Tremendous

An angel investor's take on life and business

  • Off-the-shelf email agents draft nonsensical replies that sound nothing like me. So I built my own…

    My new Grok Automation is saving me serious time managing my inbox. The key: giving Grok extremely specific instructions with examples.

    The Problem With Email Agents

    Tons of different tools claim to manage your inbox. I’ve tried Upstream, Town, and more. 

    They read through your emails and try to draft replies in your voice. 

    But despite reading my messages, the agent didn’t really understand what I do. It drafted responses that didn’t sound like me and didn’t make sense in context.

    So I built my own with Grok. Here’s how it works…

    Teaching Grok How to Manage My Emails

    First, I showed Grok how to categorize my messages:

    1. Too early, ask founder to follow up later
    2. Not an area I invest in
    3. Good prospect, want to book a meeting

    For example, a pre-revenue company goes into Bucket 1. A US based software startup with 3 customers goes into Bucket 3.

    Then, I gave Grok example messages to send in each case. 

    For the pre-revenue founder, I had Grok say: “I don’t do pre-revenue, but feel free to shoot me a message when you have 3 paying customers, and I’d be happy to take another look. Thanks!”

    This way, I know Grok will sound like me. 

    Taking My Agent Out on the Road

    I was astounded to find the agent actually works! 

    It parsed a founder email, found the company was pre-revenue, and politely declined. It found another message from a startup that has several customers and asked to book a meeting.

    Success! 

    Not every draft reply is usable, but around half are. I hope to improve the agent’s performance over time. 

    Maintaining the Human Touch

    My Grok agent is making it easier for me to stay on top of my messages. But I never want to drain the humanity out of my relationship with founders.

    I always look over every draft before I send it. I want AI to help me, not take over. 

    There are also tons of edge cases that my agent isn’t ready for: someone inviting me to an event or a founder who wants an intro.

    It’s tough to make an agent work in every single case. What matters to me is handling the more common message types.

    Building Your Own Email Agent With Grok

    If you’re struggling to get through your emails, try building your own email agent with Grok!

    Maybe some of your messages are spam and don’t require a response. Others are from sales prospects — you want to book meetings with these.

    Once you explain the categories and give Grok example messages, it should be able to manage many of your emails. 

    Wrap-Up

    I’m used to prompting AI by just giving it a general idea of what I want.

    Then I realized: I’m not being an effective teacher. If I was trying to teach this to a human, they probably wouldn’t get it. 

    No wonder AI doesn’t either!

    Giving Grok a clear framework and example outputs made all the difference.

    If you’re struggling with your inbox, try Grok Automations! 

    More from the blog:

    I’ve Seen Thousands of Founder Pitches. These 5 Mistakes Keep Showing Up.

    Building a Deal-Tracking App in Just 4 Minutes with Grok 4.6

    Fundraising Friction is Killing Your Round – Here’s How to Remove It

    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!

  • I have a new personal trainer: Arnold Schwarzenegger. And I’m finally having fun in the gym! 

    For the last 16 years, I’ve designed my own strength training programs. The results: a mediocre physique. 

    A couple of weeks ago, I saw a post from Arnold Schwarzenegger on X. He was running a special on his new workout app, Arnold’s Pump Club

    I’ve been a huge fan of Arnold Schwarzenegger for years. What did I have to lose? 

    Doing My First Workout 

    I’ve never used a fitness app before. Would I even be able to figure out how to do these workouts?

    Fortunately, Pump Club makes it easy. Every single exercise has an awesome instructional video. 

    You can even swap out exercises if you don’t have the right equipment or you have an injury. I replaced squats with stiff leg deadlifts, which are much easier on my back. 

    Tracking Workouts the Easy Way

    My first workout was rough!

    I was pouring sweat and out of breath. But that’s how you know you’re getting somewhere, right? 

    Pump Club makes it super easy to track workouts. There’s spots to put in pounds and number of reps.

    Then the next time you do that exercise, the app pulls in your prior weight and rep count. 

    Lifting 2.5x As Much, Having 10x More Fun!

    I never knew if the programs I designed were good or not. That left me less motivated to work out. 

    Outsourcing everything to Arnold has made a huge difference.

    Arnold still looks great at 79 years old. Whatever he’s doing is working. 

    Since I’m confident the workouts will pay dividends, I’m much more motivated to do them. 

    Pump Club has gotten me to increase my weight workouts from two to three times a week. My workouts have gone from 45 minutes to around 1 hour 15 minutes.

    I’ve 2.5x-ed my training volume. And I’m having a lot more fun! 

    Pump Club Is a Friendly Place

    The internet is filled with negativity. Pump Club is one place where I never see that.

    If you put up a post saying you crushed your workout, people rush in to congratulate you! 

    I’ve tried to encourage others as well. It feels good to know that somebody, somewhere may be a little more motivated because I cheered them on. 

    Wrap-Up

    I really encourage you to try this app! I’ve recommended it to all my friends.

    Pump Club has programs for everyone. It works for people who’ve never exercised all the way to advanced weightlifters. 

    The club includes people of all ages. Arnold himself is almost 80! 

    Click this link to get your first month free! After that, the price is $150 a year, with up to $100 in rebates if you complete 4 programs.

    More from the blog: 

    My New AI Assistant is Finding Me Cheap Flights to Japan

    Using Grok Socratic Mode to Learn About Health

    Building a Deal-Tracking App in Just 4 Minutes with Grok 4.6

    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!

  • I’ve looked at thousands of founder pitches. Here are 5 mistakes I keep seeing, and how you can avoid them…

    1. Don’t Ask Investors to Sign an NDA. No investor worth their salt is going to sign an NDA.

      Every year I look at thousands of decks. Can I sign thousands of NDAs? No one could ever keep on top of that many different legal agreements.

      Instead, just send the materials, sans legal agreements.
    2. Don’t Have a Minimum Check Size. I recently got a message asking for angel funding. Minimum check size: $500,000

      It doesn’t make sense to pitch angels and ask for a $500,000 minimum. Very few angels write checks that big.

      A couple of years ago, I was in a round with a billionaire angel. That person only wrote a $250,000 check.

      So, what minimum should you have?

      If a person is helpful, I wouldn’t have a minimum check size. Many founders tell me their most helpful investors were their smallest.
    3. Don’t Follow Up Immediately. Sometimes a founder will email me and then message again an hour or two later to see if I have looked at their deck.

      I try to get respond to everyone in under 24 hours. But I can’t always look at your message instantly.

      Give us at least three days before you follow up.
    4. Don’t Write Long Messages. Many founders write extremely long messages — hundreds of words. The longer your message is, the less likely an investor will read it.

      A good cold message is around 30 to 50 words. Craft your cold message according to the guide I wrote here. Stick to facts on customers, team and product.
    5. Don’t Hide Your Deck. Some founders only want to send their deck once there’s a meeting booked. This is a bad approach.

      The deck is there to help you get a meeting.

      Don’t treat your deck like it contains the nuclear launch codes. Instead, send the deck so we can learn more about your startup and get excited! 

    Wrap-Up

    Fundraising is sales.

    When I meet a founder who’s good at fundraising. I picture him crushing one sales meeting after another. 

    If you want to get good at fundraising, avoid these common mistakes. Send brief, clear, compelling messages.

    If you can do that, your round will fill up before you know it!

    More from the blog: 

    38 Words Got This Founder on My Calendar — Here’s the Cold Email Formula That Wins

    Fundraising Friction is Killing Your Round – Here’s How to Remove It

    When Is It Time for a Startup To Do Huge Layoffs?

    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!

  • The 0 to $100 million stories only happen in AI infra. What about the rest of the economy? 

    You can still build an amazing business while growing more slowly. You just need to do things a little differently… 

    Building In a Boring Industry 

    A while back, I met with a startup selling to food prep companies. It’s a huge market.

    But no startup in that market is going to go from 0 to $100 million in a year. 

    Big food companies just aren’t fast moving. Expect lengthy pilots and slow rollouts. 

    On the bright side, they rarely churn.

    The same is true in healthcare, education, and most of the economy. These are still fertile areas to build in.

    Just don’t expect growth that looks like an AI infra company. 

    Being Breakeven Gives You Options 

    If you know your startup isn’t going 0 to $100 million in a year, just run it breakeven. 

    To raise capital today, you need ridiculous growth. If you don’t have it, just assume you’ll never raise a dime. 

    If your startup is breakeven or profitable, those crazy expectations from VC’s don’t matter. You don’t need them. 

    How Slow Is Too Slow?

    Even in boring industries, you still need to grow. It’s the best sign that someone actually cares about your product.

    Set your growth bar at tripling for three years, then doubling for three years. That gets you from $1 million to $216 million ARR in just six years. 

    That’s incredible growth. You’re now a multi-billion dollar company.

    Wrap-Up

    Maybe you didn’t go from 0 to infinity ARR in 3 seconds. That’s okay!

    You can still build a massive, enduring business — especially in slower moving industries that control trillions of dollars.

    Set your growth bar at an ambitious but reasonable level. Then, go make your customers happy. 

    And if the VC’s don’t like it? That’s their problem.

    More from the blog: 

    You Finally Closed Your Funding Round — Time to Panic?

    Why Short Decks Raise Millions

    Why Some Founders Raise Millions with a Text — And Others Can’t Get a Single Check: Traction vs. Track Record

    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!

  • “We went from 120 people down to 12. Laying them off was incredibly hard.” We’ll call this founder “Jim.” When I spoke with Jim recently, he looked tired but determined. 

    Jim was doing everything to keep his company alive. That meant getting rid of most of his team.

    Cutting Off a Finger to Save a Hand

    “Have you ever seen the old TV show Kung Fu?” I asked. 

    “I don’t think so.”

    “Master Con says ‘Sometimes a finger must be cut off to save a hand.’ That’s what you did. If you hadn’t laid those folks off, no one would have jobs.”

    Why Jim Laid Off 90% Of His Company

    When we read news stories about layoffs, we think, “What a bunch of meanies. How could they take away those poor people’s jobs?” 

    Wait until you sit on the other side of the table.

    Growth is flat. Cash is running out. 

    Jim was already taking a sharply reduced salary. It was barely enough to get by. 

    You either cut payroll, or the whole ship sinks.

    How Layoffs May Save Jim’s Startup

    I actually encouraged Jim to lay off even more people. 

    But even at 12 employees, the smaller payroll bought the company time. 

    Jim was able to close some additional investors. It looks like the company has a good chance of surviving.

    When To Do Layoffs

    If your company isn’t growing and is running out of cash, you’re not doing your employees any favors by keeping them on the payroll. In fact, you’re risking everyone’s jobs. 

    For startups in this position, the only solution is taking an axe to the cost structure. And costs are mostly humans. 

    You can be popular and keep everyone on board until the cash runs out. Or you can be a leader and save the company.

    Wrap-Up

    When you started your business, you dreamed of ringing the bell at the NASDAQ. A few years in, you’re laying off most of your company.

    How the heck did you get here?

    Finding product-market fit is extremely difficult. Along the way, you may over-hire and have to cut back. 

    When a company is in trouble, sometimes the choice is between 90% layoffs and 100%.

    If you’re running out of cash, don’t wait until it’s too late. Take decisive action now.

    With any luck, you’ll be able to rehire your team soon.

    More from the blog: 

    You Finally Closed Your Funding Round — Time to Panic?

    Why Some Founders Raise Millions with a Text — And Others Can’t Get a Single Check: Traction vs. Track Record

    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!

  • “Missionaries, not mercenaries.” How many times have you heard that? But before he started a career in technology, my friend Jesse was a real missionary. And in Mexico, he had a terrifying experience.

    I’ll let Jesse tell you the rest…

    I was staring straight down the barrel of an AK-47.

    On the other end was a corrupt Federale.

    Or at least someone dressed like one.

    I was in my early 20s, bright-eyed and stupid enough to think this was all somehow part of the adventure.

    At the time, I was a missionary in Mexico, working at an orphanage caring for children with disabilities. It remains one of the most incredible seasons of my life.

    Every once in a while, a group of us would pile onto an old school bus and head into neighboring towns to share food, clothing, and the Gospel.

    This particular trip was taking us toward Ensenada.

    We didn’t make it very far.

    About half a dozen Federales — or men dressed exactly like them — pulled us over. Suddenly there were AKs shoved into our faces. They roughed us up and demanded money.

    Then came the part I’ll never forget:

    “Give us the money, or we’re taking the girls.”

    We gave them the money.

    Obviously.

    And somewhere in the middle of this completely insane situation, this bus full of twenty-something missionaries started praying and singing.

    I realize how bizarre that probably sounds.

    But that was missionary work to me.

    Not the AK-47s. Thankfully.

    It was the idea that when the world around you gets ugly, you show up anyway. You bring whatever you have—food, clothes, encouragement, hope — and try to leave people with a little more than they had before you arrived.

    I had no idea that lesson would eventually become my career.

    Zero to Animator

    Years later, I started a nonprofit called Brayhaus.

    The idea was simple: teach creative and technology skills to kids who otherwise might never have access to them.

    One Saturday, I called a local library with an experiment.

    “Can I borrow your computer lab and teach people how to make an animation in an hour?”

    I called it:

    Zero to Animator.

    The library said yes.

    I figured a handful of people might show up.

    Instead, the computer lab was standing room only.

    We had people from about six years old to sixty sitting at computers together, and within an hour they weren’t just watching me animate.

    They had made actual animations they could share with someone.

    More importantly, they had learned something about storytelling.

    The library loved it.

    Then other libraries started calling.

    Before long, I was getting requests from across the state to come teach Zero to Animator.

    Fortunately, I’d asked that first library for permission to record the workshop. We got the appropriate waivers, put a camera in the room, and afterward I posted the class online.

    I didn’t think much of it.

    Then the company that made the animation software found the video.

    They lost their minds.

    They flew me from Portland, Oregon, to Boston.

    And essentially said:

    We want you to build this.

    So I built an entire learning management system from the ground up and turned that little library experiment into a free online animation school.

    It ultimately taught more than 60,000 students.

    The company’s user base grew past 100,000 users, and we reached roughly $3.5 million in revenue in less than six months.

    Then they gave me possibly the greatest job title I’ve ever had:

    Software Evangelist.

    And I’m not exaggerating when I say it may have been the greatest job I’ve ever had.

    I literally got paid to travel, eat with people, talk about animation and software, teach, give talks, and get people excited about making things.

    I even gave TED-style talks about it.

    My job was basically:

    Go make people fall in love with this thing you love.

    Which is when I realized something funny.

    I’d spent years thinking I’d stopped being a missionary.

    Apparently, I had just changed what I was evangelizing.

    The AK-47s were thankfully gone.

    But the lesson I’d learned in Mexico never really left.

    Go where people are.

    Bring them something useful.

    Teach them something they didn’t know they could do.

    Care about them before you ask them to care about what you’re building.

    Sometimes that’s food and clothing from the back of a school bus.

    Sometimes it’s teaching a six-year-old how to make a cartoon in a public library.

    And sometimes, apparently, doing that for one room full of people is enough to accidentally reach 100,000 more.

    — Jesse

    I hope you enjoyed Jesse’s amazing story. For me, seeing how scary the world can get puts life in perspective. What we’re worrying about probably doesn’t matter!

    What’s more, those terrifying experiences can become something positive in the future.

    We’ll be back to our regularly scheduled programming tomorrow. Thanks for reading!

    More from the blog:

    You Finally Closed Your Funding Round — Time to Panic?

    Ghosted by a VC? Here’s What to Do.

    Nobody Knows the Future

    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!

  • The right images can get millions of eyes on your startup. This morning, I used the new Grok Imagine 2.0 to make creative for a fake startup: Chamath’s sweater emporium. 

    Round #1: Making an Ad for the Grand Opening

    I’m picturing blonde wood, Nordic design, and endless piles of buttery soft white turtlenecks. Let’s see if Grok can make us an ad for the grand opening… 

    I seeded the prompt with the Chamath sweater meme. Grok did a great job of rendering the smooth wood and nubby sweaters. 

    I reprompted it to make the grand opening sign larger. Eventually, I got the look I’m going for.

    Imagine 2.0 does a great job of making images for an event. You could use this for real events, like a product launch party. 

    Who needs Canva when you have Grok? 

    Round #2: Making a Logo

    Now that we have an ad for our product, let’s make a logo!

    I asked Grok to make a logo for Chamath’s new sweater line. I told it to include a line drawing of a vicuña, source of the finest wool on earth.

    Grok gave me four great options. I picked the most minimal, with just the company name and a lovely pencil drawing of a vicuña.

    This logo looks so good you could use it on a major brand. Gone are the days of hiring random people on Fiverr.

    Round #3: Creating an AI Model to Wear Chamath’s Finery

    Chamath is a handsome fellow, but we need a beautiful woman to really make these sweaters sell. And I don’t want to pay a human…

    I had Grok create an image of a classy brunette wearing one of Chamath’s turtlenecks. I want her on a sun-drenched street in the West Village, living the glamorous life that only vicuña makes possible.

    Grok’s first effort was solid, but a little generic. I reprompted it to have her look straight at the camera on a street flooded with sunlight. 

    Success!

    Reprompting Grok was a heck of a lot easier than directing a human and a lighting crew, not to mention thousands of dollars cheaper.

    If you’re thinking of using a human model to promote your product, think again. AI can do it for next to nothing.

    Wrap-Up

    Overall, I’m giving Grok Imagine 2.0 an A-. 

    It produced some beautiful images. But occasionally, I needed to re-prompt it to get what I wanted. 

    If Grok could interpret my intent a bit better, I’d bump that up to an A. 

    Imagine 2.0 is a very powerful tool for your marketing. Give it a shot and get more eyes on your startup! 

    More from the blog:

    China’s GLM 5.2: The Most Powerful Open-Source Model Yet — But Does It Deliver in Real Life?

    I Tested Mira Murati’s New Open Model. Here’s Where It Wins (and Loses)

    How I Keep Tabs on 42 Portfolio Companies with One Grok Project

    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!

  • I’m heading back to Japan in early 2027. But Madonn, are those flights expensive! Fortunately, I got early access to an AI assistant that can help…

    Instinct Becomes My Personal Travel Agent

    Instinct is a new AI personal assistant. You talk to it via iMessage or WhatsApp. 

    It’s in private beta right now, but I got an invite from one of its investors.

    I gave Instinct a difficult challenge: finding non-stop flights that are close to 90 days apart without going over (visa restrictions). Let’s see if this puppy can find me a cheap flight!

    Finding Solid Deals in Seconds, All Via Text Message

    In under a minute, Instinct found some great itineraries. It sent me one for around $2,100 on American Airlines, a solid value. 

    But that has me going out of JFK. I live in North Jersey. 

    Would it cost me much more to fly out of Newark?

    Instinct found that it was a mere $8 more to fly out of Newark, which is quite a bit easier for me. Score!

    I verified all these itineraries on Google Flights. Unlike so many travel planning apps, Instinct pulled real, available itineraries. Many apps hallucinate fares that don’t exist. 

    How Instinct Is Going to Save Me Even More

    I asked Instinct what else it could do, and it suggested texting me when the fare drops. So cool!

    I told Instinct to text me if the price drops by $100 or more. This is a lot more flexible than Google Flights notifications, which don’t handle long trips well. 

    Wrap-Up

    Handling all my travel planning via iMessage is absolutely awesome. But Instinct does a lot more than travel. 

    It can manage your calendar, draft emails, do most anything a human assistant can. It does all this through your messaging app, where you spend all day anyway. 

    I’m giving Instinct an A. The accuracy and ease of use beat any other AI assistant I’ve tried.

    I’m excited to see this awesome tool go to general release. Our days of noodling around on Google Flights may be over! 

    Join the Instinct waitlist here…

    More from the blog:

    Llama 3.1 8B: $0.05 per Million Tokens, Still Crushes Everyday Tasks

    How I Built a Slick Landing Page in 28 Seconds with Grok 4.5, Elon’s New Coding Agent

    China’s GLM 5.2: The Most Powerful Open-Source Model Yet — But Does It Deliver in Real Life?

    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!

  • Elon dropped his most powerful AI model ever last week: Grok 4.6. I just used it to make a slick app for angel investors in minutes. 

    Building My First App with Grok 4.6

    I want an app to track all the deals I pass on. 

    Right now, I track them all in a spreadsheet. It’s getting long and janky. 

    I used Grok 4.6 via Grok Build and gave it a detailed prompt. I asked for a simple, MS-DOS-like interface…a lot like this blog. I told it all the possible reasons I pass on a deal and my possible deal sources.

    Grok Creates a Prototype in Minutes

    Grok finished my new app in just 4 minutes and 7 seconds!

    The app works beautifully. 

    I can easily enter a new startup without having to scroll to the bottom of some giant spreadsheet. It did everything exactly the way I told it to, from pass reasons to deal sources.

    How Long Would This Have Taken Without AI?

    I asked Grok how long it would’ve taken a skilled engineer to build this pre-AI. The answer: 2-3 days. 

    I think a top engineer could do it in 1 day. But either way, the productivity improvement with AI is off the charts. 

    No wonder we’re investing trillions of dollars in this!

    Grok’s Model Is Powerful, But Usability Needs Work

    Grok did a really nice job on this app. But I’ll probably wind up sticking with my spreadsheet. 

    Grok doesn’t make it easy to publish the app and start using it. I need hosting and a Supabase database to make this a real, working product. 

    That’s so time consuming that I just fall back to my Excel sheet. 

    If Grok Build could do everything in one click, I’d use it way more. This shows how important the actual application (or “harness”) is, as opposed to the model alone.

    Wrap-Up

    Overall, Grok 4.6 is the best vibe coding experience I’ve seen. I’m giving it an A.

    To get an A+, Grok needs to make it easy to turn this prototype into a real product. It should provide the database and hosting so you can get everything up and running in seconds.

    If Elon did that, he’d crush the competition.

    More from the blog:

    Llama 3.1 8B: $0.05 per Million Tokens, Still Crushes Everyday Tasks

    How I Keep Tabs on 42 Portfolio Companies with One Grok Project

    Qwen 3.8-Max: A+ at Building Apps, F at Telling the Truth

    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

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  • I run the world’s tiniest venture fund. And it’s beating almost everyone. 2.38x TVPI, 35.5% IRR. 

    I think of my angel investments as the world’s smallest fund. This morning, I dug into some numbers to see how I’m doing…

    What Metrics Should We Look At?

    My “Fund 1” contains 36 primary investments made from mid 2021 to mid-2025. I also wrote a couple follow-on checks, the last of which went out in July.

    For a newer fund like mine, we’re looking for two numbers: Total Value to Paid-In (TVPI) and Internal Rate of Return (IRR). 

    TVPI is the portfolio’s total value on paper. This takes into account markups in later funding rounds.

    IRR measures my annual return on capital. This accounts for how long it has taken each investment to reach its current value. Faster growth means higher IRR.

    For older funds, Distributions to Paid-In (DPI) is a key metric. But for a newer fund, it’s not very meaningful. 

    In a five-year-old pre-seed and seed fund, your biggest winners usually have not exited yet. 

    How My Fund Stacks Up on the Numbers

    For 2021 funds, top decile performance is 1.54x TVPI and 15.2% IRR, according to Carta. I’ve beaten that handily.

    2021 was an unusually bad vintage. Valuations were high, and AI was about to change the industry forever.

    Mine is one of the few funds that weathered the transition. 

    Doing the Numbers Like Sequoia

    To arrive at these valuations, I only counted priced rounds as markups. This is in line with the best practices from top funds like Sequoia.

    Some people count any raise at a higher valuation as a markup, even if it came on a SAFE. 

    Had I done that, my returns would be almost three times as high.

    What’s Driving the Returns?

    Like most venture funds, almost all my returns are coming from a couple companies: Micro1, Rilla and North. 

    I’m in awe of these founders. Without them, I would be nowhere. 

    I’ve piled additional investments into these companies whenever possible.

    Slow Deployment Wins the Race

    One of the biggest reasons my fund is outperforming almost everyone in the 2021 vintage: I took my time.

    In 2021, many people were deploying a fund in 6-12 months. I took five years.

    That’s at the very slow end for most funds. But I want to do the job right. 

    This is my own money. I’m not trying to hoover up as much cash as possible and charge a management fee on it. 

    I’m actually trying to get a return!

    If you deployed your entire fund in 2021, you’re in pre-AI companies at sky-high valuations. Those investments probably aren’t looking too great today.

    I have a few of those too! But I also have AI-native companies at better prices from 2022 and 2023’s down market. 

    Those investments are driving my returns now.

    The Risks are Real

    There are two big risks here: concentration and illiquidity

    Almost all the gains are coming from three companies. Problems at one of those companies would hit my portfolio hard. 

    What’s more, we can’t eat markups. This portfolio is marked high, but this isn’t real money we can spend.

    For a newer fund, that’s normal. It usually takes 10-15 years for a company to reach billions in valuation and IPO. 

    But there’s no guarantee these paper gains will ever hit my bank account. 

    What’s Next?

    So what’s next for the world’s tiniest venture fund? 

    The 3 winners don’t need much help from me at this point. I just sit back and let the returns roll in. 

    I’ll be spending more time with the struggling companies. If I can help them even a little, it could change those numbers from a zero to a 1-3x. 

    Meanwhile, I’ve started investing out of “Fund 2”. 

    This fund will contain 40 companies. I’ve already got 7 names in it, and I’m itching to add more.

    Wrap-Up

    When I started angel investing, I committed to myself to invest for 10 years.

    I’m a little over halfway through that 10 year commitment. And I’ll tell you, I’m having way more fun than when I started! 

    The obvious direction to take this is to raise money from outside LP’s and form a real venture fund.

    I’m conflicted on whether I want to do that or not. It’s a lot of fun answering only to myself. Plus, all that time spent fundraising is time I’m not spending with founders. 

    On the other hand, more money means more impact.

    Who knows what the future holds? All I know is I’m having a heck of a time! I’m grateful I get to do this every day. 

    If you want to be the next investment in my tiny little venture fund, shoot me a DM on X!

    More from the blog: 

    You Finally Closed Your Funding Round — Time to Panic?

    38 Words Got This Founder on My Calendar — Here’s the Cold Email Formula That Wins

    Why Some Founders Raise Millions with a Text — And Others Can’t Get a Single Check: Traction vs. Track Record

    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.

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    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!