Tract Postmortem

Introduction

Between May 2023 and March 2025, Tract attempted to build a
venture-backed company to address Britain’s housing crisis by
improving the planning permission process. After raising a
£744,000 pre-seed round in April 2024, we explored several
business models: a site-sourcing tool for developers (Tract
Source), a free land-appraisal tool for landowners (Attract),
becoming tech-enabled land promoters ourselves, and finally, an
AI-powered platform to assist with drafting planning documents
(Tract Editor).

Despite significant technical progress, building tools like Scout
and the well-received Tract Editor, our journey taught us critical
lessons from failing to secure a viable, venture-scale business
model in the British property market. We learned the difficulty of
selling software into a conservative sector, experienced the
operational complexities and timelines of land promotion, and
encountered a low willingness to pay for useful tools.
Furthermore, we came to understand how the market’s conservatism
and fragmentation limited its potential for venture-backed
disruption. After nearly two years without revenue or committed
paying customers, we realised we lacked a clear path to the
necessary scale and returns. This prompted the decision to cease
operations and return capital, sharing our experience as a case
study.

In retrospect, it’s easy to see ways we could have approached
things differently. This document is a post mortem, explaining
what happened and why it went wrong. Our aim in writing this is:

1. Codify and share what we’ve learned for our benefit and
   hopefully others.
2. Document the story for posterity.
3. Produce an artifact to explain, if not justify, the time and
   money spent.
4. Exorcise our demons.

We want to stress from the start that the ultimate failure of the
company lies with us. Some issues were within our control and some
were beyond it. At times, we’ll describe external factors in ways
that sound negative. This isn’t an attempt to pass blame. We want
to tell the story as matter-of-factly as possible. Most
importantly, we’re extremely grateful to everyone who supported us
over the last couple of years, in money and in time.

Jamie Rumbelow
and
Henry Dashwood
April 2025, London

Table of Contents

This document is long; this table of contents also functions as a
bullet-point summary. The
Advice for Founders section
contains the main lessons we hope people take from our experience,
so feel free to only read that and skip the rest.

You can also

summarise this page with ChatGPT.

Introduction
jump to

• In May 2023, Tract was founded to build software to fix
  Britain’s housing crisis.
• We raised a £744,000 pre-seed round in April 2024.
• We decided to wrap up operations and return capital to investors
  in March 2025.

Mission and worldview
jump to

• Housing in Britain is expensive because getting planning
  permission is difficult.
• Granting permission takes the median hectare of land from
  £20,000 to £2.4 million – a 139x uplift.
• If we can reduce the costs and uncertainty of this process by
  any reasonable amount, we can build a business and help solve
  the housing crisis.

Reflections
jump to

Things we did well:
jump to

• Raised capital for an unusual business in a difficult market.
• Built good technology and solid products.
• Pivoted quickly in December when we realised our strategy wasn’t
  working.
• Learned a lot about a complex industry quickly.

Reasonable errors:
jump to

• Overestimated British market size and receptiveness.
• Raised venture capital for a model that probably should have
  been funded differently.
• Focussed too much on technology over business development.
• Built out the team too early.
• Didn’t consult land agents early enough.
• Failed to capitalise on Scout’s success.
• Spend lots of time and money on non-essentials.
• Didn’t focus on getting to revenue.

Advice for founders:
jump to

• Get to the US – larger, higher-quality market, better ecosystem
  for building companies.
• Focus on market quality – receptive customers, clear
  decision-makers, fast learning cycles.
• Stay lean until you have proven revenue.
• Be aggressively commercial from day one.
• Test hypotheses quickly and thoroughly.
• Always ask yourself, “what have I learned from customers?”

What’s Next?
jump to

Appendices
jump to

• Further reading
• Things that should exist
• Things that already exist

The Mission

Many young people have had to delay forming families and often
take poorly paid, insecure jobs that can barely cover rent and
living costs as the price for living in culturally attractive
cities. They see opportunity as limited and growth as barely
perceptible. Meanwhile, older generations sit on housing
property worth many times what they paid and, stuck in a
zero-sum mindset, often prioritise the protection of their own
neighbourhoods over the need to build more homes. Can you blame
young people who resent older people, and the West’s economic
system itself, when this is what it offers them?

Myers, Bowman and Southwood,
The Housing Theory of Everything

Housing in Britain is expensive because of artificial supply
constraints – specifically, the difficulty of obtaining planning
permission to build more. Planning permission is Britain’s
regulatory approval that landowners must secure before developing
land or changing a building’s use. When permission is granted to
build homes on agricultural land, its value increases dramatically
(often 140x or more), creating enormous wealth for landowners.

This looked like a business opportunity: if we could help more
sites get planning permission, we could capture some of that
uplift. The market size looked compelling – billions in Britain
alone, the political winds seemed favourable, and there seemed to
be few modern software solutions.

We were driven by a mix of moral outrage and technological
optimism. It seemed absurd that bureaucratic obstacles were
holding back so much potential value, especially when millions
were being spent on documentation that could be automated. With
the rise of LLMs, we believed we could transform this inefficient
process.

Timeline

Tract Source (May 2023 – October 2023)

Strategic land teams are groups within property development
companies responsible for identifying and acquiring land with
long-term development potential. They focus on finding sites that
don’t yet have permission for development but possess
characteristics that suggest it could be obtained in the future.
The earlier they can identify and secure control of these sites,
the greater their competitive advantage and profit potential.

This felt like a software-shaped problem and could form the basis
of a larger platform for planning, moving elsewhere along the
value chain. When Jamie began working on Tract, this site sourcing
problem was the first thing he looked at.

Some sourcing tools existed, but the popular options seemed poorly
built: badly designed, built atop untrustworthy data sources, and
not built around the sourcing workflow.

Jamie had ideas to improve the product experience and began
building them out. He started to lean on industry advisors for
introductions. He read The Mom Test (more on which later)
and had dozens of calls with whoever would take them.

During these calls, he realised his intuitions about the existing
products’ problems were correct (“I don’t trust it”, “I need to
check the numbers, it’s annoying”). This was exciting: he thought
he was onto something.

But he didn’t ask why users tolerated it (“It’s fine”, “Does what
I need”, “We went with [competitor] because, to be honest, they’re
nice guys”). It was unlikely whatever he built could be 10-100x
better at solving this problem without radically changing their
workflow, which was tough for a solo developer working on savings
– Henry began helping in his free time from late summer but
wouldn’t come on full time until mid-December.

Jamie also began to find more competitors, some
well-resourced, all of whom appeared to be competing on price.
These were already cheap contracts: a few hundred pounds per month
for a small/medium-sized team. And they were getting cheaper.

We concluded that this was a difficult market to sell into, with
race-to-the-bottom pricing dynamics, and no obvious way to make a
SaaS tool that helped strategic land teams do site selection so
well that these factors wouldn’t matter. It was time to pivot.

Learnings

This process gave us:

1. a better understanding of the problem space and competitive
   environment;
2. the basis of a network;
3. and time in which the early data infrastructure which would
   support our subsequent products was built.

However, it took too long to reach the pivot
point. A more thorough competitor analysis would have revealed the
market problems earlier, rather than being distracted by writing
code. None of what we needed to learn required writing code to get
there.

The biggest lesson here:
getting time-to-validation as low as possible matters more than
anything else. If there are ways faster to get there, you should take them.

Interlude: Attract (October 2023 – November 2023)

Our site appraisal tool, Attract, emerged from discussions with
our design partner Paul and from Tract Source’s challenges. The
concept was simple but promising: instead of selling land
information to developers, we’d provide it to landowners for free.
The greatest constraint for any promoter or developer is access to
developable land, so we imagined a tool encouraging landowners to
reveal their openness to development would be valuable. The
generated appraisals would allow us to rapidly qualify sites and
identify potential opportunities.

Initially, we considered selling this tool to developers and land
promoters seeking strategic land opportunities. However, we
quickly recognised two fatal flaws in this approach:

1. The economics didn’t work—we couldn’t charge more than
   £50/month/customer, and there weren’t many customers.
2. We’d face the same sales challenges as Tract Source, compounded
   by the fact that this was an unconventional solution with no
   market precedents.

Despite this, Jamie completed the conversion work and launched a
white-labelled version on Paul’s company’s website in early
November. It delivered impressive results: he received more
submissions and higher-quality leads. This quick win validated our
technical approach, but the underlying business model remained
insufficient to build our company.

This experience taught us something valuable: we could create
genuinely useful tools that solved real problems. However, we
still hadn’t cracked how to transform that utility into a
venture-scale business model.

November 2023 – January 2024

With the white-labelled version of Attract online, we entered a
period of exploration and uncertainty. We had a call with a major
surveyor where we showed them a mocked-up tool for writing a
planning application using an LLM and the information about a site
in our database. But after the demo, we were ghosted.

Market concerns loomed large. The pricing dynamics made us
question our ability to raise capital with our current approach.
In retrospect, we may have been closer to viable products than we
realised. Multiple British prop-tech companies have been funded,
including in the US, during the lifetime, suggesting alternative
paths we could have taken.

Despite challenges, we continued experimenting. In December, we
created a ‘Tinder for Buildings’ demo with inpainting models that
received positive feedback. We continued scoping ways to build a
business on our planning data work. We were awarded an
Emergent Ventures grant, validating our mission if not our approach.

January 2024 – May 2024

In January, we began fundraising while working on extracting Local
Planning Authority validation checklists—technical work to support
our evolving vision.

A February visit to a developer proved illuminating, though not as
hoped. Their skeptical in-house planner admitted: “To be honest,
the system being broken helps us.” This comment crystallised a
tension in our market: many established players benefited from the
inefficiencies we aimed to solve.

This realisation prompted us to revisit our fundamental problem
statement. The facts were compelling: land with planning
permission becomes dramatically more valuable, and this value
creation stems from the friction and uncertainty in the planning
process—friction that good software could reduce.

We faced a dilemma. Selling software into this market would be
tough, and it seemed wasteful to capture only a small slice of the
value we could create. If we could facilitate 100x value increases
in land, why sell this capability to others for modest SaaS fees?
What B2B model could compete with capturing that uplift directly?

We considered a radical pivot: becoming land promoters ourselves.
We’d partner with landowners or acquire land, secure planning
permission using our technology, and sell with permission
granted—capturing the value uplift directly.

We found another opportunity: promotion costs don’t scale linearly
with site size, making many smaller sites economically unviable
for traditional promoters. We could counterposition by targeting
these ignored sites and sell them to SME developers.

This model offered significant advantages:

1. We avoided selling software to a resistant market.
2. The potential revenue and profit margins were substantial,
   especially if we could reduce costs through automation.
3. We had a clear technological roadmap: automate the existing site
   selection and planning application processes.
4. As our own customer, we could optimise an industry that
   underutilised modern technology.

Implementation would be challenging—some aspects like site visits
couldn’t be fully automated—but we believed we could create a
durable advantage by controlling the critical fulcrum point where
planning permission is granted.

This became our fundraising narrative:

During the fundraising process however, we identified a
bottleneck: access to land. Without reliable land access, our
growth would be constrained. How would we:

1. put ourselves in front of landowners,
2. identify the ones open to selling,
3. get them over the line?

One investor – who ultimately passed – described this challenge as
requiring extensive “hand-cranking”—an apt analogy. But at the
time, we thought Attract could solve our top of funnel problem.

Rather than white-labelling the tool for strategic land teams, we
could own it, market aggressively to landowners, keep the sites we
want to develop ourselves and pass the rest to strategic land
teams for a referral fee. Appraising land and advising on its
development potential is part of what a land agent does. We would
be automating that.

Why would a landowner use our tool? Partly out of curiosity like
taking personality quizzes, but also because our information was
genuinely useful. Land agents bill hundreds of pounds for
appraisals with the same information we could pull
programmatically. Henry had recently commissioned two appraisals
for sites following advice his family had received. They were £600
each and contained:

• A summary of planning constraints for the site (e.g.
  conservation areas, nearby listed buildings, where the village
  sat in the settlement hierarchy).
• Relevant local plan policies (e.g. what development to
  encourage/discourage).
• Previous planning applications for the site.

We already had this information or plans to collect it. We could
generate these appraisals, give them to landowners for free, and
use this to solve the top-of-the-funnel problem.

We made a subtle but critical error here – we assumed the problem
was limited to the top of our funnel (identifying landowners and
sites). In reality, as we’d discover, no part of the funnel was
robust enough to build a venture-scale business in our required
timeframe.

Had we recognised this earlier, we might have concluded this
business lacked venture-scale potential, or we could have examined
how to modify our approach.

Learnings

We still agree with the principle behind this pivot; that the next
generation of billion-dollar companies may
sell work, not just software, and that this is especially true in UK
proptech. We’re happy with the reasoning. But we were entering an
industry to do something we had no experience in, and without any
commercial traction.

Paul Graham has an essay where he says the most efficient question
to ask founders is “What have you learnt from users?”. One problem
this question would have exposed if we’d asked it was that we
hadn’t spoken to the people using Attract and who would develop
their land with us. The people we were speaking to and learning
about planning and development from weren’t our actual users. This
meant we couldn’t begin testing our product’s commercial traction
by asking if a user would pay for it.

Although we erred by not getting relevant user feedback while we
had months of savings, the focus in the latter part of the raise
to build a business plan was probably correct. We were working on
Tract unpaid. As the deadline to raise money approached, our focus
was (not unreasonably) on getting the funding to survive.

These weeks were a success: we raised capital in a tough situation
when the alternative was to shut down and get jobs. However, we
had backed ourselves into a corner, not taking advantage of the
previous time to run a rigorous market and product-discovery
process.

The Fundraise (January 2024 – April 2024)

Since raising capital, we’ve learned our fundraising experience
was unusual. VCs operate with a fundamental asymmetry: it costs
them virtually nothing to stay in touch with a company without
investing, but missing the next unicorn can be catastrophic to
their portfolio returns. This creates a dynamic where they’ll meet
hundreds of companies annually, rarely delivering outright
rejections.

Contrary to the “VCs never say no” stereotype, most were capable
of clear passes: “not a market we know enough about” or “we’re not
convinced about this aspect of the pitch.” The key insight is
this: if a VC sees potential, they move quickly. If you’re stuck
in a holding pattern of positive but non-committal feedback, their
current position is likely “no”—they’re leaving the door open in
case you gain traction or pivot to something more compelling.

We found ourselves in this holding pattern. One VC was interested
but nervous about leading the round, while at another, the lead
partner wanted to write an angel check but wouldn’t commit to
funding institutionally. This created a frustrating cycle of
meetings yielding positive feedback followed by requests for “just
one more” spreadsheet or one-pager to clarify something. During
this period, we worked to integrate early Attract usage data into
our narrative about targeting small sites as land promoters.

Through delicate back-channeling between the two firms, we got
them as joint leads, with five angels joining the round. We then
experienced that classic founder moment where, after securing a
term sheet, several other firms expressed interest.

The process from term sheet to closing took over a month. Despite
being a straightforward priced round, we had to pay both teams
lawyers to negotiate minor details. In San Francisco, a deal this
size would have been done with a quick SAFE note, so it was
frustrating to spend £25,000 out of the £744,000 we raised on
legal fees.

Learnings

Warm intros are 100x better than cold outreach –
maybe one or two VCs set up calls from a cold email, out of ~50,
whereas nearly every warm intro was happy to talk to us. These
came from former colleagues who became investors or had startups
and introduced us to their VCs. People want to make and receive
introductions. So, assuming you make a good impression, feel free
to ask for help. If they don’t feel comfortable (maybe they don’t
they don’t feel comfortable (maybe they don’t know the person
well, or they’ve recently taken up a lot of their time, or they’re
busy) they will politely explain why.

Running a well-organised raise is better than not, but you
can’t really plan it.
Unless you have hockey-stick growth and a surplus of investor
interest, you need to work whichever angle you have, even if it
means abandoning your existing plans.

Try to raise early rounds on a SAFE/ASA – even in
tranches, even if it means accepting less cash or a lower
valuation, even if it complicates your cap table. Despite capping
legal fees at each stage, we spent £25,000 on lawyers – capital
that should have gone toward building our business. We waited over
a month for the money and were distracted figuring out legal
terms.

Not every business suits VC – If you’re
interested in technology or startups, you’ll hear lots from
venture capitalists. This is partly because they engage in content
marketing and thought leadership to attract dealflow and partly
because being a VC requires optimism and interest in the future.
So their interests will overlap with yours as a startup founder.
But before you raise money from them, consider if your business
fits their financing model. Venture investments follow a power law
model. Venture investments follow a power law where a few pay off
so well that they cover the others that go to ~zero.

A good pitch to a VC should acknowledge the risks of the company
failing, but not eliminate them. The focus should be on the huge
opportunity if you overcome them. For decades, software companies
fit this model. There’s a risky startup stage,but if a company
survives, they can build moats through network effects (the most
useful platform is the most popular) and switching costs
(migrating data and workflows to a new system is hard).

Not every business is like this. In real estate, you may have a
thesis about where demand is going. You may make speculative
acquisitions or invest in site improvements before selling. It’s
unlikely these bets will pay off 100 to 1000x like the best
venture investments. However, a good thesis and execution can
generate an internal rate of return of 10 to 20% – more than
keeping pace with a VC fund’s aggregate return. There are
investors interested in these opportunities but they make less
noise than VCs. They are often family offices, and may be the LPs
of venture funds.

Some companies try to balance being a high-risk bet with high per
deal costs by raising money from VCs for an operating company and
property investors for a property company. The former bet on the
company growing to process many deals,while the latter bet on the
success rate of those deals. These complex deals require careful
alignment of everyone’s incentives.

If these last paragraphs resonate, check out Brad Hargreaves or
Nick Huber’s writing. See the further resources section for useful
posts from Brad’s Substack for anyone considering financing
options.

April to November 2024

Marketing to landowners proved difficult. An appraisal tool for
farmers doesn’t go viral. We identified things like niche Google
searches e.g. specific DEFRA forms with low ad competition, but a
few thousand pounds of ad spend generated minimal activity.

The challenge: landowners might pay hundreds for an appraisal, but
rarely need one. Identifying and reaching them at their moment of
need was nearly impossible.

We made two critical mistakes:

1. We spent three months rebuilding the Appraisal tool before
   contacting landowners who had submitted sites through our MVP.
   These existing submissions represented our only real users, yet
   we failed to nurture these relationships or learn from them
   immediately. We didn’t take them seriously enough as potential
   customers.
2. Second, we failed to understand the basic economics of land
   agency—the business we were trying to replace. When we spoke
   with established land agents, we discovered uncomfortable
   truths: they completed very few referrals, and each took 18-24
   months minimum to process.

Land agents are fragmented: many serve small geographic areas. A
birds-eye view of this market suggests you can roll it up for
economies of scale. We liked this logic, so we pursued it.

We didn’t consider if the fragmentation was a feature rather than
a bug. Each agent spends a lot of time building the social
infrastructure – going to fairs, drinking in pubs, befriending the
parish council – needed for these deals. Landowners are a small-c
conservative customer, and they don’t respond well to audacious
pitches and fast timetables. These deals take 18-24 months because
these are emotional decisions, not scalable ones.

Two or three phone calls could have revealed this reality and
neutered any delusions about revolutionising this industry.
Instead, we wasted six months—three building software and three
wondering why nobody used it.

Compounding these errors, we hired extra marketing and operations
staff based on flawed assumptions:

1. We had no evidence that more marketing would help without a
   proven customer acquisition strategy;
2. We weren’t constrained enough to justify these hires—we should
   have pushed ourselves harder first.

We found a few promising sites where the landowner was eager to
collaborate. However, further investigation revealed unique
complications that would require bespoke work taking months to
resolve before we even got onto the steps we aspired to automate.
This wasn’t a deal breaker, but it would mean using nearly all our
capital to bet on four sites over the next couple of years. If we
got them through the system, we could make enough money to repeat
the process at a greater scale. However, it was also possible that
we wouldn’t. We would have spent two years working as conventional
land promoters, which others could do better.

As we considered the sites we had and ways to increase
submissions, we explored higher leverage ways to use our skills.
What was our comparative advantage? We could build software. So we
dove back into the murky world of pure proptech.

Interlude: The Grid (December 2024)

The state of our electricity grid is an important story. Whenever
we met a developer, residential, commercial, or energy, the
uncertainty about how long they would be stuck in the
interconnection queue and how much they might pay in first or
second comer charges would come up. Delays or unexpected charges
could run into the millions.

We lack good tools for modelling the grid. At the time of writing
the
National Energy System Operator’s map
thinks that Didcot is on the Isle of Wight, and Sizewell B is in
Scotland. If you want to build something that will draw from or
inject significant power into the grid, you need to know:

1. What is the current capacity around your proposed site?
2. What will the capacity be in the next few years?

We already had a map with layers like power line and substation
locations, voltages, and official headroom capacity.

DNOs publish their actual headroom monthly in tables called the
embedded capacity register. It wouldn’t be hard to add that.

We were scraping planning applications to build a model of future
generation and demand growth.

At the year’s end, we explored whether this was a worthwhile pivot
opportunity. We found a couple of developers who hired
consultancies to build internal tools at great expense. We found a
couple of start-ups whose demos didn’t justify the huge prices for
features on our roadmap. We had exciting conversations with one
energy developer about a design partnership. They wanted a
platform to find companies in the connection queue open to selling
their spot.

Our idea was speculative, requiring us to negotiate deals in an
unfamiliar industry. Meanwhile, we were making progress with the
Editor project. So we shelved this idea.

Interlude: Scout (December 2024)

While attempting to build a land promoter, we started using
Landstack, a site sourcing tool, with good quality datasets that
we hadn’t ingested. We had no desire to compete with them or steal
their data. We made the mistake of asking for API access. They saw
this as a red flag, investigated us, realised we were technical,
and booted us off the platform. So we needed a replacement.

We decided to build it ourselves. We had all the needed
components: data ingestion and map layers. It took about one
developer-week to create the first version.

Why not release it? Allowing people to explore our data might:

• encourage inbound traffic;
• crowdsource the debugging and interrogation of our data for
  internal use;
• and help test the interface for a grid capacity discovery
  product, if we pursued that.

We launched the tool, called Scout, shortly before Christmas.

Scout did well, with a few hundred visitors, some acclaim on
Twitter and LinkedIn, and emails and comments thanking us for it;
it was our most-used product.

We’d like to think we caused a stressful Christmas at Landstack,
who released Landstack Lite, a free version, in early February.

Learnings

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.

There was some accidental product-market fit. We found an organic
audience for our side project; making our data free and easy to
access provided genuine value.

Tract Editor (December 2024 – March 2025)

During the same tech sprint that produced Scout, we started
considering reviving the planning applications platform.

We had all this information in our database – most required for
the desk reports for planning applications – but were only using
it for appraisals. To drive down the cost of planning
applications, we needed to automate as much of the process as
possible, including writing these reports.

Since we abandoned the idea of doing property development
ourselves, we considered selling the tool directly. Many US
startups help draft documents in development and construction, so
there was some precedent.

A demo came together quickly. We dumped our appraisal output into
a JSON blob. We parsed policies from an LPA’s local plan. We built
a document editor using open source components. We chained LLM
prompts with our planning information – and got good results. A
vision for this product began to form. We’d sell an LLM wrapper to
planning consultants and developers to speed up document drafting.
Then we’d expand to become the platform for managing all their
projects, each with dozens of documents – hundreds with revisions.
Hundreds of thousands of planning applications are submitted
yearly, but no tool captures the institutional knowledge that
compounds from project to project.

This felt promising. It played to our strengths as software
developers. There was a sales playbook we could follow and our
investors would understand for the next round. Preliminary
discussions suggested the market was more open to our product:
even planners realised they needed an answer to the AI question.

There was also a path to apply our technology to the US market,
particularly California, which has its own housing crisis and
legal hurdles.

We could build tools to help people navigate applications like lot
subdivisions or rezoning petitions, or a tool for searching trial
court rulings. Developers sometimes sue the city council, and
these rulings don’t automatically become planning policy like
Planning Inspectorate rulings in England, but they’re useful.
Developers pay land use attorneys a lot of money to research them.
Or we could help multijurisdictional landlords keep up with
different regulations.

The common thread was our ability to ingest large numbers of
documents, map their content onto a geospatial layer, and ask
meaningful questions. Our technical foundation could support
multiple business models in the UK and US.

Expanding internationally would require significant resources and
market knowledge. We decided to focus on validating our core
product with UK customers before pursuing US opportunities.

Setting up design partnerships

Towards the end of 2024, we set up calls with several planning
consultants. We asked about their workflows and what tools. We
described our vision and showed them our demo. The responses were
all positive.

Narrowing focus to pre-app letters

After a month of calls and building, we realised our product was
too general-purpose. We needed to focus on a specific problem. We
had little evidence of selling this software and wanted a clear
use-case to ground our offering.

We focused on pre-app statements. Most local authorities ask major
developments to get pre-application advice: feedback on an initial
proposal before submission, to ensure the basics are solid. It was
the simplest document we saw. Most applications go through pre-app
first – about 80%, according to one customer – it’s usually step
one. We knew the costs and timelines, so we could anchor the
pricing. And we had most of the information to generate them.

This led to a product called Tract Editor. Users would draw their
site boundaries on a map, and we would pull existing site
information. We could generate and reuse our appraisal output, so
this was easy. We could pass this information into an LLM to
produce a first-draft pre-app statement.

We’d add normal document editor features – comments, versioning,
WYSIWYG, etc. – to integrate it into their workflow and avoid
needing a perfect first draft. It could get you a reasonable
starting point, like a junior planning consultant, which you could
refine in a familiar environment.

We built a good tool that produced compelling first drafts from
minimal information. It had a smart Q&A UI allowing the model to
ask the user questions and regenerate sections based on the
answers. It treated the planning system as a first-class citizen
of the document editor, rather than focusing on the AI. It cited
its sources and provided references for the quoted planning
policy.

Our design partners seemed happy. We had made a marketing website
and received good feedback from industry people. We chose a price
of £99/user/month. We were ready to start selling.

Learnings

By this stage, we knew to talk to customers before, during, and
after building a demo, and we didn’t spend too much time coding
before getting positive feedback. What we did wrong was assume
‘positive feedback’ meant ‘desire to purchase’.

Customer switching costs have a psychological as well as
economic logic.
Better alone doesn’t mean people will use it. You’re competing
with another workflow plus any status quo bias, which can be
significant.

The Decision To Stop (March 2025)

When we offered a 50% discount to our design partners and asked
what would get them to commit, their response was telling. Despite
positive feedback, they wanted significant additional features
like full planning statements before signing. This forced us to
confront several hard truths:

1. Despite positive feedback, customers weren’t ready to commit,
   even with steep discounts.
2. After nearly two years, we had zero revenue to show for our
   efforts. (We clearly weren’t great at this!)
3. Our opportunity cost was rising as the tech landscape evolved
   rapidly.
4. While we might build a business that could support us, we
   couldn’t see a path to the venture-scale returns our investors
   deserved.
5. The British market was too small, fragmented, and resistant to
   change for us to progress at the speed and scale our investors
   required.

Any one of these challenges could have been addressed. But
collectively, they showed we faced months of struggling to secure
small revenues through manual sales processes in a market with no
clear path to venture-scale growth.

We considered pivoting to the US and drastically reducing our burn
rate. Ultimately, we chose to return the remaining capital to our
investors and walk away.

Reflections

Things we did well

Fundraising

We raised capital for an unconventional business model in a
challenging sector. In a difficult fundraising environment, we
secured funding from institutional investors and angels who
believed in our vision to transform the British housing market.
This is no small feat for a pre-revenue company in an industry not
known for technological innovation.

Technical Execution

We built good technology and solid products:

• Our data infrastructure effectively ingested and processed
  complex planning and geographic information.
• Scout became a useful tool with recurring users and positive
  feedback.
• Our Appraisals product was fast, well-designed, and provided
  useful information for its hundreds of users.
• Tract Editor produced high-quality planning document drafts that
  impressed industry professionals.

These products were built upon useful primitives that enabled
quick experimentation.

Pivoting

When we recognised our land promotion strategy wasn’t working, we
decided to pivot quickly. We parted ways with the non-technical
employees not involved in building Tract Editor. We found design
partners enthusiastic about our product and committed to giving us
feedback, while keeping our investors informed about our strategic
shift.

Closing Down

There are many ways in which we wasted time and money. But we are
proud of the fact that we closed down the company because we
couldn’t see a way to make it work for our investors, and I think
we can all sleep well knowing that we made the right call.

Learning and building relationships

We developed valuable relationships. From planning consultants to
developers to land agents, we built a network that provided
insights, feedback, and opportunities that would have been
invaluable had the business continued.

We knew little about planning before this. But learned enough to
build something that impressed the industry experts. This isn’t a
complete win – we didn’t convert them to paying users. But they
took us seriously. That’s not something we were certain we’d
manage at the outset and gives us confidence moving forward.

Reasonable Errors

By ‘reasonable’, we mean mistakes that were understandable given
the available information and our natural inclinations as
founders.

Our technical and product execution was strong. Our ultimate
challenges were market selection, business model fit, and the
British planning system’s dynamics rather than our ability to
build useful technology.

Overestimating the British market’s size and receptiveness

The British proptech and planning market seemed substantial, given
the dramatic land value increases from planning permission. There
seemed to be a venture-scale opportunity, especially as several
British proptech companies secured funding during our journey.

Building a venture-backed real-estate company

If our software could help many sites secure planning permission,
it made sense to capture as much of that value as possible. But we
underestimated the uniqueness of each site’s challenges and the
“hand-cranking” needed to get landowners over the line. The way to
run a business like this is to use off-the-shelf tools and raise
money from institutions seeking a less risky 10 to 20% IRR.

Focusing on technology over business development

As technically-oriented founders, we gravitated toward building
solutions. When faced with challenges, our impulse was to solve
them with better technology rather than rethink our market
approach. This technical optimism is common among founders with
our background and was reinforced by the emergence of powerful new
AI tools.

Building a team too early

Conventional startup wisdom encourages bringing on talent to
accelerate growth. With funding secured and ambitious goals,
adding team members seemed logical.

This is a classic startup dilemma: you need people to build and
sell your product, but adding headcount increases burn rate and
creates complexity before validating your revenue model. The error
wasn’t in hiring – many successful startups scaled their teams
pre-revenue – but rather that we didn’t have a clear hypothesis
about how these hires would validate our core assumptions.

There’s no perfect formula here. Too little hiring can mean missed
opportunities and founder burnout; too much creates financial
pressure and overhead. Our mistake was not ensuring each hire was
tightly coupled to the critical path to revenue.

Not entering the US market

This might have offered more opportunities. Many VC-backed
proptech companies founded before and during Tract’s lifetime
(e.g. LandTech, SchemeFlow, PermitPortal) expanded to the US. Land
use and zoning varies across US states, but traction in one may
have been enough to raise the money to fund others.

But our challenge was understanding users deeply enough to build
something they’d pay for. If we struggled in our home market with
networks and cultural understanding, it’s not obvious we’d have
fared better in the US.

Unforced Errors

Not taking more advantage of Scout’s early success

We could have done more here to take advantage: collected more
emails; added more datasets and features; been louder.

Not talking to landowners from the Attract prototype immediately

We had a chance to learn a lot about our key market months before
we did, and we didn’t.

Not talking to land agents immediately

We assumed a big, slow, fractured market could be fixed without
understanding why it was that way.

Time and money spent on non-essentials

These included an office, website and branding, a trip to America,
contractors, and unnecessary employees. All of this was to appear
to be running a startup – LARPing as founders – rather than
building a business.

We also worked on side projects – including some open source work
– that we wanted to exist but weren’t on the critical path to
revenue.

Other possible factors

Cofounder fit

We get along well, but our skill sets aren’t especially
complementary. There’s significant overlap, and we didn’t hire
thoughtfully enough to correct that.

Energy levels

As mentioned in the ‘rising tides’ learning below, the past year
has felt challenging, and neither of us feel that we have been our
most productive or maintained the high energy and urgency needed
to make progress.

Remote work vs. IRL

We started with a strict in-office policy, but this was disrupted
by a remote hire, and we let it slip. This affected focus and
morale.

Advice for founders

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”.

Arnaud Schenk

Get to America

The US is the largest and most dynamic market. Even niche
industries are large enough for venture-scale companies to exist.
This is rarer in Britain.

If your value proposition is built around saving labour costs or
augmenting productivity, Britain’s lower median salaries are a
ceiling on both the value you can create and the portion you can
capture as a vendor.

Prioritise finding users in America if you want to raise money
from American VCs. They will invest in European companies but
heavily discount non-US revenue.

Choose your market wisely

Consider the market size, but also assess how receptive your
target users are to new products and workflows. Questions to ask:

• Does the market have early adopters willing to try new
  solutions, or is it dominated by late majority/laggard customers
  who wait for proven technologies?
• Can you easily identify and access decision-makers? Markets with
  clear purchasing authority and shorter sales cycles allow faster
  iteration and learning.
• Do potential customers engage with product demos, respond
  promptly to communication, and provide actionable feedback?
• Are there self-contained pain points you can start selling a
  solution for, or a long tail of features customers need before
  they’ll pay?
• Is the customer base concentrated enough to build momentum
  through reference customers, or so diffuse that each sale
  requires starting from scratch?

Stay lean

We hired too soon, rented an office, and spent money on
branding/design before having a clear revenue route. Money gives
you more latitude, which means more opportunities to avoid
necessary actions.

Be aggressively commercial

We focussed too much on building a theoretically sound business
model and too little on testing it in the market. If we had asked
“what have we learnt from users?” throughout 2024, it would have
exposed that very little informing our product decisions came from
conversations with our target market. Get traction with your
target users before raising money.

We were distracted by Tract’s potential to help solve the housing
crisis. But since we never made any money, we couldn’t keep going,
making it irrelevant. It’s great to have a mission beyond making
money. But if it doesn’t contribute to making your business
sustainable, it will need to take a back seat for a few years.

The adage that ‘a rising tide lifts all boats’ is true, but
incomplete. Success not only lifts you, but it changes you. It
gives you more confidence, energy, and a faster learning rate.
Conversely, treading water in a low-tide harms you. It saps your
energy, forces you into strange epicycles. Beware treading water.

Test your hypotheses

We often learned something that showed us we had to change, but it
took months to ask the right questions or perform the test. When
considering an idea, think of ways to instantly find out if it’s
flawed. For instance, it took too long to realise referring sites
to developers through Attract wasn’t an easy way to get short-term
revenue. We knew people who did referrals on the side and how the
process worked but never drilled down into how long it took and
what made the conversations drag on.

What’s Next?

Jamie

I’m open to new projects, opportunities, jobs, or ideas.

I’m open to relocating to San Francisco.

My priority is to find truly excellent people working in a culture
of high performance. Otherwise, I’m agnostic with respect to
sector, stage, size or role.

My website is
jamierumbelow.net. My Twitter is
@jamierumbelow. You can email me at
[email protected].

Henry

I’m spending the next few weeks writing and attending to life
admin. I’m tempted by the thought of another startup while the
lessons from the last one are fresh. I’m giving thought to ways I
can be useful before committing to the next path. Some things I’m
interested in:

• Buildings and urbanism. Similar to Tract’s
  mission. I’m cautiously optimistic that we are going to increase
  the rate of building in the next few years in the places where
  it is most needed.
• I’m increasingly concerned by our shrinking industrial
  base. 
  In Britain, I think high energy costs are a major factor. And in
  both Europe and America I’m worried about what we can rely on if
  relations with China worsen.
• AI. Obviously the biggest story this decade the
  area in which I have the most professional experience.

I’m open to relocating to the US.

You can view my website and socials at
henrydashwood.com.

My email address is
[email protected].

Appendices

Further Reading

Here are some resources for those interested in the problem space:

General startup reading recommendations:

Some pieces from
Thesis Driven
about alternative funding models to venture capital that better
fit real estate plays:

Things that should exist

• Appeals and planning apps search. The industry
  leader,
  COMPASS, is overpriced and
  pissing everybody off. Proper appeals and planning application search, including
  semantic search (“give me every planning application in this
  borough within the last decade that was rejected because of a
  disagreement about materials”) could be a nice product.
• An accurate grid capacity map and trading platform.
  See Interlude: The Grid above.
• Better industry-specific content. Most planning
  media is rubbish; an LLM could do just as good a job; thoughtful
  humans could do much better (who’s the Matt Levine of planning?).
• LLM-powered web scraping. Frameworks like
  scrapy and its
  long
  tail
  of
  ancillary
  services
  are valuable, but many use cases need more intelligence, which
  modern LLMs could provide.
• A tech-enabled land promoter.
  We still think somebody should do this – just not via VC funding
  – but there are ways to reduce planning application costs and
  make this business work.

Things that already exist