7 Strategies That Helped Me Get A Lower Federal Prison Sentence

When we talk about human values, we consider things like equality, security, and tradition. Arguably, the most precious value is freedom which is usually taken for granted unless you don’t have it. If you are facing a prison sentence, you have to create a mitigation strategy to enable your best chance for freedom.

As many of our readers know, I found myself in a predicament back in January of 2005 which ultimately led to a federal prison sentence. I am going to give you 7 strategies that helped me to get a lower federal prison sentence. These and many other ways to help create sentencing mitigation strategies can be found at: www.whitecollaradvice.com. You can also see the full video of me discussing it at: https://www.youtube.com/watch?v=aKbJwmAJYpg&t=48s.

I learned early on that you can handle any challenging situation in one of three ways. You can leave it, accept it, or change it. Well, I knew I couldn’t walk away from it and I certainly didn’t want to accept the prison terms that I was looking at. So I decided to be proactive and see how I could help my outcome. Maya Angelou once said, “You may not control all the events that happen to you, but you can decide not to be reduced by them.”

As I mentioned earlier, you have to have a mitigation strategy. The earlier in the process you develop one, the better. After a strategy is developed, it must be translated into a comprehensive execution plan by weighing the pros and cons. It should then be focused on what actions to take, who will do it, when it must be done, what results are to be achieved, and how progress is measured. Every decision made comes with a consequence and you need to understand and vet each scenario. Understand the concepts I’m suggesting, practice good judgement, and take immediate incremental daily action. In the book I wrote, Lessons from Prison, I stress that the most important lesson to be learned is that slow and steady wins the race. This good old tortoise and hare fable applies when preparing for sentencing. You have to continuously be active in this long arduous process. Each strategy listed below will point out the main pros and cons so you can make informed decisions and execute them with aggressive action.

Get A Lower Federal Prison Sentence – PURPOSEFUL PRODUCTIVITY

The first strategy to consider is to force yourself to continue to work and find purpose despite your circumstances. I lost my job in January 2005 as a stock broker for UBS after making decisions that got me fired and ultimately sent me to federal prison. Early on I realized that I had to work, both to pay the lawyers and to continue to pay my bills. My case went on for three years and during that time I continued to work albeit not in my field. I certainly had my fair share of going to In-N-Out Burger, putting on weight, playing online chess, and the self-loathing nights as well described in my book. However, I chose to be very proactive knowing that white-collar crime investigations can take a long time to play out. So besides the money that you’ll need and the idea of feeling productive, working provides a wonderful opportunity to begin creating a new record as a law-abiding citizen. How you’re using your time during this lengthy process, can be a huge pro by showing the government, probation officer, prosecutor, and judge that you were able to make decisions that allowed further distinction from who you were in the past.

So what is the con of this strategy? Some people looking to work before prison may have to find a job that is beneath their skill set. As stated, I was a stockbroker by trade but was fortunate to be hired by a friend to help sell real estate. It is times like this when you have to lean on your friends, family, and network to support you. It will be humbling, in some cases, downright embarrassing, but you do whatever you have to help support a family. The idea of having employment could go a long way towards your mitigation strategy.

Get A Lower Federal Prison Sentence – COMMUNICATE COOPERATIVELY

The second strategy to consider is to work openly with the government. Once investigators show up to your home or place of work, make no mistake, they will be fully prepared to question you as they build their case. Unfortunately, initially I wasn’t ready to speak openly about my conduct and I lied during my interview. Looking back now, I feel like I missed out on a crucial step towards my mitigation strategy. In time, I was given a second chance at veracity after my co-defendant got indicted on a different charge.

Due to the fact that I lied to the government, I didn’t get the coveted 5k1. You can obtain a shorter federal prison sentence with a 5k1 and it requires active and ongoing cooperation against other defendants. I forfeited that right due to lying. I did, however, spend 100 hours with the Securities and Exchange Commission in advance of my sentencing to help them understand the corporate culture at UBS. It ended up mitigating my sentence as I helped them understand why I did what I did. This is why if you are ready to proffer, you should be open and honest about your role. It can help to minimize your losses. I was initially being held to damages of around nine million dollars. After speaking with the Securities and Exchange Commission, and having them being able to vet and verify my role, they found that UBS was complicit in this conduct and so they wrote a check for the damages. The pro of this strategy is that it brought down the total loss amount against me which in turn reduced my sentencing guidelines. In time, all the victims were paid back and I was then only held to half a million dollars in restitution.

What is the con of this strategy to get a lower federal prison sentence?

Well you have to be prepared to spend many hours with the government under the guidance of expensive lawyers. In my case it was about 100 hours at $500 an hour, you can do the math. One of the biggest mistakes I made was when I signed my plea and attorney retainer agreement, I didn’t realize it only covered my criminal investigation. Everything beyond that was additional. I didn’t read the plea agreement properly, being that this was my first time, and I was ready to sign anything to keep from going to prison. You have to humble yourself, be active throughout the whole process, and not just take the lawyer’s words for it.

Community Service to Get A Lower Prison Sentence:

A strategy that can be a huge pro is concentrating on doing community service well in advance of sentencing. Some may interpret this as just being opportunistic for the judges and prosecutors to consider mercy. They are very smart and know you are doing this because you want a certain outcome. However, the key is that the service is documented, preferably, over a lengthy period of time. Rather than go to the soup kitchen once a month and post it on Facebook as if you’re some hero, I’m not saying that’s not noble, it makes more sense to have community service work that is very specific and measurable to where you can demonstrate how the work helped people.

Never forget, you are trying to show your willingness to continue to help people despite your circumstances and get letters that then become a metric to show how you are trying to make amends. I have great templates at www.characterletters.com where you can enroll in free character reference courses. There you will see a letter from the community service organization I volunteered with and the amount of time I authentically spent actually doing. This was certainly a mitigating factor that helped me when it came time to the sentencing.

How can there be a con in volunteering? You actually have to do the work. You have to invest the time and create sweat equity. You must undergo the process that demonstrates how you’re helping people and do so despite the fact that you are already undergoing mental and financial stress. Pushing through this struggle will not only make you feel productive and give you purpose, but will also go a long way in the journey for mitigation where the endgame is a favorable sentencing. It is a win-win knowing you are helping people and yourself for the right reasons. Just make sure it can be documented and measured.


A fourth strategy you should really work on is to plan on having a solid probation interview. Developing and properly presenting your redemption story can show a cynical bureaucrat, whose job is usually to parrot the government, what your life is really about. In what could possibly be a short interview, they should understand your background, life plans for the future, and how you plan redemption once you are out. All this has to make its way into the report. The probation officer may come in with a biased view and have preconceived judgments. They already have your stats and reason for conviction so you have already been portrayed negatively. They may think you have a privileged upbringing, and it is your job to have them understand that nothing was handed to you. They need to understand that you worked hard despite where you live and what silver spoons you were assumed to have gotten. In my interview, I got a smirky response once my probation office found out I grew up in Encino, California. It took me to tell my story of how hard my parents worked as small business owners and sought further education to create better opportunities for their children. I had to make it a point to state that nothing was handed to us. It gave the officer a better understanding of how we ended up in this very wealthy neighborhood, kind of by luck, and my parents worked hard to maintain their lifestyle and provide. I feel like my probation officer got a sense of the real shame that I felt but most importantly, understood the plans I laid out for the rest of my life ethically. Remember, your past mistakes are meant to guide you, not define you.

The con to the probation interview is that it may require you to say some things you may not feel. For example you may not really feel remorse or ashamed for your conduct at the time of your interview, or that you were railroaded and forced into signing a plea agreement. You need to look at this experience like a business deal. Some business deals suck and you just need to complete them. In order to do this, it may require you to say and do some things you may not agree with at the moment but are good for the greater cause. You will be forced to identify your value system and if you are like me, the highest value should be placed on freedom and family which may require you to convey a level of remorse and shame in that interview. Understanding this will create the most favorable situation for your sentencing mitigation and could go a long way on where you may possibly serve your time as well.


You have to strategize and be invested in the whole process from the beginning when dealing with your counsel. If not, you will flush money down the toilet. Do not let lawyers give you boilerplate responses and dismiss your input. The initial law firm I retained was told that UBS, my former company, was complicit but they disagreed. Despite that, I still relied on their advice due to not having the wherewithal to know differently. Many months later, they called to tell me they represented UBS in a similar matter and that they now have a conflict of interest and can no longer represent me. Despite the fact that they knew UBS was involved when I first hired them, they stated that at that time they didn’t believe that was the case. They stated that it was not only until after they interacted with the government did they realize the conflict of interest. It took years to get my retainer back, but I did. The next law firm that I dealt with I used a more educated, informed, and due diligent approach. I was not going to get railroaded and exploited again. I held my lawyer accountable as best I possibly could by scheduling regular meetings and calls. I demand weekly and bi-weekly status updates. I expected documentation and a sentencing memorandum that wasn’t boilerplate. With my lawyer’s help, I was able to create a fantastic narrative and turn it into a beautiful story that really got past the templated stuff judges see. I stayed involved and engaged in every step of the way and it helped me get a shorter sentence.

With every pro, of course, there is a con. Sometimes, it’s hard to be direct with lawyers.They may not want to be constantly scrutinized and held accountable for every step in the process. Some attorneys may not value your feedback and it can be an uncomfortable relationship. In order to ensure that you are creating the optimum mitigation strategy, you have to take on responsibility and realize that this is your life no one should be more invested in it than you.


All the other strategies involve action by you on what you can do. The sixth strategy is specifically meant to be a result of an action on who you are as seen by someone else. You have to procure excellent character reference letters to advocate for your mitigation. Again, if you are not sure what I mean, you can see sample templates at www.characterletters.com. A big part of your letter strategy should be understanding what your specific judge preferences are. In my case, under counsel advice, I excluded immediate family letters and focused on the mitigation strategy of creating a new record as a law abiding citizen that spoke to my character and that I was making better decisions. It is important you compile character reference letters that are not templated but authentic. Nobody cares whether they are from a senator or a celebrity, just make sure you pick the ones that stay true to your character.

The con is you have to be proactive. You actually have to reach out to your network and speak openly about your conduct and what it is that you’re going through. You can’t sit back and take the position that you don’t want to bother people and bring them into your business. You have to pick up the phone and say you made some really bad decisions and rather than running from it, you would be grateful if they could spend a few minutes together with you to learn what you are doing differently to make amends. Explain to them how you are helping those that have been hurt through your actions and that you are humbly asking for their help. This requires you to invest the time to be proactive, reach out, and understand how to properly tell your story.

Get a lower prison sentence by making a restitution payment:

This could be a very sensitive and delicate topic. It is certainly unique to each individual. A lot will be asked of you financially when you are dealing with your situation. Between lawyers, family obligations, bills, restitutions, and fines, your money has to be strategically spent. Lawyers will say their only job is to keep you out of prison, as they should. Some may compel and convince you to part with every last penny. If you buy-in, you could go totally broke.

Unfortunately, to add insult to injury, you could still find yourself getting the same prison sentence. It’s important to have a mitigation strategy and understand the guideline ranges. We had a client that got 37 months, but was home in 10 months. Another one of our clients got sentenced to 33 months, but was home in 10 months. We analyze all these cases and study their outcomes so that we can apply it to future cases and recommend the best practices for a favorable outcome. Paying back restitution is definitely a strategy to consider, if you are able to make it before sentencing. In federal prison sentencing, judges will not treat you differently because you paid the money back. They know not everyone has that ability. That said, you want to show steps of making a wrong right by paying towards it. Also, paying a significant enough amount will go a long way with the judge by showing you are trying to make amends despite your circumstances.

The con is you actually have to come up with the money. If you do deplete a lot of your finances prior to going into prison, it could really impact your lifestyle and comfort while you are in there. It could also affect your ability to bounce back when you come home. The clients mentioned above got home earlier than anticipated. So in some instances, it is worth considering not paying initially so that you have financial stability when you get out. Looking back now, I wish I had the hundred thousand dollars I initially paid prior to my incarceration. I may have done an extra few months in prison, but I would have been better positioned to get back on my feet once I was out. You’ve got to use your own judgment and determine what makes the most sense for you. Paying your restitution should be a part of your mitigation strategy to get home earlier as I know my early payment certainly shortened my sentence by a few months.

So here they are again, the seven strategies that helped mitigate me get a lower prison sentence:

Purposeful Productivity
Communicate Cooperatively
Serve Others
Intentionally Interview
Absolute Attorney Accountability
Character Speaks Volumes
It’s Payback Time

I hope that you can use all of them, but even if one of them helps, you will improve your chances for a better outcome. There will always be lawyers who say the guidelines are the guidelines and there’s nothing you can do. Remember, you are your best advocate. Even if you follow every strategy I’ve presented here, you could still get the recommended guideline sentence. Look at the upside though, you’ve been working, you’re developing your network by procuring character reference letters, you’re holding lawyers accountable, and you’re doing community service. These beneficial acts can impact your early release from probation and supervised release. The important thing is to play an active role because at the end of the day no one will look out for you but yourself. Only you can choose to change your conditions. When you go within and do the internal work, you can possibly alter your outcome and tilt it in your favor. For more information about us and one-on-one consulting, please schedule a call.