10 Things I Wish I Knew Before I Started My Business

In 2005, I wrote my first blog post on an unknown personal finance blog that would eventually grow beyond my wildest dreams. A few years later I would quit my comfortable stable job in the defense industry to work on a “blog” full-time.

In the ten+ years since, there are a few things I wished I knew. While I wouldn't change anything in the last decade, a few of these lessons would've made the ride a little less of an emotional roller coaster and more of an exhilarating rocket ship ride. 🙂

To give you a bit of context, when I started my first blog I never intended for it to become a business. I thought it could make a few bucks, I'd learn more about personal finance, pay for a nice vacation each year, and have a fun little hobby. It wasn't until two years in that it dawned me that this could become a business…

1. It's hard. Really hard.

Like Sisyphus pushing that boulder up hill, running your own business is hard. There are a lot of three steps forward, two steps back type of situations… and some zero steps throw in for good measure. Sometimes that boulder doesn't budge an inch.

And you spend a lot of time on the brink. Sometimes it's a financial brink, sometimes it's an emotional one, but you end up living on that edge. If you're doing well and hiring, you run into cash flow problems since employees get paid every week and vendors only pay you after 30 or 60 days.

When you talk about it with other people, you'll share the good stuff because no one likes to hear the bad stuff and there's no fun in reliving the challenges, especially the emotional ones that sound silly when you say it out loud. The only people who understand those are those folks in your industry.

The solution: Find other business owners you can talk to, preferably in a variety of businesses. Build your own community or find one to join, it'll help your sanity in ways you can't imagine. If nothing else, find at least one person in a similar situation you can talk to. Just one will change your entire outlook.

2. It's lonely.

I've learned and grown a lot the last ten years running my own business, take a minute to learn some the lessons I wish I knew before I started!There's no foxhole mentality like you have with a regular job. Whether you're tapping away in an office, pouring drinks at a bar, or packing crates in a warehouse, there's a sense of community. You're in it together.

When it's you're business, it gets pretty lonely. You have a lot of responsibility and it's yours alone. It helps if you have co-founders or business partners, but even then the buck will stop with one person and that person will carry that burden alone.

You combine that with the difficulty of the task and it's easy to see why so many businesses fail.

The solution: The solution to this is the same as before — find at least one other business owner you can relate to and, if nothing else, be able to safely vent to. 🙂

3. Growth is bumpy. Very bumpy.

When I look back on the growth of my businesses, it looks so smooth. Each month is higher than the last month.

Dig deeper and the daily numbers jump all over the place. Sometimes one month is saved because of a single good day of sales. One day out of thirty made the month. Or one month out of the year made the year. The month looked great and the year looked great because of a single day! (then there's the pressure of having to repeat next year so your year over year results are increasing!)

Whether you measure growth by revenue, traffic, or some other measure – realize that it'll be bumpy.

The solution: Once you realize that life isn't this smooth curve that goes up and to the right, you give yourself permission to not freak out when it just goes to the right like a Geiger counter. You take that bias out of your thinking and now you can stop beating yourself up because you didn't make progress. Progress is messy, especially if you look at the numbers!

4. Your friends & family won't be customers.

There are no free lunches in life. Your friends and family will want to support you, sometimes financially by being customers, but you shouldn't count on them day in and day out. It's not that they don't love you or they don't support you, it's that they have lives too and their job isn't to keep you in business.

In the beginning, I joked that the only people that went to my website were me at home, my girlfriend (now lovely wife!), and me at work. My friends asked about it and said they visited, but I knew they didn't. And at first it bothered me a little… until I realized there are no free lunches. If I want them to visit, I have to give them a good reason to. I don't get a free pass just because we're friends.

The one exception to this is your mom. She'll remember. Love you Mom!

Nowadays, I enjoy getting the occasional email from a friend who said they saw something I wrote because it popped up on a Google search or on social media.

The solution: You cannot assume that your friends and family will remember but even if they did, it's not like their patronage alone would sustain your business. Make a business that demands their attention and not only will you get it, your business will thrive because of it. And you won't be upset at them for something as stupid as this.

5. Find something to fuel your drive.

When I first started, I told my friends all about it. One of them would ask me, every time I saw him, how it was doing. It wasn't a friendly “things going well?” type of ask, it was a “heh, how's the blog doing, making any money yet?”

I remember the last time it happened too, like it was yesterday, and whenever I feel down on myself because things around going as well as I'd like — I think back to that moment. It's like Popeye squeezing that can and getting his spinach, I'm ready to push even harder.

We all have this fire in our belly to do more, it's why you may have started a business, but sometimes the challenges of the work dims the light. Keep motivation at the ready to get it roaring again.

6. There's a safety net. But it sucks.

You may think that there's no safety net when you start a business, but there is. It's called going back to work. It's not a good safety net, because it's really hard once you are on your own to go back to reporting to someone else, but it's there.

And while your friends and family won't automatically become visitors and customers, they will be there to pick you up if you happen to fall.

This means that you can afford to take calculated risks. Don't play it conservatively, especially in the beginning when you're trying to make a name for yourself, and be willing to try things that are outside your comfort zone.

6. Reinvest in the business.

Your goal with your business should be to grow it to a size and then sell it. To that end, you should be trying to grow it as much as possible in the ways that will appeal to a future financial or strategic buyer. Reinvesting your profits back into the business is the best way to grow it.

Do not conflate business income with your personal income (beyond your salary). Remember, capital gains tax is much much lower than ordinary income tax so if you can grow your business to a point where you sell it, and get a balloon payment at the end rather than a regularly constant drip, you win.

7. Pay attention to the numbers.

Numbers will tell you everything. If you want to understand a business, ask for the numbers.

How much does it cost to get a customer? How much is that customer worth to the business? If the cost is greater than the worth, you have yourself a problem. If the cost is less than the worth, you need to invest in ways to get more customers!

If you don't know those numbers, you're in big trouble.

And don't be afraid of the numbers. If you're one of those people who says “I'm not good with numbers.” then you need to save yourself some heartache and not try to run your own business. Or get better at it and the only way to get better is by running towards them and not away.

8. Celebrate little victories.

A business is a grind. It's a lot of the same thing over and over again, even if you focus on innovating, and, especially in the beginning, the little victories will be few and far between. Sometimes it'll be a good financial day, sometimes it'll be a good PR day, and sometimes it'll just be a customer telling you that you're business is awesome or that you helped improve their life in a small but meaningful way.

As your business grows, the victories become relatively bigger, more frequent, and hopefully you reach an escape velocity where things start to soar. But to reach that point you have to continue grinding onward and upward, celebrating those little victories so you remain emotionally invested.

With my first blog, it took nearly 7 months before I earned enough advertising money from Google to have them cut me a check ($100 payment threshold). And that was only because I was featured in the New York Times and received a nice flood of traffic.

Financially, not a big deal… but I celebrated the crap out of that little victory.

9. You need to know when to quit.

Know when to hold em, know when to fold em, know when to walk away… this is the hardest decision to make. After pouring all your time, energy, sweat, blood and tears into a business, there comes a time when you have to say goodbye. Maybe you're fortunate and it's a sale, so the business is replaced with a pile of money (still sad, but something positive came of it). Maybe you're not and you have to shut it down.

How you reach that decision emotionally will vary from person to person but usually if you are no longer passionate and energized about the business, it's time to shut it down. You can be dispassionate at a 9-to-5 without the risk and sacrifice!

Sometimes the decision will be made for you, financially, and those are often easier to take because there's not much ambiguity. If you don't have the money and can't get more, it's time to shut the doors.

10. Have fun.

I originally had #9 as the final thing but I didn't want to leave on a down note! So here's the last one.

HAVE FUN.

It's hard to celebrate little victories and have fun while you're in the trenches. When you have your head down and you're working hard, taking a break and having a little fun seems counterproductive. Why take a vacation when I need to keep pushing?

But those vacations keep you sane. Those breaks give you the opportunity to think about your business instead of just grinding away and working in your business. When you're sitting on the beach or hanging out in a cafe, the down time will give you a chance to re-energize, re-focus, and think about your business. You'll realize a lot of things because much like how you can think of solutions to a problem while you're in the shower, your brain will keep working on the problems while you relax. 🙂

Good luck and if you ever need a friend to talk about business, let me know!

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Jim Wang

About Jim Wang

Jim Wang is a thirty-something father of three who is a frequent contributor to Forbes and Vanguard's Blog. He has also been fortunate to have appeared in the New York Times, Baltimore Sun, Entrepreneur, and Marketplace Money.

Jim has a B.S. in Computer Science and Economics from Carnegie Mellon University, an M.S. in Information Technology - Software Engineering from Carnegie Mellon University, as well as a Masters in Business Administration from Johns Hopkins University. His approach to personal finance is that of an engineer, breaking down complex subjects into bite-sized easily understood concepts that you can use in your daily life.

One of his favorite tools (here's my treasure chest of tools,, everything I use) is Personal Capital, which enables him to manage his finances in just 15-minutes each month. They also offer financial planning, such as a Retirement Planning Tool that can tell you if you're on track to retire when you want. It's free.

He is also diversifying his investment portfolio by adding a little bit of real estate. But not rental homes, because he doesn't want a second job, it's diversified small investments in a few commercial properties and a farm in Illinois via AcreTrader.

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  1. Tracie Fobes says

    And, just when you think you have it figured out and things are going well, the rug might be pulled out from underneath you! That happened to me a year ago and I’ve had to rethink my entire blog strategy and change what I was doing.

    I’ve recovered for the most part. While in that moment I was terrified, it actually was the best thing that happened to me. It forced me to think outside of the what I was currently doing and be willing to try something new. That is leading to good success.

    • Jim Wang says

      Yes – that’s the thing about running your own business, you need to continue to evolve or you’ll be left behind. It might be gradually or it might be suddenly, but it happens. Good on you that you were able to regroup and recover!

  2. Matt Warnert says

    Good post Jim. I feel exactly like that first paragraph you put up. I have no expectations for my blog. I started it more as a personal branding project, but now it has made a few bucks and you start to wonder. I’m curious what you are doing to reinvest in your business?

    • Jim Wang says

      I reinvest it into infrastructure, to make the things I’m doing on a daily basis easier and faster so I can focus on growth, and reader acquisition, which may be advertisements or other similar marketing opportunities and partnerships. I hope that answers your question?

      • Matt Warnert says

        Kinda, you are investing time to automate processes, right? I’ve only been writing for a few months and I couldn’t think of anything off hand I would “invest” into my website other than upgraded hosting. Do you have a specific example you would mind sharing?

        • Jim Wang says

          Yes, I invest time to automate anything that can be done better/faster/cheaper through automation.

          Wallet Hacks is new too so there’s no automation help required at the moment, I am investing in services that might help me do research. For example, I might use a backlink tool to do backlink research and identify places I could reach out to for links.

          I also pay for a little advertising on Facebook to drive traffic to certain pages. That’s probably a better example than automation.

          Upgraded hosting will make sense if you start making more money and site responsiveness and uptime become a bigger factor.

  3. Corian001 says

    I find that the hardest thing about my business is sharing the decision making with the other partners. While having partners provides a safety network and is economically advantageous, it is always a struggle to reconcile different points of view, different sets of fears, baggage etc.
    Not sure a partnership is the best way to go…
    Almost ready to throw in the towel and go on my own.

    • Jim Wang says

      I agree 100%, there are pluses and minuses to partnerships. I’ve found that if you have the right partners, it’s fantastic. If you don’t, it can be very difficult. I’m sorry you’ve had a bad experience so far but perhaps it’s salvageable… or at least it’s a learning experience.

  4. Susan Lowell says

    Your point about knowing and understanding your numbers is spot on! I’m working on this now, and hoping you might do something at some point on double entry bookkeeping, which has a fascinating history (why all those Italian merchants got so fabulously wealthy in the 1500’s), and a steep learning curve. I’m doing lots of YouTube videos at the moment, and also found a translation of Luca Pacioli’s 1494 Summa de Arithmetica for grounding & balance (hah!).
    Thanks again for keeping me inspired!

  5. Phil Osborn says

    I’ll add one: Being in [small] business is like being on a roller coaster.
    You do some good work; someone notices. Pretty soon you have several projects or products (my experience is professional services–architecture, engineering, graphic design, public relations, etc; but it applies almost universally). You and your staff find yourselves driving full steam to get the work out. One week several of those projects finish up and you look around to discover there’s not much in the pipeline. So you say, Hmm, I guess I’ll go sell something. You spend the next six weeks in full on marketing and sales mode, and in another month some of those prospects come home to roost. The cycle repeats. The boom and near-bust roller coaster is very hard to get off. How do you?–In my experience, it’s important to commit to a habit of making at least one hour every day all about marketing: whether it’s working on a section of a proposal, working on a page of that web site revision, a Facebook or (and) Twitter post or two, or having lunch with a prospect or a customer you haven’t heard from in six months. Again, make it a habit. It’s hard. But it’s really, really important.

    • Jim Wang says

      Yes! So I view it as wearing two hats — you need to have your worker bee hat on to do the work, to execute on your promises, and deliver the goods. You also need to put on the queen bee hat to go out and sell the work so you will always have work in the pipeline. It’s hard to do that when you start off because those two jobs don’t seem to obvious at first…

      There are a lot of tools nowadays to help facilitate that, especially the keeping in touch part.

  6. Suze Wannabe says

    I would worry about these things:
    1. Valuation
    What do I expect my company (llc) to be worth in 5 years compared to similar bloggers?
    Valuation=Net profit *5-7

    2. Federal tax-Am I still making more despite having to pay the extra 7.5% my former company paid?

    3. 401ks-Can I still create a retirement t savings vehicle where I can save the max possible? How much am I missing in future value of a 20 year 6% match?

    4. Healthcare-are my premiums the same or higher? Out of pocket costs?

    • Jim Wang says

      1. Valuation is more like net profit – $100k (salary) & X, with X being a very fluid number and depends on how good of a fit the blog is with the business buying it (strategic vs financial buyer). But honestly, build a nice business that can’t sell and you still have a nice business.

      2. That extra in taxes gives you freedom. :))

      3. This I can’t answer 🙂

      4. Out of pocket medical is very expensive!

  7. Latoya @ Femme Frugality says

    The bumps are crazy insane and if it’s not something you’re aware of when starting out it can be discouraging. This list will definitely be helpful I someone starting out and it’s encouraging to me because I know it all is true!

    • Jim Wang says

      It can be very discouraging and since much of business ownership is emotion management, not knowing can kill a business. 🙂

      I’m glad it’s helpful!

  8. Financial Samurai says

    I agree in reinvesting in the business, but my goal is to definitely NOT sell it. I purposefully created a lifestyle business to have fun and make some money.

    With interest rates so low, having an income generating asset is extremely valuable now. Check out how REITs, bonds, and rental properties have done. As you know, blogging is one of the biggest cash cows with the highest operating profit margins around. There is no way I’m selling my business to reinvest in securities that only have a 2-3% yield.

    If we’re talking about selling the business for10X+ operating profits, maybe. But to sell for under 5X operating profits to reinvest in the S&P 500 that trades at ~24X earnings doesn’t make sense. The hardcore finance geek in me ain’t having it!

    Sam

    • Jim Wang says

      There’s something to be said about running a lifestyle business but there’s always as end. If you aren’t preparing for it, that can be a big issue. That end game might be 40 years in the future, but it’s there.

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