Purging the inner teenager - A journey from adman to entrepreneur

The American branch of life coaching strongly promotes confidence as a pillar for success in business. And if there were ever two types that are seen to have their fair share of the stuff it is admen and entrepreneurs. These two swashbucklers positively relish the hand-to-hand combat of their exciting and glamorous lives. The adman is an amalgam of sophistication and bravado, while the entrepreneur adds a dash of the adventurer to the mix. So what easier swing to make for an ad-monkey than from one high-flying branch to another?

“Don’t judge an adman by his cover,” which is blown the minute he steps out of his stylishly coiffed offices (designed to intimidate, I mean, ‘impress’ clients) and battalion of primpers, producers and presenters.

Like bankers and hacks, admen are, in fact, a nervous and flighty bunch, afflicted with profound self-scrutiny. They are bred to be just a little ahead of the curve so as to profit from it. So when things don’t go their way they quickly fall into deep cycles of anxiety and fear, which they pass onto those in their vicinity. This includes the consumer who is perennially bombarded with promises that abruptly switch to threats. “Buy this as it will bring you happiness.” “On second thoughts, buy it or your children won’t get an education.” Some may protest that this is due to an even twitchier client, but agencies play a prominent role as they sit at the front line.

So as a new boy thrown into the world of startups one’s frail constitution is tested. Leaving the lush fields of advertising to scavenge for your own nuts and berries doesn’t sound like a choice one would willingly make were there not some external force that necessitated it. In my case it was similar to the instincts that compelled me to leave home as a late teenager. The protective support system of the parental home was recast as a restrictive plastic bag over the head that I needed to pop…loudly. I was a teenager again in more ways than one.

I didn’t choose to form a startup. It chose me. I’d outgrown advertising and the adult world of business beckoned.

However, once free of the ad world, I felt naked. Stripped bare of my ‘creative briefs’ and brand triangles, I felt unprepared for a world without supporters, debaters and producers. Who would be impressed by my pithy selling propositions and artfully constructed engagement models?

I would have to train muscles that had been neglected for over a decade. In advertising, planners rarely even peep a producer, let alone a programmer. Our flights are booked, phones paid and taxes accounted for. Quitting advertising is like leaving home and realizing how awesome your parents were all along.

The palpable lack of ‘family’ was stronger than anticipated. Advertising invests a great deal into on socializing and building strong culture. The last agency I’d worked at even had sit-down dinners at 8pm every night around a big oak table for those who were working late. Birthdays are taken very seriously, and industry events regularly united me with my extended family. This family didn’t go away, but they could only watch from the sidelines as I grappled with new and cumbersome problems.

These problems were structured around relatively foreign entity too. Hard, cold cash. This doesn’t mean that a client’s commercial objective wasn’t at the centre of every marketing brief, but a strategist is like the Queen in that he or she doesn’t handle money in the day to day. It is not the object of every discussion and does not flood his every waking thought. We are protected from such worldly concerns so as to focus on the ‘higher orders’ of awe-inspiring creativity.

While I relished this more tangible world I missed the more subtle, metaphorical one where a stylish debate could win over my audience. In advertising we sell the product of communication, so story, poise and oratorial panache were my weapons, and ones I had mastered. On the new battleground, I was promptly robbed of my mastery and of my audience. I was now one of a million groveling startups competing for the attentions of very different suitor — the investor.

New and unfamiliar HR challenges presented themselves too. In advertising one may suffer substandard staff, but hiring, firing and training can remedy these. Roles are practiced, salaries are normalized and the potential workforce is finite. From within a startup, roles and motives are blurred. Unpaid collaborators are essential so one is in a constant state of covert recruitment. At any moment you could be talking to your next co-founder or client. Friends are put under new scrutiny for their partner potential. An almost feral vigilance develops, as one grows hungrier. Where will my next deal come from? Who to invest time into and whom to abandon? In any businesses human resource is a significant investment. In a startup, where one forever scopes, scrutinizes and scrounges, the cost is even higher. That cost is emotional as well as financial as relationships undergo a thorough pounding. Advertising, with its two-way mirrored focus groups, had not trained me for this caliber of hand-to-hand emotional wrestling.

Today I am 3 years into our venture. Blind, barefaced confidence I believed I needed is not what I have accrued. In fact it is the opposite of blindness. I see people more clearly, thanks to the honing of a new instinct (as well as making some perilous staffing decisions). I can see what I’m doing, where it fits into the world. And I can see how my old colleagues and industry were, and are, a significant and integral part of my future. The business I have built now actively collaborates with and enables advertising. And several of my investors are even from the industry.

Building a company is an eternal battle with ego. The angry teenager that harrumphs out of advertising to ‘be their own boss’ will struggle to see his own faults at first. Consequently it may be hard to truly see what is of most value in the product that materializes. Sometimes it might not be a tangible element, but simply the lessons themselves.

Recently my co-founder at Sympler and I found ourselves engaged in the exercise of removing features from our product to see what was left. After a series of intellectual pivots, it was slightly alarming to find we’d whittled down our precious creation to literally nothing. After a moment of panic, we realized that it was showing us exactly what we were made of, which was both humbling and liberating. Now we could go forward with mindfulness and a pure confidence that we’d earned.

Ben Jenkins is the CEO and co-founder of Sympler — a pop-culture video sampling platform. This piece represents a Maker essay as part of our new series of Hacker, Maker, Teacher, Thief essays. You can buy the book that inspired the series here.