How I Became an Accidental Entrepreneur

What’s up, y’all!

Stumbled across this old interview I did a few years ago for on how I became an entrepreneur/blogger full-time, and thought it had a lot of good financial and career nuggets in it that you might like. It’s also a great overview of my story in general for those new to the site, and it’s even in bite-sized A.D.D. chunks too! Only the best for my people! Haha…

Hope it helps :)

PS: For the audio version, check out episode #1 of our new podcast – M.O.N.E.Y. – which goes over a lot of it too… As well as the fascinating background on my beautiful counterpart, Paula Pant.


You have two blogs (Budgets are Sexy and Rockstar Finance) as well as consulting. Do all these provide enough income to replace a job, or do you have other businesses?

Yes, they provide enough income to replace “a” job, but not always “my” job all depending on what’s going on in my life ;) Like, right now as my wife is not working and we’re about to have baby #2 (woo!) (since born!). So due to this I also manage a handful of other projects as well here and there on the side for extra money. All mainly online stuff.

How do you balance all your businesses?

I hustle my a$$ off and sleep only when everything’s done for the day. Which could be 11pm one day, and 3am the next. But it all comes down to prioritizing and constantly working towards my end goals. And it doesn’t hurt when it’s all FUN stuff too :) It’s amazing how many hours you can put in when you’re working on stuff you love!

(I no longer stay up super late with my Ben Franklin 5 am schedule (today marks 6 months already!) but the part about not ending the day until the necessary stuff’s done still remains very much true)

Why did you start a side business in the first place? Why choose a side business, instead of quitting your job first?

I actually had no intention of starting any type of business whatsoever. I was tired of wasting time on YouTube and MySpace (remember that?), so thought I’d just try out blogging for a while and see how it goes. And as luck would have it, there was money and opportunity to be made :) So here we are 5 8 years later!

As for quitting a job first, there’s no way I’d ever advise that. Unless you had tons of money saved up AND something worth trading your time for. Most “businesses” fail early on, so I always advise to build and grow it on your spare time, and then once it’s successful (aka it *makes money*), start making the game plan to leave your 9-5. For me it was supposed to match 100% of my income before I left and went on my own, but as fate would have it I got laid off and jumped in feet first at around 80% of my old salary. Not perfect, but it did give me the push to finally give self-employment a try.

How did you organize your schedule when you were working full time so you had enough time for your side business?

I worked on my lunch hours, on my down time, during parts of the work day I probably *shouldn’t* have been working, haha, and then as soon as I got home until I went down for bed. At least that’s how it turned out after the first couple of years of blogging. I started with one hour a day, then moved to two, then three, and eventually 7-8 a night (on TOP of my 8 hours of work each day) when I knew what I finally wanted to do – go on my own.

That’s really what it all comes down to at the end of the day – how bad you want it. If all you want to do is work and build your business, then you gotta do whatever it takes to get to that point. Which means a lot of hard work and sacrificing. But again – “hard work” with a business you love vs hard work with one you don’t are totally different beasts. Doing stuff you love makes it a lot easier to see the light at the end of the tunnel :)

How did you keep your side business private from your boss and coworkers?

I kept everything as anonymous online as possible, and I didn’t tell a soul. And most of the times I did stuff/made notes/etc through my Gmail account or on my iPhone which wasn’t as trackable as it would be on a computer that the higher-aboves monitor. This is probably way different than other side businesses out there which has nothing to do with a computer, but for me that’s how I ran with everything. Having a business online makes your life incredibly easy!

Do you think part time entrepreneurs should be open with their employers about their side business?

I think it all depends on what type of job you have, and how good your relationships are with your bosses/colleagues. But more times than not I’d highly suggest not mixing the two just in case anything funky starts happening with either of your two “jobs.” It’s similar to your sex or political life – some things should be kept to yourself!

How did you create a plan to save enough money to quit your job?

As a money guy at heart, it was pretty easy – I just figured out a) How much I needed in my savings account to cover me for a good 6 months (the time where I agreed to get a new job if all went to $**), and then b) how much I needed stashed away to have a stress-free sleep every night. Luckily they both coincided and were the same amount: $50,000.

Now as you may recall, I got fired before I was 100% ready to jump in, but fortunately I had already reached about $40,000 in savings so I was pretty confident that it was time to push GO and rock it. I’ve left other jobs in the past to pursue dreams with no money saved up, and let me tell you – it makes a DRASTIC difference.

How did you determine your quit date?

By the amount of money I wanted to have saved up: $50,000. But I should also note that I needed my business to be generating most of my normal salary in terms of money too. So it was really a combination of both those which made me comfortable to go self-employed. Having one or the other is still nice, but for me – a conservative money guy – I needed both. But at the end of the day I got fired anyways, so…. :)

How long did it take for your side business to make enough income for you to consider quitting your job?

About 2-3 years. Once I realized there was money in blogging, I started working harder and faster which helped to speed up the process. It really was a matter of falling into something that I thought was only going to be a hobby, but turned into a money-producing business. But what better way than that?!

What advice would you give someone who wants to earn side income, but doesn’t know where to start?

Start by making a list first of all the stuff you LOVE to do – no matter what it is (I once had “drink beer” “meet girls” “travel” on mine – which helped me to work for the airlines so that I can drink beer and meet girls, haha…), and then make a list of the stuff you’re GOOD at it. Anything that crosses over from those two lists are good starting points of building businesses around.

Working on stuff you love AND you’re good at is a pretty good mash up. Rarely do I know anyone who starts a business *just* for the money, but in either case the whole world is really open to look into. And I suggest starting with our side hustle series  :)

What do you consider to be the quickest way to generate income?

Asking someone right now on any social media platform if they’d pay you for X. Have a product idea? Try selling it first and THEN making it if anyone buys. Have something you want to offer up as a service? Tell people you’re offering it right NOW and see if anyone bites!

I did this when I wanted to start consulting and started getting results (good and bad) within seconds. I can’t remember the term for this strategy, but there’s no point in spending the time and energy building something out if no one wants it. So by reversing the “rules” and offering it out there as if it was already built can make for good proof of concept right away.  But of course then be prepared to hustle the second someone takes you up on it!


Moral of the story? Carve out a little time every day to work on stuff you love as you never know what can come of it. And if you’re fortunate, it might just change your life.

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  1. Chris @ Flipping a Dollar February 10, 2016 at 5:34 AM

    Awesome that you’re still doing the 5AM wakeup.

    Do you think you’d take the same risks now that you have kids? I have way more stashed away than you do right now, yet I wouldn’t feel comfortable dropping everything to work from home. Obviously my blog is nowhere as popular as yours, and even with my eBay income, I wouldn’t be close. I can’t decide if the kids just make it harder or if there’s the fact that I make a really good salary at my job too.

    1. J. Money February 10, 2016 at 6:48 AM

      Today actually marks 6 months since starting the 5 ams – crazy! It was only supposed to last a week! Haha…

      RE: Risks – I probably would have been much less confident going into it all, but yes – I still would have gone for it. Mainly because we had the savings and my blog business was already working and supplying income. I would never just quit and then pray I could figure out how to make money online though, so that would be the major key to it all. Also in my case I was terminated anyways so it wasn’t about staying at a nice job vs quitting, but rather “looking for a new job” vs blogging full-time. And I just had to know if I could make it or not so I would have gone for it and then just made the testing window shortened in case I had to go back to a 9-5 again.

      I will say this though – If your dream is to retire early more so than work a fun/dream job like blogging, then I’d lean more towards sticking to the kick-ass income and banking as much as I can in order to reach that epic milestone sooner. It took me quite a few years to break even, and then start saving again – which was a huge difference from having a surplus of money from the 9-5 and blog on the side! So really all goes back to priorities and what makes you happy at the end of the day…

  2. Ashley February 10, 2016 at 7:13 AM

    Great advice! I used to do a 6 am wakeup in college and getting up early is totally effective to get things done. Working out first thing in the morning is helpful to get the blood flowing to the top floor as well but some days that is just too ambitious. ;)

    1. J. Money February 10, 2016 at 10:34 AM

      haha, yeah- now you’re just talking crazy ;)

      I don’t know how you did the college wake-ups – half the time I went to bed at 6!

  3. Roy Largo @ Band of Savers February 10, 2016 at 7:13 AM

    Thanks J. Your story is always inspiring to hear. It’s nice to hear about people who can find their dream and actually find a way to live it. I’m still trying to figure out where my “what I enjoy doing” and “what I’m good at doing” circles intersect.

    1. J. Money February 10, 2016 at 10:47 AM

      It can take a while :) Took my 28 years to stumble across it – and it was an accident!

  4. Penny @ She Picks Up Pennies February 10, 2016 at 8:22 AM

    I love the idea of looking at what you love to do and what you’re good at. That’s great advice for a side hustle, and that’s even better advice for a full-time career. Totally loving the podcast, too!

    1. J. Money February 10, 2016 at 10:32 AM

      I’m so glad!! We’re having a blast doing it :)

      Yeah – the part about ENJOYING it is most important in my books. It can be a grind getting stuff off the ground, and if your heart isn’t into it the odds of giving up/burning out go through the roof. I don’t know anyone who’s started a blog purely just for the money – you gotta love it (other industries are different, of course, but still gotta put your heart into it!)

  5. Brian @ debt discipline February 10, 2016 at 8:29 AM

    I like the early AM wake up too. I find I can get a lot accomplished without distraction during that time of the morning. I got a chance to listen to the M.O.N.E.Y podcast episode #1 this weekend it was a great overview. Love the format too, very conversational.

    1. J. Money February 10, 2016 at 10:36 AM

      Love to hear that! Exactly what we’re going for – like you’re having a beer or coffee with friends, only talking about something most people don’t in real life – money ;) I think we tend to go off course a bit, and I’m realizing I say “like” just about every 3 seconds!, but we’ll get better over time… Just proud of us for actually getting it out the door :)

  6. Bobby@ Millennial Money Man February 10, 2016 at 8:38 AM

    Wow this is really cool J! I didn’t really know much about your story other than what I had read in your “I Just Got Fired” post. This is going to sound weird because I know you have kids and are super busy now…do you ever get bored blogging and working online? It’s been a weird experience for me when basically everyone in the world is at work all day and I’m not (technically). Thanks for sharing my man!

    1. J. Money February 10, 2016 at 10:55 AM

      Definitely! Some days I could care less about money or blogging or twitter, or just being self-employed as a whole really. I often joke that the 9-5’ers might have it right where you put in your time and then enjoy life on the nights and weekends – something most hustlers are bad at ;) I also get tired of always making decisions left and right with articles and advertising and partnerships and design and yada yada yada… I’m not naturally a leader/manager so those parts aren’t something that excites me much.

      All that said though, I love and believe in what we’re all doing here and 90% of it IS all fun/exciting, so I push through and do my best to not dwell on the sucky parts too much… I also have no idea what else I’d do w/out this blog & my projects so that alone keeps me put! Haha… Good problems to have, I suppose :)

      But yes – it’s not always rainbows and unicorns as you know… Getting out and working at coffee shops or co-working spaces helps a lot to connect back to the real world for sure. I’m typing from a cafe as I write this!

  7. Broke Millennial February 10, 2016 at 8:39 AM

    I don’t think you mentioned you worked during “down time” or lunch (totally passable) at work on the podcast, because that’s what I do! Great to know I’m in good company. Now I know I need to be pushing myself to wake up earlier, I’d just rather be a night owl. Maybe I’ll try the Benjamin Franklin crazy pants schedule you’ve been on.

    1. J. Money February 10, 2016 at 10:39 AM

      Try it just for a week and see what you notice! It does suck having to go to bed earlier in the beginning, but I’ve found I actually enjoy being in bed and having that down time to relax and just chill without having *work* be the last thing on my mind (and first thing when I wake up). I’ve actually stopped snacking so much and eating junk food too at night! I trick myself by brushing my teeth after I put my kids down (8:30/9’ish) and then I’m too lazy to re-brush them so I just stop eating :) So it’s had some interesting side effects over time, haha…

  8. Mortgage Free Mike February 10, 2016 at 9:18 AM

    Incredible story. All of the specific details (thank you) are very helpful for us wannabes! Continued success…

    1. J. Money February 10, 2016 at 10:40 AM

      thanks man! got your email btw – starred to read/respond soon :)

  9. ESI February 10, 2016 at 10:06 AM

    I recently finished a book called “The Miracle Morning”. It’s main point is the same as Ben Franklin’s: get up early and get things done.

    There’s actually a pretty active Facebook group dedicated to it as well.

    I can’t say that I’ve implemented it fully yet, but I am getting up at the same time EVERY day (even the weekends) and get much more done those days as a result.

    Time will tell if I begin getting up earlier or not. :)

    1. J. Money February 10, 2016 at 10:42 AM

      I’ve heard that’s a great book! I think it’s one of those things that just happens when it’s time and you really care, or won’t. I’ve heard it’s smart to wake up early for 35+ years and only now did I finally try it. Guess the same with paying attention to money, stopping smoking, exercising,etc.. Just hits us when we care enough to finally do something about it!

  10. Abigail @ipickuppennies February 10, 2016 at 10:11 AM

    I definitely agree that it’s better not to tell your employer about your side hustles. It’ll help your anonymity (if you go that route) — and then they’re not snooping to see if you’re saying anything about them.

    My employer already knew I had a blog. He actually checked out a couple of pieces to see my writing style. But that’s kind of a different story than you.

    Ah, how the time has flown, eh?

    1. J. Money February 10, 2016 at 10:43 AM

      You and I have known each other for a bulk of these years too, eh? Pretty cool :) 99% of my current friends all came from online! Haha… we’re such nerds!

  11. Mr. Tako @ Mr. Tako Escapes February 10, 2016 at 3:39 PM

    Great story J. Money. How long did it take from when you first started blogging until you saw significant money coming in? (say $1,000/month)?

    1. J. Money February 11, 2016 at 2:05 PM

      I think around the year and a half mark? I remember hitting $700 total after about 8 months, and then from there it kinda started to take off… It really went into overdrive though when I started scooping up other financial blogs and cross-advertising everywhere. So a bulk of my money over the middle years came from a combination of sites, not just Budgets Are Sexy for what it’s worth.

  12. Tracy @ Financial Nirvana Mama February 10, 2016 at 7:10 PM

    Crazy awesome that you can wake up at 5 am. I have a tendency to goto sleep late, like 1 to 2 am, and wake up at 7 ish. I don’t drink coffee either, causes heart palpitations so I’m on tea most of the time. I started my blog more than a year ago to share everything about real estate, now I’m taking the blog much more seriously and it’s a huge time commitment! And it is inspiring to see your journey evolve from it as fuel for me to continue. Question for you, do you miss the social interaction? I remember being incredibly lonely when I took a year off and I yearned to be around people all the time, to talk to people in person. I realized that i don’t like working alone, ever, and I hate working in my pjs. How do you get around that?

    1. J. Money February 11, 2016 at 2:07 PM

      Yes – I get lonely all the time so I’m constantly at coffee shops or co-working spaces/etc to be energized around people.. Doesn’t even matter if I talk to them or not either, haha.. it just feels good being around others! :)

  13. Stockbeard February 10, 2016 at 7:42 PM

    Sounds a lot like my story, except that my side gig is far from replacing my salary, even after 8 years!

    1. J. Money February 11, 2016 at 2:07 PM

      But isn’t it nice having a million dollar salary? ;)

  14. Tyler @ Oddball Wealth February 11, 2016 at 1:16 AM

    Sometimes the best things happen by accident. Awesome post. Keep up the great work!

    1. J. Money February 11, 2016 at 2:08 PM

      You know it! Good luck w/ your blog too! :)

  15. Megan @ Prioritized Living February 11, 2016 at 2:42 PM

    So true that you need to hustle and want it. No one else will build your business for you, and you have to be motivated to make it happen. Jumping out of — or getting dumped out of — a 9-to-5 job definitely does that! Thanks for the inspiration!

  16. Mortimer February 12, 2016 at 1:16 AM

    So awesome that you could turn a side passion into a self-sustaining income stream. Sounds crazy scary and also totally exhilarating to be totally self employed AND supporting kids. I guess for now I’m happy to have the stability of an office gig but maybe when the debt is all gone I will feel differently… Cheers for another inspirational post!

    1. J. Money February 29, 2016 at 4:49 PM

      The awesomeness def. helps make up for the scaryness at times :)

  17. Chris "Stasher" February 15, 2016 at 10:13 AM

    Nice background story my friend , always enjoy the insight. It’s actually valuable for you as well to reflect and review what you did in the past. It gives both perspective and opportunity to look at things that may have been missed back then. Keep hustlin’

    1. J. Money February 29, 2016 at 4:50 PM

      Thanks man. Looking forward to meeting up with you one day up in V-town!

  18. Paul Dabuco February 16, 2016 at 6:28 AM

    Great post. Although I never believe about being an “accidental” entrepreneur. It is exaggerated.

    Being an entrepreneur requires hardwork and it doesn’t happen overnight or with a great idea. The reality is entrepreneurs stand through test of time and the implementation of great ideas.

    No matter how great your idea is if you’re not doing it in action it will “just” be another idea

    1. J. Money February 29, 2016 at 4:51 PM

      True true… more “accidental” in only the beginning when I didn’t mean to become an entrepreneur :) Or even knew I had the bone in me.