Tag Archives: Reading

The Power Law (Part Three): Angels and VC’s

In the world of venture capital, there are two species: great white shark VC’s and goldfish angel investors. They dwarf us in size and power as we wiggle about looking for an insect to eat.

So I was surprised to learn that in some of the hottest deals, angel investors actually have the advantage.


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In his superb new book The Power Law: Venture Capital and the Making of the New Future, Sebastian Mallaby recounts how the greatest tech companies found their first supporters. Time and again, the hottest companies rejected entreaties to meet from the top venture firms.

Instead, they went to angel investors to raise money quickly and easily with a minimum of oversight.

Mark Zuckerberg refused to meet with Accel early on. He even showed up at the offices of heavyweight Sequoia Capital in his pajamas!

Sequoia founder Don Valentine recognized the stunt for what it was: a provocation. Zuckerberg wanted the princes of Sand Hill Road to know he didn’t need them.

Instead, he turned to Peter Thiel and other angels for his first funding. Unlike the slow moving investment committees of venture firms, they could write a check on the spot.

But Zuckerberg was not the first great entrepreneur to shun VC’s. Google founders Larry Page and Sergey Brin had every firm in the Valley breathing down their necks.

Instead, they met angel Andy Bechtolsheim on their front porch.

After a brief pitch, Betcholsheim raced back to his Porsche and returned with a checkbook. He invested $100,000 when the company wasn’t even incorporated.

Along with angels, lesser known venture firms also back many of the greatest companies. As Mallaby notes:

“…the idea that venture capitalists get into deals on the strength of their brands can be exaggerated. A deal seen by a partner at Sequoia will also be seen by rivals at other firms: in a fragmented cottage industry, there is no lack of competition. Often, winning the deal depends on skill as much as brand: it’s about understanding the business model well enough to impress entrepreneurs; it’s about judging what valuation might be reasonable. One careful tally concluded that new or emerging venture partnerships capture around half the gains in the top deals, and there are myriad examples of famous VC’s having a chance to invest and then flubbing it.”

I was very surprised to learn that being at a top firm isn’t the advantage it may seem. No wonder Sequoia still cold messages founders!

In this competitive environment, I look for ways for us to cooperate.

VC’s can benefit if angels bring them great early stage deals. Angels benefit by being able to help their portfolio companies.

In the end, if we can work together to build the greatest companies of the future, everybody wins!

What are your experiences raising from angels and VC’s? Leave a comment at the bottom and let me know!

More on tech:

The Power Law (Part Two)

The Power Law (Part One)

Managing a Crisis the Sequoia Way

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Photo: Google founders Larry Page and Sergey Brin. “File:Google page brin.jpg” by Ehud Kenan is licensed under CC BY 2.0.

The Power Law (Part Two)

“When in doubt, take the shot.”

Doug Leone, Managing Partner, Sequoia Capital

The partners from prestigious venture firm Accel stood outside an office in Palo Alto, waiting to take theirs.

These were the offices of a young startup called thefacebook.

Most startups would’ve killed to meet them. But thefacebook’s young founder gave the Accel partners the cold shoulder.


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This didn’t stop them. They lurked outside and buttonholed any thefacebook employee they could find.

Eventually, they got the meeting with founder Mark Zuckerberg. And they won the deal, a $10 million check into the company’s Series A round.

To this day, it remains one of the greatest investments in the history of venture capital.

As an angel investor, I always assumed that the prestigious firms like Accel or Sequoia had it easy. The best founders must be falling all over themselves to meet them!

Nothing could be further from the truth. As Sebastian Mallaby chronicles in his superb new book The Power Law: Venture Capital and the Making of the New Future, the greatest firms are also the scrappiest.

Sequoia Capital, perhaps the greatest VC firm in history, wrote their own code to find the most downloaded new iOS apps. One day, it flagged a small program called WhatsApp.

Sequoia partner Jim Goetz sent e-mail after e-mail to WhatsApp’s founder. For months, he never heard a word.

Finally, Goetz was able to get a meeting with WhatsApp’s founder, Jan Koum. In time, Sequoia won the deal.

The investment made Sequoia $3 billion, and WhatsApp is now ubiquitous throughout the world.

So what does this mean for small fries like me?

Even the greatest have to vigorously pursue deals and handle rejection, so don’t give up on an awesome company! If Sequoia isn’t too cool to cold-message a founder on LinkedIn (psst: they’re not), neither am I!

And when I find that rare, incredible startup, I’ll be repeating Leone’s words to myself: “take the shot.”

More on tech:

The Power Law (Part One)

Managing a Crisis the Sequoia Way

Talking Startups and Today’s Fundraising Pullback

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Photo: Doug Leone, Managing Partner, Sequoia Capital. “_SJP1148” by TechCrunch is licensed under CC BY 2.0.

The Power Law (Part One)

“Reasonable people…routinely fail in life’s important missions by not even attempting them.”

The Power Law

Every day for the last 15 months, I’ve sat down in front of my computer and tried to find the next great tech company. Being immersed in the daily details of e-mails and deal memos made me wonder about the history of this most unusual of industries, venture capital.


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So I grabbed a copy of Sebastian Mallaby’s excellent new book The Power Law: Venture Capital and the Making of the New Future. Mallaby traces the history of venture capital from its first deal to today, and explores the principles that drive its success.

The fundamental principle of venture capital is the power law — a small percentage of winners generate almost all the returns:

“Anytime you have outliers whose success multiplies success, you leave the domain of the normal distribution for the land ruled by the power law — from a world in which things vary slightly to one of extreme contrasts. And once you cross that perilous frontier, you better begin to think differently.”

Since just a few companies drive most of the returns, the entire business becomes about finding and investing in those very few companies:

“…each year brings a handful of outliers that hit the proverbial grand slam, and the only thing that matters in venture is to own a piece of them.”

So how should investors identify those rare businesses? Arthur Rock, who was arguably the first venture capitalist, liked to ask open-ended questions like “Who do you admire?” or “What mistakes have you learned from?”

Rock looked for founders who were realistic and determined. He avoided those who were prone to wishful thinking or who tried to please instead of being honest.

Rock’s inquisitive style led him to back Fairchild Semiconductor in the 1950’s in what was the first modern-style venture capital deal.

Founder traits are important, but hard numbers also matter. Google, eBay, Facebook and YouTube all had staggering growth figures early on.

Andy Rachleff, Benchmark partner and early investor in eBay, looks at an even more sophisticated growth metric:

“‘When companies grow exponentially, they don’t suddenly stop,’ Andy Rachleff observed later, adding that it is the ‘second derivative —the changes in the rate of growth of a company’s sales — that really tell a venture investor whether to back it.’”

Once an investor finds that diamond in the rough, he needs to own a piece, even if the price is high. Mallaby notes that Google’s seed round valuation was around $10M, high for its time.

Prone as I am to analysis, I often undervalued actually meeting investors and founders. This book taught me a lot about the importance of networking to the venture industry.

Don Valentine, founder of Sequoia, went to a Silicon Valley bar every Wednesday and Friday to chat with engineers about the next big thing. In the world of startups, investors are the specialists in connecting people with each other.

The more interesting people we meet, the better we’ll be at our job!

Mallaby provides so much great information that I’ll save the rest of the book for another post soon. In the mean time, if you’re interested in startups and venture capital, I urge you to grab yourself a copy!

More on tech:

What I Learned From an Investor Who Turned $100,000 into $100,000,000

Amp It Up

Managing a Crisis the Sequoia Way

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Photo: “Don Valentine, Sequoia Capital” by jdlasica is licensed under CC BY 2.0.

Amp It Up

“Only the government can print money; the rest of us have to take it from somebody else.”

Frank Slootman

Frank Slootman has been the CEO of three companies: Data Domain, acquired for $2.4 billion, ServiceNow, market cap $94 billion, and now Snowflake, market cap $52 billion. His track record has few parallels.

But Slootman wasn’t always a big success. As a teenager in the Netherlands, he cleaned toilets for a living. When he moved to the United States, he had his heart set on joining IBM.

They rejected him. 12 times.

So how did Slootman go from obscure Dutchman to one of the biggest names in tech? By bringing a warrior’s mentality to business.


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Slootman focuses like a laser on destroying the competition, on breaking their will to fight. And the most powerful weapon in his arsenal is growth.

When you grow much faster than your competitors, it demoralizes them. And as you become the winner, you can begin poaching their best people, causing the rest to lose all confidence.

The importance of growth to Slootman’s approach is impossible to overstate. It’s also born out by data:

“‘Grow Fast or Die Slow’ is the title of a 2014 McKinsey & Co study that examined thousands of software and services companies between 1980 and 2012. It concluded that growth trumps everything else as a driver and predictor of long-term success. ‘Super grower’ companies, which McKinsey defined as 60% or more annual growth, had five times higher returns than medium growth companies (which had less than 20% annual growth). Super growers also had an eight times greater likelihood of reaching $1 billion in annual revenue. “

So how do you grow fast? Slootman recommends focusing on one key thing.

Many priorities means no priority.

You should also push everyone to move faster at all times:

“Leaders set the pace. People sometimes ask to get back to me in a week, and I ask, why not tomorrow or the next day? Start compressing cycle times.”

Frank Slootman

But not just any team can achieve this. Finding the very best talent will make or break your business:

“Hire more for aptitude than experience and give people the career opportunity of a lifetime.”

Frank Slootman

This talented group of people also must be motivated by an important mission. Snowflake is making data queries 10-100x faster, leading to a total revolution in how humans use data to make decisions.

That’s the kind of mission that will put pep in your step!

Slootman also has some interesting info for investors in startups, such as myself. The way he spotted “super grower” companies to take the helm of was by looking for a fast growth track record, a huge market, and extremely happy early customers.

We can use the same criteria to find great investments.

Slootman’s book is energizing, exciting, and a true page turner. That’s rare in the world of business books.

I strongly recommend getting this slim volume for yourself! After reading Slootman’s words, I felt ready to run through a wall.

You will too!

Let’s close with a great quote from Frank:

“Only in hindsight will you truly realize what your experiences have meant. That is why it’s okay to embrace your inevitable challenges and setbacks as part of your journey. They are there for a reason.”

Frank Slootman

What do you think Slootman got right, and did he leave out?

Leave a comment at the bottom and let me know what you think.

Have a great day everyone!

More on tech:

Hedge Fund Giant Tiger Global Losing $28 Million an Hour

The Startup Pitch Checklist

The Lean Startup

Photo: “Frank Slootman” by Thomas Hawk is marked with CC BY-NC 2.0.

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How the Bulls Dominated the NBA

Michael Jordan plays basketball better than anyone else in the world does anything else.

Scott Turow, quoted in Playing for Keeps: Michael Jordan and the World He Made

The Chicago Bulls dominated their league like no other team in no other sport during the 1990’s. They won 6 NBA championships, an astounding record. 

I just finished reading the outstanding book Playing for Keeps: Michael Jordan and the World He Made. It’s an insightful look into what made Jordan and his Bulls so special. 

Here are some of their secrets:

1) Hard work. Jordan came to practice before anyone and left last. This got him from being rejected for the high school varsity to dominating the pros. 

2) Coachability. Anyone who coached Jordan, even in baseball, said he was unusually coachable. His willingness to learn from others, rather than think he knew everything, set him apart. 

Consider that for a player of his stature, it would be easy to dismiss a coach’s suggestion! But he didn’t. 

Even the quirky Dennis Rodman listened carefully to coach Phil Jackson’s lessons.

3) Love of the game. Both Jordan and Scottie Pippen stood out for truly loving basketball. 

Jordan even had a highly unusual clause in his contract. He could stop at any basketball court in the world, any time, and play a pickup game.

And he did so, frequently! I like imagining Jordan pulling up at a playground in a fancy car, lacing up his sneakers, and heading out onto the court.

I just wouldn’t want to have to guard him!

This type of clause is highly unusual due to the risk of injury, but Jordan insisted on it.

It’s hard to work at something so intensely for so many years if you don’t love it! And that’s what it takes to excel. 

4) Ability to see others strengths, not just their weaknesses.

Jackson was upset when Pippen refused to play at the end of the Eastern Conference Finals.  But he didn’t let that incident sour him on Scottie as a player.

Instead, he viewed it in the context of all of Scottie’s great work over the years.  Even the exacting Jordan became more aware of his teammates’ strengths over time.

This is an area I struggle with. If someone does one thing wrong, I tend to view them negatively, forgetting all their great work. 

I plan to take a lesson from Coach Jackson on this in the future! 

5) Never giving up. Jordan was famously cut by his high school team. 

Rodman didn’t even make the team at all. And Pippen started college basketball at a no-name school as the team equipment manager. 

These are not people you would think would’ve ever even made it to the NBA, much less won 6 championships. 

Their perseverance made the difference!

Check out this excellent book along with the addictive Netflix series The Last Dance. Even if you’re not a basketball fan, you can learn a lot from the Bulls about excellence in any field! 

More on leadership:

From Anticommunist to Navy SEAL: “I Owe Everything to America”

Jocko on Leadership: “Ownership Is the Most Valuable Compensation”

The Best Motivational Speech of 2021

Photo: “Michael Jordan” by simplistic.designs is licensed under CC BY-NC-ND 2.0

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The High Growth Handbook: Scaling Startups from 10 to 10,000 People

Elad Gil is a Silicon Valley legend. After selling his startup to Twitter, he helped the company scale from 90 to 1500 people in under 3 years.

He’s also had enormous success as an angel investor, investing in startups like Airbnb, Coinbase, Square and Stripe.

So I was very excited to dig into his book, The High Growth Handbook. In it, Gil lays out his best tips for scaling a company at warp speed, along with interviews with a who’s who of tech.

Here are some of the best pieces of advice I found:

How to Hire

“Hire only after there’s a burning need for that person.”

Naval Ravikant

Gil’s approach to hiring is carefully structured. He suggests writing a job description for every position and asking each interviewee the same questions.

But even better than questions are actual tasks. The best way to assess someone’s skills is to have them complete a task similar to what they’ll do on the job.

He also counsels interviewers to write down their opinion of the candidate before speaking with other interviewers, to avoid groupthink. This is the same process used at Amazon.

And when you do find the right person, move fast!

How to Lead

So you’ve got your ideal employees. Now what?

In an interview with Sam Altman, Altman says that setting the company’s direction is just 5% of a CEO’s job. The other 95% is making sure it happens.

“Delegation is not abdication.”

Gil also recommends holding skip level meetings with junior employees that don’t report to you. They tend to have their finger on the pulse of the market and are closer to the customers.

How to Rest

Gil used to work every weekend and even on “vacations.” But now, he tries to fully unplug.

This is something I struggle with! I was meeting with a company founder at nearly midnight on my vacation in Barcelona while my wife waited patiently upstairs.

We have to remember that if someone as successful as Gil can unplug for a few days, we can too!


In all, I found this book a very practical guide to building startups. My only criticism is that with the mix of interviews and Gil’s writing, and the jumping between topics, the book feels disjointed.

I think it would be more effective if it followed a company from birth to IPO, examining the challenges it faces on the way.

Nonetheless, if you’re interested in startups, Gil’s advice will help you. Check it out!

More on tech:

What I Look For in Startups

How Startup Founders Turn Investors Off

The Top 3 Startup Pitch Mistakes

Photo: “Elad Gil” by jdlasica is licensed under CC BY 2.0

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This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 and returns have been good so far. More on Fundrise in this post.

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Liftoff: How Elon Musk Built SpaceX

At 1310 East Grand Avenue in El Segundo, just south of Los Angeles, sits a large white building. In 2002, it housed only about a dozen people. There wasn’t even a receptionist.

Deep in this building was a small group of cubicles, staffed by about a dozen men. This tiny group had an audacious goal: sending the first humans to Mars.

Their leader was a young internet entrepreneur named Elon Musk. He had just made $180 million from the sale of PayPal. Many men in his position would buy an island and relax, or perhaps begin a career in philanthrophy. But Elon toiled away in this nondescript warehouse instead, building the future.

This is the subject of an outstanding new book I just finished called Liftoff: Elon Musk and the Desperate Early Days That Launched SpaceX.

From this tiny team, Musk built SpaceX, which now does two thirds of all commercial satellite launches in the world and owns the most powerful rocket on earth, the Falcon Heavy. That small group of employees has mushroomed to nearly 10,000.

To go so far so fast, Musk needed the best people in the business, and he focused like a laser on finding them. One engineer’s wife got a job at Google in the Bay Area, which meant he couldn’t accept Musk’s offer to work at SpaceX. Undeterred, Musk called the CEO of Google and got the engineer’s wife a transfer to Los Angeles. Sure enough, he got the engineer he wanted.

Musk went so far as to personally interview the first 3000 people SpaceX hired. Musk paid less and his company was unproven, but he excelled at inspiring people to join him to revolutionize space travel.

Even with Musk’s drive and a superb team, SpaceX faced many struggles. By 2008, they had three failed flights and barely a month’s worth of cash left. Even Elon’s considerable fortune had run dry supporting both SpaceX and Tesla. But Musk and his team stayed focused and successfully launched a rocket into orbit in the nick of time. This achievement won them a NASA contract that kept the company alive.

SpaceX questioned everything about how business is normally done in aerospace. Most companies buy parts from established suppliers, but SpaceX built almost everything itself, substantially lowering its costs. For the parts it did buy elsewhere, SpaceX ignored common practice as well. Instead of paying in 30 days, SpaceX paid in as little as 24 hours. This got their orders prioritized, which helped them move faster than other rocket companies.

Today, only one other private company, Rocket Lab, has reached orbit. Jeff Bezos’ Blue Origin, despite all his money, has never reached orbit. Indeed, SpaceX is so dominant that customers sometimes spread around a few of their orders, just to make sure its competitors don’t all go out of business.

If I had seen Musk in that empty warehouse twenty years ago, I would never have believed what SpaceX would become. But Musk saw it, and stopped at nothing to get there.

When the first man steps on Mars, will it be Musk?

Dig into these posts for more on Elon Musk and space:

Photo: “SpaceX Dragon Propulsive Descent Landing Test” by NASAKennedy is marked with CC PDM 1.0

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Amazing Drugs Are Going from the University to the Graveyard, While Patients Pay the Price

Was the cure for cancer invented in a university, only to be shelved for a lack of funding?

University labs are creating incredible drugs on a regular basis. Unfortunately, most will never get to the patients that need them so desperately. This is the conclusion of an intriguing book I just read, Preserving the Promise: Improving the Culture of Biotech Investment, by Scott Desain and Scott Fishman.

The problem is that universities don’t have the massive funds it takes to bring a drug candidate through clinical trials to FDA approval. What about Big Pharma? Well, they’ve been cutting their R&D budgets drastically for years.

This leaves early stage biotech investors to fund much of the commercialization of new drugs, and there simply aren’t enough of them to fund all the good candidates. Indeed, the number of investors specializing in this area is shrinking. This doesn’t surprise me given that most early-stage investors focus on software startups and have a software background themselves.

This does leave the few angel investors who specialize in biotech in an enviable position though: more great companies out there than there are angels to fund them means big slices of great companies for less money, and thus higher returns. This is an area that I may be branching out into in the future. Being even a tiny part of creating a new lifesaving drug or medical device would be incredible.

University policies also hinder the effective commercialization of research, the book notes. Technology Transfer Offices own the patent, but sometimes are hesitant to license it unless they can get lots of revenue for it right away, which is hard for a fledgling company to provide. In other cases, they bury the patent, thinking it unpromising. And university conflict of interest policies can often stop the inventor from continuing to work on the research with company funds. This separates the technology from the person who is best positioned to advance it.

In all, this seems like a neglected area with a lot of problems. That we rely on it for virtually all new drugs is scary. But investors like myself should eye the area with interest, especially given rich valuations in software startups.

For more posts on biotech, check these out:

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Photo: The co-founders of BioNTech, a biotech success story. “Forschungszentrum der Biotech-Unternehmen BioNTech AG und Ganymed Pharmaceuticals AG” by MWKEL-RLP is licensed under CC BY-NC 2.0

What I Learned From James Watson, Co-Discoverer of the Structure of DNA

We wish to suggest a structure for the salt deoxyribose nucleic acid (DNA). This structure has novel features which are of considerable biological interest.

So begins the famous Nature paper by James Watson and Francis Crick, who discovered the structure of DNA in 1953. Their discovery revolutionized biology and won them both the Nobel Prize.

I just finished reading Watson’s book The Double Helix, and as a layman I found the inside view of the process of scientific discovery intriguing. What struck me most was the importance of collaboration.

We are used to thinking of scientists as lone geniuses hunched over a lab bench until they exclaim “Eureka!” But Watson’s book makes clear how important the many scientists surrounding him at the University of Cambridge were to his discovery. He repeatedly checks his findings with others more experienced than he in a particular area, like structural chemistry. And without the long conversations with Crick, the discovery would never have happened in the first place.

Being in the right environment was so important to Watson that he left the University of Copenhagen, against the terms of his fellowship, when he realized he needed the expertise of the Cambridge circle to make a real breakthrough. He did what was necessary and asked for permission later. What would’ve happened had he sat around waiting for permission?

The casual sexism with which Watson treats Rosalind Franklin, the expert in X-ray photography that wound up playing a major part in the discovery of the double helix, was striking to me reading the book in 2021. Watson tends to characterize her opinions and insights as obstinancy or rudeness. He doesn’t view his male colleagues the same way.

If cooperation is so critical to science, I can’t help but wonder what Watson could’ve achieved with a more collaborative attitude toward Franklin. Would the breakthrough have come even sooner? Would they have been able to make even more discoveries together if Watson had been more open to her expertise?

I loved getting a view of what is in a scientist’s mind as they make a major breakthrough. Watson was by no means certain he was right at first, but he worked methodically to prove what he suspected. That even such a genius has doubt in his ideas can cheer the rest of us!

The great chemist Linus Pauling had suggested a different structure of DNA, which turned out to be incorrect. But when he saw the elegance of Watson and Crick’s double helix, he was in awe and thrilled, rather than upset at being proven wrong.

I find that attitude to be one of the great things about science. There is both collaboration and competition, but in the end, everyone is working toward one goal: understanding.

In all, I found Watson’s book interesting and instructive. Since it was written in 1968, I’m not sure how many people are still reading it, but it’s worth a look. Check it out!

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What I Learned From an Investor Who Turned $100,000 into $100,000,000

Above: Angel investor Jason Calacanis

The angel investor Jason Calacanis got in on the ground floor of Uber, Thumbtack, and other highly successful software companies, multiplying his $100,000 investment into $100,000,000 in just 6 years. With results like that, you know I had to read his book!

The idea of helping, even in a very small way, to build the future appeals to me a great deal. And if my investment multiplied many times over, well, I wouldn’t mind! 🙂 In this superb and brief book, Calacanis lays out a detailed game plan on how to achieve results like his.

He suggests beginning with syndicate deals, in which an angel investor invests alongside more experienced angels. You can begin with as little as $1,000 per investment, and such syndicates can be found at AngelList, SeedVest, and elsewhere. In fact, the author has his own syndicate, here. Unlike most investment managers, the syndicate lead only gets paid if he scores for you. There is no management fee at all, but the lead does keep 20% of any profits for his/her trouble.

You can build your skills, experience and connections in those syndicate deals, and then move on to deals on your own. Calacanis explains that you have to evaluate the founder himself/herself more than the product. It’s the person behind the company that will make or break it. Products can change a lot more easily than people can. What are is the founder’s chances of suceeding in this business, and in life?

I was struck by how similar the approach to finding investments is to podcasting, journalism, or for that matter, blogging. Calacanis advises asking short questions and writing down the founder’s answers at length. Then, you write deal memos when you invest, to lay out the thinking behind the investment. These could help remind you of your reasoning if times get tough for the company, and also guide future investments.

There’s a ton of actionable details in this book, and I won’t get into all of them here. But if you’re even remotely considering investing in early stage companies, I strongly suggest giving this entertaining and highly readable book a look!