What Dating Has in Common with the LeanStartup

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(Note: This post was originally written in 2010, before the Tinder Revolution. That said, I think a lot of the ideas are still relevant today)

The other night I had the unexpected pleasure of sitting in on a #LeanStartup Presentation by Eric Ries at TechStars Boulder.  As he was talking, I couldn’t help but compare everything he was saying about Startups, to my current dating life.  Let’s examine this in more detail.

Stop Wasting People’s Time

This is the first rule of the LeanStartup, and if you’re out in the dating game this should be your #1 rule of thumb.  Life is short, don’t spend time dating people you’re not really into, just so you don’t have to sit home alone on a Friday night.  I’ve been guilty of this (more than once), and in the end you only end up creating false hope and setting up false expectations.  No one likes having their time wasted.  It’s better to be open and honest.  Yes, sometimes you might hurt the other person’s feelings, but it’s better to tear off the band-aid with one quick tug, then to painfully and slowly peel it away.

They say that “Software is imagination made tangible” in that same light, “Relationships are dreams made practical“.  But just like with building software, the question should not be “Can it be Built?” but instead, “Should it be built?”.  Should we build a relationship together?  Any two people off the streets could meet tomorrow and decide to have a relationship, and if they are both committed to it working, it will.

90% of Startups Fail

Turns out that the odds might be slightly better in dating, but not much.  That’s why dating is a numbers game.  The more people you date, the better chance you have of falling into the 10% that make it out alive.  So get out there and date, date, date.  Take risks, try new ways of meeting people, but above all – keep at it. The 10% of Startups that make it, are the ones who get up after each failure and try again.

Entrepreneurship = Awesome

According to Ries, it’s the “Best Time in the World to be an Entrepreneur” – and it’s also the best time in the world to be dating.  There are more ways to meet people online and off than ever before.  And online dating sites like Thread, OKCupid, and Chemistry.com have revolutionized the way we meet, interact, and communicate with potential partners.  A lot of these sites like OKCupid and Plenty of Fish are even 100% FREE.

If you’re a little more old-fashioned like me, you might also consider hiring a Matchmaker. I highly recommend Nina Friedman (Yenta Girl).

Entrepreneurs Want To…

Turns out that most Entrepreneurs want to do 3 things:

  1. Change The World
  2. Build An Organization of Lasting Value
  3. Make Customer’s Lives Better

Hmmm…that’s exactly what I’m looking for in a relationship. I want a partner who’s going to Change My World (hopefully Rock It too), who wants to build a valuable Lasting Relationship with me, and someone who makes my life better.  And I bet you’re looking for the same thing too, right?

What’s A Startup?

Startups try to create something new under conditions of Extreme Uncertainty.  Startups are an Experiment. If that doesn’t describe dating, I don’t know what does? At the beginning of a new relationship, all there is is uncertainty. Does he like me? Do I like him? Are we a good fit? Will this work? Should I call? Will he call? What if she never calls? Lots of unanswered questions. Lots of worry that we might say or do the wrong thing and kill the relationship before it’s even begun. But if we think like Entrepreneurs, then we’ll quickly realize that the key to a great dating life is to become comfortable with uncertainty. To not only accept it, but to embrace it. To remain open, and most of all flexible. Trust me when I say things won’t always go according to plan – and that’s why it’s important to learn how to Pivot .

Successful Startups Have Mastered The Pivot

I have GeekADD so I might be a little too good at The Pivot. Anytime I see a shiny object, I drop whatever I’m doing and start chasing after something new. “Look – A Squirrel”. But doing The Pivot effectively is less about chasing shiny new objects, and more about understanding what’s working and what’s not and making small (and sometimes large) adjustments to your current plan. Just like a pilot flying to Hawaii has to make small adjustments to his course to meet his destination, Startups have to periodically re-evaluate their current plan and make course corrections as necessary. In some cases, this means completely abandoning a current idea and trying something radically different.

The same is true in dating. We can’t hold on too tight to any one person or any one projected future. We can’t put all our eggs in one basket and just hope it works out for the best. If we want to be successful, if we want that IPO, we’ve got to be willing to change directions while at the same time remaining grounded in what we’ve already learned.

Speed Wins

And it’s not enough to just learn how to Pivot. We’ve got to learn how to decrease our time between pivots. If you hang on to a losing idea for too long because you’ve become attached – there is no question that you’ll fail. You’ve got to let go and move on quickly. Don’t stay in bed crying over what might have been, take what you’ve learned and get out there and try again. The quicker you move on – the better your odds of success.

The Gartner Hype Cycle


Finally let’s take a look at the Gartner Hype Cycle. If we compare this to relationships, we can see that dating starts with an “Attraction Trigger” (Technology Trigger). In the beginning everything is champagne and roses. We tend to idealize our potential partners, putting them up on a pedestal, and creating expectations that they will never be able to live up to (Peak of Inflated Expectations). As time goes on, we begin to realize that our potential partners might not be perfect afterall, and this sends us into a slump (otherwise known as The Trough of Disillusionment). Many relationships never recover from this failure to meet unrealistic expectations and end here. Couples that do make it through this slump are the ones who remain flexible and open to new ways of seeing their partner and their relationship (Slope of Enlightenment). And over time, these same couples find themselves in a steady, safe, and secure partnership (Plateau of Productivity).

18 Comments on “What Dating Has in Common with the LeanStartup”

  1. I find it interesting that the graph of the Gartner Hype Cycle resembles the display on an ECG of the last heartbeat. Up, down, flatline.

    Your comparisons of startups and relationships are revealing. In fact, the overarching lesson, that getting back up after a knockdown is worth it and a requirement if you are going to engage in low-success-rate activities, is applicable to very lengthy job searches. That's my own example which fits the patterns you recognize.

    Thanks for this. Great article!

  2. hmmm wonder what a girl would say if i told her that we needed to optimize her, as she wasn't working out for me. or that i was looking for a more optimal fit and needed to pivot away from her, and onto a new sample, but if the new sample doesn't work out, i'll come back…. how about a/b testing for dating…. ah man the comparisons are endless, and i doubt i could find a girl with a good enough sense of humor to appreciate them. or rather a series of girls.

    great post E

  3. Erica. Love the great insights and comparisons that you made to dating. In the end, most of what we do comes down to the making the most of the relationships that we build and treasure. Giving and getting..they go hand in hand. You are a great asset-based thinker and have helped reinforce for me that the best and most treasured relationships are those in which we feel we give more than we get.

    Keep on reinventing and sharing, my wonderful friend.


  4. is it possible to "start up" a relationship" with someone and "start up a business" at the same time? does something have to give? do you need to wait until one of them is "successful" before stating the other?

    1. Is it possible? Yes. Recommended…maybe? I think it really depends on the maturity and commitment level of the people involved.

      I'd say just start a business with the person you want to have a relationship with. Kill two birds with one stone 😉

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  7. Good post. I find that it is so easy to relate a startup to a lot of things. And this is a good one. @Brian's comment about optimizing is funny as hell. I know a few who can stand to be a bit optimized. Hope your enjoying your time offline. Your whole 'I don't do speed bumps' thing popped in my head today and I had to come see where you went.

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