Seed Fundraising 101: The best articles, blog posts, and Quora threads

When I launched The Startup Textbook a month ago, I had grand visions for a beautiful textbook of the web’s best startup content.

I enjoy curating, reading, and summarizing startup content. But unfortunately, I didn’t enjoy the process of creating a textbook from scratch.

That’s why the newsletter has been going well (and is FUN to work on), but the textbook effort has languished.

So, instead of a complete textbook, I’m publishing a series of “101” posts with the best links that I’ve collected. Starting with seed fundraising, then tackling topics like culture, CEOs/leadership, legal issues, product, hiring and more.

Don’t let perfect be the enemy of the good, as Voltaire says.

So here’s the first 101, Seed Fundraising. I’ll publish a new one every few weeks, and will continually update each page since there’s always more great stuff.

Be warned: this is a LONG post so I’ve provided links to jump back-and-forth.

Bitcoin please? Donations always help. Use Venmo or Paypal. Thanks and enjoy!

Kevin

P.S. Please send me links. My asks: #1, they’re free, and #2, they’re educational (for example, a news article about a startup raising $2mm from top seed investors is relevant if it includes fundraising advice from the founders).

P.P.S. If you want a daily email recommending, and summarizing, a great startup article, subscribe to 1-Read-A-Day.

P.P.S. The second 101 is Startup CEOs. All of them are here.

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Seed Fundraising 101: Common questions

Total links: 97!!

Question 1: Do I need to raise a seed round?
Question 2: How much should I raise?
Question 3: Will I be able to raise?
Question 4: How do I put together a great pitch deck?
Question 5: What are the different types of investors?
Question 6: What am I looking for in seed investors?
Question 7: How do I hire an entrepreneur-friendly lawyer?
Question 8: How do I meet investors (angels and VCs)?
Question 9: Should I raise from angels or VCs?
Question 10: Should I use AngelList, and what are best practices?
Question 11: Should I apply to incubators like Y Combinator or 500 Startups?
Question 12: Once I start fundraising, what is the process like?
Question 13: What advice do you have on scheduling, running, and following-up on investor meetings?
Question 14: What questions will investors ask?
Question 15: What financing terms should I know? How do I read a termsheet?
Question 16: How do I follow-up with investors?
Question 17: How do multiple fundraising rounds work?
Question 18: How do I negotiate terms like valuation cap and discount?
Question 19: Should I do reference checks?
Question 20: They said yes! How do I get money in the bank?
Question 21: Should I create a board of directors? Board of advisors?
Question 22: How do I work well with my investors?
Question 23: Should I announce that I raised a round? How do I get PR from Techcrunch, Pandodaily, and other news outlets?
Question 24: When should I raise another round?

Question 1: Do I need to raise a seed round?

Shoehorning startups into the VC model by Chris Dixon

A startup should raise venture capital (or “venture-style” angel/seed funding) only if: 1) the goal is to build a billion-dollar (valuation) company, and 2) raising millions of dollars is absolutely necessary or will significantly accelerate growth.

Here’s the email summary from 1-Read-A-Day.

Notes on raising seed financing by Chris Dixon

Best thing is to either never need to raise money or to raise money after you have a product, users, or customers. Also helps a lot if you’ve started a successful business before or came from a senior position at a successful company.

20 Questions To Ask Yourself Before Raising Money by Elad Gil

1. Why are you raising money? It is for vanity purposes or does your business really need it?
3. What are your goals as founders? How will raising money impact these goals?

Is Your Startup A Cash or Equity Business? by Elad Gil

There are, broadly speaking, 2 types of ways to build value in a business.
(a) An “equity” based business in which the stock value will grow significantly with time
(b) A “cash” based business, in which the company will generate a lot of cash on an annual basis, but the value of the stock will remain a low multiple of earnings.

The Value of Fundraising by David Hornik

The fundraising process forces you to better define and defend your business strategy…A defensible strategy is not something you can fake…No matter what the outcome, the conversation is a valuable one.

Here’s the email summary from 1-Read-A-Day.

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Question 2: How much should I raise?

How to do seed fundraising right by Kate Endress

Put together a detailed monthly model in Excel and project your cash burn as best you can. Raise enough money to hit meaningful milestones. For my company, the seed round milestones were to take the technology risk off the table by moving from a virtual fitting prototype to a web-based product and to sell 1,000 pairs of glasses.

What’s the right amount of seed money to raise? by Chris Dixon

Short answer: enough to get your startup to an accretive milestone plus some fudge factor. “Accretive milestone” is a fancy way of saying getting your company to a point at which you can raise money at a higher valuation.

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Question 3: Will I be able to raise?

How to Raise Venture Capital by Neil Patel

So why didn’t Crazy Egg get funded? Crazy Egg wasn’t an idea that had the potential to be sold for anywhere near 100 million dollars.

Why You Shouldn’t Raise VC by Mark Peter Davis

For medium-sized VCs, a large opportunity equates to a $1 billion addressable market; big VC funds need to believe your market is in the billions of dollars, typically $5 billion to $10 billion (or more).

High Resolution Fundraising by Paul Graham

Fundraising is an extremely momentum-based process. Hardest part is getting “anchor” investors. These are people or institutions who commit significant capital (>$100K) and are respected in the tech community or in the specific industry you are going after (e.g. successful fashion people investing in a fashion-related startup).

[…]

By far the biggest influence on investors’ opinions of a startup is the opinion of other investors. There are very, very few who simply decide for themselves. Any startup founder can tell you the most common question they hear from investors is not about the founders or the product, but “who else is investing?”

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Question 4: How do I put together a pitch deck?

The 10/20/30 Rule of PowerPoint by Guy Kawasaki

I am evangelizing the 10/20/30 Rule of PowerPoint. It’s quite simple: a PowerPoint presentation should have ten slides, last no more than twenty minutes, and contain no font smaller than thirty points. While I’m in the venture capital business, this rule is applicable for any presentation to reach agreement: for example, raising capital, making a sale, forming a partnership, etc.

Size markets using narratives, not numbers by Chris Dixon

For early-stage companies, you should never rely on quantitative analysis to estimate market size. Venture-style startups are bets on broad, secular trends. Good VCs understand this…The only way to understand and predict large new markets is through narratives. Some popular current narratives include: people are spending more and more time online and somehow brand advertisers will find a way to effectively influence them; social link sharing is becoming an increasingly significant source of website traffic and somehow will be monetized; mobile devices are becoming powerful enough to replace laptops for most tasks and will unleash a flood of new applications and business models.

6 Tips To Get Your Startup Off The Ground And Score A Seed Round by Anthemos Georgiades

We spent 50 percent of our time in VC meetings discussing one of our 14 slides. This particular slide – in simple graphics – portrayed the uptick we’d created for clients using our alpha site. That one slide dominated every conversation and helped us pitch the end-game of where we could be in five years.

How To NOT Write A Business Plan by David Cowan

Your presentation should not exceed 10 slides. The appendix can include as many slides as you want. Nothing beats responding to some VC’s question with a slide from the appendix. Sales productivity? Here are the historical numbers. The competitor’s software? Here’s a screenshot. Most operating details will remain safely ensconced in the appendix, eliminating unnecessary friction in the presentation.

365 Days, $10 Million, 3 Rounds, 2 Companies, All With 5 Magic Slides by Tim Young

Normally, in a pitch meeting, you and the investor sit on opposite sides of the conference table. But by sharing a screen and sitting in close proximity to each other, the environment naturally becomes more comfortable and relaxed.

Here’s the email summary from 1-Read-A-Day.

How To Raise A $1M Seed Round by Sunil Rajaram

No matter how you size the market, be ready to get ripped to shreds. It goes without saying that VCs want to see a multi-billion dollar market, but how a VC reacts to your numbers could depend on what they ate for breakfast that morning.

How to do seed fundraising right by Kate Endress

Get a LOT of feedback on your investor deck from friends, advisors, and investors. Make sure it’s perfectly formatted and that you know backup details for every single number in your presentation.

How to Analyze Your Startup Like A VC in 15 Minutes Or Less by Tom Tunguz

The BMC describes the key operations of a business: the Value Proposition, the Key (Operating) Activities, Partners, Assets/Resources, Customer Relationships, Go-To-Market Channels, Customer Segments, Cost Structure and Revenue Streams.

Here’s the email summary from 1-Read-A-Day.

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Question 5: What are the different types of investors?

A SuperAngel’s Investment Guide by Fabrice Grinda (angel investor and entrepreneur)

Jose and I have successfully been doing international idea arbitrage for 12 years in the businesses we run. We apply the same principles to many of the companies we invest in. A large portion of our investments, and our seemingly most successful investments, are localized versions of successful US concepts for Brazil and Russia.

Here’s the email summary from 1-Read-A-Day.

Notes on raising seed financing by Chris Dixon (a16z)

Types of capital: strategic angels (industry experts), non-strategic angels (not industry experts, not tech investors), tech angels, seed funds, VCs. VCs can be less valuation sensitive and have deep pockets but are sometimes buying options so come with some risks (more). Industry experts can be really nice complements to tech investors (especially in b2b companies). Non-strategic angels (rich people with no relevant expertise) might not help as much but might be more patient and ok with “lifestyle businesses. Tech angels and seed funds tend to be most valuation sensitive but can sometimes make up for it by helping in later financing rounds.

How Funding Rounds Differ: Seed, Series A, Series B, and C… by Elad Gil

Series Seed: Figuring out the product and getting to user/product fit
Series A: Scaling the product and getting to a business model. (AKA getting to true product/market fit)…you typically have figured out your product/userbase, and need capital to…

The 7 types of angel investors – what is right for your startup? by Elad Gil

1. Connectors
2. Product people
3. Tacticians & builders
4. Smart business people
5. Domain expert
6. The brand
7. The filler (aka dumb money)

How to select your angel investors by Chris Dixon

The most common mistake entrepreneurs make is to base their choice solely on the investors’ “celebrity” value (by “celebrity” I generally mean in the TechCrunch sense, not the People magazine sense). Picking celebrity angels might help you get a little more buzz when you announce the financing and a few SUL tweets, but that’s about it. A startup is a long trip — what you should care about is whether, through the ups and downs and after the buzz dies down, the investors will actually roll up their sleeves and help you.

Angel Funding Advice by Mark Suster

Quick caveats: having fewer investors (3-5) is better than many investors (10-15) and PLEASE make sure you hire a great lawyer who has experience in doing start-ups to avoid pitfalls that will make VC harder down the line.

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Question 6: What am I looking for in seed investors?

Angel Investing Skill 2 – Domain Knowledge by Mark Suster

So many deals seem like obvious money makers. But then I talk with my partner Brian McLoughlin who has worked in the field for 20 years and he’ll run through the 10 reasons why similar companies haven’t succeeded. Not in a cynical way – he just has the domain knowledge to know what has been tried before. It’s sort of like having an Encyclopedic history book before just launching your product and seeing whether anybody uses it.

Angel Investing: Skill 3 – Relationships with VCs by Mark Suster

First Round Capital & True Ventures seem to spend as much time cultivated relationships with “second round capital” as they do entrepreneurs. Keith Rabois (mentioned in my previous posts on angel investors) is on record on GigaOm as saying how important VC backed deals are to him. Why? Because he doesn’t look to invest in quick flips. He believes that returns are derived by industry-changing companies and as an investor in LinkedIn, Yelp & YouTube (to name a few) I guess he’s got the credibility to say that.

Angel Investing 4 – Why You Need Deep Pockets to Win Big by Mark Suster

The second scenario is the one we’ve already discussed – the ability to “lean” on deals that are doing well. In the worst case you want to protect your prorata investment as much as possible (e.g. avoid being diluted). But the best investors are those that spot their best hands after the flop and find a way to increase their ownership before the turn or river.

Angel Investing – The Most Underrated Skill: Access to Buyers by Mark Suster

Imagine that you funded Larry & Sergey, Chad Hurley & Steve Chen, Mark Zuckerberg, Mark Pincus or Evan Williams. Or eBay / PayPal, Salesforce.com, Skype, etc. Imagine the kind of relationship you’d have with these folks and your ability to discuss their needs as well as your portfolio successes at which they should be looking. Or imagine that you were colleagues with any of these individuals before becoming an investor.

Raising Angel Money by Mark Suster

As an entrepreneur you should raise money from the most experienced people possible – period. If you have the opportunity to raise a small amount of money from a group of experienced investors who have a track record of helping companies get from that tricky idea stage to being a well-formed company with a good product and solid market-entry strategy I would take the money – even if it were priced.

Pick Your Angel Investors Wisely by David Hornik

It is true that money is fungible. But investors are not. The choices you make when raising seed capital can have a meaningful impact on the long-term success of your startup…Find investors with the time and inclination to help you. Find investors who will increase your chances of raising additional capital, not diminish those chances.

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Question 7: How do I hire an entrepreneur-friendly lawyer?

Ideal first round funding terms by Chris Dixon

There is no reason you should pay more than $10K for the financing (including both sides). I personally use Gunderson and think they are great. Whoever you choose, I strongly recommend you go with a “standard” startup lawfirm (Gunderson, Wilson Sonsini, Fenwick etc). I tried going with a non-standard one once and the results were disastrous.

You Should Read Every Word of Every Legal Doc (Especially Funding Docs) by Elad Gil

Reid Hoffman was one of my company’s (Mixer Labs, acquired by Twitter) investors. One piece of advice he gave me was to read every word of every contract I signed on behalf of Mixer Labs (including the crazy ALL CAPS parts and legalese). This is one of the better pieces of advice I received.

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Question 8: How do I meet investors (both angels and VCs)?

Notes on raising seed financing by Chris Dixon

Make sure you have good Google results (this is your first impression in tech). Have a good bio page (on your blog, linkedin and about.me) and blog/tweet to get Google juice. Get involved in your local tech community. Join meetups. Help organize events. Meet every entrepreneur and investor you can. Entrepreneurs tend to be more accessible & sympathetic and can often make warm intros to investors.

Getting Access to the Old Boys’ Club (how to approach a VC) by Mark Suster

I remember asking for advice from a law firm in 1999 (before my first fund raising exercise) the best way to approach VCs. He told me that “most VC’s will figure that if you are truly an entrepreneur you’ll find somebody that knows them, develop a relationship with that person and find a way to get them to introduce you to the VC. If you can’t do that then you’re probably not really an entrepreneur.

How to Optimize Your Startup’s Web Presence for Investors by Andy Sparks (Mattermark cofounder)

LinkedIn is also a great source for investors to track how fast your company is growing in terms of employment, so once you create a page for your company make sure you (the founders) and your employees list your startup as their current place of employment…

How To Reply to Angel Investor Intro Emails by Elad Gil

1. Move the introducer to BCC. They don’t want to be on the 15 emails it takes to schedule the meeting.
2. Put social proof up front. All these great investors are part of the round! Angela angel will want to be part of the club and invest too. It also means you are more legit than the other random companies trying to talk with the same investor.
3. If you have good traction or a key stat, explain it in 1-2 lines. This is additional proof that they need to rush to talk to you.

Investors don’t want to meet you. They wanted to be introduced to you. by Jason Freedman (42 Floors CEO)

One day, I met a prominent VC at a conference. I started my elevator pitch. But in a rare moment of candidness, he told me that he doesn’t go to conferences to meet new startups. He told me, “By the time they get here, they’re already picked over.”

Seed Startups & Fundraising by Jared Tame

The smart founders are going to identify these investors quickly by how excited they get and how decisive they are. Being more decisive will be a key indicator of how valuable an investor will be at the seed stage—even if it’s a quick pass.

Startup Advice: How Entrepeneurs Gain Credibility by David Hornik

The best way to earn credibility with investors is to have good answers to the questions you are asked. […] That doesn’t mean that you need to have all the answers. You don’t. You just need to be thoughtful when you don’t and explain 1) how you intend to get the answer, 2) what you predict the answer to be, based upon what you do know, and 3) how you expect to gain the answer over time.

Getting Peter Thiel’s Attention–and His Money by Christine Lagorio

Bannon: How about a game of blitz?
Thiel: What?
Bannon: How about a game of blitz?
Thiel: Now?
Bannon: Yeah, I have a table set up over there.
Thiel: Give me five minutes.

How to get meetings with people too busy to see you by Steve Blank

The meeting requests that now jump to the top of my list are the few, very smart entrepreneurs who say, “I’d like to have coffee to bounce an idea off of you and in exchange I’ll tell you all about what we learned about xx.”

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Question 9: Should I raise from angels or VCs?

The problem with taking seed money from big VCs by Chris Dixon

when you take any money at all from a big VC in a seed round, you are effectively giving them an option on the next round, even though that option isn’t contractual. And, somewhat counterintuitively, the more well respected the VC is, the stronger the negative signal will be when they don’t follow on. […] Basically big VCs are spending 5% of their budget generating captive leads for their real business: investing $10M into a companies at the post-seed stage.

VC Signaling Coming Home To Roost by Elad Gil

A large number of seed rounds in the last 12-18 months have included traditional venture funds as investors. Sometimes having a VC in your seed can be super helpful. However, a number of the the companies who raised from VCs are now regretting it, as having a VC in your seed round can backfire. There are a number of ways to mitigate this signaling risk.

Financing approaches most likely to kill your company (if it is already on the edge) by Elad Gil

Your Funding Structure Today Impacts Whether You Are Middle of The Pack or Dead Tomorrow […] The line between “Middle of the pack” and “Dead” will be a fine one. One of the characteristics that may tip companies from Middle of the pack into Dead is the existing cap table/financing structure of the company.

Understanding a VC’s Seed Funding Policy is Critical by Mark Suster

4. The signaling affect is overrated. Everything you do is a signal. Investors will look at which angels you chose, whether old bosses invested, whether you were an EIR somewhere and did they invest, etc. Future investors will also look at whether your angels “re-upped” if you hit a bump in the road. VCs are just one of many signals future investors at which future investors will look. If you don’t understand the concept of “signaling” please read the blog post I wrote on Understanding VC signaling.
[…]
6. So the biggest issue for entrepreneurs IMO is not “to VC or not to VC” but rather “what chemistry do I have with my funding sources, how aligned to I feel we are on how to build a company, how much do they understand my specific opportunity and importantly what can I find out about them from referencing previous people with whom they’ve worked and do they have a well defined seed program strategy.

Jump back to the ToC

Question 10: Should I use AngelList, and what are best practices?

A PRIMER FOR FUNDRAISING ON ANGELLIST by Aaron Hall

I quickly decided that becoming a “trending” startup, or getting featured on AL, was the quickest path to increase our reach. This was the first step in the fundraising process for us. […] Next, I wanted to figure out how to get “reach”. Each Sunday, AL sends out an email to all investors promoting the top four trending companies. I knew from talking to investors that they keep an eye on the trending list to find new companies. I wanted to make sure Boatbound was one of them.

AngelList’s Big Four Benefits for Investors by Ty Danco (Vermont-based angel investor)

Either way, I often find following either senior or beginning VCs creates too low a signal to noise ratio, so I concentrate mostly on active angels I respect. There are exceptions: some micro-VCs associated with incubators (e.g., Dave McClure) work AngelList hard to promote their companies…but you need to recognize that that is part of the brand strategy for their companies and their incubators.

How we built Shyp on AngelList and raised $2.1M by Kevin Gibbon (Shyp founder)

AngelList is not only about fundraising — it is a recruiting beast! Jack Smith reached out to us after we were featured to see if he could help out in any way. Joshua and I later convinced him to join as a late co-founder. Our first employee Andrew Wyatt, who is a fucking rockstar, also reached out via AngelList.

The AngelList by Fred Wilson

I am on AngelList. I see all the deals come together. I don’t personally invest in angel deals in the web/tech space because of potential conflict with USV down the road. But even so, I find it immensely useful to see what companies are getting traction in the angel market. It’s part of my radar/early warning system.

Why I Deleted My AngelList Account by Bryce Roberts

I tend towards a more concentrated approach to seed investing where we make fewer, larger, investments and take an active role in working with the companies we fund. Frankly, I just don’t buy the notion that making an investment is akin to throwing a dart in the dark. Worse, I think its a dangerous idea to promote. The best angel and venture investors are consistently good. Think Mike Moritz, John Doerr, Jim Breyer, Fred Wilson, Peter Fenton, Danny Rimer, Reid Hoffman and the like are just exceptionally good at throwing darts in the dark? I don’t.

What’s The Real Deal With AngelList? by Mark Suster

I cannot stress enough, though, that I believe getting access to the right investors in critical and spending time getting to know who these investors are is equally critical. Far from being a waste of time, the fund-raising process introduces you to a lot of experienced entrepreneurs and VCs who will offer opinions on your business and approach. It should be a continual process. Just don’t use AngelList as a short-cut for the hard work. But to be clear, used properly there is NO downside to AngelList for entrepreneurs.

Jump back to the ToC

Question 11: Should I apply to incubators like Y Combinator or 500 Startups?

The most important question to ask before taking seed money by Chris Dixon

The best programs don’t have sponsors who are even capable of further funding the company. Y Combinator simply doesn’t do follow ons, so there is no way they can positively or negatively signal by their follow on actions…The most dangerous programs are the ones run by large VCs. I would love for someone to prove me wrong, but from my (admittedly anecdotal) knowledge, no companies that have been in large VC seed programs where the VC then stopped supporting the company went on to raise more money from other sources.

The Start-up Guru by Max Chafkin

I recall that a number of founders have warned me that Graham has the habit of throwing out business ideas at a rapid clip, without really thinking through what he’s saying. Still, says Kan, “you always come away feeling energized. You could be working on the most boring piece of software, and you talk to Paul and you think, Man, I’m excited to go back to work.”

Everything you need to know to succeed after (YC) Demo Day by Ash Rust

On our demo day we had just eight investors express interest in us using YC’s online voting system. Some of our batch mates had upwards of 50. We were a simple app, in an unsexy space but we still desperately needed investment to keep going. We had no choice but to work the floor for the whole of demo day collecting business cards. We followed up with most investors that day and had our first meeting scheduled for 9 a.m. the next day. The strategy proved effective.

Jump back to the ToC

Question 12: Once I start fundraising, what is the process like?

If you aren’t getting rejected on a daily basis, your goals aren’t ambitious enough by Chris Dixon

To investors, the sexiest word in the English language is “oversubscribed.” Sometimes it makes tactical sense to start out raising a smaller round than you actually want end up with.

How to do seed fundraising right by Kate Endress

If you are raising venture money, your first meeting will likely be with one representative. If that goes well, you can expect to get called back to meet with 2-3 partners. If that goes well, you will be called back in to do a partner-wide meeting, where they will make the final investment decision. It can be a few weeks between meetings, which is why fundraising requires patience.

High Resolution Fundraising by Paul Graham

By far the biggest influence on investors’ opinions of a startup is the opinion of other investors. There are very, very few who simply decide for themselves. Any startup founder can tell you the most common question they hear from investors is not about the founders or the product, but “who else is investing?”

How To Raise A $1M Seed Round by Sunil Rajaram

Looking back at my inbox, it looks like we received a total of around 120 intros to individual angels and institutions – a little over 10 folks invested in our round.

A Guide to Using Authority & Social Proof in Fund Raising by Mark Suster

So what you really need to get an angel round together are your “anchor tenants.” These are the people who make the early commitment to you to fund your round before having any social proof. You should seek to get people who are respected by others in your field and who will therefore make it easier to raise the rest of your angel round.

Party Rounds: How To Get a High Valuation For Your Seed Startup by Elad Gil

In the not-so-distant past, there were a handful of major angels or funds who would lead rounds. An entrepreneur would have to negotiate terms such as valuation with this small set of potential leads…Today, it is increasingly typical that the entrepreneur raises a round without a lead investor. Furthermore, the entrepreneur can get much better terms (e.g. a much higher valuation) in a Party Round…

WTF is Traction? A 6-Step Relationship Guide to VC by Mark Suster

If you wait until you’re “ready” to fund you’re too late. Funding is about developing a relationship over time. Most of us wouldn’t get married on the first weekend we met someone in Vegas. And most VC’s wouldn’t fund the first time we meet you. Given that many VC’s base their decision on the team, the longer they have to get to know you the better. […] The people who get funded are the people who actually get things done. They tell you that they’re working on biz dev deals with distribution partners and they get the deals signed. They tell you they’re going to ship product and they do. They get their widgets embedded or their products piloted…

Fundraising Will Take You ~3 Months by Elad Gil

4. Putting together the syndicate.
Once you have a set of interested investors, you need to:
a. Gauge valuation. What valuation will get the best people on board without you giving away too much of the company?
b. Determine allocations. How much should each person invest in the round? E.g. do you want any one investor to control the voting privileges of an equity round?
c. Close the first dollars in. The first few committed investors are always the hardest. Once the round starts to come together, everyone will fall in quickly.

Jump back to the ToC

Question 13: What are best practices for scheduling meetings, running meetings, and following-up with investors?

How To Raise A $1M Seed Round by Sunil Rajaram

It goes without saying that the best VCs will not take your meetings unless you get a referral from a strong source. We learned early on that entrepreneurs who have successfully raised or exited companies are the best way to get in the door. We were fortunate enough to put together a really strong advisory board before we went out for our raise, and it helped quite a bit.

How to Present to Investors by Aaref Hilaly (Sequoia partner)

We think of it as being similar to a James Bond movie. Everyone who watches Bond loves the opening sequence, before the titles come on. There’s suspense, action, and unbelievable stunts – in essence, those first 5 minutes bring home why you love Bond, and that keeps you going through the next 2 hours of nonsensical plot twists.

How to Present at Big Meetings without Going Down a Rat Hole by Mark Suster

Make sure you discuss this expectation with your sponsor before the meeting. Understand how knowledgeable the room will be around your industry and your product and importantly – agree a plan with your sponsor on how to play the meeting. Getting his / her buy-in to your approach is important as they can help you steward the meeting in the right direction.

Pitch yourself, not your idea by Chris Dixon

What you should really be focused on when pitching your early stage startup is pitching yourself and your team. When you do this, remember that a startup is primarily about building something. Hence the most important aspect of your backgrounds is not the names of the schools you attended or companies you worked at – it’s what you’ve built. This could mean coding a video game, creating a non-profit organization, designing a website, writing a book, bootstrapping a company – whatever.

VC’s care about the upside case, not the mean by Chris Dixon

Investor sentiment, the old saying goes, is a horse race between fear and greed. The fear and greed in venture capital is all about investing in or missing out on the next Google. No VC stays up at night worrying about missing the next startup that’s flipped to Google. The way you get VCs interested is to convince them there’s a small but non-negligible chance you’ll create a billion dollar (valuation) business.

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Question 14: What questions will investors ask?

Questions VCs Will Ask You by Elad Gil

Who is your team?Why is your team uniquely qualified to solve this problem? What unique insight do you have?
What is your business model? How will you make money? How big of a market is your specific market really (i.e. the market or customers from which you will extract direct value, not “Local is huge, and we are in local, so of course we will be huge”)?
Who is the competition? Why will you beat them?
Why do users care?
How has distribution worked so far? What has worked/not worked?
What milestone will the capital get you to?
Why can this be a billion dollar business?

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Question 15: How do I read a termsheet?

Converts versus equity deals by Chris Dixon

There are two kind of rights that investors get when they put money in company. The first are economic rights: basically that they make money when the investment is successful. The second are control rights: board seats, the ability to block financings and acquisitions, the ability to change management, etc. Converts give investors economics rights with basically zero control rights (legally it is just a loan with some special conversion provisions).

Everything You Ever Wanted To Know About Convertible Note Seed Financings (But Were Afraid To Ask) – Part 1 by Scott Edward Walker

What are Some of the Other Advantages of Issuing Convertible Notes?
Speed, simplicity and cost. Indeed, a startup could close a convertible note round in a day or two by merely issuing a 2-3 page promissory note, which could cost as little as $1,500-$2,000 in legal fees (or a little more if a note purchase agreement is also executed, which is customary)

Is There a YCombinator Valuation Bubble or Not? by Jason Calacanis

(b) Valuation caps: A convertible note “”converts”” in two different ways (typically). First, the loan can come due and the investors can get their money money back, typically with interest, or convert to an agreed upon valuation (guess who has the power in that situation!). That doesn’t happen often; the company will typically shut down by that point. Second, another investor (typically a VC) can price the next round at a specific value. The investors who made the loan in the convertible note are forced to accept that new valuation up to, you guessed it, the valuation cap. There is typically a 20% discount given to note-holders for taking the risk. For example, a capped note at $10M would yield a $10M valuation for the angels if the valuation of the next round was > $12.5M. Search blogs like www.venturehacks.com, www.avc.com or www.bothsidesofthetable.com for more details on these issues. ]

Founder vesting by Chris Dixon

1) All startup employees – including founders! – should vest over 4 years from their start date (with a one year “cliff”).
2) Founders should always have acceleration on change of control! In particular, you should have full acceleration on “double trigger” (company is acquired and you are fired). In addition you should have partial acceleration on “single trigger” (company is acquired and you remain at company).

Convertible Debt in Plain English by Barrett Sheridan

Another common element of a convertible note is a discount. This is kind of like a floating-rate cap. It basically means that, whatever the value of your company when you take your first equity investment, I get to invest as if it’s happening at a lower valuation. So if a $100,000 note has a 25% discount, and you raise money at a $1 million valuation, your note holder gets $100,000 / ($1 million * 0.75 = $750,000) = 13.3% of your company (rather than 10%).

First Round Funding Terms and Founder Vesting by Mark Suster

If you have founder vesting and protection on change of control + protection against losing your shares of you’re fired then we’re completely aligned. I’m protected against your walking (as are your co-founders protecting each other). You’re protected against my asking you to go or a company buying you and taking away your value.

Seed Stage Valuation Guide by Jordan Cooper

Things change quickly, and it’s been 2+ years since Jordan’s post, but his thought process is a good starting point.

Startups: Give Your Family Stock In Your Company by Elad Gil

When you set up your company, the stock is really cheap (e.g. 0.0001 cents per share or the like). This is your opportunity to give your family, spouse, or other loved ones the equivalent of a tax free gift that could have a major financial impact long term (i.e. the taxes they will need to pay on the gift at this point could be either zero or very low in dollar terms).

Jump back to the ToC

Question 16: How do I follow-up with investors?

Signs A VC Is Just Not That Into You by Elad Gil

Does not suggest next steps at the end of your meeting.
Makes endless data requests, without any in-person follow up set up.
Only has you deal with a junior associate.
Is not responsive to your emails
Does not try to sell you on her firm.

I emailed a VC and never heard back by Mark Suster

If you’re pitching me specifically and I haven’t emailed you back send me a polite reminder a week or two later. If you’re on a tight timeline try also sending me an @msuster message on Twitter, trying leaving a polite voice message with my assistant and/or trying sending me a message on Facebook. As long as your polite about it, say words like, “I’m really sorry to hassle you with multiple emails / voicemails but I’m going to be in town for just 2 days and would love to know whether you’re interested to meet,” then I can’t see how any VC would be put off. And if they are you’re pitching the wrong VC.

Saying No In Less Than 60 Seconds by Brad Feld

I can figure this out from the first interaction at least 50% of the time and my first email response is (hopefully a polite) version of “no” that usually consumes a total of less than 30 seconds from beginning to end. Another 25% of the time I need a little more information and request it via mail. This has the side effect of eliminating another chunk of interactions since the person on the receiving end never bothers to respond. For those that do respond, I can usually figure out from the response whether or not I want to spend more time or not; if not, I’m still probably under 60 seconds for saying “no”.

Jump back to the ToC

Question 17: How do multiple rounds work?

How Do I Do Multiple Closings for an Angel Round? by Brad Feld

A: For a convertible debt round, you can keep it as simple as issuing a promissory note for each investor…You can do as many closings as you want by simply issuing a separate promissory note for each investor. The best way to do multiple closings on an angel equity round is to raise the early money using the convertible debt approach above with an automatic conversion into a pre-negotiated equity financing once a certain amount of money is raised.

Jump back to the ToC

Question 18: How do I negotiate terms?

6 Tips To Get Your Startup Off The Ground And Score A Seed Round by Anthemos Georgiades

First, don’t be afraid to ask investors to match the best offer you have. We improved our valuation cap by 50 percent in 48 hours by rallying our investors behind the most favorable term sheet on the table. It’s tough to go up against big VCs, but if they like you, they like you. The negotiation on valuation means less to VCs in the early stages than it will to you and your team. Play up to that imbalance. It favors you, not them.

First Round Funding Terms and Founder Vesting by Mark Suster

If you have founder vesting and protection on change of control + protection against losing your shares of you’re fired then we’re completely aligned. I’m protected against your walking (as are your co-founders protecting each other). You’re protected against my asking you to go or a company buying you and taking away your value.

How to Negotiate Valuation With a VC by David Pakman

1) The first is to understand the VC firm’s philosophy on price and term sheets. Some VCs are flexible on price but will introduce other terms to essentially manipulate the effective price (such as participating preferred, the size of the option pool, anti-dilution provisions, etc.) Other VCs, such as Venrock, prefer to deliver vanilla term sheets but have a clear agreement on price.

The Equity Equation by Paul Graham

One of the things the equity equation shows us is that, financially at least, taking money from a top VC firm can be a really good deal. Greg Mcadoo from Sequoia recently said at a YC dinner that when Sequoia invests alone they like to take about 30% of a company. 1/.7 = 1.43, meaning that deal is worth taking if they can improve your outcome by more than 43%. For the average startup, that would be an extraordinary bargain. It would improve the average startup’s prospects by more than 43% just to be able to say they were funded by Sequoia, even if they never actually got the money.

Jump back to the ToC

Question 19: Should I do reference checks?

YES.

How Do You Reference Check a VC? by Mark Suster

Make sure to call the companies in that VCs portfolio that didn’t succeed. Feel free to ask the VC after they give you the official list for a list of 3 CEO’s where the company stumbled. Do a web search to find companies that they didn’t give you. Ask the CEO’s about the VC when the chips were down. Do research and find some CEO’s who were fired by the VC. That would be instructive. I’ve met some that actually say positive things about the VCs. I’ve heard others that say the opposite.

Jump back to the ToC

Question 20: They said yes! How do I get money in the bank?

6 Tips To Get Your Startup Off The Ground And Score A Seed Round by Anthemos Georgiades

“yes” does not mean “yes.” Put the Champagne back on ice. It took us four times as long to close our seed round as it did to get verbal commitments. The whole process took five months. That’s quite skewed as we had a series of VCs in our round – a different proposition to having a couple of angels – but in general it’s a fair warning. The legal back and forth takes time. Investors can be less responsive about the ‘boring’ stuff. Move quickly and get it done.

You Should Read Every Word of Every Legal Doc (Especially Funding Docs) by Elad Gil

One of the most important set of contracts you will ever sign in the life of your startup are your financing documents. I am surprised by the number of entrepreneurs who depend on their lawyers to read through and decide on key business points of their funding rounds. I will often ask an entrepreneur who is running into an issue about a key issue impacted by their prior funding rounds or employment agreements and their answer will be “I don’t know”.

Jump back to the ToC

Question 21: Should I create a Board of Directors? A Board of Advisors?

How To Choose A Board Member by Elad Gil

The members of your board are the most important people you will ever “”hire”” for the company. For an early stage company, your board will often:
1. Select the CEO of the company. This means the board may be able to fire you from the company you started. Part of the board’s job is to hold the CEO accountable for deadlines, plans, and deliverables.
2. Block or push for major events in the company’s life (future fundraises, acquisitions, selling the company etc.)
3. Provide great strategic advice or become pain in the butt, medling overhead.
4. Help with recruiting senior executives or key hires.
5. Teach you about nuts and bolts of the business, or processes as you scale.

Ideal first round funding terms by Chris Dixon

A board consisting of 1 investor, 1 management and 1 mutually agreed upon independent director. (Or 2 VCs, 2 mgmt and 1 indy). As an entrepreneur, the way I think of this is if both my investors and an independent director who I approved want to fire me, I must be doing a pretty crappy job and deserve it.

Jump back to the ToC

Question 22: How do I work well with my investors?

Angel Investing – The Most Underrated Skill: Access to Buyers by Mark Suster

Send monthly updates to your investors. Hang out at their events and get to know them. And don’t be scared to ask for help. I’m sure Zumper’s investors would agree that I’ve been pretty aggressive about asking them for support. Investors will respect you more as a founder if you admit there are various problems you need their help to solve.

Put Your Investors To Work For You by Elad Gil

Ask your angels what they are good at, and what they can help with. When the time comes to close your first employee, negotiate that business deal, or figure out the best channels by which to buy traffic, contact the right angel or investor and ask them for help.

Jump back to the ToC

Question 23: Should I announce that I raised a round? How do I get PR from Techcrunch, Pandodaily, and other news outlets?

How To Get PR For Your Startup: Fire Your PR Company by Jason Calacanis

When I started Silicon Alley Reporter in New York City, I had stacks of the magazine with me at ALL TIMES. If you saw me at a party I had 25 copies in my backpack, or 200 on a broken-down luggage cart, and you had one shoved in your face within a minute of meeting me. […] Additionally, if you met me in the last 90s, chances are I was wearing a tight black Silicon Alley Reporter shirt. Stacks of them littered my loft on 26th street, and I would toss them only if they started to fade on the edges.

HOW I PITCHED @TECHCRUNCH AND 13 WAYS TO GET PRESS WHEN YOU LAUNCH YOUR STARTUP by Jason Baptiste

So when we pitched TechCrunch, we didn’t pitch it as a WordPress plugin company. That’s just not big news and though it’s a very cool, it doesn’t provide excitement. We gave a taste of the future of being available to All CMS’s, a hosted platform, and helping pave the way for the future of media via tablet publishing.

Jump back to the ToC

Question 24: When should I raise another round?

The Expanding Birthrate Of Web Startups by Fred Wilson

So, if you are an entrepreneur you should be very focused on either getting to profitability or getting a VC firm or two with deep pockets into your company (or both).

Raising Angel Money by Mark Suster

Your chances of raising money from a VC are significantly greater if you have raised money from prominent people. In most cases we probably don’t care whether the deal was priced or convertible debt. We would, however, look to make sure that you didn’t take too much dilution, which would be a negative. If you have many angels (say a group of 10-15 people) and if these people are not sophisticated serial angel investors it could cause problems.

Jump back to the ToC

A summary of Paul Graham’s 18 mistakes that kill startups

Those of you that subscribe to my startup newsletter are familiar with my habit of summarizing the best long-form startup articles.

PG has arguably the most comprehensive, well-written set of essays for inexperienced entrepreneurs. Many of his lessons will naturally be acquired when you start companies, because in starting companies you will make mistakes and from mistakes you will learn these lessons, but if you want to avoid at least some of those mistakes, or make different ones instead, you should be reading his essays.

This essay, The 18 Mistakes That Kill Startups, is one of the best and it’s included in the startup newsletter. (subscribe here)

Like most of my blog posts, I write it in part to share advice with readers and in part to remind myself of what’s important.

This sums up the essay:

In a sense there’s just one mistake that kills startups: not making something users want. If you make something users want, you’ll probably be fine, whatever else you do or don’t do. […] So really this is a list of 18 things that cause startups not to make something users want. Nearly all failure funnels through that.

Here are the 18 mistakes:

1. Single Founder – all of the great technology companies had 2 founders (Apple, Microsoft, Google). Although I would argue Mark Zuckerberg and Jeff Bezos have come closest to breaking this rule

2. Bad Location – if you’re serious, be in the Valley (this includes SF)

3. Marginal Niche – avoid small markets, and focus on big problems in big markets

4. Derivative Idea – don’t take an existing success and tweak it in a small way. I think a lot of the “Airbnb for X” or “Heroku for Y” have this problem, too

5. Obstinacy – your original business plan is probably wrong, but it’s important not to change too quickly, either

6. Hiring Bad Programmers – self-explanatory; implied: starting a company as a business founder, without a strong technical cofounder

7. Choosing the Wrong Platform – platforms include Windows, Apple’s App Store, and Facebook; choose carefully since they’re your partner, whether you like it or not

8. Slowness in Launching – get your product into users’ hands as soon as you have a “quantum of utility”, then iterate quickly

9. Launching Too Early – less important than #8, but if you launch too early, you risk hurting your reputation

10. Having No Specific User in Mind – can you envision EXACTLY what your ideal user looks like, how she behaves, and what she wears?

11. Raising Too Little Money – raise enough to get to the next step, and then 50-100% more for buffer

12. Spending Too Much – happens when you hire too many people, and/or pay too much salary (give equity instead)

13. Raising Too Much Money – when this happens, you’re expected to spend it quickly, and your company becomes less nimble

14. Poor Investor Management – ignore them, and they’ll be upset; heavily involve them, and they may wind up calling the shots

15. Sacrificing Users to (Supposed) Profit – we were guilty of this: too much emphasis on finding a business model and earning revenue, before we had a product that users wanted

16. Not Wanting to Get Your Hands Dirty – the best founders do whatever’s necessary to grow the company, in particular understanding their users and acquiring more of them

17. Fights Between Founders – most unresolvable disputes are due to differences between people, not due to the particulars of a situation, so choose your cofounder(s) carefully

18. A Half-Hearted Effort – quit your day job, and be obsessed with your startup

1-Page Cheatsheet: Language Intelligence by Joseph Romm

Language Intelligence by Joseph RommYou’ll get a lot from reading this one: 1-page cheatsheet to Language Intelligence by Joseph Romm [Amazon Kindle].

Why Language Intelligence

It’s well-written, reads fast, and includes famous things like the Bible, Lincoln, Shakespeare, Lady Gaga.

Unless making a conscious effort, we tend to take language for granted. I use “language” here to mean the use of words in communication.

We write, we read, we speak, we listen, and like driving a car, 80% is done in a sort of cruise control. Yet those who are GOOD at controlling words wield enormous power. Romm explains WHO those people are, HOW they do it, and WHY it works.

Read his summary if you read nothing else:

1. Use short, simple words.
2. Repeat, repeat, repeat. Repetition is the essential element of all persuasion.
3. Master irony and foreshadowing. They are central elements of popular culture, modern politics, and mass media for a reason—they help us make sense of the stories of our lives and other people’s lives.
4. Use metaphors to paint a picture, to connect what your listeners already know to what you want them to know. Metaphors may be the most important figure as well as the most underused and misused.
5. Create an extended metaphor when you have a big task at hand, like framing a picture-perfect speech or launching a major campaign.
6. If you want to avoid being seduced, learn the figures of seduction. If you want to debunk a myth, do not repeat that myth.

From Romm’s Wikipedia:

Romm is an American author, blogger, physicist and climate expert who concentrates on methods of reducing greenhouse gas emissions and global warming…Romm was elected a Fellow of the American Association for the Advancement of Science. In March 2009, Rolling Stone magazine named Romm to its list of “100 People Who Are Changing America”. In September 2009, Time magazine named him one of its “Heroes of the Environment (2009)”, calling him “The Web’s most influential climate-change blogger”.

Lessons and Highlights

Insight #1: rhetoric is used by the greatest thinkers and in the greatest works of all-time

Similarly, every great songwriter—our modern bards—inevitably masters rhetoric since rhetoric itself came from the oral tradition of the great bards like Homer.

In ancient Athens, all citizens needed to excel at public speaking because every citizen was required by Greek law to speak in his own behalf in court.

The King James Bible (KJV) is a masterpiece of rhetoric:

That the King James Bible did become a textbook of rhetoric will soon be evident: Many of the most famous examples of every figure of speech can be found in its pages. That the Bible would be a textbook of rhetoric was ordained, since the translators were every one a university-trained language scholar with a far more extensive formal education in rhetoric than Shakespeare, who, after grammar school, was purely self-taught.

Among our presidents, Lincoln was the most active student of rhetoric:

Lincoln worked hard to teach himself elocution and grammar. He studied the great speechmakers of his time, like Daniel Webster, as well the great Elizabethan speechmaker, the Bard of Avon. Lincoln continued his passion for poetry and Shakespeare throughout his entire life. He spent hours reading passages from Shakespeare to his personal secretary, John Hay, and the artist F. B. Carpenter.

Insight #2: shorter words are better

“The shorter words of a language are usually the more ancient,” as Churchill explained.

At the end of the debate, Reagan introduced a key question, a rhetorical question, that has since been repeated by countless candidates. He asked the audience to imagine itself at the polls and about to make the key decision. His words are worth repeating at length to hear just how much you can say with short words repeated often: “I think when you make that decision, it might be well if you would ask yourself, are you better off than you were four years ago”

Insight #3: repeat your words repeatedly; rhyme is sublime

The most watched YouTube video of all time is “Baby,” in which teen sensation Justin Bieber repeats the alliterative title an astounding fifty-four times.

Michael Deaver, the Karl Rove of the Reagan presidency, said in 2003 of the Bush White House: “This business of saying the same thing over and over and over again—which to a lot of Washington insiders and pundits is boring—works. That was sort of what we figured out in the Reagan White House. And I think these people do it very, very well.”

All these years after the 1995 O. J. Simpson murder case, defense attorney Johnnie Cochran’s phrase “If it doesn’t fit, you must acquit” still sticks in the mind.

It works brilliantly to rally a nation at war in Churchill’s famous 1940 speech: “We shall fight in France, we shall fight on the seas and oceans, we shall fight … in the air…. We shall fight on the beaches, we shall fight on the landing grounds, we shall fight in the fields and in the streets, we shall fight in the hills….” We can hear these powerful words echo in our heads because Churchill understood that “every speech is a rhymeless, meterless verse.”

Perhaps the most elegant—and certainly one of the most popular—figures of repetition is chiasmus: words repeated in inverse order. Chiasmus is a great source of aphorisms. Mae West famously said, “It’s not the men in my life, it’s the life in my men.” Ray Bradbury advised writers, “You have to know how to accept rejection and reject acceptance.”

Insight #4: great speakers and writers use irony, from Shakespeare to Seinfeld

4 types of irony: Socratic irony, Verbal irony, Dramatic irony, Irony of Fate (poetic justice)

Socratic irony is the strategy of the master orator who denies eloquence, claiming to be an ordinary Joe, a plain-spoken man of the people.

Cleverly, Antony himself uses the word “honorable” ten times in this one speech. He repeatedly says Brutus is an honourable man and that all of the conspirators are honourable. His irony is increasingly blatant: “When that the poor have cried, Caesar hath wept; Ambition should be made of sterner stuff: Yet Brutus says he was ambitious; And Brutus is an honourable man.” With this drumbeat, Antony convinces the crowd that there was no justification for killing Caesar, which in turns means the murder was a dishonorable act.

Dramatic irony applies mainly to audiences—such as theatergoers or TV watchers—who know (or are told) the significance of words and actions when the characters do not. […] For instance, Shakespeare’s Iago tells the audience plainly in several early soliloquies that he is a dangerous liar plotting to destroy Othello and the other major characters. So we hear dramatic irony each time one of those characters calls him honest Iago or trusts him. We, the audience, know what’s going on, but Othello and the others don’t.

Poetic justice of all kinds is extremely common in popular culture. At the most basic level, in the vast majority of TV shows, movies, plays, and books, good triumphs over evil. Good is rewarded, evil is destroyed, criminals are captured, boy gets girl.

Insight #5: foreshadowing works well because…well, keep reading to find out ;)

The golden rule of speechmaking is “Tell ’em what what you’re going to tell ’em; tell’em; then tell ’em what you told ’em.”

Foreshadowing and ominatio are the foundation upon which the Bible’s scaffolding of rhetoric was built […] Jesus himself makes many prophecies.

Ultimately, the reason foreshadowing works, and the reason we can expect more of it in popular culture and political coverage is that we like to believe that people’s individual lives have a circularity, a consistency—a pattern.

Insight #6: use metaphor to enter the language Olympics

“To be a master of metaphor,” Aristotle writes in Poetics, is “a sign of genius, since a good metaphor implies intuitive perception of the similarity in dissimilars.”

Metaphors are one of the best ways to verbally connect to visual people, and those with high language intelligence are good at painting pictures with words—the green-eyed monster that is jealousy. […] Metaphors aid in memory a second way: They require the hearer or reader to think more, to light up more brain circuits, to figure out the connections and what they mean.

Elton John says in his tribute to Princess Diana (a revision of his tribute to Marilyn Monroe) that she lived her life “like a candle in the wind.” Lady Gaga’s uber-hit “Poker Face” is an extended metaphor of love as a poker game.

Insight #7: use extended metaphor to win a Gold Medal

Extended metaphor is, for me, the most important rhetorical device. This figure is at the heart of some of Lincoln’s greatest speeches. It pumps the life blood into Shakespeare’s greatest plays.

The Gettysburg Address may be the greatest extended metaphor in the English language, with Lincoln turning the bloody battle into a symbolic national crucifixion, although that facet of the speech is rarely taught.

In 2011, Lady Gaga explained her song-writing philosophy: “I just like really aggressive metaphors—harder, thicker, darker and my fans do as well.”

The power of frames and extended metaphors—the reason why smart orators use them—is that they cannot be overturned merely by presenting contrary facts. Let me repeat that: Facts cannot fight false frames. You must fight metaphorical fire with metaphorical fire. “One of the fundamental findings of cognitive science is that people think in terms of frames and metaphors,” writes linguist Lakoff.

Insight #8: rhetoric – like all tools – can be used for “good” and “bad”

The dark side of rhetoric was well-known—and well-feared—in ancient Greece. The term “Sophists” originally applied to those who taught rhetoric (and other subjects) for pay. The Sophist Protagorus boasted he could make the weaker cause appear to be the stronger. Hence sophistry, the term for disingenuous arguments.

Seduction, like persuasion, is a two-step dance for a master of rhetoric. First, a seducer must convince you that he or she is a trustworthy person, a person who shares your values and speaks your language. […] Once a would-be seducer has established he is trustworthy, that he is a plainspoken, straight-shooting person who means what he says and says what he means, then he can safely start saying what he doesn’t mean.

Rumsfeld is particularly good at asking questions that he then answers: “Is it [post-war Iraq] going to be as efficient as a dictatorship? No. Is it going to be vastly more desirable? You bet.”

The authors found that rather than deny a false claim, it is better to make a completely new assertion that makes no reference to the original myth. It takes a lot of message discipline to do this, but if you want to debunk a myth, you need to focus on stating the truth, not repeating the myth. Richard Nixon said, “I am not a crook,” and only his final word still rings in our ears.

General tips

I’ve come to realize that the single most important part of any blog post is the headline.

The second most retweeted tweet of 2010 was from the rapper Drake: “We always ignore the ones who adore us, and adore the ones who ignore us.”

We should all minimize the use of negative suggestions in everyday life. […] when you make an important phone call to someone who is busy, don’t ask, “Are you busy?” or, “Is this a bad time to talk?” as the words “busy” and “bad time” will ring in their ears. Ask, “Is this a good time to talk?”

That’s it, folks

Here’s a list of all 1-page cheatsheets, and a list of all books!

August Quotes: “It’s worth noting that you can devote your life to community service and be a total schmuck. You can spend your life on Wall Street and be a hero” – David Brooks

Homer Simpson the vegetarianSee all previous ones here. Tucker Max writes a monthly quotes post which is great.

Love the way this sounds:

Poems are made by fools like me, but only God can make a tree. – Joyce Kilmer

From a favorite Brooks article:

I saw young people with deep moral yearnings. But they tended to convert moral questions into resource allocation questions; questions about how to be into questions about what to do…It’s worth noting that you can devote your life to community service and be a total schmuck. You can spend your life on Wall Street and be a hero. – David Brooks

Even other cultures, millenia ago, were thinking about habits:

Watch your thoughts; they become words. Watch your words; they become actions. Watch your actions; they become habit. Watch your habits; they become character. Watch your character; it becomes your destiny. – Lao Tzu

Reminds me of the rage to master:

The dirty little secret of every creative workshop or motivational seminar is simply this: The person who is going to change is going to change anyway. She has no choice. She is impelled by inner necessity. – Steven Pressfield

I don’t like when people say that something is “strictly business” or that they’re “being logical”. Your emotions are to thinking like bread is to a sandwich, without which it cannot exist.

Reason is and ought to be only a slave to the passions, and can never pretend to be any other office than to serve and obey them. – David Hume

Certainly feels true, no?

Every great cause begins as a movement, becomes a business, and eventually degenerates into a racket – Eric Hoffer

Meditation is helping me with this:

Infinite patience gets you immediate results – James Altucher

I suck at this:

Love your enemies, for they tell you your faults – Ben Franklin

I agree with the below. Sometimes overly so?

The only path to amazing runs directly through not-so-amazing – Seth Godin

Like the old saw, “a fox knows many things but the hedgehog knows one big thing”…

Fanaticism is the only way to put an end to the doubts that constantly trouble the human soul – Paulo Coehlo

Haha:

If most of your courtship attempts have succeeded, you must be a very attractive and charming person who has been aiming too low – Geoffrey Miller

Why I stay away from email and social media in the evening:

Arguing with people is like reading your email at 4am in the morning. There is absolutely no good that can come of it. It’s just scratching an itch – James Altucher

This Hemingway guy, really something:

This too to remember. If a man writes clearly enough any one can see if he fakes. If he mystifies to avoid a straight statement, which is very different from breaking so-called rules of syntax or grammar to make an effect which can be obtained in no other way, the writer takes a longer time to be known as a fake and other writers who are afflicted by the same necessity will praise him in their own defense. True mysticism should not be confused with incompetence in writing which seeks to mystify where there is no mystery but is really only the necessity to fake to cover lack of knowledge or the inability to state clearly. Mysticism implies a mystery and there are many mysteries; but incompetence is not one of them; nor is overwritten journalism made literature by the injection of a false epic quality. Remember this too: all bad writers are in love with the epic.
-Ernest Hemingway

Will automation render human workers obsolete? Daniel Akst explains

Dilbert on automationY’all know I’m a big fan of reading stuff and then summarizing it. I’ve been doing CliffsNotes for books with my 1-page cheatsheets, and for startup articles with 1-read-a-day.

Wilson Quarterly is a new find. Their articles are long (3,000+ words), well-researched, and written in a “scholarly journalist” voice like The Economist.

Daniel Akst writes the weekly R&D column for WSJ. His essay, Automation Anxiety, is perfectly timed with some questions on my mind, such as:

  • As U.S. jobs are increasingly concentrated in technology and knowledge, what happens to workers who are left behind?
  • How will the U.S. maintain its global leadership, as we increasingly see signs of strain in its economy, its cultural influence, and its moral authority?
  • What will the “job of the future” look like?
  • How many of today’s jobs will be automated, and in what way?

My bias is to write down insights that are new to me, as opposed to what I think will be most interesting to the widest swath of readers. Treat it like a Costco free sample: if you enjoy it, go and read the whole thing.

CliffsNotes for Automation Anxiety by Daniel Akst

His main question:

But now, with the advent of machines that are infinitely more intelligent and powerful than most people could have imagined a century ago, has the day finally come when technology will leave millions of us permanently displaced?

A big part of his thesis:

Notice Bloom’s insights: first, that technology could obviate arduous manual labor; second, that this would cost somebody a job; and third, that it would also create a job, but for a different person altogether.

Some stats

  • US shed 6.3mm manufacturing jobs between 1990 and 2010
  • Unemployment is at 7.5%, 4 years after our “Great Recession”

Akst goes on to compare our situation today to similar automation and job market fears in the 1950s and 1960s (the Kennedy, LBJ eras). Unemployment was high (hitting 7% at one point)

The prominent economist Robert Heilbroner argued that rapid technological change had supercharged productivity in agriculture and manufacturing, and now threatened “a whole new group of skills—the sorting, filing, checking, calculating, remembering, comparing, okaying skills—that are the special preserve of the office worker.”

And here we get to the second piece of Akst’s argument:

some of its most important effects were felt not in the economic realm but in the arena of social change

In the 1950s and 60s, we mistakenly assumed that there was a ceiling to demand for goods and services (hah!):

Although the principle that human wants are insatiable is enshrined in every introductory economics course, it was somehow forgotten by intellectuals who themselves probably weren’t very materialistic, and who might only have been dimly aware of the great slouching beasts of retailing—the new shopping malls—going up on the edge of town

Interestingly, there was also concern that – with consistently shorter working days – we’d hit a point where we hardly worked at all. What would we do with the leisure time??

In the first half of the 20th century, the number of hours worked per week had shrunk by a quarter for the average worker, and in 1967 the futurist Herman Kahn declared that this trend would continue, predicting a four-day work week—and 13 weeks of vacation.

Some writers got it right:

Simon wrote, “The world’s problems in this generation and the next are problems of scarcity, not of intolerable abundance. The bogeyman of automation consumes worrying capacity that should be saved for real problems—like population, poverty, the Bomb, and our own neuroses.”

The people most affected were middle-aged, working class men (as they are today):

The economists Michael Greenstone and Adam Looney found that from 1969 to 2009, the median earnings of men ages 25 to 64 dropped by 28 percent after inflation. For those without a high school diploma, the drop was 66 percent. This is to say nothing of lost pensions and health insurance.

Why such declines? #1, entrance of women and immigrants into the workforce, #2, increased global trade, #3, rising use of technology

In fact, the proportion of men who were not in the formal labor force tripled from 1960 to 2009, to a remarkable 18 percent

Sociologist Daniel Bell was particularly prescient:

Bell acknowledged that there would be disruptions. And he was accurate about their nature, writing that “many workers, particularly older ones, may find it difficult ever again to find suitable jobs. It is also likely that small geographical pockets of the United States may find themselves becoming ‘depressed areas’ as old industries fade or are moved away.”

Bell also foretold the social impact of such changes:

“creating a new salariat instead of a proletariat, as automated processes reduce[d] the number of industrial workers required.” He accurately foresaw a world in which “muscular fatigue [would be] replaced by mental tension”

Like some thinkers in the 50s and 60s, Akst believes that the big problem is (re)distribution:

“The economy of abundance can sustain all citizens in comfort and economic security whether or not they engage in what is commonly reckoned as work,” the committee continued, arguing for “an unqualified commitment to provide every individual and every family with an adequate income as a matter of right.”

Why? Because automation presents us with a windfall, and the hard question is how it’s shared:

This doesn’t mean we must embrace the utopianism of the Triple Revolution manifesto or return to the despised system of open-ended welfare abolished during the Clinton years. But inevitably, if only to maintain social peace, it will mean a movement toward some of the universal programs—medical coverage, long-term care insurance, low-cost access to higher education—that have helped other advanced countries shelter their work forces from economic shocks better than the United States has, and control costs while they’re at it.

And a couple insightful comments:

It seems to me that unless we can invent a new kind of labour – post-physical, post-mental – we will have to come up with a new kind of wealth creation mechanism that allows for 1) the use of fewer workers and 2) a fair distribution of the wealth created. – idespair

Akst devotes an anemic, apologetic two paragraphs to the central fact of his essay – the adaptation required this time is fundamentally political rather than technological. And to most eyes that political solution can hardly be described as anything but radical. – civisisus

Thanks for reading, folks. Here’s the full article.