In a 10‑minute talk at HustleCon 2015, Adam Draper—founder and managing director of Boost VC and a fourth‑generation venture capitalist—shares the hard‑earned lessons from his own fundraising experience and from evaluating over 130 portfolio companies. He opens by emphasizing how fundraising is exceptionally difficult, citing his own 12‑month, 3,000‑email, 350‑meeting, 35‑investment journey. He then outlines seven actionable principles: (1) accept the difficulty and prepare mentally; (2) treat each investor meeting as a long‑term networking opportunity; (3) pitch relentlessly, rehearsing with friends and aiming for multiple daily pitches; (4) remember that no money is committed until it lands in the bank, warning against premature optimism; (5) understand that investors invest in a founder’s trajectory (“lines”) rather than a single interaction (“dot”), and keep them updated with regular reports; (6) focus on the three core investment criteria—team, real traction, and hype—while recognizing that genuine product traction outweighs hype; and (7) always have a Plan B, viewing fundraising as a tool for growth rather than a marker of success. Draper concludes that modest capital can still fuel massive impact, urging founders to prioritize solving problems over raising large rounds.
Chapters
HustleCon's pretty cool. Yeah! My name is Adam Draper. I'm founder and managing director of Boost VC, and I'm going to talk to you about fundraising. How many people— sorry, these lights, I can't really see everyone, but How many people have started a business? And how many people have actually gone through the fundraising process? OK, so less of you. So this is going to be relevant to most of you. That's great. And it'll be relevant to all the people who have actually raised their hands. So my name's Adam Draper. I'm a fourth-generation venture capitalist. I'm a founder of— I founded a company called Expert Financial in 2009. I founded Boost VC in 2012 from Basically, I help entrepreneurs not make the mistakes I made with Expert Financial. And then I've invested in about 130 companies at this point. Collectively, they've raised about $300 million. And I see about 1,200 pitches every year. So I've also— it's not up here, probably because it wasn't relevant, but I was on Nickelodeon at one point. Nailed it. But so basically all this means is my ancestors raised money and helped people raise money. I've raised money for different things, and I really enjoy helping entrepreneurs get better at what they do. So today's talk, I have 10 minutes to tell you all I know about fundraising, which it could be a longer conversation, but I'm going to give you about 7 points. That I believe might help in the fundraising process. It's more like concepts to wrap your head around when you're going through the process. My first, my first piece of advice is fundraising is very difficult. It took Christopher Columbus 7 years to raise money from Queen Isabella in order to travel across the ocean in order to find India, and he failed epically. At that. And he found— I always picture like Christopher Columbus like going back and saying like, "Oh man, I didn't find India." But fundraising is really difficult. Fundraising is incredibly difficult. When I was pitching to raise money for Boost, I emailed 3,000 people. I met with 350 of those investors. 3,000 investors, met with 350. And I ended up with over about 35 investors. And so it was about a 10% decline. And it took 12 months to do this. So it was 12 months, November 2013 to November 2014 I was fundraising. And that's really, really hard. It's mentally trying. So yes, 35 people said yes to me. That means that 315 people said no. And dealing with that is a really, really difficult thing every day. And so I— so really just start. If you're going through that process, just know going into it that's going to be really difficult and make sure that you're ready for the trying trials and tribulations you're going to be going through. OK, number 2, once you've wrapped your head around the fact that it's going to be difficult, use these meetings to meet cool people. I got to meet everyone on Sand Hill Road up to Fortune 500 CEOs. And I used every meeting just as a connection. The most important thing that you can get out of a fundraising meeting is a connection to someone, because that's not going to be the first time you run into that person. I have a later one, later piece of advice that's going to be about how no one invests the first time. But basically, you should be thinking about this as a connection for a a long period of time, someone who you will be able to ask for advice if you have a really good connection with them. So just use fundraising as a way to meet a bunch of really, really great people over the course of a very long period of time. It's literally like running into a wall repeatedly for 12 months. Getting rejected 315 times in a year is not really all that fun. It's literally like I spent the year just getting rejected. And then someone said yes. I was like, oh my God, thank you. OK, third, pitch your company to everyone. This means— so basically, VCs and angel investors love having prepared entrepreneurs. And in order to be prepared for your angel investor and VC meetings, have your friends— pitch your friends. Have your friends ask you questions. It turns out VCs and angels aren't the only ones who ask good questions. Actually, we probably ask worse questions than anyone else. And you can learn about your business and how people are perceiving your business. And I really think that a lot of entrepreneurs don't do this before they get into a meeting with someone. Test it. And if you're not willing to actually test your pitch on one of your friends, you're not going to be doing well in an angel or VC meeting. That's just generally how it goes. If you feel embarrassed by your product, you're I have to pitch Boost every single day. You have to be pitching your business 3 to 10 times every day in order to really get good at it and formulate your entire concept. OK, this is an unfortunate consequence of fundraising. You have no money until it's in the bank. So when I went through the fundraising process, you will meet a lot of yes-men investors. And you will get them to say yes in that meeting. And that's fantastic. And then, like, you will try to follow up with them, and then they might be late on replying. And then, you know, you have a couple emails back and forth, and then all of a sudden, like, it's been 2 months, and they're not going to be wiring you any money. And like, that's very disheartening because they gave you, like, they gave you that moment where you're like, oh man, this person said yes, and then they ripped it away from you, which is the worst feeling in the world. So just know, like, again, this is a part of like fundraising is difficult, but just know you have no money until it's in the bank. No money is committed. And so what this should do is make you feel once someone says yes, some of our investors actually, I don't necessarily recommend this, but basically what they do is they have convertible notes of different amounts in their backpack and they literally will push it across the table and be like, if someone says yes, they're like, how much? And, and, and, and it's like, but it's literally the concept is there where it's like You have a ticking time bomb of getting that money from their bank account to your bank account. So just know that it's nothing until the money's in the bank. Clicker. Does that work? It did for this entrepreneur, for the record. OK, 5. This is the one. Investors invest in lines, not dots. The first time you meet an investor, that is the first time you exist. You did not exist previously for that investor, for anyone in their minds. And so they're thinking, OK, so now I want to see this entrepreneur start a track record. This is day zero for this entrepreneur. And so over the course of time, the reason accelerators like Boost, YC, all these other accelerators are really good is that you have 3 months. Investors trust us, and we help companies build a track record over the course of 3 months. And so what you want it— so lines, not dots. I'm stealing this from a really great entrepreneur. His name is Jeff Siebert. Forgot to say that at the beginning of the slide. I always want to give credit where credit's due. He's awesome. But investors invest in lines, not dots basically just means you cannot think that an investor is going to invest the first time that you meet them. Do not ever think that. It is the first time that— yeah, just don't think that. So over the course of time, just keep that investor updated. The best entrepreneurs, they email me every month and update me on what has gone well and what has not gone well over the last month. That is all the best entrepreneurs, literally. And they're very consistent about it. And also, if you do a monthly report, basically it gives you an idea of what happened over the last month for yourself. You're able to summarize it for yourself. But it's really important to keep investors updated. I'm sort of running out of time, but— Investors invest in team, traction, or hype. So basically, team I've referred to. Traction is really, really important. Get your product out there. Hype is something that, like, I've seen entrepreneurs do this. And it's basically you convince an investor and all of the investor's friends that you are the coolest thing at a moment in time. And it is really, really difficult to do. I do not recommend trying, like going out and being like, "I'm gonna raise off of hype." I mean, the best way to do it, like the best way to fundraise is to have a good product and good traction that is like real traction. And yeah, so that's that. Okay, the 7th point is have a plan B. Assume, I mean, you really don't want to assume you're not gonna raise money, but realistically you might not. You still need, if you are truly setting out to solve a problem in the world and you really want to make that difference happen, money should not be the reason that that difference doesn't get, happen. So you should have a plan B on cutting costs, on making sure that everything happens the way that you want it to. And yeah, so, okay, here I am, skim me through this. Okay, fundraising is a means to an end. Basically, make sure— that wasn't— yeah, I don't need to explain it. I'll explain it if anyone wants to ask me later. But the fundraising is a means to an end. You need to grow faster. You need to hire someone. You need to get an engineer. You need to— there are a lot of things that you need to do and you need that money for. You should not be thinking that it's an element of success. There's a weird mentality in Silicon Valley right now where If someone fundraises, it makes them feel that they have been successful. It should not be— that is not the mentality that you need to have. You are using that money as a tool to grow your business. That's one of the most important things that you should be able to walk away from this presentation with. In addition to that, something to think about if you are in that fundraising process, Microsoft, eBay, Viva Systems collectively raised $11 million when they were fundraising. And that is now on the NASDAQ stock exchange worth $420 billion for market cap. You don't need to raise a lot of money to make a big impact. I'm an investor, and the best companies don't raise all that much money. It's a really important thing. Don't think that fundraising is the end goal. Fundraising is not the end goal. The end goal is building— solving the problem you set out to solve. And that's all. That's my presentation. Hopefully you enjoyed it.
