Turning a Dream Into a Career: How Will Didn’t Take the Easy Route to VC
Will McDonald needed a bit of luck and a way to prove he knew how to hustle to get a crack in one of the most competitive industries on the planet: venture capital. As luck would have it, Will learned the value of a ton of cold calls and create ways to open doors in his book Vested — and that was enough to stand out from the crowd and land him a desk at a venture firm in New York City. Read our full interview.
Signal Class (Eric Koester): Tell us your name and a little bit about your book.
I’m William McDonald. I’m the author of Vested: The Millennial’s Guide to the Next Generation of Investing.
Did you ever think you’d write a 200 plus page book?
No, I didn’t. I certainly didn’t. I hoped I would but I don’t think especially in the stage of my life where I thought it would have been possible, which is pretty amazing and I’m excited to see when the time comes that the physical copies come in, how those look. It’s still not completely real. Even just going through the cover process is pretty amazing to see the end of the long process that it’s been.
What is the reaction from your family?
They’ve been following along the whole time of the process. I think it’s real to them when they see a raw manuscript over Christmas break but still I don’t think any of them had an idea of what that would look like, if it’s just going down the FedEx store and getting that bound up from printed pages or what.
But as I sent out that first iteration of cover drafts, I think it really clicked and became real and for myself especially, too. At that point, it was words on paper versus I can see the end result of this, I can see a book coming out, which has been pretty amazing to see just the transformation of that process along the way.
How has the book affected your career path?
I worked for a couple of start-ups in the past but being a finance major at Georgetown, I was really curious of how I could combine the two worlds and being deeply involved in the start-up community here. I’ve always known venture capital in some capacity.
Going back to the last winter break, I think, I was really curious of how I could possibly find a job in the space. I went and talked with a bunch of guys who were active at these and just picking their brain on how someone even an undergrad can get a job in the space. The response I was getting is it’s not possible. You need to come with an MBA or you need to do a two year stint in investment banking. Even then, they’re going to be competitive and most likely won’t even get a job there.
I’ve always been really interested. When I found equity crowdfunding this last summer, how you could have the ability to act in the same role as a venture capitalist but with a lot less capital overhang, it certainly piqued my interest.
Going and being able to build the book on what this emerging world of everyman’s VC would be really helped reshape how I now have a job for this summer, where I was surprised to find as we’re going through the process of the book early one, one group Lead Edge Capital is a growth equity investment group posted a job listing for undergrads here. I saw it immediately and sent an application.
I was not really sure I was going to end up getting and was able to lever the book experience. The job itself is due diligence. It’s going out and vetting, finding companies of interests. You’re finding interesting investment opportunities. You’re calling the companies up and you’re really seeing it as good business model, do I believe it in the team and do I think for the group that it makes an interesting investment.
I was able to lever this whole process of calling the Dan Macklins of the world, the Ron Subers over at Prosper and saying, “Hey guys I found these companies and I found a way on the door to get on the phone and I’m comfortable doing it and I’m happy to do it and it’s actually of great interest to me.”
They’re pretty amazed that I was able to just pick up the phone and call these guys up. It ended up landing me a job this summer which I’m excited about. It’s exciting what it goes to show you, I had no idea what I could do with the book beforehand. But it’s really been completely transformative in my entire trajectory there.
How has your book unlocked a new opportunity in venture capital for you?
The firm itself has not have any FinTech focused investments. Coming in from my interview, I had mentioned that maybe I could focus on it a little bit more. While I haven’t had the conversations yet with some of the partners and other principals of the group about really levering the book, I know they found an interest that there are connections in the space right now with those guys, any of those major FinTech companies. I haven’t fully fleshed out how that’s going to look but I’m excited to see how I can lever it for sure.
What did you think when you heard “you’re going to write a book”?
I was thinking how could we possibly in this one semester? But was intrigued for sure to see how everything would play out. I was not sure how the semester would go but was intrigued to see over the couple of weeks how things developed. Obviously being the beta test for everything was unique but worthwhile.
Why did you pick your book topic?
I’d say that it’s important to make your money work smarter for you. I think we as millennials value an intimate connection with whatever we do, whether it’s social media and constantly being able to be updated with your friends or just being able to custom curate your newsfeed. I think people value a deeper connection in. I think to date the stock market hasn’t adjusted to that level of intimacy that’s needed. Looking towards outlets where you can support your peer down the road for your business down in the town next door is big.
The question that I pose to millennials as they’re looking to invest is where do you really want your money to work better for you? It’s not a matter of not necessarily generating the same returns as much as it is understanding exactly how you want to put your money to work.
I’d say explore equity crowdfunding. Explore the opportunities out there. Explore peer-to-peer lending as an opportunity to do almost a social good as well because you’re helping whether it’s small businesses or people who just couldn’t afford it or been given the opportunity for mortgage or something else to support them and show faith and also generate possible return on the same end.
How did you pick your book topic?
I remember one of our first exercises was coming up with hundred different business ideas which I thought would be more of a daunting challenge than it was. I know we had divided it up by type of business and category based on our interest. I wanted to not go deep into one specific niche but see what the possibilities were.
Where the broad types of businesses came out, I just wanted to explore any idea and see what ended up in the end. It made it a lot more helpful coming from 100 down to 5 to 7 ideas but it was definitely an interesting process.
I attended a panel this summer in Chicago at the Incubator out there on Finance 2.0. At that time, I’ve been working in probably one of the more traditional finance route working at wealth management. I had big interest in start-ups in the past. I was curious what this next generation of finance panel would be and exposed me to the world of peer-to-peer lending and crowdfunding.
I spent the majority of that week really diving deep into this new space was. It piqued my interest but I really haven’t followed through it too much the rest of the summer. Come time to really dive deeper into new ideas for where we’re going to start a business or interest in a space, I remember back to that panel on alternative investments.
I wanted to see where it went. I really had no insight on the space or little about it but just dived deeper and see where it took us.
What did you learn interviewing people for your book?
It’s interesting here in Georgetown. We obviously have a big finance presence. A lot of students in one way or another are involved in the world of investing. But still with my peers outside of the business school, I noticed that a lot felt disconnected from the business they’re making. They’re either going through traditional stock brokerage or even some tech savvy enough are using app like Robinhood which let them trade for free but in reality was their money was being put aside and not a ton of thought was being put into it, whether putting it in a couple of indexes or more passive funds. They saw it and just put it away, let it sit and I don’t think it’s going to make more than it would make me in the bank.
But then I exposed them to this idea that you can have a little bit more direct impact and plenty of them have seen Shark Tank and understood the idea of what it would be like to invest in a real estate company and were intrigued by the possibility that even small amount of money could potentially roll the dice and invest in the small business down the road, or the app they had on their phone, that potentially have legs in it rather than just putting $100 to work in just another fund in the market.
I think they’re intrigued. Most of them haven’t heard of the idea in the past that you could actually do this but were definitely interested in exploring it more, which was fascinating for my part because I realized that we were really at an inflection point in that development, obviously. Equity crowdfunding has only been around since last spring for the masses.
And so, diving deeper into it, I realized that I was able to get experts on the phone who were some of the top minds in the space of pretty growing and massive space while it was still new and not really as exposed to the public yet.
Who did you meet while writing your book?
It was really interesting. At the beginning, obviously you tasked us of going and trying to find people to reach out to on the phone whether we find their email or LinkedIn or something else and finding a way to get a connection and get them on the phone. I remember the daunting challenge of having 20 interviews in a short period of time.
Where I had friends who could maybe even just go interview their own friends who had experience on the topic they’re writing, I kind of wanted to shoot higher for that and the guys I wanted to interview were the founders and co-presidents or co-founders of these big financial institutions. And so, I compiled this list of SoFi and Prospers and lending clubs of the world and build a hierarchy.
I didn’t think that I was going to really be able to get anyone on the phone but I remember one of my first emails going out to Dan Macklin who is one of the co-founders of SoFi now valued at a billion dollars. I just shot an email out of the blue. I didn’t really expect any response.
I think within 15 minutes he got back to me saying that he could schedule a call the next Tuesday. And so I went and called him up that Tuesday kind of intimidated about the fact that I was about to talk to the co-founder of this company I have been following so much in the past. He couldn’t have been a nicer guy explain the story of the class, what we’re doing and what the vision was when at that point it was still an idea for this book. We weren’t even sure if we’re even going to get it off the ground but he couldn’t have been more helpful.
What was supposed to be a 15-minute long interview ended up being 45 minutes as he’s running from end of San Francisco and another in a car. It was pretty amazing. We’ve actually been going back and forth via email since and he’s been very supportive with the whole process. But stories like that are getting guys who are pioneers of the space and had been so pivotal and so influential in the development of this massive industry, you’re just going to pick up the phone and call and really pick their brain with has been pretty incredible having those connections.
Did you have doubts while you were writing your book?
I actually don’t see myself as a writer, really which is definitely pretty unique. But I think the process of being able to transcribe our audio recording helped tremendously along the way. I know towards the end there, the last leg of the book was really done over break. It was a daunting task thinking that ten days out from the deadline, I still have a big amount of content to push out.
I think at that point I had a moment where I wasn’t really sure if it was going to get done. I knew I had the ideas to put forward in a book but I couldn’t possibly see how 10 days would go by and I have a finished manuscript. I think using that unique method of really being able to synthesize your ideas and record yourself speaking it out for 10 or 15 minutes and being able to transcribe that content and using it as a backbone I know helped along the way because I was able to push forward a ton of content in a short period of time, which is pretty amazing.
How does it feel to publish your book?
It’s pretty crazy. It’s crazy to believe that we’ve come this far in just a couple of months and excited to see and do the first launch.
How have you grown from writing a book?
I think a lot. I think what’s been crazy is that there’s been a whole shift in my mindset of what we can do as students in a short period of time specially during that last call to 10 day stretch really needing to go and generate a lot of content for the book. It’s made me look at my time a lot more valuably and see what I can do with my time, that when I had a down hour and I somehow can kill it on some form of social media, I realized exactly how much value I could have generated out of that.
Away from that, it’s given me a lot more confidence to call up whoever and realize that as a student but just in general, there’s always a way in the door for anyone whether it’s Dan Macklin at Sofi or anyone else. I know my peers have interviewed other people. They’ve interviewed some pretty fascinating people. It’s interesting that you can always shoot a cold email out. The worst they say is no. But I think far too often people realize that you can’t even make the ask in the door. Even going with blurbs, you never know who’s going to say yes.
I remember the CFO of Airbnb actually came and spoke — he’s a Georgetown Alum — a couple weeks ago and we were in the midst of this blurb process. I really had no idea who I was going to ask besides the people I interviewed. But I thought, what the heck. I’ll print out a manuscript and hand it to him. While I haven’t heard back or seen anything from that, you never know. He’s a Georgetown guy and said he’ll be supportive but it’s like, just make the ask maybe they’ll say yes.
It’s been interesting enough, been fortunate to get a bunch of guys who I was able to interview to say yes to blurbs. I actually just got a great paragraph blurb back from one of the co-founders of the biggest peer-to-peer lending conferences in the world, Lend It, who I sent the manuscript to and he gave me a great blurb and hopefully I’ll be able to include so I’m looking forward to it.
What advice would you give to someone starting out this process?
I actually have a couple of friends who are taking the class now and I was thinking about that a lot as they were going in and looking for some advice. The biggest advice I probably would give myself before was make sure to pick the right idea and invest yourself fully because it’s such an opportunity to create a lot of value that doing it wrong or not doing the right one I think would have been painful.
I’m glad I did what I did. Obviously, it’s been beneficial since. It’s really opened up this whole potential venture capital opportunity, which has been pretty amazing as I’m sinking my teeth deeper into it. I just keep finding more and more opportunities to expand and we’ll see where it goes come book launch on what we’re able to do with the vested investor backend media site and everything else. I’m excited to push forward.
Even going before, just realizing that you may not think you’re able or capable of putting a book together but it’s a testament that step after step you can build something pretty remarkable in the end.
Give us the short pitch for the book.
Okay. I’m William McDonald and I’m the author of Vested, a guide for millennials to learn how to invest in the new sharing economy.
Who should read your book?
The book is for millennials who are looking to make their money work harder and smarter for them and learn how they can lever the new technology of today truly find the innovative uses for their investments.
Who do you hope reads your book?
You know what, probably my family at first. I think showing the end product will be pretty cool. I’m excited to be able to share that with those guys first and foremost. Obviously giving it to Steve Case or someone else will be pretty amazing but I think seeing the end of this whole process, they’ve seen late nights back at home over break, pushing out the manuscript and iteration of the publishing process, being able to show the end result of everything can be pretty special there.
Watch the full interview here:
To connect with Will for speeches, presentations, interviews or consulting work, wrm29@georgetown.edu. Purchase Vested on Amazon. Watch his interview on Youtube at Signal Class.
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