Flirting amp; Dating Startups Ideas

Working at a Startup Studio has given me a new appreciation on how to select an idea, build a startup and make it successful. Actually, not so much what makes a startup successful, but what makes good people pick bad ideas or bad strategic directions.

First of all, let me say I believe there is no correlation (or a very weak one) between an idea that *sounds* good versus an idea that *is* good, and by good, I mean something that customers want and that you can capture value from it.

If I could pinpoint one mistake that seems to afflict too many entrepreneurs is optimism. More precisely, blind optimism. You believe your idea is so good that you have a Confirmation Bias for it. You avoid turning stones that might conflict with your views, or, you simply rationalize the bad news into some positive version of it (“Yes, there are another dozen companies doing the same thing, but we’ll have a feature X and that changes everything”).

Did you marry the first person you dated?

If you imagine all decisions you make in life, the bigger the decision, the more careful and thoughtful you are about it. Picking a meal or a gas station doesn’t take too much time. Picking a laptop or a car to buy takes a little bit of research. Picking a house or college to attend, a lot more research and thoughtfulness. Picking a spouse, pretty big deal.

So why picking a startup idea is done so haphazardly?

Here is a typical founder’s story plot: Find something you are trying to do and don’t find a solution. Ask a few other people if they had this problem and they say yes. Lightbulb! “I need to fix this problem”. Confirmation Bias kicks in and all signs point to “Go”. Sink 3 years of your life. Write a Medium post telling why you failed.

That’s the equivalent of meeting someone at your first day in college and by week two asking them to marry you.

Flirt, Date, In-Relationship, Engage, Marry

Just like dating, I believe there are different phases of the relationship and for each of those phases, there is a different level of commitment and approach you should use to make sure it’s working and when to take it to the next level.

Flirting: This is when you want to do something, but you don’t know what exactly, yet. You might have your preferences. You are throwing some ideas out there and asking people about it. In this phase, you want to be ambiguous, open, and as broad as possible. Don’t close doors. Don’t assume things. Flirting with ideas is important to see how excited or not you get about them.

Dating: Well, you found one or two ideas that seem to be the most promising ones. It’s time to take them out for coffee. That is, it’s time to start telling people, particularly potential customers, investors, and partners. Avoid confirmation bias at all cost. Don’t push it to make it work. Negative signals not necessarily mean it won’t work, but it’s better to know the flaws and concerns around your idea.

In-Relationship: Time to start spending some serious time. If of all the ideas you flirted with, and out of the few you dated in the last few months, this one feels like the one with the highest chance, go for it. Your mental commitment right now shouldn’t be that you’ll spend the next 4–7 years of your life with it, but that you’ll give it a good 3–6 months to test many hypothesis. It’s important to live in the moment during this phase. Don’t make investments that only might pay off a year or two down the road (you wouldn’t book a cruise in the Mediterranean Sea a year from now if you just started in a relationship with someone, would you?)

Engaged: Bam! It’s working. Your prototype is working. People are giving feedback, you are iterating fast, and you might even have a few paying customers (or high engagement if it’s a consumer business). It’s time to ask your Startup to marry you. I mean, it’s time to say that you do want to spend the next 4–7 years building this. Time to fundraise, or bootstrap for real this time. Give your 100%.

Married: The moment you’ve got investors, or paying customers with long term contracts, you married your idea. Focus should be on learning in the cheapest way possible how to improve and grow your business — all metrics, up and to the right. The kids of this relationship is a sustainable (hopefully growing) business that doesn’t depend on you to survive.

The Warning Signs

I’ve seen (and personally experienced) many bad “relationships”. They come in many flavors, but these are somewhat common:

  • Founder never flirted with the idea. He immediately jumps to the Dating phase and from there on, he doesn’t even stop to question if that’s the one.
  • Founder goes from Flirting to In-Relationship without dating. This is pretty much heresy in the Lean Startup religion. Never telling anyone or asking for anyone opinions and “just knowing” is risky business.
  • Founder has low self-esteem issues and when he’s flirting with an idea he picks an idea that’s too small, but that he feels he could succeed on it. He ends up building a tiny business and resent it because he can’t breakthrough it.
  • Founder is polygamous and is In-Relationship with two different projects, or worse, he’s married, I mean, has raised funds to a startup, and start dating another idea. This is actually more common than you might think. A lot of founders like the initial chase and have a hard time committing to a single product/business.

The bottom-line is pretty obvious: Take the right amount of time — not too much or too little — at each phase and have a good thought process of when to move to the next phase or drop the idea.

Marcelo Calbucci

Marcelo Calbucci

I'm a technologist, founder, geek, author, and a runner.