QuickBooks Killer: The AI Bookkeeping App for Solopreneurs

Joyce Medeiros came into the room and admitted right upfront:

“We built the entirely wrong product.”

Her team had just wrapped Techstars when they realized their debt-tracking tool was solving a surface-level issue. The real pain for users wasn’t managing debt. 

It was not knowing where the money was going in the first place.

So they pivoted.

And built Investrio, an AI-powered bookkeeper for solopreneurs.

It’s Mint + QuickBooks for solopreneurs. Plug in your business and personal accounts, and get 92% accurate categorization, clean reports, invoicing, tax-ready exports, and an AI assistant named Vestie to guide you.

The question is: can they actually take on QuickBooks?

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The Problem: Spaghetti Finances

Joyce Medeiros told the story of Lena—a solo photographer making six figures but drowning in credit-card debt because she had no system for managing her finances. Her business was growing, but her financial health was falling apart.

“This isn’t a debt problem. This is an accounting issue,” Joyce said.

That insight led to the pivot: Investrio became a $20/month AI bookkeeper for one-person businesses—offering budgeting, invoicing, expense categorization, and AI support via “Vestie.”

In 5 weeks post-launch:

• ~500 signups

• ~25 paying users

• ~$5K ARR

Not a bad start. But the VCs in the room took issue with her target customer.

Charles Hudson’s Solopreneur Segmentation

Charles broke down the 42M solopreneurs market into three buckets:

1. Wantrapreneurs — just getting started exploring an idea for a new business.

2. Side-hustlers — making a few hundred a month. No budget for software.

3. Operators — serious founders running real businesses solo.

Only one of those groups actually has the willingness and ability to pay consistently.

His advice? "Find a way to achieve your goal of making the product available for the people who are up and coming, actually, by charging more for the people who will pay more."

The problem with targeting “all solopreneurs” is that you end up building something too basic for power users and too complex for casual ones.

Elizabeth Yin echoed the concern: “I don’t know who the ICP is here.”

The Pricing Squeeze

Even if you narrow to serious operators, you still have to make the economics work.

Investrio charges $20/month. Which sounds okay until you factor in:

• High support burden

• Low conversion from free to paid

• Solopreneurs churning when side-hustles fizzle

• The marketing cost of educating the customer on why they should switch from QuickBooks

And if acquisition depends on organic reach (posts, local events, newsletters) that still costs time and money to produce.

How to Make the Math Work

The VCs saw two directions that Investrio could go to make the math work. 

1. Choose a narrow ICP
Example: Solo professionals with $75K–$250K in annual revenue, Schedule C filers, paying for tax help today. Build onboarding, feature defaults, and support around that user.

2. Go wide and own the whole stack
Once you've nailed the narrow ICP, expand to become a full operating system. Platforms like Squire win by owning the entire workflow, not just one feature. For Investrio: CPA consultations, in-app filing, ACH payments, partner upsells (bookkeeping, banking, insurance).

The Takeaway

Build for someone specific:

• Their business model

• Their ability to pay

• Their pain point/frustration with QuickBooks

• The tools they’re already using

When you nail this, everything else falls into place. Retention climbs. Your product becomes essential. Customer acquisition gets cheaper. Lifetime value grows. 

That's when investors take notice.