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.

1. The 7 Habits of Highly Effective People — Stephen R. Covey

Have a mission statement that outlines your goals, character traits, and impact on others.

1. Deep Work — Cal Newport

Focus is a rare skill; master it. Deep workers will succeed in our hyper-connected, distracted world.

1. 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.

1. 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.

1. 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!

This is how to build a car while driving.

Building a high-growth startup is compared to building a car while it's speeding down the highway.

How to plan without going crazy? Or, without losing team, board, and investor buy-in?

I just delivered our company's product roadmap for the rest of the year. Complete. Thorough. Page-long. I'm optimistic about its chances of surviving as everything around us changes, from internal priorities to the global economy.

It's tricky. This isn't the first time I've created a startup roadmap. I didn't invent a document. It took time to deliver a document that will be relevant for months.

Goals matter.

Although they never change, goals are rarely understood.

This is the third in a series about a startup's unique roadmapping needs. Velocity is the intensity at which a startup must produce to survive.

A high-growth startup moves at breakneck speed, which I alluded to when I said priorities and economic factors can change daily or weekly.

At that speed, a startup's roadmap must be flexible, bend but not break, and be brief and to the point. I can't tell you how many startups and large companies develop a product roadmap every quarter and then tuck it away.

Big, wealthy companies can do this. It's suicide for a startup.

The drawer thing happens because startup product roadmaps are often valid for a short time. The roadmap is a random list of features prioritized by different company factions and unrelated to company goals.

It's not because the goals changed that a roadmap is shelved or ignored. Because the company's goals were never communicated or documented in the context of its product.

In the previous post, I discussed how to turn company goals into a product roadmap. In this post, I'll show you how to make a one-page startup roadmap.

In a future post, I'll show you how to follow this roadmap. This roadmap helps you track company goals, something a roadmap must do.

Be vague for growth, but direct for execution.

Here's my plan. The real one has more entries and more content in each.

Let's discuss smaller boxes.

Product developers and engineers know that the further out they predict, the more wrong they'll be. When developing the product roadmap, this rule is ignored. Then it bites us three, six, or nine months later when we haven't even started.

Why do we put everything in a product roadmap like a project plan?

Yes, I know. We use it when the product roadmap isn't goal-based.

A goal-based roadmap begins with a document that outlines each goal's idea, execution, growth, and refinement.

Once the goals are broken down into epics, initiatives, projects, and programs, only the idea and execution phases should be modeled. Any goal growth or refinement items should be vague and loosely mapped.

Why? First, any idea or execution-phase goal will result in growth initiatives that are unimaginable today. Second, internal priorities and external factors will change, but the goals won't. Locking items into calendar slots reduces flexibility and forces deviation from the single source of truth.

No soothsayers. Predicting the future is pointless; just prepare.

A map is useless if you don't know where you're going.

As we speed down the road, the car and the road will change. Goals define the destination.

This quarter and next quarter's roadmap should be set. After that, you should track destination milestones, not how to get there.

When you do that, even the most critical investors will understand the roadmap and buy in. When you track progress at the end of the quarter and revise your roadmap, the destination won't change.

Wishing for Lasting Companies, Not Penny Stocks or Goodwill Write-Downs

Get me a NASCAR-style company-logoed cremation urn (notice to the executor of my will, theres gonna be a lot of weird requests). I believe in working on projects that would be on your tombstone. As the Homebrew logo is tattooed on my shoulder, expanding the portfolio to my posthumous commemoration is easy. But this isn't an IRR victory lap; it's a hope that the firms we worked for would last beyond my lifetime.

Venture investors too often take credit or distance themselves from startups based on circumstances. Successful companies tell stories of crucial introductions, strategy conversations, and other value. Defeats Even whether our term involves Board service or systematic ethical violations, I'm just a little investment, so there's not much I can do. Since I'm guilty, I'm tossing stones from within the glass home (although we try to own our decisions through the lifecycle).

Post-exit company trajectories are usually unconfounded. Off the cap table, no longer a shareholder (or a diminishing one as you sell off/distribute), eventually leaving the Board. You can cheer for the squad or forget about it, but you've freed the corporation and it's back to portfolio work.

As I look at the downward track of most SPACs and other tarnished IPOs from the last few years, I wonder how I would feel if those were my legacy. Is my job done? Yes. When investing in a business, the odds are against it surviving, let alone thriving and being able to find sunlight. SPAC sponsors, institutional buyers, retail investments. Free trade in an open market is their right. Risking and losing capital is the system working! But

We were lead or co-lead investors in our first three funds, but as additional VCs joined the company, we were pushed down the cap table. Voting your shares rarely matters; supporting the firm when they need it does. Being valuable, consistent, and helping the company improve builds trust with the founders.

I hope every startup we sponsor becomes a successful public company before, during, and after we benefit. My perspective of American capitalism. Well, a stock ticker has a lot of garbage, and I support all types of regulation simplification (in addition to being a person investor in the Long-Term Stock Exchange). Yet being owned by a large group of investors and making actual gains for them is great. Likewise does seeing someone you met when they were just starting out become a public company CEO without losing their voice, leadership, or beliefs.

I'm just thinking about what we can do from the start to realize value from our investments and build companies with bright futures. Maybe seed venture financing shouldn't impact those outcomes, but I'm not comfortable giving up that obligation.

Most don't understand the issue until it's too late.

My first startup was what entrepreneurs call the hardest. A two-sided marketplace.

Two-sided marketplaces are the hardest startups because founders must solve the chicken or the egg conundrum.

A two-sided marketplace needs suppliers and buyers. Without suppliers, buyers won't come. Without buyers, suppliers won't come. An empty marketplace and a founder striving to gain momentum result.

My first venture made me a struggling founder seeking to achieve traction for a two-sided marketplace. The company failed, and I vowed never to start another like it.

I didn’t. Unfortunately, my second venture was almost as hard. It failed like the second-hardest startup.

What kind of startup is the second-hardest?

The second-hardest startup, which is almost as hard to develop, is rarely discussed in the startup community. Because of this, I predict more founders fail each year trying to develop the second-toughest startup than the hardest.

Fairly, I have no proof. I see many startups, so I have enough of firsthand experience. From what I've seen, for every entrepreneur developing a two-sided marketplace, I'll meet at least 10 building this other challenging startup.

I'll describe a startup I just met with its two co-founders to explain the second hardest sort of startup and why it's so hard. They created a financial literacy software for parents of high schoolers.

The issue appears plausible. Children struggle with money. Parents must teach financial responsibility. Problems?

It's possible.

Buyers and users are different.

Buyer-user mismatch.

The financial literacy app I described above targets parents. The parent doesn't utilize the app. Child is end-user. That may not seem like much, but it makes customer and user acquisition and onboarding difficult for founders.

The difficulty of a buyer-user imbalance

The company developing a product faces a substantial operational burden when the buyer and end customer are different. Consider classic firms where the buyer is the end user to appreciate that responsibility.

Entrepreneurs selling directly to end users must educate them about the product's benefits and use. Each demands a lot of time, effort, and resources.

Imagine selling a financial literacy app where the buyer and user are different. To make the first sale, the entrepreneur must establish all the items I mentioned above. After selling, the entrepreneur must supply a fresh set of resources to teach, educate, or train end-users.

Thus, a startup with a buyer-user mismatch must market, sell, and train two organizations at once, requiring twice the work with the same resources.

The second hardest startup is hard for reasons other than the chicken-or-the-egg conundrum. It takes a lot of creativity and luck to solve the chicken-or-egg conundrum.

The buyer-user mismatch problem cannot be overcome by innovation or luck. Buyer-user mismatches must be solved by force. Simply said, when a product buyer is different from an end-user, founders have a lot more work. If they can't work extra, their companies fail.

Jobs' secret emails became public due to a litigation with Samsung.

Steve Jobs sent Phil Schiller an email at the end of 2010. Top 100 A was the codename for Apple's annual Top 100 executive meetings. The 2011 one was scheduled.

Everything about this gathering is secret, even attendance. The location is hidden, and attendees can't even drive themselves. Instead, buses transport them to a 2-3 day retreat.

Due to a litigation with Samsung, this Top 100 meeting's agenda was made public in 2014. This was a critical milestone in Apple's history, not a Top 100 meeting. Apple had many obstacles in the 2010s to remain a technological leader. Apple made more money with non-PC goods than with its best-selling Macintosh series. This was the last Top 100 gathering Steve Jobs would attend before passing, and he wanted to make sure his messages carried on before handing over his firm to Tim Cook.

In this post, we'll discuss lessons from Jobs' meeting agenda. Two sorts of entrepreneurs can use these tips:

1. Those who manage a team in a business and must ensure that everyone is working toward the same goals, upholding the same principles, and being inspired by the same future.

2. Those who are sole proprietors or independent contractors and who must maintain strict self-discipline in order to stay innovative in their industry and adhere to their own growth strategy.

Here's Steve Jobs's email outlining the annual meeting agenda. It's an 11-part summary of the company's shape and strategy.

Steve Jobs outlines Apple's 2011 strategy, 10/24/10

1. Correct your data

Business leaders must comprehend their company's metrics. Jobs either mentions critical information he already knows or demands slides showing the numbers he wants. These numbers fall under 2 categories:

Metrics for growth and strategy

• As we will see, this was a crucial statistic for Apple since it signaled the beginning of the Post PC era and required them to make significant strategic changes in order to stay ahead of the curve. Post PC products now account for 66% of our revenues.

• Within six months, iPad outsold Mac, another sign of the Post-PC age. As we will see, Jobs thought the iPad would be the next big thing, and item number four on the agenda is one of the most thorough references to the iPad.

• Geographical analysis: Here, Jobs emphasizes China, where the corporation has a slower start than anticipated. China was dominating Apple's sales growth with 16% of revenue one year after this meeting.

Metrics for people & culture

• The individuals that make up a firm are more significant to its success than its headcount or average age. That holds true regardless of size, from a 5-person startup to a Fortune 500 firm. Jobs was aware of this, which is why his suggested agenda begins by emphasizing demographic data.

• Along with the senior advancements in the previous year's requested statistic, it's crucial to demonstrate that if the business is growing, the employees who make it successful must also grow.

2. Recognize the vulnerabilities and strengths of your rivals

Steve Jobs was known for attacking his competition in interviews and in his strategies and roadmaps. This agenda mentions 18 competitors, including:

• Google 7 times

• Android 3 times

• Samsung 2 times

Jobs' agenda email was issued 6 days after Apple's Q4 results call (2010). On the call, Jobs trashed Google and Android. His 5-minute intervention included:

• Google has acknowledged that the present iteration of Android is not tablet-optimized.

• Future Android tablets will not work (Dead On Arrival)

• While Google Play only has 90,000 apps, the Apple App Store has 300,000.

• Android is extremely fragmented and is continuing to do so.

• The App Store for iPad contains over 35,000 applications. The market share of the latest generation of tablets (which debuted in 2011) will be close to nil.

Jobs' aim in blasting the competition on that call was to reassure investors about the upcoming flood of new tablets. Jobs often criticized Google, Samsung, and Microsoft, but he also acknowledged when they did a better job. He was great at detecting his competitors' advantages and devising ways to catch up.

• Jobs doesn't hold back when he says in bullet 1 of his agenda: "We further lock customers into our ecosystem while Google and Microsoft are further along on the technology, but haven't quite figured it out yet tie all of our goods together."

• The plan outlined in bullet point 5 is immediately clear: catch up to Android where we are falling behind (notifications, tethering, and speech), and surpass them (Siri,). It's important to note that Siri frequently let users down and never quite lived up to expectations.

• Regarding MobileMe, see Bullet 6 Jobs admits that when it comes to cloud services like contacts, calendars, and mail, Google is far ahead of Apple.

3. Adapt or perish

Steve Jobs was a visionary businessman. He knew personal computers were the future when he worked on the first Macintosh in the 1980s.

Jobs acknowledged the Post-PC age in his 2010 D8 interview.

Will the tablet replace the laptop, Walt Mossberg questioned Jobs? Jobs' response:

“You know, when we were an agrarian nation, all cars were trucks, because that’s what you needed on the farm. As vehicles started to be used in the urban centers and America started to move into those urban and suburban centers, cars got more popular and innovations like automatic transmission and things that you didn’t care about in a truck as much started to become paramount in cars. And now, maybe 1 out of every 25 vehicles is a truck, where it used to be 100%. PCs are going to be like trucks. They’re still going to be around, still going to have a lot of value, but they’re going to be used by one out of X people.”

Imagine how forward-thinking that was in 2010, especially for the Macintosh creator. You have to be willing to recognize that things were changing and that it was time to start over and focus on the next big thing.

Post-PC is priority number 8 in his 2010 agenda's 2011 Strategy section. Jobs says Apple is the first firm to get here and that Post PC items account about 66% of our income. The iPad outsold the Mac in 6 months, and the Post-PC age means increased mobility (smaller, thinner, lighter). Samsung had just introduced its first tablet, while Apple was working on the iPad 3. (as mentioned in bullet 4).

4. Plan ahead (and different)

Jobs' agenda warns that Apple risks clinging to outmoded paradigms. Clayton Christensen explains in The Innovators Dilemma that huge firms neglect disruptive technologies until they become profitable. Samsung's Galaxy tab, released too late, never caught up to Apple.

Apple faces a similar dilemma with the iPhone, its cash cow for over a decade. It doesn't sell as much because consumers aren't as excited about new iPhone launches and because technology is developing and cell phones may need to be upgraded.

Large companies' established consumer base typically hinders innovation. Clayton Christensen emphasizes that loyal customers from established brands anticipate better versions of current products rather than something altogether fresh and new technologies.

Apple's marketing is smart. Apple's ecosystem is trusted by customers, and its products integrate smoothly. So much so that Apple can afford to be a disruptor by doing something no one has ever done before, something the world's largest corporation shouldn't be the first to try. Apple can test the waters and produce a tremendous innovation tsunami, something few corporations can do.

In March 2011, Jobs appeared at an Apple event. During his address, Steve reminded us about Apple's brand:

“It’s in Apple’s DNA, that technology alone is not enough. That it’s technology married with liberal arts, married with the humanities that yields us the results that make our hearts sink. And nowhere is that more true that in these Post-PC devices.“

More than a decade later, Apple remains one of the most innovative and trailblazing companies in the Post-PC world (industry-disrupting products like Airpods or the Apple Watch came out after that 2011 strategy meeting), and it has reinvented how we use laptops with its M1-powered line of laptops offering unprecedented performance.

A decade after Jobs' death, Apple remains the world's largest firm, and its former CEO had a crucial part in its expansion. If you can do 1% of what Jobs did, you may be 1% as successful.

Not bad.