Tremendous

An angel investor's take on life and business

  • In the AI Era, Technical Founders Are Running the Table

    14 companies founded in the 2020’s have hit $500M ARR. 13/14 have a technical founder. This is why I back builders.

    Analyzing the Top Startups of the 2020’s

    Here is a list of every company founded in the 2020’s that has hit $500M ARR, along with the founder and CEO’s background:

    Only one non-technical founder makes the list: Brendan Foody. He studied Economics at Georgetown but dropped out to start Mercor.

    Brendan may be non-technical, but he has an exceptional background. Before Mercor, he was a Thiel Fellow. 

    Inside a Top Startup: My Investment in Micro1

    Take the example of Ali at Micro1, my most successful investment so far. Ali has degrees in Comp Sci from Berkeley and Stanford, two of the top programs.

    Because Ali is deeply technical, he knew what AI systems were capable of. He was able to build the right product at the right time.

    When the company was just getting off the ground, Ali could write a lot of the code himself. This surely saved a lot of money, ensuring survival until they hit product-market fit. 

    How This Data Informs My Investments

    I’m not likely to back a non-technical CEO. The data shows us technical founders are winning.

    A non-technical founder would need some exceptional accomplishments. Even then, he’d need at least one technical co-founder. 

    If we’re starting a pizzeria, somebody has to know how to make pizza! 

    Wrap-Up

    If you’re deeply technical with no business background, you should still consider starting a company. Technical founders have an amazing track record.

    If you’re non-technical, don’t give up! Amazing founders like Brendan show us it’s still possible to succeed.

    Just make sure you get some serious engineers around you. Together, you can build something great.

    More from the blog: 

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

    You Finally Closed Your Funding Round — Time to Panic?

    The Unsexy VC Skill That Actually Matters: Answering Your Emails

    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!

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

    28 founders asked me for a meeting — on a single Sunday! I can’t meet 28 people a day. Here’s how I decide who gets a meeting…

    How I Decide Which Founders to Meet

    To pick which founders I should meet, I look for the most viable startups. Here’s how I assess that:

    • Launched product
    • Builder founders
    • At least 3 paying customers
    • Located in a region I cover (US/Japan/Canada/UK/Ireland/Sweden/Australia/New Zealand)
    • Incorporated properly (Delaware C corp)

    If a startup checks those boxes, I’ll generally meet with them. If not, I’ll explain why they don’t meet my criteria and ask them to follow up if anything changes. 

    What to Do If You Can’t Get Meetings

    Are you struggling to get meetings? Go through my checklist and see if you meet the criteria.

    If you do, and you message investors that invest in your country and stage, you should get meetings.

    But if all you have is an idea, don’t expect to get on a VC’s calendar. 

    Everyone has ideas. If they met with everyone who has an idea, they’d never sleep!

    Wrap-Up

    Just because you can’t get a meeting right now doesn’t mean your company is doomed. 

    The company that doesn’t look strong right now could be a big winner in the future! 

    Get together a team of builders, launch a product, get a few customers. If you can do that, investors will be fighting to meet you.

    More from the blog:

    You Finally Closed Your Funding Round — Time to Panic?

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

    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!

  • The 3-Hour Wire: How Investors Should Close

    Some investors commit to a startup, then take forever to send the money. I wrapped up my biggest investment ever in just 3 hours and 14 minutes:

    11:14am: SAFE and wiring instructions received

    2:28pm: SAFE signed, wire sent

    Too Many Investors Leave Founders Hanging 

    I’ve seen investors take weeks or even months to wire. One investment of mine waited 2 months for $150,000 an investor promised. 

    This is one of the worst screwups an investor can make.

    If you don’t want to commit to a company, don’t! But once you’re committed, you need to follow through ASAP.

    How to Close An Investment Properly

    Take my latest check. It’s not that I did all my research in just 3 hours.

    I had already done my diligence and decided I wanted to put in a check. Once I had the documents, it was just a matter of going through them, signing, and setting up the wire. 

    There’s no reason this should take more than a few hours. 

    The Dirty Little Secret About Some VC’s: They’re Broke

    One reason investors take forever to send the money: they don’t have it.

    Some newer funds will commit to investments, then go try to raise the cash. This is a bait and switch that no investor should ever do to a founder.

    I once saw a European-based syndicate commit to lead a pre-seed round. But they didn’t have the money and never succeeded in raising it.

    They had to pull out, leaving the company wounded. 

    If you say you’re in, be in. It shouldn’t be contingent on raising the money later.

    If you’re a new investor looking to make a name for yourself, this is the exact wrong way to do it. 

    Practical Advice for Founders

    If you’re a founder, ask investors how long it takes them to sign and wire. Ask for specifics on their latest investment. 

    If they’re leading your round, you need to do even more diligence. Talk to several of the founders they’re invested in.

    Did this VC actually follow through in a timely manner?

    It’s a lot easier to do this diligence now than find out the hard way later. 

    Wrap-Up

    The best founders have tons of options. 

    If you have a good reputation, they might be willing to deal with you. If you don’t, you’ll get ghosted.

    So when you commit, follow through right away. No more than 24 hours.

    If you can do that, you have a shot at working with the best founders in the world.

    More from the blog:

    How to Build a Data Room for Your Startup

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

    Fundraising: The One Thing You Can’t Outsource

    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!

  • How a $10,000 Angel Can Help Close Your Round

    Two of my best startups are raising right now. I’m probably their smallest investor. I earn my keep by introducing them to multibillion dollar funds.

    Let’s take a look inside these two funding rounds…

    The Hot AI Infra Startup

    One of my recent investments is growing faster than anything I’ve ever seen. Now, they’re raising a big new round.

    So far, I’ve introduced them to 11 funds. Three of those have over $1 billion under management.

    It’s been easy to get them meetings! It helps when I have something fantastic to sell. 

    Since this company is already big, I avoided investors that only do early stage. This way, the meetings are more likely to convert.

    I think one of those firms will give them a term sheet. Even if not, the company should pull in lots of big follow-on checks. 

    The Deep Tech Wizard

    I invested in an amazing deep tech company last year. The founder has an incredible engineering background.

    Now, he’s ready to raise a seed round. 

    I’ve been careful to only pick investors experienced with deep tech. If I introduce him to a bunch of SaaS guys, it’s going nowhere.

    I’ve introduced him to 9 investors for this round, including two funds with over $1 billion AUM. 

    I’ve emphasized his exceptional background to every VC I contact. That’s what will persuade investors here.

    I helped him raise $500,000 of his pre-seed last year. I expect to help bring in millions this time.

    Wrap-Up

    A guy writing $10,000 checks has to earn his way into great deals. I do that by helping founders raise money.

    I meet a new VC or two just about every week. I write down what kind of deals they like. 

    Then, I contact them when I have the perfect startup for them.

    If you need help closing your round, look for some great angels! Ask them for concrete examples of how they’ve helped other startups.

    If you bring on the right partners, your round will oversubscribe before you know it.

    More from the blog:

    Why Early Stage Startups Don’t Need Multiple Products

    My Three Early Favorites in YC F26

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

    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!

  • The Unsexy VC Skill That Actually Matters: Answering Your Emails

    Grok just pulled my median email response time this week: 8.3 hours. Some VC’s take 3 weeks. When I see that, I think, “Not gonna make it.”

    I can’t compete with huge VC’s on check size. So I’m developing a different edge: customer service.

    8 hours is solid, but I’d like to get that down. My email agent that drafts replies should help!

    I’m balancing responsiveness with avoiding distraction. If I check my email constantly, I can never do focused work.

    So I follow the Tim Ferriss rule: 2 passes through the inbox per day. Sometimes, I stretch that to 3 or 4…don’t tell Tim. 😉 

    I keep notifications for new messages off. I learned that trick at an all-staff meeting with Judy Faulkner, the founder of medical software giant Epic and my first employer.

    “If you want one piece of practical advice, go into your Outlook settings. Find the one that pops up email notifications and turn it off.”

    If Judy can run a $100 billion company that way, it should work for me too!

    Sometimes, one of my founders needs a faster response. So I give them all my phone number.

    I usually respond to texts within minutes.

    The most successful investors respond quickly. The laggards take their sweet time.

    I want to win in this business. And winning comes down to nailing the simple stuff, like answering messages.

    Now, I’m off to clean out my inbox…

    More from the blog:

    Meet My Latest Investment: Brick

    Why Early Stage Startups Don’t Need Multiple Products

    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!

  • The 3 Companies Apple Should Buy Now

    Apple hasn’t released a compelling new product since the iPhone in 2007. It’s time to take radical action. 

    Here are 3 startups John Ternus should acquire today…

    Instinct

    Siri sucks. Apple Intelligence does nothing.

    It’s time for John Ternus to buy Instinct.

    Instinct is everything Siri isn’t. It’s an assistant that’s actually helpful and easy to use.

    On Sunday night, I booked a flight home for Christmas that Instinct found for me. It cost about half what I was expecting to pay!

    Instinct is valued at $10 billion today. For $20-50 billion, Apple could easily pick it up. 

    In addition to a great product, Apple gets one of the strongest teams in AI. Ternus could appoint Instinct founder Noah Shinn as the head of Apple AI, like Zuck did with Alexandr Wang. 

    At under 1% of Apple’s market cap, this deal is a no brainer. 

    Wispr Flow

    I have a sore throat today. So for the first time in forever, I’m actually typing instead of using Wispr Flow.

    It’s so painful! I resent every key stroke. 😂

    But you know what sucks? When I turn on Wispr Flow, I have to switch between the Wispr app and the app I’m writing in.

    Wispr Flow can’t control this. It’s an Apple security thing.

    Why doesn’t Apple just buy Wispr Flow?

    Apple could integrate it and replace the garbage dictation tool they have now. This would make every iPhone way more valuable. 

    Wispr Flow is valued at $2 billion. For $5 billion, Apple could swallow it whole. That’s just 0.1% of market cap.

    Figure

    My last acquisition idea for Apple is a wildcard…a humanoid robot.

    Of all the humanoids out there, Figure is the most advanced. They’ve done demos in 30 houses — something I’ve never seen from any other robot.

    Apple could buy Figure for around $100 billion, a healthy premium to its current $40 billion valuation. Figure becomes the new iPhone — the key product that makes the company.

    Imagine an Apple robot in every house. It cooks, cleans, and answers questions. 

    Apple leases us the robot for $500 a month. This could be the biggest business in the world.

    And at 2% of Apple’s $5 trillion market cap, why not?

    Wrap-Up

    Three checks. About $150 billion — just 3% of Apple’s market cap.

    Instinct becomes your assistant. Wispr Flow is the interface. Figure takes care your home. 

    Or, Apple can just keep selling iPhones and wait to be disrupted.

    Your move, John.

    P.S. Kudos to This Week in Startups for giving me the idea for this post. See the 5 companies Jason and Lon think Apple should buy here. 

    More from the blog: 

    Request for Startups: Low Cost Missiles, Easy Calcium Scans, and Pill Robots

    The Best Founders Take Time to Rest

    You Finally Closed Your Funding Round — Time to Panic?

    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!

  • How I Get Allocation in the Hottest Startups

    I’m about to write my biggest angel check ever. I’ll be investing in the fastest growing startup I’ve ever seen. 

    How do I get access? Simple: be helpful.

    Helping A Top Startup Raise Their Next Round

    We’ll call this company ABC Corp. I invested in ABC’s seed round, when they were doing $1 million ARR. 

    ABC has scaled to $100 million ARR faster than any company in history. So naturally, I want to invest more!

    And I’m in luck…they’re about to raise a huge new round.

    I’ve introduced ABC to nine different venture firms to fill out their round. After I made those intros, I sent the founder a little note. 

    “Would love to invest $50k in the new round!”

    It’s the biggest check I’ve ever written, but it’s still tiny. In terms of dollars and cents, the founder has zero reason to accept this money.

    But he’s taking it! We should be signing the papers soon.

    I got this access because I worked hard to help him. And he knows I can help more in the future. 

    Being an Early Cheerleader Pays Dividends

    Intros aren’t the only way to help a startup. Sometimes just being a cheerleader makes a real difference.

    Take XYZ Corp, another of my most successful investments. I made sure to give a very positive, specific response to every update they’ve ever sent.

    The founder put those responses into the company Slack. It hyped everyone up! 

    People see XYZ today and they only see success. But it took a ton of hard work.

    When you’re grinding away with no guarantee it’ll pay off, having someone to cheer you on helps. 

    I also helped by being one of the first testers of their new product. I was blown away by how powerful it was!

    Helping with testing and moral support was fun. It also gave me unusual access.

    Little old Francis was able to slide $45,000 into their recent funding round, which was dominated by huge venture firms.

    Wrap-Up

    If you make just a slight effort to help a founder, they’ll remember you.

    Most investors do nothing. So it’s easy to stand out!

    But helping founders goes way beyond money.

    It’s a very long road to IPO. Most companies never make it.

    We need to have some fun along the way! Helping a founder is one of the best ways to do that.

    It just makes me feel all warm and gooey inside.

    More from the blog: 

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

    The Best Founders Take Time to Rest

    Fundraising: The One Thing You Can’t Outsource

    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!

  • How to Build a Data Room for Your Startup

    One of my startups is about to raise a big Series A. But first, they have to build their data room. Here’s how it works…

    Your data room should include everything a VC needs for diligence. Here are some items to include: 

    • Deck
    • Certificate of Incorporation and Bylaws 
    • One pager and/or deal memo 
    • Cap table
    • Prior SAFEs and term sheets
    • IP assignments 
    • Founder share agreements
    • P&L
    • Financial projections
    • Board minutes (if you have a board)
    • Bank statements
    • Copies of customer contracts
    • Patent documentation

    These documents help VCs verify that your company is legit, your customers are real, and the money in the bank actually exists. 

    Without this info, most VCs won’t write a check. So before you get a term sheet, get your data room together. 

    Organize each type of document in a folder — all the contracts go in a “Customer Contracts” folder, for example. Tools like Google Drive, Docsend, or Agree.com are great for sharing these documents. 

    You may already have some of these documents in your Gmail or Google Drive. Try using an LLM connected to those tools to gather the info you need. 

    Digging up your Certificate of Incorporation isn’t anyone’s idea of a good time. But if you want to raise big money, it’s a must. 

    Once your data room is set up, you’ll be ready to close that multimillion-dollar check.

    More from the blog: 

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

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

    Fundraising: The One Thing You Can’t Outsource

    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 Wire for an SPV Until You Ask These Two Questions

    Some of my best investments have come through SPVs. But SPV’s can also get you burned. Here’s how to invest in SPVs the right way…

    (Note: I am not a lawyer. If you need specific legal advice on an SPV, contact an attorney.)

    A Special Purpose Vehicle (SPV) is a company that gathers a bunch of checks from investors to invest in a company. Typically, SPVs are a Delaware LLC. 

    SPV’s have a lead, usually a more experienced investor who is managing the investment.

    Before you invest a dime in an SPV, ask the lead these two questions:

    1. Is the SPV buying stock directly from the company? Buying stock straight from the company is critical.

      Many companies restrict transfer of shares. Right of First Refusal and other restrictions can invalidate the transfer of shares from another investor into an SPV.

      This happened recently to some Anthropic investors. Just as they were probably shopping for beach houses, they found out that their investment was ruled invalid.

      They won’t make a dime.
    2. Does the SPV sit directly on the cap table? If you’re direct on the cap table (list of company owners), your SPV definitely owns part of the company. If you’re not direct on the cap table, your SPV may just own shares in another SPV.

      Did that SPV buy the shares properly? Who knows?

      This is why I never touch layered SPVs. 

    Wrap-Up

    SPVs are a great way for smaller angels like me to get access to awesome startups.

    But if we don’t handle things correctly, the purchase can be overruled. Our gains vaporize before our eyes. 

    Don’t let that happen to you. 

    These little details seem wonky. But when a company becomes a huge success and there’s millions of dollars at stake, they make all the difference.

    More from the blog:

    How My Teeny Tiny Venture Fund Is Beating Almost Everyone

    Meet My Latest Investment: Brick

    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!

  • Who Should I Vote For? I Texted Instinct to Find Out.

    I opened my ballot this week. Half the names, I didn’t recognize. Instead of Googling them, I texted Instinct a picture of my ballot.

    Maybe you’ve used Instinct to book flights or manage your calendar. But I may be the first person to use it to help me vote.

    Here’s how it works…

    Instinct: My Political Researcher

    I took a picture of the ballot and sent it to Instinct. I told Instinct to fill me in on the positions of each candidate, focusing on AI, public safety, and immigration. Those are the issues that really matter to me. 

    With just these basic instructions, Instinct produced an incredible report. In only about two minutes, all the info was right in my Gmail. 

    Senate: Booker vs. Murphy

    Senator Booker has opposed new funding for ICE. Instinct’s info is accurate — I verified it on Booker’s website.

    That’s a dealbreaker for me. We need to get illegal criminals out of this country.

    Republican Justin Murphy, on the other hand, called for an end to sanctuary cities and sending the U.S. military to the southern border. 

    I’m going with Murphy!

    House: Menendez vs. Everyone

    Rep. Rob Menendez is running for his 3rd term here in Hudson County. 

    Menendez wants the power for data centers to be 75% renewable by 2035, which is likely impossible. I verified this on his website.

    This means no new data centers and losing the AI race to China.

    He also wants to abolish ICE. This guy is the Jersey AOC!

    No thanks.

    But there’s no Republican running. So whom should I vote for?

    Da’Shone Hughey’s campaign is all about AI. And unlike most politicians, he’s not bashing the technology right before the election in a cheap ploy for votes. 

    Hughey advocates AI education so kids can take advantage of this revolutionary new technology. That’s the energy I want to see in the House. 

    Wrap-Up

    I’m giving Instinct an A+!

    Every bit of information that Instinct gave me was accurate. I also loved the highly readable, bulleted format.

    Until recently, I had only ever used Instinct to find cheap flights. But lately, I’ve been offloading more tasks to this amazing tool. 

    It’s so nice having a genius that lives in your iMessage! If you haven’t tried Instinct, take a few minutes right now and give it a go!

    More from the blog:

    Was the Iran War a Mistake? And What Do We Do Now?

    Why German Industry Is Failing

    Request for Startups: Removable Brain-Computer Interfaces, Chatroulette for Pets, and Doggie MRI’s

    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!