Fools Venture where Angels Fear to Tread

My journey into entrepreneurship officially kicks off today. After nearly twenty years of employment, I've joined the ranks of the voluntarily unemployed. And April Fools Day seems like an oddly appropriate marker to start a new venture. After all, entrepreneurship requires a certain degree of foolhardiness with respect to resources not controlled.

What you don't learn about a business when you are an employee

I've discovered, over these last couple of weeks, that wannapreneurship, the state I was in for the better part of the last decade, is a world away from actually doing it. You discover so many things, you don't really think hard about before you start a venture, only after you begin it. This is one reason why, I suppose, it makes sense to start entrepreneurship early in life. There is only so much learning value in employment. In the brief period I've committed myself to a venture, there's been a tremendous amount of learning. Here are some of the insights I felt might serve a larger audience well:

  1. All decisions are emotional: The act of quitting and starting out is a fundamentally emotional one. No matter how much you've planned it out, there is never a good time to quit your job and start a business. The final decision to pull the plug comes from the gut. It is rarely rational, since even a rudimentary analysis of the economics of the decision will show you that many of the assumptions you'll have to make to pull it off, are deeply unreasonable. So, if you are considering entrepreneurship, recognize that analysis won't get you very far. Indeed, there seems to be evidence that all decisions, even those made by large corporations, have an emotional component that is critical to the final moments leading up to the point when the decision is actually made. So, do the rational analysis, and then also prepare for the emotions: yours as well as others', before your pull the plug. One way to prepare for the emotional component is to rehearse the act of making the decision irreversible (e.g. submitting your resignation) -- first by yourself, and then with people you trust.
  2. Your loved ones are your first and most important investors: Even if you don't take a single penny from them, your family, after you, are the people most invested in your business. They've committed to hitch their lives to your fortunes. And unlike, that of cofounders, angels, employees, and VCs, their investment is often involuntary. i.e. they would not have thought of making it, if you had not, in some way, forced their hand. Their support, your spouse's support in particular, is so critical, and consequential, that not securing his or her forbearance with your risk taking, can have catastrophic consequences for more than just your venture. I know. I write from the personal experience of having gone through such a failure before.
  3. Entrepreneurship is lonely: In the very early stages, starting a business is a lonely endeavor. There are no daily or weekly status meetings. No scrum to attend. No exec reviews. Marissa Mayer doesn't give a damn whether you dialed into your VPN or not. No late night conference calls. You can't complain about how busy you are, and how full your Inbox is. No one needs anything from you. You are completely and totally dispensable. For a whole day, the only messages I got were junk mail and commercial messages. I've never opened a promotional offer from Flipkart with as much enthusiasm as I did last week. I spent a great deal of time during my 'wannapreneurship' days figuring out how wonderful it would be to do exactly what I wanted. Only to discover that on day one, no one wanted anything from me. You have to start from zip.
  4. Not having a boss is a double-edged sword: For twenty years, I've always had bosses: some, not so good, and some great ones. It is hard to understand the value a boss brings to your career, until you stop having one. For one, he or she usually drives your agenda. Much of your workday is driven ultimately by the goals of your management hierarchy and that makes planning significantly easier, than starting with a blank slate. There are benefits to not having a boss, of course. You get to do exactly what you think is the right thing to do. And prioritize on what makes sense to you. But unless you get very disciplined about researching and setting goals, tracking progress against them, and most importantly validating that the goals being set are the right ones to focus on, you can get lost in unproductive activity very easily.
  5. Nothing, absolutely nothing, happens without your effort: In a large company, one gets used to things just happening. For example, email and calendaring systems, just work. On my second week out of a job, I realized that I was depending on a Google sync program that is no longer supported. There was no IT department to fix the problem. I had to figure it out myself (I'm now using Google calendar directly, instead of Outlook, by the way.) When you start out, every thing, and I mean absolutely every thing, needs to be initiated, and often completed by you. Need uninterrupted power? Get the appropriate UPS and generators installed. (If you're not in India, this won't make sense to you.) There is no corporate campus. Need to travel? Make your own arrangements. There is no corporate travel department. Need a product mock? Get cracking with Photoshop/Gimp, or hire a UX designer quickly. Need a prototype? Build it or hire a programmer to build it. Need to see a doctor? Pay out of pocket or go shopping for insurance. There is no corporate group insurance policy you can rely on. Need to hire an employee? Draft employment contracts, find lawyers to do it, check labor laws etc. No HR. Yup You didn't think you'd miss HR did you? And most importantly: Need money? Find customers to sell your product to. There are no "idiots in sales and marketing" for you to curse. (This is from the engineer's perspective of course. If you're the sales type, then you won't have any "idiots in engineering" to curse either.) You'll have to initiate each of these actions yourself, or outsource smartly and follow up yourself. Things won't get done until you make them done.
  6. Time is the most valuable resource you have: The irony of day zero is that while you do not have to do anything, the clock is ticking. Unless you just quit Facebook after having joined it around the time Eduardo Saverin was booted out, you don't have an unlimited runway. Yet, plunging into frenetic activity isn't necessarily the best thing to do. Choosing what to do and more importantly, what not to do is critical. And that requires introspection.
  7. Knowing yourself is a pre-requisite to knowing your business: Peter Drucker was never so right. For those of us used to boasting our way through performance evaluations, managing ones' self can be a difficult task. It is critical to really know both your strengths and your limitations across various functions and activities. This will not only enable you to separate truly consequential tasks from trivial ones, it will also help you find employees and cofounders who compliment you. On a related note, I'm looking for a cofounder! If you have deep operational skill in running a cloud-based infrastructure, I'd love work with you.
  8. Take the time to smell the roses: The travails of entrepreneurship loom large early in a venture. (I suspect they never go away.) And there is lot of drudgery. But the joys come in very tiny, almost imperceptible doses. If you're not paying attention, you will miss those joys and ultimately the point of entrepreneurship itself. For example, I was reading an article on Forbes early this morning, when I was prompted to take an online survey. I clicked into it out of curiosity, and amongst the questions was one that asked about the role that I played in purchase decisions at work. Out of habit, having taken these sorts of surveys many times before, I clicked the option that said "Some or no influence on the corporate budget." But then, I did a double take. Nope that wasn't right any more. Was it? The relevant option for me was "Final approver of all purchase decisions." Okay. Granted, that the only purchase decision I'll be making this week is, whether to pay the electrician to install an AC in my home office, it still felt good to realize that I'm the 'final approver'. To paraphrase William Ernest Henley, I was the master of my fate. The captain of my soul.

Happy April Fool’s Day. Happy 0th Birthday, Milestone42! This one's for real.