Tag Archives: Venture Capital

The Power Law (Part Four): The First Venture Deal

They were the best and brightest young engineers American could produce. But they had one problem: their boss was a tyrant.

Shockley Semiconductor Laboratory founder William Shockley shouted at his talented engineers, recorded all phone calls, and even demanded they take lie detector tests. All refused.

Instead, they did something few engineers in the 1950’s had ever done: struck out on their own. But how could these men of modest means start a semiconductor company?


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Enter Arthur Rock, perhaps the first venture capitalist. Rock invested and also brought in entrepreneur Sherman Fairchild, who put in a cool $1.5 million.

The “traitorous eight” engineers were off to the races. The company called itself Fairchild Semiconductor.

This was the first modern-style venture capital deal. This fascinating history is recounted in Sebastian Mallaby’s new book, The Power Law: Venture Capital and the Making of the New Future.

Like today, the Fairchild deal involved equity investment. What’s more, the founders and employees continued to own much of the company.

That employee ownership was a critical advantage.

Its engineers interviewed customers about what they needed before building anything. This made sure the new company’s products were useful.

The engineers had a strong incentive to make sure they built products that sold well. Big sales meant their stock went up!

Fairchild prospered, making huge advances in semiconductors and racking up millions in sales. Rock’s investment proved to be a home run.

His first fund went from $3.4 million to $77 million in just 7 years. This 23-fold return would be absolutely off the charts, even today.

What’s striking about the story of Fairchild is how unlikely it was.

The culture of the 1950’s was all about big institutions, from major corporations to the army. Finance was highly conservative, more concerned with avoiding loss than reaching for enormous gains.

Without this new form of investing, the Fairchild engineers would’ve kept laboring miserably for Shockley. Or perhaps they’d have moved to some lumbering bureaucracy with little interest in their ideas.

Either way, they probably wouldn’t have been able to make the huge technical advances they did at Fairchild.

The impact of what some call “liberation capital” has only grown with time.

Just a fraction of 1% of US firms raise venture capital. But that tiny group of companies accounts for 76% of the market value of IPO’s and 89% of R&D spending in America.

The most valuable assets are increasingly intangible. They are not smoke belching factories but lines of code.

This is why the venture industry will only become more important with time. It’s the only one that’s good at financing these intangible assets.

Most other investors are conservative and want collateral young firms don’t have.

When I meet with an ambitious founder today, I sometimes wonder where they’d be without venture capital. Perhaps they’d be toiling away miserably in some large bureaucracy indifferent to their talents.

And I want to free them.

More on tech:

The Power Law (Part Three): Angels and VC’s

The Power Law (Part Two)

The Power Law (Part One)

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Photo: The “traitorous eight” at the Fairchild Semiconductor offices

The Power Law (Part Three): Angels and VC’s

In the world of venture capital, there are two species: great white shark VC’s and goldfish angel investors. They dwarf us in size and power as we wiggle about looking for an insect to eat.

So I was surprised to learn that in some of the hottest deals, angel investors actually have the advantage.


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In his superb new book The Power Law: Venture Capital and the Making of the New Future, Sebastian Mallaby recounts how the greatest tech companies found their first supporters. Time and again, the hottest companies rejected entreaties to meet from the top venture firms.

Instead, they went to angel investors to raise money quickly and easily with a minimum of oversight.

Mark Zuckerberg refused to meet with Accel early on. He even showed up at the offices of heavyweight Sequoia Capital in his pajamas!

Sequoia founder Don Valentine recognized the stunt for what it was: a provocation. Zuckerberg wanted the princes of Sand Hill Road to know he didn’t need them.

Instead, he turned to Peter Thiel and other angels for his first funding. Unlike the slow moving investment committees of venture firms, they could write a check on the spot.

But Zuckerberg was not the first great entrepreneur to shun VC’s. Google founders Larry Page and Sergey Brin had every firm in the Valley breathing down their necks.

Instead, they met angel Andy Bechtolsheim on their front porch.

After a brief pitch, Betcholsheim raced back to his Porsche and returned with a checkbook. He invested $100,000 when the company wasn’t even incorporated.

Along with angels, lesser known venture firms also back many of the greatest companies. As Mallaby notes:

“…the idea that venture capitalists get into deals on the strength of their brands can be exaggerated. A deal seen by a partner at Sequoia will also be seen by rivals at other firms: in a fragmented cottage industry, there is no lack of competition. Often, winning the deal depends on skill as much as brand: it’s about understanding the business model well enough to impress entrepreneurs; it’s about judging what valuation might be reasonable. One careful tally concluded that new or emerging venture partnerships capture around half the gains in the top deals, and there are myriad examples of famous VC’s having a chance to invest and then flubbing it.”

I was very surprised to learn that being at a top firm isn’t the advantage it may seem. No wonder Sequoia still cold messages founders!

In this competitive environment, I look for ways for us to cooperate.

VC’s can benefit if angels bring them great early stage deals. Angels benefit by being able to help their portfolio companies.

In the end, if we can work together to build the greatest companies of the future, everybody wins!

What are your experiences raising from angels and VC’s? Leave a comment at the bottom and let me know!

More on tech:

The Power Law (Part Two)

The Power Law (Part One)

Managing a Crisis the Sequoia Way

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Photo: Google founders Larry Page and Sergey Brin. “File:Google page brin.jpg” by Ehud Kenan is licensed under CC BY 2.0.

The Power Law (Part Two)

“When in doubt, take the shot.”

Doug Leone, Managing Partner, Sequoia Capital

The partners from prestigious venture firm Accel stood outside an office in Palo Alto, waiting to take theirs.

These were the offices of a young startup called thefacebook.

Most startups would’ve killed to meet them. But thefacebook’s young founder gave the Accel partners the cold shoulder.


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This didn’t stop them. They lurked outside and buttonholed any thefacebook employee they could find.

Eventually, they got the meeting with founder Mark Zuckerberg. And they won the deal, a $10 million check into the company’s Series A round.

To this day, it remains one of the greatest investments in the history of venture capital.

As an angel investor, I always assumed that the prestigious firms like Accel or Sequoia had it easy. The best founders must be falling all over themselves to meet them!

Nothing could be further from the truth. As Sebastian Mallaby chronicles in his superb new book The Power Law: Venture Capital and the Making of the New Future, the greatest firms are also the scrappiest.

Sequoia Capital, perhaps the greatest VC firm in history, wrote their own code to find the most downloaded new iOS apps. One day, it flagged a small program called WhatsApp.

Sequoia partner Jim Goetz sent e-mail after e-mail to WhatsApp’s founder. For months, he never heard a word.

Finally, Goetz was able to get a meeting with WhatsApp’s founder, Jan Koum. In time, Sequoia won the deal.

The investment made Sequoia $3 billion, and WhatsApp is now ubiquitous throughout the world.

So what does this mean for small fries like me?

Even the greatest have to vigorously pursue deals and handle rejection, so don’t give up on an awesome company! If Sequoia isn’t too cool to cold-message a founder on LinkedIn (psst: they’re not), neither am I!

And when I find that rare, incredible startup, I’ll be repeating Leone’s words to myself: “take the shot.”

More on tech:

The Power Law (Part One)

Managing a Crisis the Sequoia Way

Talking Startups and Today’s Fundraising Pullback

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Photo: Doug Leone, Managing Partner, Sequoia Capital. “_SJP1148” by TechCrunch is licensed under CC BY 2.0.

The Power Law (Part One)

“Reasonable people…routinely fail in life’s important missions by not even attempting them.”

The Power Law

Every day for the last 15 months, I’ve sat down in front of my computer and tried to find the next great tech company. Being immersed in the daily details of e-mails and deal memos made me wonder about the history of this most unusual of industries, venture capital.


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So I grabbed a copy of Sebastian Mallaby’s excellent new book The Power Law: Venture Capital and the Making of the New Future. Mallaby traces the history of venture capital from its first deal to today, and explores the principles that drive its success.

The fundamental principle of venture capital is the power law — a small percentage of winners generate almost all the returns:

“Anytime you have outliers whose success multiplies success, you leave the domain of the normal distribution for the land ruled by the power law — from a world in which things vary slightly to one of extreme contrasts. And once you cross that perilous frontier, you better begin to think differently.”

Since just a few companies drive most of the returns, the entire business becomes about finding and investing in those very few companies:

“…each year brings a handful of outliers that hit the proverbial grand slam, and the only thing that matters in venture is to own a piece of them.”

So how should investors identify those rare businesses? Arthur Rock, who was arguably the first venture capitalist, liked to ask open-ended questions like “Who do you admire?” or “What mistakes have you learned from?”

Rock looked for founders who were realistic and determined. He avoided those who were prone to wishful thinking or who tried to please instead of being honest.

Rock’s inquisitive style led him to back Fairchild Semiconductor in the 1950’s in what was the first modern-style venture capital deal.

Founder traits are important, but hard numbers also matter. Google, eBay, Facebook and YouTube all had staggering growth figures early on.

Andy Rachleff, Benchmark partner and early investor in eBay, looks at an even more sophisticated growth metric:

“‘When companies grow exponentially, they don’t suddenly stop,’ Andy Rachleff observed later, adding that it is the ‘second derivative —the changes in the rate of growth of a company’s sales — that really tell a venture investor whether to back it.’”

Once an investor finds that diamond in the rough, he needs to own a piece, even if the price is high. Mallaby notes that Google’s seed round valuation was around $10M, high for its time.

Prone as I am to analysis, I often undervalued actually meeting investors and founders. This book taught me a lot about the importance of networking to the venture industry.

Don Valentine, founder of Sequoia, went to a Silicon Valley bar every Wednesday and Friday to chat with engineers about the next big thing. In the world of startups, investors are the specialists in connecting people with each other.

The more interesting people we meet, the better we’ll be at our job!

Mallaby provides so much great information that I’ll save the rest of the book for another post soon. In the mean time, if you’re interested in startups and venture capital, I urge you to grab yourself a copy!

More on tech:

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

Amp It Up

Managing a Crisis the Sequoia Way

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Photo: “Don Valentine, Sequoia Capital” by jdlasica is licensed under CC BY 2.0.

Managing a Crisis the Sequoia Way

Control what you can control. Be steady but decisive. And most importantly, build a sustainable business where you are in control of your destiny.

Roelof Botha, Sequoia Capital



Lately, I’ve been seeing something I’ve never seen before in the eyes of some of the founders I meet: desperation.


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Fundraising is increasingly difficult, tech has gotten crushed and the economy is almost surely in recession. Companies that were doing great just a few months ago are staring death in the face.

With that in mind, I spent this afternoon digging into Sequoia Capital’s recent presentation on what the downturn means for startups.

It offers the best advice available for startups navigating this difficult market. Sequoia’s partners advise startups to be prepared to cut back to ensure survival, if necessary.

If your runway (time until you run out of money) is getting short, you may have to make painful cuts in spending.

Do the cut exercise (projects, R&D, marketing, other expenses). It doesn’t mean you have to pull the trigger, but that you are ready to do it in the next 30 days if needed.

Doug Leone, Sequoia Capital

Sequoia also emphasizes that this crisis offers many opportunities. Many companies are more focused once they cut back and hunker down for a bear market.

What’s more, recruiting, which has been extremely difficult for many startups, is about to get much easier. As Leone notes, all of the FANG companies have hiring freezes.

This means startups can have their pick of the best possible people.

Even better yet, some of your competitors are about to go out of business! But if you carefully manage cash, you’ll survive and have a chance to dominate your market.

Look at this as a time of incredible opportunity. You play your cards right and you will come out as a strong entity.

Roelof Botha

This downturn doesn’t mean that you have to stop growing. But it may mean paring back side projects to focus like a laser on driving efficient growth in your core business.

You can still sign up customers in a downturn if you have a strong value proposition. Since I mostly invest in SaaS, I found this passage on proving value to business customers especially helpful:

Three reasons why people buy regardless of market conditions (enterprise POV):

● Drive growth

● Save money (real, hard ROI)

● Reduce risk

● Everything else is fluffy “

Carl Eschenbach, Partner, Sequoia Capital

Finally, it’s important to remain hopeful even if things get hard!

“Whatever we are facing today, it can’t be any worse than the uncertainty we faced at the beginning of the pandemic. We will prevail.”

Alfred Lin, Partner, Sequoia Capital

You created your company for a reason. You have a mission to fulfill.

A downturn doesn’t change that. You just have to manage it correctly and seize the opportunity it presents.

The very best of luck to all you brave founders!

What challenges are you seeing in startupland today? Leave a comment at the bottom and let me know!

More on tech:

TALKING STARTUPS AND TODAY’S FUNDRAISING PULLBACK

TALKING ABOUT TODAY’S STARTUP MARKET ON THE ACCELERATOR PODCAST

THE BURN MULTIPLE: WHAT IS IT, AND WHAT CAN IT DO FOR YOU?

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Photo: “Sequoia Capital” by isriya is licensed under CC BY-NC 2.0.

Dealgrace: Uber for Everything Else

Uber is great for rides and food. But what if you need an oil change?

You’re stuck wading through Google listings and making phone calls, trying to find an affordable option that isn’t 20 miles away. Until now.

Dealgrace is basically Uber for everything else. Request an oil change through the app and you get a text within minutes with an excellent price at a shop near you.

Dealgrace can help you with auto repair, home repair, moving, even finding a dentist! It replaces the painful, time consuming process of comparison shopping with a slick app that gets you what you need right away.


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The team at Dealgrace carefully vets every business on the platform to be sure you get awesome service. And the prices are very hard to beat.

I think the opportunity for Dealgrace is huge and I’m delighted to be an investor in their recent seed round. They’re live in over a dozen cities so far and are adding more every day!

Check out Dealgrace and save yourself time and money!

More on tech:

Have a great weekend everybody! 👋

Why Tech Stocks Are Oversold

Talking Startups and Today’s Fundraising Pullback

The Autonomous Weapons of the Future…and Present

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Hedge Fund Tiger Global Losing $136 Million a Day, Down 52%

The pain continued in May for Tiger Global Management. The hedge fund giant is losing money at a rate of over $130 million a day and most of its capital is gone.

From a Bloomberg report that broke this morning:

Losses at Tiger Global Management reached 52% this year, prompting the firm to cut management fees and create separate accounts for the illiquid wagers of customers who want to redeem. 

The firm’s hedge fund sank 14.2% last month, buffeted by losses in several stocks and substantial markdowns in its private assets, according to an investor letter seen by Bloomberg and a person with knowledge of the matter. 


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This comes after massive losses in April:

By April, the hedge fund’s 44% tumble, along with losses in its long-only and crossover funds, wiped out about $16 billion.

These figures put Tiger’s capital at the beginning of 2022 at around $36 billion. After April’s loss, a further 14% slide in May represents a $2.9 billion wipeout for the month.

May’s losses came to about $136 million per trading day. Every day.

As colossal as these losses are, they may be an underestimate of the true damage. Tiger has taken markdowns on its shares in private tech startups, but we have no way of knowing if those markdowns reflect reality.

Another large late stage investor, Fidelity, has taken only minor markdowns on its portfolio, including a 13% haircut on Stripe. Block, a similar fintech giant that happens to be publicly traded, is down 70% from its August high.

Tiger too may be engaging in this sort of wishful thinking.

If that wasn’t bad enough, Tiger may soon face attack from other hedge funds. It has allowed investors to pull out more money than usual, which will require huge stock sales.

Other funds are likely to short Tiger’s positions, knowing that Tiger has to sell regardless of price. This could make Tiger’s losses even worse.

So what’s next for Tiger? Their high-water mark means that until the fund recoups all its losses and a lot more, fees will be minimal.

Those fees pay the fat bonuses hedge funders are used to. Without them, many employees may jump ship.

Indeed, Tiger could shut down completely, daunted by the need to more than double their fund just to get back in the black. Melvin Capital Management recently closed after facing a long future with no juicy performance fees.

I expect to see Tiger’s losses grow as other funds attack its positions. However, a sudden, major run-up in tech stocks could save them at the last minute.

One thing I do know: I’m glad I don’t have any money in Tiger.

What do you think lies ahead for Tiger? And what hedge fund will be next?

Leave a comment at the bottom and let me know!

More on markets:

Hedge Fund Giant Tiger Global Losing $28 Million an Hour

$6B Hedge Fund Cut Off from Trading As Investigation Looms

Citadel Adds Millions to AMC Options Bet

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Photo: Tiger Global CEO Chase Coleman

Why Tech Stocks Are Oversold

It’s no secret that tech stocks have gotten kicked in the face in the last 6 months. The NASDAQ index of tech stocks is down 26% since November:

I’m convinced that public tech stocks are oversold right now. That’s been my gut feeling for at least a month, but today I came across some fascinating statistics.

Sequoia Capital, the best venture capital firm in history, released some stunning figures in a recent presentation to its founders:

– “61% of all software, internet and fintech companies are trading below pre-pandemic 2020 prices”

– “That’s despite many of these companies more than doubling both revenue and profitability”

– “⅓ are trading below COVID lows, when uncertainty and fear was peaking”

“- Growth-adjusted multiples [valuation divided by revenue] have fallen even further and are well below the 10-year average and pushing the 10-year lows”


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If a company doubles its revenue and profits but actually trades for less money than before, that is a bargain! If you liked it at $100 a share and $10 a share in earnings, for example, you have to love it at $75 a share and $20 in earnings!

But what about interest rates?

The NASDAQ is actually cheaper now than it was when the federal funds rate hit its recent peak in July 2019. At that time, the NASDAQ had a PE ratio of around 30 with the federal funds rate at 2.4%.

The current federal funds rate is a paltry 0.33%. Even if you look at rate expectations, they’re only around 2.8%.

Meanwhile, today’s NASDAQ PE is just 22.

And don’t forget, the Fed may not raise rates as much as expected.

Companies are laying off workers, the economy is on the edge of recession, a war is raging in Europe and COVID may return in the fall. There are many potential reasons why the Fed could back off.

Could tech stocks fall further? Absolutely.

But with every company and household pulling back at once, I think inflation will begin to moderate soon. And if it does, the Fed has a lot less reason to raise rates further, putting more pressure on tech stocks.

Fundamentally, here’s the question you have to ask yourself:

“Do I think the value of technology companies will be greater in 20 years or less in 20 years? Will they have more innovative products and paying customers, or fewer?”

The answer is obvious. Technology has transformed every industry and will continue to do so, resulting in massive profits.

And I want to be there when it happens.

What do you think is ahead for tech stocks? Leave a comment at the bottom and let me know!

More on markets:

Hedge Fund Giant Tiger Global Losing $28 Million an Hour

$6B Hedge Fund Cut Off from Trading As Investigation Looms

Credit Suisse May Need Up to $1 Billion After Huge Losses

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Photo: “Nasdaq Take 4” by bfishadow is licensed under CC BY 2.0.

Talking About Today’s Startup Market on The Accelerator Podcast

I had the pleasure of chatting with angel investor Michael Conniff on his The Accelerator podcast recently! We talk about how to find a great startup to invest in, some of my recent investments, and the robot pizza future.

I’ve provided some links to key parts below. Enjoy!

3:28: What I look for in a startup

4:50: The technique for judging startups quickly that I learned from Jason Calacanis

6:31: Why I like SaaS

7:00: Problems with D2C companies

9:00: Why I invested in VADE, which is changing parking forever

13:29: My recent investment in Fathom, which is letting us search podcasts the way we do text

15:52: Why I invested in Capbase, the best way to start your start-up

19:17: Will robots make our pizza in the future? 🍕

22:35: Why I started this blog

25:06: What sectors I invest in

What did you like about the podcast? What did we miss?

And would you like to see more podcast content like this? Leave a comment at the bottom and let me know!

More on tech:

Talking Startups and Today’s Fundraising Pullback

Why Investors BS You

Robot Pizzas and the Future of Fast Food

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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. 

Talking Startups and Today’s Fundraising Pullback

Hey everyone! 👋 Hope your Monday is going great.

I gave a talk at the Starta Accelerator in NYC last week. It was a lot of fun!

I talk about how the venture capital market works, my investing approach, and today’s pullback in fundraising. And a lot more!

Here are some interesting parts:

9:06: When I invest without traction, and David Sack’s latest startup, Callin.

20:01: How long I take to make a decision to invest

23:11: Why Jason Calacanis’s syndicate is the best one out there

29:07: Fundraising in a tougher environment for startups

34:09: Conspiracy theories on Peloton and Sex and the City’s Mr. Big. 🙂

41:02: Why investors BS you

45:21: How I help the startups I invest in

52:37: Jason’s book Angel and other great books on venture capital and startups

59:00: Why single founders are sometimes ruled out by investors, and why they shouldn’t be.

What information here was most useful to you? What did I miss?

Leave a comment at the bottom and let me know!

Have a great week!

More on tech:

Why Investors BS You

Inside Today’s Early Stage Venture Market

The Burn Multiple: What Is It, and What Can It Do for You?

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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.