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.

Writing for readers:

14 years of daily writing.

I post practically everything on social media. I authored hundreds of articles, thousands of tweets, and numerous volumes to almost no one.

Tens of thousands of readers regularly praise me.

I despised writing. I'm stuck now.

I've learned what readers like and what doesn't.

Here are some essential guidelines for writing with impact:

Readers won't understand your work if you can't.

Though obvious, this slipped me up. Share your truths.

Stories engage human brains.

Showing the journey of a person from worm to butterfly inspires the human spirit.

Overthinking hinders powerful writing.

The best ideas come from inner understanding in between thoughts.

Avoid writing to find it. Write.

Writing a masterpiece isn't motivating.

Write for five minutes to simplify. Step-by-step, entertaining, easy steps.

Good writing requires a willingness to make mistakes.

So write loads of garbage that you can edit into a good piece.

Courageous writing.

A courageous story will move readers. Personal experience is best.

Go where few dare.

Templates, outlines, and boundaries help.

Limitations enhance writing.

Excellent writing is straightforward and readable, removing all the unnecessary fat.

Use five words instead of nine.

Use ordinary words instead of uncommon ones.

Readers desire relatability.

Too much perfection will turn it off.

Write to solve an issue if you can't think of anything to write.

Instead, read to inspire. Best authors read.

Every tweet, thread, and novel must have a central idea.

What's its point?

This can make writing confusing.

️ Don't direct your reader.

Readers quit reading. Demonstrate, describe, and relate.

Even if no one responds, have fun. If you hate writing it, the reader will too.

During the dot-com bust, I started my internet career. People used the internet intermittently to check email, plan travel, and do research. The average internet user spent 30 minutes online a day, compared to 7 today. To use the internet, you had to "log on" (most people still used dial-up), unlike today's always-on, high-speed mobile internet. In 2001, Amazon's market cap was $2.2B, 1/500th of what it is today. A study asked Americans if they'd adopt broadband, and most said no. They didn't see a need to speed up email, the most popular internet use. The National Academy of Sciences ranked the internet 13th among the 100 greatest inventions, below radio and phones. The internet was a cool invention, but it had limited uses and wasn't a good place to build a business. 

A small but growing movement of developers and founders believed the internet could be more than a read-only medium, allowing anyone to create and publish. This is web 2. The runner up name was read-write web. (These terms were used in prominent publications and conferences.) 

Web 2 concepts included letting users publish whatever they want ("user generated content" was a buzzword), social graphs, APIs and mashups (what we call composability today), and tagging over hierarchical navigation. Technical innovations occurred. A seemingly simple but important one was dynamically updating web pages without reloading. This is now how people expect web apps to work. Mobile devices that could access the web were niche (I was an avid Sidekick user). 

The contrast between what smart founders and engineers discussed over dinner and on weekends and what the mainstream tech world took seriously during the week was striking. Enterprise security appliances, essentially preloaded servers with security software, were a popular trend. Many of the same people would talk about "serious" products at work, then talk about consumer internet products and web 2. It was tech's biggest news. Web 2 products were seen as toys, not real businesses. They were hobbies, not work-related. 

There's a strong correlation between rich product design spaces and what smart people find interesting, which took me some time to learn and led to blog posts like "The next big thing will start out looking like a toy" Web 2's novel product design possibilities sparked dinner and weekend conversations. Imagine combining these features. What if you used this pattern elsewhere? What new product ideas are next? This excited people. "Serious stuff" like security appliances seemed more limited. 

The small and passionate web 2 community also stood out. I attended the first New York Tech meetup in 2004. Everyone fit in Meetup's small conference room. Late at night, people demoed their software and chatted. I have old friends. Sometimes I get asked how I first met old friends like Fred Wilson and Alexis Ohanian. These topics didn't interest many people, especially on the east coast. We were friends. Real community. Alex Rampell, who now works with me at a16z, is someone I met in 2003 when a friend said, "Hey, I met someone else interested in consumer internet." Rare. People were focused and enthusiastic. Revolution seemed imminent. We knew a secret nobody else did. 

My web 2 startup was called SiteAdvisor. When my co-founders and I started developing the idea in 2003, web security was out of control. Phishing and spyware were common on Internet Explorer PCs. SiteAdvisor was designed to warn users about security threats like phishing and spyware, and then, using web 2 concepts like user-generated reviews, add more subjective judgments (similar to what TrustPilot seems to do today). This staged approach was common at the time; I called it "Come for the tool, stay for the network." We built APIs, encouraged mashups, and did SEO marketing. 

Yahoo's 2005 acquisitions of Flickr and Delicious boosted web 2 in 2005. By today's standards, the amounts were small, around $30M each, but it was a signal. Web 2 was assumed to be a fun hobby, a way to build cool stuff, but not a business. Yahoo was a savvy company that said it would make web 2 a priority. 

As I recall, that's when web 2 started becoming mainstream tech. Early web 2 founders transitioned successfully. Other entrepreneurs built on the early enthusiasts' work. Competition shifted from ideation to execution. You had to decide if you wanted to be an idealistic indie bar band or a pragmatic stadium band. 

Web 2 was booming in 2007 Facebook passed 10M users, Twitter grew and got VC funding, and Google bought YouTube. The 2008 financial crisis tested entrepreneurs' resolve. Smart people predicted another great depression as tech funding dried up. 

Many people struggled during the recession. 2008-2011 was a golden age for startups. By 2009, talented founders were flooding Apple's iPhone app store. Mobile apps were booming. Uber, Venmo, Snap, and Instagram were all founded between 2009 and 2011. Social media (which had replaced web 2), cloud computing (which enabled apps to scale server side), and smartphones converged. Even if social, cloud, and mobile improve linearly, the combination could improve exponentially. 

This chart shows how I view product and financial cycles. Product and financial cycles evolve separately. The Nasdaq index is a proxy for the financial sentiment. Financial sentiment wildly fluctuates. 

Next row shows iconic startup or product years. Bottom-row product cycles dictate timing. Product cycles are more predictable than financial cycles because they follow internal logic. In the incubation phase, enthusiasts build products for other enthusiasts on nights and weekends. When the right mix of technology, talent, and community knowledge arrives, products go mainstream. (I show the biggest tech cycles in the chart, but smaller ones happen, like web 2 in the 2000s and fintech and SaaS in the 2010s.) 

Tech has changed since the 2000s. Few tech giants dominate the internet, exerting economic and cultural influence. In the 2000s, web 2 was ignored or dismissed as trivial. Entrenched interests respond aggressively to new movements that could threaten them. Creative patterns from the 2000s continue today, driven by enthusiasts who see possibilities where others don't. Know where to look. Crypto and web 3 are where I'd start. 

Today's negative financial sentiment reminds me of 2008. If we face a prolonged downturn, we can learn from 2008 by preserving capital and focusing on the long term. Keep an eye on the product cycle. Smart people are interested in things with product potential. This becomes true. Toys become necessities. Hobbies become mainstream. Optimists build the future, not cynics.

Full article is available here

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

Product game mindsets? How do these vary from Project mindset?

1950s spawned the Iron Triangle. Project people everywhere know and live by it. In stakeholder meetings, it is used to stretch the timeframe, request additional money, or reduce scope.

Quality was added to this triangle as things matured.

Quality was intended to be transformative, but none of these principles addressed why we conduct projects.

Value and benefits are key.

Product value is quantified by ROI, revenue, profit, savings, or other metrics. For me, every project or product delivery is about value.

Most project managers, especially those schooled 5-10 years or more ago (thousands working in huge corporations worldwide), understand the world in terms of the iron triangle. What does that imply? They worry about:

a) enough time to get the thing done.

b) have enough resources (budget) to get the thing done.

c) have enough scope to fit within (a) and (b) >> note, they never have too little scope, not that I have ever seen! although, theoretically, this could happen.

Boom—iron triangle.

To make the triangle function, project managers will utilize formal governance (Steering) to move those things. Increase money, scope, or both if time is short. Lacking funds? Increase time, scope, or both.

In current product development, shifting each item considerably may not yield value/benefit.

Even terrible. This approach will fail because it deprioritizes Value/Benefit by focusing the major stakeholders (Steering participants) and delivery team(s) on Time, Scope, and Budget restrictions.

Pre-agile, this problem was terrible. IT projects failed wildly. History is here.

Value, or benefit, is central to the product method. Product managers spend most of their time planning value-delivery paths.

Product people consider risk, schedules, scope, and budget, but value comes first. Let me illustrate.

Imagine managing internal products in an enterprise. Your core customer team needs a rapid text record of a chat to fix a problem. The consumer wants a feature/features added to a product you're producing because they think it's the greatest spot.

Project-minded, I may say;

Ok, I have budget as this is an existing project, due to run for a year. This is a new requirement to add to the features we’re already building. I think I can keep the deadline, and include this scope, as it sounds related to the feature set we’re building to give the desired result”.

This attitude repeats Scope, Time, and Budget.

Since it meets those standards, a project manager will likely approve it. If they have a backlog, they may add it and start specking it out assuming it will be built.

Instead, think like a product;

What problem does this feature idea solve? Is that problem relevant to the product I am building? Can that problem be solved quicker/better via another route ? Is it the most valuable problem to solve now? Is the problem space aligned to our current or future strategy? or do I need to alter/update the strategy?

A product mindset allows you to focus on timing, resource/cost, feasibility, feature detail, and so on after answering the aforementioned questions.

The above oversimplifies because

Leadership in discovery

Project managers are facilitators of ideas. This is as far as they normally go in the ‘idea’ space.

Business Requirements collection in classic project delivery requires extensive upfront documentation.

Agile project delivery analyzes requirements iteratively.

However, the project manager is a facilitator/planner first and foremost, therefore topic knowledge is not expected.

I mean business domain, not technical domain (to confuse matters, it is true that in some instances, it can be both technical and business domains that are important for a single individual to master).

Product managers are domain experts. They will become one if they are training/new.

They lead discovery.

Product Manager-led discovery is much more than requirements gathering.

Requirements gathering involves a Business Analyst interviewing people and documenting their requests.

The project manager calculates what fits and what doesn't using their Iron Triangle (presumably in their head) and reports back to Steering.

If this requirements-gathering exercise failed to identify requirements, what would a project manager do? or bewildered by project requirements and scope?

They would tell Steering they need a Business SME or Business Lead assigning or more of their time.

Product discovery requires the Product Manager's subject knowledge and a new mindset.

How should a Product Manager handle confusing requirements?

Product Managers handle these challenges with their talents and tools. They use their own knowledge to fill in ambiguity, but they have the discipline to validate those assumptions.

To define the problem, they may perform qualitative or quantitative primary research.

They might discuss with UX and Engineering on a whiteboard and test assumptions or hypotheses.

Do Product Managers escalate confusing requirements to Steering/Senior leaders? They would fix that themselves.

Product managers raise unclear strategy and outcomes to senior stakeholders. Open talks, soft skills, and data help them do this. They rarely raise requirements since they have their own means of handling them without top stakeholder participation.

Discovery is greenfield, exploratory, research-based, and needs higher-order stakeholder management, user research, and UX expertise.

Product Managers also aid discovery. They lead discovery. They will not leave customer/user engagement to a Business Analyst. Administratively, a business analyst could aid. In fact, many product organizations discourage business analysts (rely on PM, UX, and engineer involvement with end-users instead).

The Product Manager must drive user interaction, research, ideation, and problem analysis, therefore a Product professional must be skilled and confident.

Creating vs. receiving and having an entrepreneurial attitude

Product novices and project managers focus on details rather than the big picture. Project managers prefer spreadsheets to strategy whiteboards and vision statements.

These folks ask their manager or senior stakeholders, "What should we do?"

They then elaborate (in Jira, in XLS, in Confluence or whatever).

They want that plan populated fast because it reduces uncertainty about what's going on and who's supposed to do what.

Skilled Product Managers don't only ask folks Should we?

They're suggesting this, or worse, Senior stakeholders, here are some options. After asking and researching, they determine what value this product adds, what problems it solves, and what behavior it changes.

Therefore, to move into Product, you need to broaden your view and have courage in your ability to discover ideas, find insightful pieces of information, and collate them to form a valuable plan of action. You are constantly defining RoI and building Business Cases, so much so that you no longer create documents called Business Cases, it is simply ingrained in your work through metrics, intelligence, and insights.

Product Management is not a free lunch.

Plateless.

Plates and food must be prepared.

In conclusion, Product Managers must make at least three mentality shifts:

1. You put value first in all things. Time, money, and scope are not as important as knowing what is valuable.

2. You have faith in the field and have the ability to direct the search. YYou facilitate, but you don’t just facilitate. You wouldn't want to limit your domain expertise in that manner.

3. You develop concepts, strategies, and vision. You are not a waiter or an inbox where other people can post suggestions; you don't merely ask folks for opinion and record it. However, you excel at giving things that aren't clearly spoken or written down physical form.