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A Postmortem of a Startup

A Postmortem of a Startup

127 comments

·April 16, 2025

shalmanese

When I coach startup founders, I walk them through a very simple 4 step process when we meet:

1. What have you learnt since we last met and how has that altered your priors?

2. What do you now believe is the most important problem you should be solving?

3. What's currently blocking you from solving that problem?

4. How do we overcome those blocks?

Crucial to this process is that Q1 is not what have you done, it's what have you learnt. I do not give a shit about anything you've done if it's not in the service of learning.

I also run a retro every 3 months with founders where we ask the following questions:

1. What would you want to tell yourself 3/6/12 months ago (essentially, all the lessons learnt in italics) to save the maximum amount of pain?

2. When did you learn each specific thing?

3. When was the earliest you could have learnt that thing?

4. What changes can we make going forward to minimize that delta?

Extremely simple things but extraordinarily powerful when applied consistently over a long enough span of time.

hermitShell

Do you steer them away from ‘bad ideas’? Trying to recall pg’s essay, which was admitted sw focused, but the core idea is both worthless on the open market and essential to the ultimate success. Is this coaching ‘don’t become a statistic’ or ‘better luck next time’

shalmanese

Whatever my private opinion of the idea, that they're pursuing it means they believe it. It's about getting whatever information fast enough to evaluate whether it truly is a bad idea or not.

Startups are contrarian, many of the most successful ones are the ones "experts" are convinced are bad. I think in terms of the retrospective, assume we're at the point where the startup has shut down and the post-mortem is done and the reason was because it was a bad idea, how do we get there as fast as possible so there's time to pivot.

mrweiner

Thank you — the way you frame this is helpful.

monkeydust

This is good especially 1. bit of Bayesian thinking thrown in.

I find a lot of founders ask for feedback, advice and just carry on doing what they were going to do anyway, perhaps convince themselves that the advice backs up their thinking when it doesn't. Not everyone of course but a lot, hence why I like your question.

shalmanese

I think the linked tweet from the article explains it better than I could:

> The more time I spend advising founders, the clearer it gets that 80% of my value is repeating "don't die, don't lie to yourself"

https://x.com/_ArnaudS_/status/1805638715739619679

morsecodist

This is interesting and they make some good observations but I can't help but think the deck was stacked against them because they are trying to come up with a technical/business solution to what is fundamentally a political problem.

OccamsMirror

Yeah "founded to build software to fix Britain’s housing crisis."

There was literally zero hope for success.

hinkley

I know of an ISP that wrote a custom CRM/ERP solution in order to harass the less well behaved telecom company in town into doing their jobs when they said they would do them. So it would do things like send you a reminder to see if the approval or the hookup they promised you Wednesday was done so you could meet you customer’s expectation of having their Internet turned on by Friday.

That’s probably the best you can do. Make it obvious to everyone including the bureaucracy what their externalities are doing, and either nudge them to go faster or divest some responsibilities to someone else.

mytailorisrich

Planning permission is partly a political issue, partly down to expertise. You need experience, you need to know the rules, you need to know the tricks, you need to know how to draft the application. You need to know the game. Indeed this is not something that is waiting for a technical solution.

It's great that they tried, though. But it strikes me that they seem to be 20 something students (not meant disparagingly) with no experience in this so perhaps lacked the insights and understanding of the pain points. It does seem that VCs were happy to fund based on an AI play, though ;)

hinkley

My ex worked at a government contractor and they started paying the guy who wrote grant proposals more than the CEO because without grants they were fucked, and the grant writer was getting wistful for other horizons.

Talking to government is a highly compensated skill set. That’s all lobbyists are.

dccoolgai

Bingo, and most engineers have zero clue or respect for this skillset. Even traditional PMs / business dev types don't know what they don't know about how to talk with government or government-adjacent businesses. I've worked for at least 3 companies who had high hopes for building on state/municipal/higher-ed revenue and talked it up in their internal meetings, but when you would ask the CEO/CFO where their government affairs team was, they would look at you like you were speaking Latin. They basically just planned to take their consumer sales motion and apply it to these areas, which fails hilariously almost every time.

trelane

That is a lot of what to know.

I don't doubt that at least as important is who you know, and especially how well they know you.

mike_hearn

They say that in the article where they talk about social technology and the importance of drinking in pubs.

gopher_space

The deck was stacked against them because nobody understood why the conversion process was so expensive or even there in the first place. It would have been easier to identify the handful of organizations that'd benefit from labeling this a political problem and embed themselves as vendors.

Their business model made sense for America, where sprawl is embraced.

AJRF

Thanks for writing this!

> Housing in Britain is expensive because getting planning permission is difficult.

Isn't the real problem that supply is artificially constrained because house prices and the economy are interlinked in a way in a special way in the UK economy, such that the majority of home owners don't want it changed (because more supply == downward pricing pressure)

I think the only entity that could meaningfully change this situation is government, and well it's easier to not upset your donors.

Edit: To be fair to the author, they do mention artificial supply constraints but I think my point stands - it is there by design, too much inertia forcing it to be that way that won't be changed by streamlining the bureaucratic elements

AJRF

NIMBYism is not unique, but the importance of house prices to the UK economy is more severe than other countries.

- The UK has a very strong household wealth affect (consumption is tied to house price growth / decline). The US and UK borrowers borrow at a rate against household wealth not seen in other nations (look at the chart on page 6 - https://www.ecb.europa.eu/pub/pdf/scpwps/ecbwp1117.pdf)

- It has had dramatic, sustained house price growth (400% real price growth since 1980) vs US (200%), France (200%), Germany (150%), Spain (Collapsed in 2008), Italy (Stagnant since 2008)

Some Links:

- https://www.bankofengland.co.uk/-/media/boe/files/working-pa...

- https://www.imf.org/en/Publications/CR/Issues/2016/12/31/Uni...

immibis

It's been said about the New Zealand economy that it mainly consists of five people trading houses with each other for ever bigger numbers.

mytailorisrich

Supply is somewhat constrained and demand is also artificially inflated (at national level it is 100% caused by immigration, which is kept high by the successive governments).

Everyone relies on the property market going up. Beyond the obvious reasons, another important one is that fixed rate mortgages are not fixed for the life of the mortgage but only for, usually, 2 to 5 years after which rates jump so everyone is continuously worried about remortgaging.

spacebanana7

It's curious to think about what house prices in the UK would be like without immigration.

With a sustained negative fertility rate over the past few decades, there could've feasibly been stable prices with no new houses built at all.

mytailorisrich

The UK population would have started to decrease naturally I believe around 2024 without immigration. It so happens that the past few years have also seen record high immigration and population growth...

Obviously the property market would be looking very differently if population was decreasing. The whole economy would.

n4r9

Well, house prices outside of London have increased roughly in line with inflation over the last couple of decades.

ONS data states that the average house price outside of London and the South East rose from £134k in 2005 to £192k in 2019 [0].

The Bank of England's inflation calculator states that £192k in 2019 costs £139k in 2005 [1].

Looking at London specifically, house prices more than doubled from £303k to £684k over the same period [2]. That's a 63% increase in real terms. Immigration would have some effect on this, but so would UK citizens moving to London or foreign nationals buying up property as an investment.

[0] https://www.ons.gov.uk/economy/inflationandpriceindices/adho...

[1] https://www.bankofengland.co.uk/monetary-policy/inflation/in...

[2] https://www.home.co.uk/guides/house_prices_report.htm?locati...

pyb

It's true that the general public have a revealed preference for the housing crisis to continue forever.

However in principle, as with many social issues, a motivated actor such as a startup could still have a chance of fixing it.

lalaithion

One of the ways in which supply is artificially restricted is that getting planning permission is difficult, so you’re not actually disagreeing with OP

kijin

It looks like this startup tried to hack the system by streamlining one of the key mechanisms of artificial constraint: the difficulty of getting permits.

Not a fundamental cure, of course, but it sounds like a promising hack to squeeze out a few more building permits than would otherwise have been issued.

rob74

I agree with you that that's probably the real problem, but not that the situation is unique to Britain (although maybe it's worse in Britain then elsewhere)...

Destiner

I think you're describing NIMBY, which is more of a US/SF thing (but also is a case in Europe to some extent).

zihotki

NIMBY is an universal human concept, it's present everywhere - Europe, Asia, South America. It may come in different flavours but it's everywhere. People don't welcome changes to the surrounding environment if it doesn't benefit them more or less directly.

amy214

It's one of those things like littering or tragedy of the commons - one instance, by itself, is not a big deal so it's understandable why people might not think much of NIMBYing. But en masse these behaviors are ruinous

nemomarx

is that a very special thing? it seems like that in the US too imo

clpm4j

If a government truly wanted to fix a housing "crisis", wouldn't a ban on any type of corporate entity from buying single-family homes be an efficient solution? E.g., LLC's can no longer purchase single-family homes. Only real, live human individuals can purchase single-family homes. They could also try to implement some type of ban on any single individual person from purchasing more than 1 (or choose a number) single-family home.

ketzo

Depends on whether you think renting a home is a way to solve the housing crisis.

If your definition of “solved housing crisis” is “everyone can buy a home,” a ban on corporate ownership could help a little.

If your goal is instead “everyone has a place to live,” no, corporate ownership is not inherently problematic.

poulsbohemian

I am a realtor and sit on my state's realtor association legislative steering committee, which this year sough to work with legislators on a bill that would limit mass corporate control over housing units... it's surprisingly more complicated than it first appears, and an area where realtors take a view that might be contrary to consumer expectations - we generally like the idea of limitations on corporate ownership, as it in theory creates the greatest opportunity for individual homeownership...

Anyway, some of the scenarios we ran into are things like the 2008 mortgage crisis - what happens if you end up in a market where there is a lot of inventory that no one can afford to hold? In my market, it's starting to look like a lot of builders (read: corporations) built too many houses either that weren't what consumers wanted or demand has shrunk (it is a town with a lot of federal jobs that are evaporating at the moment...). So can a builder hold that inventory indefinitely (assuming they can afford that) as a corporation? Likewise, people often don't want to hear this, but landlords do create efficiencies in the market - there are people out there that either don't want to own a home or can't qualify for a mortgage, and a landlord makes it possible to provide housing for those people as a kind of intermediary. We can argue over what it takes to qualify for a mortgage, but that's really a separate issue. We of course get into the issue of vacation homes or even situations like can I as an individual own a place for my business and a home - after all, they are both real estate, so how tight can we make these rules around ownership? Point being - the basic idea is sound, and some states like CA apparently already have laws on the books, but it's a more complicated matter than just one person == one house.

socalgal2

Why would that be a solution? What's the difference between the LLC that buys a bunch of homes and the LLC the builds bunch of homes. When the homes are done being built the LLC has morphed from an LLC that builds homes to an LLC that bought a bunch of homes.

The solution to me is to stop preventing people and companies from building homes.

https://www.youtube.com/watch?v=cjWs7dqaWfY

Effectively, goverments and nimbyism prevent houses from being built. Even when some laws change to supposedly allow it other laws continue to prevent it. It's got nothing to do with LLCs buying existing houses, it's got to do with not enough houses period.

clpm4j

The solution lies in eliminating the entire concept of investment properties, and to classify single-homes as purely places to live. You do realize that part of "not enough" houses is due to corporate entities / investment vehicles / investors owning many properties.

And the types of cities (dense, highly-desirable urban cities like SF, London, Paris) where the NIMBY people complain most often also happen to be the most common markets for these investors to purchase/own multiple homes.

morsecodist

I agree that the core problem of housing affordability is that housing serves a dual role as an investment and a place to live. But I think this policy will not do very much and in isolation would even be counterproductive.

Why focus on single family homes? If corporate ownership is as bad as you are framing it then why is it OK for someone who lives in an apartment to be advantage of? Worse still, these entities would still want to invest in real estate so presumably they would invest even more in multi-family properties. If their ownership is what causes unaffordability, are you not making things even worse for people who live in multi-family housing?

DrBazza

One cause of the UK's 'housing crisis' (or rather un-affordability), just like other countries I suppose, is simply that if I buy other properties, I get: capital appreciation on the asset, and return on investment (by renting it out).

Offer me a £500k passive investment that makes the same returns with the same guarantees, and I'll take that over a house.

Except they don't. No other investment comes close for the British middle classes with that sort of extra cash. And the UK government will tax you to the hilt on everything else.

Exacerbating the problem, is that you can get a bank loan for additional properties.

antisthenes

The solution to the housing crisis is letting people build "not quite up to code" structures and relaxing zoning.

This means heavy handedly forcing local municipalities to change zoning.

A lot of people don't like that.

DrBazza

Zoning is a US thing. The article refers to the UK housing problem and we don't really have that problem, but I suppose that might fix the US market.

UK houses are a good investment, in fact the best investment for £500k, and also their price is additionally inflated by 'cheap money' and dual incomes.

Can't quite afford that house that's current 'under offer' at £500k? You might be able to find a bank that will lend you just that little bit more. 5.5x your salary? No problem. Congratulations, the bank has just helped push house prices that little bit higher. In the UK in the 1970s the single income 3x mortgage multiplier was on its last legs. Now it's 4+ times your joint salary. Madness.

dukeyukey

Why would that solve a housing crisis? Functionally making it impossible to rent a SFH seems like a dick move.

philipallstar

> Housing in Britain is expensive because getting planning permission is difficult.

It's true that planning departments are very expensive, don't do much positively, and still seem to allow awful-looking things to be built, and I'd probably happily do away with them, but the fundamental driver is the incredible onboarding of people from overseas for years that crushes the combination of the existing population and the new people into a number of dwellings that isn't that dissimilar to the previous year.

You can't take on a net number of people each year that would require a new city the size of Nottingham to be built to accommodate, and say "well, it's all the planning process' fault."

froddd

Reducing the problem to ‘people coming from overseas’ is an equally reductionist argument.

There are properties going unused, for very many reasons. Second homes, holiday homes, etc. This also drives the price of properties up. This is one of the inputs to the problem. Planning permission laws is another input. The size and change of size of the people needing housing is another input.

spacebanana7

Is it not the dominant factor, at least in the short term? It's much faster for 150k people to enter/leave the UK than for a corresponding number of homes to built/demolished.

macrocosmos

It’s obviously the dominant factor to anyone with the eyes to see it.

chippiewill

It does, but occupancy rates in the UK are already incredibly high compared to countries like France.

There are simply too many people and not enough houses.

matt-p

reductionist in this case is not a bad thing. We need a major change to fix this situation and doing some little tweaks like increasing taxes on second homes or holiday homes does not actually fix this (we already tax those specific cases, with things like second home stamp duty or in some areas second home council tax).

You have

A - Demand (immigration of 1 Million per year)

Or

B - Supply (building only 120,000 houses per year)

We MUST fix one or both of these sides of the equation. Holiday homes aren't going to add up to a row of beans quite frankly (and will have very negative effects on the tourism industry, not so bad in London - but might be quite an impact in cornwall for example).

froddd

Holiday homes have quite the impact in many parts of Wales.

Occupancy ratings per house seem to be quite low on average [1], but weirdly I can’t seem to find any figures for overall occupancy.

[1] https://www.ons.gov.uk/peoplepopulationandcommunity/housing/...

Edit: clarification

mattmanser

The people have been saying pretty clearly for 20 years that they want A fixed.

But the politicians just ignore that for "growth" and keep granting 100,000+s of visas and then blame asylum seekers.

And then complain that there's mysteriously low productivity in the UK.

mattmanser

Nottingham city, the pure "legal" definition, is actually quite small and not what most people think of when you say "Nottingham".

For example, it doesn't include Beeston, West Bridgford, Stapleford, Clifton, Ilkeston, Arnold, Long Eaton, Hucknall and more.

Even though no outsider could draw a line where Nottingham city stops and most of them start.

djoldman

I looked for a source for this statement in the article:

> Granting permission takes the median hectare of land from £20,000 to £2.4 million - a 139x uplift.

I couldn't find one. However, I did run into some interesting viewpoints by a certain Paul Cheshire, Professor Emeritus of Economic Geography at the London School of Economics... "one of the world’s pre-eminent housing economists"

He has this to say about "Green Belts":

> Britain imposed its first Green Belt in 1955 and now, if re-zoned for building, farmland at the built edge of London has an 800-fold mark-up. There was no secular trend in housing land prices in Britain until the mid-1950s, but after Green Belts were imposed real prices increased some 15-fold. More than houses because you can substitute land out of house production. There is a similar pattern in Canada, New Zealand or the West and East coasts of the United States where policies restrict land supply.

https://www.newgeography.com/content/006358-lse-economist-pa...

gnfargbl

> I couldn't find one.

A parliamentary publication from 2018 estimated the uplift factor to be 93x outside London and 287x inside [1]. Found via ChatGPT.

I would think that the north-south variation has flattened a little bit by now, but I can't immediately find any similar document from the last couple of years.

[1] https://assets.publishing.service.gov.uk/government/uploads/..., page 12.

[2] https://www.progressive-policy.net/publications/gathering-th...

matt-p

I have not researched this but someone I know at one of the big house-builders pegged the cost of building a 3 bed at around £35-40,000, so in the south east land with PP is 10X more valuable than what's sat on it.

"Farm" land, even in the SE is about 12K an acre, and you get 6-8 houses to the acre so you should be able build a three bed and sell it for £50K on the outskirts of London, Cambridge, Oxford or Brighton (just by example) still making a profit if we liberalised planning in those areas. That shows you how extreme this situation of fake constraint is.

It could therefore never be allowed to happen. The big house-builders wouldn't build and sell at that price, the locals wouldn't allow it as they've bought their houses for 500K, 10X as much and would literally all go personally bankrupt...

ejsdev

I wrote something similar to this last year - it was an incredibly cathartic writing experience. It's extremely weird to realise that you're hung up on a business venture from years before, but made a lot of sense.

FWIW I am never doing a 3-way marketplace again, hellish.

If anyone is interested - https://edjs.dev/blog/my-first-startup/

dzonga

well written. I think your fatal mistake even though you folks are smart was not understanding the complete value chain of your business.

What I mean by understanding the economics of the value chain is you've to understand how your customers make money, how their customers make money & how their suppliers make money. From there - you can workout your value proposition - are you saving your customers money (means there's a cap on how much value you can extract) or are you allowing your customers to make more money (how much value you can extract is kinda uncapped - depending on mechanics)

The other mistake - which you correctly kinda alluded to is not understanding the incentives / dynamics of the industry. UK land is tricky since most wealth / power is packed into UK land. hence your part about emotion etc.

final mistake was equating success to raising money. Profit, if not revenue growth is the only measure of success. Raising money is not.

immibis

Success is when you get paid. If the product is unprofitable, you lose out on a bunch more money, and your investors lose out on most of their money, but you did your job and got paid for that, and as long as it was a reasonable rate, what's the failure on your part?

Etheryte

I don't think the last paragraph is correct, many unicorns don't generate profit, yet are hugely successful by any other metric. In many cases, generating profit is actually undesirable for tax reasons.

mytailorisrich

Generating profit is highly desirable for any business.

For tax purpose you need to differentiate between "profit" and "taxable profit". You can try to lower your taxable profit to minimise tax, e.g. by re-investing your profits, but ultimately it is better to turn a profit and to have to pay some tax on it that to have an unprofitable business.

Etheryte

Not necessarily, this is a classic misunderstanding. As a famous example, Uber did not make a profit for 14 years, all the way up to 2023. For taxable profit it's even more severe, they've built up a considerable backlog of losses, so they'll pay very little in taxes for the foreseeable future, even though they're now profitable.

frankdejonge

I believe that why they said "if not revenue growth". Those successful, yet unprofitable companies do have revenue growth, or market share growth.

mleonhard

> We want to stress from the start that the ultimate failure of the company lies with us.

This statement discounts how much random chance contributes to success & failure. Could the world's best founding team find and build a successful business in that field? Maybe. And even if they could, is it failure to be less good than the best? Not at all.

> Stay lean until you have proven revenue.

They raised a pre-seed round and used it to search for business opportunities. This seems like the normal way of doing a startup.

> TIME AND MONEY SPENT ON NON-ESSENTIALS - These included an office, website and branding, a trip to America, contractors, and unnecessary employees.

Having an office can boost energy and productivity. Taking a trip to US to connect with new advisors, investors, and other founders seems like a pretty normal thing to do.

I think these founders are being too hard on themselves. They got an amazing education in entrepreneurship. They don't need to feel bad about it.

monkeydust

Nice writeup, wish more startups who didn't succeed did this though understand not easy thing to write so kudos.

One factor to success is timing, as someone who lives in UK around London and is seeing (slowly) greenbelt getting developed on perhaps the market might be moving towards you in the next 5 years.

ktallett

I would agree but I doubt it will become more of a thing, too many seem to not be willing to accept failure or show vunerability. This will always be rare in the start up market as long as bravado and fake it till you make it is still a thing, which it is.

pyb

A good question to ask before starting a startup is : "Do I see myself working 10 years on this problem?". Looks like they ran out of steam, rather than out of runway.

bad_username

Why 10 years? Is it not typical with startup founders to plan a lucrative exit in a much shorter time frame?

drdrek

7-10 years is the realistic time frame for a moderately successful exit, usually those that are "Bought" after 1-3 years are actually failed ventures with all or most of the money going back to the investors to recoup their loses.

_fat_santa

It seems high at first but take a look at practically any successful startup (Slack, Dropbox, Notion, etc) and they all were around for 8-12 years before the founders cashed out.

flessner

> "Good startups usually take 10 years." - Sam Altman

It also aligns with other Y Combinator teachings, such as targeting growing markets.

pyb

No, where did you get this idea? Good startups do not think this way.

kengoa

Very interesting read, I wish more startups did postmortems like this. It seems like the authors managed to build a set of tools that provided real value that ultimately did not make commercial sense, but would've been interesting to see if this learning:

> Scout was our most-used product. Its users weren’t our target market, but some were. We had vague ambitions to use it as an inbound marketing tool, but we never capitalised on it. This was a missed opportunity.

was applicable in a conservative industry like real estate and government as lots of open-core companies operate on this model (e.g. free open-source software and marked-up hosted solutions).