It's ok and even desired to be unprofitable if you're gaining revenue at a reasonable cost and have 100%+ net dollar retention, meaning you never lose customers and expand them. To estimate the acceptable cost of new SaaS revenue, we compare new revenue to operating loss and payback period. If you pay back the customer acquisition cost in 1.5 years and never lose them (100%+ NDR), you're doing well.

To evaluate payback period, we compared new revenue to net operating loss for the last 73 SaaS companies to IPO since October 2017. (55 out of 73). Here's the data. 1/(new revenue/operating loss) equals payback period. New revenue/operating loss equals cost of new revenue.

Payback averages a year. 55 SaaS companies that weren't profitable at IPO got a 1-year payback. Outstanding. If you pay for a customer in a year and never lose them (100%+ NDR), you're establishing a valuable business. The average was 1.3 years, which is within the 1.5-year range.

New revenue costs $0.96 on average. These SaaS companies lost $0.96 every $1 of new revenue last year. Again, impressive. Average new revenue per operating loss was $1.59.

Loss-in-operations definition. Operating loss revenue COGS S&M R&D G&A (technical point: be sure to use the absolute value of operating loss). It's wrong to only consider S&M costs and ignore other business costs. Operating loss and new revenue are measured over one year to eliminate seasonality.

Operating losses are desirable if you never lose a customer and have a quick payback period, especially when SaaS enterprises are valued on ARR. The payback period should be under 1.5 years, the cost of new income < $1, and net dollar retention 100%.

Or the “lie to me” method.

I can predict a startup's success in minutes.

Just interview its founder.

Ask "why?"

I question "why" till I sense him.

I need to feel the person I have in front of me. I need to know if he or she can deliver. Startups aren't easy. Without abilities, a brilliant idea will fail.

Good entrepreneurs have these qualities: He's a leader, determined, and resilient.

For me, they can be split in two categories.

The first entrepreneur aspires to live meaningfully. The second wants to get rich. The second is communicative. He wants to wow the crowd. He's motivated by the thought of one day sailing a boat past palm trees and sunny beaches.

What drives the first entrepreneur is evident in his speech, face, and voice. He will not speak about his product. He's (nearly) uninterested. He's not selling anything. He's not a salesman. He wants to succeed. The product is his fuel.

He'll explain his decision. He'll share his motivations. His desire. And he'll use meaningful words.

Paul Ekman has shown that face expressions aren't cultural. His study influenced the American TV series "lie to me" about body language and speech.

Passionate entrepreneurs are obvious. It's palpable. Faking passion is tough. Someone who wants your favor and money will expose his actual motives through his expressions and language.

The good liar will be able to fool you for a while, but not for long if you pay attention to his body language and how he expresses himself.

And also, if you look at his business plan.

His business plan reveals his goals. Read between the lines.

Entrepreneur 1 will focus on his "why", whereas Entrepreneur 2 will focus on the "how".

Entrepreneur 1 will develop a vision-driven culture.

The second, on the other hand, will focus on his EBITDA.

Why is the culture so critical? Because it will allow entrepreneur 1 to develop a solid team that can tackle his problems and trials. His team's "why" will keep them together in tough times.

"Give me a terrific start-up team with a mediocre idea over a weak one any day." Because a great team knows when to pivot and trusts each other. Weak teams fail.” — Bernhard Schroeder

Closings thoughts

Every VC must ask Why. Entrepreneur's motivations. This "why" will create the team's culture. This culture will help the team adjust to any setback.

How did his money blind me?

Like most fledgling entrepreneurs, I wanted a mentor. I met as many nearby folks with "entrepreneur" in their LinkedIn biographies for coffee.

These meetings taught me a lot, and I'd suggest them to any new creator. Attention! Meeting with many experienced entrepreneurs means getting contradictory advice. One entrepreneur will tell you to do X, then the next one you talk to may tell you to do Y, which are sometimes opposites. You'll have to chose which suggestion to take after the chats.

I experienced this. Same afternoon, I had two coffee meetings with experienced entrepreneurs. The first meeting was with a billionaire entrepreneur who took his company public.

I met him in a swanky hotel lobby and ordered a drink I didn't pay for. As a fledgling entrepreneur, money was scarce.

During the meeting, I demoed the software I'd built, he liked it, and we spent the hour discussing what features would make it a success. By the end of the meeting, he requested I include a killer feature we both agreed would attract buyers. The feature was complex and would require some time. The billionaire I was sipping coffee with in a beautiful hotel lobby insisted people would love it, and that got me enthusiastic.

The second meeting was with a young entrepreneur who had recently raised a small amount of investment and looked as eager to pitch me as I was to pitch him. I forgot his name. I mostly recall meeting him in a filthy coffee shop in a bad section of town and buying his pricey cappuccino. Water for me.

After his pitch, I demoed my app. When I was done, he barely noticed. He questioned my customer acquisition plan. Who was my client? What did they offer? What was my plan? Etc. No decent answers.

After our meeting, he insisted I spend more time learning my market and selling. He ignored my questions about features. Don't worry about features, he said. Customers will request features. First, find them.

Putting your faith in results over relevance

Problems plagued my afternoon. I met with two entrepreneurs who gave me differing advice about how to proceed, and I had to decide which to pursue. I couldn't decide.

Ultimately, I followed the advice of the billionaire.

Obviously.

Who wouldn’t? That was the guy who clearly knew more.

A few months later, I constructed the feature the billionaire said people would line up for.

The new feature was unpopular. I couldn't even get the billionaire to answer an email showing him what I'd done. He disappeared.

Within a few months, I shut down the company, wasting all the time and effort I'd invested into constructing the killer feature the billionaire said I required.

Would follow the struggling entrepreneur's advice have saved my company? It would have saved me time in retrospect. Potential consumers would have told me they didn't want what I was producing, and I could have shut down the company sooner or built something they did want. Both outcomes would have been better.

Now I know, but not then. I favored achievement above relevance.

Success vs. relevance

The millionaire gave me advice on building a large, successful public firm. A successful public firm is different from a startup. Priorities change in the last phase of business building, which few entrepreneurs reach. He gave wonderful advice to founders trying to double their stock values in two years, but it wasn't beneficial for me.

The other failing entrepreneur had relevant, recent experience. He'd recently been in my shoes. We still had lots of problems. He may not have achieved huge success, but he had valuable advice on how to pass the closest hurdle.

The money blinded me at the moment. Not alone So much of company success is defined by money valuations, fundraising, exits, etc., so entrepreneurs easily fall into this trap. Money chatter obscures the value of knowledge.

Don't base startup advice on a person's income. Focus on what and when the person has learned. Relevance to you and your goals is more important than a person's accomplishments when considering advice.

Security, privacy, and a strategy!

How to manage digital assets in worst-case scenarios is a perennial crypto concern. Since blockchain and bitcoin technology is very new, this hasn't been a major issue. Many early developers are still around, and many groups created around this technology are young and feel they have a lot of life remaining. This is why inheritance and estate planning in crypto should be handled promptly. As cryptocurrency's intrinsic worth rises, many people in the ecosystem are holding on to assets that might represent generational riches. With that much value, it's crucial to have a plan. Creating a solid plan entails several challenges.

• the initial hesitation in coming up with a plan

• The technical obstacles to ensuring the assets' security and privacy

• the passing of assets from a deceased or incompetent person

• Legal experts' lack of comprehension and/or understanding of how to handle and treat cryptocurrency.

This article highlights several challenges, a possible web3-native solution, and how to learn more.

The Challenge of Inheritance:

One of the biggest hurdles to inheritance planning is starting the conversation. As humans, we don't like to think about dying. Early adopters will experience crazy gains as cryptocurrencies become more popular. Creating a plan is crucial if you wish to pass on your riches to loved ones. Without a plan, the technical and legal issues I barely mentioned above would erode value by requiring costly legal fees and/or taxes, and you could lose everything if wallets and assets are not distributed appropriately (associated with the private keys). Raising awareness of the consequences of not having a plan should motivate people to make one.

Controlling Change:

Having an inheritance plan for your digital assets is crucial, but managing the guts and bolts poses a new set of difficulties. Privacy and security provided by maintaining your own wallet provide different issues than traditional finances and assets. Traditional finance is centralized (say a stock brokerage firm). You can assign another person to handle the transfer of your assets. In crypto, asset transfer is reimagined. One may suppose future transaction management is doable, but the user must consent, creating an impossible loop.

• I passed away and must send a transaction to the person I intended to deliver it to.

• I have to confirm or authorize the transaction, but I'm dead.

In crypto, scheduling a future transaction wouldn't function. To transfer the wallet and its contents, we'd need the private keys and/or seed phrase. Minimizing private key exposure is crucial to protecting your crypto from hackers, social engineering, and phishing. People have lost private keys after utilizing Life Hack-type tactics to secure them. People that break and hide their keys, lose them, or make them unreadable won't help with managing and/or transferring. This will require a derived solution.

Legal Challenges and Implications

Unlike routine cryptocurrency transfers and transactions, local laws may require special considerations. Even in the traditional world, estate/inheritance taxes, how assets will be split, and who executes the will must be considered. Many lawyers aren't crypto-savvy, which complicates the matter. There will be many hoops to jump through to safeguard your crypto and traditional assets and give them to loved ones.

Knowing RUFADAA/UFADAA, depending on your state, is vital for Americans. UFADAA offers executors and trustees access to online accounts (which crypto wallets would fall into). RUFADAA was changed to limit access to the executor to protect assets. RUFADAA outlines how digital assets are administered following death and incapacity in the US.

A Succession Solution

Having a will and talking about who would get what is the first step to having a solution, but using a Dad Mans Switch is a perfect tool for such unforeseen circumstances. As long as the switch's controller has control, nothing happens. Losing control of the switch initiates a state transition.

Subway or railway operations are examples. Modern control systems need the conductor to hold a switch to keep the train going. If they can't, the train stops.

Enter Sarcophagus

Sarcophagus is a decentralized dead man's switch built on Ethereum and Arweave. Sarcophagus allows actors to maintain control of their possessions even while physically unable to do so. Using a programmable dead man's switch and dual encryption, anything can be kept and passed on. This covers assets, secrets, seed phrases, and other use cases to provide authority and control back to the user and release trustworthy services from this work. Sarcophagus is built on a decentralized, transparent open source codebase. Sarcophagus is there if you're unprepared.