I recently met with a friend, and the topic of the ideal work environment came up. He’s a successful entrepreneur and investor. Like many, he’s worked from home quite a bit during the last few years.

He’s learned that working from home isn’t ideal for him. He can focus well, but he believes it comes at a cost. It’s harder for him to do his best work without interacting with other people. He says the buzz and energy level are polar opposites at home and the office. The office’s energy helps him get into the zone where he has his best ideas and can do his best work.

He recognizes that things have changed and flexibility is a high priority now for people on most teams, and he thinks hybrid setups offer the best of both worlds if implemented well. They satisfy the needs of folks like him while giving others flexibility.

I hadn’t thought about this lately until he brought it up, but I think the ideal work environment depends on the company’s culture and stage. Hard-charging start-ups trying to find product–market fit whose founders feed off each other for ideas might be better suited to in-person work. Slower-growth companies with mature offerings, a steady customer base, and an established culture may do well in a hybrid or even fully remote environment.

More interesting details came out today in an article about Reddit’s potential IPO. A few points reported by Bloomberg caught my attention:

• Revenue increased more than 20%, from $666 million in 2022 to over $800 million in 2023.
• The company is unprofitable. Adjusted EBITDA is negative $69 million.
• Its listing is closely watched and a bellwether for tech IPOs.
• It’s expected to unveil a public IPO filing as soon as this month.
• It could start marketing its IPO as soon as March.

These assertions can’t be confirmed as accurate until the company files its S-1 with the SEC (reporters, being human, can make mistakes).

Assuming the info is accurate, I have a few thoughts:

• This IPO will likely be a bellwether given Reddit’s brand awareness among tech and non-tech investors and the timing—if it happens, it will be the first tech IPO of 2024. This means it will be watched closely by VCs and founders. Its performance will influence other companies considering an IPO in the first half of this year.
• Last year’s fall IPOs of Instacart and Klaviyo haven’t performed well to date. Both are still trading below their IPO offering prices, even as the NASDAQ is nearing all-time highs (more on that here). What about Reddit’s offering will be different and get enough investors interested in purchasing shares?
• Reddit is most likely free cash flow negative and burning cash—I’m not sure at what rate or how close they are to being cash flow breakeven. But I wonder how this will impact public-market investor receptiveness to this listing. Instacart and Klaviyo both reported positive free cash flow for the 2023 quarters proceeding their IPO, and those listings haven’t performed well.
• I suspect public-market investors are rethinking revenue multiples for technology companies. I’m curious to see how investors value Reddit given that it’s likely consuming cash.

I’m looking forward to Reddit filing its S-1 so I can dig in. If the company decides to proceed with the listing, I’m really curious to see how investors receive this company.

Today I read in an article that Reddit picked the New York Stock Exchange for its initial public offering. Reddit is a social platform that allows users to create digital communities based on niche user interests. It’s probably best known to mainstream America for the events of 2021, when a community named WallStreetBets played a role in the GameStop saga. I visit Reddit periodically and find it helpful. I enjoy being able to get the unfiltered, crowdsourced views of others on specific topics.

Reddit is a well-known tech company. Picking an exchange is a sign it’s seriously considering going public soon. But anything could happen. The company could decide not to list (as it did in 2021). If it does go forward with a listing, that could be helpful in gauging public-market investor appetite for new technology companies. If it lists and is successful, other companies might follow its lead.

Today I read an interesting fact. In the 1860s, there was a unique group of successful stock market investors. They went against the grain and were thought of as outsiders by their investing peers. They were called “panic birds.”

Here’s what they did that was so different from what other investors did:

• You had to physically visit Wall Street to buy or sell stock then. Most investors were on Wall Street daily, regardless of whether they were buying, selling, or just observing the market. The panic birds, though, stayed far away from Wall Street when conditions were normal. They didn’t want to get caught up in the prevailing group think or speculative mindset that prevailed among investors on Wall Street. They wanted to be able to see things clearly and think objectively.
• They went to Wall Street only when the market and other investors were in a panic or desperation was rampant.
• They bought only when two conditions were met: prices had crashed and liquidity was scarce (i.e., they were getting the bargain of a lifetime).
• When they did buy, they didn’t buy broadly; instead, they bought carefully in only the highest quality companies.
• They held their investments long term. This wasn’t common—people regularly bought and sold in those days.

This list describes some successful investors alive today. For example, Warren Buffett has a panic-bird investing style. He’s had outsize success, and he’s well respected on Wall Street. Yet he lives in Omaha, Nebraska. He buys only when companies are trading at a material discount from what he believes their intrinsic value is. He’s been known to buy large positions in a handful of companies during times of crisis, and he usually holds those positions for a long time.

I found all this interesting. It showed me that most good ideas aren’t new. They’re borrowed from people who came before us, figured things out through trial and error, and went on to achieve outsize success. I suspect that Buffett and other successful investors studied history and borrowed from the most successful and timeless ideas as they formulated their investing approaches.

This is my two-hundred-first weekly reflection. Here are my takeaways from this week:

• Curveballs – This week, I was thrown a few curveballs. It was a reminder that the unexpected can happen anytime. Flexibility and focus helped me navigate the week.
• Optimism – Entrepreneurs I’ve talked with are very optimistic about 2024. Most have plans to grow businesses or launch new ones. Entrepreneurial sentiment appears to be starting the year off strong.
• History – I learned some fascinating things from historical events and people in business this week. As I read, I was able to see how current times are mimicking history.

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

I’ve been learning about business models in different industries for a few years. SEC filings of publicly traded companies have been great for companies I’ve wanted to take a dive deep into, but I wanted an additional resource. One that would help with discovery of companies and industries I’m less familiar with. One that could help me efficiently learn about new business models at a high level.

This week I found the Business Breakdowns podcast and have enjoyed listening to several episodes. It breaks down public and private companies, which I really like, and covers a broad range of industries. Some of the companies profiled I would have never thought to research, or wouldn’t have been able to because they’re private. The episodes I’ve listened to have been helpful and have gotten me thinking more about various ways of charging for the value you provide to customers.

If you’re interested in learning how different companies generate revenue and think about their business, consider giving the podcast a listen.

A few months ago, I started thinking about what traits founders/CEOs who take a company from idea to public-market company worth billions possess. It’s a small group of people, as the number of companies that reach hundreds of millions or billions in annual revenue is small relative to the total number of companies founded.

After spending time learning about people who’ve accomplished this, I see one clear trait. These people were obsessive about a single problem. They weren’t entrepreneurs who wanted to build a company but weren’t sure what problem they wanted to solve. Rather, they’d been thinking about a problem intensely and decided they wanted to solve it.

It's hard to scale a company to billions and take it public. Along the way, founders will usually get an offer to sell if the company is doing well. To reject the offer and the financial windfall associated with it and take a company public is a hard decision. To continue as a public-company CEO and endure all the scrutiny from public-market investors isn’t for the faint of heart, either. This requires a vision and level of commitment that founders aren’t likely to have if they weren’t obsessive about the problem they’re solving.

I’ll keep looking as I study more founders/CEOs of public companies, but I’ve yet to find a founder of a public company who was a founder in search of problem before starting their company.

Mark Twain is known for saying:

“History doesn't repeat itself, but it does rhyme.”

I was chatting with a friend about this quote, and he added something that stuck with me:

“The reason history rhymes is because human nature doesn’t change. People don’t change, but circumstances do.”

That’s why knowing history is important, he said.

I’m no history buff, but I do enjoy reading historical accounts of major business events and the journeys of people who achieved outsize success. I consistently read the latter and randomly read the former. This year, I want to be more intentional about identifying important events in business and monetary policy history and reading long-form content to better understand them and decisions related to them. Hopefully this will help me see patterns in human behavior that will help me understand and navigate similar future events.

I was chatting with a friend about this quote, and he added something that stuck with me: “The reason history rhymes is because human nature doesn’t change. People don’t change, but circumstances do.”

That’s why knowing history is important, he said.

I’m no history buff, but I do enjoy reading historical accounts of major business events and the journeys of people who achieved outsize success. I consistently read the latter and randomly read the former. This year, I want to be more intentional about identifying important events in business and monetary policy history and reading long-form content to better understand them and decisions related to them. Hopefully this will help me see patterns in human behavior that will help me understand and navigate similar future events.

During a meeting with an entrepreneur, the topic of unique work styles came up. He has a long track record of success, so I was interested in hearing about his approach. He almost burned out early in his entrepreneurial journey and realized that he’s a sprinter, not an endurance entrepreneur.

He learned that he isn’t wired to run hard 24/7/365. Instead, he’s more effective when he goes all out for a while and then recovers before repeating the cycle. He’ll work intensely for a few months and then take two or three weeks off to rest and recover. Recharging and recovering are key to how he operates best. He comes back refreshed, energized, and full of new ideas.

He went on to share that the key to this working style is his productivity when he’s in work mode. He works intensely—so much so that he’s able to get more work done during his sprint than most people would accomplish during his sprint and recovery period. He essentially gets the same or slightly more work done in a year, even with his breaks, than people who don’t take these kinds of breaks do.

He isn’t the first person to share this type of work style with me. I know a successful angel investor who focused intensely on investing for three or four months and then took a month or two off to recover and travel. He could do this because he was investing his own capital, so he could deploy it at a pace that suited him. He too works intensely when he’s in work mode but needs time off to recover.

Sprinting as a way of working isn’t available to everyone, but for those who are intense but not wired for endurance, it’s a work style to consider.

Today I listened to a podcast on which the guest talked about her research on focus. The gist was that it’s getting hard for people to focus for more than one minute (yes, one minute!) while we’re working because of all the distractions we’re inundated with. That one-minute figure was based on a study she’d done over a few years. I knew focus was a problem, but the one-minute stat was surprising.

My college had a Center for Academic Success. Sadly, most students never used it. Honestly, I don’t think many people even knew it existed. Serendipitously, I met the center’s director my first semester, and she impressed me. I told her about my heavy course load that semester, and she urged me to visit her center. When I took her up on her offer, I learned study techniques that proved invaluable. A lot of it was about habits that help you focus. I’ve always been able to focus on things I’m interested in, but the things I learned at that center turbocharged my ability and taught me how to focus on things that are less interesting to me (which a lot of early college classes were).

My ability to focus has played a big part in the wins I’ve had in life. Learning techniques for focusing and practicing them took my natural abilities and habits to the next level. As I think about the one-minute attention statistic, I’m concerned about people’s diminishing ability to focus. If you’re aiming for outsize success, focus is something to consider learning about (just as you would any other critical topic) and practicing so you can develop or enhance your ability to focus. Being able to focus won’t guarantee you outsize success, but not being able to all but guarantees you won’t achieve success.