Wishing for Lasting Companies, Not Penny Stocks or Goodwill Write-Downs

Get me a NASCAR-style company-logoed cremation urn (notice to the executor of my will, theres gonna be a lot of weird requests). I believe in working on projects that would be on your tombstone. As the Homebrew logo is tattooed on my shoulder, expanding the portfolio to my posthumous commemoration is easy. But this isn't an IRR victory lap; it's a hope that the firms we worked for would last beyond my lifetime.

Venture investors too often take credit or distance themselves from startups based on circumstances. Successful companies tell stories of crucial introductions, strategy conversations, and other value. Defeats Even whether our term involves Board service or systematic ethical violations, I'm just a little investment, so there's not much I can do. Since I'm guilty, I'm tossing stones from within the glass home (although we try to own our decisions through the lifecycle).

Post-exit company trajectories are usually unconfounded. Off the cap table, no longer a shareholder (or a diminishing one as you sell off/distribute), eventually leaving the Board. You can cheer for the squad or forget about it, but you've freed the corporation and it's back to portfolio work.

As I look at the downward track of most SPACs and other tarnished IPOs from the last few years, I wonder how I would feel if those were my legacy. Is my job done? Yes. When investing in a business, the odds are against it surviving, let alone thriving and being able to find sunlight. SPAC sponsors, institutional buyers, retail investments. Free trade in an open market is their right. Risking and losing capital is the system working! But

We were lead or co-lead investors in our first three funds, but as additional VCs joined the company, we were pushed down the cap table. Voting your shares rarely matters; supporting the firm when they need it does. Being valuable, consistent, and helping the company improve builds trust with the founders.

I hope every startup we sponsor becomes a successful public company before, during, and after we benefit. My perspective of American capitalism. Well, a stock ticker has a lot of garbage, and I support all types of regulation simplification (in addition to being a person investor in the Long-Term Stock Exchange). Yet being owned by a large group of investors and making actual gains for them is great. Likewise does seeing someone you met when they were just starting out become a public company CEO without losing their voice, leadership, or beliefs.

I'm just thinking about what we can do from the start to realize value from our investments and build companies with bright futures. Maybe seed venture financing shouldn't impact those outcomes, but I'm not comfortable giving up that obligation.

Steve Jobs' initial mission at Apple in 1997 was to destroy. He killed the Newton PDA and Macintosh clones. Apple stopped trying to please everyone under Jobs.

Afterward, there were few highly targeted moves. First, the pink iMac. Modest success. The iPod, iPhone, and iPad made Apple the world's most valuable firm. Each maneuver changed the company's center of gravity and won.

That's the idea behind Schwerpunkt, a German military term meaning "focus." Jobs didn't need to win everywhere, just where it mattered, so he focused Apple's resources on a few key goods. Finding your Schwerpunkt is more important than charts and analysis for excellent strategy.

Comparison of Relative Strength and Relative Weakness

The iPod, Apple's first major hit after Jobs' return, didn't damage Microsoft and the PC, but instead focused Apple's emphasis on a fledgling, fragmented market that generated "sucky" products. Apple couldn't have taken on the computer titans at this stage, yet it beat them.

The move into music players used Apple's particular capabilities, especially its ability to build simple, easy-to-use interfaces. Jobs' charisma and stature, along his understanding of intellectual property rights from Pixar, helped him build up iTunes store, which was a quagmire at the time.

In Good Strategy | Bad Strategy, management researcher Richard Rumelt argues that good strategy uses relative strength to counter relative weakness. To discover your main point, determine your abilities and where to effectively use them.

Steve Jobs did that at Apple. Microsoft and Dell, who controlled the computer sector at the time, couldn't enter the music player business. Both sought to produce iPod competitors but failed. Apple's iPod was nobody else's focus.

Finding The Center of Attention

In a military engagement, leaders decide where to focus their efforts by assessing commanders intent, the situation on the ground, the topography, and the enemy's posture on that terrain. Officers spend their careers learning about schwerpunkt.

Business executives must assess internal strengths including personnel, technology, and information, market context, competitive environment, and external partner ecosystems. Steve Jobs was a master at analyzing forces when he returned to Apple.

He believed Apple could integrate technology and design for the iPod and that the digital music player industry sucked. By analyzing competitors' products, he was convinced he could produce a smash by putting 1000 tunes in my pocket.

The only difficulty was there wasn't the necessary technology. External ecosystems were needed. On a trip to Japan to meet with suppliers, a Toshiba engineer claimed the company had produced a tiny memory drive approximately the size of a silver dollar.

Jobs knew the memory drive was his focus. He wrote a $10 million cheque and acquired exclusive technical rights. For a time, none of his competitors would be able to recreate his iPod with the 1000 songs in my pocket.

How to Enter the OODA Loop

John Boyd invented the OODA loop as a pilot to better his own decision-making. First OBSERVE your surroundings, then ORIENT that information using previous knowledge and experiences. Then you DECIDE and ACT, which changes the circumstance you must observe, orient, decide, and act on.

Steve Jobs used the OODA loop to decide to give Toshiba $10 million for a technology it had no use for. He compared the new information with earlier observations about the digital music market.

Then something much more interesting happened. The iPod was an instant hit, changing competition. Other computer businesses that competed in laptops, desktops, and servers created digital music players. Microsoft's Zune came out in 2006, Dell's Digital Jukebox in 2004. Both flopped.

By then, Apple was poised to unveil the iPhone, which would cause its competitors to Observe, Orient, Decide, and Act. Boyd named this OODA Loop infiltration. They couldn't gain the initiative by constantly reacting to Apple.

Microsoft and Dell were titans back then, but it's hard to recall. Apple went from near bankruptcy to crushing its competition via Schwerpunkt.

Rather than a destination, it is a journey

Trying to win everywhere is a strategic blunder. Win significant fights, not trivial skirmishes. Identifying a focal point to direct resources and efforts is the essence of Schwerpunkt.

When Steve Jobs returned to Apple, PC firms were competing, but he focused on digital music players, and the iPod made Apple a player. He launched the iPhone when his competitors were still reacting. When Steve Jobs said, "One more thing," at the end of a product presentation, he had a new focus.

Schwerpunkt isn't static; it's dynamic. Jobs' ability to observe, refocus, and modify the competitive backdrop allowed Apple to innovate consistently. His strategy was tailored to Apple's capabilities, customers, and ecosystem. Microsoft or Dell, better suited for the enterprise sector, couldn't succeed with a comparable approach.

There is no optimal strategy, only ones suited to a given environment, when relative strength might be used against relative weakness. Discovering the center of gravity where you can break through is more of a journey than a destination; it will become evident after you reach.

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.

DeCap is DeFi's killer app.

“Software is eating the world.” Marc Andreesen, venture capitalist

DeFi. Imagine a blockchain-based alternative financial system that offers the same products and services as traditional finance, but with more variety, faster, more secure, lower cost, and simpler access.

Decentralised finance (DeFi) is a marketplace without gatekeepers or central authority managing the flow of money, where customers engage directly with smart contracts running on a blockchain.

DeFi grew exponentially in 2020/21, with Total Value Locked (an inadequate estimate for market size) topping at $100 billion. After that, it crashed.

The accumulation of funds by individuals with high discretionary income during the epidemic, the novelty of crypto trading, and the high yields given (5% APY for stablecoins on established platforms to 100%+ for risky assets) are among the primary elements explaining this exponential increase.

No longer your older brothers DeFi

Since transactions are anonymous, borrowers had to overcollateralize DeFi 1.0. To borrow $100 in stablecoins, you must deposit $150 in ETH. DeFi 1.0's business strategy raises two problems.

• Why does DeFi offer interest rates that are higher than those of the conventional financial system?;

• Why would somebody put down more cash than they intended to borrow?

Maxed out on their own resources, investors took loans to acquire more crypto; the demand for those loans raised DeFi yields, which kept crypto prices increasing; as crypto prices rose, investors made a return on their positions, allowing them to deposit more money and borrow more crypto.

This is a bull market game. DeFi 1.0's overcollateralization speculation is dead. Cryptocrash sank it.

The “speculation by overcollateralisation” world of DeFi 1.0 is dead

At a JP Morgan digital assets conference, institutional investors were more interested in DeFi than crypto or fintech. To me, that shows DeFi 2.0's institutional future.

DeFi 2.0 protocols must handle KYC/AML, tax compliance, market abuse, and cybersecurity problems to be institutional-ready.

Stablecoins gaining market share under benign regulation and more CBDCs coming online in the next couple of years could help DeFi 2.0 separate from crypto volatility.

DeFi 2.0 will have a better footing to finally decouple from crypto volatility

Then we can transition from speculation through overcollateralization to DeFi's genuine comparative advantages: cheaper transaction costs, near-instant settlement, more efficient price discovery, faster time-to-market for financial innovation, and a superior audit trail.

Akin to Amazon for financial goods

Amazon decimated brick-and-mortar shops by offering millions of things online, warehouses by keeping just-in-time inventory, and back-offices by automating invoicing and payments. Software devoured retail. DeFi will eat banking with software.

DeFi is the Amazon for financial items that will replace fintech. Even the most advanced internet brokers offer only 100 currency pairings and limited bonds, equities, and ETFs.

Old banks settlement systems and inefficient, hard-to-upgrade outdated software harm them. For advanced gamers, it's like driving an F1 vehicle on dirt.

It is like driving a F1 car on a dirt road, for the most sophisticated players

Central bankers throughout the world know how expensive and difficult it is to handle cross-border payments using the US dollar as the reserve currency, which is vulnerable to the economic cycle and geopolitical tensions.

Decentralization is the only method to deliver 24h global financial markets. DeFi 2.0 lets you buy and sell startup shares like Google or Tesla. VC funds will trade like mutual funds. Or create a bundle coverage for your car, house, and NFTs. Defi 2.0 consumes banking and creates Global Wall Street.

Defi 2.0 is how software eats banking and delivers the global Wall Street

Decentralized Capitalism is Emerging

90% of markets are digital. 10% is hardest to digitalize. That's money creation, ID, and asset tokenization.

90% of financial markets are already digital. The only problem is that the 10% left is the hardest to digitalize

Debt helped Athens construct a powerful navy that secured trade routes. Bonds financed the Renaissance's wars and supply chains. Equity fueled industrial growth. FX drove globalization's payments system. DeFi's plans:

If the 20th century was a conflict between governments and markets over economic drivers, the 21st century will be between centralized and decentralized corporate structures.

Offices vs. telecommuting. China vs. onshoring/friendshoring. Oil & gas vs. diverse energy matrix. National vs. multilateral policymaking. DAOs vs. corporations Fiat vs. crypto. TradFi vs.

An age where the network effects of the sharing economy will overtake the gains of scale of the monopolistic competition economy

This is the dawn of Decentralized Capitalism (or DeCap), an age where the network effects of the sharing economy will reach a tipping point and surpass the scale gains of the monopolistic competition economy, further eliminating inefficiencies and creating a more robust economy through better data and automation. DeFi 2.0 enables this.

DeFi needs to pay the piper now.

DeCap won't be Web3.0's Shangri-La, though. That's too much for an ailing Atlas. When push comes to shove, DeFi folks want to survive and fight another day for the revolution. If feasible, make a tidy profit.

Decentralization wasn't meant to circumvent regulation. It circumvents censorship. On-ramp, off-ramp measures (control DeFi's entry and exit points, not what happens in between) sound like a good compromise for DeFi 2.0.

The sooner authorities realize that DeFi regulation is made ex-ante by writing code and constructing smart contracts with rules, the faster DeFi 2.0 will become the more efficient and safe financial marketplace.

More crucially, we must boost system liquidity. DeFi's financial stability risks are downplayed. DeFi must improve its liquidity management if it's to become mainstream, just as banks rely on capital constraints.

This reveals the complex and, frankly, inadequate governance arrangements for DeFi protocols. They redistribute control from tokenholders to developers, which is bad governance regardless of the economic model.

But crypto can only ride the existing banking system for so long before forming its own economy. DeFi will upgrade web2.0's financial rails till then.

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!