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There’s the challenge of dealing with uncertainty, where you’re operating in the weird zone that you’re making decisions that have significant long term impact or that are difficult to reverse or course-correct in the face of great uncertainty.

Uncertainty is often unnecessary in the sense that you could, in principle, reduce the uncertainty. You could go research the question more. You could obtain more information, or run an experiment.

It’s not cosmic uncertainty, without absolute knowability. When there’s true, deep, un-mitigatable uncertainty then it’s not to hard to say, “we’re just going to choose something and make the best decision we can.”

“Don’t be so hard on yourself when things go badly and don’t be so proud of yourself when they go well.” I think this is one of the hardest pieces of advice to follow. Chance is an important contributor to any outcome. sometimes we just get lucky. That recent crypto trade in which you made 25% in an hour. The time you met your significant other for the first time. The hiring decision in your startup that was a wild guess, but worked out beautifully.

The venture capital markets are flush with capital. We’re approaching the heady days of the dot com era. In that epoch, despite the record volumes of venture dollars, startups went public quickly, in 4-5 years. Today, that timeframe is no longer realistic. In fact, the surfeit of private dollars delay IPOs.

From 2000-2005, the “typical” IPO-bound startup listed on an exchange 5 years after founding. After the Lehman collapse and the crisis of 2008, the IPO closed, and startup age spiked to 16 years median.

“When I die, I want all the people with whom I worked on group projects to lower me into my grave, so they can let me down one last time.” Someone once sent me this e-card as a joke. I laughed and laughed, and never forgot it. I can’t remember a school group project which teammembers contributed equally. Paradoxically, I bet everyone in the group felt the same way.

There’s a good reason I bristled in those group projects. Every person in a team overestimates his or her contributions to the team. The bigger the team, the greater the overestimation - “especially when group members’ unequal responsibility allocations are made explicit.” Add an egocentrist, someone who takes more credit, and the social dynamics boil.

Ten years ago, Guy Kawasaki took this photograph of me. I was attending my first YCombinator Demo Day, maybe three months into my time at Redpoint. Much has changed. I’m am not as young or as green. YCombinator has thrived and scaled. And the startup demo has disappeared.

At that August Demo Day, each pitch lasted eight minutes. Without fail each featured a demonstration of the product. It was the height of the Web 2.0 era. The iPhone was just a year old and mobile hadn’t blossomed yet. The web was still the center of innovation. And the demo provided founders a chance to explain these innovations. I felt like I was seeing a wisp of the future incarnated in code.

The average English sentence has been shortened by half over the last five hundred years. Read the first sentence of the Declaration of Independence to see why. It is 71 words long and contains 8 recursive clauses. I read it ten times before I understood it. I have 48 seconds with you, my reader. No time to mince words. To reach more people with your content, shorten your sentences and ditch the jargon.

A dollar today is worth more than a dollar tomorrow. This statement underpins all of finance. The idea has a fancy name: the Time Value of Money. It applies to all types of investments, including startups. Time Value of Money is the economic argument for startups to raise money when it’s available.

If I give you a million dollars today, you can invest it. You might buy 151 bitcoins. Or invest in a certificate of deposit at 1.5%. Or pay a team of four engineers to build a feature for your software startup. Each of these are investments with some risk and some potential reward.

Yesterday, Salesforce announced it will acquire Mulesoft for $6.5B. A recent addition to the list of public software companies, Mulesoft is a tremendous business. The company generated $297M of revenue in 2017 at a 73% gross margin, and grew by 58%. Salesforce is acquiring the business for an astounding 21x enterprise value to trailing twelve months revenue multiple - nearly 2x the next closest.

Recently, people have been asking just where are we in the SaaS valuation cycle. I last updated the chart above more than six months ago. The answer is close to ten year highs.

The chart above shows the median enterprise value to forward revenue multiple to multiple. Enterprise value is the market of a publicly traded company minus the available cash the company holds. Forward revenue is the sum of the next 12 months’ revenue.

In the US, the median seed round has nearly quadrupled over the past seven years. In the mean time, seed investment has grown more than 7x and then fallen to a bit more than half of the high. As the market has grown and retrenched during that time period, I’ve been wondering about the geographic diversity of these seed dollars. Throughout these cycles, are startups in other states benefitting? Are they increasing their share of investment dollars?