Startup 101 Series: Updated links and what’s next

Just added ~20 new reads to the startup 101s (collections of great startup reads). Removed a few, too:

I’m also working on a simple ebook which will combine these 101s with some new material and an edited collection of my 1-Read-A-Day lessons (you can subscribe here; warning: it’s a lot of content :)

I’ve also started a new, related project — trying to iterate to something truly useful. So far, the feedback has been great. More on that soon. Still startup content, still about saving you time and finding you the best. I love Joe Wikert’s idea of the content concierge.

Would you pay for some combination of curation and summarization? I’d love to know!

1-Read-A-Day: what I learned running a newsletter, October edition

Every month, I share what I’ve learned running the 1-Read-A-Day newsletter. Here’s the first month.

How well is it doing?

  • Subscribers: 230 (only 10 new subs since September)
  • Open rate: 22.6%
  • Click rate: 2.5%
  • Most opened email: Lesson 5, Making Yourself a CEO by Ben Horowitz
  • Most clicked email: Lesson 39, How Mint beat Wesabe by Noah Kagan

What did I learn in October?

  • Readers were quiet this month. Several commented that they enjoyed the 10-question quiz after Lesson 50
  • I recorded three short audio summaries for Lessons 1, 2, and 3. Just experimentin’. They’re around a minute each. You can hear them by clicking the big blue button near the top
  • I published another 101, Startup Mistakes and Failures. 27 great links featuring Max Skibinsky, Siqi Chen, Derek Sivers, and more
  • I wish there was an easy, effective way to convert emails into blog posts. There are plugins that convert RSS feeds into emails, but I can’t find a good plugin to do the opposite. With email newsletters growing in popularity, I hope this problem is solved soon
  • I wish Mailchimp allowed me to better manage autoresponder emails in bulk. Right now, if I make a design change to one Lesson, I need to manually repeat that change more than 50 times!

What’s coming up

  • More 101s: Hiring, Product, and Stories
  • Once I hit 100 lessons, I’ll create a draft Startup Textbook (a well-designed PDF file featuring the 101s and the summaries). Hope we’ll be there by December
  • I haven’t marketed the newsletter (beyond blog posts and tweets), but subscribers are not growing (5% since September). I’ve been unwilling to make a big push, and I’m not sure why (perhaps I don’t think it’s good enough?)

Thanks to all subscribers for your feedback. It’s been a pleasure to do this. Here’s to showing up and getting to work. Cheers!

PS. If you run an email newsletter, I’d love to hear what you’re doing and what you’ve learned

1-Read-A-Day: what I learned running a newsletter, September edition

Every month, I share stats and learnings on the 1-Read-A-Day newsletter. Here’s the launch post.

How well is it doing?

Subscribers: 220 (last month: 161)
Open rate: 22.9% (22.8%)
Click rate: 2.6% (2.2%)

Thanks to Kale’s feature, I got 27 signups in a single day. By far the largest jump since the July launch. I highly recommend subscribing to his Hacker Newsletter and also enjoy his Wayback Letter, a nice way to re-surface classic content that has disappeared from the interwebs.

What did I learn in September?

1. Per Tommy’s advice, I customized the Gmail preview snippet.

Open rates have increased, but it’s correlation, not causation. The change makes me feel better, though.

To customize the snippet and not harm the email’s readability, I explored several options but went with this one: the text snippet is placed it at the top of each email, then the font size is set to 1 and font color to white, so it’s invisible to readers.

2. Readers complained they couldn’t distinguish direct quotes from my color commentary. So I added a quote symbol inside each yellow box. This has received positive feedback, but there is a downside: before, each email was image free and did not require you to click “Display images below” (if you’re using Gmail) to load the quote-symbol-image. Another lesson: product “improvements” are often double-edged swords

3. Quizzes are the most complimented feature, so I added more questions to each quiz. I will also have a big, 10-question quiz after Lesson 50. I’m even thinking of launching startup quizzes as a separate project. “test your startup IQ” sort of thing

4. There’s a tension between esoteric and popular content. Well-read startup folks appreciate the esoteric content, but it’s often esoteric for a reason (niche appeal, out-of-date, too technical). However, I do agree that I’ve relied heavily on popular content, so going forward, I will feature more esoteric/lesser-known articles and bloggers (such as this thoughtful essay from Max)

What’s coming up – niche email courses and audio lessons

My goal was 50 lessons before I began to widely market the newsletter and release topic/problem-specific email courses (eg, 20 email lessons on hiring engineers, or 35 email lessons on raising a VC round). I’m on lesson 50 (congrats if you’ve read all of them), so these are coming soon.

I’m also planning to record 60-second podcasts for each lesson, for those who enjoy audio learning and have time to kill on the daily commute or while at the gym.

Thanks to all my subscribers for your participation and feedback. Keep it coming, it’s been a pleasure to do this. Here’s to showing up and getting to work. Cheers!

PS. If you run an email newsletter, I’d love to hear what you’ve learned, what works, and what doesn’t.

Entrepreneurs as predators, not risk-takers: Malcolm Gladwell’s The Sure Thing

Malcolm Gladwell in high school trackAnother classic article from the Gladwell archives.

Gladwell argues that the conventional view of entrepreneurs as hot-headed risk-takers is wrong. The most successful entrepreneurs are actually cold-blooded, calculating predators. From Ted Turner to John Paulson to Sam Walton, Gladwell arrives at the conclusion that the most successful entrepreneurs aren’t taking risks at all – they simply see an opportunity that others miss or undervalue, and consistently minimize chances for failure along the way.

Full article here.

The write-up below is included in my 1-Read-A-Day newsletter.

Highlights from the article

Gladwell starts by explaining how Ted Turner bought a local broadcast station and built it into TBS – against the advice of everyone around him:

“We tried to make it clear that—yes—this thing might work, but if it doesn’t everything will collapse,” Mazo said, years later. “Everything you’ve got will be gone. . . . It wasn’t just us, either. Everybody told him not to do it.”

[Turner] was a drinker, a yeller, a man of unstoppable urges and impulses, the embodiment of the entrepreneur as risk-taker. He bought the station, and so began one of the great broadcasting empires of the twentieth century.

The character portrait is a romantic one, but inaccurate. Turner had significant advantages from day one: the billboard company he inherited from his father gave him plenty of cash and excess inventory to advertise the new network.

Further, Turner paid a reasonable purchase price and didn’t put a penny down.

The truly successful businessman…is anything but a risk-taker. He is a predator, and predators seek to incur the least risk possible while hunting.

Examples of other risk-minimizing entrepreneurs include:

  • Giovanni Agnelli (the founder of Fiat) who kicked out his initial investors to gain majority control
  • George Eastman (the founder of Kodak) who shifted early financial risk to his wealthy friends
  • Ingvar Kamprad (the founder of Ikea) who had his furniture built in Poland instead of Sweden – at half the cost

Then there’s hedge fund manager John Paulson. By 2004, Paulson was managing $2B and was,

“Zuckerman writes, a “solid investor, careful and decidedly unspectacular.” The particular kinds of deal he did were “among the safest forms of investing.”

In the housing boom of 2004-2005, Paulson began shorting subprime mortgages – to the tune of $25 billion dollars (!).

Most people thought the trade was too risky; they believed Paulson was crazy. But Paulson – through meticulous research – saw an something they missed.

“There’s never been an opportunity like this,” Paulson gushed to a colleague, as he made one bet after another. By “never,” he meant never ever—not in his lifetime and not in anyone else’s, either…In 2007 alone, Paulson & Co. took in fifteen billion dollars in profits, of which four billion went directly into Paulson’s pocket. In 2008, his firm made five billion dollars. Rarely in human history has anyone made so much money is so short a time.

Paulson and Turner are PREDATORS. They’re not braver or crazier than the rest – they’re MORE ANALYTICAL. They see opportunities that others miss and they act immediately and aggressively.

In Turner’s case, he even became physically sick when his family purchased a competing billboard firm, a deal he considered too risky:

It was a good deal, not a perfect one, and that niggling imperfection, along with the toll that the uncertainty was taking on his father, left Turner worried sick. “During the first six months or so after the General Outdoor acquisition my weight dropped from 180 pounds to 135,” he writes. “I developed a pre-ulcerative condition and my doctor made me swear off coffee. I’d get so tired and agitated that one of my eyelids developed a twitch.”

When you look at the winning hedge funds in the subprime mortgage collapse, they all shared the same behavior: predators who did their homework, found a marketplace anomaly, and made a big, calculated “bet”.

You could even argue that the entrepreneurs who take the most risks are most liable to fail.

Taking over an existing business is always the best bet; failed entrepreneurs prefer to start from scratch. Ninety per cent of the fastest-growing companies in the country sell to other businesses; failed entrepreneurs usually try selling to consumers, and, rather than serving customers that other businesses have missed, they chase the same people as their competitors do. The list goes on…a good many of these risks reflect a lack of preparation or foresight.

And some science to back it up:

When the sociologists Hongwei Xu and Martin Ruef asked a large sample of entrepreneurs and non-entrepreneurs to choose among three alternatives—a business with a potential profit of five million dollars with a twenty-per-cent chance of success, or one with a profit of two million with a fifty-per-cent chance of success, or one with a profit of $1.25 million with an eighty-per-cent chance of success—it was the entrepreneurs who were more likely to go with the third, safe choice.

Gladwell’s a tremendous writer, social theorist, and story-teller. Highly recommended article.

What I learned starting a newsletter (1-Read-A-Day)

I think you misinterpreted...In July, I launched a newsletter called 1-Read-A-Day.

Every day, I recommend and summarize one article on some aspect of starting or growing companies.

Entrepreneurs – especially CEOs – rarely have time to learn. But they are constantly checking email.

I ask them to spend 2 minutes reading my email, and in return they’ll learn something that will make their startup better. If they want to dig, they can read the original article.

The original articles feature well-known guys like Paul Graham and Chris Dixon. They also feature lesser-known people who are in the trenches, struggling every day to build something great.

Like I mention on the signup page, it’s Cliffnotes for startup essays.

Enough pitching. I hope you subscribe :)

Starting today, I’m going to write a monthly post that shares what I’ve learned running this newsletter. I’ll be transparent and include subscribers, analytics, experiments, and general observations.

Please keep in mind that this is a side-project. I’ve spent an hour a day working on it and have no plans to increase my time commitment.

What is it?

  • It’s an autoresponder sequence (also known as a drip sequence) which sends emails on a pre-determined schedule. If you subscribe today, you’ll receive the same first email that a subscriber 2 months from now will receive
  • I’m the only one curating and summarizing the content. Some of the articles I use are influenced by the Hyperink list. Others are sent to me by friends and colleagues
  • I use Mailchimp for everything: from design to sending emails to managing subscribers
  • My goal is 100 of these email lessons. After that, who knows?

How well is it doing?

  • Subscribers: 161
  • Open rate: 22.8%
  • Click rate: 2.2%

The subscriber # is low. Once I hit 50 email lessons, I will start marketing the newsletter more aggressively. For now, I’m content with referrals and pimping it on this blog.

What have I learned?

  • Your subject line heavily influences your open rate. When I mention “CEO” or “VC” in the subject line, the open rates are noticeably higher
  • People enjoy quizzes. I send a 2-3 question quiz after every 5 lessons, to help people retain what they learned. The quiz emails get the highest open rates and positive responses
  • Design matters. My design is simple, but on the sucky side of simple. Look at Sacha Greif’s newsletter then look at mine. I’ve made small improvements but this is a weak area. I will eventually seek help from those much better at design than me
  • I enjoy finding great educational content and summarizing it. This is a central lesson I’ve learned about myself: to keep doing anything, I need to enjoy the meat-and-bones of the work. It seems an obvious insight from simpler pursuits (after all, don’t all successful painters enjoy painting?) but becomes less obvious in more complex pursuits (if you’re growing an enterprise software company, what is the meat-and-bones of the work and do you enjoy that? in that case maybe the meat-and-bones is the actual growing of the company)
  • Email newsletters are in. Old-school online marketers (they of the David DeAngelo and Frank Kerns variety) have known for years that email converts. Everyone hates on email, but its still the #1 online communication tool. My favorite newsletters like Sinocism and Hacker Newsletter just keep growing, and are a favorite part of my daily media consumption routine

I really like this quote from Chuck Close:

Inspiration is for amateurs — the rest of us just show up and get to work. And the belief that things will grow out of the activity itself and that you will — through work — bump into other possibilities and kick open other doors that you would never have dreamt of if you were just sitting around looking for a great ‘art idea.’ And the belief in that process, in a sense, is liberating and that you don’t have to reinvent the wheel every day.

I’ve discovered this truth while building 1-Read-A-Day. Adding emails, listening to feedback, and doing the work has really opened up other possibilities. For example, I plan to launch an audio complement for each email (so you can listen to it while you’re on the road). I will also launch more focused drip sequences, on common problems like “how to raise a seed round” or “how to hire great engineers”.

Here’s to showing up and getting to work. Cheers!

PS. If you run an email newsletter, I’d love to hear what you’ve learned, what works, and what doesn’t.