The Not-So-Sexy Step That Every Profitable Entrepreneur Must Take

There’s a specific step every entrepreneur needs to take that isn’t talked about nearly enough.

The news likes to cover the “overnight” success stories like Facebook buying Instagram for a billion dollars or Angry Birds selling millions of copies, but they don’t share the key first step that the people who built these stories took.

So, what is this secret phase that almost every successful entrepreneur has gone through, but that no one cares to mention?

Keep reading and I’ll tell you.

The First Step Towards Entrepreneurship

You might think that all entrepreneurs are generally risky people. You picture them:

  • In Vegas putting all their chips on red and letting the roulette wheel spin.
  • Speeding sports cars down the highway, dodging between traffic.
  • Constantly jumping off of things with parachutes attached to themselves.

From what I’ve seen, that couldn’t be further from the truth.

Recently at the College Investor, Robert asked five highly successful bloggers about how they made the leap to self employment. The trend in the answers below may surprise you.

  • Pat Flynn had a $12,000 emergency fund when he lost his job as an architect, before he started Smart Passive Income or even earning money online.
  • Leo Babauta saved up two months worth of expenses before he took the leap to work on Zen Habits full-time.
  • Sam from Financial Samurai saved up 15 YEARS of expenses before making the leap to semi-retirement/self-employment.
  • David Risley always keeps his emergency fund high with investments in both cash and gold.
  • And our own Corbett Barr worked in the corporate world for close to a decade while amassing savings that he could have lived off of for a few years.

If you are sensing a trend, that’s because there is one.

Most successful entrepreneurs got their financial shit together before they ever made the leap.

Why Is This?

The reason that entrepreneurs need to have their personal finances in order before they start taking risks is the freedom and flexibility it offers.

When you aren’t spending every waking moment worrying about making ends meet or paying off your debt you free up energy to tackle your bigger problems:

How are you going to make this world better through the work that you do and how are you going to get paid handsomely doing so?

When your own money is not an issue you stop thinking about fixing your own problems and start solving other peoples’ problems (which is the basis of most businesses).

Not Everyone Gets Angel Funding

It is hard enough to bootstrap a profitable business from the ground up when you have capital to work with, but when your own finances are in ruin, it can be close to impossible to turn a profit.

Yes, there are businesses that you could start on the cheap, but most are going to take a decent amount of cash to get off the ground and even more to actually start earning a living from them.

And eventually you’ll want to make the leap to work on your business full-time. This will probably happen before the business can support you entirely. Without a safety net, this won’t be possible, and you may never get enough momentum to push your new business over the hump to success.

I’m sure you could easily list ten things you’d like invest in that would make your website or business bigger/faster/stronger/smarter that you haven’t bought yet because you can’t afford to.

Well, there is just one piece of advice I have for you: do something about it.

What You Should Do About Your Money Woes

If you want to turn your personal finances around there are four simple steps to take.

1. Learn

You have to become educated. Money is one of the most complex and intimidating aspects of life. Not learning how to manage your money before you build a business is like not knowing how to drive a car and then going on the German autobahn. Prepare for flames.

When I started my first full-time job after college, I was deep in student loan debt and was suddenly making more money than ever before. I spent a bunch of my free time learning about saving, investing, and earning. Without that foundation I would have never gotten out of debt or been able to leave my unfulfilling corporate gig.

“Anyone who stops learning is old, whether at twenty or eighty. Anyone who keeps learning stays young. The greatest thing in life is to keep your mind young.”
- Henry Ford

Action #1: Pick a new personal finance resource this week to start learning from.

2. Plan

Planning is the step that most people quit on. There are thousands of personal finance books, blogs, and podcasts but they often don’t tell you where you should start.

Does debt come first? What about saving? How can I earn more? What in the world is an IRA?

This why I created Make It Rain, which I’m launching today. It has ten weekly plans, each with ten action steps for you to turn your finances around. You don’t have to spend time deciding what you should do to get a handle on your money because it is all right there for you.

Action #2: List the specific problems you have with money and pick one to tackle first.

3. Act

If you don’t take action, steps one and two were a complete waste of time.

“An ounce of action is worth a ton of theory.”
- Ralph Waldo Emerson

Unless you start changing your spending and saving habits your plan will fail. Use either physical or mental hacks (such as freezing your credit card in ice or using a 30 day “wait to buy” list) to keep yourself from spending all of your discretionary income.

Action #3: Figure out your five worst spending habits (big or small) and quit doing them.

4. Become an Expert

Here at Think Traffic we’re huge fans of becoming an expert at things and personal finance is no different. Once you get past the basics of how to manage your money and get a handle on the pyschology behind it, there are plenty of advanced tips and tricks that you’ll pick up.

One of the “pro tips” I mention in Make It Rain is that the specific retirement funds that you invest in, such as an S&P or International index, through a 401(k) or a Roth IRA all have management fees associated with them. Investment firms will try to get you to pick their funds that are highly “managed” by actual teams of employees, but these will have much larger fees on them. Some as high as 3% or 4%.

This fee eats directly into any return on investment you get, but it is also charged even if the fund loses money! The alternative to this is to go with funds that have low fees like the low-cost funds at Vanguard (aim for less than 0.25%).

Be on the lookout for money hacks like this to maximize your savings over time.

Action #4: Look up all of the fees associated with the investment/retirement funds you have and switch to options with lower fees.

Do It For The Freedom

If you are completely overwhelmed by money or even if you’re on the right track, I challenge you to take a hard look at your finances more often than you do now and make the decision to improve them.

Whether you use a course like Make It Rain or some other resource, give your financial life the attention it deserves.

It will not only help your personal life; it will give you more freedom to let your website and business grow too.


Do you agree that aspiring entrepreneurs should fix their own financial problems before they start a business? What personal money issues keep you from investing more (time or money) in your own business?

Tell us in the comments, we’d love to hear your answers.

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  • Mitch

    I am one of those lucky basterds that started my online carreer when I was living with my parents. Right now, I have everything working out for me, and I don’t have any financial problems at all.

    I don’t know about first fixing financial problems before starting your business. Sometimes I think it is motivating to make your business work so you can fix your personal problems also.

    If you have something (a plan) in which you believe than I think you should just go for it and don’t look back.

    • Caleb Wojcik

      Great point Mitch. When you absolutely need the income, you may be motivated to work harder, but at what cost? Will you sacrifice your values or do things that make the biggest buck instead of what you really want to do? That is something I think you would need to be careful of.

  • Ernie Dempsey

    You nailed it. I tell people all the time that if they are worried about your financial responsibilities, they will be so caught up in thinking about making money that they won’t produce a good product or service.

    Also, they will constantly be pressing, trying to push something out that ends up being half-assed or completely un-needed by the audience or customer base.

    Thanks again. Great thoughts.

    • Caleb Wojcik

      Absolutely Ernie. In my opinion you have to get your finances in order first.

  • Linda Esposito

    I absolutely think it’s imperative to get your financial affairs in order (or at least have your debt at a reasonable amount) before you venture into an online biz full-time.

    At its core financial intelligence implies discipline, frugality, and the ability to delay gratification. In my line of work (a brick and mortar), the clients who are most distressed about life, have substantial debt. A lot of this is due to poor choices and impulsive purchases or fads, but it speaks to the use of money as a balm, or substitute for what you lack inside.

    It’s difficult to dream of the freedom that comes with a location-independent online biz, if stress keeps you awake at night.

    Love the message, Caleb. Good luck with the product :).

    • Caleb Wojcik

      I love the perspective here Linda. Not only are discipline and frugality helpful personal finance habits, they are traits that are extremely important if you want to run a successful business as well.

      Thanks! :)

  • Tom

    I started investing in real estate 3 years ago and have almost enough to live on passively. Part of my plan is to buy 3 more properties before I quit my job next year. Cashflow is awesome. Mutual funds are awful by the way. You don’t need to buy real estate if it’s scary for you but please for Your own good avoid mutual funds like the plague

    • Caleb Wojcik

      Hey Tom, I think both types of investments (real estate and mutual funds) have their pro’s and con’s depending on the situations. People have both made a living and lost a fortune on both. Being educated about your decisions and having a little bit of luck help too. ;)

  • Laura Lee Carter aka the Midlife Crisis Queen

    My favorite quote about business comes from Laurence Welk: “It takes ten to twenty years to become an ‘overnight sensation.’”

    Those of us past age 50 know that having your own money is where entrepreneurship begins. First solve your own problems! That is the only time you can presume to “start solving other peoples’ problems.” Most of us have had decades to build up our own capital through investment.

    I could teach anyone the principles of accumulating money, but most youngsters have no time or interest. Live and learn!

    • Caleb Wojcik

      Perhaps it takes a mid or quarter-life crisis for someone to “wake up” and be interested in learning about finance?

  • Chris Green

    I started out freelancing when I had just got married and got myself a big mortgage.

    What I did before I made the leap though was to build up a bank of clients that I could get some regular design work from. It wasn’t groundbreaking amounts of money, but I knew it would partly cover me.

    The challenge I had though was that I knew I couldn’t build up the clients I would need to replace my income straight away while I was working full time. So I just picked a date (with my gut and built in instincts) and made a leap into it…

    I’ve never looked back. In the last 10 years i’ve had some shaky moments. Had some months when i’ve delayed mortgage payments to get by… but all in all I doubt I will ever work for anyone again and I love the freedom I have (when I manage my time correctly).

    • Caleb Wojcik

      This is a great plan to follow. Instead of just jumping off the income cliff you bridged the gap being employed and self-employed. I recommend that most people take this approach if possible. Thanks for sharing Chris.

  • Joe Piroli

    The major problem people have when wanting to start a business online is that they do so because they need money and usually they get caught up in buying so many opportunities based on the instant gratification of wanting to make money fast!

    Making money is a long term experience the real difficulty is finding something that works and you can go with and that usually requires spending money learning what works and what doesn’t.

    Expertise is essential but all that means is understanding how things work which can only be found through trial and error.

    Avoiding debt and being able to invest money you can afford to lose is the name of the game.

    If your struggling financially then you either sink or swim in business. It’s a matter of personal chioce and situation.

    I’m at my best when I have no major financial woes and I simply want to make money to get wealthier.

    If I’m in the s**t I tend to panic and die, so i have to get my s**t together before I can make money.

  • Thomas @ Mobile App Tycoon

    One of the added benefits to making sure you have some sort of safety fund or even working a job while starting your businesses is that you aren’t forced to monetize early on. Nothing is more of a turn-off for me when I visit a website than seeing a newbie blogger with ads littered all over the place – trying to monetize the 2 visitors per day he or she gets. When you have some security, you aren’t forced to try and make a quick buck online but to instead work hard now for little to nothing so you can generate lots of income later.


    • Caleb Wojcik

      Very important argument here Thomas. Most of the “quick tricks” to earn money aren’t sustainable or earn enough to be worth what they end up doing to your brand, especially ads on a new blog.

  • Cubicle Free Man

    I left the cubicle 10 years ago and I too was pretty conservative I guess. I saved up about $20k before I made the leap to online business. Although I think financial planning is important, I believe starting a business does not require savings or security for some people. A buddy of mine had nothing except a part-time job and he quit college to build and sell his businesses for many millions of dollars a few years later. Before he started his business he asked me if I would like to be his partner. I declined thinking it was too risky. However, I did create my own successful business years later. The answer really lies in the individual: Their risk appetite and personal circumstances at the time. You really have to ask yourself the right questions. Working part-time on an online business (after work) I believe is a terrific way to get started.

    • Caleb Wojcik

      Well said. It really depends on the person and what they level of lifestyle they keep for themselves until things get off the ground.

  • J. Delancy

    I’ve skydived, parasailed, swam with sharks. I have two profitable hobbies (Not yet businesses). Before I began taking business or personal risks I made sure to have an Emergency Fund that covered living expenses for at least six months.
    In general the media focuses too much on the glamour of risk-takers but not on how they built strong financial foundations.

  • LaptopLifeLisa

    Just chiming in with support. I was debt-free when I started my businesses and truly believe it’s the only way. If you have huge debt and are living beyond your means (with the sympathetic understanding that it is possible to have debt without living beyond your means) I can only assume that you don’t have visibility in to your money situation. Money is one of the resources you need to get you to your dream lifestyle – so if you don’t have a handle on your money you don’t have a handle on your dreams. Who knows maybe if you were clear on your dream lifestyle and you sorted out your financial life, you might discover that you didn’t need to start a business after all.

  • Tony

    I would have to say some of the greatest businessmen and women have started with less than nothing. It can be a great motivator for some. People have come from poor countries to the US to make millions. I for one started in my parent’s garage with nothing 35 years ago.

    Trust me, It is way easier to start now, during these times, with nothing, broke, and in debt. These are good times if you see the comparison. Yes, getting your s*** together is one way, however, it’s not the only way. Why wait? do it now!

    The question is, “How bad do you want it?” If you want it bad enough, debt won’t stand in your way. Actually, debt can be a launching pad. Life is a physiological game, it’s how you see things based on your experiences and belief system.

    Change your way of thinking, and your whole world will change. Go on Youtube and do some research on how people that were challenged physically, mentally, and financially, created and manifested miracles.

    Where you are right now, challenged in any way, you can do it. If you’re reading this, you already have enough to become successful. Being broke and in debt is only an excuse.

    Where else can you start a business on 15 bucks. I mean really, how easy can it be? Go get a domain name and start writing and researching. Google? We never had Google when I was younger. Google is a goldmine for research. In comparison, you have the resources at your fingertips.

    As I lay here on my bed with my laptop thinking, if I was broke and in debt what would I do? I would borrow 15 bucks and start, that’s what I would do! I would change my way of thinking and be so determined that nothing would stand in my way. I would know I was born with all the tools I need to succeed, we all are!

    You want inspiration, check out this video:


  • Iris

    “If you are sensing a trend, that’s because there is one.” Haha :)

    “Not learning how to manage your money before you build a business is like not knowing how to drive a car and then going on the German autobahn. ”
    TRUE! Going on the German Autobahn is even dangerous when you are a German and have learned how to drive in Germany. You have to be prepared.

    I think what you say is true, you should have your finances in order before you take the big leap and quit your job. I’m not so sure though if you have to have it all figured out when you start your business on the side. That’s what I’m currently doing. But I’m a college student, so things might be different.

    I have 3 simple rules that I live by:
    1. Put 10% of your money into savings (aka the piggy bank. I don’t trust real banks anymore. I guess that’s because I live in Europe).
    2. Make a must-be-spent plan in the beginning of the month to figure out how much money you can spend on food etc.
    3. Put any leftover money from the last month into savings ASAP or they will somehow miraculously be spent.
    4. Only buy clothes on sale.

    That’s it.

    I really enjoyed reading the post. Good luck with your launch! :)

  • Sheyi |

    Caleb, many thanks to you for your make it rain project here in Africa. I’m a Nigerian and glad to see someone like you doing good thing for my continent.

    This article is so good and thought povoking. Many people entered the internet biz hoping to make one gazzilion dollar within 3 months after investing $50 in some crappy ebooks.

    It does not work like that.

    Let’s make it rain!


  • Andrew Youderian

    THANK YOU for saying this, Caleb! So true it’s one of the non-sexy elements of success that so often goes un-talked about. If you’re not willing to work hard to build a safety net so that you can give your self the opportunity to succeed, it’s likely never going to happen.

    I’ve found this concept to be 100% true in my own life as I’ve come to work full-time online, and it’s great to hear examples of others where it was pivotal to their success.

  • Maeg

    Great, great post. Excellent reminder that you don’t have to be a huge financial risk-taker in your personal life in order to have entrepreneurial spirit.

    Reminds me of a quote I heard recently (and wish I could attribute): “Think of your day job as your first angel investor.” Love that.

    I definitely agree that having your financial affairs in order before you take the leap will help you make sound (instead of desperate) business decisions. At the same time, there’s only so much day-job-working and saving you can do (at least for me) while growing a business. My husband and I are constantly toeing that line and living simply.

    I’m not naturally a risk-taker; I’m okay with not taking the leap before we are ready. We also have children–there’s no greater impetus for financial responsibility than being responsible for their lives, too. (At the same time, they’re also a huge motivation for getting our businesses off the ground, too.)

    Thanks for the thoughtful post, Caleb!

  • Mari

    I put up with a pain in a client from hell for 5 years in order to save up enough to walk away. I wanted to have 2 years of income set aside before I started my own business. It was hard, and there were times when I almost gave up. But then the client would do something to make me mad and I was inspired again to stick to my plan. The day I walked away (Nov 30th 2010) was the sweetest EVER. Worth all the sacrifice and it leaves me with the piece of mind to build my business without the financial headaches.

  • Rachael

    I think this post is absolutely spot on.
    I myself have been having that debate with my partner during the last few days. See I graduated from Finance at university last year and live in a small town. While I LOVE the lifestyle here (beaches, motorbike riding etc), the jobs available are not great.
    I am not even sure whether I want to work full time in the 8-5 employment setting.
    So I did the ‘Start a blog that matters course’ and I’ve read a lot of books. I’ve nearly finished my first site and soon to be live.
    My partner is very supportive, but I want to work on other online ventures rather then working. SO the deal we’ve made is to save up $X amount and then I can have a go at it full time. If it doesn’t work out well initially, I’ll be getting some casual work to assist with financial commitments.
    The great thing about the topic, is that it does take common sense most times. At uni I lived very frugally and had a lot in savings. We’ve just bought a house but one that is inexpensive and needing repairs that we can do ourselves over time. By living smart with your disposable income, it works out well in the future.
    I agree with the saying that perhaps the ‘pressure’ of blowing caution to the wind works well for motivation. But sometimes if you want to take a step back and go after your passion conservatively, that works too. Motivation can be a question of perspective. If you want to do it, you will.
    Love the post and love reading all the great comments. Enjoy the lovely day.

  • Richard Santos

    Good post! It’s a valuable lesson that sometimes you learn the hard way. When trying to start your own business, you must have an emergency plan in place. You have to have at least 3 months of savings because you never know when a client might come back to you and say they won’t be able to pay you on time.

  • Betsy Talbot

    We left the US and our careers in 2010 for a life of world travel and writing books. When we left, we were debt-free and had 5 years’ worth of expenses in savings to tide us over until our writing could pay the bills. It was not a sexy step (or a quick one), but it allows us to now live a damn sexy life and I’m so glad we made it a priority.

    One tip – we travel for part of the year and settle down to work for part of it. We do little “test runs” of livability during those work periods and cut ourselves off from our savings. We are only allowed to live on what we make during those months, and it is a definite motivator to continue building our business toward total sustainability.

    We’re almost there after 2 years, and the patience and focus of saving money and erasing debt before is helping us on the flip side of building a business and spending our money wisely now.

    Good skills to have on top of the freedom of knowing you’re going to have food and shelter with or without clients!

  • Robert @ The College Investor

    Caleb, thanks for highlighting my article. It really was interesting to see that pretty much all of them had their financial house in order before jumping to self employment. I think the financial diligence also translates into work diligence, and the same character traits allow success in both.

    • Caleb Wojcik

      Of course Robert. When Corbett brought your post to my attention it gave us the idea for this exact post. :)

  • Zivana

    Hi Caleb – awesome article and so true that we have to be emotionally responsible and in tune w our relationship w money. I eventually got myself a coach for a while and it was amazing the beliefs / self destructive habits I had around it.
    And I super-beyond-adore how you’ve linked this to giving back and the Africa water project. Thank you for that wonderful generous gesture!

    • Caleb Wojcik

      Thanks Zivana for the kind words. :)

  • Moe

    For every story of that strategic entreprenuer that prepared and made sure they had a nice financial padding before they quit there corporate job and leaped into internet marketing, there will be a story for the flipside of that coin.

    There are endless stories of people that were jobless or quit their miserable jobs and started their venture on a shoe string. And due to the pressure of a do or die situation, rose out of the ashes to become successful.

    Planning and preparing for that perfect break-away probably prevents more people from ever taking action then the other way around.

    I would only agree with this statement “The Not-So-Sexy Step That many Profitable Entrepreneurs took”

  • Izzy

    Caleb I couldn’t agree with you more.

    I think it is mission critical to get our finances in order before we take a leap to try and run a business on our own.

    Sometimes people think that if they had more time they could use that to get more done but there is a problem with this thinking. If we want to successfully run our own business we have to be extremely creative, resourceful, focused, and committed.

    Worrying about finances is extremely stressful and energy sucking. All the energy that needs to go towards building the business is used on worrying instead. Then soon the business becomes an extra stress as it becomes the end all and be all solution to solve the money issues.

    For me, I have saved up well over 6 months worth of income and I am doing part time work to cover my basic expenses. I work under 20 hours which gives me load of time to focus on building my business. But more importantly I have zero stress or worries. Which allows me to give my full focus and commitment to building the business.

  • Duncan Fawkes

    Hey Caleb,

    I couldn’t find an email for you so thought I’d post my question here. I’m interested in this course, you have my attention!

    However before taking the plunge I’d like to better understand the actual contents. I would expect one of your pieces of advice would be to “spend wisely”, so having fallen into the “sounds promising, buy buy buy!” trap before I was wondering if – without sharing all of your secrets! – there was a way you could share a preview of the 10 week content? Do you have a table of contents or some such?

    I’m not completely money unwise, so I’m kinda just wanting to see if I’m buying something I already know or something that’s new to me. I know you’ve got the 30 day guarantee, but we’d probably both want to avoid the hassle of that if possible! :)

    Thanks in advance!


    • Caleb Wojcik

      Of course Duncan. I just sent you an email with the table of contents and a free lesson of the course. Let me know if you have any questions. :)

  • Daryl Mander

    I can empathise with the point you’ve made in this article, I got my financial sh*t together by investing in a flat and then renting it out before starting my adventure into webpreneurship. My monthly rental income along with the small cache of personal savings I put together before making the leap should mean I’m taken care of for a while, at least until the business becomes profitable. Best thing I ever did!

  • Ayaz

    Hello Caleb!

    Certainly I have found the way of earning for living is the way that how you managed and learned new things in you niche or business to grow further. That’s a big challenge as some people learned few things and expecting lots of big things would be happen for them.

    For me, Learning is not stop and it should be continuously improving.

  • Andrew @ Blogging Guide


    I spent the first 30 years of my career in the corporate world. Climbing the career ladder, travelling the world and earning good money. I loved it!

    However, after 25 years the downsizing of companies started. I survived numerous lay-offs/redundancies but thought I needed my own “plan b”.

    That’s when I started my own internet business while still working full-time in the corporate world. I would work evenings and weekends to build the on-line business. It took 3 years before I could take the leap due to the financial situation I was in.

    Move on 4 years and the on-line business now provides me with a full-time income.

    As you say…don’t take the leap until you have a good financial foundation and if you are starting today, that could be 6 months’ worth of income.


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  • Jonpaulh

    I never normally comment but what a great article. I will definitely be checking out every article on here.
    I earn a decent amount of money just above average really, but until I set a budget I was living month to month spending precisely the amount in my bank every month. Then I set a budget and a target amount to save per month. The amount I’ve saved in such a short period of time is phenomenal. Once you save you want more in the bank and are encouraged to save more. Sorting out your finances and budgeting, planning to a reasonable extent is a must if you want any kind of freedom. How I regret every cent I wasted and the fact I can’t even remember on what it was spent.

  • Cliff

    Nice article really true, a basic necessity for the entrepreneur is perfect financial management, I have personally experienced d downsides of financial mismanagement

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  • Caleb Wojcik

    I should have phrased it a little better as “most that I know”. I love hearing that it wasn’t the case for you and the people you know. Can work a lot of different ways. (And it can also NOT work with or without a cushion.)

    Thanks for sharing! :)

Up Next:

10 Questions to Ask Yourself Before Raising Money to Fund Your New Business

Back when Fizzle launched, Corbett said, “We believe the Internet has started a revolution in entrepreneurship. It has never been less expensive or more possible to build an online business, to create an honest, innovative, true, fulfilling and valuable business.”

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