3 Life-Changing Lessons I Learned For Business While Dating

Often, lessons learned from one aspect of my life end up making sense for ALL the other aspects. This holds particularly true in business and dating. I’ve been dating longer than I’ve been in business but dating has taught me some extremely valuable lessons that I still apply to my business each day.

Some background, I grew up in a weird way as a childhood. I changed schools almost every school year, K-12, until I finally graduated high school. Some people say change is good but in my experience, it can also develop other problems. By the time I got to high school, I had trouble developing emotional connections with people. I mean who can blame me? A kid who’s naturally extroverted gets his heart ripped out because he makes friends with people who he thinks will be his friends for awhile.

At least for more than one school year. This happened every year. I’d fall in love with where I was and end up getting taken away elsewhere before I can stick my toes in the sand. It hurt. Like a bad breakup. Year after year. This caused me to stop developing deep relationships with people because in the back of my mind, I’m never gonna see you again. It remained surface-level. For me as a high school sophmore, it was about sex, fun, and good times. Nothing more.

Being extroverted, I never had a problem making friends. I was quite good at it. Especially because I had to do it year after year. Socializing and vibing became second nature for me. The problems came when I was in a committed relationship. I was being held accountable for my actions. What I did or didn’t do affected her in some way. Eventually, I lost a great girl due to my undying attraction for one of her teammates. That brings me to my first lesson:

1. Commiting To The Cause

You’re purpose for dating someone or starting a business has to have deep resonance with you. It has to be more than about the pleasure of making money or sex. Emotions are fleeting.

And if you don’t have a deeper meaning to why your committed to this person or project, you’ll start to look elsewhere out of sheer boredom. Most people get into commitments because it’s exciting and trendy. Ever started a projected you proceeded to ignore a week or month later? It’s because you lacked a deeper purpose for why you were doing it.

Your expectations fail to meet reality and you end up blaming others or moving on to something that excites you again. Excitement and passion share the same energy with two very different intentions. Excitement burns quickly while passion simmers consistently over the long term with flashes of intensity every once in a while.

Passion burns slowly in the background, maintaining it’s flame. It’s what you’re doing consistently week after week, sometimes, unintentionally. When it comes to dating, only time can tell whether you’re genuinely passionate about someone or just excited to fuck. Nothing wrong with either. Know the difference.

If you’re single, commitment yourself to a deeper cause than just getting laid and having fun. Yes, it is fun while it last but just like the business owner who’s cause was to make $1 million, once he makes it, it doesn’t gratify her anymore. Maybe you can commit yourself to building stronger social skills, creating a better circle of friends, developing a harum, or structuring a polygamous relationship. Whatever it is, make it deeper than just sex.

2. Be Bold

You hear this alot but I often see people get sidelined by fear way too easily, including myself. I forget to be bold, always. Every high quality girl that I’ve dated did not just fall into my lap. It took work, skill, and persistence. Not to chase her but to just approach her. Its okay to feel intimidated by your desires. Fear of potential loss is human nature. Every logic in my mind tried to convince to not approach her. It all stemmed from one thing: REJECTION. REJECTION. REJECTION. Fear of loss.

No one wants to deal with rejection head on. It can be painful to watch your fragile ego crumble before your hands. It’s why some guys can’t handle being told no by a girl without berating her. His ego lies crumbled in his fingers and the quickest way to put the pieces back together is to put someone down.

Boldness is a skill to be developed. It’s built over time. Being an entrepreneur, fear is hiding around every corner you turn. It comes from the fear of the unknown. The journey lacks certainty, one of the basic human needs. Entrepreneurs are attractive in most people’s eyes because of the fear and ambiguity that they tolerated over the long term to create great success in their respective field. As an entrepreneur, everyday, MAKE THE CALL.

While single, I dedicate time to meet new girls. Aside from going out on tinder dates, I cold approach women I find attractive. Nightclubs, bars, malls, you name it, I did it. This was me building boldness and confidence in my character, something that could not be faked. While this scared me shitless for the next 12 months, I did it almost everyday. Why? Because I knew in order for me to meet a high quality girl, I had to 1. go out A LOT. 2. I had to be bold. You think Beyonce would be married to Hov if he was scared to drop an album because of what other people thought about him? HELL NO.

He’s bold and she loves that about him among other things. And besides, what says you’re bold more than approaching a total stranger on the street, letting them know how you feel, and starting a conversation to get to know them? Most women were thrown off guard initially but later thanked me for approaching them. Done correctly, its seen as a positive gesture and women are often flattered by it.

Being bold opens you up to opportunity that’s always been there waiting for you to hurdle over your fears. That girl you dream of probably frequents your local bar or coffee shop. Are you bold enough to approach her just to see how it goes or will your mind convince you that you’re not good enough? Are you bold enough to make that sales call? Enough to power through the tough times in your first 2 years in business? BE BOLD.


I can’t tell you how many times I’ve missed an opportunity because I didn’t go to a networking event or cancelled a date. My excuses we’re always the same: “I’m tired.” Which may be true but is it a valid reason to not capture opportunity? Sure this world is a place of vast opportunity but does that mean to devalue present moment situations that can benefit you? Hardly not. The funny thing is when I run into someone and they say “Dude, you missed it, you should’ve came.” Know what I hate more than rejection? Missed opportunity. It stings.

Like the time I was too afraid to kiss a beautiful girl after our date. I ended it with a strong hug which I’m sure telegraphed how horny I was but too afraid to SHOW UP and BE BOLD. I could tell she liked me but fear lied and crippled me once again. She never returned any of my texts again and I don’t blame her. Why would a great girl like herself waste time on someone who doesn’t have the balls to make moves. I surely wouldn’t want a business partner like that. Painful but it taught me a valuable lesson. If I had simply show up, I could have been potentially dating her right now, who knows. In dating and in business, seizing windows of opportunity is key. Never take them for granted. Most times, once it’s closed, it’s closed for good.

Successful business owners resonate with the now mentality because they understand that it’s vital to seize opportunity as it arises. Today, for example, is an opportunity for you to spend your time contributing to something that’s meaningful. Whatever that may be. This day is a opportunity, are you going to show up?

Pros show up to their craft everyday no matter how they feel. We all have days where we just wanna hide under the covers to avoid our struggles but it may also be the day you get the result you were looking for. You never know and that’s why it’s important to just show up anyway. Life can be simple. You either show up everyday or don’t. The world is not a crazy enough place for it to start rewarding a bunch of undeserving people. I’m not perfect myself but I use my writing as a daily reminder for this exact principle.

If I had simply decided to show up regardless of how I felt, I could be $100,000 richer with a great partner by my side. But I don’t, simply because I decided not to show up and choose self-acceptance.

I hope you enjoyed this article! Hit the like button, if so. Every heart means a lot to me! Thanks!