People of Landscape - Ash Phillips

Meet Ash. Founder at Dffrnt. Startup advisor. Consultant on community, comms, brand positioning, and B2B GTM strategy.

How long have you been an investor for?

  • 10 years in startups as a serial founder
  • 5 years as an advisor
  • 18 months angel investing via Ada Ventures

What's your backstory on how you came to be an investor?

I dropped out of university 6 months in to start my first business (I actually deferred for two years and while this isn’t as glamorous as the usual dropout story, I suspect it’s the same for many others). This was a marketing agency focused on visual disciplines, i.e. Branding, graphic design and web design. I chose this as I had a combined passion for visual arts as well as computers and so it was a natural fit for me.

I worked part time for 3+ years before I’d learnt enough and build enough opportunities to earn enough work to consider it a job. Around this time I partnered with another agency in what can only described as a ‘tiny merger’ of sorts and we subsequently grew the agency over a period of 2 years.

Along the way I had met countless people in business but 99% of them were my senior in age and experience, by far. Meanwhile my friends never really understood what I did for a living and my parents probably never will. As a result, I decided I wanted to meet other people who were more closely linked to my circumstances, i.e. were a similar age and involved in business in some way.

I created a meetup originally for ‘young entrepreneurs’ and a few people turned up. They really enjoyed it and asked when the next event was so I suggested the following month and since then, we’ve been growing a community of creators through events and online ever since.

Pre-covid we were running events in 21 cities across 9 countries and (are slowly bringing those back now that restrictions have eased). As a result of that events community, we created an ecosystem of support for creators (founders, freelancers, etc) and have been developing it ever since. That is what became Dffrnt, the business we are now.

What has been your highlight as a founder and as an investor?

Honestly, I don’t think I can just pick one, but as an overarching theme I have to say that many founders often take for granted just how far they’ve come, relative to where they’ve started. The very fact that I grew up outside of this kind of environment and my first job was stacking shelves in Sainsbury’s, that I get to do what I do every day and have – in the good times and the bad – been able to continue doing so for 10 years now, is a highlight in itself. Most businesses fail in that time. I promised myself when I began that “I wouldn’t let myself fail” and here we are today, still going. So that makes me really appreciate the journey to date and all it’s ups and downs.

What about a lowlight?

Being just days from being bankrupt, at least twice. Ironically, both months ended up being my best month for sales both those years; I guess there’s something about being backed into a corner that brings out the best in me (something to discuss with a therapist, no doubt), but that doesn’t mean those times were easy by any stretch of the imagination. The cold sweats, sleepless nights, nigh-on panic attacks that are experienced in those moments of struggle are what make me scoff when people say “more money, more problems”. Sure, money brings challenges, but not having any feels like a claustrophobic trap where you’re rapidly running out of oxygen. It is not pleasant and I can certainly empathise with every business owner who goes through mental health struggles as a result.

How did you came across Landscape?

I actually met Joe a number of years ago, way back before he started Landscape at one of our meetups (our Manchester one). I have a terrible memory for many things, but I remember the people I meet at our events well and Joe and I got speaking at the bar in Lock91 - our meetup venue at the time, and stayed connected but didn’t speak often after that. Then, when Landscape started, it resonated so well with everything I had done since then that I reached back out on Twitter and here we are!

What is the biggest challenge you need help with right now?

Taking my own damn advice. It’s so easy now to give timely advice to startups and I think I’m pretty good at doing so (at least the Mentor of the Year award I won says so!) but it’s so difficult to take that advice myself. While I know that knowing what I do now, makes me a better founder all-round by default, it still is so easy to forget and/or embody the things I tell founders about confidence, timing, focus, etc. It’s why I’m putting together a formal advisory board for what I’m working on next.

Biggest mistake you’ve made so far and what did you learn from it?

Ooh there’s a few but probably not setting clear enough expectations with team members. Hiring is tough as it is. I’ve found you can develop skill but attitude is so hard to do the same with, so hiring for that first, makes sense. However, in 2022, where flexibility is a default, I’ve previously fallen foul to providing too much of that, which has meant creative team members have had no direction in which to point their talent and – in some cases – has meant lost time & money. Not a mistake I’ll make again and an experience that has undoubtedly made me a better manager over time.

Any good advice to other founders?

Don’t sweat the small stuff. At the end of the day, a sustainable business sells things and delivers them to expectations. Repeat that time and time again and you’ve got something. Only then should you look at improving efficiencies, etc. Working on your business can either be something left until later or an addictive distraction vs working in the business. Try to avoid either and build in some balance, while making sure you sell and deliver.

Most frustrating thing you find about the startup fundraising ecosystem at the moment?

The narrative and expectations are all wrong. An investor will invest in a startup if they represent the best possible–albeit high risk–opportunity for an ROI on their cash. If that’s true, then founders feeling like they’re “begging” which is often the case shouldn’t be the status quo. In fact, the inverse should be true and investors should be fighting to get into the company. This is especially true when you consider that, I believe, statistically more VCs fail than startups. If founders understood that dynamic then it would level the playing field a bit more and provide the much-needed confidence that can ultimate make or break a company during fundraising and beyond.

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

Democratisation of dealflow, and capital, i.e. money finding it’s way to the best & most deserving opportunities, regardless of circumstances, geography or networks. The technology exists to solve this. ‘Hubs’ no longer need exist in the age of the internet. This won’t be an overnight change, but I think platforms like Landscape and the work I’m doing on Dffrnt and my new project can help to be part of this change.

You can connect with Ash on LinkedIn here and follow his Twitter here. He's happy to be contacted via both social media sites or you can email him at Just drop him a DM or an email 💬 🙌.

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