Tremendous

An angel investor's take on life and business

  • Tasklet: The Easiest Agent Builder I’ve Ever Used

    Tasklet was one of the hottest companies in YC P26. This morning, I used it to build an agent that preps me for my founder meetings. The hype is justified!

    Automating One of My Most Annoying Tasks: Meeting Prep

    Digging through emails to find information on the folks I’m meeting is an annoying task. 

    Where did that message go? How many customers did they have?

    I want to see all the information in one place. This lets me focus on actually talking to the founder.

    I built an automation to do this in Grok Projects. It works okay, but sometimes misses important information.

    Can Tasklet do better? 

    Building My First Tasklet Agent

    Tasklet has a very simple interface. You just type in a prompt, like ChatGPT.

    Tasklet whips up an agent to follow your instructions. You don’t need to write a single line of code.

    I told Tasklet to look through my Google Calendar and Gmail and prep me for each day’s meetings. I told it to use info from the open internet to supplement its research.

    I had it send a message to my Gmail with the information at 7:00 am each day. I also had it send a test message now.

    The Moment of Truth — Does It Actually Work?

    I’ve got three meetings on Monday. Let’s see how Tasklet did…

    For my first meeting, Tasklet had a lot of emails to go on. It collated them beautifully. 

    It would have taken me at least 20 minutes to do it this well. Tasklet did it in seconds.

    For my second call, Tasklet wasn’t able to find much info about the founders. I thought Tasklet screwed up.

    But when I Googled the founders myself, I couldn’t find anything either!

    Turns out, Tasklet was working just fine. Sometimes, there’s only so much data out there.

    My final meeting was the best test…

    Tasklet had a couple emails to go on, but not much more. Still, it summarized my conversations with the founder in a very readable format.

    Verdict: Tasklet Is the Real Deal

    My days of getting frustrated searching through emails are over! 

    What struck me most about Tasklet is how easy it is to use. It isn’t any different than typing a prompt into ChatGPT or Grok. Tasklet handles the API connections and task scheduling. 

    Best of all, it formats its outputs beautifully. They’re very easy to read. 

    I’ve tried a couple of different agent builders. Tasklet is definitely the best I’ve seen.

    Will the Base Models Win the Agent Race?

    As a user, Tasklet is fantastic. But I wondered: is this something foundational models are going to do soon?

    You can already build agents with tools like Claude or Grok. They don’t work as well as Tasklet does. With Grok for example, I have to prompt and re-prompt, being very specific. 

    But with the enormous resources of the AI labs, I expect them to catch up.

    Agent builders is a brutally competitive market. But whoever wins, users like me benefit. 

    Wrap-Up

    Tasklet is a great product!

    My new agent makes sure I’m well prepared for meetings. No more frantic searching and scribbling. 

    If you’re a intimidated by the idea of building an agent, don’t be! If you can type, you can build an agent on Tasklet.

    AI is automating the frustrating parts of our jobs. This frees us up to do the fun stuff!

    Give Tasklet a shot and build something to make your life easier.

    Have a great weekend everybody!

    More on tech: 

    The Simple Automations That Let Me Meet More Awesome Founders

    My Top 3 YC S26 Startups So Far: Robot Maids, AI Health Insurance, and AI-Proof Security

    China’s GLM 5.2: The Most Powerful Open-Source Model Yet — But Does It Deliver in Real Life?

    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!

  • I Looked at 431 Startups to Write 1 Check — Here’s What Actually Gets Founders Funded

    Here’s how my latest deal came together: 431 companies, 74 meetings, 1 check. Raising money is brutally competitive. Here’s how to win…

    A Look Inside My Deal Funnel

    I wired for a new investment on June 29th. To find it, I looked at over 400 companies and did 74 Zoom meetings. 

    Finding great investments is not easy. Neither is raising money for your startup.

    Founders start thousands of startups in America every year. Only around half successfully raise a seed round.

    Bottom line: there’s too many startups chasing too little money. 

    Investors Are Dying to Eliminate You

    Investors are looking for a reason to eliminate you. They say no to hundreds of people for every check they write.

    Founders not builders? Pass.

    No revenue? Pass.

    No product built? Pass.

    Any obvious problem gets you disqualified instantly. 

    It’s harsh, I know! But that’s the way the market works.

    Before You Raise, Ask Yourself “Am I Fundable?”

    Don’t get disqualified right off the bat. Before you go out to raise, make sure you’re fundable.

    Do you have these 3 key elements?

    1. Team of builder founders
    2. Launched product
    3. Couple of customers

    If you have those 3 things, you’re ahead of 90% of startups. You’re going to get meetings, and you should grab at least a few checks.

    Putting Your Fundraise on Pause 

    Not getting anywhere with your fundraise?

    Put it on pause. Go out and sign three more customers.

    You don’t need funding for that. You just need to message leads, show your value proposition, and close them.

    Then, try raising again. Watch how much easier it gets.

    Wrap-Up

    To raise that round of funding, you’ve got to beat hundreds of people. 

    Be undeniable.

    Assemble a team of builders. Launch a product. Get paying customers. 

    With those 3 elements in place, you can start to bank some real cash.

    More on tech: 

    What Actually Counts as Traction When Raising Money

    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!

    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!

  • What Actually Counts as Traction When Raising Money

    “Get back to us when you have more traction.” Bet you’ve heard that before! But what the heck is “traction,” anyway? 

    Traction is evidence your company is succeeding. 

    Traction comes in many forms. Some types of evidence are more persuasive than others.

    Here are 6 common types of traction, from most compelling to least…

    1. Recurring Revenue

    This is the gold standard.

    Top-tier seed stage deals today usually have between $500,000 ARR and $1.5 million ARR. That’s a lot higher than when I started doing this. A couple of years ago, $200,000 would have been quite impressive.

    But everything is accelerating with AI. Like it or not, standards are going up.

    2. Paid Pilots

    This is still real money. But it’s valued lower than recurring contracts because pilots typically end after a few months.

    Still, paid pilots are a lot better than no revenue at all! Just be clear that they’re pilots, not normal contracts.

    A couple of paid pilots could get you into an accelerator. You might even be able to raise a pre-seed round. 

    But a full seed round isn’t likely unless you have a killer track record 

    3. Unpaid Users

    This is very relevant for consumer startups. For everyone else, it doesn’t matter.

    If you’re building a new consumer social app, monthly active users and retention are going to be key metrics. But if you’re building a SaaS app, paying customers are what count. 

    4. Launched Product

    Maybe you don’t have any revenue yet. But just launching a product puts you above most startups.

    A launched product may be enough to get you into an accelerator. But a product alone probably isn’t enough to raise a full funding round.

    5. Prototype

    A prototype and a strong team in place is usually enough to raise a seed round for a deep tech startup. Last summer, I invested in an awesome robotics startup with just a prototype. 

    For software startups, the bar is higher. You probably need to launch a product and get a few customers before you can raise money.

    6. Team in Place

    You don’t have any revenue. Your product isn’t finished.

    Do you at least have a team of builders in place?

    That’s a form of traction. Strong builders working full-time on the startup is one of the key things I look for.

    Having a good team in place could get you into an accelerator. But unless you have an incredible track record, you’re probably too early for a full funding round. 

    I’ve done 42 investments. I’ve never written a check without at least a prototype. 

    Wrap-Up

    Honestly assess what traction your startup has today. 

    Do you have several hundred thousand in ARR? You might be ready for a seed round.

    Do you have a solid team of builders but no product yet? Try an accelerator.

    Being realistic about traction will save you months spinning your wheels. Put that time into building product and getting more customers.

    When customers are flocking to you, raising money is a lot easier. 

    More on tech: 

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

    From Cold DM to Wire in 5 Days: Why I Move Fast on Great Startups

    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!

    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!

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

    Some founders raise millions with a single text. You’re struggling to get one check. The reason? It comes down to traction or track record…

    Track Record

    We’ve all heard crazy stories of founders raising millions in a weekend without even a deck. Behind those headlines, you’ll usually find a founder with an incredible track record.

    Maybe they sold their last company for $500 million. Maybe they were an early employee of a top startup.

    Last year, I invested in two founders who had co-founded billion dollar companies in the past. Founders like that go to the top of any investor’s list. 

    Sometimes, track record comes in unexpected places. 

    Demis Hassabis, the founder of DeepMind, was the second ranked chess player in the world as a teenager. This isn’t an accomplishment in business, but it still shows exceptional ability.

    Traction

    So what about the other 99% of founders? To raise money, you need to show real traction. 

    Think $500k-$1M ARR in the first 1-2 years. Founders with traction like that can raise a multimillion dollar seed round. 

    Traction looks different for different sectors. 

    In deep tech, a good prototype and a strong team can be enough. For consumer social, investors are looking more for user numbers than revenue.

    Wrap-Up

    Traction and track record are two sides of the same coin. 

    Track record proves you’ve won before. Traction proves you’re winning now.

    I’ve bet on unknown entrepreneurs with incredible traction many times. Some of them have become huge wins.

    There’s nothing wrong with being unknown. You just need to bring more to the table.

    If you’ve racked up huge wins in the past, let investors know! If not, go all out to show explosive growth in the company you’re building now.

    Show you’re extraordinary, and investors will start chasing you.

    More on tech: 

    You’ve Got Your First Customer. Now, How Do You Raise Money?

    From Cold DM to Wire in 5 Days: Why I Move Fast on Great Startups

    Is Y Combinator — Gasp! — Actually a Bargain Now?

    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!

  • The Simple Automations That Let Me Meet More Awesome Founders

    I want to meet as many awesome founders as I can. So I’m automating the busywork. Here are the automations I’ve got running my investment business…

    Summarizing Decks

    I built a great little tool in Grok Projects to summarize decks in the exact format I like:

    • Vision in one simple sentence
    • Team
    • Traction 

    Instead of paging through a 40-slide deck, Grok finds this info in a few seconds. 

    Grok Projects are great. They’re basically an elaborate, saved prompt. But they work a lot like an agent. 

    If you haven’t experimented with them, I really recommend it. 

    Meeting Prep

    My volume of meetings was getting heavy in June. So I built another Grok Project to prep me for my whole day. 

    I connected this project to my Gmail so it can see all my messages with each founder. It pulls info on each company’s team and traction. It even gives me some great ideas of questions to ask. 

    Making the prep work easier lets me focus on the actual meetings!

    Wispr Flow Snippets

    Do you find yourself saying the same thing over and over to different people? I know I do.

    So I built some wonderful Wispr Flow Snippets to make it easy.

    Snippets are saved blocks of text you can trigger with a single word or phrase. I have Snippets asking founders to send their deck to my Gmail, Snippets explaining I only invest in Delaware C corps, and a lot more.

    This lets me get through my messages in half the time.

    Fathom Video Recording and Note Taking

    I used to scribble like crazy during meetings. But for the last year, I’ve been using Fathom instead.

    I’ve tried every meeting note tool, and Fathom is by far the best. It takes notes, generates a transcript, and even records the video of the entire meeting.

    Fathom frees me to actually have a conversation. I still take a couple of notes on paper for key points. 

    When I’m researching a company more deeply, I’ll re-watch the whole meeting. 

    Wrap-Up

    Every one of these automations is incredibly simple. But put them together, and I’ve sped up every element of my investing.

    Messaging, reading decks, prepping for meetings, documenting meetings — everything is moving faster. I’m planning to add more complex automations over time. 

    When my entire business runs faster, I can meet more great founders. It only takes one Travis Kalanick or Brian Chesky to change everything. 

    What automations are you using that I should try? Leave a comment and let me know!

    More on tech: 

    My Top 3 YC S26 Startups So Far: Robot Maids, AI Health Insurance, and AI-Proof Security

    From Cold DM to Wire in 5 Days: Why I Move Fast on Great Startups

    You’ve Got Your First Customer. Now, How Do You Raise Money?

    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!

  • My Top 3 YC S26 Startups So Far: Robot Maids, AI Health Insurance, and AI-Proof Security

    YC S26 kicked off last week. 56 startups have already launched. Here are my top 3 so far, from robot maids to cheaper healthcare…

    Prescience

    Just this morning, my Christian health share emailed me. My discount for staying fit? Gone. 

    Traditional insurance is even worse. Premiums through the roof, no increase in quality. 

    Prescience is fixing this mess. 

    Prescience runs employee-funded health plans. They use AI to prevent illness and lower cost.

    Prescience pulls data from wearables, gets you doctor visits same-day, and even prescribes GLP-1’s proactively.

    If this company succeeds, the upside is unlimited.

    Nori Robotics

    What if you could buy a robot maid for $1,300? That’s the vision for Nori Robotics.

    These are robots on wheels, rather than legs. On my recent trip to Tokyo, wheeled robots brought my breakfast at my favorite diner. Wheels are stable and practical.

    Best of all, when you teach Nori a new skill like pouring a drink, that skill becomes available to everyone.

    Rock-bottom price. Network effects. I love everything about this business.

    Nebula Security

    Ever since the Anthropic Mythos announcement, the technology industry has been terrified of hackers using AI to break into their systems. Nebula Security may be the company to stop it.

    Founder Eten Zou and the team recently found a critical exploit of Android. These guys have serious cybersecurity chops.

    As AI finds one security hole after another, there will be a mad race to patch them. Nebula is the right company at the right time.

    Wrap-Up

    I’ve got cold messages out to all three of these startups. I’m itching to learn more about what they’re doing! 

    We can whine about YC’s valuations. But who else is backing so many ambitious companies in so many areas? 

    I’m excited to see more awesome S26 startups launch. I just might find my next investment…

    There will be no blog tomorrow. Have a wonderful July 4th and Happy 250th Birthday, America! 🇺🇸 

    More from the blog:

    You’ve Got Your First Customer. Now, How Do You Raise Money?

    Is Y Combinator — Gasp! — Actually a Bargain Now?

    From Cold DM to Wire in 5 Days: Why I Move Fast on Great Startups

    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!

  • From Cold DM to Wire in 5 Days: Why I Move Fast on Great Startups

    An amazing founder DM’ed me last week. I knew this deal wouldn’t last. Here’s the exact timeline — from cold X message to wire transfer in just five days…

    Tracking a Recent Investment, Minute by Minute

    Tuesday, June 23:

    1:42pm: Cold X message received

    4:49pm: I reply and ask for Calendly link

    10:22pm: Calendly link arrives

    11:00pm: I book first open slot

    Wednesday, June 24:

    10:30am: Meet with founder, promise a decision by EOD Thursday

    Thursday, June 25:

    3:47pm: I request allocation

    4:17pm: Founder confirms allocation received

    Saturday, June 27:

    2:30pm: Docs and wiring instructions received

    Sunday, June 28:

    5:24pm: Docs signed, wire transfer initiated

    Why Speed Is Critical for Investors

    I’ve been at this for five years now. I know what I’m looking for.

    When I see it, I move fast.

    Some investors take 3 weeks to respond to an e-mail. At that point, you’re not competitive.

    Is a great founder going to wait 3 weeks? By that time, the round will be full.

    But What About Due Diligence? 

    Diligence still matters. I looked into this startup quite a bit, reading reviews, digging into team backgrounds, etc. 

    But for a small, early stage check, diligence can’t drag on forever. 

    When I see a great deal, I work late into the night doing diligence. Then, I sleep on it.

    That’s a trick I learned from Hetty Green, the “Witch of Wall Street”. She never made an investment without sleeping on it first. 

    By the next day, I have an answer.

    Wrap-Up

    Founders are used to hearing “no.” What’s worse is hearing nothing. 

    If I’m not ready to invest, I give a quick “no” or “not yet”. I don’t want to waste their time. 

    But when that rare deal makes my heart race, I’m not waiting around.

    More on tech: 

    You’ve Got Your First Customer. Now, How Do You Raise Money?

    Is Y Combinator — Gasp! — Actually a Bargain Now?

    I Left $157,000 on the Table: How I Missed a Great Investment

    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!

  • Is Y Combinator — Gasp! — Actually a Bargain Now?

    We all love to whine about YC valuations. But lately, YC has quietly become one of the best deals for investors…

    Getting More for Your Money

    When I was meeting YC companies 2-3 years ago, this is what the best ones looked like:

    • $100k ARR
    • $20-25M valuation (200x to 250x ARR)

    Here’s what I’m seeing now in the top startups:

    • $1-3M ARR
    • $30-40M valuation (10-40x ARR)

    The price is up a little. But traction has exploded, and revenue mutliple has dropped around 90%.

    Why I’m Looking More Closely at YC

    You’re paying a little more, but getting a lot more in return. This makes investing in YC a better value than it’s ever been.

    I’ve made a bet in each of the last two batches. Given the stronger value proposition, I’m going to be looking at future batches more closely.

    When I Can’t Make the Numbers Work

    There are still two types of deals I avoid, whether from YC or anywhere else:

    • < $200k ARR, $25-40M valuation (too early)
    • White hot startups raising at $200-500M valuations (not enough upside)

    Angel investing is a business of outliers. So naturally, there are exceptions: a startup building in an area I’m obsessed with, or a founder with an incredible track record.

    Why Are These Startup Growing So Fast?

    How the heck have startups gone from $100K ARR to millions in the same short program? 

    You guessed it: AI.

    The best startups are using agents to recruit a team, build a product, and find customers at warp speed. 

    Wrap-Up

    “Long ago, Ben Graham taught me that ‘Price is what you pay; value is what you get.’ Whether we’re talking about socks or stocks, I like buying quality merchandise when it is marked down.” – Warren Buffett

    I love a good bargain. And I’m starting to find them where I’d least expect: the world’s top accelerator.

    If you’re investing and you’ve stepped away from YC due to valuations, I encourage you to take another look. 

    And if you’re in YC and you’re building something amazing, shoot me a message! I’d love to hear about it. 

    DMs open. 

    More on tech: 

    I Left $157,000 on the Table: How I Missed a Great Investment

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

    Meet My Latest Investment: Perfectly

    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!

  • China’s GLM 5.2: The Most Powerful Open-Source Model Yet — But Does It Deliver in Real Life?

    China just dropped the first open source SOTA model: GLM 5.2. It crushes the benchmarks, but struggled in my real world testing.

    Today, I ran GLM through a three-round test: building a pitch deck, teaching me about data centers, and designing a website. 

    GLM showed some powerful capabilities. But it also made surprising mistakes…

    Round #1: Making a Startup Pitch Deck

    For our first round, I had GLM 5.2 make a pitch deck for Uber.

    I turned on Wispr Flow and rambled on what I wanted the deck to cover: team, traction, and vision. I gave GLM some style pointers, like putting high-contrast text on a black background. 

    GLM produced a beautiful deck! 

    I’ve seen the original UberCab deck. It didn’t look nearly as slick. If only Travis had had GLM! 

    This round gets an A+. Every founder should make their deck with GLM. 

    Round #2: GLM Teaches Me About Data Centers

    I was excited to use GLM’s Knowledge/Teaching Material mode to learn about AI data centers. But it made me switch models 4 times due to high usage, landing on the weaker GLM-5-Turbo.

    Rotten UX!

    Eventually, GLM produced some solid info. I learned that five 1 gigawatt data centers consume as much electricity as all of New York City. 

    Power really is the bottleneck!

    The report was great, but getting it was a pain. I’m giving this round a C.

    Round #3: Designing a Website

    GLM 5.2 claims to be strong in coding and design. Can it make a better design for this blog?

    I gave GLM a vague prompt for a DOS-like interface, but cleaner and fresher. It switched to GLM-5-Turbo again, ran slowly, then outputted a blank page. 

    I told GLM to redo it. This time, I got a very nice homepage. 

    But I shouldn’t have to ask twice. Lovable nails this on the first try.

    I’m giving this round a B-. 

    Wrap-Up

    Overall, GLM earned a B- in my testing.

    It excels on pitch decks, but struggles to make a basic webpage. Overall, it did not feel nearly as powerful as Claude or Grok.

    Still, GLM 5.2 makes a lot of sense for startups. 

    Download it, post-train it on your data, and run it dirt cheap. The outputs will be good enough for most products. 

    If token bills are killing you, give GLM 5.2 a try!

    More on tech: 

    AI Agent Hype Meets Reality: The Product Doesn’t Work (And Churn Is Coming)

    No Crew, No Budget: How Grok Imagine 1.5 Helped Me Create Slick Startup Marketing Videos

    Meet My Latest Investment: Perfectly

    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!

  • I Left $157,000 on the Table: How I Missed a Great Investment 

    I just missed out on $157,000. Last year, I passed on a startup that is now raising at 25x the valuation. Here’s how I blew this deal, and what I’ll be doing differently next time…

    Why I Passed 

    We’ll call this startup Supercorp. In April 2025, I had an opportunity to invest in their seed round.

    They had solid growth of 3.5x year over year. The founder had a good technical background, and tthey were nearing $2 million ARR.

    What worried me was the market. Their segment had fewer than 2,000 potential customers, according to my research. 

    Even at Supercorp’s healthy ACV, that produced a TAM of just $500 million. What’s more, their growth was a little below what I was seeing in some other startups.

    What I Missed

    The biggest thing I missed here: focusing too much on their initial customer segment.

    They soon expanded way beyond it. Now they’re building for many industries, shipping new products, and massively expanding their TAM.

    I also didn’t pay enough attention to the founder’s background. His decades of experience in the market he’s serving gave him a huge advantage. 

    Unconscious Bias?

    There may be another reason I missed Supercorp. The team doesn’t look like your typical startup.

    They’re not 22. They don’t live in San Francisco or New York.

    Did that bias me unconsciously? Hard to say. 

    But it’s possible. When I meet less traditional teams in the future, I’ll have to look at them extra closely.

    What This Miss Cost Me

    The seed stage deal was done around $20 million. Now, they’re raising at $500 million. 

    This was a syndicate deal, and it had some significant fees on it. But after fees and dilution, my typical $10,000 check would still be worth $157,000. That’s a 16x return in 14 months.

    Instead, I made nothing. Yeah, it sucks.

    Wrap-Up

    In the end, I got hung up on TAM math. What I didn’t see was a strong team with a great product who’d find someone to buy it. 

    Every investor misses deals. This one stings, but there’s always another. 

    Hopefully I’ll nail the next winner.

    I’m off to the woods for a camping trip. ⛺ Have a great weekend, everybody!

    More on tech: 

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

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

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