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.

Inspired by someone I never met

Inspiration is good and bad.

Paul Jarvis inspires me. He's a web person and writer who created his own category by being himself.

Paul said no thank you when everyone else was developing, building, and assuming greater responsibilities. This isn't success. He rewrote the rules. Working for himself, expanding at his own speed, and doing what he loves were his definitions of success.

Play with a problem that you have

The biggest problem can be not recognizing a problem.

Acceptance without question is deception. When you don't push limits, you forget how. You start thinking everything must be as it is.

For example: working. Paul worked a 9-5 agency work with little autonomy. He questioned whether the 9-5 was a way to live, not the way.

Another option existed. So he chipped away at how to live in this new environment.

Don't simply jump

Internet writers tell people considering quitting 9-5 to just quit. To throw in the towel. To do what you like.

The advice is harmful, despite the good intentions. People think quitting is hard. Like courage is the issue. Like handing your boss a resignation letter.

Nope. The tough part comes after. It’s easy to jump. Landing is difficult.

The landing

Paul didn't quit. Intelligent individuals don't. Smart folks focus on landing. They imagine life after 9-5.

Paul had been a web developer for a long time, had solid clients, and was respected. Hence if he pushed the limits and discovered another route, he had the potential to execute.

Working on the side

Society loves polarization. It’s left or right. Either way. Or chaos. It's 9-5 or entrepreneurship.

But like Paul, you can stretch polarization's limits. In-between exists.

You can work a 9-5 and side jobs (as I do). A mix of your favorites. The 9-5's stability and creativity. Fire and routine.

Remember you can't have everything but anything. You can create and work part-time.

My hybrid lifestyle

Not selling books doesn't destroy my world. My globe keeps spinning if my new business fails or if people don't like my Tweets. Unhappy algorithm? Cool. I'm not bothered (okay maybe a little).

The mix gives me the best of both worlds. To create, hone my skill, and grasp big-business basics. I like routine, but I also appreciate spending 4 hours on Saturdays writing.

Some days I adore leaving work at 5 pm and disconnecting. Other days, I adore having a place to write if inspiration strikes during a run or a discussion.

I’m a part-time creator

I’m a part-time creator. No, I'm not trying to quit. I don't work 5 pm - 2 am on the side. No, I'm not at $10,000 MRR.

I work part-time but enjoy my 9-5. My 9-5 has goodies. My side job as well.

It combines both to meet my lifestyle. I'm satisfied.

Join the Part-time Creators Club for free here. I’ll send you tips to enhance your creative game.

Open to ideas or acquisitions

Failure is an unavoidable aspect of life, yet many recoil at the word.

I've worked on unrelated startup projects. This is a list of products I developed (often as the tech lead or co-founder) and why they failed to launch.

Chess Bet (Betting)

As a chess player who plays 5 games a day and has an ELO rating of 2100, I tried to design a chess engine to rival stockfish and Houdini.

While constructing my chess engine, my cofounder asked me about building a p2p chess betting app. Chess Bet. There couldn't be a better time.

Two people in different locations could play a staked game. The winner got 90% of the bet and we got 10%. The business strategy was clear, but our mini-launch was unusual.

People started employing the same cheat engines I mentioned, causing user churn and defaming our product.

It was the first programming problem I couldn't solve after building a cheat detection system based on player move strengths and prior games. Chess.com, the most famous online chess software, still suffers from this.

We decided to pivot because we needed an expensive betting license.

We relaunched as Chess MVP after deciding to focus on chess learning. A platform for teachers to create chess puzzles and teach content. Several chess students used our product, but the target market was too tiny.

We chose to quit rather than persevere or pivot.

BodaCare (Insure Tech)

‘BodaBoda’ in Swahili means Motorcycle. My Dad approached me in 2019 (when I was working for a health tech business) about establishing an Insurtech/fintech solution for motorbike riders to pay for insurance using SNPL.

We teamed up with an underwriter to market motorcycle insurance. Once they had enough premiums, they'd get an insurance sticker in the mail. We made it better by splitting the cover in two, making it more reasonable for motorcyclists struggling with lump-sum premiums.

Lack of capital and changing customer behavior forced us to close, with 100 motorcyclists paying 0.5 USD every day. Our unit econ didn't make sense, and CAC and retention capital only dug us deeper.

Circle (Social Networking)

Having learned from both product failures, I began to understand what worked and what didn't. While reading through Instagram, an idea struck me.

Suppose social media weren't virtual.

Imagine meeting someone on your way home. Like-minded person

People were excited about social occasions after covid restrictions were eased. Anything to escape. I just built a university student-popular experiences startup. Again, there couldn't be a better time.

I started the Android app. I launched it on Google Beta and oh my! 200 people joined in two days.

It works by signaling if people are in a given place and allowing users to IM in hopes of meeting up in near real-time. Playstore couldn't deploy the app despite its success in beta for unknown reasons. I appealed unsuccessfully.

My infrastructure quickly lost users because I lacked funding.

In conclusion

This essay contains many failures, some of which might have been avoided and others not, but they were crucial learning points in my startup path.

If you liked any idea, I have the source code on Github.

Happy reading until then!

This report from Mark Gurman has stuck with me:

In the News and Stocks apps, the display ads are no different than what you might get on an ad-supported website. In the App Store, the ads are for actual apps, which are probably more useful for Apple users than mortgage rates. Some people may resent Apple putting ads in the News and Stocks apps. After all, the iPhone is supposed to be a premium device. Let’s say you shelled out $1,000 or more to buy one, do you want to feel like Apple is squeezing more money out of you just to use its standard features? Now, a portion of ad revenue from the News app’s Today tab goes to publishers, but it’s not clear how much. Apple also lets publishers advertise within their stories and keep the vast majority of that money. Surprisingly, Today ads also appear if you subscribe to News+ for $10 per month (though it’s a smaller number).

I use Apple News often. It's a good general news catch-up tool, like Twitter without the BS. Customized notifications are helpful. Fast and lovely. Except for advertisements. I have Apple One, which includes News+, and while I understand why the magazines still have brand ads, it's ridiculous to me that Apple enables web publishers to introduce awful ads into this experience. Apple's junky commercials are ridiculous.

We know publishers want and probably requested this. Let's keep Apple News ad-free for the much smaller percentage of paid users, and here's your portion. (Same with Stocks, which is more sillier.)

Paid app placement in the App Store is a wonderful approach for developers to find new users (though far too many of those ads are trying to trick users, in my opinion).

Apple is also planning to increase ads in its Maps app. This sounds like Google Maps, and I don't like it. I never find these relevant, and they clutter up the user experience. Apple Maps now has a UI advantage (though not a data/search one, which matters more).

Apple is nickel-and-diming its customers. We spend thousands for their products and premium services like Apple One. We all know why: income must rise, and new firms are needed to scale. This will eventually backfire.

A reading list for successful people

Elon Musk reads and talks. So, one learns. Many brilliant individuals & amazing literature.

This article recommends 3 Elon Musk novels. All of them helped me succeed. Hope they'll help you.

Douglas Adams's The Hitchhiker's Guide to the Galaxy

Page Count: 193
Rating on Goodreads: 4.23

Arthur Dent is pulled off Earth by a buddy seconds before it's razed for a cosmic motorway. The trio hitchhikes through space and gets into problems.

I initially read Hitchhiker's as a child. To evade my mum, I'd read with a flashlight under the covers. She'd scold at me for not sleeping on school nights when she found out. Oops.

The Hitchhiker's Guide to the Galaxy is lighthearted science fiction.

My favorite book quotes are:

• “Space is big. You won’t believe how vastly, hugely, mind-bogglingly big it is. I mean, you may think it’s a long way down the road to the chemist’s, but that’s just peanuts to space.”

• “Far out in the uncharted backwaters of the unfashionable end of the western spiral arm of the Galaxy lies a small unregarded yellow sun. Orbiting this at a distance of roughly ninety-two million miles is an utterly insignificant little blue-green planet whose ape-descended life forms are so amazingly primitive that they still think digital watches are a pretty neat idea.”

• “On planet Earth, man had always assumed that he was more intelligent than dolphins because he had achieved so much — the wheel, New York, wars, and so on — whilst all the dolphins had ever done was muck about in the water having a good time. But conversely, the dolphins had always believed that they were far more intelligent than man — for precisely the same reasons.”

the Sun Tzu book The Art Of War

Page Count: 273
Rating on Goodreads: 3.97

It's a classic. You may apply The Art of War's ideas to (nearly) every facet of life. Ex:

• Pick your fights.

• Keep in mind that timing is crucial.

• Create a backup plan in case something goes wrong.

• Obstacles provide us a chance to adapt and change.

This book was my first. Since then, I'm a more strategic entrepreneur. Excellent book. And read it ASAP!

My favorite book quotes are:

• “Victorious warriors win first and then go to war, while defeated warriors go to war first and then seek to win.”

• “Engage people with what they expect; it is what they are able to discern and confirms their projections. It settles them into predictable patterns of response, occupying their minds while you wait for the extraordinary moment — that which they cannot anticipate.”

• “If you know the enemy and know yourself, you need not fear the result of a hundred battles. If you know yourself but not the enemy, for every victory gained, you will also suffer a defeat. If you know neither the enemy nor yourself, you will succumb in every battle.”

Peter Thiel's book Zero to One

Page Count: 195
Rating on Goodreads: 4.18

Peter argues the best money-making strategies are typically unproven. Entrepreneurship should never have a defined path to success. Whoever says differently is lying.

Zero to One explores technology and society. Peter is a philosophy major and law school graduate, which informs the work.

Peters' ideas, depth, and intellect stood out in Zero to One. It's a top business book.

My favorite book quotes are:

• “The most valuable businesses of coming decades will be built by entrepreneurs who seek to empower people rather than try to make them obsolete.”

• “The next Bill Gates will not build an operating system. The next Larry Page or Sergey Brin won’t make a search engine. And the next Mark Zuckerberg won’t create a social network. If you are copying these guys, you aren’t learning from them.”

• “If your goal is to never make a mistake in your life, you shouldn’t look for secrets. The prospect of being lonely but right — dedicating your life to something that no one else believes in — is already hard. The prospect of being lonely and wrong can be unbearable.”

The world's most prestigious vintage vehicle show included amazing autos and record-breaking sums.

This 1932 Duesenberg J Figoni Sports Torpedo earned Best of Show in 2022.

David Paul Morris (DPM)/Bloomberg

2022 Pebble Beach Concours d'Elegance winner was a pre-war roadster.

Lee Anderson's 1932 Duesenberg J Figoni Sports Torpedo won Best of Show at Pebble Beach Golf Links near Carmel, Calif., on Sunday. First American win since 2013.

Sandra Button, chairperson of the annual concours, said the car, whose chassis and body had been separated for years, "marries American force with European style." "Its resurrection story is passionate."

Pebble Beach Concours d'Elegance Auction

Since 1950, the Pebble Beach Concours d'Elegance has welcomed the world's most costly collectable vehicles for a week of parties, auctions, rallies, and high-roller meetings. The cold, dreary weather highlighted the automobiles' stunning lines and hues.

DPM/Bloomberg

A visitor photographs a 1948 Ferrari 166 MM Touring Barchetta. This is one of 25 Ferraris manufactured in the years after World War II. First shown at the 1948 Turin Salon. Others finished Mille Miglia and Le Mans, which set the tone for Ferrari racing for years.

DPM/Bloomberg

This year's frontrunners were ultra-rare pre-war and post-war automobiles with long and difficult titles, such a 1937 Talbot-Lago T150C-SS Figoni & Falaschi Teardrop Coupe and a 1951 Talbot-Lago T26 Grand Sport Stabilimenti Farina Cabriolet.

The hefty, enormous coaches inspire visions of golden pasts when mysterious saloons swept over the road with otherworldly style, speed, and grace. Only the richest and most powerful people, like Indian maharaja and Hollywood stars, owned such vehicles.

Antonio Chopitea, a Peruvian sugar tycoon, ordered a new Duesenberg in Paris. Hemmings says the two-tone blue beauty was moved to the US and dismantled in the 1960s. Body and chassis were sold separately and rejoined decades later in a three-year, prize-winning restoration.

The concours is the highlight of Monterey Car Week, a five-day Super Bowl for car enthusiasts. Early events included Porsche and Ferrari displays, antique automobile races, and new-vehicle debuts. Many auto executives call Monterey Car Week the "new auto show."

Many visitors were drawn to the record-breaking auctions.

A 1969 Porsche 908/02 auctioned for $4.185 million. Flat-eight air-cooled engine, 90.6-inch wheelbase, 1,320-pound weight. Vic Elford, Richard Attwood, Rudi Lins, Gérard Larrousse, Kurt Ahrens Jr., Masten Gregory, and Pedro Rodriguez drove it, according to Gooding.

DPM/Bloomberg

The 1931 Bentley Eight Liter Sports Tourer doesn't meet its reserve. Gooding & Co., the official auction house of the concours, made more than $105 million and had an 82% sell-through rate. This powerful open-top tourer is one of W.O. Bentley's 100 automobiles. Only 80 remain.

DPM/Bloomberg

The final auction on Aug. 21 brought in $456.1 million, breaking the previous high of $394.48 million established in 2015 in Monterey. “The week put an exclamation point on what has been an exceptional year for the collector automobile market,” Hagerty analyst John Wiley said.

Many cars that go unsold at public auction are sold privately in the days after. After-sales pushed the week's haul to $469 million on Aug. 22, up 18.9% from 2015's record.

In today's currencies, 2015's record sales amount to $490 million, Wiley noted. The dollar is degrading faster than old autos.

Still, 113 million-dollar automobiles sold. The average car sale price was $583,211, up from $446,042 last year, while multimillion-dollar hammer prices made up around 75% of total sales.

Industry insiders and market gurus expected that stock market volatility, the crisis in Ukraine, and the dollar-euro exchange rate wouldn't influence the world's biggest spenders.

Classic.com's CEO said there's no hint of a recession in an e-mail. Big sales and crowds.

Ticket-holders wore huge hats, flowery skirts, and other Kentucky Derby-esque attire. Coffee, beverages, and food are extra.

DPM/Bloomberg

Mercedes-Benz 300 SL Gullwing, 1955. Mercedes produced the two-seat gullwing coupe from 1954–1957 and the roadster from 1957–1963. It was once West Germany's fastest and most powerful automobile. You'd be hard-pressed to locate one for less $1 million.

DPM/Bloomberg

1955 Ferrari 410 Sport sold for $22 million at RM Sotheby's. It sold a 1937 Mercedes-Benz 540K Sindelfingen Roadster for $9.9 million and a 1924 Hispano-Suiza H6C Transformable Torpedo for $9.245 million. The family-run mansion sold $221.7 million with a 90% sell-through rate, up from $147 million in 2021. This year, RM Sotheby's cars averaged $1.3 million.

Not everyone saw such great benefits.

Gooding & Co., the official auction house of the concours, made more than $105 million and had an 82% sell-through rate. 1937 Bugatti Type 57SC Atalante, 1990 Ferrari F40, and 1994 Bugatti EB110 Super Sport were top sellers.

The 1969 Autobianchi A112 Bertone. This idea two-seater became a Hot Wheels toy but was never produced. It has a four-speed manual drive and an inline-four mid-engine arrangement like the Lamborghini Miura.

DPM/Bloomberg

1956 Porsche 356 A Speedster at Gooding & Co. The Porsche 356 is a lightweight, rear-engine, rear-wheel drive vehicle that lacks driving power but is loved for its rounded, Beetle-like hardtop coupé and open-top versions.

DPM/Bloomberg

Mecum sold $50.8 million with a 64% sell-through rate, down from $53.8 million and 77% in 2021. Its top lot, a 1958 Ferrari 250 GT 'Tour de France' Alloy Coupe, sold for $2.86 million, but its average price was $174,016.

Bonhams had $27.8 million in sales with an 88% sell-through rate. The same sell-through generated $35.9 million in 2021.

Gooding & Co. and RM Sotheby's posted all 10 top sales, leaving Bonhams, Mecum, and Hagerty-owned Broad Arrow fighting for leftovers. Six of the top 10 sellers were Ferraris, which remain the gold standard for collectable automobiles. Their prices have grown over decades.

Classic.com's Calle claimed RM Sotheby's "stole the show," but "BroadArrow will be a force to reckon with."

Although pre-war cars were hot, '80s and '90s cars showed the most appreciation and attention. Generational transition and new buyer profile."

2022 Pebble Beach Concours d'Elegance judges inspect 1953 Siata 208. The rounded coupe was introduced at the 1952 Turin Auto Show in Italy and is one of 18 ever produced. It sports a 120hp Fiat engine, five-speed manual transmission, and alloy drum brakes. Owners liked their style, but not their reliability.

DPM/Bloomberg

The Czinger 21 CV Max at Pebble Beach. Monterey Car Week concentrates on historic and classic automobiles, but modern versions like this Czinger hypercar also showed.

DPM/Bloomberg

The 1932 Duesenberg J Figoni Sports Torpedo won Best in Show in 2022. Lee and Penny Anderson of Naples, Fla., own the once-separate-chassis-from-body automobile.

DPM/Bloomberg