More on Entrepreneurship/Creators

Rachel Greenberg
3 years ago
The Unsettling Fact VC-Backed Entrepreneurs Don't Want You to Know
What they'll do is scarier.
My acquaintance recently joined a VC-funded startup. Money, equity, and upside possibilities were nice, but he had a nagging dread.
They just secured a $40M round and are hiring like crazy to prepare for their IPO in two years. All signals pointed to this startup's (a B2B IT business in a stable industry) success, and its equity-holding workers wouldn't pass that up.
Five months after starting the work, my friend struggled with leaving. We might overlook the awful culture and long hours at the proper price. This price plus the company's fate and survival abilities sent my friend departing in an unpleasant unplanned resignation before jumping on yet another sinking ship.
This affects founders. This affects VC-backed companies (and all businesses). This affects anyone starting, buying, or running a business.
Here's the under-the-table approach that's draining VC capital, leaving staff terrified (or jobless), founders rattled, and investors upset. How to recognize, solve, and avoid it
The unsettling reality behind door #1
You can't raise money off just your looks, right? If "looks" means your founding team's expertise, then maybe. In my friend's case, the founding team's strong qualifications and track records won over investors before talking figures.
They're hardly the only startup to raise money without a profitable customer acquisition strategy. Another firm raised money for an expensive sleep product because it's eco-friendly. They were off to the races with a few keywords and key players.
Both companies, along with numerous others, elected to invest on product development first. Company A employed all the tech, then courted half their market (they’re a tech marketplace that connects two parties). Company B spent millions on R&D to create a palatable product, then flooded the world with marketing.
My friend is on Company B's financial team, and he's seen where they've gone wrong. It's terrible.
Company A (tech market): Growing? Not quite. To achieve the ambitious expansion they (and their investors) demand, they've poured much of their little capital into salespeople: Cold-calling commission and salary salesmen. Is it working? Considering attrition and companies' dwindling capital, I don't think so.
Company B (green sleep) has been hiring, digital marketing, and opening new stores like crazy. Growing expenses should result in growing revenues and a favorable return on investment; if you grow too rapidly, you may neglect to check that ROI.
Once Company A cut headcount and Company B declared “going concerned”, my friend realized both startups had the same ailment and didn't recognize it.
I shouldn't have to ask a friend to verify a company's cash reserves and profitability to spot a financial problem. It happened anyhow.
The frightening part isn't that investors were willing to invest millions without product-market fit, CAC, or LTV estimates. That's alarming, but not as scary as the fact that startups aren't understanding the problem until VC rounds have dried up.
When they question consultants if their company will be around in 6 months. It’s a red flag. How will they stretch $20M through a 2-year recession with a $3M/month burn rate and no profitability? Alarms go off.
Who's in danger?
In a word, everyone who raised money without a profitable client acquisition strategy or enough resources to ride out dry spells.
Money mismanagement and poor priorities affect every industry (like sinking all your capital into your product, team, or tech, at the expense of probing what customer acquisition really takes and looks like).
This isn't about tech, real estate, or recession-proof luxury products. Fast, cheap, easy money flows into flashy-looking teams with buzzwords, trending industries, and attractive credentials.
If these companies can't show progress or get a profitable CAC, they can't raise more money. They die if they can't raise more money (or slash headcount and find shoestring budget solutions until they solve the real problem).
The kiss of death (and how to avoid it)
If you're running a startup and think raising VC is the answer, pause and evaluate. Do you need the money now?
I'm not saying VC is terrible or has no role. Founders have used it as a Band-Aid for larger, pervasive problems. Venture cash isn't a crutch for recruiting consumers profitably; it's rocket fuel to get you what and who you need.
Pay-to-play isn't a way to throw money at the wall and hope for a return. Pay-to-play works until you run out of money, and if you haven't mastered client acquisition, your cash will diminish quickly.
How can you avoid this bottomless pit? Tips:
Understand your burn rate
Keep an eye on your growth or profitability.
Analyze each and every marketing channel and initiative.
Make lucrative customer acquisition strategies and satisfied customers your top two priorities. not brand-new products. not stellar hires. avoid the fundraising rollercoaster to save time. If you succeed in these two tasks, investors will approach you with their thirsty offers rather than the other way around, and your cash reserves won't diminish as a result.
Not as much as your grandfather
My family friend always justified expensive, impractical expenditures by saying it was only monopoly money. In business, startups, and especially with money from investors expecting a return, that's not true.
More founders could understand that there isn't always another round if they viewed VC money as their own limited pool. When the well runs dry, you must refill it or save the day.
Venture financing isn't your grandpa's money. A discerning investor has entrusted you with dry powder in the hope that you'll use it wisely, strategically, and thoughtfully. Use it well.

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 ;)

Keagan Stokoe
3 years ago
Generalists Create Startups; Specialists Scale Them
There’s a funny part of ‘Steve Jobs’ by Walter Isaacson where Jobs says that Bill Gates was more a copier than an innovator:
“Bill is basically unimaginative and has never invented anything, which is why I think he’s more comfortable now in philanthropy than technology. He just shamelessly ripped off other people’s ideas….He’d be a broader guy if he had dropped acid once or gone off to an ashram when he was younger.”
Gates lacked flavor. Nobody ever got excited about a Microsoft launch, despite their good products. Jobs had the world's best product taste. Apple vs. Microsoft.
A CEO's core job functions are all driven by taste: recruiting, vision, and company culture all require good taste. Depending on the type of company you want to build, know where you stand between Microsoft and Apple.
How can you improve your product judgment? How to acquire taste?
Test and refine
Product development follows two parallel paths: the ‘customer obsession’ path and the ‘taste and iterate’ path.
The customer obsession path involves solving customer problems. Lean Startup frameworks show you what to build at each step.
Taste-and-iterate doesn't involve the customer. You iterate internally and rely on product leaders' taste and judgment.
Creative Selection by Ken Kocienda explains this method. In Creative Selection, demos are iterated and presented to product leaders. Your boss presents to their boss, and so on up to Steve Jobs. If you have good product taste, you can be a panelist.
The iPhone follows this path. Before seeing an iPhone, consumers couldn't want one. Customer obsession wouldn't have gotten you far because iPhone buyers didn't know they wanted one.
In The Hard Thing About Hard Things, Ben Horowitz writes:
“It turns out that is exactly what product strategy is all about — figuring out the right product is the innovator’s job, not the customer’s job. The customer only knows what she thinks she wants based on her experience with the current product. The innovator can take into account everything that’s possible, but often must go against what she knows to be true. As a result, innovation requires a combination of knowledge, skill, and courage.“
One path solves a problem the customer knows they have, and the other doesn't. Instead of asking a person what they want, observe them and give them something they didn't know they needed.
It's much harder. Apple is the world's most valuable company because it's more valuable. It changes industries permanently.
If you want to build superior products, use the iPhone of your industry.
How to Improve Your Taste
I. Work for a company that has taste.
People with the best taste in products, markets, and people are rewarded for building great companies. Tasteful people know quality even when they can't describe it. Taste isn't writable. It's feel-based.
Moving into a community that's already doing what you want to do may be the best way to develop entrepreneurial taste. Most company-building knowledge is tacit.
Joining a company you want to emulate allows you to learn its inner workings. It reveals internal patterns intuitively. Many successful founders come from successful companies.
Consumption determines taste. Excellence will refine you. This is why restauranteurs visit the world's best restaurants and serious painters visit Paris or New York. Joining a company with good taste is beneficial.
2. Possess a wide range of interests
“Edwin Land of Polaroid talked about the intersection of the humanities and science. I like that intersection. There’s something magical about that place… The reason Apple resonates with people is that there’s a deep current of humanity in our innovation. I think great artists and great engineers are similar, in that they both have a desire to express themselves.” — Steve Jobs
I recently discovered Edwin Land. Jobs modeled much of his career after Land's. It makes sense that Apple was inspired by Land.
A Triumph of Genius: Edwin Land, Polaroid, and the Kodak Patent War notes:
“Land was introverted in person, but supremely confident when he came to his ideas… Alongside his scientific passions, lay knowledge of art, music, and literature. He was a cultured person growing even more so as he got older, and his interests filtered into the ethos of Polaroid.”
Founders' philosophies shape companies. Jobs and Land were invested. It showed in the products their companies made. Different. His obsession was spreading Microsoft software worldwide. Microsoft's success is why their products are bland and boring.
Experience is important. It's probably why startups are built by generalists and scaled by specialists.
Jobs combined design, typography, storytelling, and product taste at Apple. Some of the best original Mac developers were poets and musicians. Edwin Land liked broad-minded people, according to his biography. Physicist-musicians or physicist-photographers.
Da Vinci was a master of art, engineering, architecture, anatomy, and more. He wrote and drew at the same desk. His genius is remembered centuries after his death. Da Vinci's statue would stand at the intersection of humanities and science.
We find incredibly creative people here. Superhumans. Designers, creators, and world-improvers. These are the people we need to navigate technology and lead world-changing companies. Generalists lead.
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Joseph Mavericks
3 years ago
5 books my CEO read to make $30M
Offices without books are like bodies without souls.

After 10 years, my CEO sold his company for $30 million. I've shared many of his lessons on medium. You could ask him anything at his always-open office. He also said we could use his office for meetings while he was away. When I used his office for work, I was always struck by how many books he had.
Books are useful in almost every aspect of learning. Building a business, improving family relationships, learning a new language, a new skill... Books teach, guide, and structure. Whether fiction or nonfiction, books inspire, give ideas, and develop critical thinking skills.
My CEO prefers non-fiction and attends a Friday book club. This article discusses 5 books I found in his office that impacted my life/business. My CEO sold his company for $30 million, but I've built a steady business through blogging and video making.
I recall events and lessons I learned from my CEO and how they relate to each book, and I explain how I applied the book's lessons to my business and life.
Note: This post has no affiliate links.
1. The One Thing — Gary Keller

Gary Keller, a real estate agent, wanted more customers. So he and his team brainstormed ways to get more customers. They decided to write a bestseller about work and productivity. The more people who saw the book, the more customers they'd get.
Gary Keller focused on writing the best book on productivity, work, and efficiency for months. His business experience. Keller's business grew after the book's release.
The author summarizes the book in one question.
"What's the one thing that will make everything else easier or unnecessary?"
When I started my blog and business alongside my 9–5, I quickly identified my one thing: writing. My business relied on it, so it had to be great. Without writing, there was no content, traffic, or business.
My CEO focused on funding when he started his business. Even in his final years, he spent a lot of time on the phone with investors, either to get more money or to explain what he was doing with it. My CEO's top concern was money, and the other super important factors were handled by separate teams.
Product tech and design
Incredible customer support team
Excellent promotion team
Profitable sales team
My CEO didn't always focus on one thing and ignore the rest. He was on all of those teams when I started my job. He'd start his day in tech, have lunch with marketing, and then work in sales. He was in his office on the phone at night.
He eventually realized his errors. Investors told him he couldn't do everything for the company. If needed, he had to change internally. He learned to let go, mind his own business, and focus for the next four years. Then he sold for $30 million.
The bigger your project/company/idea, the more you'll need to delegate to stay laser-focused. I started something new every few months for 10 years before realizing this. So much to do makes it easy to avoid progress. Once you identify the most important aspect of your project and enlist others' help, you'll be successful.
2. Eat That Frog — Brian Tracy

The author quote sums up book's essence:
Mark Twain said that if you eat a live frog in the morning, it's probably the worst thing that will happen to you all day. Your "frog" is the biggest, most important task you're most likely to procrastinate on.
"Frog" and "One Thing" are both about focusing on what's most important. Eat That Frog recommends doing the most important task first thing in the morning.
I shared my CEO's calendar in an article 10 months ago. Like this:

CEO's average week (some information crossed out for confidentiality)
Notice anything about 8am-8:45am? Almost every day is the same (except Friday). My CEO started his day with a management check-in for 2 reasons:
Checking in with all managers is cognitively demanding, and my CEO is a morning person.
In a young startup where everyone is busy, the morning management check-in was crucial. After 10 am, you couldn't gather all managers.
When I started my blog, writing was my passion. I'm a morning person, so I woke up at 6 am and started writing by 6:30 am every day for a year. This allowed me to publish 3 articles a week for 52 weeks to build my blog and audience. After 2 years, I'm not stopping.
3. Deep Work — Cal Newport

Deep work is focusing on a cognitively demanding task without distractions (like a morning management meeting). It helps you master complex information quickly and produce better results faster. In a competitive world 10 or 20 years ago, focus wasn't a huge advantage. Smartphones, emails, and social media made focus a rare, valuable skill.
Most people can't focus anymore. Screens light up, notifications buzz, emails arrive, Instagram feeds... Many people don't realize they're interrupted because it's become part of their normal workflow.
Cal Newport mentions Bill Gates' "Think Weeks" in Deep Work.
Microsoft CEO Bill Gates would isolate himself (often in a lakeside cottage) twice a year to read and think big thoughts.
Inside Bill's Brain on Netflix shows Newport's lakeside cottage. I've always wanted a lakeside cabin to work in. My CEO bought a lakehouse after selling his company, but now he's retired.
As a company grows, you can focus less on it. In a previous section, I said investors told my CEO to get back to basics and stop micromanaging. My CEO's commitment and ability to get work done helped save the company. His deep work and new frameworks helped us survive the corona crisis (more on this later).
The ability to deep work will be a huge competitive advantage in the next century. Those who learn to work deeply will likely be successful while everyone else is glued to their screens, Bluetooth-synced to their watches, and playing Candy Crush on their tablets.
4. The 7 Habits of Highly Effective People — Stephen R. Covey

It took me a while to start reading this book because it seemed like another shallow self-help bible. I kept finding this book when researching self-improvement. I tried it because it was everywhere.
Stephen Covey taught me 2 years ago to have a personal mission statement.
A 7 Habits mission statement describes the life you want to lead, the character traits you want to embody, and the impact you want to have on others. shortform.com
I've had many lunches with my CEO and talked about Vipassana meditation and Sunday forest runs, but I've never seen his mission statement. I'm sure his family is important, though. In the above calendar screenshot, you can see he always included family events (in green) so we could all see those time slots. We couldn't book him then. Although he never spent as much time with his family as he wanted, he always made sure to be on time for his kid's birthday rather than a conference call.
My CEO emphasized his company's mission. Your mission statement should answer 3 questions.
What does your company do?
How does it do it?
Why does your company do it?
As a graphic designer, I had to create mission-statement posters. My CEO hung posters in each office.
5. Measure What Matters — John Doerr

This book is about Andrew Grove's OKR strategy, developed in 1968. When he joined Google's early investors board, he introduced it to Larry Page and Sergey Brin. Google still uses OKR.
Objective Key Results
Objective: It explains your goals and desired outcome. When one goal is reached, another replaces it. OKR objectives aren't technical, measured, or numerical. They must be clear.
Key Result should be precise, technical, and measurable, unlike the Objective. It shows if the Goal is being worked on. Time-bound results are quarterly or yearly.
Our company almost sank several times. Sales goals were missed, management failed, and bad decisions were made. On a Monday, our CEO announced we'd implement OKR to revamp our processes.
This was a year before the pandemic, and I'm certain we wouldn't have sold millions or survived without this change. This book impacted the company the most, not just management but all levels. Organization and transparency improved. We reached realistic goals. Happy investors. We used the online tool Gtmhub to implement OKR across the organization.

My CEO's company went from near bankruptcy to being acquired for $30 million in 2 years after implementing OKR.
I hope you enjoyed this booklist. Here's a recap of the 5 books and the lessons I learned from each.
The 7 Habits of Highly Effective People — Stephen R. Covey
Have a mission statement that outlines your goals, character traits, and impact on others.
Deep Work — Cal Newport
Focus is a rare skill; master it. Deep workers will succeed in our hyper-connected, distracted world.
The One Thing — Gary Keller
What can you do that will make everything else easier or unnecessary? Once you've identified it, focus on it.
Eat That Frog — Brian Tracy
Identify your most important task the night before and do it first thing in the morning. You'll have a lighter day.
Measure What Matters — John Doerr
On a timeline, divide each long-term goal into chunks. Divide those slices into daily tasks (your goals). Time-bound results are quarterly or yearly. Objectives aren't measured or numbered.
Thanks for reading. Enjoy the ride!

The woman
3 years ago
Why Google's Hiring Process is Brilliant for Top Tech Talent
Without a degree and experience, you can get a high-paying tech job.
Most organizations follow this hiring rule: you chat with HR, interview with your future boss and other senior managers, and they make the final hiring choice.
If you've ever applied for a job, you know how arduous it can be. A newly snapped photo and a glossy resume template can wear you out. Applying to Google can change this experience.
According to an Universum report, Google is one of the world's most coveted employers. It's not simply the search giant's name and reputation that attract candidates, but its role requirements or lack thereof.
Candidates no longer need a beautiful resume, cover letter, Ivy League laurels, or years of direct experience. The company requires no degree or experience.
Elon Musk started it. He employed the two-hands test to uncover talented non-graduates. The billionaire eliminated the requirement for experience.
Google is deconstructing traditional employment with programs like the Google Project Management Degree, a free online and self-paced professional credential course.
Google's hiring is interesting. After its certification course, applicants can work in project management. Instead of academic degrees and experience, the company analyzes coursework.
Google finds the best project managers and technical staff in exchange. Google uses three strategies to find top talent.
Chase down the innovators
Google eliminates restrictions like education, experience, and others to find the polar bear amid the snowfall. Google's free project management education makes project manager responsibilities accessible to everyone.
Many jobs don't require a degree. Overlooking individuals without a degree can make it difficult to locate a candidate who can provide value to a firm.
Firsthand knowledge follows the same rule. A lack of past information might be an employer's benefit. This is true for creative teams or businesses that prefer to innovate.
Or when corporations conduct differently from the competition. No-experience candidates can offer fresh perspectives. Fast Company reports that people with no sales experience beat those with 10 to 15 years of experience.
Give the aptitude test first priority.
Google wants the best candidates. Google wouldn't be able to receive more applications if it couldn't screen them for fit. Its well-organized online training program can be utilized as a portfolio.
Google learns a lot about an applicant through completed assignments. It reveals their ability, leadership style, communication capability, etc. The course mimics the job to assess candidates' suitability.
Basic screening questions might provide information to compare candidates. Any size small business can use screening questions and test projects to evaluate prospective employees.
Effective training for employees
Businesses must train employees regardless of their hiring purpose. Formal education and prior experience don't guarantee success. Maintaining your employees' professional knowledge gaps is key to their productivity and happiness. Top-notch training can do that. Learning and development are key to employee engagement, says Bob Nelson, author of 1,001 Ways to Engage Employees.
Google's online certification program isn't available everywhere. Improving the recruiting process means emphasizing aptitude over experience and a degree. Instead of employing new personnel and having them work the way their former firm trained them, train them how you want them to function.
If you want to know more about Google’s recruiting process, we recommend you watch the movie “Internship.”

Aparna Jain
3 years ago
Negative Effects of Working for a FAANG Company
Consider yourself lucky if your last FAANG interview was rejected.
FAANG—Facebook, Apple, Amazon, Netflix, Google
(I know its manga now, but watch me not care)
These big companies offer many benefits.
large salaries and benefits
Prestige
high expectations for both you and your coworkers.
However, these jobs may have major drawbacks that only become apparent when you're thrown to the wolves, so it's up to you whether you see them as drawbacks or opportunities.
I know most college graduates start working at big tech companies because of their perceived coolness.
I've worked in these companies for years and can tell you what to expect if you get a job here.
Little fish in a vast ocean
The most obvious. Most billion/trillion-dollar companies employ thousands.
You may work on a small, unnoticed product part.
Directors and higher will sometimes make you redo projects they didn't communicate well without respecting your time, talent, or will to work on trivial stuff that doesn't move company needles.
Peers will only say, "Someone has to take out the trash," even though you know company resources are being wasted.
The power imbalance is frustrating.
What you can do about it
Know your WHY. Consider long-term priorities. Though riskier, I stayed in customer-facing teams because I loved building user-facing products.
This increased my impact. However, if you enjoy helping coworkers build products, you may be better suited for an internal team.
I told the Directors and Vice Presidents that their actions could waste Engineering time, even though it was unpopular. Some were receptive, some not.
I kept having tough conversations because they were good for me and the company.
However, some of my coworkers praised my candor but said they'd rather follow the boss.
An outdated piece of technology can take years to update.
Apple introduced Swift for iOS development in 2014. Most large tech companies adopted the new language after five years.
This is frustrating if you want to learn new skills and increase your market value.
Knowing that my lack of Swift practice could hurt me if I changed jobs made writing verbose Objective C painful.
What you can do about it
Work on the new technology in side projects; one engineer rewrote the Lyft app in Swift over the course of a weekend and promoted its adoption throughout the entire organization.
To integrate new technologies and determine how to combine legacy and modern code, suggest minor changes to the existing codebase.
Most managers spend their entire day in consecutive meetings.
After their last meeting, the last thing they want is another meeting to discuss your career goals.
Sometimes a manager has 15-20 reports, making it hard to communicate your impact.
Misunderstandings and stress can result.
Especially when the manager should focus on selfish parts of the team. Success won't concern them.
What you can do about it
Tell your manager that you are a self-starter and that you will pro-actively update them on your progress, especially if they aren't present at the meetings you regularly attend.
Keep being proactive and look for mentorship elsewhere if you believe your boss doesn't have enough time to work on your career goals.
Alternately, look for a team where the manager has more authority to assist you in making career decisions.
After a certain point, company loyalty can become quite harmful.
Because big tech companies create brand loyalty, too many colleagues stayed in unhealthy environments.
When you work for a well-known company and strangers compliment you, it's fun to tell your friends.
Work defines you. This can make you stay too long even though your career isn't progressing and you're unhappy.
Google may become your surname.
Workplaces are not families.
If you're unhappy, don't stay just because they gave you the paycheck to buy your first home and make you feel like you owe your life to them.
Many employees stayed too long. Though depressed and suicidal.
What you can do about it
Your life is not worth a company.
Do you want your job title and workplace to be listed on your gravestone? If not, leave if conditions deteriorate.
Recognize that change can be challenging. It's difficult to leave a job you've held for a number of years.
Ask those who have experienced this change how they handled it.
You still have a bright future if you were rejected from FAANG interviews.
Rejections only lead to amazing opportunities. If you're young and childless, work for a startup.
Companies may pay more than FAANGs. Do your research.
Ask recruiters and hiring managers tough questions about how the company and teams prioritize respectful working hours and boundaries for workers.
I know many 15-year-olds who have a lifelong dream of working at Google, and it saddens me that they're chasing a name on their resume instead of excellence.
This article is not meant to discourage you from working at these companies, but to share my experience about what HR/managers will never mention in interviews.
Read both sides before signing the big offer letter.
