in entrepreneurship

Words of Wisdom from a Newbie Entrepreneur

So you want to be an entrepreneur? You want to leave the day job and start your own business? You want to work from home, sitting at home in your PJs watching Mrs. Doubtfire for the 37th time? More and more people are leaving the daily grind in pursuit of doing their own thing – call it Gen Y entitlement, call it a product of the recession and a rise in employee-layoffs, call it the new American Dream. Entrepreneurship is on the rise – the question is – are you ready to walk down that path? Do you even want to?

I get a lot of e-mails from folks asking how I ended up where I am today. 24 years old and running my own business. I tell them that…

1) I got fired and was thrown toward this path, so maybe it’s best not to follow in my footsteps…

2) I am by no means an expert or any sort of ‘model of success’. Each day is an exciting and often times stressful challenge, but each day I’m focused and driven by making today great and tomorrow even better for me and my family. I’ve been doing this (full-time) for 4 months. That hardly makes me an expert.

With that air cleared (because I truly don’t want anyone to think I’m an expert at giving any of this advice) here are some nuggets of wisdom I share with folks who are considering starting their own business:

Identify and Understand Your Worst Case Scenario

This point is huge. So many people I see aren’t “ready” for entrepreneurship because they’re not willing to accept the fact that things might not work out perfectly. You may not find yourself swimming in coins like Scrooge McDuck. If things don’t go according to plan – do you have a backup plan? Regardless of how much you’re bringing in, the bills don’t stop coming – they don’t care if you can afford to pay them or not.

Are you willing to take a step back to move forward? Are you willing to work retail or wait tables to make ends meat? Are you above going BACK to a nine to five if your freelance life isn’t panning out?

What I did, and what I tell other people to do, is to figure out what your ABSOLUTE worst case scenario is. Let’s say you quit your job today and start your own business. If it doesn’t work and you’re out of money – what happens next? What’s YOUR worst case scenario?

Is it moving home? Is it cutting the cable and phone bill? Is it waiting tables to make ends meat? So many are afraid to take the leap because they THINK their worst case scenario is much worse than it actually is.

Don’t Be (too) Proud

This goes hand in hand with my first point. If you’re not willing to take a step back and accept that things may not be perfect – if you’re telling yourself you absolutely will not ever go back to ‘corporate America’ – you may not be cut out for life as an entrepreneur. Scratch that, you’re NOT ready to run your own business. Unexpected things can and will happen – often times things that will be completely out of your control. If you’re business isn’t going as planned, are you willing to work at Best Buy to pay the bills while you work nights and weekends to get your business off the ground? Are you willing to suck it up and go back into an office? Something to think about before you take the leap.

Offer Something Tangible

It’s extremely hard to transition from a job with steady pay to the unexpected path of an entrepreneur without having something tangible to offer. ‘Consulting’ is something that is thrown around my world a ton these days – everyone calling themselves a consultant (even me). The problem with consulting is it’s somewhat intangible – you may not be giving a client something they can ‘touch and feel’.

So maybe your tangible something is web design – maybe it’s an info product you develop – maybe you write and self publish a book. You need that foot in the door to pair with other things you may offer. That tangible something may not be your focus down the line, but having something to help you get off the runway is the easiest way to get your plane up in the air at 30,000 feet.

Don’t Chase Money

If you’re thinking about going at it alone just to ‘make a lot of money’, you have the wrong attitude. You should only break away if it’s truly what you want to do. Don’t chase after the almighty dollar. Becoming money-hungry will almost always lead to disaster (I’ve seen some people around me fall into this trap). It’s going to be easy to say ‘YES’ to everyone – but you can’t be everything to everyone, you can’t take it all on. You’ll run yourself ragged and there simply aren’t enough hours in the day. Go into your own business because you have a passion for what you do, the paycheck will follow.

It’s OK to go back to a nine to five

When I decided to go full force with my own business four months ago, I didn’t tell myself that I’d “never go back to a nine to five” – and I’m still not opposed to it. There are many things to LOVE about the office environment, and great opportunities to be had in that world. I know MANY people who are much older and more experienced than I who have run their own successful startups, have gone back to a ‘corporate’ job – and vice versa.

There is NO right or wrong. Entrepreneurship isn’t for everyone – and even if it does make sense for you right now, it might not 5 years from now, and that’s OK. I see a lot of ‘either/or’ arguments happening out there and it doesn’t make any sense to me.

Go do what you want to do – or if it comes down to it – what you NEED to do. That’s the ONLY thing that matters.

Add Your Voice



  1. GREAT points here, Matt, especially the first. If you identify that ABSOLUTE worst scenario (barring family/medical situations and similar circumstances beyond your immediate control), you can have a much clearer picture of what can work for you. Knowing where rock bottom is is so important.

    While I agree with the offer something tangible point wholeheartedly, there are unfortunately thousands of idiots out there (most of them social media consultants) making money (supposedly lots) by selling absolutely nothing tangible (mostly complete bullshit). I don't think that's sustainable though, so actually, your point here is crucial too, if you want to stay in business. In a year, all these flash in a pan social media folks will need to find actual jobs.

    The one piece of crucial advice I would add to your (great) list is JUST DO IT. I'm not a sports fan by any means but that Nike slogan is killer. JUST DO IT.

    You're proof. You just did it and 4 months later, look at what you've learned. Of course you're still learning immensely (we all are), but by simply doing it, you learned a shitload.

  2. Great stuff Matt. I find an open attitude towards what can and may happen – allows you to work without a sense of undue stress.

    Having a “whatever it takes” attitude makes business building fun and exciting – In my humble opinion.

  3. All great points. Chasing after money and/or multiple projects and saying yes to everyone is definitely a sure fire way to crash and burn.

    I also loved Tim's points up there. We had the smarmy come out of the woodwork during the first dot-com boom ten years ago. Those people fizzled out and the people who truly were passionate about building good products are the ones with longevity written all over them.

  4. I love the post and I totally agree with 90% of your points. Especially:

    “This point is huge. So many people I see aren’t “ready” for entrepreneurship because they’re not willing to accept the fact that things might not work out perfectly.”

    All accept for “It’s OK to go back to a nine to five.”

    In my humble opinion not burning the boats once you've hit the shore is a fatal mistake. It leaves the open the door of mediocrity. It gives you the ability to “rationalize” why quitting your venture is ok. In my experience you haven't really decided to commit if that option is still open.

    I'm not saying that changing directions or backing up isn't an option. Such as even doing a different venture. But leaving the door open to something you didn't want to do in the first is not in your best interest.

    Not to mention long term unemployment is up at 46% right now. The most it's ever been in U.S. history.

    My point is, the job market is crazy upside down right now and not even really that much of an option. Hence why there are more people starting up their own businesses right now. Even more than when the Dot Com explosion hit.

    The wisest thing to do is as you pointed out is to do what it takes and start up your business “while” you have a job. Don't walk away from it. (Whether waiting tables or whatever) Transition and walk away from your job once you've replaced your income and have at least 6 months of expenses put away with your “part time” venture.

    Good article, I just don't care for the “commitment” trap door of a 9-5.

  5. Matt, I'm so glad you wrote this post! After our Skype conversation a few weeks ago, your words, “What's the worst that can happen?” have been floating around my head. And guess what, as of Monday I signed a small contract project with a company and bought my business license. What's the worst that could happen? This could actually work…

    So there you have it, Matt Chevy, I'm a newbie entrepreneur and I'm in. I'm still trying to figure out what this “business” will look like, but hey, both feet are in the water now :)

    There was a post on Itty Biz yesterday that speaks to the fears of being an “itty biz” owner. I think you'll enjoy it:

  6. My favorite piece of advice was something I realized when I recently read How To Stop Worrying And Start Living by Dale Carnegie — your worst-case scenario is rarely as bad as you imagine it. We tend to blow things out of proportion and leave ourselves paralyzed as a result.

    I'm glad this article was written by someone close to my age (I'm 25), and you give me hope that maybe I'll hit my groove one day and try my own thing. Great post, Matt.

  7. “In my humble opinion not burning the boats once you've hit the shore is a fatal mistake. It leaves the open the door of mediocrity. It gives you the ability to “rationalize” why quitting your venture is ok. In my experience you haven't really decided to commit if that option is still open.”

    Completely agree. Go big or go home. If you're not 100% dedicated, it's not going to happen.

  8. Wonderful comments above.
    I especially like Tony Teagarden's rationale about the “escape hatch”

    For the past 50 years I have encouraged clients to move through the Business development process following Clear Roadmaps.
    It is best to HAVE sustainable Income (or the capitalization form Savings-never borrowed) while putting the pedal to the metal.
    I fondly remember working with clients in Garages at night shipping sprinkler parts, etc, AFTER the 9-5 job and 5 years later enjoying 40,000 sq ft mfg plants (paid for) and 100+ employees…
    Surveys I've conducted have indicated major faults in the new Entrepreneur Mentality are:
    Lack of Awareness (time spent researching)
    Lack of Planning (Plan of Action plus Cash Flow Projections and BUDGETS)
    Lack of willingness to discipline MASSIVE ACTION NOW!
    I feel it really boils down to:
    Lack of the MINDSET of a Business Person
    and that IS a learned Skill Set.
    Voice you opinion
    Thanks again Matt for the Great post.
    Love to see your generation on Top of The Main Thing
    And then Selling the company to start all over, but much easier the second time around

  9. Great point here Tony. I don't disagree with you here. Telling yourself “I'll try but if it doesn't work out, oh well” is an attitude that,as you said, really smells of mediocrity. However, I do think it's critical for any entrepreneur to understand that things may NOT work out, and that if they don't – they shouldn't be too proud to, say, go back to waiting tables while they pay the rent and perhaps continue their freelance work on the side. It could very well happen to me – I don't know. No entrepreneur or freelancer knows what paycheck tomorrow will or will not bring.

    My point above was that, if you are being idealistic going into starting your own business, thinking that there is absolutely no way you will EVER do anything except run your business, that arrogance can lead to disaster. You never know what life with throw you way. Of course go full speed ahead, but realistically, if things don't pan out, you still have bills to pay.

  10. I learned very VERY quickly that you cannot be successful by saying yes to everything that comes your way. The power of 'No' is something that has to be tapped into very early on. Setting realistic expectations is critical. Thanks for the comment, Stacy – good to see you around here!

  11. Yes. The 'Whatever it Takes' attitude is necessary for anyone to be successful as an entrepreneur, in my mind. It's not about 'preparing for or expecting' the worst, but understanding that shit happens and sometimes you'll have to face it head on.

  12. That is great to hear Laura. I loved our conversation a couple weeks ago and congratulations on taking that step – it could actually work! I like your attitude. Getting your feet into the pool is half the battle – swimming is he easy part, right? To be determined…

    Also, great article you linked to. Thanks for sharing!

  13. I'm not throwing an “Oh well” in there on the end of “If it doesn't work out.” There are always going to be setbacks, challenges and issues that arise as a self employed solopreneur/entrepreneur.

    This is why I've coached the vast majority of people I've worked with to make sure they have already put in place a plan, replaced their income on the side with their business and are moving sensibly forward without risk of not paying their bills or feeding their family. To speak of otherwise would be irresponsible.

    My point is going in with any amount of uncertainty and saying I've still got a 9-5 thing option if it doesn't work out is setting oneself up for just that. That's not arrogance mind you, that's me saying, “Ok if I'm going into this thing with a plan, one that is flexible and able to be accomplished before the battle ever starts then how can I lose?

    A free lancer or home based business individual should be building their business “on the side” prior to jumping in cold turkey anyway in my humble opinion. I've been self employed for 20 years now. Full commission, never a salary. In the beginning did I have my challenges and nights where I sweat paying the bills tomorrow? Sure!

    Did I learn how keep that from happening? You bet.

    “Realistically” is in the eye of the persons perception. I ideally don't leave things to chance and you'll find most entrepeneurs who have gone through this process are some of the least “risk takers” you'll find.

    I still don't stand moved on the subject and based on your reply I realize you may think my mind set as unrealistic or arrogant. Far from it really. I just believe if you go into this process with the right plan you'll risk little and going backwards won't need to be an option. You won't have to. That's me being realistic after 20 years of doing it. A plan can replace proud any day in my book.

    I'm extremely excited for you and wish you of course the most badass success ever.

  14. Hey Tony. You hit the nail on the head here:

    “Ok if I'm going into this thing with a plan, one that is flexible and able to be accomplished before the battle ever starts then how can I lose?”

    I completely agree – and this is exactly what I did. I freelanced on the side for 8 months or so before I made the jump (even though the jump was involuntary). Doing this allowed me to create a plan (quickly mind you – but a plan nonetheless) that turned the risk into a calculated risk with as you say, a backup plan to make sure I can support myself and my wife.

    I hate the word 'realistic' too – Shame on me for throwing that out there. I understand the need to be 'realistic' (whatever that means to you) but it is far too synonymous with mediocrity and selling yourself short.

    I don't think your arrogant or wrong or anything like that – I'm glad we're having this back and forth – it helps me and everyone else taking the time to read our 'banter' put some things into perspective. Cheers!

  15. Well congratulations for you man for stepping into your greatness and doing it. I've got mad respect for you for it and never the less you've given some outstanding info here for new people.

    I've come across countless people who have been unemployed for 2 and even 3 years. You've put yourself in the mix to make things happen and I believe more people will be looking to your wisdom in the coming months.

    I'm glad you take a healthy outlook on our “banter” as it's awesome material to discuss. Thank you a ton for the platform to do so and again, wishing you nothing but awesome success along with healthy challenges to grow from.

    Rock on!

  16. Just went back to being on my own, and I was surprised when telling others how many said “I wish I could do that but ___”. It isn't for everyone, you have to be able to motivate yourself and power through those days where things can get overwhelming.
    I love the don't chase money advice. So true, and I have seen it destroy others as well. The best advice I have ever received was “don't be afraid to say no to a customer.”

  17. Matt,

    I 've been looking over this post for the last few days and giving alot of thought to all the points you bring up here. I think once you have actually experienced your worst case scenario you often realize it's not the catastrophe you have made it out to be. We do alot of mental projecting when we go down that route, but I think it's necessary.

    Don't be Too Proud: It's funny that you brought this up because it was one of the topics of our chat, and I think one of my personal favorite ones. I think this is something that's really hard for us, especially if we feel like we're overeducated, underpaid, and underappreciated. Fortunately, I'm not in that boat. But, in the 8 months of searching for a job I liked there were times where I had to considering doing things like getting a job working retail, which seemed insane after getting an MBA. I think that you have a balance between humility and standards (a post I'm working on). But in the end those who are willing to do what it takes will succeed.

    Offering Something Tangible: This is really where the hardest part of the work as an entrepreneur comes in. Many of us do consulting work and it's true that it's not something tangible. I spoke with Dave Navarro from The Launch Coach the other day and we definitely hit on this. One thing with getting tangible stuff together is that it is alot of work in beginning for a pay off later on. So really it's about frontloading time as Dave described it.

    Chasing Money: At 32, I've spent my whole life chasing money and being a paycheck player. The irony is that when I stopped opportunities to make money and money have showed up in my life. The other thing is that I'm doing something I love so I guess it makes sense that opportunities are much more abundant.

    The 9 to 5: I'm more or less a 9 to 5 employee with a dream job and flexible schedule. I learn alot from it and I don't have the pressure of wondering if I'm going to make enough to cover everything the following month. I've been fortunate to end up in the hybrid role of entpreneur/employee because I can work on my passions without the pressure of generating an income from my passion. It's a hard thing to find, but I think it is possible for everybody if they are willing to look for it.

    Solid stuff as always Matt.

  18. Matt – great site and excellent post. “Have a passion for what you do and the paycheck will follow.” That's my favorite line and it's great advice. But like you said, you have to identify and understand what the worst case scenario can be….and if you think you can stomach that, then dive on in and take your passions with you. Despite the debate, I think your point that it's OK to return to a 9-5 gig is good advice. I don't think it's showing a lack of dedication or opening yourself up to mediocrity. It's just part of your point of understanding that that is likely the worst case scenario…that you give XYZ your all…and if it doesn't work OR if you get bored with it and want a new adventure, you can then bring even more experience to the table at a gig working for someone else. Or maybe that gig can supplement your income while you build XYZ. I'm a big believer that the entrepreneurial SPIRIT is the key…not just working as an entrepreneur. Looking at it that way, you can bring your mindset and skills to your own thing OR to an existing company's thing. Every company needs that spirit if they want to thrive…and you can help them keep that edge and thrive by bringing that spirit. There can be a lot to be gained from working at companies (teamwork, meeting people you wouldn't otherwise meet, getting to work with and learn from experts you would otherwise have to hire for the big bucks, etc.). So I don't think there is anything wrong with going back and forth between solo and corporate gigs. I've gone back and forth and have enjoyed both routes.

    As for chasing money, I've never seen that make anyone happy. When I was an attorney recruiter with an LA-based search firm, I found that many young associates at law firms were miserable because they didn't like the practice of law….they just liked the fat paycheck. So they stuck around for that. And their misery stuck around too! One of my college friends went to Wall Street to make money. Even when he was pulling in $1 million/year, it wasn't enough….he always wanted more because someone down the hall was making more….and that cool new car is really expensive, etc. Like you said, chasing money should not the motivator for choosing work or going the entrepreneurial route.

    Good job with the post. OK, gotta run – Mrs. Doubtfire is starting.

  19. Don't be too proud was the advice that resonated the most with me. I have vowed to myself never to work the 9 to 5 again, so I guess my only option is to try to build a business.. Haven't really started on that yet.. enjoying a career break sabbatical for now :P Thing is though, I vowed NEVER to go back to a 9 to 5.. I never thought of this as a source of pride, and a recipe for failure! Thanks for reminding me that sometimes sucking it up for awhile to make ends meet is all part of the bigger picture.

  20. Saying “no” and being OK with it is one of the first things I've learned. Starting out, you see dollar signs and you want to say yes to everyone – you want to be everywhere for everyone all the time and…you just can't do it. You have to be able to manage expectations and, sometimes, be OK with saying “no” and moving forward.

    Thanks for coming by Rachel. Hopefully out paths will cross here in Chicago one of these days.

  21. It is all a part of that big picture – just don't get too caught up in being discontent while you're doing what you've got to do to get by. Yes, sometimes life will throw a curveball and you'll be working a less-than-glamorous job, but as long as you're working toward your dreams, personally, professionally, whatever, you're doing the right thing, and there's absolutely nothing to be ashamed of.

  22. The reason why I work an extra 25-30 hours on the Yakezie Network and Financial Samurai because it is fun. It has never been about the money. And the funniest thing is, after the sites grew, and the Alexa Ranking went sub 100,000, then sub 50,000… the money just started coming left and right.

    IT’s like… HUH… weird. You want to pay me $200 a month to put up your banner? Ummmm… OK! Ill take it and donate it away, or use it to sponsor the Yakezie Writing Contest. Blogging really is one of the craziest “do what you enjoy and the money will come” examples. Kinda nuts.