“Genies are not easily persuaded to return to their bottles, progress is not going away, and change is not going to slow because humanity would like a mental health break.”
— Walter Russell Mead
“If the path before you is clear, you're probably on someone else's.”
― Joseph Campbell
“You must unlearn what you have learned.”
— Yoda, Star Wars: The Empire Strikes Back
Keep your hands and feet inside the ride
You jump out of bed Monday morning and charge down the hall to your new “office” — your kitchen table. You and your co-founder left behind the plump paychecks and posh benefits of your big company jobs and can pursue your startup full-time beginning today. You have no boss and no meetings to distract you, just uninterrupted time, all day, every day, to turn your startup dream into reality.
A month later, no customer has responded to your LinkedIn meeting requests, you have made glacial progress on your product, you are one month closer to draining your savings account, and the hum of your refrigerator is driving you mad.
You’ve been pitching angel investors all week, every hour on the hour. You pop into your tenth Zoom of the day and finally get a nibble. The investor says he understands your vision, knows your market, and wants to call some of your prospects to start due diligence.
A week later, the investor has ghosted you. Every other investor meeting ended with, “You’re too early” (which means “that’s a no from me, dawg”). Now your family is asking how much longer you’ll do “this startup thing” before you return to the bosom of your big company job.
A prospect converts their free trial to a paid subscription — your first dollar of revenue! You frame the order form, tack it to your wall, and head into the city with your co-founder to celebrate with burritos and Dos Equis. Your startup is officially legit! Fame and fortune will surely follow.
The following week, a competitor announces $10 million in Series A funding. Your first and only customer calls to tell you they like the competitor’s approach. They want a pitch, on the spot, on why they should stick with you.
You pay an executive search firm a month of your cash to help you hire a VP of Sales. After six months, dozens of interviews, and twelve reference checks, your new VP starts next week!
On Monday, the VP ghosts you. He ignores your calls until the next day when he tells you he had misgivings about your business and took a better offer at a more established company. Now you’ve lost six months, have no other candidates in your pipeline, and have to convince the search firm to redo the search for free.
You open a tiny office in New York City and hire a handful of new team members to take care of your East Coast customers. You are now a bi-coastal company!
The next week, one of your fresh New York hires launches a rant to a coworker about how he hates working with women. You jump onto a red-eye to fly 3000 miles to fire him the next day. He screams at you as you escort him out of the building.
You close a Series B at double the valuation of last year’s Series A. You finally feel like you can breathe, with enough cash to last the couple of years it will take to launch your startup into hypergrowth. On paper, your net worth has climbed well into seven-figure territory.
A year later, the financial markets have crashed, the economy is going into recession, your sales pipeline is drying up, and peer startups are raising money at a third of last year’s revenue multiples, if they can raise at all. You must cut half your team to make your cash last long enough to weather the downturn, and that’s if you hold onto your customers, who are calling you to renegotiate their contracts.
You wake up to an eight-figure wire transfer hitting your bank account from the large public company that just bought your startup. All you have to do is join the BigCo for a couple of years to vest the rest of your stock and mesh your team safely into the cogs of the corporate machine.
Three months later, you are spending your hours in endless meetings fighting political battles with BigCo middle managers who want to break up your team and grab your people like they are chopping up a stolen car. You set a timer to count down the days until you are done vesting your stock, after which you can return to your kitchen table to work on your next project, naturally another startup.
Yeah, this is what it’s like
Over my 30-year startup career, each of these stories has happened to me or to someone I’m close to. When you spend time with startup founders, you won’t hear tales of launch parties, podcasts, and conference keynotes. You’ll hear about getting whipsawed between the highs and lows of toiling in the trenches of a tiny company, building something no one has built before, with failure always looming.
If you start or join a startup, you’ll write your own stories, but they’ll echo these. You’ll swing between moments of elation, watching your vision take shape, and visions of doom, when you stay awake all night worried that you are going out of business, probably because you might.
I wouldn’t have it any other way, and most startup founders will tell you the same. The hard work, risk of failure, and emotional rollercoaster are worth it because:
Nothing is more fun than a startup that is working
I’ve been lucky to be involved in a few startups that achieved liftoff, and it’s a blast. You win new customers daily, watching your revenue and, thus, the value of your stock options soar. You welcome great new team members, like watching luminous guests arrive at a raucous party you are throwing. The hallways buzz with the excitement of a small team trying to do something great, like a sports team fighting for a championship. The rush is so addictive that many people, once they get a taste, return to early-stage startups, again and again, hoping for another hit.
I've worked with startups worldwide as an advisor to venture capital firm Point Nine Capital in Europe. I can walk into a startup in Berlin, San Francisco, Copenhagen, or Barcelona, and feel that same buzz. The energy from a small group banding together to create something new transcends geography.
Startups are the ultimate act of creativity
A startup doesn’t just invent a new product, as thrilling as that is on its own. You build a team, a culture, and your own way of working. You define a market and rewrite the rules for the industry you sell to. You craft messaging to build urgency with prospects, agonizing over every word, like writing poetry. You blend data, anecdotes, and intuition (guesswork) to make risky bets, track them to see if they pay off, and quickly pivot when they don’t.
Everything you deliver only exists because you and your team made it happen. You get the satisfaction of making your “ding in the universe.”1
Startups build careers
A startup generates a continuously growing pile of work but never has the people or expertise to do it all. On any given day, you might find yourself closing a deal with a customer, designing a user interface, creating a sales pitch, training a new team member, or pitching investors, most of which you have no training or experience doing. Everyone has to jump in and solve problems they’d never be allowed to touch at a larger, more respectable company.
As a startup grows, it creates new roles, and since most startups try to promote from within, your team is first in line to fill those roles. A junior employee can move into a senior management role in just a few years because you launched them onto such a steep learning curve that they are ready to take on whatever you throw at them.
Startups build relationships
Startup teams build strong camaraderie while working long hours on hard problems side-by-side in the trenches. People who worked together at an early-stage startup will share tales from their startup’s early days in the way a sports team swaps tales about the year they made a championship run. They relive the victories but have even more fun laughing at the defeats, especially those that required foolish audacity even to take on.
Startup teams also work directly with customers, partners, investors, and even the board of directors, building valuable connections they can call upon for future endeavors. That network often crosses paths at subsequent startups, creating a benevolent “mafia”2 who can rely on each other for support for the next project.
Startups build wealth
Early startup team members can quickly capture enormous wealth by owning a percentage of a valuable company they helped build. It’s the wealth that comes from building something new and valuable the world needs, not from financial engineering, rent-seeking, or zero-sum games fighting for market share in no-growth legacy markets.
The kind of people who start startups rarely blow their newfound wealth on yachts and Rolexes, and you probably won’t either. After ensuring their families are secure, many founders donate their time and money to causes they believe in and to live a life that aligns with their values. They often start another startup, invest in other startups, and help the next generation of founders forge their own paths.
Startups create new products and industries
Most innovations we enjoy, like automobiles, PCs, smartphones, search engines, and mRNA vaccines, happened when a few people with a great idea formed a new company to launch that idea into the world. Even the innovations brought to market by larger companies often come from acquiring a startup or partnering with startups to provide critical building blocks.
We have a long way to go. We need an energy revolution to address climate change. We need new drugs and treatments to cure physical and mental diseases. We need platforms and products to grow our economy and bring as many people into the global marketplace as possible. Startups make that happen.
Startups drive economic development
As of this writing in 2024, seven of the ten largest companies in the world by market capitalization were started within the last few decades — companies like Tesla, Meta, Amazon, Nvidia, Apple, Alphabet, and Microsoft. They represent millions of jobs and trillions of dollars of added value. Looking a bit further into the past, almost every large company you can name, whether it’s BMW, General Electric, or Pfizer, started with a few founders sitting in a garage or around the kitchen table.
Historically, startups have concentrated in a few superstar cities like San Francisco, New York, and Berlin, but startups are now proliferating worldwide, and many startups hire remote employees who can live anywhere. As those startups succeed, they generate the next generation of founders and investors who spread expertise and investment capital to parts of the world that need more of both.
The gap between theory and reality
Although startups can be a force for good, most startups never create much impact. They either fail outright or fall far short of their potential for a few reasons:
The founders are inexperienced
People who start or join early-stage startups are rarely polished corporate executives with expensive MBAs and years climbing the ladder at large corporations like GE or IBM. They are more likely to be a ragged bunch of misfits early in their career, sometimes straight out of school or even dropouts. Many are engineers, designers, or researchers with little experience in “the business stuff” like sales, marketing, and finance.
The founders have the wrong experience
Founders who do have experience at larger companies can have the opposite problem: that experience hurts them as much as it helps them. Lessons learned from selling a mature product to an established market don’t apply to startups. Those founders can flail for a few years as they realize that what worked at Merck or McKinsey doesn’t help a three-person company with no brand and no customers.
The founders are human
As brilliant and determined as many founders are, they have the same mental barriers, emotional roadblocks, and conceptual biases as the rest of us. They dismiss bad news, delay hard decisions, and avoid difficult conversations. The stress of the startup triggers anxiety, imposter syndrome, or burnout. Some let their ego prevent them from responding to feedback. Some ignore the wealth of useful startup advice now available, or they go too far the other way, endlessly reading books and blogs looking for the “right answer” as a way to delay making decisions.
The founders hit a ceiling
Even when a startup does manage to build a good team and get some customers, it can still fail when the business grows faster than the founders’ skills. They might struggle to hire after exhausting their immediate network. They make bad hires and are slow to replace them. They can’t train new sales reps to pitch the product as successfully as the founders could. They find themselves racing their own startup, trying to learn new skills just before they are needed, like they are laying down tracks ahead of a moving train.3
The founders are working on the wrong thing
Every startup has a core belief, or ''hypothesis,” about a market, a problem that market has, and a solution for that problem. Few people can reliably predict the market’s reaction — if it were obvious, it would have already been done. You never know if the dogs will eat the dog food.
If your hypothesis is wrong, you won’t get anywhere unless you pivot to one that’s right. But even if you are right, you’ll probably still fail if the hypothesis is too obvious, since obvious ideas attract too much competition. Investors and founders call this “non-consensus and right.”4
Non-consensus is why so many startup ideas seem ridiculous at first. Would you have invested in “let strangers sleep in your spare bedroom,” “the world’s 20th search engine,” or “upload your source code to the cloud?”
The founders don’t found anything
The main reason a startup “fails” is that it is never started. True, most people should not start a startup, but the number of potentially great founders who don’t take the leap must far exceed the ones who do. They may not know credible founder role models, advisors, or investors. They may live somewhere with a social stigma against working for a tiny, unknown company rather than landing a coveted big company or government job. Or they may not work up the nerve to take such a massive leap into the unknown.
Uninvent’s mission is to help close these gaps. We need more successful startups, so we need more great founders willing to start them, need more of those startups to succeed, and we want anyone who starts or works at a startup to have such a great experience that they can’t wait to do it again.
My story
I won’t talk much about myself in Uninvent or share a series of war stories from my career, although those can make excellent reading.5 But I do want you to know where I’m coming from.
I’ve been a founder or the first employee at five startups and have invested in or advised about 50 more. I’ve been through an IPO, on both sides of several acquisitions, on the executive teams of two public companies, and I ran one startup into the ground. I’ve been a CEO, General Manager, Chief Product Officer, VP of Engineering, CTO, VP of Customer Success, board member, advisor, and investor.
My current company is Gladly, which sells customer service software to retail and e-commerce companies. I’m also an advisor to Point Nine Capital, and I angel invest and advise other startups.
I’ve helped raise over half a billion dollars, have hired a few thousand people, and have let go or laid off a few hundred more. I’ve sat through a thousand executive team meetings, several hundred board meetings, and thousands of one-on-ones and staff meetings. I’ve given a few dozen conference keynotes, lectured at Stanford, Harvard, and ESADE, written 2,000 Quora answers, and was nominated for a Webby (yeah, that was a thing for a hot moment).
I’m also proud that in my 30-year startup journey, I've built a fantastic family, made great friends, and maintained my health, logging thousands of miles running, hiking, open water swimming, mountain biking, and cross-country skiing in San Francisco and Lake Tahoe. My family has taken several sabbaticals between startups, spent in Europe, where I’ve invested and advised several startups and became an advisor at Point Nine Capital, where I work with their portfolio.
Am I telling you this to convince you that you should listen to me because I’m an expert? Not exactly.
I know nothing about most markets, including B2C, gaming, biotech, cleantech, or anything other than my specialty, B2B software. I’ve failed several times because I didn’t follow the same advice I’ll share here. I still make mistakes, like delaying letting a bad hire go or not checking that one last reference for a critical hire. I’m still on a steep learning curve. I cringe at things I believed just a year ago, and a year from now, I’ll probably be scrambling to update some of my opinions here. I’ve had advantages I probably don’t fully appreciate since I’m a white male who graduated from a good school at the right time.
Most of all, I don’t know you, which highlights a recurring theme in Uninvent, which is to acknowledge the limits of startup advice. Founders are bombarded with suggestions about how to run their startups, much of which amounts to, “Here’s what I did, just do the same thing.” Some of this advice is excellent, but much of it depends on context. I’ll discuss guidelines for filtering advice and work to understand the first principles that underlie it.
Most importantly, Uninvent explores the gap between knowing the right thing to do and doing it. I can’t tell you if you should fire your VP of Marketing, but I can tell you that you’ll wait way too long to do it, you’ll lose sleep over it, and you’ll delude yourself that maybe he’ll improve with just a little bit more time (he won’t).
What Uninvent does not cover
An excellent way to describe what Uninvent is about is to start with what it’s not about:
The secret playbook
When an intelligent person asks an interesting question, the answer is, “It depends.” It depends on the people, the market, the product, and the timing. Every decision comes with tradeoffs and compromises. No playbook, checklist, or recipe guarantees success, or else we’d all be billionaires.
“It depends” is not a great way to get subscribers, but that’s not the goal. Uninvent wallows in the gray areas, helping you absorb the firehose of advice coming at you, extract the deeper principles that underlie it, and then use them to carve a path to success that works for you.
Fundraising
Startup fundraising has been covered to death, partially because so many venture capitalists blog to build their brands. You can find hundreds of blog posts, sample pitch decks, demo day videos, and books on how to raise funding for a startup. I won’t toss more onto that teetering pile.6
I don’t cover fundraising for a more basic reason, though: it’s less important than you think. Founders usually think their idea is so good that their only barrier is money. They think that once the funding rolls in, they’ll hire some engineers and build their product, and it will fly off the shelves. This almost never happens. Founders who raise money from good investors fail all of the time, usually because of problems that money couldn’t have solved.
Regardless, the best way to raise funding is to build something worth funding: a compelling team building a great business. Once you’re on the path to doing that, you can easily learn how to connect with investors and share your story with them.
How to get ideas
A great startup seldom happens because a would-be founder woke up one day, decided a startup would be cool, brainstormed some ideas on a whiteboard, and picked the most plausible one. “Whiteboard ideas” are usually picked over, generic, and obvious, managing to be both consensus and wrong.7 The founders who pursue them seldom have unique insight into the problem or passion for solving it.
The best startups come from a compelling set of founders who lived a set of experiences that gave them insight into a market and a problem that market had. They start a company to get a solution into the hands of those customers.
You hopefully already know the startup you are building and are looking for help to build it better and faster. If you don’t, this can motivate you to find that idea and give you a preview of your life once you do. We’ll also help you learn why you need to be “all in'' on your idea; startups are so hard that you probably won’t stick with yours for long if you don’t find an idea you want to live and breathe for a decade.
Functional advice
Uninvent won’t discuss how to design a sales compensation plan, A/B test your landing pages, compute your net dollar retention, or shepherd a drug through clinical trials. We’ll focus on the more universal and timeless problems all founders have, regardless of whether they work in software, biotech, cleantech, or consumer businesses.
What Uninvent does cover
Uninvent has about 60 chapters, each covering an aspect of founding a startup. I’ll publish a new one about once per week. You can see a preview in the Table of Contents.
Each chapter includes:
Stories
We start with a vignette about founders facing typical challenges and opportunities. These stories are “truthy” in that they are inspired by real stories or at least mash-ups of them. Many start with our founder heroes lying awake at night, agonizing over a tough dilemma. You might find these fictional founders to be a bit neurotic, nothing like the decisive and steadfast leader you plan to be. To this, I say: just you wait.
Counterintuitive advice
We call this “Uninvent” for a reason — startups don’t always make sense, and you can’t always rely on your instincts. Founders need to uninvent much of what they think they know about business, especially lessons learned at larger companies. We’ll talk about leaving your comfort zones, risking failure, staying agile, and living with ambiguity and chaos.
Core principles
Instead of stopping at superficial advice like “hire good people” and “be authentic,” Uninvent digs deeper and asks what lower-level principles underlie that advice and what tradeoffs and compromises that advice entails. Great founders learn to make decisions that balance the upsides and the drawbacks.
Great resources
Many successful startup founders and investors are also the best thinkers and writers in the industry. They’ve produced fantastic blog posts, books, videos, and classes. Uninvent links to the best from investors like Paul Graham, YCombinator, and First Round Capital, from founders like Naval Ravikant, as well as more classic sources of business advice like Michael Porter, April Dunford, and Geoffrey Moore.
What’s next
Uninvent has three sections, each of which will resonate differently based on the stage of your startup:
Part One: Leading Yourself
An early-stage startup is its founders. They decide what market to tackle, and they incorporate a company to make it happen. New hires join, investors invest, and customers buy only if they want to do business with those founders. As they build their team, the founders are under a microscope, admired for their strengths but with their blind spots, insecurities, and anxieties magnified.
I’ll discuss how you can get on a rapid learning curve, avoid conceptual biases and sloppy thinking, and leverage your emotions without letting them control you. We’ll see how you can “get shit done,” pushing through procrastination, making hard decisions, and being willing to risk failure, criticism, and ridicule. Most of all, we’ll ask how you can stay sane, calm, and clear-eyed enough to execute at a high level, pushing your limits but not so hard that you blow a gasket and veer off track.
Part Two: Leading Your Team
Once your startup has a product and a few happy customers, your success is driven by the team you build and how well you lead them. You’ll spend most of your time hiring and managing people, and your team will provide you with both your peak moments and greatest heartaches.
Uninvent will examine hiring, paying, and building a strong culture. It will also examine communication, transparency, and removing friction so your team can do its best work. It will ask how you can trust your team and delegate to them while staying close enough to the work to ensure its excellence. We’ll discuss how to challenge your team to get the best from them without stressing them out so much that they disengage.
Part Three Leading Your Startup
Even compelling founders with a great idea and a great team will get nowhere if that team isn’t working on the short list of things that matter. Uninvent discusses strategy, focus, positioning, planning, goal setting, decision-making, and the nuts and bolts of fast but effective execution as you scale.
Let’s jump into Part One: Leading Yourself.
Steve Jobs coined “ding in the universe” in his 2005 commencement speech, which is required viewing for anyone who works with startups (and pretty much anyone else).
The “PayPal Mafia” is the best-known startup network, but almost any startup with a strong culture produces a tight network of people who cross paths for decades.
Once you watch this video of Gromit laying tracks in front of a moving train, it will pop into your head daily. You can thank me later: Gromit Placing Rail Tracks for 10 Hours.
I first heard “non-consensus and right” from legendary Benchmark Capital investor and Stanford Business School lecturer Andy Rachleff. Peter Thiel refers to a similar concept in “Zero to One” when he discusses the “secrets” of great founders.
“The Hard Thing About Hard Things” provides one of the best from-the-trenches views into the psyche of a startup founder and leader.
When it comes time to raise money, you’ll want to read Venture Hacks, Venture Deals, much of the content from YCombinator, and sample pitch decks and critiques of them. Just please don’t watch “Shark Tank.”
Paul Graham’s “How to Get Startup Ideas” is the best writing I’ve found on where founders get their ideas. One of the conclusions might be discouraging: the best ideas often happen when the founders aren’t even looking for them.
Also, check out the Stanford courses “CS183: Startup” (Peter Thiel) and “How to Start a Startup” (Sam Altman). Read SaaStr, especially if you are a B2B startup. Read the Marc Andreessen blog series and the entire series of essays from Paul Graham.
Good post! I think this will be a rich vein for founders to absorb and live by!