Sarah Fraher, a woman who had an outsized impact on my life, died yesterday. She was my best friend Shelton’s mother, and beyond that, she played an outsized role in my life as my “landlord” during most summers in high school (unofficial, just crashing) and college (official).

She was an incredible leader, which she put to work as both a school principal and a family matriarch. She taught me a form of leadership that I try to embody when I can, and I want to share it here.

Sarah led in a quirky way: she was ironclad and crystal clear in her demands but almost never issued a punishment of any kind.

You never had a doubt in your mind what Sarah expected of you and if you let her down, you heard about it in no uncertain language. I was as scared of her as any person on earth. However, I can’t remember a single time she punished Shelton or me, and I can promise you we did plenty of...

“It never hurts to ask!”

I get this advice a lot. It’s bullshit and we all know it.

We hate getting asked for things. It’s painful at a visceral level to have to say no. We generate narratives about the ask-er to justify the “no” we have to deliver. “They are CRAZY to ask me for this” or “what a snake to ask for something so out of bounds”.

It doesn’t matter that they were “just asking” and that we’re free to push back or say no - the emotional damage of the ask is done when the ask is made. Recently, an investor told me they’d received bad feedback about a close friend of mine during DD reference checks. The bad feedback stemmed entirely from two “asks” he made in previous compensation negotiation. I can’t think of a worse reason to harbor bad feelings against a startup executive, but I’m not surprised. Because it hurts to ask.

Beyond the personal toll asks take, each ask has an...

Kids are obsessed with fairness. The consistency with which children will say “that’s not fair” given the opportunity is impressive. If a situation can possibly be put into terms of “fairness”, a child with use fairness as a weapon of protest - everything from their sibling getting something the child didn’t get to being told they can’t go to a particular event that their friends are going to.

Adults are tempted to respond to these pleas for fairness with a dose of reality. “Life isn’t fair,” they’ll often say, and it’s true! There is almost nothing about life that is fair, and while humans do make efforts to inject fairness into an otherwise unfair world, fairness is the exception, not the rule. It doesn’t work though, at least it didn’t on me. I remember being a child obsessed with fairness and what snapped me out of that obsession. It wasn’t when I realized the world isn’t fair...

Investors love traction. Even at the early seed stage, almost every investor has “traction” near the top of their list for what they look for in an investment. And for good reason! Even with a great founder, a plausible idea in a big market, and a team to execute on the vision, there is a lot risk that nobody actually wants what the founders are building. A “launched” product with some early growth is considerably less risky than a pre-launch product. Entrepreneurs have heard the call for “traction” many times and naturally assume it is always better to launch before trying to raise VC or angel money.

There are two problems with this assumption. First, launching isn’t the only way to get traction. Second, and more importantly, there are real risks involved in waiting to raise money until after your product is fully launched. In reality, there are two types of companies

• Companies that...

In 2010, a multi-featured location-based app called Burbn pivoted and became a simple photo-sharing app called Instagram. Less than 2 years later, Instagram sold to Facebook for 1 billion dollars, and may be worth as much as 35 billion dollars today. Many people hailed as victory for the lean startup method¹ of product development, where launching quickly, learning, and iterating is said to be the key to startup success. And those people were right! The Burbn founders launched (although not quickly), observed via analytics that the photo-sharing features were the most popular, and doubled down by iterating into an app (Instagram) that contained ONLY photo sharing and commenting. Classic lean startup story.

However, there’s another equally important takeaway from the Instagram story: Burbn had every single bit of functionality that Instagram has and more, and yet Instagram is the better...

When the founder of VISA Dee Hock joined the advisory board of Bitcoin startup Xapo, it seemed pretty strange to me. After all, Bitcoin’s very existence appears to be a reaction to VISA’s shortcomings. VISA represents everything bitcoin fans hate: fees, centralization, archaic design, and more. The VISA network, it seems, is designed to make the banks more money by charging high fees to businesses that have little choice but to accept them. Bitcoin, on the other hand, is designed to empower people to use their money with no intermediary, no fees, and no central authority to get in the way. So what could the founder of VISA want with Bitcoin, and more importantly, what could Bitcoin want with him? It turns out the story of Dee Hock and VISA is more complicated (not to mention stranger) than the dominant narrative today would suggest. In fact, VISA is arguably the best example in the...

Average people do not love fintech. In fact, in many cases they hate it. I’ve seen this first hand since I took the (currently on pause) dive into fintech a little over two years ago, but two posts by Pascal Bouvier of Route 66 Ventures got me thinking about how deep this problem really is. Pascal’s example of the relative lack of progress in modernizing remittances (sending money home from, for example, the US to Mexico) is a great one: remittances SHOULD be done electronically, they ARE incredibly horrible/expensive/broken, there are MANY players trying to disrupt the market; yet, the incumbent (Western Union) is still cleaning up. Why? Because nobody is winning their users’ hearts. Nobody loves their bank, but nobody LOVES fintech startups either.

This is a problem in almost all of the major markets getting disrupted right now to some degree: banking, money transfer, credit...

What does my company need to look like to raise X amount of money?

Almost every founder I know has this question. The founders have a vision and some unique knowledge of the market while investors have heuristics derived from the market as a whole that they use to make investment decisions. Coming to terms with these two things to define “success” for your next round of funding is critical, and founders are looking for an answer. Here’s the thing: investors won’t tell you. It is the exceedingly rare case when an investor is willing to say “if you have 10 more customers in the next 2 months, I’ll invest”. Why? Two reasons: they don’t know the answer and they want to see if you can figure it out.

Investors don’t know what success looks like

Investors aren’t omniscient geniuses, even the great ones. Further, very rarely does any single investor have the ability to define what they...

I’ve been thinking about fan death a lot lately. Many of the recent news stories I’ve been following have centered around powerful cultural myths and institutions, with defenders of the entrenched cultural forces dismissing the critics outright as ridiculous or evil. Each time I find myself caught up in these conversations, I find my mind wandering back to “fan death” and how so many people can’t shake their belief in it.

Sorry: let’s back up. What the hell is “fan death”?

“Fan Death” or “Sudden Fan Death” is a widely believed urban legend that running a fan in a closed room can kill you. I’ve heard multiple second hand accounts of a Korean person explaining their relationship with the fan death myth, each following this format:

I know fan death isn’t real, it’s ridiculous of course…… but you know it does happen sometimes right?

They are acutely aware that fan death is absolutely...