Why I Finally Started Outsourcing Everything (Including This)
The math that convinced me to stop being my own accounting department
Running two companies has taught me a brutal lesson: your attention is finite, but your ambitions don't have to be.
Welcome back to everyone who's been here since May, and hello to the 100+ new subscribers who joined during my summer sabbatical. I took three months off from this newsletter to focus on what matters: building ModernTax to $1M EBITDA (and launching new verticals and marketplace), launching a stealth AI startup this fall (announcement coming soon), and ironically, drowning in the exact back-office work I should have been outsourcing.
At 38, with two kids under 4, I'm laser-focused on three things: ModernTax's path to profitability, the stealth startup's October launch, and growing both this personal newsletter and ModernTax's business content. Big thanks to TaxFyle for sponsoring this comeback issue - their timing couldn't be better.
That's when I finally admitted what I should have known years ago - I can't do it all. More importantly, in 2025, the winners won't even try.
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I've seen too many founders burn out trying to be their own accounting department. Don't be that founder.
The Wake-Up Call
Last month, I was on a critical customer call - the kind that could define the next decade of my stealth startup. Mid-pitch, I glanced at my desk: IRS notices, compliance paperwork, quarterly filings for ModernTax. All critical. None of it is moving the needle.
That's when it hit me: I'm spending 40+ hours a month on tasks that someone else could do better, faster, and probably cheaper than I.
The $125 Billion Reality Check
Here's something wild: The tax and accounting industry spends $125 billion annually just on salaries and wages. That's not revenue - that's just what the companies in the industry pay professionals to navigate this Byzantine system.
At ModernTax, we've been in the trenches for four years helping lenders access tax records as opposed to using the IRS's antiquated IVES program. Nothing about this process has gotten easier. If anything, it's gotten worse. Address verification issues, signature authorization nightmares, the whole 4506-C process - it's still broken.
But here's what I've learned: You don't have to fix every problem yourself. You just need to know which problems are worth YOUR time.
The Math That Changed Everything
Simple example from last week: I needed our quarterly tax filings done.
Option A: Spend 10 hours figuring it out myself (because "I run a tax company, I should know this").
Option B: Pay our CPA $400 to handle it perfectly.
Option C: Utilize AI tools to help do it myself (my favorite option lately)
Those 10 hours? I used them to close two enterprise deals worth $35K combined.
That's not outsourcing. That's arbitrage.
Why 2025 Is Different
We're in the post-ChatGPT era of professional services. Look at what's happening:
Handshake AI hit $50M ARR in 6 months, building an expert network
Mercor is allegedly raising at a $10B valuation
Every CPA firm I talk to is drowning in work, but can't find talent
The old model - hire more people, bill more hours - is dead. The new model? Leverage technology and strategic outsourcing to do 10x the work with the same team.
What This Means For You
If you're a founder: Every hour you spend on non-core professional services - bookkeeping, legal docs, tax compliance, HR paperwork - is an hour you're not building product or talking to customers. These are solved problems. Outsource them and focus on the unsolved ones that define your business. I plan to write a breakdown on the impact of AI in these areas soon.
If you run a CPA firm: Your best clients absolutely care that YOU handle their complex situations - that's why they pay premium rates. But those Schedule C filers paying $500? The ones eating up your March weekends? Strategic outsourcing lets you serve more high-value clients while maintaining quality across your entire book.
If you're in tax tech like me, TurboTax owns the DIY filing market. Although a company I've written about before, Column Tax, is up over 1 million filings this past tax season, Intuit is still the $187B market cap company that dominates. We don't win by building another bookkeeping tool or tax filing app. For my company solving the messy, complex problems they ignore - tax verification for lenders, resolution services for businesses in trouble, and planning tools for growing companies is where the opportunity is. Focus on the long tail where the real pain (and margin) lives.
The Plot Twist
Here's the thing nobody tells you about outsourcing: It's not about the money you save. It's about the focus you gain.
Since I started outsourcing aggressively:
ModernTax hit profitability by focusing solely on tax verification and resolution - the complex problems TurboTax won't touch
Our product velocity doubled because I'm in customer calls, understanding real problems, not buried in compliance paperwork
The founders crushing it in 2025 won't be the ones doing everything. They'll be the ones who know exactly what NOT to do.
Your Turn
What are you still doing that someone else should be doing? Seriously - hit reply and tell me. I read every response, and I've gotten some of my best insights from these conversations.
Next week: The controversial truth about solo founders vs. co-founder teams. Had dinner with a partner at a multi-billion-dollar fund last week, and his take completely changed my perspective. You're probably not going to like it.
Until then,
Matt
P.S. - Still manually tracking Reddit for 4506-C complaints via Zapier. Some habits die hard, as this is huge customer discovery for ModernTax. 😅