033 – Sales and Dating: There’s Always More Fish in the Sea | Kai Yu Hsiung

033 – Sales and Dating: There’s Always More Fish in the Sea | Kai Yu Hsiung

It might look pretty similar each time. You go to the bar, sit down, order your drink of choice and contemplate your next step. You people watch. You strike up some conversations with strangers.

And, more often than not, you move on either by your choice or theirs. The process is something Kai Yu Hsiung said he knew well once upon a time. That’s why he also said, without a doubt, that sales is a lot like dating.

Kai calls the ability to deal with rejection an artform all its own, and learning how to approach the art of rejection the key to his success.

It’s a powerful message coming from someone with as interesting a background as he has.

The now-Chief Revenue Officer at Silverline started his career at IBM, has raised jellyfish in his office, is obsessed with Legos and actually enjoys doing taxes.

When he started his first real sales job selling life insurance for New York Life, it didn’t take him long to learn the shocking truth. It’s okay to be rejected. It’s what you do next that matters. Hearing no is a part of the business, but there are more fish in the sea.

Eventually, something will click. And when it does, you’ll look back and understand that failure helped make you who you are today and wouldn’t trade that for anything.

You’ll find value in the art of rejection.


  1. Be Unconventional: If something isn’t working, consider your options. Instead of trying the same thing again, get creative and find a way to approach the situation differently. How else could you work the sale? In what other venue? Would a conversational tweet open the door? What about a cocktail party to help break the ice? Thinking about different ways to sell your product is one of the best ways to react to the inevitable “no” situations you will encounter.
  2. Think Like an Entrepreneur: Whether you’re working for a big company or a startup, a sales career is your own business to run. You may have certain constraints or expectations placed on you by your employer, but you don’t have constraints put on you in terms of how you approach the situation. As you learn the art of the rejection, should be able to firmly own and manage your career trajectory.
  3. No (Sales)Person is an Island: No matter how it might feel at any given moment, you’re not in this alone. In fact, it’s better that way. Why? The more you can surround yourself with quality resources that are genuinely interested in seeing you succeed, the better. You may be great at a single job,, but if you’re truly dedicated to scaling your business, you need partners to help along the way. Identify those people and figure out the win/win scenarios.

Book Recommendation


  • Octiv – Transform the way your sales assets are created, distributed and tracked around the world. Because a better sales process is a better buying experience.

Subscribe to SalesTuners