Why Do Apple iOS Mail and Calendar Apps Suck?

Before I get into my rant of the morning, if you have a gluten intolerance, or just want less gluten in your life, we just invested in a company called Nima that can help you.

Today, as I was going through my daily reading, I read Fred Wilson’s Feature Friday: GBoard about Google’s new third-party keyboard app for iOS. I clicked on the link to download and try it and, as it was doing it’s thing, though to myself “why does Apple iOS Mail suck?” And then I thought “why does Apple iOS Calendar suck?”

When I’m using my iPhone, I spend a lot of time in Mail and Calendar. I’ve always been unhappy with Apple’s Mail and Calendar. I’ve gone through using lots of other ones, but in most cases, once the Mail or Calendar app is acquired by another, bigger company, it eventually stales out and vanishes. About a year about I started using Outlook on My iPhone and used it for a long time. I can’t remember what happened, but at some point I abandoned it and switched back to Apple Mail and Calendar.

As Gboard was downloading, I decided to try Gmail and Google Calendar on iOS for a while. I used them when they first came out and they were inferior to Apple’s Mail and Calendar. I tried them again about a year ago and they were good, but for some reason I didn’t stay with them.

I know that if I don’t use something for at least some extended period of time it won’t stick. Some I’m going to try having Google World on my iPhone until at least June 1st. At that point I’ll re-evaluate.

If you have any hints or suggestions, I’m all ears.

What Is Your Next Career?

I was recently asked the question “What is your next career?” as part of a discussion with an LP.

I thought it was the best diligence question that I have ever been asked. Upon reflection, the LP was clearly asking me indirectly about my long term commitment to venture capital and, without asking “how much longer are you going to do this VC thing?” she was looking for how I answered the question to get an understanding for how I thought about what I was currently doing along with an indication of how much longer I’d be doing it.

My quick answer was “I don’t have one.” I then unpacked this a little, explaining that I’ve never really thought about what I did as “a career.” While I have a LinkedIn profile, I’ve never had a resume, nor do I really feel like I’ve been on a career path.

But I realized that wasn’t an answer so I continued reflecting out loud in real time. I stated that when I think about it, VCs typically end up doing three different things after they stop being VCs: (1) be a CEO of a company, (2) politics, or (3) academia.

None of these appeal to me. I’ll never be a CEO of a company again – I did this for seven years between age 21 and 28. I was a good CEO but I never enjoyed the job. I have exactly 0.000000% in ever running for a political office. And, I was kicked out of a PhD program when I was 24 and have no interest in ever being a professor or an administrator.

I’m sure there are other things VCs do after stop being VCs, but I’m quite clear that I don’t have a next career in me.

Try On The Decision For 30 Days

I’ve made a lot of major decisions in my life – both personal and professional. For the professional ones, I’ve come up with an approach that I now use consistently. I try on the decision for a period of time – the more significant the decision, the longer the period of time. For the really major decisions, I try them on for 30 days.

Here’s an example. In 2003 I seriously thought about quitting Mobius Venture Capital. I was tired, burned out, and very frustrated. While I’d been a partner in Mobius from the beginning, I hadn’t really been engaged in managing the overall firm. I had my office and a small team in Boulder. I did my deals. I flew to the bay area often (where everyone else was located) but focused most of my energy on the boards I was on and the investments I’d made.

My whole world blew up in 2001. My portfolio melted down with the bursting of the Internet bubble. I was on way too many boards (over 25 – including four public company boards) so the entire thing was a total shit show. In addition to being miserable at work every day, I was 30 pounds overweight, drinking too much, traveling constantly, and involved in laying off thousands of people and shutting down over a dozen companies.

Then, on 9/11, all Americans participated in a massively traumatic event. I was in New York for it, having taken a redeye the night before from San Francisco. I was never in harms way, but 9/11 triggered a major depressive episode for me. When I got home to Boulder the night of 9/12 (after driving all night on 9/11 and all day on 9/12) I shut down all travel through the end of the year.

The depressive episode only lasted three months, but the shit show continued through 2002 as most VCs and Internet companies suffered a massive collapse. While my world started to settle down in mid-2002, the rest of Mobius started to more aggressively fall apart. There was no joy anywhere.

In early 2003, I started to think about leaving Mobius. While I was trying to be helpful in general to the firm and my partners, I didn’t like the way we were operating. I felt like we had way too many people, too much denial about the reality of our situation, and were making many bad decisions simply to defer the inevitable pain that was resulting from the collapse of the Internet bubble.

I woke up one morning in February 2003 and decided to spend a little time each day pretending like I had quit Mobius. I allowed myself to think about it twice a day – when I first woke up and when I went to bed at night. During the day I continued to work my ass off on everything I was doing for Mobius. But I gave myself two periods a day where I contemplated what a different work life might look like.

During these periods, I wrote down what I was relieved about. As the month went on, at the end of the day I started writing down what I was unhappy about at Mobius. In the morning I’d clear my mind as though I didn’t have anything in front of me to deal with that day, and then go into battle and deal with whatever was in front of me. At the end of the day, I’d repeat the thought process. And, at least once a week, I talked to Amy about what I was thinking about.

A clear pattern emerged for me. I didn’t dislike the work, even though most of it was not very fun. I felt a strong sense of responsibility for Mobius since I had helped create and contribute to the mess we were in. I felt a deep obligation to all the various people involved – the founders we had invested in, our LPs, and all the people who were still working for Mobius. But I didn’t feel engaged in the decision making that we – as a firm – were doing to get out of the ditch we were in.

After 30 days, I had a clear understanding that quitting Mobius was not the right answer for me. Instead, I needed to commit to engaging completely and taking responsibility for the whole firm, not just my corner of it. This didn’t mean taking over everything, but it did mean going all in on trying to make things better, whatever that meant.

In March 2003 I fully engaged in Mobius. While 2003 – 2006 was an incredible grind, I look back on that time period as one that I am satisfied with as we did manage to get Mobius to a stable place. I learned an incredible amount about running a VC firm through the work I did in that time period. And, with my partner Jason, we still manage what is left of the portfolio (still several hundred million of assets) simply because it is the right thing to do for the LPs.

When I reflect on the decision, I was only able to make it because I gave myself 30 days to really consider the decision and the various options. I’ve used this approach many times since, for decisions large and small, and it has served me well.

Book: Dark Money: The Hidden History of the Billionaires Behind the Rise of the Radical Right

Last week I was on vacation and off the grid. Amy and I decided to stay home, rest, just hang out, and read.

Dark Money: The Hidden History of the Billionaires Behind the Rise of the Radical Right was first on the list. I have a very cynical attitude toward politics, especially in the context of big money, so I was fascinated by this book. I’d read snippets about it and had read the New Yorker article Covert Operations: The billionaire brothers who are waging a war against Obama by Jane Mayer in 2010 that was the inspiration for her to write this book.

After 450 pages, my cynicism had evolved from significant to profound. I kind of knew what I was getting into when I started reading the book, but the rabbit hole is very, very, very deep. I know that there are many people, especially in politics, who don’t care about the truth and that one person’s truth is not necessarily “the truth.” But the extent of the manipulation, strategies surrounding it, lies supporting it, and the money financing it were extreme even for my already cynical perspective.

I’ve never really engaged financially in politics. While I’ve contributed here and there to candidates that I support, I’ve always done it in the context of personal contributions to the campaign. While I’ve supported specific issues like patent and immigration reform, I don’t think I’ve ever given to a candidate through an organization designed to support one of these issues, but instead I have always given my gifts directly to activities around the specific issues.

With the emergence of Super PACs, it’s gotten more confusing, but I’ve tried not to support PACs, Super PACs, or bundlers. I’ve fallen into the trap of this several times, but always made sure that what I did wasn’t tax deductible or characterized as a charitable gift. I’m not trying to be a goody two-shoes, but rather just follow the rules and play by them.

While Mayer’s book focuses on the Koch’s, a bunch of their friends in their extended network, and the rise of the radical right, she alludes to similar dynamics going on now on the liberal front. While it’s easy to paint it as extremes of the Republican party, label it the rise of the libertarians, or describe it as a takeover of the Republican party, it’s clear to me that the financial dynamic described covers the entire political spectrum.

But that’s not the disturbing part to me, as money, influence, and power have always been wrapped up together. Instead, I ‘m bothered by the characterization of the activities as charitable, the blatant tax evasion from the contributors, the disingenuous behavior by the principles and their proxies, and the fundamental disrespect for a system that is supposed to be representative of the people.

Regardless of your political leanings or attitude, this book is worth reading, if only to have a perspective on how far we have gone into some alternate reality that now is driving how things work. Or maybe it’s always been this way, and we are just now noticing how much money is, and can be, involved.

Work Hard. Be Kind.

For your Sunday video watching, I encourage you to spend ten minutes of your life and watch Chris Moody‘s Commencement Address to the Auburn 2016 graduates.

His message is simple: Work Hard. Be Kind.

Having worked with Chris for many years, it’s a great summary of how he lives his life. And he ends with a magnificent Dalai Lama quote. “Be kind whenever possible. It is always possible.”