All posts are my own opinion and do not represent any organization I am affiliated with.

Skiing Into the Night

This past Friday night my friend Marco Vienna and I started running up Mt. Crested Butte on skis at midnight in a bid over Star Pass to end up in Aspen. This route is 37 miles, part of a Ski Mountaineering race called The Grand Traverse. We estimated the trip would take us 12 hours. Our friend (and support team) Danni Perri took this photo before the start of the race. Thank you so much for the support Danni!

For the first 5 hours of the race, we were doing great. We made it over Death Pass with plenty of time to spare and were actively passing other participants. Yes, it is actually called Death Pass - 2 people died on this section of the route while training for the race this year. There was a memorial on the racecourse.

We were heading up a high elevation valley called the Brush Creek Drainage. It was about 5 degrees out and I felt warm because we had been moving non-stop. Around this time we stopped for a few minutes to eat and drink water. And I got cold. It's not clear exactly what happened but my best guess is that I contracted mild hypothermia in my lungs which from then on made it extremely difficult to breathe.

We continued for the next two hours towards the next checkpoint, but my pace was much slower. Around six and a half hours in, I could only move a dozen meters before being forced to stop and catch my breath. This was a demoralizing rhythm, but we continued up the mountain. We made it to the Friends Hut checkpoint about 10 minutes before the cutoff. This checkpoint is right before a difficult climb over Star Pass, followed by the most difficult descent of the route.

While the rules of the race would have let us continue, at this point, I was pretty worried about how difficult it was for me to breathe. And there was no way I would have felt safe taking myself and friend up the pass. If my condition worsened at all, it would have put us both in an unacceptable amount of danger. If I couldn't get down under my own power, it would have been bad.

It was disappointing not to finish. But I am so happy we were able to get out there and try something truly difficult for our ability. Right as we decided not to continue, the sun finally rose after 7 hours of skiing in the dark, and we were rewarded with this view. It was the best silver lining.

Last fall I dragged Marco to Aspen for the Mountain Bike version of the Grand Traverse and this Spring he dragged me to Crested Butte for the ski version. Continuing the tradition we will be running this route in the fall (kidding... hopefully)

How Convertible Notes Convert, Template

Convertible notes and SAFEs are great because they allow startups and investors to defer the difficult process of valuing an early stage company and quickly close funding. This is at the cost of putting the burden on later investors determine the value of the company, generally, once the company has more metrics to base a valuation on. With the convertible note holders getting some type of discount for investing early. If you want to read more about the mechanics of convertible notes I recommend Brad Feld's series of blog posts -> read here.

I've been involved with a number of companies who have raised multiple rounds of convertible note financings, without really understanding how all the rounds will convert when a priced round occurs. Over time I have developed a generic Google Sheet template which given a cap table and convertible note terms calculates Series A conversion scenarios providing insight on how everything will play out.

To access the template - > Click Here and go to File -> Download As an excel copy. From there you can re-upload the file to your own Google Drive.

In the first tab 'Pre-Investment Cap Table' add your current cap table. Usually only contains founders and maybe some early employees.

The tab 'Convertible Notes' is where you input your convertible notes. It is ok to leave either cap or discount blank. SAFE's can also be input in this sheet, they are functionally equivariant to convertible notes. Inputting multiple rounds of convertible notes here is also ok, just add them with different dates and terms.

The next tab 'Series A Inputs' is where you input a Series A scenario based on the pre-money valuation and round size. This sheet also allows you to calculate an employee option pool expansion concurrent with the Series A fundraising (this is common).

The final tab 'Series A Cap Table' shows both pre and post Series A cap tables side by side. Showing the effect of the convertible notes on the final cap table.

If you find this sheet valuable, please leave a comment. I am happy to take suggestions or discuss unique fundraising scenarios that don't fit in this template.

Why I Don't Actively Invest On Public Markets

I do not actively trade any stocks or bonds on the public markets. I've also avoided cryptocurrencies, which trade on a public market.

I avoid public market trading for a couple of reasons:
1) It's been empirically shown that holding a diversified portfolio of investments for a long period of time is a better strategy than attempting to identify individual stocks that will outperform the market. This is because any additional gains you get by actively trading, on average, will be canceled out by the value of the effort put into achieving those gains. This leaves you, the average person, no better off than just passively holding diversified investments over a long period of time. Weathfront has a great explanation of why this is the case: in this blog post.

2) It's stressful. At any given time you could be doing better if you had more information on the companies you are trading. At any given time you could be doing better if you buy and sell at just the right time. At any given time... When actively trading this constantly was in my head, I became obsessive about research. This was emotional stressful. While probably not applying to everyone, it is not worth the stress to me.

3) Success attribution. It's really difficult (or maybe impossible) to identify the signal of why certain stock picks performed well and why others performed poorly. Which would be necessary to consistently pick well-performing stocks.

If you want to be investing more of your money but don't know where to start, I recommend checking out Wealthfront. They give you very good diversification without any fees on your first $10k, they encourage good long-term thinking, and they are not paying me to say any of this. Investing is important to wealth building, and active investing is one of the traps many first time investors will get caught in.

It would be disrespectful not to mention Jack Bogle, founder of Vanguard investments, who pioneered bringing low cost diversified investment instruments to regular investors. Before Vanguard, if you wanted to match the performance of the S&P 500 you would need to buy every stock in the S&P 500. Vanguard created the first widely available index funds. By doing this Vanguard democratized access to index investing, by lowering the cost and complexity of making index investments. This gave regular people access to sophisticated investing techniques. What Wealthfront does is the modern continuation of these ideas, with added features such as Tax-Loss Harvesting and Automatic Rebalancing.

What is a Great Friend?

"A great friend is someone who helps you become the best version of yourself." I read this in Sheryl Sandberg's forward for the book Originals by Adam Grant. I love this quote.

It is a profound insight into what makes many relationships great. Beyond friendships, partners in business should share this quality. Instead of everyone working to outdo one another, everyone working to bring out the best in their peers is far more productive for the collective. This is also a useful lens while dating, as long as the effort is reciprocal.

Again what a wonderful notion of for friendship "A great friend is someone who helps you become the best version of yourself."

Update: Boulder Skyline Traverse #fail

Last year I wrote a blog post detailing a running route I wanted to run in Boulder.

I failed. More accurately, I didn't even try. Other priorities took over my time for the remainder of the warm days last year, and I didn't attempt the route that I set as my goal. Not completing the goal I set was disappointing. I had spent time training on the route, doing each section at least once during separate runs.

By the end of the summer, I was very confident I could complete the entire route in one go. There were two primary reasons I didn't go for it:
1) It would hurt. It's a long run, and by the end of it, I would effectively be injured just from wear and tear.
2) Once I realized I could do it, I lost interest in actually doing it. Has anyone else experienced this? Happens to me all the time. I often don't feel the need to prove something is possible, which I already know is possible.

I failed, moving on. It only feels right to try a different set of goals this year. So I've set two fitness goals: 1) Grand Traverse Ski Race and 2) Leadville 100 MTB

The Grand Traverse Ski race is a 34-mile ski race from Crested Butte to Aspen. I've done the reverse route twice on a MTB during the summer racing series. It's exciting, and scary, to think about going back into the Maroon Bells wilderness in the heart of winter, on skis, in the middle of the night. The Leadville 100 MTB is a 100-mile mountain bike race which is potentially even more intimidating because of the distance combined with a very difficult course that tends to beat down first timers.

I am not confident that I can finish either of these races and that's what makes them fun :)