by Tracxn as approximately $150K.[12][13]
- 2020 (post-Demo Day) — No follow-on funding raised; YC remains sole institutional investor.[14]
- 2020 (date unknown) — Peter Saxton moves on to DID.app, a passwordless authentication venture.[10]
- 2023 — Peter Saxton is building EYG (Eat Your Greens), a new programming language, indicating full departure from the communication space.[11]
- 2024 — sendmemo.app resolves to a parking page; Crunchbase lists Memo as permanently closed.[4][15]
What They Built
Memo was a messaging application designed for asynchronous, rich-media communication between individuals or small groups. Its core premise was that existing tools had optimized for the wrong things: email for formality and volume, Slack for speed and presence. Memo aimed to occupy a middle ground — structured enough to support thoughtful communication, lightweight enough to feel personal.
The product's most distinctive feature, per its BetaList listing, was the ability to "comment on any word, sentence or paragraph in Memo messages."[19] This annotation-layer approach to messaging was meaningfully different from standard chat: rather than replying to an entire message, a user could anchor a response to a specific clause, creating a threaded, document-like conversation structure. This was closer to how people annotate Google Docs than how they use iMessage or Slack.
Beyond annotation, Memo included a set of UX features designed to reduce friction and increase clarity:[7]
- Quote-in-reply: Users could quote a specific portion of a message when responding, preserving context in longer threads.
- Rich link previews: URLs shared in messages rendered as visual cards with metadata, reducing the need to click through to understand context.
- Highlighted questions: The product could surface or visually distinguish questions within a message, making it easier to track what needed a response.
- Media galleries: Images and videos could be shared in a structured gallery format rather than as raw file attachments.
The overall design philosophy, as described in Memo's YC listing, was to make communication feel "good" — a subjective but coherent design goal that implied slower, more deliberate interactions than a real-time chat interface encourages.[6] Crunchbase categorizes Memo under Apps, Messaging, and Mobile Apps, suggesting the product had a mobile component, though whether it was mobile-first or cross-platform is not documented.[17]
The product operated at sendmemo.app, a domain that now resolves to a parking page.[3][4] No archived screenshots of the live product are publicly available, which limits any assessment of the actual UX quality relative to the described features. Whether the product was targeted at consumers, small teams, or enterprises is not documented. No pricing model or monetization strategy has been disclosed publicly.
The Tracxn alias "Plum Mail" and the description of Memo as an "email services" provider raises the possibility that the product went through an early iteration focused more narrowly on email before broadening to a general messaging paradigm, but this cannot be confirmed from available sources.[16]
Market Position
Target Customers
Memo's positioning — "forget laborious old email and hyperactive Slack" — implied a target user who was already using both tools and dissatisfied with both.[6] This is a large and real population: knowledge workers who find email too slow and formal for internal communication, but find Slack too interruptive and ephemeral for substantive discussion. The product's annotation and async features suggest a lean toward small teams doing collaborative, text-heavy work — writers, designers, developers, or distributed teams across time zones.
Whether Memo pursued a consumer or B2B go-to-market is not documented. The "feel-good communication" framing reads as consumer-oriented, but the feature set (highlighted questions, quote-in-reply, structured threads) has more natural utility in a professional context. This ambiguity — consumer emotional appeal, professional feature set — may itself have been a positioning problem.
Market Size
The business communication software market was large and growing rapidly in 2020. Slack reported approximately 12 million daily active users in 2020 before its Salesforce acquisition, and Microsoft Teams reached 75 million daily active users by April 2020, accelerated by COVID-19 remote work adoption. Email remained the dominant communication medium for most organizations globally. The total addressable market for team communication tools was plausibly in the tens of billions of dollars annually, but the relevant question for Memo was not market size — it was whether any portion of that market was reachable by a two-person team with $150,000 in funding.
Competition
Memo entered a competitive landscape that was structurally unfavorable along every axis that mattered.
Distribution reach vs. product depth: Slack and Microsoft Teams had distribution advantages that were not merely large but self-reinforcing. Enterprise IT decisions, SSO integrations, and existing workflow automations created switching costs that no feature improvement could easily overcome. Memo's annotation-layer messaging was genuinely differentiated, but differentiation only matters if users can be reached — and reaching enterprise teams requires sales infrastructure that a two-person team cannot build on $150,000.
The platform absorption risk: The specific features Memo offered — rich link previews, threaded replies, media galleries — were features that incumbents were actively building. Slack introduced threaded replies in 2017. Microsoft Teams added rich media and annotation-adjacent features progressively through 2019–2021. The risk that Memo's differentiators would be absorbed by incumbents before Memo could achieve scale was not hypothetical; it was the default trajectory of the market.
The cold-start problem as a structural moat: Communication tools are among the most network-dependent products in software. A messaging app with no contacts is worthless. This means that every new entrant must solve the cold-start problem — convincing a critical mass of users to switch simultaneously — before the product delivers any value. Incumbents benefit from this asymmetry: their existing user bases make their products more valuable every day, while challengers must overcome inertia before delivering any value at all. Memo's async, annotation-based approach did not offer a wedge strategy (a specific use case where the cold-start problem is smaller) that would have allowed it to build density in a defined community before expanding.
COVID-19 as a competitive accelerant for incumbents: The pandemic, which began just as Memo was entering YC, drove mass enterprise adoption of Slack and Microsoft Teams at a pace that would not have occurred organically. Teams that had been deferring communication tool decisions were forced to standardize quickly, and they standardized on established platforms. Memo was attempting to recruit users from a pool that was simultaneously being locked into competitor products by organizational mandates.
Business Model
Memo never publicly disclosed a revenue model, pricing structure, or monetization strategy. The absence of any revenue documentation — no pricing page, no press coverage of paid tiers, no founder commentary on business model — is itself a signal. For a company that raised only $150,000 and had two employees, the most likely scenario is that the team was focused entirely on product development and user acquisition, deferring monetization questions to a post-traction phase that never arrived.
Inferred unit economics (labeled as estimates): With $150,000 in total funding and a two-person team based in Exeter, UK — where engineering salaries are substantially lower than in San Francisco or London — the company's monthly burn rate was likely in the range of £5,000–£10,000 ($6,500–$13,000 at 2020 exchange rates), implying a runway of roughly 12–24 months from the YC seed close in August 2020. These are inferences based on regional salary benchmarks and team size, not disclosed figures.
If Memo had pursued a SaaS model — the natural fit for a team communication tool — a plausible pricing structure would have been $5–$10 per user per month, consistent with Slack's pricing at the time. At that rate, reaching $1 million in annual recurring revenue would have required 8,000–17,000 paying users. There is no evidence that Memo approached this scale. The company never disclosed user counts, revenue, or growth metrics in any public forum.
Y Combinator was the sole institutional investor, with no angels, no Series A, and no follow-on funding of any kind recorded.[14] The failure to raise beyond the YC seed is the clearest available signal about investor confidence in the company's trajectory.
Post-Mortem
1. The Cold-Start Problem Was Insurmountable at the Available Funding Level
The most fundamental structural challenge Memo faced was the cold-start problem endemic to all communication tools: a messaging app delivers zero value to a user with no contacts on the platform. Unlike a productivity tool (which a single user can adopt independently) or a marketplace (which can be seeded with supply-side inventory), a communication network requires simultaneous adoption by multiple parties before it delivers any value to any of them.
Solving the cold-start problem requires either a viral growth mechanism (WhatsApp's phone-number-based contact discovery), a captive community (Slack's initial focus on gaming communities and developer teams), or significant marketing spend to drive coordinated adoption. Memo had none of these. Its $150,000 in funding was insufficient to fund a meaningful paid acquisition campaign, and no viral growth mechanism is documented in any public source.[13] The BetaList listing in August 2020 suggests the team was pursuing organic early-adopter discovery, which is a reasonable strategy for a consumer product with strong word-of-mouth potential — but there is no evidence it generated meaningful user density.[19]
The attempted remedy — YC Demo Day exposure and BetaList listing — was appropriate for the resources available but structurally insufficient for a communication tool. Demo Day generates investor interest, not user adoption. BetaList reaches early adopters who are, by definition, willing to try new tools but unlikely to recruit their colleagues onto a new platform. Neither channel addresses the core problem: getting enough people in the same network to use Memo simultaneously.
2. The Competitive Timing Was Structurally Unfavorable
Memo entered YC in mid-2020, precisely when COVID-19 was driving the fastest mass adoption of enterprise communication tools in history. Microsoft Teams grew from 32 million to 75 million daily active users between March and April 2020 alone. Slack's user base expanded rapidly through the same period. Organizations that had been slow to standardize on communication tools were forced to make decisions quickly, and they chose established platforms with enterprise security certifications, IT integrations, and vendor support relationships that a two-person YC startup could not offer.
This was not merely a matter of bad luck. The pandemic created a structural lock-in event: once a team standardizes on Slack or Teams under organizational mandate, the switching cost rises dramatically. IT has configured SSO. Workflows have been built on integrations. Historical message archives exist on the platform. Memo was attempting to recruit users from a pool that was simultaneously being locked into competitor products by forces entirely outside Memo's control.
The team's attempt to address this — positioning Memo as an alternative rather than a replacement, emphasizing emotional resonance over feature parity — was a reasonable strategic response but insufficient to overcome the organizational inertia created by mass enterprise adoption of incumbents.
3. The Product Differentiation Was Real But Not Defensible
Memo's annotation-layer approach to messaging — commenting on individual words, sentences, or paragraphs — was a genuinely differentiated feature that no major incumbent offered at the time.[19] The problem was not that the feature was bad; it was that the feature was the kind of incremental UX improvement that incumbents could absorb without strategic disruption.
Slack's threaded replies (launched 2017) had already demonstrated that the incumbent could add structured conversation features without losing users. Rich link previews, media galleries, and quote-in-reply were all features that Slack, iMessage, and WhatsApp were building or had built. The annotation feature was the most distinctive element of Memo's product, but it was also the most niche: the use case for commenting on a specific sentence within a message is real (editorial feedback, legal review, detailed technical discussion) but narrow. It was not a feature that would drive mass adoption from users who were otherwise satisfied with Slack.
No evidence exists that the team attempted to pivot toward a more defensible niche — for example, targeting a specific vertical (legal, editorial, academic) where annotation-based communication had established workflow value. The broad "alternative to email and Slack" positioning left Memo competing on every dimension simultaneously against incumbents with vastly superior resources.
4. The Two-Person Team Lacked Go-to-Market Infrastructure
Saxton and Shepherd were technically capable founders — a developer with infrastructure and API experience, and a full-stack developer with agency sales background.[8][9] What the team lacked, based on available evidence, was dedicated go-to-market expertise: a growth marketer, a community builder, or an enterprise sales function. For a consumer product, this might be survivable if the product has strong organic virality. For a B2B communication tool competing against Slack, it is a critical gap.
The YC S20 batch's fully remote format may have compounded this problem. The in-person YC experience typically generates introductions to potential design partners, early customers, and angel investors through the physical proximity of founders, partners, and alumni. A remote cohort compresses these interactions into scheduled video calls, reducing the serendipitous relationship-building that often produces a startup's first ten customers.[20] Whether this materially affected Memo's outcome is speculative, but the remote format was a headwind for a product that needed community density to demonstrate value.
5. No Follow-On Funding Signals Insufficient Demo Day Traction
The absence of any follow-on funding after YC Demo Day is the clearest external validation of the failure thesis.[14] YC Demo Day in 2020 attracted significant investor attention despite the remote format; many S20 companies raised substantial seed rounds. Memo raised nothing. This indicates that investors who saw the pitch — and who were actively deploying capital into communication tools during a period of unprecedented remote work adoption — did not find Memo's traction, team, or market position compelling enough to fund.
No public record exists of what metrics Memo presented at Demo Day, what investor feedback was received, or whether the founders attempted to raise from angels or seed funds outside the YC network. The silence is complete. Peter Saxton's subsequent pivot to DID.app (passwordless authentication) and then to EYG (a programming language) suggests the founders concluded that the communication market was not the right arena for their skills, rather than that Memo's specific execution was the problem.
Key Lessons
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The cold-start problem requires a wedge, not just a better product. Memo's annotation-layer messaging was a genuine UX improvement over Slack, but it was positioned as a general-purpose communication tool rather than a solution to a specific, high-value use case where a small community could achieve network density quickly. Slack succeeded by starting with gaming communities and developer teams — groups with high communication frequency and low switching costs — before expanding. Memo launched broadly against entrenched incumbents with no defined wedge community, making the cold-start problem nearly impossible to solve on $150,000 in funding.
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Launching a Slack alternative in mid-2020 meant swimming against a structural tide, not just competitive headwinds. The COVID-19 pandemic created a mass enterprise lock-in event between March and August 2020, the exact window in which Memo was going through YC. Organizations that standardized on Slack or Teams during this period built integrations, archives, and IT configurations that raised switching costs dramatically. Memo's window to recruit teams before lock-in occurred was measured in weeks, not months — a timeline incompatible with organic community growth.
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"Feel-good communication" is a positioning strategy, not a switching argument. Memo's emotional framing — making users "love communication again" — resonated as a description of a real problem but provided no concrete reason for a team to migrate away from Slack. B2B communication tool adoption is typically driven by IT decisions, security requirements, and integration compatibility, not by individual users' emotional relationship with their inbox. A positioning strategy built around emotional resonance needed either a consumer go-to-market (where individual adoption decisions are possible) or a concrete enterprise value proposition (cost reduction, compliance, measurable productivity) — Memo had neither clearly defined.
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Incremental UX differentiation in communication tools is a feature, not a moat. Memo's most distinctive capability — paragraph-level annotation — was the kind of improvement that incumbents can absorb in a product update cycle. The history of communication tools is littered with companies that built genuinely better UX (Quip, Stride, HipChat) only to find that incumbents either acquired them or replicated their features. A durable competitive position in communication requires either a network that incumbents cannot replicate (WhatsApp's phone-number graph) or a vertical lock-in (Figma's design workflow) — neither of which Memo pursued.
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A two-person technical team building a network-effects product needs a third founder for growth. Saxton and Shepherd were capable of building the product; the gap was in distribution. For a communication tool, where value is entirely dependent on adoption by groups rather than individuals, the go-to-market function is as important as the product itself. The team's documented backgrounds — infrastructure development, full-stack development, agency sales — did not include the community building, growth marketing, or enterprise sales expertise that a communication platform requires to escape the cold-start trap.
Sources
- Y Combinator — Memo company listing
- Richard Shepherd portfolio — Memo project
- Crunchbase — Memo organization profile
- Crunchbase — Memo profiles and contacts
- Tracxn — Plum Mail / Memo profile
- BetaList — sendmemo listing
- sendmemo.app — product domain (now parking page)
- Peter Saxton personal website
- TechCrunch — YC S20 shifts to fully remote format (April 20, 2020)