The Doubting Entrepreneur

There’s one thing of which I’m certain . . . I think. Have you ever had this kind of feeling? We entrepreneurs are a pretty confident lot. We are scrappy and tough. There’s nothing we can’t do including leaping over tall buildings in a single bound. Throw us a challenge and we’ll whip it with one hand tied behind our back and blindfolded to boot. Right? Well, maybe. And most of the time.

Entrepreneurs have several “thought enemies,” one of them being gnawing and nagging doubts. Here’s a not-so-fictional example. Let’s say that things have been going pretty well in our business and we’ve had some nice wins along the way. Then we hit a little speed bump – perhaps a contract doesn’t get signed that we thought we had in the bag. Or an important customer stops doing business with us. In other words, we get knocked off our game a bit. That part we can handle with aplomb as we go on to sign another contract or we fix the problem with our important customer. It’s what happens next that can be perplexing.

After we’ve been bucked off the horse so to speak, we begin to have feelings of doubt. For example, we are ready to introduce a new product or service, but we wonder if it might flop. In the past, we would have launched without any trepidation, but now it feels different. Could something else go wrong that that might cause everything to come unraveled? We know that these gnawing and nagging doubts aren’t healthy and could become self-fulfilling prophecies. Yet still they are there and hard to push out of our mind.

Why is our confidence shaken, and doubts have entered the picture? I’ve thought about all of the times this has happened in my life and believe it centers on a rather recent failure in the past. The earlier example that I gave where the contract or customer was lost illustrates this notion. Coming off of a failure makes us wary and more sensitive. As entrepreneurs we have winning in our DNA. Failure is for losers. And yet we do fail, and we do lose. Sure, we’re resilient, but we can’t ignore what it felt like to fail and lose, and we don’t want to experience it again. And so, we’re vulnerable to doubt and uncertainty. Subconsciously we’re thinking, “I’m sure what I’m doing now is going to work, but if it doesn’t, I don’t want to be hurt again.” We find ourselves moving forward but wondering . . . always wondering when the other shoe will drop.

Here’s what I’ve learned about myself when these insidious doubts start creeping into my consciousness. I step back and take inventory of all of the positive successes that I know lay in front of me. I may have just lost a deal, but there are ten more that I believe with all my heart will succeed. Now here’s the key – even if only half of the ten deals actually succeed, I’m still way, way ahead. In other words, I’m not looking at the glass half full, but I’m looking at multiple glasses and every one of them is overflowing. Immediately my mindset changes and all is right with my world again. I’ve accepted the fact that I had a prior setback. I’ve accepted the fact that I’ll have more setbacks in the future. But I know that the pluses will always far outweigh the minuses and the winning score will be in my favor – overwhelmingly!

Gnawing and nagging doubts are usually a product of a recent failure. We get past such feelings by looking at the scoreboard and realizing that we are way ahead in the game. Ultimately this makes us unbeatable.

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 Adaptable Entrepreneur

Major league baseball pitchers throw some amazing pitches. Their repertoire includes the breaking ball, changeup, forkball, screwball, slider, curveball, knuckleball, four-seam fastball, split-finger fastball, cutter, sinker, two-seam fastball and probably some other customized versions of all the above. These pitches range in speed from 70+ to over 100 miles-per-hour. How a batter can even see a pitch that is screaming in at speeds above 90 and dancing all over the place is an incredible feat. And the fact that such pitches can be hit for home runs is even more stupefying. How do they do it?

Major league batters expect to adapt. They know that they are going to see a wide array of pitches that are surgically placed in different locations in the general area of home plate. Thus, every at-bat requires them to adapt to a host of variables. Top-flight big leaguers have an uncanny knack for successfully adapting their vision and their swing to hit the ball and get on base. They go to the plate knowing with absolute certainty that they must be able to adapt, or they will strike out, fly out or ground out.

As entrepreneurs we would be well-served to study successful major league baseball players and observe how they adapt. Sometimes they shorten their swing. At other times they become supremely patient. They may try and push the ball to the opposite field; they may bunt, and they might also time their swing in order to pull the ball. All of this happens within a split second.

We entrepreneurs often work hard to create elaborate strategies and back-fill with a host of tactics. We plan and we create extensive systems and processes. All are absolutely necessary to succeed. But sometimes we forget that we must expect to adapt. There is nothing negative about holding this expectation. The game plan provides a road map for us to follow, but it doesn’t account for every possible instance where we may need to be flexible.

With the disruption caused by COVID-19, our ability to adapt will be tested more than ever before. Businesses have been turned upside down along with the rest of our lives. Having a playbook is important but being able to turn on a dime and act entrepreneurially is critical to adapting to what may be the new normal. Over the years I’ve tried to muscle my way through a plan that I was convinced was the only way to go. Most of the time it led to failure or at least results that were less than stellar. I realize that I was being resistant to adaptation.

What I wish I had understood at the time is that the need to adapt can offer some incredible opportunities. And my resistance caused me to miss those opportunities. It’s easy to say, “OK, I have a plan and undoubtedly something will knock me off-course.” What goes unsaid is the thought that, “Then I’ll do whatever it takes to get back on-course.” But what if we had a mindset of expecting the need to adapt and actually turning it into a desire?” Think about all the wonderful inventions that have occurred in the past. If you’ve ever read the story of Steve Jobs, you’ll know that he was a master of adaptation. Through his flexible nature he embraced the chance to make changes to the iPhone and the result was, “WOW!” It’s well-documented that the initial vision for this technology would not have been nearly as phenomenally functional as what was eventually developed.

When we rejoice at the prospects of adapting our ideas, our creativity increases exponentially. Then we are positioned to achieve greatness in whatever we choose to do.

 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.

COVID-19 and the Entrepreneur’s State of Mind

This is surreal. It was a little bit like this after 9/11. But this time the uncertainty seems unprecedented. Many are locked down in their homes – some for weeks and maybe even months. Certain elements of society have decided that it’s a good idea to hoard toilet paper, water and other everyday staples. The reason for this is unclear. COVID-19 is turning out to be a major test of our collective resolve and common sense. Entrepreneurs have a lot riding on the resolution of this crisis. Much is out of our control. But one thing is for certain – our state of mind will be a major factor in the level of our success or failure.

OK, where to start? We acknowledge our fears and anxiety. It’s normal to feel this way. But we need to put this in perspective. For whatever reason, the human mind tends to gravitate to the most extreme and adverse outcome. Hence all the very dire predictions about casualties and economic cataclysm – few if any based upon a shred of solid evidence. We need to ignore the noise and understand that we can’t know all that is going to happen. However, it’s likely that things won’t be as bad as we conjure them in our minds. And, we’re all in this together. It’s not as if anyone is going to win from this situation.

We have a choice to make. It’s the most important choice that we can make during this unfortunate circumstance. We make a choice as to our mindset going forward. There’s no doubt that we’ll face significant challenges. Guess what? Everyone is going to face significant challenges. If we choose a mindset of panic, we won’t be productive. If we choose to dwell on loss, lack and limitation – that’s what will manifest. I’ve said it a million times – our mind is an incredibly powerful organism. Thus, we must take great care in how we form our thoughts.

We are entrepreneurs. Our middle name is “Resilience.” While others may wring their hands in despair, we will be strong and positive. We will not dwell on that which we can’t control. To maintain a strong mental state, we will reach out to others – family, friends and colleagues – to offer a shoulder to lean on. We will listen and comfort. We will listen and reassure. We will get out of ourselves by figuring out ways to serve others. In so doing, we build the strength of our character and demonstrate a resolve and commitment to not only endure the crisis but use the experience to be as creative as possible.

We wake up each morning in a spirit of gratitude. We express our appreciation to everyone around us for all that they mean to us and do for us. We smile and laugh. We take care of our bodies through continuing to exercise and eating in healthy ways. Developing a daily routine is important to our physical and mental wellbeing. We avoid spending an inordinate amount of time on social media for it is filled with misinformation and hyperbole. We spend our time working remotely if that is necessary, as effectively as we can. And we use a portion of our time to develop ways that we can deliver our products and services in an even more efficient and effective manner and provide an amazing experience for our customers. Think about it. It’s like an auto race. Every so often, we need to make a pit stop, but we don’t want to fall behind in the race. Right now, all drivers are under a caution flag. The race hasn’t been cancelled, but we’re driving slowly behind the pace car. We can take a little time to plan on new and improved ways to work ON our business, rather than always working IN it.

We are entrepreneurs. COVID-19 is our yellow caution flag but we’re not quitting the race. Far from it. We’re maintaining a positive mindset – always! We’re looking for ways to serve others each and every day. We don’t obsess over that which we can’t control. While times may be very different for a while, we adapt and are productive in the most positive of ways. We are entrepreneurs and we will survive . . . and then we will thrive.

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.

Entrepreneurs Beware!

We live in a hypersensitive society today. It seems as though every time we turn around someone is being offended by something. It may be words, actions, facial expressions or even the way someone looks. The whole notion of being offended stems from a belief that we are somehow victims. Victims of what, I’m not really sure. But our culture is at a point where it promotes victimhood and all that goes with it. This is a very dangerous place for entrepreneurs to be.

Many of us Baby Boomers raised our children in an environment where everybody wins and there were no losers. I remember sporting events in which our daughters participated, and each child received a ribbon or a small trophy. Obviously in the real world there are winners and losers yet somehow, losing has become linked with victimization. I’m not saying that this is the sole reason for the hypersensitivity we are experiencing but it may be a contributing factor.

Entrepreneurs are in a tough spot. On the one hand we want to be sufficiently sensitive to saying or doing things that others could perceive as a slight. And yet we are in a rough and tumble business world that takes no prisoners. Unfortunately, it’s not enough to simply treat others as we would like to be treated. I’ve grown pretty thick skin over the years and as others will attest, it’s pretty hard to offend me. A few years ago, I took a computerized test that measured resilience among a number of traits and tendencies. My score was 97 out of 100 which I’m told indicates that I have very strong self-acceptance. My point in sharing is to demonstrate that I may be somewhat oblivious to attempts by others to offend me. So, what to do?

First, we need to measure our intent when we are interacting with others. Do we say certain things to another person because we want to make them feel inferior? Do we take certain actions because we want to “send a message” to a specific individual that we expect could result in hurt feelings? A compassionate leader will communicate honestly and openly while doing so with sufficient empathy. His or her ego will be totally eliminated from the interaction. If our intent is pure and we’ve separated from our ego, then it is less likely that we will offend someone.

Second, it’s important to understand what behavior is unacceptable. This is especially challenging from a generational perspective. A young female colleague of mine was at a luncheon recently. She shared that she sat next to an older man (Boomer generation) who was nice but commented as they were leaving that he was pleased to have been able to sit next to such an attractive young woman. My colleague was not offended but related that she thought the comment was unnecessary and inappropriate. What was intended as a compliment by an older man was interpreted as mild condescension by a younger woman. While I doubt that it was his intent to be condescending, it was clear that he has not learned that you just don’t say things like this.

I’m not advocating for political correctness. We’ve gone completely overboard with PC and it’s causing huge problems in our country. But I do think that we need to pay closer attention to how we might be perceived by others. And let’s do our own gut check. Do we find ourselves being offended with any frequency? If so, we might benefit from exploring what we see when we look in the mirror. Do we have a positive or negative self-image? Are we preoccupied with conflict or feelings of inferiority? If so, we may be prone to being easily offended.

As entrepreneurs we must develop thick skin through a strongly positive self-image. At the same time, we need to measure our intent when interacting with others as well as understand what is unacceptable to society. Doing so will minimize the likelihood that we will offend others.

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.

Farewell to an Iconic Entrepreneur

On January 3, 2019, one of the legendary icons of entrepreneurship stepped on a rainbow. Herb Kelleher died at age 87 after living a storied life. Kelleher famously co-founded Southwest Airlines in the late 1960s. He was practicing law in San Antonio when a client brought him an idea to launch a new airline in 1967. Competing airlines did everything they could to prevent the new airline, originally incorporated as Air Southwest Company, from getting off the ground. Lawsuits were the only thing flying for several years, and at one point the board told Kelleher that the venture needed to be shut down. Kelleher offered to fight the lawsuits and pay the court costs out of his own pocket at which point the board agreed to stay in business. It took four years and victories at both the Texas and the U.S. Supreme Courts – twice – before Southwest Airlines flew for the first time on June 18, 1971. His resilience and tenaciousness are credited for enabling Southwest to persevere and become the major airline that it is today.

Kelleher was general counsel and served on the board of directors, becoming chairman in 1978. In 1981 he became the full-time CEO and built the airline into a powerhouse as a result of his vision. At the time, the airline industry was highly regulated and when an airline started losing money, it would petition the Civil Aeronautics Board (CAB) to allow for a fare increase. As a result, it became exceedingly expensive for the public to fly – something that Kelleher saw as the opportunity of a lifetime. Initially Southwest was an intrastate carrier flying within Texas, making flying between Dallas, San Antonio and Houston affordable through ultra-low fares. Over the years the airline started flying outside the state of Texas but was hamstrung by the Wright Amendment – legislation designed to help the legacy carriers and hurt Southwest. The law required that Southwest could not fly from another state directly into Dallas’ Love Field without first stopping in an immediately adjacent state including Arkansas, Louisiana, Oklahoma and New Mexico. I can remember flying from Kansas City to Dallas and having to stop in Oklahoma City to change planes because of this requirement. Eventually the Wright Amendment was defeated in Congress and Southwest was able to operate like any other airline in the country.

Kelleher was a marketing genius and employed numerous outrageous stunts that endeared Southwest to its employees and to the public. He never took himself too seriously and is well known for his love of Wild Turkey bourbon and a daily dose of five packs of Marlboro cigarettes. When it came to compensation, Kelleher chose to take less in cash salary and more stock options. This approach helped considerably with the Southwest labor force (where the CEO was not receiving an exorbitant level of pay) and made him a billionaire two-and-a-half times over. He claims to have been a “flamboyant marketer but was fiscally conservative.” His shrewd financial prowess put Southwest on a path to profitability that is unmatched by any other airline – and few public companies in any industry. Since 1973, the company has been profitable every single year.

For decades, the culture at Southwest Airlines has been studied under a microscope by business schools and business leaders. It’s safe to say that Kelleher defined and sustained that culture for the 20 years he was the CEO and even after he retired in 2001 (he remained chairman of the board until 2008). He spent an enormous amount of time talking to employees and gaining understanding for what was working and what needed to be fixed. He loaded baggage onto planes every Thanksgiving Day; met technicians at 2:00 AM in a maintenance hangar; visited operators at reservation centers and spent time as a gate agent. According to Terry Maxon, in a 2015 article for the Dallas News, Kelleher dressed up like Elvis Presley, a woman, the Easter bunny, a leprechaun and a flight attendant to promote Southwest. Maxon went on to explain the corporate culture was that of a 1) scrappy underdog to the public; 2) fierce warrior to its competitors, and 3) warm, supportive and protective atmosphere for the employees.

Herb Kelleher was a larger-than-life model for us as entrepreneurs to emulate. He had all the requisite entrepreneurial traits – vision, tenacity, resilience, marketing skills, financial acumen, a cultural leader and a genuine love for people. Above all he had a passion for life. They broke the mold when Herb Kelleher left this planet. R.I.P.

You can also listen to a weekly audio podcast of my blog. What you hear will be different than what you read in this blog. Subscribe on iTunes or wherever you get your podcasts. You can also click on this link –

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.

Mickey Mouse’s Father – An Amazing Entrepreneur

I recently re-read a terrific biography by Bob Thomas called Walt Disney: An American Original. Thomas was a reporter and biographer who authored multiple biographies focusing on Hollywood celebrities. The Disney story is fascinating and is packed with incredible entrepreneurial anecdotes. As a kid in the 1950s and 1960s, I watched Walt Disney Presents and Walt Disney’s Wonderful World of Color on ABC and NBC. I remember attending the Disney movie Babes in Toyland in early 1962 at the local theater. And then of course there was Mary Poppins starring Julie Andrews and Dick Van Dyke in 1964. The pièce de résistance was a visit to Disneyland in Anaheim, California, with my family. Of course as a boy I had no idea what entrepreneurship was all about.

Roll the tape forward several decades and I find myself in awe of this amazing man. He epitomizes so many positive traits of a successful entrepreneur. For starters, he was one of the most optimistic individuals I’ve ever studied. Walt Disney was born in 1901 and began his career at age 18, and in the 1920s moved to California and launched Disney Studios with his older brother, Roy. The early days were lean – sometimes very lean. There were many weeks when the Disneys were scrounging for enough money to make the payroll. Roy took this very seriously and fretted considerably over their plight. But Walt was the eternal optimist. He would smile and say he never worried about money. He believed they would always figure out a way to survive. And he was right! Somehow the studio inevitably pulled a rabbit out of a hat and came up with the cash. Without Walt’s optimism and positive mindset, there would be no Disney legend that we know today.

Walt understood grit and perseverance better than anyone else. The Disney organization was just starting to come into its own when the Great Depression came crashing down upon the country. And yet Walt continued fine tuning his craft and creating cartoons that were well received by theater audiences everywhere. His optimism fueled this perseverance and every time he was knocked down, he was able to pick himself up, dust himself off and go back at it. This resilience combined with perseverance and a positive attitude was the key to surviving the dark days of the 1930s.

Creativity was another Disney hallmark. Walt got the idea to create a feature-length animated movie and introduced the world to Snow White and the Seven Dwarfs in 1937. No one in the film industry had every produced a feature-length animated movie and everyone doubted that such a production could succeed. Walt Disney proved the skeptics wrong and followed with additional masterpieces such as Pinnochio (1940), Fantasia (1940), Dumbo (1941) and Bambi (1942). When World War II took away many of his talented animators, he made movies under a contract with the federal government. While not nearly as profitable, the Disney organization was able to endure the war and remain in business. Walt’s creativity and ability to adapt to his circumstances were more entrepreneurial characteristics that led to his success.

He was a true visionary in every sense of the word. After succeeding with motion pictures, Walt foresaw the opportunity to create an amusement park that embodied the magic he had been delivering through his animated films. I can still remember that trip to Disneyland when I was five or six years old. I was overwhelmed by such an amazing experience. After Disneyland came his ideas for Disney World and Epcot in central Florida. Unfortunately, Walt Disney died from lung cancer in 1966 at the age of 65. The tragedy of this was the fact that he never witnessed the finished product of the Florida projects.

Walt was obsessed with detail and would often snoop after hours and look at the animator boards to see what his team was producing. Often the animators would arrive the next morning to find notes from Walt suggesting changes that would improve their work – and he was usually right about what he wanted. He demanded the highest level of quality for everything that bore the Disney brand. This was one of the major differentiators that enabled the Disney organization to consistently outpace the competition.

We entrepreneurs would be well-served to use Walt Disney as a role model. Wrapped into a single human being are the entrepreneurial traits of optimism and positivity; grit, perseverance and resilience; adaptability; creativity; vision; attention to detail and demand for quality. The impact he has had on our culture is indelible. The impact he has had in blazing a trail for entrepreneurs is profound.

You can also listen to a weekly audio podcast of my blog. What you hear will be different than what you read in this blog. Subscribe on iTunes or wherever you get your podcasts. You can also click on this link – Click here to listen to Audio Episode 114 – Exactly What is Accountability?

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.

Existential Threats to the Entrepreneur

That’s an ominous sounding title for this blog – right? But not necessarily for reasons you might be thinking. When most entrepreneurs think about what can “kill them” – in a metaphorical sense – they might list undercapitalization, the inability to hire a qualified and competent workforce, or chronic issues with their product. While these can be serious problems, they are much less severe than the existential threats I’m going to discuss.

I believe that the most menacing threat to an entrepreneur’s existence is his or her own mindset. Do we truly believe we can succeed, or do we feel victimized and constantly under siege? Great entrepreneurs are eternal optimists. We know we can win – there’s no doubt about it. We will pivot when we have to, but we are absolutely convinced that we will reach the Promised Land – whatever that might represent for our endeavor. Entrepreneurs who are too skeptical or pessimistic are destined to fail. They become tentative and can be paralyzed when making important decisions. Negative Nellies will usually crash and burn. They live in a world of lack and limitation. They can’t escape the negative energy that always surrounds them and eventually impacts their team.

Hand-in-hand with the negative mindset is another existential threat – that of low resilience. Look, we entrepreneurs get beaten up a lot. We make a ton of mistakes. We hear from plenty of people who don’t like us or what we are doing. If we can’t get up off the ground when we’re knocked down, then we’ll die lying there – again, metaphorically speaking. And it’s not just the ability to bounce back that’s critical. We do so with a smile on our face and new resolve that we have actually taken a step toward success with our setback. Does that sound contradictory? It’s this kind of thinking – that we’re actually moving forward when it seems that we’re failing – that is the real definition of resilience. The existential threat melts away when we are always tougher than the problems we encounter.

The next existential threat is that of a lack of vision. Entrepreneurs absolutely must be able to see into the future. The ability to be a visionary also leads us to think more strategically and work on our business more than in our business. An entrepreneur who is a good operator but lacks vision will eventually “die.” It may be a slow death, but death nonetheless. Why? Because without a vision – especially one that inspires our team – we are simply stirring the pot. Over time, things begin to unravel. Key people leave because the future is unclear. Important customers leave because a competitor (with vision) has offered a more innovative product or service. Rather than create a clear vision, the operator-entrepreneur takes tactical actions to try and solve the problem. This may include belt-tightening measures or price increases, neither of which addresses the underlying issue. R.I.P.

Poor communications skills are another existential threat to entrepreneurs. This encompasses many elements. The entrepreneur who can’t persuade through artful communications won’t be able to sell his or her ideas to customers, team members or anyone else. The entrepreneur who is unable to communicate effectively will have difficulty building important relationships. When communications are non-existent or garbled at best, misunderstandings will occur and feelings are hurt. I have found that a very large percentage of challenges that we encounter are the result of inadequate communications. Entrepreneurial leaders must communicate clearly, concisely and constantly to eliminate this existential threat.

There’s one more existential threat that’s a biggie. Entrepreneurs who operate without integrity will eventually die. Our stock in trade is our integrity. It matters not how positive and optimistic we are, how strong our ability to bounce back, how grand our vision might be, and how well we communicate, if we lack integrity we’re dead as a doornail. Customers want to do business with entrepreneurs who are honest and forthright. Team members want to work for entrepreneurs who always do the right thing. Of course there are examples abound of CEOs and companies that seem to have “gotten away” with underhanded behavior. It may take a month, a year or even longer, but eventually the jig is up. Maybe it’s karma or there’s some other explanation, but the entrepreneurs who don’t play it straight will lose in the end.

There are many existential threats to entrepreneurship. A negative mindset, low resilience, a lack of vision, poor communications skills and a deficiency in the integrity department, top the list.

You can also listen to a weekly audio podcast of my blog. What you hear will be different than what you read in this blog. Subscribe on iTunes or wherever you get your podcasts. You can also click on this link – Click here to listen to Audio Episode 112 – Asshole Self-Test.

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.