I’ve been learning about successful entrepreneurs who happen to be investors—I call them “investor entrepreneurs.” They invest as their full-time profession, but not by working for someone else. I’ve been reading as much as I can about these people, including biographies about them.

 A biography, of course, is written by someone who spends a lot of time learning about their subject—in this case, an investor entrepreneur. They talk to family members and coworkers. They read files. They interview the investor entrepreneur. All to get a better understanding of the life of the person they’re writing about.

Sometimes the author can’t fit everything they learned in the book, or the investor entrepreneur won’t agree to certain information being published. Sometimes these missing pieces of information can clarify what made the person exceptionally successful.

Biography authors sometimes talk about what didn’t make it to print. Whenever I read a well-researched biography, I search for recordings of interviews and speeches the author gave about the book. This simple hack has led to stories and facts that helped me better understand some of the greatest investor entrepreneurs.

I recently came across the 10-10-10 process of Suzy Welch. It’s a framework to help consistently improve decision-making by identifying regret before a decision is made. It works like this:

• Crystalize the decision you’re making.
• Understand the options available to you.
• Identify the consequences of each option in the immediate future (10 minutes).
• Identify the consequences of each option in the medium future (10 months).
• Identify the consequences of each option in the long-term future (10 years).

Thinking about the consequences forces mental time travel. You’ll understand how “future you” will feel about the consequences of each option you’re considering. If you’re likely to regret a decision (i.e., an outcome doesn’t align with your vision of your future), you can factor that into your decision-making process and pick the decision (and likely outcome) that best aligns with the future you want to create.

An easy example of applying this is working out:

• Decision: Should I work out now?
• Options: Work out or don’t work out.
• 10-minute impact of not working out: relaxed, comfortable, do something enjoyable, etc.
• 10-month impact of not working out: feel bad, look bad, lack self-confidence, etc.
• 10-year impact of not working out: increased risk of long-term health issues, etc.

Using this framework, it makes sense to push through the immediate discomfort and exercise to reduce your risk of health issues in the future and enjoy the other medium- and long-term benefits of working out. I know that’s easier said than done, but you get the idea.

I like Suzy’s approach. It’s a simple tool that most people can use to make consistent, rational decisions.

For more on her 10-10-10 method, watch this video.

This past weekend I had the opportunity to attend two unrelated social gatherings on the same day. They were hosted by great families who happened to be at opposite ends of the economic spectrum. The hosts’ cultural backgrounds were different from each other’s and from mine, and they lived in different parts of Atlanta.

Everyone I encountered at both events was great, and I’m appreciative of the invites. I learned things about a culture I’m not familiar with, tasted new foods (which were amazing), and met interesting people from cultures different than my own.

The weekend reconfirmed something I’ve known for some time. I get a lot out of my time around good people with experiences and backgrounds different from mine. I really enjoy it. It helps me understand other people’s perspectives, which doesn’t come naturally to me. It’s also a fun and interesting way for me to learn about new cultures, experience unfamiliar traditions, and acquire wisdom not available in my usual circles.

Living in a bubble isn’t for me. I enjoy meeting a variety of people and having new experiences.

I’ve been posting daily for about three-and-a-half years. At the end of each day, I stop to reflect and write a post.

Recently it was suggested that I consider writing a few posts ahead of time. It’s akin to completing posts and banking them. I wasn’t a huge fan of the idea initially. It’s challenging enough to come up with one post every day. Writing multiple posts in a single day sounded like a herculean task.

I thought about it and reached the following conclusions: If I tried to stack posts and failed, I could keep doing what I’d been doing, writing my post at the end of each day. If I succeeded, I wasn’t sure what the benefits would be, but I suspected they would outweigh the effort. In the end, I decided there was zero downside to trying and it would be fun to challenge myself. So, I gave it shot.

I’m happy to report that I’ve been able to write and bank multiple posts in a day. I don’t do this every day, but I’ve done it a few days now. As with anything, the first time I had to write multiple posts in a day it was hard. But it got easier.

It’s early, but I’ve noticed three benefits so far. First, I feel less pressure to write because I have one or two completed posts to fall back on, just in case. I still write at least one every day, but I feel less pressure to do so. Second, I’ve started to write posts as insights come to me instead of at the end of the day. I’ve written more posts in the morning or early afternoon, which was rare before. The third benefit is harder to explain, but I’ll try. Being under less pressure to write a daily post has allowed my mind to wander a bit more, which has led to some interesting insights that I don’t think I would have had otherwise.

I’m glad this challenge was suggested to me, and I’m hoping I can keep writing multiple daily posts when insights warrant.

I read a quote recently that stuck with me:

Success is getting what you want. Happiness is wanting what you get.

                                               ~ Dale Carnegie

Simple, but thought provoking.

Are you successful, happy, both, or neither?

This week, Atlanta-based LeaseQuery announced that it has acquired Stackshine. LeaseQuery is a software company that was started to help accounting teams accurately record lease obligations in their financial statements. It has since created additional solutions that simplify accounting. Stackshine is spend management software. It helps organizations detect and manage software subscription spend and usage organization-wide.

George Azih has built an amazing company with LeaseQuery. He’s one of the smartest entrepreneurs I know. He has an incredible founder story that includes bootstrapping the company to around eight figures in revenue before raising outside capital.

Congrats to George, the LeaseQuery team, and the Stackshine team! I can’t wait to see what’s next for LeaseQuery!

This is my one-hundred-seventy-sixth weekly reflection. Here are my takeaways from this week:

• Founders’ mindsets are changing – More early-stage founders are thinking about customer revenue as a source of funding. This forces them to build something customers will pay for—not something they can pitch to VCs. Regardless of what happens in the fundraising environment, this is a good mental shift for founders.  
• Exposure gap – Some people haven’t been exposed to certain concepts or ways of thinking, which puts them at a disadvantage. To reach the same destination as people who’ve benefited from wide exposure, they must travel further. It isn’t fair, but it’s the way the world is. Acknowledging the gap and working hard to close it is often the best approach to minimizing its long-term impact on one’s trajectory in life.
• I don’t feel like it – This week was a reminder that the things I don’t “feel like” doing are exactly the things I “should” be doing.

Week one hundred seventy-six was another week of learning. Looking forward to next week!

This week WeWork included a warning in its quarterly results report:

[A]s a result of the Company’s losses and projected cash needs, combined with increased member churn and current liquidity levels, substantial doubt exists about the Company’s ability to continue as a going concern.

Translation: WeWork is struggling to survive. It may or may not make it through a rough patch. To turn things around over the next 12 months, management has a plan that includes the following elements:

• Reducing rent by renegotiating lease terms
• Increasing new sales and reducing churn
• Scrutinizing expenses and capital expenditures
• Raising capital by taking on debt, selling equity, or selling assets

Crunchbase says that the company has raised over $22 billion in equity and debt financing over the years. Its valuation peaked in 2019, when it raised a reported $6 billion from Softbank at a $47 billion valuation. As of Wednesday, August 9, 2023, its public market capitalization (i.e., valuation) is $272 million. Dropping from $47 billion to $272 million is about a 99.5% reduction in valuation in roughly four years.

I’m not sure what the future holds for the company, but its fall from grace is stunning. I’m curious to see what impact WeWork’s struggles will have on start-ups who depend on it for office space and on the owners of office buildings that house WeWork’s locations.

Over the last few weeks, I’ve chatted with several emerging VC fund managers who are preparing to raise their first or second funds. They’ve seen the headlines about established mega funds cutting their fundraising targets. And they’ve chatted with their peers who went to market in 2022. There’s lots of uncertainty about what to expect if they go out to raise in the second half of this year.  

The fundraising environment for emerging VC fund managers has been difficult for the last eighteen months for several reasons. But one of the variables has changed, I think: the NASDAQ stock index. In 2022, the index was down over 30%. It declined most of the year and no one knew when it would bottom. The sentiment toward tech (and public equities in general) was negative in 2022, with many potential LPs reluctant to make new investments in emerging funds. Through the end of July of this year, though, the NASAQ is up ~35%. I wouldn’t call sentiment in 2023 optimist, but so far it’s better than it was in 2022.

I’m not sure what the NASDAQ will do—or what fundraising environment emerging VC fund managers will face—the rest of this year. If the NASDAQ rises further or at least stays in positive territory, I wouldn’t be surprised if LPs are more receptive to pitches from emerging VC fund managers than they were in 2022. I’m curious to see how the fundraising environment for emerging managers shapes up for the rest of the year.

I was at a social event where aggressiveness in deal negotiations was discussed. The main questions being asked were how aggressive should a party be in negotiations and when have they taken it too far.

This gathering was attended by founders (early-stage and mature), VC investors, people in the start-up ecosystem, people not involved in start-ups, and a few non-start-up lawyers. The perspectives were diverse, which made for an interesting conversation.

After a while, people mostly ended up in one of two camps:

• There’s a point in deal negotiations where you can be too aggressive and jeopardize the long-term viability of a deal. Negotiate to that point but don’t take it further (even if you have the leverage to do so), because it will have negative consequences down the road.
• Deal negotiating is an example of what has applied to humans for a long time: survival of the fittest. You must fiercely negotiate for your best interest in any deal. Not doing so leaves an opening for others to take advantage of you. Negotiate like your survival depends on it.

The conversation was much more involved than that, but I’ve tried to simplify it. I really enjoyed hearing the different perspectives. At the end of the conversation, most agreed that how people thought about aggressiveness was influenced by their upbringing and professional experiences.

I don’t think there’s a right or wrong way to think about aggressiveness. I’ve come to believe that the answer to how aggressive one should be in negotiations is it depends. It depends on the dynamics at the time, on what you’re negotiating, on what leverage you have, and on the parties you’re negotiating with.

One thing holds true in all negotiations. Be mindful of this when deciding how aggressive to be: no one will look out for your interest more than you will. If you don’t look out for yourself, don’t expect the other party to do so.