Kirk Kerkorian’s charter airline, Trans International Airlines (TIA), was doing well—so well that in 1962, Studebaker Corporation offered to acquire it by assuming all Kirk’s debt and giving him $1 million in Studebaker stock, for a total deal value of $10 million. Kirk agreed and became a millionaire.

Kirk's biography says Studebaker fell on hard times and sold TIA back to Kirk two years later, in 1964, for just $2.5 million. He borrowed $2 million from Bank of America and closed the deal. By now having a better understanding of the stock market, Kirk took TIA public in 1965. As the company’s performance improved and the Armenian community supported the stock, it soared. In a few months, Kirk paid off the bank loan and owned stock worth $66 million at the age of 48. Three years later, in 1968, he sold TIA to Transamerica Corporation in a deal that gave him $100 million in Transamerica stock.

To recap, Kirk started his first flight school and charter company around 1945. Roughly twenty years later, he’d turned that idea into a publicly traded company in which he had a personal ownership worth $66 million. Three years later, he was Transamerica Corporation’s largest individual shareholder with ownership exceeding $100 million. That’s a remarkable accomplishment, especially considering his humble beginnings.

During this period, Kirk evolved. He transitioned away from being solely a hands-on aviation operator and builder, learning and acquiring skills around mergers and acquisitions and navigating the stock market. He used those skills to add public market investing to his resume. Kirk was no longer just an aviation entrepreneur.

His ability to level up stood out to me, especially considering that the above was only part of what he juggled during this period. He was also beginning to acquire land and consider entering the casino market.

Prefer listening? Catch audio versions of these blog posts, with more context added, on Apple Podcasts here or Spotify here!

Because I’ve received feedback that others got value when I shared the struggles from my current personal project, I’ve decided to build this project in public and share my ups and downs openly.

Current Personal Project: Reading Books about Entrepreneurs and Sharing What I Learned from Them via Blog Posts and Audio Recordings Distributed as a Podcast

What I struggled with:

• I added editing twelve recordings to my workload. That, combined with reading two books, writing seven blog posts, and recording seven audio posts to distribute via podcast, was too much. I was behind and pushing hard this past weekend to hit my goals. The quality of the blog posts and recordings started declining late in the week.

What I learned:

• People’s time is valuable. My goal is to provide as much value per minute as possible when someone reads or listens to what I share about books. I learned that I need to keep this top of mind and find the right balance of reading, distilling, writing, recording, and editing. This week I was too heavy on reading because of my two-book goal and editing because I had a new toy to play with.
• A few weeks back, I stopped editing recordings and focused on getting reps by publishing unedited recordings. Then, researching successful YouTubers and podcasters highlighted that editing is key to making content concise. The editing tool also makes a difference. I was using GarageBand and hated it. A few people mentioned Descript. I started using Descript this week, and it made a material difference. This software makes editing audio as easy as editing a Word doc.
• Knowing I can edit recordings has decreased my frustration. Before, I would get frustrated when I made an error because I knew I had to start from scratch and rerecord.
• I listened to the early episodes of a few popular podcasts. They weren’t great. This was a good reminder that even the greats started on shaky ground and worked to continually improve. Comparing myself to the latest episode of a seasoned provider of audio content isn’t realistic.
• When I set reading goals, I need to consider the length of books and my available bandwidth. All books aren’t equal. One of the books I read this week was 400 pages, and I shouldn’t have read it in the same week as another book.
• My concerns about Amazon affiliate links being perceived as tacky were unfounded. I don't want the commission; I want the data on purchases. During feedback sessions, people said they thought a commission (that doesn’t cost them anything extra) would be fair if I helped them discover the book they purchased. They also highlighted it as a common practice that people expect now.
• When I’m face-to-face with entrepreneurs, my project resonates well, and they get excited about listening. I also learn a lot about their reading habits and pain points. I need to lean into more face-to-face interactions to discuss my project.
• The quality of my insights is greatest when I’m mentally fresh. On the days I was tired, my insights weren’t of the quality I know I’m capable of.

Those are my struggles and learnings from this week!

Prefer listening? Catch audio versions of these blog posts, with more context added, on Apple Podcasts here or Spotify here!

This is my two-hundred-nineteenth weekly reflection or update.

Two weeks ago, I changed my weekly reflection to a weekly update on a current project. For more on why I made this change, see here.

Current Personal Project: Reading Books about Entrepreneurs and Sharing What I Learned from Them via Blog Posts and Audio Recordings Distributed as a Podcast

Metrics (since 4/1/24):

• Total audio recordings published: 49 (+7)
• Total blog posts published: 69 (+7)

What I completed this week:

• Read a book written by Felix Dennis and the biography of Kirk Kerkorian (see here and here)
• Had four additional feedback sessions—I missed my target by one for the second straight week
• Compiled and sorted feedback from sessions completed the week of 5/27/24
• Tweaked podcast titles
• Crystallized my “why” for this project in writing
• Decided to move forward with Amazon affiliate links for books I’ve read
• Identified two YouTube channels focused on sharing insights from non-entrepreneurial books and studied what makes these channels appeal to listeners
• Began testing Descript for recording and editing audio

Content:

• Audio content changes: Sharing how I discovered a book, referencing other recordings in the series, and highlighting what questions I’m seeking to answer as I read the book
• Edited episodes 37 through 48 using Descript to make them more concise
• The average recording length is still roughly 12 minutes

What I’ll do next week:

• Read one biography or autobiography
• Write seven blog posts and record seven audio posts
• Compile feedback from sessions completed the week of 6/3/24 and identify insights
• Make changes to audio content based on feedback
• Edit Jim Simons series using Descript
• Complete five feedback sessions
• Implement Amazon affiliate links for books

Asks:

• Listen to my most recent audio recordings and provide feedback on how I can improve them

Week two hundred nineteen was another week of learning. Looking forward to next week!

FYI: I’m still playing with the format for this weekly update. I’ll add and remove stuff until I settle on a format I like.

Prefer listening? Catch audio versions of these blog posts, with more context added, on Apple Podcasts here or Spotify here!

In Sumner Redstone’s autobiography, he told us about his epic battle with Kirk Kerkorian over MGM/UA Home Entertainment Group. I know nothing about MGM/UA or Kerkorian, so I started reading William C. Rempel’s biography of him, The Gambler: How Penniless Dropout Kirk Kerkorian Became the Greatest Deal Maker in Capitalist History. I’ve read a third of the book so far, and it’s an incredible entrepreneurial story.

Kirk’s first business was cleaning up old cars and reselling them for a profit. After getting the flying bug, he became a pilot for the Royal Air Force Ferry Command (RAF) during World War II, earning hefty hazard pay of $1,000 a month to deliver warplanes across the Atlantic. He did all this despite having only an eighth-grade education.

After World War II, the aviation industry took off, as did the demand for pilots. In 1945, Kirk started a flight school and eventually a charter airline, too. His customers flew frequently to Las Vegas, a desert city of saloons and small casinos. Kirk loved the excitement of the city, something he’d missed since flying dangerous missions for RFA.

Kirk decided he wanted his own airline, but he was short on capital. He started buying surplus World War II military planes, refurbishing them, and reselling them. At roughly age thirty-five, Kirk was making over $100,000 a year. He learned that pilots don’t make big money, but businessmen do. He became a major player in the used airplane brokerage and charter businesses between his home base in Los Angeles and Las Vegas.

Kirk’s chartering niche to Las Vegas led to friendships with celebrities and casino bosses (including Bugsy Siegel). His clients schooled Kirk on the lucrative casino business. He wanted in and, in 1955, invested $50,000 for a roughly 1% stake in the Dunes Hotel & Country Club, which ran into trouble. Kirk’s investment went to zero, but by then he was making roughly $300,000 a year from aviation. The loss was a painful and important lesson about the casino business.

By 1962, commercial airlines were moving to jetliners, and Kirk recognized an opportunity to become the first charter service using jetliners. He wanted to be the first government contractor to move cargo worldwide via jetliners. The planes cost $5 million, money he didn’t have. He convinced Bank of America to loan him $2 million and for the aircraft manufacturer to finance the remaining $3 million (unheard of at the time). He was officially in the postwar charter business, flying loads between US military bases worldwide. The move was lucrative. His company’s annual profits soared from $250,000 to $1.1 million in year one.

By his forties, Kirk was wildly successful. A key to his success was recognizing trends early. He repeatedly found and capitalized on them, often finding other trends in the process. His relationships and early understanding of Las Vegas and the casinos would play a major role in his future.

I’m looking forward to reading the rest of this book.

Prefer listening? Catch audio versions of these blog posts, with more context added, on Apple Podcasts here or Spotify here!

I finished reading How to Get Rich: One of the World's Greatest Entrepreneurs Shares His Secrets by Felix Dennis today.

This book isn’t just about getting rich. It’s about succeeding as an entrepreneur. Riches are a byproduct of building a successful company. That mental framing was helpful as I read the book.

Here are my takeaways from the last third of the book:

Part Three: Succeeding as an Entrepreneur

• Focus – Felix Dennis’s goal was to create wealth for himself. After stumbling into magazines and succeeding, he believed he was “born a magazine publisher.” He regrets lying to himself. Focusing on something he didn’t love but happened to be good at “cut me off from more lucrative endeavors,” he said. Magazine publishing is a mature business, so outsize success was harder to achieve and took longer. He advises staying focused on your objective (for him, wealth) and picking the best path to that goal (i.e., an industry with a tailwind).
• Luck – Dennis and a partner decided to write a biography of Bruce Lee. Sadly, Lee unexpectedly died young just as they were finishing the book. International demand for their biography rocketed, and that led to several other opportunities. Their focus on Lee’s biography put them in a position to capitalize after his tragic passing. This morbid story highlights Dennis’s psychology (for better or worse) and how luck isn’t always blind. Focus and hard work often precede lucky breaks.
• Do an outstanding job – Your company should always do an outstanding job. High-quality people are attracted to quality products and services, so you’ll attract and hire the best talent. The company will make fewer errors, which will reduce costs. If your company is known for quality, it will get a premium valuation and you’ll be wealthier (on paper). And doing a good job is just more fun.

Part Four: The Endgame

• Closing costs – The cost of shuttering a business can be material, and founders underestimate that fact. Selling the business for anything is better than shutting it down.
• Selling a failing business – Determine your financial runway. Think about ways competitors can use what you’ve built. Think of ways you can modify the business. Articulate how your business could add value to acquirers as-is or in a modified form. Start letting people know the business is for sale and how it can add value to their operations. Two interested parties equal a sale process. It takes only one to close a deal.
• Shuttering the business – Closing is the last resort. Pursue this path only after you’ve tried to sell the business. Never announce the business is winding down until you’ve exhausted all options for selling.

I now understand why Dennis wrote this book. He genuinely wanted to help other people become successful entrepreneurs and achieve financial independence. Sharing what he learned the hard way was his way of giving back.

Dennis was a colorful, mercenary entrepreneur. He started multiple businesses, and I didn’t pick up on a burning passion for any of them. He wanted financial freedom and everything that came with it, which wasn’t always good for Dennis.

Prefer listening? Catch audio versions of these blog posts, with more context added, on Apple Podcasts here or Spotify here!

I’ve read two-thirds of Felix Dennis’s book How to Get Rich: One of the World's Greatest Entrepreneurs Shares His Secrets. Dennis pairs the wisdom he gained with entertaining stories from his journey. Dennis was a colorful person, and I’m starting to get a feel for the type of founder he was.

As I said yesterday, this book is about how to succeed as an entrepreneur, not just how to get rich. That mental framing was helpful as I read the book. I’ll keep swapping the two terms in this post.

Here are my takeaways from the second third of the book:

Part Three: Succeeding as an Entrepreneur

• Persistence – Persistent people have the conviction that they’re right and that that will be confirmed shortly. Stubbornness is persisting even when there’s plenty of evidence that you’re wrong or that you shouldn’t. Acknowledging a mistake and realizing a new plan is needed are signs of clear thinking and help focus your persistence on the right activities. The most successful people I know are persistent but also rational and clear thinkers.
• Instincts – Trusting your own judgment is essential to success. Always be on high alert and looking for opportunities. When you find one, trust your instincts and move fast. Making judgment calls quickly is instinctual. If you deliberate too much, it’s hard to develop your instincts or trust your judgment.
• Evolve or die – Learning to evolve is essential to survival. If someone is going to “strangle your baby,” it’d better be you. If your product is going to be cannibalized, it’d better be by you, not your competitor.
• Listen and learn – Talking to team members and industry friends is necessary, but the real learning happens when you talk to people you don’t know, or who work in an obscure corner of your industry you’re less familiar with. If you’re not learning, you’re slowly dying. Make listening and learning priorities, or your days are numbered.
• Luck – Two things are part of getting lucky. Preparation is required to capitalize on an opportunity. “Do the heavy lifting work and homework in advance.” You must also recognize an opportunity when it happens. Don’t be so buried in the details you can’t see an opportunity that’s right in front of you. Luck tends to evade micromanagers and people who can’t let go. Stay alert and on the lookout for your lucky break.
• Balance of weakness – In negotiations, usually, both parties have a weakness—to one degree or another. Determining which weakness is most pressing and “potentially catastrophic to which party” is key. The “immediate balance of weaknesses may well prove more decisive than any long-term balance of strengths.” Weaknesses are usually hidden. Make it your top priority to determine the balance of weakness in negotiations. If their need outweighs your greed, you’re in a great negotiating position.
• Delegation – People are your most precious asset. Delegation is a tool to incentivize your people and bring out the best in them. They’ll make mistakes as they learn, but as your people succeed, your company succeeds.

Dennis’s wisdom is simple but not easy. I’m looking forward to finishing this book.

Prefer listening? Catch audio versions of these blog posts, with more context added, on Apple Podcasts here or Spotify here!

Today, I started reading a book that’s outside my norm. Felix Dennis, the founder of Dennis Publishing and Maxim magazine, wrote How to Get Rich: One of the World's Greatest Entrepreneurs Shares His Secrets. The book is a collection of lessons Dennis learned during his journey. The title isn’t my favorite, but it matches the author’s personality.

Instead of how to get rich, I think this book shares how to succeed as an entrepreneur. I used this mental framing as I read the book. I’ll swap the two terms in this post.

Here are my takeaways from the first third of the book:

Part One: Pole Positions

• Young, penniless and inexperienced – People in this state are more likely to succeed for a few reasons. Because they lack experience, they’re likelier to learn new problem-solving methods. They have more stamina. Their risk tolerance is higher because they have almost nothing to lose. Dennis suggests that seasoned professionals considering entrepreneurship partner with someone young, broke, and inexperienced.

Part Two: Getting Started

• Fear of failure – People often fail to launch a company because they’re afraid. Failing publicly highlights mistakes and errors in judgment to others, which is embarrassing. I believe that entrepreneurs will experience a lot of failures as they experiment, so a thick skin and viewing failures as opportunities to learn are essential. Also, winning fixes everything. Success is what people remember, not failure.  
• New industries – New or rapidly growing industries increase your chances of success. Often, more risk capital is available from investors seeking large returns, which can lead to founders maintaining more control. Not much is known in new industries, so you can establish yourself as an expert quickly (if you work to learn), and a rising tide masks mistakes.
• The trifecta – Look for opportunities that align with your inclinations, aptitude, and fate. Inclinations are your natural interests. Aptitude is something you’re naturally good at (ask others if you’re unsure). Fate is luck or serendipity. When an opportunity aligns with all three, ignore the naysayers and quickly seize it before it’s gone.
• Reinforcing failure – A common start-up error. Knowing whether to keep pushing when something isn’t working or give up is difficult but important. Success may be just around the corner, or it may never come. Dennis believes timing plays a big part in success. Looking at the data beneath the surface level for signs of being too early or too late can help you avoid reinforcing a failure.
• Thinking small and acting big – Another common start-up error. Never disregard bold or new ideas (thinking small). Never think you’re above doing the things that lead to your success (acting big). Dennis regretfully shares a crazy period in his life when he spent over $100 million within ten years thinking small and acting big. Keep doing the things that led to your success (acting small) and thinking of bold ways to succeed (thinking big).

So far, this book is colorful and full of entrepreneurial wisdom. I’m looking forward to finishing it.

Prefer listening? Catch audio versions of these blog posts, with more context added, on Apple Podcasts here or Spotify here!

I finished reading Sumner Redstone’s autobiography, A Passion to Win. The book gave me insight into Redstone as a person. It describes how Redstone took National Amusements, Inc. (NAI) from a family-owned, drive-in theatre business to a publicly traded media empire worth tens of billions of dollars. At the time of the book’s publication in 2001, Redstone’s empire included cable channels, movie theatres, radio stations, broadcast stations, and much more.

Redstone recognized that he needed to be in the content business. Drive-in theatre growth was slowing because of cable, and he was tired of fighting studios. If he couldn’t beat them, he would own them—partially at least. He used NAI’s cash flow to buy substantial ownership in publicly traded movie studios such as Disney and MGM. Redstone scored profits of tens of millions of dollars each on several investments. He profited by $26 million—a roughly 100% return—when Coca-Cola bought Columbia Pictures in 1982. Redstone’s ownership in studios was profitable, educated him on the business, and deepened his industry relationships.

When the leveraged-buyout craze began in the 1980s, Redstone found himself battling with raiders and others who were trying to buy public companies he owned at valuations he thought were too low. In 1986, at age 63, he found himself in a battle over Viacom International, a cable and television programming business that owned MTV, Lifetime, and other assets. After digging into the company’s potential, he decided to buy it outright. He learned to raise debt and fought ferociously to secure the deal (crazy story in the book!). In 1987 he closed the deal. After spending $3.4 billion, he was finally in the content business.

The deal proved lucrative. MTV ended up being a cultural force with a young audience. The channel was the cornerstone of Viacom, “providing more than 50 percent of Viacom’s cashflow” annually in the 1990s. The Cosby Show was another amazing asset. In 1989, its syndication sales were $4 million for each of its 125 episodes. The syndication of that show brought in $500 million to Viacom that year, a record at the time.

Redstone took things further in 1994. He acquired Paramount Pictures for over $10 billion after a brutal battle against Barry Diller and John Malone (another crazy story!) while simultaneously acquiring Blockbuster Video. At roughly age 71, he was in the business of creating movies and producing broadcast television shows (e.g., MacGyver). He owned a library of almost 800 classic films, including The Godfather and the Indiana Jones movies. He also owned the leading video rental company, which would quickly become a thorn in his side.

In 1999, at age 76, Redstone acquired CBS Broadcasting Inc. for $32 billion. CBS was an advertising powerhouse offering radio, cable, and broadcast channels and outdoor advertising (billboards). Surprisingly, this mega deal didn’t involve any battles.

He was number one in radio, cable programming, and outdoor advertising and “would own the number-one audience deliverer both nationally and locally in television.”

Sumner was “the king of content as well as king of distribution.” He had finally won.

Read my first and second parts of this series on Sumner Redstone here and here.

Note: If you’re interested, the book provides granular specifics on negotiations and financials for each deal mentioned above.

Prefer listening? Catch audio versions of these blog posts, with more context added, on Apple Podcasts here or Spotify here!

Because I’ve received feedback that others got value when I shared the struggles from my current personal project, I’ve decided to build this project in public and share my ups and downs openly.

Current Personal Project: Reading Books about Entrepreneurs and Sharing What I Learned from Them via Blog Posts and Audio Recordings Distributed as a Podcast

What I struggled with:

• Reading two books, writing seven blog posts, and recording eight audio posts to distribute via podcast is a lot. I hit a wall toward the end of the week. Finishing out the week was tough.
• This week felt harder than last week. The above weekly goals I’ve set have me in a state of discomfort. I recognize this because I experienced this feeling when I started blogging daily in 2020. My brain feels overloaded, and I’m mentally tired some days. I’m pushing my limits and expanding them each consecutive day I do this. Said differently, the discomfort I’m feeling is likely growth. Hopefully this will get easier as my brain realizes this is our new normal.
• I’m still not as concise as I want to be in communicating insights from books. The series on Ed Thorp highlighted this for me. Even though I’ve read this book twice, I struggled to balance getting the recordings done and communicating my points clearly. “Done is better than perfect” won. But I did record a bonus episode for Thorp because it bothered me that much and this is one of my favorite books.

What I learned:

• The difficult part right now is what I do between reading a book and sharing what I learn by writing and recording—that is, distilling a large amount of information down to what I want to convey.
• Sumner Redstone’s autobiography was hard to write and record about. I didn’t describe the wisdom from it clearly at first, so I needed to think about it more. I ended up thinking about what I had read for a day before recording (I’d already written my post), and that was helpful. More time to process helped me connect the dots on insights that weren’t obvious and draw parallels to my experiences as an entrepreneur. I want more buffer time between reading and recording to process. I think what I share will be more valuable if I have it.
• There’s no consistency in the format of my recordings. It’s early, and I’m experimenting, so this makes sense now. But I’m not a freestyle-it-every-time kind of person. A consistent format could help me prepare to record (I’ve decided to work toward this), increase the likelihood that each recording is valuable to listeners, and set listeners’ expectations.
• During a feedback session this week, I learned that someone purchased a biography because I’d recorded about it. I would never have known that without that conversation. Someone purchasing a book is the ultimate sign I’ve given them value, but I don’t have any insight into this. I want data! Amazon’s affiliate program seems like the best (and only) way to see this data.
• Google NotebookLM is an impressive AI tool. I’m really excited about it. I can see lots of value in using the power of AI to search specific documents and your own notes. If it would allow users to query the documents and notes of others (with their permission, of course), that would be game changing. I’ll be watching closely to see how this product evolves.
• Extracting my highlights from books I’ve read is something I’m excited about, but it’s a lower priority right now. I believe I’ve found a good partner for this when the time is right to tackle it.

Those are my struggles and learnings from this week!

Prefer listening? Catch audio versions of these blog posts, with more context added, on Apple Podcasts here or Spotify here!

This is my two-hundred-eighteenth weekly reflection or update.

Last week, I changed my weekly reflection to a weekly update on a current project. For more on why I made this change, see here.

Current Personal Project: Reading Books about Entrepreneurs and Sharing What I Learned from Them via Blog Posts and Audio Recordings Distributed as a Podcast

Metrics (since 4/1/24):

• Total audio recordings published: 42 (+8)
• Total blog posts published: 62 (+7)

What I completed this week (a holiday week):

• Read autobiographies of Ed Thorp and Sumner Redstone (see here and here)
• Published eight recordings—one was a bonus episode on Ed Thorp (#40 Ed Thorp Part 4)
• Had four additional feedback sessions—I missed my target by one
• Compiled and sorted feedback from five sessions completed the week of 5/20/24
• Tested Google NotebookLM
• Evaluated a candidate for extracting my highlights from books
• Updated podcast titles—added series number (e.g., “Part 2”) and other tweaks
• Researched metrics for podcasts

Content:

• Audio content changes: I now include the series number, how I discovered the book, an intro including what the recording will be about, more context throughout, personal insights and takeaways, and a closing.
• The average recording length increased from roughly 5 minutes to 12 minutes
• My current goal for each book is a three-part series

What I’ll do next week:

• Read two biographies or autobiographies
• Write seven blog posts and record seven audio blogs
• Adjust podcast titles
• Compile feedback from sessions completed the week of 5/29/24 and identify insights
• Make changes to audio content based on feedback
• Complete five feedback sessions
• Identify two people to study who has successfully shared book insights via solo podcasts or YouTube channels (the books can’t be about entrepreneurs)
• Make a decision on whether to use Amazon affiliate links for books
• Crystallize, in writing, my “why” for doing this project

Asks:

• Listen to my most recent audio recordings and provide feedback on how I can improve them. The more candid the better! Email me at hello [at] jermainebrown.org.

This week was hard. In my post tomorrow, I’ll share more about what I struggled with and what I learned.

Week two hundred eighteen was another week of learning. Looking forward to next week!

FYI: I’m still playing with the format for this weekly update. I’ll add and remove stuff until I settle on a format I like.

Prefer listening? Catch audio versions of these blog posts, with more context added, on Apple Podcasts here or Spotify here!