Following the Money: Dream Jobs Probably Don’t Interview On Campus
Without question, one of the toughest jobs to land in the finance industry is in venture capital. Will McDonald knew it was a long-shot for a guy who didn’t know anything about venture capital but he found a seam, and then hustled and wrote his way into his own dream job — and now he’s pretty sure that’s how he’ll stay there.
“How’d it go?” I asked as Will McDonald walked in on Monday after his weekend in New York City interviewing for a job.
“I got it,” he responded. “They offered me the job on the spot. Crazy.”
I was silent (quite frankly shocked).
He must have seen the surprise on my face as he continued, “Yeah I know — I was totally blown away. The interview went way over and all they kept wanting to know about was how I’d gotten to talk to Dan, the founder of SoFi and Ron from Prosper. I mean I saw the interview schedule and it was packed with all these super smart MBAs from Harvard and Stanford, kids who had founded companies — and they hired me.”
He smiled.
“Yeah I know,” he said shaking his head through the smile. “It’s crazy. Totally crazy.”
“I want to get into Venture Capital. Do you think you can help me?”
Venture Capital. Investing other people’s money in the hottest startup companies on the planet. Venture capital is the finance equivalent of being the sports agent or the Hollywood manager to a star. And these people — venture capitalists or VCs — who occupy these roles are often referred to as the kingmakers. Think I’m kidding? Forbes has an annual list of the best venture capitalists called the “Midas List”.
To say getting an “entry-level” job at a venture firm is tough is like saying it ‘might be a little challenging’ to climb Everest. There are plenty of pithy blog posts (usually aimed at MBAs) about how to break into VC as an associate or an analyst but none of them are particularly inspiring (unless you yourself happen to be inspirational on your own resume). A recent thread on Quora offered the following routes into VC:
- Work for 1–4 years at a top-3 management consulting firm (McKinsey, BCG, Bain) or at a top-5 investment bank
- Join a trendy, fast-growing growth tech startup in a product, business development, or corporate development role and dominate for 3–4 years
- Get an MBA from Stanford (or maybe Harvard) and join a bunch of tech/entrepreneurship clubs while there.
- (And my personal favorite) “Be born really wealthy, preferably the child of a rich VC. You can maximize your chances if you go to Stanford in this case.”
When Will McDonald came to me and shared that his heart was set on getting into VC, I ran through that mental checklist and tried to suppress my urge to be patronizing with a “that’s cute” response.
Will wasn’t getting his MBA — and wasn’t even pursuing a quant-type degree from a Wharton or Columbia. He had ‘worked at a startup one summer’ but let’s be honest, if it wasn’t high profile enough to mention the company by name, then it wouldn’t matter to any VC firm. He hadn’t even interned — let alone worked for 3–4 years — at a big consulting or investment banking shop. The sad truth was, Will wasn’t someone they’d typically look at for an interview, let alone hire.
“I just feel like it’s the perfect thing for me — I love startups and I’m a finance major.”
“Ugh”, I thought to myself.
In his new book Vested, Will captures the zeitgeist of the millennial generation and applies it investing. If the rumors, stories and musings are to be believed, this generation looks at the world differently and perhaps as Will describes in his book: “With more skepticism than their parents ever had — we don’t take anything at face value.”
In some ways, his insights were a happy accident — but an accident that he then turned into his dream job in venture capital.
“I’d been fascinated by investing in companies and predicting who would thrive because of X, Y or Z. So I started playing around with new apps and tools and fell in love with Robinhood. It was beautiful and easy and let’s me invest small dollars in companies. I was immediately hooked. And then as I started asking around, I realized that a bunch of other people I knew were using it too.”
“The reason I found so many people like me who were all pumping our college beer money into these non-Wall Street tools like Robin Hood: none of us trusted the financial system.”
Will knew there was something here, but didn’t quite know what it meant until he kept pulling the thread. What he discovered has taken nearly every sophisticated investor and wealth manager he’s spoken with by storm:
Millennials and Gen Z aren’t going to invest like prior generations
And with Vested Will is offering a vision for the future that allows this generation to:
- invest in new asset classes
- invest with the crowd
- invest in things they believe in
- invest in smaller amounts
- use technology to compete
- invest in private companies like they see on Shark Tank
- be active in their investing
“In Vested, I’m really looking to expose my generation 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 amounts 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 has legs in it rather than just putting $100 to work in just another fund in the market.”
In some senses, Vested is a book describing a walking dichotomy; a ‘how to’ guide that explores this highly and recently regulated industry, and dives into the rules and requirements to participate for a generation that has yet to amass large piles of investable funds. At the same time, it examines some of the fastest growing technology companies, products and services in the world. It’s a little bit like reading a book titled “How to Make Money from Facebook” written when Zuckerberg was still living in his college dorm. So just how did Will accidentally stumble into the convergences of some of the largest trends in our country?
“Whether it is through individuals starting companies to solve major problems, or politicians actually pushing for change, I think I have always been drawn to areas where you can actually lead change through your own initiative.”
That reads like a stump speech my friend. And worse still, isn’t it at odds with the emphasis on that well-paying, fancy position with a big corporation or investment institution you wouldn’t mind yourself? “How are you going to make this real?” I thought as he shared that with me.
But as I quickly learned, Will has quite the personal motivation to be drawn to this emerging trend within a huge, regulated and evolving industry.
Will’s mom? Worked in the White House under Reagan. His dad? State Department. It goes on from there,
“I have been fortunate enough to see the workings of Washington from the inside through my uncle who has serves as a congressman for several years from the north side of Chicago. Having long been a role model for me it was really interesting to see the back side of Washington and how honest leaders could make an impact. He showed that although the media likes to show a fully broken system, that at times the right people with the right vision can push forward real change in an often chaotic and divided system. Having run the family small business in the past, he came into the position in his early forties, the father of three, and was able to make a real impact early on.”
Will believes small teams can work for good even within governments perceived to be too big and too corrupt. And with investing, his book describes the potential for beneficial and big changes in government to be translated to the equally bloated and corrupt Wall Street. Some may see the JOBS Act or Dodd-Frank as missed opportunities. Will recognized that maybe the real opportunities were just being missed. Or were missing the people like himself who were most drawn to them.
Will decided to dig in, even as he wondered how he could possibly address the dissatisfaction of his peers.
“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 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.”
Will’s take is that the while this generation doesn’t have huge amounts to invest today, they are already making different types of bets and are even starting to influence people like their parents. Not only do millennials require more personal and direct involvement in everything, approaching investment in an involved way will address their lack of trust in financial institutions having lived through crashes and corruption galore.
“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.”
And while the Crowdfunding, Crowdlending and CrowdInvesting movement are still in their early days, Vested offers a compelling narrative as to why it’s the future, and how people can get started playing now even with small dollar amounts. McDonald began observing his classmates and environment to see where he could bring this new and necessary angle.
“It was interesting to observe my peers at Georgetown. They 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 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.
As you’ve read by now Will did in fact land his dream job in venture capital and now brings the credibility to his writing, investing work and (as you’ll see) future books. But it’s worth noting Will didn’t expect to be here either. And whether or not Will leads with this in conversations with other VC investors at fancy cocktail parties, in the back of his mind he admits that his own early toying with Robinhood, AngelList, Lending Club, SoFi and other crowdinvesting/crowdfunding platforms were mostly a hedge against the realities of his VC career aspirations: a true back-up plan.
“If I can’t get into VC,” he shared “then maybe I can play around with these new finance or investing tools, make a little money, get smart on this stuff, learn the game and one day convince someone I know what I’m doing or maybe launch my own thing.”
Confidence is admirable, and Will was clearly willing to work, and had taken some of the right steps to get there. But the problem was Will didn’t check the boxes required to break into the big game of venture capital. He certainly said all the right things and I admired his clear direction (different than many others I’d met), but it was probably more hot air than reality.
But give him credit, once he set his mind to it he was AT LEAST going to try.
“I leveraged the Georgetown name, our campus startup club and networked any way I could — events, phone calls, emails, whatever. I was going to talk to anyone that might know anything about VC and just learn.”
“I remember sitting down with guys like Jim O’Connor, a Georgetown Grad and the founder of 1871, and Kevin Willer of Chicago Ventures, and getting their advice on how an undergraduate could possibly enter into the competitive venture scene. The advice that I was constantly getting was that the only way I could get a job in venture capital was to (a) either be coming out of my MBA, (b) coming out of a two-year analyst program at one of the big investment banks, or (c) having spent a good deal of time in some sort of a project management capacity at a highly successful growth company.”
But undeterred he continued to have these conversations — talk after talk receiving the same advice about being patient and waiting his turn. If he paid his dues, he might earn a seat…in a few years.
“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 was 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.”
“My plan was hopefully I could use that [an analyst program] to get into the typical investment banking program and somehow gain enough experience to get into the venture world at some point down the road. I knew I would have to bust my tail to get into it and that it would take a couple years but I was determined to follow that path if it meant that I could “cash in my chips” and get the job that I had been hoping for in venture investing in the end.”
But he was smart enough to always ask if they knew of any opportunities he could ‘jump the line’, and continued to share the unique insight he’d drawn about ‘millennials seeing the finance and investing world differently.’ He reasoned that if he could get his foot in the door, good things would happen.
His ‘foot in the door’ break finally came from a smartly worded cold application to a venture firm hiring in New York — he’d offered a snapshot into his insights convincing them to bring him to the office for an interview. He’d hinted at his thesis — big opportunities existed to bet on startups and new technologies leveraging this changing impression the younger generation had for the finance and investing sector.
And they’d taken the bait.
As Will prepared for his interview — the only one he’d landed in the venture capital space — he knew he was behind the game. He hadn’t taken a venture finance course, didn’t know anything about liquidation preferences, pre-money valuations and couldn’t even rattle off the names of any hot NYC-based startups. He came to me and said, “I’ve got two weeks, how would you prepare?”
In one hand, Will was carrying Brad Feld and Jason Mendelson’s seminal text on venture capital funding and financing: Venture Deals. In the other was a draft of the next chapter of the manuscript for his book he was working on. He was asking me to help him choose.
“You got your foot in the door by being different,” I replied. “My bet is to go in completely blind about anything related to venture deals, financing lingo and go deep on your book. There are million MBAs that all know the same things about finance — but you’re probably the only one who has a unique thesis on the future and is writing a book on it.”
I could tell my answer wasn’t what he was looking to hear — partially because I hadn’t given him an excuse to skip two weeks of assignments, but partially because it was totally contrary to what he thought they wanted.
Hire a venture associate who knows nothing about venture capital? Are you crazy?
To Will’s credit he never cracked open the book and instead kept on writing his own. Peter Drucker, the great management consultant and author wrote “The best way to predict the future is to create it.” And that’s what Will set out to do.
And sure as hell, Will landed the job.
How?
You guessed it — the book.
“My firm, Lead Edge Capital, are pretty amazed that I was able to just pick up the phone and call these guys up. They are investors and they’d love to talk to the founders and executives and CEOs and investors I’ve interviewed in my book. That’s why I stood out to them. All we talked about was the book.”
In a world of talkers, and credentials, and boxes to check, Will stood out because he knew what he wanted, honed in on something unique and demonstrated by doing. Sure he was only halfway through writing his manuscript when he’d landed his job, but that was enough — he’d proven he could create something and offer a unique and contrarian take on the world.
Will McDonald was a venture capitalist.
“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.”
And for Will, it’s not just about landing the job — it’s now about winning the game. And for him, he’s focused on extending his insights on millennials and emerging trends:
“It’s funny, but I’m already working on my next book,” Will offers less than two months after publishing Vested. “I see the same things going on with my friends and people like me with respect to blockchain. So I’m starting the script again — going out and talking to the smartest people I can find, the founders, funders and investors. We’ll see, maybe this becomes my way to stand out.”
A lot of this success for Will resulted from his confidence. Distinct from bravado no different than that of any other high-aiming business student, Will was empowered by the realization of his unique perspective he unearthed through the personal examination that went into his book. This is what ultimately turned a unordinary desire for a career into an opportunity to reach out as an extraordinary resource to the very companies others once told Will he would have to jump through years of hoops to even get to glance his way.
The confidence writing Vested has fostered for Will goes beyond landing a single job.
“I think what’s been crazy is that there’s been a whole shift in my mindset of what anyone can do in a short period of time. 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. Even going with blurbs, you never know who’s going to say yes.”
Will plans to leverage his insights, knowledge and connections earned and built creating his book to open new opportunities for investing to his firm. As it turns out — he’s learning — being an investor who is researching, writing and publishing about one of the hottest startup sectors on the planet has its perks:
Startup founders want to talk to him and pick his brain about what’s ahead.
Will’s story isn’t unique — in fact every day and every year people bemoan the fact they don’t have their dream job and don’t love what they are doing. Knowing what you want to do is one thing. But if you know and it’s competitive, challenging or prestigious, you’d better be willing to do whatever it takes to earn it.
The story may look like “lucky guy lands job at a VC firm” but that overlooks the hours and hours Will spent talking with anyone about venture capital, when none of them were ever likely to open any direct doors to VC. And you’d also miss the depth he developed calling strangers to get their insights for his book. That is the real story here.
I’ve realized my students who not only know what their dream job is, but are pursuing a “big” one are often confronted with an unfortunate paradox. Particularly in Will’s case, because of the status and high-volume desire for his pathway it’s presented in a very narrow and limited way. And success in venture capital, let alone getting hired, is a pipe dream in the most literal of senses.
Yet McDonald has does not need to narrowly package himself in the way so many with his same goals feel they must. And, I firmly believe this same realization can apply across vocations, making it all the more exciting for the crazy potential of its applicability.
Will has proven to himself, to me, and now to employers that nothing is more valuable than someone unafraid to figure out what their unique contribution to their dream is, and then chart their own course to it.
Now, Will is all to ready to encourage others in the same way.
“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.”
His advice applies just as much to opportunities for investment in equity crowdfunding and peer-to-peer lending as advice on investment of talents and interests into the future careers of his peers. Where will skills and experiences they have, what they are most passionate about, translate into the most good for a prospective employer?
Found something you love? Dig in, talk to people, share your learning— you never know where it might lead.
For Will, it led to a New York City office with three other colleagues, evening delivery of Chinese food and 9:15 pm conference calls.
“I couldn’t be happier — it’s addicting,” he confided three weeks into his role.
Quite the back up plan.
The substance Will has brought to his job search through this process of interviews and developing his personal experience as a launching point has fine-tuned his hustle. Will is no longer hoping to be someday picked from a sea of candidates pushing for a role in venture capital. Will McDonald is set to win a race he once thought he was miles from the starting line of.
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.
To learn more about Signal Class visit www.SignalClass.com or to apply for an upcoming experience, visit www.SignalClass.com/apply.
