From Broke Phi Broke to Financially Woke – Organized by Josh

Today, I am excited to share with you the latest interview in the From Broke to Financially Woke series!  The purpose of this series it to give hope to those struggling to escape from the not so secret group Broke Phi Broke.  A group whose chant is, “We ain’t got it. Broke, Broke, Phi Broke! We ain’t got it. Broke, Broke, Phi Broke!”

To help me accomplish this goal, I have invited the best and brightest of the financial independence community here to share their stories.  As you read their interviews, pay close attention to the mistakes they made.  Take mental note of the success principles they used to turn things around.

When trying to apply these principles to your own life, realize that success in life is rarely linear.  You will encounter some struggles.  But stay persistent.  Keep moving forward.

Our special guest today is Josh from Organized by Josh! At his lowest point, he had over $50,000 in debt (car loan, student loans, and credit cards.).

As of today, he’s been debt free for over five years! How did he turn his financial life around? I’ll let him tell you…

Introduce yourself.  Where do you blog?  What are some of your interests outside of financial independence?


My name is Josh Stine and I’m a serial entrepreneur & coach that helps people find financial freedom and achieve their financial goals through personalized one-on-one coaching. As an entrepreneur, I’ve started and grown two companies to reach over $1M in annual revenue in the live event and sports industry. I blog on my website at:

 Outside of FI my interests include attending sports and concerts, entrepreneurship, travel, spending time outside, and fitness/running. 


Tell us about a time where you were a member of Broke Phi Broke.  How did living paycheck to paycheck make you feel as a person?  At your lowest point, how much debt did you have?


Broke Phi Broke

I graduated college in 2014 and moved to DC to start working at a Big-4 consulting firm. I was excited and had never seen this kind of money in my life. I didn’t understand money at all and right after graduating bought a nice car, new clothes, and so much more. I realized quickly I was living paycheck to paycheck and trying to keep up with my consulting buddies. Eventually I realized none of this was bringing me joy and I needed to make a change after making so many financial mistakes. At my low point I had over $50,000 worth of debt between student loans, car, and credit cards. I hated the feeling of being stuck with this debt and tied to a job I didn’t enjoy.


What are some of your biggest financial mistakes?


One month after graduating college I bought a fully loaded Honda Civic for $24,000. I thought I needed a car to commute around DC and to get to clients, but I never truly needed it because I would take public transit to work and chose to live in Arlington, VA which has one of the highest walkability scores in the country. My monthly car payment really slowed down my ability to pay off my other debts and save and invest my money. If you’re moving to a city with good public transit you should try ditching the car and see just how much you can save.


Describe your upbringing.  Where did you grow up?  What did your parents or teachers teach you about money?


I grew up in State College, PA (home of Penn State University) in a middle-class family. I had a wonderful childhood, but I really didn’t enjoy school until college. My family and teachers never educated me about money growing up, so I’ve had to learn everything on my own. My parents went into debt to give us a better life similar to most everyone else in the family and neighborhood but thankfully they are doing much better today. 

As a first-generation college graduate in my family, I’ve witnessed family members make so many financial mistakes, but I never understood them at the time until I learned on my own. In college I also discovered entrepreneurship, which made me realize your income earning potential is unlimited. 


How important is becoming financially woke to you?  What steps have you taken to increase your financial knowledge?


I first started my financial transformation when I discovered Dave Ramsey and used his snowball method to pay off my student loans. It was exciting but after I paid off my student loans in 10 months, I needed bigger money goals like financial independence. My decisions in life then started revolving around frugality for a while until I grew my income with the startup company I joined to help grow. 

My finances became one of the most important things in my life when I started to create an exit strategy to get out of Big-4 consulting. I committed to paying off all my debt before making my next career move, which ended up being entrepreneurship. I’ve been debt-free for over 5 years now and have grown multiple companies from $0 to $1M+ in annual revenue.

What are some of the key principles you have used to improve your financial life?
Success Principles

Since 2015 I’ve followed these money practices:


  1. No new debt, unless it’s to buy a house or rental property.
  2. Live on 50% of my income to save and invest the rest. If you can’t do this try to live below your means whenever possible to increase your savings rate.
  3. Credit cards are king so long as you pay them off in full each month. I use them to maximize cashback and travel rewards and since 2016, I’ve earned more than $50,000 from credit cards.
  4. Don’t own a car – I haven’t had a car payment or owned a car for years and it’s been a great financial decision. Choosing to live in a city with good public transit is key if you want to go car-free, but you must consider the cost of living difference.  
  5. Start your own business or side hustle to increase income and build new skills.


How often do you consume personal finance information?  Name 3-5 of your favorites sources (books, podcasts, blogs, etc.). 


I consume personal finance information daily since it’s my business to always be learning. Even if I wasn’t a financial coach, I would still be consuming content daily as there is always something new to learn. 


Here are some of my favorite books and podcasts:


  • ChooseFI
  • Afford Anything

[Editor’s note: These two podcasts made my 7 Peerless Money Podcast Recommendations list!]


[Editor’s Note: After reading this interview, check out my chapter 4 review of Grant Sabatier’s Financial Freedom.

Is there any advice/encouraging words you can give those who are struggling to escape Broke Phi Broke?


The first thing I suggest to anyone is to start tracking your spending with a monthly budget. I use YNAB to do this and use it with all of my coaching clients to make it easy. No matter where you are at financially you need to understand what you spend on each month. You’ll likely find ways to cut back on some spending and spend more on the things you value. This process of budgeting and tracking my spending is what changed my relationship with money, pay off $50,000 of debt, and helped me start saving and investing 50% of my income

Just like any other kind of goal you want to achieve you need to start doing something to get better. In the case of money and financial goals, you need to know how much you spend versus how much you make. If you spend more than you make you need to make a change. If you make more than you spend, that’s great, but what can you do with the surplus? 

Changing your habits and financial practices may seem challenging at first, but if you can do the basics right you’ll be on your way to financial freedom before you know it. 


How can the readers contact you?

You can contact me on my website here or via email at

You can find me and connect on social media:

Twitter: @StineJosh

Read more interviews in the From Broke to Financially Woke Series.

Please share this From Broke to Financially Woke interview on social media with the hashtag #escapebrokephibroke

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Author: Jerry

Jerry is a Business Insider Contributing Writer who is obsessed with personal finance. He believes you can improve your financial situation by applying principles taught by the financial independence community to your financial life.

If you are having trouble saving, he recommends that you join the SaverLife Savings program where you can get a $60 reward after six months (no income requirement). All you have to do is put a minimum of $20 a month into a savings account. Easy, right?

For a fun read, check out his article 10 Signs You’re a Personal Finance Addict to see if you are a personal finance nerd.

Before you go, check out the new From Broke to Financially Woke Interview Series.

Also, please subscribe below if you found his content valuable and want to continue following him as he documents his own journey from Broke to Financially Woke!

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