What I Learned About Dating That Will Transform Any Business…


I was a huge geek in high school, so I failed to learn the art of dating until much later in life. I watched my peers with envy as they wore their sweethearts’ letterman jacket or passed notes across the room. The trick of winning the affection of my suitor completely escaped me until the age of 30, but then, it finally clicked.

During the same year, I had decided to leave my cushy job practicing law to start my own tech startup, and I found myself on the fateful path of having to raise equity capital. I consider it a blessing that I didn’t learn how to date until later in life because as I learned my newfound dating skills, I saw how seamlessly they translated toward winning the attention of an angel investor or VC.

Related: 7 Mental Shifts That Allowed Me to Become a Millionaire at 22

Follow these three simple tips to catch your target’s eye, whether inside or outside the business arena.

1. Be the football player. Be seen.

As my girlfriends coached me on catching another’s eye in dating, they taught me an important lesson: “Everyone wants to date the football player because everyone wants to date the football player.” This reasoning may seem circular at first, but when you spend some time with it, there is much to be learned. You and your company must become the football player.

Attend meetups for your industry and in the startup scene. Sign up for accelerator programs (which are often funded by angels and venture funds). Participate in pitch competitions (the judges are usually investors and there are several that have cash prizes, making this serve a dual purpose). Find a way to set yourself apart, and then get active.

The more you participate, the more likely you are to find yourself in front of your target investors on multiple occasions, or even better, as a topic of conversation among them.

Related: 25 Common Characteristics of Successful Entrepreneurs

2. Create a competitive playing field.

Being the football player requires more than showing up to practice. If you want to catch your suitor’s eye, you must also make yourself sought after. If you don’t have multiple offers on the table, make them think you do.

Become a “Celebrity CEO.” Reach out to your local newspaper, anyone who covers your industry in the national press and anyone else who will listen. Find a spin about yourself and your company that will catch their eye. Read what they have written in the past, and pitch them in a similar way. This makes your company their prime next story.

Also, name drop as much as you can! In the fundraising game, investors appreciate knowing that other investors are also interested in your company. When one investor tells you they are interested in learning more, note their name and use it in your other investor pitches. Look your targets up on CrunchBase to see who they have co-invested with in the past, then reach out to pitch each of them as well. This not only creates safety in numbers for your investors, but also it causes them to think they may miss out if they don’t jump at the opportunity to work with you.

Related: How to Become a Millionaire by Age 30

3. Close deals with urgency.

The best way to close any deal in business or life is to create a sense of urgency. Communicate your excitement (if you aren’t excited about your company, no one else will be), name drop wherever possible, create buzz in your industry and the press and then close the deal.

Letting your suitors know that you may pursue another path outside of them is the best way to get their attention and get them to move quickly. Be clear about your interest in proceeding with them, but let them know that you are receiving pressure from others to close. This will often get them from a soft circle commitment to a term sheet, or from a term sheet to closing.

In the game of life, business and love, it never hurts to play the field. In fact, it may be necessary to catch the perfect match.

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