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In the first year or two of a company’s formation, it’s not unusual to have co-founders hit a wall in their relationship and have it become a point of division that if dragged out, ultimately leads to the company’s demise. Co-founders hitting a wall isn’t an uncommon occurrence; however, I believe many of these situations are not only preventable if addressed early enough, but also reversible if handled with grace and patience by everyone involved.

Going through the process of resolving a founder dispute isn’t as simple as reading a blog post — however, hopefully the below points will help…

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Internal (and external) communication are likely the most critical aspects that a startup leader has to develop to both get alignment and clarity on next steps from their team, as well as assistance from those around them.

To help with that communication process, the Skype team came up with a weekly reporting structure called the PPP, which stands for Plans, Problems, and Progress. In it, team leaders, using this skeleton structure, share updates with those above and below them in the organization for more clear communication. …

All good box-sets have a start and an end.. and “Legal Hour with Tom and Carlos” was one of the fun series Tom Wilson & I set out to do in 2020.

The idea was simple.. if we could capture all the key questions and points we get asked in a mini-series… what would that look like? … and out came Legal Hour.

For your viewing convenience, I’ve put all the episodes below in order of how we published them (you can also go to Soundcloud to listen to the series in audio). We cover deal terms, deal structures, valuations…

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One of the key lessons you learn in startup life quickly is: you measure what matters and then make decisions from that. OKRs, and KPIs are born from this philosophy.

However, we are all equally well versed in the dark side of this, where one wrong KPI can lead to a worse outcome for all. The classic example of this is incentivising a sales team to sell as much as possible, but not qualifying customers and therefore you end up having runaway costs to acquire customers and churn can sky rocket after. …

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Investors frequently get a bad rap for how they communicate between themselves and more importantly, with the founders they back, but luckily this is changing globally at a rapid pace and today more and more founders and investors communicate as peers.

Whilst no one is perfect, part of the reason this bad rap happens, is due to a lack of contextual empathy (understanding the circumstances the other person might be in) and perceived power dynamics between investors and founders. …

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Making tough choices are part of the day-to-day at any startup or investment fund. However, how those choices are made varies greatly. Decision making within an organisation can range from hyper-gut-feel to hyper structured and rigid.

Whilst I don’t profess to be an expert on the subject, having now done over 350+ investments, one of the areas we needed to innovate to scale was around was how to best make good decisions efficiently and quickly. …

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When presenting/pitching, do you know & can you spot your company’s ‘Elephant in the room’?

From our favourite online encyclopaedia:

The expression “elephant in the room” (usually “the elephant in the room”) is a metaphorical idiom in English for an important or enormous topic, problem, or risk that is obvious or that everyone knows about but no one mentions or wants to discuss because it makes at least some of them uncomfortable or is personally, socially, or politically embarrassing, controversial, inflammatory, or dangerous.

It is based on the idea/thought that something as conspicuous as an elephant can appear to be…

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In a previous blog post, I covered how an early stage investor values a startup, but felt like there is likely more that can be said on the subject so consider this a ‘part 2’ to that blog post if you will. With the focus of this ‘part 2’ around how you can maximise your valuation and what are the drivers behind the boundaries of possible valuations for your company.

In my previous post, I covered how macro and geo contexts, amongst several factors, determine the relativistic value of a company to an investor on exit, and how traditional finance-driven…

Recently, I had the chance to catch up with Mridula, CEO of Peppy Health* and we spoke about the real cost of lost human capital at work and beyond, the future of insurance that employers provide their teams and everything in between.

*For some background about what Peppy does, it gives employers a totally new range of employee benefits that have a huge impact on staff attraction, productivity and loyalty — benefits that people actually want. Their first products support new parents and women dealing with the challenges of menopause, with more in the pipeline.

We often forget that throughout…

Carlos E. Espinal

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