Founder 1: Runs startup for five years. Sells for ~$100M. Makes $30M.
Founder 2: Running startup for ten years (and counting). Valued at ~$1B. Founder shares valued at $30M.
Which founder would you rather be?
/🧵
Huge amount of data analysis and work with leadership behind this. Bottom line: TikTok does not merely reflect pre-existing sentiment—it is shaping views, creating a dangerous environment for Jews. TikTok ratio differs from opinion polls, which show sentiment among Americans aged
A new survey suggests TikTok is a meaningful driver of a surge in antisemitism.
#TikToxic
Spending at least 30 minutes a day on TikTok increases the chances a respondent holds antisemitic or anti-Israel views by 17% (compared with 6% for Instagram and 2% for X).
Since last Sunday, I’ve been locked in my study with a dry cough/fever/headache. Despite trying since Monday, I was tested Friday - extended family had same symptoms and tested positive for COVID19 on Wednesday
It wasn't been a good week, but it’s given me time to think.
/1
We spend a lot of time trying to figure out what makes startups explode out of the gates, and not nearly enough on what drives the “overnight successes, a decade in the making.” e.g. Lynda/MailChimp/Olo
Some quick thoughts on what powers that type of entrepreneur:
1/12
"We learned a lot"
This phrase is almost always a euphemism for “We've spent nearly all of our capital, don’t have traditional traction, but need more money.”
Those four words that will chill a VC’s soul - here's what you *should* say if you're running out of cash/time. 1/9
If you’re a founder of a startup transitioning from seed to Series A and beyond...
🚨 You 🚨 Must 🚨 Start 🚨 Prioritizing 🚨 Professional 🚨 Development 🚨 Now!
What got you to this point isn't enough to ensure success at the next stage.
Some tips on taking the leap:
/1
Revenue from paying customers is by far the best source of capital for a startup.
The goal of founders should be to turn VC funding into customer funding as rapidly as possible.
Today, pre-seed rounds are being raised based on a deck, an impressive CV, and sometimes little else.
Founders could avoid many dilutive mistakes with a year of experimentation on nights/weekends ....
You need less than you think.
To IPO or not to IPO, that is the question ...
I’m currently in the unforeseen but very fortunate position of having near front row seats in multiple companies that are IPO candidates. The related discussions are equal parts thought-provoking and stressful. Some thoughts: /1
Both my wife and I have tested positive for COVID19 (test results received 11 days post initial symptoms ...). I'm feeling much better and she is hopefully not far behind now. Thanks for all wishes received. So appreciated.
Since last Sunday, I’ve been locked in my study with a dry cough/fever/headache. Despite trying since Monday, I was tested Friday - extended family had same symptoms and tested positive for COVID19 on Wednesday
It wasn't been a good week, but it’s given me time to think.
/1
⌚️ Moreover, my
@Ouraring
and
@Whoop
apps spotted my temp/restlessness before symptoms fully manifested. Is it out of the realm of possibility to think that companies may require employees to wear devices that measure biometrics as a pre-condition of employment?
/5
For most founders, a “humble” $10M payout would represent a huge windfall after a five-year period.
What is considered a poor showing in VC circles – a $50-100M exit – can set up founders (& their children) for life.
Entrepreneurs should guard this class of exit jealously.
/7
I have no idea yet what the future holds, but I’m absolutely confident great entrepreneurs will help build a world that incorporates the lessons of this very difficult time to build a better world for everyone.
/End
With every dollar of venture capital you take, you’re also implicitly committing to a sale of your company at >3X the post-money valuation.
That calculus should help inform your strategic decision-making process.
In terms of probability, the most efficient way for startup founders to secure generational wealth is:
1⃣ Raise a single round of funding
📈 Create as much value as possible with it
💰 Sell the startup relatively early
Founders often don't get to deliver the most important pitch for their startup: the 2-3 line summary that a VC uses to socialize the opportunity with their partners.
Here's how to help them craft one that will resonate:
/1
Early in my career, a lawyer cost me millions of dollars.
Not in legal fees.
Not by doing a bad job
But by doing their job too well.
Here's a cautionary tale about why it's essential to manage your lawyers – closely.
/🧵
Reminder:
Raising venture capital increases the theoretical value of a startup and the paper wealth of its founders.
It also reduces the number of potential buyers for the startup and increases the risk that no buyer can be found, limiting the real wealth of its founders.
100 years ago, World War I and the Spanish Flu together claimed ~100M lives.
At a time when the world was in tatters, Guccio Gucci began to stitch together a business that would become a byword for beauty.
He wasn't alone in seeing opportunity...
/1
Venture capital is a magical tool that allows you to play by different rules – for a while.
However, if growth slows, it can vanish instantly and leave you with the everyday realities of running a small business.
In the graveyard of dead startups, the epitath "great product and poor distribution" is 100X more common than "amazing sales team that got beat on product."
In terms of pure probability, the most efficient way for founders to secure generational wealth for themselves is to raise a single round of funding, create as much value as possible with it, and sell the startup relatively early.
/6
🗣️ Voice and gesture will also become increasingly important in the built environment, as
@Balajis
noted early in February. What were once novelty technologies may soon become prerequisites.
/4
All elevators, doors, faucets, and handles will go to voice or gesture based activation as standard.
The technology now exists for hands-free everything. This is going to be hygiene 2.0 across society, at least in Asia.
As every founder finds out on every funding round:
Lead investors are golden.
Followers are a dime a dozen.
Those who are prepared to lead quickly with conviction on fair terms deserve more time and gratitude than the others.
With every dollar of venture capital you take you’re also implicitly committing to a sale of your company at ~10X the post.
That calculus should help inform your strategic decision-making process.
💼🔂 A Brief Memo on the B2B2C Model 🔂💼
B2B2C business models, where a startup sells to an enterprise with the intent that the enterprise sells to consumers can be a power strategy.
It’s also a dangerous approach for startups that can lead to total disaster.
Here’s why:
/1
There is no easy – or correct – answer to this question. These founders have different life situations and ambitions. However, I don’t think VCs do enough to highlight the financial risks founders take by getting on the fundraising treadmill.
/2
Raising venture capital increases the theoretical value of a startup and the paper wealth of its founders.
It also reduces the number of potential buyers for the startup and increases the risk that no buyer can be found, limiting the real wealth of its founders.
/3
🌡️ The idea of wearing an activity tracker in exchange for lower insurance premiums has been piloted for years, will fear of severe illness mean an out of range temperature blocks your key card access at the office? I wouldn’t be surprised to see this in our “new normal.”
/6
High-quality startup problem: company starts to scale but one of the co-founders can’t grow at the same pace as the other. Good problem but a real challenge nonetheless. Here are some thoughts on how I’ve seen it handled well (and not). /1
📺 Video conferencing has been the obvious winner this week, but I don’t think people fully appreciate how widespread it can become under quarantine - e.g. my wife and I are isolated separately and are video chatting with our kids — not a use case Zoom has optimized for.
/3
Not every tech product or service should be a business.
An even smaller set should be venture-backed startups.
Plenty of potential $100M companies fail because they raised capital as if they would become billion-dollar unicorns.
It’s always possible to raise more money to pursue a bigger goal.
However, once you’ve taken money, you can’t accept many smaller but still life-changing exits.
VC ratchets in one direction, and founders should be exceedingly confident before they add more pressure.
/End
“Just Survive.”
This is the most common piece of advice that I’ve shared with portfolio CEOs over the last month.
Three additions to it:
🙈 *So far* isn’t a long-term solution.
🎱 If you’re feeling confident, stop!
❓ Who is your customer’s customer?
/1
This way of thinking runs counter to conventional VC wisdom that founders should focus on the "size of the pie", or their startup's overall value, rather than the "size of their slice", or the founder's ownership ......
I'm here to tell founders to guard their slices.
/8
I’ve had the good fortune to be an investor for almost 15 years and have backed 100s of startups. Only one company in all that time deliberately defrauded its VCs. Catastrophes like Theranos (not an investor) are shocking in part because outright fraud is mercifully rare.
/1
VCs evaluate startup pitches along four dimensions:
⚙️ Business/Team: Are the founders/model/metrics strong?
📣 Pitch: Is the story compelling?
💵 Deal: Are the terms attractive?
👂Audience: Does the VC know/like this space?
So, how can founders improve their odds?
/🧵
I recently shared a thread urging founders to preserve their exit optionality by limiting the amount of capital they raise.
Read this next part … if only because you would prefer to own more of your startup.
Skip it if you want to help your VC to buy another yacht.
/🧵
Founder 1: Runs startup for five years. Sells for ~$100M. Makes $30M.
Founder 2: Running startup for ten years (and counting). Valued at ~$1B. Founder shares valued at $30M.
Which founder would you rather be?
/🧵
So much of the “dream” seems to be to build a startup and sell to a larger strategic/tech company.
If you thought your company might survive a thousand years, what might you do differently?
What would you build if you could hand your stock down to your grandchildren?
/1
Beyond the financial consideration, these startups are intrinsically rewarding in the extreme. In an industry that includes jargon like "flips" and "quick wins", seeing a founder's true vision come to life is so extremely gratifying. 12/12
A "humble" $15M windfall from the sale of a startup is life-changing for most founders.
$75M-$100M startup exits are rarer than you might think.
Be careful when trading away substantial exit opportunities for easy venture capital and unicorn valuations.
👓 Bi-focal Vision
All entrepreneurs claim to have "vision." It's easy to wax poetic about how tech will change the world in the coming years. Rare is the ability to pair that perspective with views on how to make the cash register ring in the next 30 days. 2/12
Today
@Coupang
becomes $CPNG. 11 years after being invited by Bom Kim to participate in Coupang's seed round, its astounding trajectory reminds me of three key facts:
🤝 Founders > Markets
🏁 Velocity = Victory
☎️ Always take
@billackman
’s call
/🧵
How long will you wait for your startup to succeed?
🗓️ A year? Easy.
⛳️ Five? Par for the course.
🧓 A decade? Requires dedication.
🪦 20?! This is your life's work now.
Startups are hard to schedule, but here's why you need to consider the question of time on day one.
/⏳
9/11 is probably the closest analog to this kind of event in my living memory and that horrific event transformed the meaning of “normal” dramatically. Pat-downs and invasive body scans were once the stuff of sci-fi, but we accepted the trade-off of safety and convenience.
/10
The most valuable things VCs can do for founders:
💰 Assist with the next funding round
🎯 Coach founders through an M&A process
☎️ Help close key hires
Everything else is a bonus.
As my fever dreams pass and my ability to process critical thought returns, I’ve been spending a lot of time wondering what the world is going to look like when we return to “normal,” and what that might look like, exactly.
A few thoughts:
/2
Today
@Olo
becomes $OLO. I’ve had the honor and privilege of being alongside
@nhglass
from the get-go. Today’s IPO is a major milestone, and I want to share a couple of small reflections:
⏳ You can't be too early
👣 You have to prepare for a long journey
/🧵
I hope the direct impact of this disease is short-lived, but its impact will be long-lasting. The scope of change we accept as normal will be decided in large part by the length and magnitude of this pandemic.
/8
Granting options to your employees is a wonderful perk of being a startup CEO.
It’s a rare thing to be able to offer an employee a potentially life-changing sum of money!
But in order to get options approved you need to work with your board.
Here is how to do it right:
/🧵
🏖️ Perspective
The difference between a $100M exit and a $1B exit is often just a three-week vacation. Some founders get burnt out after a decade of struggle and take the 1st credible offer for their startup. Just as their growth is about to go exponential. 8/12
Luckily, not all founders are motivated primarily by money.
That said, most do care about the value of their equity and, ceteris paribus, would prefer to avoid a decade of all-consuming stress if there is not a larger pot of gold at the end of the process.
/5
I believe ownership percentage – the slice – and not exit value – the pie – will drive financial returns for the majority of startup founders.
Only in extreme outlier cases is the advice to grow the pie the most enriching goal.
/9
You Can’t build a $5B startup without a bias towards action.
&: Patience is a virtue but it’s one rarely associated with entrepreneurship.
@Olo
CEO
@nhglass
recently shared some lessons about how *not* doing things, or sequencing them strategically, helped deliver success.
/🧵
Finally: I promise you won't be the first founder to go back to their investors with hat in hand. However, how you handle the process will determine whether you'll be written off or reinvested in. Understanding the dynamics at play now is half the battle. 9/9
This thread is advice given against our own interest.
Our model works best when the startups we back have $1B+ exits. We want every company we back to reach that threshold.
It’s just not possible, and for founders, not necessary.
/11
I’m still waiting for the results of my test.
COVID-19 or not, I am grateful to have weathered it quite well.
I hope drastically more testing in the USA happens quickly, along with the required treatments.
But I truly can’t imagine things ever go back to “normal.”
/11
This scenario also assumes that the startup is consistently able to justify its valuation.
It never needs to raise capital on a flat or down valuation and the ultimate buyer pays a premium at sale.
None of these facts are given or believed until “the moment”.
/4
💊 Pain tolerance
These founders lose key hires to better-funded, higher-profile startups. Competitors raise more money and grow faster (until their faulty models fail). Family asks these entrepreneurs when they’re going to get a real job?
It can be painful.
For years. 6/12
⛏️ Willingness to toil
Being early means not having the luxury of easy capital. It usually means an endless stream of tough pilot projects & test deployments. Grabbing revenue wherever it can be had. It's hard, often demoralizing, but necessary. 4/12
A step as large as this may seem unlikely, but digital thermometers are already widely used in airports for passengers who pass through customs. Why shouldn’t we expect them to be part of the social contract at a workplace?
/7
"Technical Debt" is a term that gets thrown around quite a bit by engineers but unfortunately tends not to percolate up to the executive level/board of directors until it reaches crisis point.
Here are some insights/thoughts re keeping your technical debt load in check:
/1
Over-optimizing on ownership can lead some founders to make short-sighted decisions too.
Remember, the goal isn’t to save a few percentage points by shortchanging employees in the ESOP but rather to avoid the 50%+ dilution that will be sold in future funding rounds.
/12
The conventional wisdom about "startup geography" often misses the mark.
@josephflaherty
and I have tried to move the conversation from civic boosting to ~empirical footing with data from 200+ exits.
We were surprised by the results!
No single blog post can prepare a founder for the ultra-marathon of fundraising, but this step-by-step guide from
@epaley
is a great place to start:
#CollectiveWisdom
🐢 Patience
These companies are usually absurdly early entrants into their markets. The kind of founder who tries to solve mobile ordering two years before the iPhone. The SaaS merchant in an on-prem world. They often have more faith than sense. 3/12
"This startup is a natural acquisition for…"
That short phrase has justified the creation of countless startups and many billions of dollars of venture capital investment.
However, it's a dangerous line of thinking for founders and VCs for three reasons:
/🧵
Two VC concepts that can be tough to grasp:
1. The exponential potential of small investments.
2. How long it takes for those investments to mature.
Congrats to our friends at
@firstround
@chrisfralic
@joshk
for their uncommon vision and exceptional patience!
@firstround
's investments in Roblox, Square and Uber were in the same fund, but their journeys looked very different. Roblox was more of a slow bake—and a reminder of the importance of patience in company building.
My partner
@joshk
made this slide, which captures it well:
🔎 Late stage diligence is a science. Audited financials provide evidence that is modeled to make semi-accurate predictions about the future.
At Seed and Series, it’s more of an art, akin to abstract expressionism.
Here are some tips to help entrepreneurs nail the process:
/1
A few tips on building enterprise startups – healthcare, big co. tools, etc.
📈 The sales uptick won’t come until year six
🙄 Don’t be a subject matter snob
🤝 Everyone has to sell
📜 Pick VCs with long track records
🧑🎓 Prepare to teach
🐌 Move slowly and get buy-in
/🧵
If COVID-19 runs its course quickly, perhaps we will snap back to the status quo ante.
But we should also prepare for a world where many tragically perish across the globe, the economy is thrown into turmoil for months upon months and all looks quite different indeed.
/9
Raising VC increases the theoretical value of a startup and the paper wealth of its founders.
It simultaneously reduces the number of potential buyers for the startup.
This *increases the risk* that no buyer can be found, limiting the real wealth of its founders.
Many $100 million companies fail because they raised capital as if they would become multi-billion-dollar unicorns.
So how should a startup that is unsure about its ultimate scale proceed?
Carefully.
🃏 Reputational risk tolerance
All startups are risky. But there's a big difference between spending two years at a startup that fails and 10+. These founders define "all-in" and leave little room for "pivoting" their personal brands. 9/12
Startups measure their survival quarter to quarter, while big companies plan in five-year increments.
It’s often shocking how ... slowly big company partners move on everything from email to product roll-outs.
Keep this in mind before signing big deals with behemoth partners.
Does your startup have an impressive cash stockpile?
If so, the following will soon be plentiful:
⭐️ Talent
🥊 Competitors looking for soft landings
📣 Affordable customer acquisition
Are you ready to take advantage of this moment?
A few thoughts on how to prepare:
/🧵
🔥 Cheerleading
I've been involved with a company in this mold for 14 years. TBH, I nearly wrote it off multiple times in the first six years. But whenever I got close, the founder reignited my excitement and did the same for the team. A true super power. 7/12
It's hard to spot these entrepreneurs. Aside from being "too early", many of these traits only present themselves well into the journey, but we should be more mindful about supporting them as they develop. 10/12
Product-led Growth is an amazing thing – when it works.
The stories of founders who toiled on products for years before the market recognized their genius are the stuff of legend – because they’re just so rare.
/1
“We’ve identified a specific customer”
Sure, you might have flailed around in the process of finding a route to market, but now you’ve identified a specific person willing to pay. Not a category, not a company, but the individual that will write you a check. 2/9
This is a hard path for most founders to navigate.
Getting to the point of sustainability can be difficult.
But getting to an exit is even more challenging and only becomes more complicated with larger and larger valuations.
/10
“It’s time to build,” is the new tech mantra & rightly so.
We are unequivocally beset by challenges that require action but the best founders always seem to solve problems by maniacally focusing on:
💼 Use cases
🥇 Talent
🛣️ Go to market
/1
From humble acorns...
Proud to have written the first check into
@PillPack
in 2013, so grateful to have been on this journey with
@tjparker
&
@elliotcohen
The 2008-2009 Global Financial Crisis was a tough time to raise capital for a startup or a new VC firm.
However, those dark days also gave us Uber, Airbnb and minted over 20% of the VCs on this year’s Forbes Midas List. I don’t think that’s pure coincidence.
/1
One of the secrets of B2B entrepreneurship is that a good enough product with exceptional distribution will win more often than an exceptional product with mediocre distribution.
The key question is, “Do they want to grow this company for the next few decades of their life?”
That is the primary reason to consider an IPO. IPOs are not liquidity events for founders.
I repeat:
🚨🚨🚨 IPOS ARE NOT LIQUIDITY EVENTS FOR FOUNDERS 🚨🚨🚨
/5
⚙️ M-A-N-A-G-E-M-E-N-T
VC-backed startups often have a laissez faire mode of management, but these founders believe in it and invest in it. They’re not micromanagers, but they do try instrument the business from its earliest days. Their survival depends on it.
5/12