Reflection on the past four years of running iFly.vc as a start-up founder

After seven years in VC, I became a start-up founder in 2016. The start-up is a micro-VC firm called iFly.vc. Over the past few weeks, LinkedIn has kept reminding me of the fund’s fourth anniversary, which prompted me to think it is time to reflect on the key lessons that were learned and reinforced over the past four years of running iFly.vc as a start-up founder. Here are the takeaways I would like to share.

Fundraising is a humbling experience.

Between 2016 and 2019, I logged 680,000 miles and 1,500 hours of flights, a major chunk of which was for fundraising. More than 350 prospective LPs turned me down on Fund I between 2016 and 2017. I hope this figure helps all other start-up founders feel less discouraged when they are turned down by investors. Fundraising is hard but it still boils down to the process of finding the right fit in a persistent way. In the early days, iFly encountered all sorts of setbacks but I told myself that “I am the captain of the ship. I am not abandoning the ship, and the ship must continue sailing forward.”

Underdogs need their own playbooks.

Start-ups are always surrounded by the 800-pound gorilla: the bigger, better resourced, and longer-running companies. Simply defying the incumbents, boasting the tech, or working extremely hard alone is insufficient to compete and win. In the case of iFly as a start-up fund, it is clear that we do not possess the kind of resources at big funds where I used to work. At the same time, it is hard to differentiate or even outperform other micro VCs by mimicking them or by trying to be incrementally better. Rather than chasing the hot, buzzy stuff, and the fleeting, we chose to focus our energy to back entrepreneurs to address the unglamorous, underserved, and underappreciated demands. (In a separate post, I will review iFly’s investment playbook in more detail.) The strategy has worked well for us and our portfolio companies. The performance of Fund I was rated among the top tier of 2016 vintage VC funds, according to Cambridge Associates’ benchmark report as of 9/30/19.

The CEO is the bottleneck of every start-up’s growth.

I am the key bottleneck of iFly’s growth, and I believe it is fair to say, every CEO is his/her start-up’s key bottleneck. As a start-up grows, the CEO’s vision, leadership and management skills, time management and learning curve must evolve to match the company’s growth. Therefore, we are in a continuous effort to help our founders/CEOs grow themselves. We are fortunate to have a group of highly successful entrepreneurs (including some of our own LPs) interacting with our founders directly and sharing their experiences and wisdom. (Note to myself: Perhaps we should ask for their permission to publish the notes from the conversations with them to share their insights and advice.)

As a founder myself, I have found a strong motivation to continue learning. It has been enormously beneficial to exchange ideas and learning with others. This year, my goal is to foster more learning among founders, friends, and partners.

(When I shared the draft of this write-up with friends, some of them suggested I deliver the message in a positive tone. How about “iFly.vc helps CEOs avoid becoming a start-up’s bottleneck”? I thought about it and decided not to change it because I wanted to unequivocally make the point. This is the harsh reality that every founder and start-up must not ignore.)

Grit, tenacity, and resilience are crucial attributes.

The world has no shortage of founders with amazing profiles and charisma but neither the profile nor charisma in and of itself leads to the success of start-ups. Every startup faces ups and downs. When things get difficult, how founders judge, behave and act makes a huge difference. I have watched founders used their houses as collateral in order to collect enough cash to turn around the business, and I have seen founders who blamed everyone else and everything else in the post-mortems, e.g., “Amazon is just too hard to beat.” “We’re a strong team but we’re too much ahead of our time.” “We can’t fight the macro condition because of the US/China trade tension.” Sorry, but I cannot invest in the next start-up founded by the latter with such an attitude.

SEL can benefit many adults including founders.

Social-Emotional Learning (SEL) has become a popular part of the educational curriculum for kids these days. I believe many adults including founders can benefit from the SEL to understand and manage emotions, set and achieve positive goals, feel and show empathy for others, establish and maintain positive relationships, and make responsible decisions. Although building iFly has been mostly a great experience, I have indeed run into situations that could have been quite traumatic if I did not learn how to manage my emotions and stress. I am glad I have managed to sleep well when sh*t ever happened in the past four years.

Be generous with goodwill.

At iFly, we have moved beyond the paradigm that limits “the deal” to a transaction-centric view and binary outcomes. Every start-up founder deserves respect. Whenever we can help by making an introduction, or through candid, constructive feedback, we should do it. About five years ago I connected with an entrepreneur in Palo Alto but did not invest in his startup. Nevertheless, we both recognized the potential of a mutually respectful relationship and kept in touch. Five years later, the entrepreneur introduced me to a family office on the East Coast, which ended up becoming an LP of iFly Fund II. Nothing can be necessarily planned or even contracted in this way, but the goodwill, in this case, was powerful and rewarding.

Thank You!

This write-up has lots of I’s because it was about my personal opinions. However, the progress of iFly is indebted to the team and all those who have been generously helping us. I am deeply grateful for the tremendous support I have received from every friend and ally. Most of our LPs were referred by friends. Without the help of our friends and the investment of our LPs, iFly.vc would not have taken off in the first place. Every portfolio company has also greatly shaped who we are. Even though the iFly.vc team is small, everyone’s impact and work ethics are incredible. This is a shared journey that I hope everyone benefits from. And I look forward to growing with everyone in the years to come.