Tremendous

An angel investor's take on life and business

  • The Top 5 Reasons I Pass On a Startup

    I looked at 4000 deals I’ve said no to in the last 3 years. Here are the most common reasons I passed…

    1) No revenue. This is by far the most common reason why I pass on a startup.

    Cash is king. If a company can get people to plunk down their credit card, it means their product really is valuable.

    I like to see $200-500k ARR when I invest. But unfortunately, most startups never make a dime in revenue.

    2) Wrong Industry. The next most common reason I pass on a startup is that it’s in an area I don’t generally invest in.

    Thus far, I’ve mostly stuck to software. I’m planning to branch out to a few biotech and defense deals, but there are many areas I don’t know about and don’t touch.

    Think stuff like satellites, semiconductors and agtech. I don’t know a lot about those fields and they’re not the areas I’m most interested in. These may be great companies, but I leave them to other investors.

    3) Revenue Growth Too Low. The 3rd biggest reason is that a company has revenue, but it’s not growing very fast.

    If I look at my most successful investments today, they all had incredibly high growth when I invested. I look for at least 3x YoY growth in revenue.

    4) Too Late Stage. While many companies are too early for me, others are already much too big.

    Since I focus on early stage, I don’t write a check into something like SpaceX. In the last year or so, secondaries in major startups have become more and more frequent. There are some great opportunities here, but it’s just not where I focus.

    5) Not a Delaware C Corp. When it comes to raising from US investors, there’s only one way to go: a Delaware C Corporation.

    This entity lets you do important things a startup needs to do, like issue stock options. You’d be amazed how many companies get this wrong. Give yourself an advantage: incorporate properly from Day 1.

    Wrap-Up

    Here’s what you, as a founder, can learn from this…

    Focus on investors that invest in companies like yours. Anything else is a waste of time.

    Before you pitch an investor, make sure they invest at your stage. If you’re a biotech company, see if they’ve invested in other biotech companies. If you’re in Australia, find out if they invest in Australia.

    Targeting your investors like this will take extra time at first. But you’ll save countless hours pitching people who are never going to write you a check.

    With a carefully honed list of investors, you can raise fast and get back to building.

    More on tech:

    Up to $15 Million, Tax Free — QSBS Changes in the BBB

    Where I’m Finding the Best Startups Now

    My Biggest Losses as an Angel Investor

    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. 

  • Memos from the Chairman

    “I have just informed the purchasing department that they should no longer purchase paper clips. All of us receive documents every day with paper clips on them. If we save these paper clips, not only will we have enough for our own use, but we will also, in a short time, be awash in the little critters.“ – Alan “Ace” Greenberg

    Why would the Chairman of a top Wall Street bank care about paper clips? Because it sends a message: be frugal.

    Ace Greenberg rose from a lowly clerk to Chairman and CEO of Bear Stearns, one of the top firms on the Street. During his time at the helm, he regularly wrote short letters to his staff, goading them toward success.

    These entertaining letters form the book Memos from the Chairman. When I heard Warren Buffett recommend it recently, I had to pick up a copy.

    Frugality? On Wall Street?

    “At last weeks partners meeting. Haimchinkel pointed out to me that the hors d’oeuvres had been upgraded considerably from peanuts. You will be happy to know that we are now back to peanuts.”

    Greenberg cut expenses relentlessly. Snacks, envelopes, stamps — everything. His partner in this crusade was Haimchinkel Malintz Anaynikal, a charming invented character always advising sobriety and common sense.

    Wall Street is more known for steak dinners and limos than frugality. Maybe that’s why Greenberg never stopped pushing his staff to cut costs.

    Little expenses add up, and every expense comes straight out of your bottom line. If Greenberg let the firm become undisciplined in how it used paper clips and envelopes, soon employees would be wasting much larger sums.

    Pick Up the Phone!

    “…the harder you work, the luckier you get.“

    Wall Street banks deal in some exotic stuff: derivatives, mortgage backed securities, you name it. But no matter how complex the business got, Greenberg always emphasized the basics.

    Answer the phone. Return calls promptly. Show up to meetings on time.

    These are basic things. But too often, we forget these basics, especially if we start to think we’re important.

    In the end, any business is about serving the customer. That starts with being responsive and punctual.

    So many of us in venture capital have long since forgotten these basic rules. A recent founder meeting I had is a case in point:

    “Thank you so much for being on time!” the founder began. Later in the meeting, he thanked me again for showing up at the time we agreed.

    Shouldn’t that be a bare minimum that any founder expects? You’d think. But evidently a lot of VC’s aren’t getting it right.

    I may not be the biggest investor. I may not be the smartest.

    But darn it, I can show up on time.

    How Bear Lost Its Way

    Today in 2025, Bear Stearns is known as a cautionary tale, if it’s known at all.
    The company collapsed during the financial crisis in 2008. JPMorgan wound up swallowing Bear for a pittance.

    If Bear had continued to follow the wise counsel of Ace Greenberg and Haimchinkel Malintz Anaynikal, this never would’ve happened.

    Greenberg ordered his staff to be in the office during business hours, no exceptions. But when Jimmy Cayne ousted Greenberg from the CEO role, those standards began to slip.

    Cayne often left on Thursday afternoons to play golf or bridge. Predictably, other executives followed his lead.

    No one at the top seemed to realize how bad the firm’s finances were getting during this time. No wonder — they barely worked!

    Bear’s collapse shows how the tone at a company is set from the top. Without strong leadership, a great company can cease to exist in just a few short years.

    Wrap-Up

    Greenberg practiced hard work, client service and frugality. If Bear had kept to those lessons, it might still be among America’s great banks.

    But it didn’t. And now it’s gone.

    It’s not complicated to put Greenberg’s lessons into practice. It’s all about doing basic things: returning messages, showing up on time, and watching expenses.

    Anyone can do these things. But most people don’t.

    That’s a great opportunity for the rest of us. It gives us a chance to stand out!

    I learned a lot from Memos from the Chairman and had quite a few good laughs too. Pick up a copy!

    More on books:

    Street Fighters: The Last 72 Hours of Bear Stearns, the Toughest Firm on Wall Street

    Hetty Green: The Witch of Wall Street

    Gambling Man: Masayoshi Son (Part Two) 

    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. 

  • Up to $15 Million, Tax Free — QSBS Changes in the BBB

    Angels can make up to $15 million tax free thanks to changes in the One Big, Beautiful Bill Act. This is part of a huge expansion of Qualified Small Business Stock (QSBS) in the new bill.

    What’s New With QSBS

    These changes to the rules around QSBS apply to shares acquired from July 4th onward. Here are some of the key provisions:

    • Maximum tax free gain is now $15 million (up from $10 million)
    • Max tax free gain is now indexed to inflation.
    • Tax benefits come sooner. You get 50% of your gains excluded from tax within 3 years and 75% within 4 years. At 5 years, 100% of your gains up to $15 million are excluded. (Before the bill, you only got exclusions after 5 years.)
    • Maximum assets of the startup you’re investing in can be up to $75 million (up from $50 million).

    This is a massive expansion of QSBS.

    Making startups with up to $75 million in assets eligible for QSBS means that the vast majority of angel investments should qualify. Startups usually don’t have that much in assets until Series B or C at the earliest. Meanwhile, angels are usually investing from pre-seed to Series A.

    The benefit is also indexed to inflation for the first time ever. That means Congress won’t need to revisit this any time soon.

    Is QSBS a Giveaway to the Rich?

    Getting $15 million tax free is pretty awesome for us. But is it good tax policy?

    My view is that QSBS is a critical way to build America’s economy and ensure we remain #1 in tech. Startups are a huge engine of job creation in America. Venture-backed startups create jobs at 8x the pace of other companies!

    QSBS is a giveaway to the rich, no doubt. I don’t need this benefit, and neither do most angels.

    But QSBS gives investors a strong incentive to back startups. Without QSBS, they might invest their money in private credit, real estate, or the good old S&P 500.

    And if you let me keep $15 million in gains tax free, what am I going to do with it?

    I might buy a house. But most of the money will go to…you guessed it…more startups!

    “And on and on it goes, this thing of ours,” as Paulie Gualtieri said in The Sopranos.

    Tax savings under QSBS may be unfair in some ways, but they benefit all Americans in the end.

    Wrap-Up

    Critical caveat here: don’t rely on me for tax advice!

    I’m not a tax or financial advisor. In fact, I use an accountant who is well versed in startup investments and QSBS.

    You should do the same. If you want to evaluate an accountant’s knowledge of QSBS, just ask him to explain the law to you. He should be able to explain it clearly and correctly.

    With the right advisor, you’ll have the best shot at getting the most out of this huge expansion of QSBS!

    More on tech:

    Where I’m Finding the Best Startups Now

    My Biggest Losses as an Angel Investor

    Do Non-Founders Make Better Investors?

    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. 

  • Where I’m Finding the Best Startups Now

    Lots of people want to become angel investors. But where do you find great deals? Here’s where I’m sourcing deals now…

    I looked at all 35 names in my portfolio thus far. For each one, I noted where I first heard about the company.

    Where My Deals Are Coming From

    Here are the results…

    Jason’s Syndicate: 23
    Demo Day: 3
    Fellow Investor Referral: 2
    Used Product: 1
    Tom Williams Syndicate: 1
    Mana Ventures Syndicate: 1
    Founder Referral: 1
    Mercury Raise: 1
    OpenVC: 1
    Twitter: 1

    One source stands out far beyond the others: Jason Calacanis’ syndicate. It’s an amazing source of deal flow.

    The fella who found Uber and Robinhood will probably find the next big company too. When he does, I want to be there.

    How My Dealflow Is Changing Today

    When I first started as an angel, I didn’t know anyone in startupland. So I only did syndicate deals.

    Now I’ve been investing for a little over 4 years. I have my own dealflow, and I also cold message interesting companies regularly.

    Here’s where I’ve sourced my 6 most recent deals…

    Jason’s Syndicate: 3
    Founder Referral: 1
    Mercury Raise: 1
    Twitter: 1

    I’ve gone from all syndicate deals to 50% of my deals being direct. I expect that percentage will rise to at least 75% over time as my network grows.

    That said, I love doing syndicate deals. Sometimes, the lead will see a company I don’t.

    I like having that flexibility to still invest. And if it’s an Uber, giving up 20% of the gains doesn’t bother me at all.

    Why I Cold Message Founders

    In two of these 6 cases (the founder referral and the company I found on Twitter), I cold messaged the founders. That’s something I do more and more.

    In fact, most of my meetings these days are companies I contacted. That way, I know I’ll be interested in what they’re doing!

    I like to tell the founder exactly why I found their company compelling. I definitely do not send the same message to everyone.

    If my message is carefully tailored to the specific company, I’m more likely to hear back. I also message the same company repeatedly if I don’t hear.

    I’m a small fry. I can’t expect the best deals to come to me.

    But I’m in good company. Sequoia cold messages companies regularly.

    In fact, that’s how Jim Goetz won the WhatsApp investment. If you out hustle the competition, you win.

    Wrap-Up

    Of the countless companies founded every year, only a few will matter. The one thing that matters in venture capital is to own a piece of those companies.

    So I cast a wide net and meet lots of companies. Of the startups I see, I put a check into 1 in every 250 deals on average.

    I’m always looking for new sources of great deals. So if you have one you love, let me know!

    There will be no blog tomorrow for the holiday. Have a happy July 4th and God Bless America! 🇺🇸

    More on tech:

    My Biggest Losses as an Angel Investor

    Do Non-Founders Make Better Investors?

    The Coming Wave of Job Losses

    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. 

  • The Coming Wave of Job Losses

    Microsoft just announced they’re laying off another 9,000 people. With AI and offshoring rapidly eliminating jobs, are we about to see a new wave of unemployment?

    AI Eats Engineering Jobs

    New comp sci graduates have one of the highest unemployment rates of any major. Big Tech companies are doing hiring freezes and layoffs.

    AI is driving this rapid slowdown in engineering jobs. An engineer skilled in AI can produce far more than before.

    In fact, coding is what AI does best. But LLM’s are coming for other cognitive tasks.

    I expect routine work in customer service and legal to be automated soon. And once AI masters driving, watch out. Truck driver is the most common job in 29 states.

    But it’s not just computers that are coming for your job. It’s humans — overseas.

    Our Man in Cairo

    Whatever companies can’t automate, they’re offshoring.

    “We have a guy in Egypt that does all our cold calls for us now,” a friend in sales told me this weekend. “He speaks perfect English. And it’s only $500 a month.”

    A couple of years ago, his company would’ve hired an American fresh out of school. Not anymore.

    The quality of talent available overseas is insane. We can hire the best students in their whole darn country for a fraction of what mediocre Americans cost. They work harder and turnover is lower too.

    Adapting Is Harder Than It Looks

    Between automation and offshoring, lower end desk jobs are rapidly disappearing. If prior waves of job losses are any indication, it will be hard for laid off Americans to adapt.

    In 2008, Janesville, Wisconsin lost their GM plant. It employed 7,000 people at its peak, perhaps 1/6th of the town’s workers.

    I was living just up I-90 from there in Madison at the time. I remember the plant closure being all over the news.

    I recently read a book about Janesville. It turns out that despite the workers’ best efforts to retrain, 3/4 of them said they were worse off 5 years later.

    Half the laid off families struggled to afford food. Children became homeless.

    This is the future for a lot of laid off Americans. Adapting is harder than it looks.

    Wrap-Up

    AI and offshoring will decimate the lower end of the job market over the next decade.

    Many of the displaced workers will struggle. They could form a potent political force.

    My best advice on how to win in this new era is to embrace AI. Use it every day for every task.

    If you can do that, you’ll be one of the winners in this new world.

    More on tech:

    My Biggest Losses as an Angel Investor

    Did a Robot Try to Attack Humans?

    Testing Gemini’s New Models

    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. 

  • Why Businesses Should Leave NYC Now

    If you run a business in NYC, you should only be focused on one thing right now: finding office space in Jersey City. With anti-police mayoral candidate Zohran Mamdani about to take over, this is the most important thing you can do for your company.

    Back to the Bad Old Days

    We saw the results of defunding the cops under Bill De Blasio.

    Crime shot up like I’ve never seen in New York. Random people threatened me on the street. I saw people passed out with needles in their arms.

    In 11 years out here, I’d never seen anything like it.

    With the election of Mayor Eric Adams, New York is on the mend. But with Mamdani running away with the primary, we’re headed back to the bad old days.

    Mamdani has repeatedly called for defunding the police. Now that he’s trying to get elected, he’s attempting to walk that back.

    If you’re buying that, I have some swampland in Florida you’re gonna love.

    Why Businesses Have to Leave Now

    Mamdani will likely win. Even if he doesn’t, his primary victory shows how far left the NYC electorate has gone.

    Soon, either Mamdani or someone very much like him will take power. They’ll defund the police and crime will skyrocket.

    Once that happens, it will be hard to recruit employees to NYC.

    Who wants to pay $4,000 a month for a closet and get robbed on their way to the grocery store? No one.

    The best talent will go elsewhere. They’ll go to your competitors outside NYC.

    Once you can no longer attract the best people, your company is done.

    It’s important to leave now while there’s still space available. If you’re streaming out with everyone else, the limited office space in the surrounding area will be taken.

    Why Jersey?

    Here’s why you should move to Jersey City: it’s close, but not too close.

    You’re safely across the river and away from NYC’s ultraliberal policies. But you’re close enough to the city that not all your workers need to move at once.

    They can trickle in over time on their own schedule. They won’t need to take their kids out of school, at least not right away.

    Asking everyone to move to Miami or Austin is a much harder sell. Asking them to hop on the PATH train is only a minor change to what they do now.

    Jersey City has some lovely office space. This weekend, I looked around online out of curiosity and found this beautiful co-working space right across the street from the Newport PATH station. There are also some great spots in Hoboken and Secaucus, close to major train stations.

    Wrap-Up

    The lifeblood of any business is talent. And in a couple of years, the best talent will not want to be in New York.

    You don’t wait until the roof collapses to leave a burning building. Don’t wait until you or your employees are being assaulted to leave NYC.

    I hope I’m wrong about New York’s future. But I wouldn’t want to bet my company on it.

    More from the blog:

    Just Write the Poor a Check

    ChatGPT Helped Me Pick Our Next Governor

    Big Money, Politics and Polarization: Krysten Sinema at the All-In Summit

    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. 

  • Just Write the Poor a Check

    When I was a kid, my family was on food stamps. But sometimes, what we really needed was money to pay the light bill. Why not just give people cash?

    Right now, Congress is voting on Medicaid cuts in the hopes of balancing the budget. I have a much easier way to fix these programs: just write people a check.

    A Grab Bag of Inefficient Programs

    The US government has countless welfare programs. Some of the largest are Medicaid (health insurance for the poor), SCHIP (health insurance for poor kids), SNAP (food stamps), and TANF (cash welfare).

    We spend about $750 billion on these programs in total. About 6% of that goes to admin costs: $45 billion.

    Compare that to Social Security. Social Security is much larger, at $1.5 trillion a year in spending. Admin costs are just 0.5%, or about $8 billion a year.

    It’s no wonder Social Security has way lower admin costs than programs like Medicaid. Medicaid has complex eligibility requirements and only pays for certain services. Handling applications and claims is time consuming and labor intensive.

    What Happens If We Just Give Them a Check?

    What if instead of all these complex programs for the poor, we did what Social Security does: give them cash?

    The poor would have much more flexibility. They’d be able to buy diapers when they need diapers, instead of wishing that SNAP card could be used for Pampers.

    The admin costs of these programs would also fall precipitously. If we got the admin costs on welfare programs down to the level of Social Security, we’d save about $40 billion a year.

    That’s a ton of money! That $40 billion could be used to help more poor people or reduce the deficit.

    The Power of Responsibility

    Being on welfare isn’t great. I know: I’ve been there.

    We don’t want people becoming dependent on the government for the rest of their lives. That is not a happy life.

    Don’t believe me? Visit any urban ghetto and see the results of these welfare programs. Or visit a poor, rural area like the ones I lived in as a kid.

    We should help folks get back on their feet if they’re having a rough patch. But we should time limit these programs to 5 years in a person’s life.

    This is incredibly generous.

    If you’re struggling, your fellow citizens will be happy to help you. We’ll cover your bills for a whole 5 years!

    But if you’re able bodied, you eventually need to work. Five years should be more than enough time to find something.

    And if you’re truly disabled, we’d be happy to support you for life. In a society as wealthy as ours, we have that luxury.

    Wrap-Up

    One big objection to sending the poor cash is that they’ll spend it on the wrong things. Drugs, alcohol, you name it.

    Let’s be honest: some will. But let’s also not fool ourselves: people sell food stamps for cash and buy drugs as it is.

    We shouldn’t penalize decent families down on their luck by treating them like children.

    They know what they need better than we do. Giving them cash is the easiest way to meet those needs.

    But another part of treating the poor like adults is responsibility. That’s why welfare must end after 5 years.

    Give folks cash. But enforce a time limit.

    This is how we can fix welfare in America.

    More on government:

    ChatGPT Helped Me Pick Our Next Governor

    Three Priorities for the Trump Administration

    Big Money, Politics and Polarization: Krysten Sinema at the All-In Summit

    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. 

  • Where Men Win Glory: The Pat Tillman Story

    Pat Tillman walked away from a $3.6 million NFL contract to join the Army after 9/11. What makes a man do something like that? As I headed off on vacation a couple of weeks ago, I cracked the book Where Men Win Glory to find out.

    Tillman was one of the best defensive players in the NFL at the turn of the millennium. But after the September 11 attacks, he was not content to sit back and let others fight al Qaeda. He decided to enlist himself.

    Tillman At War

    His base pay as a private in the Army was a long way from his NFL millions: just $1,290 a month. And Tillman put himself in grave danger, requesting an infantry billet.

    Tillman served in Iraq briefly but never saw combat. Soon after, he was deployed to Afghanistan.

    Sent to patrol remote villages near Afghanistan’s border with Pakistan, Tillman and his unit wound their way up remote mountain passes. As darkness began to fall that night, some of the Rangers in Tillman’s unit mistook him for a Taliban insurgent.

    Despite his efforts to signal to them, they shot him dead.

    The Cover Up

    At first, the military and the White House claimed that Tillman fell bravely resisting the Taliban. This was despite internal reports that he died in friendly fire.

    The truth was that Tillman’s death was a colossal screw-up by the military. Another soldier shot him dead at a distance of just 120 feet. It wasn’t even entirely dark when it happened.

    Soldiers even destroyed some critical evidence, including burning his uniform, which is against military rules.

    In time, the truth came out: Tillman was killed by his own.

    His death appears to have been an accident. Chalk it up to the fog of war: nervous men, many of whom had never been in combat, fired wildly and Tillman paid the price.

    Why Did Tillman Walk Away From Millions?

    Very few people would walk away from fame and millions of dollars to risk their life in Afghanistan. So why did Tillman do it?

    Tillman was a man of principle. He didn’t think others should have to fight while he sat on his NFL millions.

    But he was also a thrill seeker.

    Many times in college, Tillman made dangerous jumps from high cliffs into bodies of water. Some of the jumps could’ve killed him.

    I’ve never jumped off a cliff. I’ve also never served in the military.

    Principles shape our behavior. But so do more obscure personality traits.

    Preventing Friendly Fire: How Startups Can Help

    These days, I view a startup as the solution to every problem. And there’s a great startup to be built here.

    Sadly, what happened to Tillman is not rare. In Iraq and Afghanistan, the percent of casualties caused by friendly fire reached as high as 41% and 13% respectively.

    Nearly half of all casualties, caused by our own forces! This is unacceptable.

    Soldiers need a beacon that will broadcast their location and the fact that they’re friendly. Other soldiers could see this in a heads-up display or on a device. We could also put these beacons on friendly vehicles.

    This product would save untold lives. If you’re building it, contact me.

    Wrap-Up

    As I sit here writing this 21 years after Tillman‘s death, the Taliban is back in control of Afghanistan. 

    Tillman could have stayed home, played football, and enjoyed his family. They would’ve been better off. He would’ve been better off. And the situation in Afghanistan would’ve been no different. 

    I respect what Tillman did. But I wish he hadn’t done it.

    Sometimes, answering the call of duty isn’t the thing to do. Sometimes, we’re better off taking care of our own.


    More on books:

    Nuclear War: A Scenario

    Unit X

    Empty Planet (Part One)

    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. 

  • What Percent of Companies Pivot?

    “The initial idea doesn’t matter — most companies pivot.” I’ve heard that 100 times. But is it really true? Today, I dug into my portfolio to find out.

    I looked at investments at least a year old. This way, they’ve had time to pivot.

    Here’s what I found…

    Of 29 companies in the sample, 10 pivoted. 19 are still working on the same idea they had at the time I invested 1-4 years ago.

    Are pivots more successful? Or is pivoting something only a failing company does?

    To answer this question, I looked at the 3 most successful companies in my portfolio. Of those 3, one is a pivot.

    If I expand that to the top 5, I still have only 1 pivot. This makes sense — if you’re crushing it with your initial idea, why change?

    Since I’ve only been investing for around 4 years, my sample size is small. I searched for data on how common pivots are but couldn’t find anything useful. So for now, you’ll have to content yourself with my study, small though it may be!

    The bottom line is most of my investments don’t pivot. This is especially true for the most successful companies.

    As investors, it’s our job to challenge conventional wisdom. And from what I’ve seen, the commonplace that “the idea doesn’t matter” is wrong.

    I pay close attention to both the team and the product. Odds are, they’ll still be slinging this thing for a long time.

    More on tech:

    My Biggest Losses as an Angel Investor

    Don’t Give Answers. Ask Questions.

    Do Non-Founders Make Better Investors?

    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. 

  • My Biggest Losses as an Angel Investor

    I lost my entire investment. Twice. These are my worst losses as an angel investor.

    Everyone online wants to talk about their wins. But you really want to learn something? Lose some money and feel the sting.

    Here’s the mistake I made and why I’ll never do it again…

    Two Strangely Similar Companies

    A couple of years ago, I made two investments that looked rather similar.

    Both founders were wonderful. Deeply committed, incredibly hardworking.

    Both products were very innovative. Had they worked, they would’ve been giant outcomes.

    But both startups had the same problem: their bank accounts were running low.

    These companies didn’t have an active round going. So, at that particular moment, my money was the only investment cash coming in.

    Since both these startups were breakeven or slightly profitable, I didn’t worry about it. But here’s what I didn’t realize…

    How These Bets Went Bad

    A small profit can turn into a big loss pretty quickly. A customer churns, a usage-based scheme doesn’t get the usage you imagined, etc.

    When that happens, you need a cash cushion. If you don’t have it, you’re toast.

    Had I invested in these startups alongside a lead, they’d have had a few million dollars to fall back on. But I didn’t.

    Both founders held on much longer than I ever expected. But eventually, they had to admit reality and close up shop.

    The One Thing I Did Right

    As dumb as my decisions were, I did one thing right: bet sizing.

    I made tiny feeler bets on both these companies. As painful as these losses felt at the time, they were actually quite small in the context of my portfolio.

    Let’s take the “fund” of 36 companies I’m investing out of right now. These losses represent just 2% of it.

    I don’t make a larger investment until the company sees some real success. My biggest investment is 11% of my portfolio, and that company is doing a lot better than these two.

    What I Learned

    If I had invested in these 2 companies alongside a lead who put up millions, they might still be operating today. Not waiting for a lead was the key mistake I made.

    Fortunately, I only made that mistake twice in 35 investments. I won’t be making it again.

    Today, I look for a lead putting a minimum of 12 months runway or $1 million (whichever is more) into the company. I’m also fine with a party round so long as the company has that same amount of cash signed and wired. In fact, my most successful investment to date was a party round.

    With that kind of cash coming in, the company can weather some serious hits without going out of business.

    Wrap-Up

    These two founders did nothing wrong. They’re wonderful entrepreneurs.

    They worked incredibly hard to make those companies work. But it just wasn’t possible.

    I’d back either of these guys again in a minute.

    It was me who made the mistake. I shouldn’t have invested without a lead.

    Mistakes happen. They’re the cost of doing anything ambitious. We just need to learn from them.

    And this is a mistake I won’t make again.

    More on tech:

    Working for Jimmy

    Don’t Give Answers. Ask Questions.

    Do Non-Founders Make Better Investors?

    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.