It was 2:00 AM and I was still sitting in ‘The Cave’ — the name we affectionately gave to the cubicles in the bowels of Wean Hall  at Carnegie Mellon. It was called ‘The Cave’ because it’s all under ground, with no natural light portals whatsoever. The cave was kinda like Vegas — once you enter you lose track of time. Day or night it looked the same, and smelled the same (and not too pleasant at times!).

I was in the cave late that night because I was firefighting. A couple of weekends ago, on a whim to teach myself Java I had written up software for hosting chat rooms. The server was the decrepit little Pentium 200 sitting under my desk. The problem was that the server was crashing under the load of all the people using it. I could just go home and sleep, but the problem was that if the server crashed, I would end up with a ton of email the next day from the disgruntled users. In hindsight, I should have used Moore’s Law to solve the scalability issue. But I was a student and buying machines in 1996 was still expensive.

I was chatting with one of the frequent and loyal users of my site that night and explaining to him how I didn’t have enough resources to keep up with the growth of the service. Running thousands of concurrent users was pushing the limits of what the Java VM could handle on the P200. That’s when he suggested, maybe I should start a company — and start charging for the chat rooms. The bit flipped — I went from being a hacker, to being an entrepreneur.

There is nothing like your users telling you to charge for your service, because they want it and need it. At the time when I started my first company, I had one of the few Java-based chat solutions available, and was one of the first to offer what are now known as embed tags so that people could create their own rooms. SneakerChat, as I called it, had over 20,000 concurrent users with well over 50,000 registered users (registration was optional).

Starting my own company sounded cool. I knew it was something I wanted to do eventually anyway. It’s what I had always considered doing, right from the time that I was building and selling musical doorbells to my parents friends. (That’s a whole other story for another time). But, I knew nothing about starting a company and I knew even less about what it meant to start a company in the United States. I hadn’t grown up here, I was only here as a student and that too on a student visa. And I didn’t have any extra money I could use as capital to start a company with — but when did that ever stop anyone!

I decided I needed to learn about what it meant to start and run a company. Some of my classmates had taken a course on entrepreneurship at the business school across campus. I asked them which class it was and who the professor was. They recommended taking the class appropriately called ‘Entrepreneurship I’ taught by Professor John R. (‘Jack’) Thorne, who was the Director of the Donald H. Jones Center for Entrepreneurship at the business school. In the next couple of days, I walked over to the business school and into the Don Jones Entrepreneurship Center. Jack’s assistant (whose name eludes me right now, but I think it was Suzanne) was great at calming my nerves as I was probably visibly nervous when I walked into my first meeting with Jack.

I told Jack that I wanted to take his class on entrepreneurship. Jack suggested that I take a different class — Technology-based Entrepreneurship, which was offered the following semester. He explained to me that his class was only for students of the business school and on top of that, it was already over-subscribed with a long waiting list. I was somewhat disheartened, but didn’t know what else I could say or do. Though I was despondent, I decided to at least show up for the first lecture for Jack’s class to see what it was like. Later that week, I snuck into Jack’s class and found myself a corner I could stand in without being noticed much. I was at least 5-10 years younger than everyone else in the class, I wasn’t from the business school, and didn’t want to ruffle any feathers.

The first slide Jack put up that day was his definition of entrepreneurship: ‘Insane Perseverance in the Face of Complete Resistance.’ That was it! I was hooked. It took a couple of seconds for it to all come together, but then it just clicked. Jack had just given me the perfect way to get into his class. It was the first test on the way to becoming an entrepreneur. I decided right there, on the first slide of his first lecture, that the only way I could be successful as an entrepreneur was to first convince Jack Thorne that I should take his class!

I scheduled a followup meeting with Jack and in his office. I told Jack that he had already given me what I needed to take his class: Insane Perseverance. I told him that I was not going away. That I would keep showing up to his class and hiding in the back listening in. I wouldn’t ask any questions or say anything so as not to disrupt the class, but I was going to be there for every lecture, and the only way Jack could get rid of me would be to have me thrown out!

Needless to say, Jack relented and he welcomed me into his class. I got to take his class when several other people on the waiting list didn’t. I took every single class Jack Thorne taught at the business school. Entrepreneurship I. Entrepreneurship II. Entrepreneurship Project. Entrepreneurial Management. If it had the word entrepreneur in it, I was there. I wrote the business plan for my company as a class project for Jack’s class. I incorporated my first company, SneakerLabs, Inc., while I was still a student in Jack’s class. I was 20.

Jack Thorne

Jack Thorne passed away last year. He was one of my mentors, without whom, I would have never gotten one of the most important lessons of my entrepreneurial life — Insane Perseverance in the Face of Complete Resistance. Those words were at times the only things to fall back on when things got tough. And while there are lots of other experiences and stories that got me there, that first day in Jack Thorne’s class is the day I started my journey as an entrepreneur — one with Insane Perseverance.

Thanks to my wife and Ron Yeh (@ronyeh) for proofreading the above post.

We (me and presumably anyone who reads this post) are startup people. That’s what we do. Day in and day out. I think about startups every day, 7 days a week — even though I know I probably shouldn’t. The Valley is a fascinating place for startups. Honestly, you absolutely cannot find a better ecosystem than what exists here. I realized this only after being here and seeing what it is like everyday. I still kick myself for not moving here in 1996, when I started my first company. Don’t get me wrong, Pittsburgh, PA was very good to me and I love, respect and admire the people I met there. I wouldn’t have been able to make it without all the coaching and guidance I received along the way. But the Valley is still its own beast.

However, sometimes I feel that in all the hubub of startup life, we lose perspective of one thing: Starting up is hard. It is hard not because it is intellectually hard or that it takes a lot of work. And yes, it takes both of those. But is is especially hard because of the emotions that surround the process of starting up. Though I’ve known this for a while, it only surfaced in my mind when a young graduate student at Stanford posed the question to me more directly: “How did you deal with the emotions of doing a startup?” In particular his question was directed towards whether he should take the safe route and go get a job or whether he should take the entrepreneurial leap of faith. This made me think back to my experience of startup up 12-13 years ago and also reflect upon what I am doing today. The punchline first: Starting up is hard. And it doesn’t get a whole lot easier.

Starting a company is as much a personal decision as it is a professional one. Yes you need to be smart, yes you need to have an idea, but, yes you also need to think through all the emotions of venturing out on your own. For someone coming out of a good graduate program (like I was at Carnegie Mellon when I started and like the person who inspired this post is at Stanford) there is no dearth of job opportunities. Even in a market as bad as today’s, companies still salivate over students from top schools. So starting a venture right out of school comes with an opportunity cost. You can either take the safe route of going to work at a company where someone else is paying you and you do your job, and make big bucks right off the bat. By contrast, if you chose to start your own company, you have to figure most of it out on your own. You possibly will not get a paycheck for a long time and you will be stressed out of your mind with all the decisions you need to make but feel that you aren’t qualified to make. Things like choosing a law firm, finding an accountant, hiring people, finding an office, figuring out equity structures, raising money. And that’s just the list from the top of my head, there is a lot more than that too.

In this scenario, when you’re starting out right out of school, I say: “The greatest position of strength is when you have nothing to lose.” You’ve already been living on a meager stipend. You haven’t started earning the big bucks and your lifestyle has a low burn rate. That’s the best time to start a company, because you’re making a lateral move and not taking a step down as you would if you try to start a company after going to work somewhere else. And if things don’t work out, you know all you have to do is raise your hand and job offers will come. Your startup experience won’t be held against you, and you will still have your academic training to fall back on. That was part of my thinking when I started. I had all of $5,000 to my name when I started my first company. There wasn’t much to lose.

But, once you do decide to start a company, that’s when things get really tough — emotionally. In my analysis, most of the stress stems from the fact that starting up requires making lots of decisions. A decision to not take that cushy job. A decision to hire someone when you don’t know how you’re going to pay him/her yet. A decision to rent office space before you have the money for it. A decision to pick a law firm. A decision to pick your co-founders. A decision to pick your advisors. Decisions, decisions and more decisions. And this is something people can give you advice on, but ultimately it is your decision. And it’s hard because you second guess yourself. You don’t really know whether what you are doing is going to work. Sometimes you get this sick feeling in your stomach which makes you think “What am I really doing here?”

That emotional distress is only complicated more when someone close to you begins to question you. In a lot of cases it’s parents, but it could also be your spouse or your best friend. While they aren’t actively trying to make your life complicated, they inevitably do — because they have your best interest at heart. They’re also usually very risk averse. They may not even understand your vision and think that you’re just building castles in the air. That one question: “Do you really think this is a good idea?” Or “Don’t you think that <insert hot company name here> would be a nice place to work for a while before you go out on your own?” feels like a stake going through your being. If you’re lucky they will be behind you no matter what. It’s part of their job to question you. To make you think twice.

An entrepreneur’s life is full of stress. While I don’t have any scientific data to back this up, anecdotally, I have known several entrepreneurs who have all developed similar physiological manifestations of the stress they are under. The stress of starting up is one of the reasons why 2-founder teams have a higher likelihood of success than and single founder — because you get to load balance and spread the stress. When one person is down, the other person can pick up the slack. You boost each others confidence. Sometimes just knowing that someone else shares your vision is just the moral support you need in order to get going. I started my first company as a solo-founder and I can tell you from first hand experience, it is way harder than it would have been with a co-founder. But, finding a co-founder can be just as hard. As an entrepreneur, you make the best of what you have. You make lemonade.

K9 Ventures is my new startup. It’s a meta-level startup — a startup that helps to start other startups. And even today as I do what I consider is my 4th real entrepreneurial venture (there have been others along the way that I don’t count) I can feel the same stresses that I went through when starting my first company. You learn to recognize it, but you still have to deal with it. So the best advice I can offer to fellow entrepreneurs is to surround yourself with good advisors who have done it before (not consultants or VCs, but real entrepreneurs). People who have had a similar experience and can help to guide you through the process. They may not be able to get you to your destination — that’s something you have to do internally, in your own mind, but they can certainly point you in the right direction.

For all the glorification of the invincible, unshakeable entrepreneur just remember that when they started out, they went through all the same turmoil in their heads that you are going through. It’s part of the process. It is the essential part of the journey that makes real entrepreneurs empathize with others and willing to help. It is what ultimately makes you a better human being. The best entrepreneurs are humble, yet determined. Humble because they don’t know how they ever did it before and because if they had to do it again, it would still be hard. And they are determined because it does take insane perseverance in the face of complete resistance to do a startup.

Ultimately doing a startup is about passion and perseverance. It is an experience of a lifetime that cannot be replicated in any other setting. No educational program can even come close to what you learn in doing your own startup. And regardless of whether you succeed or you fail, no one can take that experience and that learning away from you. That is your true gift.

Yes, starting up is hard, but don’t let that stop you.