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What Fantasy Football Taught Me About Business

Ah, can you smell it? Yes, I think you can. That's right. Football season.


As I weigh my options and strategies in the Dynasty Football World Championship, I recognized my learnings in this nerdy simulation of football have provided several bricks in the foundation on which I conduct business.


I began playing fantasy football in high school. One of my friends wore a suit to our inaugural draft (this, the same guy who wore a suit to my high school games, clipboard in hand, hair combed over so as to best mirror a slimy college basketball scout).


In 1 A.B. ("After Basketball"), I had much more time on my hands. I interviewed around Wilmington, including at Suncoast. The interviewer asked me to list the five most powerful Russell Crowe movies and why each made the cut. I named Gladiator and LA Confidential and then went silently blank. An awkward moment, but it was Christmas time so he still offered me the job. I couldn't do it.


I pillaged video games from yard sales and wholesaled (wholesold?) small electronics all the way to 1000+ transactions and a 99.9% satisfaction rate on eBay. Shipping packages in/out of an apartment where the employees hated their job was no small feat.


I also played more fantasy football - a lot more. Now, 10 years in the game, I'm an improving veteran. Anything I commit time to is something I find interesting and enjoy improving upon.


A few things I have taken with me:


1. A valuation is just that, a valuation - There's many, many ways to value a product, service, person, company, or football player. Because something is priced a certain way does not mean you have to buy it at that price. The valuation may be so laughable that you walk the aisles quickly, not lifting your eyes from your phone, and walk away never to enter the store again.


2. Negotiating is fine, to an extent - If, in the instance above, the service/product/player is desirable but overpriced, then counter offer. A counter offer is a necessary aspect of business, but finding business partners who trust you are bringing a reasonable offer to the table from day 1 is an important relationship to find. Those who negotiate just to negotiate may find deals dry up as time passes and the landscape evolves - don't negotiate yourself out of strong business connections.


3. Avoid doing business with undesirable business partners - Some people are naturally difficult to deal with and the only way to keep sane is to avoid doing business these people. There are enough avenues for value generation to not force relationships. We are better off doing business with people we enjoy rather than with someone who leaves us tired and weak.


4. Price aggressively - When you are trying to sell something, you are at the mercy of the market you face. If you set the price poorly, you're screwed. Perhaps you may have even left a poor taste in a consumer's mouth. Fair pricing is crucial. That undoubtedly does not mean you must be the lowest cost provider. As others learn you offer a good product/service/trade offer, you won't have to waste your efforts in negotiation - you have built trust by doing good business.


5. The cost to buy and cost to sell varies by consumer - Simply put, every consumer has different opportunity costs to weigh when buying or selling anything. The value of a business acquisition is going to mean something different for a highly liquid company seeking market dominance versus a cash-strapped buyer. The value of an aging Larry Fitzgerald depends on the direction of the team.


6. Burned bridges are tough to mend - A bad deal leaves a very poor taste in the mouth of both parties. It's a mutual parting that takes two sides letting bygones be bygones and coming back together. That's pretty rare after trust has been violated, especially when money/value is involved. You are as good as your last deal, and those are high stakes.


7. Transparency always wins - You don't want others to question your integrity. The way to expedite trust is, well, giving someone a person they can trust. We do this by letting our own guard down, take a step toward openness and confirm your fairness with action rather than simply words. Do good by others, the rest works itself out.


8. Trust your valuations - If something holds value, be willing to pay for it. Do not avoid premium prices simply because they are premium prices. Many investments come with a hefty price tag but the value brought to the table justified that premium. Lose the idea that you cannot ever overpay what the market indicates you should pay. And if the cost doesn't line up with the value, we must create an investment opportunity elsewhere.


9. Fear of losing helps nothing - The concern that you're not walking away a victor only serves as an energy block. The worry that you've made the wrong choice generates an unnecessary amount of anxiety that we want to avoid. Freeing the mind of negative energy is a must in anything we do, business and fantasy football are merely two examples.


10. A contrarian mindset brings opportunity and invention - On average, people are risk averse. A façade exists that the unknown should frighten us, and thus we often invest our efforts in a safe haven rather than a "counterintuitive" product or opinion (counterintuitive from the market's perspective, that is). Empowering our intuition and reflecting on the results ensures constant improvement. We outpace replication by reinvention - what do you do that your competition does not?


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