It’s been interesting to watch the last few years of venture capital. The number of firms raising larger funds appears to be increasing. This sounds good until you consider the math of venture capital funds. Most early-stage funds consider an investment a winner if it returns the entire fund or more. If you raise a $500 million fund, you’re looking for an investment in a single company to return $500 million or more. The number of companies capable of such a return is small, so when you find one, you must capitalize on it. If you don’t, a fund is less likely to generate a meaningful return for its investors when the companies that will fail are factored in.

Instagram is a well-known acquisition. It was founded in 2010 and acquired in 2012 by Facebook (now known as Meta) for $1 billion. Andreessen Horowitz invested $250,000 in Instagram’s early seed round and realized $78 million at the time Instagram was sold. That’s a 312x return. The challenge is that Andreessen made the investment from a $1.5 billion fund. Instagram was the investment of a lifetime, but it didn’t return the fund. It returned less than 6% of the fund. That means Andreessen would need to make 19 investments like this one to return its fund. That’s not likely. Do note that Andreessen made decisions specific to this situation that reduced the firm’s return, but this nevertheless illustrates the challenge of large funds investing at the ground level of a company.

The larger the fund, the larger the check the fund needs to write (unless it increases the number of checks) for a single investment to return the fund. When VC firms raise larger funds, many choose to invest at a slightly later stage (think seed instead of pre-seed or series A instead of seed) because the larger check size makes sense given the number of checks they want to write out of that fund. I think this leaves a void to be filled. The question is, what’s the optimal way to fill that void AND still generate a meaningful return?

Today marks the end of my one-hundred-twenty-third week of working from home (mostly). Here are my takeaways from week one hundred twenty-three:

• Tough decisions – This week was a reminder that tough decisions require a balance of IQ and EQ.
• Good people – I spent time connecting with other investors at an event this week. Good high-quality people in a fun environment. This was another reminder that good people know other good people.
• Shower thoughts – I’m thinking more about a particular problem—even in the shower. The last time I thought about a problem this much, I started a company to solve it.‍
• Downtime – I have some downtime coming up. Looking forward to spending time with friends and family.

Week one hundred twenty-three was a busy week. Looking forward to next week.

The rise of no-code tools has made it easier than ever to get early versions of products into the hands of users for validation. What used to take months and a technical leader can now be done in a weekend by almost anyone. No-code tools are a founder’s friend for this part of the journey—but they can’t be relied on much beyond that.

I chatted with a founder who has a few enterprise customers paying to use a solution he built via no-code tools. He’s now looking to raise capital off this validation so he can scale. The challenge is that he doesn’t have a full-time technical leader on his team. I explained to him that his situation carries high execution risk that could hinder his fundraising. He hasn’t shown he can build a technical product. Nor does he have a technical leader with a track record of building products. Investors will give him credit for solving a valid problem because customers are paying, but there will be questions about technical execution. Can he build a technical solution and scale it?

No-code tools are great for validating the problem, but they aren’t the goal. If you’re a founder using or considering using a no-code tool, have a plan to start building your own proprietary product so you can remove concerns around execution and build something scalable.

I chatted with a founder who’s building an impressive software company. He’s bootstrapped his growing—and profitable—company to $2 million in annual recurring revenue. And he’s done it without proximity to success, since he lives in a tier 3 city. He’s been figuring it out as he goes. I could tell he didn’t understand the significance of what he’s built to date. Sure, there are things that need to be cleaned up, but the results are impressive given his resources and environment. He’s thinking about raising capital now and isn’t sure how to go about it or whom to talk with.

I think of him as an outlier founder. He’s outside the purview of traditional start-up and venture capital networks and ecosystems. Yet he’s demonstrated that he has many of the traits that make a great founder, including resilience in a suboptimal environment. If he were surrounded with the right resources and advice, this founder has the potential to build a huge business that customers love.

Outlier founders (and markets) really interest me. They’re solving unique problems that are overlooked by most people. I believe there’s a ton of opportunity to have a huge impact on society by getting resources to outlier founders and markets.

I talked to a friend today who’s in a fortunate position. He’s an executive with start-up experience, and several companies are recruiting him. All the opportunities look good on the surface, and all the founders are trying to move the process along quickly. He’s trying to figure out how to make the best decision for his family. He asked for my thoughts.

I think I know which company he’ll end up with. From the initial pitch, everything sounds promising. The market is big, the product is great, customers love the solution, and the team is strong. My feedback was simple: Don’t fall in love with any opportunity until the deal is signed. Continue to move all the opportunities forward with a focus on diligence to better understand each and gauge for fit. The recruitment process is bidirectional—treat it as such. Understanding the market and the team (especially the culture) and talking to customers are some ways to gain insight. As you dive deeper, you’re bound to uncover things that didn’t make the sales pitch; you’ll have to determine if they’re deal breakers or not.

I’m excited for my friend and can’t wait to see where he lands!

I was chatting with a founder about his fundraise. He’s frustrated because it isn’t going as planned—he wanted to be through with the fundraise by now. He’s deep into conversations with a few investors and asked for some thoughts.

I view fundraising as a momentum-building process. Once you get a little momentum going, you’re rolling. I suggested that instead of asking how to complete the fundraise, he should step back a bit and think about how could get some visible momentum. Is there an angel investor or firm that’s close to a decision that he can persuade to close? If so, that’s momentum he can use to instill a sense of urgency in others.

Momentum is a powerful force and a fundraising founder’s friend.

I listened to a friend criticize a founder’s decision on an important issue. The founder originally told his staff they would do X. A few weeks later, he changed his mind and decided to do Y. I was curious why he changed his mind, so I asked. In short, the data changed. His initial decision was based on a projection that had materially changed since then. If he’d stayed the course, the result could have been serious challenges for his company in the future. The initial decision was well communicated and well received. But when the decision was reversed, there was no official communication; people heard about it through the grapevine.

Hard decisions must be made when you’re leading others. There’s no way around them. Making difficult or unpopular decisions isn’t what gets leaders in trouble; it’s the way they’re communicated—or not—that can land leaders in hot water. Some leaders avoid delivering unpopular news for fear of upsetting their teams. What they don’t realize is that people are often OK with whatever happens if they know why it’s happening. And people don’t like uncertainty. They want to hear from their leader when there’s important news that could affect them.

If you’re a founder, there’s nothing wrong with changing your mind or making unpopular decisions. It comes with the territory. But be aware that how you communicate your decisions can have a lasting impact on your team’s confidence in you as a leader.

I listened to an interview given by the CEO and co-founder of Coinbase. This cryptocurrency marketplace is publicly traded and, as of this post, has a market cap (i.e., valuation) of almost $14 billion. Brian Armstrong co-founded the company in 2012 and has been the CEO from zero to $14 billion public company, so I was curious to hear what he had to say.

It’s a lengthy interview with lots of great nuggets, but one especially stuck with me. Asked for advice on surviving the early days (when you have a team of five or fewer), Armstrong said, “If you’re pre-product–market fit, the best advice from that period is action produces information. Just keep doing stuff.”

Armstrong elaborated: doing something, even if it’s wrong, will produce information. Whatever you do will be proved to be either a good move or a failure. If it’s a failure, you’ll learn from it and get a better idea of what you need to do to achieve success—the right next step or solution to the problem. If you do nothing, though, you get no information and make no progress.

Some people are hesitant to act because the path to success is unknown. Armstrong addresses this with an analogy. Trying to do something great is like being at the base of a mountain shrouded in fog. You look up to the top and ask yourself how you can get there. You can see only three or four steps ahead because of the fog—the path to the top is hidden. When you take a few steps into the fog, you can see another three or four steps ahead but no more, because the fog is still there. The only way to uncover the path to the top is by taking steps into the unknown, which reveals the path a few steps at a time.

I enjoyed Brian’s thoughts, and I agree. If you want to hear this part of the interview, take a listen here.

Today marks the end of my one-hundred-twenty-second week of working from home (mostly). Here are my takeaways from week one hundred twenty-two:

• July – Today is the last business day of the month. July flew by, and the end of summer is fast approaching. I want to make the most of these last few summer weeks.
• Good people – This week was a reminder that the world is super small and good people know other good people. I connected with someone in another country, and it turned out that we have many unexpected mutual acquaintances. Those people helped me quickly understand that my new connection is a quality person.
• Hustle time – I had conversations with a few friends working on new ideas that they’re hustling to get off the ground. Being around other people also in hustle mode energized me.

Week one hundred twenty-two was calm. Looking forward to next week.

I read a quote today that I like:

“There are those that look at things the way they are, and ask why? I dream of things that never were, and ask why not?”

~ George Bernard Shaw

Perspective has an outsize impact on our decision-making and actions. Accomplishing the impossible is the result of asking “why not?”

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