Breaking down the schedule, tools, and team members that make this efficient entrepreneurial arrangement possible

When you hear that a person runs a passive, automated business that generates 6+ figures in just a few hours, there’s often a bit of skepticism. When you hear that person does so alongside other profitable ventures and stealth cash-flowing creative endeavors, while advising startups and exploring acquisition opportunities, that doubt heightens. I’d know, because when my own friends stumble upon my secret ventures, they ask that very question: How do you have time to do all that?

What they don’t ask is how I have time to do all that with only one hour of weekly business obligations. That’s because I don’t usually explain my entire business models, automation setup, active versus passive offers, team, and long-term plan. However, for those of you reading this, I’m going to do just that.

Why? Because if I’m honest, my schedule could appear pretty cushy to some people. If I don’t do anything but fulfill my 4-hour-work-month obligation — the only client-facing commitment I allow — my businesses will still run themselves just fine. Thus, it might surprise you that I was up until 4:32 am last Wednesday working on a project for a strict self-imposed deadline that has nothing to do with that 4-hour obligation. Yet, that rigid schedule is a key component of my collective entrepreneurial success.

There’s a saying about busy schedules that goes something like this: If you want something done, ask a busy person.

Along those lines, Parkinson’s Law posits that tasks expand or contract to fill the time allotted.

In other words, too much free time can instigate a slow, lazy work ethic, while a jam-packed schedule can maximize a person’s efficiency. While the solution seems to be to leverage the latter (the jam-packed schedule), there’s a major problem far too many people overlook: Fast doesn’t equal good.

Booking yourself to the gills may incite the adrenaline required to hasten your productivity, but that doesn’t mean the quality will catch up with the increased quantity. Plus, sometimes simply producing isn’t actually the best, most lucrative, or most productive use of time, as ironic as that sounds. Thus, I have an alternate preferred system:

I chunk my week into three different categories to ensure I don’t shirk or delay future products, projects, ventures, and revenue streams. In other words, work for projects that are months or even years away from launching publicly makes it onto my schedule this week, generates concept-testing cash flow, and bolsters my future marketing and expansion plans for those stealth endeavors.

Obligations: We all (for the most part) have obligations; these are the tasks or responsibilities we absolutely have to fulfill or face grave consequences. For some, this is client work, for others a 9-to-5 job; for me, it’s that hour per week dedicated to my only client-facing commitment. In my case, it falls on a Saturday, so I technically have the rest of Saturday and the remaining six days per week “off” or unspoken for.

New Production: This is what some consider side hustles, others optional or experimental projects. I consider them neither, since they generate more income in the pre-launch stage than some full-time jobs. I typically earmark Monday through Wednesday for these projects, with a goal of completing my week’s to-do list (across multiple stealth projects-in-progress) by Thursday.

Less-structured learning: This is the task most people — especially busy side-hustlers or multi-passionate entrepreneurs — leave off their agenda, yet this is one of the most crucial to their success. Once you graduate from university, there’s seldom someone orchestrating or requiring your continued education, and that’s where so many aspiring entrepreneurs and creatives stagnate.

If you aspire for outsized success in your entrepreneurial endeavors, then creating products, services, or content shouldn’t be the only “to-do” on your list. Whether you’re learning about industry developments, forging inroads with potential collaborators or advisors, or pouring over expert deep dives to improve your craft, product, or service, you’re invariably improving the odds of major success.

Sometimes, my learning has to do with marketing, sometimes technology, sometimes the gatekeepers of an industry of focus, and sometimes it comes down to improving one of my venture’s own products or creations. No matter the topic of choice that day, I come away materially more valuable to myself, my current ventures, and my future pursuits. Producing 24/7 at the expense of skill-expanding education is a fool’s errand, and one you may only regret once it’s too late.

There is one tiny factor I omitted from my initial equation, though I do consider it an important staple in my life and weekly agenda: Fun.

You can hustle, grind, network, and learn seven days and nights a week, but if you don’t make time for some spontaneous, joyful escapism, you may miss critical opportunities for the greatest organic inspiration to strike when you least expect it and change everything.

Every business is different, but there are a few key tools that maximize my entrepreneurial efficiency and enable the diversity of ventures I simultaneously run, grow, and explore.

• Email CRM: Some people build an email list and send a weekly newsletter with a veiled sales pitch inconspicuously embedded. My company operates differently in that we’ve created hundreds of diverse, highly-customized, cadence-varied email sequences that deploy year-round on auto-pilot, serving as a passive marketing tool that supersedes ads and social media.
• Automation integration software (like Zapier): My company’s marketing isn’t the only thing employing the “set it and forget it” school of thought; our entire product delivery and customer-servicing engines are built with automation. The only human involved was me, years ago, when I first set it up.
• Shareable, collaborative backups: Whether you use OneDrive, iCloud, Google Drive, or anything else, shareable, collaborative tools that back up your content and important files can be efficiency-enhancing lifesavers. I leverage these cloud backups for customers, collaborators (like assistants, partners, vendors, etc.), and my own peace of mind.

Of course, these aren’t all the tools that power my businesses, so I’ve listed a few more relevant ones below:

• Trusted website host plus email, backups, and security
• Sideline or Voxer (texting or voice memo app for clients or team members)
• Conversion-optimized checkout software
• Product, content, and marketing creation apps

My businesses and stealth ventures largely rely on three things: Marketing, operations, and new content creation. Thus, the majority of the tools I rely on address those core aspects, freeing up my time to do what AI and automation software can’t.

There are two schools of thought when it comes to teams:

1. Automation and technology should replace or minimize team members
2. The larger the team, the more successful and likely growing the business

My experience running teams ranging from yours truly to 20+ employees has cemented a slightly different perspective:

• A small, mighty team can accomplish more than a clunkier low-value one
• Automation and technology are great, but there are some roles and enhancements they simply can’t out-human

After hiring and firing countless in-house and outsourced team members and agencies over the years, I’ve learned that two principal groups optimize my ventures.

In-house: The old adage “two brains are better than one” isn’t always true, but when those two brains offer intelligent, diverse perspectives representing the broad spectrum of customer interests, they sure can dodge bullets. I have a trusted in-house partner/assistant (she toes the line of both) who regularly infuses my launch planning, content and product creation, and marketing strategies with viewpoints I’d never consider. She’s the last sign-off on my pre-launch products and half the reason I’ve been able to create cash-flowing stealth ventures without a dime spent on marketing.

External: Having slashed 80% of my marketing team (and budget) in favor of cheaper in-house automated strategies (which provide a better return), I’ve kept one expert team that sits at the intersection of marketing and technology. While I know this team’s ROI pales in comparison to the in-house marketing I conduct, it’s nice to diversify into other channels that have a more long-term emphasis, and I’d rather do so with an expert in my corner. That said, if crisis struck and heads had to roll, you can bet theirs would be high on the chopping block.

As one person running multiple ventures, I’ve single-handedly created at least 90% to 95% of the cash-flowing products, services, and content we offer. I’ve also learned and implemented close to 90% of the operational and marketing systems we use. Nonetheless, a high-value, responsive, well-aligned core team can make all the difference in quality, reach, customer reception, and success.