Here are ten of my favourite insights from the book:
- What angel investing and the lottery have in common.
I buy lottery tickets for a living, but unlike the normal schmucks on the street, I get to buy tickets that are in the top 1 percent of the winning pool.
2. The people that dare to take more risks intelligently are typically luckier in life.
If you learn anything from this book, it’s that you must take risks as an angel investor and in life if you want at least the chance of an outsized outcome.
You can make your own luck in this life by putting yourself next to the people who are already winning.
3. The business of angels
If these businesses didn’t look completely crazy, then everyone would want to invest in them and there would be no need for angels. In fact, the term “angel” is used because we are the investors who come to a founder’s rescue in their hour of need— when nobody else believes in them.
The best angels in the world have four qualities, giving them the ability to (1) write a check (money), (2) jam out with the founders over important issues (time), (3) provide meaningful customer and investor introductions (network), and (4) give actionable advice that saves the founders time and money— or keeps them from making mistakes (expertise).
Your job as an angel investor is to block out the haters, doubters, and small thinkers, because if you think small you’ll be small. I’d rather see my founders fail at a big goal than succeed at a small one.
Remember there are a hundred reasons why these things fail, so you’re not going to have a hard time saying no, and there are typically only one or two reasons to say yes.
Founders always share investor meeting details with each other and your reputation is everything in our industry. If you are helpful, present, and considerate, then you’re going to get a great reputation. If you are unprofessional, cavalier, or conceited, or use your position of power in any way that isn’t in service of the founder, then you’re toast.
4. The best deals are not available to just anyone.
The best deals are typically not on platforms like AngelList or at incubators like Y Combinator or 500 Startups. The best deals never see the light of day. They’re quickly filled by insiders who are sharing deal flow, and by elite founders with killer startups tapping their existing network.
5. On the best investment, you can make.
I passed on investing in Twitter because I was, at the time, a founder of companies. I stupidly thought that the best investment I could make was in my own company.
It was at that point I realized that I didn’t need to know if the idea would be successful. I only needed to know if the person would be. It was clear as day to me that whatever Ev worked on would be successful, but my own ego and my need to be right and understand everything got in the way of me hitting my first big home run.
6. There’s no difference between the founder and their company
As you go through your angel investing life, take some time to evaluate the person and their motivations. Ask yourself a simple question: “Would I buy stock in this person if I could?” If you wouldn’t buy stock in a founder, you shouldn’t buy stock in their company— because there is no difference between the founder and their company; they are one and the same.
7. Why are you doing this?
If folks are building a startup for money, they will eventually quit when they realize there are many better ways to make money faster and with more certainty. If you want to make a lot of money, you’re better off being a world-class programmer on a very esoteric and in-demand vertical and getting Google or Facebook to give you $ 1 million-plus a year in stock and cash for ten years in a row. You have no downside, you can work a couple of hours a day, and you get unlimited free food.
8. Why startups fail
The number one reason a startup shuts down is not actually running out of money, which is what most people believe. The number one reason a startup fails is that the founder gives up.
9. On communication between founders and angels
“If a startup isn’t sending you monthly investor updates, it’s going out of business.”
The more concise and professional the updates, the greater the chances that angels will be able to help you, including investing more money and introducing you to their friends as a responsible founder who’s a delight to work with. Angels want to feel needed, and founders who don’t make their angels feel needed have lost their most likely source of follow-on funding— their current investors.
10. The market is constantly changing
What worked when I started investing, when there were one-tenth as many startups being formed every year, doesn’t work today. It was wise to invest in great teams, pre-product back then, where today you almost universally want to wait for the founders to finish their product and get to market before investing.
Source: Calacanis, Jason (2017-07-18). Angel: How to Invest in Technology Startups—Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000. HarperCollins. Kindle Edition.
Further reading: Fred Wilson on What It Takes To Be A Great Angel Investor
There are two main concepts one needs to understand and maybe learn the hard way, before becoming consistently profitable:
- Different setups work in different markets.
The same setup that can deliver outsized profits on one trading environment might lose you money in a different market. For example, buying strong stocks in hot industries in anticipation of a breakout works great during market uptrends, but it is a system with no edge at best during range-bound markets. Buying breakouts after a few days of a general market rally in a range-bound environment is not a profitable approach. Swing trading is a lot more challenging during corrective markets when correlations between stocks are very highs, volatility is ginormous and the market changes its direction frequently. Intra-day trading is a lot more profitable during fast corrective markets than during low-volatility steady market uptrends, when swing and position trading provide more lucrative alternatives.
Edges come and go because markets are constantly changing – sometimes, in a predictable, cyclical manner; other times, in a completely new and unexpected way. The path to survive and grow is to constantly experiment with new ways to make money and protect capital.
2. The concept of holding power.
Many novice market participants trade with too much size and get easily scared out of sound positions.
Holding power comes from two things:
a) A good entry – this means picking the right setup for the current market. A good entry helps to keep our potential loss small, while it provides the opportunity to make multiples of our initial risk. Risking a dollar to potentially make three dollars per share.
b) The right position size – I risk between 0.5% and 1% of my capital depending on the market.
Leverage and trading too big have ruined not one or two accounts. I became much better and consistently profitable trader once I cut my position size to reflect my current trading capital and the current market environment. Not all markets provide equal opportunities for profit. There are times to be aggressive. There are times to protect capital and confidence.
Some books deserved to be read more than once. Not only to capture and better understand their concepts but mainly to devise a plan how to apply their wisdom in your life. Barking Up The Wrong Tree is Eric Barker’s personal manifesto of how to feel adequate in today’s fast-paced global world. It is not based on the subjective personal experience of one. It is built on top of hundreds of scientific studies.
Here’s are some of the interesting concepts I managed to find in Eric’s first book:
“We spend too much time trying to be “good” when good is often merely average. To be great we must be different. And that doesn’t come from trying to follow society’s vision of what is best because society doesn’t always know what it needs. More often being the best means just being the best version of you. As John Stuart Mill remarked, “That so few now dare to be eccentric, marks the chief danger of our time.” In the right environment, bad can be good and odd can be beautiful.”
Focus on strengths
Many people struggle with this. They aren’t sure what their strengths are. Drucker offers a helpful definition: “What are you good at that consistently produces desired results?” To find out what those things are, he recommends a system he calls “feedback analysis.” Quite simply, when you undertake a project, write down what you expect to happen, then later note the result. Over time you’ll see what you do well and what you don’t. By figuring out whether you fall into the filtered or unfiltered camp and by knowing where your strengths are, you’re miles ahead of the average person in terms of achieving both success and happiness.
Pick the right pond
Once you know what type of person you are and your signature strengths, how do you thrive? This leads to Mukunda’s second piece of advice: pick the right pond.
You’ve got to pick the environments that work for you . . . context is so important. The unfiltered leader who is an amazing success in one situation will be a catastrophic failure in the other, in almost all cases. It’s way too easy to think, “I’ve always succeeded, I am a success, I am successful because I am a success, because it’s about me, and therefore I will succeed in this new environment.” Wrong. You were successful because you happened to be in an environment where your biases and predispositions and talents and abilities all happened to align neatly with those things that would produce success in that environment.
Ask yourself, Which companies, institutions, and situations value what I do?
Feeling powerless actually makes you dumber.
Being powerless at the office— having little control or discretion over your work— is a bigger risk factor for coronary artery disease than obesity or high blood pressure. Feel underpaid? That increases risk for a heart attack too. Meanwhile, ass kissing results in a reduction of workplace stress, improving happiness as well as physical health.
Bad behaviour is infectious
Once we see others getting away with something, we assume it’s okay. Nobody wants to be the sucker who plays by the rules when no one else does. Studies show expecting others to be untrustworthy creates a self-fulfilling prophecy. You assume they’ll behave badly, so you stop trusting, which means you withhold effort and create a downward spiral. It’s not surprising that work teams with just one bad apple experience performance deficits of 30 to 40 percent.
Ruut Veenhoven said, “The quality of a society is more important than your place in that society.” Why is that? Robert Axelrod, a professor of political science at the University of Michigan, explains, “Not being nice may look promising at first, but in the long run it can destroy the very environment it needs for its own success.”
Givers, Matchers, and Takers
Givers often take it on the chin in the short term, but over the long term— when they can meet other Givers and gain the protection of Matchers— their reputation becomes known, and boom. They go from the bottom of success metrics to the top.
Matchers tend to wait until others do something nice before they respond in kind. This passive attitude drastically reduces the number of interactions they have. Meanwhile, Givers run around handing out favors, losing a little to Takers, getting a fair share back from Matchers, and winning the lottery whenever they meet another Giver. Givers can be great networkers by merely being themselves, while the hesitant Matchers wait for an engraved invitation to the party.
When Harvard Business School’s Deepak Malhotra teaches negotiation, the first thing he says isn’t “Be tough” or “Show the other side you mean business.” His number-one recommendation to students is “They need to like you.”
This doesn’t mean you need to give twenty-dollar bills to everyone you meet. Favors can be quite small. We also often forget that something quite easy for us (a thirty-second email introduction) can have enormous payoffs for others (a new job). Doing quick favors for new acquaintances tells other Givers you’re a Giver and can earn you the protection of Matchers.
Pick your environment carefully
The people who surround us often determine who we become. When we see others around us perform altruistic acts, we’re more likely to act altruistically ourselves.
When you take a job take a long look at the people you’re going to be working with— because the odds are you’re going to become like them; they are not going to become like you. You can’t change them. If it doesn’t fit who you are, it’s not going to work.
About Positive Self-Talk
In your head, you say between three hundred and a thousand words every minute to yourself. Those words can be positive (I can do it) or negative (Oh god, I can’t take this anymore). It turns out that when these words are positive, they have a huge effect on your mental toughness, your ability to keep going.
While you may think that the key to being a good salesperson is people skills or being extroverted, research shows that salespeople can be hired based on optimism alone. Researchers found that “agents who scored in the top 10 percent [of optimism] sold 88 percent more than the most pessimistic tenth.”
Pessimists vs Optimists
Pessimists tell themselves that bad events: will last a long time, or forever (I’ll never get this done); are universal (I can’t trust any of these people), and are their own fault (I’m terrible at this).
Optimists tell themselves that bad events: are temporary (That happens occasionally, but it’s not a big deal ); have a specific cause and aren’t universal (When the weather is better that won’t be a problem); and are not their fault (I’m good at this, but today wasn’t my lucky day).
Optimists told themselves a story that may not have been true, but it kept them going, often allowing them to beat the odds. Psychologist Shelley Taylor says that “a healthy mind tells itself flattering lies.” The pessimists were more accurate and realistic, and they ended up depressed. The truth can hurt.
“We are what we pretend to be, so we must be careful about what we pretend to be.” So instead of merely focusing on intentions, make sure that in your day-to-day actions you are being the main character in your perfect story.
Everything we do in life is a trade-off. Choosing to do one thing means not doing something else.
As Henry David Thoreau said, “The price of anything is the amount of life you exchange for it.”
The irony is by not quitting unproductive things ASAP we are missing the opportunity to do more of what matters or try more things that might.
As the old saying goes, “You can do anything once you stop trying to do everything.”
There’s a science to luck.
It turns out luck isn’t just serendipity or due to the paranormal. A lot of it is about the choices people make.
Studying over a thousand subjects, Wiseman found that lucky people maximize opportunities. The study showed they are more open to new experiences, more extroverted, and less neurotic. They listen to their hunches. Most of all, Wiseman says, lucky people just try stuff. It makes intuitive sense: if you lock yourself in your house, how many exciting, new, cool things are going to happen to you? Not many. Is this some genetic gift? Hardly. After seeing that luck was largely a function of choices, Wiseman tried another experiment: Luck School. If he got unlucky people to behave more like lucky people, would they get the same results? Turns out they did. Afterward, 80 percent of Luck School graduates felt their luck had increased. And they weren’t just luckier; they also came away happier.
Experimenting and Strategic quitting
The things you should quit, are things you do every day or week that produce no value. What we’re talking about here are limited duration experiments. Giving something a shot. Taking a yoga class— but not signing up for a yearlong membership just yet. This is what spurs new opportunities and creates good luck. As Ralph Waldo Emerson said, “All life is an experiment. The more experiments you make the better.” In other words: Fail fast, fail cheap.
Spending 5 percent of your time trying new things, knowing you will quit most of them, can lead to great opportunities.
Positive thinking by itself doesn’t work
Not only did dreaming not bring you your desires; it actually hurt your chances of getting what you want.
When you dream, that grey matter feels you already have what you want and so it doesn’t marshal the resources you need to motivate yourself and achieve. Instead, it relaxes. And you do less, you accomplish less, and those dreams stay mere dreams. Positive thinking, by itself, doesn’t work.
After you dream, think, What’s getting in the way of my fantasy? And what will I do to overcome that? The fancy psych term is “implementation intentions.” You and I can just call it “a plan.”
How to be a leader
Research shows that you don’t actually need to know more to be seen as a leader. Merely by speaking first and speaking often— very extroverted behavior— people come to be seen as El Jefe. Meanwhile, other studies show that those who initially act shy in groups are perceived as less intelligent. As Pfeffer pointed out, to get ahead you need to self-promote. This comes naturally to extroverts and is actually more important than competence when it comes to being seen as a leader.
Mark Granovetter’s groundbreaking work on the importance of “weak ties” showed that you don’t usually find out about that next great opportunity from close friends. You tend to hear about the same things they do. People who have more peripheral acquaintances are more plugged in and learn about emerging possibilities. Having a big network also pays off when you get that job.
Choose your company wisely
“The groups you associate with often determine the type of person you become. For people who want improved health, association with other healthy people is usually the strongest and most direct path of change.”
Over and over we’ve seen that the people around you affect you. They can make you happier, healthier, and more successful— or the opposite. Most of this influence is passive and gradual. You won’t notice it. Mom told you not to hang out with the bad kids, and she was right. Research by Nicholas Christakis at Yale shows a network amplifies anything in it, good or bad. So surround yourself with the people you want to be.
Why self-compassion is better than confidence
Many studies show faking it also has positive effects on you. In Richard Wiseman’s book The As If Principle, he details a significant amount of research showing that smiling when you’re sad can make you feel happy, and moving like you’re powerful actually makes you more resistant to pain. Other studies show that a feeling of control reduces stress— even if you’re not in control. The perception is all that matters.
On the other side,
Faking it can be a very bad strategy because when you fool others you can end up fooling yourself.
Overconfidence makes you feel good, gives you grit, and impresses others— but can also make you an arrogant jerk who alienates people, doesn’t improve, and possibly loses everything because of denial. Being less confident gives you the drive and tools to become an expert and makes other people like you . . . but it doesn’t feel so good and can send a lousy signal to others about your competence.
Compassion for yourself when you fail means you don’t need to be a delusional jerk to succeed and you don’t have to feel incompetent to improve. You get off the yo-yo experience of absurd expectations and beating yourself up when you don’t meet them. You stop lying to yourself that you’re so awesome. Instead, you focus on forgiving yourself when you’re not. Research shows increasing self-compassion has all the benefits of self-esteem— but without the downsides. You can feel good and perform well while not turning into a jerk or being unable to improve. Unlike self-confidence, self-compassion doesn’t lead to delusion.
Hard Work Doesn’t Always Mean Good Work
Author Tony Schwartz says, “Energy, not time, is the fundamental currency of high performance.” It’s a qualitative lens instead of a quantitative one. All hours are not created equal. We’re not machines, and the time model is a machine model. Our job isn’t to be a machine— it’s to give the machines something brilliant to do.
Expectations vs happiness
You need a personal definition of success. Looking around you to see if you’re succeeding is no longer a realistic option. Trying to be a relative success compared to others is dangerous. This means your level of effort and investment is determined by theirs, which keeps you running full speed all the time to keep up. Vaguely saying you want to “be number one” isn’t remotely practical in a global competition where others are willing to go 24/ 7. We wanted options and flexibility. We got them. Now there are no boundaries. You can no longer look outside yourself to determine when to stop. The world will always tell you to just keep going.
Source: Barker, Eric (2017-05-16). Barking Up the Wrong Tree: The Surprising Science Behind Why Everything You Know About Success Is (Mostly) Wrong. HarperCollins. Kindle Edition.
Most people (passive and active investors) don’t get average market returns. The market averages, the S & P 500s of the world, have actually achieved a lot better than average market returns.
Many passive investors achieve below average returns because they are over-diversified, receive bad advice, and pay high fees to financial advisors. Keep in mind, many financial advisors are not in the performance business. They are in the business of providing sound financial planning services. It is not something that you cannot do by yourself, but let’s face it – most people simply lack the knowledge, the desire or the time to do it. The question is how much is a good financial advisor worth? One percent of your capital every single year? On a 500k, this is 5k a year. There should not be a big difference between allocating 500k and 5 million to index funds. Why are financial advisors not charging a flat fee after a certain minimum capital requirement is met?
Most hedge funds are not able to achieve average market returns over a long period of time after fees. 2 and 20 or even 1 and 15 can be hard to overcome if you manage a substantial amount of capital. If it is practically impossible, why should investors even bother? Considering the much bigger risk that you are taking, the leap of hope, the tax implications, hedge funds and managed accounts’ benchmarks should be a lot higher than S & P 500, the Russell 2000, the Vanguard Emerging Markets Index Fund, the S & P Global 1200, etc. So don’t gloat if your fund managed to beat the market by 200 basis points last year. You need to deliver a lot more to justify the risk people are taking with you. How much more? I’d say 1.5X their usual benchmark. The worse case scenario should be average market returns after fees with a smaller drawdown than the market averages.
What about active traders? We should take into account not only our return on capital but also our return on time and efforts spent. The time we devote to trading is a time we cannot use to acquire other skills. Therefore, we should require from ourselves a lot bigger than market average returns. 2x, 3x, 4X than what a market average can do for us. If we cannot achieve them and statistics show the vast majority of traders and investors cannot, there are better options for our time, intellect and money.
The way I see it, you have the following options:
a) Dollar-cost average in a cheap, well-diversified index fund and never read another financial article or watch financial TV.
b) Find a reasonably priced financial advisor who can earn his keep by providing a personalised financial plan. This is a good option if you are already rich and your goal is to remain rich.
c) Find smaller money managers with a great track record after fees. It is not impossible. I personally know half a dozen smaller managed account managers that have done a good job.
d) You can pay for education, strategic direction and ideas. There are quite a few amazing trading and investing services out there that more than pay for themselves. You save time, gain skill, and improve your odds of achieving substantial returns by spending very little money.