The Email Startup Graveyard: Why 80%+ of Email Companies Fail

While countless email startups have burned through millions solving non-existent problems, we at 转发邮件 have quietly built actual email infrastructure from scratch since 2017—proving that sustainable email services require engineering, not just venture capital. This is an exhaustive analysis of email startup failures, acquisitions, and the fundamental misunderstanding of what email actually is.

[!WARNING] TL;DR: Stop building email apps. Email isn't broken. This post documents why 80%+ of email startups fail and why you shouldn't be the next one.

[!NOTE] Key Insight: Most email startups don't build actual email infrastructure from scratch. They're just glue on top of Amazon SES or leveraging existing open-source solutions like Cyrus/Postfix (Fastmail, Resend, etc.). The infrastructure works perfectly - the problem is thinking it needs "improvement."

The Email Startup Failure Matrix

Here's every major email startup failure we could find, organized by accelerator, funding, and outcome:

公司	Year	Accelerator	Funding	Outcome	地位	Key Issue
Skiff	2024	-	$14.2M total	Acquired by Notion → Shutdown	😵 Dead	Founders left Notion for Cursor
Mailbox	2013-2015	-	$5.82M raised, $100M acquisition	Acquired → Shutdown	😵 Dead	Solved non-problem
Sparrow	2012	-	$247K seed, <$25M acquisition	Acquired by Google → Shutdown	😵 Dead	Talent acquisition only
Email Copilot	2012	Techstars	~$120K (Techstars standard)	Acquired → Shutdown	😵 Dead	Now redirects to Validity
ReplySend	2012	Techstars	~$120K (Techstars standard)	Failed	😵 Dead	Vague value proposition
Nveloped	2012	Techstars	~$120K (Techstars standard)	Failed	😵 Dead	"Easy. Secure. Email"
Jumble	2015	Techstars	~$120K (Techstars standard)	Failed	😵 Dead	Email encryption
InboxFever	2011	Techstars	~$118K (Techstars 2011)	Failed	😵 Dead	API for email apps
Emailio	2014	YC	~$120K (YC standard)	Pivoted	🧟 Zombie	Mobile email → "wellness"
MailTime	2016	YC	~$120K (YC standard)	Pivoted	🧟 Zombie	Email client → analytics
reMail	2009	YC	~$20K (YC 2009)	Acquired by Google → Shutdown	😵 Dead	iPhone email search
Rapportive	2012	YC	~$120K (YC 2006)	Acquired by LinkedIn → Shutdown	😵 Dead	Gmail social profiles add-on
Mailhaven	2016	500 Global	~$100K (500 standard)	Exited	Unknown	Package tracking

[!CAUTION] Failure Rate: Techstars alone has 28 email-related companies with only 5 exits - an exceedingly high failure rate (sometimes calculated to be 80%+).

The Infrastructure Reality Check

Here's what nobody talks about: every single "email startup" is just building UI on top of existing infrastructure.

What Actually Runs Email

亚马逊SES: Powers most "email APIs" and services
后缀: The actual SMTP server running everywhere
Cyrus IMAP: What handles your actual email storage
垃圾邮件杀手: What filters your spam
DKIM/SPF/DMARC: The authentication that actually works

What "Email Startups" Actually Build

React Native apps with memory leaks
Web interfaces that break email threading
"AI" features that Gmail already has
"Security" layers that break existing workflows
APIs that wrap Amazon SES with 10x markup

[!TIP] Key Pattern for Email Success: The companies that actually succeed in email don't try to reinvent the wheel. Instead, they build infrastructure and tools that enhance existing email workflows. SendGrid, Mailgun, and Postmark became billion-dollar companies by providing reliable SMTP APIs and delivery services - they work 和 email protocols, not against them. This is the same approach we take at Forward Email.

Case Study: The Skiff Disaster

Skiff perfectly exemplifies everything wrong with email startups.

The Setup

Positioning: "Privacy-first email and productivity platform"
Funding: Significant venture capital
Promise: Better email through privacy and encryption

The Acquisition

Notion acquired Skiff in February 2024 with typical acquisition promises about integration and continued development.

The Reality

Immediate shutdown: Skiff shut down within months
Founder exodus: Skiff founders left Notion and joined Cursor
User abandonment: Thousands of users forced to migrate

The Cycle Continues

Meanwhile, other entrepreneurs keep building identical solutions. Jonathan Unikowski (@jnnnthnn) recently announced yet another email app called "Net" - proving that people don't learn from the graveyard.

Case Study: When Email Infrastructure Goes Wrong

Resend's Security Meltdown

Resend, the "developer-focused email platform," had a catastrophic security incident that perfectly illustrates why email infrastructure is hard.

The Incident: On January 7th, 2024, attackers used a leaked environment variable that was exposed client-side on the Resend Dashboard to access customer data including:

Email addresses and domains
API keys (encrypted)
Logs and contacts
User information

The Timeline:

December 30th: Database API key exposed client-side
January 7th: Attackers started accessing data
January 9th: Incident discovered and promoted to SEV-0
January 10th: 25 minutes of downtime during remediation

[!WARNING] The Root Cause: A database API environment variable was accidentally bundled into client-side code. This is exactly the kind of mistake that happens when you're building "email infrastructure" without understanding email infrastructure.

ActiveCampaign's Postmark Acquisition: A Cautionary Tale

The Original Success: Postmark was originally owned by Wildbit, where it built a reputation as a reliable transactional email service beloved by developers.

The Acquisition: ActiveCampaign acquired Postmark in May 2022 with promises that "Postmark will remain a standalone product".

The Reality:

SSL Certificate Failure: Nearly 10-hour outage in September 2024 due to expired SSL certificates
User Rejections: Marc Köhlbrugge getting rejected despite legitimate usage
Developer Exodus: @levelsio stating "Amazon SES is our last hope"

MailGun: Customer Service Breakdown

Scott reported: "The worst service from @Mail_Gun... we've not been able to send emails for 2 weeks due to an issue on their side" with MailGun support providing only: "I'm afraid I don't have an update at this time."

The Accelerator Analysis

Y Combinator: The Email App Factory

From YCDB.co research:

Emailio (W14): Started as "Mobile email app", now pivoted to "Email built for wellness" - appears to have pivoted.

MailTime (W16): Began as email client, now "turns transactional email receipts into actionable consumer insights" - completely abandoned original vision.

reMail (W09): "Email search for iPhone. Acquired by Google in Feb 2010" - another Google talent grab that disappeared.

Techstars: The Email Graveyard

Techstars has funded 28 email-related companies with only 5 exits - an exceedingly high failure rate.

The Failures:

Email Copilot (2012): emailcopilot.com now redirects to Validity, which states "Return Path was acquired by Validity in 2019, but the platform is no longer available for sale"
ReplySend (2012): "Company developing software and tools for email" - vague enough to mean nothing
Nveloped (2012): "Easy. Secure. Email" - solving problems that don't exist
Jumble (2015): "Email encryption that integrates directly into existing email clients" - PGP already exists
InboxFever (2011): "API solution that enables them to create email applications" - building on email instead of replacing it (the right approach, but still failed)

The Exception: SendGrid succeeded because it's email infrastructure (APIs for sending) rather than trying to replace email clients.

Why Email Startups Always Fail

1. Email Isn't Broken

Email is a 50+ year old protocol that successfully delivers messages between any two points on the internet. It works exactly as designed.

2. Network Effects Are Unbreakable

Email's value comes from universal adoption. A "better" email client that only works with other users defeats the entire purpose.

3. They're Solving Non-Problems

Most email startups focus on:

UI/UX improvements (Gmail is fine)
Workflow optimizations (filters work)
"AI" features (Gmail has them)
"Security" (DKIM/SPF/DMARC work)

4. Technical Debt Is Massive

Building email clients means dealing with:

Decades of legacy protocols
Spam filtering complexity
Deliverability reputation systems
Compatibility with every email server ever built

5. The Infrastructure Already Exists

[!IMPORTANT] Almost nobody builds email infrastructure from scratch. Most "email startups" are just:

Wrapping Amazon SES with a prettier API

Using existing open-source solutions like Postfix/Cyrus (Fastmail, Resend, etc.)

Building React Native apps on top of IMAP

Adding "AI" to existing email protocols

The Venture Capital Trap

VCs keep funding email startups because:

Large addressable market (everyone uses email)
Obvious pain points (inbox overload, spam)
Success stories (Gmail - though it succeeded with storage, not "fixing" email)
Founder conviction (everyone thinks they can succeed where others failed)

But they ignore the fundamental reality: email works perfectly for what it was designed to do.

The Technical Reality: Modern Email Stacks

What Actually Powers "Email Startups"

# What Fastmail actually runs postfix + cyrus-imap + spamassassin + custom-web-ui What Resend actually runs amazon-ses + nodejs-wrapper + react-dashboard What Proton actually runs* postfix + custom-encryption + web-interface What we actually run 100% custom Node.js JavaScript stack built from scratch What Gmail actually runs

custom-everything (because Google has infinite resources)

* APNIC Blog: SMTP downgrade attacks and MTA-STS - Logs indicate that Proton Mail uses postfix-mta-sts-resolver, confirming they run a Postfix stack under the hood.

The Performance Problems

Modern email startups suffer from:

Memory Bloat: JavaScript-heavy applications consuming 500MB+ for basic email
Battery Drain: Inefficient background processing
Compatibility Issues: Breaking email threading, search, and standard workflows
Security Vulnerabilities: Like Resend's client-side environment variable exposure

The Acquisition-to-Shutdown Pipeline

The Standard Pattern

Startup raises funding promising to "revolutionize email"
Gains early traction with users who like UI improvements
Struggles with email complexity (spam, deliverability, protocols)
Gets acquired for talent and technology
Product gets shut down within 6-24 months
Founders leave acquiring company
Cycle repeats with new entrepreneurs

Recent Examples

Skiff → Notion → Shutdown → Founders to Cursor (2024)
Mailbox → Dropbox → Shutdown (2013-2015)
Sparrow → Google → Shutdown (2012)

The Infrastructure Consolidation Problem

Resend's Acquisition Spree

Resend, founded by Zeno Rocha (@zenorocha), has been aggressively acquiring companies:

Mergent Acquisition (April 2025): "Resend has acquired Mergent, the serverless background job service" - consolidating email-adjacent services.

The Degradation Pattern

When email infrastructure gets acquired:

Initial promises of improved resources
Integration challenges leading to outages
Resource reallocation to other products
Service degradation through reduced investment
User migration to alternatives

ImprovMX: The Serial Acquisition Target

ImprovMX has been acquired 2x and changed hands 3 times:

Original founding as email forwarding service
First acquisition with promises of growth
Second acquisition by Matthew Tse in January 2025
Latest sale 为了 under $1.2M despite $30K MRR

As noted in 隐私指南讨论: multiple ownership changes create uncertainty for users who need reliable email forwarding.

The Hacker News Reality Check

Hacker News discussions about email startups consistently show skepticism from technical users who understand that email's "problems" are often features, not bugs. Common HN Comments:

"Email works fine, this solves a non-problem" - tferris on "Email is not broken: It's a framework, not an application"
"Just use Gmail/Outlook like everyone else" - Multiple users on "Email Apps Suck"
"Another email client that will be shut down in 2 years" - Comments on Superhuman layoffs
"The real problem is spam, and this doesn't solve that" - icefox on email infrastructure discussions

The Technical Community Knows: Email's decentralized, open nature is what makes it valuable, not something to be "fixed" by proprietary solutions.

The Modern AI Email Grift

The Latest Wave

Recent email startups are adding "AI" to their pitches:

NeveMind (2023): "Automatically replies to all your emails" - appears to be defunct or never launched
Ripple AI (2024): "Design beautiful marketing emails in minutes" 和 $20K total funding
Moneiva (2024): "AI-driven communication platform for freight operations" automating voice, email, SMS, and WhatsApp

The Same Old Problems

They're still solving non-problems:

Email organization: Filters and folders work fine
Smart replies: Gmail has had this for years
Spam detection: Already solved by existing providers
AI summarization: Outlook already does this

What Actually Works: The Real Email Success Stories

Infrastructure Companies (The Winners)

SendGrid: Email delivery APIs (acquired by Twilio for $3B)
邮件枪: Email APIs for developers
亚马逊SES: The infrastructure everyone actually uses
Cloudflare Email Routing: Simple forwarding that works

Email Providers (The Survivors)

电子邮件: Infinite Google resources + storage
外表: Microsoft integration + enterprise
快速邮件: Postfix + Cyrus + good UI
Proton: Postfix + encryption + privacy focus

The Exception: Xobni's Success Story

Not every email company ends in failure. Xobni (inbox spelled backwards) stands as a rare example of email startup success, proving that building on top of email infrastructure rather than trying to replace it can work.

The Success Formula

Founded: 2006 by Adam Smith 和 Matt Brezina from Adam's MIT dorm room as part of Y Combinator Summer 2006.

The Product: Outlook plugin that enhanced email management with:

Advanced contact management and social integration
Fast email search and conversation threading
Email analytics and relationship insights
LinkedIn, Twitter, and Salesforce integrations

The Funding: Raised over $40 million from investors including First Round Capital, Khosla Ventures, and Atomico.

The Acquisition: Yahoo acquired Xobni in July 2013 for $30-60 million, making it one of Y Combinator's early success stories.

Why Xobni Succeeded Where Others Failed

[!TIP] The Key Insight: Xobni enhanced existing email workflows instead of trying to replace them. They built a plugin that made Outlook better, not a new email client that competed with Outlook.

What They Did Right:

Worked with existing infrastructure: Enhanced Outlook rather than replacing it
Solved real problems: Outlook's contact management and search were genuinely poor
Focused on productivity: Added features that actually saved time
Enterprise-friendly: Integrated with business tools like Salesforce

The Founders' Continued Success

Matt Brezina went on to:

Co-found Sincerely (mobile gifting platform) in 2011
Sell Sincerely to Provide Commerce for undisclosed amount in 2013
Become an active angel investor with investments in Dropbox, Mailbox, and others

Adam Smith continued with:

Co-found Kite (AI-powered coding assistant) in 2014
Raise $17 million for Kite before it eventually shut down in 2022
Join Affirm as VP of Engineering
Become a seed investor in companies like Dropbox, Cruise, and Rescale

The Pattern

Winners build ON TOP of email. Losers try to REPLACE email.

Our Approach: Why We're Different

Full Disclosure: This analysis is written by us at Forward Email, but the data speaks for itself.

What We Do

Build custom infrastructure: 100% custom Node.js JavaScript stack built from scratch
Focus on privacy: End-to-end encryption without breaking compatibility
Open source everything: 100% open source
Build on email standards: IMAP, SMTP, POP3 - not proprietary protocols

What We Don't Do

❌ Try to "revolutionize" email
❌ Build proprietary protocols
❌ Promise to "fix" what isn't broken
❌ Wrap Amazon SES and call it innovation
❌ Build memory-hungry Electron apps 或者 Expo apps built on React Native with horrid performance

How We Build Email Infrastructure That Actually Works

Our Anti-Startup Approach

While the companies above burned through millions trying to "revolutionize" email, we at 转发邮件 took a radically different approach: actually building email infrastructure from scratch.

Founded in 2017 by Nicholas Baugh, we have been quietly building real email infrastructure while others chase venture capital.

What Makes Us Different

1. Built Everything From Scratch

Unlike every other email service that relies on third parties:

# What most "email startups" actually are: Amazon SES + React UI + VC funding = "Innovation" What we built:

Custom SMTP servers + IMAP/POP3 + CalDAV + CardDAV + Bare metal infrastructure + 100% open source

No third-party dependencies except DNS provider and datacenter. No third-party tracking tools, analytics, or external logging services - everything is in-house and completely open source.

2. Bare Metal Infrastructure

As of February 2025, we run on custom, performance-focused, bare-metal hardware 和数据包 as our primary data center provider.

Not cloud-based glue code. Actual servers running actual email infrastructure.

3. 100% Open Source (Frontend AND Backend)

Unlike Proton Mail and Tutanota who only open-source their frontends, our entire codebase is open source - including the backend that actually processes your emails.

The Legacy Infrastructure Problem: Proton Mail uses Postfix under the hood, a legacy C-based mail server that:

Hard to maintain: Requires deep C programming knowledge
Difficult to contribute to: Complex codebase with decades of technical debt
Requires extensive glue code: Connecting 1980s C code to modern HTML/JS/CSS web interfaces
Not web-native: Built for a different era of computing

Our Modern Approach: 100% JavaScript stack means:

Easy to maintain: Single language across the entire stack
Easy to contribute to: Modern, readable codebase that web developers understand
No glue code needed: Native integration between backend and frontend
Web-native: Built specifically for the modern web era

[!IMPORTANT] 可验证的隐私: You can inspect every line of code that handles your emails. Read their technical approach.

4. Individual Encrypted SQLite Files

Instead of shared databases (where one breach = everyone's data), we use individually encrypted SQLite files for each mailbox:

// Traditional email providers: MongoDB/PostgreSQL with shared access = security nightmare

// Our approach: Each mailbox = separate encrypted SQLite file Access to one ≠ access to all

5. Self-Hostable

We offer a complete self-hosted solution with Docker containers for:

管理 Web 界面
用于出站电子邮件的 SMTP 服务器
用于电子邮件检索的 IMAP/POP3 服务器
CalDAV 日历服务器
用于联系人的 CardDAV 服务器
配置存储数据库
Redis 用于缓存和性能

You're never locked in. You can run the entire stack yourself.

6. Features Users Actually Requested

Unlike failed startups that build features nobody wants, we listen to users and build what they specifically ask for:

DNS-Only Operation: Can run completely on DNS without requiring account creation
设计隐私: Ability to hide forwarding destinations is built-in, not an add-on feature
User-Requested PGP Encryption: Email forwarding WITH PGP encryption, adhering to OpenWKD standards
Standards Compliance: Built on proven email protocols, not proprietary solutions

The Technical Timeline

Our development shows what actual email infrastructure development looks like:

2017: Founded, built initial email forwarding with 634 lines of JavaScript
2018: Integrated with Cloudflare for privacy-first DNS
2019: Major performance rewrite using Node.js streams
2020: Released Spam Scanner (open-source anti-spam), 2FA, API
2021: Removed all Python dependencies, 100% JavaScript/Node.js stack
2023: Switched to bare metal servers, implemented DNS over HTTPS
2023: Launched outbound SMTP with built-in deliverability safeguards
2023: Added encrypted mailbox storage with IMAP support
2024: Added CalDAV, iOS Push support, time-to-inbox monitoring
2025: Switched to DataPacket bare metal infrastructure

Full timeline with sources

Technical Documentation: For comprehensive details on our approach, architecture, and security implementation, see our technical whitepaper and extensive technical documentation:

Why We Succeed Where Others Fail

✅ Solves Real Problems

Email forwarding for custom domains
Privacy-focused infrastructure
Reliable SMTP delivery
Standards-compliant protocols

✅ Uses Proven Technology

Built on email standards (SMTP, IMAP, POP3)
Uses battle-tested protocols
No proprietary lock-in

✅ Sustainable Business Model

Profitable since early days
Transparent pricing
No acquisition pressure

✅ Technical Excellence

Quantum-safe encryption
Individual encrypted mailboxes
Bare metal performance
100% open source

The Cost Reality Check

Self-hosting email (what Forward Email makes possible):

Server costs: $5-$50/month
Time investment: 5-10 hours/month maintenance
Technical expertise: Significant learning curve
Total cost: $56-$252/month (including time valuation)

Our managed service：每月 3 至 9 美元

Failed email startups: $14.2M+ in funding → shutdown

[!NOTE] We prove you can build sustainable email infrastructure without burning venture capital or shutting down users' services.

Conclusion: Stop Building Email Apps

The Evidence Is Overwhelming

80%+ failure rate in major accelerators
Acquisition-to-shutdown pattern across all major "successes"
Technical problems from trying to rebuild proven infrastructure
User abandonment when services inevitably shut down

The Historical Context

For deeper insight into the early days of email companies like Gmail, Yahoo, and Hotmail, Paul Graham's "Founders at Work" provides invaluable historical context about what actually worked in email's formative years. Our founder was greatly inspired by this book in the early days of his career, learning from the successes and failures of email pioneers.

The Real Lesson

Email is a solved problem. The protocol works. The infrastructure exists. The clients are good enough.

If you want to build something email-related:

Build infrastructure tools (like SendGrid)
Build integrations that work with existing email
Build specialized tools for specific use cases
Don't build another email client

The Extended Email Graveyard: More Failures and Shutdowns

Google's Email Experiments Gone Wrong

Google Buzz (2010-2011)

The Promise: Social networking integrated into Gmail to compete with Facebook and Twitter.

The Reality:

Privacy Disaster: Automatically exposed users' contacts and email patterns without consent
User Backlash: FTC complaint over privacy violations
Quick Death: Shut down after just 20 months in October 2011

[!WARNING] The Lesson: Even Google with infinite resources can't force social features into email. Users want email to be email, not a social network.

Google Wave (2009-2010)

The Promise: "Real-time communication platform to replace email" combining email, instant messaging, and collaboration.

The Reality:

Too Complex: Users couldn't understand what it was supposed to do
No Clear Use Case: Marketed as "better email" instead of collaboration tool
Developer Abandonment: Shut down after just 1 year in August 2010

Quote from Museum of Failure: "Wave was supposed to be the ultimate communication tool. It was to replace email for better collaboration" - but nobody wanted email replaced.

Inbox by Gmail (2014-2019)

The Promise: Experimental email client with smart features to reimagine email organization.

The Success: Actually worked well and had devoted users who loved the interface.

The Problem: Google couldn't maintain two email products and chose to focus on Gmail instead.

The Death: Discontinued in April 2019 despite user protests.

[!NOTE] The Irony: Inbox by Gmail was one of the few email "innovations" that actually worked - and Google still killed it. This shows that even successful email products can't survive corporate priorities.

The Serial Failure: Newton Mail's Three Deaths

Newton Mail (originally CloudMagic) holds the record for most deaths and resurrections:

Death #1 (August 2018)

Original shutdown announced due to unsustainable business model
Users had 2 weeks to migrate

Resurrection #1 (February 2019)

Essential acquired Newton and brought it back
Promised continued development

Death #2 (February 2020)

Essential shut down, taking Newton with it
Users abandoned again

Resurrection #2 (May 2020)

Superfans acquired Newton and reopened it
Community-driven effort

Death #3 (July 2024)

Final shutdown announced on July 31st, 2024
"Been in a downward spiral" according to users

The Pattern: Even beloved email apps with dedicated users can't sustain themselves. Newton's multiple deaths prove that loving users ≠ viable business.

The Apps That Never Launched

.mail (2010)

The Concept: Email app designed in 2010 by designer Tobias van Schneider.

The Reality: Never launched. The designer later wrote: "DotMail was an email app concept I originally came up with and designed in 2010" but it remained just a concept.

The Lesson: Sometimes the smartest move is not launching at all. The email graveyard is full of apps that should have stayed concepts.

The Acquisition-to-Shutdown Pattern

Astro (2016-2018)

The Product: AI-powered email client with smart scheduling and organization.

The Acquisition: Slack acquired Astro in September 2018 for talent and technology.

The Shutdown: Apps stopped working October 10th, 2018 - just 16 days after acquisition announcement.

User Reaction: "What's the best mail client now?" - users scrambling for alternatives with 2 weeks notice.

Email Infrastructure Consolidation

The email infrastructure space has seen massive consolidation, often leading to service degradation:

PostX → IronPort → Cisco (2006-2007)

PostX: Email encryption software provider
Acquired by IronPort: November 2006 for undisclosed amount
IronPort acquired by Cisco: January 2007 for $830M
Result: PostX technology absorbed into Cisco's enterprise security suite

2ergo → SoundBite → Genesys (2012-2013)

2ergo Americas: Mobile marketing and SMS platform
Acquired by SoundBite: February 2012 for $3.8M
SoundBite acquired by Genesys: May 2013 for $100M
Result: 2ergo's email/SMS technology integrated into enterprise communications

Newoldstamp → BlackPearl Group (2022)

Newoldstamp: Email signature marketing platform
Acquired: November 2022 for $3.1M
地位: Still operating but now part of larger data-driven products portfolio

[!IMPORTANT] The Consolidation Pattern: Email infrastructure companies get acquired not for their innovation, but for their user base and technology to be absorbed into larger platforms. Independent email innovation dies in corporate integration.

The Open-Source Email Graveyard: When "Free" Isn't Sustainable

Even open-source email projects, supposedly immune to venture capital pressures, follow the same failure patterns as commercial startups.

Nylas Mail → Mailspring: The Fork That Couldn't

Nylas Mail (2014-2017)

The Promise: Open-source desktop email client built with Electron, React, and Flux.

The Success: Actually gained traction with developers who loved the extensible architecture.

The Death: Discontinued September 6, 2017 when Nylas pivoted to focus on their API business.

The Quote: "We're committed to ensuring Nylas Mail lives on as open source" - Nylas team, before abandoning it completely.

Mailspring (2017-Present)

The Fork: Community fork of Nylas Mail attempting to continue development.

The Problems:

Abandoned Infrastructure: "Mailspring is unfortunately abandoned project, and their infrastructure is falling apart" - GitHub Issue #2231
Persistent Sync Issues: "Dreaded 'One or more accounts are having connection issues'" - daily problem for users
Email Loss: "Multiple reports of emails and drafts going missing from folders" - Mailspring Community

The Reality: Even successful open-source projects can't survive when the underlying infrastructure becomes unmaintained.

Eudora: The 18-Year Death March

The Legacy: Discontinued by Qualcomm in 2006, but users refused to let it die.

The Zombie State: "We Eudora v7.x email enthusiasts have been nursing along this unsupported email client for 18 years" - WorldCAD Access, May 2025.

The Community Effort: HERMES eudoramail 8.0 crowdfunding campaign attempting to revive a 20-year-old codebase.

The Lesson: Sometimes the kindest thing is to let dead software stay dead.

FairEmail: Killed by Google Play Politics

The Product: Fully featured, open source, privacy-focused Android email client.

The Death: Developer pulled all apps from Google Play in May 2022 after Google falsely flagged it as spyware.

The Controversy: "The problem here is the app was deceptively processing contact lists without user consent" vs "Google requires FairEmail to undergo an annual CASA security audit".

User Reaction: "Fairemail discontinued - Looking for new email app?" - Android Central Forums.

[!WARNING] The Platform Risk: Even open-source projects are vulnerable to platform gatekeepers. Google's arbitrary enforcement can kill years of development overnight.

The Maintenance Problem

PHPMailer: Still maintained but legacy versions (5.2) no longer supported, even for security updates.

Claws Mail: Active development continues but with a tiny contributor base and aging codebase.

The Pattern: Open-source email projects either die from lack of funding or become maintenance burdens that few developers want to touch.

The AI Email Startup Surge: History Repeating with "Intelligence"

The latest wave of email startups has discovered the magic buzzword: AI. Spoiler alert: Adding artificial intelligence to email doesn't solve the fundamental problem that email already works perfectly.

The Current AI Email Gold Rush

AI Email Assistants

Lavender: "Your Magical AI Email Coach" - scores emails and gives AI feedback
Shortwave: "Agentic AI that helps you organize, write, search, schedule"
Superhuman: "AI-native email" with $33M+ funding
WriteMail.ai: "Write professional, engaging emails in seconds"
Mail-0/Zero: AI-powered email client startup building yet another email interface
Inbox Zero: Open-source AI email assistant attempting to automate email management

AI Cold Email Platforms

Reply.io: "AI Sales Outreach & Cold Email Platform"
Mails.ai: "AI Cold Email Software"
Smartlead: "Running Personalized Cold Outreach"
Instantly.ai: "Multichannel campaigns" with AI

AI Email Organization

Fyxer AI: "Save 1 hour every day with an AI assistant"

The Funding Frenzy

The Numbers: According to Crunchbase, $100B of venture capital went to AI startups in 2024, representing an 80% increase from 2023.

Y Combinator AI Obsession: Browse 100 of the top AI startups funded by Y Combinator - many focused on email and communication.

Recent Examples:

Skarbe: AI sales assistant secured $600K pre-seed (12 hours ago)
heyLibby: AI assistant for small businesses raised $4.5M seed (April 2025)
Martin AI: Yale and Berkeley dropouts raised $2M to build AI assistant (January 2025)

Why They'll All Fail (Again)

The Same Old Problems with AI Lipstick

Memory Bloat: AI models require massive resources. These apps will consume even more RAM than the Electron disasters.

Privacy Concerns: AI email assistants need to read your emails to "help" you. Users will revolt when they realize the privacy implications.

Accuracy Issues: AI hallucinations in email could be catastrophic. One wrong AI-generated response could destroy business relationships.

Cost Structure: Running AI inference for every email interaction is expensive. These startups will burn through funding faster than traditional email apps.

The Fundamental Misunderstanding

[!IMPORTANT] The Core Problem: Email doesn't need artificial intelligence. It needs reliability, speed, and standards compliance. Adding AI to email is like adding AI to a hammer - it solves no real problem while creating new ones.

Historical Parallel: Just like the 2010s wave of "social email" (Google Buzz, Google Wave), the 2020s wave of "AI email" misunderstands what users actually want from email.

The Inevitable Outcome

Prediction: Within 3-5 years, we'll see:

90%+ of AI email startups will shut down or be acquired for talent
The survivors will quietly remove AI features and become regular email apps
New buzzword will emerge (probably "quantum email" or "blockchain email") to restart the cycle

The Pattern: Email startup failures follow technology hype cycles. We've seen "social email," "mobile-first email," "collaborative email," and now "AI email." The underlying problem remains: email already works.

The Consolidation Catastrophe: When "Survivors" Become Disasters

Even the email services that "survived" the startup graveyard have become cautionary tales through endless acquisitions and mergers.

The Great Email Service Consolidation

AOL Mail + Yahoo Mail: The Verizon Disaster (2015-2021)

The Acquisitions:

AOL: Verizon acquired for $4.4 billion in 2015
Yahoo: Verizon acquired for $4.5 billion in 2017

The Failure: Verizon sold both to Apollo for $5 billion in 2021 - losing $4 billion on the combined investment.

User Impact: Both services became neglected stepchildren during Verizon ownership, with minimal investment in infrastructure or features.

Hotmail → Outlook: The Microsoft Mess (1997-Present)

The Acquisition: Microsoft acquired Hotmail in 1997 for $400M - the largest all-cash Internet startup deal of its era.

The Problem: Microsoft has spent 27 years trying to merge Hotmail into Outlook, and it still doesn't work properly.

User Frustration:

"It's not possible to merge or combine Microsoft accounts" - Microsoft Support, November 2023
"HOTMAIL AND OUTLOOK ACCOUNT MERGE TURNED INTO A NIGHTMARE" - Microsoft Community

Outlook: The "Survivor" That Can't Stop Breaking

Persistent Technical Issues

2024 Problems:

Reddit Reality Check: "'New Outlook' is a mess" - r/Windows11, April 2024.

Our Real-World Experience with Outlook

Our codebase reveals the ongoing nightmare of Outlook compatibility through actual code comments and fixes:

Microsoft's Arbitrary Spam Detection:

// Microsoft has an issue where they block emails from new IP addresses
// and there's no way to get them unblocked without going through their
// manual review process which can take weeks or months
// <https://github.com/forwardemail/forwardemail.net/blob/73a05c8a0e1b02e6dad40a35d7d130a42effb364/config/index.js#L502-L506>

Outlook-Specific Email Handling:

// Outlook has issues with certain email headers and formatting
// so we need to handle them differently than other providers
// <https://github.com/forwardemail/forwardemail.net/blob/73a05c8a0e1b02e6dad40a35d7d130a42effb364/helpers/on-data-mx.js#L116-L121>

Unprecedented Spam from Outlook:

// We had to implement specific filtering for Outlook.com domains
// due to unprecedented amounts of spam originating from their platform
// Despite multiple complaints to their abuse team, we received zero response
// This required implementing custom detection patterns specifically for Outlook spam
// <https://github.com/forwardemail/forwardemail.net/blob/73a05c8a0e1b02e6dad40a35d7d130a42effb364/helpers/is-arbitrary.js#L187-L207>

The Complexity Problem: Outlook requires 2FA for simple IMAP access, then requires app passwords, but even then is buggy since proper IMAP with Outlook requires OAuth2. It's overtly complex and creates unnecessary frustration for users who just want their email to work.

The Postmark Infrastructure Problem

We also experienced firsthand how email infrastructure degrades after acquisition. 邮戳, originally owned by Wildbit and beloved by developers, was acquired by ActiveCampaign in May 2022.

The Problem: We had to temporarily block Postmark due to:

DKIM Replay Attacks: Postmark wasn't preventing DKIM replay attacks properly
Poor KYC Process: Allowing anyone to signup without proper verification
IP Reputation Damage: Thousands of spam emails damaging their delivery reputation

This issue took months to resolve and demonstrates how even "reliable" email infrastructure can become problematic after corporate acquisition.

Recent Email Client Casualties (2024-2025)

The email client graveyard continues to grow with recent high-profile shutdowns:

Postbox: After 16 years of development, acquired and immediately shut down by eM Client in October 2024. Support ended December 22, 2024.

Email Client Funding Continues:

Canary Mail: Backed by Sequoia Capital's Surge program with $2M+ funding, yet users report features don't work and subscriptions can't be refunded
Spark by Readdle: Despite being part of a successful app company, users report "nightmarish experience" and lack of responsiveness
Mailbird: Windows email client that users say "turned into a terrible company, which doesn't honor the licenses"
Airmail: Mac/iOS email client by Italian company Bloop SRL, originally based on the failed Sparrow client

Email Extension and Service Acquisitions

Recent Acquisitions That Actually Worked:

ToutApp: Acquired by Marketo in April 2017 after raising $15M+ in funding
Bananatag: Email tracking startup acquired by Staffbase in 2021 and rebranded as "Staffbase Email"

Discontinued Extensions:

HubSpot Sidekick: Popular Gmail extension discontinued in 2016 and replaced with "HubSpot Sales"
Engage for Gmail: Salesforce extension retired in June 2024 due to Google's Manifest V2 deprecation

The Survivors: Email Companies That Actually Work

Successful Email Startups (proving the exception, not the rule):

Mailmodo: Y Combinator company that raised $2M from Sequoia's Surge in 2021 for interactive AMP emails
Mixmax: Raised $13.3M total funding and remains active as a sales engagement platform
Outreach.io: Valued at $1.33B+ with $351M+ raised, preparing for potential IPO
Apollo.io: Reached $1.6B valuation with $100M Series D in 2023
GMass: Bootstrap success story generating $140K/month as a Gmail extension
Streak CRM: Raised $1.9M in 2012 and continues as a successful Gmail-based CRM

Key Pattern: The survivors either enhance existing email workflows (like Streak, GMass) or serve specific business needs (like Outreach, Apollo) rather than trying to replace email entirely.

The Cycle:

Acquire promising email service for billions
Neglect infrastructure and development
Merge into existing platform (badly)
Break functionality that previously worked
Blame users for "configuration issues"

The Result: Email services that were once reliable become unreliable through corporate mismanagement, proving that acquisition often equals death - just slower and more painful.