It’s paradoxical.

Everyone knows how significant a brand’s personality is, and what an impact it can have in highly-competitive industries like finance and tech. Even VC firms — #goals for emerging startups — go out of their way to convey their core values to tech founders and potential investment partners.

For example, Andreessen-Horowitz, the VC money behind stalwarts like Twitter, Facebook, and Skype, takes a minimalist approach — in streamlined black and white — to suggest the end results are what really matters. In contrast, General Catalyst — which has put more than a billion dollars behind consumer-facing product and lifestyle companies like Airbnb, Warby Parker, Snapchat and Stripe — uses sizzling color to illustrate its founder-focused enthusiasm for great ideas. Two completely different outlooks, both recognizing the importance of communicating key information to the people they hope to connect with.

Here’s where the paradox comes in.

While successful individuals can agree that dynamic communication skills are essential in the marketplace, some of these same individuals will actually put aside those skills when it comes to their personal lives, and instead expect some kind of magical chemistry to guide their dating lives. I see it so often in my work as a relationship consultant and matchmaker. And often, it’s high-achieving, successful men who fall into this trap. The problem is that many men have been told by popular culture time and again that romance is a byproduct of financial success, or that deploying little tricks and gimmicks is the secret to finding someone to share your life with.

The reality is lot simpler, thank goodness.

The same skills and values you use in business to establish and secure a connection with a customer or investor are the same skills you should be using everyday in your personal life, especially in your dating life. Here are my top three to get you started:


As 19th century writer and psychiatrist Karl Menninger beautifully put it: “Listening is a magnetic and strange thing, a creative force. [Those] who listen to us are the ones we move toward.”

In the tech world, listening is the best way to find your product market fit. Asking potential customers what they want and need, iterating through user testing, and knowing the market helps you ultimately get your product into the right hands and scale your business.

And while you aren’t exactly trying to scale yourself in your personal life, you are essentially “on the market,” and trying to find the right fit when it comes to love.

Listening and being open will help you notice those you’re most likely to genuinely connect with. Being present on dates, and just interested in learning more, will help you identify whether a connection is possible, particularly on a deeper level. And most importantly, listening is an excellent way to solidify a connection if you’re feeling a spark!


I think Richard Branson nailed this one when he said, “Be authentic and organic. It can’t be forced, or it won’t work. And most importantly, have fun.” He was talking about business, of course. But take it from an expert, the same is true in love.


Now before you object to this, when I say “value,” I probably don’t mean what you think I mean. Keep in mind this is just a fun way of looking at the soft-skills you use in business, and exploring how they can help you level up in your dating life. And we all know providing value is key to success, especially in the tech, where multiple startups compete to be the go-to solution for any need.

Here’s what I mean by value in the context of dating and relationships:

What are you like to spend time with? In other words, what might make someone actually enjoy your company?

It’s not about being more impressive, more successful, more educated, more talkative, or more entertaining. It’s really about making a human connection and seeing if a spark ignites. Sharing a positive experience together requires nothing more than being pleasant and attentive. See where that takes you.

There you have it! It’s not rocket science, I know. And yet, I frequently see people fail to give themselves permission to just enjoy dating and be human while meeting other people. If you’re at a point in life where you are looking for a lasting connection, put aside the stereotypes and games, and start with these three skills.

Not every date will turn into a forever situation. But at the very least, you’ll find yourself leveling up in the quality of people you attract, having more memorable dates, and enjoying the process more.