Less than 2 years after starting a new business in a new industry, I had my first $10K month. I’ve been trying to run my own business for about 5 years, and I’ve messed up a lot. I’m starting to think I’m doing some things sort of right.

So I sat down and thought about what I’ve learned over the past 2 years. What have I done that has worked? I boiled down my thoughts to 5 key lessons. Everyone has their own situation, so don’t take these as the end-all-be-all commandments of videography freelancing. They’ve worked for my particular situation, and my hope is that some of them can be applied to help you.

First, you should understand that $10K/month is not special. It’s basically the same as $5K/month, except that you’re paying more people to help you, you have a few more balls to juggle at a time, and you have more things to worry about on a daily basis.

It’s important to define what your actual goals are. Are you just picking that number because it sounds satisfyting to say? Is there a certain thing you want to purchase that will cost that much? Do you want people you don’t know to be impressed by your accomplishments?

Don’t set this goal unless you have a private, personal reason for hitting it. Otherwise you’ll get there and realize you’ve been playing the wrong game, and all the questioning you should have done at the beginning will catch up with you at once.

For me, I set a goal to pay off all my debt by the end of 2019, so I’ve been in a mad dash to make as much money as possible. After I pay it all off I’ll need to reflect a bit, take stock of my priorities, and figure out where I want to go next.

Here are my five lessons.


  1. Say yes to everything until you can’t anymore.

This one is pretty simple. At the beginning, you should say yes to every opportunity, free or paid. If you have any extra time in your work day, you should be doing only one of two things: selling videos or making videos.

Offer to make videos for everyone you meet. If you can’t get anyone to pay you, it’s because you haven’t demonstrated a skill level in videography that’s worth paying for.

So make something for free and post it on your social media. And keep doing that. Eventually your friends and acquaintances will notice that you’re the person who is doing videos.

You can create a cycle of momentum for yourself. The more work you do, the more opportunities will come to you. The more opportunities that come to you, the more work you can do. The more frequently you say yes at the beginning, the faster you’ll start and accelerate this cycle of momentum.

And as long as you don’t stop, the opportunities on your plate will exceed the time you have available. It might take 6 months or a year, but be patient, put your head down, keep doing it, and it will happen.

Then, you can raise your prices (see #5).


  1. Work for someone else as a contractor.

This was really hard for me because I’ve always wanted to be the founder of my own company. There has been a constant tension between my egotistical drive to do everything myself and the more tempered side of me that recognizes the infinite number of things I need help learning.

It’s ironic because for me, the quickest way to having my own business was by working for someone else first. Tagging along with a business that had an existing platform allowed me to step up my game very quickly without learning everything slowly and painfully through trial and error.

I’m trying to avoid giving you the vague advice to “find a mentor,” but that is another way of saying this. You need an apprenticeship. I broke my experience down in depth in this article, and I’ll cover some of the highlights here.

Email or FB message every single media company in your city. Just google “video production companies in *city*” and go down the list, emailing away. Find the email of the founder (usually you can find it on their website) and be honest with them. Tell them you’re just getting started, you want to learn, and you want to hear how they got started. To lower the burden of asking for a response, ask a simple and thoughtful question. Something like, “When you first got started, did you spend more time pitching clients or just making videos for fun?”

If they respond, that means you’ve opened the door for future contact. Now you can ask for a quick phone call, or a coffee meeting, and build the relationship from there.

There isn’t a perfect email script or pitch for this — whether they respond or not largely depends on timing. If the company is well-established, bringing you on do even free work can be more of a burden than a value. Just be real with people.

When you do start the relationship, enthusiastically take on the grunt work. Take everything off your mentor’s plate that distracts him from doing the high level work he wants to do. Offer to handle scheduling, sales, logistics, prepping equipment, etc. Slowly work your way into the processes of his business, and you’ll become invaluable over time.

On top of that, you’ll get a front seat view at how the person you’re shadowing works. You’ll learn more through osmosis than you could in any filmmaking school, and you’ll find yourself atop a platform that would have taken you years to reach.


  1. Organize your money.

I’m obsessive about cash flow. This habit started out of pure necessity.

It wasn’t so long ago that my debit card was declined at the grocery story every month or two.

In fact, if I had a nickel for every time this happened, I might actually have enough to pay for a full cart of groceries. It was quite an embarrassing experience that was totally self-inflicted.

One day I finally put my foot down and decided to get organized. It wasn’t helping anyone that I had no idea how much money I was making and spending.

There are so many ways to track income and expenses, it can become overwhelming. It’s good to invest in a good accounting software like Quickbooks, but when you’re first getting started, the cheapest and most effective way is to make a simple spreadsheet. Tracking your cash flow manually can be tedious, but it also forces you to be on top of it and know exactly where you sit. Here’s an example of the spreadsheet I still use to track my cash flow:

It’s broken down by each individual transaction. After I’ve physically collected the payment, I turn the row green. No preliminary counting allowed.

It’s so simple. You can highlight all the cells in white to see exactly how much you have booked that you need to collect. Then if you’re tight on money, you can prioritize finishing those projects or following up with those clients, or selling more work if that’s what’s needed.


  1. Do work for fun.

If you’re like me, the reason you got into video was because you have original ideas for videos or ads or films that you want to create. But you don’t know where to start nor can you afford to just make things for fun all day.

The nature of the business is that you need to do things for other people first. You need to build up a structure that provides people with the videos they want, and that brings in cash for you. The process of building this structure is the same process that develops your actual skill level (do better work), your portfolio (get more work), and your tacit knowledge of your industry.

Each of these is a core pillar that will create the foundation for your success and your career in the industry. But you can’t lose sight of why you’re doing it in the first place.

This is the item on this list that I struggle with the most. It’s crucial to carve out time for creating what you want to create, otherwise you’ll find yourself unfulfilled working on client projects that don’t give you a true outlet for your creativity.

My colleague Matt dedicates every Thursday to work on dream projects.

Have fun with it.


  1. Raise your prices.

My good friend Geno DiMaria gave me this advice and it stuck with me.

Pricing yourself is a common question in any creative field. Some people do it by the hour, some people work it back from market rates, but for me it’s always been a gut feeling.

For every project, I ask the question: What number would make me genuinely excited to give my all to this project?

As you become more confident in your abilities, as you create more opportunities for yourself, your gut will respond differently to this question. There comes a point where it isn’t worth your time to take on a free project, or even a $4,000 project for that matter.

Remember in #1 when I told you to say yes until you can’t anymore? When you can’t say yes anymore, you need to say no. Otherwise you’ll be pulled in all directions and you’ll be a pawn of anyone who wants something from you.

A great way to raise your prices is to set a project minimum. If anyone asks you to do a project for less than your minimum, politely tell them you don’t have the bandwidth and refer them to someone who might be able to help them.

You’ll notice that people respect you and your time more for this, and they will come back when they have higher budgets. Letting go of smaller projects invokes a feeling of scarcity in the short term, especially when you’re used to saying yes to everything. But you’ll quickly realize that the extra time you have for bigger projects (which will come up) quickly drowns out that scarcity.

I hope this was helpful in some way. Happy shooting!