L-R (including background): Gordon Meadows, me aged ~17 [#6], Jonny Harker, Steve Ferguson [#10], can’t remember [#11], Adrian Bennett, mum(!), Tom Critchlow (table official)

Things I wish I’d known

Will Critchlow
Life, Distilled
11 min readJun 16, 2016

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I can’t believe it’s been five years.

Five years ago — a lifetime in entrepreneur-land — I was invited back to my old school to give a talk to a bunch of 16 and 17 year olds. At this point I was a little over five years into the Distilled journey.

The topic I ended up choosing was “things I wish I had known” when I was at school.

I was looking back through old presentations recently and was surprised to realise that I’d never written about it — and I thought it was interesting to look back at it through the lens of another five years.

Here’s the presentation:

The presentation I gave in 2011

Context

It starts with an introduction about my co-founder (Duncan) and my brother (Tom) whose personal and professional lives are intertwined with mine — and who both went to the same school. It teases with some photos from our early conferences and then goes back to some of our earliest web-based entrepreneurial adventures:

  1. The time when we picked a company name already in use by a company just down the road in Leeds and it got all legal (in our defence, we were 16 or 17, and it was before Google existed!)
  2. The time when we built a business plan / model in Excel to quit our jobs and start selling website design and build services. We couldn’t even make the mechanics of cold-calling / selling websites door-to-door work on paper, but we said “screw it” and went ahead anyway. We made £36k in revenue that first year — roughly a salary between us

Into the lessons

Overnight success takes years

We’d grown past £1m in annual revenue by this time, and so I could present a nice chart showing how long it took, and how tiny those first few years were:

Overnight success takes years

We came of age during the dotcom bubble and bust, and so had some crazily unrealistic expectations of what business growth could be like when we were dreaming about starting our company in 2000 / 2001. I feel like those expectations were dashed in the bust, stomped into the ground by our first couple of years toiling, but that ultimately that made the growth that we had to work for all the more sweet.

Stop worrying what others think

We were not the cool kids at school. We were kind of almost tolerated by the cool kids because of basketball, but were very definitely on the geeky fringes. Geek stuff seems to have turned out OK for us though.

It’s funny looking back — I don’t know if it’s changed now — I remember feeling as a teenager that business wasn’t the place for academic thought or geeky technology. This might have been a uniquely British perspective (Bill Gates was at the helm of a Microsoft at the pinnacle of its influence after all) but everything about business at our northern state comprehensive in 1996 was about the anti-academic market trader who left school at 16 and sold his (always his) way to the top.

Anyway, hopefully Page, Brin, Zuck, Mayer etc. have changed the narrative — but regardless, I wanted to make the point that the dynamics that exist in high school aren’t lifelong.

Hang out with people who are smarter than you

For me, this was a lesson I learned at university (I recently came across this brilliant post about the experience of being at a great university). It’s actually a continuation of the previous point though — which is that a) you get to choose who you hang out with once you’re outside the constraints of school and b) that means you can choose what you spend your time thinking about and your days talking about.

Business friends rock

In the early days of our company, we had no network. We were 25, had no industry experience, and knew basically no-one. I knew we needed to change that, but the early things I did to build a network (largely going to networking events) weren’t effective. What did work was hanging out in places full of smart people who were interested in the same things I was interested in and genuinely getting to know them.

I love looking back at the image I used to illustrate this point:

Business friends rock

That’s me, my daughter Rachel (about 6 months old at the time) and Rand. Separated by almost 5,000 miles and 8 timezones, Rand remains someone I look up to, someone I learn from, and someone I can turn to about anything business or personal.

We initially met because I hung out in the early moz community (my 6,000+ mozpoints would have me in the top 5 community members if the associate deal we later did hadn’t removed me from the running). The friendship grew the same way my non-business friendships grew — over conversations, broken bread, and shared ups and downs.

No, you can’t have a pony

No you can’t have a pony

It felt like there was a lot less nonsense being spouted about millennials back in 2011 than there is today, but at this point, I was trying to fast-track the audience to a realisation it took me a couple of years in the workplace to reach.

I chafed against wanting more responsibility and more ownership throughout the 2.5 years I worked for other people after university. But at the same time, I wasn’t the greatest employee. I needed to prove it in my current job and take accountability for doing the things I wanted to do next. It wasn’t until the first day working for myself that I really got it — that I really understood that you don’t need permission to lead.

Curiosity is your best asset

One of the most enduring lessons from my entire school career (probably second only to the time Gordon Meadows told me he’d cut me from the basketball team if I was ever thrown out of a maths lesson again) was the quote from Mr. Wilson who taught design, technology and electronics:

Always ask yourself ‘how does that work?’

He encouraged us to ask it about office chairs that go up and down when you press a lever, about what went on when you requested money at an ATM, and about many other things. It’s really stuck with me — and it leads to the (most likely mistaken) belief that there is nothing you can’t understand. And the brilliant thing when it comes to computers — and specifically to software — is that if you can understand it you can build it.

You don’t need to want to become a developer or an engineer to get value from learning how to build things.

Don’t listen to careers advisors

I phrased this narrowly at the time — all about getting hired — but the real lesson is that:

  • You don’t have to be an actuary if you’re good at mathematics
  • Many of the best jobs aren’t advertised
  • Many of the biggest opportunities come without applying for a job
  • What you’ve done is more important than how you present a CV / resume

Ed Fry can tell the story of how, aged 16, he 3D-printed our logo to impress us and the incredible things he’s gone on to do since then:

Read these books

  1. Good to Great [Amazon UK|Amazon US]
  2. Getting Things Done [Amazon UK|Amazon US]
  3. The E Myth [Amazon UK|Amazon US]

Get past cold calls as fast as you can

The story of our journey to learn sales is a tale for another day (TL;DR — Selling to Win [Amazon UK|Amazon US] and its author Richard Denny). But the one thing that we had to break free of was the insistence that cold outbound approaches were the only way we could grow our business:

Get past cold calls

In that first 12–24 months we sent a lot of letters, made a lot of cold calls, and knocked on a lot of doors (literally). Our business really took off when we started eating our own dogfood, blogging, and growing our presence and reputation.

Once you leave college it’s not cheating any more

There’s a backstory here about the college part that I’ll tell you over a beer one day, but the critical part is the “unfair” advantages part. There are plenty of unethical and immoral temptations that will come your way in the world of business — and it’s worth remembering that a reputation is more easily broken than built. BUT there are so many things that are inappropriate at school (like looking up the answers, doing mutually-beneficial deals, and generally standing on the shoulders of giants) that are to be encouraged once you are out there in the real world. There are no marks for effort, nor for showing your working once you’re being judged on results.

Give yourself unfair advantages

From here on out, do something you love

This one’s self-explanatory I think

No-one knows what they’re doing

Never compare your inside to someone else’s outside

I don’t recall where I first saw this quote (which is now attributed to so many people), but it’s similar to the company-level version in this post from Mark Suster.

Not only have I found it useful in managing my own psychology, but I’ve also found it useful in thinking about whether I’m “ready” for certain milestones in my life. The short version is that there are so many things you’re unlikely to feel ready for in advance (a non-exhaustive list of things I didn’t feel ready to do: hiring someone, getting married, buying a house, having kids). I vividly remember the desire to call a grown-up to get “permission” before the first of those — hiring our first employee.

What have I learned in the subsequent five years?

I set out to write this post as a quick task to host that old deck. It’s already become much longer than I anticipated it would. So I’m not going to illustrate all my newer lessons right now — but here are the main ones that spring to mind now:

You can’t overstate the importance of alignment

You don’t always have to agree on everything with the people you work with (in fact, you should vigorously dig out conflict — see five dysfunctions of a team below). Five years ago, the team was so much smaller, and so much newer, and we hadn’t really experienced misalignment. Some of it is obvious (people who actively have a different vision or who detract from your own will be incredibly hard to work with), but some is more pernicious — in particular, it takes a lot of experience to realise how much it saps energy to be around those who won’t commit to decisions and directions, and who either continuously revisit old debates or engage in political games to backchannel their displeasure.

Do everything you can to avoid ending up in those situations, and to get out of them as fast as possible when they accidentally arise.

It’s really hard to get honest and helpful feedback

We believe that:

communication solves all problems [Distilled manifesto]

One of the ways this plays out is in feedback — and the critical importance of seeking out the feedback you need to improve your work and your capabilities as well as actively seeking out those people who will tell it to you straight. This latter point is especially important as a company grows and the perception of “management” or “leadership” can build artificial walls preventing people from sharing honest opinions. (Practical tips and advice from one of our experienced consultants here).

Getting good at giving and receiving feedback has been most evident internally in our ability to craft public presentations. I recently looked up the feedback we received at our first conference (which felt to us to be a real step up in quality from similar events we’d spoken at before). Across all sessions back in 2009, 13% of all session ratings were “average” or “poor” (45% were “excellent”!). At our most recent Boston conference, across all sessions, 2.2% of all session ratings were “average” or “poor”.

You’re going to be most proud of things done by other people

I wrote a whole post about this — including a whole bunch of reasons why you should come and work at Distilled.

It’s emphasised and highlighted by this amazing post that ex-Distiller John Doherty wrote recently about Distilled entitled the greatest entrepreneurship incubator you’ve never heard of:

Thank you Distilled and those there who took a chance on me. I am forever grateful. — John Doherty

Us too John. Us too.

I’m proud of those who’ve left Distilled to great things. I’m incredibly proud of those who’ve worked their way up at Distilled — from analyst to VP, from EA to head of department etc. The list goes on. And I’m already proud of the next generation — can’t wait to see what they do over the next 5 years.

There’s some more books you should read

…and tons more

It’s really hard to remember what things were like in even the relatively recent past. I was looking back through old emails recently to find some significant internal memos and I found a whole load of documentation of some financial decisions we had to make in early 2012 when we were still paying for opening an office up in NYC, had a big corporation tax bill to pay in the UK, needed to pay a huge deposit on new office space in London etc. It must have been a stressful time. I don’t remember it particularly well. That’s part of the reason that I try to write these things from time to time — they’re snapshots of a state of mind.

I’ve also left out all of the personal and family lessons (which are legion — my daughter was only 1 when I gave that last talk and now she’s 6, going into year 2 at school, and my son starts school in September). We’ll save those personal stories for another day.

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Founder and CEO at SearchPilot. Previously founded Distilled (acq by Brainlabs). Views may not be orgs'.