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.

Brittanica Chatbot: A More Reliable AI?

October 14, 2025

Ever ask AI a question and get an answer from a random Reddit thread? Sick of bad answers, I tested the Encyclopedia Brittanica Chatbot.

Brittanica Chatbot uses articles from the Encyclopedia Brittanica to answer your question. These articles are written by experts in their fields.

This morning, I ran it through 3 tests…

Round #1: Teach Me About the Navy

Later today, I’m meeting with a startup that produces parts for naval ships. So I wondered, how does the navy handle repairs at sea?

Brittanica explained that sailors do many repairs themselves. A repair ship can come and do more complex maintenance.

The answer was helpful, but Brittanica didn’t cite any encyclopedia articles. I have no way of verifying Brittanica’s answer.

I’m giving this round a C.

Round #2: Learning About Knee Injuries

Half the people I know have knee problems. What’s the state of the art in fixing a bad knee?

Brittanica gave a thorough answer, digging into technologies from stem cells to gene therapy.

But again, Brittanica didn’t cite its own wonderful articles! Instead, it kicked the query to ChatGPT. I can’t verify if the response is accurate.

I’ll give this round a B.

Round #3: AI with a Green Thumb

For our last test, let’s do something fun!

My friend is turning his lawn into a carpet of wildflowers and other plants. Which plants work best?

This time, it cited several great Brittanica articles with specific recommendations. I love the periwinkle!

Brittanica’s answer was helpful. But I’d like to see specific plant recommendations right in the response, instead of making me click through.

I’ll give this answer a B+.

Wrap-Up

Overall, I’m giving Brittanica Chatbot a B-.

The concept is awesome. I‘d love to use a chatbot trained on articles written by experts.

But Brittanica Chatbot doesn’t deliver consistently. It often fails to cite Brittanica articles or any reliable source.

I’m excited to see how Brittanica Chatbot develops. With more expert-written articles and better indexing, it could become a real ChatGPT competitor.

Give Brittanica Chatbot a try and let me know what you think!

More on tech:

Stopping Mass Shootings with Technology

GPT-5 Fails Again

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.

How to Calculate Your IRR

October 10, 2025

Are my angel investments beating the market? Today, I crunched the numbers to find out. TL;DR: I’m at a 25% IRR.

This beats stocks by a large margin.

Let’s back up a little. What does this number mean, and how did I calculate it?

What Is IRR?

To know if I’m beating stocks, I have to calculate my Internal Rate of Return, or IRR. This number shows my annual percentage gain.

Let’s take a simple example…

You invested $10,000 on January 1st, 2024. On January 1st, 2025, the company was acquired and you got back $20,000.

Your IRR is 100%. In other words, you doubled your money in a year.

How IRR Works In My “Fund”

When you add more investments, things get more complicated. But it’s the same idea: figure out when I invested, when I exited, and derive a rate of return.

Most of my investments have not exited yet. For those, we use their current valuation and a date of today.

I am very conservative about valuations. I only mark up a company when they raise a new priced round, not when they raise a SAFE at a higher price. This is how the top VC firms operate.

I also accounted for the likely fees in my syndicate investments and for any dilution thus far.

What Data Do We Need?

I keep a spreadsheet of all my investments. This is the info I need for the IRR calculation:

Date investment made
Amount
Exit value of investment (if exited)
Date of exit
Current value of investment (if not exited)

For this calculation, we’ll look at my “Fund 1” of 35 companies. This is a typical number of companies for a venture fund. “Fund 1” includes investments made from June 2021 to August 2025.

Crunching The Numbers

I used Grok 4 Expert to crunch the numbers for me.

You can also use the XIRR function in most spreadsheet programs. But I like the step-by-step, carefully explained work that Grok does, so I went with that.

I fed Grok a spreadsheet with the data I mentioned above. Now, the moment of truth…

Grok found a 24.7% IRR!

Beating the Market

A 25% IRR beats the market handily. And it better — investing in startups is risky and illiquid!

The S&P 500 has averaged a 10% annual return in data going back to 1957. The NASDAQ Composite has hit an 11% return over the last 20 years.

The difference between a 25% IRR and 10% has a huge impact over time.

If you invest $1,000 at a 10% growth rate, you have $2,594 dollars in 10 years. Invest that same $1,000 at a 25% growth rate, and you have $9,313, or 3.6 times as much.

Wrap-Up

I was really surprised my results were this good!

There’s a huge caveat here: this IRR is based on paper gains. Converting paper gains to actual cash isn’t easy.

But for a portfolio that’s only a little over 4 years old, this is great progress.

Now, time to meet more founders and find that next great investment…

More on tech:

How My “Fund” Is Beating Over 90% of VC’s

Yes, You Can Angel Invest $5k Direct

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.

Yes, You Can Angel Invest $5k Direct

October 9, 2025

You don’t need to write a $50k or $100k check to invest directly in a startup. I’ve written tons of $5k and $10k checks. Here’s how it works…

Starting out, I did all syndicate investments, paying 20% carry each time. Now, most of my investments are direct.

When I made my first direct investment, I was intimidated. It sounded mysterious and difficult.

But it’s not.

It all starts with finding the right startup and getting a spot in the round.

How I Get a Spot, Even as a Little Guy

I’m upfront with founders about check size. If they only want huge checks, I’m not the investor for them.

When I meet a startup I love, I help them as much as I can. I make a bunch of intros to VC’s, helping them line up meetings.

I also tell the founder exactly why I love their company.

Take Nick at Verustruct. His 3D printing robot will build the homes to solve the housing crisis. That’s incredibly exciting!

The founder sees I can help him. He also sees that I care about the mission.

Helpful investors who care about the mission — that’s what founders want. So although my checks aren’t huge, I rarely miss a deal.

How The Investment Works

On the settlement date, the founder sends me the paperwork and wiring information. I e-sign the paperwork and wire the money.

It’s very simple and takes maybe half an hour. I confirm they got the money, in case the bank messes up.

But What About Legal Fees?

Early on, I heard you couldn’t invest less than $50k directly because of legal fees. This isn’t true.

At pre-seed and seed, everyone raises on SAFEs. All documents are standard.

I run the docs through an LLM to be sure I’m signing a standard SAFE.

I haven’t incurred any legal costs doing deals. Neither have other angels I know.

Wrap-Up

Small investors absolutely can invest directly.

It’s not difficult. Many great founders will be happy to have you.

I still invest through syndicates too, paying 20% carry for the privilege. I want the best deal, wherever it comes from.

But I’m no longer afraid to go direct. And if I save that 20%, even better!

More on tech:

Meet My Latest Investment: Verustruct

Investors: Get Your Wires In ASAP!

The Best Way to Share Your Deck with Investors

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.

Investors: Get Your Wires In ASAP!

October 8, 2025

8:32am: Wiring info received. 10:00am: Wire sent. I wire promptly to make your life easier.

Investors, don’t make founders chase you!

The Problem: Wasted Founder Time

I’ve watched founders chase investors for months. These are investors who committed to the company!

This wastes precious founder time.

They’re supposed to be building the next billion dollar company, not e-mailing an investor for the 5th time.

The Solution: Be Faster Than Other Investors

I saw a chance to differentiate from other investors here.

I wire as quickly as possible once I receive the documents from the founder. This usually occurs on the settlement date, when all investors are supposed to send their wires.

If founders have an easy time dealing with me, more great founders will come my way.

The Risks of Delay

When you drag your feet, you make more work for the founder. You risk exclusion from the round. And you hurt your reputation.

If you don’t want to invest in a startup, don’t! But if you do commit, follow through in a timely fashion.

Wrap-Up

The longer I do this, the more I realize what I really am: a customer service agent.

The startups are my customers. I have to give them good service.

If I don’t, they’ll go elsewhere.

Give founders good service, and you might be surprised the deals that come your way!

More on tech:

The Best Way to Share Your Deck with Investors

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 Best Way to Share Your Deck with Investors

October 7, 2025

You’re sending your deck to an investor. Millions of dollars are on the line. Here’s how to do it right…

An Oldie But a Goodie

The best way to send your deck is the simplest: a PDF attachment.

One click, and the investor is in your deck. Once he’s there, he’ll see your amazing traction and write you a check!

If he wants to forward your deck to other investors, a PDF makes that easy. This can result in a cascade of money.

The Dangers of Docsend

A Docsend link works, but it’s not as easy to save and forward. And why should you pay Dropbox and manage another product?

If you insist on Docsend, never require an e-mail, password, or one of those awful “magic links.” They encourage the investor to say, “Who cares?” and move on to the next.

You don’t want to make an investor’s job harder. You want to make it easy for them to give you money!

But What If My Competitors See It?

Some founders insist on e-mails and passwords because they’re afraid their competitors will see their deck. This isn’t worth worrying about, especially for an early stage company.

Your biggest problem will be getting anyone to care! What’s most important is to get the right people involved, ASAP.

Wrap-Up

We all love buying stuff on Amazon. One click checkout makes it easy.

You want one click checkout with your deck.

You’re competing with thousands of startups to get funded.

Give yourself every advantage you can. Make your deck easy to work with.

Make it a PDF.

More on tech:

Beware the Hot Deal

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.

What the Heck Is Going on in France?

October 6, 2025

France just lost its 5th prime minister in three years. What the heck is going on over there? Today, I decided to find out…

Another Government Falls

Prime Minister Sébastien Lecornu resigned today after several parties threatened a no confidence vote. That vote would’ve required Lecornu to resign.

The major parties can’t agree on a budget. The left wants more generous pensions and a wealth tax. The center and right support less spending and lower taxes.

A Nation Drowning in Debt

Behind all this political fighting is a country that’s deeply in debt.

French government spending accounts for 57% of GDP. Its budget deficit and debt to GDP ratios are among the highest in the EU.

After Lecornu’s resignation, French stocks are down and bond yields are up. Markets are telling us that France looks like a shaky bet.

How long can the government spend a majority of the country’s output?

A Deteriorating Economy

France’s economy is struggling, making it hard to pay all that debt.

Its unemployment rate is over 7%. Youth unemployment is 18%.

Those rates are much higher than in America. Our overall and youth unemployment rates are 4.3% and 10.5% respectively.

France isn’t growing because it isn’t innovating.

Of the top companies in the world by market cap, France doesn’t appear until #37, with LVMH. And in AI, France is lagging. Mistral, its only significant AI company, is way behind OpenAI, Anthropic and xAI.

Is America Next?

In America too, debt is leading to political upheaval. Right now, the government is shut down as Congress fights over health spending.

We don’t spend as much as France, but spending still hit 40% of GDP last year. Our debt to GDP ratio is even higher than that of France.

But America has huge advantages that make our debt more manageable.

It’s easier for our government to cut spending. The two party system means we don’t need to form coalition governments. We also don’t have no confidence votes.

Most importantly, we innovate. Innovation can help us grow out of our debt.

19 out of the top 25 largest companies in the world are American. So are almost all the top AI labs, along with SpaceX and Neuralink.

We need to reduce our spending, no question. But a strong economy makes handling this debt much easier.

Wrap-Up

France is looking at a bleak future. It’s deeply in debt and isn’t innovating enough to grow its way out.

There’s only one way to fix France: cut spending. Stop letting the government suck up the entire economy.

If France can’t do that, it will continue to cycle through governments. Nothing will really change.

And every year, it will get a little poorer.

P.S. Thanks for bearing with me last week as I was on vacation. New Orleans was wonderful! Glad to be back.

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: Memelord

September 26, 2025

Something weird happened to me recently: I had fun using SaaS. So of course, I invested in the company.

Memelord finds trending memes from all over the internet. Then, it helps you make hilarious versions of them to promote your business.

I always try to use products before I invest. But with Memelord, I found myself coming back over and over, long after I’d tested it sufficiently.

This thing is fun to use!

Founder Jason Levin plans to build the Palantir for Memes.

Palantir sends Forward Deployed Engineers to help customers configure the software and get the most out of it. Jason offers consulting to customers to help them make awesome memes.

Call it Forward Deployed Memelords.

Jason’s approach hit home. I used to work for an Electronic Medical Records company called Epic. Like Palantir, they send staff to customer sites.

I was one of those people. I learned that software plus services can be an incredible combination.

But in the end, the reason I invested in Memelord isn’t really about any of this. It’s about Jason.

The man defines “scrappy.” His energy is boundless, his understanding of marketing instinctive.

He’s just the man for the job. And although I may be the smallest investor he has, I’m delighted to be in business with him.

Check out Memelord and make some awesome memes!

The next blog will be on Monday, October 6. I’m headed to New Orleans next week on vacation! 🥳

More on tech:

Meet My Latest Investment: Verustruct

Beware the Hot Deal

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: Verustruct

September 25, 2025

My number one lesson from 4 years angel investing: it’s all about the founder. The founder of my latest investment is one of the best I’ve ever met.

Nick Callegari is the founder of Verustruct, the company that is going to solve the housing crisis.

Verustruct is developing a 3D printer that makes houses. The printer will build cement walls and embed the mechanical, electrical and plumbing along with them.

This will let us build faster and cheaper than ever before.

Before Verustruct, Nick led a team of engineers at SpaceX. He developed the extravehicular activity structure for the Polaris Dawn Crew Dragon mission.

This structure enabled the first commercial spacewalk. If Nick’s structure had failed, those astronauts would’ve died.

Here’s my thinking: if Nick can pull that off, 3D printing a house should be easy!

It’s no secret that housing in America today is obscenely expensive. The median house price is $447,000. And if you want a newly built house, the average is $515,000.

Add in 7 percent mortgage rates, and who the heck can afford this?

If Verustruct can print houses en masse, quickly and cheaply with less skilled labor, those prices will fall off a cliff.

Finally, the average person will be able to afford a decent home.

I’m incredibly excited about what Nick is doing at Verustruct. Some day, I hope to live in one of their houses myself!

More on tech:

Your Next House Will Be Built By Robots

The Question No Founder Asks

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.

Beware the Hot Deal

September 24, 2025

The hottest startup is a great place to lose your money…

Theranos
FTX
WeWork
Clubhouse

Investors threw cash at these companies.

Theranos and FTX turned out to be frauds. WeWork and Clubhouse struggled to make a viable business.

Either way, the investors got torched.

When Investors Get Sloppy

When a startup is hot, investors don’t do diligence. This lets bad investments slip through.

Normally, a VC talks to customers to see if the product is as good as it looks. They also review bank statements, revenue and burn.

In a hot deal, investors throw that diligence checklist out the window.

In the case of Theranos, investors put in millions without ever seeing the device. Even when I invest $10,000, I want to see a prototype!

Are We About to Fund the Next FTX?

Markets are as hot as in 2021. I’m seeing seed rounds at $75 million.

I can feel it all happening again.

In a hot market, another FTX or Theranos can slip through. It feels like everyone’s making money. You don’t want to be left behind, do you?

So you skip your diligence, just this once.

All the top investors are in this company. It must be a winner!

How I Approach Hot Deals

I do the same diligence for every company.

I work quickly. In fact, I can usually get a founder a decision within 24 hours.

But I’m definitely looking into product, revenue, and burn. I’m also going to research the team.

If I skip those steps and the company implodes, I’ll be kicking myself. If I did my research and the company dies, at least I tried my best.

Wrap-Up

Everyone wants to be in the hottest deal.

We’re afraid to miss a big winner. We don’t want to seem insignificant.

But odds are, you’re not missing anything.

I’m staying focused on real businesses raising at reasonable prices. If the rest of the market wants to go crazy, let it.

More on tech:

How Top Startups Break the Rules

The Question No Founder Asks

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!