Startup entrepreneurs assume what risks when pitching?

Last week I signed four NDAs.

Four!

NDA stands for non-disclosure agreement. A legal document given to someone receiving confidential information. By signing, the person pledges not to share the information for a certain time. If they do, they may be in breach of contract and face legal action.

Companies use NDAs to protect trade secrets and confidential internal information from employees and contractors. Appropriate. If you manage a huge, successful firm, you don't want your employees selling their information to your competitors. To be true, business NDAs don't always prevent corporate espionage, but they usually make employees and contractors think twice before sharing.

I understand employee and contractor NDAs, but I wasn't asked to sign one. I counsel entrepreneurs, thus the NDAs I signed last week were from startups that wanted my feedback on their concepts.

I’m not a startup investor. I give startup guidance online. Despite that, four entrepreneurs thought their company ideas were so important they wanted me to sign a generically written legal form they probably acquired from a shady, spam-filled legal templates website before we could chat.

False. One company tried to get me to sign their NDA a few days after our conversation. I gently rejected, but their tenacity encouraged me. I considered sending retroactive NDAs to everyone I've ever talked to about one of my startups in case they establish a successful company based on something I said.

Two of the other three NDAs were from nearly identical companies. Good thing I didn't sign an NDA for the first one, else they may have sued me for talking to the second one as though I control the firms people pitch me.

I wasn't talking to the fourth NDA company. Instead, I received an unsolicited email from someone who wanted comments on their fundraising pitch deck but required me to sign an NDA before sending it.

That's right, before I could read a random Internet stranger's unsolicited pitch deck, I had to sign his NDA, potentially limiting my ability to discuss what was in it.

You should understand. Advisors, mentors, investors, etc. talk to hundreds of businesses each year. They cannot manage all the companies they deal with, thus they cannot risk legal trouble by talking to someone. Well, if I signed NDAs for all the startups I spoke with, half of the 300+ articles I've written on Medium over the past several years could get me sued into the next century because I've undoubtedly addressed topics in my articles that I discussed with them.

The four NDAs I received last week are part of a recent trend of entrepreneurs sending out NDAs before meetings, despite the practical and legal issues. They act like asking someone to sign away their right to talk about all they see and hear in a day is as straightforward as asking for a glass of water.

Given this inflow of NDAs, I wanted to briefly remind entrepreneurs reading this blog about the merits and cons of requesting investors (or others in the startup ecosystem) to sign your NDA.

Benefits of having investors sign your NDA include:

None. Zero. Nothing.

Disadvantages of requesting investor NDAs:

• You'll come off as an amateur who has no idea what it takes to launch a successful firm.

• Investors won't trust you with their money since you appear to be a complete amateur.

• Printing NDAs will be a waste of paper because no genuine entrepreneur will ever sign one.

I apologize for missing any cons. Please leave your remarks.

A fascinating business conversation.

This week at Web Summit, I had mentor hour.

Mentor hour connects startups with experienced entrepreneurs.

The YC-selected founder who mentored me had grown his company to $100 million in 18 months.

I had 45 minutes to question him.

I've compiled this.

Context

Founder's name is Zack.

After working in private equity, Zack opted to acquire an MBA.

Surrounded by entrepreneurs at a prominent school, he decided to become one himself.

Unsure how to proceed, he bet on two horses.

On one side, he received an offer from folks who needed help running their startup owing to lack of time. On the other hand, he had an idea for a SaaS to start himself.

He just needed to validate it.

Validating

Since Zack's proposal helped companies, he contacted university entrepreneurs for comments.

He contacted university founders.

Once he knew he'd correctly identified the problem and that people were willing to pay to address it, he started developing.

He earned $100k in a university entrepreneurship competition.

His plan was evident by then.

The other startup's founders saw his potential and granted him $400k to launch his own SaaS.

Hiring

He started looking for a tech co-founder because he lacked IT skills.

He interviewed dozens and picked the finest.

As he didn't want to wait for his program to be ready, he contacted hundreds of potential clients and got 15 letters of intent promising they'd join up when it was available.

YC accepted him by then.

He had enough positive signals to raise.

Raising

He didn't say how many VCs he called, but he indicated 50 were interested.

He jammed meetings into two weeks to generate pressure and encourage them to invest.

Seed raise: $11 million.

Selling

His objective was to contact as many entrepreneurs as possible to promote his product.

He first contacted startups by scraping CrunchBase data.

Once he had more money, he started targeting companies with ZoomInfo.

His VC urged him not to hire salespeople until he closed 50 clients himself.

He closed 100 and hired a CRO through a headhunter.

Scaling

Three persons started the business.

1. He primarily works in sales.

2. Coding the product was done by his co-founder.

3. Another person performing operational duties.

He regretted recruiting the third co-founder, who was ineffective (could have hired an employee instead).

He wanted his company to be big, so he hired two young marketing people from a competing company.

After validating several marketing channels, he chose PR.

$100 Million and under

He developed a sales team and now employs 30 individuals.

He raised a $100 million Series A.

Additionally, he stated

• He’s been rejected a lot. Like, a lot.

• Two great books to read: Steve Jobs by Isaacson, and Why Startups Fail by Tom Eisenmann.

• The best skill to learn for non-tech founders is “telling stories”, which means sales. A founder’s main job is to convince: co-founders, employees, investors, and customers. Learn code, or learn sales.

Conclusion

I often read about these stories but hardly take them seriously.

Zack was amazing.

Three things about him stand out:

1. His vision. He possessed a certain amount of fire.

2. His vitality. The man had a lot of enthusiasm and spoke quickly and decisively. He takes no chances and pushes the envelope in all he does.

3. His Rolex.

He didn't do all this in 18 months.

Not really.

He couldn't launch his company without private equity experience.

These accounts disregard entrepreneurs' original knowledge.

Hormozi will tell you how he founded Gym Launch, but he won't tell you how he had a gym first, how he worked at uni to pay for his gym, or how he went to the gym and learnt about fitness, which gave him the idea to open his own.

Nobody knows nothing. If you scale quickly, it's probable because you gained information early.

Lincoln said, "Give me six hours to chop down a tree, and I'll spend four sharpening the axe."

Sharper axes cut trees faster.

Christopher Janz of Point Nine Capital created the SaaS napkin in 2016. This post shows how founders have raised cash in the last 6 years. View raw data.

Round size

Unsurprisingly, round sizes have expanded and will taper down in 2022. In 2016, pre-seed rounds were $200k to $500k; currently, they're $1-$2m. Despite the macroeconomic scenario, Series A have expanded from $3m to $12m in 2016 to $6m and $18m in 2022.

Valuation

There are hints that valuations are rebounding this year. Pre-seed valuations in 2022 are $12m from $3m in 2016, and Series B prices are $270m from $100m in 2016.

Compared to public SaaS multiples, Series B valuations more closely reflect the market, but Seed and Series A prices seem to be inflated regardless of the market.

I'd like to know how each annual cohort performed for investors, based on the year they invested and the valuations. I can't access this information.

ARR

Seed firms' ARR forecasts have risen from $0 to $0.6m to $0 to $1m. 2016 expected $1.2m to $3m, 2021 $0.5m to $4m, and this year $0.5m to $2.5m, suggesting that Series A firms may raise with less ARR today. Series B minutes fell from $4.2m to $3m.

Capitalization Rate

2022 is the year that VCs start discussing capital efficiency in portfolio meetings. Given the economic shift in the markets and the stealthy VC meltdown, it's not surprising. Christopher Janz added capital efficiency to the SaaS Napkin as a new statistic for Series A (3.5x) and Series B. (2.5x). Your investors must live under a rock if they haven't asked about capital efficiency. If you're unsure:

The Capital Efficiency Ratio is the ratio of how much a company has spent growing revenue and how much they’re receiving in return. It is the broadest measure of company effectiveness in generating ARR

What next?

No one knows what's next, including me. All startup and growing enterprises around me are tightening their belts and extending their runways in anticipation of a difficult fundraising ride. If you're wanting to raise money but can wait, wait till the market is more stable and access to money is easier.

Blockchain validates transactions with consensus algorithms. Bitcoin and Ethereum use Proof-of-Work, while Polkadot and Cardano use Proof-of-Stake.

Other consensus protocols are used to verify transactions besides these two. This post focuses on Proof-of-Time (PoT), used by Analog, and Proof-of-History (PoH), used by Solana as a hybrid consensus protocol.

PoT and PoH may seem similar to users, but they are actually very different protocols.

Proof-of-Time (PoT)

Analog developed Proof-of-Time (PoT) based on Delegated Proof-of-Stake (DPoS). Users select "delegates" to validate the next block in DPoS. PoT uses a ranking system, and validators stake an equal amount of tokens. Validators also "self-select" themselves via a verifiable random function."

The ranking system gives network validators a performance score, with trustworthy validators with a long history getting higher scores. System also considers validator's fixed stake. PoT's ledger is called "Timechain."

Voting on delegates borrows from DPoS, but there are changes. PoT's first voting stage has validators (or "time electors" putting forward a block to be included in the ledger).

Validators are chosen randomly based on their ranking score and fixed stake. One validator is chosen at a time using a Verifiable Delay Function (VDF).

Validators use a verifiable delay function to determine if they'll propose a Timechain block. If chosen, they validate the transaction and generate a VDF proof before submitting both to other Timechain nodes.

This leads to the second process, where the transaction is passed through 1,000 validators selected using the same method. Each validator checks the transaction to ensure it's valid.

If the transaction passes, validators accept the block, and if over 2/3 accept it, it's added to the Timechain.

Proof-of-History (PoH)

Proof-of-History is a consensus algorithm that proves when a transaction occurred. PoH uses a VDF to verify transactions, like Proof-of-Time. Similar to Proof-of-Work, VDFs use a lot of computing power to calculate but little to verify transactions, similar to (PoW).

This shows users and validators how long a transaction took to verify.

PoH uses VDFs to verify event intervals. This process uses cryptography to prevent determining output from input.

The outputs of one transaction are used as inputs for the next. Timestamps record the inputs' order. This checks if data was created before an event.

PoT vs. PoH

PoT and PoH differ in that:

• PoT uses VDFs to select validators (or time electors), while PoH measures time between events.

• PoH uses a VDF to validate transactions, while PoT uses a ranking system.

• PoT's VDF-elected validators verify transactions proposed by a previous validator. PoH uses a VDF to validate transactions and data.

Conclusion

Both Proof-of-Time (PoT) and Proof-of-History (PoH) validate blockchain transactions differently. PoT uses a ranking system to randomly select validators to verify transactions.

PoH uses a Verifiable Delay Function to validate transactions, verify how much time has passed between two events, and allow validators to quickly verify a transaction without malicious actors knowing the input.

Skip this if you don't want to discover why your lively, no-brainer pitch isn't making $10k a month.

You don't want to be repulsive as an entrepreneur or anyone else. Making friends, influencing people, and converting strangers into customers will be difficult if your words evoke disgust, distrust, or disrespect. You may be one of many entrepreneurs who do this obliviously and involuntarily.

I've had to master selling my skills to recruiters (to land 6-figure jobs on Wall Street), selling companies to buyers in M&A transactions, and selling my own companies' products to strangers-turned-customers. I probably committed every cardinal sin of sales repulsion before realizing it was me or my poor salesmanship strategy.

If you're launching a new business, frustrated by low conversion rates, or just curious if you're repelling customers, read on to identify (and avoid) the 6 fatal errors that can kill any sales pitch.

1. The first indication

So many people fumble before they even speak because they assume their role is to convince the buyer. In other words, they expect to pressure, arm-twist, and combat objections until they convert the buyer. Actuality, the approach stinks of disgust, and emotionally-aware buyers would feel "gross" immediately.

Instead of trying to persuade a customer to buy, ask questions that will lead them to do so on their own. When a customer discovers your product or service on their own, they need less outside persuasion. Why not position your offer in a way that leads customers to sell themselves on it?

2. A flawless performance

Are you memorizing a sales script, tweaking video testimonials, and expunging historical blemishes before hitting "publish" on your new campaign? If so, you may be hurting your conversion rate.

Perfection may be a step too far and cause prospects to mistrust your sincerity. Become a great conversationalist to boost your sales. Seriously. Being charismatic is hard without being genuine and showing a little vulnerability.

People like vulnerability, even if it dents your perfect facade. Show the customer's stuttering testimonial. Open up about your or your company's past mistakes (and how you've since improved). Make your sales pitch a two-way conversation. Let the customer talk about themselves to build rapport. Real people sell, not canned scripts and movie-trailer testimonials.

If marketing or sales calls feel like a performance, you may be doing something wrong or leaving money on the table.

3. Your greatest phobia

Three minutes into prospect talks, I'd start sweating. I was talking 100 miles per hour, covering as many bases as possible to avoid the ones I feared. I knew my then-offering was inadequate and my firm had fears I hadn't addressed. So I word-vomited facts, features, and everything else to avoid the customer's concerns.

Do my prospects know I'm insecure? Maybe not, but it added an unnecessary and unhelpful layer of paranoia that kept me stressed, rushed, and on edge instead of connecting with the prospect. Skirting around a company, product, or service's flaws or objections is a poor, temporary, lazy (and cowardly) decision.

How can you project confidence and trust if you're afraid? Before you make another sales call, face your shortcomings, weak points, and objections. Your company won't be everyone's cup of tea, but you should have answers to every question or objection. You should be your business's top spokesperson and defender.

4. The unintentional apologies

Have you ever begged for a sale? I'm going to say no, however you may be unknowingly emitting sorry, inferior, insecure energy.

Young founders, first-time entrepreneurs, and those with severe imposter syndrome may elevate their target customer. This is common when trying to get first customers for obvious reasons.

• Since you're truly new at this, you naturally lack experience.

• You don't have the self-confidence boost of thousands or hundreds of closed deals or satisfied client results to remind you that your good or service is worthwhile.

• Getting those initial few clients seems like the most difficult task, as if doing so will decide the fate of your company as a whole (it probably won't, and you shouldn't actually place that much emphasis on any one transaction).

Customers can smell fear, insecurity, and anxiety just like they can smell B.S. If you believe your product or service improves clients' lives, selling it should feel like a benevolent act of service, not a sleazy money-grab. If you're a sincere entrepreneur, prospects will believe your proposition; if you're apprehensive, they'll notice.

Approach every sale as if you're fine with or without it. This has improved my salesmanship, marketing skills, and mental health. When you put pressure on yourself to close a sale or convince a difficult prospect "or else" (your company will fail, your rent will be late, your electricity will be cut), you emit desperation and lower the quality of your pitch. There's no point.

5. The endless promises

We've all read a million times how to answer or disprove prospects' arguments and add extra incentives to speed or secure the close. Some objections shouldn't be refuted. What if I told you not to offer certain incentives, bonuses, and promises? What if I told you to walk away from some prospects, even if it means losing your sales goal?

If you market to enough people, make enough sales calls, or grow enough companies, you'll encounter prospects who can't be satisfied. These prospects have endless questions, concerns, and requests for more, more, more that you'll never satisfy. These people are a distraction, a resource drain, and a test of your ability to cut losses before they erode your sanity and profit margin.

To appease or convert these insatiably needy, greedy Nellies into customers, you may agree with or acquiesce to every request and demand — even if you can't follow through. Once you overpromise and answer every hole they poke, their trust in you may wane quickly.

Telling a prospect what you can't do takes courage and integrity. If you're honest, upfront, and willing to admit when a product or service isn't right for the customer, you'll gain respect and positive customer experiences. Sometimes honesty is the most refreshing pitch and the deal-closer.

6. No matter what

Have you ever said, "I'll do anything to close this sale"? If so, you've probably already been disqualified. If a prospective customer haggles over a price, requests a discount, or continues to wear you down after you've made three concessions too many, you have a metal hook in your mouth, not them, and it may not end well. Why?

If you're so willing to cut a deal that you cut prices, comp services, extend payment plans, waive fees, etc., you betray your own confidence that your product or service was worth the stated price. They wonder if anyone is paying those prices, if you've ever had a customer (who wasn't a blood relative), and if you're legitimate or worth your rates.

Once a prospect senses that you'll do whatever it takes to get them to buy, their suspicions rise and they wonder why.

• Why are you cutting pricing if something is wrong with you or your service?

• Why are you so desperate for their sale?

• Why aren't more customers waiting in line to pay your pricing, and if they aren't, what on earth are they doing there?

That's what a prospect thinks when you reveal your lack of conviction, desperation, and willingness to give up control. Some prospects will exploit it to drain you dry, while others will be too frightened to buy from you even if you paid them.

Walking down a two-way street. Be casual.

If we track each act of repulsion to an uneasiness, fear, misperception, or impulse, it's evident that these sales and marketing disasters were forced communications. Stiff, imbalanced, divisive, combative, bravado-filled, and desperate. They were unnatural and accepted a power struggle between two sparring, suspicious, unequal warriors, rather than a harmonious oneness of two natural, but opposite parties shaking hands.

Sales should be natural, harmonious. Sales should feel good for both parties, not like one party is having their arm twisted.

You may be doing sales wrong if it feels repulsive, icky, or degrading. If you're thinking cringe-worthy thoughts about yourself, your product, service, or sales pitch, imagine what you're projecting to prospects. Don't make it unpleasant, repulsive, or cringeworthy.

ZERO GRACE/ZERO MALICE

Big companies and wealthy people make stupid mistakes too.

Your ancestors kept snakes and drank bad water. You (probably) don't because you've learnt from their failures via instinct+, the ultimate life-lessons streaming network in your head. Instincts foretell the future. If you approach a lion, it'll eat you. Our society's nuanced/complex decisions have surpassed instinct. Human growth depends on how we handle these issues. 80% of people believe they are above-average drivers, yet few believe they make many incorrect mistakes that make them risky. Stupidity hurts others like death. Basic Laws of Human Stupidity by Carlo Cipollas:

1. Everyone underestimates the prevalence of idiots in our society.

2. Any other trait a person may have has no bearing on how likely they are to be stupid.

3. A dumb individual is one who harms someone without benefiting themselves and may even lose money in the process.

4. Non-dumb people frequently underestimate how destructively powerful stupid people can be.

5. The most dangerous kind of person is a moron.

Professor Cippola defines stupid as bad for you and others. We underestimate the corporate world's and seemingly successful people's ability to make bad judgments that harm themselves and others. Success is an intoxication that makes you risk-aggressive and blurs your peripheral vision.

Stupid companies and decisions:

Big Dumber

Big-company bad ideas have more bulk and inertia. The world's most valuable company recently showed its board a VR headset. Jony Ive couldn't destroy Apple's terrible idea in 2015. Mr. Ive said that VR cut users off from the outer world, made them seem outdated, and lacked practical uses. Ives' design team doubted users would wear headsets for lengthy periods.

VR has cost tens of billions of dollars over a decade to prove nobody wants it. The next great SaaS startup will likely come from Florence, not Redmond or San Jose.

Apple Watch and Airpods have made the Cupertino company the world's largest jewelry maker. 10.5% of Apple's income, or $38 billion, comes from wearables in 2021. (seven times the revenue of Tiffany & Co.). Jewelry makes you more appealing and useful. Airpods and Apple Watch do both.

Headsets make you less beautiful and useful and promote isolation, loneliness, and unhappiness among American teenagers. My sons pretend they can't hear or see me when on their phones. VR headsets lack charisma.

Coinbase disclosed a plan to generate division and tension within its workplace weeks after Apple was pitched $2,000 smokes. The crypto-trading platform is piloting a program that rates staff after every interaction. If a coworker says anything you don't like, you should tell them how to improve. Everyone gets a 110-point scorecard. Coworkers should evaluate a person's rating while deciding whether to listen to them. It's ridiculous.

Organizations leverage our superpower of cooperation. This encourages non-cooperation, period. Bridgewater's founder Ray Dalio designed the approach to promote extreme transparency. Dalio has 223 billion reasons his managerial style works. There's reason to suppose only a small group of people, largely traders, will endure a granular scorecard. Bridgewater has 20% first-year turnover. Employees cry in bathrooms, and sex scandals are settled by ignoring individuals with poor believability levels. Coinbase might take solace that the stock is 80% below its initial offering price.

Poor Stupid

Fools' ledgers are valuable. More valuable are lists of foolish rich individuals.

Robinhood built a $8 billion corporation on financial ignorance. The firm's median account value is $240, and its stock has dropped 75% since last summer. Investors, customers, and society lose. Stupid. Luna published a comparable list on the blockchain, grew to $41 billion in market cap, then plummeted.

A podcast presenter is recruiting dentists and small-business owners to invest in Elon Musk's Twitter takeover. Investors pay a 7% fee and 10% of the upside for the chance to buy Twitter at a 35% premium to the current price. The proposal legitimizes CNBC's Trade Like Chuck advertising (Chuck made $4,600 into $460,000 in two years). This is stupid because it adds to the Twitter deal's desperation. Mr. Musk made an impression when he urged his lawyers to develop a legal rip-cord (There are bots on the platform!) to abandon the share purchase arrangement (for less than they are being marketed by the podcaster). Rolls-Royce may pay for this list of the dumb affluent because it includes potential Cullinan buyers.

Worst company? Flowcarbon, founded by WeWork founder Adam Neumann, operates at the convergence of carbon and crypto to democratize access to offsets and safeguard the earth's natural carbon sinks. Can I get an ayahuasca Big Gulp?

Neumann raised $70 million with their yogababble drink. More than half of the consideration came from selling GNT. Goddess Nature Token. I hope the company gets an S-1. Or I'll start a decentralized AI Meta Renewable NFTs company. My Community Based Ebitda coin will fund the company. Possible.

Stupidity inside oneself

This weekend, I was in NYC with my boys. My 14-year-old disappeared. He's realized I'm not cool and is mad I let the charade continue. When out with his dad, he likes to stroll home alone and depart before me. Friends told me hell would return, but I was surprised by how fast the eye roll came.

Not so with my 11-year-old. We went to The Edge, a Hudson Yards observation platform where you can see the city from 100 storeys up for $38. This is hell's seventh ring. Leaning into your boys' interests is key to engaging them (dad tip). Neither loves Crossfit, WW2 history, or antitrust law.

We take selfies on the Thrilling Glass Floor he spots. Dad, there's a bar! Coke? I nod, he rushes to the bar, stops, runs back for money, and sprints back. Sitting on stone seats, drinking Atlanta Champagne, he turns at me and asks, Isn't this amazing? I'll never reach paradise.

Later that night, the lads are asleep and I've had two Zacapas and Cokes. I SMS some friends about my day and how I feel about sons/fatherhood/etc. How I did. They responded and approached. The next morning, I'm sober, have distance from my son, and feel ashamed by my texts. Less likely to impulsively share my emotions with others. Stupid again.