The Low Hanging Fruit Strategy

When Yohei and I initially started raising our fund, our first step was to approach famous angel investors. Many of these angels could only write us $300K — $1m checks. But for a $30m fund target, that wasn’t going to move the needle very much. We would have probably needed 30–60 angels to top up our fund. It would have been a very inefficient fundraising process, and a huge pain to manage so many investors afterwards.

So why did we approach them first?

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What Makes an Enduring Founding Team?

My co-founder for launching 500 Startups Japan is Yohei. We like to joke sometimes that we are essentially exact opposites.

  • Yohei is a Japanese that can speak English. I am an American that can speak Japanese.
  • I care a lot about practicality and speed of execution. Yohei cares more about detail and precision.  
  • I trust Yohei with all things finance. He trusts me with all things management.
  • I tend to be a stronger negotiator. Yohei tends to be more diplomatic. Both are useful, depending on the situation.
  • I am a morning person. He is a night owl. I basically wake up when Yohei goes to bed (so we can support both our founders and LPs 24 hours a day!).
  • When we fly, I prefer window seat. He prefers aisle seat.
  • Yohei loves attending and speaking at events. I honestly get tired of them and prefer meeting one-on-one or in small groups.
  • I love writing. Yohei takes forever just to write a short message on a birthday card.

I could go on, but the point is that we are very different people. However, that difference is what makes us a great team. There is hardly any overlap between us. We are complementary in almost every way.

Overlap is something you want to avoid in founding teams because it can create points of friction. More specifically, ideally you should have no overlapping core strengths, while having a deep respect for the other’s ability in theirs. I say “core” because it is inevitable to have some overlapping strengths, but a core strength is something in which you particularly excel. When something is your core strength, you tend to have absolute confidence in your own judgement. And when two people who are extremely confident about their competency in a certain area clash, it is very hard to find common ground without a Pyrrhic victory. One side can feel slighted, and this emotional toll will eventually compound and damage the relationship. Both sides don’t want that.

What you should have though, is the same values. You should have the same standards of what is important in life and what is right and wrong. You should have the same ultimate mission. That way, you’ll be able to adapt together and work cohesively in the same direction. Only then will 1 + 1 truly equal 3.   

Venture Capital Dilemma: The Short-Term KPI vs Long-Term KPI

Sometimes entrepreneurs forget that (independent) venture capitalists have to raise money too. We know exactly how it feels to get rejected over and over and over again. Fundraising is hard! We know, because we have to raise a new fund every 2-3 years.

In venture capital, you can think of Fund I as the seed round, Fund II at the Series A, and Fund III as the Series B, and so on and so forth. For each fund we have to show traction. We have to deliver solid KPIs after each fundraise, just like how entrepreneurs have to do the same. But one thing that is challenging about venture capital is that the relevant KPIs in the short term are very different from the long term.

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