Hermitage and habit

No.004 - The importance of persistence

I prefer to write infrequent long-form newsletters. I want them to be worth your time. Today I’m experimenting with an introductory summary for you to choose which parts you want to read, and when, upfront.

If you’re new to Designance, it’s a newsletter I write while exploring the principles of design and finance, pitting my investing skills against creating a product of my own. If you’ve been reading from the start you may have noticed they’re structured in three parts: recent events, an exploration of a subject and product research insights.

In this edition

  1. I invest in Cowboy bikes via Crowdcube and learn about the downsides of crowdfunded investments the hard way.
  2. There’s a lesson in the importance of persistence and habit forming (and a brief aside into the commercial model behind film festivals).
  3. I talk through some of my research insight and decisions I’ve made about my product, and how to take it to market.

Grab a ☕️ – 15 minute read

I. Cowboy investing

About a year ago I heard a first-hand account of a product made by a Belgian e-bike startup. My friend, a keen cyclist, explained how this product had solved one of the major problems e-bikes suffer from; lack of smooth power delivery1. I’d not seen or tried their product, but when I saw they were raising on Crowdcube last year, I made an investment.

Making an investment armed with only a slither of ‘good authority’ and the investment thesis ‘never bet against a good product’, placed it firmly on the scale of risk somewhere between pretty speculative and plain daft:

very risky investment as the only realistic chance of a return is if the company gets bought or does an IPO, neither of which is planned anytime soon. In case of liquidation all other investors come first, so realistically in that case you end up with nothing”, aforementioned friend via Twitter

Before I get to the inevitable conclusion of this story, I want to explain what crowdfunding platforms offer, what makes investments on these platforms particularly risky, and in my view not particularly worthwhile.

For the sake of this story there are two types of company; private and public. As a retail investor, buying shares in a public company is a fairly simple process that involves opening up an account with a financial services company and then instructing them to buy shares in a publicly traded company on your behalf. Anyone can do this. As an example, buying one share of Microsoft would cost me £1702. So far so simple.

Investing in private companies tends to be a more complex process and typically involves larger sums of money. One way to invest in private companies is to invest in a Venture Capital Trust - effectively an investment in a VC firm who invest in private companies. A foot in this door usually costs £5k and up, and although tax incentives exist, these are considered high-risk investments3.

This is where crowdfunding platforms like Crowdcube fill an interesting gap. The risk profile doesn’t change – they’re still privately-held, often early-stage companies – but the cost of entry is considerably lower, often starting at around £10.

I’ve previously written about wanting to invest for the long term. Rather than big IPO paydays, I’d prefer to receive small dividends. 


Most of the companies pitching for equity on the Crowdcube website are start-ups or early-stage companies, and these companies will rarely pay dividends to their investors. This means that you are unlikely to see a return on your investment until you are able to sell your shares”, Crowcube’s “Risk warning

This is my first issue with crowdfunding and brings me back to the point of this story.

I completed a (small) investment in Cowboy’s “Series A” in January 2020. Less than 6 months later several thousand others and I discovered that unbeknown to us, Cowboy had wrapped up a Series B “down round”.

In essence, Cowboy took (significantly) more investment at a surprisingly lower valuation4, and having the effect of reducing the value of my shares by some 34%5.

Worse still, the terms of the new investment reduced the rights of Cowboy’s crowd investors. If a liquidity event6 were to occur now, Series A investors are further back in the queue, or without preemption rights7 should another round of funding occur. Comically, we were asked to vote on this while simultaneously being informed that the outcome of the vote didn’t actually matter and the new raise would go ahead regardless. 

To raise a second round so soon, and from a weakened negotiation position is surely indicative of something having gone wrong. To find out why, I attended Cowboy’s first ever investor call on 9th September 2020. Sadly, no satisfactory reason was given8, which pushes the next paragraph into speculation territory.

It seems to me that Cowboy’s choice to raise money via Crowdcube was less about crowd investing, and more about collecting proof of market confidence in their value proposition. The mistake they made was offering the crowd Series A terms (ie. pretty good terms), then failing to treat them with respect as investors. 

Still, better that the shares exist on worse terms, than not exist at all. The company lives to fight another day.

If few options exist to easily invest in private companies in early anticipation of IPO, then fewer still exist for companies that want to bootstrap and achieve profitability without an “exit strategy”9. Perhaps the only way is to do this is to create and invest in a company of my own.

II. The importance of persistence

In 2008 I was living in a shared house with three friends. You’ll remember 2008 as the year that the sub prime mortgage crisis brought the financial system to its knees. We experienced a similar problem on a smaller scale; a rent crisis caused by one friend quitting their job on principle. 

I say “on principle”. Eventually it transpired that he’d booked a haircut one afternoon in anticipation of the time off work being approved. His boss, apparently “high on power”, refused to approve it. Rather than change their plans, my friend and regular rent contributor quit. 

Once we’d worked out how to pay the rent it was hard not to be quietly impressed. Values aren’t worth anything until they’re costing you money, and it was costing him more than us.

It wasn’t a great year to be looking for employment, and 2008 seemed like an even poorer time to consider starting a venture. So for all his wisdom, he took our City’s name, appended the words “film” and “festival”, bought a domain and set about creating a film festival.


Over the last 12 years I’ve listened to countless bold and incredulous plans – even participating in a few while always suspicious that the festival would work:

“You can’t just use the name of a city without permission! Can you?” Yes; turns out that’s fine - it’s good promotion for the City

“Film Festivals are run for the love of it, they don’t make money! Do they?” Yes; the commercial model is odd, but it exists10

**“There’s no chance you’ll get to support and promote your festival! Is there?”** Yes; fantasy-dinner-guest-type people will, in fact, do just that.

I have many more examples, and they each represent a challenge overcome through persistence. I got this text last summer11:

Do you remember all those years ago when I was dicking about and unemployed and decided to set up a film festival for a bit of a laugh… well, we’re now a fully fledged BAFTA qualifying festival, on a par with […] Raindance

It’s all the encouragement I need to keep going with this project. I’m not returning to office-based working any time soon and winter is on its way. I plan to take full advantage of enforced hermitage by building daily habits around my newly-found persistence.

III. Designing developer tools

Every product has an interface, a mechanism to interact with a product as a human. To take an example from the physical world, the interface for a door is its handle. In the digital world, the interface is typically a graphical representation of a real-world concept (like a buttons, or fields on a form) produced on a screen.

These graphical user interfaces (GUIs) are created by people who think about several aspects as they design their product. In the case of an App a designer considers everything from the visual experience and interaction design, to the overall product experience (“UX”). Designers have their own products and tools to help them do design work for GUI products.

Products made for software developers – imaginatively called “Developer tools” – are different. Their user interfaces are generally text-based, and use interaction concepts that are abstract from the real-world.

Developers interact with these products through things like configuration files where your desired settings are defined, or command-line interfaces (“CLIs”) where you instruct the product to do its thing, right through to application protocol interfaces (“APIs”) which allow you to write software to tell the product what to do.

Because these interaction mechanisms are abstract, designing developer tools is a hard job usually left to software developers. If there’s one Tweet that sums up the state of design for developer tools, it’s this one:

I’m a product manager of a developer tool. Believe me, the design challenge doesn’t stop at the implementation of the interface, or even the interaction design. It’s an unsolved problem that goes deeper. Much deeper; algorithm design deep; AI systems design deep; machine learning capability design deep. 

I’ve done my time as a user experience designer – I left having got tired of framework fetishisation – but I haven’t stopped caring about it as a discipline. It frustrates me that I’m yet to find a designer who’s even mildly interested in the developer tools design problem, let alone willing or able to solve it.

want to design software that’d enable your average UX Designer to put down their GUI design tools, and become capable of designing for non-GUI products. I doubt there’s even one designer out there dreaming of the day they can give up Figma to design in SysML12

The key to launching any product is to begin with an unrelenting focus on solving the problem for the type of person who most readily recognises it, and who has an incentive to alleviate it. In other words, I’ll produce a design product for Developers13.

Since this product is aimed at helping software developers develop developer tools, you might reasonably expect I’d need to create some software. A sort of “Sketch for API design” that’ll plug nicely into GitHub. Except I can’t code (not well, anyway).

I don’t think I need to.

Getting meta for a moment (yes, more meta than ‘helping developers develop developer tools’), you can think of software simply as a mechanism to capture human knowledge. Anyone who can get hold of that software is now in possession of that knowledge. For example, you know how to send email because you have a Gmail account. Implicitly you hold the knowledge of how MX records and servers work, you just didn’t know it (or likely care!).

In my case I understand the principles of product design, and I understand the technical makeup of developer tools. All I need to do is capture that knowledge – without codifying it in software. 

There are lots of ways to capture and transmit knowledge including videos, books, slide decks, email, and conference talks. The trouble is, these formats lend themselves more to academic study than, necessarily, practical application. Without an easy route to practical application, all you’re really selling is aspiration (which, by the way, is the true job-to-be-done of a design conference).

So I need something with the structure and practicality of software, but with the ease of delivery of a book. Luckily it’s 2020 and “No Code” tools exist. There are several to choose from, and there are examples of product being built on top of each:

All I need to do is choose one to build on top of and get making.


  1. In the EU, electric assistance in e-bikes is limited 15.5mph. Beyond this speed the assistance cuts out. It’s (relatively) easy to hit that speed on a geared road bike, which makes finding the right gear to maintain that assisted speed quite difficult and the cut-outs annoying. Cowboy solved this. 

  2. This is made up of the share price (£160 at the time of writing), plus a transaction fee of around £10 from my provider) 

  3. Most venture capital backed businesses fail. You’re also handing your investment decisions to someone else. I suspect the primary purpose of a VCT is for their tax advantages. 

  4. It’s worth reiterating that Cowboy is an eBike manufacturer operating in strong market driven by the global pandemic. 

  5. From a Cowboy shareholder update on Crowdcube: “Your shares are worth €13.48. This is a 34% decrease relative to the Crowdfunding round you participated in because the pre-money valuation for the Series B round was lower than the post-money Crowdfunding valuation (€48M vs €66M).” 

  6. A liquidity event turns your share ownership in to cash. Here I’m using it to cover two cases: voluntary (Eg. through the issuing of dividends), and compulsory (Eg. via insolvency) 

  7. Pre-emption rights was a new one to me too; simply it’s a right to first-refusal on newly issued shares; a way of preventing share dilution 

  8. Cowboy simply said that they “needed to raise money quickly” and that the terms were due to macroeconomic conditions making VC investment harder to get 🤷‍♂️ 

  9. I considered writing about TinySeed and AngelList Syndicates here, since they make the sort of investments I’d quite like to make and they are trying to make this “asset class” more accessible to investment. That said, entry into TinySeed’s latest fund appears to start at ~$100k, and both require you to be an accredited investor. 

  10. Film makers pay to submit their films for judging, among other revenue streams (tickets, sponsorship etc). As an example, The Toronto International Film Festival made a CAD$3.9MM profit on a CAD$44.8MM revenue in 2019 

  11. In reality, I knew it had paid off when I heard the festival mentioned while casually listening to Ep. 115 of the Adam Buxton podcast over Christmas 2019. It’s 06m:20s in if you’re interested… 

  12. I know there are designers thinking about this challenge in the abstract though – like Ryan Singer via Synthetic A Priori

  13. Longer term I suspect the end user will change and the barrier to use will lower, to the point where designers are using my product to design non GUI products. I actually think it’ll take a major shift in the design market – Ie. fewer jobs for GUI designers – for this to happen. 

© Jonathan Roberts 2020
I occasionally update articles to fix typos, improve readability or modify content when new information is available to me. View revisions for this article.