Eli Portnoy


My First VC Meeting — A Tale Of Brutal Rejection

I vividly remember my first VC meeting like it was yesterday, even though it happened over 10 years ago. I was awed and intimidated to meet an industry insider, someone who with a single decision could transform my business prospects. I prepared for weeks, polishing my deck, practicing my talking points, and rehearsing answers. I couldn’t sleep the night before I was so nervous, anxious, and excited.

For the past year I had sacrificed an incredible amount to build my business. I had quit my consulting job, I had spent almost all of my savings, I was sleeping sporadically and not enough, and I had spurned social events and family obligations. In other words, I was living the startup dream and loving every second of it. But that didn’t make the sacrifices any less real. I had put it all on the line and I was now about to meet with a VC who could make it all worthwhile. The magnitude of the meeting was huge for me.

I got to my meeting a full hour early and waited in my car. As I counted down the minutes I day dreamed about all of the incredible ways the meeting would go. I finally walked out and made my way up to the office. When I got there a very friendly person walked me over to a conference room where I set myself up. I expected the meeting to start on time, but the partner was 20 minutes late. He was cordial and nice, but clearly wasn’t nearly as excited to see me as I was to see him.

The meeting started and I began my perfectly rehearsed presentation. I hadn’t finished the first sentence when the VC interrupted me with an idea. I hadn’t even said what I was working on, yet he already knew how to improve my business. He pontificated for a full five minutes and then let me continue with my presentation. Within one slide he was already tuned out. At the end of the meeting he told me all of the reasons why my business wouldn’t work, why my concept was obviously terrible. He then highlighted all of the brilliant companies in his portfolio and why they were so much better than mine. We parted ways with him asking me to stay in touch.

I left feeling like I had been punched in the stomach repeatedly and then kicked for good measure. The entire weight of failure fell on my shoulders as I grappled with what had happened. I was prepared to be told no. I knew VC’s say no to 100 businesses before they say yes to one. I knew it was my very first pitch and that I would get better. I understood the odds were widely not in my favor. And yet, I hadn’t expected this. The meeting felt the way I imagine an artist would feel if someone not only didn’t appreciate his art, but went out of their way to criticize every last brush stroke without ever looking at one of his paintings. Why couldn’t he have just said it wasn’t for him? Why couldn’t he have just listened and then given me feedback as to how I could improve my business or my pitch? Why did he have to make it so painfully obvious that he had no interest in my business and zero respect for me.

Ten years later the memory of that meeting is still vivid, but I think I have a much better perspective for why it was so painful and what I hope VCs consider as they reject entrepreneurs. First and foremost there is a massively asymmetrical importance to the meeting. To the VC, the meeting is just another one of many in the day, to the young entrepreneur it is THE meeting. Every word you speak he or she will hold onto for years (and they may even write a blog post about it 10 years later). More importantly, entrepreneurs make massive sacrifices to build their business. It might not be a great business, they might not present it well, and they maybe have zero chance of actually succeeding, but as humans they have worked tirelessly, tried hard, and built something. If nothing else, I hope VCs can respect and empathise with the incredible work and dedication it takes to be an entrepreneur.

At the end of the day VC’s have a hard job. They have to say no over and over and over again. That can easily desensitize someone and make it hard to have the level of empathy required for the job. Fortunately there are many VCs who are exceptional people who treat every entrepreneur well (I know firsthand because I get to work with incredible VC partners everyday at Sense360). That said, I still come across VCs who lack basic empathy when they deal with unknown entrepreneurs. They are late, they check email constantly during the meeting, they pontificate, they interrupt constantly, they don’t respond to emails, they don’t follow-up after the meeting, they are unnecessarily harsh in their criticism, and many other bad behaviours. I really hope that the next time they reject an entrepreneur they consider the sacrifice and hard work the person across the table put in. They don’t have to love them, their idea, or their business, but remember that the founder probably slept on a coach, spent their life savings, and risked a lot personally to try and make it happen. Hopefully every VC can at least respect the commitment and love for entrepreneurship.

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