#22. Optimism reversal

plus Dan Hockenmaier, Happy Valley 3, Babel (again), Jetty Broadstairs

Hello!

I’ve had a week of making big renovation decisions and writing a funding application. We’ll hear about the funding decision at the same time as we’re moving back into the house. Locking these two things together has been a lot.

I ended last week’s newsletter saying that “I’ve noticed that everyone apart from Esther in this post is a man. Not good enough. Going to fix this for the future”.

My friend Anna Goss pointed out that this is the second time I’ve ended a newsletter like this (she’s right). She agreed that it wasn’t good enough and suggested a different solution - that I shouldn’t have sent the newsletter until I’d fixed it.

She’s right about that too. I shouldn’t have sent it. I should have fixed it.

I wouldn’t speak at an all-male conference or panel. So why is it OK for me to create an all-male platform when I literally control it myself? It’s not OK.

It was tough to hear this. Being held to account around your own values by the people you love is hard. But it’s also, for me, a wonderful thing when people are brave enough to say what needs to be said. Friends say these things to friends. And friends listen even when it’s uncomfortable.

Plus these moments are the kind of thing that I remember forever. Thanks Anna 🙏🏻

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Optimism reversal

I met up with Fi Roberto last week for a drink in Highbury. We worked together for six months at GDS and had a wonderful product/delivery partnership.

As an aside, this was the first time we’d met in person. It felt so natural! I’ve found that working closely together on screens builds the same kind of rapport you get from face to face contact. Although it was definitely nice to have a drink and a chat.

We talked about the balance of our partnership while we worked together. Fi pointed out that I was always trying to push the team to do more ideas, bigger things, take more risks - and that she balanced this by helping me understand that we only had so much capacity, should do fewer things, and should work with the reality of the constraints we had. This was the core of our partnership. It worked because we trusted each other, talked LOADS, and found a shared path. I learned so much from working with Fi. And with Elisse before her.

But what made me stop and think was that it’s the exact opposite at CastRooms.

At CastRooms the core partnership is with my co-founder Mitali. In this partnership it’s Mitali that is pushing us to do more ideas, bigger things, take more risks - and me that’s constantly urging her to do fewer things and operate within our constraints! This partnership also works beautifully - again because we trust each other, talk every day, and make a shared path.

At GDS I was seen as optimistic but at CastRooms I’m seen as pessimistic. Yet inside I’m the same person, making the same judgements, with the same attitude to risk. What’s unsettling is that it feels like my identity has changed. My self-image was always that I’m super-optimistic until I started working with startup founders :)

Founding a startup needs someone with off-the-scale optimism like Mitali (or Ben at Local Welcome) to take that enormous leap. It might even be that these kinds of founders need to be blind to the true nature of the challenge. Or they’d never do it. I’ve been saying for years that I wouldn’t found a startup because I’m not made like that and I think it’s true. I needed Mitali to make that leap and only then corral me onboard.

Stepping back, it’s made me realise that an organisation’s appetite for risk has a huge impact on not only the kind of work that gets done but also how I feel about my own role in doing the work. I hadn’t understood this until now. In cautious places I’m a naive optimist. In gung-ho places I’m a stick-in-the-mud realist. It’s yet another example of how deeply the context of work changes my experience of it.

Anyway, me and Fi had a good laugh about my optimism reversal. And she pointed out that we’re going to need people like her and Elisse pretty soon if we’re successful.

I’m looking forward to the day when that’s true. For all the reasons.

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Listening

Dan Hockenmaier talking at length about the key differences between B2B SaaS startups and Marketplace startups is the most useful thing I’ve heard this year. Perfect timing for the pitch deck we’re writing for CastRooms. We are a marketplace!

Watching

We inhaled Happy Valley 3 in two nights to avoid spoilers. Makes me want to watch everything Sally Wainwright’s written and Sarah Lancashire’s acted in. I love how it makes you feel for every character at some point. Even the awful ones.

Reading

Getting closer to the end of Babel by R F Kuang. It is not only a rip-roaring tale but it’s also making me feel all sorts of things about colonialism in that way that fiction does. These are not comfortable feelings.

Eating

The highlight of our anniversary trip was eating a lunch at Jetty Broadstairs surrounded by views of Viking Bay, the Kent coast and endless sea. You can see the Jetty in the last couple of sunrise photographs below.

Will Myddelton @myddelton

Sometimes the universe provides 🌅

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Right. That’s it. I’m off to visit kitchen worktop showrooms on the other side of London in Acton. Wish me luck.

Also, I love nothing more than getting a reply that says hello. Just saying :)

Will