3 Apps I Use to Run my Business in My Sleep, from Anywhere in the World

Dylan Ogline
4 min readAug 12, 2021

When people ask me what apps I use to run my business, I sometimes feel like they are looking for a “magic bullet.” The one app that, once purchased and installed, will build, monetize, capitalize, staff, operate, and sell your business, all while you drink margaritas on the beach.

Of course, no such app exists. I hate to break it to you, but you’re actually going to have to build, run, and grow the business. There’s no skipping that step. That being said, apps can help you make certain tasks a lot easier.

The first thing I recommend when picking a tech stack for a business is–use as few apps as possible. This advice is complicated by the fact that there are a million apps out there, each promising a unique value proposition to run your business in your sleep.

Resist! Resist the temptation to download and/or buy every app that catches your fancy. You will end up with 50 apps and an operational mess. Try not to buy an app until you have a business need that the app specifically fills.

If you do find yourself with a zoo of apps, be relentless and merciless in editing them out wherever possible. Remember what I say — lean, mean, and scrappy. This doesn’t just mean your team — it also means your tech stack. If you can consolidate several processes down from three apps to one, do it. If you can eliminate a process altogether, eliminate the app!

So … considering what an app hater I am, what apps do I depend on? Here are three apps I use to run my business in my sleep. Your business might be different, and different apps might be right for you, but these work for me.

1. Boomerang

Boomerang is an add-on to Gmail that makes email management a thousand times easier. It adds a ton of cool features to my basic Gmail inbox. I’m completely addicted to those fixtures.

For one thing, it allows me to schedule emails. If I want an email to go out on a specific date and time, I can use Boomerang to schedule it. Boomerang also adds one-click Google Calendar integration, making it easy to manage my appointments directly from my inbox.

Boomerang also allows me to “pause” my inbox so emails don’t arrive in my inbox until I’m ready for it. This can help me focus on work, free me up to take a hike, or simply delay receipt of emails until I am ready to see them … without them getting pushed down my inbox where I will lose them.

The signature feature of Boomerang, though, is the “Boomerang” feature, which allows you to set email threads to “return” to your inbox, so you never lose a deal for lack of follow-up. The email keeps returning to your inbox like a Boomerang (get the name now?) so you can keep the conversation alive.

2. Teamwork

Remember when I said you should ruthlessly edit apps down to the precious few you really need? Never get three apps when one app would do? At the end of my own ruthless editing process, Teamwork.com was the last app standing for team management. It’s the one app I could never edit out.

Teamwork is an end-to-end client-services solution. They set out to provide every feature that a digital services agency like Ogline Digital could ever want, and I have to say they knocked it out of the park.

It’s the most complete project management environment on the market. It enables time tracking and workload management, with project updates in board view, Kanban view, Gantt chart view, and portfolio view depending on what you need.

You can assign project owners, set milestones, create task lists, generate reports, and manage risk. With this workflow management system, my team knows exactly what to do. I could be fast asleep or climbing a mountain, and my critical tasks would get done.

The collaboration environment also completely eliminates the need for my team to have a Slack channel. I don’t want to rag on Slack too much, but if a client asks you to join their team’s Slack channel, take my word for it and politely decline. No good can come of that.

3. Stripe

As you probably know, I tell my students that the most important thing they can do as entrepreneurs is to make the cash register ring. To do that, you need a cash register.

We depend on Stripe Invoicing for our cash register. Stripe is a dominant name in the online payment processing space — thousands of eCommerce stores and online sales funnels use Stripe to process their credit card payments. You have probably entered your credit card number into Stripe portals hundreds of times without realizing it.

Stripe also offers an industry-best invoicing platform for service-based businesses like mine. My team can build invoices in minutes, and our client gets an optimized experience where they can pay us right on the invoice.

Stripe Invoicing also offers automations so we can remind clients to pay us, without having to hound them by phone or email. It really can happen while I sleep on the other side of the world.

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