My First 3 Startups Failed. Here’s What I Learned.

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Hey people, today I have the utmost pleasure of presenting you a guest post from Vasso Kalaitzidou. I had the chance of meeting Vasso a few months ago and was impressed by her professionalism and her tenacity. Vasso is an “engineer camouflaged as marketer” and she is focused on getting things done! She was Head of Marketing and Operations at a Greek aspiring startup named Fieldscale for almost 3 years. She has tons of experience in early startup operations, and today she will be sharing some of her lessons with us. Take it away, Vasso!

Hi, I’m Vasso. I’m 29, and I’ve been working in startups for the past 6 years. I was fortunate enough to fail fast in the first three. Before I dive into the juicy details and the most valuable lessons, let me first give you a high-level overview of what those startups were about.

Startup #1

Online Platform hosting creative contests for advertising e-shops

Value Propositions: High engagement rate, Diversification of marketing spending, Virality factor

Cause of death: 6 co-founders

Startup #2

Software for testing physical behavior of CAD models

Value Propositions: Fast and accurate results, Solving previously unsolvable physics problems

Cause of death: Trying to sell everything to everyone

Startup #3

Mobile App that connects one’s wardrobe to nearby fashion retailers

Value Propositions: Remove complexity of everyday life, Save time when shopping

Cause of death: Lack of commitment from the team

Startup #4

Simulation Software to help design the new generation of Touchscreens

Value Propositions: Easy-to-use Simulation Software, Results up to 60X faster using the Cloud

Raised $1.5M, selling to the world’s best companies, doing great so far

Cause of avoiding death to date: The mistakes in the previous 3, plus some more

Now, let’s agree on something. Let me skip what we all already know about startups. I mean the basic stuff, like startups should “Solve a real problem”, “Provide the value the user needs,” “Test their idea before spending months on implementation,” “Follow the lean method” etc. OK? I bet you already know all of those, right? Great!

Moving to the juicy stuff I promised earlier, I have summed up eight bits of wisdom that I’m sharing with you, in the hopes of not making the same mistakes as I did. Please be innovative and make your own shiny new ones.

1) (Team) Size matters.

One founder is not enough; two can be a crowd. Make sure that your partner in crime has complementary competencies with you, but your voices sound as one in about 75% of the time. You can’t spend half of your time in strategy meetings just because you two want different things. Sort it out right away, alright?

The 25% of the debate will ensure your company explores all the available options. If you always agree by default, it’s an alarm. What’s a better way of finding leaks and holes if not having to justify and defend it against your brilliant and stubborn partner?

2) I was a perfectionist. Well… too bad for me.

The world isn’t perfect. Neither is your product. And it will never be. This lesson reads: Stop trying to decide what you need to fix but let users decide what needs fixing. They usually know better. Once, we spent a 60-minute meeting to decide on the color of a button. Yes, a bunch of people arguing over orange or red. Seriously, it happened and I’m ashamed.

3) I wanted to be accurate on my predictions. Hahahahahahahhaha.

You won’t know the details about your market unless you spend way too much money and time on it. And at that time, you will already be too late. Go with your best educated guess. Improve it as you go. Don’t ignore red flags because you’ve already invested too much on a market. A good poker player knows when it’s best to fold. You can’t bluff the market, you can only bluff yourself and your investor, but what good will that do?

4) I had this great idea! Let’s pitch it to investors! #not

Investors don’t care about your ideas. Do not waste your time hunting bears with a flapper. Start flying solo in small scale to prove your point. There is a good time to go to investors, and that is when you can impress them with something you have achieved that was out of your control, yet it worked for you. Early revenue and traction being the best for B2C and a few letters of intent from your target market or some trial users with great testimonials for B2B.

5) People will often think that you are as successful you claim you are.

This is something we actually did right since day one: Present the facts from the Mary Poppins angle. I’m not saying you should lie, but stay as positive as you can. Assume that the answer to the question “What’s up with your company” is always “Great” and then find the arguments to support this claim. If you don’t feel it, fake it until you make it. No one wants to work with the grumpy guy. I practiced that technique to an investor I casually met once. He thought we were sinking. Long story short, they invested 150K after a couple of months.

6) Pick a message that sounds “too much.”

I’ve faced the option of using a bold message a handful of times. I can say with absolute certainty that whenever I followed the risky approach, the results were positive or worst-case neutral. Dare. It works more often than it doesn’t. Especially when it comes to marketing and outreach. People appreciate new approaches that make you stand out. Innovation can be found at different levels, not just the product. Check out some of them here.

7) What if it doesn’t work?

It won’t. At least not all the time. Expect failure. Embrace it. Learn from it. The best mindset I’ve seen during a potential crisis was from our CEO at the time: “Of course there would be downturns. So, here’s one. I was expecting it. It’s not the end of the world. Relax, we are still on plan.” It was a huuuuuge relief to hear him talk like that. We avoided the panic and the disaster it would bring on top of the other failure.

8) Is that all?

No. Can you keep a secret? Shhh… Have a plan B. Never talk about it. It should only serve as a pillow for your late night chaotic thoughts. But it will give your psychology the soft, safe support to follow your instinct and the risky options every entrepreneur should be following on their way to success.

What are the most valuable lessons you learned working in a startup? Leave them in the comments or send them to me on LinkedIn. If there are more than 10 good tips that I haven’t mentioned here, I’ll make a Μedium post mentioning you and your company.

Every week day I am dropping short-form value-bombs on LinkedIn. Connect with me now!


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