How to Turn Your Bad Dates into Powerful Business Lessons

casey-newventureescrowCasey LeBlanc

CEO | Investor | Entrepreneur

Casey LeBlanc is the CEO of New Venture Escrow. He is a serial entrepreneur that has led several small to medium sized businesses that have experienced rapid growth and scale. He is also a business development addict that thrives off of innovation and promotes healthy leadership.


My usual process for picking a topic to write about starts with jotting down thoughts that permeate in my mind and for some reason continuously linger.

From there, I think through the ideas, write some outlines, form some basis for a conclusion as to why those thoughts occupy my brain space, and begin to evaluate whether or not they would be interesting enough to explore.

From there, I float the ideas over to a few coworkers, friends, and maybe even family. For this particular topic I floated the idea of “business and dating” to someone (I will leave the name out to protect the guilty) and she responded back instantly “Oh GOOD –

“Can’t wait to read your thoughts on the difference between something you’re good at and something you’re terrible at!”

Alas, the support has been nothing short of underwhelming.

But that’s not stopping me. I think funny dating stories should be shared, enjoyed, and used for good versus evil.

So as I put together my outline, I thought of the best (which by most standards actually means the worst) dates I’ve been on and how I translated them into career insights.

This is fun. It is meant for entertainment. So please spare me the judging.

Warning to all who read – It really is a zoo out there.

The stories you are about to read are 100% real.

These actually happened. I am not creative enough to make this sh** up, and frankly is even a little embarrassing to open up about.

I am often surprised at the level of interest and questioning I get about the single/dating life in my business interactions. So I figured why not have some fun with the topic, and open up the discussion on dating and business to see if my coworker was right.

So let’s try and have some fun with this one. People take themselves way too seriously, so I am going to try and make some lighthearted fun out of my dating and business adventures.

I would be lying if I told you I was not fascinated with what I had discovered.

Frankly, as you will soon learn, I don’t know sh** about successful dating, so please do not expect a “how to fall in love” post

For some perspective I am, however, a true believer and practitioner in the following:

  • Learning from everything I do
  • Consistent self-development
  • Not taking myself too seriously
  • Believe that life is short and live every day
  • & have a Relentless drive for improvement in everything I do

I swear there is a point to all of this, so keep reading until the end. Please and thank you.

So what business lessons could I possibly draw from my dating life?

Well, for starters, both dating and business nowadays typically include people, technology, and results.

Is one easier than the other? Let’s take a look at what the statistics say.

For starters, the California divorce rate is said to be above 60% for the first time ever. Over half of the “I do’s” in the country’s biggest state are destined to crash and burn.

How about running a business– any easier?

Surprisingly, the statistics for that are just as bleak.

In an SBA study, with years of research behind it, only one out of three small businesses survive 10 years of operation.

The point?

Both dating and business are fuc**** difficult.

And if I am going to spend a big chunk of my time (which is our most precious asset) pursuing real relationships and lucrative business opportunities, I might as well explore and learn how these worlds coexist and even overlap.

Here are a series of three of my personal dating stories that actually happened and how those damn stories continue to haunt… I mean, occupy my mind.

Lesson #1: Know Your “Why” (But It’s OK If It Evolves)

Simon Sinek says, “Our visions are the world we imagine, the tangible results of what the world would look like if we spent every day in pursuit of our WHY.”

Dating Story

I found myself unexpectedly single in my 30’s.

Dating, it turns out, is not like riding a bike where you have a simple set of timeless instructions that can be summoned naturally whenever needed.

So, after a 12-year hiatus from this single world, I found out quickly, sh** had changed.

Online dating changed everything and the general perception of dating was all bad. Mostly, I remember, people squeamish and nervous every time I mentioned being single. However,  I approached it with my usual optimism, and boy was I in for a treat.

One of my first dates was a memorable one. After a few texts exchanged, we agreed to a dinner (how original right?). We met at the restaurant and began the typical small talk.

I knew I was in for a long night from the very first question when I plainly asked what she did for a living. She responded that she was an author and had written 3 books. My next obvious question was what her books were about. No joke, she responded with details on how to buy them on Amazon and that I needed to read these damn books just to get that question answered. Rough start.

That was just the FIRST Red Flag.

Half way through this painful dinner, I figured I would move the conversation to past dating (this can sometimes be a real hazard but I at this point I didn’t care).

She proceeded to tell me she had been on a date with a billionaire 2 weeks prior to our dinner. She raved about the date and the outing she had.

Curious now, I asked how old her date was – as billionaires are rarely young, rarely single, and rarely in San Diego.

Mind you she was 29. He turned out to be 78. Shocker right?

It Gets Better.

My 29-year-old date then looked me dead in the eyes and said, “Casey, I have one thing decided. I will not date a billionaire. Too much pressure. Casey, my husband only needs a net worth of 200M. Two hundred million is less stressful and satisfies all my needs.”

My response after spitting my (what now felt cheap) wine out? “Check PLEASE!!!”

But you know the weirdest part?

I know it sounds weird (and it even feels somewhat disgusting to type) but I almost respected her for being honest. She knew her why. She clearly knew her “what.” I am pretty sure she just hadn’t quite figured out the “how” but was working on it one date at a time.

My initial response was disgust and annoyance, but as I look back and laugh at so many failed dates, she was actually the one who was MOST clear with her “why” for dating. She was straight up with her intentions and laid it all out on the table from the get-go. I clearly had not met her qualifications and we mutually parted ways.

Side note: The restaurant required valet parking. We came separately so I, of course, politely paid and had her car pulled up first. No joke, it was a 1984 beat-up Honda Accord with mismatched wheels and broken glass windows. I said goodbye and quickly realized that the book sales must not be going well.

Business Lesson

Just like the dating world, you need to know your “why” in order to grow your business. And just like in the dating world, my “why” had greatly evolved.

When I first started my journey in business, I wanted to make money and LOTS OF IT. That was my focus and I was obsessed with the challenge. Then, the “why” changed.

Now, my “why” is to make an impact. I not only want to make a difference in my industry but also in people’s lives. I want to inspire and lead so people can achieve more than they ever thought possible.

My “why” in dating has shifted/evolved to investing in quality relationships that energize, motivate, and require that I level up as a man to be the best version of me which in turn would  make the best version of a possible “us.” (Que the eye rolls from many of my guy friends)

Lesson #2: Be Slow to Hire, Quick to Fire.

You know how you should never hire an employee on a whim? Same applies to dating.

I had to learn this the hard way.

Dating Story

Ok, let me paint this picture. I was set up on a blind date.

A mutual friend figured he had found my match.

I pick her up one evening (which turned out to be a really bad idea) and took her to a bar for sunset drinks on a Friday night.

An hour and a half in, she grabs my arm and tells me she has something serious to tell me.

Oh, boy. Here we go. Important to note, we are only 1.5 drinks in.

She proclaims to never tell anyone this on a first date, but she said our date was just that special and she could no longer contain this secret.

Holding my arm, glaring in my eyes, holding a tequila drink with a Del Mar sunset behind her, she tells me:

“There are 9 stages of life. I am on stage 8, I am a REAL ALIEN. You, Casey, are just on stage 3. You are merely flesh and bones. I like you, I like you a lot. I want this to work, but we are going to have to work very hard to get you to my alien level.”

This actually happened. This cannot be made up.

I realize there are many questions, but the story must move on.

Business Lesson

Be selective. And when you make a mistake, hit the eject button and never look back.

Bad shit happens. We make errors. We have bad experiences. We must pivot and move

quickly away (from all aliens).

I realize I can be too nice. I hold on to employees and opportunities too long.

The alien really woke me up. I needed it.

I now know that I only want “A” players, and preferably from this galaxy.

As such, I need to find a bunch of them and get them working together to do cool sh**.

Nick Sabean, the greatest college football coach of all time, has a great quote:

“Mediocre people don’t like high achievers. And high achievers don’t like mediocre people.”

Don’t settle for “meh”.

So if you ever find yourself out with an alien on a Friday night, don’t be afraid to pull a runner and never look back. You can always call an Uber for your alien date and peel out of the valet by yourself (trust me this was done for security purposes – safety first).

Lesson #3: Innovate or Die (or Just Be Single, or out of Business, or Boring)

Today, everything moves so quickly and most people simply struggle to keep up, both in business and in dating. We are busier than ever and because of it we make excuses and have strong rationale as to why the status quo is fine, how it is even good.

Dating Story

Ok, I will admit it, I am lazy when it comes to planning dates.

If I go on 10 dates, then rest assured I will be buying 10 dinners, usually even at the same few places. At this point, I may even know (ok I know them all) names of every waiter and bartender in the few I frequent.

I remember one week, in particular, I was on a second first date in a week (this is not normal for me, but bear with me).

I was at the same restaurant as the date three days earlier, entertaining the same ridiculous small-talk, and staring down at the same pasta I had ordered just a few moons ago. Then it hit me.

I found myself regurgitating the same dumb a** questions I had asked on every first date since becoming single.

I had officially entered groundhog day.

Worse yet, I had become the absolute most terrifying thing any guy could ever be called when he is single – boring, predictable, dull. You name it, I had become it.

I was BAD and getting progressively worse. I was the problem. No more aliens or psychotic authors to blame. It was me, and worse yet, I had prescribed myself as a boring date. Yikes.

Business Lesson

We stagnate in business, and in our careers, and even life from time to time.

Yes, it happens.

Our trajectories of success are not linear lines, moving straight to the right with predictable growth at each axis point.

We progress more like a cardiograph machine with ebbs and flows that look like a child learning to write for the first time.

And by the way – if you flatline, you’re dead.

In the above, I caught myself flatlining when I realized that even I wouldn’t want to date myself (and I love me some me so this was a shocking revelation).

I recognized an awful pattern of boredom, a pattern that would make any young female contemplate giving up on dating altogether. I was the problem and flashed back to all the initial responses I got when discussing the dating world when people used to describe the worst.

Time to mix it up.

I needed to innovate (in my own way) and plan, do things differently and think outside the box.

Truth be told – this is still a major work in progress, but I will always be committed to not being boring and predictable. Committed to unique questions or adventures even when time is scarce.

Like dating, the same is true in my business.

I work in an industry that has “tried and true” methods that several industry veterans swear by. I was in the escrow business (at a former company) for five long years when I realized I was becoming boring. Again, I was the problem and needed to do something about it.

So I left.  I began to innovate and built an app. I went paperless and created my own e-sign platform. I started to recruit and hire energetic talent that believed in something different. I did all of this in 2011 when it had never been done in the escrow space.

The key takeaway? Innovation is tough, progress takes time, and development is expensive – but the results can change lives.

Easy for me in business, a struggle for me in dating.

But at least I recognize it, and the next girl who is crazy enough to date me can bet that we’ll be doing a creative activity, filled with unpredictable small talk and (hopefully) some fiery spontaneity.

Wake up. If you’re not innovating, you’re dying. Business. Dating. Life. Yes.

So how can we apply our dating experiences to business?

Dating and business have similarities but also remain worlds apart in some respects.

At the end of the day, your success is determined by you.

Is it money, freedom, love, and/or legacy? You decide. You choose how to keep score.

But at the end of the day, isn’t life all about the story?

In the true spirit of self-improvement, many of the lessons that I’ve applied to my dating life have also spilled over into my business practices:

  • Clearly defining my “why”
  • Taking my time before diving into relationships or opportunities
  • & Constantly innovating my process

Overall, I believe that I have made my share of blunders in both business and dating. I look back at it all and am thankful for the process, the experience, the memories, the laughs, the wins, and the losses.

After a week of putting this blog together, this one truth has become abundantly clear:

I am dating my business.

We are exclusive and I have never been happier. That is all. The (HAPPY) End.

So what the fu** does this have to do with escrow?

Nothing, it’s funny and fun and we should work together because, based on my dating resume, I need all the escrow business I can get.

Like this post? Share it!


Subscribe to My Blog!

Leave a Reply