5 Fundraising Rules for Raising Money When Investors Get Careful.

Seven companies took more than two-fjords of the money this week. At the end of September, I scored fifteen U.S. startup funding rounds with my Eisen Fundability score, and each between five and a hundred million dollars. Seven of them had one thing in common: an investor who had already put money. Ian came back and invested again. Those 7 raised $47.5 million on average. The other 8 raised $19 million. That's 2.5 times more money in the same week and same market. The other 8 were not worth companies. They were strangers to the people writing the checks. In this episode, 5 rules for raising money when investors get careful, a 5-step playbook, and what I'm watching next. I'm Leon Eisen. I'm a venture partner at Network VC, a 4-time founder, and the author of Invisible Game: The Secrets of the Term Sheet, magnet on Amazon. Every week I publish a report on the US venture market with playbooks you can put to work. So if this is useful, subscribe, like the video, and leave me a comment. Let's start. So why do so many founders start a raise by chasing new investors? Most raises start in the wrong place. Founders build a list of 100 investors they have never met. Their current investors just get their monthly update. They already said yes once, so asking again feels like asking for a favor. But every new investor has one quiet question. Your current investors sit in your board meeting and see the real numbers. Are they investing again? If yes, the people who know the most want more. If no, they probably know something the new investor doesn't. Founders treat their current investors as the past, and the market treats them as proof. There is one answer current investors love to give When the next round comes up. We are very supportive. It's not a number. Ask a current investor about your next round and you will probably hear again something like this. We are very supportive. We will look at our share once there is a lead investor. Let's see how the round comes together. Founders hear warmth and count it as a commitment. A new investor hears something else. The people who know this company best are waiting for someone else to go first. Interest is not conviction. Supportive is what waiting sounds like. Before we go one by one, here are many— 5 of my 5 fundraising rules for when investors get careful. Fundraising rule 1: fewer deals with bigger checks is not a hot market. It's a consolidating one. Fundraising rule 2: renewals get funded. Sales get discounted. Fundraising rule 3: Own one fact you don't control, then build your round around it. Fundraising rule 4: A corporate check is a multiplier, not a substitute. Fundraising rule 5: Come back fast and come back bigger. All 5 points the same way: money follows a yes that already happens. Fundraising rule 1: start with a number that looks like good news. Bigger average checks don't mean a better market. I've seen the number of funding rounds fall by half in 2 weeks while the median check jumped 46%. That looks like a hot market, but it isn't. The checks didn't grow because investors were paying more for each company. They grew because the smaller, earlier rounds stopped happening. So don't set your ask based on the market median. Compare yourself to companies at your stage with your current backing. Fundraising rule one: fewer deals with bigger checks is not a hot market; it's a consolidating one. The midsize market didn't shrink eventually. One stage lost round every week: fourteen, nine, eight, six. That how many Series A rounds? I counted each week through September 2026 in the midsize US market. In the last of those weeks, every Series B had an early investor coming back, and only 2 of these 6 Series A rounds did. A Series B is usually a second decision by people who already know you. A Series A is usually a first decision by people. Who don't? When investors get careful, first decisions are the first to go. The door didn't close. It got narrower right where newcomers walk in. Fundraising Rule 2. It explains where the money goes, goes when investors get careful. Every funding round is either A renewal or a sale. A renewal is when someone who already invested in you invests again. A sale is when you ask someone new to go first. When money is tight, these 2 get priced very differently. In my recent data, renewals raised about 2.5 times more per round than sales. And the gap grows as investors get more careful. Over 3 weeks, I tracked the score gap between renewals and sales more than doubled. Fundraising Rule 2: Renewals get funded, sales get discounted. Renewals win, so who do most founders call first? Usually the wrong people. Most founders ask their own investors last. They meet new investors first. 20 meetings, then 30. Only when the process stalls, they go back to the people who already know them. The current investors can see the stall, and it shapes their answer. And every new investor along the way asked the same question. What are your current investors doing? The founder had no clear answer. 3 months of this selling to strangers, and the one question they all asked was about the people the founder never called. Fundraising rule 3. Sometimes the yes that moves investors doesn't come from an investor at all. For example, a rocket that has never flown beat a $97 million round. The rocket company is Hope Aero. An $11 million seed round. It had done one test flight tied to the ground with a small prototype. The other company already makes its chips in volume. It raised $97 million. On my fundability score, the rocket company still came out ahead. Why? The Air Force Research Laboratory had already reviewed its technology and paid for more work. That doesn't prove the rocket works. It proves the customer has already shown up. Investors found that's possible. They move faster on what someone else has already checked. And outside approval has a catch there. I tested how much it's really worth. Take their approval out. See what's left. When I score rounds, I run one extra test. I remove the points a factor earns on its own and check whether the, the advantage is still there. Rounds with an outside approval, like a clinical trial, a license, or a government grant, Scored about 8 points higher. Remove the approvals on points, and only half a point was left. Rounds with the returning investors stayed far ahead. An outside approval opened the door. A returning investor and a clear deal carry the round. Fundraising rule three: Own fact you don't control. When then build your round around it. Fundraising rule four is about the big corporate name almost every founder wants as an investor. A big corporate name on your cap table will not carry your round. When I score rounds with corporate money in them, they barely beat the rest. Take away the point for the corporate check itself, and they score lower. In one round, a large private credit firm invested and signed a partnership in the same announcement. It still scored in the bottom half. The corporate rounds that did well had something underneath— an outside approval or an investor coming back. A corporate check proves you have a customer. It doesn't prove you have a round. Fundraising Rule 4: A corporate check is a multiplier, not a substitute. Fundraising Rule 5: is about timing, and it works for you or against you. 11 months, more than twice the size. That's how fast Flow Engineering, which builds AI tools for hardware engineers, came back, back for its next round. Sequoia, which led its previous round, invested again. A quick return at a bigger size sends a strong signal: the people who know the company best saw enough to buy more. In my data, the rounds that came back within 18 months at a bigger size scored about 11 points higher. If your next round is farther away than that, you need a real milestone. to justify the bigger number. Fundraising Rule 5: Come back fast and come back bigger. Now, the fundraising playbook that puts these 5 rules to work. 5 steps to raise money when investors get careful. Fundraising playbook step 1: The dates milestone headline. Your first slide says that the round buys, by when, and who decides. Step 2, the approval plan. Start the outside approval before you start the raise. Step 3, score yourself before an investor does. And step 4, commit your current Investors in writing 4 weeks before you open. Step 5, the 14-day close. Every follow-up brings a new fact. Do them in order. You walk in with proof instead of a pitch. Fundraising playbook. Step 1, start with your very Your first slide should be one sentence. Fundraising playbook, step 1, the date milestone headline. This round pays for one clear milestone by a set date, and an outside party decides if we hit it. The strongest round I scored read exactly like that. For example, $94 million to run a final-stage drug trial. Busy investors back the rounds they can understand in one line. Most pitch decks start with a big vision. Reach the milestones on slide 12. Slide 12. Turn that around. Milestone, date, and who decides. That turns your raise from a request into a plan. Fundraising playbook step 2 is for when nobody outside has signed off on your company yet. Your strongest proof can take 6 months to get. So, the approval plan. Start the application. Before you start the race, take one page and make 4 columns: the approval, the body that grants it, the earliest date they could decide, and the person on your team who owns it. List every option in your field: a regulatory clearance, a government research grant, certification, A government contract. Pick the one you can get fastest. Give it an owner this week and put the submission date on the same calendar as your race. The clock starts now, not when you start pitching. Fundraising playbook step 3 is the one most founders skip. Score your round before an investor does. My eyes on fundability score has five parts out of the hundred points. Your relationship with investors, thirty points. Traction that outsiders have already confirmed, twenty-five points. Your story, twenty points. How the deal is built, twenty points. Your plan for the money? 5 points. Above 60, in sum: with a current investor committed, run a fast process with a firm deadline. Between 45 and 60, fix your weakest part before you start. Below 45, the problem is deeper. You are a returning investor, no outside approval, No named customer or partner. A better pitch deck will not fix that. So fundraising playbook step 4 pays off more than any other. Make your hardest calls 4 weeks before the start— you start fundraising. Commit your current investors. Picture a founder planning your next round. Before she meets anyone new, she calls every current investor with a board seat or a real stake. She asks 2 questions: How much exactly will you put in, and will it be more than your current share? And if a new investor sets the price, will you lead the round with them? She gets both answers in writing. Only then does she make a short list of newer investors. If a current investor says no, she asks what would have to change for them to say yes. Now she starts with money already promised, not hope. Fundraising Playbook Step 5. Turns interest into decision. Every follow should bring a new fact, not a reminder. So the 14-day close, what we're talking about it, put every interested investor on the same 14-day schedule. Day 1, the first meeting with a 1-page milestone summary. Day 4, a short update on a real thing: a new customer, a filled application, a test result. Day 8, a reference call with a named customer or a committed current customer. Day 11, a second update tied to your milestone date. And day 14, a clear decision date. If you hit the milestone during the process, offer a second closing at the same price for a short window. Urgency should come from facts, not pressure. Here are what I'm watching over the next few weeks. For the next six weeks, expect money to go to people investors already know. September ended. With the fewest midsize rounds I would count since mid-August. It was also the end of the quarter when investors finish deals with companies. They are already back. If rounders climb back above 15 a week and the median check drops toward $30 million, that was just quarter-end timing. If rounds stay around $11 million and the median stays about $35 million, this is the new normal for the quarter. Either way, call your current investors now while they are still deciding how much to set aside. By November, that money is already spoken for. And one surprise I'm watching because it could become a model. They raised less than last time and it worked. A New York biotech last raised money in 2022, $236 million. More than 4 years later, it came back with a new name, 3GMx Bio and a narrower focus, one drug in a final-stage trial. This time it raised $94 million. One of its very first investors from 2015 helped lead the round. Someone with 11 years of inside knowledge wanted more. It was the second-highest score of its If your last round was more than 3 years ago, stop defending its size. A smaller round with an old believer is easier to back than a bigger round with a new story. I've talked about fundraising, but changing strangers first isn't only a founder habit. Asking a stranger feels braver. It usually isn't. A job seeker sends 100 applications before calling the old boss who saw their best work. A salesperson chases new clients before asking a happy customer to buy more. A founder books 30 new meetings before calling The investors they already have. As strangers, no costs almost nothing. Someone who knows you can say no with full information. That's the conversation we avoid. The call you keep putting off is usually the one that matters most. Let's bring it all together. Fifteen rounds, seven renewals, eight strangers. The seven companies those investors came back took more than two-thirds of the money. Money. The eight without returning investors average nineteen million. Those eight were not bad companies. They worked in us. Strangers in a market that paid more and more for what is already new. You cannot make a stranger know you by Friday, but this week you can make the calls you have been putting off and start the one application you haven't. Before you chase a new yes, go back to the people who already said yes. Here is my question for you: which of these 5 rules is hardest for you? Tell me in the comment. Subscribe, like, and see you next one. Thank you.