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Huffington Post: Diary of a Silicon (V)alley CEO

Huffington Post: Diary of a Silicon Alley CEOThis post originally appeared here in The Huffington Post and documents the trials and tribulations of  my experiences as an Internet entrepreneur selling the dream, which are sometimes embarrasing, sometimes funny and never boring.

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It’s a well kept secret that startup CEO’s spend an inordinate percentage of their time selling.  From raising money to recruiting talent to landing new customers and even negotiating an office lease, CEOs sell something to someone every day. To prove my point, I started keeping a diary of my day-to-day as an Internet startup CEO.  Here’s a sampling of my week:

Monday: Murphy’s Law

I have a meeting with one of the largest banks in the world. It’s only a 7-minute cab ride from our edgy downtown office in Union Square to their imposing glass tower on Park Avenue, but it feels like I went through a time space continuum under the Helmsley Hotel.  As the cab lets me out I see suits pouring in and out of the building and become painfully aware that I am wearing the standard issue startup uniform of dark blue jeans, a button up shirt and a sports jacket.  I just broke a basic sales 101 rule – dress to mirror your audience. Feeling underdressed and a little self-conscious, I shoot up to the 50th floor in one of a maze of elevators.  To appreciate this story it’s important to know that we are in the business of selling web-based applications that help companies socialize sales across their company and customers, so having Internet access to demo our apps is kind of critical.  We sit down in a meeting room with a window that peers freakishly into the next building where dozens of meetings are on display seemingly for our entertainment.  I fire up my Mac to start a demo, only to discover there is no WiFi in the building. I spot an Ethernet cord on the wall and plug it in, but its dead. I whip out my Verizon wireless card, but the buildings’ thick walls render it useless.  As we turn the corner my host’s office to try her computer I see what looks like a government issued mainframe sitting on her desk and can’t help but think of that scene from the movie A Christmas Story where the kid drops the lug nuts and blurts out “Ohh Fuuuuddge”. She turns on the big white box and I half expect a few clunks and some smoke to pour out. Instead, something far worse – a five-year-old version of the Internet Explorer browser struggles to come to life. The Internet connection is so slow the page slowly paints from left to right across the screen. I type our URL into the browser to see what looks like a war-torn version of our slick new website that clearly isn’t built to backward support a five year old browser. That’s it; I shut her computer off, open PowerPoint on my Mac and give her an old school presentation.  As I leave her office I take comfort knowing I am headed back to my George Jetson high-tech world downtown alive to sell another day.

Tuesday: Dirty Sexy Money

I spend the morning working on my book Dirty Sexy Money – How to Build Sales at a Startup. In addition to being provocative, the title pokes fun at the fact that the internet startup world is full of entrepreneurs who dream of making lots of money, but who naively think they don’t need to sell their wares because if they build it customers will come. Anyway, I get on a call with our public relations consultant to sell her on my idea of throwing an underwear-only book launch party for the New York tech community at the Penthouse Mansion, now owned by someone from my business school alma-mater.  After picking her jaw up off the floor she spends the next 15 minutes telling me why that is not such a great idea. We’ll see who wins that sale in a month or two.

Meanwhile, I’m shocked to get an email from the woman at the bank asking for a copy of the presentation to send to her team – redemption is at hand, or so it seemed.  I send her a link to the presentation using our own application that tracks when someone opens it and the number of minutes and seconds they send on each slide, like Google Analytics for presentations.  But she can’t open it on the “oh fudge” computer.  So I send her a link to our super fun animated demo video on YouTube, but the bank bans employee access to social media.  It’s a scary reminder that  social media marketing isn’t as mainstream as the propaganda machine would have us believe.  Alas, I am forced to email a PowerPoint and miss another opportunity to demonstrate our own product.

Wednesday: Sky’s The Limit

Our law firm Cooley gave me a conference room on the 48th floor of the Grace building across from Bryant Park. I walk into the room to see New York City sprawled out in front of me; the Empire State Building reaching for the sky, the sun glimmering off the Hudson River and the Statue of Liberty is off on the horizon dwarfed by the distance. I am thankful I can do my job from anywhere in the world (except a bank) and that I don’t have a “real job” where I have to show up at a cubicle at 9am everyday. The sweeping view of New York is the perfect inspiration to work on my book totally undistracted.

Of course, I’m distracted an hour later by my attorney Bo, but it’s a welcome distraction as I asked him to stop by to talk about SiliconCEOs, a peer group I am putting together and want Cooley to sponsor.  The idea is to get CEO’s of fast growing venture backed Internet companies in New York (Silicon Alley) and the Bay area (Silicon Valley) together each month so we can candidly and confidentially help each other build amazing companies. My company has the good fortune of being backed by top tier investors like First Round Capital and Accel Partners, so we have access to plenty of great CEO’s. We just need a sponsor so we can pay for gatherings. Before I leave Bo agrees to allocate a good chunk of his marketing budget for the cause – score one for the team!

Thursday: A Window Closes

I wake up to an email from Jeremy Stopplemen, founder & CEO of Yelp. I asked him to come speak at our next SalesSchool event and talk about how he built Yelp’s inside sales team to over 300 salespeople that now drive most of Yelp’s reportedly $100M a year in revenue. Not surprisingly, the Yelp sales machine never came up in any of the press a few months ago around Yelp refusing Google’s $500M buyout offer.  I tried to sell Jeremy on the idea that this was the perfect venue to give back as well as give the Yelp sales team the credit it deserves.  We did a similar event at NYU in December that was a huge success with almost 400 RSVPs from the New York tech community.  Unfortunately, Jeremy’s response was “I don’t think this is a fit for us, but appreciate you reaching out”. Oh well, you win some and you lose some.

Friday: A Few Doors Open

I wake up to two great emails. One is from MIT offering to host the next SalesSchool on campus next month. The second is from the VP, Sales at Boston based Hubspot Mark Roberge accepting my invitation to build the event around Hubspot’s amazing sales team.  We agree the event will likely sell out in an hour of releasing tickets.

High off that bit of good news and a little too much Starbucks I grab a cab to met one of our advisory board members for breakfast at the Pain Quotidian on 5th Avenue and 8th Street.  It’s one of my favorite blocks of Greenwich Village lined with beautiful pre-war buildings and anchored at one end by the Washington Square Park Arch. The fact that the arch, modeled after the Arc de Triomphe in Paris, has been standing in that spot since 1892 acts as a sort of pinch reminder that I live in this amazing city. Our advisor is the President of popular and fast-growing online media company and I am meeting with him to ask him to speak at the first SiliconCEO event about how his company socialized selling throughout the company. They literally made sales everyone’s job from founder down through the ranks, culminating with the announced sale of the company for several hundred million dollars. He agrees to do it – score!

I am off to my next meeting with a serial entrepreneur friend that writes a popular blog to get his advice on writing a regular post about what its like to sell the dream every day as founder & CEO of an Internet startup. He proceeds to warn me that to do so successfully would require writing in the first person, exposing intimate details about myself and being on the opposite side of safe.

Saturday:  Exposure or Exposed?

Inspired by friend’s advice and story I start writing this diary.  I try to reveal as much as possible about just a few of the best and worst things that happened to me this week. I am taking a lot of risk by sharing these intimate details. I have to admit that I am a bit worried that I might tip my hat to our competition, piss off the people I mention (sorry Jeremy) or that my investors will think I’m an idiot for showing my cards.  This is why there aren’t any other CEO’s writing this type of stuff for public consumption while they are still in office. But I am equally excited not only by the idea that exposing my day-to-day can help other current or aspiring entrepreneurs realize they are not alone on the startup roller coaster, but also we might gain far more than we have to lose by tapping into the wisdom of the crowds, open sourcing solutions to some of our initiatives and challenges and race past our competition.  At least, that’s the story I’m going to sell to my board if all hell breaks lose after this article is live for all to see.  Wish me luck!

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