The first write-off

Reelmonk was a video-on-demand platform for Malayalam film, with a mechanism to stop the piracy that was eating regional Indian content. We invested in 2014 and wrote it off in 2015. The company wound down.

It is still on my portfolio page, struck through — one of four now. A track record with the failures removed isn't a track record.

I have told a tidy version of this story before — the kind you give in an interview, where the causes are neat and none of them are yours. This is the longer version, with a decade of distance and rather more of the blame in the right place.

The original sin: I was the customer

I was a user. I wanted this product to exist. I had the problem it solved, I understood the frustration it addressed, and I was introduced to the company through the idea rather than through the business.

Being the customer is usually sold to investors as an edge. In my experience it is at least as often a blindfold. I was not evaluating a company; I was agreeing with a premise I already held. Everything I would normally look hard at, I looked at softly, because the thing I cared about — does this need to exist? — I had already answered before the first meeting.

Almost every specific mistake below follows from that one.

The team was set up wrong from the start

The founder was technically very strong. Genuinely good at the engineering, and that was never the problem.

What he did not have was experience building a business, or any route into the market he was selling to. Those are two different gaps and the second one matters more than people think. It does not mean a founder needs a decade in the film industry before starting a film company. It means being able to name your customers, get to them, talk to them, and keep track of what they tell you. Having no way in at all is a different category of problem from being inexperienced — and it is much harder to fix once the money is in.

When that became apparent, more co-founders were brought in to fill the gap. That is when the real trouble started. What had been a capability problem became a people problem, and the friction that followed looked like the cause of the failure when it was actually a symptom of a structure that had been wrong since the beginning.

What we discounted

Reelmonk needed the film industry to change its behavior. Specifically, it needed producers to treat internet rights as a separate, negotiable asset — rather than something bundled away with satellite rights and not worth arguing over. Producers were unwilling to challenge that. It wasn't that they disagreed with us; the question simply wasn't live for them.

We understood this and thought we could work around it. We could not. You cannot force an industry to renegotiate its own conventions because your portfolio company needs it to.

What eventually changed it was COVID. Theaters shut, producers had no other route to an audience, and the value of OTT became impossible to ignore. Internet rights are now negotiated separately as a matter of course.

The thesis was right. It arrived about five years early.

The cap table, and how we caused it

Our angel group ended up holding around thirty percent of the company between us.

We didn't ask for it. It was offered, and we took it, and at the time it felt like we had got a good deal.

It was a serious mistake, and it was ours. Thirty percent to an angel group at that stage makes a company much harder to fund later — every subsequent investor looks at the table, sees founders diluted early, and draws the obvious conclusion about how much upside is left for the people doing the work. A founder-friendly investor should have refused it, or taken less. We didn't understand that yet.

Cap table structure is now an explicit criterion in how we look at deals. That one we learned the expensive way.

And I got involved operationally

I thought I could help with business development. I tapped my own network to make introductions to producers and people in the film industry.

It did not work.

I have since been strict with myself about this. When an investor steps in to close a capability gap in the team, two things happen: you lose the ability to see the company clearly, because you are now part of it, and the founders lose the pressure to solve the problem properly. Being useful in the short term usually costs both sides something in the long term.

The one that matters more than the rest

Timing.

You can have the right idea, a capable team and a working product, and still fail because the market isn't there yet. It is like catching a wave — being in the right water with the right board is necessary and nowhere near sufficient. You have to be there when it forms.

Reelmonk got that wrong. Not by being foolish; by being early. And "ahead of its time" is normally a self-serving diagnosis, which is why I hesitate to use it — except that in this case it is checkable. The market did arrive. We can point at when. We just weren't there for it, because a company that is early needs runway to wait, and this one had raised too little to wait with.

That is the real shape of it, and it took me a decade to see. The capital plan and the timing aren't two separate failures. Being early is only fatal if you haven't funded the wait.