Conor McCarthy

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10 (more) things I wish I knew earlier about starting businesses.

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The First 10 things I wish I knew are here.

Like anyone who works for themselves, I have a litany of things I learned the hard way.

All of them have taught me things that now are a part of my subconscious judgement when making decisions.

They help me be less wrong in the future.

In speaking with founders on The First 10 Podcast about how they found their first 10 customers, I have discovered that some of these mistakes and failures are universal.

The only way to learn from your mistakes is to reflect on them and the only thing to do with your failures is to juice them for all they are worth.

Don’t let them leave with the building without picking their pockets.

Here is a shortlist of 10 (more) things I’ve learned along the way that might help you improve your decision-making process and general judgment.

1. Waste time to save time

This is a steal from Amos Tversky, the late collaborator of Nobel-winning psychologist Daniel Kahneman, who once said “the secret to doing good research is always to be a little underemployed. You waste years by not being able to waste hours.” I used to think that being busy was the best and only way to succeed. Cram it in and figure out a way to squeeze the most from every minute of every day. And yet, on reflection, it was the breaks I took, the holidays, the days off, the long walks with friends, sometimes even the time cleaning the house, that led me to have “new” thoughts, new breakthroughs. Having some slack in the system means your brain can do what it does best. Think.

2. 2 ears, one mouth

Back in the days when I thought my ideas were the best ideas solely because I had them, I had many conversations where I pitched people on new business ideas. I started with me and I talked about myself. Not only was this pitch approach a bad (the worst) one, I’m pretty sure I missed a ton of insights from customers that could have helped me pivot my idea, or simply create new businesses based on their true needs (and not what I thought their needs were). Listen first (and second).

3. Backwards/Forwards

I used to sit down and start my day by opening my email. Oops! The day would inevitably lead to me living in the wrong Eisenhower Quadrant, and over the long term, not really getting much done (or getting a lot of the wrong things done). Over time, I have built a solid framework of reflecting and planning that not only helps ensure I’m doing the right things but helps me better visualize the trajectory I’m on, and the progress I’m making. I spend just one hour per week reflecting and planning, and that compounds immensely.

4. Alphabet Planning

Related to “Backwards/Forwards” mentioned here, and using what I know (the humble alphabet), I use a simple AZB framework for tracking progress.

  • A = Where am I now

  • Z = Where do I want to go

  • B = What can I do next

This works because it helps me to truly see where I’m at (when projects can be multi-faceted), it reminds me of where I’m going (because if I don’t know that how will I know when I get there) and most importantly, it helps me focus on the next step. Not all the steps, just the next one.

Then I use the acronym “FST” to help me plan my actual days. My theory is that if I get just 3 worthy things done every day that move my projects along, that will all add up over time. It seems to be working so far. It’s pretty simple:

  • F = First Thing (ie the most important thing that day. Do not proceed to the next one until this is done)

  • S = Second Thing (ie the second most important thing that day. Do not proceed to the next one until this is done)

  • T = Third Thing (only do when First and Second things are done)

I know. It’s like “planning for kids” but keeping it simple works

Note: I stole the ABZ part from this short video.

5. Start small and perfect

The early years of the Street Performance World Championship, which became one of Irelands largest outdoor events, were filled with stories of near failure, and subsequent learning. One that sticks out came from my brother. At one crucial point, when it looked like all was lost and we wouldn’t get the funding we needed, and the previous year's work was going down the drain, I told my brother what was happening. He replied and simply said, “Even if you have to put on a festival in your back garden, do something. Don’t let the work go to waste. It doesn’t matter if it’s small, just that it happens”. Now when I work with people who are trying to build something big and are in danger of overwhelm, I always pose the question “What does small and perfect look like here?”.

6. Experiment more

Make little bets. Not everything has to be huge, not every decision will crash and burn your business. Do some fear setting and keep going. “An experiment is never a failure solely because it fails to achieve predicted results. An experiment is a failure only when it also fails adequately to test the hypothesis in question, when the data it produces don’t prove anything one way or another.” — Robert Pirsig, Zen and the Art of Motorcycle Maintenance

7. Maybe it’s the market, maybe it’s the medium, maybe it’s the message

I’ve made mistakes in all of these areas. I’ve neglected to find a market first (See “Market needs are your fuel” here), I’ve failed to approach the right market in the right way, and most of all, I’ve failed to use what my customers were telling me, to communicate with them. That last one deserves the biggest facepalm of all. First listen to understand, then communicate that shared understanding.

8. There is no there, there

Projects lead to more projects which lead to even more projects. Further to that, collaborations lead to more collaborations which lead to even more collaborations. Despite the fact that each new project or collaboration feels like it could be the last one, it never is. I play to keep playing, and that’s been a really helpful way for me to frame my entrepreneurial journey. (See “The Relationships Rule” here).

9. Steal Like An Artist

“The only art I’ll ever study is stuff that I can steal from.” David Bowie.

When I work with new business builders, I often discover an unnoticed desire to create something brand new, something the world has never seen before and will gulp down because it’s so different. But speaking as a member of the world, a lot of the time, I just want something to work better, faster, or be cheaper. I don’t necessarily need new and shiny things. (In fact, really really new and shiny has to be managed carefully). I usually need substance. My advice in these situations is usually to see what's working and artfully steal that. Everything can be an inspiration, and often we can get 90% of what we need by noticing and learning from what has gone before.

10. It’s simpler than it looks

Related to “Steal Like An Artist”, I find that I often stick with the products and services I pay for because they are simple in some way. Easy to use. Easy to understand. Easy to share. And on reflection, this one rule could be best friends with any of the rules that have gone before. Keeping it simple feels like an easily ignored cliche, but it’s pretty powerful if you give it a minute. I mean, if Einstein said it, it must be true, right?

The lessons learned here were learned through careful reflection. I had to chase them a little to get the true essence of what they meant to me. Many of them could have been easily missed, but I spent time figuring out what didn’t work or how I could do things better. I also stole aplenty.

Now that you’ve had a glimpse into what I’ve learned over the years (and a reference you can return to over and over again), let me know where you are getting stuck! I’ve learned these things the hard way so you don’t have to. Clearly, I do my homework, and I bet you do, too. I help founders, bootstrappers and freelancers find their First 10 Customers, so make sure to get your free First 10 Customers checklist and book a call with me here to chat about finding your First 10 Customers and grow your business.


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