Tremendous

An angel investor's take on life and business

  • Working for Jimmy

    Yesterday morning, I didn’t want to get out of bed. I was on 4 hours sleep. But then I thought, “Jimmy needs me”.

    Who’s Jimmy? Jimmy is the name I’ve given to that anonymous founder out there who needs help.

    Jimmy is just starting out. Nobody believes in him, but he has a killer idea that’s going to make life better.

    Jimmy is my customer.

    Learning from Michele Ferrero, Chocolatier

    Who doesn’t love those little Ferrero Rocher chocolates? Whenever I go to the pharmacy for a flu shot or some other unpleasant task, I pick one up at the checkout counter.

    But it wasn’t until yesterday that I found out Ferrero is a multibillion dollar empire!

    Turns out they make Nutella, Kinder, and a zillion other things. The company is worth at least $40 billion, and founder Michele Ferrero was the richest man in Italy.

    In a wonderful episode of the Founders podcast, host David Senra explains how Michele kept himself laser focused on the customer. He gave her a name: Mrs. Valeria.

    Mrs. Valeria was Michele’s boss. She would decide the success or failure of his business and the livelihood of thousands of employees.

    Every decision he made, he made with Mrs. Valeria in mind.

    Inventing Jimmy

    As I listened to this podcast, I thought to myself: how can I take Michele’s lesson and apply it to angel investing?

    I realized I needed my own Mrs. Valeria. A representative founder.

    I decided to call him Jimmy.

    Jimmy is loaded with skills. Jimmy has a couple of hardcore builders working with him. And Jimmy is about to create something huge.

    But nobody believes in Jimmy. He’s an outsider. And he needs my help.

    What Does Jimmy Need?

    So what does Jimmy need? I came up with a list:

    1. Cash.
    2. Prompt responses. Jimmy is trying to move fast. He cannot wait for a week for me to reply to an email — all too common amongst VC’s.
    3. A clear yes/no. Jimmy needs to know where he stands.
    4. Clear rationale for a no. This will help him find out what he needs to do to get funded.
    5. Intros. Jimmy is an outsider. He needs intros to other investors, customers, and key employees.
    6. Occasional advice. Sometimes, Jimmy needs someone to kick around ideas with. But he doesn’t need meddling.
    7. Help boosting social posts. These are the key to customer acquisition for many companies. So I take some time each day to like and comment on posts from my founders. It’s fun to see what they’re working on!

    Wrap-Up

    It’s really hard to think of “founders” in general. It’s much easier to think of one person.

    That’s why I created Jimmy.

    Maybe Michele Ferrero faced the same thing. He created Mrs. Valeria.

    No matter what business you’re in, the customer is king. Or as they say in Japanese, okyakusama wa kamisama — “the customer is God.”

    So when I’m tired and my behind is dragging, I think of Jimmy.

    Jimmy’s tired too. But he needs me to clock in and get to work.

    Together, we have a chance to achieve something great.

    More on tech:

    Don’t Give Answers. Ask Questions.

    Do Non-Founders Make Better Investors?

    Hot Categories I’ve Never Invested In

    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. 

  • Don’t Give Answers. Ask Questions.

    “Should we keep selling to the mid-market, or go after the whales?” a founder recently asked me. Instead of giving her an answer, I asked her a question…

    “What’s the difference in sales cycles between the two?” I asked.

    “That’s just it!” she responded. “The sales cycles are basically the same. But the big customers are 5 or 10 times larger ACV’s.”

    “It sounds like you’ve got a solid argument for going after the big guys,” I said.

    “That’s what I was leaning towards,” she responded.

    “I think you should go with your gut,” I told her. “You’re in this every day. I’m parachuting in for a half hour. You know better than I do.”

    Why Asking Questions Is Better Than Giving Answers

    After our chat, she started going after the larger customers. And sure enough, revenue growth went way up, hitting 3x year over year!

    The traditional startup advice is to go after smaller customers first. They usually have shorter sales cycles and are more likely to do business with startups.

    As soon as she asked me this question, I was sorely tempted to parrot that cookie cutter advice.

    But I didn’t. Instead, I asked her a question.

    The Answer Is Within You, Grasshopper

    Turns out, the cookie cutter advice did not apply to this company.

    And no wonder! Every company’s different.

    This is why I rarely give founders a straight answer. Since I don’t actually work at the company, I only have so much context.

    Usually, the founder already knows what to do. They just need a sounding board and some validation.

    How VC Advice Can Hurt Companies

    Asking questions does a better job at revealing the truth than just making a statement.

    We investors love to think we have all the answers. You’ll never see anyone make more pronouncements with less knowledge than a VC.

    But we don’t have all the answers. Every startup is different.

    The problem is, founders tend to give our opinions undue weight. We have the playbook to success, right?

    In truth, each founder is the best expert on her company. If anyone has the answer, it’s her.

    The investor can help by listening and teasing the right answer out of her. But when he short circuits that process and gives an opinion based in minimal knowledge, he’s hurting, not helping.

    Wrap-Up

    If you’re an investor, try asking questions of your founders. If you’ve picked your founders well, the answers are already within them!

    If you’re a founder, encourage investors to ask you questions. These questions help you refine your thinking.

    The right answer is out there. Together, you can find it.

    More on tech:

    Do Non-Founders Make Better Investors?

    Hot Categories I’ve Never Invested In

    Small Investors Lead to Big 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. 

  • Do Non-Founders Make Better Investors?

    I’ve never been a founder. This gives me one advantage: I’m never tempted to tell founders what to do.

    The Problem Board Member

    A while back, I was chatting with a great entrepreneur I know. We’ll call him Hal.

    Hal is crushing it. His SaaS company is growing rapidly with incredible cash efficiency.

    But Hal had a problem.

    His board member, whom we’ll call Jim, was becoming a hindrance.

    Jim wasn’t just listening, asking questions, and giving a little advice like a good board member. Jim wanted to tell Hal how to run the company.

    Hal politely explained why they don’t do things Jim’s way. But Jim couldn’t let it go.

    I wondered, why was Jim acting this way? Why did he think he knew better than Hal?

    How Not Being a Founder Helps Me As an Investor

    I’ve never founded a startup. And I don’t intend to.

    Being a non-founder makes it easier for me to avoid doing what Jim does. I am not tempted to think I know better than the CEO.

    How could I possibly know better? I’ve never done his job.

    Founders often find it hard to stand on the sidelines. But that’s exactly what investors need to do.

    I’m eager to help the founder however I can. But I’m comfortable letting him run the company.

    Instead of dictating strategy, I like to ask questions. I want the founder to refine his own thinking, not substitute my judgment for his.

    Who’s Better at Investing — Founders or Non-Founders?

    There are great investors who have been founders. There are great investors who haven’t.

    Michael Moritz was a journalist before he became a VC. Doug Leone was an executive at Sun Microsystems. Bill Gurley was an investment banker.

    Maybe the fact that they never founded a company made them more comfortable advising the founder, instead of dictating to him.

    On the other hand, there are some amazing founder-turned-investors like Peter Thiel, Marc Andreessen, and Paul Graham.

    They have advantages of their own. They can provide better advice to a founder since they’ve been in his position.

    Both founders and non-founders can make great investors. Either way, you take your advantage and press it.

    Wrap-Up

    Hal wound up working things out with Jim.

    Hal and the rest of the board explained to Jim that these decisions are Hal’s to make. Jim seemed to accept that.

    But I had to wonder, how much of Hal’s time was wasted on this pointless dispute?

    I don’t do things like Jim.

    I try to help the company along the margins. But mostly, I get out of the way.

    And because I’ve never been a founder myself, getting out of the way is a little bit easier.

    Great to be back from vacation! I hope you guys are getting some rest this summer too.

    See you again on Monday!

    More on tech:

    Tools My Startups Love

    Hot Categories I’ve Never Invested In

    Small Investors Lead to Big 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. 

  • Tools My Startups Love

    If you want to know where technology is headed, look at what the smartest founders use. Here are the tools my startups are loving right now:

    Delve

    Delve automates compliance for SOC 2, HIPAA and more. Delve can get you compliant and ready to close big deals. 

    I first heard about Delve when one of my startups used it a while back. Now, that startup is closing huge enterprise deals. 

    Without compliance certification from Delve, they couldn’t have done it. 

    Cursor

    The most crazed builders I know use Cursor. Crazed in a good way: the kind of guys who work 14 hours a day and ship new features constantly. 

    Cursor uses AI to make coding easier. Cursor has helped my startups massively increase productivity. Any company not using it is risking their entire business. 

    Anthropic

    A marketplace startup I invested in recently started automating some of their onboarding and customer support. They chose Anthropic as the best tool for the job. 

    Anthropic’s API’s tend to produce better, more natural sounding results than other models. And since Cursor uses Anthropic as well, this AI lab scores twice on this list!

    SimpleClosure 

    I hope you don’t have to use this one. 

    But the reality is, most startups don’t make it. And if it’s time to close your company, you want to make sure it’s done right. 

    SimpleClosure can handle all the legal aspects of closing your startup. I had a company go through this process recently and SimpleClosure made it quick and easy. 

    Leaving the corporate entity hanging around can mean you still need to do tax and regulatory filings. Spare yourself that and handle it the right way!

    Wrap-Up

    Highly successful early stage founders are the earliest of early adopters. They’re looking for any advantage over their competition. Watch what they’re doing, and you’ll see the trend before everyone else does. 

    When you help my startups, you help me. So I’m grateful to these companies!

    I’m heading off on vacation today. The next blog will be next Friday, June 20. 

    Talk to you soon!

    More on tech:

    My Favorite Tech Tools

    Hot Categories I’ve Never Invested In

    Small Investors Lead to Big 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. 

  • Testing Mistral’s Latest Model

    Everybody forgot about Mistral. But I just used their new model and let me tell you: don’t sleep on these guys.

    This morning, Mistral released its most powerful model yet: Magistral. Today, I took it on a test drive.

    I asked 3 questions using Magistral Medium via Mistral’s Le Chat. Let’s see how it does!

    Helping Francis’ Poor Throat

    I’ve been dealing with a sore throat for the last few days. I’ve tried a few home remedies, but is there anything I’m missing?

    Let’s ask Magistral…

    Magistral gave me some good ideas, including honey and saltwater gargling. The suggestions had great citations, including Penn Medicine’s website.

    Magistral was also incredibly fast, giving me a response with sources in just a couple of seconds. Magistral did that faster than any other model I’ve seen.

    I’m giving this round an A! Time for some honey tea…

    Learning About Anti-Drone Tech

    Ahh, that’s better. Now, let’s give Magistral something a little harder.

    I’m researching a startup that stops drones. So I wondered, what’s the current state of anti-drone technology?

    Maybe Magistral can help…

    Magistral gave me a beautiful table with all the information I wanted. I didn’t even tell it to give me a table, but that worked quite well for organizing the info.

    I’ve heard of shooting drones down and hitting them with lasers. But it turns out there are many other ways to neutralize them, from GPS spoofing to RF jamming.

    Magistral gave me a great overview of the key technologies and also included some useful sources. And all this data came out in only 1 second!

    The only thing I’d change is I’d like to see citations in the table on each key technology. But overall, this was great work.

    I’ll give this round an A-.

    Digging Into the Medical Tourism Market

    Lately I’ve been working with a startup that’s making medical tourism easier. So I wondered, how big is the medical tourism market in America now, and what are the most popular procedures?

    Let’s ask Magistral…

    Magistral’s answer surprised me. Turns out almost a quarter of all medical tourism is for cosmetic procedures!

    Another procedure many Americans do abroad is IVF. That’s an opportunity I’m excited about. With folks having kids later, the demand for IVF is likely to grow a lot in the coming years. And unfortunately, getting IVF in America is terribly expensive!

    Magistral gave a great overview, complete with sources, in just 1 second. But most of the sources were websites I’ve never heard of, so I’m not sure about the quality.

    I’m giving this round an A-.

    Wrap-Up

    Overall, I’m giving Mistral’s latest model an A-. That’s a lot of progress from where Mistral was before!

    When I tested Mistral in April, it was well behind the best American models. Now, it’s getting close to the top tier.

    ChatGPT and Grok still find better sources than Mistral does. But for most tasks, Mistral is more than sufficient.

    Mistral is especially useful in applications where speed matters. If your users are complaining about latency, you should give this model a try.

    It’s easy to write off Mistral. They’re small. They’re French.

    But these guys just turned out a top tier model. Leaders like OpenAI and Anthropic better watch out.

    More on tech:

    Testing Mistral’s Le Chat

    Using Grok 3 to Manage My Stock Portfolio

    Talking AI, Biotech and More at the Single Family Office 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. 

  • Talking AI, Biotech and More at the Single Family Office Summit

    Can AI help us live decades longer? How should businesses adapt to AI? I dug into that and more on a panel at the Single Family Office Summit in New York City.

    Here are some of my favorite moments:

    8:07: How AI plus biotech will change human health: KJ’s story.

    11:56: My investment in Sent and why they will kill Twilio

    29:59: My best advice on how to adapt to AI

    Many thanks to the Family Office Club for putting on this great event!

    More on tech:

    Is Biotech Having its ChatGPT Moment?

    Hot Categories I’ve Never Invested In

    Small Investors Lead to Big 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. 

  • ChatGPT Helped Me Pick Our Next Governor

    If you live in New Jersey, I don’t have to tell you we’re choosing a new governor. But how should I vote? I used ChatGPT to help me learn about the candidates and make an informed decision.

    The primary election is tomorrow, June 10. Incumbent Phil Murphy is term limited. While Mikie Sherrill leads, it’s anyone’s race at this point.

    In local elections, it can be tough to find information about the candidates. But AI can do the research for me, scouring the internet for every piece of info on these pols.

    I used a heavily “engineered” prompt to find info on the candidates. I told ChatGPT my priorities in terms of issues. Then I instructed it to give me the info in a table format. This will let me easily compare the candidates.

    Here’s what ChatGPT found…

    Crime, Bail Reform, and ICE

    My #1 issue is crime. If we’re not safe, nothing else matters.

    So first, I asked ChatGPT about crime and bail reform. The details here were slim, but Fulop stands out for his record of reducing crime in Jersey City. Score one for the mayor!

    Cooperation with ICE has been controversial in New Jersey, with Newark mayor and gubernatorial candidate Ras Baraka getting arrested in a protest at a detention facility. I want to see full cooperation with ICE, removing dangerous illegal aliens from our state.

    None of the Democratic candidates are taking a strong pro-ICE stand. Steve Sweeney seems a bit better than most, opposing a bill to stop ICE cooperation. But none are pledging to work closely with Trump on this issue.

    Overall, none of the Democrats align with my views exactly. But given his great work reducing crime as mayor, I’m giving this round to Fulop.

    The Housing Crisis

    New Jersey is one of the most expensive states in America. Next, ChatGPT gave me an overview of how each candidate will address the housing crisis.

    Most candidates don’t have a clear plan. Here’s my plan: build like crazy.

    The only candidate who stood out in this round was Fulop. If you look at Jersey City’s skyline, you can see Fulop’s work — it’s grown enormously in his 12 years in office.

    Fulop wants to double the rate of affordable housing statewide, which would do a lot to help the average man. All that construction also creates a ton of jobs.

    I’m giving this round to Fulop as well.

    Taxes

    NJ has much higher taxes than most of America. That makes it hard to compete with no tax states like Texas and Florida.

    Sweeney has pledged not to increase taxes. Josh Gottheimer goes further, with plans for a 15% property tax cut.

    Fulop seems to be the only candidate who wants to raise taxes.

    He wants to extend a 2.5% tax on business profits over $1 million. This discourages companies from doing business in our state and takes jobs away from our neighbors.

    This round goes to Gottheimer.

    Education

    Only one candidate has made education a core message: Sean Spiller.

    Spiller is the president of the state teacher’s union. It’s safe to assume he’d increase school funding. He also wants free pre-kindergarten statewide.

    While Spiller’s plans could have some benefits, they’d also cost us a fortune. What’s more, a teacher’s union president is not going to advocate for needed reforms, like charter schools.

    I’m calling this round a draw.

    Wrap-Up

    Given the lack of substantive info out there on these elections, ChatGPT did a great job. Having a tool to do research and put the results in a standard format in one place is incredibly valuable.

    If you use AI to help you vote, I encourage you to read through the sources it cites and do some Googling as well. This helps you verify the info AI is giving you.

    We need more reporting on these elections. We also need politicians to answer tough questions. This will make it easier for citizens to decide.

    So, who did I vote for?

    With strong stances on crime and housing, Steve Fulop got my vote. He may not be perfect, but if he can do for the state what he’s done for Jersey City, he’ll go down in history as one of our greatest governors.

    I’m also looking forward to hearing from the Republicans in the general election. I just might switch teams come November!

    More on politics:

    Three Priorities for the Trump Administration

    Six Ways Trump’s Win Will Change America

    How DOGE Can Destroy All Opposition

    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. 

  • 3D Printed Guns: How Big Is the Threat?

    Less than 4 miles from where I sit, UnitedHealth CEO Brian Thompson was murdered with a ghost gun. So I wondered, how big of a threat are 3D printed firearms?

    A Rapidly Advancing Technology

    Unfortunately, 3D printing firearms has become increasingly easy. There are entire YouTube channels devoted to it.

    The guns they’re printing are increasingly sophisticated. Weapons that were once made of failure prone plastic parts are increasingly made out of much stronger aluminum.

    In the video above, you can see the creator of the PSR channel firing a Czech-designed Nexus Evo 3 Gen 2.

    I’m no gun expert, but it looks a lot like a typical assault rifle. He puts round after round through the weapon at high speed with no apparent issues.

    3D printed guns like these are difficult or impossible to trace. And laws meant to stop the spread of firearms don’t catch these “ghost guns.”

    How Big Is the Risk?

    Seeing a masked man on YouTube firing a ghost gun is disturbing, no question there. But how much worse are ghost guns than the normal ones?

    In most of America, it’s laughably easy to get a firearm. Where I grew up in Wisconsin, you can buy a shotgun at Wal-Mart just like you were buying milk.

    Most states and cities allow handguns and even assault rifles like the AR-15. The 3D printed weapons are no more dangerous than what’s for sale in countless stores nationwide with few if any controls.

    Take Luigi Mangione, the accused killer of Mr. Thompson.

    He used a 3D printed pistol. But if he had been almost anywhere else in America other than New York City, he could’ve bought a pistol legally.

    Remove every 3D printed gun, and Mangione probably still would’ve committed this awful crime.

    How to Regulate Ghost Guns

    Although it’s easy enough to buy normal guns in this country, we still don’t want every Tom, Dick and Harry printing weapons with zero oversight.

    The government should work with 3D printer manufacturers to ensure their devices cannot print firearm parts. The 3D printer could have software that recognizes key firearm components, such as the receiver or trigger group, and stops the printing process. It could even notify authorities of the attempt.

    This could prevent guns from falling into the hands of criminals and minors.

    Wrap-Up

    We need better regulation to stop ghost guns. If government works with 3D printer manufacturers, we could make a big dent in the ghost gun problem.

    But we should also keep in mind how easy it is to get the normal ones.

    I’m not saying take everyone’s guns away. But there has to be some middle ground between “take everyone’s guns away” and “unlimited, military grade firearms for the criminally insane.”

    It’s our job to find it.

    Have a great weekend, everyone!

    More on tech:

    Did a Robot Try to Attack Humans?

    How to Build a Drone Botnet for World Domination

    Why We Must Ban Chinese Robots

    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.

  • How to Get Inside Information on Startups

    If you trade on inside information in the public markets, you go to prison. In the private markets, all we do is trade on inside information. Here’s how to do it…

    How to Get Exclusive Startup Data

    Last year, I met with an amazing founder we’ll call Jim. The company was pre-revenue, but for a pre-revenue business, this was as good as it gets.

    I wasn’t ready to invest yet. But I asked if he could put me on his investor update.

    Fast forward a year…

    New e-mail in my inbox. It’s Jim’s latest update.

    Acting on Superior Information

    When I opened that e-mail, my jaw dropped. Jim had hit several hundred thousand in ARR in just a couple of months since launch. He was growing over 40% month over month.

    I replied, asking him to meet. We got on Google Meet and he gave me the latest on the company.

    These guys were absolutely crushing it. But could I get a taste?

    I asked Jim to invest, and he happened to have a bit more space in the round he was closing up. I quickly wired over the money, eager not to miss the opportunity.

    I was able to place this bet because I had inside information.

    Only a few dozen people got those updates. I was one of them.

    The average investor had no idea how fast this company was growing. But I did, and I was able to profit from that knowledge.

    A Scalable Model

    Being on the investor update of promising companies gives me a proprietary information flow.

    Every month, I get a bunch of e-mails with non-public financial info for awesome early stage startups. I pick the best and write them a check.

    This is a repeatable and scalable model.

    Just last week, I got an update from another company I met last year. They’ve begun to grow like crazy, and I’m setting up a meeting with them now.

    If you want to outperform other investors, you need some advantage. Better information is one of the most powerful advantages you can have.

    Because almost all information about private companies is private, there is nothing illegal or improper about acting based on private information. That’s the only information there is!

    Take advantage of that. When you meet an awesome founder, ask to be added to their investor update.

    And if you’re a founder, add investors you like to your update list. This gives them an easy way to follow your company. It also means you’re going to get crazy inbound if your growth up-shifts, which saves you a lot of time in fundraising.

    Wrap-Up

    “All I ever wanted in life was an unfair advantage.” That’s what Frank Costello said. I couldn’t agree more.

    Getting on the update list for great startups is an easy, legal way to get an advantage. There’s no reason not to do it.

    As I write this, we’re 5 days into June. Soon, a raft of new updates will hit my inbox.

    Among them just might be my next investment. I can’t wait!

    More on tech:

    Hot Categories I’ve Never Invested In

    Small Investors Lead to Big Investors

    Why It’s Easier to Raise $3 Million Than $300,000

    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. 

  • Hot Categories I’ve Never Invested In

    Are you sick of getting those automated messages on LinkedIn? So am I. AI Sales Development Reps is one of the 5 hot categories I’ve never invested in.

    Each cycle has a hot idea that 100 startups pursue. Most of the time, they all flame out.

    Here are the hot categories I’ve never touched…

    AI SDR’s

    This market is incredibly crowded. There are hundreds of these companies, and they seem to have no differentiation.

    Worse yet, the products don’t work.

    I was just chatting with a founder yesterday and he showed me his LinkedIn messages. He got a note that said “Hi [blank], I see you’re Founder | CEO of…” It couldn’t find his name and it transcribed his job character-for-character from his LinkedIn bio.

    No one’s responding to a message like that. So the AI SDR product doesn’t drive any sales.

    Hello, churn! And sure enough, these products churn like you wouldn’t believe.

    AI Note Takers

    I use an AI note taker, and I love it. But there are 1,000 of these and one isn’t all that different from the next.

    Also, an AI note taker is a feature, not a product. The product is the videoconferencing system.

    You’re already seeing AI note taking embedded into Zoom. I’m sure Meet and Teams will have it soon.

    Bye bye AI note taker.

    AI Image Generators

    I loved the image of Pope Francis in Balenciaga and ice. But I don’t love AI image generators as an investment.

    We will probably do image generation using foundational models. Grok and OpenAI already do it well.

    What’s more, there are about 1,000 AI image gen tools. None of them have any real differentiation.

    It’s hard to build a $1 billion business that way.

    NFT’s

    I love art, but I don’t collect it. So why would I buy NFT’s?

    I think owning digital art could become a thing. But the prices for Bored Apes and the like made no sense.

    When I see incredible froth in a category, I like to take a step to the left and find another place to play.

    Creator CRM’s

    Like NFT’s, Creator CRM’s were all the rage in 2021. Now, most of those startups are dead or dying.

    The problem is, only a full time creator is likely to buy SaaS products to manage their business. And there aren’t that many full time creators.

    Even among full timers, most don’t make much money. This means LTV’s will be low and churn will be high.

    Wrap-Up

    What do all these categories have in common? They’re all obvious.

    Sometimes, 100 people have the same idea and go build the same startup. Each product has a slightly different spin on the problem, but fundamentally they’re the same.

    I go toward the non obvious ideas.

    Take Prandtl Dynamics. They’re building an ultrasound system to stop drones. In the future, every soldier will carry one.

    That’s transformative tech. And it’s not something 100 companies can do.

    That’s the type of thing that gets me excited!

    If you’re a founder, don’t make a me-too product. Make something transformative.

    Do it even if everyone tells you it’s stupid. That could be the best sign that you’re on to something.

    More on tech:

    Get Rid of Your Investment Minimum

    Small Investors Lead to Big Investors

    Why It’s Easier to Raise $3 Million Than $300,000

    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.

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    Misfits Market

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