Stop Getting Screwed by the Back Office: The Complete Infrastructure Guide for Fractional Executives

This blog post is a detailed account of our podcast episode with Mark Jackson, co-founder and CEO of Besolo, where we dive deep into the operational infrastructure that makes or breaks fractional businesses.

You're crushing it as a fractional executive. Six-figure contracts, clients who actually value your expertise, and the freedom to work from anywhere. But here's the dirty little secret nobody talks about: while you're busy being a strategic genius for your clients, your own back office is probably held together with digital duct tape and prayer.

Sound familiar? You're not alone. According to our guest Mark Jackson, 90 to 95% of solopreneurs are living in some type of fear of a compliance, tax, or benefits issue. And that fear? It's what's driving 3 million new solopreneurs back to W2 jobs every year, despite making great money as independents.

Mark should know. As a former fractional CRO turned founder of Besolo, he's seen both sides of this equation. His company now serves thousands of solopreneurs who were tired of "walking around in a jungle at night with a flashlight, hoping they don't fall into a pit or get bit by a snake."

The $29,000 Wake-Up Call That Changed Everything

Mark's journey to solving the solopreneur infrastructure problem started with his excavation contractor father, who spent every tax season "upstairs swearing at 1040 schedule C's." But the real catalyst came during his own fractional career.

"I had an okay year and then had a really good year," Mark recalls. "I didn't realize that my CPA was calculating my quarterly estimated taxes by just taking the previous year's tax and dividing it by four."

The result? A brutal $29,000 tax bill in April that nearly sent him back to corporate life.

But the final straw wasn't taxes - it was healthcare. When his wife needed a kidney transplant (costing north of $1 million), Mark realized that in Arizona, their specialty medications alone would cost $70,000-$80,000 per year as independents. "I felt abandoned by my government," he says.

That's when Mark had his lightbulb moment: What if solopreneurs could pool together to create strength in numbers?

The Business Structure Decision That Makes or Breaks You

Before we dive into solutions, let's get clear on the fundamental choice every fractional executive faces: How do you structure your business?

Mark breaks it down into a simple framework:

Sole Proprietor vs. LLC: The Risk Question

This isn't about taxes - it's about legal protection. As a sole proprietor, you're contracting as yourself. "If something goes wrong in your business, that risk is tied to you as an individual," Mark explains.

For high-level fractional executives working with venture-backed startups or companies with significant stakeholders, the risk is real. Data leaks, contract disputes, even a car accident while driving to a client meeting - any of these could put your personal assets at risk.

The Besolo recommendation? Check the LLC box. It's not expensive, it's not that hard to maintain, and it creates a protective barrier between your business activities and your personal life (including your cats, as Mark likes to joke).

S-Corp Election: The Tax Optimization Play

Here's where most advice gets oversimplified. Everyone says "make above X amount, elect S-Corp." Mark's approach is more nuanced, using three key considerations:

1. Revenue Threshold: You need to be making at least $80,000-$100,000 annually to make the operational burden worth the tax savings.

2. Revenue Consistency: S-Corp requires running payroll for yourself. If your revenue swings wildly month to month, you're going to struggle with what Mark calls "the payroll treadmill."

3. Your Freedom Values: This is the big one everyone ignores. S-Corp means more structure, more compliance, cleaner books, zero mixing of business and personal finances. If you value the chaos and flexibility of the pure solopreneur lifestyle, S-Corp might not be worth the savings.

"For some people who want to go to Bali for six months out of the year, make 150 grand in the first six months doing some focused project and then bail out to work at a bar in Bali - S-Corp is probably not a great fit."

The Complete Operational Stack Every Fractional Executive Needs

Beyond business structure, here's the full back office infrastructure you need to run a legitimate fractional business:

Business Banking

Separate business and personal finances. Non-negotiable if you want to maintain your liability protection and make accounting manageable.

Accounting System

Connected to your business bank account, categorizing expenses automatically, and calculating quarterly estimated taxes in real-time. The days of shoebox receipts are over.

Compliance Calendar

LLC statement of information, quarterly estimated taxes, annual tax filing, S-Corp additional requirements - there are dates that matter, and missing them costs money.

Benefits Recreation

How do you replace the benefits package you had at your corporate job? Solo 401(k), health insurance access, disability insurance - these aren't nice-to-haves at the fractional executive level.

Here's the kicker: Most fractional executives spend their first 12-24 months in choice paralysis, trying to piece together this stack from 10 different providers. As Mark puts it, "Choice paralysis is brutal when you're trying to put together your operational stack."

Why Smart Fractional Executives Still Fail

The infrastructure piece is table stakes. But Mark identified two bigger reasons why successful fractional executives still end up back in corporate jobs:

The Lifestyle Trap

"I think the idea of the portfolio career is becoming more acceptable," Mark notes. The all-or-nothing approach - either you're 100% independent or you're not - is outdated. Smart fractional executives "pendulum" between independent work and W2 opportunities based on what makes sense for their situation.

The key: Keep your fractional infrastructure intact even when you take a W2 role, so you can swing back when the right opportunity presents itself.

The Revenue Model Problem

Here's the big one: fractional executives who stay sustainable long-term figure out how to productize their offer.

Mark's breakthrough came when he created "The Foundation Sprint" - a productized way to help companies become SEO/SEM-capable. Instead of selling hours, he was selling a repeatable methodology with predictable outcomes.

"If you're just trying to do that one-to-one hours-to-money relationship, that can lead to a situation that is not sustainable," Mark warns. The most successful fractional executives move beyond custom consulting to productized offerings that can scale.

The One-Decision Solution

After seeing thousands of solopreneurs struggle with this complexity, Mark's team at Besolo built what he calls the "one-decision solution." Instead of piecing together 10-15 different tools and providers, fractional executives can get their complete operational stack - formation, compliance, accounting, taxes, payroll, benefits - in one integrated platform.

"Let's just check all those boxes in one decision and give you human beings you can talk to as things come up," Mark explains.

The sweet spot? Fractional executives in their first 12-18 months who are overwhelmed by the infrastructure side and want to focus on what they do best - delivering results for clients.

Your Next Move

Here's the bottom line: You didn't leave corporate life to become a part-time accountant, tax preparer, and benefits administrator. You left to do high-level strategic work that moves the needle for businesses.

If you're spending more than a few hours per month on back office infrastructure, you're doing it wrong.

The most successful fractional executives treat their operational stack like any other business investment - they either build deep expertise in-house (which takes years) or they delegate it to specialists who can handle it better, faster, and cheaper than they can.

As Mark puts it: "At the end of the day, we're just trying to be the guides in this space to get this done right and make it easy and sustainable."

The fractional executive lifestyle isn't going anywhere. With 3 million new solopreneurs entering the market annually, the question isn't whether this model works - it's whether you'll build the infrastructure to make it sustainable long-term.

Ready to stop getting screwed by the back office? The most successful fractional executives make one decision to solve the entire operational stack, then get back to doing what they do best - commanding premium rates for strategic expertise.

Want to learn more about Besolo's approach to fractional executive infrastructure? Check out their free consultation and see how they're helping thousands of solopreneurs build sustainable, compliant businesses without the operational headaches.

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