Tremendous

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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!

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When Can You Quit Your Job?

April 15, 2025

I recently met an amazing founder. His company had incredible potential. But he was afraid to quit his job and pursue it full time. So, when is the right time to go all in?

Just like a startup, people have runway. Your runway is the amount of time until you run out of cash at your current burn rate.

For startups and for individuals, I recommend 18 months runway. 12 months is the bare minimum.

When to Quit Your Job

Let’s say you spend $8,000 a month. 18 months runway is $144,000. Save up $144,000, and you have enough runway to go full time on your own business.

That may sound like a lot of money. But many of the folks who start tech startups work in FAANG companies making huge salaries. At those rates, you can save up $144,000 pretty quickly.

But there’s another trick that can get you your freedom sooner: cut your spending!

What if you could get that $8,000/month down to $5,000? Maybe you cut some trips and eating out. Perhaps you move to a cheaper place.

Now, you only need $90,000. That could mean pursuing your dreams a year sooner!

And of course, if you can raise an accelerator check of perhaps $125,000, you may not need any personal savings at all.

How to Handle Your Finances as an Entrepreneur

Here’s how these 18 months will work…

For the first year, just go all-in on your business. Do everything you can to make it a success.

The hours will be long, but you’re working for yourself on your own dream. That helps a lot.

After 1 year, assess where you’re at financially. Are you making enough to cover your personal burn? If not, can you cut the burn further?

Let’s say that after the first year, you’re not making anywhere near enough. Perhaps your business is paying you $2,000 a month and you need $5,000.

In that case, it’s time to start looking for a job. You’ll still have at least 6 months to do that, which should be enough time.

My Experience Quitting My Job

In 2019, I quit a great job in tech. I wanted to invest full time.

Those 6 years have been some of the best of my life!

I was lucky to have that job and my co-workers were great. But to tell you the truth, I never missed that office for a day. I don’t think I’ll ever forget the moment I walked out for the last time.

I maintain my freedom by keeping my spending reasonable. I live very comfortably, but I don’t live in a huge mansion or cruise down the Hudson on a yacht.

That freedom makes me way happier than fancy stuff ever could. And every morning, as I see folks at the bus stop headed to New York City to work for someone else, I’m grateful that I can do what I want.

Wrap-Up

You may be terrified to quit your job. Society tells you that you have to work for someone and bring home a paycheck.

But in reality, you don’t.

If you have a business you want to pursue, save your pennies and get yourself in a position to quit your 9-5. If that involves cutting your spending, so be it.

Having the freedom to pursue what you love beats a Mercedes any day.

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.

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How to Diligence VC’s

April 14, 2025

VC’s will diligence the heck out of you. But you should be diligencing them too. Here’s how to do it…

Don’t ask the VC for references. He can just cherry pick the founders in his portfolio that are the most likely to say something nice about him.

Instead, go to his portfolio on the firm’s website or on Crunchbase. Pick a few companies and contact the founders yourself.

Don’t pick companies that are a big success. Instead, pick obscure ones that haven’t caught on. And if you can find a few that failed, even better!

It’s easier for everyone to get along when a startup is crushing it. It’s when things aren’t going well that tempers are likely to flare.

Once you’ve found perhaps 5 startups, send the founders a short message:

“Hi Mike! I see that Jim at ABC Ventures led your seed round. I’m considering having him lead mine. Do you have 5 min to discuss your experience working w/ Jim?”

Founders like helping other founders. If you ask politely and make it clear it won’t take long, you should be able to get plenty of references.

No reputable investor will mind you diligencing them. In fact, they’ll respect you for being smart and thoughtful.

I hope every founder I’m planning to invest in talks to other founders I’ve worked with!

I’m pretty sure they’ll hear something positive. That will improve my odds of getting into the deal.

I recommend getting references for anyone you let onto your cap table. But at a minimum, you have to diligence your lead investor.

As a founder, you’re extremely busy. It would be easy to let references slide, especially if someone is dangling $1 million over your head.

Don’t. Getting rid of an investor is practically impossible.

You could be stuck with this guy for 10 years or more. You want to make sure he’s someone you can work with without tearing your hair out.

A few minutes of diligence now could save you untold painful hours in the near future! Do yourself a favor: get those references.

More on tech:

When an Investor Pulls Your Term Sheet

The Best Service Providers for Startups

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 Service Providers for Startups

April 11, 2025

Most lawyers and accountants have no idea how to work with tech startups. So where should founders go? Here are my favorites…

Incorporation: Capbase. Capbase can get you properly incorporated in minutes for less money than others. It’s just $999/year.

Full disclosure: I have a small investment in this one. I invested in it because I think it’s a fantastic service.

How you incorporate is really important. If you choose the wrong corporate form, like an LLC, you’re cutting yourself off from funding.

All Capbase does is work with startups, so you can be sure they’ll do it right.

Bookkeeping and Tax: Kruze Consulting. Kruze specializes in bookkeeping and taxes for startups. This makes them a much better choice than a typical accounting firm, which will not understand your business.

Because startups are all they do, they’re on the lookout for tax provisions that could help you, like R&D credits. You won’t get that from the accountants down the street.

Many of my investments have worked with Kruze and they’ve always been happy with the service.

Legal: Goodwin. Goodwin works with startups all the time. They understand your needs: things like funding rounds, IP issues, and more.

They’re also really good about giving free or discounted work to early stage startups. They want to build a relationship for the long term.

Shutting Down: Simple Closure. Hopefully, you’ll never have to use this. But let’s be honest: most startups fail.

If you do fail, you need to shut the company down correctly. Simple Closure makes it really easy.

I recently had a startup fail and SimpleClosure handled the process beautifully. I just got the final K-1, an important tax form. It came before most of my other investments, which shows you how efficient SimpleClosure is.

Wrap-Up

Having the right service providers to help you makes your life so much easier. This is true for individuals and it’s true for startups too.

Startups are weird creatures. They incorporate differently than most companies, face different legal issues, and have unique tax considerations.

That’s why these providers are the best — they work with startups every day. You’ll sleep better at night knowing your taxes, legal and accounting are being done right.

Have a great weekend everybody!

More on tech:

When an Investor Pulls Your Term Sheet

Five Things Founders Should Never Pay For

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.

When an Investor Pulls Your Term Sheet

April 10, 2025

This $750,000 term sheet was going to save the company. The founder was elated. And then, a phone call. The investor was pulling out.

Investors can pull a term sheet for any reason. It’s rare, but when it happens it can leave a company crippled.

Worst of all, it can have nothing to do with the startup.

Losing Your Lead

In a great post on Reddit’s r/entrepreneur sub, a founder describes how an investor gave them a $750,000 term sheet. This term sheet was a lifeline. The startup had practically nothing left in the bank. The founder had drained his personal funds as well.

But in due diligence, the investor said the customer references were negative and gave that as their reason for pulling the term sheet. Many of the commenters say there could be more to the story, and I agree.

The founder probably chose his happiest customers as references. I doubt they’d give such poor feedback.

My suspicion is the lead may not have had the cash to begin with.

Some funds commit to a round before they’ve actually raised the money from LP’s. This is a rotten thing to do, but it happens.

My Experience With a Lead Pulling Out

I’ve only seen this once in my 4 years investing. The lead was a syndicate that didn’t raise what it expected from its members. So, they couldn’t fulfill their commitment to the startup.

The startup had been counting on that money. Now they were left with a dwindling bank account and no money on the way.

Since the round was no longer happening, I didn’t invest either. I’m not sure what happened to the startup, but Crunchbase has no data on them raising further cash.

I’m guessing the company probably folded. This failed round probably contributed to that.

How to Protect Yourself

Legally, investors can pull out for any reason or no reason. But there are ways to avoid this situation and to limit the damage if a round does fall apart.

VC’s that pull out of rounds tend to be no-name investors. They probably didn’t have the cash to make the investment to begin with.

It’s fine to include some obscure names in your round. But having one as the lead is risky.

Similarly, having a syndicate lead your round is a crapshoot. Maybe they can raise the money for the deal, but maybe they can’t.

When the round I was in fell apart, the lead had both these red flags. They were an obscure syndicate based in Europe.

That’s definitely not a good choice for a lead investor.

But there’s an even better way to protect yourself than choosing a good lead: getting to break even.

If you’re at break even when you raise money, you’re in a position of strength. You can dictate the terms. And if the round doesn’t happen, it’s no big deal.

Wrap-Up

Losing a lead investor can devastate a company. And unfortunately, it often has more to do with the investor than it does with the startup.

Protect yourself! Choose a lead with a track record and a good reputation. And get to break even before you start fundraising.

This way, whatever happens, you will survive.

More on tech:

Is Your Vision Big Enough?

Five Things Founders Should Never Pay For

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.

Is Your Vision Big Enough?

April 9, 2025

Most startups will never be a huge success. Their vision isn’t big enough.

Let’s take a look at 3 of the most successful startups of the 2020’s. All have reached valuations of over $10 billion.

Each of these founders imagined a radically different world, then went out and made it happen.

Colossal Biosciences — $10.2 billion. Yesterday, I was listening to an interview with the founder, Ben Lamm, on the Joe Rogan podcast. Listen to Ben for 10 minutes and you’ll see how ambitious he is.

Ben plans to bring back the woolly mammoth and other extinct species. If he realizes his vision, the world will be full of animals none of us have ever seen.

Already, they’ve created the woolly mouse and resurrected the dire wolf. And the company is just 3 years old.

Do you see how different this is from the typical startup? A typical startup tries to help you find sales leads a little more easily, something like that. Incremental change.

Ben doesn’t care about incremental change. His vision is radical.

Figure — $39.5 billion. Figure is developing humanoid robots. Founder Brett Adcock plans to make one for every human being in existence.

This is a radically different world. Robots would be doing manufacturing, farm work, even cleaning our houses.

Compare this to a typical startup. Maybe that startup is making meeting notes easier or scheduling a little smoother.

That just doesn’t change things the way Figure could. So it simply cannot grow as large.

Cursor — $10 billion. The other two startups on this list are deep tech. But pure software can be transformative too. Cursor is a great example.

Cursor lets anyone create software, no coding background needed. If you had an idea for a software tool in the past, you had to find a coder to build it for you.

Now, everyone is free to build their own tools that are perfect for them. Imagine the 1,000 businesses that could enable.

Cursor is a powerful, general purpose tool. Software startups like that can become massive.

Wrap-Up

I had a chance to invest in Figure’s seed round in March of 2023. I passed on it, concerned about the valuation and how capital intensive the business would be.

That turned out to be a huge mistake. I’d be sitting on a 100x return in only 2 years if I’d had the brains to put a check into it.

Since then, I’ve been thinking about how to catch the next Figure. My conclusion: I need to look for giant opportunities.

When a company’s ambitions are small, even the best case scenario isn’t that great.

Startups with a giant vision usually bite the dust too. But at least I have a chance of a big success.

And one is all it takes.

More on tech:

Five Things Founders Should Never Pay For

How to Build a Relationship 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.

Testing Mistral’s Le Chat

April 8, 2025

There’s an AI model that’s 13x faster than ChatGPT. The cost: $0. But can Mistral’s Le Chat beat the best tools from the US?

This morning, I put the French model through its paces. I asked it 3 questions I actually need the answer to. I posed these same 3 questions to Grok 3 on the blog recently, and it produced the best responses I’ve seen.

Can Mistral’s Le Chat do better? Let’s find out…

1) Le Stock Analyst. I recently had Grok help me with my index fund allocation. But maybe Mistral can give me some even better ideas.

Here’s the prompt I used:

“Assume I have a portfolio of index funds. My goal with this portfolio is long term growth. How should I allocate this portfolio across different types of index funds? Consider options like US index funds, foreign stock index funds, etc. I am 39 years old, so my time horizon is long. My risk tolerance is high. What would be the best allocation, given all this information? Use the best research you can find to support your answer.”

Let’s see what Mistral advises:

Mistral gave a thorough and well reasoned response. It advises a split between US and foreign index funds with a small allocation to bonds.

However, Mistral doesn’t consider a 100% stock portfolio, which can make sense for a younger person with a high risk tolerance. And while it cites relevant sources, there are only 6. Grok searched over 40 different sites.

Mistral’s answer was better than what I’ve seen from Gemini, Claude or Alibaba’s Qwen. But Grok 3 takes this round.

2) Le Startups. With fertility rates on the decline, I’m looking for startups that make it easier for women to have children later in life.

Let’s see if Mistral can help. Here’s my prompt:

“What are the most interesting startups at pre-seed stage working on solutions to increase fertility? Consider startups to lower costs and improve effectiveness of IVF, and also startups to improve egg health for older women, among other possible ways to boost fertility. Please only show me startups that have raised $750,000 or less in funding.”

Here’s what Mistral found:

Mistral found some good candidates, like Gameet, and others that were too late stage. Grok produced a similar response, finding some good candidates and others that were outside my search criteria.

I’ll call this round a tie.

3) Le Meetings. I’ve got a meeting with an interesting AI tutoring startup set for this afternoon. So how do I get the most out of my time with the founder?

Here’s the prompt I used:

“As an angel investor, I meet with a lot of startup founders. I want to do the best job I can in those meetings. What are some tips to perform better, be more helpful, and learn more about the startups I meet with?”

Let’s see what Mistral advises:

Mistral gives some great advice here. It reminds me to be empathetic to the difficult job these founders are doing. It also emphasizes how important it is to be transparent about my decision, whether it’s a yes or a no.

When I posed this question to Grok, it told me to watch the founder’s body language. That was an especially useful tip that Mistral didn’t include.

This round is close, but I have to give it to Grok.

Wrap-Up

Mistral’s Le Chat is a very impressive model. For answering general questions, it’s better than Gemini, Claude, or Alibaba’s Qwen.

But Grok 3 is still the best model I’ve used. It scours the internet for information, analyzes it intelligently, and presents it in seconds. Le Chat just can’t compete.

It’s amazing that a little French startup is beating giants like Google and Alibaba. But Mistral has a way to go before they take the #1 spot.

More on tech:

How Good is Grok 3?

Testing Google’s New Gemini 2.5 Pro Model

Testing Alibaba’s New Qwen Model

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.

Markets Are Overreacting to Tariffs

April 7, 2025

Some of the greatest companies in the history of capitalism are selling at ridiculously low prices right now.

How would you like to have Warren Buffett as your personal money manager? Today, he’s available at a discount: just 12 times earnings. And Berkshire isn’t the only blue chip that’s on sale.

Stocks in the Bargain Bin

Trump’s big tariff announcement Wednesday has spooked markets. The S&P 500 is down 10% and markets worldwide are falling in sync.

This is leading to some incredible bargains in stocks.

Let’s take a look at 5 of the best companies in history. Here are their current price/earnings multiples:

Google: 19
Berkshire Hathaway: 12
Merck: 12
Bank of America: 11
Samsung: 11

Google is the greatest money machine ever invented by man. You could easily justify a 25 PE on that.

As for Berkshire and Merck, these are tried and true companies, the bluest of blue chips. They could jump by 50% and still not be overvalued.

This is how tough markets end. You begin to see some ridiculous bargains like these. Then, a few folks tiptoe into the market and scoop them up.

Is the Whole Market Cheap?

Despite the drop since Trump’s tariff announcement, stocks on the whole are not especially cheap. The S&P PE ratio sits at 25, still above the historical average of 15-20 times earnings.

The market is dominated by the Magnificent 7 stocks, many of which are still trading at rich multiples:

Tesla: 113
Nvidia: 32
Amazon: 31
Microsoft: 29
Apple: 29

These stocks have come down, but their prices were so high at the market peak that they’re still expensive. Less fashionable companies, however, are trading at very low valuations.

But What About Tariffs?

Even if the tariffs stay on, the valuations of some stocks are incredibly low. But what if they’re only temporary?

The White House is already beginning negotiations with dozens of countries on lowering tariffs. If our trading partners cut their rates, Trump may cut ours, perhaps all the way down to zero.

Relief on the tariff front would be a massive tailwind for the market.

And don’t forget about tax cuts. Congress is working on a major package as we speak. Lower taxes could give markets a significant boost.

Wrap-Up

Investors are manic depressive.

When they’re excited, they bid stock prices too high. When they’re scared, they panic sell and prices fall through the floor.

We’re seeing amazing bargains right now in some of the best companies of all time. I expect buyers to pop up for those companies, supporting the market.

As for me, I’m holding all my positions.

Tariffs or no tariffs, companies will continue to innovate. I intend to own a piece of it.

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.

Testing Google’s New Gemini 2.5 Pro Model

April 4, 2025

Google recently dropped its most advanced model yet, 2.5 Pro. This morning, I put it through 3 real world tests to see if Google can beat the best model I’ve used so far: Grok 3.

I asked it 3 questions I actually need the answer to. These are the same questions I posed to Grok 3 recently.

Let’s get started!

1) Optimize My Stock Portfolio. I recently had Grok help me fine tune my index fund portfolio. But maybe Gemini can do better.

Here’s the prompt:

“Assume I have a portfolio of index funds. My goal with this portfolio is long term growth. How should I allocate this portfolio across different types of index funds? Consider options like US index funds, foreign stock index funds, etc. I am 39 years old, so my time horizon is long. My risk tolerance is high. What would be the best allocation, given all this information? Use the best research you can find to support your answer.”

Let’s see what Gemini says:

Gemini’s response was smart and well-reasoned. Like Grok, it recommends a portfolio of 90-100% stocks with a split between domestic and foreign.

But there was one big problem with Gemini’s answer: it had no sources.

Gemini mentioned that Modern Portfolio Theory supports its answer. But there’s no link to any research and no way to verify its claim.

Grok 3, by contrast, cited over 40 high quality sources. I’m giving this round to Grok.

2) Find Me Some Startups. I’m really interested in startups that could help us with our baby bust in America. So, I set Gemini to work on it.

Here’s the prompt I used:

“What are the most interesting startups at pre-seed stage working on solutions to increase fertility? Consider startups to lower costs and improve effectiveness of IVF, and also startups to improve egg health for older women, among other possible ways to boost fertility. Please only show me startups that have raised $750,000 or less in funding.”

Here’s what Gemini came up with:

Gemini’s answer was useless. It gave me a startup, Gameto, that has raised $73 million in funding. This is a clear violation of the instructions I gave. Similarly, Alife has raised over $30 million.

Then, it gave me some general ideas of types of startups to look at. This isn’t useful either — I asked for specific companies.

Grok, on the other hand, gave me some actual early stage startups to research. Once again, the round goes to Grok.

3) Making My Meetings Better. Finally, I asked Gemini to help me with a problem I struggle with daily: how to do my best when I meet with founders.

I want to be present and helpful. I want to ask good questions and learn a lot about the founder’s vision.

Here’s the prompt I used:

“As an angel investor, I meet with a lot of startup founders. I want to do the best job I can in those meetings. What are some tips to perform better, be more helpful, and learn more about the startups I meet with?”

Let’s see what Gemini advises…

Gemini’s advice is spot on. It tells me to be sure I’m on time and to offer constructive feedback when I pass on a company. Those are things I already try to do, but it’s good to have that emphasized.

Gemini’s answer was just as good as Grok’s here. So, I’ll call this round a tie.

Wrap-Up

Grok 3 beat Gemini 2.5 handily, winning 2 out of 3 rounds.

If Google wants to dethrone the leaders like Grok and ChatGPT, they’re going to have to do better than this. I expect more out of a $2 trillion company.

This model is actually worse than their existing Deep Research model, which gives precise and well sourced responses. With Gemini 2.5, Google is actually going backwards.

If you need answers to your questions or want to build AI into your product, Gemini isn’t it. Grok 3 is a better choice.

Have a great weekend everybody!

More on tech:

How Good is Grok 3?

Testing Alibaba’s New Qwen Model

DeepSeek vs. Gemini Deep Research: Which Model Is King?

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.

As Tariffs Hit, Lower Interest Rates Could Cushion the Blow

April 3, 2025

Trump’s new tariffs are making headlines. But a less noticed trend could be a lot more important: a recent fall in interest rates.

Tariffs raise the cost of imported goods. Interest rates determine what we pay to borrow for a home, auto, or credit card loan.

For most startups, the positive effect of lower interest rates will matter more than the negative impact of tariffs.

A Broad Fall in Interest Rates

The 10 year Treasury bond rate has fallen from a recent high of 4.79% in mid-January to 4.17% today. This rate serves as the benchmark for mortgages.

Other rates are down as well. The prime rate is down from 8% to 7.5% in the last few months. The 5 year Treasury rate has fallen around 70 basis points. These rates drive the cost of auto and credit card loans.

Rates Matter More Than Tariffs For Most Startups

Tariffs will have little effect on most software startups. They don’t import anything to make their product. But lower rates will help many companies.

For prop tech startups, lower rates are a godsend. The 10 year Treasury is so important to this market that a CRE broker friend of mine checks it every day. Those lower mortgage rates make people much more likely to buy a house.

Similarly, lower rates for car loans help startups in the auto sales sector. And a lower prime rate should be great for fintech startups generally.

Even for hardware startups, the impact of tariffs should be limited.

Most make their product here in America. Their main concern will be an increase in the cost of some components, which may be sourced abroad.

Wrap-Up

My hope is that Trump uses these tariffs as a negotiating tool to get us better terms of trade with other countries. If tariffs help us sell more to the rest of the world in the long term, they could be a net positive.

But if the tariffs stay on for too long, they could be a drag on economic growth. We should use tariffs as a tool, not an end in themselves.

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!