Would you do Business with a Felon?

Providing an overview of how the criminal justice system works, this article brings plea bargaining, conviction and sentencing into focus, while highlighting the negative impact of discrimination on convicted individuals and society at large.

A few years ago, I met a potential client who ran a private equity firm. In full transparency, I shared with him a link to my presentation at the California Women’s Conference. In this presentation, I talked about my prison experience and responding to violence with love. 

I wanted my prospective new client to know that I had been in prison and to understand what the experience had meant for me, my growth as a man, and as a human being. In the email title I wrote, “How I found freedom through 19 months in federal prison.” 

His response felt like a punch to the gut, ”At face value, I don’t have an interest in working with somebody who at any point in their career has broken federal law.”

My previous company, Wise Funding, coached and assisted small business owners who required funding to grow their businesses. Wise Funding was very successful, and we had a lot of satisfied customers. I had a great company and built the life I always dreamed about. 

Unfortunately, I had taken on a less-than-reputable business partner and the consequences came crashing down on me. 

I hired a company to help me get a business loan. As I was going through the loan process, I realized that they were doing some shady things to acquire the loan and I had a feeling what they were doing was illegal. I didn’t, however, think it was a problem for me to obtain a loan that I was going to use for legal purposes through this company. This was my mistake. When the authorities caught up to them, I was charged with conspiracy to commit bank fraud and paid a steep price for my misjudgment. At the time, I didn’t have the massive resources I needed to fight a federal indictment, so I took a plea deal. 

While I was in prison, I learned Spanish, worked out, and meditated. I treated others; guards and inmates alike with respect and dignity. I made friends with people from all walks of life and did not hesitate to help inmates in need. In my talk at the California Women’s Conference, I discussed my prison experience, and how I responded to violence with love. The potential client who had rejected me didn’t take the time to understand any of the above. He immediately judged me because I had been to prison. 

His response surprised me, and the rejection hurt. Feeling misunderstood hurt even more. This was not the first (or the last) time that I faced rejection due to my past circumstances. I’ve experienced different levels of judgment around this from a wide variety of different sources.

The judgment behind his response and the rejection I felt inspired this article. I want to share a broader perspective of our justice system, those who have been labeled as a felon and my life learnings. 

How the Justice System Works

Do you think that our government, or any government for that matter, is 100% effective in how it implements justice? I think it is easy to see how dysfunctional the government and its systems can be, particularly in today’s political climate. 

Injustices within the system

With 2.3 Million people behind bars, the United States is the most incarcerated country on the planet. Many of those incarcerated individuals broke the law and should be in prison, however, some of them broke the law due to desperation and others as a result of trauma. The truth is, a lot of people receive harsh sentences irrespective of mitigating circumstances. 

Then there are others who did not violate the law. Too many incarcerated individuals are victims of circumstance or targets of the government who were either cornered into a guilty plea or found guilty at trial.  

There are even those who unintentionally broke the law. Harvard Professor, Harvey A. Silverglate discusses overcriminalization in his book, Three Felonies a Day: How the Feds Target the Innocent in which he says, “it is only a slight exaggeration to say that the average busy professional in this country wakes up in the morning, goes to work, comes home, takes care of personal and family obligations, and then goes to sleep, unaware that he or she likely committed several federal crimes that day.” 

The Washington Post outlined a case in Georgia from 1979, where human error carried serious consequences. The victim of a brutal rape case wrongly identified an innocent man in a lineup as the perpetrator. He was found guilty of the crime. Decades later DNA evidence not only proved the man was innocent, but investigators also discovered that the guilty individual had stood in the lineup with the innocent man.

Meanwhile, there are many people who commit crimes but because they have great legal defenses, money, and connections they are able to defeat the charges, if charges are brought against them at all. 

Only 2% of federal criminal defendants go to trial

An illuminating article written by Clark Neily, vice president for criminal justice at the Cato Institute (and adjunct professor at Antonin Scalia Law School at George Mason University), highlights how widespread the problem of coercing plea deals is and the crippling impact it has on the criminal justice system. 

He refers to data released by the PEW Research Institute in-which, “Only 2% of federal criminal defendants go to trial, and most who do are found guilty.”

Neily provides several examples of cases in which prosecutorial misconduct was revealed during the trial process. He raises an important point, “Defenders of the status quo claim that examples like these are unusual and that prosecutors rarely commit misconduct. But how can we possibly know that when only two percent of federal prosecutions go to trial?”

Why people take plea deals

“Though it was once believed that a confession in open court — a guilty plea — was proof-positive of a person’s guilt, we now know that simply isn’t true.”

Clark Neily, VP Cato Institute 

A prosecutor’s career trajectory is linked to his or her conviction rate. Those with high conviction rates tend to move up the political ladder faster. It doesn’t really matter how a prosecutor attains convictions. All types of strategies, from intimidation to threats, are used to obtain confessions and to cut plea deals. 

The fact that prosecutors, instead of pursuing the truth, pursue convictions out of self-interest, creates a perversion of justice. 

According to Jed Shugerman, Professor, and Author of The Rise of Prosecutor Politician, the emergence of the prosecutor’s office as a stepping stone for higher office has dramatic consequences in American criminal law and mass incarceration. He says, “The office of prosecutor has become a stepping stone to higher office in America. Thus, the office tends to attract a more political animal, a more ambitious type. Anecdotally, law students with political aspirations tend to gravitate towards prosecutors’ offices.”

Furthermore, “Prosecutors who see their professional goal as strategically maximizing convictions, or punishments, are more likely to use their charging and plea-bargaining discretion to secure guilty pleas and excessive sentences.” says Eric S. Fish, a Federal Public Defender in San Diego, California. 

Former Chief Judge for the U.S. District Court of Massachusetts, William Young, has taken a strong position on the matter saying, “Our entire criminal justice system has shifted far away from trials and juries and adjudication to a massive system of sentence bargaining that is heavily rigged against the accused citizen.”

When I was in prison, I heard story after story about how the government was unjustly holding defendants’ mothers, girlfriends, and loved ones in order to force inmates into a plea deal. 

“Though physical torture remains off-limits, American prosecutors are equipped with a fearsome array of tools they can use to extract confessions and discourage people from exercising their right to a jury trial. These tools include charge-stacking (charging more and more serious crimes than the conduct really merits), legislatively-ordered mandatory-minimum sentences, pretrial detention with unaffordable bail, threats to investigate, and indict friends or family members and the so-called trial penalty,” writes Neily in an NBC News piece.  

Unfortunately, most of the time prosecutors don’t even need to resort to strong-arm tactics. Defendants who cannot afford a lawyer are appointed a public defender. While some public defenders are excellent attorneys, others are not. What you end up with is a roll of the dice. 

According to the New England Innocence Project, “Defendants are guaranteed a right to counsel, but an ineffective defense attorney can lead to the wrongful conviction of a factually innocent person. Inadequate defense lawyering can include the overall failure to prepare for trial, to investigate the crime and the defendant’s alibi, and to challenge witnesses and experts.”

Having little faith in their state-appointed-attorneys, defendants take the deal they’re offered because they believe they will serve less prison time. 

Understanding the impact of Trial Penalty

Defendants who go to trial and lose serve much longer sentences. This is referred to as the “trial penalty” which according to the National Association of Criminal Defense Lawyers, is the “substantial difference between the sentence offered prior to trial versus the sentence a defendant receives after a trial.

In Silverglate’s words, “We are in danger of becoming a society in which prosecutors alone become judges, juries and executioners because the threat of high sentences makes it too costly for even innocent people to resist the prosecutorial pressure. That is why nearly all criminal defendants today plead guilty to “reduced” charges rather than risk a trial with draconian sentences in the event of a conviction.” 

Convictions are often the end of the road, with less than 1% of appeals actually getting brought back to court. 

My experience with the US justice system is that it is far from just. The system is set up to force outcomes of guilty pleas, even if the person may not be guilty of the crime charged. A plea deal is often seen as the path of least resistance. People don’t want to take the chance of losing at trial due to a lack of resources because it will result in a longer sentence. 

While the system itself is grounded in self-serving and self-perpetuating principles that many times undermine the very purpose of its existence, we find that government imperatives also impact how cases are handled. 

Government imperatives 

The government doesn’t play fair; it has its own motivations, intentions, and objectives. Many times those motivations lead to a path that is not in alignment with the highest good of those it intends to serve. 

The war on drugs, for example, has had far-reaching consequences for minorities. “Incarceration has increased by roughly 500 percent,” writes Julia Felsenthal, in a 2018 article on criminal justice reform. Felsenthal links this increase in incarceration to federal drug prosecution policies over a forty-year period. 

According to Law Professor Wadie E. Said, “Wielding the power of federal criminal prosecution on a global scale is a natural result of characterizing the anti-drug and anti-terror campaigns as ‘wars,’ yet with such power comes essentially limitless police and prosecutorial discretion.”

If the powers that be want to show that they are intolerant of the drug trade, there will be a high number of drug-related arrests and convictions. If they want to show that they are hardliners rooting out corruption, there will be a rise in fraud and other corruption-related convictions and so on and so forth.  

Why do people want to judge and push away someone who has been convicted of a crime? 

People trust the system 

There are several reasons that I can think of, the most obvious being that people tend to have faith in the justice system. Those with limited exposure to felons or the justice system live in the bubble that the government knows what they are doing. Many people think that if the government found a person guilty, they must be guilty. It is easier to defer trust placed in authority than to use one’s own reasoning abilities and question it. 

“Human beings are naturally predisposed to trust—it’s in our genes and our childhood learning—and by and large it’s a survival mechanism that has served our species well… Recent evidence, moreover, shows that trust plays a critical role in the economic and social vitality of nations,” says Stanford Professor and Social Psychologist, Roderick M. Kramer.

In a 2018 paper titled, “My Trust in Government is Implicit, Automatic Trust in Government, and System Support.” Stephen Nicholson, Assistant Professor at the University of California, Merced proposes that, “Although large majorities of Americans express distrust in government… most of these same individuals also possess an implicit, gut-level trust in government. Using a common method to measure attitudes that people are either unwilling or unable to self-report, we found that most respondents implicitly trust the government.”

On the other hand, even if you were to ask a skeptic, “do you trust our government?” and they answered “no” to that question, and you then asked them, “would you do business with a felon?” they would still answer “no.” It’s ironic that even those who do not trust that the government knows what they’re doing will take a conviction at face value. 

When we rely on societal standards or government standards, it is because we have not learned to think for ourselves. Learning to question these things leads to a healthier way to navigate complex issues. 

Discrimination upon discrimination 

Once you have served time in prison, you are labeled a felon and there is a stigma attached to this term, which severely limits your opportunities. 

According to Simmons University, “Once ex-offenders are released, it is more difficult for them compared to the general populace to find gainful employment, secure a consistent source of housing, and generally function in society.” 

The alienation, rejection, and judgment of those who have been labeled as a felon or criminal is a form of discrimination. It is the same as judging or rejecting someone based on the color of their skin or sexual orientation. Assigning a group of negative qualities to someone based on a single known fact, be it the color of their skin, gender or the fact that they have a criminal record is stereotyping. 

Anyone who has been convicted of a crime will face discrimination long after their sentence has been served, and minorities, who are already subject to discrimination will have the added burden of being discriminated against because of their conviction. 

There are laws in place to protect citizens from discrimination, however, legal enforcement of those laws rests with the same body that declares someone a felon based on its own flawed processes. For this reason, it will take a long time for criminal justice reform to become a reality. It is encouraging, however, that some states are looking at changing the language around criminal offenses and people who have committed crimes

Where to from here?

Institutional Change

From corruption to discrimination to overpopulation, the criminal justice system as it currently stands is riddled with challenges. Criminal justice reform will need to be made a national priority. It is my hope that those who have the power to bring about institutional change will begin the work of shaping a new system, one that truly rehabilitates lives rather than destroys them. 


It is easier to hold on to incomplete perspectives and external labels when we have internal insecurities and fears. One of the biggest reasons we judge people with criminal convictions and steer clear of them is out of a place of fear and self-preservation. We fear what we don’t understand. We fear loss, and if we think that associating with the formerly incarcerated will somehow cause us loss, we will turn away.

Becoming aware of our own tendency to judge and push away what we don’t understand helps us to create the space for understanding and compassion to rise. 

Letting go of moral ego

There is a perception that making a moral mistake is unacceptable. This is based on a seat of righteousness, that so many try unsuccessfully to maintain. It also promotes cancel culture and leaves little room for inclusion, or for bringing those who have failed back into society. 

When we keep rejecting individuals based on their past mistakes, we continue to perpetuate judgment and discrimination. I personally believe that if we include the previously incarcerated, as opposed to selecting only those who have a seemingly perfect track record, we would have a more just, kind, and non-judgemental society. 

Whenever you have the opportunity to work with someone who has a criminal record, you have the potential to help create a more kind, inclusive, and embracing society. 

Love the one who has failed

I had already begun a spiritual journey before I went to prison, and one of the things I learned about judgment was that we judge things in others because there are parts of ourselves that we have not fully embraced, loved, or accepted. Often when we label someone or pass judgment on them, it is because we have not loved some aspect of ourselves. 

When I was in prison, I found myself surrounded by people I would not normally associate with. At first, it felt uncomfortable to be around so many different people, some of whom were violent offenders. After spending many hours loving myself, I began to energetically embrace everyone I came into contact with. 

When you love yourself and when you have been kind to yourself, it becomes easier to extend love, kindness, and compassion to others. Increasing your love quotient (LQ) changes the way you interact with others. It enables you to embrace others, even those whom society has judged or labeled. In doing so, you can be a part of bringing forward a more loving, peaceful and compassionate society. 

It is essential for us to forgive others and help them heal. In helping others, we not only help those that need the support, but we help ourselves and raise our LQ in the process.

By bringing awareness to your LQ, you are able to contribute more positively to society. An increased LQ leads to a higher level of social awareness or consciousness. This heart-centered approach leaves you better equipped to address social issues like discrimination and racism.  

Rehabilitation is a two-way street

According to the National Institute of Justice, “Within three years of release, 67.8 percent of ex-offenders are rearrested, and within five years, 76.6 percent are rearrested.” This is explained as being due to “Systemic legal and societal barriers.”

Having a purpose can be life-changing for a person who has been released from prison. If you know someone with a criminal record who is a good fit to work with and you choose to overlook their past mistakes, you can be a catalyst for positive change. 

Setting a good example for inclusion is an advertising agency called ConCreates who are fully staffed by individuals who have been or are currently incarcerated. According to this FastCompany article, “The agency operates on a crowdsourcing model, tapping into a network of 436 men and women currently behind bars, and 319 former prisoners on the outside, for skills depending on the work needed.”

Whether you hire someone who was previously incarcerated or partner with a vendor looking to start over, you become a part of their road to re-entry and rehabilitation, benefitting both society and the individual.

Final Thoughts 

Most people already have an idea that there are problems with the justice system. There is a general awareness of overcriminalization, overpopulation in prisons, judicial racism and corruption however, when meeting a formerly incarcerated person, there is a tendency to revert to a snap judgment. As a result, people often misjudge, stereotype, and discriminate against someone who has been in prison. 

My hope is that through this article, I have brought you a better understanding of the reality of this issue and helped you see how your judgments actually have a negative impact on society. 

When someone discriminates against me, I know it’s because of their own fears, misunderstanding, or limiting beliefs, but it still doesn’t feel good. I send them a blessing and I keep moving forward.

When you are able to look beyond the label, beyond somebody’s past, and see the situation for what it is, you can move past fear and discrimination and bring greater compassion and understanding into the world. 

Doing business with a felon might be the best and most rewarding deal you do this year. 

16 Responses

  1. Thank you for sharing this information. In 2017 I was accused of sexual assault. Over the next 2 years I faced high bail and legal costs. I am so grateful that my baileman and my lawyer took payments. During that entire time every decision I made was held up against the fact that I might be going to federal prison. Like you, I have spiritual practices practices. I could see that if I went to trial there was a good chance I good chance I would be going to prison or have to take a plea deal and still go to prison. Luckily, the case got thrown out. I’m still waiting over a year later to get my record sealed because I have an arrest for sexual assault and I’m concerned about how that will affect my housing opportunities if I need to move.

  2. So well written Chris! Your article should be promoted and shared on a large scale for such an eye opening piece of education. We all deserve to receive this knowledge, yet it unfortunately is all too often overlooked in our society. Thank you for creating and sharing.

  3. Chris, I’m so glad to know you. Thank you so much for helping educate us all of the bitter truths in our legal system. God willing, your extraordinary article will be read by many, and can help move hearts and minds to effective change and transformation. God bless you always.

  4. Very insightful and well written Chris! I more than understand about moral judgment by others. It is very difficult for people to separate the label of ‘criminal’ from the human being. We have seen numerous examples of this, especially where there was discrimination. So sorry this happened to you. At the same time you are a positive example of how a person can rebuild a life. You will probably always face some form of discrimination for narrow minded people but that is on one part of our society. There are plenty of others that look at you as a human and build trust based upon your character NOW. Good job, continue your good work. Jimm

  5. Congratulations on having the courage to share your journey, Chris. Many people are unaware of the failures within the justice system, and highlighting them as you have is very powerful and can hopefully lead to change. Blessings to you!

  6. I found your article very interesting and educational. I do not doubt there are people who do not deserve to be imprisoned and I know wealthy criminals can often use their power to get off or get a deal. There are lawyers that do not do their job and their client does not get a fair trial. Unfortunately the system will always be flawed because humans are fallible and motivated by wealth and power. I appreciate your desire to help people see that those who have served time deserve a second chance. I believe I would have some issues myself doing business with someone who served time unless I knew more of their story. I would hope I would be open to hear their story. However, there are those who are criminals who know how to pretend they have been reformed and then when they get out, they commit the same offense again. That is why I would want to know why they went to prison. Knowing you as I do I would do business with you. If it was a total stranger, I would have to find out if they could be trusted. If it was a violent crime I would be very careful.

  7. Sooo appreciated reading this post and gaining much needed insight. Meting out justice… oh what a concept. As Spiritualists we trust to believe that in Creation there are ultimately no iinjustices. Can Divinity get it wrong? Especially as we move toward a digital social s score world. Anyone who hasn’t seen the Black Mirror episode called “Nosedive” is in for a wake up call. Thanks for writing, Chris.

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