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

After 10 years of working in scale-ups, I've embraced a few concepts for scaling Tech and Product teams.

First, cross-functionalize teams. Product Managers represent the business, Product Designers the consumer, and Engineers build.

I organize teams of 5-10 individuals, following AWS's two pizza teams guidelines, with a Product Trio guiding each.

If more individuals are needed to reach a goal, I group teams under a Product Trio.

With Engineering being the biggest group, Staff/Principal Engineers often support the Trio on cross-team technical decisions.

Product Managers, Engineering Managers, or Engineers in the team may manage projects (depending on the project or aim), but the trio is collectively responsible for the team's output and outcome.

Once the Product Trio model is created, roles, duties, team ceremonies, and cooperation models must be clarified.

Keep reporting lines by discipline. Line managers are accountable for each individual's advancement, thus it's crucial that they know the work in detail.

Cross-team collaboration becomes more important after 3 teams (15-30 people). Teams can easily diverge in how they write code, run ceremonies, and build products.

Establishing groups of people that are cross-team, but grouped by discipline and skills, sharing and agreeing on working practices becomes critical.

The “Spotify Guild” model has been where I’ve taken a lot of my inspiration from.

Last, establish a taxonomy for communication channels.

In Slack, I create one channel per team and one per guild (and one for me to have discussions with the team leads).

These are just some of the basic principles I follow to organize teams.

A book I particularly like about team types and how they interact with each other is https://teamtopologies.com/.

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.

The trick Notion could use is simply Facebook-ing the hell out of them.

*Time travel to fifteen years ago.* Future-Me: “Hey! What are you up to?” Old-Me: “I am proofreading an article. It’s taking a few hours, but I will be done soon.” Future-Me: “You know, in the future, you will be using a google chrome plugin called Grammarly that will help you easily proofread articles in half that time.” Old-Me: “What is… Google Chrome?” Future-Me: “Gosh…”

I love Grammarly. It’s one of those products that I personally feel the effects of. I mean, Space X is a great company. But I am not a rocket writing this article in space (or am I?)…

No, I’m not. So I don’t personally feel a connection to Space X. So, if a company collapse occurs in the morning, I might write about it. But I will have zero emotions regarding it.

Yet, if Grammarly fails tomorrow, I will feel 1% emotionally distressed. So looking at the title of this article, you’d realize that I am betting against them. This is how much I believe in the critical business model that’s taking over the world, the one of Notion.

Notion How frequently do you go through your notes?

Grammarly is everywhere, which helps its success. Grammarly is available when you update LinkedIn on Chrome. Grammarly prevents errors in Google Docs.

My internal concentration isn't apparent in the previous paragraph. Not Grammarly. I should have used Chrome to make a Google doc and LinkedIn update. Without this base, Grammarly will be useless.

So, welcome to this business essay.

• Grammarly provides a solution.

• Another issue is resolved by Jasper.

• Your entire existence is supposed to be contained within Notion.

New Google Chrome is offline. It's an all-purpose notepad (in the near future.)

• How should I start my blog? Enter it in Note.

• an update on LinkedIn? If you mention it, it might be automatically uploaded there (with little help from another app.)

• An advanced thesis? You can brainstorm it with your coworkers.

This ad sounds great! I won't cry if Notion dies tomorrow.

I'll reread the following passages to illustrate why I think Notion could kill Grammarly and Jasper.

Notion is a fantastic app that incubates your work.

Smartly, they began with note-taking.

Hopefully, your work will be on Notion. Grammarly and Jasper are still must-haves.

Grammarly will proofread your typing while Jasper helps with copywriting and AI picture development.

They're the best, therefore you'll need them. Correct? Nah.

Notion might bombard them with Facebook posts.

Notion: “Hi Grammarly, do you want to sell your product to us?” Grammarly: “Dude, we are more valuable than you are. We’ve even raised $400m, while you raised $342m. Our last valuation round put us at $13 billion, while yours put you at $10 billion. Go to hell.” Notion: “Okay, we’ll speak again in five years.”

Notion: “Jasper, wanna sell?” Jasper: “Nah, we’re deep into AI and the field. You can’t compete with our people.” Notion: “How about you either sell or you turn into a Snapchat case?” Jasper: “…”

Notion is your home. Grammarly is your neighbor. Your track is Jasper.

What if you grew enough vegetables in your backyard to avoid the supermarket? No more visits.

What if your home had a beautiful treadmill? You won't rush outside as much (I disagree with my own metaphor). (You get it.)

It's Facebooking. Instagram Stories reduced your Snapchat usage. Notion will reduce your need to use Grammarly.

The Final Piece of the AI Puzzle

Let's talk about Notion first, since you've probably read about it everywhere.

• They raised $343 million, as I previously reported, and bought four businesses

• According to Forbes, Notion will have more than 20 million users by 2022. The number of users is up from 4 million in 2020.

If raising $1.8 billion was impressive, FTX wouldn't have fallen.

This article compares the basic product to two others. Notion is a day-long app.

Notion has released Notion AI to support writers. It's early, so it's not as good as Jasper. Then-Jasper isn't now-Jasper. In five years, Notion AI will be different.

With hard work, they may construct a Jasper-like writing assistant. They have resources and users.

At this point, it's all speculation. Jasper's copywriting is top-notch. Grammarly's proofreading is top-notch. Businesses are constrained by user activities.

If Notion's future business movements are strategic, they might become a blue ocean shark (or get acquired by an unbelievable amount.)

I love business mental teasers, so tell me:

• How do you feel? Are you a frequent Notion user?

• Do you dispute my position? I enjoy hearing opposing viewpoints.

Ironically, I proofread this with Grammarly.

Calendars are great unpaid employees.

After using Notion to organize my next three months' goals, my days were a mess.

I grew very chaotic afterward. I was overwhelmed, unsure of what to do, and wasting time attempting to plan the day after it had started.

Imagine if our skeletons were on the outside. Doesn’t work.

The goals were too big; I needed to break them into smaller chunks. But how?

Enters Google Calendar

RescueTime’s recommendations took me seven hours to make a daily planner. This epic narrative begins with a sheet of paper and concludes with a daily calendar that helps me focus and achieve more goals. Ain’t nobody got time for “what’s next?” all day.

Onward!

Return to the Paleolithic Era

Plan in writing.

Not on the list, but it helped me plan my day. Physical writing boosts creativity and recall.

Find My Heart

i.e. prioritize

RescueTime suggested I prioritize before planning. Personal and business goals were proposed.

My top priorities are to exercise, eat healthily, spend time in nature, and avoid stress.

Priorities include writing and publishing Medium articles, conducting more freelance editing and Medium outreach, and writing/editing sci-fi books.

These eight things will help me feel accomplished every day.

Make a baby calendar.

Create daily calendar templates.

Make family, pleasure, etc. calendars.

Google Calendar instructions:

• Other calendars

• Press the “+” button

• Create a new calendar

• Create recurring events for each day

My calendar, without the template:

Empty, so I can fill it with vital tasks.

With the template:

My daily skeleton corresponds with my priorities. I've been overwhelmed for years because I lack daily, weekly, monthly, and yearly structure.

Google Calendars helps me reach my goals and focus my energy.

Get your colored pencils ready

Time-block color-coding.

Color labeling lets me quickly see what's happening. Maybe you are too.

Google Calendar instructions:

• Determine which colors correspond to each time block.

• When establishing new events, select a color.

• Save

My calendar is color-coded as follows:

• Yellow — passive income or other future-related activities

• Red — important activities, like my monthly breast exam

• Flamingo — shallow work, like emails, Twitter, etc.

• Blue — all my favorite activities, like walking, watching comedy, napping, and sleeping. Oh, and eating.

• Green — money-related events required for this adulting thing

• Purple — writing-related stuff

Associating a time block with a color helps me stay focused. Less distractions mean faster work.

Open My Email

aka receive a daily email from Google Calendar.

Google Calendar sends a daily email feed of your calendars. I sent myself the template calendar in this email.

Google Calendar instructions:

• Access settings

• Select the calendar that you want to send (left side)

• Go down the page to see more alerts

• Under the daily agenda area, click Email.

Get in Touch With Your Red Bull Wings — Naturally

aka audit your energy levels.

My daily planner has arrows. These indicate how much energy each activity requires or how much I have.

Rightward arrow denotes medium energy.

I do my Medium and professional editing in the morning because it's energy-intensive.

Niharikaa Sodhi recommends morning Medium editing.

I’m a morning person. As long as I go to bed at a reasonable time, 5 a.m. is super wild GO-TIME. It’s like the world was just born, and I marvel at its wonderfulness.

Freelance editing lets me do what I want. An afternoon snooze will help me finish on time.

Ditch Schedule View

aka focus on the weekly view.

RescueTime advocated utilizing the weekly view of Google Calendar, so I switched.

When you launch the phone app or desktop calendar, a red line shows where you are in the day.

I'll follow the red line's instructions. My digital supervisor is easy to follow.

In the image above, it's almost 3 p.m., therefore the red line implies it's time to snooze.

I won't forget this block ;).

Reduce the Lighting

aka dim previous days.

This is another Google Calendar feature I didn't know about. Once the allotted time passes, the time block dims. This keeps me present.

Google Calendar instructions:

• Access settings

• remaining general

• To view choices, click.

• Check Diminish the glare of the past.

Bonus

Two additional RescueTimes hacks:

Maintain a space between tasks

I left 15 minutes between each time block to transition smoothly. This relates to my goal of less stress. If I set strict start and end times, I'll be stressed.

With a buffer, I can breathe, stroll around, and start the following time block fresh.

Find a time is related to the buffer.

This option allows you conclude small meetings five minutes early and longer ones ten. Before the next meeting, relax or go wild.

Decide on a backup day.

This productivity technique is amazing.

Spend this excess day catching up on work. It helps reduce tension and clutter.

That's all I can say about Google Calendar's functionality.