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.
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.
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!
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.
You may need it. But does anyone want to give it to you?
So many founders treat venture capital like a gas station. When you’re out, come in for a refill!
That worked in 2021. It doesn’t work now.
What you need is not the investor’s problem. Their problem is taking their capital and getting a return on it.
Banks don’t give money to those who need it. Same with VC.
When I started investing in startups in 2021, the standard was 3x year-over-year growth. If you could show that, you were fundable.
Those days are over.
The standard today is 10x year over year.
For any other than the fastest-growing companies today, another round may not be there.
Stop assuming another round will be there. Whether they know it or not, many startups today have raised all the venture capital they ever will.
Money is concentrating into a handful of extremely high-growth startups.
I see it every day. A $50 million Series A at $500 million, not a $10 million Series A at $50 million.
That $50 million going to the fast-growing company means four other traditional Series A’s didn’t happen. That leaves those slower-growth companies out in the cold.
That might not be fun, but it’s survivable. Unless, of course, you’re burning a lot of money.
Always have a plan to get to breakeven, fast. Or better yet, simply be there by the time you’re raising!
Then you don’t need investors like me.
If the terms are favorable, you can take our money. If they’re not, you can tell us to sod off and keep building on your own.
Don’t let your company die! Always be within spitting distance of breakeven.
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.
Ever dreamed about building a viral app? My buddy Jesse Bray did it.
Jesse had an idea for an app called TimTalk — a hillbilly Twitter. People loved the demo…but building a scalable app proved more difficult than Jesse expected…
We Won $5,000 for an App That Didn’t Exist
How a fake trailer, a fictional hillbilly, and two million AI credits taught me that stories spread faster than software.
Everyone wants to know how to build a viral app.
I wish I had a sexy answer.
I don’t.
Because I never set out to build one.
I set out to make myself laugh.
That’s a very different goal.
In fact, the app that eventually landed me a $5,000 grant, two million AI credits, a spot in Create.xyz’s 30-Day App Store Bootcamp, and more traffic than I knew what to do with…
…didn’t exist.
Not when I entered the competition.
Not when I pitched it.
Not even when people started asking where they could download it.
I had built a trailer.
Not the software.
The software came later.
Looking back, that’s probably the biggest startup lesson I’ve learned in the last twenty years.
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.
“They said a $5 million valuation was way too high.” I was chatting with a great founder from Tokyo last night. And I could hardly believe what I was hearing…
Dealing With Investors With Crazy Expectations
We’ll call her Sarah.
Sarah is raising for a SaaS company with some strong early traction. They’ve jumped out to $300,000 ARR in just a few months.
But even for a strong startup like this, raising money in Japan is really hard. If you’re raising anywhere outside SF or New York, you might be having the same problem.
“They were looking for a $2 million pre-money valuation,” Sarah said.
“But if you’re raising $1 million, you’d be selling a third of the company!” I said.
“I know! That’s what I tried to explain to them.”
Find Yourself Some New Investors!
When the investors you’re pitching just don’t get it, it’s time to find some new ones. Here’s what I suggested…
“You need to broaden your funnel of investors.” I said.
“Find everybody in Japan that invest at your stage. You also want to look for VCs in the US that write checks in Japan.”
Finding Better Investors
I recommended using OpenVC to find new investors. It’s a great way to find the right investors for your company.
Look for people who invest in your country, stage, and market.
Sarah will filter for investors who write checks into early stage SaaS in Japan. She’ll want to avoid pitching folks who only invest in America or only do late stage.
How to Run a Fundraising Process
Fill your investor funnel with 200 names — a mix of VC’s and angels.
Work your way down the list. Send a brief, personalized message to each one. Here’s a guide I wrote on how to do that.
Stack all the meetings in one week, if possible. Create a sense of urgency.
If you’ve got a team of builders and some early traction, you should get at least one term sheet.
Wrap-Up
Maybe you’re not in SF or New York. Maybe you feel like you’re on the outside, looking in.
But there are investors looking for companies like yours! You just have to find them.
If the investors you’re talking to have unrealistic expectations, don’t worry. You don’t need them.
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.
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.
You started your own business. But your family and friends aren’t buying it — why not get a real job? If no one believes in you, here’s what to do…
Stop expecting them to!
It’s not other people’s job to believe in you. That’s your job.
People Don’t Believe What They Don’t Understand
Most of the people around you have no experience with entrepreneurship. They’ve never been out on their own.
They don’t believe you can build your own business. But this has very little to do with you.
They don’t believe they can start their own thing, either!
It’s hard to believe in something you haven’t personally experienced. If you’ve spent your whole life working a safe job, that’s what you believe is possible.
Don’t Take It Personally
If the people around you don’t understand, try not to take it too personally.
They can still be wonderful parents, siblings, or friends. You can have a great meal together and laugh about old times.
But in this new part of your life, you’re going to be on your own. And that’s okay!
All you have to do to make a successful business is identify a problem someone is having and solve it. Then you have to get that person to pay you.
Where does the belief of friends and family fit into this? Nowhere.
Finding Your People
I’m really lucky. My friends and family have always been supportive of everything I do, no matter how odd. When I quit a safe job in tech seven years ago, I never heard a single negative word.
But no matter what anyone said, I would’ve done it anyway!
If you don’t have anyone supportive around you, make new friends that understand entrepreneurship.
That doesn’t mean you have to distance yourself from the friends and family you have today. Just add more!
Every city has countless events for entrepreneurs. If you feel isolated as a founder, try popping into one.
Wrap-Up
In time, your friends and family will come around. If you build your business into a big success, they’ll accept it.
But whether they do or whether they don’t isn’t anything you need to worry about. Just do the work and achieve what you dream of.
In the end, this is your life, not theirs.
I’m heading up to Wisconsin to see some friends and family, so this will be the last blog until Friday, August 14. See you again soon!
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.
Are you spending a fortune on tokens? How does $0.05 per million sound? This morning, I tried one of the cheapest LLM’s in existence. Turns out, it’s surprisingly powerful.
Llama 3.1 8B on Groq costs just $0.05 per million input tokens and $0.08 per million output tokens. That’s over 100x cheaper than frontier models.
I was shocked at how capable this little LLM is! From basic coding tasks to parsing documents, Llama crushed one task after another.
Let me show you what this bargain basement model can do…
Round #1: Making a Basic Landing Page
For our first round, I had Llama make me a basic landing page. I told it to give me a simple MS-DOS format.
Llama gave me a nice, simple page in a jiffy. I’m impressed that such a cheap model can handle coding tasks this well!
The page I made with Grok Build was a little prettier. But if appearance is less of a concern than cost, Llama works nicely.
I’m giving this round an A-.
Round #2: Extracting Details from a Document
Lots of founders use AI to extract info from documents. This is a repetitive task where a cheaper model could really help.
Can Llama extract info reliably?
I gave Llama my blog post on Digital Ocean’s seed round. I asked it to tell me the amount of money they raised in their funding round: $3.2 million.
Llama nailed it! I’m giving this round an A.
Round #3: Summarizing a Document
Another common task for AI is summarizing documents. On high-volume tasks like this, token costs can really add up.
Can Llama help?
I fed Llama an article from The Japan Times about surging sales of portable air conditioners. Llama gave me an excellent summary, explaining that low prices and easy installation have made portable AC’s very popular in Japan.
Llama produced this summary incredibly quickly: just 256 milliseconds. Llama gets an A+ on this round!
Wrap-Up
Llama 3.1 8B earns an A overall in my testing.
This little model really impressed me. On task after task, it gave me great outputs with incredible speed. I’ve gotten worse results from more expensive models!
If you’re doing something really complex, like debugging a huge codebase, you’re better off using one of the frontier models. But for many common tasks, Llama is more than sufficient.
If you’re struggling with token costs, try embedding Llama into your application!
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.
If you’re old enough to have had a flip phone, you probably remember that images looked terrible on that tiny screen. But a friend of mine, Jesse Bray, figured out how to stream HD video to those little screens as early as 2005.
How he did it is the story of today’s guest post. Enjoy!
We Tried to Beat YouTube — and Streamed HD Video on a Motorola Flip Phone
In 2005, I worked for a startup that was trying to compete with YouTube.
We also had an algorithm that could stream HD video on a Motorola flip phone.
Yes, actual HD.
On a flip phone.
That is usually the point where people assume I am exaggerating.
I am not.
The company was called Alpha Omega, and the entire experience now feels like a half-remembered fever dream from the early internet: a wealthy, eccentric Italian investor, two young musicians from Portland, a trip to Mesa, Arizona, a prototype for an all-in-one handheld device, public-domain movies, sock puppets, and the sincere belief that we were building the future of media.
Somehow, all of it really happened.
How We Ended Up in the Room
My roommate, best friend, and bandmate was working on Alpha Omega with me.
We met the investor through my mother, who had worked as a model and actress and seemed to know an endless supply of unusual and fascinating people.
The investor was a wealthy Italian man with a diplomatic or ambassadorial air about him. Even now, I am not completely sure how to describe what he had going on. He seemed to exist somewhere between international businessman, patron of ambitious young people, and character from a movie nobody else had seen.
He was spearheading Alpha Omega and eventually flew us from Portland to Mesa, Arizona, to help work on it.
We were not famous engineers.
We were not seasoned founders.
We were young musicians who had somehow gotten into the room.
But the room was doing real things.
We Were Building for a Future That Barely Existed
Online video in 2005 was still awkward.
Bandwidth was limited. Video quality was unreliable. Mobile phones had tiny screens, weak processors, little storage, and internet connections that felt almost ceremonial.
YouTube had only just launched.
Most people were not yet carrying devices designed to stream video all day. The idea of watching high-quality entertainment on a phone still felt futuristic.
Alpha Omega was trying to change that.
We had an algorithm capable of streaming HD video on a Motorola flip phone.
That was the magic.
It was not a sketch, a pitch-deck claim, or a prediction about what might eventually be possible.
We did it.
Watching high-definition video appear on that tiny device felt completely absurd. The hardware looked incapable of supporting the experience, yet there it was.
Today, streaming video on a phone is invisible technology. Nobody thinks about it.
In 2005, it felt like science fiction.
Naturally, We Also Designed a Device
We were huge Star Trek nerds, so merely building a streaming platform was not enough.
We also mocked up an all-in-one handheld product called the Alpha Omega Device.
It would function as a:
Phone
Music player
Video player
Calculator
Internet device
This was before the iPhone had been announced.
No, we did not invent the smartphone.
We did not manufacture the device, and Steve Jobs was never forced to call an emergency meeting about us.
But we were imagining the same convergence that would soon transform everyday life: communication, media, music, computing, and the internet all collapsing into a single object people carried everywhere.
Our name may have lacked Apple’s elegance.
Our ambition did not.
Our Streaming Service Had Sock Puppets
Alpha Omega also created a streaming platform featuring public-domain films.
We were trying to compete in the emerging online-video world, but we did not have the money to license a major Hollywood catalog.
Public-domain movies gave us something legitimate to stream.
The problem was that old public-domain films were not exactly an unstoppable viral-marketing strategy.
So we made sock-puppet parodies of them.
Each film had a ridiculous puppet version designed to make fun of what the audience had just watched.
It was cheap, strange, and memorable.
More importantly, it was our attempt to create original content around a larger media library — to give people a reason to share the platform rather than simply use it.
Long before every company had a “content strategy,” we were trying to build one out of old movies and socks.
I Was Also Trying to Become a Folk Singer
At the same time, I was fronting the Jesse Bray Band and trying to become some version of a folk and indie singer-songwriter.
I was not exactly a major star.
But I was in the room, and the room occasionally did things.
Through my mother, I was connected with a sitcom pilot and wrote a theme song for it called “I’ll Take You Back.”
The pilot never went anywhere, which is the fate of most pilots, but I recently rescued the song from the archives.
That part of my life mattered to how I viewed Alpha Omega.
I did not see online media only as a technology problem.
I saw it as a creator problem.
I Thought YouTube Might Become Video’s Napster
Napster had already demonstrated how quickly technology could transform an industry.
It made music nearly frictionless for audiences while creating chaos for the musicians, labels, and businesses that depended on controlling distribution.
When YouTube appeared, I saw enormous potential.
I also saw another Napster.
I worried that filmmakers, animators, musicians, comedians, and small independent creators would generate the value while a centralized platform controlled the audience, the discovery system, and eventually the economics.
I was young, earnest, and probably a little too convinced that I could become a folk hero for the little creators.
But the concern was not entirely wrong.
Who controls distribution?
Who owns the audience relationship?
Who benefits when creative work travels farther than ever?
What happens when a platform becomes more powerful than the people whose work made it valuable?
Those questions became central to what is now called the creator economy.
We were asking them before the creator economy had a name.
We Saw the Future, but We Did Not Own It
Alpha Omega did not defeat YouTube.
We did not launch the Alpha Omega Device.
Our public-domain streaming service did not become a global destination.
The sock puppets, tragically, did not become entertainment icons.
But we saw several things clearly.
People would watch video online.
They would stream it on phones.
Music, video, communication, and computing would converge into a single handheld device.
Original creators would become essential to the growth of digital platforms.
And those creators would spend the next several decades struggling over ownership, compensation, reach, and control.
Seeing the future, however, is not the same as building the company that owns it.
Timing matters.
Capital matters.
Distribution matters.
Leadership matters.
Execution matters.
And sometimes you can be standing directly in front of what comes next without having the resources, structure, or luck required to carry it into the world.
What stayed with me was not the belief that we had secretly invented YouTube or the iPhone.
We had not.
What stayed with me was the experience of being invited into a room where people were sincerely attempting things that sounded impossible.
We were streaming HD video on a flip phone.
We were imagining an all-in-one media device.
We were building a streaming platform around public-domain films and sock-puppet comedy.
We were trying to protect small creators while simultaneously convincing ourselves we might become successful musicians.
It was messy, ambitious, ridiculous, and real.
I may not have been the most accomplished person in that room.
But I was there.
And the room did stuff.
That may be one of the most important lessons of my career.
Sometimes your first great opportunity is not being the genius who controls the room.
It is simply getting inside, paying attention, contributing what you can, and allowing the impossible things happening around you to permanently expand your sense of what can be built.
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.
Do you have a list of customers or prospects you want to monitor news for? Here’s how to build an easy automation with Grok Projects…
For me, my founders are my customers. And since I’ve got 42 investments now, it’s hard to keep track of what’s going on with all of them!
So I made a little tool to find those big news stories and launch announcements…
The setup is simple. I told Grok Projects to pull news stories from the last 90 days for each company and put them in a bulleted list with links.
I pasted in a list of my investments from a spreadsheet. You could even have Grok look to a live spreadsheet on Google Drive if you like.
Let’s see what Grok can do!
Grok did a nice job of finding interesting stories about my portfolio companies. It picked up a Forbes interview with Ali from Micro1 that I missed!
In one instance, Grok returned stories from a startup with a similar name. To avoid this, try giving Grok the website of each company so it knows the exact company to target.
This tool could be great for monitoring news about companies in your sales pipeline.
If one of them raises a huge round of funding, it’ll show up here. That could make them an enticing sales prospect.
Any task that involves repetitive Googling is now something we can automate in minutes.
Try setting up an agent that looks for news stories on your customers or top sales prospects. You might be surprised what you find!
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.
Tremendous 