All posts are my own opinion and do not represent any organization I am affiliated with.
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
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.
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.
"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."
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.
The Grand Traverse Ski race is a 34-mile ski race from Crested Butte to Aspen. I've done the reverse route twice on
I am not confident that I can finish either of these races and that's what makes them fun :)
This is particularly apparent when talking about difficult subjects. Especially during difficult conversations, I have made a concerted effort to listen to intentions over words. David Cohen wrote a great blog post a few months ago titled Assume Good Intent. Assuming good intent is a powerful concept. Next time someone says something your gut perceives as critical ask yourself "what is their intention?" Their intention is often to be helpful. Some conversations are difficult by nature. Choose to work with people who have good intentions. Listen to their intentions not words, especially when they are critical.