Tremendous

An angel investor's take on life and business

  • Why Nicotine Pouches Are Unsafe

    Techbros love nicotine pouches. But these pouches are terrible for your health. Here’s why you want to avoid them…

    Nicotine pouches put you at risk of cancer, heart disease and dental problems. Nicotine is a vasoconstrictor, meaning that it narrows your blood vessels. This is very bad for your cardiovascular health. 

    I’ve heard many people say that cigarettes are dangerous but nicotine is not. This just isn’t true.

    How I Quit Nicotine

    If you love nicotine, I get it! I used to smoke cigarettes for years.

    On January 20th, 2015, I quit. It’s one of the best things I ever did in my life.

    It’s not worth the health risks. Life’s too short to be a slave to nicotine.

    I didn’t think I could quit, but it turned out to be much easier than I thought.

    Within a couple of days, I started to feel healthier, more energetic, even exhilarated.

    I quit by slowly decreasing my nicotine consumption. I went from 20 cigarettes a day to 10 the next week, then 5, then 0.

    For other people, quitting cold turkey works better. There is no right or wrong way, so long as you quit.

    Nicotine Isn’t Helping You

    I used to think nicotine gave me an edge. It didn’t.

    Nicotine withdrawal made me jittery. Then, I used nicotine to kill the jitters.

    Nicotine was creating a problem and then solving it. But when I threw the cigarettes away, the problem was gone!

    Wrap-Up

    If you’re reading this, you’re probably building something ambitious. If nicotine ruins your health, you’ll never reach your goals.

    I can’t tell anyone what to do. 

    But I want everyone to know that nicotine pouches aren’t safe. And you really can quit. 

    Whatever decision you make, I wish you the best. 

    More on health:

    How I Quit Smoking

    How I Learned to Cook

    Using Grok as My Personal Trainer

    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. 

  • 3 Things I Hate Seeing in a PItch

    Here are 3 things I hate seeing in a pitch…

    1. Letters of Intent (LOI’s). Also known as Letters of Nothing. Prospective customers sign these letters, saying they “intend” to buy your product. But will they really? Who knows.

      These letters may sound good, but they mean absolutely nothing.

      Some founders spend months chasing an LOI. This is wasted time.
    2. “Line of sight.” As in “We have a line of sight to $10 million ARR.” I see this phrase all the time in pitch decks.

      What on earth does it mean?

      You think that maybe someday you’ll have $10 million ARR? Fine, but that is meaningless today.

      Talk about where you actually are now.
    3. “Pipeline.” As in “We have over $100 million ARR in our pipeline.”

      If you send a cold e-mail to someone that is never returned, they could be counted as part of your “pipeline.” This is another meaningless metric.

      What matters is the customers you have today, not who’s in your CRM. 

    What to Focus On Instead

    Instead of LOI’s, “lines of sight,” and pipeline, talk about where your business is today. 

    “We have 3 customers paying $100 a month.” That’s not a lot of money. But it’s concrete and it’s a start!

    Maybe you don’t have any customers yet. In that case, focus on your product and team. You could say something like this:

    “We are a team of 3 engineers shipping new product daily.” 

    Now that’s exciting!

    You just gave me useful info on your skills and what you’re building. That would impress me more than an LOI for $100 million. 

    Wrap-Up

    There’s nothing wrong with being an early stage company!

    But focus on the things that matter. Sell your team’s skills, your product, and your first customers.

    That beats LOI’s and “lines of sight” any day.

    More on tech:

    Meet My Latest Investment: Mozi

    How Top Startups Break the Rules

    How Founders Can Improve Their Pitch by Watching Game Film

    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. 

  • How Top Startups Break the Rules

    Two co-founders in an office in SF — that’s our image of a successful startup. But many of my best investments don’t look like that…

    The best companies often break a rule. Let’s look at some of those rules and how successful companies break them.

    You Need a Cofounder 

    We tell everyone they have to have a co-founder. But my most successful investment so far was in a solo founder, Ali at Micro1.

    Look at Amazon, Facebook or Oracle. All solo founders.

    Maybe having one person making decisions forces a company to move faster. 

    There are benefits to having co-founders. They bring skills you lack and share the workload.

    But never rule out a great solo founder.

    You Have to Be In Person 

    Everyone is rushing back into offices. But my most successful investment has a lot of its team remote. Coinbase, Airbnb and Wiz are remote too.

    Remote work lets you hire the best talent no matter where they live. That’s a huge advantage.

    In-office work has benefits too. It can be easier to cooperate in person.

    But you’re giving up a global talent pool. 

    You Have to be in SF

    One of my best investments, Rilla, is in New York. And they’re not even in Manhattan — they’re in Long Island City!

    Those guys work as hard as anyone in San Francisco. And they’re growing really fast.

    A great founder will succeed in any town in America. 

    Wrap-Up

    There’s nothing wrong with having a co-founder, an office, and living in SF. I have some awesome investments that check all those boxes.

    But great companies tend to break the rules. My job is to find those outliers.

    What rules are you breaking, and why?

    More on tech:

    How Founders Can Improve Their Pitch by Watching Game Film

    Why Short Decks Raise Millions

    The Question No Founder Asks

    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. 

  • How Founders Can Improve Their Pitch by Watching Game Film

    Founders: have you ever watched yourself pitch? Peyton Manning spent 20 hours a week watching game film. Here’s what you can learn from him…

    Careful study of game film gave Manning a huge advantage. But when most founders pitch investors, they just do meeting after meeting with little idea how they performed. 

    How to Use Game Film

    Here’s how founders can use game film to get an edge…

    1. Get the right tech. I record every single meeting I do using a tool called Fathom. It’s free and easy to use.
    2. Replay key meetings. You don’t have to re-watch every meeting you do. But re-watching some important meetings shortly afterward, while they’re fresh in your mind, can help you a lot.
    3. Are you talking too much? Fathom shows you the exact percentage of time you spoke. In my experience, fundraising meetings go best when the founder speaks about 60% of the time and the investor speaks around 40%. Most founders talk way more than that. That’s a mistake — it doesn’t allow investors enough time to ask questions.
    4. Look at the investor’s body language. Are they leaning forward with interest? Are their arms crossed in a defensive or skeptical pose? This tells you how they’re receiving your message.
    5. Ask AI for help. Fathom lets you easily copy the full transcript of your meeting. Dump that transcript into Grok or ChatGPT. Prompt it like this: “I’m a startup founder pitching an investor. Here’s a transcript of a meeting. How can I improve my pitch?”

    Investors Should Be Watching Game Film Too!

    I watch game film of my most important founder meetings. 

    When there’s a company I’m really interested in, I re-watch our call after so I can pick up on any details I may have missed. And sometimes, I dump the transcript into Grok and ask how I can improve.

    Grok told me to be more explicit about what I liked when I meet a startup. Sometimes I’m so eager to ask question after question that I forget to do that!

    Wrap-Up

    Pitching is a skill. Like any skill, you get better with practice.

    Watching yourself is one of the best ways to learn. You see what you do well and what you do poorly.

    Whether you’re Peyton Manning, a startup founder, or me, watching game film gives you an advantage. Your competitors aren’t doing it. 

    Press that advantage and raise more money!

    More on tech: 

    Why Short Decks Raise Millions

    How to Run a Pitch Meeting

    How to Tell If Investors Are Really Interested

    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.

  • How My “Fund” Is Beating Over 90% of VC’s

    This angel investing thing just might work! My “fund” is beating well over 90% of VC’s, according to AngelList data.

    How My “Fund” Stacks Up Against the Competition

    So far, my “fund” sits at 1.65x TVPI. This means that the total value of all my investments is 65% more than what I paid.

    Here’s how that stacks up against other funds…

    I made my first investment in June of 2021. That puts me in the 2021 Vintage.

    For 2021 funds, the 90th percentile for TVPI is 1.58x. At 1.65x, I’m well above the threshold for the 90th percentile. 

    AngelList doesn’t break down returns any more finely than that. So, we don’t know if my exact percentile is 93rd, 95th, etc. 

    Cracking the the 90th Percentile

    There are 35 investments in this “fund,” in total. That’s a typical number of names for an early stage venture fund. I closed “Fund 1” last month and now I’m investing out of “Fund 2.” 

    I still have about 15% of “Fund 1” remaining. That cash will go as secondary bets into the best companies, which should further increase my returns.

    So far, only 2 companies in Fund 1 have gone out of business. That really surprises me. I figured most of them would be gone by now!

    Avoiding those zeroes has helped the portfolio. But what has really moved the needle is the 3-4 most successful companies.

    So far, the best among them is Micro1, which recently announced its Series A at a $500 million valuation. 

    Three other startups in “Fund 1” have crossed $10 million ARR, a key milestone. I’m hoping to get multiple unicorns out of this fund, and I think it’s achievable.  

    How I Picked My Investments

    My method for picking startups is pretty simple.

    I look for builder founders working on huge problems. If I see early signs that their product is catching on, I place a bet.

    I look carefully at market size and traction. I also only invest in founding teams that can build a great product in-house.

    To find the 35 startups in Fund 1, I probably looked at 5,000 or more. That’s what the job is: a relentless winnowing of companies to find the very best. 

    Going from Markups to Cold, Hard Cash 

    Having strong TVPI is nice, but we can’t eat markups. So far, all my returns are on paper.

    That’s typical for a fund as new as mine. Most 4 year old funds have little or no actual cash returns, or DPI.

    If you invest at pre-seed and seed like I do, it can take 10-15 years for your best companies to finally hit an IPO. So, I would not expect DPI at this point.

    But eventually, those paper markups need to convert to cash. I’m watching carefully for opportunities to get liquidity sooner through secondary sales.

    Wrap-Up

    I have a long, long way to go with this portfolio. Good returns today don’t guarantee anything in the future.

    But for now, this is good progress.

    Even though I’m a small investor, I want to do the best job I can. That’s why I think of my investments as a “fund,” even though they’re not exactly Sequoia.

    I want to learn the business using small sums of money. Later on, I’ll be able to deploy larger sums intelligently using what I learned. 

    You want to learn poker at the penny ante table. Once your game is strong, you’ll be ready to join the high rollers. 

    More on tech: 

    Three Things Investors Should Never Do

    Meet My Latest Investment: Mozi

    My New Investment Strategy

    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. 

  • Three Things Investors Should Never Do

    Three things investors should never do during a founder meeting…

    1. Don’t be late. Seems obvious, right? But you wouldn’t believe how many people get this wrong.

      Founder time is the scarcest resource in the world. Do not waste it.

      I like to show up a little early. Then, I know I won’t keep anyone waiting.
    2. Don’t use your phone. Either give this founder your full attention or don’t meet with them at all.

      That means putting your phone down.

      I also don’t want to see you on e-mail, X, or anything else. Give the entrepreneur the respect he deserves.
    3. Don’t have side conversations. I saw a particularly bad example of this at a pitch event this week.

      As the founder presented, the investors couldn’t stop talking among themselves. It got so bad that I could barely even hear the founder anymore.

      This is very rude behavior. When the founder is talking, be silent.

      When it’s time for questions, by all means ask some! But don’t chat with the person next to you while the entrepreneur is speaking.

    Wrap-Up

    These 3 don’ts come down to one easy rule: give the entrepreneur your attention and respect.

    This pitch could be the most important moment of their professional life.

    You don’t have to invest in their company. But you do need to take this meeting seriously and treat them right.

    If you treat founders with respect, you can go to bed at night knowing you did the right thing. And as your reputation spreads, you might be surprised at the awesome deals that start coming to you. 

    Have a great weekend, everyone!

    More on tech: 

    How to Get Into Hot Startups

    3 Ridiculously Easy Things Every Investor Should Be Doing

    My New Investment Strategy

    Meet My Latest Investment: Mozi

    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. 

  • Goodbye Charlie

    This morning, I watched the sun come up over New York City. Twenty-four years ago, we were attacked. Today, we attack each other.

    “Where’s Dad?”

    To tell you the truth, I don’t know much about Charlie Kirk. But I do know that his wife and two small children are now alone.

    When a tragedy strikes a family, that family is never the same again.

    How is his wife Erika supposed to tell those two children that dad isn’t coming home?

    Violent Speech Leads to Violent Actions

    Charlie’s murder is the predictable consequence of violent rhetoric. For 10 years, the media has been screaming that conservatives are fascists and Nazis.

    Most people ignore them. But a few radicals actually believe it.

    Those radicals tend to be of low intelligence. They also tend to be mentally ill and struggling in life.

    They don’t have much to lose anyway. 

    “This is my chance to stop the next Hitler,” they probably think. If you truly believe that, violent actions are the logical next step.

    Stop and Think

    Of course, believing that Charlie Kirk or Donald Trump is Hitler is ridiculous.

    Hitler murdered millions of people. Charlie and Donald represent a moderately right leaning political movement in a democratic nation.

    But some people will adopt illogical, absurd beliefs. And they will act on them.

    So remember, the next time you’re tempted to say that Republicans are fascists or Democrats are traitors…

    Your violent speech may result in someone else’s violent actions. Even if you did not intend that, it can happen anyway.

    Think of Charlie’s little kids. Think of the next Charlie.

    FInal Thoughts

    A few nights after 9/11, we all walked out onto our sidewalks. As far as I could see, neighbors held candles.

    No one spoke.

    No one needed to.

    I will never forget that moment. And I hope that we Americans can remember how much we love our nation, and each other.

    “Charlie Kirk” by Gage Skidmore is licensed under CC BY-SA 2.0.

  • How to Get Into Hot Startups

    “How are you getting into seed rounds with just a $10k check?” Here’s how…

    Help a Founder, Win a Deal

    A couple of months ago, I met an amazing founder I’ll call “Jim”. Jim had recently left one of the best hard tech startups in the world.

    Now he was kicking off a fundraise for his new company.

    As soon as I met Jim and saw what he was building, I got really excited. And I was pretty sure other investors would be too. So I asked him…

    “Are you looking to meet other investors?”

    “That would be a big help!” he replied.

    How a Tiny Investor Squeaks Into a Great Deal

    Within a couple of hours, I had messages out to VC firms all over America. Soon, Jim had half a dozen VC pitches on his calendar.

    Fast forward a month…

    When I first met Jim, his round was in the early stages. Now, it was oversubscribed. I guess he crushed those pitch meetings!

    “Can I invest $10k?” I asked Jim.

    “Sure!” he said. Not long after, I had the wiring info in my inbox.

    Passive Investors Get the Scraps 

    Now, imagine if I had played this another way…

    What if after I met Jim, I just told him to let me know if he gets a lead investor. No help, no intros, no nothing.

    Would Jim have ever come back to me?

    Maybe.

    But I don’t like my odds.

    But I wasn’t passive. I did all I could to get Jim lots of meetings and help him close his round.

    Reputation Is Access. Access Is Everything.

    My help was just a tiny part of getting the round closed. The credit goes to Jim and his incredible team of builders.

    But as the Beatles say, “I get by with a little help from my friends.” 

    And if Francis helps you before he’s even an investor in your company, wouldn’t you want to let him onto the cap table?

    My check being probably the smallest in the entire round didn’t matter. It was the help I could offer that won me the deal, not the cash.

    This is how you get into great deals. Give the founder a reason to take your money!

    Helping Founders Isn’t Just for Little Guys

    And never forget, the big boys have to demonstrate value too.

    Do you think a super talented founder just takes any term sheet a VC throws at him? Not likely.

    The best companies often get multiple term sheets. The founder then picks which VC firm he wants to work with.

    The most helpful VC usually wins the deal.

    Wrap-Up

    Helping founders raises your chances of getting into great deals. It’s also a lot of fun.

    If Jim becomes a big success, I can say to myself, “I had a tiny hand in making that happen.” 

    If you want to invest in great companies, help a promising founder. You might be surprised the access that you get in return.

    Founders: What help do you need? Investors: how do you help founders?

    More on tech: 

    3 Ridiculously Easy Things Every Investor Should Be Doing

    My New Investment Strategy

    Meet My Latest Investment: Mozi

    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 Short Decks Raise Millions

    I just saw a founder raise $5 million with a 7 slide deck. Here’s how you can do it too…

    1. Title
    2. One sentence vision
    3. Team
    4. Traction
    5. Market size
    6. Competitors
    7. Ask

    Short decks raise more money, not less.

    People just flip through pitch decks. Make them easy to flip through!

    Highlight the most important info and get rid of everything else. That other stuff obscures your message and stops you from raising money.

    Of course, there are many other things you want to tell investors. But that’s what the meeting is for!

    This deck gets you that meeting.

    Don’t edit your existing deck. Flush it down the toilet.

    Start fresh and make a 7 slide deck the way I showed you above. Then, send it to some investors.

    You’ll be surprised how many more meetings you get!

    How long is your deck right now?

    More on tech:

    Your Deck Probably Sucks. Here’s How to Fix It.

    How to Run a Pitch Meeting

    How to Tell If Investors Are Really Interested

    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. 

  • Janesville — Or Why AI Will Be a Disaster for Jobs

    AI will replace millions of workers. Drivers, customer service agents, accountants. Creating good jobs for those laid off people is one of the most important things we can do. 

    I used to think the displaced workers would find new jobs on their own and wind up better off. I no longer think that.

    What happens when a huge number of people lose their jobs, suddenly? To find out, let’s take a look at what happened in 2008 in my home state of Wisconsin…

    Learning from Janesville

    Janesville, Wisconsin. Two days before Christmas, 2008. 

    Last vehicle rolls off the line. Black Tahoe.

    85 years of history and thousands of jobs, gone. I lived just up the road when it happened, in Madison. 

    The GM plant employed 7,000 people at its peak. They all lost their jobs.

    Many years later, those workers have never fully recovered.

    What happened to those hard working people is the subject of an excellent book called Janesville. 

    Trying and Failing to Adapt

    After they were laid off, many of the former GM workers signed up for job training. This is what you’re supposed to do, isn’t it? 

    And yet, the workers who signed up for retraining actually made less than the workers who didn’t.

    Five years after the factory closed, 3/4 of the workers said they were worse off financially than before.

    Proud People Struggling

    Unemployment in Rock County, where Janesville sits, reached 13%. Half the families hit by the layoffs struggled to afford food. 

    Janesville, once a prosperous community, began to have homeless children.

    The laid off workers were not lazy people. They had worked hard, year after year.

    But that didn’t matter anymore. 

    The economy had moved on, and they were no longer needed.

    What the Heck Does This Have to Do with AI?

    What happened in Janesville is about to happen everywhere.

    Millions of people will lose their jobs.

    In 2008, it was a financial crisis and offshoring. This time, the cause will be AI and robotics.

    The displaced workers will look for other jobs, and many will probably find them. But the new jobs will pay much less.

    We’ll also create new jobs that pay a fortune: Machine Learning Researcher, Robotics Engineer. But the displaced workers won’t be qualified for those.

    This means a permanent loss of income for the workers whom AI replaces.

    Kicked Down the Economic Ladder

    Let’s say you’re an accountant…

    Accounting is probably your best skill. If you had a better one, you’d use it and make more money, right? 

    In 5 years, software may replace most of what accountants do. That means many accountants will be laid off.

    What will these laid off accountants do? 

    Any new job will probably pay less. Their most valuable skill isn’t valuable anymore. They’re forced down the value chain to lower paid work.

    Maybe the former accountant will find himself at Wal-Mart or taking care of a disabled person as a home health aide.

    Those jobs are honorable. But they don’t pay very well. 

    Wrap-Up

    The AI revolution is a foregone conclusion. Our most important job today is figuring out how to deal with the fallout. 

    How to create jobs for displaced workers. How to help humans find meaning in a world of machines.

    If we do that successfully, we can reap the benefits of AI without creating instability.

    But if we fail, America is headed for a dark future.

    More on tech: 

    The End of Human Drivers: 7 Million Jobs at Risk

    Meet BMW’s New Factory Workers

    The End of Human Food Delivery

    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.