People of Landscape - Alex Rainey, Founder of Pluto.

Alex is the Founder of Pluto, a mobile app that provides a home for all your travel plans and is building a community of travel lovers. He is based in London.

How long have you been a Founder for?

4 years.

Are you a first-time or serial Founder?

First time :)

What's your backstory. How did you come to be a Founder?

As long as I can remember, I’ve always wanted to start my own company. And I’ve also always been fascinated by tech of all shapes and sizes. So naturally these two things would collide eventually, in the best way possible. I made the leap to being a founder after spending too long in management consulting, a great place to learn, but also where dreams go to die. I reached a point where I felt I knew enough to build my own company, I met my co-founder and we had an idea we both believed in.


What has been the highlight of your Founder career so far?

Hiring our first employees was a real ‘pinch yourself’ moment. It made everything feel very real and was the culmination of so many things – getting the product off the ground, raising our first investment and growing to the point where we needed more people.

What has been the lowlight?

We were weeks if not days away from closing a new funding round, term sheet in hand, when a pilot we were doing with Monzo didn’t transpire into a full partnership. Our lead investor viewed this as a huge knock to potential to succeed and immediately pulled out of the round. I then had to proceed to tell everything to the other investors in the round that our lead was out. The molehill became a mountain and we lost 80% of the committed investment overnight.

How did you come across Landscape?

When looking around for potential investors for our next round, I wanted to see what background I could dig up on potential investors. Crunchbase, Signal, LinkedIn all help, but it hides all the genuine feedback about a VC. Then I found Landscape and you can see what real founders are saying about a fund.

What's the biggest mistake you’ve made so far and what did you learn from it?

Focusing on the wrong thing when telling the story about your business to a VC. The story is so different to how you’re used to telling it to get new hires, customers or friends excited. That seems pretty obvious. But the story also changes when telling it to Angels vs. VCs. I’ve learnt so much from many failed pitches to VCs and going on to read much more deeply into how they operate and what they look for, this has been invaluable.

What piece of advice would you give to other people in similar position as to you?

As a huge fan of Stoicism – don’t be put off by the classical sounding name – one of the most important lessons it teaches you is to focus on the things you can control, and not focus or become emotional about the things you can’t control. Easier said than done. But this is such an invaluable reminder for founders.

What is the most frustrating thing you find about the startup fundraising ecosystem?

Fundraising can drive the highest highs and the lowest lows. What makes fundraising particularly challenging – aside from having to get used to rejection – is the feedback you can get from many VCs is either vague or non-genuine. If you put yourself in their shoes, you can understand why they wouldn’t want to say ‘your idea stinks’ or ‘your team is too inexperienced’. But the lack of honest feedback is something that is really missing from the startup world.

What you would like to see change in the startup fundraising ecosystem within the next 5 years?

Super honest feedback from VCs – see my last answer above – it’s what founders want, even if it isn’t nice. We’re not going to hold it against you!

Secondly, easier access to VCs. As a white middle-class male, I already have a huge step up, but I still find it incredibly difficult to reach out to new investors. Many have no way of contacting them easily, many say they only want warm intros and many don’t even reply if you can get in touch. I can’t even imagine how much more difficult this is for other groups that don’t have the same privilege as me. The whole ecosystem could benefit so much from more open access to investors.



Alex is the Founder and CEO of Pluto. His LinkedIn profile can be found here. His email address is alex@pluto.travel and he is happy to be contacted.

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