Guest Interview: Life and Money Lessons from Jail Part 2

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Last Monday, I talked to Billy B, a friend I met at FinCon who has one of the most inspiring stories I’ve ever heard. You can read his story in Part 1 here.

As promised in Part 2 our guest interview, we’ll find out:

  • How he managed to save $40K in 2 years on a $9/hour salary stacking boxes
  • How he managed to build his quarter million net worth in just 5 short years, and
  • What advice he has for people who are stuck in bad situations they don’t think they can get out of

Take it away Billy B!


Having $40K in your first 2 years of freedom is amazing, considering your $9/hour salary. How did you do that?

So I left a lot of little details out of the Budgets Are Sexy post, just because I assumed the reader didn’t want to get bogged down with details on how I saved my first $40K.

This is how I “accidently” saved my first $40K.

My last 1.5 years in prison, I was actually in a minimum prison camp on a work release program for inmates who no longer were a “threat” to society. So my last 18 months of prison, I actually got out of prison for 8 hours a day and worked at a real job making $9.25 an hour. I just couldn’t leave my job, and I had to return to prison every night. So I was released from prison with around $10,000 I had saved from that program.

I lived in my parent’s basement for the first 2 years so I really had few large expenses. My parents always believed in helping their kids have the tools to succeed, so the “unwritten rules” in the house were, I could live there rent-free as long as I was doing everything I could to save money and be successful on my own. I also qualified for a federal college grant to help low income adults like me so I had very few education expenses as I graduated college.

So my first year out, I graduated college and worked some side-hustles and got that $9 an hour job. But then once college was over, I now had the time to interview for better jobs, because I once saw an Ashton Kucher video of him saying that he never left a job, until he had a better job. So I used that advice as a guide on how to succeed. Get one job, then plan for a better job.

I really only worked that $9 an hour job for a few months, until I decided to start my own business selling branded apparel (hats, t-shirts, that kind of thing). I knew the $9 an hour job was never a “career” job that could get me ahead, so I quit that, and started my first business in my parents basement. I made like $1000 in my first 6 months in business going door to door doing business to business sales, and almost gave up because I knew I couldn’t live off of $1000. But then, all the work I put in started clicking, and I started selling more, and I made like $24,000 in my next six months. I think I made $40,000 in my next year, and $60,000 in my third year… or something close to that.

I met my wife starting my second year out, and she was also working and living at her parents house for cheap rent, so we had two incomes we could save with.   We shopped at Good Will, and had that attitude that “an egg McMuffin at McDonalds was a big purchase for us until we could move out of our parents house” and at the end of my second year, we decided we were financially stable enough to start our life on our own. We had a $40,000 down payment on a house. We planned a wedding in 3 weeks in my parents living room, and moved out January 17th, 2013 and have never looked back since.

Love that Ashton Kusher video! I think the take away from it is something that we can both relate to. When he says “I was not better than any job” and “opportunity looks a lot like hard work,” that really spoke to me because it’s exactly what you have to push through to get places in life.

And in your case, you went from making $9/hour to $1000 in 6 months, and then $24,000 in your next six month. And now you were pushing $60,000/year in your 3rd year. WOW. And you did this going door to door, even though the pay out was so low in the beginning. Which is exactly why so many people give up whenever they start businesses. You end up working for years (or in your case 6 months) without any rewards. It was like that with us too, with writing. In the beginning, we made negative money (because we actually spent money on writing classes, conferences, etc), but if hadn’t done that hard work for years with NO monetary rewards, we would’ve never learned to write and this blog wouldn’t even exist.

With all that hard work, starting your own business and along with your wife’s income, you ended up saving $40,000 toward down payment and that was 5 years ago. You’ve now managed to build up your assets to a quarter million in just 5 years. How?

A couple of things:

I like to say “We’re frugal, but we’re not cheap.”

Even with a quarter million in assets, we still believe “An egg McMuffin at McDonalds” is still a big purchase if we DON’T NEED IT!!!!   Everything is a big purchase if you DON’T NEED IT!!!!!!”

And then the things we do need, we research what we want, and buy quality so it’ll last and we’ll love it. But our trick is, we almost never pay retail prices. We look to buy quality used stuff off Craigslist, or clearance sales, or eBay, or if we want to go shopping, we never go to the mall. We go to our local Goodwills and thrift stores and look for diamonds in the rough.

Also, most of our entertainment comes from cheap or free activities such as exploring parks, bike riding, cross-country skiing, cooking for friends, etc…

That’s how we play defense with our money and try to save 50%+ of it.

We build wealth by investing it.

I’m just a standard Index Fund/Target Retirement Account guy through Vanguard.

But Real Estate investing has also been super good to us to keep my cost of living low, and to provide us some pretty sweet cash flow and appreciation investments.

Real Estate investing has worked for us because we believe in large down payments to keep our payments and debt/equity risk low. I am also very picky about my properties. I only buy them if I LOVE them and want to own them for the long haul. I may flip stuff eventually, but I am not ready to take those risks yet.

My strategy for real-estate investing was inspired by something I heard Warren Buffet say. Rather than buying into lousy companies for rock-bottom prices, he learned to buy fantastic companies at fair prices. This view helped inspire my investing strategy with real estate: I pass on the so-so properties being sold at a discount, and look for fantastic properties even if I pay a little more. Why? I want real-estate that rents easy, is easy to upkeep, and attracts a good crowd of tenants. I feel better owning property I think is cool and am proud of. I just don’t want to deal with the headaches that lousy properties bring.

We put 20% down on our first house. 25% down on our second house. Our goal is to put 35-55% down on our next house, or even surpass our goals and buy real estate for cash if we can.

Real estate also works well for me, because I personally enjoy getting dirty and working on projects one day of the week.

I own 2 properties with about $150,000 in equity.

$30K in our retirement accounts.

$25K in an individual stock.

$25K in cash.

And other small investments here and there.

What you describe here: how you value quality over quantity, how you enjoy being hands-on with the maintenance of your properties, how you love real-estate investing, seems like you are a true investor, and that’s the right path to fit your personality on the 3 paths to FI

Since I’m a Optimizer and a control freak, I loath having to deal with real-estate (with the exception of REITs) I would be a horrible fit since I wouldn’t bother ever swinging a hammer or fixing a sink but in your case, this seems like the perfect fit for you. Which just goes to show that everyone needs to find their own path to FIRE. What works for one person won’t work for another.

Thanks for sharing your numbers with us! It’s truly amazing what you can accomplish if you put your head down and work. After all, “opportunity sure looks like hard work!”

Other than your exceptional worth ethic, I’ve noticed something else that has gotten you this far is your positive attitude. Do you think things would’ve turned out differently if you’d never gone to jail? What if you could erase that experience? How differently do you think things would’ve turned out?

I’ve often thought about the answer to your question now that a successful life is a reality for me, and not just a dream. I can think of 3 possibilities of what would have happened to me if I didn’t go to prison:

1) I could have died the next night at the next party and my life would have ended.

2) I could have struggled with a secret, functional addiction and just “gotten by” in a job for 5, 10, or 30 years.

3) I could have eventually grown out of my partying adolescence like my best friend did who now owns 12 properties and is retired at 36. We’ll probably never know what would have happened.

I did have a good friend tell me this once, and it’s what DID happen to me. He said, “Sometimes, when you hold certain types of personalities back from what they are meant to do, that energy builds up inside of them like they’re being held in a slingshot that’s pulled all the way back, so when they are finally released, they shoot ten times as far as they would have if they simply rolled through their life.” Who knows what would have happened. I can only speak of what did happen.

That’s deep. It’s very conceivable and terrifying to think that you could’ve died the next night if you had kept partying. Often we only focus on the bad things that happen in our lives, we don’t focus on how sometimes it could be a blessing in disguise. And to your point about what your friend said about holding back the a person from what they were meant to do, and that energy pushing them to shoot ten times as far as what they were meant to do, I know exactly what that feels like. When you finally go from doing something that society dictates that you do to what you actually REALLY REALLY want to do, without worrying about money, the sky is the limit.

Your story is so inspirational, I feel like it should be written into a book. That’s why I was super excited when you mentioned you wrote a book called, Spark, with Gary Paulsen, the bestselling author of “Hatchet.” Tell us about that.

I just started writing journals in the beginning of my time in jail, because I felt this force inside of me telling me that I would one day want to remember these moments, and I needed something to fill my time.

But writing became an addiction for me, and it became my life every day. My journals turned into short stories, and then I just progressed into writing novels because I loved the feelings of achievement it gave me and I had all the time in the world and nothing better to do.

Gary read some of my writing through a family friend, and immediately sensed I had something to say and thought he could help me, so he reached out and asked if he could help.

He was/is just a writing mentor to me. But since we needed work to talk about, I just wrote stories for him to teach me, and some of those became actual novels and manuscripts I have sitting in my home office.

What do you hope to accomplish with this book?

My goal, when I create any piece of writing or art, is to just hopefully have the reader find a deeper meaning, purpose, understanding, or reason to live in their life.

I had the manuscript sitting in my office for the last few years. It was already done and written, and just thought it’s better to publish it, and help some people, rather than hide it in my safe.

It’s also an example to show that I can do this, and there’s going to be even more, and even better stuff coming from me in the future. I play the long-game in life.

I’ve already gotten a couple of cool comments like this which provides a great deal of meaning, purpose, and personal achievement for me (which is ultimately the feelings of wealth):

Thank you for sharing your story and being vulnerable. I’ve forwarded this to a few people. I just finished reading your book and have assigned it to my son (homeschool!). Now following your blog. 🙂


Wow. Comments like that really makes writers like us realize that it’s all worth it. #WhyWeWrite.

Okay, for our readers out there, if you want to read Billy B’s book, Spark, that he’s giving away for free, you can enjoy it here.

In addition to running your own business, managing your properties, and writing a book, you’ve also been doing inspirational talks to local high schools. In fact, I saw that you’ve recently been invited to be the feature speaker at one of the high-schools you visited. Tell us about that.

Last year a Facebook friend who is a professional speaker asked on Facebook for anyone with a story to join her visiting a local high school. I jumped at the opportunity, and was her guest last year.

This year she is pregnant, so the school asked if I could come and just lead the entire presentation.

Since it was a high school, there was strict rules on what I could talk about last year like non-religious stuff so I didn’t veer too far away from just my prison and “don’t do drugs” story.

The feedback from the kids last year, was that they wished I had more time to explain how I became so successful after prison, so this year I am going to go out talking about everything I mentioned above… and really hit home on this message….

“Prisons come in all sorts of shapes and sizes. There’s real prisons. But there’s also self-esteem, addiction, and financial prisons you can get trapped in. This is how you stay out of all the prisons you WILL encounter!!!!”

I love doing this and have a lot of practice doing it. I was on a panel in prison who talked to high school kids once a week for about 4 years. I’d do it for free I love it so much.

Ultimately, what I am trying to accomplish with money and my life is this:

“Some people want to create cool art to get rich. I want to get rich so I can spend my life creating cool art.”

Well said. Over the years, we’ve realized that money really is just a tool that frees you to go out there and create cool shit. Of all the best things I’ve ever done, building things that help other people is definitely the thing I enjoy the most.

Okay, so now that we’ve talked about your story and how far you’ve come, what advice do you have for people who are in bad situation they can’t seem to get out of?

Start small. See a vision of who you want to be, and then take small steps to become that person living that life. Master the small things, and then set new goals, and start adding bigger responsibilities and bigger steps to your plate.

Play the long game. The long game combined with talent, hard work, and quality character ALWAYS, ALWAYS, ALWAYS WINS.

I like to see it as the “Stages to Your Dream Life”.

Stage 1: Create Stability:

  • At this beginning stage, you need to realize that your life is not a black hole. You need to do everything you can do create stability. Without it, you can’t get to the next stage.

Stage 2: Create Comfort

  • Once you’re at this stage, finally life feels good and you’re not worried about survival anymore. At this point, you can start looking toward the next level.

Stage 3: Create Happiness

  • Now that you’re comfortable, you have work on your happiness. You can be grateful and happy to be alive.

Stage 4: Create Wealth

  • Now that you are stable, comfortable, and happy, it’s time to create wealth and use that to follow your dreams.

Stage 5 : Attack Your Dreams

  • You’ve made it! You can achieve your dreams!

Look at me, it took me 10 years of studying, planning, and preparing everyday not making a cent. But then when my opportunity came, and I was released into the real world, I was ready for anything, and I shot way beyond any of my dreams or what people thought was possible for me.

Become the person who loves practicing, and preparing, and executing, as much as you do achieving, and you can become a person who succeeds in any environment or any challenge.

Incredible! Thank you for taking the time to tell us your story, Billy B, and inspire us all to be better. You are living proof that even in the worst case scenario, there is still a way out.

For those of you who are struggling and can’t seem to get ahead, know that you are not alone. Start small, set goals, and then work hard and play the long game to achieve your dreams. Billy went from serving 10 years in jail, to making $9/hour stacking box, to a business making $60,000/year, and then finally amassing $250,000 net worth from his investment properties. Use this story as inspiration to drive you!

And to hear more from Billy B, check out his blog WealthWellDone.

What do you think? Have you ever been in a tough situation you thought you couldn’t get out of? What did you do?

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22 thoughts on “Guest Interview: Life and Money Lessons from Jail Part 2”

  1. Great to hear more of Billy’s story guys!

    You know what strikes me as being one of the big elements to success in stories like this? Taking that first step. He had nothing to lose when starting his business, so that first step wasn’t a big leap.

    People are often afraid to take chances in life because they have so much to lose. I bet Billy wasn’t worried about that when he started his first business.

    1. I really like this comment Mr Tako! I loved how you picked up on the little insights and “human truths” in the article. My story isn’t just about saving money, investing it, and becoming rich. The bigger lesson are how I fought my fears, and I learned how to embrace and overcome fear, and never be afraid of life again.

      You are so dead on that I felt like I had nothing to lose when I first got out of prison, and as I look back on those years, that fearless attitude was one of my biggest assets. I was like, who cares if I try to start a business and it fails? I’ve already failed in life on a massive scale, and yet I was still young, alive, and had a second chance to try again!!!! Once I had failed on such a massive scale, I realized that I had also learned on a massive scale. In fact, I started to see failure as the gateway to massive opportunities to learn and grow.

      I did know I didn’t want to put alot of money into a business, because I didn’t have that money to risk. But I was willing to risk tons of time and effort into building a business, because I had plenty of time and effort to risk. And if it didn’t work out, I was ok with losing my time because I would at least learn some valuable life lessons along the way, and would be better prepared for my next job interview or business opportunity.

      I also had alot of good, smart people around me, like my parents and girlfriend (now wife) who supported and encouraged me during this time. They were not entrepreneurs, but they saw I was a hard-working, honest, and talented guy, and all I needed was one lucky break to make it, and so they encouraged me to keep trying different things until I got my lucky break. Fortunately, my first business was my first lucky break. It just took me a year of hard work and rejection to get lucky. Haha!!!

      I will say overcoming fear is one of the biggest skills to learn to create wealth. I was afraid when I started my first business. But I overcame that fear, and now that I have successfully started a business, I don’t have that fear anymore. I know starting businesses just takes profitable ideas, good people, and time and effort. I also felt fear when we bought our first investment property. I’d never been a landlord before and I was nervous about it. But now that I have done it, and overcome the fear of that unknown, I realize it’s easy and I’ll have no problem doing it again. In some ways, fear is a choice. Choosing to overcome your fears to make something magical happen in your life is always the best choice.

    2. Great insight, Mr. Tako! When you’re at the bottom, there’s no way to go but up. Sometimes it’s a blessing in disguise when losing everything forces you to take a risk. In this case it really paid off.

  2. My spouse and I are currently sitting at stage 5 and totally agree with the statement “Some people want to create cool art to get rich. I want to get rich so I can spend my life creating cool art.” that has been my spouse’s life goal is to make cool art. He spent the last 15 years working full time and doing art as a hobby, now that he has the financial freedom to quit his job and focus on his art he actually have the time to try out new tools and mediums and make even better art. It has never been about money for him, he turns down most commission offers he gets so he can just focus on his own projects. He’s always just wanted to get his creations out into the world for people to see.

    1. Super cool Liz!!! It’s really exciting to see that I am not alone out there, that other people share my purpose and world-view. I’m currently sitting between stage 4 and 5 right now, so I look up to you at stage 5!!! (I still manage my money-making business that is not my dream life 50% of my time(stage 4), but then I work on my blog and real-estate projects the other 50% of my time which is my dream life so I am getting there. (stage 5)

      Like your husband, my dream is to just get my art out into the world, and I think if I can create good enough art, I’ll have plenty of opportunities to make money at it eventually. It may take me 2, 5, 10, or 20 years to do it, but since this is my dream life, I am totally in it for the long haul and can be patient before I have to make a profit.

      Even though my writing isn’t profitable now, I see my writing as “the business I want to retire at,” so I am deciding to start that business now in my 30’s, and let it slowly take over my life, rather than wait until I am actually retired at 65 and then try to start my dream business when I am old and tired. I don’t know if it will work or not, but a lot of my ideas in life have worked, so I may as well try and see what happens. Follow me at Wealth Well done to see how far I get. You’ll never know how far you get if you don’t try. 🙂

    2. Yup. I love that statement. Getting rich first, THEN spend your life creating art. That way your art is much better because you’re doing it for love and not money.

      Congrats on getting to stage 5!

  3. Amazing interview series. Love your 5 stages to your dream life. So glad that you put creating happiness ahead of creating wealth. If we’re not happy, it doesn’t matter how much money you have in the bank. Happiness is something we should all focus more on.

    1. Bam! You hit a home run out of the park with this comment Tawcan: “So glad you put creating happiness ahead of wealth.” Totally. Money won’t change who you are inside, so trust me, you’ll be alot happier as a happy person who creates alot of money, than an angry person who has alot of money.

      Focus on your happiness first. Then, once you learn how you become happy, learn how to dump piles of cash on to your passions to help you become even happier. 🙂 These are just the steps that worked for me. I learned how to be happy in prison, so now that I am free and am starting to collect alot of money, I use my money to buy the time and opportunities to make me even happier. All dreams that take a million steps, all begin by taking that first step.

    2. So true, Tawcan. If you’re not happy, it doesn’t matter how much you have in the bank. Money helps you have enough so you’re comfortable but after that, additional money can’t buy happiness.

  4. “Since it was a high school, there was strict rules on what I could talk about last year like non-religious stuff so I didn’t veer too far away from just my prison and “don’t do drugs” story.”

    Isnt that called censorship? So you can’t talk about religion, what can you talk about?

    When you write, don’t let them tell you what to say… just speak the truth.

    – spaceman

    1. We had this rule at work too. People weren’t allowed to solicit donations for religious reasons. I think it’s because they don’t want to end up fighting about religion and make the issue divisive so it’s easier just to remove that topic all together.

  5. Hey @Spaceman! I just got back from the speaking event today. I am doing the afternoon hours tomorrow. The censorship problems didn’t turn out nearly as bad as I originally thought. Going into it last year, I had been invited to do it by my friend who told me about the rules, so since I was her guest, and wanted to make sure she looked great, I didn’t want to say anything that she could get in trouble with.

    But after doing it last year, I found that the teachers and program leaders were totally cool. After meeting me, and hearing my story, they told me I could talk about whatever I wanted. Those non-religious program rules were probably just in place so guest speakers wouldn’t go off the deep end talking about Chrisitan or Muslim or Hindu or Jewish or Satanic rhetoric, when really the goal isn’t to give a religious lesson. It’s to inspire the kids to make the best possible decisions with their lives, which I was easily able to do without having to go deep into religious rhetoric and get into an argument with the kids about what religion is right. I’ll pass on that conversation!!!

  6. This is such an inspiring story.

    I loved when you said “I made like $1000 in my first 6 months in business going door to door doing business to business sales, and almost gave up because I knew I couldn’t live off of $1000.”

    So many people just give up too soon because it’s so hard to work for yourself and not making enough money. But if you have the guts to keep going, all the hard work starts to pay off.

    And I completely agree: money is not the goal, the goal is to be free and money is just the tool to get there as quickly as possible!

    1. I loved that part too, Sara! It’s great to think back to Billy’s inspirational story whenever I start a new passion project and it doesn’t go anywhere in the beginning. We all need a reminder that you need to bust your ass the beginning but what you’ve built pays dividends exponentially if you don’t give up.

  7. Hey Thanks Sara: On that note, I remember after 6 months and so many opportunities and sales that fell through, I was so discouraged. I was just about ready to throw in the towel, and try something else. But I remember going to church that weekend, and the sermon was on not giving up when things get hard. It was all about how so many people give up on their marriage, and their job, and dream life right before things could start turning around for them. That inspired me to give it another month. I had been working so hard for 6 months, I felt right on the verge of a breakthrough. In that next month, I went on a cold-call, and I got a $10,000 order. Two months later, I landed a $32,000 order. And all those on-the-fence clients started calling me for new projects and to place re-orders and my outlook and future totally began to change. I learned from that experience to give all new passion projects and businesses 6 months to 3 years to build them correctly before I judge them.

  8. What an inspirational story Billy! Your achievements despite the terrible start you had in life would put most of us who were privileged (relatively) to shame. It’s not surprising that people like us achieve FI but people who’ve had a bad hand to deal with and yet achieve success are the real heroes whose story the world needs to hear more of.

    1. Well, thanks. I totally get your feelings, and I even struggle with wondering if life is fair with some of the privileges I have even had. I mean, I am still a Caucasian male with a college education. Those privileges definitely helped me as a child. However, I think you can see from when all of those privileges were taken away from me, it was my work-ethic, positive attitude, and commitment to excellence and developing my talent that got me back to the top. In modern America, I truly believe those are the skills and traits that lead you to success no matter who you are, what you look like, or how you grew up. That’s the message I want to spend my life sharing.

  9. Love your story Billy, so incredible and inspiring! I’m pumped for you that you’ve come so far and have such a bright future ahead of you. Love all the ways you’re giving back and sparking others with your story to create a better life for themselves. Thanks again for sharing this with all of us. Since your initial post on Budgets Are Sexy, your story has come to my mind dozens of times.

    1. I love your comment!!!! You nailed the mission I am on! It really has little to do with money. It’s all about changing your mind, and then applying action to create a better life and reality for yourself. Once you are happy, then dump money into your passions, to inspire others and create opportunities to live your dream life. Thanks for letting me know that original story stuck with you. It brings me great happiness that it probably stuck with alot of people, and probably changed some lives I’ll never meet out in the great wild blue yonder of the internet.

  10. in 1992 i had the misfortune of living in a boarding house outside boston, which is a very expensive city for rent. this joint was full of real degenerates but mostly harmless by my standards. i was barely making enough as a lab tech to pay 100/wk and to eat and mostly rode a bike a couple of miles to my job. long story short: after a night of budweiser and cheap vodka with the other residents, i woke up on the roof outside the bathroom window with the sun heating me up with my blanket and pillow and a puddle of green bile vomit nearby.
    that was about when i thought: i better get the hell out of here and this dead end place and at least be poor among friends, which i did. being around decent people you can trust was about enough boost to get out of that and get at least to stability and eventually comfort. fast forward to the early 2000’s and meeting mrs. smidlap gave more of a purpose to reach financial independence as somebody else was now depending on yours truly not to f’ it up. p.s. we made it.

    good stories, B.

    1. Awesome story of realizing you were at a rock bottom you didn’t like, and making the choices to get out of that place. That’s what life is all about: Finding out what you don’t want, and then making plans to get what you do want.

      My wife has also inspired my sobriety. I never want to overdose, or experience psychological trauma because of drug use, and become a cripple and leave her an invalid for a husband. I know the chance is very small that could happen, but I’ve already lived a 1-in-a-million nightmare. The fear of that inspires me to be careful with the risks I take.

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