November 1936 changed Roy Thomson’s business life. That’s the month when Jack Kent Cooke, a 24-year-old traveling salesman, asked for a job at Roy’s radio station CJKL. Roy was having problems with a newly acquired station, CJCS, in Stratford, Ontario, and hired Jack to turn the station around. Within six months, the station was profitable, and Roy decided to sell it for $10,000 for a profit of $6,000. Roy became fond of Jack and hired him to oversee sales in a newly created Toronto office.

Jack’s superior sales skills took that responsibility off Roy’s plate. He spent more time “figuring,” as he called it. In 1938, Roy convinced Jack to move to Timmins to manage all aspects of all five radio stations. Everything was going well until a fire in April 1939 burned down the building that housed station CKGB and the Press newspaper in Timmins. Roy was underinsured, but he bounced back. He borrowed to build a building for both his companies.

The world was on the cusp of World War II, and rumors circulated that paper would be rationed and sent to the United States. Roy figured this would lead to more advertising dollars flowing to radio, especially since more people were listening to their radios to receive war news. Not wanting to share the profits he envisioned his stations would produce in 1940, he bought back as much of his company stock as he could.

By 1940, the radio stations were running smoothly under Jack’s management. As Roy had predicted, the war was good for his radio business. Jack also found reinvestment opportunities for the profits that Northern Broadcasting and Publishing was generating. He and Roy partnered to buy their first French-language radio station in Quebec for $21,000. Two other purchases followed. Roy owned 66% of the partnership, and Jack owned 33%.

Roy and Jack expanded their radio empire by agreeing to manage Ontario radio stations owned by a senator. This capital-light approach gave the two partners 49% ownership in them.

The war, after it began, became a massive tailwind for Roy’s newspaper, too. Paper rationing made advertisers buy space in smaller rural papers, like the Press, because papers in big cities like Toronto were limited in pages and ad space.

The war had put Roy’s empire on solid financial ground for the first time. The depression years had conditioned Roy to keep salaries and expenses within budget, which boosted his profitability when wartime ad revenue surged. Roy standardized his accounting, making comparing the performance of his stations, apples to apples, easy.

Eager to reinvest profits, Roy upgraded his stations, paid off bank debt, and bought back outstanding stock in his company from outsiders. In 1943, Roy spent $880,000 to buy four newspapers with a $375,00 bank loan; the rest was seller financed. He owned eight radio stations and five newspapers after that deal closed. He and Jack agreed to a partnership in which they shared in each other’s deals; Roy got 66% and Jack 33%. The two started sourcing deals independently and evaluating and investing as a team.

Jack, eager to do more radio deals, found a Toronto radio station he could buy for $500,000. He didn’t have the money, so he convinced Roy to sell their Quebec stations. When those stations were sold, Jack's share of the proceeds provided him with capital he used to complete the purchase of the Toronto station. Roy declined to be part of the deal to buy the Toronto station, but within a few months, Jack had turned the station from unprofitable to solidly profitable. Jack became known as a radio station entrepreneur.  

Roy bought two more newspapers in small towns for $750,000 and realized there was a big opportunity to purchase more small-town newspapers. Families had owned them for generations, had underinvested in them, and had to pay inheritance tax each time the ownership transferred to the next generation. Roy worked with investment bankers and issued $1,000,000 in bonds so he could go on a buying spree. Roy’s economic blueprint for buying and running rural newspapers would make him the millionaire he’d dreamed of being years earlier.

After Jack successfully managed the Ontario radio station for the senator, ran Roy’s stations, and turned around his Toronto station, a prominent media family approached him. They offered him a massive contract to manage their Ottawa radio station. On one condition: Roy could not be part of the deal. Jack accepted, and when he told Roy he wasn’t part of the deal, it was the end of their decade-plus friendship and partnership. Feeling betrayed and cut out by his young protegee, Roy started seeing Jack as a rival. The two divested themselves of ownership in each other’s companies and went their separate ways. Jack would later call that deal “one of the great mistakes in my life.”

With a thriving empire, Roy would soon begin to set his sights on taking his empire international.

According to the biography about him, Roy Thomson was determined to learn how to start a radio station. He tracked down the company that owned the license to broadcast in his area and struck a deal to acquire the license for $1. He struck another deal to set up his station in a building owned by a theatre company, paying in advertising time, not dollars. Station CFCH went live in March 1931.

Roy had solved his problem. Radio orders began rolling in. But he needed cash to pay for radios he’d gotten from the manufacturer on consignment. He landed a big contract with a large store in a rural community and leveraged that purchase order to borrow enough money to pay the manufacturer. Roy narrowly avoided bankruptcy.

Things remained tight for a few years, to the point that Roy’s employees knew they couldn’t immediately deposit their paychecks. Despite the shaky ground his business was on, Roy was elected North Bay alderman in 1931 and lost a bid to become mayor of North Bay in 1932. He then refocused his energies on expanding his business and eyed Timmins and Kirkland Lake, both in Ontario, as promising cities. Roy borrowed money from a bank and launched station CKGB in Timmins.

With CKGB flourishing, Roy partnered with a politically connected friend to get a radio license in Kirkland Lake. He raised money from wealthy Kirkland Lake residents and launched CJKL, which was well received. Roy was on a roll but still on thin ice financially.

When the local newspaper in Timmins, the Citizen, attacked Roy’s station CKGB for running ads for a competing newspaper, Roy offered to buy the unprofitable Citizen for $6,000. The owner, a gentleman named Bartleman, accepted, and Roy financed the deal by providing $200 at closing and giving Bartleman twenty-eight promissory notes for $200 each, payable over twenty-eight months. Roy sold his supply store to an employee. He changed the Citizen to the Timmins Press, and in 1934 Roy was a publisher.

To learn best practices for newspapers, Roy looked up the names of a hundred American cities the size of Timmins and ordered a copy of each one’s paper. He measured the layout of each paper and estimated the earning power of a small rural paper. Using his analysis, he optimized the size of each section of the Press to maximize its earning power.

Roy also realized that he had to publish more frequently to beat the competing town paper. He went from weekly to twice a week and, finally, daily in September 1935. Going daily was painful for his staff to execute. Readers got their papers late for a few months until his team got the hang of things. Roy ended up having to borrow $4,000 to upgrade his equipment to make daily publication feasible, but the investment paid off. Readers enjoyed having a daily paper, and the Press became the popular town newspaper.

Roy wasn’t able to pay the promissory notes, so he made Bartleman and his associate directors on his board and gave them ownership stakes in his company. With an eye on growth, Roy bought another station, CJCS, in Stratford, Ontario. The fact that he never had enough money in his accounts to cover payroll didn’t stop Roy from acquiring to grow.

By this time, Roy was managing four radio stations, a paper, and team members in various cities. He didn’t have a partner, so he worked sixteen or seventeen hours a day, negatively impacting his time with his family. He lost some of his connection with them. But Roy was 42, and in his mind he was twelve years behind on becoming a millionaire, so the sacrifice was worth it. Little did he know he was about to meet someone who would help him take his company to the next level and improve his personal life.

A few weeks ago, I listened to an interview with Syed Balkhi, founder of WPBeginner and Awesome Motive. He recommended the trilogy of books on Roy Thomson, who founded what became the Thomson Reuters media empire and whose family is one of the wealthiest families in Canada. I wanted to learn more about Roy, so I read Roy Thomson of Fleet Street by Russell Braddon.

Roy was born in 1894 and raised in Toronto, Canada, by working-class parents. As a kid, he developed a love for numbers. For fun, he manually calculated the statistics of all baseball players from information he found in newspapers. At age 14, to help his family, he dropped out of school and started working full-time doing administrative work for local businesses.

Roy’s aunt was a shrewd investor. But Roy was shocked to learn she didn’t keep any records. He used his newly acquired bookkeeping skills to record her investments. She rewarded him by loaning him money to invest alongside her. Roy was obsessed with making money and was excited to invest with his aunt. At 17, he proclaimed to coworkers he’d be a millionaire by age 30.

The investments with his aunt did well, and Roy reinvested profits to buy his employer’s stock. He built an impressive $15,000 portfolio. Roy excelled at work. He became a branch manager and did outside sales for a local company. That role was pivotal because it taught him how to sell and, more importantly, helped him discover his passion for doing deals.

In 1917, Roy married Irma, and by the end of 1918, they had two children. Anxious to get rich, he took his $15,000, quit his job, and moved his family to remote Saskatchewan to become a farmer. The decision to purchase and farm 640 acres was a disastrous mistake. Roy lost much of his investment when he gave up farming within a year. He was 25, and he realized he couldn’t take losses like that if he wanted to become a millionaire by 30.

Automobile sales were exploding in 1920. Roy and his brother Carl pooled their money to start a company selling replacement parts to garages. To expand, they bought a machine shop, and by 1924 they’d grown the company to $700,000 in sales.

Roy was buying parts from manufacturers and selling them to garages. Expanding this business required inventory, which required capital, which Roy and Carl didn’t have. When the garages were slow to pay their bills, Roy and Bill had cash flow issues. They almost went bankrupt.

The brothers reworked their debts, and Roy left Toronto for Ottawa, which he saw as an untapped market for automotive parts. He and Carl set up a new Ottawa company, Service Supplies Limited. At the same time, in 1925, radios were new. Manufacturers were eager to sell them to businesses that sold to consumers. Trying to dig himself out of debt, Roy started selling radios too. By 1928, the new company was doing $80,000 a year in sales and the debts from their shuttered business had been paid off.

Roy wasn’t satisfied. He wanted to grow the company more. Hearing about Trimmis and Kirkland Lake, two rural cities thriving because of gold mines in Ontario, Roy moved his family to North Bay, Ontario, in 1928. Roy realized he had to help rural dealers. They didn’t know how to sell radios to consumers. Roy devised a door-to-door sales strategy that let consumers test radios for a week. If they liked them, he hoped they’d buy them. The strategy was innovative, but there was a significant problem that Roy and his dealers had overlooked: there was no radio signal in this remote area. There was nothing for people to listen to on the radio.

With the depression beginning to affect Roy’s dealers and payments from them to Roy slowing, Roy started to ponder how he could solve this problem. The more he thought about it, the more he realized there was only one way to solve it. He had to start a radio station.

Current Project: Reading books about entrepreneurs and sharing what I learned from them via blog posts and audio podcasts

Mission: Create a library of wisdom from notable entrepreneurs that current entrepreneurs can leverage to increase their chances of success

Metrics (cumulative since 4/1/24):

• Total book digests created: 9 (+0)
• Total blog posts published: 133 (+7)
• Total audio recordings published: 97 (+5)
• Recent digest length: no digest completed this week
• Recent recording length: 12 min (+0)

What I completed this week (link to last week’s commitments):

• Read the biography of Roy Thomson, founder of what became Thomson Reuters
• Began creating the digest of the biography of Roy Thomson
• Had two additional feedback sessions with podcast listeners

Content:

• No material changes

What I’ll do next week:

• Read the biography of either Michael Bloomberg or Jack Kent Cooke.
• Finish creating a digest of the Roy Thomson biography.
• Write and publish blog posts about one book: roughly five posts
• Record audio podcast about one book: roughly five recordings
• Publish audio podcast about one book: roughly five recordings
• Complete three feedback sessions

Asks:

• No asks this week

Week two hundred twenty-nine was another week of learning. Looking forward to next week!

Current Project: Reading books about entrepreneurs and sharing what I learned from them via blog posts and audio podcasts

Mission: Create a library of wisdom from notable entrepreneurs that current entrepreneurs can leverage to increase their chances of success

What I struggled with:

• No material struggles this past week.

What I learned:

• It takes much more work to turn an excellent entrepreneurial journey into a compelling blog post and audio podcast series that resonates with others if it was captured poorly in a biography. Sometimes it’s worth it, and sometimes it’s not.
• Newsletters are another way to distribute what I’m learning from books.
• I’ve learned in feedback sessions that most listeners multitask when they listen to the podcast. Therefore, sometimes they don’t make connections between what I’m sharing from a book to their situation. When I talk with them individually, I make the connection for them, and it changes their perspective on that podcast series. I could do a better job of connecting the dots in my recordings. I could share examples from my experiences or hypothetical ones. That might kick-start listeners to generate their own ideas on how to apply what they’re hearing.
• Reading and digest creation are habits I need to do daily because they build the library. A high-quality library is the most valuable component. As the library expands, its value increases.
• I need to consistently capture my insights, personal experiences, and links to stories of other entrepreneurs in each digest.  

Those are my struggles and learnings from the week!

This week I reflected on my personal project around reading books and sharing what I’m learning via blog posts and audio podcasts. Creating a digest of each book I read has been the focus of the last few weeks. I’m currently reading older books that don’t have a Kindle or other electronic version available, so the digest must be created 100% by hand. The more I create these digests, the more I realize how foundational they are and how important it is to make them high quality. They serve as the foundation for my blog posts and podcasts. They also allow me to review concepts from a book quickly. Creating digests is something new for me, so it’s painful and slow now. But it should become easier as I get more reps.

Right now, I’m reading daily, working on a digest daily, and blogging daily about what I read. These feel like good habits that I can sustain. But I haven’t settled on a recording frequency. Daily doesn’t feel appropriate anymore. I want to focus on quality more, and it’s hard to do that and publish a recording every day.

Today, I decided to test a different approach for a few weeks. I’m a big fan of turning my goals into habits as much as possible, so I’ll try setting a goal and figuring out what frequency is needed to turn it into a habit. Instead of focusing on recording frequency, I’m focusing now on how often I publish a podcast series. For context, I publish a series of five episodes for each book I read. I’m starting by aiming to publish a series every other week, which means I’ll publish roughly two series per month. From there, I’ll test and figure out what recording and editing frequency make sense to make that happen. This will also allow me to improve the quality of the recordings intentionally.

So, to recap, this is what I’m aiming for over the next few weeks:

• Reading  – daily
• Digest creation – daily
• Publishing blog – daily
• Publishing audio podcast series – every two weeks

This feels like a good change. I’m curious to see how it plays out over the next few weeks.

When I began recording audio podcast episodes in April, the recordings were awful. I figured the more practice I got, the better the episodes would be, so I set a goal to record 100 episodes by the end of summer and then reevaluate. I’m at 92 episodes and will be at 100 soon.

The series I’m most proud of is the John H. Johnson series. I felt I’d made a breakthrough. I figured out my content format, and things started to click. I’m proud of the quality of that series, which isn’t the case for prior series. I recorded another series after Johnson’s and then took a break from recording to focus more on improving my process to create a digest of each biography I read.

I’m back recording this week. I listened to the John H. Johnson series for the first time in a few weeks. I wasn’t as impressed as I had been. The quality was better than that of prior series, but I picked up on many areas where I need to improve. I must improve my delivery, connect the dots for listeners, and do various other things. I’m still proud of this series, but it’s not the Mona Lisa I thought it was a few weeks ago.

What happened? Recording those first 92 episodes, I published one almost daily. This aggressive schedule put me deep into the weeds of creating recordings. I got lots of reps, which was needed and helpful. But it made it harder to see where I needed to improve and to gauge the quality of my recordings. Now that I’m not publishing every day, I can see things more clearly. The areas where I need to improve are more obvious.

This reminded me that when I’m aggressively doing something new, I must avoid getting caught up in hitting metrics or the minutia of execution. I need to take time to zoom out and consider the big picture.

For this project, stepping back and focusing on another part of it was helpful. I returned with a fresh perspective and could see the forest, not just the trees.

This week I’m doing more test runs before I record an episode, so the recording process is a bit slower. I hope the quality of the recordings will be higher. I’m also testing some other ideas to help me be more relaxed when I record.

Current Project: Reading books about entrepreneurs and sharing what I learned from them via blog posts and audio podcasts

Mission: Create a library of wisdom from notable entrepreneurs that current entrepreneurs can leverage to increase their chances of success

Metrics (cumulative since 4/1/24):

• Total book digests created: 9 (+1)
• Total blog posts published: 126 (+7)
• Total audio recordings published: 92 (+0)
• Recent digest length: 8% of the book’s length (+4%)
• Recent recording length: no recordings this past week

What I completed this week (link to last week’s commitments):

• Created a digest for the second biography I read about Billy Wilkerson, founder and publisher of The Hollywood Reporter and founder of the Flamingo Hotel in Las Vegas
• Finished the digest for Ted Turner’s autobiography
• Had three additional feedback sessions

Content:

• No recordings this past week

What I’ll do next week:

• Read the biography of Roy Thomson, founder of what became Thomson Reuters
• Create a digest for one book
• Write and publish blog posts about one book: roughly seven posts
• Record audio podcast about two books: roughly ten recordings
• Publish audio podcast about one book: roughly five recordings
• Complete three feedback sessions

Asks:

• No asks this week

Week two hundred twenty-eight was another week of learning. Looking forward to next week!

Current Project: Reading books about entrepreneurs and sharing what I learned from them via blog posts and audio podcasts

Mission: Create a library of wisdom from notable entrepreneurs that current entrepreneurs can leverage to increase their chances of success

What I struggled with:

• Last week I focused on honing my process of distilling a book down to a digest and testing a progressive summarization method. It’s painful to do this with books that don’t have an EPUB (i.e., e-book) file—it must be done by hand. I’m trying to find the right balance between capturing too little and too much in a digest. And trying to figure out a good length for a digest relative to a book’s length. And trying to figure out where it makes the most sense to add context and links to external sources in the digest without disrupting the flow of the story. Lots of work to do here. The quality of the digest affects the quality of what I can share with others.    
• Reading, creating a digest, and publishing blog posts for one book a week is doable. Adding on top of that recording, editing, and publishing a pod series the same week has been a struggle.

What I learned:

• I’ll start measuring the number of book digests I create and their length (relative to the book’s length). If I don’t measure this, the quality of these digests likely won’t improve.
• If an entrepreneur endorses a biography, that’s a good sign that the biography is high quality and worth reading.
• I must screen books continually. I must identify high-quality books I want to read while I’m still reading another one. Waiting until I finish a book to start screening for the next one has led to spending too much time on books that aren’t excellent.
• Biographies that include specific information about how entrepreneurs solved problems and specific financial information are more likely to include actionable insights that other entrepreneurs will find useful.
• Not creating or listening to my podcast episodes for a few weeks had an unexpected benefit. When I listened again after a break, I was able to pick out areas of improvement I’d missed before.

Those are my struggles and learnings from the week!

I finished reading a second biography on William Richard “Billy” Wilkerson’s life. Unlike the first one, this one detailed his entire journey until his death in 1972. It also focused more on what led to his founding The Hollywood Reporter and his various entertainment and restaurant ventures.

I shared many of my concluding thoughts on Billy’s journey in an earlier post after reading the first biography. This post is about additional insights from the second biography.

How Did Billy’s Earlier Years Impact His Journey?

The death of his father led to Billy working in the film industry. Over roughly fifteen years, he worked in various roles at various companies in film production and distribution. He also managed his friend’s nickelodeon (i.e., theatre) and sold ads and wrote for a motion picture trade paper. These years of experience schooled Billy on the industry from various perspectives and led to key insights about himself and the industry. First, he was an entrepreneur and wanted to be his own boss. Next, the owners of movie studios amassed more of the industry’s profits than anyone else. Last, trade publications could wield immense power over an industry. These three key insights shaped his trajectory.

Billy’s first wife leaving him scarred him deeply. He was married five times. He wasn’t particularly close with wives two through four because he put his work ahead of them. Only after he had children with his fifth wife did he make spending time with his family a priority.

How Did Billy Become So Successful?

This book details Billy’s questionable actions and associations with criminal figures. It painted a picture of someone who didn’t mind using illegal means to accomplish a goal or obtain wealth. Partly this may be a sign of his time and place, but it’s clear that Billy’s comfort with doing things that weren’t aboveboard led to financial success and outsize influence. Billy was willing to do things and go places others weren’t to get what he wanted. This approach came with a cost. Billy went into hiding in Paris to avoid being killed by Bugsy Siegel, he owned several bulletproof cars, and his house was stocked with guns.

Billy was driven to succeed by hatred for movie studio bosses. Movie studio heads ran monopolies and operated similarly to robber barons. Billy felt wronged when they didn’t give his film a chance and held that grudge for decades. His desire to topple the studio bosses fueled his passion to make the Hollywood Reporter successful and dismantle what he viewed as an unfair studio system.

Billy was naturally gifted at understanding the psychology of the rich and famous. He repeatedly used this understanding to create content in the Reporter and numerous successful entertainment and dining venues that resonated with this group and made them want to be associated with Billy.

What Kind of Entrepreneur Was Billy?

Billy was a founder who enjoyed taking an idea from inception to an operating business, but he got bored easily and didn’t enjoy managing businesses. He ruled with an iron fist, which wasn’t uncommon for that period in history. This book highlighted Billy’s ability to weather massive misfortunes. Billy refused to be taken out of the game regardless of what life threw at him. He simply took the hit and kept going.

What Did I Learn from Billy’s Journey?

Billy’s journey is a cautionary tale. He had outsize success and impacted the movie industry, but the costs of operating unethically were high. His relationships, personal and professional, weren’t healthy. He was hated by many people whose lives he harmed. And the book never described a man who lived a happy life.

Billy had an outsize impact on Hollywood and Las Vegas. He was a complex man who lived a complicated life. Anyone interested in learning more about Billy or old Hollywood may enjoy this book.