Reflection on the Past Eight Years of Growing iFly.vc as a Start-up Founder
Shared Journey with iFly.vc
This month marks the 8th anniversary of iFly.vc, and what an incredible journey it has been. I want to extend my deepest gratitude to our LPs, current and former team members, portfolio companies, and all of the friends and allies who have contributed to the growth of our funds and the businesses we support. (Thank you!)
I vividly remember the moment we completed the first close of Fund I. While there was a brief sense of joy, 99% of my thoughts were, “Wow, this just got real.” Fundraising is humbling, but closing a fund is only the starting line. The real challenge is in delivering exceptional performance. My mind was immediately focused on how to make the fund succeed.
It is hard to believe that eight years have passed since the launch of iFly.vc. I want to share a few key takeaways from the journey so far in this newsletter.
Crafting your playbook: Achieving top-right dominance in the competitive landscape
It is common for startups to showcase their positioning on a competitive landscape slide. Predictably, they always place themselves in the upper-right corner, with half a dozen competitors scattered across the rest of the 2x2 chart. But if an emerging VC fund attempted such a chart, it would be overwhelming, filled with thousands of dots representing other emerging funds. In fact, Silicon Valley Bank has tracked over 2,000 VC funds with less than $100 million in assets under management.
For iFly.vc, we cannot do everything or be everything. We should just focus on a few and do it very well. iFly.vc came to focus on a tech-enabled consumer playbook. We are passionate about empowering exceptional founders to transform how people eat, live, play, and work across the $17 trillion U.S. consumer economy. We recognize multiple growth drivers reshaping the landscape and creating fresh opportunities for VC investment.
We thrive on conducting in-depth research to understand industries, value chains, pain points, and the applications of new technologies. If the fit is not right, we pass. But when we have strong conviction, we act decisively, guided by our independent judgment. We are comfortable leading rounds or even being the sole investor. On average, we make two to three new investments per year, with the most we have done in a single year being four. Since our inception in 2016, we have invested in just fifteen startups.
Our approach is intentional and focused. We aim to thoroughly understand why we should be excited about an investment opportunity while also recognizing why we deserve a seat at the table—especially when asking for a meaningful share of equity. This commitment has led us to build a concentrated portfolio, ensuring we have the bandwidth to actively support the growth of our companies.
Currently, Fund I is performing in the top tier of VC funds from its vintage year, and Fund II has already seen emerging winners with substantial value creation.
Grit is not enough
I emphasized a founder's grit during my venture investment career's early years. After all, many successful founders have experienced highs and lows before their businesses finally took off. However, over time, I have adjusted my perspective on grit when evaluating founders because grit alone is not enough.
If a founder or CEO sets a startup on the wrong path, hires the wrong people, or makes strategic missteps, the damage can be so severe that there may not be a second chance to recover.
As a company grows, the founder or CEO must continuously evolve in leadership, strategic thinking, and team-building. If they cannot keep pace with these increasing demands, they inevitably become the bottleneck to the company’s growth.
In my investment career, I have experienced both wins and losses. None of the failures occurred because the founders lacked motivation or simply became lazy. On the contrary, they all worked incredibly hard. But at some point, it became clear that their skills hit a ceiling. The outcome was often fatal without the right person to replace them and with the company still burning cash.
At iFly.vc, we place great importance on helping our founders learn and grow. Since starting iFly.vc as a start-up founder, I, too, have been driven to improve continuously. Kauffman Fellows and Coolwater have been invaluable in helping me navigate the “known unknowns” and gain insights into the “unknown unknowns.” My colleague Martin Salomon has also completed his part-time MBA program at UT Austin while staying busy at work and raising his family.
Start-up founders must learn how to sell
Throughout the journey of raising and managing iFly.vc funds, I was rejected by at least 500 potential LPs. Raising capital as a GP is like raising capital as a startup founder—it is fundamentally a sales job. To be an effective founder, one must be reasonably good at selling.
Selling goes far beyond pitching to customers. It applies to business partners, job candidates, investors, and key stakeholders. As an investor, if I am not impressed by how a founder articulates their vision or plan, I cannot help but question how they will do it with others to build a successful business.
As far as I know, none of the top-tier business schools teach MBA students how to sell, yet it is a crucial skill. Selling is not rocket science; I believe anyone can learn and improve.
To excel at selling, you must first excel at listening—understanding your audience, building rapport, and identifying their needs. The same goes for an investor who wants to persuade his founder.
Fundraising, particularly for a VC fund, often involves achieving a “product-market fit” between the GP and LP. The sooner a GP can recognize when that fit is not there, the sooner he can adjust how he allocates his time across the prospect pipeline.
Selling inevitably involves hearing many “no’s,” and becoming comfortable with rejection is essential. Each rejection is an opportunity to refine your skills. Building relationships, even after a no, can be valuable. In my case, I have maintained strong relationships with potential LPs who initially turned me down. I learned much from their wisdom and insights into the capital markets. In some instances, those LPs later returned to invest or introduced me to others who were incredibly helpful to iFly.vc.
Let’s not ignore our health and wellness
Building a startup is no easy task; as the saying goes, it is a marathon, not a sprint. That is why founders must prioritize their physical and mental health throughout the journey.
In my fifteen years in venture capital, including the eight years spent building iFly, I have seen several founders in the startup community burn out. Some became so overwhelmed by stress that they were hospitalized. I have also lost friends in the same community to illnesses like late-stage colon cancer—lives that could have been saved with earlier testing.
I have always taken pride in my ability to sleep well, no matter where I am. However, during the first three years of building iFly, I neglected my health and wellness routine, especially with the constant travel. Recognizing this, I consciously tried to exercise more and take small breaks to manage stress.
Learning to play piano, even at a slow pace, became a late-night escape for me, and this past summer, I submitted a video for my ABRSM Grade 3 exam. I have also improved my freestyle swimming, doubling my speed from a year ago. These days, I feel more energized and refreshed, ready to continue the journey ahead.
The road ahead
Over time, I have come to appreciate the notion of a “shared journey” more and more. The path to building something meaningful is rarely a solo endeavor; it is shaped by the people we meet, the conversations we have, and the collaborations we forge along the way. I am deeply grateful to those who have been part of this journey with iFly.vc. As we continue to grow, I look forward to exchanging ideas, learning from one another, and discovering new opportunities. The road ahead is full of promise, and I am excited for what the future holds. Thank you for being part of this shared journey, and I look forward to the years to come.
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