#25. Startup reflections

It's 15 months since I started working on CastRooms - the startup that I co-founded with Mitali - full time in April 2022. We're bringing the energy of crowds to music livestreaming and - honestly - it has been a intense trip.

I’ve felt weirdly blocked from working in the open at CastRooms - and given how much my brain is focused on CastRooms there hasn’t been much else to write about.

Working in the open has been a big part of my life over the last decade. It's how I process things that I'm learning. It's how I try and give back to the communities that nurtured my career. And it's how I connect with the world outside our four person team and my tiny work-from-home office. This life can get lonely at times.

Sure, working in the open is tricky when things are commercially sensitive. But that's not the whole story. I’ve also been feeling a ghost pressure not to say things that might make us less attractive to investors. The work is so intense that there's barely time take a breath, let alone reflect. And the journey is so up and down that in the lows - when I'm overflowing with doubt - the last thing I want to do is share anything.

But thanks to the wonders of a one week holiday at the end of May I've been in a great place recently. And with that comes a growing desire to reflect. So here goes.

Looking back to April 2022 it feels like I had a naive view - or perhaps, more kindly, a narrow one-dimensional view - of what it meant to do a startup. Something about my background in the design world manifested as the simplistic belief that if you can make an experience so powerful that people love it then everything else will fall into place. 15 months later it's clear that building this kind of experience is necessary but nowhere near sufficient. There’s so much more going on that I was missing.

One big thing that I was late to realise is just how important it is to have protectable technology. If you're going to raise investment from venture capitalists they care way more about protectable technology than I realised. I kind of thought that would happen naturally as we figured out the experience and grew. But the question we get asked all the time is "what’s stopping someone from copying you?". It's taken us a while to have a good answer to that question.

Another big thing that I was missed was the importance of early revenue. My lazy mental model of consumer startups was that they started with loss-making growth and strapped on revenue years later. Like - Facebook didn't figure out its advertising platform for years, YouTube didn't put video ads on everything for ages, Spotify still doesn't make money, and on and on. These stories now seem like wishful thinking and even straight-up denial! Perhaps in the heyday of low interest rates and high investor confidence this attitude would have been....fine?....but it's definitely not OK today.

This all came to a head when we wrote our first pitchdeck and started pitching investors. In the same week that Silicon Valley Bank collapsed. Fun fun fun.

Writing a pitchdeck is hard because you have to tie together answers from many angles into one story. I can write, I can communicate, I can think - but putting together our pitchdeck is one of the hardest things I've ever done. Sure those 12 slides don't look like hard work! But they're the pretty little desert island that only exists as the tip of an undersea mountain of thought stretching to the continental shelf below.

These things have made the last six months of pitching investors a wild ride. There were highs. There were (many) lows. And there was utter dejection at times.

But…

…despite all of this…

…I've kinda loved the last six months.

I've slowly realised that everyone knows you're going through this process of figuring it out. No one knows it all. People expect you to struggle with it. So it's not about knowing it all upfront. Instead it's about letting the experience - the sometimes bruising experience! - teach you what's wrong and what you need to do to address it.

And that is EXACTLY like the design world that I come from. In the design world you have an idea, make a thing, put it in front of people, and observe people reacting to it to figure out how to make it better. In the startup world it's the same process with different objects - a business rather than a design, investors as well as users, months rather than weeks for the iteration cycles, revenue rather than delight as the metric.

So here we are, 15 months later, iterating CastRooms based on what we've learned along the way. A radical go-to-market pivot refocused on early revenue. A deep understanding of how to build and protect our unique tech. A beautiful pitchdeck that gets more compelling each time we update it. A vibrant pipeline bursting with wild commercial opportunities. And - of course - a core product that our users love.

Yes, it’s stretched me to my limits. Yes, it gives me the fear. But the thing I love to do most is to figure out what’s wrong with my mental models and then go about adjusting them to a new reality. CastRooms is definitely the vehicle for that :)

Originally posted on Substack along with Are we not drawn onward to new erA, These Times / Past Present Future, Some Assembly Required, two egg omelette. Say hello or ask questions on @myddelton.

#24. Gall’s Law

A lot of my career has been focused on bringing new things into the world. In all the reading and learning that I’ve done over the last 15 years there is one short, profound paragraph that has embedded itself deep in my worldview:

“A complex system that works is invariably found to have evolved from a simple system that worked. The inverse proposition also appears to be true: A complex system designed from scratch never works and cannot be made to work. You have to start over, beginning with a working simple system.”

Gall’s Law

I’ve been thinking a lot about Gall’s Law this week. It feels like a good time to try and capture my thoughts about why it’s so foundational to me in making new things.

So let’s give it a go.

We swim in complex systems

The mundane truth is that we are surrounded by complex systems. Enmeshed in them. Pretty much anything that makes up our daily life - food supply, PAYE taxes, internet wifi hardware, organisations’ hiring processes, social media networks, rave culture and club promotion, and on and on - is a complex system. Anyone who’s read Donella Meadows will recognise the prevalence of complex systems in our world.

Gall’s Law says that none of these sprang into being fully formed. All of them evolved from simple systems that worked. But we don’t see this. And that costs us.

We don’t see it because - as Daniel Kahneman tells us - What You See Is All There Is. And what we see is complex systems! Unless you are paying deep attention to the history of system evolution for everything - impossible given how many systems there are and how difficult each one is to comprehend - then you’re blind that the working complexity you see everyday evolved from simple working systems in the past.

We dream complex dreams

Fine. This is just another cognitive bias. Until you try and make something new.

When we start thinking about making something new we tend to model the new thing on what we can already see around us. And what we see is complex systems! This leads us to dream of creating new complex systems without even knowing we’re doing it. Anyone who’s imagined a different future knows how easy it is to “see” our dream system in our mind. It feels so clear to us how it will work, how this feature will be useful, how this this risk-mitigation will be essential. It feels so real.

With this clear image in mind we unwittingly set out to design and deliver a complex system. We invest time and effort in thinking through all the facets of the dream system - the brand, the support model, the edge case features, the safety measures, the financial model, the internationalisation, and on and on and on.

Complex dreams fall apart

But this is a trap. And it’s a trap that limits our dreams.

Every new facet that we add to our dream system makes it more complex. Every change we make in the dream system has ripple effects throughout the whole. The work takes longer and costs more - and in taking longer new actors enter and add more facets with their own ripple effects. Before we know it our dream system - which once seemed tangible and real - is compromised, over-budget and long overdue.

Worst of all, not only has it taken ages, but when we launch it Gall’s Law tells us that it won’t work. That we might even have to start over, beginning with a simple system.

The unspoken tragedy of this is that the biggest dreams - the kind of dreams we need most in our society today - are exactly the dreams that are the most susceptible to these compromised, overdue, over-budget failures. The bigger the dream, the more likely you are to end up designing a complex system that simply does not work. And in the process you often burn your financial, political and social capital too. Argh.

Time is on your side

The answer isn’t to stop having big dreams.

I think that the answer is that once you have a big dream you need to step back and remember Gall’s Law. Specifically, you need to clear your head and figure out a pathway that starts with a simple system that works. And then put your trust in the evolution of that simple system.

It’s hard to trust in that evolution though.

One reason we find it hard to trust in evolution is because we’re bad at “seeing” time. When Darwin suggested that humans (complex systems!) evolved over thousands of generations from earlier life forms (simple systems!) many Victorians found it preposterous because they couldn’t visualise the ‘deep time’ of geology. In the same way, many 21st century knowledge workers can’t visualise the ‘rapid time’ of iteration and so find it preposterous that goals will be achieved in an unknown future.

Another reason we find it hard to trust in evolution is that it doesn’t feel intentional enough. Too random. But the evolution of a simple system doesn’t have to mimic the random mutations of biological evolution. Every time we learn about our simple working system - from observing usage, gathering data, talking with colleagues - we equip ourselves to evolve it in ways that lead towards our complex dream.

A simple working system plus time and guided evolution is radically powerful.

Gall’s Law runs deep

I spend my life trying to make new things. My fundamental role on teams is to plot a path to the complex dream we have for the future but that - somehow - starts with a simple working system. This is why Gall’s Law resonates so much for me.

So much of the world pushes back on this. We want our complex dream and we want it NOW! We are too sophisticated for this simplicity! In large organisations each functional discipline brings a default wishlist that creates high complexity before we even get started. Paradoxically, it’s often harder to get agreement on a simple working system than it is to get buy-in for the all-singing, all-dancing complex version.

As an aside, you might be thinking that Galls’s Law is just a rehash of Agile or Lean. I think it’s the other way around. Yes, Gall’s Law is part of what makes Agile and Lean powerful. But, for me at least, it’s a more fundamental philosophy that applies way beyond software development. Also it was written in 1975 :)

I’m sure there are domains and instances where Gall’s Law doesn’t apply. In fact, I don’t actually think it’s a ‘law’ at all. For me it’s just a powerful thinking tool when you’re trying to work out how to make a complex dream come true.

And, for me, that IS the work.

Originally posted on Substack along with Fleishman Is In Trouble, Luke Una, Perdido Street Station, birthday feast. Say hello or ask questions on @myddelton.

#23. Selling books

I spent last week going through books from my loft and selling them. It’s been a cathartic experience. If not a wildly profitable one.

It’s been cathartic because I’ve got a deep relationship with books. My mum didn’t let us have a TV until I was 14 so books were my entertainment. I studied a bookful subject at university - history - which was one big reading list. When I switched to be a designer I did this by reading every book about design I could get my hands on.

But that deep relationship changed. I stopped reading fiction books in my 20s and when I restarted in my 30s it morphed into Kindle and then audiobooks. I haven’t had a reading list for academic study for nearly 25 years. And in switching careers to be a product manager it’s not been books that have guided me this time around.

The one lingering connection is aesthetic. I grew up in a house with books spilling off shelves and piled up on the floor. Multicoloured spines have always been decoration. Texture. Colour. Pattern. At our flat in Haringey I made floating shelves with my friend Jeff to hold the books I loved most. I know people see this as ostentatious smugness - fair enough! - but for me these books also felt like chapters from my life.

Then in 2016 we left Haringey and the floating shelves. Sadface.

The books got boxed into the loft until “after the renovation”. We didn’t renovate for years. And now, six years later, my books are out of sync with my life. I switched to Kindle and audiobooks and the books just…stopped. New shelves would be partial, incomplete. (Sometimes I even daydream about buying loved Kindle books as physical copies to keep the illusion going! Absurd.)

So, long after my reading habits changed, I’ve let go of my lingering aesthetic too. Our renovated space won’t have rows of battered books for texture, colour, pattern. I’ve had to figure out what else might do that job (hello tiles?) and develop a new aesthetic. This has been tricky. But also kind of fun once I accepted and embraced it.

So last week I found myself scanning and sorting books into piles for WeBuyBooks, Sellitback and Ziffit (prices vary wildly across all three so multiple scans is the way).

It made me sad to let these chapters of my past go. But I’m happy that I’ve noticed a different thing. In emptying and refilling my loft I’ve spotted that I operate with two fundamentally incompatible behaviours. On the one hand I keep all sorts of things - books, music equipment, keepsakes - to return to in the future. On the other hand - now that I’ve lived in this ‘future’ - I’ve realised that I never do return to the past.

It just takes time for me to let things go. Not just books. Habits that once helped but now hinder. Friendships that formed before lives diverged. Beliefs that felt immovable until new stories and evidence showed up to change my mind. As I move through my 40s it feels like this breaking-and-remaking only gets more important. I don’t want to get stuck as any version of myself. I’m not quite sure why that’s so important to me?

Finally, just in case you think I’ve got monstrous resolve, I should be clear that I haven’t sold ALL my books. Some were just too painful to let go. For now anyway :)

Originally posted on Substack along with The English, Algorithmic Injustice, The Destroyer of Worlds, bubble and squeak. Say hello or ask questions on @myddelton.

#22. 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.

Originally posted on Substack along with an intro/outro, Dan Hockenmaier, Happy Valley 3, Babel (again) and Jetty Broadstairs. Say hello or ask questions on @myddelton.

#21. Good enough

One of the stark things I’ve learned over the last nine months is how different things are at a violently early-stage startup like CastRooms than in bigger organisations.

What’s jarring is that so much public wisdom around research, design, marketing, development and data doesn’t work well at our early stage. Forget having product-market fit - we are still pre-customer! So Twitter, blogs, books and podcasts leave me feeling lesser-than because I’m so clearly out of step with my peers.

I’m slowly finding early stage wisdom - guests on Lenny’s podcast talk about ‘zero-to-one’, Kent Beck talks about Explore, Simon Wardley talks about Explorers. But it’s rare.

My own shaky early-stage wisdom comes from Local Welcome and CastRooms. What strikes me is just how much there is to do (everything!), how few people there are to do it (4-6), and how little time there is before the money runs out (months not years).

The best response I’ve found is ‘good enough’ across the board.

But ‘good enough’ does NOT actually ever feel like ‘good enough’! This is non-obvious until you live it. The actual feeling is more like ‘this is appalling and I’m embarrassed to show my peers because they’ll laugh at how terrible I am on all levels’.

So today I’m talking about what ‘good enough’ decisions look like at CastRooms, how they often make me feel embarrassed, and why I’m mostly OK with that.

Good enough research

Let’s start with user research. We didn’t test any of our designs with users for six months at CastRooms. I’m a former lead user researcher FFS. We could have mocked up prototypes and tested with users in less than a week. When we did test our designs with users we found loads of usability issues. WTF was I doing leaving it so long?

Well, CastRooms is a social streaming product. I felt we could find and fix usability issues later (true). Our riskiest assumptions were actually all about group dynamics. How do people behave in our novel social setting? ‘Good enough’ here was the fastest route to get to real tests in a novel social setting and that took us six months to build. Bluntly, even fast research cycles and iterations take time, so we traded them in.

I lived with early-stage user researcher embarrassment for six months until we could test CastRooms in the context-of-use that would answer our most important questions.

Good enough design

Then there’s design. The graphic design of our product is barely more than a glorified wireframe. It ugly. Our website doesn’t match the product - neither does it match the promo sites we make OR the ticketing platform our users go through. None of that matches the emails we send or our social media posts. Beautiful design is a key part of consumer products like ours so how is this remotely OK?

This time it’s about money. We don’t have a graphic designer in our tiny team. We do have money set aside for design work but only enough for one pass. Spend that money too early and we risk blowing it on the wrong approach. Spend it too late and we look like amateurs when we pitch. So until now ‘good enough’ design has been about making sure that people aren’t blocked from participating in our test parties by design. We traded in beautiful, consistent design for rapid, messy iterations.

Early-stage design embarrassment is the hardest. I hate showing our work to designer friends the most! But we’ve protected that precious budget for when we need it most.

Good enough marketing

Closely related is marketing. Our messaging is all over the place. Our proposition shifts from week to week as we experiment with different takes. We’ve been through at least three different positioning stances since September. Worse, these changes often mean that one part of our journey has different messaging from the other parts! How can we expect to generate the traction we need without strong marketing?

Well, brutally honestly, we don’t quite know who our customers are yet. We have hypotheses and strong leads but we’re in discovery mode. Great marketing needs a clear audience so our marketing has been…not great. ‘Good enough’ marketing is doing enough to book three DJ interviews a week and get enough people into our parties to test the experience. We traded in performance for short term expediency.

The difficult thing about early-stage marketing embarrassment is everyone telling me what’s wrong. Like I don’t know. But we get the people we need so I grin and bear it.

Good enough development

I’ll touch on development. We don’t have any automated tests so we have to do pure manual QA when we release new things. Ouch. Me and Tommy do it together and it’s boring, repetitive and we miss things. Worse, we don’t support iOS or Android yet even though that’s half the people that come to our parties. What kind of modern web product doesn’t have automated testing or support mobile devices?

The truth is we’re not a proper product yet. Looks like a product to users - website, join journey, social experience. Looks like a product to the business - codebase, deployment pipeline, Linear tickets. But it’s really a series of prototypes / MVPs / RATs to test our riskiest assumptions. ‘Good enough’ development is making this pretty complex thing that lets us run experiments in novel social settings with distributed participants. We made harrowing tradeoffs to build the thing in time for us to learn massive, important things before we start pitching investors.

I find early-stage development embarrassment easier to live with cos I’m not Tommy! But I see what we learned from the sketchy thing we built and I breathe easy.

Good enough data

Finally, let’s talk about data. We didn’t have basic web analytics on our join journey for 90% of the test parties so far. We didn’t add event tracking to let us see what users were doing inside the product until two weeks ago. We’ve collected attendance data since October but didn’t look at it until this year. This feels egregious for a product manager. Isn’t our core skill to be data-led, or at least data-informed?

Well, yes. Except that data - for me - isn’t just numbers. The whole point of running test parties - with real people using a real thing in the actual context of use - was to observe how people behave in this novel setting. We have tons of observational data that has driven product iterations ever since our first test party. ‘Good enough’ data that led to huge intuitive leaps in product design. We traded access to robust quantitative data for better visibility of humans using our complex thing.

I felt lots of early-stage data embarrassment because ‘data-led’ is a truism. But now I’m peaceful with leaving it late because numbers weren’t actually important early on.

Risky assumptions and speed

Those are five areas where ‘good enough’ in theory has felt embarrassing in practice. They made me feel lesser-than whenever I heard about the wonderful work other people are doing. All these compromises ended up making me feel…compromised.

But I grit my teeth and do it anyway. For two big reasons.

First, at a deep fundamental level, I think early-stage startup life is ALL about finding ways to test our riskiest assumptions as quickly as we can. That’s where we learn the biggest and hardest stuff that leads to quantum leaps. Cantlin put me onto Marty Cagan’s Four Big Risks and that’s a helpful way to think about this. At this early stage I am obsessed with Value Risk (whether customers will buy it or users will choose to use it) and Feasibility Risk (whether our engineers can build what we need with the time, skills and technology we have). Until we’re solid on those I’m not that worried about Business Viability Risk (whether this solution also works for the various aspects of our business) because we don’t have a business until we have something valuable and feasible. And I don’t care Usability Risk (whether users can figure out how to use it) because with numbers this low we can do manual support (we do!) and I trust us to figure out and fix major problems when we test (we did!). Of course, as we get deeper, this risk focus will radically shift.

Secondly, the need for speed is simply overwhelming at this early stage. There are four of us. We have £X in the bank which lasts until Y date and when it’s gone we’re done. We have to make things that give ourselves a chance to find insights that will persuade investors to bet on our future. It’s incredibly stark. It focuses the mind. Suddenly the harrowing tradeoffs don’t only seem possible but essential. Given how much clearer these tough decisions feel it makes me wonder how we might simulate these conditions in larger organisations?

One final thing about speed. Venkatesh Rao recommended the The Perils of Prudence by Abraham Thomas and this paragraph leapt off the page at me:

This is wildly counter-intuitive to me. I’ve burned out several times. Yet despite working just as fast - if not faster - at CastRooms I don’t feel remotely burned out yet.

I wonder if there’s a hidden side effect of making these ‘good enough’ decisions all the time - that I am no longer trying to deliver something to someone else’s expectations of what ‘good’ looks like? Yes, it’s hard work to figure out what ‘good enough’ looks like myself. Yes, it’s hard living with all the embarrassment. But perhaps the act of making ‘good enough’ decisions is protecting me by stopping me working late to polish details that don’t really matter?

Anyway.

This is how ‘good enough’ plays out for me at CastRooms. I’m not saying I’ve made the right decisions every time. I have, as always, made plenty of mistakes. But constantly finding our answer to ‘what is good enough’ is the way I’ve coped with how much there is to do, how few of us there are, and how little time we have.

Originally posted on Substack along with an intro/outro, The Perils of Prudence, Julian Shapiro, The Witcher and Jamie's vegetable lasagne. Say hello or ask questions on @myddelton.

#20. Writing style

In the weird quiet of recent-Twitter I’ve been trying to discover more voices by spending time in the “For You” section. This is where the algorithm suggests tweets from people that I don’t already follow who it thinks I’ll like.

Occasionally I find interesting stuff. Most of the time it’s trash.

One reason it’s trash is that the algo loves tweets from People With Opinions. My tolerance for tweets that start with “Unpopular opinion” or “Handy reminder” is low and falling further by the day. It’s probably time for muting these phrases.

I’m increasingly tired of listening to People With Opinions shouting loud certainties into the void. Don’t tell me what to think! But it also got me thinking about my own writing style. Because I used to do this too.

Looking back it’s clear that I wanted to be part of the People With Opinions crowd when I was younger. My early writing often reads like I was trying to instruct readers about the one true way of how to do things - from how to work with clients to ways of thinking about success and even down to what words to use.

Stylistically, these posts are full of what “you” should do and what “you” should think. Reading them back they sound way too certain and even veer into feeling aggressive at times. Any valid or interesting points get a bit lost in this over-confidence.

I was imitating the confident style of blog writers and conference speakers that I looked up to as an early career designer. I hadn’t worked in enough places or environments to understand that good advice is contextual and the quest for a universal truth is often futile. Most embarrassing I can catch an echo of the schoolboy who is eager to get top marks by sounding ‘right’ about things. Ouch.

A change in style

Sometime around 2017 my writing style started to change. I clearly still had Opinions (not sure that’ll ever change!) but stylistically these posts are now peppered with what “I” had done and what that made “me” think about things. Much less “you”.

This change in writing style happened through three conscious shifts.

First, I started to position blog posts as accounts of my own experiences rather than wider truths. My most-shared posts ever - user research is a team sport and three ways to run better discoveries - are both explicitly framed as personal stories in the introductions. I have John Waterworth to thank for this. He told me to stop writing “the manual” and instead to share personal stories from the ways I’d been working.

Secondly, I started to provide more personal context about who I was, what I was interested in, and what career experiences I’d had. This came from Caroline Jarrett the night before my first big conference talk about research heresies. Her simple feedback was to stick in a slide about personal context. Her rationale was that this helped people figure out whether they should be taking advice from me or not!

Finally, I learned to be more vulnerable in my public writing. Amber said that she’d learned the most from me when I talked about the (many) things I’d got wrong. I wrote I’ve made mistakes in response. Re-reading it still makes me shiver about some of the things I owned up to. The response convinced to be a little more open than I was comfortable with being in my writing. I think 40 lessons showed this new openness.

Easier to write

After these changes I found it easier to write. Not easy, but easier. For a few reasons.

  1. I’m no longer grasping for out-of-reach universals. My writing is just about my own specific experiences. It’s easier to write about specifics! I’ve found that being more specific makes my writing resonate more widely too. Not every reader will match my specifics but it’s surprising how many of them strike a related chord.

  2. I’m not trying to be ‘right’ any more. I don’t worry about making my writing ‘right’ for all situations and instead I leave it up to readers to decide for themselves. It’s easier to write like this! I’ve found this stance has helped me with my life’s work of moving from competitive schoolboy to humbler adult too. That road is long.

  3. I don’t mind it being focused on ‘me’. I used to feel self-indulgent using “I” and “me” but I’m over it. It’s easier to write from the first person for me! I realised that using “you” was also a hangover from my writing-for-the-web days when I wrote copy as the voice of the organisation. I am not an organisation.

  4. I’ve had a LOT of accidental practice writing in this style. I’ve written morning pages since 2012. Mine are full of specifics (not universals), reflections on what’s gone wrong (not right), and peppered with “I” and “me”. Bashing out 750 words each day - 1.1 million words and counting - has made me fluent at this style of writing. I didn’t start morning pages to evolve a writing style but maybe that’s what has happened?

So I find it easier to write these days. Never easy - as my hiatus shows! - but easier.

One final thing. I said the trash tweets from People With Opinions got me thinking about my writing. That was a half-truth. What actually started me on this rabbit hole was a touching piece of feedback I got from a friend after I restarted this newsletter:

Every writer wants to find their voice. Me included. I’m sure my voice will change and shift over the years. But I’m closer to finding my voice than I once was. And that feels like something worthy of reflection and - perhaps just a tiny little bit - of celebration.

Originally posted on Substack along with an intro/outro, Fabio and Grooverider, Happy Valley 2, The Status Game, DrinkAware. Say hello or ask questions on @myddelton.

#19. Startup guilt

We’re about to start raising money for CastRooms. 2023 is going to be a wild year for us. Make or break. But before that starts I want to spend a little time looking back.

One theme that stands out from 2022 for me is feelings of guilt. Before we started CastRooms I imagined our journey would be exciting and scary. But one of the dominant feelings that I ended up experiencing was various flavours of guilt.

So this is my weird story of last year in terms of rolling waves of guilt :)

From April to June we were figuring out our initial positioning in the market and planning the foundations of our product. I did lots of competitor research at the same time as firing up a user research pipeline and speaking to tons of DJs. My instinct was that I didn’t know the landscape well enough to build the right product or create a useful strategy. So I spent time exploring and asking lots of questions.

This was when the first round of guilt kicked in. From my second week at work. It was weirdly hard for me and Mitali to get up and running even though we’d been looking forward to this for six months. Our excitement at the open-road freedom of starting our own company didn’t magically translate into a sense of momentum. Spending time asking questions and exploring, rather than cracking on with ‘making things’, felt complicated in an unusual way. I think because the days and weeks were intimately connected to spending the actual limited money we had from our investors.

Looking back, it seems I forgot how difficult it is to form a new team, to build trust, to understand the competitor/user landscape, and to generate the shared understanding needed for progress and momentum. Of course it takes a while to find your feet. So despite feeling guilty for three months by July we were starting to run nicely…

From July to September we focused on building the prototypes necessary for our first tests with real users. We were making a multi-person experience where a bunch of people - some of them friends, some not - would gather online to watch and listen to a live performance from a DJ that they loved. A small online party! We wanted to make this experience from scratch to start running and observing test parties.

My guilt here was a user researcher guilt. Why was it taking us six months to test things with users when it’s possible to prototype and test in days? I had made a conscious decision not to test static mockups and a single-person experience because our riskiest assumptions were about behaviours in a group context. I felt that our biggest learning would come from prototyping a more realistic context-of-use and I accepted a ton of usability risk to get to this situation. But even though I’d made a conscious decision to do this I still spent six months feeling like I was ‘doing it wrong’.

Looking back, I’m OK with this decision despite six months of researcher guilt. We started test parties in September and the group behaviours we observed taught us all sorts of unexpected things core to our proposition. It’s true that we found usability issues that we could have caught earlier with static mockups. But in our extreme early stage startup I don’t think usability risk was the right focus. We were mostly interested in value risk and a little bit of feasibility risk. (Also I realised later that my user researcher guilt was ignoring the multiple customer interviews we were doing every week. It wasn’t like we’d done six months with no user research.)

From October to December we ran test parties every week and added in the final technical element of our product. Our test parties gathered a small crowd to watch a DJ they loved playing a live set - which turned us into small-scale promoters and meant spending a LOT of time on logistics. At the same time me and Tommy were building the final element we needed to complete our intended context-of-use. This would let us observe important behaviours before pitching in January.

The guilt during this period came from all angles. With limited time we chose to sacrifice important things - automated testing, multi-browser support, smooth join flow, mobile support, data collection, accessibility - to get the element done before Christmas. My user researcher guilt now expanded to add designer guilt, developer guilt, analyst guilt and inclusion guilt. Not to mention strategist guilt that came from being so head-down I had no time to look up and see the bigger picture. I don’t think I’ve ever felt like such a fraud and a sham at work as I did during this period.

Looking back, getting that element in place was transformational even with all the sacrifices. The tests we’ve done with it advanced our understanding of our product possibilities tenfold. All the pitch-preparation we are doing now references that element as the central plank. We sacrificed things to get there, and bits of our product are held together by string, but we tested our riskiest assumption in time to pitch.

And that’s where we are now. 2023 and time to pitch.

It’s strange to realise how much of my feelings about the startup have been guilt. Before I wrap this up I want to reflect on how I feel about these guilty feelings.

Some guilt was to do with my personality. I am an agoniser, a re-thinker, a sceptic, a questioner. I hold things too close and worry too much. There are things that I could and should do to work on this. To be honest writing this piece is one of them. It helps to contrast my feelings of in-the-moment guilt with the knowledge from hindsight :)

Some guilt was about not knowing what to do and feeling like a fraud. There’s a knowledge gap around the early stages of a startup when you are pre-customer and getting to product/market fit is a distant dream. Lots of product wisdom is about optimising existing products, with known customers, in defined markets - as this is where most products and their teams find themselves. I found myself hungry for the moments in Lenny’s podcast when a speaker would go off-script and talk about how things are different early on and collecting these gems. They call it the zero-to-one journey and I’m hoping that now it’s got a name it might be easier to talk about?

But most of my guilt comes from feeling out of step within a culture of conformity. People on Twitter/blogs/conferences/podcasts speak so loudly about their ‘one true way’ to do things - develop a product, do user research, be data-driven, avoid exclusion by design, set up your development environments - that it makes me feel lesser-than when I’m not doing things their way. Early in my career I accepted these loud opinions as truth. As I’ve got deeper and worked in all sorts of contexts - agency and in-house, large organisations and startups, public / private / voluntary sectors, designer / researcher / product manager roles - I’ve turned sceptical about orthodoxy and doctrine. These things are only useful inputs if you are thinking for yourself. And yet, despite this being so central to me that I did a talk about research heresies in 2018, I still somehow feel guilty when I see loud doctrine and compare myself to it.

This tweet from Edo van Royen sums it up nicely.

Anyway, that’s my story of CastRooms in 2022 through the lens of my unexpected feelings of guilt. It’s a weird frame but it crept up on me as an intriguing way to reflect on a year of big decisions and associated responsibilities.

Perhaps my goal isn’t to eliminate guilt but instead recognise and understand it better? Perhaps guilt is a built-in balance against becoming blasé and overconfident? Perhaps guilt is one of the mechanisms that keeps me focused on whether or not we’ve made the right big decisions? And perhaps guilt is the cost of having the freedom and the privilege to reach my own decisions in the first place?

Either way I think the guilt is here to stay. And I’m OK with that. Mostly.

Originally posted on Substack along with an intro/outro, Facing Heaven, The Bear, Obviously Awesome, Babel. Say hello or ask questions on @myddelton.