Tremendous

An angel investor's take on life and business

  • They Invented the iPad in 1989 — And Lost it All

    “Still, I had to accept the impossible, final truth: GO was gone. Six years, hundreds of jobs, $75 million — all gone.”

    Jerry Kaplan

    ‘It Was Pure Magic’

    In 1989, GO Corporation created the first tablet computer: the PenPoint. Twenty-one years before the iPad, PenPoint took computing from clunky towers right into the palm of your hand.

    “It was pure magic — no one had ever before seen this much computing power packed into a diminutive, four-pound frame. Someone snapped a Polaroid. I wrote on it ‘6/20/89 — First Working Unit’.”

    In his book Startup: A Silicon Valley Adventure, GO Founder & CEO Jerry Kaplan gives us the PenPoint story from the inside.

    The Best and the Brightest

    Kaplan built a team of some of the best and brightest engineers in Silicon Valley. Above all, he selected for enthusiasm:

    “We soon developed a simple technique for selecting candidates: check their credentials, tell them about the project, and then observe their immediate reaction. We judged their suitability by gauging their level of enthusiasm.”

    Great team assembled and flush with venture capital, GO looked hard to beat.

    With Friends Like These…

    But the reality inside the company was far less rosy. GO burned money rapidly to create its cutting edge hardware.

    Needing support with vendors and customers, not to mention more capital, GO was forced into a partnership with IBM. From day one, IBM made Kaplan nervous.

    Nonetheless, Kaplan did the deal. He would come to regret it.

    “…what mattered was not how much we liked the partner, but how much weight they could throw behind our bid to establish our operating system as the standard.”

    IBM soon hamstrung GO with bureaucracy. Security reviews and committee approvals proliferated.

    Soon, IBM went from an incompetent partner to a malign one. Knowing GO was running out of cash, it dangled financing over Kaplan’s head with one hand while trying to steal his invention with the other.

    Kaplan was eventually able to get financing from AT&T instead. But the red tape and bullying proved to be IBM-all-over-again.

    GO was making solid progress on its product. But it was also bleeding money and making almost no sales.

    The End of the Line

    Seven years in and once again low on cash, the team began to lose faith.

    “…as I looked around the room, I realized for the first time that money wasn’t the problem. It was a loss of faith…”

    With an exhausted team and shrinking bank balance, GO was forced into a merger with AT&T-controlled EO in January 1994.

    Shortly thereafter, AT&T shut down both EO and GO. This was the end of PenPoint.

    What Went Wrong?

    “In looking back over the entire GO-EO experience, it is tempting to blame the failure on management errors, aggressive actions by competitors, and indifference on the part of large corporate partners. While all these played important roles, the project might have withstood them if we had succeeded in building a useful product at a reasonable price that met a clear market need.”

    Kaplan zeroes in on job #1 for a startup: solve a problem, and get paid to do it. Despite tremendous effort, GO was never able to do this.

    The PenPoint was far ahead of its time. In technology, sometimes too early is just as bad as too late.

    Developing a brand new hardware and software platform may be too much for a startup. New hardware platforms and operating systems in recent decades have come from big incumbents like Apple and Google, not startups.

    Wrap-Up

    GO proves an enduring truth of startupland: hardware is hard.

    Jerry Kaplan and his team did everything to make their revolutionary computer a success. But it just wasn’t enough.

    Startup made clear to me just how hard it is to build a great company. And it also made me a little wary of IBM. 🙂

    Although PenPoint never made it, I admire Kaplan’s bold vision. PenPoint helped inspire a future generation of handheld computers, from the iPad to smartphones.

    Maybe GO wasn’t a failure after all!

    What do you think about PenPoint? Leave a comment and let us know!

    If you enjoyed this post, subscribe for more like this!

    More on tech:

    Why I Love a Down Market and More at Starta VC

    The Secrets of Sand Hill Road (Part One)

    The Secrets of Sand Hill Road (Part Two)

    Save Money on Stuff I Use:

    Fundrise

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

    More on Fundrise in this post.

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

    Misfits Market

    I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

    I wrote a detailed review of Misfits here.

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

    Photo: Jerry Kaplan

  • China’s Jobless, Childless Youth

    As China’s economy reels, youth unemployment has hit 21% — on par with Italy.

    A Dollar An Hour – With a College Degree

    From a Financial Times report:

    Job opportunities scream from posters at an employment fair in central China’s Zhengzhou. “Join us for the future!” urges one advertising positions for graduates to sell electric vehicles. Others seek “courageous” candidates or “attractive females” to sell medical equipment.

    But many of the jobs require 70 hours of work a week and command salaries as low as Rmb3,000 ($400) a month. Wang, a commerce graduate, struggles to get enthused.

    Zhengzhou, the industrial capital of a province of about 100mn people and home to the world’s largest Apple iPhone factory, ought to be able to offer its graduates better career prospects, said Wang, who did not want his full name to be published.

    At $400 a month with seventy hour work weeks and 2 weeks vacation, Wang’s pay would be just $1.37 an hour.

    We’re used to viewing Italy as an economic basket case. But now China, the biggest growth story of the 21st century so far, has reached comparable levels of unemployment at a much lower level of income. China’s youth unemployment also exceeds that of other trouble economies, likes France or Portugal.

    A multiyear Covid lockdown, real estate crisis, and crackdown on private business have all contributed to China’s woes. But demography may be the biggest challenge of all.

    China — The Next Japan?

    China’s fertility rate dropped to 1.09 children per woman in 2022. China’s population is falling, and India has recently surpassed it as the world’s most populous nation.

    Japan went down this road a long time ago. However, Japan was much richer when its population began to fall. What’s more, China’s former one child policy means that the demographic decline will be even steeper.

    I’ve spent a lot of time in Japan and speak the language conversationally. I’ve often asked young Japanese why they don’t have more children.

    They mention the same 3 things every time: low wages, long work hours, and unaffordable child care. China faces the exact same problems.

    Wrap-Up

    China’s jobless generation is also the best educated in the nation’s history. A large group of well educated and unemployed youth is a political powder keg.

    If the Communist Party can’t create decent jobs for them, China’s youth may rebel. Perhaps the only way to fix China is to give the people a voice.

    What do you think the future holds for China? Leave a comment and let us know!

    If you enjoyed this post, subscribe for more like this!

    More on markets:

    China’s Decline Has Begun

    Carl Icahn Loses $1.7 Billion in a Day

    From AI to Satellites, US Dominates All Competition

    Save Money on Stuff I Use:

    Fundrise

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

    More on Fundrise in this post.

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

    Misfits Market

    I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

    I wrote a detailed review of Misfits here.

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

    Photo: “Youth looking for a new job, Guangzhou, China” by ILO in Asia and the Pacific is licensed under CC BY-NC-ND 2.0.

  • China’s Decline Has Begun

    The Chinese social contract is simple: give us a good economy, and we’ll stay out of politics. The problem is, that contract is breaking down.

    The Chinese economy has 3 pillars. Today, all 3 are under extreme stress.

    The 3 Pillars

    1. Exports. Exports are down on a weak world economy.

    Meanwhile, the US, China’s biggest trading partner by far, is decoupling from China. China is now only America’s third largest trading partner, behind Mexico and Canada.

    1. Real estate. After years of over-investment, China’s real estate sector is crumbling.

    One of China’s largest developers, Country Garden, is nearing bankruptcy. Evergrande, another large developer, has already defaulted on its debt.

    Half-built apartments litter second tier cities across China. No one knows if they’ll ever be finished.

    1. Tech. China’s government is cracking down hard on its technology sector, previously one of the world’s most vibrant.

    Top entrepreneurs like Jack Ma simply disappear. Entire sectors are nationalized overnight.

    China’s Economy Sputters

    No wonder China’s economy is running on fumes. Recent data shows China has fallen into deflation.

    Deflation can lead to a brutal cycle of lower prices, wage cuts, and declining economic output. A similar spiral has trapped Japan for a generation.

    China’s economy is so bad, the government has simply stopped publishing many forms of economic data. After youth unemployment and consumer confidence hit worrying levels, it stopped reporting numbers entirely.

    The Future

    China’s population has begun to decline. Long the world’s most populous country, it lost that distinction to India this spring.

    China is aging even more rapidly than Japan. The Communist Party’s one child policy all but assures a huge drop in population in the coming decades.

    Fewer people means fewer workers and less economic output. With no history of immigration and a language that is hard for foreigners to learn, China is unlikely to make that up with workers from abroad.

    Meanwhile, the best and brightest have a strong incentive to leave. Why work for a lifetime to build a great business, just to be disappeared like Jack Ma?

    Wrap-Up

    China’s economy is under assault on all fronts. And even if current challenges like the real estate crisis fade, demographics will hobble its economy for many years to come.

    As China becomes weaker economically, it may lash out in anger.

    Russia’s decline began long before China’s. Today, it is asserting the only power it has left, its military.

    China may do the same in the coming years, attacking Taiwan. That would cost China a great deal — but it would cost the rest of the world, as well.

    What do you think the future holds for China? Leave a comment and let us know.

    If you enjoyed this post, subscribe for more like this!

    Here are a few of my favorite recent articles to hold you over for the weekend!

    From AI to Satellites, US Dominates All Competition

    The Secrets of Sand Hill Road (Part Two)

    The Secrets of Sand Hill Road (Part One)

    Save Money on Stuff I Use:

    Fundrise

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

    More on Fundrise in this post.

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

    Misfits Market

    I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

    I wrote a detailed review of Misfits here.

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

  • Gig Work Dominates Largest Employers

    Who do you think are the largest employers in America? General Motors, McDonald’s, maybe Starbucks?

    Just 14 years since the launch of Uber, gig work platforms are now 3 out of the top 5 employers in the country.

    Here’s Forbes’ list of America’s largest employers:

    1. Walmart
    2. Amazon
    3. Home Depot
    4. Fedex
    5. Target

    Let’s add gig work. The list now looks like this:

    1. Walmart
    2. Doordash
    3. Amazon
    4. Uber
    5. Instacart

    For an entry level job, gig work pays a decent wage. A typical rate is around $15-25 an hour, higher than entry level jobs at McDonald’s or Walmart.

    Is it any wonder you can’t get a waiter today? Who’s going to work for a server’s wage of $5.26 an hour when Uber is paying $20?

    Gig work can be flexible with good pay, but it can also be unstable. And depending on where they live, gig workers may not be eligible for unemployment insurance or worker’s compensation benefits.

    Over time, gig work may take over more and more fields. Last mile delivery and food and beverage jobs could be prime candidates.

    As more Americans depend on gig work for their living, I expect to see unions try to organize these workers. Governments may also regulate the sector more heavily.

    Politicians in California tried to get gig workers reclassified as employees. So far, their efforts have failed.

    But more states are likely to do the same. This could upend the business models of companies like Uber and Doordash, raising costs and limiting flexibility.

    On the whole, I think platforms like Uber are a great thing for workers. If your job is treating you like crap, you can always walk out and fire up the app.

    What’s more, massive new employers means lots of demand for workers. No wonder wages for low skilled employees are rising fast, even after inflation.

    The era of big plants, lunch pails and the noon whistle are over. Today, work happens when and where you want.

    I call that freedom.

    Is gig work good or bad for workers? Leave a comment and let us know what you think!

    If you enjoyed this post, subscribe for more like this!

    More on tech:

    AI Seed Funding Down 50%

    Why I Love a Down Market and More at Starta VC

    From AI to Satellites, US Dominates All Competition

    Save Money on Stuff I Use:

    Fundrise

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

    More on Fundrise in this post.

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

    Misfits Market

    I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

    I wrote a detailed review of Misfits here.

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

    *One caveat is that some gig workers work for multiple platforms. A driver might do Instacart during the week and Uber on busy weekend nights out. But even with some overlap, app-based platforms would be some of the nation’s largest employers.

  • Meaningless Metrics and Why I Hate Them

    “We have $20 million worth of LOI’s with major companies in the space.” Whenever I see a phrase like that, I roll my eyes.

    Letters of Intent (LOI’s) are one of a series of what I call “meaningless metrics.” They’re supposed to show that a startup is doing well, but they actually make a company look weak.

    When founders rely on meaningless metrics, they are giving a negative signal to investors. Why would you use them if you had something more substantive?

    The Metrics That Don’t Matter

    Let’s run through a few of these meaningless metrics:

    1) Letters of Intent (LOI’s). Angel investor Jason Calacanis calls these “letters of nothing” for good reason.

    LOI’s have no legal force. A big company can give you an LOI for $100 million, but good luck ever collecting on it.

    An LOI is basically just a press release. It makes a big company look innovative without actually having to commit.

    Whenever a startup mentions LOI’s, I assume they’ll never collect a penny of it.

    2) Cumulative revenue. Whenever I see this, I suspect the founder is trying to pull the wool over my eyes.

    Cumulative revenue is how much money your company has taken in throughout its entire history. It’s a number that always goes up, by definition.

    Some founders love this number. It always produces a chart that’s nice and uppy-to-the-righty.

    That’s why it’s meaningless. Every startup shows the same cumulative revenue chart.

    Any investor worth his salt will pick up on this. And he’ll ding you for trying to pull a fast one.

    3) Pipeline. Pipeline is companies you might some day sell to.

    I could list 100 companies I might sell a product to someday. It doesn’t mean it’s going to happen.

    Tell us about the sales you’ve actually made, not just who’s in your CRM.

    4) Startup competitions. You could win 100 startup competitions, but it doesn’t mean you’ll get one customer. It also doesn’t mean you’ll raise a penny in capital.

    Your time is much better spent finding customers. The real startup competition happens in the market, every day.

    That’s the one you need to win.

    5) Forbes 30 Under 30. Please Forbes, I beg of you, get rid of this list!

    A magazine putting you on some list doesn’t put money in your company’s bank account. It also doesn’t tell investors whether your product is good or bad.

    Win in the market, not in meaningless competitions.

    Meaningful Metrics

    If these 5 metrics are meaningless, what would be meaningful?

    Customers are meaningful. Real customers paying real money for your product.

    Team is meaningful. Show investors that you’ve assembled an awesome team perfectly suited to taking on the problem you’re facing.

    Product is meaningful. Show me a product with world class design, and I’m all ears.

    Focus on those 3: customer, team, product. Everything else is nonsense.

    What metrics matter to you? Which ones make you cringe?

    Leave a comment and let us know!

    If you enjoyed this post, subscribe for more like this!

    More on tech:

    AI Seed Funding Down 50%

    Why I Love a Down Market and More at Starta VC

    Google Search AI vs. GPT-4: Smackdown!

    Save Money on Stuff I Use:

    Fundrise

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

    More on Fundrise in this post.

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

    Misfits Market

    I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

    I wrote a detailed review of Misfits here.

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

  • AI Seed Funding Down 50%

    Seed investors are souring on AI startups. Seed funding for AI and machine learning startups is down by over 50% year over year, according to a new report by Fortune:

    “I think investors are growing a little bit fatigued with the seed investments they made two to six months ago that are almost going to zero overnight due to a single tech release, or what have you…because so many of them are OpenAI wrappers,” [Redpoint Ventures Principal Meera] Clark believes, referring to companies whose businesses rely on A.I. models like GPT.

    How the Mania Happened

    Shortly after OpenAI released ChatGPT, I saw a ton of startups like this. They amounted to ChatGPT with a slightly different look and feel.

    That’s not defensible. But it is easy to pop up quickly.

    Investors are always afraid of missing the next big thing. So people threw money at these companies. No revenue and a fat valuation were par for the course.

    How to Spot a Good AI Startup

    Now that founders have had more time to build, I’m seeing much higher quality AI startups. And as the initial buzz has begun to fade, valuations are looking enticing.

    So how do we know a good AI startup from a bad one? I like to ask two questions…

    1) How much of this can be done with ChatGPT?

    This is why I don’t like most blogging tools. You can write a solid blog post on ChatGPT. You don’t need custom software to do it.

    Even if your tool is a little better, people are used to using ChatGPT. The only way you’ll get them to switch is if you’re 10x better — a high bar to clear.

    2) How easily can an incumbent add this feature?

    Take the example of a generative AI startup that helps you make slide decks. It’s useful — but is it defensible?

    Today, many people use Powerpoint or Canva to make a deck. Microsoft or Canva can just add an API call to OpenAI and pop up some generative AI features.

    Once that happens, you’re in trouble.

    You’re asking people to change their habits and switch to your platform. And you’re trying to charge for what Powerpoint is giving away.

    You’re going to lose that battle.

    An AI Company That Got it Right

    If you can’t do the job with ChatGPT and incumbents can’t easily take your business, now I’m interested. A good example would be my latest investment, Micro1.

    Micro1 finds top engineers by scanning their resumes with GPT-4. Then, it teaches them to be more productive coders by using GPT-4.

    You can’t do this with ChatGPT, and there’s no easy way for incumbents to match Micro1’s offering. These thoughtful implementations of AI make great bets.

    Wrap-Up

    Investors shouldn’t lose hope in AI. The opportunity is massive — perhaps the biggest in our lifetimes.

    We just need to evaluate each company soberly, like any other investment.

    Does it deliver real value to the customer? Is it defensible? Does the price make sense?

    If I can answer yes to all three, I’m making the bet.

    Are you investing in AI? Why or why not?

    Leave a comment and let us know!

    If you enjoyed this post, subscribe for more like this!

    More on tech:

    Why I Love a Down Market and More at Starta VC

    Google Search AI vs. GPT-4: Smackdown!

    The Secrets of Sand Hill Road (Part One)

    Save Money on Stuff I Use:

    Fundrise

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

    More on Fundrise in this post.

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

    Misfits Market

    I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

    I wrote a detailed review of Misfits here.

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

  • Google Search AI vs. GPT-4: Smackdown!

    While I was doing some Googling last week, a little box popped up. “Use generative AI?” I was skeptical…could it really compare to GPT-4?

    But I had to give it a shot!

    For the last few days, I’ve been running one query after another through the new Google Search Generative Experience (SGE). The results have been impressive.

    But can Google compete with the AI heavyweight, GPT-4? To find out, I ran a series of head-to-head tests using the same prompts.

    Let’s see how they do…

    Round 1: Market Research

    One of my favorite uses for GPT-4 is market research. This morning, I was researching the market for movers as preparation for a meeting with a startup in that area later this week.

    I wanted to know how big the moving market is. Let’s ask GPT-4…

    GPT-4 gives an excellent result, totaling residential and commercial moves. It even provides projections for the future.

    Let’s try Google SGE…

    Google doesn’t understand the question. Rather than give me stats about moving, it just shows stats about the residential real estate market in general.

    The fact that a fifth of all the value of real estate in America is in California is an interesting stat, but it has 0 relevance to my question.

    GPT-4 takes this round.

    Round 2: Legal Research

    Startups like Harvey are making huge inroads in legal research. So I turned to AI to answer a legal question of my own on inspection rights.

    GPT-4 gives us a great answer, explaining how inspection rights work under Delaware law. Inspection rights let shareholders examine books and other business records, so long as its for a legitimate purpose.

    Let’s see what Google has to say…

    Google also gives an excellent response. It clearly explains what rights shareholders have in Delaware, and how they’re exercised.

    We’ll call this round a tie. And wow….lawyers are in trouble.

    Round 3: Technical Research

    For the last few days, I’ve been researching an e-commerce software startup for potential investment. When I met with the founder, a term came up that I wanted to know more about: “headless e-commerce.”

    Let’s see what GPT-4 can tell us…

    GPT-4 gives a detailed explanation of how headless e-commerce works. It fills us in on all the key tools and explains the benefits in flexibility they provide.

    On to Google SGE…

    Google’s response gives a little bit better detail on why merchants use headless e-commerce architecture. It lets them provide a more flexible and better user experience.

    But it gives us less detail on the actual tools they use to accomplish that. I’m going to call this round a tie as well.

    Wrap-Up

    Both Google SGE and GPT-4 do a great job of answering most questions. And for a company that was woefully behind a few months ago, Google’s showing is impressive.

    But GPT-4 is still better. It understands my questions at a deeper level, and the information it provides is more relevant.

    Google does have one huge advantage: distribution. Unlike OpenAI or Microsoft, Google can put it’s SGE in front of billions of people instantly.

    Google could win the AI race, despite its late start.

    Have you tried Google SGE? What do you think?

    Leave a comment and let us know!

    If you enjoyed this post, subscribe for more like this!

    More on tech:

    Professor GPT

    Why I Love a Down Market and More at Starta VC

    The Secrets of Sand Hill Road (Part One)

    Save Money on Stuff I Use:

    Fundrise

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

    More on Fundrise in this post.

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

    Misfits Market

    I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

    I wrote a detailed review of Misfits here.

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

  • Why I Love a Down Market and More at Starta VC

    Why do I love down markets? What do venture capitalists and Hasidic diamond merchants have in common?

    I dug into that and more at a great Q&A session recently with interns at Starta VC in NYC. Here are some of my favorite moments:

    10:13: How pro rata rights work.

    12:16: Why I prefer a down market.

    18:54: The only thing that matters for investors.

    20:35: My take on AI.

    23:38: What venture capitalists and Hasidic diamond merchants have in common.

    31:08: Why I love SaaS.

    43:40: When I’m expecting a recovery in the venture market.

    44:55: What I want to see in a startup.

    47:34: Why ideas don’t matter.

    49:03: Are AI startups overvalued?

    53:02: Why angel investing is the best business degree on earth.

    56:58: Why Twitter will 10x in 10 years.

    What were your favorite moments? What did I get wrong?

    Leave a comment and let me know!

    Have a great weekend everyone!

    If you enjoyed this post, subscribe for more like this!

    More on tech:

    The Secret to Selling Your Product: Vision

    The Secrets of Sand Hill Road (Part Two)

    The Secrets of Sand Hill Road (Part One)

    Save Money on Stuff I Use:

    Fundrise

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

    More on Fundrise in this post.

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

    Misfits Market

    I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

    I wrote a detailed review of Misfits here.

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

  • The Secret to Selling Your Product: Vision

    Jim* had an interesting product, but I was having trouble following his pitch. He skipped from idea to idea and feature to feature, leaving me confused.

    Jim: “SaaSy is a sales tool for teams. Here’s the messages screen. This is where you go to book a meeting. We’re planning on adding a Slack integration once we get enough resources from this fundraise.”

    I sat there, quietly stumped.

    “What’s the real value proposition here?” I thought to myself. “And if I can’t understand it, how will a customer?”

    Sell a Vision, Not Just a Product

    Some founders have a solid product with decent traction. But they just can’t tell the story.

    I pay close attention to a startup’s metrics. But if the founder can’t sell the vision, I’m out.

    Scott Kupor, Managing Partner of Andreessen Horowitz, emphasizes how important a great pitch is in his excellent book, The Secrets of Sand Hill Road.

    “….VCs are trying to determine whether this founder will be able to create a compelling story around the company mission in order to attract great engineers, executives, sales and marketing people, etc. In the same vein, the founder has to be able to attract customers to buy the product, partners to help distribute the product, and, eventually, other VCs to fund the business beyond the initial round of financing. Will the founder be able to explain her mission in a way that causes others to want to join her on this mission?”

    So much of being a founder is selling — to customers, employees or investors. If you can’t do it, you’ve got big problems.

    How to Get It Right

    How could Jim do better? Here’s what I’d like to see…

    Jim: Our product, SaaSy, will change the way sales is done forever. Salespeople can close deals 10x faster.

    Me: Can we run through a demo?

    Jim: Sure! The customer comes to the dashboard, where he sees a list of top prospects from LinkedIn. These are the people most similar to those who have bought in the past.

    Me: Cool!

    Jim: Then, he can send automated messages to each of them to book a meeting. Each message is personalized.

    And it all happens with one click.

    Now, he can spend less time sending cold messages and more time meeting with great leads.

    Jim has clearly shown not just what his product does, but why it matters.

    No one is going to be impressed with a tour of features. But show them you’re solving a real problem they have, and they’ll be reaching for their wallet.

    Keep Your Presentation Tight

    In early stage startups, the founder does most of the selling. If he rambles and can’t quickly show his product’s value, he won’t make many sales.

    Keep your pitch tight and focused. Clearly tell me what the company does and why it matters.

    You should be able to demo a product in about 3 minutes. Save lots of time for questions.

    When you answer a question, don’t go into a long story. Your answer should take about as much time as it took to ask the question.

    Wrap-Up

    When a founder presents a compelling vision and shows me how he’ll get there, I get excited. So do customers and employees.

    Get lost in details, and you’ll lose your audience as well.

    What do you think makes a great pitch? Leave a comment and let us know!

    If you enjoyed this post, subscribe for more like this!

    *Jim is a composite, not an actual person.

    More on tech:

    The Secrets of Sand Hill Road (Part One)

    The Secrets of Sand Hill Road (Part Two)

    From AI to Satellites, US Dominates All Competition

    Save Money on Stuff I Use:

    Fundrise

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

    More on Fundrise in this post.

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

    Misfits Market

    I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

    I wrote a detailed review of Misfits here.

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

  • The Secrets of Sand Hill Road (Part Two)

    In 2009, a small startup called Square was raising its Series A. Andreessen Horowitz saw the deal and passed. That mistake cost them $4.8 billion.

    The Pitch

    Square (now Block) had a big idea: make it easy for small merchants to take credit cards. It had an awesome product: a little dongle you could plug into your phone and accept credit card payments anywhere, any time.

    But there was one problem.

    Although Jack Dorsey of Twitter fame was a co-founder, he wasn’t the CEO. That spot was held by Jim McKelvey, a childhood friend.

    “…we didn’t know Jim nor did we have a good way to evaluate his skills as a CEO for the company, and we wondered whether Jack might prove to be a better long-term CEO for this business.”

    Scott Kupor, The Secrets of Sand Hill Road

    Andreessen liked the concept, but wasn’t sure if Jim was CEO material. So they passed on the deal.

    A $4.8 Billion Mistake

    The Series A instead went to Khosla Ventures. They invested $10 million at a $40 million post-money valuation in November of 2009.

    Today, that stake would be worth approximately $4.8 billion, assuming 50% dilution.

    For any investor, our biggest mistakes aren’t the deals we did. It’s the ones we didn’t.

    $10 million is a lot of money to you and I, but to Andreessen Horowitz, it’s nothing. But holding on to that money because the deal wasn’t perfect cost them one of the great investments of all time.

    Scott Kupor, Managing Partner of Andreessen Horowitz, recounts this fascinating story in his book The Secrets of Sand Hill Road.

    What Went Wrong?

    Where did Scott and a16z mess up here?

    They should’ve taken one look at this deal and dropped a massive pile of cash on Jack’s head.

    His other company, Twitter, was already a unicorn by September of 2009. He was clearly one of the great entrepreneurs of his generation.

    Maybe a16z would’ve preferred Jack in the CEO slot. But no deal is perfect!

    If these startups had every single thing figured out, they’d be in the Fortune 500 and they wouldn’t need us. Every deal will have its imperfections.

    But when one of the greatest entrepreneurs of his day gives you the opportunity to be in business with him, you take it. End of story.

    When Opportunity Knocks…

    I put this theory into practice in the summer of 2021.

    The deal memo for Callin was at the top of my inbox. I worked late into the night researching the company, a social app for audio.

    Callin hadn’t hit all the benchmarks I usually look for. But in the end, only one detail really mattered.

    David Sacks, the co-founder of PayPal, started it. I was in.

    Ultimately, I didn’t get an allocation. The deal was massively oversubscribed. And in the end, Callin was acquired for a modest sum, never having quite found an audience.

    Nonetheless, I would make that bet again any day.

    Wrap-up

    The opportunity to invest in Jack Dorsey seems like the perfect deal to me. But we can pick holes in even the best pitch.

    We have to remember to not just think about what could go wrong for a startup. We have to think about what could go right!

    Would you have invested in Square? Why or why not?

    Leave a comment and let us know!

    If you enjoyed this post, subscribe for more like this!

    More on tech:

    The Secrets of Sand Hill Road (Part One)

    What I Learned From an Investor Who Turned $100,000 into $100,000,000

    Zero to One

    Save Money on Stuff I Use:

    Fundrise

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

    More on Fundrise in this post.

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

    Misfits Market

    I’ve used Misfits for years, and it never disappoints! Every fruit and vegetable is organic, super fresh, and packed with flavor!

    I wrote a detailed review of Misfits here.

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

    Photos: “Jack Dorsey” by magerleagues is licensed under CC BY-SA 2.0. and “square dongle close up” by adafruit is licensed under CC BY-NC-SA 2.0.