10 things I’ve learned after almost 11 months of running a startup

Charles Douglas-Osborn
10 min readMay 18, 2017

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It’s been over 2 months since my last post (and 2 months before that). So I thought it would be good to write up some thoughts I’ve had on my learnings over the past 11 months. It comes at an interesting time:

Cue over the top stock image… I mean its a clickbaity subject line so what do you expect?

I promised I would give Merlin Guides (or Merlin Onboarding as it was known then) 12 months. If, after that time, I felt it was on the path to success then I would continue for at another year. If it wasn’t then it would be time to close it down and start working on something else. It also happens to be my birthday tomorrow which also always puts me in a reflective mood so writing this seemed to make sense.

Anyway so here are my top level items that I’ve learned over these past months:

1. Being a solo founder is really hard

In the VC world, people often state they rarely invest in solo founders. There are many reasons for this, but the main one is just how hard it is to start a company. The ups & downs, in particular, are tougher. Not only do you not have someone to confide in, but because you are the solo founder your identity gets wrapped up in the product so every yes or no often hits more personally than viewing the company as a separate entity. It also creates time management paralysis: I could literally be doing any of the 50 jobs at a company, which makes it impossible to choose which one. With a cofounder at least there are half (or less) of these, so its easier to work out what to focus on next.

My Advice:

If you’re still going for the solo founder; Ensure you have a great network of friends & family, a few other founders (they know what you’re going through so be honest with them!) & advisors (that know the business). Also hire someone, even if part-time, to be accountable to as well.

2. Picking a market I’m not an expert on slowed things down

It was very easy when I started to view training as something I had good knowledge over (I mean… I’ve done training at companies). But starting a company in that area meant I had to ramp up quickly (believe it or not training has more ‘buzz’ words than programming!). It also meant my connections weren’t directly in that area, which has lead to less advice, less initial customers & a worse understanding of the motivation that these teams run into.

I’m definitely passionate about the idea, and how Merlin is definitely the right solution for this market (Native Micro Learning… What a corporate phrase). However before Merlin was I that passionate about training? Do I read every blog post on the market? Did I know exactly the problems training teams were running into? Alas not, and I feel this has hindered.

My Advice:

Either pick a market that you are in yourself (and have a good amount of expertise) or spend one month reading every book, blog and podcast that 50+ people in that market recommend to you after you ask for their advice.

3. Fundraising is a full-time job

Although we ended up not closing our round, I spent over 3 months trying (and got about 30% of the target). Fundraising is exactly the same as sales in many ways: Find leads, try to work out the best way to convert them, meet in person, try to give them the incentive to get started ASAP, try to learn from each interaction. Similar to sales, if you are only doing it for a couple of hours a day/week, you’re not going to get any better. I ended up speaking with 86 Venture Capital funds, 120 phone calls, 43 in person meetings. On top of this the probably 500+ emails sent, including asking people for introductions, following up, giving updates, sending additional information…etc. This also excludes all the networking and scoping out that was spent before even getting to the first email. This reflects on how tough it is as a single founder — hard to spend 5 days a week on this while running a business.

My Advice:

Don’t fundraise until you have a full business. What I mean by this is that you are making $5–20k per month (for B2B). This way you are much more likely to convert people and thus not waste time (which should be spent on your business). A VC once said to me “My job is to put gasoline on the fire not to help you start it”.

4. I should have spoken to more potential customers

As a product/eng type guy, my focus is almost always to solve a problem. However, the problem that I first think about is often:

  1. Not a big problem for others
  2. Not a problem people will pay for
  3. Not the actual problem

This is where talking to more customers is important. The more you talk to them the more themes you pick up on, the more issues and the more you can dig deep into exactly what the issue is (and whether they would pay to fix it). Often I’ve had an initial meeting and ended up just pitching Merlin rather than really hearing their issues, which often come up in future meetings or are reasons that you don’t get the sale. A few things I would have saved time on if I had:

  • Internet Explorer is still a priority for most companies
  • Simulations for training are often top of mind
  • Ability to have ‘decisions’ inside of Merlin is key to many teams’ workflows

Instead, we focused on some ‘cool’ features I thought would be really useful. But you know what? No one has asked for them, so this was probably a bad use of time.

Advice:

Talk to as many customers as possible. I would even use this as a cold email to someone “I want to help solve X for companies and I’d love your expert advice”. I’d do a 15-minute call if someone emailed me that!

5. The highs and lows are more extreme than expected

This is one that people mention in almost any article on running a company. So, of course, I expected it, but it’s much more. Each client meeting was so great when it was booked, but terrible when it didn’t convert. On one day I lost my top client pilot, got approved to be a vendor for a government organisation, broke the server for 15 minutes and an old client asked to be re-enabled. It’s a crazy ride! I’ve generally tried to reduce this using meditation, exercise, talking with folks and I’ll admit probably a bit more alcohol than I should have. I think it’s particularly hard as a single founder too because your identity can be so closely tied to it that it becomes even more extreme.

Advice:

Try not to take things too personally, that goes for the good and the bad. View the bad as a learning experience… and the good as well. Work out in each case how you could have done it better!

6. There are a million startup events and I shouldn’t go to most of them

This is a hard one, because if you are just starting out then… Go to as many of these as possible. Networking is key at the start, I got a considerable amount of introductions from people I met at these events and some are even close friends now. However, there are a million things you need to be doing in a startup and really, most of these events are a waste of your time. I try to not go to as many now, there are a few I found useful and have led to things and I will keep doing them, but generally, if I’m not sure about going, then I won’t. There are 2 main reasons I think of when deciding to go to an event:

  1. Will this improve my product (i.e. is a speaker a key part of sector and insights would be huge?).
  2. Will this get me a customer (i.e. will there be 10+ potential customers there)

The last one is hard, especially at the start but realise that if the event name has ‘startup’ in it , then most people there are… startups and probably don’t want your product. They’d much prefer you used their product instead!

Advice:

When starting out, sign up to everything, but learn to cull newsletters and events regularly. Your time is worth more than 3 hours stuck chatting to a lawyer looking for a job (happened to me 3 times now!).

7. Being accountable was the main driver in progress

YCombinator (a startup accelerator) always forces you to choose one metric and focus on that. Everything you do should be moving that forward, and you have a clear date where you want there to be progress. I found that having a date for when I wanted feature X to be available, that either came from:

  • Telling a friend
  • Promising a customer
  • Setting a date with a post it on the wall

It is so important when you have low motivation, something goes wrong or you’re stuck on a problem that you have a timeline. You’d be amazed how much you can get done in 6 hours if that is all you have. I’ve had several long weekends and evenings to get something out on time (or early) that have moved things forward more than the last 2 weeks combined.

Advice:

Ideally have a date that you tell a customer about (and aim to finish in half the time), otherwise tell someone (and get them to force your hand) and finally accountable to you— set goals, targets and hold yourself to them. Try making things smaller though so you are still making progress at the start.

8. The US has many advantages but just as many disadvantages

Moving here from the UK was a tough decision, but it was partially fueled by the desire to start something new. There are some major advantages here though:

  • More VC money (for when you’re ready)
  • More of a startup culture (a founder is not “unemployed”)
  • One giant market all speaking the same language

However, it comes with some major downsides:

  • Healthcare costs take a huge amount of my monthly costs
  • More expensive to hire (because people have so many options)
  • One giant market all speaking the same language (means you are missing out on other cultures, ideas and potentially a better market for your product)

We are actually considering an accelerator based in the UK at the moment which focuses on the government sector. This is something I would never have considered if I’d been from here.

Advice:

You can create a company anywhere nowadays, not being in the states is not a reason to be an entrepreneur.

9. Learning the right work-life balance has been hard for me

After a cushy job over at Google, it was hard to enter a space where I was solely dependent on myself. No more feeling like I could take 1 hour lunches, stop working in the evenings… or even view the weekend as… well, the end of the week. There are definitely times when I am in a state of “flow” and I am just crushing everything, but there are times when nothing seems to work and walking over to play on the XBox seems like a better option.

I’ve definitely not figured this out yet, as sometimes I’m so drained from working or depressed for saying No to another vacation or fun activity. And the opposite occurs to where I will just take the day off because I need it, and things will fall off with the rest of the team.

It seems that work-life balance is even harder when you can’t quite tell the difference between them. Working from home has also not helped in this regard but it does not seem worth the money to pay to be somewhere else (at least the cost of having a quiet work environment is just as important to me).

Advice:

Learn to understand your body and motivation. This is a marathon, not a sprint and sometimes you need time off. I think it’s important not to lose touch with others in this time so ensure that you book a couple of times a week where you can stop working and just be present. Meditation & planning your day helps me a lot here.

10. There is plenty more still to learn

It may have been only 11 months but in that time I’ve learned many things. I’ve also gained some key skills:

  • Sales & Marketing Knowledge
  • PMing on very limited time
  • Understanding myself and my body
  • Know the training market well
  • Better at recruiting for 5+ roles
  • Getting out of ‘funks’

However, being an entrepreneur, as a friend said, is a career, not a job. This is still the start, and I’ve made many mistakes but I’ve also learned a lot.

Advice:

Keep reading, trying, failing and remember that everything is a learning experience.

A bit different than my previous blog posts, but would love your feedback on the below (please add a comment!).

Also, if you read all of this on the 19th of May, it’s my birthday :). If you’d like to send me a birthday message: I’d love it if before you do you could help me out by signing up for a free account on Merlin Guides here, and sending me 1 thing you liked and 1 thing you didn’t. I’ll love you forever (or at least until my next birthday).

On that note I want to thank everyone that has helped me get to this point. In particular to Keith, Tony, Luke, George, Fred, Jordan, Jacint and of course my girlfriend Paige for putting up with me! There are many more too, that I could mention.

Keep hustling everyone and speak soon!

Charles, CEO of MerlinGuides

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Charles Douglas-Osborn

Previous Head of Product at NewtonX, Founder of Haystack and Merlin Guides, ex-Google, Entrepreneur, Pun-dit.