The PhD Dropout Who Built, Sold, and Still Can't Sit Still

With a background that spans engineering, economics, and startup grit, this Cambridge Angels member embodies the true spirit of entrepreneurial curiosity. From writing to companies on the Cambridge Science Park before he could legally work, to co-founding and exiting a tech startup long before online booking became mainstream, his journey is one of grounded ambition and relentless experimentation. Now an experienced angel investor with a diverse portfolio and a passion for helping founders grow, Matthew Cleevely shares candid insights on what makes a great founder, why wavelength matters, and how Cambridge Angels fosters a uniquely supportive ecosystem for early-stage startups.

Can you give a bit of background about yourself?

I'm an angel investor and a member of Cambridge Angels. My academic background is in engineering and economics – I did a Master’s in engineering, followed by a Master's in economics (here in Cambridge), and then started a PhD before dropping out to help start a business called 10to8, which built appointment scheduling / reminding system - in the days well before online booking was a thing.

The entrepreneurial side began much earlier. Since before I was legally allowed to work, I spent every summer writing to companies on the Cambridge Science Park that I thought were doing interesting things, asking for jobs. Occasionally the person I’d write to would be unwise enough to let me do something. This led to incredibly varied experiences – from designing mouse mats to conducting statistical analysis on medical data, building accounting databases, and working on any kind of tech projects. Whilst studying at Cambridge, I spent far too much time developing potential business plans with friends - whom I would end up starting 10to8 with which eventually led to dropping out of the PhD to focus full time on startupland.

After a very rocky road – we rebooted once – we eventually achieved a successful exit with very happy investors. Now I do a mixture of things: working on more academic pursuits (I still think about finishing that PhD), working with portfolio companies, and being an active angel investor advising several startups and sitting on boards.

How long have you been angel investing? What made you apply to join Cambridge Angels and what do you think makes it different?

I’ve been an angel investor for ages. If we include sweat equity – getting paid in shares instead of salary – I've been investing since I was a teenager, so roughly 25 years. My first cash investment was probably 15+ years ago, though it was very small. Today, my investing has grown substantially, and I have a portfolio of about 25 companies. I've also been part of managing a successful family portfolio for much longer, which has given me insight into different portfolio management approaches, strategies and exposure to a lot of potential investments.

What I love about Cambridge Angels is that the majority of members have all built and exited successful businesses themselves. They know what the founder journey is really like and are willing to open themselves up to supporting that journey again. This means you can get advice on virtually any business challenge – whether it's vetting suppliers, finding expertise in specific sectors, or getting brutally honest feedback.

I think what sets Cambridge Angels apart is that it's not a membership organisation in the traditional sense. Members don't charge pitching fees or success fees and ‘the Cambridge Angels’ doesn’t really exist as entity. It's entirely run by membership fees, which gives the organisation tremendous freedom to be genuinely helpful and the investors choose what to get involved in and what to pass on. Most investors' job is to say no, but Cambridge Angels is really focused on: How do we help? How do we ensure that even if we don't invest, companies get something valuable from the experience? So I guess I’d say it's a loose collection of experienced angels and entrepreneurs who are there to help people start businesses, rather than a formal organisation looking to extract fees for survival. That creates a much more collaborative and supportive environment.

Can you give a couple of examples of Cambridge Angels deals you've invested in that you're currently excited about?

This is really difficult because - apart from the ones that aren’t - they're all my favorites! With angel investing, you have to make peace with potentially over 10 years between taking a position and seeing either commercial returns or real-world impact and the majority of investments failing.

I think I’ve trained myself to not get too excited about any of the early stage investments because it’s always too early too tell (until it isn’t). The gap between technology development and actual deployment with customers is enormous, and usually underestimated by founders and investors alike.

Do you have any sector focus and if you do, why?

I don't have a rigid sector focus, but there are areas where I have more expertise and experience and where I can genuinely add value through my experience and network. The most important factor for me is usually the founding team and whether we're on the same wavelength – if we can talk to each other and have a common understanding of what we're discussing & that I feel I can help in some way.

In Cambridge it’s mostly about ‘tech’. It tends to be Cambridge's particular strength and the model that the ecosystem is most familiar with and best at building. Often people refer to this as ‘deep tech’ - but it’s really just whether something is at the forefront of possible and so no one has any particular advantage in building something commercial that takes advantage of it.

How do you tend to get involved with your investments?

I usually get involved at a few different stages, mostly advice, investment, sometimes recruitment decisions and I've even ended up helping with M&A in quite a few deals, advising on structuring sales and acquisition processes. Often, companies reach out during crisis moments, but the really well-run companies maintain regular dialogue.

What's telling is which companies maintain a positive working relationship outside of crisis moments – that's usually an indicator that the business is much better run and has better prospects. I try to be available to any company I've invested in for advice and thoughts, and companies know they can reach out when they need support.

What have you learned about being an angel investor since you've started?

I've learned a lot about investor strategy – how much to invest at what stage, how to approach investments, and the importance of having other people help you make decisions. Having a clear investment strategy and regularly reviewing what went well and what went badly is crucial for avoiding similar mistakes in the future.

I think the most important thing I've learned relates to two key concepts: grounded ambition and wavelength.

Grounded ambition means having very ambitious goals while knowing what steps you're taking now to work toward those goals and having clarity on the path forward. This is tremendously important in founders and a real skill that’s very hard to acquire or teach.

The wavelength concept is about being able to discuss what founders are doing and truly understand each other. A great example of this were two meetings I had with Botty, founder of Tenyks, years ago. The first was a friendly discussion about potential strategy. The second was months later, where he explained all the things I suggested and why they were wrong based on real customer conversations. That was wonderful because he had understood what I said, gone and tested it, taken concrete steps toward his goal, and found out what the right steps were – including discovering what the wrong steps were. I’ve learned that’s the behaviour of great founders.

What is the investment exit you are most proud of and/or an investment horror story you would be prepared to share?

The exit I'm most proud of is my own company. There's something special about building a company, growing it, and being able to repay the investors' trust in you. Successfully delivering on that trust and building real value is incredibly rewarding, as is seeing something you built be valuable elsewhere and be used and scaled.

The horror stories usually involve unplanned founder fallouts or mismatched expectations between boards, investors, and founders. The worst case I've seen involved founders disagreeing about strategy, withholding intellectual property, and essentially sandbagging the business into the ground. No names here. Though selling my own company was also one of the worst horror stories in terms of process complexity and how long it dragged on.

For more details about the horror stories – buy me a pint and maybe sign an NDA in the pub!

The best part of building businesses and working with founders is seeing extremely capable people thrive and solve challenges you couldn't possibly imagine; working with brilliant founders who don't really need my advice but talk to me anyway. Watching great people grow, take on responsibility, and achieve scale and success is stupidly rewarding.