Tremendous

An angel investor's take on life and business

  • Brave Beats Safari in Security

    Today, I saw something that would really piss Steve Jobs off.

    Let me explain.

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    Websites are constantly trying to track us. Meanwhile, every browser seems to claim to protect our privacy — but do they really?

    Today, I ran an identical test on two leading browsers: Apple’s Safari, which I use every day, and Brave.

    Safari is second only to Chrome among internet users, with a 19% share. Brave is much smaller but claims to have 50 million monthly active users, doubling every year.

    I tested Safari and Brave using an awesome tool called Cover My Tracks. This tool shows how easy it is for trackers to identify you.

    Safari

    Safari produced mediocre results. It only blocked some trackers and allowed websites to “fingerprint” me.

    A browser fingerprint is the unique combination of characteristics your browser has.

    What add-ons do you use? What fonts are installed?

    When you look at these and other factors, it turns out two browsers are rarely the same. When you see my unique combination on the internet, you can be pretty sure it’s Francis.

    Brave

    Brave crushed it. It blocked trackers and stopped fingerprinting cold.

    Brave does this by randomizing your browser’s fingerprint.

    Remember all those characteristics about your browser that make you unique? Brave slightly modifies them, making you very hard to trace.

    Imagine if every time you touched a doorknob, your fingers left a slightly different print. You’d be pretty hard to track down!

    I’m appalled that a multitrillion dollar corporation that talks about privacy nonstop gives you worse security than a tiny startup. If Steve Jobs were here, he’d be screaming at the Safari team and having them escorted from the building.

    It’s no wonder Brave does such an awesome job at protecting our privacy. Its founder and CEO Brendan Eich created Javascript and co-founded Mozilla.

    With such a great product, awesome founder and rapid growth, I only wish I were an investor in this one!

    Test your browser’s privacy here. And check out Brave to see how it compares!

    How do you protect your privacy online? Leave a comment at the bottom and let me know!

    More on tech:

    I Pitched a Robot VC

    Where Are All the Startup Acquisitions?

    Mark Twain: Venture Capitalist

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    Fundrise

    This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 with great returns.

    More on Fundrise in this post.

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    Misfits Market

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  • Hedge Fund Manager’s Arrest Shows How Market Manipulation Works

    Hedge fund manager Neil Phillips has been arrested in Spain this week.

    He is charged with masterminding a market manipulation scheme that reached from the UK to Asia. His strategy shows how hedge funds manipulate markets from currencies to stocks.

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    From a new report in Bloomberg:

    Phillips was charged with conspiring to manipulate the US dollar-South African rand exchange rate in late 2017. The indictment, which was returned in March but previously sealed, describes at least two co-conspirators, raising the possibility of charges against more people.

    Neil Phillips

    Phillips faces up to 20 years in prison if convicted. His scheme involved buying an option on the dollar-rand exchange rate, then manipulating the exchange rate to make his option pay off:


    With the option set to expire, Phillips began making spot trades in an effort to push the exchange rate lower late on Christmas Day, while directing a Singapore-based employee of an unidentified bank to sell $725 million in exchange for more than 9 billion rand, according to prosecutors. That pushed the exchange rate below the barrier, triggering the $20 million option. Phillips collected more than $15.6 million from the deal and also allocated $4.34 million to an unidentified client.

    Phillips’ moves show us how market manipulation works.

    He took advantage of thin trading late Christmas Day. Markets are easier to manipulate when trading is light.

    He also used trades in an underlying asset to benefit an options position. The same approach is likely common in stocks.

    Phillips even went as far as involving a co-conspirator on the other side of the world in the hopes of hiding his illegal trades. But he was foolish enough to discuss the whole thing in chat messages on his Bloomberg terminal.

    Bloomberg routinely gives chat records to the government in subpoenas. Phillips might not be facing prison had he used an encrypted app like Signal.

    I find the Phillips case fascinating for how it trains us to spot hedge fund manipulation of markets.

    If we suspect price manipulation, we should look for big trades at odd times. Major sell order right before the close on the last trading day of the year?

    It might be worth a look.

    Where do you see signs of market manipulation? Leave a comment at the bottom and let me know!

    There will be no post on Monday for the holiday. Have a great Labor Day weekend everyone! 👋🥳

    More on markets:

    AMC Fails to Deliver Pass 700,000 in New Report

    Why Hedge Funds May Pile into APE Shares

    Is Melvin’s Gabe Plotkin Headed to Prison?

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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 with great returns.

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    Photo: “prison fence” by Brad.K is licensed under CC BY 2.0.

  • I Pitched a Robot VC

    Every day, founders pitch me on their startups. This morning, I thought “Why not turn the tables for a change?”

    So I pitched 3 VC’s on a startup idea. But they weren’t your usual investors — all 3 were robots. 🤖

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    These robot VC’s live on a new platform called PitchExpert. They use GPT-3, a form of AI, to ask questions and help you refine your pitch.

    I started with an elevator pitch:

    It costs $10,000 or more to move into an apartment in many cities. The average person can’t afford that. We provide a loan so you can move into a great apartment today!

    Here’s what the grizzled veterans had to say:

    VC 1:

    I like it! You’re onto something with this idea. Here are a few suggestions to make your firm more attractive to investors and increase its valuation:

    1. Make sure you have a solid business model in place. Figure out how you’re going to generate revenue and profit from this service.
    2. Do some market research to validate your assumption that there is indeed a need for this service. Talk to potential customers and get feedback on what they think of the idea.
    3. Put together a strong team of co-founders and employees who can execute on the business plan and grow the company successfully.

      Hey hey, not a bad reception! And talking to potential customers and figuring out an exact revenue model are great suggestions.

      VC 2
    1. Make sure you are clear on your target market. Who is your ideal customer?
    2. Do your research on the competition. What are they doing and how can you differentiate yourself?
    3. Have a solid plan for how you will make money. How will this business be profitable?

      Not quite as sunny but probably even more useful. Knowing everything about potential customers and competitors is a good tip.

    VC 3

    This is a terrible idea.

    1. Don’t try to solve the problem of high rent prices.
    2. Instead of a loan, try a subscription model where people pay a monthly fee.
    3. Use that money to help people move into better apartments.

    Jerk. I’m going to unplug this guy.

    What’s more, a subscription model when people move only occasionally doesn’t make much sense. Why would you pay for a subscription to something you use only once every 5 years, for example?

    I’m actually amazed how spot on the first two VC’s were.

    I like the mix of VC’s: Mr. Friendly (VC1), Mr. Just the Facts (VC2), and Mr. Abrasive (VC3). It mirrors real life.

    I found VC2 to be the most helpful. His suggestions made a lot of sense and could help me refine the business model.

    As an investor, I try to be closest to VC2. I mostly ask questions and don’t offer too many judgements, positive or negative.

    I am mostly there to learn, not to direct the founder.

    What do you think the robot VC’s got right? What did they get wrong?

    Leave a comment at the bottom and let me know!

    More on tech:

    Where Are All the Startup Acquisitions?

    Mark Twain: Venture Capitalist

    The Power Law (Part One)

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    Fundrise

    This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 with great returns.

    More on Fundrise in this post.

    If you decide to invest in Fundrise, you can use this link to get $100 in free bonus shares!

    Misfits Market

    I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

    I wrote a detailed review of Misfits here.

    Use this link to sign up and you’ll save $15 on your first order. 

    Photo: “Robot at the British Library Science Fiction Exhibition” by BadgerGravling is licensed under CC BY-SA 2.0.

  • AMC Fails to Deliver Pass 700,000 in New Report

    Note: This is not financial advice.

    Fails to deliver in shares of AMC Entertainment Holdings hit massive levels this month.

    Failed trades peaked at over 700,000 shares, according to a report out this morning from the SEC. They remained in six figure territory for all but two days in the period, which covers the first half of August.

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    This many failed trades is highly unusual for most stocks. Let’s zoom in on August 8th and compare AMC with some of the largest stocks in the market:

    Alphabet (Google):: 22

    Amazon: 533,744

    Apple: 379,843

    Microsoft: 0

    Tesla: 49,705

    AMC: 723,636

    Keep in mind, these other companies are dramatically larger. But month after month, little old AMC has far more failed trades.

    Fails to deliver can happen for benign reasons, like administrative errors. But why would such errors affect this stock way more than others, time and time again?

    The more likely explanation is naked short selling. This involves selling short shares you never actually borrowed.

    It’s a powerful weapon to push down a stock’s price.

    You don’t have to find any shares to borrow. And you don’t have to pay any interest to borrow them!

    This means you can sell short an unlimited number of shares. Awesome, right?

    It’s illegal for a hedge fund to do this. But that may not stop them, especially given lax enforcement.

    But perhaps the most incredible thing is that 723,636 may understate the number of trades that are failing.

    The Depository Trust & Clearing Corporation (DTCC) puts failed trades that don’t resolve for a long period into an “obligation warehouse.” At that point, they essentially disappear.

    Earlier this month, over 9 million shares worth of failed trades in AMC stock suddenly vanished.

    Maybe the DTCC were busy beavers cleaning it all up. Or maybe they just swept them under the rug.

    We won’t know until the DTCC and SEC offer transparency on what happens to failed trades.

    Something tells me we’ll be waiting a while.

    What do you think of the new SEC report? Leave a comment at the bottom and let me know!

    More on markets:

    AMC’s 9 Million Missing Shares

    Morgan Stanley Investigation Spreads to Multiple Countries

    Is Melvin’s Gabe Plotkin Headed to Prison?

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    Fundrise

    This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 with great returns.

    More on Fundrise in this post.

    If you decide to invest in Fundrise, you can use this link to get $100 in free bonus shares!

    Misfits Market

    I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

    I wrote a detailed review of Misfits here.

    Use this link to sign up and you’ll save $15 on your first order. 

    Photo: Melvin Capital founder Gabriel Plotkin

  • Where Are All the Startup Acquisitions?

    It’s tough times in startupland. Valuations are down and fundraising is hard.

    For cash-rich tech giants, it should be shopping season.

    But the big boys are sitting it out. From a report out this morning on Crunchbase News:

    The four most valuable American companies have enough capital to acquire any startup they desire.

    But despite their deep coffers, Apple, Amazon, Google and Microsoft aren’t doing a lot of buying.

    So far this year, the “Big Four” have made just five acquisitions of private, venture-backed companies, per Crunchbase data. Of those, none were known unicorns and only one had a disclosed purchase price. That indicates the rest were smaller deals by tech giant standards.

    And it’s not just a few megacaps that aren’t buying. M&A of VC-backed startups in general has fallen this year.

    This is a strategic mistake for big tech. When the prices are low, that’s the time to buy!

    A downturn is the perfect time for a company like Google to solidify its competitive advantage. It can expand its offerings, making sure it owns the products of the future.

    Let’s take an example. I recently came across a new search engine called Andi.

    Ask Andi a question, and it gives you an answer in what looks like a text message.

    It’s pretty cool! And given how popular texting is, it could be the future of search.

    Of course, Google could tell a bunch of engineers to build an Andi knockoff. But Google would start the race way behind.

    Or Google could buy Andi for a tiny fraction of its massive cash pile. If this could be the company that disrupts your massively profitable business, why not just buy it and remove the risk?

    What’s more, acquisitions are a great way to bring on a bunch of highly skilled people at once. It’s easier to hire a group of great people who are experienced at collaborating than to hire one by one.

    And those small acquisitions can have a big impact.

    Google bought Android for just $50 million. The company that became AdSense cost them just $102 million.

    And yet, big tech isn’t shying away from acquisitions altogether.

    Microsoft is acquiring Activision for $68 billion, it’s biggest deal ever. And Amazon is scooping up One Medical, Signify Health, and iRobot in multibillion dollar deals.

    With checks like that being written, big tech should pick up some startups for a song while they’re at it. After all, as Jeff Bezos said, “big things start small.”

    What are the best acquisitions big tech could make and why? Leave a comment at the bottom and let me know!

    More on tech:

    Adam Neumann Was Their Biggest Investor — Now He’s Their Biggest Competitor

    Mark Twain: Venture Capitalist

    Startups’ Secret Weapon for Recruiting: Their Investors

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    If you found this post interesting, please share it on Twitter/Reddit/etc. This helps more people find the blog! 

    Fundrise

    This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 with great returns.

    More on Fundrise in this post.

    If you decide to invest in Fundrise, you can use this link to get $100 in free bonus shares!

    Misfits Market

    I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

    I wrote a detailed review of Misfits here.

    Use this link to sign up and you’ll save $15 on your first order. 

    Photo: “Jeff Bezos” by jurvetson is licensed under CC BY 2.0.

  • Morgan Stanley Investigation Spreads to Multiple Countries

    Morgan Stanley, already under federal investigation in the US, is now facing another probe. This time, it’s in Korea.

    From a report that broke last night on Bloomberg:

    Morgan Stanley’s stock short selling practices are being inspected by South Korea as part of a broader effort by the nation’s financial watchdog to clamp down on bets against equities, according to a person familiar with the matter.

    Goldman was fined in 2018 for naked short selling in the Korean market. Regulators may be looking for similar infractions by Morgan.

    This comes as Morgan forces another executive out under mysterious circumstances. Executive Director Charles Leisure was placed on leave last week.

    From a report out over the weekend, also on Bloomberg:

    Charles Leisure, an executive director who worked on the New York-based bank’s equity syndicate desk, was put on leave this week, people with direct knowledge of the matter said, asking not to be named because the information isn’t public. He was part of a team that handled block trades — deals that have been facing scrutiny from federal prosecutors in the Southern District of New York and the US Securities and Exchange Commission. 


    Leisure worked for Pawan Passi. Both handled block trades, or buying and selling of large amounts of stock.

    Big investors rely on banks like Morgan to quietly offload huge chunks of stock. Morgan may have tipped hedge funds to the sales beforehand, giving them a chance to front-run the trades.

    Banks have an incentive to play footsie with hedge funds because of what’s called prime brokerage. A hedge fund’s prime broker handles the fund’s trades, a very lucrative relationship.

    If a bank gives them information about market-moving trades, the bank could be more likely to win that business.

    So far, nothing has been proven against Leisure, Passi or Morgan itself. Perhaps all its trades were aboveboard.

    But consider the overall picture.

    Multiple executives in the same area placed on leave. Investigations spreading from one country to the next.

    Even other Wall Street banks are raising concerns about Morgan’s activity, a rare move.

    Something tells me that where there’s smoke, there’s fire.

    What do you think is going on at Morgan Stanley? Leave a comment at the bottom and let me know!

    More on markets:

    Wall Street Banks Turn on Each Other as Federal Probe Looms

    Is Melvin’s Gabe Plotkin Headed to Prison?

    Hedge Fund Giant Tiger Loses Over $18 Billion — Long Fund Down 64%

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    Fundrise

    This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 with great returns.

    More on Fundrise in this post.

    If you decide to invest in Fundrise, you can use this link to get $100 in free bonus shares!

    Misfits Market

    I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

    I wrote a detailed review of Misfits here.

    Use this link to sign up and you’ll save $15 on your first order. 

    Photo: “Morgan Stanley Headquarters” by Alex E. Proimos is licensed under CC BY-NC 2.0.

  • Mark Twain: Venture Capitalist

    Mark Twain is one of the greatest American authors. But not many people know he was also a venture capitalist.

    A phenomenally bad one.

    Twain lost the equivalent of nearly $10 million* in a single investment: the Paige Compositor. Invented by James Paige, it was one of the first typesetting machines.

    The Paige Compositor

    The machine was a marvel, printing faster than anything else — when it worked. But with 18,000 moving parts, the Compositor was prone to breakdowns.

    Paige worked on the machine for over two decades before releasing it. Twain repeatedly doubled down on his initial $5,000 investment during this time, putting in a total of $300,000.

    In 1887, Paige finally put the Compositor on the market. By that time, its main competitor, Linotype, had already been on the market for 3 years.

    Linotype was cheaper, simpler, and less prone to breakdowns. It soon ran away with the printing market.

    Paige died penniless and Twain went bankrupt.

    What can we learn from their mistakes?

    Paige’s critical error was failing to get a Minimum Viable Product (MVP) to market as soon as possible.

    This would’ve let Paige begin to learn what customers want and what competitors were capable of. He might have soon realized that customers didn’t like his machine because it was too expensive and unreliable.

    Then, Paige could’ve simplified it, reducing breakdowns and cost. Paige and Twain just might have wound up with a huge success!

    Instead, Paige kept tinkering endlessly, divorced from the lessons of the market.

    Meanwhile, Twain should’ve never put so much money into a single company!

    You never invest more than you can afford to lose in startups. And you must make many small bets to give yourself enough chance of hitting an outlier success.

    If Twain wanted to invest in the Compositor, he should’ve placed a small bet and waited. If the company got to market and started selling lots of machines, he could place another small bet.

    Investors doubling down on winners is what we call “milestone based funding.”

    Companies get a little money to start. Then, if and only if they hit certain milestones, they get more.

    It’s the fundamental principle of Silicon Valley, like F = ma in physics.

    Today, we systematically avoid the mistakes Twain and Paige made.

    We read The Lean Startup by Eric Ries and learn to launch as soon as possible. We read Angel by Jason Calacanis and learn to make many small bets instead of one big bet.

    But let’s not judge Twain and Paige too harshly. After all, they never got to read those books.

    The lessons of early entrepreneurs and investors taught us what we know today.

    After his bankruptcy, Twain went on a world tour telling jokes and stories on stage. He traveled as far as India and made enough to pay off his debts.

    Things were looking up for Twain. And then he heard about another revolutionary invention…

    What lessons do you take from Twain and the Paige Compositor? Leave a comment at the bottom and let me know!

    Have a great weekend everyone! 👋

    More on tech:

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

    The Lean Startup

    John Doerr’s Biggest Mistake

    Note: Twain invested approximately $300,000 in the Paige Compositor, which failed in 1894. That equates to about $9.7 million in today’s dollars.

    Photo: Twain in Nikola Tesla’s lab

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    Fundrise

    This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 with great returns.

    More on Fundrise in this post.

    If you decide to invest in Fundrise, you can use this link to get $100 in free bonus shares!

    Misfits Market

    I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

    I wrote a detailed review of Misfits here.

    Use this link to sign up and you’ll save $15 on your first order. 

  • Startups’ Secret Weapon for Recruiting: Their Investors

    One of the hardest things for any startup is attracting great employees. But new research from Harvard Business School points to a shortcut:

    New research finds that job seekers are two-thirds more likely to apply to a startup if they know it is backed by a top venture capital (VC) investor, according to a new study coauthored by Harvard Business School Professor Shai Bernstein.

    To test if the name of a top investor makes a difference in luring applicants, the researchers collaborated with AngelList Talent, an online recruitment platform, to conduct a randomized experiment on the platform.

    The researchers found that exposure to information that a startup is backed by top VC investors increased job applications dramatically—by 67 percent.

    “The same startup receives significantly more interest from potential employees when it is represented with the top investor badge than when it is not,” they write.

    Early stage startups benefited the most. For companies at Series B and later, having top investors had less impact on applicant interest.

    This points to a great strategy for startups with top investors: shouting the investors’ names from the rooftops.

    If you have Sequoia, Benchmark, or any top firm on your cap table, put it in every job ad. Have your employees mention it when they recruit their friends.

    Another great way to land top prospects is press coverage. PayPal got a huge recruiting boost from media reports in its early days.

    And unlike capital from top investors, media coverage is available to anyone with a great story to tell.

    Founders: how do you recruit top employees? Investors: what recruiting strategies are working well for your portfolio companies?

    Leave a comment at the bottom and let me know!

    More on tech:

    Adam Neumann Was Their Biggest Investor — Now He’s Their Biggest Competitor

    John Doerr’s Biggest Mistake

    Talking Startup Fundraising with Travis King of Launch Point Labs

    If you found this post interesting, please share it on Twitter/Reddit/etc. This helps more people find the blog! 

    Save Money on Stuff I Use:

    Fundrise

    This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 with great returns.

    More on Fundrise in this post.

    If you decide to invest in Fundrise, you can use this link to get $100 in free bonus shares!

    Misfits Market

    I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

    I wrote a detailed review of Misfits here.

    Use this link to sign up and you’ll save $15 on your first order. 

    Photo: “Sequoia Capital” by isriya is licensed under CC BY-NC 2.0.

  • Adam Neumann Was Their Biggest Investor — Now He’s Their Biggest Competitor

    It didn’t take long for Adam Neumann to find controversy. Before starting his new residential real estate startup Flow, Neumann made a big investment in a company that’s suspiciously similar.

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    From an excellent report out yesterday in Forbes:

    When staff at real estate startup Alfred arrived at work last Monday morning, they were surprised to discover that their largest investor, former WeWork CEO Adam Neumann, appeared to have started a rival company — and raised $350 million to compete against them.

    Flow, Neumann’s splashy but mysterious new real estate venture, was aiming to build “the future of living,” influential venture capitalist Marc Andreessen wrote in a blog post announcing the investment. Alfred’s motto — “welcome to the future of living” — sounded uncomfortably similar.

    Neumann is still a major investor, though he has stepped back from the board.

    Neumann had wanted to acquire Alfred, but the terms of a new funding round blocked it. He appears to have set up Flow as a response.

    Investors in startups are not supposed to back competing companies.

    An investor is privy to tons of confidential information about a startup. Were that information disclosed to a competitor, even accidentally, it could cause serious damage.

    Starting a competing company rarely comes up, but should be out of bounds for the same reasons.

    Flow already appears to be cannibalizing Alfred’s business:

    Alfred may have already started seeing the effects of Neumann’s influence. One of the Norwalk, Connecticut, apartments where Alfred participated in the experiment with Greystar had been featured on Alfred’s site as an example of how it works with landlords. But when a Forbes reporter stopped by to speak to residents, one told them that the app the building offered for use was Carson, the Neumann-owned competitor. The Norwalk apartments have since disappeared from Alfred’s site.

    With a serious competitor that just raised $350 million, Alfred will find it hard to raise more money. Do investors want to back Alfred’s team against a more experienced and better funded rival?

    This controversy shows the danger of doing business with unscrupulous people. Neumann’s money was tempting, but the juice wasn’t worth the squeeze.

    Normally, a founder who created a multibillion dollar public company would be a great business partner — even if he’d made some mistakes. Mistakes help people learn.

    But we must distinguish between strategic errors and plain lack of ethics. You can learn strategy, but you can’t learn scruples.

    What do you think of Neumann’s return? Leave a comment at the bottom and let me know!

    More on tech:

    Will Adam Neumann Change Housing Forever?

    John Doerr’s Biggest Mistake

    Talking Startup Fundraising with Travis King of Launch Point Labs

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    Fundrise

    This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 with great returns.

    More on Fundrise in this post.

    If you decide to invest in Fundrise, you can use this link to get $100 in free bonus shares!

    Misfits Market

    I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

    I wrote a detailed review of Misfits here.

    Use this link to sign up and you’ll save $15 on your first order. 

    Photo: WeWork and Flow founder Adam Neumann

  • John Doerr’s Biggest Mistake

    In 2007, venture capitalist John Doerr met an intriguing young entrepreneur. His name was Elon Musk.

    Musk pitched Doerr on investing in his new car company, Tesla. Doerr passed.

    The mistake cost him billions.

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    The legendary investor opened up on this major regret in an interview out this morning on Bloomberg:

    The billionaire chairman of Kleiner Perkins had the opportunity in 2007 to back “an ambitious, slightly crazy entrepreneur” named Elon Musk before he became the world’s richest man, but ultimately decided against it, as new car companies traditionally fail far more often than they succeed. 

    “That’s probably the worst investment decision of all time,” Doerr, 71, said…

    Doerr did wind up investing in an electric car startup. But it wasn’t Musk’s:

    “There have been 400 new car companies in the nation’s history. Every one but one has gone bankrupt. But I was still very attracted to the market, and we had the choice of backing a brilliant car designer by the name of Henrik Fisker, or an ambitious, slightly crazy entrepreneur by the name of Elon Musk at Tesla. Well, we made the wrong decision.”

    On paper, Fisker seems like a great bet. He designed iconic cars like the Aston Martin Vantage and had deep experience in the auto industry.

    What he didn’t have was a strong background as an entrepreneur.

    Musk had no real auto industry credentials. But he had co-founded PayPal and sold it to eBay for $1.5 billion.

    Whatever he may have lacked, Musk was an ace entrepreneur. He took that experience to Tesla and built it into a colossus.

    The lesson for me here as an angel investor is to not overvalue industry expertise. Sometimes it takes someone from outside an industry to revolutionize it.

    Amazon was Jeff Bezos’ first store. Travis Kalanick never owned a cab company.

    Founders should be familiar with the market they’re operating in. But if they need deep industry expertise, they can always hire for it.

    But what’s most instructive about Doerr’s mistake is how it never mattered! He backed Google, Amazon, and countless others early, changing the modern world and making a fortune in the process.

    Doerr’s experience illustrates one of my favorite things about venture capital. You don’t have to be right all the time.

    In fact, you only have to be right once.

    Investors: how much do you value industry expertise? Founders: how important is industry background to your startup?

    Leave a comment at the bottom and let me know!

    More on tech:

    Talking Startup Fundraising with Travis King of Launch Point Labs

    Record Funding for Climate Startups in Q2

    The Power Law (Part Four): The First Venture Deal

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    Photo: “John Doerr” by Thomas Hawk is licensed under CC BY-NC 2.0.