Fundraising

“When it's average, it's super important To tell a beautiful story that's woven, like that, that, that's like a story that numbers are woven through. It's a beautiful, entertaining, interesting story with analytical numbers woven through it. And you basically g…”

“Like, if you think about it, there's two founders raising a pre-seed, and they're both fundraising, or meeting investors, Nobody's writing code. Nobody's selling to customers, right? The business is essentially shut down for the purpose of fundraising.”

“Fundraising isn't just a idea of persuasion. It's actually a way of life, that, that the actual interacting with people through the lens of them as the center of your conversation is a way of life, and that way of life requires a certain Level of responsibilit…”

“So many people do such a good job of using logos or logic to actually get somebody to a yes. And they still say no, because it's the difference between belief and trust.”

“If your first close is a billion dollars, you tend to tap out at two billion. Because your first close almost always is your hard re-elect number. That has been my experience.”

“So the first mistake that everybody makes is that they think that the logic Is where you're winning it. The logic actually is an output of a successful sales pitch, not the input.”

“I'm a big believer in like, you're either fundraising or not fundraising. There's a lot of like, oh, I'm doing these coffee chats, and like, hopefully we'll get preempted from this coffee chat, and all these, it's like, you're fundraising.”

“If you're in the market for a long time, it's a bad thing. And it's a bad thing. Maybe it's a good thing for your like valuation or for the amount of money you're raising or funds you're raising from, but I think it's a bad thing for the company because you st…”

“The fundamental truth is that's usually not where the sale falls down. Most people will believe that people are good investors. Most people will believe that the opportunity makes sense. They just don't trust the person. There's a big difference between belief…”

“If I want somebody to help me get into an account, that individual's relationship with the person they need to contact, I don't need an intimacy between them. They don't have to be close friends. It does help, obviously. That person just has to be respected. I…”

“Repeat back what they said. You want to make sure they say an objection. I think your fees are too high. Ok, that's an objection. Then you literally just have to repeat back. Ok, so hey, you just said our fees are too high. Can you give me some more color on t…”

“You need to know what you're auditioning for. Because it's not a sales pitch. It's not an interview. It's an audition. The idea that you're walking in, they know what they think they're looking for.”

“Then the law of trade-offs. It's one of the easiest and best laws to understand that you're always trading off size and terms and speed. It's size times terms times speed.”

“If the product is not worth raising money for, no matter how good you are, you can't raise money. In other words, if you have no differentiation, your track record's bad, it's a really complicated story, you're out of business. The general partners in that sit…”

“If your strategy's out of favor, if it's not in vogue, then what do you do? You raise less money.”

“A range of fundraising shows lack of confidence and A low understanding of your capital needs.”

“The two parts to it are, first part is the industrialization of the fundraising process, right? It's a liability gathering. So literally raising as much capital as you possibly can, literally as fast as you can. So that's sort of the industrialization of the l…”

“The goal for me with the podcast is to be able to create an additional stream of income because the fundraising is, is success. So if there's a moment where there's no success, then there's no money. And so while the success fees from fundraising can be very n…”

“You know, they want some level of greed to be clicked on. It's like, oh, If they do this, I can see why they would make a lot of money and make me a lot of money. And you have to then, once you do that, reduce risk, right? Basically show a through line between…”

“Twenty-twenty-six, they're still gonna skate by on, ah, on fundraising”

“Raising money is not an accomplishment, so I'm not going to say congratulations. Building a durable business is an accomplishment”

“Storytelling is more important in categories where fundraising is important in future as well. So there have been many good founders who have good, been good execution guys, but they have not been able to raise capital later. And so the company has not done ve…”

“One of the things that I remember that really transformed our pitch when fundraising was go deep on your personal story, like way deeper than you think you need to not, it's not just your resume. It's like you as a person, especially for you know, early stage.”

“Especially whenever I was in the process of either raising money or selling my company, it was these very brief periods of time, maybe three weeks, four weeks, six, six weeks, where the value of my years of effort would swing by 50%, depending on how good I wa…”

“You know, fundraising gets a gets probably too much press. In all honesty, you know, everyone talks about the company that raised capital, but not a lot of people talk about the people that bootstrapped the business to a successful exit. And I think sometimes …”

“I did not do any fundraising when I was building my first business, and I feel it could have given me a very interesting sort of insight into how to scale.”

“Fundraising is such a big thing when you know, being an intrapreneur, I come across some founders just like, I just want to operate companies, and I don't want to raise funds, and thinking that fundraising is our job, which I don't totally agree with it, but, …”

“But for the other 99%, it still takes three to six, sometimes eight months to raise capital. Oftentimes that is almost a full-time job during that time.”

“I actually think most people probably shouldn't fundraise. I think most businesses that are fundraising probably shouldn't fundraise.”

“There are two seasons of fundraising in the year. There's one in like February, March, and then there's another one that's like August, September, but that's like when they start.”

“Normally I say people don't wait, like wait until you have like maybe 14 or 12 months left and do your first attempt at fundraising or like test the waters maybe. And if it doesn't go well, you have another two shots actually. And then you can change things an…”

“I think now Jason would kind of say is like, okay, you got six months left. What can you get done in the next four months that makes your company stronger that gives you highest probability of success to close in six months and focus a 150% of your energy on g…”

“My preference and the thing I have seen work pretty well, I think when you're not, you know, I do like the concept of flip, this concept of flipping the switch. We're either fundraising or not, right? We're either on or not because you need to really devote, y…”

“People should not spend any time trying to optimize for like a fundraising outcome. And like, you should just basically wait until You're getting investors that are emailing you term sheets that are signed with like a blank for the valuation. And they say, jus…”

“Once you start to drive revenue, have real metrics, of course, you know, the fundraising pictures shift from being all about the dream, and the vision, and the market opportunity, to being about what has the business done, what is it going to do, and how much …”

“I didn't just know that you're going to build a muscle in fundraising. That's going to be, and you're going to build a muscle particularly for your portfolio companies who are doing big B to B deals, you know, seven figure deals. That muscle is the same muscle…”

“Even layoffs are simpler, because layoffs is like computation. Cut, and you're just in two or three weeks, and you continue your work. But fundraising, it's like, just like, it's each day you're getting no, no, no, no, no, no, no, no, and you're starting to lo…”

“Be conservative on how much you ask. You can always raise more. You can always raise more than you ask. And those things will just increase the odds in stressful times that you raise the money.”

“I believe that founders have three jobs. Sell, corporate development, fundraising. That's what you need to do in life, right?”

“Because, you know, in the life cycle of a company, you know, if you're doing anything worthwhile, you're going to need to raise money unless you're just one out of a million that bootstraps it and hits, you know, the big time from the start, that's very few an…”

“I very much believe you should either be in fundraising mode or not.”

“Fundraising is not to be celebrated. I mean, think about what you're saying when you celebrate fundraising. It's either a combination of Congratulations. Now the game is starting. Like, you don't get cheered for to start the game. You get cheered when you win.…”

“Generally, yes, because if you can raise a lot of money, it increases your odds of doing well dramatically and allows you to make some mistakes.”

“When you are in the process of doing any sort of M&A with your company, whether it's selling your business, acquiring other businesses, or even, like, just doing a Traditional fundraise. It becomes anywhere between, like, 50% to a hundred percent of your job, …”

“Every time I fundraise, and this is actually maybe a good tip for like startup founders that are fundraising, I actually write up like a big document with all of the objections I anticipate to get. And I write out like lengthy answers to all of them. And I don…”

“First of all, you only hear the success stories, like you only ever hear the success stories and they might sound like that, but the reality is often even that person that has a big track record wasn't that easy.”

“That's actually maybe the framework for all people who want to raise, right? Is that you're trying to build this story of like, this company is raising money regardless of you or not. You can choose to come in or not. It's your, you writing a check or not is n…”

“Here's how far we can get with two 50. Here's how far we can get with 500. Here's how far we can get with a million. They're all good places for the business to net out. There's all different strategies for them. You'll create different strategies around them.…”

“If you want to fundraise, you can gain that system. I gained that system, right? I gained school and I gained fundraising because you really can build a story and a deck and a presentation and all these other things to make you better at fundraising and to act…”

“Realize that fundraising, especially fun ones, can take time, and you have to be patient. 12 to 18 months is fine. People not meeting with you for a couple months is fine. People taking, you know, months if not sometimes a half a year to reach a decision is fi…”

“Worry less about the economic climate, and if you have to raise capital, don't be dilution sensitive. Get the capital you need, and be success sensitive.”

“It's a little bit challenging because when you're fundraising, you're a prophet, not a missionary. You have the vision, and you're trying to get people who already get it. You're not trying to convert people to your religion.”

“I think most founders treat each fundraise like a dot rather than a trend line.”

“When you're fundraising, you have to present a big picture. When you're recruiting, you have to present a big picture. When, even, even when you're just trying to keep your mental health of why is this so hard? You have to believe in that big vision.”

“I think in terms of fundraising, it needs to be like, it needs to be driven by the founder in the sense that you need to create like that typical, like FOMO situation where you can tell investors that other people are going to be making a decision like in the …”

“How the fundraising almost killed us. That's literally what happened at that moment. We raised money. We were super happy, but actually it turned out not to be the best best choice in our life.”

“I think I've been blessed by not being spoiled with a lot of fundraising from time to time, which I think really corrupts people and corrupts minds and corrupts businesses and corrupts many other things.”

“Something I didn't expect is that the way you raise Isn't so much dictated by your stage and your rounds. That's more dictated by the situation that you're in, in terms of traction, in terms of momentum, in terms of like achievements, right?”

“We had kind of a mantra, which is optimized for alignment, not outcomes. I think in many situations, people, companies can optimize for outcomes rather than alignment. And that over rotation ultimately over time leads to misalignment.”

“When you're fundraising, what you want to convince people of is inevitability. That the company or the fundraising round, its conclusion, its positive conclusion is inevitable.”