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Do you start each day feeling motivated? Are you working towards a goal you’re physically excited about? If not, you may be lacking a captivating vision.

“Vision” sounds like consultant-corporate-mumbo-jumbo. It’s actually a simple and useful tool. A good vision is an outcome that:
(1) you can picture (a vision!)
(2) excites you

If you can’t picture what you’re working towards, it’s not a vision.
If it’s not an outcome you’re excited about, it’s not good. That’s it.

Good vision: We’re going to build a colony on Mars.
Bad vision: We’re going to promote excellence and be the best company in our industry.

This doesn’t just apply to companies. If you’re not excited about your life, you may be lacking a captivating vision for yourself. Fix it now.

Your gut is often wrong. But it’s also often right. Unfortunately, being right isn’t good enough.

I find my gut is correct more often than not. And yet, if I fail to convince others, the signal is wasted.

“Something about this project feels off.”

It’s OK to trust your gut in these situations. The problem is, other people — your team, your stakeholders, your boss — won’t necessarily understand. They don’t feel what you feel.

That’s on you. Embracing your feeling is a good first step. The second one is even more important: communicate why you feel a particular way. Only when others understand your why can they be as motivated as you are.

“I feel anxious about this deadline, let’s face the possibility that we may not ship in time.”

The greatest leaders will trust their gut. And also get others feeling the same way.

Arbitrage is riskless profit — the holy grail of finance. Buying something for one price and instantly selling it at a higher price. Since there’s no risk involved, anyone will take an arbitrage. These are the most competitive opportunities.

The concept can be extended to the startup world. Businesses lie on a spectrum of arbitrage → from Arbitrage to Art. On one end, you compete to sell a commodity. One banana is pretty much as good as another, so customers take the one with the lowest price. On the other end, you have one-of-a-kind products. There’s only one Mona Lisa. What will people pay for that?

It’s easier to get up and running with a business closer to the arbitrage end. But will it get you to where you want to go?

Sriram Krishnan on the Venture Stories podcast, (my notes on Twitter), explores the different ways top consumer social startups work. Each finds success by applying totally different playbooks: whether it’s creating tools and promoting serendipity (Snap), picking a north star and optimizing (Facebook), or working to promote fundamental principles (Twitter).

There are few universal truths when it comes to startups. In fact, that may be the only universal truth. The only formula is: there is no formula. I still find studying other playbooks as valuable, of course. It shows me how much I don’t know, and how many of my assumptions may be false.

I’ve always believed trading stocks to be a socially acceptable form of gambling — still a “bad thing”. The average trader does worse than buy & hold. I should know, I built an HFT firm.

Recently, while messing around on Robinhood for fun, I’ve changed my mind about this. Trading may be a Good Thing.

In a casino, you have no edge — in the long run, you lose money. In the markets, you may not do better than buy & hold but you can still reliably make money: just make sure you stay long the market, on average.

As long as your trading leaves you generally owning stocks, you get to have a little fun and make money at the same time. Sure, it may not be the rational or optimal thing to do. But, it’s often better than the alternatives.

You have a superpower. Things that come easily to you are impossibly hard for others. And vice versa, of course.

Your superpower may still be nascent, but it often doesn’t take much to let it blossom. The key is to pay attention to what excites you. Let me put it another way: What are you obsessed about? Once you’ve identified your obsessions, see if you can find other ways where the same skills can be applied. Perhaps something with greater rewards.

Even a seemingly silly obsession, like video games, is hiding a superpower with potential. Playing a strategy game — where you plan for the future, manage resources, and make lots of small optimizations — is basically the same as operating a small business. Or a giant one.

It’s taken me years to understand the old startup mantra of: “Make something people want.” It’s simple. However, like most simple things, it’s not necessarily easy.

I have a tendency to conflate “something people want” with “something that sounds cool to me.” What are things people actually want? A good place to look is where they already spend their time. Even better is how they already spend their money. 

I once had a startup idea to make a new, better version of Mint.com. You know, one that actually worked. Sounds cool, but do people want it? Do they pay for it now? No, not really. What do they actually want/pay for? Credit cards. Bank accounts. Financial planning. Wealth advisory.

When building a company, offering something people actually want can save a lot of agony. The next step is also simple: make it 10x better or cheaper.

Sometimes I wonder why people don’t share more of their expertise online. And then I try to do it myself, and half the time I’m wondering: “Why would anyone care?” 

Daniel Vassallo’s twitter thread on building an information product and getting customers is great, and helps assuage my concerns. The gist is simple:

1. regularly share tidbits of your experience,
2. ideally around a single theme, and
3. engage with people that respond to you.

You don’t have to be an expert, but it does need to be your experience.

People follow in each other’s footsteps. Something that seems trivial or embarrassing to me may be exactly the thing that someone else needs to hear. Tell your story, bit by bit, and slowly, but surely, people tend to gather around and listen. At least, that’s been my experience.

One day, I’m going to wake up and have a book written. This kind of project typically requires months or years of tearing your hair out. My goal is to do it without any stress.

How will I do it? Easy, one brick at a time. Or in this case: 140 words.

Writing (and editing) 50,000 words makes me nauseas. But, writing 140 words a week seems doable. Some weeks I won’t feel like doing it (like right now). However, because of the low hurdle of success, I will probably do it anyway. This creates a positive feedback loop. It’s hard to fail, so I will develop momentum — a virtuous cycle of positive reinforcement. I’ve written about this concept before, calling it Minimum Viable Habits.

In this way I will build a cathedral.

​I don’t like annual reviews. I love the idea of them. I can reflect on my past year, the highs and lows, wins and losses, and make some plans for the next year. It sounds great. In practice, it feels daunting.

This year, I want to try something lighter. I will pose and answer just one question. Then, I can use that as a guide post for the next year. I invite you to do the same.

What’s one practice or principal that has served me well in 2019, and how can I double down on it in 2020?

Simplicity.

When things start getting nuanced or complicated, try to reel it back in to a single core idea. What’s the main thing? How can I state it in a way that anyone can understand? Keep it simple.