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  • Writer's pictureJohn Lim

MF 090 : Dan Raaf’s Road to Redemption and a Pivot to Entrepreneurship

Updated: Jun 17, 2022


Moving Forward is also available on Apple Podcasts, Stitcher Radio, Google Podcasts, Spotify, and Amazon Music.

Dan Raaf is an entrepreneur in the digital and social media space.  Today, he shares his story of overcoming challenges and a rock bottom moment most of us will never have to face.  Get ready to be inspired as Dan will show you that no matter how tough life gets, you can make a choice to pivot and move forward.

The best email intro:

It was an early Saturday morning, I was barely awake but like a creature of habit, I checked my phone to see what new messages and emails I had (I know, I know, I’m working on not looking at my phone first thing in the morning but Pavlovian reactions are hard to break).  Lo and behold, I have an email sent late Friday night from Leonard Kim.  Leonard has a way of sending emails w/ headlines that immediately pull you away from all the other chatter and noise.  It’s as if it’s calling out to you, saying “hey you, open me first, you know you wanna!”  The headline of this particular email was “Bank robber wants to go on your podcast.”  Don’t believe me?  Here’s a screenshot straight from my inbox:


So naturally my first thought, reading this at 6:30 am on a Saturday, was “this must be a joke.”  While Leonard does have a sense of humor, he’s not really a prankster.  He’s just honest and straightforward.  So I read the email and to my surprise, it was just as the headline said and as you’ll learn on today’s episode, Dan Raaf is a reformed bank robber who served time in prison for robbing three banks.

Dan’s story:

Now that you’ve read the above part, you probably have a bunch of preconceived notions about Dan.  Let me dispel them for you.  First, he’s quite bright.  He was gifted in school and actually went to college at age 16.  Along the way, Dan faced some tough moments.  He dropped out of school, became addicted to alcohol and prescription drugs and eventually hit a rock bottom point in his life.  With no prospects and desperate for money, Dan decided to turn to crime.  This comes to the second preconceived notion we can dispel.  Dan is not a violent individual.  In fact, you may be surprised to learn that Dan never once used a gun to commit any of his crimes.  Instead, he read some books about bank robberies and decided to take the least violent route to committing the crimes.  Now let’s get to preconceived notion number three.  While Dan did get an adrenaline rush out of robbing his first bank, there was nothing glamorous or exciting about the lifestyle, if you can call it that.  Rather, Dan was constantly paranoid and on edge from the time he robbed his first bank to when he got caught.  And when he did finally get caught, he shares that he felt a great sense of relief.

After getting caught, Dan served time in prison.  And this is where we can dispell preconceived notion number four.  He didn’t get tough or join a gang and prison wasn’t some rite of passage towards becoming a badass.  No, as Dan describes it, it was more like middle school with the inmates making immature jokes.  As you’ll learn, Dan was pretty fed up and disappointed.  So what was Dan’s turning point?  It came when the inmates and the guards taunted him; telling him that after his release he would eventually return.  As Dan shares from his own experience, prison isn’t really designed to rehabilitate its inhabitants.  It was at that point that Dan decided that when he was released, he never wanted to come back.  However, Dan also realized that he would have to start developing some useful skills and honing the ones he already had.  As one of the few inmates w/ an education beyond high school, Dan started helping inmates who were soon to be released w/ their resumes.  He also learned firefighting skills as part of an inmate fire camp program.  Dan did everything he could to occupy his time, from studying in the prison law library to playing sudoku, so that he could redirect his mindset towards a more constructive direction.

Once he was out, Dan knew that whatever challenges he had before prison, they were going to be even more daunting coming out.  Although he had served his time and his debt to society was paid in full, getting a job w/ a prison record would be difficult, if not impossible.  However, Dan’s grit, determination and his honesty about his past helped him land a sales job w/ photocopy machine shop.  In a way this was Dan’s first test of taking ownership of his story and not hiding from it.  As Dan shares, the manager looked at him for a long time before deciding to give him a chance.

After making his bones in sales, Dan transitioned to working for his brother-in-law who was managing Facebook and social media pages for clients.  Dan got immersed into this world, learning all he could.  Quite a change when you think about it.  Dan went from putting his knowledge and energy into stealing money to making it legitimately thru the advent of digital and social media.  And the cool part?  Dan got pretty good at this and saw the potential for growing a business and becoming an entrepreneur, which let’s face it, is a much better long-term prospect than being a bank robber.

So now we get to today.  Dan is an entrepreneur; taking what he has learned about social and digital media, to help businesses generate leads, customers and sales.  As of this interview, Dan has signed three clients and was able to pay himself more than what he was making, working for his brother-in-law.

Getting out of comfort zones:

So many of you reading this or listening to this week’s episode may not have gotten past the fact that Dan is a former bank robber.  I know when I read Leonard’s introductory email and realized it wasn’t a joke, that I had a similar knee jerk reaction.  But as I exchanged some emails w/ Dan and read his story, I realized that not having Dan on the show would be a big mistake.  This show is called Moving Forward.  What is the point of the show?  To inspire you to move forward.  How do we do that?  By sharing the stories of extraordinary people.  Now, some of you may think that, that means just listening to guests who have never committed a crime and are now multi-millionaires.  And yes, many of Moving Forward’s guests are famous, successful and so forth.  But are those the only guests that can inspire you?  I had to ask myself this very question when Leonard introduced me to Dan and that excited me.  The fact that here was a potential guest that shook me out of my comfort zone meant there was something here and an important story that needed to be shared.  But what’s even more amazing is how much Dan shares on this episode, especially since this is Dan’s first podcast interview.  The initial hesitation I felt is something Dan experiences everyday within himself and from the outside world.  For all intents and purposes, Dan has paid his debt to society.  And yet, many of you reading or listening to this episode still haven’t gotten over his past.  Some of you are probably hesitant to connect w/ Dan and would be even more hesitant to work w/ him.  Dan knows all of this.  He even shares on the episode how if you Google his name, there’s no hiding from his past and that several times, it prevented a prospect from turning into a client.  On top of that, Dan is just starting out on his entrepreneurial journey.  Right now, he’s living in what is basically a shed and sometimes faces the struggles of making ends meet.  As hesitant as I was to have Dan on the show, he was equally hesitant to be on the show because he didn’t feel worthy compared to some of our other guests.  But Dan came on and not only does he share his story, he takes full ownership of it.  Many of us face challenges and for some of you, those challenges may be big ones that would rattle anyone’s core.  But I’m guessing most of you have never committed a crime or served time in jail.  If you had, would you be brave enough to come on a podcast to share it, especially while taking the entrepreneurial leap?  Dan did.  Why?  Because he would rather you hear his story from him rather than learn it from a Google search.  Because, he knows it’s the elephant in the room that might make many of you hesitant to hire him, even though he has a proven track record of results.  So instead of hiding from it, Dan has decided to take ownership of it, share it here and move forward.

Dan is moving forward:

Dan isn’t just a guest w/ an interesting story.  He’s working hard and seeking to do more w/ his life and his career; all while overcoming some very big challenges.  Although many of you will never be able to understand or relate to Dan’s choices, I bet many of you you can relate to the frustration, the difficult situation and the circumstances that drove him there. What’s amazing isn’t that Dan is on moving forward but that he is moving forward.  He’s taking the entrepreneurial leap and doing so w/ full ownership and responsibility over his story.  May we all be that brave and bold when deciding to pivot or change course.

Use your discomfort to pivot and move forward:

Finally, I’m going to leave you w/ this challenge.  If you’re feeling the need to change or maybe you’ve hit rock bottom, then listen to Dan’s story.  No matter what mistakes or failures you’ve had, chances are you haven’t hit as dire times as Dan experienced in his life.  Or maybe you have.  Regardless, the question is: what are you going to do now?  I don’t doubt that there are tough days where Dan might feel it would be easier to just give up and fulfill the prophecy of his former prison cellmates and the guards who predicted a revolving door back to prison.  But Dan has made a bolder, braver choice, a path of redemption; using his gifts and talents to create a better life for himself and help the clients who have placed their trust in him, succeed.  When it comes to overcoming past failures and bad choices, Dan is doing that every single day.  So take heart and use the discomfort that you may feel now to get out of your own comfort zone, to make a change and to really move forward.

Support the Podcast:

  1. The Corporate Cliches Adult Coloring Book: makes the perfect stocking stuffer or white elephant gift.

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Connect with Dan:

  1. Dan Raaf (website)

  2. Email Dan

  3. Facebook

  4. Twitter

  5. LinkedIn

#digitalmedia #reformedbankrobber #danraaf #wwwdanraafla #secondchances #entrepreneur #redemption #SocialMedia #turnhislifearound

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