Tremendous

An angel investor's take on life and business

  • Start Your Deck the Right Way: By Selling Yourself

    I see it in deck after deck: the founder waits until slide 27 to tell me about himself. Big mistake. Here’s how to do it right…

    Right after your title slide, put a slide about yourself. Tell us your biggest accomplishments.

    Before we care about your idea, we have to believe in you! 

    Don’t Bury the Lead!

    I’ve seen some amazing founders completely bury their accomplishments. 

    One deck I looked at recently had the founder on the very last slide. This guy has some incredible accomplishments, including doing serious engineering work at a top deep tech startup. 

    But looking at the deck, you’d never know it! 

    What are the odds the investor actually makes it to Slide 41 with that information? Not high.

    That’s why you put it front and center. 

    How to Sell Yourself

    Don’t just tell us where you’ve worked. Anyone can do that. 

    Tell us the important things that you accomplished.

    Maybe you worked at Anduril. Don’t just put an Anduril logo on your slide. 

    Instead, tell us your biggest accomplishments there. Maybe you led a project to develop sensors for their unmanned fighter. 

    Now that’s exciting!  

    Not many people have done something that big. That’s okay! 

    Just sell the best accomplishments you have.

    Maybe you started a garage cleaning business in high school that paid your way through college. That’s amazing!

    Make sure investors know about it. 

    Why You Must Lead With Yourself, Not Your Idea

    You don’t want to lead with your startup idea, the market, or the product.

    Without an exceptional founder, no idea is likely to work. First, show us you’re that exceptional person.

    What’s more, many startups pivot to a totally different business. One of my most successful investments, Micro1, was a completely different company when I invested.

    Wrap-Up

    Raising money is hard enough. Don’t make it even harder by underselling yourself!

    You are the most critical asset your company has. Whether you raise money or not will depend on how investors assess you as a person.

    If you’re raising money now, open up your deck and start making some edits. Put yourself front and center.

    You’ll see the difference in how investors respond!

    More on tech: 

    How Sid From GitLab Nailed His Pre-Seed Pitch In Just 60 Seconds

    How to Write Cold Emails to Investors That Actually Get Replies

    You’ve Got Your First Customer. Now, How Do You Raise Money?

    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!

    Wispr Flow

    I used this app every single day to dictate to my computer, I’m even dictating this text using Wispr Flow! It’s way better than Apple’s native dictation.

    My productivity is up about 25% since I started dictating rather than typing. I’m also less tired and stressed.

    Get a free month of Wispr Flow Pro here!

  • How Sid From GitLab Nailed His Pre-Seed Pitch In Just 60 Seconds

    GitLab is a $5 billion company with over 50 million users. But in 2015, it was just a tiny startup. Today, I watched their original YC application video. It’s one of the best pre-seed pitches I’ve ever seen. 

    Founder Sid Sijbrandij does an incredible job of selling himself. In less than a minute, he gives us enough to get any investor excited.

    Let’s break down his pitch and see how you can learn from Sid…

    Selling Himself as a Founder

    Sid starts by telling us about his prior startup, which sold recreational submarines. He built it into the largest producer of recreational submarines in the world. 

    This tells us that Sid knows how to build a company. If we invest in him, we have a better chance of getting a return than someone who hasn’t started a business before. 

    When you pitch investors, sell them on your biggest accomplishments. Maybe you created a business in high school. Maybe you did some original scientific research. 

    Give us evidence that you’re exceptional!

    Getting the Pitch Down to One Simple Sentence

    Next, Sid explains what GitLab does: “GitLab is open source software to collaborate on code.”

    See how clear that sentence is?

    When an investor doesn’t understand what you do, he tunes out. And you don’t get a check.

    Get your vision down to one simple sentence, like Sid did. The first step in getting a check is making sure investors understand what you do. 

    Showing Real Traction

    Sid gives us strong evidence that GitLab is catching on. It’s already used by over 100,000 organizations at this point.

    Very few pre-seed startups have that kind of traction. But whatever traction you have, make sure investors know about it!

    Let’s say you have three paid customers. I know, that’s not all the money in the world. 

    But it’s a nice start! Make sure you mention it.

    Controlling Your Own Destiny

    Sid is working hard to get funding from YC. But he also makes clear he doesn’t really need it.

    GitLab is already cashflow positive. That’s very unusual for an early-stage company.

    This shows that Sid is great at getting paying customers. It also shows he’s done an excellent job controlling expenses.

    Getting to cashflow positive this early on is quite difficult. But if you and a co-founder can take minimal or no salary and build everything yourself, you have a chance to get to default alive early. 

    This sets you apart from other startups. It also frees you from depending on investors.

    Wrap-Up

    In less than a minute, Sid gives us powerful evidence that he’s an exceptional entrepreneur.

    He’s built a successful business in the past. He’s taken GitLab live and signed up lots of customers. And he’s already profitable. 

    Most any pre-seed investor would make this bet. 

    Very few pre-seed companies are as strong as GitLab was in 2015. But you can learn from Sid to make your pitch better.

    Lead with what makes you exceptional. Then, clearly explain what you do and how it’s going. Control expenses so you’re not at the mercy of VCs.

    If you can do that, you just might create the next GitLab. 

    More on tech: 

    You’ve Got Your First Customer. Now, How Do You Raise Money?

    Why Short Decks Raise Millions

    “Don’t Be Afraid to Fail” — Three Lessons from Elon That Will Make You a Better Founder, Leader, and 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!

    Wispr Flow

    I used this app every single day to dictate to my computer, I’m even dictating this text using Wispr Flow! It’s way better than Apple’s native dictation.

    My productivity is up about 25% since I started dictating rather than typing. I’m also less tired and stressed.

    Get a free month of Wispr Flow Pro here!

  • You’ve Got Your First Customer. Now, How Do You Raise Money? 

    You just signed your first customer! Is it time to raise a pre-seed round? 

    A founder on Reddit is in this exact situation. He just made his first revenue — $3,000 from one client. That’s a huge milestone!

    But it’s probably not enough to raise a full pre-seed. Here’s what he should do instead…

    The Accelerator Path

    For a founder just beginning to pull in revenue, accelerators are the best next step.

    That trickle of revenue will make it much easier to get into a good program.

    An accelerator could put this founder in a perfect position. He’ll get the $100k to $500k he needs. That gives him several months to keep growing.

    Once he hits a couple hundred thousand in ARR, he’ll be in a great position for a round in the millions. 

    Some Founders Skip the Line

    Some founders raise millions of dollars with just a couple of text messages. The caveat: they usually have an incredible track record.

    If a founder sold their last company for $1 billion, everyone will be rushing to fund them before they even make a deck. 

    Most founders don’t have that gold-plated track record. They need to prove themselves before they can raise money.

    Understanding How Fundable You Really Are 

    Every day, I meet founders who think they’re ready to raise a pre-seed round of $500k to $2 million. I often have to tell them that isn’t realistic.

    Instead, I suggest accelerators.

    I can tell a lot of them get frustrated when I mention this! They think they’re past that point.

    But with neither strong traction nor a strong track record, it’s hard to raise a full funding round. Most founders are better off raising a smaller amount now and continuing to build.

    You can still raise that fat round later. But you’re going to need a little more traction to do it.

    Wrap-Up

    If you’re a founder who just signed their first customer, my hat is off to you! But this is just the beginning.

    Even with a trickle of revenue, raising money is a hard slog for most founders. Take it step by step. 

    Build the product. Get a customer or two. Get into a strong accelerator program. 

    Bust your hump in that program and grow as fast as you can.

    When you graduate, you’ll be ready to raise millions.

    More on tech:

    How to Write Cold Emails to Investors That Actually Get Replies

    Why Short Decks Raise Millions

    “Don’t Be Afraid to Fail” — Three Lessons from Elon That Will Make You a Better Founder, Leader, and 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!

    Wispr Flow

    I used this app every single day to dictate to my computer, I’m even dictating this text using Wispr Flow! It’s way better than Apple’s native dictation.

    My productivity is up about 25% since I started dictating rather than typing. I’m also less tired and stressed.

    Get a free month of Wispr Flow Pro here!

  • How to Write Cold Emails to Investors That Actually Get Replies

    You and 100 other founders are cold messaging the same investor. Here’s how to stand out….

    You want your message to be short and compelling. The longer it is, the less likely the investor will read it.

    First, let’s cover three critical components of a great cold message. Finally, we’ll put them all together and draft a cold message for a startup.

    Part 1: Why You’re Exceptional

    Before you even tell us your idea, tell us why you’re an exceptional founder.

    Many startups pivot away from their original idea. The one thing least likely to change: the founder.

    So, sell us on you!

    Show us you’re exceptional. Give us your biggest achievements.

    Say that in high school, you created a car detailing business that made it to $1 million a year in revenue. That’s incredible! 

    Your new company might not have anything to do with car detailing. But you should definitely share that information with us! 

    Part 2: What You Do, In One Simple Sentence

    Once you’ve told us why you’re exceptional, tell us what you’re working on now.

    Get the idea for your startup down to one simple sentence. Be clear and specific. No jargon. 

    Say you’re Travis Kalanick in 2010 and you’re starting Uber. Here’s what that one simple sentence could look like:

    “Uber gets you a private driver from anywhere to anywhere.”

    Right away, it’s clear what Uber does. Now, imagine if Travis had come out with this sentence:

    “Uber is a platform for democratizing transportation through a decentralized network of individual service providers.”

    The sentence is still true. But it obscures what Uber does.

    When investors don’t understand, they tune out. 

    Part 3: Traction

    You told us why you’re exceptional. You told us what you’re working on now.

    Finally, tell us how it’s going.

    Give an annualized revenue number if you have revenue. If you don’t have revenue, give the number of monthly active users. If you don’t have that, give us the number of people on the wait list.

    You want to provide evidence that your company is growing. 

    Naturally, higher growth is better! But don’t give in to the temptation to make up numbers. 

    Putting It Together: Drafting a Great Cold Message

    Let’s put these three elements together…

    Say Jim has a company called Superstartup. It provides AI coaching to founders.

    Jim had a very successful car detailing business in high school, which shows his ability as an entrepreneur. His startup also has some good early traction. 

    Jim could write a cold message like this:

    “Hi Mr. Moneybags,

    I’m Jim. In high school, I grew a car detailing business to $1 million a year in revenue. 

    Now I’m building Superstartup — every founder’s AI coach. 

    We’ve hit $200,000 ARR in 2 months since launch.

    Deck attached.

    Worth hearing more?”

    The message is just a couple of lines. It’s factual and shows what a great entrepreneur Jim is.

    Send that message to 100 seed investors, and you’ve got yourself a hot fundraise.

    Wrap-Up

    Most of your competitors for funding will send long, meandering messages. 

    Those messages won’t include the information investors want. And they won’t get a meeting.

    You need to be different!

    Show us why you’re special. Be clear on what your company does. Give us evidence that it’s working.

    If you can hit those points concisely, you’re going to book a calendar full of investor meetings. You only need one term sheet to change everything. 

    Try writing up a draft cold message. And if you want my feedback on it, leave it in the comments!

    More on tech: 

    Why Short Decks Raise Millions

    So You Didn’t Hit $100M ARR in 6 Months — Fundraising Advice for The Rest of Us

    Yes, You Can Raise VC Money in ‘Unsexy’ Areas — Here’s What Investors Want

    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!

    Wispr Flow

    I used this app every single day to dictate to my computer, I’m even dictating this text using Wispr Flow! It’s way better than Apple’s native dictation.

    My productivity is up about 25% since I started dictating rather than typing. I’m also less tired and stressed.

    Get a free month of Wispr Flow Pro here!

  • Japan’s Top 5 Startups Right Now: AI, Biotech, and Deep Tech 

    Five companies. $9.47 billion. These are the most valuable startups in Japan now. 

    I’m scouring Japan for the next billion-dollar startup. So I wondered: What are the most successful Japanese startups so far, and what can I learn from them? 

    Japan’s Biggest Startups

    I focused on the top 5 private tech startups in Japan today. Collectively, they’re valued at over $9 billion. They range from AI labs to biomanufactured proteins:

    What struck me right away is that not all of the top five are in Tokyo! Yamagata is home to Spiber, a biotech valued at $1.2 billion.

    These companies are doing some amazing things. Sakana AI has released an AI scientist that writes academic papers. Spiber is creating proteins to replace cashmere, wool, and fur. 

    I notice a greater deep tech and research bent compared to America. More robotics and biotech, less SaaS. 

    This tells me to look for more than just software companies.

    Beyond the Top 5

    These five companies aren’t the only highly successful startups in Japan. 

    Japan has around 10 unicorns currently, give or take a couple depending on which source you rely on. They span a variety of fields, from video games to crypto platforms. 

    Japan’s startups may not be the biggest in the world. But given the lack of capital in Japan, the entry prices for most were probably quite low.

    This means a massive multiple on cash for early investors.

    Japan’s Biggest Exit

    It’s one thing to notch a high valuation in a funding round. Getting liquid is much harder.

    The biggest startup exit in the last decade in Japan is Mercari, which lets you buy and sell used goods online. It went public in 2018 and is valued at about $4.4 billion in the public markets.

    Almost every Japanese person I’ve met was quite frugal. And given the difficult economic situation, people have all the more reason to buy used and sell unnecessary possessions.

    Startups that help people save money or make extra income are good bets in Japan. I’m keeping an eye out for more like this…

    Wrap-Up

    If I can find investments where others aren’t looking, I can make a lot of money.

    When I was in Tokyo recently, I met one talented builder after another. But there isn’t enough risk capital in Japan to fund their companies.

    Companies like Sakana AI and Mercari prove Japan can produce serious returns. Bring in more American investors, and there’s no telling what Japan can do. 

    If you’re an awesome founder in Japan struggling to raise money locally, shoot me a message. I’m excited to learn about what you’re building!

    Have a great weekend, everyone!

    More on tech: 

    Inside Japan’s Startup Boom: Elite Engineers, Exploding Revenue, and Almost No Funding

    The US-Japan Hybrid Startup: Move Founders to America, Keep Talent in Japan

    So You Didn’t Hit $100M ARR in 6 Months — Fundraising Advice for The Rest of Us

    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!

    Wispr Flow

    I used this app every single day to dictate to my computer, I’m even dictating this text using Wispr Flow! It’s way better than Apple’s native dictation.

    My productivity is up about 25% since I started dictating rather than typing. I’m also less tired and stressed.

    Get a free month of Wispr Flow Pro here!

  • So You Didn’t Hit $100M ARR in 6 Months — Fundraising Advice for The Rest of Us

    You’ve seen the headlines: startups hitting $100M ARR overnight. You’re not one of them. So how do you raise money? 

    We’ve all seen the headlines about startups with ridiculous growth. But the reality for most founders is a lot less glamorous.

    Grinding out growth bit by bit. Trying not to run out of money.

    How does the average founder go about raising capital in 2026? The key is to get into a position of strength…

    Understand the Investor’s Perspective

    Imagine you’re an investor….

    It’s 9am. You’ve got a nice big cup of iced coffee next to your laptop. Time to go through your inbox.

    You’ve got 15 emails. 10 are from pre-revenue companies. 4 are from companies growing 1-2x year over year.

    And that last email? A startup that’s made it to $1M ARR in two months.

    Put yourself in the investor’s position. What deal are you going to do?

    What’s Changed Since I Started Investing

    I started angel investing in 2021. At that time, 3x year over year growth was considered incredible. You’d definitely be able to raise.

    It doesn’t work that way anymore. AI is helping some startups grow faster than anything we’ve ever seen. 

    Those supergrowth startups are competing with you for capital.

    In 2026, the bar to get investors excited isn’t 3x year over year growth. It’s more like 10x. 

    That’s a crazy bar, I know! But it’s what the market dictates.

    How to Respond: Get to Break Even

    Let’s say you’re growing, but not at those eyepopping rates. Maybe you’re scaling revenue 25%, 100%, or 200% year over year. 

    My best advice: get to break even.

    This will mean painful decisions, like big layoffs or taking a pay cut.

    But the reality is that you cannot rely on venture capital right now. The supergrowth companies will get funded. You may not.

    If you keep burning and fail to raise, you’re going to go broke. Your company will cease to exist.

    That’s a lot more painful than making some cuts now.

    Every single cost is on the menu: headcount, office space, travel. Cut, cut, cut. 

    The Position of Strength

    Once you’re at break even, you hold the cards.

    You don’t need venture capital anymore. It becomes a nice-to-have.

    If the money’s there and the terms are reasonable, take it. If not, no worries!

    And if you can re-accelerate growth to at least 5x, you may find investors getting excited again.

    But you need time to figure out a path to faster growth. Getting to break even buys you that time.

    Wrap Up

    There’s nothing easy about being a founder.

    Even before AI, entrepreneurship was a struggle. Today, it’s a mad race for customers and investor dollars. 

    In a market this competitive, the average founder can’t count on raising venture capital. So you need to learn to operate without it. 

    Get your company to break even, no matter what it takes. Control your destiny.

    Then raising capital becomes optional.

    More on tech: 

    Yes, You Can Raise VC Money in ‘Unsexy’ Areas — Here’s What Investors Want

    Inside Japan’s Startup Boom: Elite Engineers, Exploding Revenue, and Almost No Funding

    Meet My Latest Investment: Perfectly

    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!

    Wispr Flow

    I used this app every single day to dictate to my computer, I’m even dictating this text using Wispr Flow! It’s way better than Apple’s native dictation.

    My productivity is up about 25% since I started dictating rather than typing. I’m also less tired and stressed.

    Get a free month of Wispr Flow Pro here!

  • How Jon McNeill Scaled Tesla from $2B to $30B — 3 Lessons I’m Stealing for My Own Business

    Jon McNeill took Tesla from $2 billion to $30 billion in revenue as one of Elon’s top lieutenants. His secret? Total focus on a few goals, and obsession with the customer.

    McNeill recently gave up his secrets in The Algorithm. This slim volume explains how Tesla went from struggling startup to trillion dollar company. 

    I couldn’t put this book down on my recent vacation. Here are three key lessons I’m already using in my work…

    1. Set goals for meetings. “The point of this meeting is to get everyone together…” This is an actual quote from one of the bosses I encountered early in my career. 

    Right away I thought, “So the point of this meeting is to have a meeting?”

    Corporate America is filled with pointless meetings. If you add up the hourly wage of everyone there, these meetings cost many thousands of dollars per hour.

    Elon makes sure that his companies don’t waste time. They agree on a goal for a meeting up front. Anyone who isn’t needed is encouraged to simply get up and leave. 

    Try setting a goal at the beginning of all your company meetings. You can save a lot of time!

    2. Look at your product from your customer’s perspective. When the author was president of Tesla, he would go into the showrooms and go through the car-buying experience. 

    He found that the Tesla representatives often didn’t follow up with potential customers. So he instituted a new process to make sure that every lead is followed up on. 

    For me, startup founders are my customers. I think to myself, “What do they need?”

    Above all, they need prompt and clear responses from me. If you’re trying to raise money for a company, you can’t wait a week to get your emails returned.

    So I try to get back to every founder within 24 hours or less. At the end of meetings, I clearly explain what I’m looking for before I invest. 

    One place where I can improve is getting founders a meeting faster. I’m going to try to get folks on the schedule sooner whenever I can.

    3. Small teams, clear goals, accountability. Elon likes to form a small team and give them a clear goal. Then he has them report back regularly on their progress.

    If you know you’re going to have to report to the CEO in a week, you’re going to work really hard. You can’t come back to Elon next week and tell him you didn’t accomplish anything!

    In the average corporation, goals and responsibility are unclear. And with nine layers between you and the CEO, you can avoid being noticed.

    That’s not going to happen at Tesla. 

    Take the most important goal at your company and assign a small number of people to work on it. Make them report back to you weekly or even daily.

    You’ll be surprised how much gets done!

    Wrap Up

    Elon’s companies operate on a different level from most businesses: clear goals, accountability, and focus on the customer. 

    Try setting a couple key goals in your business. Make it crystal clear who’s responsible.

    In my business, I’m thinking hard about how to make founders’ experience better. I’m going to try to get meetings on the schedule faster so founders don’t have to wait.

    The better I service the founders I work with, the more great entrepreneurs will come to me. 

    What changes do you want to make at your company? 

    More on tech:

    “Don’t Be Afraid to Fail” — Three Lessons from Elon That Will Make You a Better Founder, Leader, and Investor

    Elon Musk (Part 1): Overcoming the Odds

    Three Lessons on Business from Warren Buffett

    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!

    Wispr Flow

    I used this app every single day to dictate to my computer, I’m even dictating this text using Wispr Flow! It’s way better than Apple’s native dictation.

    My productivity is up about 25% since I started dictating rather than typing. I’m also less tired and stressed.

    Get a free month of Wispr Flow Pro here!

  • Grok Skills: Generate Pitch Decks, Spreadsheets and More with AI

    AI is great for answering questions. But what if you want to generate slide decks, spreadsheets, and more? Elon has you covered…

    xAI recently dropped Grok Skills, a new tool that lets you create reusable agents. Grok Skills can create a spreadsheet, write a weekly status report, or even review code. (You can access skills by clicking the + sign next to the main prompt box in Grok.)

    I ran Grok Skills through a three round test. It’s great for creating spreadsheets or helping you learn a language, but struggles with other tasks like generating a pitch deck.

    Let me show you what Grok Skills can do…

    Round #1: Creating a Pitch Deck

    For starters, I ran one of Grok’s pre-loaded skills: creating a pitch deck. 

    Grok provides an example deck for an AI enterprise startup. This gives you an idea of the presentations Grok can make for you. 

    Grok’s example deck was mediocre. There’s way too much text crowded on each slide. This makes it hard to scan.

    But Grok does get some things right, using a minimalist design with very readable white text on a black background.

    I’m giving this round a C. 

    Round #2: Generating a Spreadsheet to Track Startups

    For our next round, I had Grok Skills generate a spreadsheet.

    I track every startup I pass on in a giant sheet. Then, if one of these startups breaks out, I can go back and see why I passed. 

    Assume a new angel investor wants to do this. Can Grok make him a passed deals spreadsheet?

    Grok made a great little sheet here, including details like founder name, valuation, and reason for passing. I’d fine-tune this by adding a data validation for common reasons to pass.

    Grok’s sheet is an excellent starting point. I’m giving this round an A-. 

    Round #3: Building a Custom Skill to Translate Japanese

    For our final round, I built a custom Grok Skill. I’m going to make Grok teach me Japanese!

    Google Translate is great at giving you the meaning of text, but it doesn’t really teach you how to understand the Japanese. It just translates for you.

    I need a tool that breaks down and explains text, so I can learn.

    I gave my new Grok Skill detailed instructions on how to teach. I’m having it break down every single word, translate it to English, write it in Roman letters (Romaji), and then explain the whole passage. 

    To test my new skill out, I gave Grok a picture I took on my recent trip. It shows a closing notice at my favorite diner, Jonathan’s.

    Grok did a really nice job of breaking down the meaning of the sign. It explained that it says the store will be closed for several days for renovations.

    I’d like to see Grok break down word by word rather than phrase by phrase. But this was still very useful!

    I’m giving Grok a B+ on this round. 

    Wrap-Up

    I’m giving Grok Skills a B overall.

    Skills are a useful way to create documents and run custom prompts. If Grok can save you a few minutes building a spreadsheet or retyping instructions, that’s a huge win over time.

    If I know Elon, he’s going to introduce more and more Grok Skills. Soon, we’ll be able to point, click, and get Grok to do a lot of our work for us.

    Give Grok Skills a try and see if you can automate some of your work!

    More on tech: 

    Grok Connectors: Elon’s New Agentic System Excels on Simple Tasks, Falls Short on Complex Operations

    What If AI Guided You Instead of Just Giving Answers? — Testing Gemini Guided Learning

    Moonshot Drops Kimi K2.6 – Cheap, Powerful, and Worth Trying for Builders

    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!

    Wispr Flow

    I used this app every single day to dictate to my computer, I’m even dictating this text using Wispr Flow! It’s way better than Apple’s native dictation.

    My productivity is up about 25% since I started dictating rather than typing. I’m also less tired and stressed.

    Get a free month of Wispr Flow Pro here!

  • Grok Connectors: Elon’s New Agentic System Excels on Simple Tasks, Falls Short on Complex Operations

    Elon recently dropped Grok Connectors, a new tool to manage your email, calendar and more. Grok excels at basic tasks like email summarization. But for more complex operations, it falls short. 

    This morning, I ran Grok Connectors through a three round test. I had it do everything from inbox management to meeting prep.

    Let me show you what Grok Connectors can do… 

    Round #1: Crushing My Inbox

    Every day, I seem to get more emails than the day before! Can Grok help me manage the chaos?

    First, I asked Grok to summarize my emails. All I had to do was type “@Gmail” and tell it to summarize.

    Grok gave me a great little summary of everything in my inbox. It’s pretty light at the moment —  I just checked it an hour ago. If I had an avalanche of messages, this would be even more useful.

    But Grok can do a lot more than summarize. It can reply to emails, move them, even delete them.

    I had Grok write a reply to a founder. It wrote a draft, but wouldn’t send it for me.

    I asked Grok if it can just send emails from now on, and it said yes. We’ll see how it goes on future emails!

    I also told Grok to delete some messages I didn’t need. That part worked beautifully.

    Overall, the Gmail Connector is great for summarization but less useful for replies. I’m giving this round a B.  

    Round #2: Prepping for my Meetings

    I’ve got a full slate of meetings next week with some great founders. So I used the Google Calendar Connector and had Grok prep me for Tuesday. 

    Grok gave me a nice calendar summary. But unfortunately, Grok said it cannot connect to my LinkedIn or X messages. I need to dig into those to prepare for my meetings.

    I’m surprised that Grok can’t connect to X. It’s the same company! Inability to read messages across platforms makes Grok Connectors a lot less useful. 

    In all, Grok didn’t give me anything I couldn’t get just glancing at my calendar. I’m giving this round a D. 

    Round #3: Helping Me Reconnect With Great Founders

    Sometimes, I chat with a great founder, but their company is a little too early. So I wondered, who I was talking to six months ago that I haven’t spoken with recently?

    I had Grok search my Gmail for founders I was corresponding with in late 2025 and haven’t spoken to lately. 

    Grok named a couple of founders that I’ve invested in. But I’ve actually corresponded with them recently. I even e-mailed one this morning!

    This round gets an F.

    Wrap-Up

    Overall, I’m giving Grok Connectors a D+.

    Connectors works well for simple tasks, like summarizing an inbox or replying to an email. But for anything more complex, it misses the mark.

    It doesn’t have many integrations yet. It also fails to understand complex prompts and act on them.

    Grok Connectors is a new product, so we can’t expect perfection. If xAI can really nail Connectors, it would make Grok 10x more useful.

    I’m excited to see future releases from xAI. I hope that in a year’s time, I can do everything in Grok.

    Have a great Memorial Day, everybody! 🇺🇸  

    More on tech: 

    Inside Japan’s Startup Boom: Elite Engineers, Exploding Revenue, and Almost No Funding

    “Don’t Be Afraid to Fail” — Three Lessons from Elon That Will Make You a Better Founder, Leader, and Investor

    Meet My Latest Investment: Perfectly

    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!

    Wispr Flow

    I used this app every single day to dictate to my computer, I’m even dictating this text using Wispr Flow! It’s way better than Apple’s native dictation.

    My productivity is up about 25% since I started dictating rather than typing. I’m also less tired and stressed.

    Get a free month of Wispr Flow Pro here!

  • My Top Japan Recs: Sushi, Castles and Samurai Graves

    Odawara Castle

    I just spent 3 weeks in Japan. Here are my top recommendations for food and awesome sights…

    Food

    Tsukiji Ginikkan

    This fantastic conveyor belt sushi bar isn’t actually in Tsukiji. It’s in a charming shopping street called Musashikoyama. But this sushi would stand up anywhere.

    You can order in English via tablet. Get the akagai, or ark shell clam.

    Ginjo Maguro Shinagawa

    The best tempura I’ve ever had. They also have incredible magurodon.

    The owner is very sweet. There’s an English menu, which is always super helpful. And there’s even a young lady waitress here who speaks perfect English!

    Centre Bakery French Toast, an amazing JCal rec

    Centre Bakery

    The finest French toast anywhere. They soak it in cream overnight. All the bread is baked in house.

    English menu available!

    Me pigging out at Jonathan’s — so awesome!

    Jonathan’s

    Last but never, ever least! This fantastic diner can get you just about food you want. It’s delicious, fast, and very reasonably priced.

    I especially love the drink bar, where you can enjoy unlimited coffee, juice, seltzer, soda and more!

    I ate here more than anywhere else on my trip! It’s the perfect breakfast spot. Try the pancakes with shaved butter.

    You can order in English via tablet too!

    I provided a link to the location I visited, but there are many across Japan.

    Sightseeing

    Koishikawa Botanical Garden

    Koishikawa Botanical Garden

    Japan has countless gorgeous gardens. But I especially enjoyed this one!

    The wooded paths are uncrowded. They branch off in every direction, giving you the feeling of being lost in nature in the middle of the city.

    Admission is just 500 yen, or about $3! An absolute steal.

    Shinjuku Gyoen

    This famous garden right near Shinjuku Station is easy to get to and filled with massive trees and beautiful flowers. Admission is a rock bottom 500 yen, or about $3.

    Be sure to check out the rose garden!

    Institute for Nature Study

    This garden is conveniently located right in Meguro. And yet, it’s so heavily wooded you’d think you were deep into rural Japan!

    The staff here are very nice, and admission is just a couple hundred yen. Please consider giving the extra donation for a total of 1000 yen.

    Odawara Castle

    Just 20 minutes from Shinagawa Station in Tokyo via Shinkansen, this beautiful castle is not to be missed. In the adjacent Samurai Museum, you can see a chain two brothers used to strangle the man who killed their father.

    The beach a couple blocks away makes a wonderful place to relax after!

    Wrap Up

    My goal is to get every single person to visit Japan. That includes you!

    You won’t find kinder people, more delicious food, or more amazing sights. I’ve been 7 times and I’m already planning an 8th trip.

    To all the wonderful Japanese people I met and who made this great society, a very hearty thank you! I look forward to joining you again soon.

    日本人の皆さん、本当にありがとうございます！すぐ戻りたいです！

    Note: I’m back in America! The blog will be back on its normal Monday-Friday schedule, with a day off on Monday for Memorial Day. Looking forward to sharing lots more cool tech and business happenings with you guys!

    More on tech:

    The US-Japan Hybrid Startup: Move Founders to America, Keep Talent in Japan

    Inside Japan’s Startup Boom: Elite Engineers, Exploding Revenue, and Almost No Funding

    Eating Breakfast With Robots in Tokyo

    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!

    Wispr Flow

    I used this app every single day to dictate to my computer, I’m even dictating this text using Wispr Flow! It’s way better than Apple’s native dictation.

    My productivity is up about 25% since I started dictating rather than typing. I’m also less tired and stressed.

    Get a free month of Wispr Flow Pro here!