Edition #36: The Hidden Cost of Optionality
The first day back after the Easter bank holiday tends to follow a predictable pattern in my opinion. Your inbox has filled up again, Brokers have restarted processes that paused last week and new listings have landed alongside deals you were already reviewing, before the break.
It feels like momentum has returned.
But when you actually look at your pipeline closely, most of those opportunities are sitting in the same place they were before the long weekend.
Reviewed and maybe even discussion has been had, but not real progress. So whilst the pipeline is working, there appears to be an optionality problem.
Busy pipelines are not productive pipelines
A large pipeline creates the impression that you are well positioned.
You have visibility across multiple opportunities. You are comparing pricing, structures, locations, and asset types. You are speaking to different brokers and maintaining access to flow.
On the surface, that looks like good discipline, but in practice, what usually happens is far less effective.
You build a model for one deal, then move onto the next before forming a view. You have early conversations with agents but do not push hard enough to uncover the real issues. You review headline numbers without getting underneath how the asset actually performs.
Each deal gets partial attention, but somehow none of them get the level of scrutiny required to make a confident decision.
More options slow decisions down
Optionality feels like flexibility, but it tends to create hesitation.
When you have multiple live opportunities, every decision becomes relative. Instead of asking “is this deal good enough to proceed?”, you start asking “is this better than everything else I am looking at?”
That comparison never resolves itself. There is always another deal still under review. Another set of numbers to run. Another conversation that might change your view.
So decisions get delayed. Offers are not submitted. Negotiations do not progress.
The bottom line of this, is that good opportunities drift because conviction never quite forms.
More analysis does not create conviction
Most investors are not short of analytical capability.
You can model income, stress test debt, adjust assumptions, and run multiple scenarios. You understand how to interrogate a deal on paper.
The issue is not the quality of analysis. It is how long you rely on it.
After a certain point, additional modelling stops producing new insight. You are no longer uncovering risks. You are just moving variables around within a range you already understand.
Conviction does not come from perfect information.
It comes from identifying the two or three factors that will actually determine the success of the deal and deciding whether those risks are acceptable.
If that is not clear, more spreadsheets will not solve it.
Decisive investors narrow quickly
Investors who are still deploying capital consistently are not running ten deals at once.
They filter aggressively.
If a deal does not clearly align with their strategy, target returns, and operational capacity, it is dropped early. Time is not spent trying to make it fit.
Once a deal passes that filter, the level of scrutiny changes.
They go deeper on income durability. They look at tenant quality, lease structure, and how resilient the cash flow is under pressure. They examine financing terms in detail, including refinance assumptions rather than just day one debt.
They also spend time understanding what the asset will require operationally over the next three to five years, not just how it looks at acquisition.
Then they make a decision.
Optionality has a real cost
Holding a wide pipeline is not neutral.
It consumes time and attention that could be spent more effectively elsewhere.
Hours are spent building models for deals that will never be pursued. Energy goes into maintaining conversations that do not convert. At the same time, genuinely strong opportunities are not being pushed forward with enough focus.
Over time, this creates a pattern: You stay busy and informed, but you don’t progress on anything. And this erodes confidence far more than a rejected deal ever will.
Where deals actually get stuck
Most deals do not fall apart at the sourcing stage. They stall at the point where they look viable but do not feel fully resolved.
The numbers broadly work. The pricing seems reasonable. The story behind the asset is coherent.
But when you look closer, there are unanswered questions.
The income assumptions rely on a tenant that has not been fully underwritten.
The operational plan depends on efficiencies that have not been tested.
The refinance assumes a market that may not be there in the same way in two or three years.
None of these issues are obvious enough to kill the deal immediately.
But they are enough to stop you committing.
That is where most pipelines quietly slow down.
Case study opportunity (2 spots only)
As part of updating our website, I am looking for two investors who want a full core deal audit on a live opportunity.
This is designed for deals that are currently sitting in your pipeline where progress has slowed, and you need a clear view on whether to proceed or walk away.
We will go through the deal in detail, focusing on where the real pressure points sit across income, structure, operations, and exit.
This will be offered at a discounted rate in exchange for being featured as a case study.
If you have a deal that fits this stage, you can apply here:
https://forms.gle/XyRMPcxBgHi3Yktj8 & DM me ‘CASE STUDY’.
A final thought
At the start of this week, most pipelines look full again.
Take a step back and look at what is actually moving.
How many of the deals you are reviewing are getting closer to a decision?
Then reduce your focus to the two or three opportunities that genuinely meet your criteria and deserve proper attention. Serious progress comes from depth of analysis on a shortlisted amount of properties.
Thanks for reading The PropTech Edit.
Melissa Lewis
Founder & CEO, ML Property Venture