Archive | March, 2011

Screwed by the Press?

After much debate, we made the decision to hire an independent public relations (PR) consultant a few months ago to help us launch SalesCrunch to the world.  PR is a very political business and a big financial investment that is very difficult to measure.  One good story can put you on the map, but more often than not companies spend tens or hundreds of thousands of dollars on PR only to add more noise to the world than signal without much to show for it.  It can literally make you or break you.  I considered handling our PR myself.  At the end of the day, PR is mostly just sales – hardcore, phone pounding, boiler room pitching till you’re blue in the face kind of sales.  I am a sales guy to theUgly Head core, so that part I get and even thrive on.  Its the other part, the ass-kissing, soul crushing politics around who writes about who, what and when, that is mind boggling to me. So we decided to pay $8,000 a month for six months for 1/3rd of an experienced PR consultant that had the contacts and patience to play the game. Two and a half ass busting months and $20,000 later, we are ready for the public launch of our flagship product CrunchConnect.  Everything was going according to plan, until disaster reared its ugly head.

We lined up several days of back-to-back press briefings and demos the week before the announcement.  The first briefing is with a New York based online news rag.  The reporter is young, fairly new to the job and shows up wearing jeans, a flannel shirt and Chucks, typical for a reporter covering the downtown tech startup beat. We get to talking and he turns out to be a nice, wholesome, Midwestern kinda guy.  We get along swimmingly and the demo goes off without a hitch. We both follow up via email with niceties and it’s pretty certain he is going to give us a good write up. Score!

You know the saying that timing is everything?  Well, that’s absolutely true of PR.  You start pitching press a week or two before you are ready to send a release on the wire to give reporters enough time to do research and write an article in advance.  As soon as the first reporter writes about your news its basically old news and the desire for other reporters to cover it plummets like a man’s labedo after age 50.  To give as many reporters as possible the opportunity to break the news while it is still news you put an embargo on the release, which basically means the reporters agree not to publish their story until a certain date and time. In our case, we have reporters agree to it, we plaster it all over the advance release, we put it in our follow up email and we shake on it. Confused by all this? Don’t worry, so was the reporter from our first briefing.  Instead of waiting till the embargo lifted Monday at 7am he accidentally released it the very next day.  Ugh, can you say “train wreck?”

Train Wreck

After I pulled my heart out of my throat, I wrote him the following email:

On Wed, Mar 23, 2011 at 12:45 PM, Sean Black wrote:
Hey Dylan,

Can you please take down the story you posted ASAP? Per the press release, it is embargoed until Monday, March 28th at 7am ET.  We really appreciate the kind coverage and great story, but we want to make sure everyone has the same opportunity to cover it.



To which I got the following response:

On Wed, Mar 23, 2011 at 1:06 PM, Dylan wrote:

Hi Sean and Kristi:

This is completely my fault and I apologize for the carelessness on my end. Please trust that there was no ill will behind it. With that in mind, it’s the policy of ours and every publication out there not to remove a post. I’m between a rock and a hard place on this, and I hope it hasn’t caused exceptional damage or grief.

Very sincerely,


OMG We're ScrewedLike any industry, the New York tech scene and the press that covers it is a pretty tight knit community. I happen to know the COO and the VP, Business Development of the company for which the reporter works and several of my investors and network know the CEO. A campaign of emails and calls ensues pleading to have the story taken down until Monday so other reporters will cover the story, but to no avail. Here is the verdict in an email from the CEO:

Sent: Wednesday, March 23, 2011 3:22 PM
Subject: Re: SalesCrunch Embargo Violated

Have now talked to everyone involved here.

Normally, in cases like this, companies reach out and ask us if we will agree to an embargo before providing us with any information. We agree or don’t agree to the embargo depending on the circumstances, and then the company decides whether or not to go forward and share the info.  My understanding is that that did not happen in this case.

My understanding is that when Dylan and Sean talked the first time, Sean did not mention anything about an embargo or the conversation being off the record.  He then followed up with an email saying that the information could be released on such-and-such a date that Dylan didn’t missed (our error).

If this is in fact what happened, the initial conversation between Sean and Dylan would be considered on the record.  And, for obvious reasons, we don’t allow folks to go on background after the fact.

We don’t ever want to surprise or burn anyone, and Dylan should have seen the language in the email and brought it to Sean’s attention (and his editor’s).  But at least from what I understand now, there was never any agreement to or mention of an embargo in their initial conversation.

If your understanding is different, please let me know.


So basically it came down to a he said, she said technicality and the decision went against us. Now, if this were any other outfit I might be upset, err livid. But then Dylan’s editor called me to apologize and assured me there was no ill-intent and said he even tried to lobby our case with his CEO.  The COO and I exchanged emails where she apologized and pretty much said the same thing. In the end I think my first impression of Dylan as a wholesome, good guy was the right one. He didn’t intentionally break the embargo, it was just a newbie mistake, as his editor assured me.  Moreover, I know the rest of the people within the organization to be of high integrity and I believe them when they tell me they took it very seriously and that it was a very difficult decision to make, but ultimately it came down to journalistic integrity for them. So in the end I wrote them all an email thanking them for tying assuring them there was no hard feelings, and I meant it.

Welcome to the roller coaster ride called a startup.  Stuff like this happens all the time, sometimes good and sometimes not so good.  You learn from it and move on better for the experience and determined never to repeat the same mistakes twice.   I’m sure this wasn’t a fun experience for poor Dylan either. Being the cause of a few hours of chaotic calls and emails from several influential people within the very tech community that you cover that involved your editor and entire senior management team culminating with the CEO had to be a pretty dreadful outcome for him.  So it looks like everyone involved learned a hard lesson this week and I am sure everyone wants nothing more than to put it behind them and move on.  So that’s exactly what we are doing.

We are not yet sure of the consequences of the broken embargo. Who knows, maybe it will turn out to be a non-event.  Then again, maybe our $20k and two and a half months of hard work will have been for not. But whatever happens, we will press on (no pun intended) and live to fight another day.

UPDATE: We ended up getting tons of press, so disaster averted after all

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Decadence vs. Dedication

Last week I was invited to an all expense paid, five-star trip to Vail, Colorado to attend the American Ski Classic with my wife. The company that invited me is wooing venture capitalists and CEO’s of fast growing technology companies (i.e. prospective clients) on the trip for five nights and four days.   We would get paired with an Olympic skiing legend on a team that will compete in two days of racing, enjoy five days of dinners with the Olympians, catered slope-side lunches after racing, tickets to watch the pros race, and a free pair of race skis. OMG!

2011 Korbel American Ski Classic

They had invited a good friend of mine and his wife a few days before me and he declined. I told him he was nuts – “how on earth could you turn down such an amazing opportunity”, I said.  When they invited me I agonized over it for 24 hours, but ultimately so no as well.  So why did we have to turn them down? Was it conflict of interest or moral obligation? Hell no! If someone wants to offer me an all expensive trip to a five-star ski resort with absolutely no strings attached other than the common courtesy of considering them when we are in the market for their services then we are free and clear to accept.  No, the reason wasn’t nearly as complicated as that.  In fact, the reason is simply that we are too damned busy building and running our companies to take advantage of the many perks people dream about when they are working their way toward the top.  Oh, and here’s the thing about those fancy lunches and dinners we get invited pretty much every day of the week – they are work!  You are almost always entertaining clients or being entertained, which is really just an elegant way of saying you are selling or being sold. When you are “on” all day it is exhausting to be “on” all evening as well.  Of course we do these events at night because its our job to see and be seen, but truth be told most CEO’s just want to go home with their significant others, climb into their PJ’s and veg in front of the TV. Sure, we absolutely appreciate the invites and the people, but after a while fancy dinners aren’t so special anymore as the novelty quickly wears off.  Ultimately there is a pay-it-forward obligation affect to being invited to these things, so everyone gets what they want in the end.

Am I sitting here writing this post eating my heart out that I am not going to the American Ski Classic to be paired with an Olympic skier, sip Champagne, and hobnob with a bunch of other CEO’s and fancy people wearing my brand new race skis?  Oh God yes!  But I take comfort in knowing that if I continue to keep my head down and execute on our plan now my investors and I will have lots more opportunities like this to turn down in the future. So in the end its just a matter of delayed gratification.

In the meantime, I’ll study the itinerary below, close my eyes and imagine myself slope-side eating fancy food with fancy people and then live vicariously through my friends that did go on the trip when they get back (and yes, I blacked out the name of the company hosting the event in the hopes of getting invited again next year). Please feel free to join me on my imaginary trip to Vail.

American Ski Classic Itinerary

American Ski Classic Itinerary 2 of 2

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Boards Aren’t for Brainstorming

I survived another board meeting on Friday.  For many people, board meetings evoke images of big important people making big important decision. Either that or it evokes images of a bunch of old white men in dusty suits and hair growing out of their ears and noses sitting around a mahogany table. Opinion varies greatly as what makes a good board and a good board meeting.  I am not expert on either, but based on my last board meeting I know brainstorming sessions do not make good board meetings

Jeff Bonforte, CEO of Xobni, gave a presentation on board meeting lessons learned at the First Round Capital CEO Summit a few months back and his top 2 tips were 1. send all the reporting as advance reading and 2. focus the conversation on the top 2 or 3 things that keeps you up at night. I took his advice at our last board meeting and it went swimmingly well.  Instead of regurgitating slides full of data, we spent the meeting discussing the “burning topics” on which I really wanted to focus a few big brains.

Board Meeting Illustration

I sent this past week’s board deck several days in advance as usual.  Except this time I decided to change the “burning topics” at the last minute to reflect a challenge that had literally kept me awake for at least the entire previous two weeks.  The result wasn’t good. Instead of well thought out problems matched with potential solutions, the board meeting turned into a brainstorm session.  Because I hadn’t prepared and synthesized my thoughts in advance, the meeting was a “swirl” of unstructured thoughts and opinions based on an overload of unstructured information and we never stood a chance of coming to a consensus on the issue.

My biggest takeaway was that board meetings are alot like business plans – its not about the plan, its about the planning.  No matter what anyone tells you, no one reads your business plan but you.  As one of my board members so poignantly stated after our meeting, the usefulness of a board meeting begins and ends with the CEO pulling herself out of the weeds long enough to think through key milestones and challenges and progress toward or over them.  In other words, its about the planning, not about the meeting, the people or finding some magic answer to everything that is going on.

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Conference Whores

I was in San Francisco last week at the Sales 2.0 Conference while a kajillion people from the Silicon Alley & Silicon Valley tech community were in Austin for South By Southwest, or SXSW as it is BoonDoogle BBQwildly known.  There was even a dedicated website of meetups and parties started by the New York tech community to make sure all the cool people could find each other.   Hashable not only threw a party, but made the event an all expense paid vacation for 15 of its most active users. No doubt this was in addition to weeks of planning and flying in a large contingent of its own employees to manage the whole thing. You can be sure something like that easily cost $100,000.  I had conference envy to be sure. Complete with live music, film stars, rock stars, naked arrests and parties galore, SXSW seems soooo much more interesting than a sales conference.  I started to feel anxiety about having chosen the wrong conference. I mean, if all the (other) cool tech startups were investing so much time and money into SXSW then there must be tons of potential customers and press there to be had right? Oh crap, I had made the wrong choice hadn’t I?

Boondoggle definitionThen my boy Mark Suster came through with a post on Both Sides of the Table from the trenches of SXSW with his 10 10 tips on basically how not to become a conference whore that relieved me of all my anxiety.  After reading his post I was super charged that while the rest of the tech scene was getting its grove on at SXSW me and Stammy at Notifo were hard at work stealing their customers.   Sales 2.0 turned about to be full of tons of potential big accounts and partners for my company. So while I am following up with them, most folks that went to SXSW are either still in Austin or are trying to sleep off the consequences.

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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.


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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