Tremendous

An angel investor's take on life and business

  • Early Stage Valuations Surge in New Report

    Valuations for early stage startups jumped in 2024, according to a new report from AngelList. Pre-seed valuations are up 20% while seed prices rose 18%.

    Median pre-seed valuations hit $10 million pre-money. Seed reached a heady $20 million.

    This marks a big increase from 2023, when the median pre-seed was $8.3 million and seed was $17 million.

    Why Are Valuations Up?

    This jump in valuations is driven by two things: AI fervor and big funds moving earlier.

    Just yesterday, I used Gemini Deep Research for the first time. It’s the most incredible thing I’ve seen since I first used the internet 30 years ago.

    No investor wants to be left behind when breakthroughs like this are happening. So, many VC’s are piling into AI startups without regard to price.

    What’s more, big multistage funds are moving earlier. If you’ve got a $1 billion fund, a $4 million seed check is nothing to you. The dealflow alone could be worth the investment.

    These funds have money to burn and are not price sensitive. That pushes up valuations across the market.

    What’s Going On In My Portfolio

    The prices I’m investing at are much lower than what’s on AngelList.

    My median pre-money valuation in 2024 for a pre-seed was $5.75 million, versus $10 million in the AngelList data. My median pre-money valuation for a seed round was $12.5M, versus $20 million on AngelList.

    My gut tells me that the AngelList valuations are a lot higher than the market in general.

    I see a ton of AngelList deals. They tend to be buzzy rounds at high prices. There is often a big name, multistage fund leading the deal.

    It makes sense that syndicates on AngelList do deals like this. It’s easier to round up investors if there’s a big name leading the round.

    But those hot rounds don’t necessarily provide the best returns.

    Wrap-Up

    I expect 2025 to be a strong year for early stage startup funding. The upward trend from 2024 is clear, and with AI excitement high as ever, there’s no reason for that to change.

    As for me, I’ll be doing what I’ve always done: investing in the best startups I can find at reasonable prices.

    I’m very excited about AI too. But we cannot completely disregard traction and entry price, no matter how promising the future seems.

    More on tech:

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

    Meet My Latest Investment: Querio

    I’m About to Close the World’s Tiniest Venture Fund

    Save Money on Stuff I Use:

    Fundrise

    This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 with great returns.

    More on Fundrise in this post.

    If you decide to invest in Fundrise, you can use this link to get $100 in free bonus shares!

    Misfits Market

    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.

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

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

    The entire world seems to be talking about DeepSeek. But how good is it really? Today, I put it up against the best I’ve ever seen: Gemini Advanced 1.5 Pro with Deep Research.

    Developers can game benchmarks. So I put these 2 models through a real world test, asking a complex question I actually needed the answer to.

    Let’s see who wins!

    Doing Real World Research

    The question I asked grew out of research I’m doing for my work as an angel investor.

    I’ve heard that there is only one size of IUD available in the United States. Some women find them too large and experience a lot of pain during and after insertion.

    Since I invest in startups, I got to thinking…”Is there a company here?”

    Not knowing much about IUD’s, I decided to ask my new friends DeepSeek and Gemini Deep Research.

    Here’s the prompt I used: “in the United States, is there only one size of Mirena IUD available?”

    Let’s see what they come up with…

    DeepSeek R1

    DeepSeek gave a good answer, but it didn’t cite any sources. It’s hard to know if the information is accurate.

    It also neglected to mention the Paragard IUD, which can be a good option for some women.

    Overall, DeepSeek’s answer is a good start but lacks depth. Let’s see how Gemini does…

    Gemini Advanced 1.5 Pro with Deep Research

    Gemini Deep Research starts by making a research plan. It lets me modify the plan if I want to before the research begins, which is an awesome feature. But Gemini’s plan sounded great, so I just approved it.

    Gemini’s result stunned me.

    It produced a 4 page report with 13 citations from highly reliable sources like the Cleveland Clinic and Mirena itself. It gave a wide range of IUD options with highly specific info on each one.

    It even dug into a section of the Mirena website that is only for health care providers, somewhere I’d be highly unlikely to go on my own.

    I checked some of this info on the websites Gemini cited. Everything I checked was 100% accurate.

    I’ve never seen anything like this. Reading Gemini’s report, I was reminded of the first time I used the internet.

    This is truly next level.

    From the research Gemini presented, it sounds like there are a variety of IUD sizes out there already. So, investing in new types of IUD may not make sense.

    Wrap-Up

    Gemini’s answer was incredibly useful. The great citations gave me confidence in the result — the confidence to act.

    That’s what so many AI tools are missing. They feel more like a toy than a useful product.

    Gemini feels like an incredibly smart and diligent research assistant. I’d have to pay someone at least $40,000 a year to do research like this for me, even if I hired in the Philippines or other developing markets.

    Gemini does it for $20/month. It also works dramatically faster than any human, 24 hours a day.

    DeepSeek isn’t bad for a new model. What’s more, it was cheap to build and it’s cheap to run. But if you’re looking for the best, DeepSeek isn’t it.

    Gemini still rules the roost.

    More on tech:

    ChatGPT Pro vs. Gemini Advanced vs. Grok vs. Claude

    Meet My Latest Investment: Querio

    I’m About to Close the World’s Tiniest Venture Fund

    Save Money on Stuff I Use:

    Fundrise

    This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 with great returns.

    More on Fundrise in this post.

    If you decide to invest in Fundrise, you can use this link to get $100 in free bonus shares!

    Misfits Market

    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.

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

  • How Are Angel Investors Like Psychiatrists?

    This weekend, I was chatting with a friend who’s a psychiatrist. She often deals with patients in crisis. I sometimes deal with founders in crisis. So I got to thinking…

    How can I apply what psychiatrists do to my work investing in startups?

    Some founders I meet with are in a very difficult period in their lives. They’re losing their business, having to lay off employees, and saying goodbye to their dream.

    So, I asked her to explain how she deals with patients in crisis. We distilled the approach into a four-part system you can apply to any human relationship: Listen, Validate, Reassure, Explain (LVRE).

    Here’s how it works…

    Listen: Listen to the person’s problem. Sometimes, what a person in crisis needs most is to be heard. What’s more, if you don’t know what’s going on with them, you cannot help them.

    Consider our world of investing….

    We investors often give ill-considered opinions. We jump in without knowing all the facts, much less how the founder is feeling.

    If we do a better job of listening, we have a better chance to help.

    Validate: Try to validate the person’s feelings and concerns, even if you don’t see things the same way.

    My psychiatrist friend sometimes deals with patients with paranoid delusions that have no basis in reality. Nonetheless, she can validate those feelings, saying that the patient must be very worried or upset given the experience they’re having.

    Founders I deal with are much more grounded, of course. But validating how they’re feeling is just as important.

    Perhaps a founder feels overwhelmed with the company’s problems. I could respond by saying, “It’s understandable why you feel overwhelmed, you’re in a tough period with cash getting short.”

    Reassure: Reassure the person that things will be all right.

    For my friend, this can be difficult. She needs to reassure someone in a mental health crisis that they will be okay and will feel better in the future.

    The situations I deal with as an angel are not as extreme. But if a founder is losing his business, he could still use reassurance.

    For example, I can tell him that he will move on to another job or another company. His career is far from over.

    In fact, the most successful founders usually have a few failures in the rearview.

    Explain: Lastly, my friend explains the treatments she is about to give a patient. If she needs to give them medication, for example, she explains why and what to expect. When a patient knows what to expect, they’re less anxious.

    So, how does this translate to our world in startupland?

    If a startup is failing, I can explain that all I expected was for the founder to try his best and keep us updated. I can also explain that historically, failure has been a step to later success for most founders.

    Wrap-Up

    Several of the most successful people I know were psychology majors. This is no accident.

    Everything in business comes down to people. No matter how technical the industry, we have to connect with other human beings.

    Try the LVRE framework along with me! The more we practice it, the better we’ll get at relating to others.

    Then, we can work together to create something great!

    More on investing:

    Meet My Latest Investment: Querio

    I’m About to Close the World’s Tiniest Venture Fund

    Poor Charlie’s Almanack

    Save Money on Stuff I Use:

    Fundrise

    This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 with great returns.

    More on Fundrise in this post.

    If you decide to invest in Fundrise, you can use this link to get $100 in free bonus shares!

    Misfits Market

    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.

    Use this link to sign up and you’ll save $15

  • Meet My Latest Investment: Querio 

    A man who comes to America alone at 17 and makes himself a success is someone I want to be in business with. More than any details of product or financials, that story drove my latest investment. 


    The founder is Rami Abi Habib. His startup, Querio, is basically ChatGPT for your data. 


    Any non-technical user can ask questions based on company data. Which products are selling well lately and which aren’t? Which sales reps give the most discounts? 


    Querio hooks into your data warehouse and gives you the answers. 

    It would’ve taken data analysts weeks to get you that information before Querio. Now, you can grab it yourself in seconds. 


    Many companies spend hundreds of thousands of dollars on Tableau, Looker, and data analysts. Querio can replace all of that at a fraction of the cost.

    A smart, scrappy guy making a product a ton of people need – that’s the kind of investment I’m looking for.

    Check out Querio and save your company time and money!

    There will be no blog tomorrow. See you guys on Monday and have a great weekend!

    More on tech:

    Meet My Latest Investment: Recall

    Test the Product!

    I’m About to Close the World’s Tiniest Venture Fund

    Save Money on Stuff I Use:

    Fundrise

    This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 with great returns.

    More on Fundrise in this post.

    If you decide to invest in Fundrise, you can use this link to get $100 in free bonus shares!

    Misfits Market

    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.

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

  • The Coming Robot War with China

    Since 1945, our nuclear weapons have made us invulnerable. Those days are over.

    Chinese companies are well ahead of us in robotics. Soon, they will turn these technologies to military uses.

    Unitree recently demoed an android that can run fast on hills, gravel, or stairs. It will cost just $16,000.

    Robot dogs on wheels from DEEP Robotics can speed through snow, streams, and rocks. Massive numbers of drones can descend on a city and surround it.

    Today, none of these robots have weapons attached. Soon, they will.

    Imagine a conflict with China in 5 years.

    They shut down our 911 and water systems with hacking. 100 million drones descend on all our major cities, dropping bombs. 10 million robot soldiers storm the coasts.

    I’m not trying to be an alarmist here. But given the incredible speed at which China is advancing in robotics, is this really that far fetched?

    All these robots will be powered by AI and Large Vision Models. They’ll simply be given a goal (“destroy the 3rd Infantry”) and will act autonomously to do it.

    No one mass produces like China. Even if we manage to field some capable robots, China may massively outproduce us and still win.

    Our fail-safe is a massive stockpile of nuclear weapons. But if we launch ours in self-defense, they will launch theirs.

    In this scenario, we would face 2 choices:

    1) Total destruction of America and much of the world in a nuclear war.
    2) Surrender to China to try to save lives.

    As awful as it would be, we would pick #2.

    The only way to prevent this scenario is to catch up with and surpass China’s advances in robotics.

    We must have better robots than China. Even more importantly, we must be able to produce them at incredible scale.

    Slow defense procurement and cockamamie environmental regulations cannot hold us back. We have to build these weapons as fast as humanly possible.

    I’m encouraged to see moves like the Arsenal-1 plant from Anduril and the $500 billion Stargate plan to build out AI data centers. We need a lot more rapid, bold action like this.

    Angel Jason Calacanis put it well on a recent episode of This Week in Startups:

    “This is now the race for the nuclear bomb, all right. This is the Manhattan Project.”

    We did it once. We can do it again.

    More on tech:

    How to Build a Drone Botnet for World Domination

    Is This the End of Manual Labor?

    Climb, Crawl, Fly, Swim: Jake Loosararian at the All-In Summit

    Save Money on Stuff I Use:

    Fundrise

    This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 with great returns.

    More on Fundrise in this post.

    If you decide to invest in Fundrise, you can use this link to get $100 in free bonus shares!

    Misfits Market

    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.

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

  • Test the Product!

    I usually help startups by introducing them to other investors. But lately, I’ve been working on a new way to help…

    It started when I got an e-mail from the founder of one of my companies. He asked the investors to test the product, a great SaaS tool.

    “Hmm, that’s unusual,” I thought. “Let’s give it a try.”

    I ran through the whole flow. It was a super impressive product, but I found a couple little glitches. I also had a few ideas on how to make it better.

    I wrote those up into a brief e-mail and sent it off. A few minutes later, I got a reply: “Added to the product roadmap.”

    That was quick!

    Fast forward about a month…

    Same founder messages me again. They’d added a ton of features, and he asked if I had time to re-test.

    I got you, pal!

    These guys have some amazing developers in-house. So why do they need me?

    Those developers already know exactly how to use the product. I don’t.

    In that respect, I’m a lot like their customers.

    You know everything about your product. You built it! But to your customers, it’s foreign and potentially confusing.

    Having a fresh set of eyes makes a big difference.

    I actually did a certain amount of product testing when I worked in medical software. I had to run through some complex workflows — everything from heart surgery to organ transplant.

    Any mistakes could have dire consequences.

    So, I learned how to test software carefully and thoroughly. I never thought that experience would come in handy for anything else. But lo and behold…

    I can’t commit to doing testing for every company. It depends on my schedule.

    But if a founder needs that fresh set of eyes, I love providing it.

    Testing the product also helps me from an investment perspective. The only way to truly understand what a startup is doing is to use their product.

    The better I understand what the company does, the more informed I’ll be when it’s time to place a follow-on bet.

    If you invest in startups, consider doing some testing for your companies. And if you’re a founder, get some use out of those money guys — put them to work!

    More on tech:

    I’m About to Close the World’s Tiniest Venture Fund

    Lessons From My 3 Most Challenged Investments

    Learning From My Top 3 Investments

    Save Money on Stuff I Use:

    Fundrise

    This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 with great returns.

    More on Fundrise in this post.

    If you decide to invest in Fundrise, you can use this link to get $100 in free bonus shares!

    Misfits Market

    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.

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

  • Inauguration Day

    “From this moment on, America’s decline is over.” Watching President Trump’s inauguration today, I felt an incredible sense of relief. I felt comfort and trust.

    But I also felt trepidation. “Will this work?”

    Our country faces huge problems right now. Fixing them will take enormous effort.

    We have to believe that we can do it.

    I was chatting with someone this weekend and she said, “Trump is a gamble.” I responded with one of my favorite quotes…

    “No gamble, no future.”

    I’m told they say that in Vietnam. It’s a motto we have to adopt.

    As I write this on the afternoon of Monday, January 20, 2025, our country is $36.2 trillion in debt. That’s growing by a trillion every 90 days.

    We are at the beginning of a debt spiral. We borrow to pay off existing debt, which drives up interest rates. Then we have to borrow even more to pay that interest.

    If we don’t do something right now, we will never get out of this spiral.

    I like Jason Calacanis’ suggestion of a 5% across the board cut, every year, for 4 years.

    We are also at the edge of World War III with Russia over Ukraine. If that conflict goes nuclear, it’s a war that no human being will survive.

    Frankly, I do not envy President Trump. I would not want to have to take on these problems.

    But he led us to peace and prosperity before, just a few short years ago. I’m confident he can do it again.

    Here’s to a great 4 years. Let’s Make America Great Again! 🇺🇸

    More from the blog:

    Three Priorities for the Trump Administration

    Why I’m Voting for Donald Trump

    114 Days

    Save Money on Stuff I Use:

    Fundrise

    This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 with great returns.

    More on Fundrise in this post.

    If you decide to invest in Fundrise, you can use this link to get $100 in free bonus shares!

    Misfits Market

    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.

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

  • How Elon Built the World’s Largest Computing Cluster in 122 Days

    I used the world’s largest computer cluster to make a picture of Donald Trump eating ramen. Good thing engineers worked day and night on this.

    But seriously, xAI’s Colossus computing cluster is an incredible sight. With 100,000 GPU’s, the cluster is 2-4x larger than anything else on earth.

    A computing cluster of this size should take years to stand up. Incredibly, the xAI team built the whole thing in just 122 days.

    How Elon and xAI pulled this off can teach us a lot about how to solve big problems.

    Go Big or Go Home

    How was Elon able to secure 100,000 NVIDIA GPU’s when the demand for these chips is so intense?

    No one knows for sure, but the scale of this project may have been a key factor. When you place a massive order from a supplier, you go to the front of the line.

    In a sense, building a huge cluster is easier than building a small one.

    Making a massive bet without regards to the odds seems to be Elon’s approach to life. As a young man playing poker with Max Levchin, he lost repeatedly. But he doubled down over and over until he won.

    That may not be an ideal poker strategy. But as an approach to life, it seems to be working for him!

    “How Can I Do It?”

    Most of us see an obstacle and say, “That means I can’t do it.” Elon sees an obstacle and asks himself, “How can I do it?”

    Power is a huge limiting factor for data centers. They need a ton of it, and with everyone building AI clusters, power is running short.

    Elon could’ve waited for years to secure a steady supply and get a million permits. But instead, he and his team came up with a creative solution: portable, methane powered gas turbines.

    These turbines use methane, a fossil fuel byproduct. Because they’re portable, they don’t need many permits.

    Despite concerns about pollution, portable methane gas turbines of this type appear to be very clean. Moreover, I expect that these turbines are a temporary solution until xAI finds a permanent power source.

    Wrap-Up

    The problems we face in our businesses are nowhere near as hard as those Elon and xAI faced when they built Colossus. If they can pull that off, what can we do?

    The key is to make an audacious goal. Then, instead of thinking of reasons why we can’t succeed, let’s start thinking of some reasons why we can!

    Have a great weekend, everyone!

    More on tech:

    Tesla FSD 13 vs. Manhattan Rush Hour

    Your First Cybercab Ride

    I’m About to Close the World’s Tiniest Venture Fund

    Save Money on Stuff I Use:

    Fundrise

    This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 with great returns.

    More on Fundrise in this post.

    If you decide to invest in Fundrise, you can use this link to get $100 in free bonus shares!

    Misfits Market

    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.

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

  • I’m About to Close the World’s Tiniest Venture Fund

    In April 2021, I started the world’s tiniest venture fund. In the next few months, I’m about to close “Fund 1” and open “Fund 2.”

    My goal for my startup investments is to learn and to make returns that beat the stock market. The best way to learn is with small bets.

    If you’re learning poker, you want to play at the penny table first. Same idea here.

    These bets are small, but I want to run this professionally. So I think of my investments as the world’s tiniest venture fund.

    Here’s how it works…

    How Fund 1 Works

    I need 35-40 primary investments in a seed/pre-seed fund like mine. That gives me enough diversification so that, if I’ve chosen well, I have a chance of hitting a unicorn.

    Most of the returns in venture come from unicorns. I will almost surely need to hit one for this experiment to work.

    If I invest about $140k, I can get into around 35 primary investments. Then, I want about the same amount for follow-on.

    In total, Fund 1 is $280,000.

    What Happens When I Close Fund 1

    So far, I have 33 primary investments. I plan to invest in 3 more companies for a total of 36. Then, I will close Fund 1 to new primary investments.

    From that point on, two things will happen:

    1. Fund 1 will only do follow-on investments in the most successful companies. I’ve already done a few of those and plan to do several more. This follow-on period will extend indefinitely, until I’ve deployed all the follow-on cash. That should take a further 2-3 years (a total of 6-7).
    2. New primary investments will come out of Fund 2. Fund 2 will work pretty similarly to Fund 1.

    I expect to close Fund 1 in the first half of this year. But it could be sooner or later. It depends on how many great startups I see.

    I will have taken around 4 years to do all the primary investments in Fund 1. That’s on the slow side. The average fund takes 2-3 years, and 5 is usually the limit.

    I’m in no rush. I want the best.

    How Fund 1 Is Doing

    Venture capital is a game of outliers. And already, several companies in Fund 1 have distinguished themselves.

    Here is the leaderboard so far, by annual revenue run rate:

    • $17 million
    • $12 million
    • $8 million
    • $7 million

    Overall, the fund is up 2.3%. This number is not very meaningful right now, since it’s all on paper. You couldn’t realize any of these gains if you tried.

    However, it shows some good progress. Most funds nearly 4 years in are in negative territory. Indeed, I expect this fund to go negative as well in the next few years before the big winners (hopefully) start to break out.

    It has helped that so far, only 2 companies have shut down. That’s pretty amazing given the early stage I’m investing at.

    But the most important thing to focus on is that revenue leaderboard. That shows which companies are beginning to break out. And that’s where the returns will be.

    Where Did This Money Come From?

    These funds are all my own cash. I do not accept any outside investors for Fund 1, nor will I for Fund 2.

    In the future, that may change. But first, I want to learn this game with my own capital, not someone else’s. I would not feel good about running a crazy experiment with someone else’s money.

    Wrap-Up

    I started investing in startups during COVID. I did it mostly because I was bored and curious about angel investing.

    It wasn’t really about making money. That said, these investments have to make money. Otherwise, I won’t be able to keep doing it.

    I committed to myself to do this for 10 years. Then, I’d see if I was any good at it.

    Now I’m almost 4 years in, and things are going well so far.

    There are no guarantees in life. But win or lose, it’s been a heck of a ride. I’ve learned a lot and met a ton of fascinating people.

    Here’s to meeting more!

    More on tech:

    How to Get Started Angel Investing

    Lessons From My 3 Most Challenged Investments

    Learning From My Top 3 Investments

    Save Money on Stuff I Use:

    Fundrise

    This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 with great returns.

    More on Fundrise in this post.

    If you decide to invest in Fundrise, you can use this link to get $100 in free bonus shares!

    Misfits Market

    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.

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

  • My Investment Process

    If you send me your company, what should you expect from me? Here’s how my investment process works…

    Qualification

    I focus on meeting companies with these characteristics:

    • Software business
    • Couple of paying customers
    • Team of multiple builder founders
    • Proper incorporation. (A Delaware C Corp is the right move — more on why here.)

    I qualify startups like this because I don’t want to waste anyone’s time. If the business is something I know nothing about (biotech, for example) or is incorporated in a way that is a dealbreaker for me, it doesn’t make sense to meet.

    When I see something interesting that meets those qualifications, I schedule a meeting, usually within a few days.

    Meeting

    When I meet with a founder, I like to do a Q&A. I’ve already reviewed the deck and any other materials before the meeting.

    My meetings are typically around 20 minutes, although we can go longer if need be. I want to get a basic idea of the vision for the company, the team, and the product.

    I never ask founders to meet multiple times. I’m a small check, and I don’t want to take up too much of their time.

    However, some founders ask me to meet with them more than once. They want to go over product updates, etc. I’ll often take that meeting.

    Decision Time

    My sweet spot is usually around $200-500k ARR, growing fast. I also like to see you closing enough funding to give you a minimum of 12 months runway.

    If you’re in that sweet spot, I can usually get you a decision within 24 hours after the meeting.

    If you’re not in that sweet spot yet, I will probably give you a “not yet.” It’s crucial to note that this is NOT a no.

    I met a great founder in mid-2023 whose company was just getting started. He really impressed me, but the startup was just too early stage for me.

    I kept in touch and at the end of 2024, I invested. He had grown the company a great deal, and it was time to place a bet.

    Check Size

    My first check is $5,000. I reserve $25,000 plus to go into the best companies, typically at Series A.

    That’s not a lot of money. But I am committed to giving you value beyond the cash.

    A while back, I met with a great SaaS founder. I introduced him to a VC firm that gave him an $800,000 term sheet.

    I’m not even an investor in that startup. I go even further for companies I have actually placed a bet on.

    Wrap-Up

    I want my process to be clear and transparent to every founder. Founders’ time is an incredibly scarce resource.

    If we’re a match, awesome! If not, we can keep in touch and we might be a great match later.

    Either way, you’ll know where you stand.

    More on tech:

    What To Do When a Company Fails

    Why It’s Easier to Raise $3 Million Than $300,000

    What Investors Ask Founders

    Save Money on Stuff I Use:

    Fundrise

    This platform lets me diversify my real estate investments so I’m not too exposed to any one market. I’ve invested since 2018 with great returns.

    More on Fundrise in this post.

    If you decide to invest in Fundrise, you can use this link to get $100 in free bonus shares!

    Misfits Market

    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.

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