Ready, Fire, Aim - Entrepreneurs Must Plan To Build Upon Their Initial Success

On April 14th, 1865, while hanging around Ford's Theatre reading his mail, Booth learned that Lincoln would be attending that evening's performance of Our American Cousin. At that moment, Booth decided to carry out his assignation plot.Once the exhilaration of successfully executing the initial phase of his plan passed, Booth quickly realized that his script had no Second Act. Much like an entrepreneur who orchestrates a successful product launch or pivotal partnership which subsequently fails due to poor execution, Booth had not planned how he would capitalize on his initial success.

As noted in Tom and Huck, some entrepreneurs are far too analytical. Such entrepreneurs devise business plans that are too complicated and often cause the entrepreneur to expend more effort and energy than is otherwise necessary.

Clearly an overly complicated approach is to be avoided. However, do not err in the other direction and assume that planning is irrelevant. Simple is good, but simplistic is bad. As with most things in life and in business, strike a balance in the depth of your planning between ineffectual and shooting from the hip.

Ready Fire Aim

If you do not have the discipline to craft a simple yet sound Huck Plan, do not use the excuse of potentially over planning to not plan at all. Many entrepreneurs do an excellent job of planning the events immediately before them, but do an inadequate job of devising a coherent plan beyond the near-term events. Such under-planning can be just as devastating as over-planning. Take, for instance, the John Wilkes Booth's assignation plan, which he hatched the day he killed President Lincoln.

The previous year, Booth and his conspirators had planned to kidnap Lincoln and exchange him for Confederate prisoners. With General Lee's surrender at Appomattox, Booth believed that a bold action was required to save the South. The kidnapping plot, which was meticulously planned, included use of the Confederate Underground of Southern sympathizers located in Maryland who would secure Booth's safe passage to Virginia and ultimately the Deep South. The kidnapping was foiled when Lincoln changed his itinerary at the last moment.

In contrast, the assignation plot was unplanned, beyond Booth's escape route out of Washington, DC. The only additional planning Booth did was to secure a fast horse for his getaway and to have field glasses and a rifle waiting at the Surratt's boarding house, which was along his escape route in Maryland. Unlike the kidnapping plan, the half-baked assignation plot would not transfer either political power or Booth himself back to the South.

Unfortunately for both the North and South, Booth's plan was initially executed flawlessly. Like many entrepreneurs, his plan was bold and daring. The only mishap was that Booth's spur caught on the bunting surrounding Lincoln's boxed seat, which caused him to break his fibula following his dramatic 11-foot jump to the Ford's Theatre stage.

Booth also had the foresight to travel light, which allowed him to race out of Washington, DC, ahead of the news of the assignation. His quick flight out of the city made it possible for him to talk his way past a guard at the Navy Yard Bridge into Maryland.

Due to his lack of planning, Booth showed up on the doorstep of a number of Southern sympathizers who were unprepared and in some cases, unwilling to lend him assistance. His broken leg forced him to spend five days in a pine thicket with no food, water or camping provisions. After attempting to cross the Potomac and going in the wrong direction, he was eventually killed twelve days after assassinating President Lincoln.

As Booth learned the hard way, bold, decisive actions must be followed by a plan to leverage your initial success. If not, your adVenture will ultimately fail.

Good Problems

You clearly do not want to repeat Booth's mistake of inadequately planning beyond the first phase of your Plan. However, you also should not spend time over-planning for good problems (e.g., too many users, not enough inventory, etc.) You will have the luxury to deal with such problems IF they arise because they are a result of your success.

Positive outcomes from your success should not be a focus of your attention. Achieving success shall be your initial focus, followed closely by steps required to sustain such success. Whenever you or a member of your team says, "Yeah, but that would be a good problem." Stop planning for it and focus on potential events which could stand in your way of getting to the point where you actually have ‘good problems'.

Many executives at BDCs and even some entrepreneurs are Tom Sawyers without freckles or a straw hat. They get caught up in the moment and execute tasks that they find exciting and fun, even when they are gratuitous and overly complex. Many technical managers enjoy solving difficult problems; the harder the problem, the more satisfying and worthy the challenge. Beware the seduction of overly complex challenges as they can distract you from executing your Huck Plan.

Other entrepreneurs share John Wilkes Booth's attention to detail. Unfortunately, their flare for the dramatic and their penchant for bold and decisive actions are often performed at the expense of properly planning how their company will leverage its initial success. Avoid this mistake by crafting a simple and sound Huck Plan that anticipates how your adVenture will build upon its initial success and ultimately become a self-sustaining entity.

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John Greathouse is a Partner at Rincon Venture Partners, a venture capital firm investing in early stage, web-based businesses. Previously, John co-founded RevUpNet, a performance-based online marketing agency sold to Coull. During the prior twenty years, he held senior executive positions with several successful startups, spearheading transactions that generated more than $350 million of shareholder value, including an IPO and a multi-hundred-million-dollar acquisition.

John is a CPA and holds an M.B.A. from the Wharton School. He is a member of the University of California at Santa Barbara's Faculty where he teaches several entrepreneurial courses.

Note: All of my advice in this blog is that of a layman. I am not a lawyer and I never played one on TV. You should always assess the veracity of any third-party advice that might have far-reaching implications (be it legal, accounting, personnel, tax or otherwise) with your trusted professional of choice.

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