I set up an introductory lunch for two entrepreneurs in the same industry. I’ve been trying to make this happen for months, and I’m glad that this week, it finally did. One of these entrepreneurs is seasoned, with deep relationships and wisdom accumulated from years of experience and learning about the experiences of others. The other is new to the industry; he’s had early successes and is trying to build upon them to scale.

The lunch was a success. My being there as a trusted party helped each of them build trust with the other. The seasoned entrepreneur readily answered all questions and was transparent. He shared details about lessons learned from painful failures and explained how changing market conditions led to the strategy he’s pursuing going forward. He gave comprehensive answers to questions about the ways he overcame hurdles the newbie is facing now. He also shared his best-kept secrets, including tools he uses to access hard-to-find information.

After the meeting, the newer entrepreneur told me that the things he learned during that lunch will save him months of time and considerable money. Before, he was unsure how to overcome certain hurdles. He now knows exactly what to do and not do and the people to call for help in specific areas. He left confident and excited. If he gets stuck, he now has someone credible he can call who’s been in his shoes and who’s willing to help.

Meetings like this are important, especially for newer entrepreneurs. They can completely change an entrepreneur’s trajectory. I’m excited for both of these people and can’t wait to see what they do. As the newbie becomes more successful, I hope he pays it forward and shares what he learns with the entrepreneurs who come after him.

Today a friend sent me a link to an interview on a topic I’m interested in. I’d never have known about this interview if he hadn’t shared it. I listened to it, and it was terrific. I got lots of ideas from it and shared it with others. We ended up having a great text exchange about the interview.

Today was a reminder of the power of sharing links to interesting information. (I define “interesting” as being about a topic the recipient has expressed interest in.) It’s such a good way to build and maintain relationships. Essentially, it’s curation. Sifting through information, selecting the most value-added items, and presenting them to others gives them something of value and leaves a positive impression of you in their mind. It also saves them a massive amount of time. Said differently, it’s a simple way to offer value to others and stay top of mind with them.

Today I had a debate with someone. We have different perspectives on an issue and how to resolve it. They feel strongly about one approach. I feel strongly about another approach. Both of us have our reasons—but neither of us has experience with the issue. I realized we were both debating from the vantage point of inexperience and likely wouldn’t resolve our differences. I suggested we get more perspectives from credible friends who’ve navigated this issue.

We picked up the phone and called a few friends. We explained that we were debating an issue we were inexperienced in and wanted perspective from experienced people. We asked them if they’d had to deal with this issue (they all had), how they resolved it, why they resolved it that way, and what they’d learned (good or bad). We were careful to not ask anyone if my perspective or my friend’s perspective was right. And we didn’t ask them how we should resolve the issue. Our focus was on their experience.

What we learned from these few phone calls helped us see the issue from the perspective of experience, which uncovered blind spots. Our debate went from unwillingness to compromise because of strong feelings anchored in ideology to productive conversation that led to a compromise.

When I finished college, I crowdsourced my transition to corporate America. I asked for advice on a blog and got a lot of great feedback. Recently, I reviewed it. This one stuck out to me:

Never turn down a weekend with friends. Use some of that new hard-earned cash to continue building your friendships from college and maybe rebuild those ones that died while you were away studying.

As a founder I sometimes followed this advice, but I ended up saying no to many social events because I was too busy building a company. I regret saying no to some of those milestone events because they ended up being once-in-a-lifetime opportunities with friends—memories I wasn’t a part of.

I now approach this differently. When close friends or family invite me to something that’s a milestone, I try my hardest to attend and be totally present. The work will always be there, but opportunities to spend time with friends or family at milestone events are closing windows of opportunity that I want to take advantage of before they’re gone.

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A few months back, I shared Reid Hoffman’s belief in keeping his expectations of meetings low to allow for serendipity. That really stuck with me, and I’ve embraced it, which has indeed led to some serendipity. Since then, I’ve been thinking about how to lean into encouraging more serendipity.

I’ve started to think about how to make room for serendipity through my normal nonwork interactions. I’ve landed on something that’s worked. When I’m doing normal everyday things, I now try to go to new or unfamiliar places to get exposure to new establishments, neighborhoods, and people. A simple example is dinner. Most people have their go-to restaurants and neighborhoods. These places are where they’re comfortable and what they know. Instead of sticking to your favorites, find new places (preferably with good reviews) in an area you don’t frequent. While you’re there, try to understand the people and the area.

I recently had dinner in a part of town I don’t usually go to. The place has good reviews, so I was excited to try it. Instead of grabbing a table, my companion and I chose to sit at the bar. Because we did, we had amazing conversations. The bartender gave us a history of the restaurant and its ownership. And we met another couple at the bar who build custom homes. They gave us a boots-on-the-ground perspective of the Atlanta housing market and shared some information we otherwise wouldn’t be aware of. We all agreed to keep in touch.

Serendipity, by definition, happens by chance, but you can be intentional about increasing the probability of it through your decisions about everyday activities.

I’ve attended many holiday parties over the years. My general thought is that the larger the company, the larger the party and the less depth there is in people’s interactions at the party. For some (not all), the party can feel like a chore. For a big company, team holiday gatherings can be a better option than a single large party. For example, if the sales team has 12 people and the marketing team has 8 people, have two separate team parties organized by the team leaders.

Small gatherings like this can bring more value. They’re more like a big family’s Sunday dinner than a huge family reunion. Teams who work closely every day can bond outside work and add a social layer to their relationships. Instead of trying to connect with people you barely know or don’t know at all at a huge party, you can strengthen relationships with people you already know in a more intimate setting.

Holidays are a great time to get team members together, and small team gatherings can be a great alternative to a huge company holiday party.

I had an enlightening conversation yesterday. I was sitting with four people I hadn’t met before, and we all struck up a conversation. We started off talking about where we’d grown up. That morphed into each of us sharing insights from our professions. We all walked away having learned something new and with new contacts. I personally learned something I plan to implement as soon as I have the opportunity.

This conversation reminded me of two things. One, serendipity is powerful. Two, your chances of serendipitous interactions like this one happening are influenced by the networks you’re a part of. If you aren’t in the right networks, “lucky” interactions like these probably won’t occur.

I had a meeting with another investor recently. His journey to investor wasn’t easy. I love hearing stories like this. They show you how people are wired and who they really are. I wanted to hear his story so I could understand him better and see if I could be of assistance.

The call began normally and was cordial, but he wasn’t opening up. Then he mentioned a small detail that made me realize we might have experienced something similar earlier in life. So, I shared my experience. Sure enough, he said he’d had a similar one. From that point on, the conversation changed. We were able to relate and get to know one another via a common thread.

I appreciate this reminder that finding ways to relate to people is important. Doing so can completely change a conversation (or start it off on the right foot). More importantly, it can be a powerful tool in helping you build relationships and understand who people really are (as opposed to how they want to be perceived).

Today I joined an intro meeting only to realize that I already know the other person. We’re not close but have been in the same circles for over a decade. Catching up, we realized that our work overlaps, so we can help each other. Here’s what I was thinking as I left the meeting:

• The world is smaller than I think.
• You never know where life will take you or others.
• Relationships matter a lot, even if they aren’t super deep.
• Being nice is easy, feels goods, and can pay dividends many years later.

I’m glad we finally got to know each other after all these years, and I’m looking forward to working with him.

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My buddy Bob called me today and described a project he’s working on. He’s having a hard time acquiring a key piece of it—he’s been searching, but he keeps coming up short. As he talked, I thought of another friend, Sarah, who deals with these kinds of items all the time. I got a picture of the item and sent it over to Sarah. She immediately responded with a product Bob might like and a source where he could view other similar products.

Bob didn’t have knowledge or experience in this area. He expended a ton of effort over countless hours trying to fill that gap. This slowed his execution of his project. Sarah, on the other hand, has the relevant knowledge and experience. She was able to point Bob in the right direction with minimal effort, which will hopefully get his project back on track.

This simple story was a reminder: knowledge gaps can impede execution. If not knowing something is slowing me down, I should find someone who can fill my gap so I can keep executing. Kudos to my buddy for reaching out. I couldn’t fill his gap, but I’m glad I knew someone who could.