Tremendous

An angel investor's take on life and business

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

  • 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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    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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  • 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

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

  • 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

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

  • Note: This is not financial advice

    This morning, new preferred shares of AMC Entertainment Holdings debuted on the New York Stock Exchange.


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    Interestingly, the new shares (ticker symbol APE) have the same ownership interest and rights as normal AMC shares. But as I write this, they trade for $5.80, versus $10.52 for AMC shares.

    The shares appear ripe for one of Wall Street’s favorite strategies: arbitrage.

    If the two share types have the same economic value, they should trade at the same price. Hedge funds often buy an underpriced security while selling short an equivalent higher priced one.

    The bet: the two prices will converge.

    I expect hedge funds to buy APE shares while shorting AMC common stock. On paper the strategy makes sense, but there’s a little problem…

    AMC shares are heavily shorted. 20% of the float has already been sold short.

    If hedge funds continue shorting the stock, they become vulnerable to a short squeeze. Huge run-ups in shares of AMC, GameStop Corp. and others have bankrupted hedge funds before, such as Melvin Capital Management.

    What’s more, both AMC and APE shares have passionate fanbases that can cause massive volatility. The human factor could cause a seemingly straightforward pairs trade to go very, very wrong.

    Hedge funds should heed the lesson of Melvin Capital and avoid shorting volatile meme stocks. But as Benjamin Franklin said:

    “Wise men don’t need advice. Fools won’t take it.”

    How do you think hedge funds will react to the debut of APE shares? Leave a comment at the bottom and let me know!

    More on markets:

    AMC’s 9 Million Missing Shares

    Is Melvin’s Gabe Plotkin Headed to Prison?

    Wall Street Banks Turn on Each Other as Federal Probe Looms

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

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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. 

  • How do angels and VC’s choose companies to invest in? Why do some founders struggle in fundraising?


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    I dug into all that and more recently with Travis King, co-founder of Launch Point Labs. Some interesting points:

    2:42: How I choose companies to invest in

    6:57: How you can work backwards from the customer to the product

    8:44: How much help do founders need? And the ways I try to add value for startups.

    14:55: Today’s market slowdown and how I’m adapting.

    17:16: How angel investors can get burned.

    19:27: Lessons from the SaaS OG, Jason Lemkin

    23:35: Why some founders have unrealistic expectations about fundraising.

    27:26: Why there’s no substitute for traction

    28:49: Why I’m being brutally honest with founders in today’s tough market

    What questions do you have? What did we miss?

    Leave a comment at the bottom and let me know!

    Have a great weekend everyone! 👋🥳🎉

    More on tech:

    Record Funding for Climate Startups in Q2

    Angels Flocking to DTC Brands: Mistake or Opportunity?

    Will Adam Neumann Change Housing Forever?

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    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. 

  • It’s been a rough August. And it’s not over.

    Short sellers in shares of AMC Entertainment Holdings have lost $653 million so far this month. From a new Bloomberg report:


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    Investors betting against the most well-known meme stocks have lost about $1.65 billion this month after the shares soared in value, prompting a short squeeze.

    AMC Entertainment Holdings Inc.’s 47% rally has pushed mark-to-market losses for short-sellers to $653 million, S3 Partners data show. Similar bets against Bed Bath & Beyond Inc. and GameStop Corp., which have surged 359% and 19%, respectively, in August, lost $1 billion combined.

    Bets against meme stocks like AMC and GameStop blew up hedge fund Melvin Capital Management, among others. But like moths to the flame, short sellers seem drawn to losing more.

    Many firms like Melvin heavily shorted multiple meme stocks. Rallies in several meme names at once multiplies their losses.

    Shorting a heavily shorted company is a recipe for a short squeeze. Add a fanatical retail following, and disaster could strike at any moment.

    The ideal short sale candidate is a failing company that isn’t heavily shorted. And you want something with no cult following.

    Or better yet, follow the counsel of a hedge fund manager I had dinner with recently:

    “Short selling is a great way to lose money.”

    I guess some are learning. As for the rest, bon chance.

    What do you think of short sellers recent losses? Leave a comment at the bottom and let me know!

    More on markets:

    AMC’s 9 Million Missing Shares

    Is Melvin’s Gabe Plotkin Headed to Prison?

    Shorts Having Their Worst Month Since January 2021

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

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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. 

  • My appointment got cancelled, so I get to spend the afternoon with you guys! And we’ve got some big news…

    As founders struggle with a down market, one corner of startupland is flush. Climate startups raised record funding in the second quarter.


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    From a report out this morning on Bloomberg:

    Carbon and climate startups have attracted record investments at a time when other industries are struggling to tap funds from venture capitalists.

    Buoyed by corporate and government pledges to cut greenhouse gas emissions, a record $1.4 billion poured into climate and carbon-focused startups in the second quarter of this year. That’s in stark contrast to the broader market for venture funding, which faces its largest quarterly percentage drop in nearly a decade, according to CB Insights.

    These startups have an incredible tailwind: $369 billion in government climate funding.

    There are billions of dollars for batteries, reducing emissions, and reforestation. A small portion of one of these categories is enough to make a $1 billion startup.

    I had a front row seat when huge government subsidies hit another part of tech — medical software. Before I became an investor, I worked on one of the leading platforms, Epic.

    When the 2009 stimulus pumped $25 billion into the sector, everything went bonkers.

    My phone started ringing off the hook with recruiters. And I started making a lot more money.

    I wasn’t any better at the job than I was before the bill passed. But all that government money had to go somewhere.

    Climate tech is about to be hit by the same kind of cash tsunami. And if you’re standing anywhere nearby, you’re going to get wet.

    I favor SaaS products with a positive climate impact. Think software to reduce a truck fleet’s fuel economy, for example.

    No scientific breakthrough needed, no messy and low margin “stuff,” just a proven business model applied to a new area. And it sells itself — even a climate change skeptic wants to save on fuel!

    I actually just invested in a climate tech company a couple of months ago. (I’ll give you more details when the deal is announced.)

    A great SaaS business is always yummy. A great SaaS business with a tailwind of government cash and regulation — chef’s kiss.

    What do you think of climate tech? Leave a comment at the bottom and let me know!

    More on tech:

    Will Adam Neumann Change Housing Forever?

    Angels Flocking to DTC Brands: Mistake or Opportunity?

    Seed Valuations Are…Up?

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    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: President Biden signs $369 billion in climate funding into law

  • Angel investors are flocking to Direct to Consumer (DTC) brands, even as venture firms have pulled back. From a report out this morning in Business Insider:

    A growing class of angel investors is now swooping in to write the early checks fledgling DTC-brand founders need to bring their products to market. While individual angel investors may not offer the large sums of cash or the pedigree and connections a blue-chip Silicon Valley VC can provide, they offer other advantages, DTC founders told Insider. Perhaps most importantly, they are willing to open their checkbooks to untested new brands as VCs analyze them more critically.

    “If you think about the early floodgates of VC money going into DTC, it was because they were using a specific playbook,” Eunice Shin, a partner at Prophet, a DTC consultancy, said. “That playbook is broken.”

    DTC brands like Peloton, Casper and Blue Apron used to be some of the best known names in tech. Now those companies are struggling and VC’s are wary.

    So founders go where they can: to angels. Angels usually ask fewer questions and may be unaware of the headwinds DTC is facing.

    Advertising, manufacturing and shipping costs have skyrocketed. Supply chains are a mess.

    Things started to go very wrong for DTC last spring. Apple released an iOS update that let users stop ad tracking, and almost all did.

    This meant apps like Facebook and Instagram had no idea who saw an ad.

    The update was a gut punch for DTC brands. A woman’s underwear startup that only ships in the US could waste its precious ad dollars advertising to men in Germany.

    Many startups saw their Customer Acquisition Cost (CAC) triple. What had been a solid business model no longer worked.

    And it’s going to get even worse. Google also plans to limit ad tracking next year.

    What happens when your advertising, manufacturing, and shipping costs skyrocket? You start bleeding red ink.

    VC’s are usually familiar with these problems facing DTC. Unfortunately, many angels are not.

    As scary as things may be in DTC land, a few companies have bucked the trend.

    Eight Sleep, which produces a heating and cooling cover for mattresses, is one great example. The cooler surface can greatly improve your sleep.

    Eight Sleep produces a highly differentiated and expensive product. Its mattress covers start at $1,845, and its mattresses are even more.

    This is the kind of consumer product that can still be a great business.

    It’s expensive enough to absorb a higher CAC. And it doesn’t have to fight it out with a dozen competitors.

    Still, I prefer SaaS. You’re not dependent on online ads, customers tend to stick around, and your product is infinitely scalable without any messy “stuff.”

    DTC brands are sexy.

    A yummy steak from Blue Apron is a lot more exciting than a SaaS revenue retention product. And it’s a service you could use yourself, unlike most SaaS products.

    But if we want to make returns, we have to focus on what’s financially viable, not just what’s exciting.

    What do you think about the DTC industry today? Leave a comment at the bottom and let me know!

    And now, I’m off to invest in some more boring SaaS companies. 🙂

    P.S. There will be no blog tomorrow. I have an appointment. See you Thursday!

    More on tech:

    Will Adam Neumann Change Housing Forever?

    Seed Valuations Are…Up?

    $500 Billion in Venture Capital is Sitting on the Sidelines

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    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.