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The funnest way to learn 6 key lessons about being an entrepreneur

Being a part of Startup Weekend keeps me motivated and excited about being an entrepreneur! (Photo credit: @ryanbibby)

I took part in my first Startup Weekend two and a half years ago. At the time, I had no idea what a startup was, much less a weekend dedicated to them.

I went on to win that first one, then my second.

I got so much out of those two startup weekends (including my current company, Textocracy) that I have gone on to volunteer with half a dozen since. One of these was in Gaza, in which 50% of the +150 participants were women.

This past weekend I coached teams in preparing for their five minute pitches in the latest Startup Weekend Sheffield. (That’s the super star facilitator of it, Chris Murray, on the far left in the photo above- next to my fellow Gaza Sky Geeks volunteer Laura IH Bennett.)

This weekend was highly unusual in that almost all of the attenders were participating in a startup weekend for the very first time. Only two out of 40 people there had done one before.

They were also from a range of ages and backgrounds, and brought lots of different experiences.

These new participants had followed my number one rule of entrepreneurialism:

You must get in the game. Things happen when you get in the game.

Now, you don’t have to participate in a startup weekend to get into the game. It was what worked for me, and I happen to believe that their format and the support you get in them is a no-brainer opportunity for getting into the entrepreneurial game. And it’s loads of fun!

In fact, this weekend I was reminded of these six key lessons that participating in my first two startup weekends taught me:

1. The art of the pitch

When you have to think carefully enough about your business idea that you can convince someone to vote for you, or invest, or simply agree it’s a great idea within five minutes, you have gone a long way toward validating it. You can state the problem you are solving in a sentence, and how you are going to make money with your solution within a few more.

And honestly, the art of the pitch is not just good for winning a Startup Weekend or securing the support of an investor, it’s a good skill for convincing almost anyone of anything!

2. The importance of forming a solid team

This past weekend we had a small team of three that suddenly lost their developer on the Friday night. By some miracle, a new participant showed up on Saturday morning and joined that team. Not only were they able to rally and get through the weekend and pitch on the Sunday night, but they went on to win first prize.

For me, that’s a sure sign of a good team, and a strong team leader. They didn’t lose their nerve, and they were able to get their new team member up to scratch quickly and keep their focus.

Only in a startup weekend can you gain that skill and practice that situation as safely and quickly as this!

I’ve written about my own experience of forming a team at a Startup Weekend. I spent 20 years as a leader and a manager of very large teams in the public sector, and still I am continuing to learn secrets of building a team– it’s one of the hardest parts of being an entrepreneur and a leader. The more practice you can get on the journey, the better.

You can read about my most painful experience of trying to build a team here.

3. If you want to play a game, go to where it is played and find a way to get in. Things happen when you get in the game. — Jamal Edwards

This is the rule I started this story with, and for good reason. Getting into the startup weekend “game” is not only a place to practice and learn some lessons, but you meet all kinds of people. These are people that could be your next co-founder, or that have an idea you are ideal to build, or where you might find the perfect designer for your latest project.

And like most games, it is just plain fun!

Things happen when you turn up and participate. And you never know just what that might be.

4. Don’t give up, or give in. Stick to your conviction and make it happen.

When you have done your homework and tested your idea (which a startup weekend is perfect for!) you will be in a strong position to know whether you have a ‘goer’ or not.

You will encounter naysayers, doubters, and underminers. But if you have truly done the background work, and taken your idea through some good processes such as described in The Mom Test, then stick to your guns.

Crises of confidence are one of the most common reasons businesses fail, or rather, fail to ever get off the ground at all. Make it happen.

5. Without an excellent problem/solution fit all the whizzy tech in the world won’t save you

Like I said, at our Startup Weekend we had almost all newbies, but a wide range of ages and skill sets. Also due to time constraints, building more than a simple minimum viable product is difficult.

Sometimes these mvps are no more than fancy pictures or simple wireframes and mockups. In fact, I won my second startup weekend with a simple black and white flow diagram on a piece of paper. And that’s perfectly ok, because a good problem/solution fit is obvious. It comes out in a pitch and the judges are canny enough to see if you’re onto something regardless of whether it has bells and whistles.

That’s true in ‘real life’ as well. Start with an mvp, don’t break the bank, and test your idea with real customers before you invest in the whizzy stuff.

6. Experience brings a lot to the table; if your startup doesn’t have it, find someone who does

While our startup weekend was full of participant newbies, we did have a good share of older people who either had experience in their industries or had started their own companies before.

We also had lots of innovative and creative students, young business people, and courageous people who just wanted to try something new.

In my experience of startup weekends, this is an excellent mix for coming up with fantastic ideas that are likely to work. Having just one or the other can mean that something is missing that might prevent your idea from having either the practical application or the innovation it needs for that competitive edge.

That’s why meeting new people somewhere like startup weekend, or meetups, hackathons, or any other forum where you will encounter people who are not just like you is so important.

My experience with startup weekend is why I have my company, Textocracy, over two years on from when I took part in my second one. I don’t reckon I would be an entrepreneur today without it. I just wouldn’t have had the nowse to even start.

Many successful entrepreneurs I have spoken to over the past few years have said that if they knew what they were going to have to go through and how hard they were going to have to work to make it, they would never have started.

That’s why in my view it is so important to just get in the game with both feet. Startup weekends are a great place to do that with no risk. It’s a great way to learn a bunch of new stuff, meet some like-minded people, and maybe even pick up a co-founder. Watch this space for news of upcoming global startup weekend events near you later this year. Who knows, you might just enjoy it!

You can sign up here https://tinyletter.com/eshassere to receive news of the launch of my first book. It is a book on leading and managing teams based on a simple four-part model that makes it possible for anyone to get a grip and do a good job. I will be sharing the first chapter to everyone on the list in the next few weeks.

I write about how I became the founder of a tech startup as a non-techie, over-40 female with no entrepreneurial experience, and all I am learning along the way. You can see more here: https://medium.com/@eshassere If you think this might be helpful for others on their entrepreneurial journey, please recommend and share by clicking the heart.