The Lost Decade | From Prison to FI | Wealth Well Done

111 | The Lost Decade | From Prison to FI | Wealth Well Done

Billy B., a writer, entrepreneur, and blogger at Wealth Well Done shares his story of finding freedom in prison, starting over in his 30s and pursuing financial independence despite the setbacks.

  • Billy was given a 10-year prison sentence at 21, just before he was supposed to graduate from college.
  • Life was electric when Billy was using drugs and attending rave concerts – he was living the life he wanted to live – but bad things can happen really quick when you take those risks.
  • The idea that gave Billy hope is that no matter what struggles someone is in, it doesn’t have to be that way forever.
  • How did Billy keep developing, even as he was surrounded by walls?
  • Discipline is hard, but in the midst of it, it can start to give you visions of who you want to be.
  • “The gap between who I am today and the person I want to be in my future is practicing the skills that could get me there.”
  • How did faith frame Billy’s mindset in prison?
  • Billy’s goals when he got out of prison:
    • Finish his college degree
    • Land a $9-$10 an hour job
  • Just because you reach your goals doesn’t mean you have to stay there.
  • Billy is an independent sales representative, which means he owns his own business and has the freedom to sell almost any products he wants.
  • How did Billy train his mind to spot opportunities?
  • The process of reconciliation began the day after Billy got arrested.
  • Success isn’t acting successful – it’s actually living it out.
  • Through a work-release program, Billy was able to pay off $15k in fines and left prison with $6-10k in a bank account.
  • How did Billy accidentally save $150k and what did he do with it?
  • From prison, Billy wasn’t dreaming of cars and clothes, he was dreaming of freedom.
  • “Do the time. Don’t let the time do you.”
  • We only control how we respond to the world.
  • Biggest financial mistake: Thinking that $10 could buy a more interesting life story or a better life experience.

Read more about Billy's story here


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8 thoughts on “111 | The Lost Decade | From Prison to FI | Wealth Well Done”

  1. This was an excellent interview. I’m so happy that you used an unfortunate event to motivate you to come out on the other side. You’ve done so well and your encouragement to others is helpful. Keep pursuing your passion and keep being faithful.

  2. Let me start by saying that I absolutely love ChooseFI podcast! However, I just couldn’t finish this particular episode. It honestly made me sick to my stomach to listen to Billy. I’m all for someone turning their lives around, but I have no sympathy for a drug dealer who was found criminally liable for another person’s death. Can you imagine how his victim’s family must feel knowing that this guy is out there becoming a successful “writer, entrepreneur and blogger”? I would honestly hate for them to stumble across this episode. Lost decade? How about a lost life?

    Brad and Jonathan, again, I love you guys. But when your show notes say Billy “was given a 10 year sentence”, it’s honestly offensive. Billy earned his 10 year sentence with his actions. He’s not the victim here – his friend who died is. This is no different than a DUI resulting in vehicular homicide/manslaughter. There are so many wonderful and inspiring stories out there about people who are down on their luck, come from impoverished communities, and yet manage to pull themselves out of economic insecurity and dig themselves out of whatever hole they are in to become financially independent. This wasn’t one of them.

    And for the record, Billy didn’t use an “unfortunate” event to motivate himself. The dude sold drugs, a lot of them, to his friends and others, in a college town, and to the point where one of his friends overdosed and died. We don’t know all the facts of the case, but a 10-year sentence should give you some indication that this wasn’t a small drug infraction on Billy’s part.

    If it was one of your kids that Billy sold drugs too, and your kid overdosed and died, would you still have him on your show? C’mon guys, I know you can do better than this. I love you two, and your podcast is super inspiring, but this episode was just so far off the mark.

  3. Hi Elizabeth:

    You have every right to feel this way. When I think back 16 years ago when this nightmare happened, I get sick to my stomach for all of the same reasons you described above. But I am also extremely grateful that we as human beings don’t have to be stuck in our pasts forever. If we did, I don’t know if I would want to live my life anymore.

    In the 6 years since I’ve gotten out of prison, 99% of the people I have met in person (tens of thousands of people) have looked me in the eye after meeting me and said, “I want to help you… How can we make this world a better place together?”
    In that time, I have appeared on dozens of blogs and podcasts, and received hundreds of comments. Your comment is the first negative comment I can remember receiving. In fact, last year was featured on nationally syndicated media channels like MSN and CNBC, and my story got hundreds of likes on their social media pages and not one single negative comment. That fact even surprised me as I was sure at least one person out there would hate former drug-users and just have a problem with me no matter what I did or how I changed my life. But I am grateful to learn that the vast majority of American’s believe in giving good people a second chance. For the 1% of people who refuse to give me a chance, I respect their opinion, but I’m not living my life for them. Fortunately for us American’s, America is a totally free county, and we all get to choose the people we want in our lives.

    When I was in my prison cell for all those years, I didn’t dream about meeting people who would hate me, try to discredit me, or wish me harm no matter what I did because of my past mistakes.

    Instead, I dreamed about the hurting and lost people I could reach and help. I dreamed about the young person like I once was. I thought just maybe they could hear my story and then second-guess making the same decisions I made. News flash to you: There’s probably some young kid (or kids) out there who listened to this episode who was doing the exact same stuff I was doing. I know because I was one of those kids at one point, and I had a lot of smart friends doing the exact same stuff as me. Young people make mistakes and don’t think clearly all the time. Maybe they heard me and totally re-evaluated their life. I also dreamed about reaching the people who had made mistakes, and were having a hard time forgiving themselves because of those mistakes. I dreamed that maybe they could hear that I was able to forgive myself for making terrible decisions, and maybe they could believe that they could forgive themselves too. Those are the people I am here for, so if you don’t like me, that’s fine. I’m not here to convince you of anything.

    You made alot of assumptions about my criminal case 16 years ago that were totally false and inaccurate. I could defend myself but I don’t have to. Nobody cares about the tiny details. I did what I said I did and that was all. It was 16 years ago, in a small town, and I was one of the first opiate cases in that county before opiates became the national health crisis it is today. In the end, I pled guilty and served my time. After doing my time, the United States of America said that I could live freely again in this country with just as many rights and freedoms as any other person alive in this country and that’s what I’m proud to do. The past is over for me, and I don’t have to relive that night, or the shame I felt, or defend myself to anyone ever again.

    I am not perfect, and my goal isn’t to reach perfect people. I am living my life for the people who want to believe that they can forgive themselves no matter what unfortunate events happened in their pasts. I want to inspire people that they can live a better life no matter what nightmare they had to live through. If you do not want to be in the 99% group of people who want to be my friend, and help make the world a better place with me, you are just as free as me to find new people who fit your life and outlook better. I wish you peace and nothing but the best.

    • Hi Billy,

      Thanks so much for your response. I think it is incredible what you have accomplished since your release and I hope that you find continued personal success and fulfillment. My complaint stems from what came across (to me at least) as a whitewashing of the crime and then holding you up as a role model. We weren’t given specific details, and rightly or wrongly, the interview seemed to gloss over what I imagine might be the darkest parts of your life, painting you as a victim of circumstances when you kind of made your own bed and then had to lie in it. It may have inadvertently occurred during editing and post-production, but it just felt like at no point did anyone address (or ask you about) your inner struggles and turmoil or feelings of guilt, so we (or perhaps just me) as an audience didn’t see that side of you.

      You have clearly been able to move beyond those events and forgive yourself, which is commendable. But it was difficult for me to focus on your accomplishments when I didn’t get to hear how you came to terms with making the mistakes you did, forgiving yourself, and then finding the inner strength to believe in yourself again and to believe that you could move forward with your life. That, to me, would have been inspiring and compelling to listen to.

      There is a difference between hating someone and being put off by the apparent downplaying of that person’s crime to focus solely on his or her successes. I don’t hate you, and perhaps I was too harsh and speaking out of anger when I said I didn’t have any sympathy for a drug dealer. I just kind of wish the conversation didn’t imply that you were a victim of your circumstances – you had an active role in what happened to you and I didn’t hear anyone acknowledge that. That was the missing piece for me.

      What I also find inspirational is that rather than perpetuating a cycle of drugs and crime and becoming another statistic for recidivism, you made the affirmative decision that that was not who you were anymore, not who you wanted to be. And you had the willpower and fortitude to right the ship after making the mistakes you did. Relating it back to personal finance, when we make financial mistakes (even really big ones) and it sets us back years, how can we come to terms with those mistakes, learn from them, and then what can we do to move forward with our financial lives afterwards?

      Again, for me at least, the elements of personal responsibility and accountability were missing from the interview, and that was something that I couldn’t get past. It was then exacerbated by the comment from R Wineck above that “you used an unfortunate event to motivate you”. Unfortunate events happen to someone, whereas a mistake is made by someone. You’ve acknowledged your mistake, paid your dues, and are working hard towards your future success and fulfillment – I wish you the best on your journey.

  4. Hi Elizabeth:
    Your response really meant a lot to me. I now see clearly see that you’re not a person wishing me any bad luck or harm. We were both just talking about a very hard and emotional subject, and sometimes it’s hard to put strong feelings accurately into words. I’m so sorry if I came off the wrong way too.

    In fairness to Brad and Jonathon, trying to encapsulate my entire life story in a 45 minute interview is an impossible task. There’s 20 years of stories to fit into 45 minutes. Everyone listening is going to have different questions, and will want to go deeper on different parts. It’s super easy to skip over vital moments as we were forced to squeeze 3 years into 3 minutes. I mean, we could have devoted an entire episode into the long process of how I came to terms with what happened, how I accepted the responsibility of it, and then how I learned to forgive myself. Honestly, I am still coming to terms with it all and getting through it. ChooseFI is about the mindset it takes to overcome challenges; how to find a new mission to live for; and how to structure your finances so that you can achieve your deepest dreams. So that’s why we went the direction we did in the episode. We did get a lot of positive feedback on social media, so I’m pleased to know it did make a positive impact in several people’s lives who told us directly.

    You brought up an important point in your first comment, about my friend who is no longer here with us. That’s the saddest part of the story. Since he’s not here to tell his side of the story, I try not to talk about him publicly because it’s not fair to him. I try to only tell the story from my perspective, and what I experienced. What happened to us was a tragedy all around. No one won. Everyone lost. Every day I wish I could have changed that night. I wish I could have been a smarter, better person, but I made a mistake and a horrible outcome occurred. I can’t change the past. I can only try to change the future. That’s what I am trying to do now.

    I’m glad we had a chance to talk about this in the comments and clear our feelings up. So that if anyone reads this after listening to the episode they can see how I really feel. I still feel sadness and shame that I made those decisions. I wish I could have handled my young adult years so much differently. I failed, but I don’t have to stay a failure forever. The one thing I can always do when I make a mistake is pick myself back up, accept responsibility, and remind myself, “I made bad decisions, but I am not a bad person. I can still make a positive difference with my life.” Thank you for understanding.

  5. Hi Choose FI!

    A friend recently recommended your podcast to me and I have enjoyed it for the past two months. Today I listened to this episode. While it was inspiring to hear of someone turning their life around after ten years of prison I had a hard time finishing it. I’m not entirely clear who the audience is for this podcast but I feel that this episode completely missed an opportunity to discuss that the issue of race may have given Billy a leg up in pulling his life back together. (If I missed the mention please let me know!!!) Don’t get me wrong, Billy did overcome many obstacles common to anyone who has spent any amount of time in prison no matter who you are. The systems we have for reintegration back into society, and the laws that limit the rights of former prisoners when they have served their time affect everyone who has been incarcerated. However, Billy had a certain degree of privilege (in many senses of the word) which no doubt helped him along his way and I do think that this warranted at least a mention. I am surprised that Billy, having likely seen this firsthand, did not make a mention of this.

    FI- I dare you to find a Person of Color who had a similar experience and to show his/her journey to FI. I think this would highlight the differences in these two paths, and different obstacles overcome to achieve FI. I am by no means saying that it is impossible, however there are many more obstacles facing men of color that I think take more than a ‘mindset’ to overcome.



  6. Hi Katie:

    This is how I answer the “privilege” or “race” aspect of how my experience may compare to others who may have a different cultural background than me.

    First off, you have to understand that I grew up in the northern progressive state of Minnesota in the 1990’s where most kids like me weren’t taught racism. We were taught that everyone is the same. African-American, Asian, and Native American kids were just as cool as the white kids in the schools I grew up in, so I wasn’t even really aware that racism existed until I became an adult and realized the world can be a cruel and unfair place at times. I still choose to view life through this in-discriminatory lens I learned as a child.

    Second, if you google, “Successful Ex-cons in America,” you’ll find a lot of articles like this one ( which show that success in America comes in all shapes, sizes, colors, and cultural backgrounds. Some of ex-con minorities on this list have attained success that make my story look like peanuts. This makes me think that success is mostly dependent on traits such as perseverance, discipline, optimism, ingenuity, talent, attitude, cleanliness, communication skills, and the overall ability to be a likeable person and team player. In my humble opinion, skin color is much further down on the list of ingredients to be a successful human being than the much more important qualities listed in the previous sentence.

    Third, please understand that I have been self-employed since I was released from prison, so I can’t really speak about what it’s like being a minority felon trying to get a job in America as I don’t have any experience doing that.

    But I can tell you that when you’re choosing a self-employment route like I did, the market really doesn’t care about what race you are. The market cares much more about your pricing, your service, and the quality of your products than your cultural background. If you have a great product, great service, at a great price, I’m not even sure if consumers pay attention to the color of your skin. I know this because I buy products on Amazon and Ebay all the time from vendors whose skin color is anonymous to me, and I don’t care what cultural background they’re from. If the reviews of the product and service are great, and the price for their product is a good value, I happily buy from them without a second thought on what race they’re from, and I’m pretty sure most people buy this way. If someone doesn’t buy this way, then there’s something wrong with them as a human being.

    Lastly, you can pick apart my life and story all you want, and judge me if that’s your prerogative. It’s true that I was able to stay with family when I was released from prison, but that’s what I saw most guys do when they got out regardless of their race. If they didn’t have family, then there were government-sponsored half-way homes available to help recently released ex-cons get back on their feet. At first I wasn’t sure if my family’s home would have been approved for me to be released to, so I had made a backup plan to move into a half-way house for 6 months or a year, and I’m sure I would have had similar success starting my freedom out there. It may have taken me a bit longer, but I still would have made it. Because ultimately it doesn’t matter where you live, you still have to choose to be drug free, ambitious enough to learn and get a job, and fearless enough to at least try to be successful. I knew I was going to do all of these things no matter where I started out.

    Finally, I am aware that racism/stereotyping does exist and this saddens me, but I personally choose to believe that these are isolated events and not the everywhere norm. I still keep in touch with a few African American friends I was incarcerated with, and they’re all doing well because they chose to have the right attitude, they chose to be ambitious, and they chose to learn from their mistakes and not repeat the same mistakes just like I did. Ultimately after being in prison, my friends and I defined success as just being a good husband to our wives, father to our kids, and an overall good human being to the community. That was our only goal. The financial success I have attained has just been a cherry on top for me because I’m naturally good at it and it’s something I enjoy achieving.

    In the end, the only people I’ve seen fail and go back to prison where the men who chose to abuse drugs and alcohol again, or embrace a bad and impatient attitude and gave up to soon. These qualities that sent these men back to prison unfortunately come in all races and cultures and have nothing to do with skin color.

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