Tremendous

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!

Use this link to sign up and you’ll save $15 on your first order.

I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

I wrote a detailed review of Misfits here.

How to Tell If Investors Are Really Interested

August 12, 2025

You just finished pitching that big VC. Did you bomb? Did you nail it? Here’s how to tell…

The Weird Way to Gauge Investor Interest

There’s a way to tell, but it’s counterintuitive…

The more questions they ask, the more interested they are. Mr. Moneybags interrogating you like a murder suspect isn’t a sign of skepticism. It’s a sign of being engaged.

Is Moneybags giving you rapid fire questions, one after another? Is he staring at you as he does it?

Then you’ve struck a chord. And now, he’s considering an investment, but he needs to check a lot of boxes first.

No two human beings are exactly alike. But all else being equal, more questions means more interest.

First, let’s go through what to do if Moneybags gives you tons of questions. Next, we’ll cover what to do if he’s silent…

How to Handle Investors That Interrogate You

Use this moment to maximum advantage. Answer each question clearly and concisely.

Here’s a simple rule: your answer should take the same amount of time as it took him to ask the question. Let’s go through an example…

Good answer:

“Moneybags: What was your MRR last month?”

“You: $12,000.”

Bad answer:

“Moneybags: What was your MRR last month?”

“You: Last month was crazy! We almost got there with Megacorp but our champion got reassigned and the deal got pushed to Q3. We’re almost at the line. And we have a huge pipeline that we’re working through. I want to hire another couple sales guys that are real killers to…”

You see what you did? Instead of a number, you gave him “blah blah blah.” Not good.

Give a clear answer. That takes Moneybags’ interest and keeps it high.

How to Handle Investors That Are Silent

Now, what if Moneybags doesn’t ask many questions? What if he doesn’t ask any at all?

First, you want to prevent this situation.

Start the meeting with a brief pitch. It should last around 5 minutes in a 30 minute meeting, and no more than 10.

Some investors, like me, want to skip straight to Q&A. Be prepared for that as well.

After you’re done pitching, never say “Any questions?” Say “What questions do you have?”

This assumes Moneybags has questions. Even if he doesn’t, it will push him to come up with some and ask them.

That gets him more engaged. When he’s asking you questions, he’s not answering emails, playing Candy Crush or staring out the window.

If he still can’t come up with any questions for you, pose some common questions you’ve gotten during your fundraise. Then answer them.

This could help overcome objections he has that he may not feel comfortable telling you.

If you keep getting a question from multiple investors, address it proactively in your pitch. This makes you more persuasive right off the bat.

Wrap-Up

Never fear an interrogation. Every question is a gift.

It means the investor is interested. And it’s an opportunity to persuade.

For each question you answer clearly and concisely, you’re that much closer to getting a check.

Now go out and meet some VC’s! 💪

More on tech:

How to Run a Pitch Meeting

The Question No Founder Asks

Take This Out of Your Pitch Now

Save Money on Stuff I Use:

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!

Use this link to sign up and you’ll save $15 on your first order.

I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

I wrote a detailed review of Misfits here.

GPT-5 Fails Again

August 11, 2025

GPT-5 sucks. I tested it Friday, bad. I tested it again today, even worse. Stick a fork in it.

Let me show you how flawed this model is.

When I tested it on Friday, OpenAI was having routing issues that may have caused GPT-5 to underperform. So this morning, I ran it through 3 more tests to see if GPT-5 can finally live up to the hype.

Here’s what I found…

Round #1: Teach Me About Medical Tourism

This afternoon, I’m meeting with an awesome startup that helps Americans arrange medical procedures overseas.

I love medical tourism! I got a full physical in Japan with a battery of tests for only $100!

So I asked GPT-5 to size up the market and its key players. I gave it a very detailed prompt. I asked for info on market size, leading companies, and more.

GPT-5 gave me a weird error, asking me to choose between a report with current data or one that stops in mid 2024. Uh, who’s choosing an outdated report?

So, I told it to give me current data. It threw the same error again. Again, I told it to find me current data.

A third error! I give up.

Any decent model can do this. I ran the exact same prompt through Gemini 2.5 Pro and got a beautiful report in minutes. But GPT-5 just flails helplessly.

I’m giving this round an F.

Round #2: Why Is Dollar General So Successful?

If there’s one store I love, it’s Dollar General.

It’s so cheap, with such great staff and selection, that I find myself there several times a week. And it’s not just for folks who are struggling: one of the richest guys I know is a dedicated DG man.

This afternoon, I’m meeting a founder who used to be a top exec at DG. So I wondered, why is this company so darned successful?

Let’s ask GPT-5…

GPT-5 gave an okay response, citing factors like a strong staff training program and small store sizes. But it didn’t cite a single source, nor did it explain why DG does better than other dollar stores.

This is a pretty basic, surface-level report. It feels like something GPT-3.5 could’ve written 2.5 years ago.

Compare that to Gemini 2.5 Pro. Gemini gave me a beautiful, carefully footnoted report in seconds.

Gemini explained that DG owns its own distribution centers, which gives it a huge advantage in logistics and cost. GPT-5 never mentioned that.

I’ll give GPT-5 a C for this round.

Round #3: My Unpaid Research Assistant

I’m starting to feel sorry for ChatGPT. So, I’ll give it an easy one…

I’m always looking up the funding history of startups. I want to meet companies before their seed round, so I need to make sure they’re early stage before I contact the founder.

This morning, I wanted to know the funding history of a startup called Rid. Rid helps you sell your unwanted junk online.

Can GPT-5 help?

GPT-5 gave a solid response, finding that Rid is part of the current YC cohort. That means they probably haven’t raised a seed round yet.

But when I ran the same question through Gemini 2.5 Pro, it gave me a better answer. Gemini explained that YC gives companies $500k and explained how that financing works. This is a fuller and more direct answer.

GPT-5 gave me what I needed, but it wasn’t as informative as I’d like. I’ll give this round a B.

A B isn’t bad. But for a supposedly frontier model, it’s not great.

Wrap-Up

Overall, I’m giving GPT-5 a grade of C- on this re-test.

That’s even lower than on Friday, when I gave it a B-. Maybe these updates are actually making it worse?

I want to get excited about GPT-5. But between weird errors, incomplete answers and generic reports, I walked away disappointed.

GPT-5 is the worst product launch I’ve seen in years. For a company valued at $500 billion that is supposedly the market leader, OpenAI did a rotten job here.

Sam is a smart guy and OpenAI has a lot of great people. They also have incredible distribution.

I’m confident they can come out with a great model. But this isn’t it.

More on tech:

GPT-5 vs. Grok 4: Which Model Is King?

Grok 4: The Best AI Model Ever?

Will Open Source Win AI?

Save Money on Stuff I Use:

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!

Use this link to sign up and you’ll save $15 on your first order.

I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

I wrote a detailed review of Misfits here.

GPT-5 vs. Grok 4: Which Model Is King?

August 8, 2025

Can GPT-5 beat the reigning champion, Elon’s Grok 4? I ran them through 3 tests to find out.

When Grok 4 came out last month, I asked it 3 real world questions that I actually needed the answer to. Grok 4 crushed it, scoring an A-.

Can GPT-5 do even better? Let’s find out…

Round 1: GPT-5 As Investment Analyst

For our first round, I asked GPT-5 to help me manage my investments. How should I allocate across index funds, bonds and cash?

GPT-5 gave a solid response, recommending a portfolio of mostly equities. This makes sense at my age, 39.

But GPT-5 also recommended something unusual: a special allocation to small cap/value stocks.

I’ve asked numerous top AI models about financial planning, and none of them recommended this.

Since total stock market index funds already contain those type of companies, this allocation seems duplicative. GPT-5’s sourcing was also weak here, pointing to a Wikipedia article rather than a reliable, primary source.

GPT-5’s recommendation wasn’t bad, but it was overly complex without much additional benefit. For this round, I’m going with Grok 4.

Round 2: GPT the VC

For its next assignment, I asked GPT-5 to find me some startups.

People are having kids later in life. This means the need for IVF is going to grow enormously.

What startups could help make IVF cheaper and more reliable? Let’s ask GPT…

I had GPT focus on pre-seed companies with under $750k in funding. It could only find one startup that met my criteria: a company called Microgenesis.

The company looks interesting, but Crunchbase shows it has raised over $2 million in funding. So, the one startup GPT could find doesn’t even meet my criteria.

Grok 4 found several startups that fit my criteria when I tested it last month. In this round, Grok blows GPT-5 away.

Round 3: Make Me a Better Angel Investor

I meet with a lot of founders. I often wonder, “how could I do a better job in these meetings?”

Let’s ask GPT-5…

GPT gave some solid ideas, like making sure to show interest in what the founder is doing. But its response was much more limited than Grok 4’s.

Grok 4 added helpful advice about how to build dealflow and diversify my portfolio. Those are great things to keep in mind, especially for newer angels.

GPT-5 gave an adequate response, but Grok 4 was much more informative. I’m giving this 3rd and final round to Grok.

Wrap-Up

Grok 4 crushed GPT-5 in my testing, winning 3/3 rounds. Overall, I’m giving GPT-5 a B-.

Compared to Grok, GPT-5’s answers were very basic. The information was sometimes inaccurate and sourcing was spotty at best.

GPT-5 is a disappointment. After a 2 year wait from GPT-4 to GPT-5, I was expecting a lot more.

OpenAI had something special in 2022. But now, they’re falling behind.

I get better results from Grok 4 and Gemini 2.5 Pro. And for coding, Claude rules the roost.

If Sam wants to justify that $500 billion valuation, he needs to step it up.

Have a great weekend folks!

More on tech:

Grok 4: The Best AI Model Ever?

Will Open Source Win AI?

Save Money on Stuff I Use:

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!

Use this link to sign up and you’ll save $15 on your first order.

I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

I wrote a detailed review of Misfits here.

The Key Difference Investors Miss: Contracted vs. Live ARR

August 7, 2025

“$800k ARR…is that contracted or live?” Most investors never ask this question. They’re making a big mistake.

Whether you’re an investor or a founder, you have to understand the difference between contracted and live revenue.

Tl,dr: Contracted ARR is signed revenue, live ARR is actual money you’re billing. Focus on live ARR.

Let’s break down the differences and how big gaps can creep up on you…

Contracted Revenue

This is the total value of all the contracts with customers you’ve signed. You may see this written as “cARR” for short.

Let’s say that you signed an $800k ARR contract with Megacorp. They’re your only customer. That means your contracted revenue is $800k ARR.

Sounds awesome right? Not so fast…

Let’s say that Megacorp manufactures bobbleheads of top VCs. They have 8 plants where they plan to take your product live.

But right now, you’re only live in their Pittsburgh plant. You’ll go live at the other 7 over the next year.

The contract states they’re only billed for plants that are live. This is typical in SaaS contracts, although there is the rare contract that lets you bill the customer immediately even if they haven’t rolled out your product.

Live Revenue

Here’s where we get down to real money…

You’re charging them $100k per plant. So right now, with just the Pittsburgh plant live on your product, you’re only getting $100k a year coming into your bank account.

That means your live revenue is $100k ARR. Each month, Megacorp sends you a check for $8,333.33. I’m assuming you actually remembered to bill them (a surprising number of startups don’t), the contract stipulates monthly payments, and you’re past their likely net-30 payment terms.

When will you get the remaining $700k/yr coming into your bank account? Well, the deployment schedule says that the other 7 sites will go live over the next 12 months.

The Dangers of Relying on Contracted Revenue

You’re expecting to see that remaining $700k soon. But what if Megacorp decides to delay the project?

That $700k you were counting as “revenue” suddenly isn’t coming any time soon.

Maybe they cancel the other sites entirely, and you only ever get the Pittsburgh plant. That would mean the $700k evaporates for good.

If you were hiring thinking you had $800k in revenue, you’ve overhired. You have people sitting around doing nothing and you can’t afford to pay them.

You also told your investors that you’re at $800k in revenue. Now, they find out that number is a little squishy…

They should’ve asked what your live revenue is. If they didn’t, that’s on them.

But there’s no guarantee they’ll see it that way. The investors could blame you for not being clear.

Where Contracted vs. Live Revenue Disparities Are Worst

Not all startups have big contracted vs. live disparities. But in certain industries, they’re everywhere.

If there’s one type of company particularly prone to huge disparities between contracted and live revenue, it’s healthcare companies.

Healthcare moves slow. Really slow.

They sign a contract today. But the rollout takes an eternity.

Don’t I know it! I used to roll out medical software products for hospitals all over America. Those projects took years!

So if you’re a healthcare investor or founder, you have to pay particularly close attention to the contracted vs. live distinction.

Enterprise SaaS startups in general tend to have big differences between contracted and live revenue. Again, it’s those long deployment periods.

Consumer/SMB SaaS companies don’t see this problem as much. Their customers usually just plunk down their credit card and start using the product.

Avoiding the Mess

If you’re an investor, always ask what live revenue is. Explain exactly what you mean: “How much cash is actually hitting your bank account now?”

If you’re a founder, always tell investors what your contracted and live revenue is. Be extremely clear which is which.

Meanwhile, don’t hire and expand based on some pie-in-the-sky contracted revenue number. You may never get that money!

Hire, expand, and spend based on what you can actually afford now. If you cannot pay those folks with your live revenue and cash in bank today, you don’t want to hire them.

Wrap-Up

Bottom line: focus on live revenue.

Part of not being a schmuck as an investor is knowing these little nuances with big implications. The same goes for founders.

I didn’t know any of this stuff when I started investing 4 years ago. But bit by bit, you start to learn the pitfalls and how to avoid them.

Contracted revenue is a promise. Promises are broken.

Live revenue is real. This is the number to watch.

In startups and in life, cash is king. 👑

More on tech:

My Secret Weapon for Helping Founders Raise Millions

My Biggest Lesson from Four Years Angel Investing

Save Money on Stuff I Use:

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!

Use this link to sign up and you’ll save $15 on your first order.

I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

I wrote a detailed review of Misfits here.

Would You Take a Pig Heart?

August 6, 2025

106,036 Americans are waiting for an organ transplant. 17 of them die each day. But what if we could give them pig organs?

From the Seventeenth Century to Modern Science

The first attempted xenotransplantation, or animal-to-human transplant, was done in 1667. Jean-Baptiste Denys gave sheep’s blood to a 15 year old boy who, somehow, survived the risky procedure. But two more of Denys’ patients soon died, and the procedure was banned.

Doctors continued to attempt xenotransplantations for centuries. They began to have some success in the 1960’s, with an American patient surviving 9 months post-op.

But it was not until the 2020’s that xenotransplantation truly accelerated. What changed was the invention of CRISPR gene editing.

The State of the Art in Xenotransplantation

Xenotransplantations are usually done with pig organs. There are lots of pigs around anyway and pig organs are about the same size as ours.

But humans tend to reject even human organs. Animal organs often face an even more intense immune response. What’s more, pigs have certain viruses called Porcine Endogenous Retroviruses (PERVs) that can be very dangerous to humans.

CRISPR lets us genetically modify pigs. We can take out the PERVs and make the pig organs more suitable for humans.

In recent years, genetically modified pigs have been the main source for xenotransplantations.

Pig Organs Save a Life

In January 2025, doctors at Massachusetts General Hospital transplanted a pig kidney into Tim Andrews.

Andrews had end stage kidney failure. He had been on dialysis for over 2 years.

This operation was his only hope for a normal life.

Luckily, Andrews’ operation was a complete success. He was discharged from the hospital just a few days later, with his new kidney functioning just like a healthy human one.

Andrews is doing so well that in June, he threw the opening pitch at a Red Sox game in Fenway Park!

Scaling Up

This is an outcome beyond anyone’s wildest dreams. What if we could scale this up to all people who need kidneys and, eventually, all organs?

Several companies are hard at work to make it happen.

Companies like eGenesis and United Therapeutics are producing genetically modified pigs. Those pigs are the source for xenotransplantations. eGenesis provided the kidney for the Andrews transplant.

In February, the FDA approved a clinical trial by United Therapeutics to evaluate its pig organs in humans. I can’t wait to see the results!

Wrap-Up

I imagine a future with farms full of genetically modified pigs. When one of your organs breaks down, you just check into the nearest hospital and they get you a fresh, new one from the farm.

Humans could live decades longer if we master xenotransplantation. And we’re closer than ever.

I’m excited to meet startups working on genetically modified pigs and xenotransplantation. If that’s you, let me know!

More on tech:

Is Biotech Having its ChatGPT Moment?

How We Can Rewrite Our Genetic Blueprint

Save Money on Stuff I Use:

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!

Use this link to sign up and you’ll save $15 on your first order.

I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

I wrote a detailed review of Misfits here.

My Secret Weapon for Helping Founders Raise Millions

August 5, 2025

I never show this spreadsheet to anyone. 54 top investors. This is my secret weapon.

My money is no greener than anybody else’s. So if I want to invest in the best founders, I need to bring something else to the table.

This spreadsheet makes it happen.

Meet “The Sheet”

Startups are always raising money. And because VC’s almost never invest in cold pitches, warm intros are critical.

So when one of my companies is raising, I consult The Sheet.

I don’t open The Sheet for every founder. This weapon is for folks I’ve invested in only.

I don’t want to be sending random dealflow to investors. Every deal I send out, I’m investing in myself.

That makes the messages valuable and rare, instead of frequent and spammy.

How I Use The Sheet to Help My Founders

Let’s say “Icetech” is raising money. They make POS systems for ice cream trucks.

I look through The Sheet and find investors that love vertical SaaS. I make sure they invest at Seed, since Icetech is at Seed stage.

Then, I ask them if they want to meet one of my investments: an incredible company called Icetech.

Most of these VC’s take me up on the offer. Soon, a founder has a raft of warm intros to VC funds in their inbox.

The reason uptake is so high is because I don’t send the same deals to everyone. I make sure that the deal fits their criteria.

I’m not going to send an American deal to an investor who only does Europe. I’m not going to send a Series A to a pre-seed fund.

Making Your Own Sheet: For Investors

If you’re an investor, keep track of every other investor you meet. Find out what they invest in and add it to a spreadsheet.

Here are some columns to include:

Name
Title
Firm
Sectors (Vertical SaaS, spacetech, etc.)
Geographies (US, Europe, etc.)
Check Size
Best contact method (e-mail, iMessage, etc.)

The best way to meet investors is to contact the folks who invested alongside you in prior deals.

Put a particular emphasis on investors who are in your best deals. Those are the most able folks you know.

Soon, you’ll have a spreadsheet with some awesome names in it. When one of your companies is raising, match them up with the right VC’s from the list.

Making Your Own Sheet: For Founders

If you’re a founder, you should be building a secret weapon too…

Put every investor you know that invests in companies like yours into a spreadsheet. Find more using an LLM or tools like Crunchbase.

Be sure they invest at your stage and in companies similar to yours. For example, you don’t want to pitch a SaaS VC if you’re a biotech startup.

Then, work your way down The Sheet and pitch those investors. If you targeted your list well, you should start closing some checks in short order.

Wrap-Up

Getting $5,000 or even $25,000 from me is not going to change anyone’s life. Getting intros to funds that invest millions…that just might.

Helping founders is a lot of fun! It lets me feel like I played a small part in building one of the great companies of the future.

That’s a lot more exciting than just sitting back and hoping for a return.

If you’re an investor, you should be creating your own secret weapon. And if you’re a founder, building The Sheet could bring in millions for your startup.

Not a bad return on a few hours work.

P.S. Want to be added to The Sheet? Drop a comment below and let me know what you invest in...

More on tech:

My Biggest Lesson from Four Years Angel Investing

Are Hackers After Your Brain? — The Rise of CogSec

Save Money on Stuff I Use:

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!

Use this link to sign up and you’ll save $15 on your first order.

I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

I wrote a detailed review of Misfits here.

Meet My Latest Investment: Zeon Systems

August 4, 2025

What happens when you lower the cost of something? You get more of it. My latest investment, Zeon Systems, is doing that for scientific research.

Zeon lets you automate experiments. Just describe the experiment in natural language in a ChatGPT-style text box. Then, the robot arms carry it out!

There are around 1 million research scientists performing experiments in America today. Training a new one takes many years. But building a robotic arm takes just a couple of hours.

I first heard about Zeon on X during its YC launch. I knew immediately that I had to meet these guys.

I cold messaged them the next day and set up a meeting. Frankly, I’d have met them at 3am on a Tuesday if that’s what they wanted.

You have to be aggressive when you see a great investment. There are only a few really special startups per year.

When I met with Founder & CEO Brontë Kolar recently, I was struck by how much she cares about this problem.

She was researching antibiotic resistance with her co-founder Tahir D’Mello after their workdays at Latch Bio. When they realized that it would take years to begin to crack the problem, they knew they needed to automate the lab work.

So they founded Zeon.

I want a future with hundreds of millions of Zeon robotic arms, all conducting experiments 24/7. Powerful AI models will direct them to the most important research problems.

If we can do that, all the dominoes will fall: cancer, heart disease, dementia, you name it. Eternal health, eternal life.

Not a bad vision for a startup.

Check out Zeon and get your lab running 24/7!

More on tech:

My Favorite Startups in YC X25 (Part 1)

Meet My Latest Investment: Sent.dm

My Biggest Lesson from Four Years Angel Investing

Save Money on Stuff I Use:

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!

Use this link to sign up and you’ll save $15 on your first order.

I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

I wrote a detailed review of Misfits here.

Why I Love the Most Hated People in Silicon Valley

August 1, 2025

These are the most hated people in Silicon Valley. But if you’re spending time trashing them, you’re wasting your life.

A young techie in San Francisco put up a picture of himself and pals having dinner at a nice restaurant. The caption: “went to a fancy dinner in SF and everybody went to Harvard (or Stanford).”

The photo has 17.6 million views and counting. Thousands of people are trashing them in the ugliest terms imaginable.

You don’t have to love these people. But any minute spent attacking them is a minute wasted.

You don’t know them. They don’t matter to you. And you don’t matter to them.

Yes, they went to elite universities. But that doesn’t take anything away from you.

I went to state school, University of Wisconsin-Madison. But that doesn’t mean I can’t be happy for these young people who went to colleges higher ranked than mine.

If they had failed, do I get something? Does a guy show up at my house with one of those giant checks?

No. So stop hatin’.

There’s an especially ugly element to this particular internet mob. Many of the comments about these young people are about the fact that they’re (almost) all Asian.

People hate successful Asians.

Many Asians have done well in America. And good for them!

But what if they hadn’t? Then, people would deride them as welfare cheats.

They can’t win.

Now, Can I claim to be St. Francis who’s never talked trash about someone? Certainly not.

I know I’ve said unkind and insensitive things in my life. I try not to, but sometimes I let myself slip into it.

In the end, the people I’m trashing probably don’t know or care what I think. But I still try to stop myself from this petty behavior.

Why? Because it’s a waste of life.

I’m 39 years old. Optimistically, I may have another 50 years on the planet. If scientists figure something out, maybe that’s 100, but we can’t count on that.

Why spend minutes, hours, days denigrating someone? Where does that get me?

Nowhere.

Hating some random people in San Francisco I’ve never met won’t help me.

I’m better off focusing on myself. And so are you.

Have a great weekend, everybody!

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!

Use this link to sign up and you’ll save $15 on your first order.

I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

I wrote a detailed review of Misfits here.

Why We Should Be Grateful for 10 Year Lockups

July 31, 2025

Figma goes public today. Seed investors were locked up for 12 years. That’s a long time to wait! But here’s why we should be grateful for lockups…

Every company goes through hard times. If we were allowed to dump our shares, we probably would!

Then, we’d miss out on enormous gains when the founder figures it out.

Figma in the Wilderness

Figma is a great example. It took founder Dylan Field over 2 years to release a product.

I don’t know about you, but if I’m an investor in a startup that’s taking that long to ship a product, I’m getting worried. “What’s the hold up? Will they ever ship?” I begin to wonder.

Of course, Figma did release a product, and it was an enormous hit. Fast forward a decade, and they’re going public for almost $20 billion.

Learning From My Top Investments

Figma is not alone in suffering hard times before becoming a major success. If I look at any successful startup I’ve invested in, it went through a rough patch.

A year of 0 growth. Loss of a major customer. Legal issues. Macro headwinds.

It’s always something. And as much as I want to think I’m a diamond hands, I might have sold my shares had there been a market for them.

That would’ve been a huge mistake. I would’ve been bailing out of the biggest successes in my portfolio.

How Long Is Too Long?

Of course, we all need liquidity eventually. I agree with Bill Gurley that companies should go public earlier, perhaps around the $100-200 million ARR mark. By that point, a company is a major success.

Going public cleans up the cap table mess of numerous share classes. It provides important liquidity for your employees and investors. And it also introduces a new level of discipline.

Without the public markets to scold him, Mark Zuckerberg might still be frittering away tens of billions on the “metaverse,” whatever that is.

Wrap-Up

Liquidity is great once a company’s a huge success. But being locked up early is a blessing in disguise.

It takes a thousand twists and turns before a company hits the big time. You see today’s success. But you don’t see all the failure it took to get there.

And during all that failure, it can be hard to keep the faith.

So the next time you look at your portfolio and bemoan the lack of liquidity, take a step back.

Being locked up can be nerve-wracking. But one day, it might put millions of dollars in your pocket.

More on tech:

Have You Seen These Valuations Lately?

The Three Metrics That Could Save Your Startup

Are Hackers After Your Brain? — The Rise of CogSec

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