My Startup vs My Girlfriend

I love my girlfriend Nicole.

But she sure didn’t feel the love when I sat her down for a little talk.

Not long ago she’d moved in with me.

It was my idea.

I told her:

“Baby, I’ll take care of you, I’ll support you, and we’ll have a wonderful life together.”

Our plan was to start a family in the near future.

But things didn’t go according to plan.

When we first moved in together Nicole and I ran on the sheer excitement of being together and building our dream life.

In a word, we ran on love.

But as my business grew I poured more of my time and money into it, my attention came under siege.

While I didn’t expect to have an easy time bootstrapping a company I honestly didn’t expect to be working so insanely hard either.

I rarely have the time to train BJJ and lift weights, almost no time to explore in nature, and worst of all - less time than ever to spend with my girl.

This makes things less lovey-dovey and more fighty-shoutey.

Nicole loves to go out to eat (and so do I) but food costs money.

Nicole loves to travel around Thailand (and so do I) but that, too, is not free.

When you bootstrap a company you try to avoid spending money on yourself because your business needs it so badly.

You then cut the inefficiencies out of your schedule in an attempt to squeeze an extra 45 minutes of work out of the day.

You used to sleep 8 or 9 hours per night but now you’re happy with a solid 6 and a half.

Stress frazzles your nerves, you lose your cool over some stupid little thing, and you feel ashamed at your outburst afterwards.

If you blow this opportunity, you can say goodbye to your girlfriend, to the family you dreamed about starting, to your team members who were depending on you, to your feelings of self worth and to the whole beautiful future you’ve built up in your mind.

“I’m a failure, a loser,” you’ll think.

“I’m 30 years old and I’ve been staring into my laptop from Thailand for the past 4 years; what have I got to show for it?

When I’m at a restaurant I still have to look at the bill and do mental calculations.

I’m sick of looking at restaurant bills, and bills in general.

It’s humiliating.

And worst of all, I have nobody to blame for my lack of success except myself.

Throughout my life I’ve had countless opportunities handed to me on a silver platter and I squandered them.

I simply made too many bad choices, too many mistakes.

How long will I go on eking out a measly $3k/month while some 20-year old punk cranks out 6 figure months?

Why does he have the money and the freedom and I don’t?


If I’m going to put everything important to me on the line then I have to go all-in with this business.

Exit or bust.

If I win, I win big.

If I lose…I won’t lose.

I can’t lose.”

With these thoughts haunting me I sat Nicole down and asked her to move out.

We’d lived together less than 60 days.

I tried to explain it cooly and logically knowing full well that she didn’t hear anything past “I think we should go back to living separately for a little while.”

My reasons were airtight:

I can no longer afford to support her and fund out of my own pocket at the same time.

I can no longer afford to be cavalier with my time; every minute counts.

I can no longer divide my limited energy and attention between two things that require a lot of both.

Do I miss the days before I started this company when we’d laze through long meals, take languorous motorbike trips together, and spend half the day in bed?

Fuck yeah I do.

But I can’t give my girl all the attention and love she needs without sabotaging my business.

And yet I can’t grow my business without taking away the food that our relationship needs to survive and grow.

Oh how God loves to troll us.

On the one hand, this business could provide us with everything we want for the future.

On the other hand, we can’t live on promises of future happiness which is not in the least bit guaranteed; quite the opposite - most startups are guaranteed to fail.

A successful business can help our relationship blossom by removing money problems, which is proven to be the #1 relationship killer.

But the very act of growing this business could kill the relationship.

Irony thy name is entrepreneurship.

Now I’m in Pai for the weekend Slicing Pie with my business partner Lesly and heading back to Chiang Mai tomorrow.

Nicole is back home in Bangkok.

We’re holding together (we’ve done long distance before) and we talk everyday.

The one thing we’ve got on our side is that we love the shit out of each other.

Everyone can see it.

I suspect we make our friends a little nauseous when we’re together.

Last night I told Lesly that even if everything turns out to not be ok, everything will still be ok.

You can’t let life kick your ass.

You’ve gotta fight for every last drop of success and happiness.

You’ve gotta earn that shit.

Jiu jitsu taught us that.

But though I’m terrified to the core that I’m going to blow my business and my relationship, a part of me has unshakeable confidence that we’re going to make it.

I don’t know why I feel that or where it comes from.

And I’m aware it’s totally irrational.

But I feel it all the same.

We’re going to make it.

We’re going to make it.

We’re going to make it.

Update 2016-12-24

Nicole broke up with me last night.

I don’t blame her.

And I’ll look back very fondly.

Onward and upward.