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Josh Maher's Blog » Entries tagged with "ESPP"

Reporting ESPP taxes

Tweet I know taxes are due any day now and you are wondering what the heck to do with your ESPP tax reporting. Maybe you’ve been participating in your companies ESPP for years or got started recently. Either way, an understanding of how to deal with ESPP tax reporting is important and it also highlights how great of an opportunity you have because an ESPP is available for you to participate in. If you haven’t started investing in your company ESPP – you should go read You have an ESPP now what, then learn to configure your account for selling ESPP shares, then read up on what to do with all those dividends and option premiums in your ESPP account, and finally read this article on how to report the profits … Read entire article »

Filed under: ESPP

Investing Lessons from the World Financial Symposium

Tweet If you haven’t been following the series on investing lessons from venture capitalists, now is a good time to start. The latest in the series comes from some great insight that was provided at the World Financial Symposium here in Seattle. The question of course that everyone has next is what the hell is the world financial symposium and why is it in Seattle? Amazingly of course the angel investors on hand at the symposium generally had the same thought in response to the always outstanding question of why isn’t Seattle a bigger startup community? Regardless of the amount of angel and venture capitalist investment that happens in the region, there is an amazing amount of talent on the entrepreneur and investor sides of the table. Some of the lessons from … Read entire article »

Filed under: Economics, Entrepreneurship, Innovation, Investing, Seattle, Startups, stocks, Technology

5 Investing Lessons from Jeff Clavier

Tweet I came across this infographic and thought it good to share in the series of Investing Lessons From Venture Capitalists series. It is interesting because it initially highlights what a tech VC looks at when evaluating an investment so of course if you are starting a new tech company and are planning to raise money for that new tech company you need to understand all aspects of the infographic. For the rest of us who aren’t creating new tech companies and just happen to work at them or are friends and family of them… this is interesting as well for a number of reasons. If you are giving any feedback to a tech startup and don’t have expertise or a strong opinion in one of the areas here – don’t fake … Read entire article »

Filed under: Entrepreneurship, ESPP, Investing, Startups, stocks, Technology

ESPP Dividend Reinvestment

Tweet I have had a few readers ask about the difference between two key strategies inside of an ESPP – Selling Covered Calls and Dividend Reinvestment. I haven’t really covered Dividend Reinvestment yet so can’t do justice with a comparison of the two here on the blog. I’ll put this post together and later do some comparison of the two ESPP strategies. Both of these strategies are ideal for ESPP where the stock has a dividend, mostly due to the compounding relationship (as any dividend paying investment provides). The idea of Dividend Reinvestment is centered on holding a stock and growing a position in the stock over a long period of time. To support this goal, all dividends (distributions of corporate earnings) are used to purchase more shares of the company. This … Read entire article »

Filed under: ESPP, Investing, Profit, stocks

Investor Training

Tweet I have a few more in the Investing Lessons from Venture Capitalists in the works and will post them in the coming weeks. Of course anyone interested in investing in public or private markets and businesses should look at more than just VCs for lessons. A few must read guides for investors – I have these on my Kindle and re-read them occasionally as the messages here are amazing reminders of what I need to focus on when evaluating companies and properties to invest in. I know that some of you just pick a few ETFs, participate in your employer’s ESPP and call it good (Don’t get me wrong – I love that strategy so long as you are not only betting on the company you work for and have … Read entire article »

Filed under: ESPP, Investing, stocks

It Takes Two to Tango

Tweet I get a lot of feedback about my Covered Call ESPP strategy from efficient market theorists. They tell me that I will make and lose money on the trades based on the efficiency of the market. They commonly forget that markets are composed of people and when it comes to individual transactions there is a buyer and a seller. Howard Marks ranted about this in a recent letter (see below). The fact that transactions have buyers and sellers means that  while the market may display efficiencies, each transaction Understanding who is on both sides of the transaction is important. If you are looking to make a new investment of any kind, an Angel investment, a Real Estate Investment, or purchasing shares of a business on a public market you need to … Read entire article »

Filed under: Entrepreneurship, Investing, RealEstate, stocks

QE Timeline and the Market

Tweet Bill McBride over at Calculated Risk has put together an interesting QE Timeline – in his post he outlines what occured at each of these stages and has included the graphic that I am linking to below. It is interesting to think about the implications that these market manipulation programs have on the overall market. If the programs truly are causal to the market direction, we should be looking at an upward market over the next time period despite the other signs in the economy. This would be despite Europe concerns, impact of healthcare, hiring, consumer/corporate spending, or any of the other indicators out there. Of course as I mentioned before most of these “market making news numbers” shouldn’t be used in retail investment decisions. Regardless it is important to understand the general … Read entire article »

Filed under: Banking, Covered Calls, ESPP, Investing, Profit, stocks

Retail Investment Decisions

Tweet There as been an increasingly interesting discussion about how retail investment is changing. Leigh Drogen (one of the guys behind Estimize), Josh Brown (Stocktwits blogger), and now TechCrunch posted a peice last week from Nick Shalek. Everyone is debating the disruption of retail investing from the likes of Wealthfront, Betterment, FutureAdvisor, etc. I have looked at all of the platforms in the past and they seem to do a good job matching the capabilities of the average broker out there. Go work with an “advisor” from Morgan Stanley and they’ll walk through all of the same risk profiling for the person looking to invest their money and then kindly recommend a nice Morgan Stanley fund that matches the profile. I haven’t exactly been shy about how crappy a deal this kind … Read entire article »

Filed under: Covered Calls, ESPP, Investing, Options, Profit, stocks