Lessons from Enduring Planet & Friends’ November 2025 Community Event

You’ve built traction, hit milestones, and proven your product — but the next round isn’t landing as fast as expected. That’s where the Bridge Round comes in: a tool that can extend your runway to success, or set the stage for harder times ahead.

At our latest Enduring Planet & Friends Community Event - Everything You Need to Know About Bridge Rounds - we unpacked the hard truths of Bridge financings — from when to fold to how to protect your cap table.

Speakers:

• Hannah Friedman, Venture Partner at Planeteer Capital (moderator)
• Dimitry Gershenson, CEO at Enduring Planet
• Ben Conte, Investment Professional at Susquehanna Sustainable Investments
• Alexandra Wood, Partner at Orrick, Herrington & Sutcliffe LLP
• Alex Gershenson, Founder at Let's Build it Better, former Founder and CEO of SupplyShift (acquired by Sphera)
  

Understanding the Bridge: When & Why It Happens

Not all Bridges are created equal. While “Bridge” isn’t a legal term of art, it’s a functional one: any round meant to carry a company from today to the next milestone — the next raise, profitability, or even an exit. “Extensions” are simply one brand of Bridge rounds. “All Extensions are Bridges, but not all Bridges are Extensions,” said Dimitry, highlighting that while Extension rounds often repeat prior valuations, Bridges may introduce new structures or terms.

Why so many Bridges now? Milestones are taking longer, rounds take 6–12 months to close, and insiders are more selective. Many companies raised at aggressive 2021–2022 valuations and now rely on Bridges — often SAFEs or convertibles — to buy time until revenue, traction, or product maturity catches up.

Bridges aren’t always the answer. Most founders never consider “not bridging,” but sometimes more capital just means more pivots and deeper burn. When fundamentals aren’t solvable with time or cash, returning capital to investors, paying out employees and paying off all accounts payable or debts can be the wiser, more ethical move. 

That said, Bridge rounds aren’t a sign of weakness. For founders who are staying radically transparent, structurally disciplined, and emotionally resilient, Bridges are fine — just make sure you’re laser clear about what you’re building on the other side of the Bridge.

Building (and Funding) the Bridge Strategically

From the investor perspective, the key question is whether a Bridge achieves mission-critical steps forward or merely delays the inevitable. Insider-led (current investors already on the cap table) Bridge rounds often happen because teams and investors believe equally the next milestone is just around the corner or build mutual confidence in proceeding to test a new hypothesis. But, optimism alone isn’t a strategy. Tightening burn, adjusting timelines, and exploring alternatives should come before defaulting to a Bridge. Read more about our session on cash management strategies here.

Transparency creates trust. Be radically, uncomfortably transparent about what’s working and what’s not. Especially lean into the “pattern of fact” that has led to the need to bridge and what can be expected on the other side. Monthly updates, scenario planning, and early outreach to key investors matter. Founders who maintain consistent updates and clear narratives well ahead of their need to raise a Bridge are far more likely to get support. Most investors will sense issues anyway — so structured candor becomes a superpower.

Structured scenarios begets consensus. “Building a new company is just a series of iterative hypothesis testing.” Remember, your investors are in the business of taking risk. Invite your investors into the decision making (or, at least, the advisory) of which branch of the decision tree to go down - with complete information about the pros, cons and cash opportunity costs. Delivering information as “Here’s what’s going well, here’s what’s going wrong, and here’s what I’m doing about it,” can be a productive way of structuring scenario planning that builds confidence. Silence erodes confidence. 

Legal, Structural & Dilution Pitfalls

You have more to give than you think. Outside interest from external investors creates room to push for terms that keep the company healthily intact (read: avoiding down rounds or sharky terms). Pricing isn’t the only lever in a Bridge round; warrants, liquidation preferences, governance, and milestone-based structures can all be traded to construct a Bridge that is actually survivable.

Model the (hypothetical) math before you sign. High caps in Bridge rounds can feel good but can ultimately be dangerous. Overpricing Bridges leads to painful dilution if and when the next round comes in priced below the cap. Too many founders underestimate how extreme that dilution can be. Modeling out simple cap table proformas about these “what ifs” can help avoid devastating surprises.

The 101: Convertible notes are not SAFEs. The instrument you use to raise your Bridge matters. Notes can introduce maturity dates, interest, governance rights, and change-of-control multipliers (2–3x) that materially shift investor leverage. These terms can quietly reshape control and economics in ways founders regret later.

Don’t optimize to perfection. If liquidity is tight, speed matters more than ideal terms. SAFEs with discounts or simple convertibles may keep the company moving without months of negotiation, ideally unlocking the next milestone that causally results in a valuation increase.

Takeaways

• Bridge ≠ failure. Many great companies use them.
• Transparency may be uncomfortable, but it’s your friend. Silence signals trouble.
• Runway is leverage; start conversations early.
• Model it. Don’t get caught with dilutive down rounds or tough terms being blinded by optimism.  
• Don’t over-rotate on dilution: A smaller piece of a bigger pie beats zero.
• Focus on strategic outcomes, not squeezing for perfect terms.