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“I’ve raised funding, how do I reimburse myself for bootstrap expenses?”

When that first VC check lands and you’ve got capital to work with, it’s natural to wonder if you should pay yourself back for the startup expenses you covered. You paid out-of-pocket for software, travel, and laptops. Should you get that money back?

If the amount doesn’t materially change your life, skip it. If it does matter, then do it cleanly.

Don’t just transfer a lump sum into your personal bank account. Submit reimbursements through Brex, Mercury, or Ramp, and make it a one-time thing.

Then, stop doing reimbursements altogether.

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Reimbursements solved an outdated problem

Back when getting a new business AmEx card took weeks, teams relied on one shared card for everything — hosting, software, contractors, and lunch. But if someone left, canceling it could disrupt critical systems like AWS. So companies asked employees to front costs and get reimbursed later, leaving them to float hundreds and sometimes thousands of their own dollars. That workaround made sense then, but modern finance tools with virtual card features make it obsolete now.

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Reimbursements create problems for early-stage companies

Reimbursements blur the line between your money and the company’s. It works if you’re building a single-owner business, but if incorporated as a C-Corp and have ambitious plans to grow, that blurred line turns into a snowball of problems.

Numbers are always off
Say you front $500 for software today but don’t reimburse yourself until next month. That expense gets recorded late, throwing off your monthly reporting. It might seem small, but if it becomes a habit, these delays distort trends, skew burn rates, and make it harder to spot issues early. Without a clear, real-time picture, every decision gets a little less informed, and a little more risky.

Erode trust with key stakeholders
Even if you mentally account for discrepancies, others won’t. Your co-founders, department leaders, and especially investors rely on consistently and accurate reports. When your numbers shift from one update to the next, it signals a lack of reliability in your books and in you. If investors can’t trust the small stuff, they’ll start questioning everything else, too.

Distraction for personal gains
Some founders are tempted to use reimbursements for personal credit card rewards. But if you’re chasing some 4% cash back instead of building your company, you’re optimizing for the wrong thing. Do you want a free personal trip once a year, or a billion dollar company where this cost is a rounding error?

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What to do instead

If your card provider doesn’t let you issue virtual cards, start there. Tools like Brex, Mercury, and Ramp let you create custom cards for one-time or recurring expenses with built-in controls. That means cleaner books, tighter security, and fewer reimbursement headaches.

For example, here’s what you can customize with Mercury’s virtual cards. You can create this in a minute and have the number ready to be used to pay.

Merchant / category controls

Spend limit and expiration

You can see more from Mercury’s demo here

Before you take out a credit card to pay, ask yourself if the purchase is business or personal. If it’s business, create the right virtual card to match the need. Only use your personal card if you’re truly out of options, and then immediately submit your reimbursement to keep your books clean.

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Reimbursements solve problems for mature companies

As your company grows, reimbursements will occasionally be necessary for edge cases. At a public company scale, you’ll see situations like an employee needing to travel last minute and no time to set up a virtual card. In those cases, they cover the cost and get reimbursed. It’s not ideal, but it’s manageable, and large companies have finance teams to handle the process. Until you reach that stage, avoid reimbursements as much as possible.