My winding road to VC in 2009–2010

How I broke into VC in the post-2008 period

(Note: This post was originally written on March 16, 2020. I’m posting it here to consolidate stories that I found resonate with many friends.)

When I enrolled in the Wharton MBA program in 2007, I didn’t follow the traditional path of recruiting for a summer internship but instead focused my entire free time on a start-up idea with a few friends in Philadelphia. But things seldom evolved as planned.

Resetting in my 2nd year at Wharton when the startup project failed, and the global economy crashed.

In September 2008, my startup endeavor hit a steel wall because of a co-founder’s health issue. Around the same time, Lehman Brothers filed for Chapter 11. The global financial crisis started.

Throughout the fall semester of my second year at Wharton, I felt completely lost. I didn’t really know what I would pursue after graduation, other than my own start-up, which I put all my efforts into. As much as I wanted to jump-start my post-MBA job search, I was too late to pursue popular tracks like investment banking or management consulting. It was the first time in my life (and the only time so far, thankfully) I lacked an objective to pursue. It felt awful.

Around Thanksgiving, some friends suggested, “Why don’t you look into venture capital?” I was intrigued by the idea right away. On the one hand, at the time I met some VCs from the other side of the table as an entrepreneur pitching them ideas, so I had a rough idea of what VCs do. On the other hand, since I didn’t know any exciting start-ups that I felt attracted to (except that they did exist), I thought maybe I could join a VC firm in Silicon Valley, spend a couple of years there, and then either find an exciting startup to join or try another start-up from scratch.

Running late in the VC recruiting process, I had to come up with my own game plan.

Soon afterward, I decided to try recruiting for VC but soon realized how naïve and underprepared I was. VC was very hard to get into for most MBAs. There’s never a structured recruiting process. Even worse, I was very late in the recruiting process compared to my classmates. A lot of them who aimed to enter VC had already interned at VC firms before the MBA program started. Some of them received well-deserved full-time offers from those firms before the beginning of the second year. I thought to myself, I had to come up with a game plan in the harsh environment.

Except for a few introductions from mutual friends, I didn’t know which VC firm was hiring or who I should approach for networking. As much as I learned from my classmates, I figured it wouldn’t work to cold-call people and ask for a “coffee chat,” since it doesn’t make sense for people to give a stranger their precious time. I anticipated it would be ineffective and disrespectful to send an email merely saying that I have a Ph.D. from U Chicago and an MBA from Wharton, that I have four issued patents, that hey, I’m awesome, and that please spare time for me and give me advice for free.

Instead, I did some homework and discovered that most VCs were very into Cleantech around that time. With my technical background in chemistry and material innovation, I can relate to many fields under the Cleantech umbrella. In addition, battery and energy storage seemed to be a topic of interest, so I did a quick study and put together a brief investment thesis. In each of my outreach emails, I introduced myself and presented my independent study. I shared the teaser deck and offered to exchange ideas. I deliberately chose the keyword “exchange,” so I wouldn’t waste people’s time, I hope.

Knocking on VC’s doors like a salesperson and keeping motivated by celebrating small wins…. But I was unable to “close a deal”.

Over the Christmas break, I sent out lots of emails. It was encouraging to see 8 or 9 out of 10 people respond to me. Starting in January 2009, I took a monthly recruiting trip from Philadelphia to Silicon Valley. (Of course, I skipped a lot of classes, but fortunately, the spring semester in Philly wasn’t heavily loaded with coursework.)

Feeling like a salesperson, I cruised back and forth on Sand Hill Road and visited quite a few VCs and their partners. Some of the meetings went really well, which led to additional meetings with their colleagues and the rest of the partnership. It did feel really encouraging.

Even though some VCs didn’t have openings, they referred me to their friends because they seemed to like my work and recruiting approach. By the time I graduated in May, I had connected with over 100 VC investors in Silicon Valley. This appeared to be a very promising “sales” pipeline. Even a 1% conversion rate would land me somewhere, I thought optimistically.

A huge benefit came from people’s questions and feedback on my deck, which encouraged me to deepen the analysis by doing more rounds of the study. Eventually, my deck evolved to over 100 slides.

However, there was still no job offer. I was unable to “close” any prospect. Many firms didn’t have the budget for post-MBA associates. Some even had trouble doing their capital calls. At the time, four funds expressed interest in my candidacy, but didn’t have the budget. I have to admit my energy level felt quite low a couple of times after getting those messages.

But I didn’t want to quit so easily. I was unwilling to take their “no” as a no. Instead, I proposed to those four funds, “If you have a smaller budget for a short-term gig, I’ll be happy to consider it.” I don’t want to work for free because I fear people wouldn't value my labor, and I wouldn't learn anything useful or get constructive feedback. More importantly, my personal bank account was running low.

The winding road trip starting from Philly didn’t set the exact route, but it did get me to Silicon Valley

By the time I graduated from Wharton in May 2009, I still saw no firm job offer. However, I made up my mind to move to Silicon Valley anyway. I wasn’t ready to give up so easily. Plus, I fell in love with the entire area. Every time my Southwest flight landed at the San Jose airport, the dry, heated mid-afternoon air mixed with jet fuel vapor smelled so good! In my memory, it smelled so “entrepreneurial” to me.

On May 29, I started a road trip across the country. The entire road trip took me 33 days and 6,700 miles. It was, of course, not the shortest route but rather a winding path. I didn’t plan the exact route from start to end, but decided to follow what felt right as long as it roughly pointed to Silicon Valley. Well, I actually entered Canada twice. Every time I crossed the US-Canada border, I was asked by the border control folks on both sides, “Where are you going?” “California.” “Then why are you here in Canada?” It was funny that my CRV was loaded with stuff, which could’ve raised some legitimate suspicion. But luckily, I made it through the border each time without any incident.

My road trip in 2009 (6,700 miles in 33 days)

I did face a serious problem. My cash was running out, and my student loan payment would start soon. I spent as little as possible on the road trip and camped at eight different national parks, which was actually awesome. My contingency plan after arriving in the Bay Area was to camp at a state park for $10 each night, take a shower at a gym like 24-Hour Fitness for $35 per month, and eat at Google’s cafeteria with my friends there for free as often as possible. Following this plan, I figured that I could survive for a while without an income.

However, a pleasant surprise changed my trip plan: when I was outside a coffee shop in Wyoming, I received a call from a partner at Mohr Davidow Ventures (MDV) on Sand Hill Road, a VC that made quite a few highly successful investments between the 1990s and 2000s. I was offered a 3– to 4-month work arrangement with a monthly stipend, with no guarantee of a full-time role whatsoever. Nevertheless, I was thrilled!

I had to cut short my road trip, but still managed to cover Seattle, Vancouver, and Victoria, BC, before heading down to the Bay Area. On June 30, I finally arrived at my friend’s place in South Bay after spending 33 days, 6,700 miles on the road. A week later, I started working for MDV. At MDV, I helped the partners evaluate a range of cleantech investment opportunities. It was very helpful to get my hands dirty in a real VC environment. Meanwhile, being in the Bay Area allowed me to continue my networking activities. After MDV, I spent a few months with ARCH Venture Partners and one of its portfolio companies.

Finally, a full-time VC job!

In Spring 2010, a Wharton alum informed me of an opening at VantagePoint in San Bruno. I went through all the interview rounds and received the offer in April, which concluded my 16-month job search. (To celebrate, I took a road trip on Route 1, through Big Sur, all the way to Santa Barbara. This time I couldn’t afford to go on for too long, so I spent only three days having fun before reporting to the new job.)

I stayed at VantagePoint till early 2012 and joined Formation 8 as the first hire on the investment team, where I further honed my VC skills and built my track record before starting iFly.vc. I’ll save the story for future write-ups.

A few takeaways

I was both unfortunate and fortunate to go through the job-hunting experience after I finished my Ph.D. in 2002 and my MBA in 2009. (Jokingly, I promised my friends and myself that I would not go back to school again. Who knows what will happen if I do? What doesn’t kill me indeed makes me stronger. The brutal job search experience taught me a lot. Reflecting on my 16-month VC job search, I have the following takeaways.

1. Do not be discouraged and focus on small and achievable steps. No matter how difficult the macro or the job market is, just don’t be discouraged and don’t give up. Before any big win can be achieved, focus on and celebrate each small win. I tend to be cheered up by every small win. Each time I learned something new from my networking chat or got another referral, I felt encouraged by such small wins. This is probably how I found the motivation to go through 16 months of uncertainty and numerous rejections.

2. Every MBA student should learn how to sell. Selling shouldn’t be a dirty word. Most business schools don’t teach students how to sell or manage the sales process, but selling is such a vital part of any business. At Wharton, several classmates and I co-founded the Wharton Sales Club (later renamed “Dealmaker”). I served as the first president. Together, we promoted sales education among fellow MBA students. I personally learned a ton and applied many of the skills to my own job search process. Selling isn’t just about me or my level of awesomeness, but it’s more about the other party, who they are, what they want, and how they feel. Selling requires the effort to build rapport and mutual respect to earn a long-term working relationship beyond a single transaction. Selling will always involve many rejections, but we must be comfortable with that.

3. Don’t cold-call people just to ask for free advice or information. Most people don’t have free time for “coffee chat” unless you have something to bring to the table. Nowadays, when I receive thoughtful notes from students who propose exchanging ideas on topics of mutual interest, I instantly feel good about them and always try to accommodate their interests.

4. Enjoy the journey even when it’s full of ambiguity. While we work hard towards our goal, we must enjoy the journey itself. The real world can be full of ambiguity, but one must get comfortable with it. The winding road trip was an unforgettable experience. Usually, I had no idea where I would spend the next couple of days in a row, but I planned the route as the trip evolved. After I reached Yellowstone National Park, I had become quite adapted to the uncertainty ahead of me. Since 2009, I’ve never had a chance to repeat such a trip. I certainly hope I will be able to do it again at some point.