How to Handle VC Rejection

"I see an opportunity here, but it wouldn't be an opportunity if everybody saw it."

Apple is going to be out Apple'd

Can a Great Software Company Produce More Than One Great Product?

For the sake of argument let's define a great software company as having at least one dominant product in a lucrative market, and great for a product as being both the dominant brand in its market and financially meaningful to its owner. I'm using "software company" in a very loose sense here to mean any company who main interaction with customers is through software - this encompasses e-commerce and digital media - and I don't care about greatness from a quality perspective.

If you only look at software, Google is all search; Facebook is all Facebook; Amazon is all e-commerce; and Apple, Oracle, Intel, HP, and IBM don't exist.

The Week of Living Gratefully

It's been an interesting week, to say the least. Hurricane Sandy has done a lot of damage, but it also made us realize what's really important in life and made me grateful for so many of the things I take for granted: cell phones, internet, even electricity and heat. ConEd is my new hero for getting their system back on the grid so quickly - and they keep providing us power, every single day. Is there really any better deal in the modern world than all the electricity we need for less than the cost of our cell phone bill? If you had to choose between your cell phone and electricity, is there really any doubt which one you'd choose?

So many people helped me out this week. I'm particularly grateful to my friend Gina Shedid, who took me in to her Brooklyn home and made it possible for me to comfortably get through the week with all of the first-world amenities that we usually take for granted: electricity, heat, and internet. Gina is an incredible hostess and I encourage you to send your friends to stay with her on Airbnb. Her hospitality even made it into the news.

Friends with whom I had quarreled put differences aside to reach out and make sure I was OK. My friend Kate McCarn and her boyfriend helped her 80 year old aunt down 17 flights of stairs, put her up in their 1-br apartment, and were still generous enough to invite me to crash with them for as long as I needed.

The security receptionist at a Class-A midtown office building let me work out of the lobby on Tuesday afternoon with my phone and laptop plugged into the front desk, when I was frantically trying to complete my application to YCombinator which was due that night (it was later postponed to Friday, but I didn't know that at the time). It turned out he had slept in the building for the past two days and was going to stay there until subway service was restored. I'm not sure if that was because he was paid hourly and needed the money badly enough to put up with the conditions or because he couldn't afford to take a taxi home, but either way it helped me realize how lucky I am to be able to enjoy what I've always thought of as a very modest lifestyle.

When my key got stuck in the lock - which of course had to happen just then - someone I had never met from a neighboring building lent me her cell phone to call a locksmith and her WD-40 when I couldn't get through.

I am going to volunteer in the Rockaways in the morning, which were hit much worse than we were here in the city and really need our help. When people tell me how great it is that I'm doing this, I just think of all the people that were there for me when I needed them. How could I do any less?

M&A in Threes

It often feels like consolidation of the middle tier of an industry happens all at once. When the first industry heavyweight makes a strategic acquisition, investment bankers, VCs, and entrepreneurs start salivating, knowing that other industry players are likely to react with defensive purchases of their own. Some recent examples at hand are health insurance for the Medicare and Medicaid programs, social CRM, human resources management software, IT services, and dynamic display ad optimization.

IT services - 16 months, $23.4Bn start to finish:

I Forgive Myself

Every year on Yom Kippur I meditate on forgiveness, and post my thoughts here. Last year I was inspired by Steve Jobs, and learned from him that forgiveness is for the forgiver, not for the forgiven. That post made me rethink my attitude towards forgiveness, not as something that I bestow on others (and only if they are really sorry and promise it will never happen again), but a gift that I give myself, regardless of how the forgivee acts or even if they accept it.

What about forgiving ourselves though?

Stop Using Lack of a Technical Co-founder As a Crutch

Why should every tech startup be one business guy and the rest engineers? Why should you always finish the product before you build the business? A true entrepreneur doesn't hold up his business because he can't find one factor input. She fakes it, makes it work, pushes forward by sheer willpower. He does it manually until it's clear that there's a business and has developers clamoring to be his CTO.

It's one thing if you are selling technology, be it hardware or software; it's another if you are a tech-enabled business using the web for greater efficiency and scale. Saying you need to be a programmer to start a web-based startup is like saying you need to be an architect and a bricklayer to start a brick and mortar business. Get your business going, then you'll find the greatest architect ever and have more than a dream to sell him on.