1/ Quick thread on trading stocks/options as a Startup Founder... should you view it as an opportunity or a hindrance overall?

2/ I think it depends a lot on a founder's personality and liquidity. Every dollar allocated to the market is a dollar less being put towards development/operating costs. Can you justify the returns from a position, or is it better to be liquid?

3/ Many Founders, including myself, are comfortable taking risks-- we're crazy enough to start a company and chase something new/exciting. What does this say about our investment style? Long-term returns of 10-15% a year are GREAT for most, but it doesn't fit startup models

4/ We'd need a 100%+ return to justify allocating any of our liquidity to the market, right? We need the money NOW. Reminds me of stories about Founders like Fred Smith that headed to Vegas to make payroll-- worked out pretty well there.

5/ The only financial instruments we have access to that could yield 100%+ returns are options, and at this point, it becomes glorified gambling. OTM options, earnings call plays, etc. become attractive as a quick source of capital

6/ But what do we know about the market? What makes us think this is a sound investment decision? This is a choice to allocate capital to something other than your business. You stop betting on yourself and bet on the public markets. Does this sound like a Founder's actions?

7/ I'm always perplexed about Founders that do not intermingle their finances and commit every dime to their company. Do they not believe in themselves? Are they risk-averse? I cannot relate too well to this type of Founder

8/ Where do I fit in? I'm a risk-prone opportunist. Sports betting, poker, and options are all areas of interest-- areas that could potentially double the capital I can allocate to our company...

9/ The issue is a loss of focus. When you place a sports bet, sit down at a poker table, or watch the market open, your sole focus becomes what's in front of you. You'll spend 4 hours managing a $1,000 options position instead of working on your multi-million startup...

10/ How does that make sense? Even with these inflated valuations, how can you justify spending time on anything else but your company?

11/ A #YCombinator guest had a great system of viewing every hour spent doing something else as "billable for $500" like an attorney. Every hour you spend on something outside of your startup should be worth $500+ of capital that can be put back in... elsewise, it's a loss

12/ So let's ask ourselves... Everything is a choice. What am I doing right now?

13/ That's a wrap on this thread. Asking myself that question helps me identify there are better uses of my time. I do believe journaling these thoughts helps clear my head a bit though. Who knows!