The Surprised Entrepreneur-Diary of new venture (Entry #4): A tale of two VC meetings.

For the last 3 months I have been very focused on sales of our Interaction Engine system and we are doing well on that score. As a result, though, I have not really shaped the business plan and the structure of our company for the inevitable VC round to come. Getting funding has not been an urgent requirement and it seemed far better to generate real revenue and then go for funding.

So as we are chugging along, our work has gotten the attention of two VCs who reached out for a meeting. This was my first introduction to the world of VCs and I confess, the meetings were startling and sobering; leaving me strangely ambivalent about the journey ahead on this front.

VC meeting number 1.

It was a rainy, NY winter day and we decided to meet at a coffee shop. I knew that this fund was more an incubator type which offered me the potential of being part of a startup community. It seemed like a good idea that I perhaps become part of the NY “Tech/ CEO club” since now, I am an outlier. I don’t hang out in Meetup sessions and I am not trekking across the country chasing the cool tech conferences (OK – I confess I am going to SXSW but only because they asked me to speak).

I enter the coffee shop with only the vaguest sense of what the VC looked like (his Twitter pix was decidedly not very useful). It took me a solid 8 minutes to spot him. As I approach I see this 30ish guy with a quirky winter cone hat that was just 2 degrees “off” – IMO wandering into “silly land.” It was hard not to laugh out loud at the effect – but I held my composure.

I sit down and we start chatting.  I was curious to understand his investing philosophy. His focus decidedly was on individual technologies – why Foursquare will be huge or how this new app model will revolutionize some trend or other. When I wondered with him about the lack of a clear business model which limits their practical use for marketers, he dismissed that concern with a wave of the hand. “Well, that’s won’t be a problem for long – once the old guard is gone.”

Wow. Clearly that meant me. I took his comment to mean that only the “newer” generation have the depth to understand new marketing technologies. I was dumbfounded and I was shaken. The gap between us was, technologically speaking, generational – perhaps never to be bridged. But mostly I was stunned at how immature his thinking was about how the business of marketing really works. I was shaken knowing his company was helping drive the evolution of marketing without a clue about what marketers really need.

The rest of the conversation was a haze TBH. I left traumatized and angry at how dismissive he was of the impracticality of his vision of marketing technology evolution.

VC meeting number 2

This CEO leads a well-respected large VC shop that does $2- 5MM deals. I had been introduced to this VC through a mutual colleague and we met at his office one snowy day.  He sat down in comfortable business casual attire that was in keeping with his experienced CEO role.

We started by talking about his company which was relocating to the East Coast from the West Coast. Interesting move and I asked him why. “Increasingly the smart money is coming to NY as this where many of the major new media and marketing operating business trends are evolving,” he said.

This was my dream VC – he understood the space and the problem my company was trying to solve – how to practically create the “many to many” marketing model. We compared notes on how the technology in this space was similar to CRM in the 1990s – full of possibility but lacking in coordinated systems to activate the technology. I suggested that we are a bit like what Siebel who, at the time, integrated all the telemarketing technologies into the system we now know as CRM. I feel that is what we are doing for the emerging “many to many” marketing model. We met for a solid 90 minutes at which point he asked me “What next?” Shockingly, I had no “ask.” I had been so traumatized by the first VC, that I had not really expected a question like that. I stumbled around and just admitted – “I don’t know.”

But then I turned it around and asked him: “How would you categorize my company? We are part system integrator, part content and media company. We are a “creative shop” in that we create customer interactions with technology. Are we a tech company, a services company?”

I could see he was sensitive to the dilemma of my question. Finally, he said, “I would put you in the digital media space.” I was shocked until he hastened to add: “You need to be defined somehow so people know to work with you and help you.” But in his gentle smile I could see his answer left him unsatisfied as well.

We parted agreeing to keeping up the dialogue. As I walked out of his office, I felt cautiously optimistic that the work we are doing is needed in the market.

One thing I learned from both meetings – the journey of starting a company will continue to be a journey of surprise. I never expected to have so dramatically divergent experiences as I tentatively start down the path of funding my company – even if I don’t know exactly what type of company I am creating.

All I know is that the “smart investment money is going towards the business operating companies” and that’s me. Cool – right?

Judy Shapiro

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2 Responses

  1. Very interesting and funny. My co workers are trying to guess which incubator / VC you were meeting with. Some interesting candidates.

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