Founder Stories: Post-mortems
Showing 16 articles for Founder Stories: Post-mortems.
How Olivia Nuzzi processed public shame and personal failure
The Daily Stoic
December 13, 2025
Post-mortems
8
Resilience & grit
7
Mental health & wellbeing
5
- Big failures are the endpoint of many small, ignored compromises
- Shamelessness is now a survival strategy — and why she rejected it
- How a journalist's trained compartmentalizing made her personally blind
14 brutal lessons every first-time SaaS founder will face
TK Kader
September 14, 2025
Post-mortems
10
Resilience & grit
8
Cash flow management
6
- Every catastrophe you fear will probably happen — and you'll survive it.
- Hiding from customers is the single fastest way to kill product-market fit.
- Belief times discipline beats perfection; the veteran just keeps steering forward.
Shutting down Hello Query: a founder's honest account
Startups For the Rest of Us
March 13, 2025
Post-mortems
10
Prospecting & outreach
6
Growth hacking
5
- Why 'nerd famous' audiences give founders dangerously false buying signals
- Co-founder departure forced a full restart, costing years of progress
- Knowing when to quit: exhaustion plus stalled traction plus opportunity cost
How Google algorithm updates wiped out a $325K DIY blog business
Ahrefs
February 26, 2025
Post-mortems
9
SEO
8
Business models
5
- Google praised their site — then killed 75% of its traffic overnight
- Diversified revenue means nothing if every stream needs the same page views
- Digital products on a subdomain earned $1,500/month with near-zero traffic
How a Google Algorithm Update Wiped Out a $1M Retro Gaming Site
Ahrefs
January 15, 2025
Post-mortems
10
SEO
8
Pivoting
7
- Google update erased 85% of RetroDodo's traffic overnight.
- Redirecting rumour pages wasted high-authority backlinks from Verge, Wikipedia.
- Recovery pivots to books, physical products, email community, search consultancy.
Groupon's rise and fall, and Andrew Mason's second act with Descript
How I Built This with Guy Raz
September 9, 2024
Post-mortems
9
Pivoting
7
- Scarcity was the business model — clones destroyed it within two years.
- Mason turned down Google's $5B offer, then lost the company anyway.
- Descript was born from internal tooling built for a failing audio tour startup.
How a co-founder coup nearly destroyed a $100M food brand
EO
December 30, 2023
Post-mortems
9
Business models
6
- Minority shareholders staged a legal coup to oust the founding CEO
- Ownership stake does not equal operational authority — conflating them kills growth
- Misaligned vision on dividends vs. reinvestment breaks co-founder partnerships
Alistair Urquhart's WWII survival story as a mental reset tool
Founders
August 27, 2023
Post-mortems
9
Resilience & grit
8
Motivation
5
- A WWII POW's story as a tool for entrepreneur stress
- Surviving torture, hellships, and Nagasaki on sheer willpower
- Having something to live for is a measurable survival advantage
Lessons from losing to TikTok: product-market fit, humility, and team
EO
June 16, 2023
Post-mortems
10
Resilience & grit
7
Product-market fit
6
- Product-market fit means nothing when a rival buys the market.
- Admitting mistakes openly to your team builds trust, not weakness.
- Relationships outlast every startup outcome — protect them.
What a spam hack taught me about startup resilience
Rob Walling
June 4, 2023
Post-mortems
9
Crisis leadership
7
- Hackers exploited a missing account-disable feature to send phishing emails
- Blacklisted IPs can kill an email tool's core value overnight
- Most startup crises aren't fatal if you stay calm and lead
Julio Lobo: the rise and fall of Cuba's last sugar tycoon
Founders
March 16, 2022
Post-mortems
10
Pivoting
6
Resilience & grit
5
- Lobo financed Castro's rebels — who then confiscated his $200M fortune
- Speculation, not bad luck, destroyed every fortune he built
- Died poor on his daughters' allowance; funeral drew a handful of people
William Shockley: genius, poor people skills, squandered legacy
Founders
February 1, 2021
Post-mortems
9
Culture building
7
Management
5
- Shockley seeded Silicon Valley but never earned a dollar from it
- Refusing to take ideas from employees destroyed his company in 18 months
- The Traitorous Eight did the opposite of Shockley and built Intel
WeWork's collapse: from $47 billion unicorn to SoftBank bailout
Acquired
October 25, 2019
Post-mortems
9
Origin stories
7
Fundraising & VC
7
- How SoftBank's $100B fund turned WeWork's founder into an unchecked liability
- A profitable real estate business disguised as a technology company
- Adam Newman walked away with $700M+ while 14,000 employees lost their equity
Steve Jobs at NeXT: eight years of strategic failure and hard lessons
Founders
June 23, 2019
Post-mortems
9
Market research
8
Management
6
- Why $250 million and eight years produced zero net profit
- Too much money at founding kills urgency and financial discipline
- The right pivot — hardware to software — came from everyone but Jobs
How to shut down a startup with integrity: lessons from Poppy's founder
Y Combinator
January 30, 2019
Post-mortems
10
Pivoting
6
Unit economics
5
- Monthly investor updates made the shutdown conversation almost painless.
- Shutting down cleanly is a skill — and it can be done with integrity.
- Grief after closing a company is real; building in recovery time matters.