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Entrepreneurs need tools to keep us organized on the go.

I’ve had a lot of people asking me about my entrepreneurial must-haves lately. This post is all about some of the essentials in my toolkit!


Plain and simple, Slack keeps my entire team coordinated. It literally saves dozens of emails per day. Email is an asynchronous communication tool, whereas Slack is real time. That’s invaluable.

We use Slack to communicate with each other, with clients, and frankly, to get shit done more quickly.


This is a Mac app that compacts everything on my menu down into one simple little toggle. I don’t like a lot of clutter on my desktop. This keeps it all in one space and helps me to focus.


This is super simple but important app. Some background: there are studies out there that show if you track the wins of your day it will transform your entire outlook. And not just on your work life but on your entire life!

There’s a subconscious level that needs to know that you are getting the right stuff done. This app allows you to record those wins so that your subconscious mindset stays in victory-mode.

Field Notes

These little notebooks are super helpful for me as I work towards getting away from screens for the majority of my day. It used to be that if I took a walk in the skywalks to clear my head, I’d have to pull out a smartphone for note taking when inspiration hit.

I’d pull out my phone and then my walk turned into screentime. Thanks to Field Notes I now have a notebook in case inspiration strikes. These guys are very helpful to clear my mind and keep me truly unplugged when I need it.

Clamcase for the iPad Mini

I just got this but I can already tell it’s going to be amazing. It actually turns your iPad into a mini computer. The best part? The hinge goes all the way around so I can go from laptop to tablet as needed. It also works really well in airplanes.

Command Bag by Timbuk2

The bag itself is a perfect travel carry-on. It’s TSA friendly so you don’t have to take your computer out, which saves a lot of annoyance. It’s also a solid computer bag. There’s tons of space.

There are also separate sleeves for your iPad and your laptop. Plus, it has a pouch on the back that can go over your carry-on handle. It stacks right on top of it and stays there!

Packing Cubes

These are 3 little pouches (small, medium, and large) that I use to organize my luggage when travelling. They organize all the stuff in your carry-on by compressing things so that you can fit more into your carry-on.

It makes it really easy to separate your items by however you prefer to categorize! Workout stuff in one, regular clothes in another, socks and other stuff in the third. However. Just put it all together and compress it down.

I can’t remember the last time I checked a bag thanks to these guys!

Unu Charging Phone Case

This is a matte black battery case for an iPhone 5, and it’s available for other models. It looks good (not clunky) and it easily adds a half day of battery. When you travel a ton, you know that’s a necessity.


Those are just some of the essentials in my toolkit. If you haven’t already, click the links above to further explore these tools.

What about you guys? What are your must-haves?

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If “it’s free” is one of your product’s best features, it’s time to get a new product.

A lot of people make “free” into an ideal that everyone should aspire to. Maybe they are trying to be altruistic. Or maybe they are trying to sound like they can throw products out like candy at a parade.

Frankly, the “we can offer our product for free mindset” is the opposite of mine. When I hear free, I hear problematic.

When Free Pays Off

Now, before we get too far I want to say that there are certain things my company will give away for free. The reason we give resources away is so that we can bring in the right people who will eventually want to purchase our products, services, and courses.

This is an intentional process and method. I am up front with it and I won’t pretend we’re trying to do something different.

Part of the problem of the “ideal of free” is that even if organizations are following the method we do, too many of them aren’t up front about it. That’s true for businesses, nonprofits, churches, small or large businesses, and entrepreneurs.

Basically, there are people out there who want to cover up that somebody is profiting from their work somewhere. There are two common costs hidden behind free products.

Less Than the Best

The first hidden cost isn’t monetary; it’s quality. An organization says that their product or service is free. They don’t charge you anything for it. But because it’s free they cannot keep that product consistent or up to date.

They can’t put in the time commitment to maintain it. Therefore they can’t spend as much time as they should creating a rock solid product.

Users may get something for free but it’s certainly not the best.

Hidden Funding

The second hidden cost is simply that someone somewhere  is actually footing the bill for the product or service. The organization says it’s free, but it is underwritten by a corporate entity or sponsor.

The service or product is free to the client but what the client doesn’t see is the sponsoring entity who is undoubtedly pushing their products or services.

I’m not against this model; what I am against is when people will say “It’s free!” and then critique others who charge for their products or services. The fact is – if they are utilizing sponsors they are charging, too.

Honestly, I’m not against either method. I just want people to be honest when they are utilizing them. The client should be able to have realistic expectations.

The Way We Do It

Think Digital Academy is a 100% commercial product. That means it’s entirely funded by client registration. We are producing the material and we are profiting from the sales and it keeps our business running.

Another of our products, Social Church Academy, runs differently. We have partnering organizations that help out. Some help offset the cost of producing the material.

Others underwrite registrations for Social Church Academy so that people who would otherwise be unable to access it have that chance. It also is driven by client registrations.

I love both of these models. Why? They both work. They work for our clients and they work to keep us moving forward as an organization.

Why Our Models Work

These models allow us to bring more resources more quickly to make a better product for our clients. Everybody wins in this scenario.

If you still think your organization can make it by relying on donations, I want to be blunt with you. Having to rely on donations is like blackmail. Saying to your clients: “Hey, we’ll update this when we get enough donations!” is hamstringing them and blackmailing them to donate to your cause.

I think other organizations can learn from the more unapologetically capitalistic ones like ours. By keeping free resources as an intentional entry point for future paying clients, we are able to provide consistent products, consistent customer service, and consistent growth as a company.

Systems are going to run your business, whether you’ve crafted them or whether they are running by default. Systems are simply how the world works!

Hopefully by now you have taken some time to analyze your current systems in place. Maybe you’ve found some things to celebrate! Maybe you’ve found some broken systems.

This post will cover 5 more critical systems. I’m confident you will be able to walk away from this post with direction to both fix and build your own network of systems.

Productivity System

A productivity system’s purpose is to manage how you work. Not enough people take this seriously! We tend to think that either we’re expert multi-taskers (multi-tasking is the sworn enemy of productivity, by the way) or we wind up running from fire to fire, with no intentionality in place.

A productivity system gives you a way to approach your work. You can find several out there if you look; I personally swear by the Pomodoro Method. It allows me to approach work in a systematic way.

The method means focusing on a specific task for a certain amount of time, say 25 minutes, and then taking a break.

Focus, break, focus, break.

On the surface this sounds dead simple, but truly focusing on only one task for 25 minutes can prove very difficult. This is coming from a guy who through who couldn’t focus AT ALL through grade school, and not much better beyond!

Yet the hardest part about sitting still in grade school was never knowing how long the task at hand would last. It was this open-ended time commitment and that was really hard for me to account for.

This system is my solution. Even if it’s the most unpleasant task on the planet, I only have to focus on it for 25 minutes at a time. Chances are I can get it done before that time limit is up. I bet you could, too!

What I have not found to be helpful when seeking productivity are apps.

Using an app opens the door to the black hole of the smart phone. Those little red notifiers are competing for attention, and before you know it you’re in a Twitter conversation, snapchatting for just a second, and miles away from your task.

A system helps automate self-control. You don’t have to conjure it up, it’s built into the system itself. You can’t be pulled into a distraction if the distractions are out of sight and mind.

Time Management

Time management systems are a way to divvy up certain types of tasks for specific days. My days are divided into catch-up days, money-making days, and free/relaxation days.

I purposefully align my week as much as possible to have the tasks that I accomplish fit into those pre-specified days.

What does your business require? What 3-4 categories do you need to chunk your week into to make sure everything is accomplished with as much focus and purpose as possible? Organizing your days to a specified rhythm will bring much more flow to your work and results.

Cash Flow System

Confession: for the first 9 months of business I had no idea what was coming in or going out financially. I had no idea of numbers keeping the business going.

I realized that if that did not change there would be no business. I used the excuses of being new, or of having time for that later. But I realized that from day one a person can have someone on board to help them manage their accounts if they prioritize it.

I’ve had a money person on board for a while now, which is how I have established a cash flow system. For me, this looks like getting 3 reports on a regular basis:

  • A daily report which shows me profit and loss for the previous day, 90 day averages for income, expenses, and cash reserve.

  • Weekly profit/loss statements, because I have weekly income to monitor.

  • Monthly profit/loss as well, to give me an overall shape of where things are heading.

Some of the numbers are redundant, but I’d rather be over-educated on my numbers than under-educated. I don’t think enough entrepreneurs realize the power of numbers!

Seeing those numbers has been a mind-shift. This system has helped me to realize that I’m running a real business and not just working on a hobby. Those numbers impact me, my family, and every single team member and their families.

Integrating my cash-flow system has been the single most important change that I have implemented since starting this business. What gets measured gets managed – money doesn’t magically show up.

Challenge Time

I want to  challenge every entrepreneur reading this to hire a bookkeeper.

There are way too many of us who simply buy a license for QuickBooks and resolve to do our own books, but it just never gets done.

Spending $30-40 an hour to have someone else do this will make you more money and reduce your stress. Yes, the smaller you are the tighter your budget may be – but that also means fewer hours (fewer dollars) going to that accountant. You need to consider it. You need to take it seriously.

Marketing System

You cannot leave your lead nurturing system up to chance. You need to outline a path and engineer a process for your leads to go through.

This can happen on many different levels and in many different ways. My company has a process for converting leads into Think Tank Sessions. We have a different process for how we get people from being social media contacts into joining the email list into becoming full-fledged clients.

Marketing systems do not have to be complex! They aren’t rocket science. But if you don’t outline yours and give it intentionality, it will default to haphazard chaos. That means no results.

On-Boarding System

It is also important to have an onboarding system for clients. This process could be a need for you if you have created an application, if you have clients, and even if you don’t have clients!

Why? Because as an entrepreneur you are serving somebody. How you onboard those folks is critical to the long term success of your business.

An onboarding system sets expectations from the get-go for whomever you are serving. It basically says, when X happens; we do Y!

If this, then that.

I have started implementing 30, 60, and 90 day checklists with every client. That way if a client is unhappy we know it as soon as possible and can fix it.

We also know if there’s room for improvement. I want to be proactive in finding out what that is and fixing it. The only way to do this consistently is by having a system in place and sticking to it.

The Goal of a System of Systems

When you approach your business as a system of systems it will allow the business to eventually run independently of you. If you want your business to be sustainable, that should be your goal!

Let’s look at it through the lens of a final analogy: your business as a person. More specifically, as your baby – which in many ways all of our businesses are!

Now, a baby needs a mother to grow and to be nurtured and to be cared for literally 24/7 for the first 9 months of its existence. Eventually, however, the cord has to be cut. Your business is the same way – if you want it to be sustainable.

Yet a lot of entrepreneurs never get to the point where they cut the cord of the business. Cutting the cord doesn’t mean that the baby doesn’t need its mom anymore! It just means that the relationship between mom and baby is different. The baby is learning how to grow and develop and function on its own.

Having a business is the exact same thing. There are way too many entrepreneurs who are 5, 10, 15 years into it and they still have the cord connected to their business. They are not allowing that business the chance to grow and develop beyond its infancy.

Personally, I don’t want a codependent business. There’s no freedom in that.

I want a business that can grow into its own with my guidance. How will I achieve that? By continuing to build my system of systems!

What systems will you put into place this week?