I recently wrote about getting VCs excited about Marketplace start-ups. SaaS founders became envious!

Understanding how people wire tens of millions is the only Series A hack I recommend.

Few people understand the intellectual process behind investing.

VC is risk management.

Series A-focused VCs must cover two risks.

1. Market risk

You need a large market to cross a threshold beyond which you can build defensibilities. Series A VCs underwrite market risk.

They must see you have reached product-market fit (PMF) in a large total addressable market (TAM).

2. Execution risk

When evaluating your growth engine's blitzscaling ability, execution risk arises.

When investors remove operational uncertainty, they profit.

Series A VCs like businesses with derisked revenue streams. Don't raise unless you have a predictable model, pipeline, and growth.

Please beat these 3 metrics before Series A:

Achieve $1.5m ARR in 12-24 months (Market risk)

Above 100% Net Dollar Retention. (Market danger)

Lead Velocity Rate supporting $10m ARR in 2–4 years (Execution risk)

Hit the 3 and you'll raise $10M in 4 months. Discussing 2/3 may take 6–7 months.

If none, don't bother raising and focus on becoming a capital-efficient business (Topics for other posts).

Let's examine these 3 metrics for the brave ones.

1. Lead Velocity Rate supporting €$10m ARR in 2 to 4 years

Last because it's the least discussed. LVR is the most reliable data when evaluating a growth engine, in my opinion.

SaaS allows you to see the future.

Monthly Sales and Sales Pipelines, two predictive KPIs, have poor data quality. Both are lagging indicators, and minor changes can cause huge modeling differences.

Analysts and Associates will trash your forecasts if they're based only on Monthly Sales and Sales Pipeline.

LVR, defined as month-over-month growth in qualified leads, is rock-solid. There's no lag. You can See The Future if you use Qualified Leads and a consistent formula and process to qualify them.

With this metric in your hand, scaling your company turns into an execution play on which VCs are able to perform calculations risk.

2. Above-100% Net Dollar Retention.

Net Dollar Retention is a better-known SaaS health metric than LVR.

Net Dollar Retention measures a SaaS company's ability to retain and upsell customers. Ask what $1 of net new customer spend will be worth in years n+1, n+2, etc.

Depending on the business model, SaaS businesses can increase their share of customers' wallets by increasing users, selling them more products in SaaS-enabled marketplaces, other add-ons, and renewing them at higher price tiers.

If a SaaS company's annualized Net Dollar Retention is less than 75%, there's a problem with the business.

Slack's ARR chart (below) shows how powerful Net Retention is. Layer chart shows how existing customer revenue grows. Slack's S1 shows 171% Net Dollar Retention for 2017–2019.

Slack S-1

3. $1.5m ARR in the last 12-24 months.

According to Point 9, $0.5m-4m in ARR is needed to raise a $5–12m Series A round.

Target at least what you raised in Pre-Seed/Seed. If you've raised $1.5m since launch, don't raise before $1.5m ARR.

Capital efficiency has returned since Covid19. After raising $2m since inception, it's harder to raise $1m in ARR.

P9's 2016-2021 SaaS Funding Napkin

In summary, less than 1% of companies VCs meet get funded. These metrics can help you win.

If there’s demand for it, I’ll do one on direct-to-consumer.

Cheers!

5 VC investment criteria

I reviewed 200 startup business concepts last week. Brainache.

The enterprises sold various goods and services. The concepts were achingly similar: give us money, we'll produce a product, then get more to expand. No different from daily plans and pitches.

Most of those 200 plans sounded plausible. But 10% looked venture-worthy. 90% of startups need alternatives to venture finance.

With the success of VC-backed businesses and the growth of venture funds, a common misperception is that investors would fund any decent company idea. Finding investors that believe in the firm and founders is the key to funding.

Incorrect. Venture capital needs investing in certain enterprises. If your startup doesn't match the model, as most early-stage startups don't, you can revise your business plan or locate another source of capital.

Before spending six months pitching angels and VCs, make sure your startup fits these criteria.

Likely to generate $100 million in sales

First, I check the income predictions in a pitch deck. If it doesn't display $100M, don't bother.

The math doesn't work for venture financing in smaller businesses.

Say a fund invests $1 million in a startup valued at $5 million that is later acquired for $20 million. That's a win everyone should celebrate. Most VCs don't care.

Consider a $100M fund. The fund must reach $360M in 7 years with a 20% return. Only 20-30 investments are possible. 90% of the investments will fail, hence the 23 winners must return $100M-$200M apiece. $15M isn't worth the work.

Angel investors and tiny funds use the same ideas as venture funds, but their smaller scale affects the calculations. If a company can support its growth through exit on less than $2M in angel financing, it must have $25M in revenues before large companies will consider acquiring it.

Aiming for Hypergrowth

A startup's size isn't enough. It must expand fast.

Developing a great business takes time. Complex technology must be constructed and tested, a nationwide expansion must be built, or production procedures must go from lab to pilot to factories. These can be enormous, world-changing corporations, but venture investment is difficult.

The normal 10-year venture fund life. Investments are made during first 3–4 years.. 610 years pass between investment and fund dissolution. Funds need their investments to exit within 5 years, 7 at the most, therefore add a safety margin.

Longer exit times reduce ROI. A 2-fold return in a year is excellent. Loss at 2x in 7 years.

Lastly, VCs must prove success to raise their next capital. The 2nd fund is raised from 1st fund portfolio increases. Third fund is raised using 1st fund's cash return. Fund managers must raise new money quickly to keep their jobs.

Branding or technology that is protected

No big firm will buy a startup at a high price if they can produce a competing product for less. Their development teams, consumer base, and sales and marketing channels are large. Who needs you?

Patents, specialist knowledge, or brand name are the only answers. The acquirer buys this, not the thing.

I've heard of several promising startups. It's not a decent investment if there's no exit strategy.

A company that installs EV charging stations in apartments and shopping areas is an example. It's profitable, repeatable, and big. A terrific company. Not a startup.

This building company's operations aren't secret. No technology to protect, no special information competitors can't figure out, no go-to brand name. Despite the immense possibilities, a large construction company would be better off starting their own.

Most venture businesses build products, not services. Services can be profitable but hard to safeguard.

Probable purchase at high multiple

Once a software business proves its value, acquiring it is easy. Pharma and medtech firms have given up on their own research and instead acquire startups after regulatory permission. Many startups, especially in specialized areas, have this weakness.

That doesn't mean any lucrative $25M-plus business won't be acquired. In many businesses, the venture model requires a high exit premium.

A startup invents a new glue. 3M, BASF, Henkel, and others may buy them. Adding more adhesive to their catalogs won't boost commerce. They won't compete to buy the business. They'll only buy a startup at a profitable price. The acquisition price represents a moderate EBITDA multiple.

The company's $100M revenue presumably yields $10m in profits (assuming they’ve reached profitability at all). A $30M-$50M transaction is likely. Not terrible, but not what venture investors want after investing $25M to create a plant and develop the business.

Private equity buys profitable companies for a moderate profit multiple. It's a good exit for entrepreneurs, but not for investors seeking 10x or more what PE firms pay. If a startup offers private equity as an exit, the conversation is over.

Constructed for purchase

The startup wants a high-multiple exit. Unless the company targets $1B in revenue and does an IPO, exit means acquisition.

If they're constructing the business for acquisition or themselves, founders must decide.

If you want an indefinitely-running business, I applaud you. We need more long-term founders. Most successful organizations are founded around consumer demands, not venture capital's urge to grow fast and exit. Not venture funding.

if you don't match the venture model, what to do

VC funds moonshots. The 10% that succeed are extraordinary. Not every firm is a rocketship, and launching the wrong startup into space, even with money, will explode.

But just because your startup won't make $100M in 5 years doesn't mean it's a bad business. Most successful companies don't follow this model. It's not venture capital-friendly.

Although venture capital gets the most attention due to a few spectacular triumphs (and disasters), it's not the only or even most typical option to fund a firm.

Other ways to support your startup:

• Personal and family resources, such as credit cards, second mortgages, and lines of credit

• bootstrapping off of sales

• government funding and honors

• Private equity & project financing

• collaborating with a big business

• Including a business partner

Before pitching angels and VCs, be sure your startup qualifies. If so, include them in your pitch.

Most don't understand the issue until it's too late.

My first startup was what entrepreneurs call the hardest. A two-sided marketplace.

Two-sided marketplaces are the hardest startups because founders must solve the chicken or the egg conundrum.

A two-sided marketplace needs suppliers and buyers. Without suppliers, buyers won't come. Without buyers, suppliers won't come. An empty marketplace and a founder striving to gain momentum result.

My first venture made me a struggling founder seeking to achieve traction for a two-sided marketplace. The company failed, and I vowed never to start another like it.

I didn’t. Unfortunately, my second venture was almost as hard. It failed like the second-hardest startup.

What kind of startup is the second-hardest?

The second-hardest startup, which is almost as hard to develop, is rarely discussed in the startup community. Because of this, I predict more founders fail each year trying to develop the second-toughest startup than the hardest.

Fairly, I have no proof. I see many startups, so I have enough of firsthand experience. From what I've seen, for every entrepreneur developing a two-sided marketplace, I'll meet at least 10 building this other challenging startup.

I'll describe a startup I just met with its two co-founders to explain the second hardest sort of startup and why it's so hard. They created a financial literacy software for parents of high schoolers.

The issue appears plausible. Children struggle with money. Parents must teach financial responsibility. Problems?

It's possible.

Buyers and users are different.

Buyer-user mismatch.

The financial literacy app I described above targets parents. The parent doesn't utilize the app. Child is end-user. That may not seem like much, but it makes customer and user acquisition and onboarding difficult for founders.

The difficulty of a buyer-user imbalance

The company developing a product faces a substantial operational burden when the buyer and end customer are different. Consider classic firms where the buyer is the end user to appreciate that responsibility.

Entrepreneurs selling directly to end users must educate them about the product's benefits and use. Each demands a lot of time, effort, and resources.

Imagine selling a financial literacy app where the buyer and user are different. To make the first sale, the entrepreneur must establish all the items I mentioned above. After selling, the entrepreneur must supply a fresh set of resources to teach, educate, or train end-users.

Thus, a startup with a buyer-user mismatch must market, sell, and train two organizations at once, requiring twice the work with the same resources.

The second hardest startup is hard for reasons other than the chicken-or-the-egg conundrum. It takes a lot of creativity and luck to solve the chicken-or-egg conundrum.

The buyer-user mismatch problem cannot be overcome by innovation or luck. Buyer-user mismatches must be solved by force. Simply said, when a product buyer is different from an end-user, founders have a lot more work. If they can't work extra, their companies fail.

A few days ago, I was discussing dall-e with two art and tech pals. One artist acquaintance said she knew a frightened illustrator. Would the ability to create anything with a click derail her career? The artist feared this. My curator friend smiled and said this has always been a dread among artists. When the camera was invented, didn't painters say this? Even in the Instagram era, painting exists.

When art and technology collide, there's room for innovation, experimentation, and fear — especially if the technology replicates or replaces art making. What is art's future with dall-e? How does technology affect music, beyond visual art? Recently, I saw "ABBA Voyage," a holographic ABBA concert in London.

"Abba voyage?" my phone asked in early March. A Gen X friend I met through a fashion blogging ring texted me.

"What's abba Voyage?" I asked while opening my front door with keys and coffee.

We're going! Marti, visiting London, took me to a show.

"Absolutely no ABBA songs here." I responded.

My parents didn't play ABBA much, so I don't know much about them. Dad liked Jimi Hendrix, Cream, Deep Purple, and New Orleans jazz. Marti told me ABBA Voyage was a holographic ABBA show with a live band.

The show was fun, extraordinary fun. Nearly everyone on the dance floor wore wigs, ankle-breaking platforms, sequins, and bellbottoms. I saw some millennials and Zoomers among the boomers.

I was intoxicated by the experience.

Automatons date back to the 18th-century mechanical turk. The mechanical turk was a chess automaton operated by a person. The mechanical turk seemed to perform like a human without human intervention, but it required a human in the loop to work properly.

Humans have used non-humans in entertainment for centuries, such as puppets, shadow play, and smoke and mirrors. A show can have animatronic, technological, and non-technological elements, and a live show can blur real and illusion. From medieval puppet shows to mechanical turks to AI filters, bots, and holograms, entertainment has evolved over time.

I'm not a hologram skeptic, but I'm skeptical of technology, especially since I work with it. I love live performances, I love hearing singers breathe, forget lines, and make jokes. Live shows are my favorite because I love watching performers make mistakes or interact with the audience. ABBA Voyage was different.

Marti and I traveled to Manchester after ABBA Voyage to see Liam Gallagher. Similar but different vibe. Similar in that thousands dressed up for the show. ABBA's energy was dizzying. 90s chic replaced sequins in the crowd. Doc Martens, nylon jackets, bucket hats, shaggy hair. The Charlatans and Liam Gallagher opened and closed, respectively. Fireworks. Incredible. People went crazy. Yelling exhausted my voice.

This week in music featured AI-enabled holograms and a decades-old rocker. Both are warm and gooey in our memories.

After seeing both, I'm wondering if we need AI hologram shows. Why? Is it good?

Like everything tech-related, my answer is "maybe." Because context and performance matter. Liam Gallagher and ABBA both had great, different shows.

For a hologram to work, it must be impossible and big. It must be big, showy, and improbable to justify a hologram. It must feel...expensive, like a stadium pop show. According to a quick search, ABBA broke up on bad terms. Reuniting is unlikely. This is also why Prince or Tupac hologram shows work. We can only engage with their legacy through covers or...holograms.

I drove around listening to the radio a few weeks ago. "Dreaming of You" by Selena played. Selena's music defined my childhood. I sang along and turned up the volume (or as loud as my husband would allow me while driving on the highway).

I discovered Selena's music six months after her death, so I never saw her perform live. My babysitter Melissa played me her album after I moved to Houston. Melissa took me to see the Selena movie five times when it came out. I quickly wore out my VHS copy. I constantly sang "Bibi Bibi Bom Bom" and "Como la Flor." I love Selena. A Selena hologram? Yes, probably.

Instagram advertised a cellist's Arthur Russell tribute show. Russell is another deceased artist I love. I almost walked down the aisle to "This is How We Walk on the Moon," but our cellist couldn't find it. Instead, I walked to Magnetic Fields' "The Book of Love." I "discovered" Russell after a friend introduced me to his music a few years ago.

I use these as analogies for the Liam Gallagher and ABBA concerts.

You have no idea how much I'd pay to see a hologram of Selena's 1995 Houston Livestock Show and Rodeo concert. Arthur Russell's hologram is unnecessary. Russell's work was intimate and performance-based. We can't separate his life from his legacy; popular audiences overlooked his genius. He died of AIDS broke. Like Selena, he died prematurely. Given his music and history, another performer would be a better choice than a hologram. He's no Selena. Selena could have rivaled Beyonce.

Pop shows' size works for holograms. Along with ABBA holograms, there was an anime movie and a light show that would put Tron to shame. ABBA created a tourable stadium show. The event was lavish, expensive, and well-planned. Pop, unlike rock, isn't gritty. Liam Gallagher hologram? No longer impossible, it wouldn't work. He's touring. I'm not sure if a rockstar alone should be rendered as a hologram; it was the show that made ABBA a hologram.

Holograms, like AI, are part of the future of entertainment, but not all of it. Because only modern interpretations of Arthur Russell's work reveal his legacy. That's his legacy.

Large-scale arena performers may use holograms in the future, but the experience must be impossible. A teacher once said that the only way to convey emotion in opera is through song, and I feel the same way about holograms, AR, VR, and mixed reality. A story's impossibility must make sense, like in opera. Impossibility and bombastic performance must be present for an immersive element to "work." ABBA was an impossible and improbable experience, which made it magical. It helped the holographic show work.

Marti told me about ABBA Voyage. She said it was a great concert. Marti has worked in music since the 1990s. She's a music expert; she's seen many shows.

Ai isn't a god or sentient, and the ABBA holograms aren't real. The renderings were glassy-eyed, flat, and robotic, like the Polar Express or the Jaws shark. Even today, the uncanny valley is insurmountable. We know it's not real because it's not about reality. It was about a suspended moment and performance feelings.

I knew this was impossible, an 'unreal' experience, but the emotions I felt were real, like watching a movie or tv show. Perhaps this is one of the better uses of AI, like CGI and special effects, like the beauty of entertainment- we were enraptured and entertained for hours. I've been playing ABBA since then.

SpaceX's Starship.

Launched last week.

Four minutes in:

SpaceX will succeed. When it does, its massiveness will matter.

Its payload will revolutionize space economics.

Civilization will shift.

We don't yet understand how this will affect space and Earth culture. Grab it.

The Cost of Space Transportation Has Decreased Exponentially

Space launches have increased dramatically in recent years.

We mostly send items to LEO, the green area below:

SpaceX's reusable rockets can send these things to LEO. Each may launch dozens of payloads into space.

With all these launches, we're sending more than simply things to space. Volume and mass. Since the 1980s, launching a kilogram of payload to LEO has become cheaper:

One kilogram in a large rocket cost over $75,000 in the 1980s. Carrying one astronaut cost nearly $5M! Falcon Heavy's $1,500/kg price is 50 times lower. SpaceX's larger, reusable rockets are amazing.

SpaceX's Starship rocket will continue. It can carry over 100 tons to LEO, 50% more than the current Falcon heavy. Thousands of launches per year. Elon Musk predicts Falcon Heavy's $1,500/kg cost will plummet to $100 in 23 years.

In context:

People underestimate this.

2. The Benefits of Affordable Transportation

Compare Earth's transportation costs:

It's no surprise that the US and Northern Europe are the wealthiest and have the most navigable interior waterways.

So what? since sea transportation is cheaper than land. Inland waterways are even better than sea transportation since weather is less of an issue, currents can be controlled, and rivers serve two banks instead of one for coastal transportation.

In France, because population density follows river systems, rivers are valuable. Cheap transportation brought people and money to rivers, especially their confluences.

How come? Why were humans surrounding rivers?

Imagine selling meat for $10 per kilogram. Transporting one kg one kilometer costs $1. Your margin decreases $1 each kilometer. You can only ship 10 kilometers. For example, you can only trade with four cities:

If instead, your cost of transportation is half, what happens? It costs you $0.5 per km. You now have higher margins with each city you traded with. More importantly, you can reach 20-km markets.

However, 2x distance 4x surface! You can now trade with sixteen cities instead of four! Metcalfe's law states that a network's value increases with its nodes squared. Since now sixteen cities can connect to yours. Each city now has sixteen connections! They get affluent and can afford more meat.

Rivers lower travel costs, connecting many cities, which can trade more, get wealthy, and buy more.

The right network is worth at least an order of magnitude more than the left! The cheaper the transport, the more trade at a lower cost, the more income generated, the more that wealth can be reinvested in better canals, bridges, and roads, and the wealth grows even more.

Throughout history. Rome was established around cheap Mediterranean transit and preoccupied with cutting overland transportation costs with their famous roadways. Communications restricted their empire.

The Egyptians lived around the Nile, the Vikings around the North Sea, early Japan around the Seto Inland Sea, and China started canals in the 5th century BC.

Transportation costs shaped empires.Starship is lowering new-world transit expenses. What's possible?

3. Change Organizations, Change Companies, Change the World

Starship is a conveyor belt to LEO. A new world of opportunity opens up as transportation prices drop 100x in a decade.

Satellite engineers have spent decades shedding milligrams. Weight influenced every decision: pricing structure, volumes to be sent, material selections, power sources, thermal protection, guiding, navigation, and control software. Weight was everything in the mission. To pack as much science into every millimeter, NASA missions had to be miniaturized. Engineers were indoctrinated against mass.

No way.

Starship is not constrained by any space mission, robotic or crewed.

Starship obliterates the mass constraint and every last vestige of cultural baggage it has gouged into the minds of spacecraft designers. A dollar spent on mass optimization no longer buys a dollar saved on launch cost. It buys nothing. It is time to raise the scope of our ambition and think much bigger. — Casey Handmer, Starship is still not understood

A Tesla Roadster in space makes more sense.

It went beyond bad PR. It told the industry: Did you care about every microgram? No more. My rockets are big enough to send a Tesla without noticing. Industry watchers should have noticed.

Most didn’t. Artemis is a global mission to send astronauts to the Moon and build a base. Artemis uses disposable Space Launch System rockets. Instead of sending two or three dinky 10-ton crew habitats over the next decade, Starship might deliver 100x as much cargo and create a base for 1,000 astronauts in a year or two. Why not? Because Artemis remains in a pre-Starship paradigm where each kilogram costs a million dollars and we must aggressively descope our objective.

Space agencies can deliver 100x more payload to space for the same budget with 100x lower costs and 100x higher transportation volumes. How can space economy saturate this new supply?

Before Starship, NASA supplied heavy equipment for Moon base construction. After Starship, Caterpillar and Deere may space-qualify their products with little alterations. Instead than waiting decades for NASA engineers to catch up, we could send people to build a space outpost with John Deere equipment in a few years.

History is littered with the wreckage of former industrial titans that underestimated the impact of new technology and overestimated their ability to adapt: Blockbuster, Motorola, Kodak, Nokia, RIM, Xerox, Yahoo, IBM, Atari, Sears, Hitachi, Polaroid, Toshiba, HP, Palm, Sony, PanAm, Sega, Netscape, Compaq, GM… — Casey Handmer, Starship is still not understood

Everyone saw it coming, but senior management failed to realize that adaption would involve moving beyond their established business practice. Others will if they don't.

4. The Starship Possibilities

It's Starlink.

SpaceX invented affordable cargo space and grasped its implications first. How can we use all this inexpensive cargo nobody knows how to use?

Satellite communications seemed like the best way to capitalize on it. They tried. Starlink, designed by SpaceX, provides fast, dependable Internet worldwide. Beaming information down is often cheaper than cable. Already profitable.

Starlink is one use for all this cheap cargo space. Many more. The longer firms ignore the opportunity, the more SpaceX will acquire.

What are these chances?

Satellite imagery is outdated and lacks detail. We can improve greatly. Synthetic aperture radar can take beautiful shots like this:

Have you ever used Google Maps and thought, "I want to see this in more detail"? What if I could view Earth live? What if we could livestream an infrared image of Earth?

We could launch hundreds of satellites with such mind-blowing visual precision of the Earth that we would dramatically improve the accuracy of our meteorological models; our agriculture; where crime is happening; where poachers are operating in the savannah; climate change; and who is moving military personnel where. Is that useful?

What if we could see Earth in real time? That affects businesses? That changes society?

This is arguably the best three-minute demonstration I've ever seen of anything. Derek Sivers turns a shaky video of a lone dancing guy at a music festival into a leadership lesson.

A leader must have the courage to stand alone and appear silly. But what he's doing is so straightforward that it's almost instructive. This is critical. You must be simple to follow!

Now comes the first follower, who plays an important role: he publicly demonstrates how to follow. The leader embraces him as an equal, so it's no longer about the leader — it's about them, plural. He's inviting his friends to join him. It takes courage to be the first follower! You stand out and dare to be mocked. Being a first follower is a style of leadership that is underappreciated. The first follower elevates a lone nut to the position of leader. If the first follower is the spark that starts the fire, the leader is the flint.

This link was sent to me by @ottmark, who noted its resemblance to Kurt Vonnegut's three categories of specialists required for revolution.

The rarest of these specialists, he claims, is an actual genius – a person capable generating seemingly wonderful ideas that are not widely known. "A genius working alone is generally dismissed as a crazy," he claims.

The second type of specialist is much easier to find: a highly intellectual person in good standing in his or her community who understands and admires the genius's new ideas and can attest that the genius is not insane. "A person like him working alone can only crave loudly for changes, but fail to say what their shapes should be," Slazinger argues.

Jeff Veen reduced the three personalities to "the inventor, the investor, and the evangelist" on Twitter.