Monthly Archives: November 2025

The “Looker” Entrepreneur

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I knew a person who always seemed to have a black cloud following over his head. He encountered some of the most bizarre situations I have ever known. His drive to work regularly was a harrowing experience. I would hear tales of near-death situations involving rogue drivers forcing him off the road. Then there was an incident at the sporting goods store. He tried to return an item he purchased and got into a massive fight with the store that involved an ongoing string of e-mails and phone calls. Finally, he always seemed to be feuding with a friend. The reasons were so banal that I never figured what was really the problem.

At one point I dug in a little deeper to try and understand why this individual was always struggling so much. And guess what I found? He had an LFT problem. If you have not figured it out by now, LFT means Looking for Trouble. He was continually loaded for bear and saw a conspiracy against him every time he turned around. Turns out he was a very aggressive driver (I rode with him once and he scared the bejabbers out of me). He could be very demanding so I imagine that in a retail store he might have been inclined to run roughshod over the salesclerk. He told me that his motto was to “expect the unexpected” and be ready to “play offense.”  

Going through life with an LFT mindset must be depressing. And it is an attitude that’s pure poison for entrepreneurs. I can see preparing for the unexpected, but intentionally expecting something bad to happen seems like it could become a self-fulfilling prophecy. I truly believe that if we see conflict and strife in every situation then that is how we will live. Those types of thoughts are like a magnet. 

I can count on two or three fingers the number of times I have had close calls in my car. I know I am vigilant when it comes to driving and while alert, I am not “waiting for the other shoe to drop.” In other words, I do not believe that there is someone out there looking to make my driving experience a miserable one. As an entrepreneur I am aware that there may be others who are looking to gain an unfair advantage. But I do not obsess with this awareness. Instead, I go into each situation with the belief that the person across the table from me is going to deal honorably and I know that we will find a mutually acceptable conclusion to our interaction.

Life is so much better when we are in LFG mode. LFG? Looking for Good.Do not be fooled by this approach. It is not naïve or Pollyanna-ish. LFG is relatively simple. We look for the good in every experience and with every person. This type of thought is also like a magnet. When we Look for Trouble, we find it. When we Look for Good . . . we find it! It does not mean that I am going to walk down a dark alley in a big city and flash a big roll of Benjamins! After all I am not bulletproof. But it does mean that until someone proves me wrong, I am going to choose to see a positive outcome in whatever I am doing.

The entrepreneur who wakes up in the morning with a siege mentality and wonders who or what is going to come at him today, is in trouble before his feet hit the floor. By contrast, the entrepreneur who wakes up and knows that today is going to be positive and productive has just set the stage for a great day. Oh sure, there will be challenges because that’s just life. But the challenges are so much easier to resolve when we do not have a nagging belief that there is someone hiding around the corner ready to whack us in the kneecap. 

So, which will it be – LFT or LFG? The choice is 100% ours to make. There is no conspiracy. And there is no “other shoe” about to drop. 

This blog is being written in tandem with my book, “An Entrepreneur’s Words to Live By,” available on Amazon.com in paperback and Kindle (My Book), as well as being available in all of the other major eBook formats.

The O-Fer Entrepreneur

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In baseball the stat line for a hitter who strikes out, flies out or grounds out in all his at-bats during a game is shown as 0 – 4 or 0 – 5. The stat sheet for a basketball player who continually shoots and misses without scoring a point might show 0 – 7 or 0 – 10. In athletic terms this is an O-fer . . . O for 4 or O for 5 . . . O-fer. Going O-fer is an ignominious experience and generally brings on scorn from the fans. In 1922, Babe Ruth faced St. Louis Browns’ pitcher Hub Pruett. The first 14 at-bats for the Babe resulted in 10 strikeouts and two walks. During the 1922 World Series, Babe Ruth hit one single and one double in 17 trips to the plate. Arguably one of the greatest players to ever step on the diamond, Babe Ruth struck out 1,330 times. That was fewer than other baseball luminaries such as Barry Bonds (1,539), Mark McGwire (1,596), Mickey Mantle (1,710), Alex Rodriquez (2,287) and Reggie Jackson (2,597). Any student of the game will tell you that all these players were some of the best in the history of baseball.

There is another side to the story. Ruth had 2,214 Runs Batted In (RBI); Bonds had 1,996; McGwire had 1,414; Mantle had 1,509; Rodriguez had 2,086, and Jackson had 1,702. And each smacked a lot of home runs during their respective careers – Ruth (714); Bonds (762); McGwire (583); Mantle (536); Rodriguez (696) and Jackson (563). I know this is a lot of statistics and if you are not a baseball fan you may not fully understand the astounding nature of these feats. But there is a point to all of this. In life we do strikeout. Baseball players strikeout. Entrepreneurs strike out. Salespeople strike out. Going O-fer is just part of the game.    

What matters is how we deal with going O-fer. When we flame out do we play the victim and blame someone else? Or do we examine our technique as well as the surrounding circumstances and look for ways to tweak our “form?” How easy would it have been for these great baseball players to have let their propensity to strikeout destroy their careers? Instead, they did something else. They figured out how to take the strikeout experience and find a way to hit the ball out of the park in a future plate appearance. Babe Ruth was number 118 in lifetime strikeouts, but he was number two in RBIs. I find this fascinating. Here is a man who drove in far more runs than he struck out – yet he had a lot of strikeouts over the course of his career. 

I listened to a podcast a few years ago about a venture capital firm that was launching its first fund. The principals were doing the typical road show and calling on prospective investors in multiple markets. They would typically be gone for a week at a time – one week they made 25 meetings in Boston, Chicago, Atlanta, Miami, and New York. During that week they were O-fer through 22 meetings. Imagine how this might feel! Yet, on their final day, they went three-for-three and netted tens of millions of dollars in commitments.

There’s more than just resilience at work here. It is critical to understand that going O-fer is just part of the game. It does not mean the game is over. With each new meeting, pitch, visit or idea, we are starting zero to zero. It is a tie game. I have learned not to look at O-fer beyond zero to zero. If we do not win the last at-bat, we simply start over with the next one. We remember the instructive elements from the encounter and discard all emotion as we make the pitch again to the next customer. We only lose if we stop playing the game. We know in our bones that eventually we will hit a home run or an RBI. So, we keep playing the game.

If we understand that O-fer is just part of the game and can maintain our positive energy, we can erase our doubts and feelings of limitation. This sets us up to ultimately connect with the ball and score consistently.

This blog is being written in tandem with my book, “An Entrepreneur’s Words to Live By,” available on Amazon.com in paperback and Kindle (My Book), as well as being available in all of the other major eBook formats.

The “Danger Will Robinson” Entrepreneur

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Lost in Space was a classic television show broadcast on CBS between 1965 and 1968. A young Billy Mumy played the part of Will Robinson who regularly interacted with the Robot. For those of you too young to remember, the plot centered on a modern-day Swiss Family Robinson, marooned in space where the goal was to somehow figure out how to return to Earth. I enjoyed watching this show in black and white, and later in color, while Will and his family would constantly encounter misadventures. One of the most epic lines was spoken in a raised voice by the Robot – “Danger Will Robinson; Danger!” whenever Will was about to be eaten by some exotic space creature, or step into an abyss that lay below some cosmic quicksand.

We entrepreneurs need our own version of the Robot to help us avoid many of the missteps that we encounter in our daily lives. One such opportunity for disaster comes when we are in the middle of negotiating. In my world, we are always buying and selling apartment properties. Let’s use the acquisition of one such property as the example for this blog. The property in question seems to perfectly fit our acquisition strategy. The location is right, the property age falls within the target timeframe, the unit mix is perfect, and historical data shows a very strong operation for the past several years. But . . . the price is significantly higher than we can pay to generate the return on investment we are seeking.

We negotiate back and forth. Offers and counteroffers ensue, but we just are not quite at the price we are looking for. Here is where we need the Robot to save us from ourselves. There is a psychological threshold at which point we are committed to getting the deal done. We are vulnerable at this point to being taken advantage of. Maybe we start looking at our projections again and tinker with the annual rent increase percentage we initially underwrote. When we do this, the numbers work, and we can close the deal. Yet are the new rent increase projections realistic? Or are we simply looking for a way to rationalize the adjustment? I have certainly done it before. My reasoning went like this, “The standard 3% increase on this property is approximately $25 per month. Another .5% pushes the rent up by $29 per month. A renter isn’t going to balk at $29 any more than at $25, so I’m comfortable using an annual rent increase factor of 3.5%.” Now, it is very possible that this line of reasoning is sound. But it is important to understand the motivation behind it. Are we modifying our projections just to get the deal done, or are we really being ultra-conservative and there really is not going to be a problem with the rent increase tweak?

There is a fine line to walk between being creative to successfully complete a negotiation and allowing our emotions to drive the terms and conditions that we are willing to accept. By establishing strategic parameters in advance, we can avoid becoming vulnerable to doing a bad deal. For example, we will only acquire an apartment property that is of sufficient size so that we are not compelled to purchase a second or third property in the same market just to gain management efficiencies and economies of scale. It is also important to remember to separate business negotiations from personal ones. Buying a piece of artwork for a personal residence is an emotional decision and it is acceptable to allow emotions to enter the negotiations. Making a business acquisition of some sort should be completely divorced of emotion in all but the rarest instances.

In a business negotiation understanding where the line is between sound decision making and being vulnerable to manipulation is critical. Establishing strategic parameters before the negotiations commence and then sticking to them during the negotiating process will help us avoid crossing this line.

This blog is being written in tandem with my book, “An Entrepreneur’s Words to Live By,” available on Amazon.com in paperback and Kindle (My Book), as well as being available in all of the other major eBook formats.

The Collaborative Entrepreneur

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Nike’s corporate tag line is “Just Do It.” And that could be the tag line for companies of all sizes. Leaders at all levels send the message of “Just Do It” to their “charges.” This notion boils down to a command and control style of management. And I probably do not need to point out how poorly this approach works with today’s Millennial and Gen Z workforce. We Boomers grew up in this environment and may tend to continue its practice. Perhaps it is time for something different.

I know that many entrepreneurs agree in principle with a more collaborative style of leadership. Yet, the language that is used may belie this agreement. Examine the following statement that rolls up many of the words used into a massive contradiction with collaboration. Mr. Smith is a senior executive with the ABC Company and he’s describing a recent business win for his company.

“My employees really came through with this project. I have a hundred people working under me and every one of them did their jobs like they were supposed to. I set their goals, and they achieved them. I’ve been focused on this opportunity for a long time. I love winning this way!”

At first blush Mr. Smith seems to be giving credit for the win to others. But the way he says it indicates that he is not yet a convert to a more enlightened style of leadership. Note the highlighted words. Clearly, he is in charge here and other people have done his bidding.

Entrepreneurs can change this narrative. When we are comfortable in our own skin, we are easily able to eliminate the unhealthy aspects of our ego from our interactions with others. It is often the case that having to take the credit for an accomplishment or reinforcing the fact that we were “at the top of the food chain” is a result of our own lack of confidence or some other insecurity. With our new level of comfort, we relax, smile, and become totally humble.

Here is another version of the previous statement. Mr. Doe is a senior executive with XYZ, Inc. and is celebrating recent success.

“The XYZ team is amazing! They worked together to establish the goal and drew upon our Core Values to develop a winning strategy. We are so appreciative of each and every one of the hundred team members who worked tirelessly on this project for more than a year. Their commitment, dedication and creativity are the reasons for our success.”

Sounds a little different, doesn’t it? There is not a single mention of the words “I,” “me” or “my.” The word “employee” has been replaced with “team member.” Mr. Doe simply delivers the message without allowing his ego to enter the picture. Clearly, Mr. Doe’s team members work “with” him – not “under” him. I have written before about how we need to be intentional about modifying our vernacular away from “I,” “me,” and “my,” and changing to “we,” “us,” and “our.” 

Collaborative leadership is not decision making by committee – as a leader we still make the ultimate critical decisions. Collaborative leadership is about seeking out team members and listening to their thoughts and ideas. It is valuing others as human beings and the contribution they make to the enterprise. It is about having empathy and creating a culture of respect. And it is about using the words we say as a reflection of all these factors.

When we think about what we write and say we can ask ourselves this simple question – “Do my words focus the spotlight on me or on others?” Doing so helps us move away from the old command and control approach of the past.

This blog is being written in tandem with my book, “An Entrepreneur’s Words to Live By,” available on Amazon.com in paperback and Kindle (My Book), as well as being available in all of the other major eBook formats.

The “My Word is My Bond” Entrepreneur

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This blog is a bit of a lament. I grew up in my industry during the 1970s and 1980s when a handshake was still as meaningful as written documentation. The proverbial handshake was not necessarily a legal contract, but it might as well have been. Once we gave our word, nothing could change the follow-through on our intent. Legal documentation was merely a formality and there was not a lot of haggling over the verbiage. Sadly, this notion of “my word is my bond” has diminished in recent times.

Sometime ago we sold two large apartment communities that were part of our portfolio for several years. We went through a painstaking process of listing the properties for sale with a national brokerage firm. The properties were marketed extensively, and we issued a call for offers. Dozens of offers were received, and we opted to have further discussions with the top ten bidders. Then we made a call for “best and final” offers. Once those offers were received, we interviewed the top four bidders and determined a winner. We then told the winners verbally that we were accepting their best and final bid. In both instances, one of the unsuccessful bidders reached out within 24 hours and increased their offer. In one case, the increase was $250,000, and in the other case it was $750,000 higher. In our minds there was no decision to be made. We had already given our word to the initial winning bidders, and we had no problem staying with their offers, even though it cost us $1 million.

Contrast that with a situation that occurred with another of our business units. This business is involved in the syndication of historic tax credits. We offered term sheets to a developer who verbally accepted our offer and confirmed the acceptance in an e-mail. A couple of weeks passed, and we had not received a return of the term sheets signed by the developer. When we reached out to the developer he apologized and said that he had decided to accept an offer from another tax credit syndicator. Legally, he had every right to do this. But it certainly left a sour taste in our mouths. For sure, his word was not his bond, and he did not even have the courtesy to let us know without being prompted.

It all boils down to the simple yet powerful premise of Integrity. Our company embraces five Core Values, one of which is Integrity. We are proud of the fact that we can demonstrate in real time that we practice what we preach. Integrity used to be a foundational principle for entrepreneurship. I believe that it still is, but it has become devalued – especially where the almighty dollar is involved. The problem is compounded by the fact that too many businesses throw around terms such as “integrity” and “honesty” but fail to deliver on them. Hearing Honest Harry yap about how you can trust him to sell you a car at “$1 over invoice” has caused society to tune out.

So, what do we do about this sad fact of life? At this point, I do not really care about whether I can believe that the word of other entrepreneurs is their bond. Instead, we will just keep doing things the old-fashioned way. If I tell you something, you can believe it whether we have a legal document or not. Hopefully, you will treat me the same way. If I screw-up, I will step up and make it right whether I have a legal document compelling me to do so or not. I cannot count the number of times over the course of my career this has happened – at a cost of literally millions of dollars. This may not be the smartest business decision, but it is the right thing to do, and I can sleep at night.

At the end of the day, as entrepreneurs we should want to be judged by the character we display over the course of our careers rather than the amount of money we will have made.

This blog is being written in tandem with my book, “An Entrepreneur’s Words to Live By,” available on Amazon.com in paperback and Kindle (My Book), as well as being available in all of the other major eBook formats.