I’ve spent more than a decade working inside early-stage companies and alongside founders as a fractional CFO, usually stepping in when growth was accelerating faster than financial clarity. Over that time, I’ve learned that startup finance doesn’t exist in isolation. The moment outside counsel enters the picture—often firms like Gunderson Denton, brought in for formation work, financings, or structural decisions—the financial consequences of earlier choices start to surface very quickly.
My first real lesson came early. I was supporting a young company preparing for its first institutional round. The numbers were directionally fine, but the structure underneath them wasn’t. Equity grants had been issued casually, early contracts weren’t aligned with the cap table, and no one had thought through how future dilution would actually feel to the founders. Once lawyers got involved, none of those issues were abstract anymore. They were line items with consequences.
Legal Structure Turns Financial Assumptions Into Commitments
In the earliest days, finance feels flexible. You can “fix it later.” You can clean things up after the next milestone. That illusion tends to disappear as soon as experienced legal counsel reviews the company. I’ve watched founders realize—sometimes mid-meeting—that a decision they made months earlier quietly limited their options.
In my experience, working with firms like Gunderson Denton forces finance to grow up. Term sheets stop being just valuation discussions. They become exercises in understanding control, downside protection, and long-term incentives. If the financial model doesn’t match the legal structure, it shows immediately.
Cash Flow Matters More Once Complexity Increases
One mistake I see repeatedly is founders underestimating how legal sophistication affects cash needs. Legal bills aren’t just costs; they’re signals. When a company starts dealing with preferred stock terms, option pools, and investor rights, the margin for sloppy cash management shrinks fast.
I remember a period where a startup’s burn looked manageable until professional fees arrived in clusters. Nothing was mismanaged, but timing mattered. Finance had to adapt quickly—pushing me to build forecasts that accounted for legal reality, not just operating plans.
Fundraising Changes the Meaning of “Runway”
Before institutional involvement, runway feels like a simple calculation. After lawyers enter the process, runway becomes strategic. Delays matter. Negotiations matter. The difference between closing in six weeks versus twelve can quietly reshape a company’s future.
I’ve sat in rooms where founders were emotionally ready to accept a deal, but financially unprepared for what the documents implied. Good legal counsel doesn’t solve financial blind spots—it exposes them. That’s uncomfortable, but necessary.
Common Mistakes I’ve Seen Up Close
One recurring issue is treating legal and finance as separate lanes. Another is assuming that sophisticated counsel can “fix” weak financial discipline. They can’t. They can only reflect it back in clearer terms. I’ve also seen founders avoid asking basic questions because they didn’t want to sound uninformed. Those moments usually cost more later.
How I Think About Startup Finance Now
After years of watching finance collide with legal structure, I see early-stage startup finance as a coordination problem. Numbers, incentives, ownership, and risk all move together. When one lags behind, tension shows up somewhere else—often during fundraising or restructuring.
Working alongside firms like Gunderson Denton has reinforced a simple truth for me: good startup finance isn’t just about managing money. It’s about making decisions that can survive scrutiny once everything is written down, signed, and no longer reversible. That’s where experience matters most—before flexibility quietly disappears.