On: Startups, Love, Life and Loss

I’ve been trying to write a version of this article for roughly 3 years. Around that time, I had already kicked off and committed myself to PaLaCart. Unlike some commitments in my life, I wasn’t going to let anything get in the way of making it successful.

The definition of success during that time has changed quite drastically. That term continues to evolve on a very frequent basis as I get to know myself, pursue my goals and live in a moment where everything is uncertain — except for the uncertainty.

I know just a few things — I know that tomorrow morning if I wake up, I’ll have a list of things to do. I know that when I go to bed tomorrow, I’ll have a list of things that I’ve crossed off my list, but also a bigger list than I originally started off with. I know that my nights are going to be spent sleeping, but also with thoughts and ways of finding success.

The morning after that, success might mean sleep.

The weekend after that, success might mean going to an office and meeting with only the people that I want to deal with — and no one else.

But, as someone who prefers to look at things in a long-term way, I know that success is a misnomer. Success doesn’t look like the famed hockey-stick chart. Success isn’t a destination. Success isn’t a day or date of accomplishment.

Success is a lot more than that.

Success is having the privilege of waking up in the morning, seeing the people you truly care about and enjoying every moment of every single day without having to worry about what tomorrow holds.

Because the one thing I’ve realized time over time is that tomorrow is not guaranteed. And not in the tragic way either.

As I’m about to draw on my 401k to fund my latest company, my definition of success today means survival.

And basic survival — to be able to eat and pay rent.

I try to live a life without any regrets. Doing that forces me to make decisions. It’s not about separating the good ones from the bad ones. It is about making them. Most days, I sit back, stare at screens, hide behind a keyboard and try to rattle off my plan for world domination.

In reality, that means realizing that it could all go away in a heartbeat. And that is not the scariest thing of all.

The scariest thing of all is to realize that life, no matter what, will go on. And it is your job to either strap in and go for the ride. Or to unbuckle your seatbelt right now and give up because you are too scared.

I’ve funded my companies in 3 different ways:

  1. by writing personal checks
  2. by asking my friends and family for money and
  3. by drawing out all my savings.

And I keep asking why. Sitting in my seat isn’t easy. It isn’t romantic.

It is heart-breaking. It is depressing. Some days get so hard that it becomes nearly impossible to see past that day.

And then I keep thinking back to why. And the answer is simple — because I want it.

I want it more than anyone else.

I am willing to go through this because at the end of the day, it means the most to me.

I hate the romanticism of start-ups and founder struggle. Because you know what? It fucking sucks. Ask any single founder if they like it. They don’t. Because you know why? It is the hardest thing they will ever do.

Day in and day out, there are a few things that I focus on:

  1. fundraising
  2. product management
  3. marketing

On the surface, that sounds incredibly simple. But, when you start looking into specifics — it is insanely hard work.

Did you know that you can only raise money from certain types of investors? Neither did I.

Did you know that in order to accept certain types of payments you have to submit a long application that may or not be approved by Visa / MasterCard? Had I known this earlier, I would have chosen a different path.

Did you know that starting from zero users and finding traction takes more time than most people want to spend? If I was aware of this, I would have raised more money the first time around.

And when you’re thinking about all of these things — it starts impacting your ability to do anything else. Your friends, who you once stood by — counseling them about their latest breakup or family emergencies — are gone.

Your family, who you saw or spoke to on a frequent basis thinks you’re chasing the wrong path.

Building something that you believe in a fool’s errand.

And at the end of the day, I’m willing to be foolish to pursue the one thing that means the most to me.

This is a screenshot that very few people have seen, but I’ve kept this more than most photos, more than most memories and more than most people.


Because that was the last day I was comfortable. To remind me that it was a new beginning. I made a very critical decision that day — I was going to all the way up or flame out into the sunset.

Most people I know of all ages are not willing to lose. They simply are stuck in this paradigm that if you accept a shitty situation, you’ll be fine.

It’s never fine. It’s never OK. That’s called giving up.

And those that give up are the ones losing not just one thing — they’re losing themselves. They’re falling away and apart. They’re dying.

Some people die at 25 and aren’t buried until 75.
— Benjamin Franklin

When I walk away from things — it’s about making decisions.

It’s about those things that I know I want, but I also know I need to wait for them.

It’s about those memories that I need to create, but I also know that I need to earn them.

It’s about those victories that I celebrate, but I also know that they come after falling flat on your face.

And with that comes a vast variety of ups and mostly downs.

But, you know what?

I wouldn’t trade any of it for the world. Not for an extra penny. Maybe the reason we lose first is so that we can do things that most people can only dream of doing.

This journey, that most people call life, is not about success. This journey is about hell of a lot more. It’s about winning when you’re down. It’s about escaping when you’re trapped. It’s about those moments that put the biggest smile on your face.

Do it because you love it. Do it because you can survive it. Do it for you — and just you. Don’t live for someone else. Not today.

So, to every entrepreneur who has gone through this and continues to go through this, I leave you with An Old Irish Blessing:

May the road rise up to meet you.
May the wind always be at your back.
May the sun shine warm upon your face,
and rains fall soft upon your fields.
And until we meet again,
May God hold you in the palm of His hand.