Funded: The Fundraising Story Most Founders Won't Tell You | Andrew Rea, TaxWire

About TaxWire

📍 New York, NY | 💰 Total Raised: ~$24M (as of the time of this interview) | 🎯 Stage: Series A | 🏢 Focus: Global Sales Tax Compliance

TaxWire is a global sales tax compliance platform that handles the full stack: calculation, filings, reporting, and the managed service layer that sits on top of it. Founded in 2023 by Andrew Rea and Steven Schmatz, the company was built for finance and accounting teams at scaling businesses who need more than a point solution.

TaxWire combines a best-in-class tax engine with dedicated account managers who are actual sales tax experts, so customers get both the software and the outcome. As of this recording, TaxWire had raised ~$24M from investors including XYZ Venture Capital, Headline, and Recall Capital, with zero churn across its customer base.

In This Episode

Andrew Rea has raised three rounds, and each one went down completely differently. In this conversation, he gives an unusually honest account of what it actually took to get each one done, from 200+ investor conversations in eight weeks to a term sheet that arrived in 24 hours.

✓ Why the pre-seed was the hardest round despite being the smallest check
✓ How TaxWire generated seven term sheets in four days for their seed round
✓ The two fundraising approaches Andrew has seen work, and why anything in between fails
✓ What it takes to recruit world-class people into a first-time founder's company
✓ How to pick a board member you'll actually want when things get hard
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Key Takeaways

1. Brute Force or Finesse: Pick One

"There's two ways to raise money, especially in the earlier stage. You can raise with finance or you can raise with brute force. I would pick one or the other. Anything in between is probably not correct." - Andrew Rea

Andrew's framework for early-stage fundraising is simple: either go wide and grind through as many conversations as possible, or play the relationship game so well that investors are ready to preempt you before you ever formally launch a process. Both work. The mistake is doing a half-hearted version of each.

For TaxWire's pre-seed, Andrew went brute force: roughly 200 investor conversations in about eight weeks. It felt like it was going nowhere for most of that stretch. Then it got hot at the end and they closed oversubscribed. The lesson wasn't that brute force is elegant. It's that if you're willing to do the volume, the reps alone will make you better. By the time the right conversation happens, you're ready for it.

The finesse route works too, but it requires real relationship equity built over time: investors who already want to back you as a founder before you ever ask. If you have that, you can let the preempt come to you. If you don't, you probably can't manufacture it on a short timeline.

2. Raise at an Inflection Point, or Before You've Done Anything

"The easiest time to raise is at an inflection point, or when you've literally done nothing and it's all a story. Anything in between is probably not correct." - Andrew Rea

Andrew's view is that the fundraising window is actually quite narrow. Pre-launch, you can sell a compelling story and a strong team. At a genuine inflection: 40-50% month-over-month growth, ripping and replacing established vendors, zero churn. The messy middle is where founders get stuck: enough traction that pure story doesn't work, but not enough momentum to create urgency.

For the seed round, TaxWire was two months into selling when they raised, but the numbers were already moving fast and the team they'd built was a strong enough signal on its own. Andrew had spent over a year flying around the country recruiting tax engine veterans from Stripe, TaxJar, Avalara, and the Big Four. Investors could look at the team and ask the obvious question: why are these people leaving good jobs to join a first-time founder's startup? That question, answered well, can be as powerful as ARR.

3. Volume Is the Whole Job in Recruiting

"I think the volume that is required to find really, really great people is just -- I think a lot of companies think that they're doing a lot of volume and they're not doing a lot of volume." - Andrew Rea

Andrew's approach to recruiting key hires mirrors his approach to fundraising: start by deeply understanding exactly what you need, then do far more outreach than feels reasonable. For TaxWire's Head of Tax, he talked to hundreds of people over several months just to understand what he was actually looking for. Once he had a precise picture, he could narrow to a short list. One of those people was Graham Martin, who had built four separate tax engines from scratch before TaxWire.

For the Head of Growth hire, the search took six months. Andrew had good finalists before he figured out what he actually needed, then started over. Most founders would have filled the role earlier. His argument: the cost of a wrong hire in a key seat is much higher than the cost of leaving it open longer.

4. Pick a Board Member Who Wants to Build the Same Company You Do

"You don't want a board member who thinks you're building a different business than you are, or wants you to build a different business than you are. Because that's going to lead to a lot of friction." - Andrew Rea

When TaxWire opened its first external board seat at the Series A, Andrew already knew who he wanted. Taylor at Headline Ventures had been following TaxWire since the seed round, understood the space more deeply than any other investor they'd talked to, and shared Andrew's conviction that taxes and accounting are generational businesses. That long-term alignment mattered more to him than brand name or check size.

His advice for founders evaluating board members: look past the firm and look at the person. Do they understand the specific business you're building? Are they oriented toward the long term, or are they optimizing for the next markup? And critically, have you seen them operate under pressure? Andrew knew the answer to all three before he said yes.

Reference Links

• TaxWire - Learn more about the global sales tax compliance platform Andrew built: https://www.taxwire.com
• CJ Gustafson's CFO Guide - The survey Andrew references showing 43% of companies with $1-5M in revenue do nothing for sales tax compliance: https://cfosimplified.com