The Most Optimistic Person You’ll Ever Meet (Four Lessons From a Career in Startups)

Photo: Marc Baskin Photo Credit: Courtesy Marc Baskin
Marc Baskin | Courtesy Marc Baskin

[This article was first published on LinkedIn here. Author Marc Baskin is a finance & operations executive for high growth technology companies, currently works at N.J. startup FlexWage Solutions, and is a cofounder of the Morris Tech Meetup.]

No doubt. Optimism has become inextricably linked with technology startups. Retelling the legends of tech companies that made billions for their founders – and what intrepid embracer of risk doesn’t see him or herself as being the next addition to the pantheon – we won’t get far without hearing how optimism over obstacle proved to be the difference. If you had a drink for every tech CEO who listed optimism as a critical trait, you would be more inebriated than listening to Sting sing ‘Roxanne’.

Of course a sunny outlook is important. Not just in an endeavor that some pundits, Henry Blodget for one, report as having less than a 1-in-10 chance of success, but in all aspects of life. Perseverance is a complementary trait, in the face of odds seemingly insurmountable, that is critical. To continue operations through dwindling or empty bank accounts, cancelled sales, paycuts, incongruous product/market fit, or to make the decision to pivot, perseverance may be at the top of the list of necessary qualities of the top management in a startup company. I’m not sure one could persevere without optimism. So I do agree that it is a quality of leadership that cannot be overlooked.

But in my fifteen years of working in web technology, digital media and software startups as a finance, operations, and strategic executive, I have actually met THE MOST optimistic person that you’ll ever come across.  Despite how that may sound like an enlightening, engaging experience, it is actually one you would do best avoiding. He or she is many things you know well. I’ve met him many times and bet you have too. Here are four lessons I’ve learned from different CEO-leader types through the highs and lows of life in a startup, including how to recognize the most optimistic person you’ll ever meet. Look familiar?

1.   Be wary of some of the Salesmen-turned-CEOs: Don’t ‘Under Promise and Over Deliver’– Can we just agree to call this what we really mean? In sports you would call this ‘sandbagging’ and for the most part it is offensive, disingenuous and lacks integrity. In golf, sandbagging applies to lying about your ability (handicap) to gain more concessions (strokes) from an opponent and then going out and crushing the course.  In billiards, it’s not unlike hustling, where you’ll ostensibly deliver an inferior level of performance when you knowingly can and will outperform it when money is on the line. The first time I heard this from a startup founder, I loved it. I thought it spoke to high ideals of working hard and delivering the best work possible. But then I heard it repeatedly, almost exclusively by founders who came from a Sales background and uttered with smug and condescension. Originally written by Tom Peters in his 1982 book In Search of Excellence, this phrase came to reside in the Fountain of Platitudes that serve Salespeople their sound bites, alongside Earl Nightengale, Dale Carnegie, GlenGary Glen Ross and Sun Tzu. I soon lost a little bit of respect from everyone who uttered this.

SOLUTION: It would seem if you under promise and then over deliver you’re back at the point of just delivering. Period. So be honest with your intentions, for what you believe and what your abilities are.  Then go out and make it happen. Let’s not try to act as if we’re superior to clients. Let’s engage in a collaborative process in which we set expectations and deliver exactly what we promise.

2.     Don’t be the ‘We are the Next Twitter’ CEO: Make Revenue As Soon As Possible (if not earlier)– This seems so obvious. But people fall in love with the romantic idea of bootstrapping, lean startups and eating ramen noodles.  Startup lore is filled with stories of people quitting their jobs or college and making millions.  You can max your credit cards and live to tell about it when you’re 23 and your credit limit is $1,000. Then you can pretend to have the startup story. But when you have a credit balance of $50,000+ or mortgage your house with kids depending on a roof, it might be best not to sink it all on your can’t miss idea until you can prove it actually is something people want. By actually making money.

SOLUTION: The founders of one company I worked for wanted to build a consumer web/mobile product but first built two service companies that generated millions to support it. Vinit Bhahara of (Quidsi), talking at NJ Tech Meetup, relayed how he didn’t quit his job until the year they made $11 million.  There are three paths you should choose: a) build something while you’re still working a legitimate job, b) quit a job if you’ve first lined up, or know exactly what your path is, to signing a revenue paying customer or c) you’re under 25, like Ramen noodles and have nice parents that support your hedonistic lifestyle.  Whatever you do, don’t quit your 6 figure job because you have a great idea and optimism.

3.     Keep your eye open for the Well-Read, Booksmart CEO: Culture is Overrated.I agree that creating an environment that instills community, engenders good feelings and provides a consistent message of the qualities expected of team members is positive and something that needs to be consciously and routinely communicated. But so many of the famed digerati overemphasize its importance to the point where disciples start companies more concerned about getting the culture right then figuring out how to generate revenue.  Time is wasted in meetings to decide how meetings will be structured in the future. Or in providing activities to force team chemistry rather than let it happen naturally.  As well, I often see people make declaratives of what is important in their company culture which could substitute as “What I learned in Kindergarten” or “Captain Obvious’ Rules of Life” such as “We embrace a culture in which our team is honest with each other and conducts themselves with the highest integrity.” Duhhh.


SOLUTION: Are you making money? Is there a tech guy next to you building your product? No? Then stop worrying about culture. It’s awesome that everybody loves to spend so much time together but unless you figure out how to bring in money, you’re just reliving your college years. If you need to solidify your culture when there are fewer than five people in your company, you’re not focused.  And when you do get around to setting down the Culture Speak, make it noteworthy

4.   OK, So the Most Optimistic Person You’ll Ever Meet? Another leader-type: the CEO of a company going bankrupt. I used to be in awe of anybody who started a company and hung on their every word, when I was in my 20s. Bold risk takers. They were all geniuses. Until you met them. Or got to know them. Or read about their sexual harassment charges in the “Industry Standard.”  Turns out, aside from the ability to laugh at risk, they were just people like everyone else.  I still respect the heck out of most founders I meet. There are few people who are willing to take the career, family, and economic risks that they do. And few are as optimistic. But it has amazed me over the years, how much more optimism and good vibes they espouse when things are at its worst. It doesn’t matter whether the staff is on a company-wide pay cut, there isn’t money in the bank for the next payroll or we just lost our biggest client. The CEO’s smile is wider, voice more boastful and declaration of ‘kicking butt’ more resounding. They never let anything crack the façade or anyone learn the truth.

SOLUTION: Put down the Sun Tzu and remember you have a team of people that are working hard to be successful. The fear of CEOs is that if the team knows the truth that they’ll all leave in a mass exodus. So they overcompensate with positivity. My experience is that while a few will leave at the first sign of trouble, most people have a vested and personal interest to try to turn around the fortunes of the company and could be more helpful knowing they are needed through turbulent times. I knew one company that was imploding in which the CEO smiled, spoke highly of a phantom pipeline and ordered a new Porsche to prove everything would be all right.  Don’t be that guy. As a leader of a startup or small business, realize we have a 1 in 10 chance to make it, put your head down and go figure out how to make your business money.

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