After the Pause | On Starting, Pivoting, and Pausing a Venture Over Two Years — Part 03: It Was Not a Lack of Direction. Reality Kept Changing the Question

There was a stretch when my pitch deck changed every few weeks.

Not in the cosmetic sense. Not just cleaner slides or sharper phrasing. The actual question I was trying to answer kept shifting.

At first I was talking about fragmented hospitality ownership, REIT-like structures, tokenisation and cross-border asset models. Then the focus moved to transferable hotel bookings. Later still, it became Nites Alliance, a much more grounded proposition around loyalty, guest data, alliance infrastructure and AI-led targeting.

From the outside, that timeline can look like indecision.

I understand why. Two pivots in a short period can easily be read as drift, restlessness, or a founder who has not done enough thinking up front.

But that is not what it felt like from inside the work.

I was not cycling through dreams. I was being corrected, step by step, by reality.

The first version was not a thought experiment. It was already a company in my head

The first version, the one that came out of my dissertation, was never just an idea I happened to like.

I was already treating it like a company.

The ambition was large: a fragmented, cross-border hospitality ownership model that sat somewhere around REIT logic, tokenisation and a new relationship between travel, ownership and usage rights.

What made it attractive was not simply novelty. It felt as though it could rewrite part of the market structure.

That is precisely why it held me for so long.

But once I started pulling it apart, the weakness became obvious. It was not that the concept lacked appeal. It was that it required a level of capital, legal sophistication, trust and credibility that I simply did not have.

I did not abandon it dramatically. I slowly ran out of convincing answers

Conversations with investors played a big role in that shift.

I do not remember every exchange word for word, but I remember the pattern. You begin by telling the big story. Then the questions arrive.

How does the supply side come in.

How do you get through regulation.

What level of trust is required before anyone participates.

How much capital is needed before the model stops being a narrative and starts becoming infrastructure.

Those were not hostile questions. They were fair ones.

The problem was that the fairer the questions became, the harder it was to pretend the idea was executable in the conditions I actually had.

That was one of the more useful corrections I received as a founder.

A venture is not just a good idea. It is a good idea placed inside a real set of constraints. If the mismatch is large enough, no amount of passion closes it.

The first pivot was an attempt to make the problem lighter

Once I admitted the original version was too heavy, I became clearer about what I needed next.

I still wanted to stay within hospitality. I still cared about rights, flexibility and the mechanics of travel. But I needed an entry point that did not depend on huge capital, huge trust and huge structural change before the first signs of traction could even appear.

That is where the idea of transferable hotel bookings came in.

Part of it was strategic. Part of it was personal. I had travelled enough to know how absurd it felt to be locked into non-refundable accommodation when plans changed. Flights can sometimes be transferred. Tickets can sometimes be resold. Hotel bookings often collapse into a much dumber binary: either use it or lose it.

So the first pivot did not feel like retreat. It felt like moving closer to a more immediate pain point.

I was shifting from asset ownership to transaction rights.

I built flows, mocked up a prototype, explored regulatory questions and spoke to potential partners and investors. It was not a passing thought.

The problem with that version was not comprehension. It was fragility

The weakness of the booking-transfer model appeared fairly quickly.

For it to work at scale, the market needed certain rigidities to remain in place. Cancellation rules needed to stay harsh enough. Transfer demand needed to remain meaningful. Platforms needed to leave a gap big enough for a secondary mechanism to matter.

But if an OTA decides to relax cancellation terms or absorb that need itself, the business gets thinner overnight.

That is not a technical problem. It is a structural one.

You can build the transaction layer beautifully, design a clean experience, and create a credible transfer mechanism. But if you are operating entirely inside someone else’s policy gap, you are never fully in control of your own business.

That was the harder lesson.

I was not trying to enter a blank market. I was trying to survive in the margins of markets controlled by very large intermediaries.

And margins like that can disappear the moment the platform changes its mind.

There was also the regulatory edge. The closer the product moved towards OTA-like behaviour, the more licensing and compliance questions started to matter. Plenty of people would probably have chosen to move fast and live in the grey area for a while. I knew I was not one of them.

So that version died faster than the first.

Not because there was no pain point, but because the pain point was too dependent on somebody else’s rules staying still.

The second pivot was when I finally touched the deeper problem

After two versions were corrected by reality, I began to notice something important.

Both of them, in different ways, were still operating near the surface.

The first dealt with ownership. The second dealt with booking rights. Both were tied to hospitality, and both had some logic behind them. But neither had reached the deeper structural problem that began to matter more and more to me.

Why is it so hard for independent hotels to build their own loyalty?

Why are they trapped not only by distribution, but by their inability to build direct relationships, retain guest data, encourage repeat stays and convert guests into something more durable than one-off bookings?

At some point I realised I was not really looking for a better transaction object. I was looking at relationship infrastructure.

That was when the second pivot became possible.

Nites Alliance did not become an alliance because I happened to like the word. It became one because I gradually realised that independent properties, if left completely fragmented, would struggle to build anything comparable to the loyalty and data advantages large brands already possess. But if you could connect them through a shared layer, something closer to an airline alliance than a chain, the picture changes.

AI was becoming more usable at around the same time. Some of the things that had previously lived as conceptual slides, segmentation, preference matching, cross-property targeting, started to feel buildable rather than decorative.

So while it looked like yet another change of direction, the second pivot felt less like change and more like contact.

I had finally reached the problem I should have been solving.

What the pivots were really doing was correcting the level of the problem

When I look back now, the two pivots seem less like separate events and more like a sequence of corrections.

The first version was too close to system-level rewrite. Too heavy for the conditions I had.

The second was lighter, but too exposed to external platform behaviour. It lacked control.

The third, Nites Alliance, was the first version that felt balanced enough to be both meaningful and at least somewhat moveable.

That does not mean it became easy. Far from it. The harder adoption questions, team problems, BD drag and runway pressure all arrived afterwards.

But if I had to reduce those pivots to one practical lesson, it would be this.

Pivoting is not evidence that a founder lacks conviction. Very often it is evidence of the opposite. It means you are willing to cut something you badly wanted to believe in.

Because the most expensive form of wasted time is not always being wrong. Sometimes it is knowing something is no longer right and still spending months defending it.

I do not romanticise pivots anymore

Start-up culture likes to celebrate pivots as if they are badges of adaptability.

I am less interested in the badge now.

A pivot, by itself, is not impressive. It usually means a previous version stopped working.

What matters is whether you understand why it stopped working.

Was the market too early.

Was the capital density absurd.

Did regulation make the path unrealistic.

Were you living inside someone else’s rule set.

Or had you simply not yet reached the underlying demand.

Without that diagnosis, a pivot is just a change of wording.

What I value now is not the fact that I pivoted twice. It is that those two rounds taught me what not to do again. Which problems are too heavy. Which demands are too thin. Which opportunities are only temporary gaps in someone else’s system. Which ideas feel exciting but would only become self-flattering narratives in my hands.

None of that guarantees success the next time.

It does, however, save some life.

At that stage I still thought the hardest part had probably been choosing the right direction. I had no idea the next, and in many ways more painful, lesson would be about people.