Tremendous

An angel investor's take on life and business

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

    Yesterday, a founder nailed a cold message in just 38 words. I put him on my calendar first thing the next morning. Here’s why short messages win…

    Investor Time Is Very Limited

    You only have 60 seconds to make an impression.

    Investors, big or small, get tons of inbound. I look at a couple thousand deals a year.

    I simply cannot spend very long looking at most deals. 

    That founder who sent me the 38-word message? I put him on the calendar first thing.

    The guy who writes me a novel? Probably not going to get the response he wants. 

    Writing a Brief Cold Message That Actually Converts

    A good cold message looks like this:

    • One sentence vision
    • Team info
    • Traction

    Here’s a fictional example:

    “I’m Jim, founder of Megastartup. I built my last startup to $5 million in annual revenue.

    Megastartup combines every YC company into one startup and automate it with agents. 

    We’re at $100k ARR.”

    Why This Message Will Get You Meetings

    See how short that was? Just 33 words.

    I just timed how long it took me to read it aloud: just 11 seconds. You can hold someone’s attention for 11 seconds, even these days. 

    In that short moment, you’ve shown you have a strong background. You’ve clearly communicated what you’re doing. And you’ve shown traction. 

    This should be enough to get you a lot of meetings.

    Long Messages Get Deleted

    What if I had written a cold message that goes on for four paragraphs and a couple of hundred words?

    The investor sees that wall of text and hits delete. There’s 75 other emails in his inbox.

    Your longer message didn’t make a better impression. It made no impression at all.

    Cut your message to the bone. I want to see 50 words, tops.

    What’s True of Cold Messages Is True of Decks

    So you’ve cut the fat from your cold message. But are you still sending investors a deck with 42 slides?

    Then you’re doing it wrong.

    Seven slides. That’s it. 

    1. Title
    2. One sentence vision
    3. Team
    4. Traction
    5. Market size
    6. Competitors
    7. Ask 

    Each slide should have just one or two sentences. Make the text enormous and easy to read. 

    People flip through pitch decks. You want to enable that. 

    Wrap-Up

    A lot of the problems founders have in fundraising come down to this: they think investors spend hours pouring over their message and deck.

    We don’t. You get a minute, maybe two.

    In those brief moments, we decide whether it’s worth meeting you. Give us some compelling facts, fast!

    Cut your cold message. Throw out your deck. 

    And watch the number of investor meetings you get go through the roof.

    More on tech:

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

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

    No, You’re Not Getting a $250k Angel Check — Here’s Why

    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!

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

    Friction is killing your fundraise. Here’s how to remove it and close out your round, fast…

    Take the example of an awesome founder I spoke with recently.

    “An investor told me to require an e-mail address to see the deck,” he said. “What do you think?” 

    “Don’t require anything. Remove all friction,” I said. “Don’t give them any reason to click off your deck and ghost you.”

    Common Friction Points to Remove From Your Fundraising Process

    Every bit of friction in your fundraise is costing you money. Here are some common forms of friction to avoid:

    • Asking for an e-mail address to see a deck
    • E-mailing back and forth to schedule a meeting (just send a Calendly link)
    • Requiring anything more than an e-mail to book a Calendly appointment
    • Requiring passwords or 2FA to see a deck or book an appointment (yes, people do this)
    • Asking for NDA’s

    Make it as easy as possible for investors to learn about your company, get excited, and book a meeting. Those meetings turn into checks.

    Any Benefits from Tracking Aren’t Worth the Risks

    Some founders think they should require an email address to see the deck so they can track who’s viewing it. 

    But you already know who you sent it to, right? What’s the point of tracking further? 

    Any possible benefit is hugely outweighed by the risk they get annoyed and move on to the next deal.

    Wrap-Up

    Fundraising is sales. If you want to sell more, make your product easy to buy.

    Amazon makes it extremely easy to buy from them. You can get just about anything in 24 hours with a couple of clicks.

    They’ve removed all friction. And who’s selling more than them?

    Learn from Amazon. Make it easy for investors to see what makes your startup special.

    What’s one piece of friction you’re removing this week?

    More on tech:

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

    No, You’re Not Getting a $250k Angel Check — Here’s Why

    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!

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

    Pattern I keep seeing in AI agent startups:

    > announce super powerful agent
    > ship agent
    > tons of sign-ups
    > insane revenue growth
    > massive funding round
    > product simply does not work
    > what now?
    > heavy churn likely

    Customers bought the dream of an agent that does everything. 

    But the product fundamentally does not work.

    Worse yet, it produces junk outputs. Useless e-mails. Robocalls that scream “robot” and never convert a customer. 

    This AI slop means more work for humans, not less. So they cancel.

    When the Sugar High of Growth Wears Off 

    As churn gets worse and worse, growth will become impossible to maintain. Eventually, revenue will trend down.

    If the startup can make the agent work before runway runs out, it could still be a success. But for a lot of agents, they’re not even close to living up to the promises.

    And because these startups have raised at such high valuations, raising more money will be hard. They’ll have to continue the crazy growth. 

    The likely outcome for these startups: death. 

    The problem with these companies is they have overpromised and underdelivered.

    Lessons From a $100 Billion SaaS Company You’ve Never Heard of

    20 years ago, I sat in the all staff meeting at Epic. 

    “What’s the best way to make sure we meet customer expectations?” founder Judy Faulkner asked.

    “Work really hard!”

    “Always put the customer first.”

    People continued giving these Boy Scout answers. Judy shook her head.

    “The key is to set expectations very low.”

    That’s how Judy built a company that the Acquired guys estimate is worth over $100 billion. 

    Nail It, Then Scale It

    AI agent startups love to claim they automate an entire job. Very few pull it off.

    A better approach: nail one small part of a job. Scale that across lots of customers.

    Then add more capabilities.

    People will happily pay for a product that does one important task well. But if you try to do everything and screw it up, they’re going to churn. 

    Wrap-Up

    Instead of building some superagent to do all things for all people, make your focus as narrow as possible. Test the heck out of your product and be sure it works in real-world conditions.

    It’s exciting to have a buzzy launch and get to millions of revenue overnight. 

    But if you want to build an enduring company, try doing it Judy’s way.

    More on tech: 

    The Secret AI Weapon That Could Close Your Round: VC Boom

    No, You’re Not Getting a $250k Angel Check — Here’s Why

    “Don’t Be Afraid to Fail” — Three Lessons from Elon That Will Make You a Better Founder, Leader, and Investor

    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!

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

    Elon just dropped Grok Imagine 1.5, his most powerful video model yet. Instead of hiring influencers and rigging cameras, I used Grok to create marketing videos out of nothing…

    I tested the new model in 3 realistic startup marketing scenarios. Here’s what works and where Imagine still needs some polish…

    Round #1: UGC-Style Marketing Videos, No Influencer Needed

    Say you’re launching a new line of smoothies. You want to produce some UGC-style ads to show off your product.

    Two years ago, you would’ve paid a gang of influencers. Today, startups are creating influencers out of thin air.

    I had Grok make a video of an athletic girl showing off our new smoothie. Grok produced a decent video, but it doesn’t look as natural as I’d like.

    Also, the maximum length is 12 seconds. That may be okay for TikTok or Reels, but it’s a little short. 

    I’m giving this round a B-.

    Round #2: Making a Launch Video Without a Camera or Mic

    Have you ever wanted to make your own buzzy launch video and get millions of views? Grok Imagine makes it easier than ever. 

    I could futz around with a fancy camera and mic setup. Or, I could just seed the prompt with a picture of me and have Grok do the rest.

    I used my X profile pic and gave it a basic prompt to produce a launch video for an app. The video was realistic and engaging…maybe more engaging than I am in real life. 😂 

    Seeding the prompt with an image made a huge difference. The video was much more realistic. 

    The screens for the app are generic. No surprise there — I didn’t give it much specifics. Had I seeded the prompt with some screens from a real app, it would’ve come out even better.

    For a short launch video, this works well. I’m giving Grok an A for this round. 

    Round #3: Product Concept Video, $0 Budget

    You’re building a robot to sort packages. You want to show how awesome your robot will be when it’s finished!

    But right now, your prototype is a janky mess of chips and wires. Can Grok help show everyone your vision? 

    I gave Grok a simple prompt, telling it to show a robot on wheels sorting packages. It came out with a great little video showing what the finished product could look like.

    You can use videos like this in fundraising and recruitment. It helps get people excited about your startup!

    Grok earns an A+ on this round. 

    Wrap-Up 

    Overall, Grok Imagine 1.5 earned a solid A-. 

    It did a great job of producing marketing videos for my imaginary startups, but the humans need a little more work to be realistic. 

    If you write your prompt carefully and seed it with images, Grok can produce awesome videos for $0 budget.

    The next thing I want to see is longer-form video. We need videos of at least 2-3 minutes — well beyond the capabilities of any AI video generation model today. 

    Give the new Grok Imagine a try and get more eyeballs on your product! 

    More on tech: 

    The Secret AI Weapon That Could Close Your Round: VC Boom

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

    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!

  • The Secret AI Weapon That Could Close Your Round: VC Boom

    I just found a secret weapon that could help you close your round: VC Boom. It grades your deck and automates investor outreach. It’s so good, I was astounded.

    The creator is Yoan Berno, a former VC — so he knows what investors are looking for. Best of all, most features are free.

    This morning, I put VC Boom to the test…

    How Chopped Is Your Deck? VC Boom Weighs In.

    I fed it the Digital Ocean seed deck that we talked about on the blog last week. Itt’s a really good deck, but it has one glaring omission.

    Can VC Boom find it?

    VC Boom nailed its assessment, giving the deck 71 out of 100. Right away, it zeroed in on the big problem: no team slide.

    VC Boom advised me to add info about the team and why they’re the best people to change cloud computing.

    VC Boom says to put the Team Slide right after traction. Personally, I’d make it number two right after the title. But why quibble?

    VC Boom did a great job on the deck. Now, can it help me find some investors?

    Making a Targeted List of Investors and Drafting Cold Messages

    I had VC Boom pull a targeted list of a hundred investors that write checks in the right industry and stage — seed stage cloud startups. 

    The list was well targeted, pulling in some awesome VCs. But VC Boom can go even further.

    I had it draft a message to Mark Nelson at Madrona, a famous early-stage firm.

    The message is decent overall, but makes one important error.

    It claims that the company’s revenue is “$1MM annual run-rate MRR”. This is very confusing wording that could mislead.

    It almost sounds like the company is making $1 million a month. It’s not. It’s actually at $1M ARR.

    Also the message is too wordy for my taste. I’d cut it down by at least half.

    Still, VC Boom gave us a solid starting point. If we do a little editing here, we’ll have ourselves a solid cold message. 

    Wrap-Up

    Overall, VC Boom is fantastic. 

    If you’re raising money now, stick your deck into VC Boom and get some advice. And once you’ve perfected your deck, use the tool to message some investors.  

    Using VC Boom could be the difference between raising millions of dollars and raising nothing at all. 

    There will be no blog tomorrow. See you guys on Monday!

    More on tech: 

    No, You’re Not Getting a $250k Angel Check — Here’s Why

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

    Investors: Stop Asking Pre-Seed Founders About Their ‘Moat’

    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!

  • Investors: Stop Asking Pre-Seed Founders About Their ‘Moat’

    “What is your moat?” This is the most pointless question investors ask pre-seed founders.

    Picture two guys in a tiny apartment, sleeping on mattresses, living off food from sponsored tech events. 

    What moat do you expect them to have? 

    Speed Is the Moat

    At this stage, it’s all about moving faster than the next guy. 

    These two have no money, no office, no employees. But they do have one advantage: speed.

    No committees. No approvals.

    They just ship. And if they listen to customers, they’ll ship the right things. 

    What to Ask Instead

    Instead of asking two guys living off ramen what their moat is, ask one of these questions instead:

    • What achievements are you most proud of?
    • Why are you working on this idea?
    • Who are your customers?
    • What are your customers telling you?
    • How many do you have?
    • What do they pay each?
    • Can you demo your product for me? 

    These questions get at things that are actually relevant: team, product, and customers. 

    Fording the Moat

    No software startup today has a real moat. 

    Two years ago, OpenAI looked unstoppable. Now, they’re well behind Anthropic. 

    Anthropic moved faster.

    If even OpenAI isn’t safe, don’t expect a moat from a 2 month old startup.

    Wrap-Up

    Too often, investors ask the same questions everyone else asks. We don’t stop to think whether the questions make sense.

    When anyone can Claude Code a product in a weekend, moats in software are rare. And at pre-seed, they’re nonexistent.

    Instead of worrying about moats, I want to know if the founder is an exceptional person. 

    Has she done something big in the past? Is she moving at warp speed?

    An exceptional founder moving fast — that’s the only moat left. 

    What’s the worst question you’ve been asked by an investor (no names)?

    More on tech: 

    No, You’re Not Getting a $250k Angel Check — Here’s Why

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

    The Digital Ocean Seed Deck: What an $18B Company Looks Like at the Earliest Stages

    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!

  • ‘Test Like You Fly’ — What You Can Learn from an Exploding Starship

    “Things being impossible is really to be determined by breaking the laws of physics.”

    Jacob McKenzie, VP of Raptor, SpaceX

    SpaceX is worth $2.7 trillion. But the real story is how they operate: massive responsibility given to young engineers, rapid iteration, and learning from failure. 

    SpaceX’s new documentary Test Like You Fly gives us an inside view of this incredible company. It’s also a playbook every startup can follow…

    Empowering Young Engineers

    Imagine that you’re a couple years out of school. You have control over a 300-foot rocket.

    How intoxicating must that be? No wonder they work around the clock. 

    But SpaceX isn’t all youngsters. There are also seasoned engineers holding many top positions.

    You can see that Elon doesn’t idolize youth like some in Silicon Valley. He just picks the best person for the job and gives them tons of responsibility.

    In our businesses, we should give the new guy an uncomfortable amount of responsibility. If we hired the right person, he’ll rise to the occasion. 

    Working Around the Clock

    SpaceX’s rocket tests continue late into the night. The offices and factories remain full. Everyone looks intently focused.

    To move as fast as SpaceX, long hours are a must. 

    I recently spoke with a former SpaceX engineer. He worked around the clock and often slept in the office. 

    “You get a message at 4am saying ‘You’re holding up the future of human spaceflight.’ And you’re expected to respond right away,” he said. 

    The most successful startups I’ve invested in all work long hours, 6-7 days a week.

    It’s not an easy life. But it does allow you to accomplish incredible things.

    Learning From Failure

    I’ve never seen a company promo video that shows the company failing so often! 

    But every time a rocket blows up, the engineers learn something. They build another prototype. That one tests better.

    Incremental progress adds up fast. Catching a rocket with chopsticks took just 5 launches. 

    In many other places, such as Europe or Japan, failure is heavily stigmatized. It’s difficult for a culture like that to produce a SpaceX.

    In my own work, I know that most of my investments will fail. But I try to learn from each one and get better for the future.

    Wrap-Up

    Someone clicks a button on her computer. A massive rocket fires up.

    Watching it is surreal. I’m only 40, and already, the world is very different from when I was a kid.

    We’re not all going to launch rockets like SpaceX. But whatever we’re doing, we can learn from these amazing engineers. 

    Do really hard things. Accept failure and learn from it. And get better every time.

    More on tech: 

    “Don’t Be Afraid to Fail” — Three Lessons from Elon That Will Make You a Better Founder, Leader, and Investor

    How Jon McNeill Scaled Tesla from $2B to $30B — 3 Lessons I’m Stealing for My Own Business

    Elon Musk (Part 1): Overcoming the Odds

    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!

  • No, You’re Not Getting a $250k Angel Check — Here’s Why

    “We’re raising an angel round. Minimum check $250k.” Here’s why that’s a mistake…

    I get messages like this every now and then. These founders don’t understand how most angel investors operate.

    Lessons From a Billionaire Angel

    Two years ago, I invested in a round that included a multibillionaire. He wrote a check for $250,000.

    If $250k is the check size for a billionaire, what do you think you’re going to get from other angels?

    That’s right…a lot less.

    How Angels Really Operate

    Typical angel checks are around $25k. 

    Some are smaller, like my $10k checks. Sometimes you even see $5k. In syndicates especially, it can go as low as $1,000. 

    On the other end, you see $50k checks often. $100k is less common, and over $100k is unusual.

    Why Minimum Check Sizes Work Against You

    If you think this person can help you, there should be no minimum check size at all. 

    Getting a helpful person on your cap table isn’t really about money. It’s about bringing on someone that makes the company better. 

    Getting Intel on Prospective Investors

    If you’re unsure about an investor, talk to a few founders they’ve backed. Ask if this angel helped them and how.

    I’ve gotten into deals directly at incredibly low check sizes by being helpful. The smallest check I’ve ever written directly was $2,500, although these days I do $10k.

    If I get a founder intros to multiple VC funds, that can be a big help in closing the round. At that point, the founder doesn’t care how much I’m investing personally.

    Wrap-Up

    If you want to raise money, my best advice is to get rid of your minimum check size and bring on the most helpful angels you can. 

    Plug into their network. Meet the big funds. Close out your round. 

    Then you can get back to what really matters: building. 

    More on tech:

    Small Investors Lead to Big Investors

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

    How to Write Cold Emails to Investors That Actually Get Replies

    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 1 Hour to 5 Minutes: How Perplexity Comet Automated My Founder Meeting Prep

    I used to burn a full hour each day just prepping for founder meetings. The messages are scattered across Gmail, X, and LinkedIn. This morning, I finally automated it with Perplexity Comet.

    My meeting prep is down to 5 minutes. And the questions Comet came up with were better than mine!

    Here’s how it works…

    Setting Up My Meeting Prep Automation

    To start, I downloaded Perplexity’s Comet browser. I signed up for the paid plan so I could access unlimited connectors, including Gmail and Google Calendar. 

    Next, I told it to look at my Google Calendar and prepare me for today’s meetings by looking at messages across all platforms. 

    Comet directly connects to Gmail and Google Calendar via API. But for LinkedIn and X, it has to dig up the messages using Perplexity Computer. 

    This is when Comet really wowed me. It opened up a new tab and started navigating LinkedIn and X. Sitting here watching it type in people’s names and look through messages on LinkedIn, I felt like I was seeing the future.

    It moves very slowly — like a grandpa using a computer. 😂 But it works! 

    The Moment of Truth — Can Comet Automate My Meeting Prep?

    Comet took about 10 minutes to run through my whole calendar and prep me for everything.

    It did an excellent job! It pulled context from Gmail, LinkedIn messages, and X DMs. There was the occasional hiccup, like when it needed my X PIN to get into my messages. But overall, it worked well. 

    The questions Comet suggested were better than mine! It found some key competitors I didn’t know about.

    Streamlining Meeting Prep for the Future

    Since the Comet Browser and Grok both have easy-to-use connectors built for Gmail and Google Calendar, I’m going to try to consolidate all of my founder messages onto Gmail.

    I created a new Wispr Flow snippet to ask founders to send their deck and incorporation info straight to my Gmail. With everything in one place, the agent should be able to prep me for my meetings a lot more quickly and easily.

    Are Agentic Browsers Too Risky to Use? 

    Comet isn’t new. Perplexity actually released it almost a year ago.

    But since these agentic browsers present some security risks, I’ve been reluctant to use them.

    In the end, you weigh risks against rewards. As the number of founders I meet grows, prepping for meetings has become increasingly time-consuming. 

    A tool to automate it is worth a little risk.

    I was also careful about what permissions I gave Comet. It can read my Gmail and Google Calendar but it can’t just delete everything. 

    Wrap-Up

    Think about where we are now…

    The founder may have created the deck using an AI tool like Gamma. I’m analyzing the deck and our messages using an AI agent.

    Have your agent call my agent!

    But even as our AI tools become increasingly capable, I don’t want to drain the humanity from the founder-investor relationship. 

    The person-to-person meetings are really important. The technology just helps handle the admin work so I can meet more founders!

    If you’ve never tried Comet, consider giving it a shot. It’s pretty amazing what you can automate!

    Have a great weekend guys! 

    More on tech:

    The Digital Ocean Seed Deck: What an $18B Company Looks Like at the Earliest Stages

    Request for Startups: Seawalls, Supertrees, and Power Saving Tech

    My Top 3 YC P26 Startups: Space Factories, Rentable Humans, and AI Doctors

    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.

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  • The Digital Ocean Seed Deck: What an $18B Company Looks Like at the Earliest Stages

    Digital Ocean is worth $18 billion. This morning, I dug into their original seed round deck from 2013. Here’s what you can learn to help you in your fundraise…

    Clearly Framing the Problem

    Digital Ocean’s value proposition is simple: we let you deploy to the cloud quicker and easier.

    See how clear this value prop is? That’s something a lot of startups get wrong.

    I’m 17 slides deep into their deck and I still don’t understand what they do or why. At that point, your odds of getting a check are minimal.

    I also loved all the testimonials from users. There’s nothing like hearing from the people that actually use the product.

    An Insane Revenue Ramp

    In this deck, it’s the Traction slide that really stands out.

    Digital Ocean was already at a $1 million annual run rate, up from approximately $200k just 4 months prior. That’s 50% MoM growth.

    You could meet with 50 startups and not find one with growth this strong. This traction is what will make investors finally pull out the checkbook.

    You could have the prettiest slides or the sickest launch video. But in the end money talks.

    Where’s the Team Slide?

    There’s one crucial thing missing from this deck: a team slide.

    Two of the founders, Ben and Moisey Uretsky, previously started a company called ServerStack. They got it to $6 million ARR.

    But that information is nowhere in the deck. What a miss!

    That would have gone a long way to convincing VCs these guys are worth betting on. But the clarity of their vision and the strength of their traction was still enough to make the sale. 

    Would I Have Invested?

    Digital Ocean in 2013 had everything I look for in a startup.

    They’re addressing a major problem. Their value prop is clear. The founders have a history of achievement. And their growth is off the charts.

    Had I been lucky enough to see this deal, I would have been knocking people over to invest. 

    Wrap-Up

    Digital Ocean’s seed deck nails the key points. They clearly explain the value prop and show us strong traction.

    The only way they could have made it better: sell the awesome accomplishments of the founders.

    Digital Ocean wound up closing $3.2 million in their seed round, led by IA Ventures. This investment helped turn IA into a top firm.

    If you’re raising money right now, learn from the Digital Ocean founders. Be crystal clear about the problem you’re solving. Show us strong evidence that it’s working.

    If you can do that, you just might be the next Digital Ocean.

    More on tech:

    Why Short Decks Raise Millions

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

    How to Write Cold Emails to Investors That Actually Get Replies

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    Fundrise

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    Wispr Flow

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

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