The 5 hardest startup lessons I’ve had to learn

One of my highlights of this busy past week was chatting with the Public Service Launchpad cohort of entrepreneurs & intrapreneurs in London and sharing with them a few of the hard lessons I learned as we were building Learning Pool.  Even though I probably scared the life out of everyone with my stories a few people have asked me to blog this session so here we go.  I’ve organised my thoughts into my 5 key learns – I’m sure other entrepreneurs out there will have more of their own to add.

PSLaunchpad-2

Lucy Knight’s amazing sketchnote of my talk.

Relentless execution is required to the exclusion of all else.  The odds are stacked against you in a startup.  70% will fail and won’t make it to the end of the first 18 months.  You have to move your project forward every day.  This means no distractions or other side projects.  No social life and the bare minimum in terms of spending time with your family.  I can remember my mum saying to me that she saw less of me in those first 2 years at Learning Pool when I was 20 miles down the road than she did when I was previously working in London 500 miles away.  If you’re only prepared to work 60 hours a week in your startup you might as well forget it as you’re wasting your time and everyone else’s.  You have to deal with exhaustion and sometimes the sheer boredom of it as you spend a lot of time doing stuff you don’t enjoy.  You have to use every minute productively.  Make all your phone calls when you’re hanging around.  Use time on planes to write blogs and website content.  If you go away on holiday, expect to work every day – even if you have a co-founder and team.  There’s no off button.  You’ll work 364 days in those first few years (everyone’s entitled to take Christmas Day off!).  You’ll also constantly iterate and pivot based on customer feedback, make endless decisions (often with insufficient info), do your damnedest to hit deadlines, overdeliver and do rework for customers without being paid for it (suck it up) and you’ll always be selling and doing a load of other stuff you’ve never had to do and are probably uncomfortable with.  It’s quite common to hear startup entrepreneurs talk about all the stuff they’ve gradually shed to make more time in their working week and in extreme circumstances that will include sleep.  I was discussing this with Mark O’Neill of Government Digital Service this morning & we concluded that kickstarting an early stage startup is like throwing cats against a wall and hoping some of them will manage to scrabble up to the top – not that Mark or I would ever do such a thing.  Also the knowledge that others out there might have cats with sucker pads instead of paws…

Financing – should you take investment or bootstrap.  Sometimes this decision is dictated by your product.  You can’t launch a new drug or build a semiconductor company without investment.  If you take investment, expect to be bitterly disappointed by the early doors valuations you receive and brace yourself for the late night calls and crazy demands of your investors.  They’ll all spin you that line about owning a smaller slice of a bigger pie.  If you bootstrap, be prepared for the pressures that will bring.  Complete focus on getting to revenue, constant running of your numbers, daily cashflow forecasts, making the awkward phone calls when you can’t pay your suppliers.  Having to borrow from the bank and then compartmentalising that worry.  Being really honest with yourself or yourselves about where you are against your business plan.

3.     Learning properly how to sell and all the boring stuff you have to do in order to sell successfully – scanning for tenders, writing responses, following up for feedback when you don’t win them, iterating your pitch, implementing and using a CRM (I know at least one startup entrepreneur who used to fire people for not keeping the CRM up to date), getting ISO accredited, building a brand, having a proper sales deck and collateral, constantly refreshing your website content.  The discomfort of making yourself pitch if you’re not a natural salesperson and (if you’re sensible) learning to sell in pairs.  Making smart decisions about what to chase with your limited time and resource.

My friends Martin Howitt and Lucy Knight from Devon County Council

My friends Martin Howitt and Lucy Knight from Devon County Council

        Dealing with your own people.  You can’t afford anyone experienced so you recruit for potential.  That then requires a lot of time (that you don’t really have) as the team doesn’t know much and therefore they run everything past you.  Not many people can write coherently so you’ll spend a lot of your time re-doing what others have done – usually after they’ve gone home or gone off on holiday.  I found a lot of time is spent trying to second guess the mistakes your team are going to make in some sort of order of priority.  In reality, not that much bad stuff happens.  It’s the excruciating moment when you see an email that’s gone out or overhear someone talking nonsense on the phone.  It’s useful to teach your team early doors how to make their own decisions.  If you don’t do that it will add to your own already massive decision burden.  Letting people go when they don’t work out.  This gets a bit easier over time and the interval between joining and leaving certainly shrinks dramatically.  Disappointment when people you’ve been good to let you down.  That doesn’t get any easier.  The realisation that you’ve become a worse person inside yourself over the years.

5.      Working out the people mix, building the culture you want and creating a cohesive team.  After all it’s your opportunity to create the sort of business you’ve always wanted to work in yourself.  Sticking to your values and not compromising on them.  It’s easy to own the moral high ground when you’re a PAYE person; you soon discover where your values limits lie when your house is on the line.  The stuff you find out about yourself that you may not necessarily like.  Burying that ego that’s been growing during your years in education and when you were climbing the career ladder.  As Jim Collins says in Good to Great, looking in the mirror when things go wrong & through the window when things go right (to see who else was involved in getting that good result).  The sheer amount of time you will spend with your co-founder(s) and team in those early years.

Gloria and Katrina from the Diverse Leaders Network, part of the PS Launchpad

Gloria and Katrina from the Diverse Leaders Network, part of the PS Launchpad

So – I hear you all ask – this sounds bloody awful so why bother?  That’s easy & I have 5 reasons why it’s worth it:

1.       The Prize – financial and other.

2.       The huge satisfaction you get from building something from scratch that you’re proud of.

3.       The highs are amazing.  When you make a big sale or you land a sale where you started out as the underdog.  When you win a big award.  I still remember how I felt the night the call came in telling us we were the Intertrade Ireland regional Seedcorn competition winners.

4.       Putting yourself out there as a startup entrepreneur means you meet some great people and have some incredible experience.

5. Nothing can touch being your own boss and taking control of your own destiny – no matter how terrifying that can be from time to time.

I h  I hope this rather long blog has been useful to someone out there and I’m dedicating it to all the people who helped us when we needed help – you know who you are.  If you have any comments or questions feel free to add them in via the comments section below and I’ll do my best to answer them.  Good luck to all the PS Launchpad projects by the way.  I’m waiting for you guys to connect with me via the usual channels!

3 comments

  1. Dear Mary,

    I am very early on the journey and already recognise some of the lessons you speak of. Have you put me off? No way!!! All I know is I can’t wait to learn more every single day.

    I think your lessons also explain why some people chose to stay a business-of-one and why founders often turn into serial entrepreneurs who pass things over after a year/18 months. Why do you think Virgin’s offer is so diverse? Todays serial entrepreneur however is more of a thought leader encouraging others into kick-starting an idea which is key in the current economy.

    Is it boredom with your own product? Or is it recognising that the product hasn’t kept up with the rest of the world? Once you are selling a product that organisations like, I would imagine that it is almost impossible to evolve it quick enough. Tricky!

    I really value this blog as it has reassured me that the journey I am experiencing is exactly what it should be to build a successful business. Thank you!

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    1. Thanks for taking the time to comment Heidi. Yeah – I don’t mean boredom with your own product. At Learning Pool and at Task Squad our product set is awesome & as you say that’s through iteration & evolution as well as a bit of innovation. I guess I mean boredom with the way of life in an early stage startup. The incessant focus you have to give it & the sheer volume of boring stuff you have to do – like the accounts & the admin. Let me know if I can help you with anything & good luck with your new business – Mary

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  2. Hello Mary. My friend Meg Peppin pointed me at your blog. So far I’ve only checked this post and it’s great thanks. I particularly love: the sketch notes, doing stuff in pairs, selling, CRM – man I need to fix that one quick! On financing, we are currently self funded and I know I need to think a little more deeply about investment and keeping honest on the numbers. I’m much better at that than previously – but not good enough yet. Such a useful post – nice work.

    After I’d been trading for a year – I wrote this. It may be useful for your readers?

    http://stopdoingdumbthingstocustomers.com/learning/hard_lessons/

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