More on Entrepreneurship/Creators

Matthew O'Riordan
3 years ago
Trends in SaaS Funding from 2016 to 2022
Christopher Janz of Point Nine Capital created the SaaS napkin in 2016. This post shows how founders have raised cash in the last 6 years. View raw data.
Round size
Unsurprisingly, round sizes have expanded and will taper down in 2022. In 2016, pre-seed rounds were $200k to $500k; currently, they're $1-$2m. Despite the macroeconomic scenario, Series A have expanded from $3m to $12m in 2016 to $6m and $18m in 2022.
Valuation
There are hints that valuations are rebounding this year. Pre-seed valuations in 2022 are $12m from $3m in 2016, and Series B prices are $270m from $100m in 2016.
Compared to public SaaS multiples, Series B valuations more closely reflect the market, but Seed and Series A prices seem to be inflated regardless of the market.
I'd like to know how each annual cohort performed for investors, based on the year they invested and the valuations. I can't access this information.
ARR
Seed firms' ARR forecasts have risen from $0 to $0.6m to $0 to $1m. 2016 expected $1.2m to $3m, 2021 $0.5m to $4m, and this year $0.5m to $2.5m, suggesting that Series A firms may raise with less ARR today. Series B minutes fell from $4.2m to $3m.
Capitalization Rate
2022 is the year that VCs start discussing capital efficiency in portfolio meetings. Given the economic shift in the markets and the stealthy VC meltdown, it's not surprising. Christopher Janz added capital efficiency to the SaaS Napkin as a new statistic for Series A (3.5x) and Series B. (2.5x). Your investors must live under a rock if they haven't asked about capital efficiency. If you're unsure:
The Capital Efficiency Ratio is the ratio of how much a company has spent growing revenue and how much they’re receiving in return. It is the broadest measure of company effectiveness in generating ARR
What next?
No one knows what's next, including me. All startup and growing enterprises around me are tightening their belts and extending their runways in anticipation of a difficult fundraising ride. If you're wanting to raise money but can wait, wait till the market is more stable and access to money is easier.

Caleb Naysmith
3 years ago
Ads Coming to Medium?
Could this happen?
Medium isn't like other social media giants. It wasn't a dot-com startup that became a multi-trillion-dollar social media firm. It launched in 2012 but didn't gain popularity until later. Now, it's one of the largest sites by web traffic, but it's still little compared to most. Most of Medium's traffic is external, but they don't run advertisements, so it's all about memberships.
Medium isn't profitable, but they don't disclose how terrible the problem is. Most of the $163 million they raised has been spent or used for acquisitions. If the money turns off, Medium can't stop paying its writers since the site dies. Writers must be paid, but they can't substantially slash payment without hurting the platform. The existing model needs scale to be viable and has a low ceiling. Facebook and other free social media platforms are struggling to retain users. Here, you must pay to appreciate it, and it's bad for writers AND readers. If I had the same Medium stats on YouTube, I'd make thousands of dollars a month.
Then what? Medium has tried to monetize by offering writers a cut of new members, but that's unsustainable. People-based growth is limited. Imagine recruiting non-Facebook users and getting them to pay to join. Some may, but I'd rather write.
Alternatives:
Donation buttons
Tiered subscriptions ($5, $10, $25, etc.)
Expanding content
and these may be short-term fixes, but they're not as profitable as allowing ads. Advertisements can pay several dollars per click and cents every view. If you get 40,000 views a month like me, that's several thousand instead of a few hundred. Also, Medium would have enough money to split ad revenue with writers, who would make more. I'm among the top 6% of Medium writers. Only 6% of Medium writers make more than $100, and I made $500 with 35,000 views last month. Compared to YouTube, the top 1% of Medium authors make a lot. Mr. Beast and PewDiePie make MILLIONS a month, yet top Medium writers make tens of thousands. Sure, paying 3 or 4 people a few grand, or perhaps tens of thousands, will keep them around. What if great authors leveraged their following to go huge on YouTube and abandoned Medium? If people use Medium to get successful on other platforms, Medium will be continuously cycling through authors and paying them to stay.
Ads might make writing on Medium more profitable than making videos on YouTube because they could preserve the present freemium model and pay users based on internal views. The $5 might be ad-free.
Consider: Would you accept Medium ads? A $5 ad-free version + pay-as-you-go, etc. What are your thoughts on this?
Original post available here

Jared Heyman
2 years ago
The survival and demise of Y Combinator startups
I've written a lot about Y Combinator's success, but as any startup founder or investor knows, many startups fail.
Rebel Fund invests in the top 5-10% of new Y Combinator startups each year, so we focus on identifying and supporting the most promising technology startups in our ecosystem. Given the power law dynamic and asymmetric risk/return profile of venture capital, we worry more about our successes than our failures. Since the latter still counts, this essay will focus on the proportion of YC startups that fail.
Since YC's launch in 2005, the figure below shows the percentage of active, inactive, and public/acquired YC startups by batch.
As more startups finish, the blue bars (active) decrease significantly. By 12 years, 88% of startups have closed or exited. Only 7% of startups reach resolution each year.
YC startups by status after 12 years:
Half the startups have failed, over one-third have exited, and the rest are still operating.
In venture investing, it's said that failed investments show up before successful ones. This is true for YC startups, but only in their early years.
Below, we only present resolved companies from the first chart. Some companies fail soon after establishment, but after a few years, the inactive vs. public/acquired ratio stabilizes around 55:45. After a few years, a YC firm is roughly as likely to quit as fail, which is better than I imagined.
I prepared this post because Rebel investors regularly question me about YC startup failure rates and how long it takes for them to exit or shut down.
Early-stage venture investors can overlook it because 100x investments matter more than 0x investments.
YC founders can ignore it because it shouldn't matter if many of their peers succeed or fail ;)
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Amelia Winger-Bearskin
3 years ago
Reasons Why AI-Generated Images Remind Me of Nightmares
AI images are like funhouse mirrors.
Google's AI Blog introduced the puppy-slug in the summer of 2015.
Puppy-slug isn't a single image or character. "Puppy-slug" refers to Google's DeepDream's unsettling psychedelia. This tool uses convolutional neural networks to train models to recognize dataset entities. If researchers feed the model millions of dog pictures, the network will learn to recognize a dog.
DeepDream used neural networks to analyze and classify image data as well as generate its own images. DeepDream's early examples were created by training a convolutional network on dog images and asking it to add "dog-ness" to other images. The models analyzed images to find dog-like pixels and modified surrounding pixels to highlight them.
Puppy-slugs and other DeepDream images are ugly. Even when they don't trigger my trypophobia, they give me vertigo when my mind tries to reconcile familiar features and forms in unnatural, physically impossible arrangements. I feel like I've been poisoned by a forbidden mushroom or a noxious toad. I'm a Lovecraft character going mad from extradimensional exposure. They're gross!
Is this really how AIs see the world? This is possibly an even more unsettling topic that DeepDream raises than the blatant abjection of the images.
When these photographs originally circulated online, many friends were startled and scandalized. People imagined a computer's imagination would be literal, accurate, and boring. We didn't expect vivid hallucinations and organic-looking formations.
DeepDream's images didn't really show the machines' imaginations, at least not in the way that scared some people. DeepDream displays data visualizations. DeepDream reveals the "black box" of convolutional network training.
Some of these images look scary because the models don't "know" anything, at least not in the way we do.
These images are the result of advanced algorithms and calculators that compare pixel values. They can spot and reproduce trends from training data, but can't interpret it. If so, they'd know dogs have two eyes and one face per head. If machines can think creatively, they're keeping it quiet.
You could be forgiven for thinking otherwise, given OpenAI's Dall-impressive E's results. From a technological perspective, it's incredible.
Arthur C. Clarke once said, "Any sufficiently advanced technology is indistinguishable from magic." Dall-magic E's requires a lot of math, computer science, processing power, and research. OpenAI did a great job, and we should applaud them.
Dall-E and similar tools match words and phrases to image data to train generative models. Matching text to images requires sorting and defining the images. Untold millions of low-wage data entry workers, content creators optimizing images for SEO, and anyone who has used a Captcha to access a website make these decisions. These people could live and die without receiving credit for their work, even though the project wouldn't exist without them.
This technique produces images that are less like paintings and more like mirrors that reflect our own beliefs and ideals back at us, albeit via a very complex prism. Due to the limitations and biases that these models portray, we must exercise caution when viewing these images.
The issue was succinctly articulated by artist Mimi Onuoha in her piece "On Algorithmic Violence":
As we continue to see the rise of algorithms being used for civic, social, and cultural decision-making, it becomes that much more important that we name the reality that we are seeing. Not because it is exceptional, but because it is ubiquitous. Not because it creates new inequities, but because it has the power to cloak and amplify existing ones. Not because it is on the horizon, but because it is already here.

Daniel Vassallo
3 years ago
Why I quit a $500K job at Amazon to work for myself
I quit my 8-year Amazon job last week. I wasn't motivated to do another year despite promotions, pay, recognition, and praise.
In AWS, I built developer tools. I could have worked in that field forever.
I became an Amazon developer. Within 3.5 years, I was promoted twice to senior engineer and would have been promoted to principal engineer if I stayed. The company said I had great potential.
Over time, I became a reputed expert and leader within the company. I was respected.
First year I made $75K, last year $511K. If I stayed another two years, I could have made $1M.
Despite Amazon's reputation, my work–life balance was good. I no longer needed to prove myself and could do everything in 40 hours a week. My team worked from home once a week, and I rarely opened my laptop nights or weekends.
My coworkers were great. I had three generous, empathetic managers. I’m very grateful to everyone I worked with.
Everything was going well and getting better. My motivation to go to work each morning was declining despite my career and income growth.
Another promotion, pay raise, or big project wouldn't have boosted my motivation. Motivation was also waning. It was my freedom.
Demotivation
My motivation was high in the beginning. I worked with someone on an internal tool with little scrutiny. I had more freedom to choose how and what to work on than in recent years. Me and another person improved it, talked to users, released updates, and tested it. Whatever we wanted, we did. We did our best and were mostly self-directed.
In recent years, things have changed. My department's most important project had many stakeholders and complex goals. What I could do depended on my ability to convince others it was the best way to achieve our goals.
Amazon was always someone else's terms. The terms started out simple (keep fixing it), but became more complex over time (maximize all goals; satisfy all stakeholders). Working in a large organization imposed restrictions on how to do the work, what to do, what goals to set, and what business to pursue. This situation forced me to do things I didn't want to do.
Finding New Motivation
What would I do forever? Not something I did until I reached a milestone (an exit), but something I'd do until I'm 80. What could I do for the next 45 years that would make me excited to wake up and pay my bills? Is that too unambitious? Nope. Because I'm motivated by two things.
One is an external carrot or stick. I'm not forced to file my taxes every April, but I do because I don't want to go to jail. Or I may not like something but do it anyway because I need to pay the bills or want a nice car. Extrinsic motivation
One is internal. When there's no carrot or stick, this motivates me. This fuels hobbies. I wanted a job that was intrinsically motivated.
Is this too low-key? Extrinsic motivation isn't sustainable. Getting promoted felt good for a week, then it was over. When I hit $100K, I admired my W2 for a few days, but then it wore off. Same thing happened at $200K, $300K, $400K, and $500K. Earning $1M or $10M wouldn't change anything. I feel the same about every material reward or possession. Getting them feels good at first, but quickly fades.
Things I've done since I was a kid, when no one forced me to, don't wear off. Coding, selling my creations, charting my own path, and being honest. Why not always use my strengths and motivation? I'm lucky to live in a time when I can work independently in my field without large investments. So that’s what I’m doing.
What’s Next?
I'm going all-in on independence and will make a living from scratch. I won't do only what I like, but on my terms. My goal is to cover my family's expenses before my savings run out while doing something I enjoy. What more could I want from my work?
You can now follow me on Twitter as I continue to document my journey.
This post is a summary. Read full article here

James White
3 years ago
Ray Dalio suggests reading these three books in 2022.
An inspiring reading list
I'm no billionaire or hedge-fund manager. My bank account doesn't have millions. Ray Dalio's love of reading motivates me to think differently.
Here are some books recommended by Ray Dalio. Each influenced me. Hope they'll help you.
Sapiens by Yuval Noah Harari
Page Count: 512
Rating on Goodreads: 4.39
My favorite nonfiction book.
Sapiens explores human evolution. It explains how Homo Sapiens developed from hunter-gatherers to a dominant species. Amazing!
Sapiens will teach you about human history. Yuval Noah Harari has a follow-up book on human evolution.
My favorite book quotes are:
The tendency for luxuries to turn into necessities and give rise to new obligations is one of history's few unbreakable laws.
Happiness is not dependent on material wealth, physical health, or even community. Instead, it depends on how closely subjective expectations and objective circumstances align.
The romantic comparison between today's industry, which obliterates the environment, and our forefathers, who coexisted well with nature, is unfounded. Homo sapiens held the record among all organisms for eradicating the most plant and animal species even before the Industrial Revolution. The unfortunate distinction of being the most lethal species in the history of life belongs to us.
The Power Of Habit by Charles Duhigg
Page Count: 375
Rating on Goodreads: 4.13
Great book: The Power Of Habit. It illustrates why habits are everything. The book explains how healthier habits can improve your life, career, and society.
The Power of Habit rocks. It's a great book on productivity. Its suggestions helped me build healthier behaviors (and drop bad ones).
Read ASAP!
My favorite book quotes are:
Change may not occur quickly or without difficulty. However, almost any behavior may be changed with enough time and effort.
People who exercise begin to eat better and produce more at work. They are less smokers and are more patient with friends and family. They claim to feel less anxious and use their credit cards less frequently. A fundamental habit that sparks broad change is exercise.
Habits are strong but also delicate. They may develop independently of our awareness or may be purposefully created. They frequently happen without our consent, but they can be altered by changing their constituent pieces. They have a much greater influence on how we live than we realize; in fact, they are so powerful that they cause our brains to adhere to them above all else, including common sense.
Tribe Of Mentors by Tim Ferriss
Page Count: 561
Rating on Goodreads: 4.06
Unusual book structure. It's worth reading if you want to learn from successful people.
The book is Q&A-style. Tim questions everyone. Each chapter features a different person's life-changing advice. In the book, Pressfield, Willink, Grylls, and Ravikant are interviewed.
Amazing!
My favorite book quotes are:
According to one's courage, life can either get smaller or bigger.
Don't engage in actions that you are aware are immoral. The reputation you have with yourself is all that constitutes self-esteem. Always be aware.
People mistakenly believe that focusing means accepting the task at hand. However, that is in no way what it represents. It entails rejecting the numerous other worthwhile suggestions that exist. You must choose wisely. Actually, I'm just as proud of the things we haven't accomplished as I am of what I have. Saying no to 1,000 things is what innovation is.
