09/27/20

CEO Shoptalk — All Risk Is Not Created Equal

If you are an entrepreneur, founder, CEO, you swim in a sea of risk, alternating amongst the butterfly, the backstroke, the breaststroke, and the crawl. You must do it all.

In the early days, you are a minnow (or a little mullet if you are feeling salty) and the dangerous waters of startup land are populated by voracious, big-toothed sharks, vicious sharks, all of whom want to devour you.

In these early, formative days every risk can eat you (kill you, destroy your company). [Worse, you don’t yet know the nature of risk. You are in that classic posture of not knowing what you don’t know.]

As you exit the size 2 Pampers, the list of things that can kill you begins to thin, but you add to it — you begin to take risk.

You visit risk upon yourself as you sharp elbow your way upward in the food chain. [Soon, you may become a shark.]

The big question is this — Do you understand the nature of the risks you are taking?

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03/9/20

CEO Shoptalk — Staffing

The subject of how companies staff their businesses, manage their employees, and administer the employer-employee relationship has been lingering in my mind for some considerable time. Today, I will try to put some order to it. Staffing.

At the core of every business is people. It starts with the founder(s) and then grows. A company cannot grow without being a capable employer, but little is said as to the system by which that happens.

Allow me to jump ahead. Assume:

 1. You are a founder/CEO who now has some semblance of a product, are struggling with product-market fit, have raised a bit of capital, and will have to hire people to drive and scale the business.

 2. Assume, in the alternative, you are a founder/CEO who has more than 50 employees, plenty of money in the bank, have achieved product-market fit, have 1,000 customers, and are now ready to really scale.

I use these two examples because I hope the logic is universal.

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10/25/19

Ownership v Stewardship For The CEO Class

Stewardship — huh?

It is cold in the ATX this morning — 48F, but it will be 62F this afternoon and 82F on Saturday. I may lay off the sunscreen today, but back on it on Saturday.

So, about a year and a half ago, I’m speaking with a recently exited CEO who is in that special place that drives the question, “What’s next? Is there a second act?”

Luckily for him, this question of a second actship (see what I did right there, made that word up) is not really a pressing issue as the financial outcome provides breathing room for a couple of centuries — maybe a millenium — at his current burn rate.

So, we get to discussing, “What did you really learn? What do you leave with other than money?”

We get into the discussion of ownership v stewardship.

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10/8/19

Chaos >>> Order

If you are a founder, entrepreneur, startup CEO then you are familiar with the notion of transforming chaos into order. [OK, let me say — “I hope you are.” However, we both know it is not as well ingrained as we might hope.]

If you are an “aspirin” startup — meaning the raison d’etre of your love child is to reduce the pain of mankind, the chaos is the pain and the order is the pain free — or lessened pain — environment that results thereafter.

If you are a “vitamin” startup — meaning the raison d’etre of your little bastard is to improve the quality of life, the chaos is the inferior quality of the before and the order is the higher quality plane of the after.

There is a decided “before” v “after” transformation.

Bit extreme, but it makes my point. Guy lost a lot of weight? What a magical transformation. I imagine he feels a lot better. Took those bad eating habits and created some order, no?

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09/14/19

CEO Shoptalk — Fragility

In the early days of a startup, when you are running on pure adrenalin, co-founders are in constant contact. Every new development is shared completely, you are likely to be in close physical proximity, and the novelty of it all creates a glue that binds the co-founders together thereby provoking a level of communication that ensures the founding team is fully informed.

At the beginning you are giddy with communication.

This chaotic time builds trust and generates confidence. It is a heady and energetic time. It is the camaraderie that soldiers create on the battlefield. Co-founders are at war against the market, so that comparison is not a great leap.

But, then the company raises money or gets traction or screams, “We have product-market fit, y’all!” and the closeness that was there at the crib side of the new baby begins to change.

Roles are more distinct, there are spheres of responsibility, employees are hired, parts of jobs are delegated, board members begin to deploy their wisdom, and the pace begins to quicken.

The ability for the co-founders to attain full communication and full knowledge of what is going on is tested by the actual progress.

It is at this junction in time — almost verifiable by a watch — that the strength of a co-founding team is tested.

And, the test is this — Is the organization robust (as it relates to co-founder communication) or is it fragile?

The answer, dear reader, 104% of the time is that the relationship is hopelessly fragile. It is the normal state of affairs because it requires specific work, organization, and that most precious of all commodities in the universe — time, to beat the fragility out of your fledgling company.

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08/18/19

CEO Shoptalk — The Founder’s Tale

In the life of the successful startup is a slightly disorganized story of its founding. It is a powerful story. It provides a keen insight into the who, what, when, why, where, how of the company. It is a story of creation. Only one person can tell it with an authentic voice.

It is a tale told best by the founder, hence the name: The Founder’s Tale.

It is a story that is the glue that binds people to the company and makes them want to follow the leadership. If you want to lead a pride of lions, then you have to tell the story of how you formed a pride.

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08/5/19

Practice Like You Play

One of the best bits of advice I ever received was to practice the same way I intended to play — good advice when pertaining to sports, the military, and business.

Startups are often given a pass for not following sound practices.

“Hell, they’re just startups.”

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