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

5 VC investment criteria

I reviewed 200 startup business concepts last week. Brainache.

The enterprises sold various goods and services. The concepts were achingly similar: give us money, we'll produce a product, then get more to expand. No different from daily plans and pitches.

Most of those 200 plans sounded plausible. But 10% looked venture-worthy. 90% of startups need alternatives to venture finance.

With the success of VC-backed businesses and the growth of venture funds, a common misperception is that investors would fund any decent company idea. Finding investors that believe in the firm and founders is the key to funding.

Incorrect. Venture capital needs investing in certain enterprises. If your startup doesn't match the model, as most early-stage startups don't, you can revise your business plan or locate another source of capital.

Before spending six months pitching angels and VCs, make sure your startup fits these criteria.

Likely to generate $100 million in sales

First, I check the income predictions in a pitch deck. If it doesn't display $100M, don't bother.

The math doesn't work for venture financing in smaller businesses.

Say a fund invests $1 million in a startup valued at $5 million that is later acquired for $20 million. That's a win everyone should celebrate. Most VCs don't care.

Consider a $100M fund. The fund must reach $360M in 7 years with a 20% return. Only 20-30 investments are possible. 90% of the investments will fail, hence the 23 winners must return $100M-$200M apiece. $15M isn't worth the work.

Angel investors and tiny funds use the same ideas as venture funds, but their smaller scale affects the calculations. If a company can support its growth through exit on less than $2M in angel financing, it must have $25M in revenues before large companies will consider acquiring it.

Aiming for Hypergrowth

A startup's size isn't enough. It must expand fast.

Developing a great business takes time. Complex technology must be constructed and tested, a nationwide expansion must be built, or production procedures must go from lab to pilot to factories. These can be enormous, world-changing corporations, but venture investment is difficult.

The normal 10-year venture fund life. Investments are made during first 3–4 years.. 610 years pass between investment and fund dissolution. Funds need their investments to exit within 5 years, 7 at the most, therefore add a safety margin.

Longer exit times reduce ROI. A 2-fold return in a year is excellent. Loss at 2x in 7 years.

Lastly, VCs must prove success to raise their next capital. The 2nd fund is raised from 1st fund portfolio increases. Third fund is raised using 1st fund's cash return. Fund managers must raise new money quickly to keep their jobs.

Branding or technology that is protected

No big firm will buy a startup at a high price if they can produce a competing product for less. Their development teams, consumer base, and sales and marketing channels are large. Who needs you?

Patents, specialist knowledge, or brand name are the only answers. The acquirer buys this, not the thing.

I've heard of several promising startups. It's not a decent investment if there's no exit strategy.

A company that installs EV charging stations in apartments and shopping areas is an example. It's profitable, repeatable, and big. A terrific company. Not a startup.

This building company's operations aren't secret. No technology to protect, no special information competitors can't figure out, no go-to brand name. Despite the immense possibilities, a large construction company would be better off starting their own.

Most venture businesses build products, not services. Services can be profitable but hard to safeguard.

Probable purchase at high multiple

Once a software business proves its value, acquiring it is easy. Pharma and medtech firms have given up on their own research and instead acquire startups after regulatory permission. Many startups, especially in specialized areas, have this weakness.

That doesn't mean any lucrative $25M-plus business won't be acquired. In many businesses, the venture model requires a high exit premium.

A startup invents a new glue. 3M, BASF, Henkel, and others may buy them. Adding more adhesive to their catalogs won't boost commerce. They won't compete to buy the business. They'll only buy a startup at a profitable price. The acquisition price represents a moderate EBITDA multiple.

The company's $100M revenue presumably yields $10m in profits (assuming they’ve reached profitability at all). A $30M-$50M transaction is likely. Not terrible, but not what venture investors want after investing $25M to create a plant and develop the business.

Private equity buys profitable companies for a moderate profit multiple. It's a good exit for entrepreneurs, but not for investors seeking 10x or more what PE firms pay. If a startup offers private equity as an exit, the conversation is over.

Constructed for purchase

The startup wants a high-multiple exit. Unless the company targets $1B in revenue and does an IPO, exit means acquisition.

If they're constructing the business for acquisition or themselves, founders must decide.

If you want an indefinitely-running business, I applaud you. We need more long-term founders. Most successful organizations are founded around consumer demands, not venture capital's urge to grow fast and exit. Not venture funding.

if you don't match the venture model, what to do

VC funds moonshots. The 10% that succeed are extraordinary. Not every firm is a rocketship, and launching the wrong startup into space, even with money, will explode.

But just because your startup won't make $100M in 5 years doesn't mean it's a bad business. Most successful companies don't follow this model. It's not venture capital-friendly.

Although venture capital gets the most attention due to a few spectacular triumphs (and disasters), it's not the only or even most typical option to fund a firm.

Other ways to support your startup:

• Personal and family resources, such as credit cards, second mortgages, and lines of credit

• bootstrapping off of sales

• government funding and honors

• Private equity & project financing

• collaborating with a big business

• Including a business partner

Before pitching angels and VCs, be sure your startup qualifies. If so, include them in your pitch.

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.

Sometimes doing everything correctly isn't enough.

In 2020, I could fix my life.

After failing to start a business, I owed $40,000 and had no work.

A $1.2 billion startup on the cusp of going public pulled me up.

Ironically, it was getting ready for an epic fall — with the world watching.

Life sometimes helps. Without a base, even the strongest fall. A corporation that did everything right failed 3 months after going public.

First-row view.

Apple is the creator of Adore.

Out of respect, I've altered the company and employees' names in this account, despite their failure.

Although being a publicly traded company, it may become obvious.

We’ll call it “Adore” — a revolutionary concept in retail shopping.

Two Apple execs established Adore in 2014 with a focus on people-first purchasing.

Jon and Tim:

• The concept for the stylish Apple retail locations you see today was developed by retail expert Jon Swanson, who collaborated closely with Steve Jobs.

• Tim Cruiter is a graphic designer who produced the recognizable bouncing lamp video that appears at the start of every Pixar film.

The dynamic duo realized their vision.

“What if you could combine the convenience of online shopping with the confidence of the conventional brick-and-mortar store experience.”

Adore's mobile store concept combined traditional retail with online shopping.

Adore brought joy to 70+ cities and 4 countries over 7 years, including the US, Canada, and the UK.

Being employed on the ground floor, with world dominance and IPO on the horizon, was exciting.

I started as an Adore Expert.

I delivered cell phones, helped consumers set them up, and sold add-ons.

As the company grew, I became a Virtual Learning Facilitator and trained new employees across North America using Zoom.

In this capacity, I gained corporate insider knowledge. I worked with the creative team and Jon and Tim.

It's where I saw company foundation fissures. Despite appearances, investors were concerned.

The business strategy was ground-breaking.

Even after seeing my employee stocks fall from a home down payment to $0 (when Adore filed for bankruptcy), it's hard to pinpoint what went wrong.

Solid business model, well-executed.

Jon and Tim's chase for public funding ended in glory.

Here’s the business model in a nutshell:

Buying cell phones is cumbersome. You have two choices:

1. Online purchase: not knowing what plan you require or how to operate your device.

2. Enter a store, which can be troublesome and stressful.

Apple, AT&T, and Rogers offered Adore as a free delivery add-on. Customers could:

• Have their phone delivered by UPS or Canada Post in 1-2 weeks.

• Alternately, arrange for a person to visit them the same day (or sometimes even the same hour) to assist them set up their phone and demonstrate how to use it (transferring contacts, switching the SIM card, etc.).

Each Adore Expert brought a van with extra devices and accessories to customers.

Happy customers.

Here’s how Adore and its partners made money:

Adores partners appreciated sending Experts to consumers' homes since they improved customer satisfaction, average sale, and gadget returns.

**Telecom enterprises have low customer satisfaction. The average NPS is 30/100. Adore's global NPS was 80.

Adore made money by:

• a set cost for each delivery

• commission on sold warranties and extras

Consumer product applications seemed infinite.

A proprietary scheduling system (“The Adore App”), allowed for same-day, even same-hour deliveries.

It differentiates Adore.

They treated staff generously by:

• Options on stock

• health advantages

• sales enticements

• high rates per hour

Four-day workweeks were set by experts.

Being hired early felt like joining Uber, Netflix, or Tesla. We hoped the company's stocks would rise.

Exciting times.

I smiled as I greeted more than 1,000 new staff.

I spent a decade in retail before joining Adore. I needed a change.

After a leap of faith, I needed a lifeline. So, I applied for retail sales jobs in the spring of 2019.

The universe typically offers you what you want after you accept what you need. I needed a job to settle my debt and reach $0 again.

And the universe listened.

After being hired as an Adore Expert, I became a Virtual Learning Facilitator. Enough said.

After weeks of economic damage from the pandemic.

This employment let me work from home during the pandemic. It taught me excellent business skills.

I was active in brainstorming, onboarding new personnel, and expanding communication as we grew.

This job gave me vital skills and a regular paycheck during the pandemic.

It wasn’t until January of 2022 that I left on my own accord to try to work for myself again — this time, it’s going much better.

Adore was perfect. We valued:

• Connection

• Discovery

• Empathy

Everything we did centered on compassion, and we held frequent Justice Calls to discuss diversity and work culture.

The last day of onboarding typically ended in tears as employees felt like they'd found a home, as I had.

Like all nice things, the wonderful vibes ended.

First indication of distress

My first day at the workplace was great.

Fun, intuitive, and they wanted creative individuals, not salesman.

While sales were important, the company's vision was more important.

“To deliver joy through life-changing mobile retail experiences.”

Thorough, forward-thinking training. We had a module on intuition. It gave us role ownership.

We were flown cross-country for training, gave feedback, and felt like we made a difference. Multiple contacts responded immediately and enthusiastically.

The atmosphere was genuine.

Making money was secondary, though. Incredible service was a priority.

Jon and Tim answered new hires' questions during Zoom calls during onboarding. CEOs seldom meet new hires this way, but they seemed to enjoy it.

All appeared well.

But in late 2021, things started changing.

Adore's leadership changed after its IPO. From basic values to sales maximization. We lost communication and were forced to fend for ourselves.

Removed the training wheels.

It got tougher to gain instructions from those above me, and new employees told me their roles weren't as advertised.

External money-focused managers were hired.

Instead of creative types, we hired salespeople.

With a new focus on numbers, Adore's uniqueness began to crumble.

Via Zoom, hundreds of workers were let go.

So.

Early in 2022, mass Zoom firings were trending. A CEO firing 900 workers over Zoom went viral.

Adore was special to me, but it became a headline.

30 June 2022, Vice Motherboard published Watch as Adore's CEO Fires Hundreds.

It described a leaked video of Jon Swanson laying off all staff in Canada and the UK.

They called it a “notice of redundancy”.

The corporation couldn't pay its employees.

I loved Adore's underlying ideals, among other things. We called clients Adorers and sold solutions, not add-ons.

But, like anything, a company is only as strong as its weakest link. And obviously, the people-first focus wasn’t making enough money.

There were signs. The expansion was presumably a race against time and money.

Adore finally declared bankruptcy.

Adore declared bankruptcy 3 months after going public. It happened in waves, like any large-scale fall.

• Initial key players to leave were

• Then, communication deteriorated.

• Lastly, the corporate culture disintegrated.

6 months after leaving Adore, I received a letter in the mail from a Law firm — it was about my stocks.

Adore filed Chapter 11. I had to sue to collect my worthless investments.

I hoped those stocks will be valuable someday. Nope. Nope.

Sad, I sighed.

$1.2 billion firm gone.

I left the workplace 3 months before starting a writing business. Despite being mediocre, I'm doing fine.

I got up as Adore fell.

Finally, can we scale kindness?

I trust my gut. Changes at Adore made me leave before it sank.

Adores' unceremonious slide from a top startup to bankruptcy is astonishing to me.

The company did everything perfectly, in my opinion.

• first to market,

• provided excellent service

• paid their staff handsomely.

• was responsible and attentive to criticism

The company wasn't led by an egotistical eccentric. The crew had centuries of cumulative space experience.

I'm optimistic about the future of work culture, but is compassion scalable?