7 schizophrenic traits every startup CEOs must adopt

CEO PSYCHOSIS The role of CEO is often described in gauzy, glowing terms espousing passion mingled with ambition that runs deep enough to change the world. All this noble ambition belies the uncomfortable reality that the inner world of a start-up CEO is often a constant state of conflicting realities that can distract from the mission at hand.

This list reflects my personal experience as the CEO of a social commerce startup. I can tell you – the dual reality can be disconcerting at first but after a while it gives you a certain edge that makes you tougher and smarter the longer you stay at it.

1) Your vision must be out there enough to generate investor interest but not so out there so as no one knows what you’re talking about. We’ve heard it from the pundits a lot – be different, don’t just iterate on another idea. Gotcha but then when you truly do go out on the limb – you may not get investor interest because you’ve too far out on that very limb they asked you climb out on.

2) Being 100% committed to do the best you can do but realizing that it might not be the best that can be done. As CEO, people want to believe you know more than you do – especially if you are chartering new territory. Unfortunately, you know that your best is probably not close to the best that can be done. You have to hope that it good enough to get by.

3) Truly believing in your vision yet living with the reality that the odds are definitely against you. I heard Brad Feld of Foundry Group remark recently that they get about 1,000 pitches a year but only invest in about a dozen ventures. So do the math. Your chances of getting funded are very small and even you do get funded – your chances of success are not in your favor. It’s a miracle anyone actually takes the plunge.

4) You are constantly recruiting even though can never afford most of the people you would love to hire. I learned never ever recruit when you urgently need to fill a job. That increases the chances for a bad hire because hiring in a moment of need won’t bring the best candidate forward – it will merely bring the most convenient one to the table. Instead, you should be recruiting ALL THE TIME. The trick is keeping the candidates you want on simmer until you are ready.

5) You must be a perennial optimist yet become exquisitely good at “productive worrying.” The grind of a startup requires a positive, upbeat attitude to get the team through the inevitable tough times. Yet, a Pollyanna attitude won’t get the job done to overcome the inevitable stumble that’s to come. For that eventuality, it best to be prepared with a Plan B and a Plan C too. In my case, I’m such a good worrier that my Plan B’s have Plan B’s (ya – I know – that’s extreme worrying).

6) You want to be fully transparent but realize there are some things you should NEVER EVER tell your VC. There is great serenity in knowing that you have been totally open and trustworthy in all your dealings with your people, your customers and your investors. Despite that – never confuse transparency with “true confessions” when dealing with investors. You need to convey confidence with a healthy dash of cautious optimism. Keep the deeper “what if’s” worries to yourself unless you have a specific ask of your VC.

7) People call you “Brilliant” and a “Visionary” but you feel like you are faking it. If you are a half articulate and just passionate enough – people will use the “B” or “V” word around you a lot. They hang on your every word waiting for the inevitable pearls of wisdom to trip off your tongue. Yet, often people confuse “Brilliance” with deep experience and a “Visionary” for someone who has a good grasp of history. Truth be told though, often you feel like you are just muddling through. That’s OK because if you admit you don’t know then others can step in to help. Otherwise the visionary, a.k.a. prophet must always have the answers. Not.

There you have it – the seven habits that are vital for any startup CEO.  I guess ya’ need just a touch of crazy to pull it off.

The Surprised Entrepreneur turns Rebel Entrepreneur

What makes a rebel.

What makes a rebel.

“Judy,” a sweet tech project manager said to me recently after I discussed some of the gaps in the social marketing ecosystem “You are on a crusade.”

I didn’t see that one coming so it stopped me dead in my tracks. What crusade was that I wondered? I probed but she dodged answering me. The word crusade is laden with meaning so it stuck with me – what had I said to give her that impression?

In hindsight it seems obvious but in the moment, I was oblivious to the shift in my thinking from simply being a Surprised Entrepreneur (as I posted here) to becoming a Rebel Entrepreneur.

My cause was simple – to put the human element back into the business of marketing that has been platform’d to a near digital death. I am driven to re-infuse marketing with the sense of wonder, joy and creativity that I had the good fortune to revel in during my earlier career days.

In those ancient days (one generation after Mad Men but before the Internet revolution had really hit) we could put hearts into our work because there were few tools or platforms or technologies to guide the work. It was pure creativity and smarts. It was hard to measure the effectiveness of the much of the work but you knew your work made a difference when the company did better – jobs were created and bonuses were happily doled out.

Over the years, technology improved how we deployed marketing but we continued to be driven by our nobler motivations to create great marketing that improved people’s lives. We knew we could make a difference.

But there’s been a shift in the industry over the past 3 years. Marketing, especially social marketing has become a tech-heavy exercise of manipulating retargeting platforms, or reward systems or algorithmically based big data platforms. Social marketing is reduced to a conversation about content syndication or sentiment analysis.

So it’s no surprise that over that period of time, inextricably, I have seen tech and platforms taking the joy and the nobility out of the system. I have become overwhelmed by the supremacy of marketing platforms over serving people and algorithms over inspiration.

My sense of alarm was quite publicly aired in the digital pages of Ad Age and Huffington Post. I ranted at Facebook when I felt defeated at using Facebook productively. I admitted frustration at the black-box techno-jargon wave that swept over us marketers drowning us in confusion. I’ve even had the chutzpah to question the funding strategies of VCs who are basing their investments on marketing principles that simply don’t apply anymore. But mostly I challenged the 20 something CEOs who created marketing platforms that are long on cool but short on practical application for real marketers.

In the process, I have been:

  • Flamed by Macboys and called a hack (look up “Judy Shapiro” and “mac security”)
  • Accused of being techno-phobic and capable of only kitchen related work, ideally pregnant at the same time thus preventing me from ever writing offending articles ever again
  • Tarred and feathered as an “old line” marketer unable to keep up with the iteration savvy tech guys
  • Harangued for questioning if the “Content as king” model was sustainable
  • And very nearly digitally lynched when I first suggested in 2010 that perhaps Facebook had jumped the shark.

And so against all odds – here I am, founder and CEO of a social tech company, readying the BETA launch of our new network called Eden for Q1.

Against all odds, this little venture that started a year ago will be introducing a different type of social marketing framework that is a based on an “opt-in” paradigm. We are going up against the big “push based” social marketing platforms and networks. It is an uphill but noble fight. In our vision, Eden is a place where users control the action – how they see content or which brands they interact with. It is a reversal of the; “It is our platform so you have to play by our ever-changing rules” social network that dominates social marketing today.

Against all odds, we managed to secure funding including from an early stage VC for which we are eternally grateful. We’ve created relationships with agencies ready to sell Eden to their clients and we’ve sealed meaningful partnerships that help us gain access to the highest levels within publishing and brands.

Against all odds, as one woman in her 50’s, I am privileged to be joined by a community of seasoned marketers to help in this crusade. Our collective goal is to right the marketing ship listing dangerously to one side from the weight of platforms and big data. I can’t express my gratitude to this brave league of fellow crusaders other than to give them full credit for their invaluable role in our noble adventure. I give them a place of honor in our company’s history:

  • Peter Hubbell, CEO of BoomAgers and former Saatchi Board member. www.boomagers.com
  • Griffin Stenger, a founding partner of Concept Farm, a leading social marketing agency [Crain’s]. www.conceptfarm.com
  • Robyn Streisand, Founder and CEO of The Mixx Group – a branding agency and an early investor in engageSimply. www.themixxnyc.com.
  • David Hoffman whose career spans four decades as a film producer and corporate strategic communicator. Wikipedia’s simply calls David: “One of America’s veteran documentary filmmakers.” http://en.wikipedia.org/wiki/David_Hoffman;
  • John Bowman, was Exec VP Strategy at Saatchi working on their premier brands and is now authoring a book about his great Grandfather, Archibald Stark Van Orden http://theassassinsassassin.com/about/
  • George Collins, a long time database expert and CEO of Research & Response – a database management consultancy. http://www.rresp.com/
  • Mark Bonchek, Founder of Orbit + Co whose strategic consultancy is “creating a new direction in business by shifting the relationship of individuals and institutions from PUSH to PULL.” http://www.thinkorbit.com/

Against the odds, I have been able to attract a seasoned management team of  marketing practitioners who had to “build it” after the consultants talked about loving it but conveniently left when the real work began. They were the ones who built those first generation eCommerce sites and created the principles that good UE designers use today. Our journalists understand SEO and our artists are offering their images for free all in an effort to be a part in the creation of an alternate social marketing reality – a fresh start called Eden.

So against all odds, I find I have become a Rebel Entrepreneur – so strange especially given my training, temperament and age. The potential high rewards of being a rebel all too often comes at a high price and we’ve seen our share of deals gone bad, betrayal by trusted colleagues and funding plans gone awry (Sandy was devastating to the startup community).

And yet, despite the odds, we are close to the launch of our network.

So I invite you all over to Bit Rebel to experience this journey with us as we sprint to Eden’s launch in Q1. Celebrate our highs and feel the unnatural lows that are endemic to startups. Share our anxiety as our burn rate increases but our funding outlook seems further out (we are doing a second round of seed funding now). Take a peek behind the startup curtain, see what’s really going on and help shape what happens. The success of Eden will be a triumph of us marketing practitioners like web designers, SEO geeks and developers over algorithmic feats of IP muscle.

Our mission is noble and our cause true.  Come join us.

I guess like any good crusade, we need a flag and a manifesto. Stay tuned – I am just learning how to be a rebel. Kinda of exhilarating actually. But

Judy Shapiro

P.S. My rebellion gets its own website: http://judyshapiro.wix.com/rebel-entreprenuer. Viva Le Rebellion.    

A time of gratitude.

The life in a startup world is intense.

Every event takes on qualities of epic proportions. Good meetings become the makings of great deals. Great meetings are like pixie dust creating a confection of billion dollars exist fantasies.

Conversely, every stumble hurts far more than the reality of the injury. Confidence gets shaken and once that is done – game over.

So in the pressure cooker of the startup world, losing perspective is a near universal experience. In the race to launch your venture before funds or faith run out, the focus is on the next milestone or the next deal you MUST close to keep the doors open.

While the grind can overcome our sensibilities, almost nothing will distract the startup CEO from their near myopic focus.

Almost nothing that is until Mother Nature forces herself onto your consciousness.

Sandy disrupted our inner sense of safety as it tore its way through the Tri-State area. The Northeast is not accustomed to a full natural disaster that was Sandy. We are used to being a terrorist target but now we also have to accept that we are as susceptible as any other area to natural disasters too. It is almost too hard to fathom.

But in the destruction and the internal turmoil comes a renewed sense of perspective. In the seismic shift of how bad things can get – a balanced appreciation for all we have asserts itself powerfully as though to ensure it can withstand the inevitable reverting back to the “not normal normal” that characterizes startups.

In the chaotic tumult caused by tress falling houses and tsunami level waters, some very true principles emerge as powerful counter forces to the forces of Nature.

1) Live widely by giving of yourself largely.

2) Remind yourself to be grateful for the chance to be grateful. Where there is life and health – everything is possible.

3) Be gracious to those in need.

4) Pay special attention to needs of the larger community. How we support our community is a true mark of our character.

5) Act as though your every action is being recorded and watched.

This tragedy will change many of us forever.  My hope is that the change of gratitude is a permanent one.

Judy Shapiro

The “turning point” moment that harkens a new beginning.

The life of an entrepreneur is an emotionally volatile one. The ups and downs are extreme because often so much is at risk.

As a newbie entrepreneur, I was especially battered recently by the wild swings of bad news and good news so as to make me ill with startup sea sickness.  Yet, as I began to get my sea legs; slowly the nausea was replaced with a serene inevitability that this little venture might, against all odds, make it.

It’s not arrogance that colors my thinking. Nor is it an irrational faith in my brilliant thinking.

But it is the realization that if I make it will be because of the community around me. The vision for Eden was to create a way for consumer’s to create a trusted web space starting with Eden Network – a social network of topic based communities that serve high search but badly served topics (e.g. karaoke).

The sheer audacity of my attempting a tech startup, in retrospective, was stunning. As a marketer, the notion of being a tech CEO was about as likely as me going bungee jumping any time soon. Sure – perhaps the opportunity may come up but it’s unlikely I would ACTUALLY do it.

Yet this venture was born of pure passion – actually passionate frustration at how there so much brilliant marketing tech innovation going on and a total lack of operational practicality in being able to use much of it.

But while frustration goes a long way towards driving me forward – it doesn’t make me a seasoned entrepreneur. I’ve made many rookie mistakes but I am encouraged to continue mainly because of the support of the community around me.

And because of the encouragement of my community, despite all the pitfalls and pratfalls, within the last week, I sense a fundamental shift.

I turned a corner.

Different key pieces are coming together in a way I could have never expected; brands are excited to participate in Eden Network; agencies are anxious to offer new social marketing options that’s easy for them to buy and monetize. Key management holes are being filled with ease and partners are approaching me with increasing volume making me dizzy with potential.

My community of friends and colleagues are the foundation upon which this venture rests. It is an honor to have such loyal and supportive friends. It is also humbling and inspiring to be sure I don’t let them down. Just a few weeks ago, I felt like I was in a free fall dive and now I am buoyed by a sense of “knowing” that we have a shot at making it.

The Jewish New Year is about to commence and for thoughtful souls, it is a time of acknowledgement and gratitude to all that we have been given.

In that spirit, it’s up to me to be sure that the community knows the depth of my gratitude.   May we be privileged to share a year of peace and awareness at how precious each one of us is within the community of humanity.

Judy Shapiro

Why the “cha ching” of the $1B Instagram sale might actually bankrupt Boomer parents.

By now, most of you have heard of Facebook’s $1Billion sale of Instagram, an app developed by a bunch of young 20 somethings that lets users post photos. Today, Instagram has about 50 million users which works out to about $20/ person. “Cha ching” for anyone involved …

Punditry aside about whether it is a shrewd deal for Facebook – instead of “cha ching” – all I hear is hissing as the air escapes from Boomers’ retirement funds.

It is alarming and here’s what I mean.

You see, I have worked with tech ventures for over a dozen years, starting at Bell Labs New Ventures and continuing to this very day. In that time, I have worked with many startups, often gratis, because it’s so rewarding when my expertise can really make a difference in the early days of a venture. CEOs have the product vision but they rarely have marketing know-how to get the product to market.  That’s where I step in. I help startups assess their market potential so they can monetize.

And in the dozen years or so I have been doing this, I see an alarming new twist to the never ending parade of venture dreams that haunts me. I liken it to the disturbing “Gold Rush” era where many more prospecting failures bankrupted folks versus the rare, outlier successes.

In today’s day and age – here is how it goes down.

Johnny or Jane are in college and – wham – they hatch an idea for a company often inspired by the innovation incubators on every campus. The idea grabs their passionate attention because at least they can try and make it happen versus trying to get a job which is tough and depressing.

Mr. and Mrs. SupportiveParents are happy their kids have found something that inspires them, so they cover more of their kids’ living expenses so the kids can commit themselves to their “passion.”

After about three or four months, their idea has some substance and the kids realize they need some money to create a “demo”. Of course, there is no cogent business plan (if a business plan even exists) but Mr. and Mrs. SupportiveParents kick in the $10,000 or $20,000 to create said demo –  on top of the extra expenses they are already incurring to keep their kids in school. (This is when you can start to hear the air escaping from Mr. and Mrs. SupportiveParents 401K accounts!)

A couple of months later said demo is “almost done” but not quite because the kids did not really do a business plan and as they worked, the idea kept changing (translation = more cost). “But I only need another $20,000 to finish it off. Then it will take off because it is so cool. Please …” Again, as we would expect, Mr. and Mrs. SupportiveParents step in and shell out what their kids need.

Slowly but surely, over time, as their kids refine their idea; there is steady attrition of the parents’ savings plans because startups need constant funds. This tableau is playing out again and again and I know it because I have met too many Mr. and Mrs. SupportiveParents in the last few months who have depleted their savings by $150,000 or more to help their kids live their passion.

It is frightening to see since most new ventures are “high risk” in the best of circumstances, making them wholly unsuitable investments for most any Boomer given their proximity to retirement.  And if that’s not bad enough, it’s even worse once you understand that kids’ ventures, proportionately, have a higher mortality rate because they are borne of 90% enthusiasm and 10% practicality despite their parents’ 100% support 100% of the time.

This is a dangerous combination – especially in frothy times like ours where opportunities for kids are limited yet perversely, the potential for untold wealth is tantalizingly possible.

And this brings me back my point. The Instagram sale was an aberration – a fluke – an outlier event – possible because of a unique set of circumstances. Yet it infused a new level of Gold Rush fervor into the passionate hearts of ambitious young entrepreneurs despite the reality that the chances of striking it rich today are about equal to striking it rich in the Gold Rush of 1848.  And just as sadly, their loving parents are funding these ventures despite the improbable odds.

So while many people hear the “cha ching” of $1B, all I hear is the air escaping from parent’s retirement funds. It is not a happy sound. Not at all.

Judy Shapiro

P.S. – I am posting this as my personal Mother’s Day present to Mrs. SupportiveParent. Be careful – please!

The surprised entrepreneur – The last moment I can allocate GRATITUDE Grants

I am surprised how fast shares go in a startup company that people are excited about. Our plan is mostly done and the investors have begun to make overtures. My total ownership has been happily whittled away to include the wonderful talent this company will need.

I gratefully allocated shares to our president who is deeply experienced as both an entrepreneur and a VC. I was deeply honored when our CTO, who gets hundreds of business ideas in a year but only considers “one or two,” signed up.

Ever so carefully, I identified the key talent we would need and one by one each person on this amazing team is coming onboard with their allocation. Yet until we officially close our first round (scheduled for February), I’ve still got ability to allocate shares pretty much as I want.

But not for long.  

Now, much to my surprise, I realized how very quickly my ability to make unequivocal awards of shares will be gone. Now is the last moment I have to express my gratitude to people who have believed in my ability to create a new way forward in marketing.

So with the urgency imposed on me by our first formal funding round, I have barely a few weeks to share these gratitude grants.

I get to tell my dear gentle creative storyteller, a giant in the business of video, how valuable his lesson was in the meaning of video to create a powerful experience.

I finally get to ‘give-back’ to my “hard core” (hehe) entrepreneur, investor and civil liberties activist friend. She taught me perhaps one of the most important lessons in this space – the focus needs to be about creating shared experiences using content rather than solely focusing on the content. It is a powerful mind-bending insight that has deeply shaped how engageSimply develops its concept.

I can go back and reconnect with some of my ex-colleagues and CEOs who, over the years, inspired me, instructed me when I just didn’t get it and generally invested in me by teaching me ever so patiently. I can’t imagine how I would be doing this without their support and faith.

In the end, each gratitude grant is my way to repay the gift of confidence that each person so unselfishly gave me. It helped me turn a blind eye to the limitations imposed by stereotypes about what a tech CEO looks like (age or gender) or should do.

Over the next few weeks, I will have the distinct privilege and (one time only) opportunity to award these gratitude grants – without justification or encumbrance. To those of you on the list – stay tuned.

Lots of people track “firsts” (e.g. first investor, first alpha) – I want to note the “lasts.” I want to acknowledge these last few precious moments when I have full control of my company and I can still allocate equity as I want. This privilege is fleeting likely not to be ever repeated.

I best be sure I don’t leave anyone out. What a happy chore.

Judy Shapiro

The surprised entrepreneur – I’m having the time of my life.

I am not sure what I expected to be doing at this point in my career. I have been blessed to have been at the center of the changing, blossoming technology landscape of the last 20+ years.  My earliest days were at an advertising agency called NW Ayer which gave me a broad perspective on Corporate America’s practices, problems and possibilities for triumph. I then gracefully made my way into the tech stars of Corporate America itself with stints at AT&T, Bell Labs, Lucent Technologies and Computer Associates. I also had the great good fortune of working at small innovative technology companies led by visionary innovative leaders. Two prime examples include Melih Abdulhayoglu, CEO of Comodo and Jason Katz, CEO of Paltalk.

This unusual combination of corporate marketing experience coupled with the feet on the streets training born of working at tech startups, gave me a balanced perspective of how the marketing business is evolving in this technology driven world.

So here we are.

The marketing business is going through a fundamental shift that throws into question almost every tactical practice built over the last 20 years. And, amazingly, it seems that just as marketing becomes this new discipline that weaves creativity into an interactive user experience that is tech heavy – it’s a perfect fit for my peculiar type of networking meets technology marketer experience.  

This seems nothing short of extraordinary. Which is why I am all the more stunned at the work I am doing today. I had not planned on any such seismic move in marketing, so I certainly did not plan on launching a marketing tech venture.

But here I am.

My journey has been one of surprising excitement at the possibilities in marketing excellence that was simply not possible before. The vision of this venture, therefore, is to take advantage of these new trends to deliver a sustainable and productive “marketing machine” (a phrase I attribute to Melih) that can turn the tables on how marketing gets done.

In our vision, we don’t approach monetization like Google or Facebook’s who are about pushing more accurate marketing messages to consumers. We are looking to deliver a marketing platform that lets consumers decide what content they see, what ads they see, how their social networks are managed, how they conduct commerce, even how they communicate within the social networks. The organizing principle for this platform is not ad-driven monetization but oriented around Judy Consumer. Our vision is to create the kind of system that we want to live with for the next 10 years . In effect, we want to give Judy Consumer the tech power to create her own personal “Trust Web.”

To the few friends we have shared our vision with – all have come to a similar conclusion – it is an ambitious (maybe too ambitious) vision. They are correct. But as I entered marketing in the 1980s most of marketing at first was human powered with marketing systems emerging later on.  

And here we are – again.

This next generation collection of marketing technologies is rich in creativity but is not organized for sustainable marketing programs for brands. This is work that I, among others, are focused on – creating v1.0 systems to operationalize the business of social marketing.  

We are all at just at the beginning of this journey and it’s a journey I didn’t expect to be taking at this point.

But here I am – and much to my surprise – I am having the time of my life.

Judy Shapiro

The surprised entrepreneur (entry #5):

The great talent hunt yields an unexpected gift that keeps giving. 

Hiring is tough on all companies.

Hiring is brutal for new companies.

One bad hire could spell irrevocable disaster.  You have to pick people who can get the job done today, have a passion for the work we are doing, be a mensche, be creative and be just quirky enough to add to the color of our community. But I also know enough though to know, practically speaking, there’s a thin line between a “quirky” and a high maintenance team member.

No wonder it scares me to death.  No wonder I put if off. I’d rather have oral surgery. Honest.

But in the past few weeks, I could avoid the truth no longer. I needed to balance out our team and I needed to find the perfect tech architect. In my view, every tech venture needs three architects – the vision architect,  the business architect and the tech/ product architect. Sometimes this is all one person, but not in our case.

So with a deep breath  - I began what I thought would be a painful process.  I was wrong.  In fact, I’ve learned much to my surprise, that the hiring process was the best gift I could give my business because I got to learn about the very essence of my venture itself.

I began the process hesitantly knowing that the type of talent I wanted can be highly selective about where they go. Quickly, I was lucky enough to get the chance to chat with the head product guy at a large, very cool social media company. He was thinking of leaving and he graciously agreed to hear my story. Then a few days later through another contact, I was put in touch with an “ex-Microsoft guy who was looking for his next project.”   I talked my heart out to convince him to see the vision.

Both of them gave generously of their time and advice. Both reminded me how much I love to talk to developers. I love how their individual creativity is reflected in their choice of languages. I love the quirky, binary-colored way they see the world.

But in talking to them during this process, I also realized I could not really express my vision with the technological crispness to satisfy these folks. I was horrified and I knew from experience, any hint of uncertainty would send the best talented developers running from the virtual room.

It was a surprisingly painful lesson I needed to learn. I thought I had created the elevator pitch suitable to satisfy any audience. I was wrong. I thought long about how they reacted and it was then I had a breakthrough. All of a sudden I could see where I had gone wrong in how I described the platform, and thus the venture. Through my openly sharing with talented people during this process, I vastly improved our architectural vision.

I confess. I would never achieved this revelation on my own or even with the team I have now.  My aversion to hiring could have deprived the company of this precious gift of clarity of technological vision.

I’ll end with a note of gratitude. To any candidate we are talking to now – my deepest thanks. To all future candidates – I can’t wait to meet :).

Judy Shapiro

P.S. – Wanna help architect the next big gig – (hey – optimism is part of job req’s :). We are working on creating The Trust Web. Interested? Drop me a line.

 

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

The Surprised Entrepreneur – Diary of new venture – Entry #3:

“Mama never told me there’d be weeks like this…”

It has been a while since my last entry and I am relieved to say it is mostly for good reasons. Over the last few months, this little venture has begun to take hold – to wit:

  • I have been on the speaking tour about The Interaction Engine capping it off with a spiel at ad:tech this month.
  • We have closed two new clients – one in the consumer electronics space and one in the mobile app space.
  • I am getting better at presenting our system in meetings – now I can kinda explain it in about 30 minutes. It still falls far short of the 2 minute elevator pitch – but hey – we are getting better.
  • A number of marketing and technology companies have contacted us to “partner” – not sure what that means though
  • We have done a few presentations to media buying agencies as they are challenged to “buy” social media. They are interested in working with us (again – no idea what that means)
  • Most important – revenue is beginning to accrue

Yet, despite the clear progress and momentum – I recognize the utter fragility of this venture. Of the dozen or so folks that are part of this company – most (but not all) are getting paid some compensation. No one is getting what they deserve – yet.

But my biggest challenge is that as we get more noticed, there are far more opportunities that need to be assessed and prioritized. Fundamentally, these opportunities run along three basic lines:

  • Technology Partnerships – there are 4 companies that we are talking to now in the marketing technology space. These companies are anxious to partner with someone like us because often these tech companies have no easy distribution channel. A cool recommendation engine is nice – but it’s hard selling a “stand-alone” technology to a big brand or agency. As a quasi “system integrator” of social media technologies – they see our Interaction Engine as solving this major channel issue for them.  thsi is not a pr 
  • Funding Options – my initial plan was to sell the Engine we have now (does not require any development) to generate about $500K in revenue. While that plan is still in play – I realize that getting to that sales threshold might take longer than I can wait to begin the second phase of this company – to develop/ sell “self-serve” integrated social media programs to SMB via web hosts. I am encouraged by experienced colleagues who tell me I can go get funding now with what we have. TBH, I am still unclear whether any VC would consider this investable. My colleagues are so confident that this can get funded that they are willing to spend their own time over the next few months to work on this. On the one hand, that’s a funding gift that I would be crazy to reject. But on the other hand, it will still require my time for an exercise that I’m not convinced will have a successful outcome. Getting VC funding is a huge time hog – not matter who helps you. I keep wanting to put it off or get a traditional loan to ease the short term cash crunch. this is since this is not any way understand how to make this spaceing this work. it is frustating to say the least but this need
  • Media Alliances – Unlike most other marketing technology companies, I focused on the technology platform but I built it within a holistic system that includes an organized set of content assets from a diversity of publishers. To me, content is not king – but rather the juicy bait to start the engagement process which is why I had to collect relevant content assets. So while I spend a considerable amount of time building these alliances – there are many more people looking to partner with us because so many content producers and writers have been caught in the tumult of “freep” (free and/ or cheap) digital content distribution. In our system, these folks have a voice and a stake, so we solve a problem for them too. The problem is deciding who we can take on.

Most interestingly (and yes – it is a surprise), it seems that our Interaction Engine System (a coordinated, tech mashup of a monetizable “community of interest”) is an approach that can integrate disparate marketing activities into an operational program. In essence, instead of pitching an individual program to a client where I have to plug into their operations – we are being seen as our own ecosystem and other marketing programs and/ or technologies have to plug into us. I won’t say I planned it that way – but I am loving how this is playing out.

Now on to my biggest “what’s keeping me up list?” for this entry:

  • Knowing which contacts are worth pursuing on the tech front, on the funding front and on the editorial front. The response to my presentations has been great – but overwhelming actually.
  • Keeping the pressure up on the sales front –  our issue now is too many great leads and not enough time to follow them all up.
  • Keeping the team motivated and monetized – always a struggle whether you are a new company or an old one

The next four weeks tend to be intense because marketing budgets are being finalized so we need to keep the pressure up – yet people’s mind are on the holidays. This requires an elegant and thoughtful approach to sales (I hope we are up to it).

Day after day, it seems the ride I am on gets more thrilling, more scary and more substantial. As the stakes keep going up, Mama never told me there would be weeks like this where too much is happening too fast. But I guess that beats the other option: too little happening too slow; by a mile.

“So dear Mama – I am grateful you taught me to appreciate a good ride when I see one which is exactly what I am doing  - even though it feels like I caught a tiger by the tail.”

I don’t intend to let go now.

Judy Shapiro

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