While researching a business, I learned that it generates significant revenue from ads. Digging deeper, I found out that it’s charging 10x more than I’d envisioned for ads. The coveted (and most expensive) ad slots are sold out for the next six months. I don’t have any inside information, but it wouldn’t surprise me if this business is generating eight figures in annual revenue from ads.

I don’t know a lot about ad-based business models, and this project has me curious. I want to learn more and will dive deeper into this space.

Today I got to watch serendipitous interactions between several entrepreneurs who didn’t know each other before today. The inevitable “What are you working on?” question came up in most of these conversations. After sharing, these entrepreneurs were able to add value to what the others were working on in some way.

My takeaway from today was that entrepreneurs have more to gain than lose from sharing their ideas and what they’re working on. The more you share, the more opportunities you provide for others to help you and the more feedback (positive and negative) you get. Both will improve your idea or project.

Yesterday I shared my thoughts on wisdom vs. knowledge. I have a daily habit of acquiring knowledge, which I enjoy. I’ve noticed a pattern as I’ve been reading more long-form content, mainly books. Some books add considerably more value than others. I’ve been thinking about why this is the case for the last few months.

The most helpful books I read last year have a common trait. They were about how people took action toward a stated goal. The books explained their thought processes as they learned by trial and error, detailing their learnings and how what they learned changed their behavior during their journey. These books were about how people acquired and applied knowledge. They were books that contained the wisdom others had accumulated (often over decades).  

This year I want to refine my reading a bit. I enjoy learning about new concepts and ideas, but I want to focus more of my time on reading books that contain wisdom, not just knowledge.

As an early-stage founder, I was part of an entrepreneurial group that taught new founders about key business functions. Each quarter we went deep into a specific business function: marketing, finances, HR, marketing, etc. At the end of each of those sessions, I better understood functions that didn’t come naturally to me (e.g., marketing). I felt educated. But I still had a problem: What do I do with this new knowledge? How do I use it in my business? I’d learned what I needed to do, but I still had no idea how to do it.

This experience highlighted the difference between knowledge and wisdom.

Knowledge is acquired by learning new information or being made aware of something. Learning about marketing is an example of acquiring knowledge. Knowledge acquisition doesn’t always equate to adding value. There’s another step.

Wisdom is the ability to apply knowledge in a manner that aligns with the outcome you desire. Wisdom means changed behavior and improved decision-making—knowing what to do and when to do it. Wisdom is acquired from experience (yours or someone else’s). Growing your company through marketing execution is the result of wisdom.

Through trial and error and talking with other successful entrepreneurs (who shared their experiences), I learned how to apply the concepts I learned in those sessions to grow my business. My problem was solved.

This experience showed me that knowledge is important. You can’t apply something if you aren’t aware of it, which is why continuous learning is so important. But wisdom is what I value most because applying knowledge well is how I achieve the outcomes I desire.

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

• Exiting venture capital – I’ve noticed an uptick in the number of VCs I’m talking with who are considering doing something outside VC. Many are looking at the prospect of returns, the number of years required to realize them, and the challenging exit environment for IPOs and M&A.
• Complexity – This week was a reminder that explaining complex concepts simply is a way to give value to others and enhance your own learning at the same time.

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

This week I chatted with a founder who wants to hire for a key role but feels he can’t afford to do so. The business is bootstrapped and hasn’t received any external growth capital. I faced the same situation when I bootstrapped my company. I was drowning and needed someone who could think strategically and execute. I wanted to hire someone in a leadership role, but the business wasn’t generating enough cash to support an additional leadership-level salary.

I ultimately realized that I would be adding this person to help grow the business, not stagnate it. If the business grew, then the incremental cash generated by the business could cover the additional salary expense.

I couldn’t afford to pay someone for a year if they didn’t help move the business forward. I also couldn’t expect them to move mountains on their first day. There would be an evaluation and ramp-up period, and at the end of it, I should know if their contributions could help grow the business and if they were a good culture fit. Because I was hiring a leader, I estimated that within three months I should know. After reframing it like this, I realized that I didn’t need to think in terms of the business’s current state absorbing this leader’s entire annual salary. It just needed to be able to absorb three months’ worth or so. Said differently, I needed to be able to invest just one-fourth of their annual salary. Since this amount was much lower, thinking of it this way made the decision seem less risky.

I ended up hiring someone, and it worked out perfectly. Within a few months, he had learned the specifics of the business and our industry and was contributing in a meaningful way. The business began generating more cash around the third month, and within twelve months the growth more than covered his salary.

My big takeaway is to not think in terms of annual salary when resources are limited at an early-stage company. Instead, think of hiring as making a three-month (or so) investment in someone to accelerate business growth (and cash generation). By the end of three months, you can usually tell if you’ve made the right decision. This isn’t a hard-and-fast rule and doesn’t work for all roles or at all companies, but it’s an alternative way to think about hiring when things are tight.

Today a friend texted me about a company I follow and sent a screenshot of a news headline. He wanted me to be aware that the company may be going through hard times. I read the headline and laughed.

The headline included company financial figures that were wrong. I know they were wrong because I’ve read the reports issued by the company. The writer clearly didn’t understand the company and had confused the details. I pointed this out to my friend and shared the correct financial figures, which show the company’s doing fine.

This exchange was a reminder of the value of getting first-source data. When you rely on other people’s interpretations, you run the risk of basing your conclusions and actions on incorrect interpretations.

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.