Posts tagged Startup
On Big Decisions

The phone rings. It's another entrepreneur. It's another pitch. It's another story. And I have a list of questions, a series of doubts and always a twinge of guilt. Why? Because even though I'm not entirely sold on this idea, entrepreneurs call me every single day - asking for advise, feedback or introductions. I'm happy to do it for each and every single one of them - if I believe their story. I feel guilty during most of these conversations because I have been through what they're going through. 

In an entrepreneur's life, there are usually 3 difficult decisions:

  1. When they give up comfort
    • Entrepreneurs are a rare breed of people - they are willing to give up everything to make themselves happy. That's the definition of an entrepreneur. They give up comfort of their current circumstances. They sacrifice relationships to form better ones. Why? Because it makes them happy. Here's the thing: for anyone to even think of these changes means that their current circumstances - professional and/or personal are wrong. But, knowing what is wrong and making the change are two different things. 
  2. When they have to ask for money
    • If you're dreaming, might as well dream big. When entrepreneurs do that, they need money - whether to pay rent or to pay salaries. You always do. And when you have to, your ego is hurt. It hurts going to people that told you once that you wouldn't make it. But, you have to put that in the rearview mirror and let it roll off of you. 
  3. When they're in an incredibly difficult situation
    • The biggest determining factor in success is making hard choices. And the only time you have to make hard choices is when you're in a difficult situation. You know what you do then? You rip off the bandaid. Just fucking do it. If you don't you're going to bleed internally. Or as Paul Graham from YC in an article perfectly titled "How Not to Die" says: "So I'll tell you now: bad shit is coming. It always is in a startup. The odds of getting from launch to liquidity without some kind of disaster happening are one in a thousand. So don't get demoralized. When the disaster strikes, just say to yourself, ok, this was what Paul was talking about. What did he say to do? Oh, yeah. Don't give up."

If you are comfortable with the 3 traits above, I'll tell you this: make the big decisions. Believe in your dream. You know why? Because no one else on this planet will. Not your partner. Not your family. Not even your employees. 

I've started a few companies. Some have liquidated. Others have not. But despite the outcome, I have yet to regret any of those decisions. Why? Because I believed in them and fought for them harder than I have ever fought for anything else. There's no point in fighting for anything UNLESS you believe that it is going to be longterm. 

And if you're not always fighting, then you're making short term decisions. Decisions for today. Not for tomorrow. And those decisions are never going to work. That's my promise. 

10,000 Hours

This past week has been a really interesting week for me. Mondays always start early and Fridays always end late. The first part of the week is pure hustle and the latter part of the week is administrative work, project work, etc. 

As of this weekend, I've spent exactly 4 full weeks in New York continuously. Being on a plane on my way somewhere, anywhere, is much more soothing for me than being in one single location. After brunch today, I was tempted to jump on the next flight to Miami and then return either Sunday night or Monday morning. I had the flights on hold. 

And as I pondered that thought, I realized that the possibilities I had in front of me were unbelievable - wine in Napa, boats in Miami, clubs in LA, etc. All of it is possible. All of it could have been done. 

And then I decided to be good and not tire myself out for the week ahead. 

However, the thing that started this thinking process is a brunch conversation that I had with a friend of mine and the COO of a portfolio company. She’s incredibly smart and has been working on her company for 3+ years. There have been ups and downs. Disappointments and failures. If I start listing out their path to this point, most people would call her crazy. 

Here’s the thing - that craziness is what will make the company succeed. Nothing else. 

Calling entrepreneurs crazy is completely OK. Belittling their ambitions is absolutely not. 

If you're working a corporate job, I will tell you a personal story that only one other person knows:

It was Fall of 2013. I had come back from a completely disastrous trip from Amsterdam after trying to close our Series A. The deal fell apart and in the most horrific way possible. I was in shock. I was scared. I was absolutely terrified to a point where I couldn't speak to anyone. I called a friend of mine. Her and I went for drinks. She’s an upcoming actor. She had gotten her first paycheck - a mere $60. She bought me drinks that night and just sat there looking at me. I had a few beers, thanked her and walked home. 

Those feelings of pure terror are meant to scare the living crap out of you. Because only at that point do you realize that there is no turning back. You can only go up from there. 

It has been nearly 2 years since that entire week and it still scares me. But, it also taught me an important lesson about startups. 

Startups are a journey. And harder than most other journeys. If you survive this journey, you can survive a lot of what the world throws at you. Paul Graham, amongst his many essays, has a great piece titled “What Startups are Really Like?” I really would like for everyone to read that piece. 

I'll add a few additional points to what Paul has said: no matter what you do, know that you are going to be challenged. Some days you're going to want to quit. But, if you see the light at the end of the tunnel - do not quit. If you don't see that light, change paths. Do not quit. Looking back at your life, nothing good has happened because it was easy. There’s a reason why people date wrong people for a decade or more.  There’s a reason why people get fired. Or quit terrible jobs. Pursue your dream without fear of failure or the option of quitting. 

And a lot of days, it will feel like this: 

“The Struggle is when you wonder why you started the company in the first place. The Struggle is when people ask you why you don’t quit and you don’t know the answer. The Struggle is when your employees think you are lying and you think they may be right. The Struggle is when food loses its taste.” - Ben Horowitz 

Secondly, find people that will support you and not your idea. Ideas are a dime a dozen. Any engineer can make a product function. Your job is to create a company. Your job is to be your cheerleader. Do it better than anyone.

Lastly, always remember that whatever you are doing - you are doing it for yourself. If you hate it, don't do it. If you don't believe in it, it won't come true. But do not ever bear the entire burden on your shoulders. You will collapse very quickly.  All of this will take time. Put in your time. Earn your freedom. Put in your 10,000 hours. 

There are people, strangers included, who will listen to you. If you ever need help or advise, my email and phone number have always been publicly available: or 201-693-4510. 

I wish you the best of luck. Get ready for the most adventurous 10,000 hours of your life. 

*The 10,000 hour rule has been deemed controversial. However, the use in this post is primarily to highlight the importance of persistence and deliberate pursuit of excellence. 

Don't Follow Your Dreams
Please do make your decisions in life and feel confident that they are right. However, if fate is involved, feel just as confident even if they aren’t.
— C. Elizabeth, Absolute Obsession

As part of my job, I see a lot of ideas come through my desk. A few of them, I get excited about and decide to pursue. Many of them are not the right fit. However, the common trend between these ideas are the people - the startup entrepreneurs. They range from 18 to 60. Their eyes are glowing and they are passionate. They want it. Who knows what it is, but it is clearly important. 

Despite most of my writing that focuses on the positive aspects of startup life, this post is not about the good things. It's about the struggle. Despite the glow in entrepreneur's eyes and the burning desire to succeed, what goes on in the background is crazy and insane. I wouldn't wish it on my worst enemies. 

These are people who have asked for money from their parents, friends and family. Yet, they have nothing to show for it. 

These are people who have closed out their savings accounts and their paycheck is still $0. 

These are people who have gone from living in a nice apartment to under their desk. 

These are people who have gone into irrecoverable debt and sometimes into bankruptcy. 

These are people who have lost family and friends because the time commitment to building this thing - which may or may not succeed - is inhuman. 

These are people who have sacrificed the best  part of their lives to focus on a dream. 

And that's what is so scary about being a founder. Dreams do come true. Only if you want them to. And the reason I say "these people" is because I have been there. And it was terrifying. It still is terrifying. It keeps me up at night. It scares the living crap out of me. 

But you know what? I am fucking happy. Every single day. Every decision I make is mine. Every word I write is calculated. Every person that has survived this shitstorm with me is family. And that to me is success. 

The world will try to mold you into something that aspirational people disagree with. Every day. Every single minute. It starts off with your GPA, then your SAT scores, then your internship and then your first job. And you realize, during this process, you hate it all. It's not what you thought your life would be. And it sure as hell doesn't make you happy. 

So, here's my advise: don't follow your dreams. It's fucking hard. Instead, follow your heart. It already knows what you can't admit.  

The Pursuit
Aurora Borealis

As I’m writing this, I’ve spent the past 24 hours between airports on both coasts of the United States and en-route to Bermuda for some much needed thawing out. 

Most people dislike the thought of traveling for long hours. I, on the other hand, love it. 

I love flying from California to New York overnight and arriving at my office in time for the first meeting of the day. And despite all my whining, I love working hard and long hours to ensure that the things that we do mean something to someone. It doesn’t matter if all I’m doing is helping someone find a cheap flight or planning a social get together or building out applications for clients. 

And the reason it doesn’t matter is because I care. 

Over the past 3 years, I’ve slowly called it quits on my previous life. No more corporate credit cards. No more counting paid vacation days. No more people, clients and projects that were just a way to the end (aka: bottle service). 

It’s been scary along the way. But, it’s been rewarding beyond my wildest expectations. Because today I’m fueled by the the very core of things I care about: good people with a side of crazy. 

I stress every single day about finances. I stress about what might happen if all of this goes away. And I’m terrified beyond belief if the people I care about the most stop believing in the future. Because if there is one thing I’ve learned is this - the people closest to you never let you quit. They inspire you to work harder than you ever have before. They inspire you to go beyond your wildest threshold.  

And that’s what makes this incredibly fun. 

There isn’t enough money in the world for me to work an all-nighter for someone else. Or to even live a life where every single day is guaranteed. But that’s what makes this worth it. It’s all about being crazy enough to believe that things that you care about will care about you when it matters the most. 

To those on the edge - don’t fret. Do it. Perhaps one small step. Perhaps a huge leap. Either way, the freedom is exhilarating. 

On 2015
2015's first sunset

As another year rolls around, I look at the calendar, pack up my laptop, iPad and various accessories that have scattered around my apartment over the past 2 weeks. It feels like the end of a school vacation. 

The end of the year is always interesting. While a lot of people take time off, startup life doesn’t really stop. It keeps plugging away. Day after day, week after week and then suddenly, 3 years later, you look back to see what you’ve accomplished. 

Running PaLaCart has been my biggest privilege. We’ve gone through so many ups and downs and if I was in any other job - I would have quit to work at another company. 

PaLaCart has also been the longest job of my career. It has been greatly rewarding, extremely challenging and truly humbling. I couldn’t have done it without the support of friends and family. 

Over the past year, I’ve also joined Genome. It is a start-up incubator and service provider. While my involvement on the service side is just starting to ramp up, looking at startups from a critical eye and then from a compassionate heart is really interesting.

2015 is going to be the year of a lot of big decisions. No resolutions at this point, but time to get things moving. 

Onwards and upwards.