Angel: How to Invest in Technology Startups by Jason Calacanis

2020, book 25: “I always tell folks that I don’t need to figure out if your product will succeed, I just need to know if you will succeed. “ — Jason Calacanis

Finished on April 19, 2020

Jason is a person that I’ve followed for a while. I don’t particularly recall how I first got exposed to him nor do I recall what my thoughts first were. However, it’s pretty difficult to debate that he is one of, if not the greatest, investing minds in recent years. He’s identified a number of gems and great companies that have expanded his wealth tremendously. Along with that, as he shared in this book, there are hundreds of losers. Yet, the winners win, and when they do, they usually win enough to overshadow everything else — as long as they win big enough. I loved learning from Jason in this book and gaining deeper insight into his investing philosophies and his journey to get to where he is today — I admire him all the more.

There are most definitely better things for the children of the world to be doing than what they are. What happens when we eliminate the low-paying, repetitive, and menial jobs? Do we take that time and energy and focus on the larger and bigger issues like sustainability and the others that Jason mentions? I find that hard to believe. The incentive structure would need to change. Science shows that humans operate on incentives and many times, the incentive structure in the US does not encourage people who come from the more menial jobs to push harder and strive for higher levels.

Pg. 5, If right now you think I’m a horrible, marauding, free-market monster, you’re only half right — I’m also a humanist who thinks there are better things for our children to do with their time.

The quicker we eliminate the low-paying, repetitive, and menial jobs, the quicker our species can get to work on bigger issues like sustainability, being multiplanetary, and perhaps retiring the last couple dozen dictators and despots who are murdering, raping, and otherwise oppressing the weakest among us.

Of course, I could be wrong.

When we eliminate all these jobs, the world might spin into a global version of the long-forgotten dry run Occupy Wall Street where a group of savvy but poorly organized hippies and millennials slammed their feet down and said, “No more! We’re not leaving until things change!”

After following Jason for a few years, I was not surprised to read the following, “I also plan to look back proudly and know that I helped propel changes that made our planet better.” I had a pretty good idea that this was his focus and this was his vision. He wants to find companies and people that are exciting and innovative and will push the world forward. It takes a special kind of person to do that effectively over a long period of time.

Pg. 6, But I don’t invest in this future because I want to sit in an ivory tower laughing at people whose jobs are replaced. I invest in this future because it’s inevitable and I think I can help accelerate the efforts of the founders and innovators who are missionaries, not mercenaries. Of course, I plan to make a great deal of money in these revolutions, but I also plan to look back proudly and know that I helped propel changes that made our planet better.

It’s simple to think about but difficult to put into motion at a tactical level. People might think that they have a great business idea — and maybe they do — but if no one wants to buy it… it’s not going to work out too well.

Pg. 14, If you can’t tell who the sucker at the poker table is, it’s you, so find another table or figure out how to be better than each of the other players. This might take time, but everything worthwhile in this life takes time and effort.

Again, this comes across very authentically and directly in the way that Jason generally communicates. I would echo this statement entirely. I don’t know what it’s like to grow up any different than I did. For the first part of my adolescence, I was part of a two parent household in the upper middle class. For all of the experiences I did have, I was very sheltered to much of the world. I wasn’t exposed to things like local crime, murder, or drug use until later on. I never had to work to resist the urge or pressure to join those things simply because they were not even there to do. By the time any of those things were within my environment, I had a strong enough foundation in my faith and personal values to largely resist and abstain. For a long time now, I’ve had a vision and a purpose — that’s a luxury I know many don’t experience. So as Jason said, I hope that this book really does have the impact on others to show what is possible and what can be done.

Pg. 15, For the real outsiders:

As much as I feel like I’m an outsider — a kid from Brooklyn who didn’t go to Stanford and was born into the bottom of the middle class — the truth is I’m a lot closer to an insider than most folks in America, let alone anyone born in the developing world.

Let’s face it, I was born a white male in New York City at exactly the right time. I owned a thousand-dollar computer with a four hundred baud modem at the age of thirteen, and I was able to pay my way through night school at a decent college based on the skills that I learned using that computer. If I didn’t have that computer, I would have ended up becoming a police officer (true story).

Someone living in poverty in small-town America — without that IBM PC — certainly wouldn’t have had the head start I did. Those facts don’t even address the larger, more complex cultural issues around gender and race in our society that I haven’t had to face.

I wrote this book to give outsiders a playbook that could level the playing field just a little bit — even if I’m not smart enough to understand or help solve the deeper, more systemic problems myself.

With my limited exposure in the angel and startup investment world, I find that these four qualities are spot on. I couldn’t even add a fifth quality to the list here, these are just spot on. Money, time, network, and expertise. What else?

Pg. 28, 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).

I love this. “The best founders are typically inflexible and unmanageable.” If you listen to what other people say, you’ll never make a decision! Everyone has a different opinion. Just think back to Henry Ford, “If I would have asked what people wanted, they would have said a faster horse.” And then later on, “You can have your car in any color you want as long as it is black.” The best founders are the people who don’t ask what you want — but rather tell you and create for you what you didn’t even know that you wanted. Airbnb, Uber, Shopify, and so many more.

Pg. 29, When someone tells me they have a founder they want to introduce me to but they’re worried because the person is a wild card, I set that meeting up for the next day. Angel investors are looking for wild cards, because the best founders are typically inflexible and unmanageable, pursuing their visions at the expense of other people’s feelings.

I wonder if this is still true. When I first read this book I was in total agreement. Now with much of the exodus of California and New York, and the corresponding movements to Texas and Florida, I wonder how this changes. Nonetheless, the setting and environment is absolutely vital.

Pg. 40, If you want to make a country album? Go to Nashville.

If you want to make a movie? Go to Hollywood.

If you want to build a startup? You’ve got to be in the Valley.

Agreed. Set big goals and chase them relentlessly.

Pg. 41, Your job as an angel investor 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.

“I invest in people who build things, not people who talk about building things.” This is the truth. If you are an investor and you are searching for a business and team that is going to positively impact the world and provide a positive ROI for you at the same time, you cannot pour your time and money into someone who just talks and thinks of ideas — anyone can do that.

Pg. 45, If the most a person can create without funding is a PowerPoint deck or an insufferable email, they have DQed themselves from running a startup — and you should tell them that in your own style.

I don’t recommend using my style, which is uniquely abrasive but works with my personal brand and goals. I typically tell wannabe founders, “I invest in people who build things, not people who talk about building things.”

My approach is to be judgmental and combative, if you haven’t figured that out. I deploy this style for two reasons: (1) It’s who I am; and (2) it is effective in repelling the weak and developing deep, meaningful relationships with the strong.

This was something that I was fairly unaware of prior to this book. I didn’t anticipate that the CEO, the main person in charge of the organization, would ultimately allocate almost a quarter of their time to appeasing the newly created board. It makes sense when there are possibly millions on the line — of other people’s money — but it was surprising to me nonetheless.

Pg. 54, Once you have a Series A, the chief executive officer (CEO) is going to spend about 20 percent of their time “managing their board.” This means, setting up a board meeting every six to ten weeks, or six to eight times a year. They will prepare a board deck, have a lawyer create resolutions around stock options for employees, and they will essentially have a boss.

I love this. It’s the same in ANY industry. Everyone says it. Ask a real estate investor how to choose your first property and they’ll tell you to go look at 100 houses (if they’re any good). It’s exactly the same with businesses. Search and search and search and DO YOUR DILIGENCE. Only then are you in a position to decide what your best first move is. And the best investors? They NEVER lose that intense granular level of examination.

Pg. 58, When you first start investing, you should meet with as many people as possible but invest in as few deals as possible.

Which are you? It should be pretty clear by reading the following which of the five categories you fit into. Beyond that, it should be fairly obvious to you which of the five categories you would like to be in. I like a few of these — well really each one except the employee. Employees have a much lower ceiling than any of the other four categories. Angels are by far the most attractive. You are able to become involved at an early stage and then help guide the organization to hopefully great levels of success in the future.

Pg. 67, As I mentioned in chapter 8, there are five types of people on the cap table of a startup: founders, employees, advisors, angels, and VCs.

Founders and employees earn their shares by working full-time on building the company. They come to the office every day and vest their shares over four years, and all of their eggs are in one basket.

Angels and VCs buy their shares in a company, they don’t go to the company’s office every day, and they split their attention between many different companies — and finding new ones.

Advisors to a company don’t pay for their shares with cash but rather by providing their resources to the company, be they skills, Rolodex, or reputation. They add their personal brand equity to a startup’s often nonexistent brand equity.

The way that he views joining a board makes a ton of sense to me. We want to think about all the options. There is great investment with joining boards and you often give up a lot as a result. Does it make sense to join a board? Many times, sure, it may. But does it make sense to give up what you have to join a board? Many times, it may not make sense. I like his qualifications here: either it’s for friends or it’s an amazing company — otherwise it’s a no.

Pg. 69, Outside of my own investments, the only way I would join a board of a startup is if the founders were friends or I were massively passionate about the company. Why? Life is short and the return of being on a board these days would be de minimis compared to my returns as an investor. Of course, it’s great to pick up another hundred or five hundred dimes as a fee for serving on the board, but considering those paydays require fifty to two hundred hours of meetings and work over two or three years, there is a serious opportunity cost to them.

People don’t often think about opportunity cost — at least not as much as they maybe should. Maybe instead of binging a new Netflix show and working for 10 hours they could get themselves a $3,000 bonus. Maybe not, but wouldn’t it be cool if they could? What are you doing with your time and energy? I often contemplate opportunity cost as I write these. Not too many people read them today — but that’s ok for now. I don’t get paid for writing these types of things — at least not much right now.

Pg. 70–71, As you read or listen to this book, you need only look around you at the countless people on the subway or bus or freeway who are thinking about the opportunity cost of their lives.

I can’t tell you how many times, as I’ve struggled to write this book, I’ve asked, “Is this the best use of my time?” What if no one reads this book that I’ve spent months writing — and will spend many months promoting? What else could I have done with the hundreds of hours I’ve put into these tens of thousands of words?

You can pay me back for sharing all these secrets collected over years and written over six months, by taking these techniques and delivering massive returns. If just one of you becomes a billionaire, centimillionaire, or decamillionaire because of this book, it would please me to no end.

One investment at a time — grind it out. That’s what Jason says. Again, he’s transparent in one of his goals; Jason Calacanis wants to be on the board of a public company. Why hasn’t that happened yet? That’s a great question. But, he knows how to get there and as with the other goals and successes he’s already shared, I’m confident that he’ll get there in the not too distant future.

Pg. 74, Being a board member or advisor is nice work if you can get it, but you have to be willing to put the work in over a decade in the tiny startups that need you before the bigger companies that don’t need you as much will let you join their boards.

Even today, with a much higher-profile reputation, I’ve yet to be asked to join a major public or pre-public board like Twitter, Snapchat, or Google. This is understandable since I haven’t done it before, but still frustrating for me since it’s on my professional bucket list and I see so many dopey people join these boards and drive companies like Yahoo! Into the ground.

Perhaps if one of my investments goes public, I will get that opportunity to join a major board, but for now I continue to grind it out one investment at a time.

Love this. Agree with this. People aren’t lucky, they just do the right things and know the right people and make it known to those people that they are doing the right things. It all works in a motion. As long as we are working in alignment with God, anything is possible. The purpose that our Creator has placed over our lives is always going to be grander and better than anything we could create by our own power.

Pg. 82, You can make you own luck in this life by putting yourself next to the people who are already winning.

AngelList is one of my favorites, and especially for startup career opportunities also. SeedInvest is one I’ve since looked into, as well as Funders Club. This type of an opportunity is exciting to me, it’s magnificent and it’s exciting.

Pg. 84, There are a number of sites offering angel syndicates here in the United States including AngelList, SeedInvest, and Funders Club

This is a great bonus. Since working for a consulting firm that focused on startups and creating the deliverables, like a business plan and pitch deck, to help them get investment, I’ve seen some of what this looks like. I’ve seen the backend to an extent. I’ve seen what it looks like for investors to come in and how they can receive the stock that they purchase. I haven’t been part of a super large investing round but it’s been cool to see the seed rounds and the documentation needed there. A SPV makes a ton of sense when the investors are small.

Pg. 86, Founders love angel syndicates because they exist as only one entity on their cap table: the SPV. This means they don’t have to collect dozens of investor signatures when doing future deals. Instead, they just need to get one signature when doing future deals. Instead, they just need to get one signature from the syndicate lead who legally represents all of the other investors in the group.

Again, a great list that is succinct, clear, and valuable. When networking with investors it’s imperative that a mutual understanding results. You want to be able to help other investors as much as possible. Learn about them, learn from them, and then introduce them and connect them to others that they could value from.

Pg. 103, When you meet with fellow investors, your goals are:

1. Figure out what they invest in and why.
2. Figure out what value they bring to startups.
3. Make sure they understand what value you bring to startups.
4. Ask them, “Have you seen anything interesting lately?”
5. Offer them, “I just invested in these two startups, which are exceptional. Would you like to get introduced to the founders?”
6. Determine if they prefer double opt-in introductions or blind introductions.

Jason is talking about how you are putting yourself in the right circles. I don’t understand the reference at all (had to look it up) but love the abruptness to which he reminds us to remain grounded. Enjoy the accomplishment, but only briefly, and then get back to work.

Pg. 106, I call this process “reputation in a box.”

Now take a moment and consider just how quickly you’ve gotten into the Star Chamber.

Okay, the moment’s over.

Get back to work.

The goal is always longevity. It doesn’t help if you qualify people based on criteria that a year or two from now will not make any sense to you. You want to be able to quickly and effectively review what you have prepared and make decisions as a result.

Pg. 106–107, I suggest putting (the twenty-five founders you’ve met with) into a spreadsheet with the words Great, Good, or Okay next to each one. These are three really easy terms to apply. Put one sentence next to each Okay, saying why you’re not going to invest. This is a candid sentence that is easy for you to look back at six, twelve, and twenty-four months from now when you check your ability to forecast.

This is a great actionable item to add to the benchmarking and forecasting that should be done regularly. It’s one thing to document things and how the companies are doing at the present state, it’s another to regularly revisit and continually reassess. If a recent company that you’ve invested in did not succeed, it’s important to understand why you thought they were a winner when they actually were not.

Pg. 107, Put a recurring calendar reminder for every six months to visit this spreadsheet and make a fifth column with notes on how the twenty-four companies you passed on are doing — specifically whether they’ve raised more money or shut down.

Forecasting is about learning from your past decisions, and you can’t forecast well if you don’t write down your thoughts and check back on them.

“How can I be more valuable?” That is an incredibly important question to ask, again, on a regular and continual basis. In the situation of a founder that is going to be presenting a company that we might be investing in, we need to set ourselves apart. More than that, it’s also important to put the founders in a position that they can control. It doesn’t do much to keep them guessing or make them cater to your every need.

Pg. 118, Now, when you get into the meeting, you should check your phone one last time, let them know if you have a hard stop, and ask them how they would like to run the meeting. Here’s what I say: “Would you like to run me through your deck, show me your product, or just talk about your business?”

This flips the script they are used to. My contemporaries are known for dictating to investments how they should do their meetings — as in the investor’s meetings. That’s reasonable — each investor has their process — but I look at those other investors and think, “How can I be more valuable than they are?”

This was a great point. Take notes in a book, make it evident to the founders that we are there for them and that we are valuing the situation and the opportunity.

Pg. 119, So, when you get in that meeting, look at it like you’re being videotaped and it will be on the local news that night. Show up focused, with a notebook and pen so you can take notes like an adult. Never take notes on your laptop, and certainly don’t be “that guy” who takes notes on their tablet with a stylus.

If you take notes in a book, you are signaling this person that their product and their vision are worthy of being commemorated in your journal for all time.

Details matter. Enough said? Focus on the little things and let them compound.

Pg. 120–121, Ever since I started going to meetings with people like Barry Diller, who has crisp, sharpened pencils and pads in the middle of the table, or at the elite banker Allen & Company, where they have a button that allows them to call a waiter without you ever knowing it, I’ve become obsessed with “conference room prep.”

I want folks to feel like meeting with me is like going to a restaurant with multiple Michelin stars. I want folks to understand that we are professionals.

I’m not trying to impress folks with expensive offices, but I do want to impress upon them that they are meeting with the best angel investor in the world — even if I’m only in the top five or ten right now.

Details matter.

Well said and an important perspective.

Pg. 126, Okay, there are two types of businesses in my world: insanely scalable ones and everything else.

The best investors are those who simply pick the best founders. The greatest companies always come from the greatest founders.

Pg. 129, “I don’t need to know if your idea is going to succeed, I need to know if you are,” is a line from my blog that has been repeated over and over again.

Before any sort of early stage investment, this makes sense to ask. We want to understand at a deeper level who we are investing in as much as we understand what we are investing in.

Pg. 132, The goal of asking these questions is not just for you to understand the business but also so you yourself can answer four critical investor questions:

1. Why has this found chosen this business?
2. How committed is this founder?
3. What are this founder’s chances of succeeding in this business — and in life?
4. What does winning look like in terms of revenue and my return?

“What is your unfair advantage?” If there isn’t one, maybe the business is not in your best interest to begin at this time. It’s all about celebrating the founders, understanding their value and if you could provide any to them. I think the exploratory phase of the conversation and the major four questions to ask each time are valuable and essential. These are the types of questions that we should really strive to answer each time we make an investment.

Pg. 134–140, When you are starting a founder meeting, ask one icebreaker question to get your subject warmed up.

0. I have a game where I try to say things with as few words as possible because it reminds me that this meeting is not about me, it’s about them. It also makes me sound wise, like Obi-Wan or a Toshiro Mifune character.

These are the exact four questions I ask every founder. The answers to these questions will give you most of what you need to make your investment decision. We spend the first half of our hour-long meeting exclusively on them. Then we go deeper,

1. What are you working on?

This celebrates the founder (the “you”) and what founders do (the “work”). It shows that you have deep empathy and you recognize that this isn’t about what the thing does, but rather it’s about people.

2. Why are you doing this?

When I ask these first two questions, I almost universally see founders melt into their chairs. They relax, let their guard down, and feel like I care about them, which I do.

3. Why now?

In some ways, “Why now?” is the most important question about the business you can ask because there are so many folks constantly trying the same ideas over and over again in our business.

Google was the twelfth search engine. Facebook was the tenth social network. iPad was the twentieth tablet. It’s not who gets their first. It’s who gets there when the market’s ready.

4. What’s your unfair advantage?

Said another way, this question is asking, in just four words, “What makes you uniquely qualified to pursue this business? What secrets do you know that will help you beat both the incumbents and your fast followers?

As Jason emphasizes, the best founders know each of these responses off hand and can share them very concisely — that’s what we’re seeking. As the leader of the organization, it should be straightforward to answer any and all of the following questions. There should not need to be much thought required because this is what you do. You are building a business and these questions should have been answered by yourself at one point or another.

Pg. 146, Finish up the meeting by getting tactical and personal by asking concise questions. You can rip through a bunch of these with a qualifier in front (or back) of them like “briefly” or “quickly,” so the founder knows that you just want the short version.

1. Tell me about the competition.
2. How do you make money?
3. How much do you charge customers?
4. How much does your average customer spend?
5. Tell me the top three reasons why this business might fail.

These questions shouldn’t take a lot of work to answer. The great founders tend to be able to answer them efficiently. Here is how Airbnb might answer these five:

1. Hotels and Home Away are our two biggest competitors. Hotels and HomeAway are both much more expensive — typically two to three times more expensive — than an Airbnb.
2. We take a transaction fee.
3. We take 3 percent from the host and charge a 10 percent fee from the guest.
4. Our average stay is 1.7 nights, with a total charge of $225, of which we keep about $40.
5. Regulations are our biggest challenge, finding inventory is our second-biggest challenge, and having a consistent, high-quality experience is our third-biggest challenge.

Now, if a founder answers a question that tightly, you should be drooling. Many founders, and most fakers, are unable to talk about their business objectively — and that’s why they have a board, a monthly update, and investors to keep them honest.

Reality check. I agree though. Founders should be able to get off the ground. They should be ready to leave the runway and take flight by the time that angels get involved. If they’re still in the airplane hangar trying to figure out which type of gas to use, they aren’t the ones.

Pg. 162, In my mind, founders shouldn’t be contacting angel investors in the idea, business plan, or pre-MVP stage. If they are reaching out to you, it’s a sign that they can’t build the product themselves, nor do they have the ability to get talented folks to build the product with them on the weekends or with friends and family funding.

Is this fair? No.

Is the world fair? No.

“Seeing a person execute on their plan over time is the best way to decide if you should invest.” I love this. Why invest in something that is not working? You wouldn’t, would you? Especially in the early stages, and with a new company, you want to be able to be confident in what you are investing in and want to be 100% in when you do invest. If you can’t do that, it only makes sense to say not yet and leave the door cracked open in case you want to step into the deal later on. Later investment might come at a premium but I’m willing to pay more if that means I’m more confident in a strong ROI.

Pg. 182–183, Say “not yet” instead of “no”

These days, I am most likely to tell founders “not yet” when they ask me if I’m ready to invest. It’s an elegant phrase that Roelof Botha taught me and it works like a charm. In addition to telling them that I’m just not there yet, I let them know that I’d like for them to add me to their monthly updates.

The second great part about the “not yet” is that I give the founder the ability to prove me wrong but still include me.

Nothing pleases me more than having a founder “show me” because that means I’m going to be able to make a bet on a stronger company.

Third , I set the tone that monthly updates are something I like to see before I give the founder my money.

Life is one giant test, and interacting with investors is one of those tests. Seeing a person execute on their plan over time is the best way to decide if you should invest.

(I wrote in the margins “SO AGREE”). If something seems like it doesn’t add up, I’m just going to leave it at that. Trust but verify is the way I live but if there is anything that leaves me feeling uneasy, I need to trust my intuition and sever ties quickly.

Pg. 195, He explained that the founder had done a bunch of things he considered unethical and I came to a simple conclusion, independent of further investigation, which I live by to this day: the appearance of impropriety is impropriety.

This is essential — setting expectations. As an investor, you’ll want to be informed and it’s important to openly communicate what level you need to be informed on. Some people are different than others but there are some fairly common expectations as Jason outlines. Things like cash levels, burn rate, etc. that especially as an investor, will be essential to be aware of at pretty much all times.

Pg. 213, You can avoid all the drama with a simple discussion, before you invest in a company, that you can strategically repeat for them at subsequent meetings after you’ve invested. The language I like to use will go something like this:

“I would like a monthly update from you that includes the key metrics for the business, as well as what you consider the wins and losses since the last email. I would like you to put requests for me and your other investors in the email as well. Every email should have how much cash you have left, your burn rate, and when you will be out of cash so that we can all plan for future raises.”

Talk yourself down. Only you have the power to calm yourself. After all, you riled yourself up in the first place. We need to get to a point where we not only hear, not only listen, but fully comprehend and understand as much as possible.

Pg. 229, When you find yourself in a completely frustrating position, I suggest you take the technique I learned from a book by Mark Goulston called Just Listen in which he advises, in a nutshell, to talk yourself down from an “Oh f***” reaction to an “Oh my God” for release and on to an “Oh Jeez,” “Oh well,” and finally a simple “Okay.”

(I loved that book also and will link my reflection to it here: Just Listen by Mark Goulston.)

This is one of the reasons that a founder’s role is the most tolling. The employees under you should only know the highpoints. If a founder is panicking, they’ll likely mirror that — and that’s not beneficial nor is it productive. As a founder, you must be the rock that others can cling to, no matter how difficult that may become in certain settings.

Pg. 230, Think about it. The reason all these people decided to quit other jobs and follow this founder is because they were swept up in the founder’s passion. So it only makes sense that they will be swept up in the founder’s panic. A CEO’s job is to smooth out the emotional roller coaster. Never let your team experience the same highs and lows you’re feeling because the odds are they aren’t built to handle these kinds of ups and downs like you are.

I touched on this earlier when I highlighted the portion about reviewing the changes in investments after 6 months. Take a look at who you invested in that ultimately lost. With hindsight, were there any yellow flags or red flags that you now notice that perhaps you overlooked or undervalued? Losing is a part of the game. There are people that you might think are great, that you might think are the best, but when trouble comes, they stumble and they fall and they give up. Invest wisely, yes, but as with anything, keep going and persevere — that’s the only way.

Pg. 236, You don’t have to obsess over the losers, but I would certainly meditate on them and look for patterns. I was able to fix some leaks in my investment strategy by doing this. The biggest leak in my early years was that I frequently assumed that if I, or my very qualified friends, could execute on a plan, then my investments could, too. I assumed that all founders were dogged and die-hard, but I learned the hard way — after a half-dozen startups gave up and gave their investors five to fifty cents on the dollar back — that not everyone is die-hard.

Sometimes in life, you have to go through it to get to it.

That’s angel investing.

If a founder that is a winner has a failing business model, they’ll pivot. If a founder that is a loser has a failing business model, they’ll lose. Which are you?

Pg. 251, I always tell folks that I don’t need to figure out if your product will succeed, I just need to know if you will succeed. If I have a gift in this angel investing game, it’s that I’m good at reading people and figuring out how meaningful winning will be to them.

It probably comes from years of trying to read the best poker players in the world — and failing often.

This quickly became one of my favorite books. If not evident from the more than 6,000 words from the book and my personal thoughts, I found great value from Jason’s book. This was a book that was incredible and highly impactful for me. I look forward to reviewing my notes again in the future and going deeper into investments at all levels.

I gave this book a 5/5

Join my weekly newsletter to see all of my writing here.

Read this article on the original source.

Leave a comment

Please note, comments must be approved before they are published