Tremendous

An angel investor's take on life and business

  • Stop Talking So Much in Meetings: 4 Techniques from 1,000 Founder Calls

    I’ve done over 1000 founder meetings. I use 4 techniques in every call. Try them in your own meetings, and watch your results improve…

    1. Be well prepared. “So, remind me how we got connected?” Whenever someone starts a meeting this way, all the energy goes out of the conversation.

    You can’t have a great call if you don’t know who you’re talking to.

    I have an agent that does my prep for me. It goes through my inbox and searches the internet for information about the person. Then it collates all of this into a summary.

    I have pasted the skill.md file into this blog post. Feel free to steal it!

    2. Don’t talk too much. If you’re doing all the talking and you think the meeting’s going well, I guarantee you’re wrong.

    The other person is sitting there, smiling politely, wondering when this ear beating will end.

    I use Fathom to track how much I talk. Periodically during the meeting, it pops up a little window that says 10%, 40%, etc.

    My best meetings happen when I talk at most 40% of the time. When I see that creeping up toward 50% and beyond, I know to shut up.

    “Show up and throw up” is the worst sales technique there is. Every meeting should be a conversation.

    3. Let the silence do the work. When I ask a question, sometimes a founder doesn’t respond right away. I never jump in and try to answer it.

    Instead, I let the silence do the work.

    Give them time to think. Show them you really want to hear their answer.

    Yesterday, I met with an outstanding founder who has a stutter. Being quiet while he forms sentences was especially important.

    4. Repeat key points in your own words. “I’m going to put the vision for ABC Corp. into one sentence in my own words. Tell me where I’m wrong, and we’ll see if I understand.”

    If you’ve ever met with me, you know that’s one of the first things I say.

    Just because you think you understand doesn’t mean you do.

    Rephrase key points in your own words. Ask them to confirm.

    You’re making sure you fully understand. You’re also showing you really care about what they’re saying.

    That goes a long way to building a relationship!

    Wrap-Up

    Whether you’re an investor meeting founders, a founder pitching VCs, or anybody selling anything, you can use these 4 techniques.

    If you do them consistently, you will make more sales.

    Rookies “show up and throw up.” Veterans have a real conversation.

    Try using my 4 techniques in your next meeting. Then leave a comment and let me know how it went!

    More from the blog:

    38 Words Got This Founder on My Calendar — Here’s the Cold Email Formula That Wins

    Why Some Founders Raise Millions with a Text — And Others Can’t Get a Single Check: Traction vs. Track Record

    Fundraising Friction is Killing Your Round – Here’s How to Remove It

    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!

  • When It’s Okay for Investors to Add Zero Value

    When is it okay for an investor to add zero value? When the expectations are clear upfront.

    Setting Expectations At the First Meeting

    We investors love to crow about our value add. But not every investor needs to help startups.

    Just be clear from the first meeting what kind of investor you are.

    “You will never hear from me. If you message me, your email will go into the great beyond.”

    If a founder hears that and still takes your money, they know what to expect. They know you’re just cash.

    And that’s okay!

    Some founders actually prefer that. They don’t want to waste time with meddlesome investors.

    This is especially true for experienced founders. They don’t need much help.

    Why I Try to Help Founders

    Personally, I like to be involved with the startups I invest in.

    It’s fun! Just wiring money and waiting is boring.

    I also want to improve the odds of success for my investments. When I introduce them to VCs or retweet their posts, that can give them a little push.

    From day one, I make it clear that I’m available to help anytime, day or night. I give founders my cell number and encourage them to use it.

    But not every investor needs to be like me!

    Money Alone Is Enough

    We investors all think we have some unique value add. But let’s be honest: the main value we add is cash.

    An investor’s job is to invest.

    When founders contact us, they’re mostly interested in money. They may pretend otherwise to flatter us, but the truth is they need cash.

    Don’t feel that you have to add additional value.

    If you enjoy helping founders, by all means do so! But don’t claim you’re going to add value just to sound good.

    What’s Not Okay: Broken Promises

    Here’s what’s not okay: talking a big game about being helpful, then disappearing.

    Unfortunately, that’s what most investors do — even of some of the biggest names.

    I heard a story about one of the most famous early stage investors. I won’t say his name.

    This guy can take 3 months to respond to an e-mail.

    Ridiculous!

    An investor like that should just be honest: “I’m not going to help you or even reply. We will never speak again. Farewell.”

    Wrap-Up

    “We go the extra mile for our founders!”

    How many times have you heard that? How often has it turned out to be BS?

    Let’s be honest, folks: the minute they wire the money, most VCs have delivered 100% of their value.

    And that’s not a bad thing! But the expectations should be clear.

    If you say you’re going to help, do it. And if you’re not, be honest about that.

    More than any “value add,” founders need honesty.

    More from the blog:

    Don’t Overstaff Your Startup

    You Finally Closed Your Funding Round — Time to Panic?

    The Best Founders Take Time to Rest

    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!

  • Obscene Growth, 3x ARR: Why Investing Today Can Be Cheaper Than Ever

    Ridiculous growth. 3x ARR. I keep seeing this combo in today’s market. Here’s why…

    Why High Growth Companies Can Be Dirt Cheap

    It comes down to AI driving incredible growth.

    A hot startup goes out to raise. They sign a term sheet at 10-20x ARR.

    But funding rounds take months to close. In the meantime, the company grows like crazy.

    What was a deal at 10-20x becomes 3-4x ARR.

    Founders: Stick to the Deal

    If you’re a founder, here’s how to play this: just close the deal.

    Yes, it’s a bonanza for investors.

    But a deal is a deal. Honor your agreement.

    If you try to re-trade, you could lose the deal entirely.

    Worse yet, this will affect your reputation in the industry. Startupland is a small world.

    By the same token, if growth slows down after issuing a term sheet, investors should never retrade the terms.

    An Incredible Time to Be Investing

    For investors, this means the deals we’re doing today will be historic.

    No one has ever seen growth like this. And the multiples look like something out of the dotcom crash.

    It also means that if a company is growing really fast, we can afford to pay a higher multiple. That multiple is likely to compress significantly by the time we wire.

    Wrap-Up

    Investing today is so much better than when I started in 2021.

    Tourist VCs were doing deals in $10 million ARR startups at 100x revenues. Those companies were growing 3x year over year at best.

    Today, we do deals at a fraction of that multiple. These startups are growing like nothing in the history of business.

    I’m loading up on as many of these companies as I can. Good deals don’t last.

    More from the blog:

    38 Words Got This Founder on My Calendar — Here’s the Cold Email Formula That Wins

    I Looked at 21 Startups This Week. Only One Got a Check.

    Fundraising Friction is Killing Your Round – Here’s How to Remove It

    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!

  • Take These 3 Things Out of Your Pitch Right Now

    Here are 3 things I hate seeing in startup pitches…

    Letters of Intent

    Also known as Letters of Nothing! Whenever I hear a founder talking about letters of intent, it’s hard not to roll my eyes.

    These letters are not enforceable. Odds are you’ll never see the millions they promise.

    If you don’t have revenue, LOIs are not a valid substitute.

    I would rather just hear you say “we don’t have any revenue”. At least you don’t sound delusional.

    Advisors

    The most useless slide in a deck is the advisor slide. It’s always a bunch of guys in suits I’ve never heard of.

    The people who will make your company a success work full time at the company. Popping in for a couple hours a month isn’t going to do much for you.

    If you want to have a few advisors help you on the margins, that’s fine. But leave it out of your pitch.

    Awards

    “We won best startup at the Eastern Idaho Regional Startup Fair!”

    Good for you. But leave it out of your pitch.

    Investors want to back unicorns, not “award-winning startups.” Unless that award came with a check, you can stick it in a drawer and forget it.

    The real wins are in the marketplace: customers giving you money.

    Wrap-Up

    Whenever you mention LOIs, advisors, or awards in your pitch, you waste time.

    You tell me you don’t have anything better to sell. And worst of all, you tell me you don’t know what’s important.

    Stick to what matters: team, product, and customers. If you’re focused on what counts, you have the chance to build an incredible business.

    More from the blog:

    You Finally Closed Your Funding Round — Time to Panic?

    Why Some Founders Raise Millions with a Text — And Others Can’t Get a Single Check: Traction vs. Track Record

    38 Words Got This Founder on My Calendar — Here’s the Cold Email Formula That Wins

    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!

  • Request for Startups: Synthetic Diesel, Climate-Proof Coffee, and an Email Bot That Actually Sounds Like You

    Diesel is over $6 a gallon. Coffee is through the roof. AI slop emails chase me in my dreams. Each of these problems is an opportunity for a startup.

    Here are 3 types of startups I’m looking for now…

    Synthetic Diesel

    Diesel is $6.29 a gallon at the gas station near my house. That’s up a good $2 since the war with Iran began.

    I live in an urban area, so I don’t need a car. But since everything we buy arrives in a diesel truck, the price of diesel affects us all.

    What if we could create synthetic diesel in unlimited quantities? We could use crops like corn. Or maybe the synthetic diesel would come entirely from other chemicals.

    Several companies are working on synthetic diesel. The big hurdle is making synthetic for less than real diesel.

    If a startup can pull this off, it will be one of the world’s largest companies.

    Coffee for All Climates

    One of my favorite things in life is my morning coffee. When I take my first sip, all is right with the world.

    But have you noticed how expensive coffee is getting?

    A lot of it is because of heat and drought in Latin America. Coffee plants like moderate temperatures and substantial rain.

    But what if we could breed coffee plants that would grow in any climate? Genetic engineering techniques like CRISPR could help make plants resistant to drought and heat.

    Nestle is working on this, among other companies. But nothing is widely available yet.

    With the right type of plant, we could grow coffee right here in America. Your morning cup would cost a fraction of what it does today.

    An Email Drafting Tool That Actually Works

    When I’m drinking that morning coffee, I’m usually going through my email. Lately, AI has made that a lot easier.

    I used Grok to build a bot that drafts emails for me. I can use about half the drafts it generates, which saves me a ton of time.

    There many tools that claim to draft emails. But none of them worked for me. The responses didn’t make sense in context and didn’t sound like me.

    So instead, I built my own bot. I gave it examples of different categories of emails I receive and example responses.

    Most people don’t have the patience or skills to build their own email bot. We need a bot that will go through your inbox, categorize the different message type, and draft replies.

    A good email bot could go massively viral.

    Wrap-Up

    When I’m trying to dream up promising startups, I look at the problems I see every day. If we can fix them, someone will pay us!

    Diesel is at record highs. Coffee is right behind it. And AI means we’re getting more emails than ever.

    Solve these everyday problems, and you have a fantastic business.

    So if you’re building in one of these three areas, shoot me a message! My DMs are always open.

    More from the blog:

    Why Some Founders Raise Millions with a Text — And Others Can’t Get a Single Check: Traction vs. Track Record

    We’ve Hit Superintelligence in Coding and Math — Physics Is Next

    My Three Early Favorites in YC F26

    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!

  • Three Startup Ideas That Need to Die

    Here are 3 startup ideas that need to die…

    1. An app to find your friends and hang out. This is everyone’s first startup idea.

    It’s been tried a million times. Nobody wants it.

    When I want to see my friends, I just send them a text. That’s what most people do.

    We don’t want to be under surveillance 24/7. I don’t need my friends knowing that I’m sneaking donuts at Dunkin.

    Even Sam Altman built a version of this idea, called Loopt. Turns out OpenAI was a better idea.

    2. Event tech. I have seen every conceivable permutation. And I’ve passed on all of them.

    This is an incredibly crowded space. There are 20 ticketing platforms to choose from.

    Worse yet, there are no great outcomes in this area. Eventbrite was recently sold for $500 million.

    That’s not an exit that excites investors.

    3. Influencer marketing platforms. I’ve seen a ton of startups try to connect brands with influencers. None of them have become major businesses.

    One problem: big influencer deals are often done directly, without a platform.

    People have tried to crack this market for a decade. No one has succeeded.

    I don’t see any reason that’s going to change.

    Wrap-Up

    I hate all three of these categories.

    But feel free to prove me wrong! Maybe you can grow incredibly fast in one of them.

    Humility is an important part of investing.

    But if you want my advice, pick a market that isn’t littered with the carcasses of dead startups.

    Try something different. Something crazy.

    And let someone else build the 1000th event tech.

    More from the blog:

    Why You Can’t Get a Meeting with Investors — And What to Do About It

    You Finally Closed Your Funding Round — Time to Panic?

    Why Some Founders Raise Millions with a Text — And Others Can’t Get a Single Check: Traction vs. Track Record

    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!

  • Don’t Overstaff Your Startup

    “Our team of 12 just reached $10K ARR.” This is a huge red flag. Here’s why…

    Before you hit product-market fit, your company should be just the founders. That’s typically 2 to 4 people, all of whom own at least 10% of the company.

    You want this team to be at least half technical — ideally 100% technical.

    Why Are Companies Overstaffed?

    Startups often overstaff because the founders don’t have the necessary skills.

    They don’t know how to build product. They’re not comfortable doing sales.

    So they hire out for these jobs.

    This is the wrong way to build a company. You need a founding team with all the necessary skills to reach product-market fit.

    If your team doesn’t have those skills, you need to develop them, Or, you need to change who’s on the team.

    Too Many Mouths to Feed

    Say you have 12 employees. If you pay them $10,000 a month in total compensation, you’re looking at a wage bill of over $1.4 million a year.

    This is a ton of money for an early stage startup.

    Even if you hire in the developing world, you’re probably still paying a minimum of $3,000 a month. That’s an annual wage bill of over $400,000.

    Don’t take on liabilities like that unless you have to. The higher your burn, the more likely your company goes bust.

    Paying People to Scroll TikTok

    In an early-stage startup, there just isn’t enough work for a big group.

    When you only have a couple users, what will half a dozen engineers do? Why would you need a customer success department when you barely have any customers?

    You will be paying people to scroll TikTok.

    Don’t Build a Bureaucracy

    Big groups of people don’t just cost you money. They cost you time.

    It’s harder to coordinate 12 employees than 4 founders.

    Every decision will take more discussion. This is time you don’t have.

    The only way a tiny company like yours beats the big guys is by moving faster. The more people you have, the slower you move.

    A Tale of Two Startups: Chubbycorp and Leancorp

    Let’s compare two fictional startups: Chubbycorp and Leancorp.

    Chubbycorp has 3 founders, but they’re all “idea guys.”

    They don’t know how to build product. They don’t like doing sales.

    So they hire 6 engineers and 6 sales guys. Now they have a seven-figure annual wage bill.

    Meetings multiply. The company moves more and more slowly.

    And they keep losing sales to this annoying startup: Leancorp.

    Leancorp has just 4 people, all founders. They’re all deeply technical.

    Content with their equity, they’re taking minimal salaries. The company’s burn is close to zero.

    Leancorp has almost no meetings. They just ship product and sign customers.

    Who do you think is going to win?

    Wrap-Up

    Be Leancorp.

    Build a team of strong technical founders. Move fast. Avoid hiring until product-market fit.

    You’ll leave Chubbycorp in the dust. They’ll be running out of money, wondering what happened.

    And with any luck, you’ll be sending a big distribution to your first investor, Francis. 😉

    More from the blog:

    In the AI Era, Technical Founders Are Running the Table

    You Finally Closed Your Funding Round — Time to Panic?

    The Best Founders Take Time to Rest

    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!

  • I Looked at 21 Startups This Week. Only One Got a Check.

    I looked at 21 deals this week. Just one got a check. Here’s a look inside my dealflow…

    Competition for Funding Is Fierce

    In the last week, I’ve looked at 21 companies. I made one new investment, a follow-on into one of my most successful startups.

    Normally, it takes me a lot more than 21 deals to find a good investment. Sometimes it takes hundreds.

    Either way, your odds of getting a check from an investor are very small. It’s a fierce competition, and most companies don’t get funded.

    Pitch Investors that Write Checks at Your Stage

    Here’s why I passed on those 20 deals…

    Too late stage: 7

    Too early: 7

    Wrong geography: 2

    Vice: 1 (alcohol-related)

    No lead investor: 1

    Not a DE C Corp: 1

    Other: 1

    Most of the time, it was because the company isn’t at the stage I focus on: pre-seed and seed. If you want to drastically increase your hit rate, pitch people who invest at your stage.

    Money Is Concentrating Into a Handful of Companies

    I said no to a bunch of early-stage startups this week. The folks who got the check: a company that’s already very successful.

    This mirrors what’s happening in the market as a whole. Money is concentrating into a handful of extremely high-growth companies.

    That’s why it’s so important to hit break-even. You no longer have to rely on venture capital.

    Wrap-Up

    It’s very hard to get a check, even from a small investor like me.

    This is why you need to pitch a ton of investors. I recommend contacting 200 in order to raise a round.

    Be sure they invest in your stage, country and market. OpenVC is a great way to build this list and contact investors.

    Raising money isn’t easy. Nothing about running a startup is.

    But if you really believe in your mission, it’s worth it.

    More from the blog:

    Why Some Founders Raise Millions with a Text — And Others Can’t Get a Single Check: Traction vs. Track Record

    38 Words Got This Founder on My Calendar — Here’s the Cold Email Formula That Wins

    My Three Early Favorites in YC F26

    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!

    Wispr Flow

    I used this app every single day to dictate to my computer, I’m even dictating this text using Wispr Flow! It’s way better than Apple’s native dictation.

    My productivity is up about 25% since I started dictating rather than typing. I’m also less tired and stressed.

    Get a free month of Wispr Flow Pro here!

  • Ken Griffin Sees a Bubble. I See Dirt Cheap Big Tech Stocks.

    Ken Griffin says we’re “almost certainly” in an AI bubble. Meanwhile, Micron is trading at 12 times earnings. Google is at 16. Is Big Tech dirt cheap?

    Of the 50 largest tech companies in the world by market cap, 15 are trading at a PE ratio of 25 or less.

    PEs this low for high-quality companies are rare.

    If we look at the PE ratio for the Nasdaq 100, we see valuations trending down over the last two years. Overall, PE’s look historically normal, and well below the peak in late 2016.

    Zooming in on specific stocks, the deals get even better.

    From Memory to Hyperscalers, Cheap Stocks Abound

    The memory chip makers have multi-year contracts locking in a significant portion of revenue. And even if their profits fall, their PEs would still be reasonable.

    Let’s look at some stocks that are less cyclical: companies like Google, Amazon and Meta.

    All are trading for 16-22 times earnings. All are growing earnings in the 10-30% range yearly.

    That’s amazing growth at that scale. Buying into growth like that for such low multiples is a rare opportunity.

    Not Everything Is On Sale

    Not every major tech company is cheap.

    Apple is at 40 times earnings. Tesla is over 400! Investors are running toward hardware in hopes it will provide a moat from AI.

    The market is not rock bottom. But as a whole, prices are reasonable.

    Digging into specific stocks, there are some unusual bargains.

    Wrap-Up

    The AI trade has a long way to run. But as worries mount, many of the leading companies are surprisingly cheap.

    Alphabet or Meta could double without increasing earnings a cent. This would provide an enormous tailwind to markets.

    AI today reminds me of medical software when I joined the industry in 2005.

    “Am I too late?” I wondered.

    I had no idea how early I was. The market kept expanding at warp speed for a decade.

    It’s time to stop worrying and love the AI trade.

    More from the blog:

    Reusable Jet Interceptors, Cheap Missiles, and Car-Repair Robots: My Favorite YC F26 Startups

    I’ve Seen Thousands of Founder Pitches. These 5 Mistakes Keep Showing Up.

    Fundraising Friction is Killing Your Round – Here’s How to Remove It

    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!

  • Reusable Jet Interceptors, Cheap Missiles, and Car-Repair Robots: My Favorite YC F26 Startups

    A jet interceptor knocks a drone out of the sky. A robot mechanic fixes your car in minutes. These are just a few of the amazing startups in YC F26.

    Last month, I covered 3 awesome companies that were among the first F26 startups to launch. Since then, 89 more startups have unveiled their products.

    Here are three of my favorites…

    Keres: Reusable Jet Interceptors

    Why is SpaceX able to launch cargo for so much less than other providers? Because of its reusable rockets.

    Using a $4 million Patriot missile to intercept a $50,000 drone gets expensive. But what if we could reuse the drone interceptor?

    That’s what Keres is building. Their reusable jet interceptors destroy a drone and then come back to base, ready to destroy another.

    Founder Christopher Palazzolo comes from Boom Supersonic, the startup making a supersonic airplane. That’s the strong technical background I’m looking for!

    Polemos Industries

    Polemos is attacking the problem of expensive, scarce missiles in a different way: making them cheaper and easier to build.

    Polemos plans to build missiles on production lines that already exist. The missile system will connect to drones and find targets to destroy.

    Rodeo Robotics

    Cars are driving themselves. But we still do maintenance the old-fashioned way, with high-priced human technicians.

    What if a robot could maintain our cars for us?

    Rodeo Robotics is building robots to repair and maintain cars. The team comes from Applied Intuition, one of the top companies in vehicle autonomy.

    Self-driving cars are spreading across the US. Fleets of Waymos and Teslas are seeing heavy use and will need a ton of maintenance.

    Rodeo can automate a lot of that. They even have human technicians to handle the tasks the robots can’t do.

    By watching the human technicians, the robot learns more skills.

    I’d much rather use a robot than pay a human mechanic $150 an hour!

    Wrap-Up

    Four times a year, YC launches hundreds of startups into the world. If even one or two become a big success, that’s world-changing.

    I’m excited about these deeply technical teams attacking hard problems, like drone defense and robotics.

    Around 100 more startups will be launching in YC’s fall cohort. I can’t wait to see the amazing products they unveil!

    More from the blog:

    My Three Early Favorites in YC F26

    I’ve Seen Thousands of Founder Pitches. These 5 Mistakes Keep Showing Up.

    Fundraising Friction is Killing Your Round – Here’s How to Remove It

    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!