How a Start-Up is like ‘Dating’

Before I got married, I had been on a few dates, had lots of crushes, and a couple of relationships. The dating dance was never my thing. I always wanted to skip the niceties and get on with it. The constant questioning of ‘maybe they’re just not that into me’ was exhausting.

I wanted both of us to be ourselves, be honest, and raw – but that is just not how it was.

The persistent games people play when it comes to playing it cool and not wanting to jump in too deep too soon.  However, through this, I learnt that a new friend was just as good as a date.

Friends make your life a bigger and better experience, you can never have too many and you never know where a friendship might lead.

Then I jumped in to the world of a start up.



The ‘dating dance’ is much like the ‘start up dance.’

It’s an analogy I have used since we were one month into our start up trip-of-a-lifetime.

We were full of optimism and surety that …

“Yes, I look great in this – let’s rock the dance floor.”


“We can use all my experience in the industry,”


I said,

“And, build a product that I would love to use and share it with those that need it too.”


We hit the ground running with the launch of our MVP (minimum viable product) and then it was time to get out there and see …

“Are they into us?”


Using our known networks, we reached out to potential customers, sought feedback …

“Do I look good in this?”


And, we flirted with the idea of spending more time together.

Then we waited for them to call.

And, waited.

And ,waited…. .

And, they did!


A call from a customer confirming a two year contract.



This has moved from dating to relationship gold.

We had hit the jackpot with our first cab off the rank!!!

Then we waited.

And, waited.

And, waited …. .



What followed was the equivalent of dating HELL.

We were flirting with many more possible admirers, but they were showing signs of just not being into us. Or were they?

I once called a guy I had a crush on when I was in 15.

He picked up the phone and we had a great conversation, ’cause he learnt a little more about me and we clicked. He wasn’t quite ready to accept all of my 15 year old awesomeness, so we moved on and stayed friends. This feels like where we are now with our start up dance: the world isn’t quite ready for our awesomeness in one fell swoop.

Enterprise sales can be long and hard. But, like some dates, we can go from initial introduction to a signed contract in just a few weeks. So, one at a time, every day, we follow up leads, meet a possible admirer in a new place, and dance the start up dance.

When we get the timing right, one more admirer sees the light in our eyes and accepts our invitation. We’re pretty persistent, and we’re good humans.  We persevere, listen, build up a solid rapport and send great gifts.

It is okay being ‘friend zoned’ in the startup world.

Friendship makes the world go around and should be based on mutual respect. Respect builds start ups into solid, profitable companies. We would prefer to be respected than liked. We want more friends because they could become customers, and there is nothing more beneficial to a start up than paying customers.



I have learnt that in the start up world, persistent start up founders will accept a “NO!” as a “not now” (“maybe later”).

This is a surefire way to build respect, trust, and friendship, that one day just might grow into …

“They really are into you!”


And, you will both mutually benefit.

Just like when I met my future husband at a friend’s 30th birthday. It was a black and white themed party and I was dressed as a railway crossing (but that’s another story). Despite the unusual costume, he persisted.  We built up a great level of trust and a solid friendship which turned in to, so far, a 12 year marriage!

Next time you’re approached by a start up, please take their call, respond to their email(s), and follow through when you say you will. If you are not into them, tell them. Let them move on to enabling their energies to go into other opportunities.

If you are a founder who finds themselves in the full swing of the start up dance, remember that perseverance and resilience are vital when it comes to identifying and attracting admirers.  Be consistent with your message, understand your market and get on out there and spread your awesomeness.


Thank you.

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