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Closing Windows of Opportunity: Milestone Events

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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How I Encourage Serendipity

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.

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Company Holiday Parties

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.

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Do Your Networks Promote Serendipity?

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.

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Looking for Common Threads

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).

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Small World

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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Knowledge Gaps Can Slow Execution

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.

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Early Founders Should Email Updates Regularly

I recently got an update email from a founder I haven’t spoken with in months. He sends them out every month to a distribution list. They’re pretty good, and this one put his company back at the top of my mind.

Update emails are a simple yet powerful tool that can benefit early-stage founders. They help with accountability and focus and they remind outsiders that the company exists. The exercise of creating the email is good for founders because it forces them to reflect on the most important things that have happened and how the company’s KPIs or other metrics look.

These emails don’t have to be long or dense. The more concise the better, in fact. I’ve seen founders create a template and change only key pieces of information each time. Most importantly, these emails should be consistent and truthful. Pick a time interval (I’d suggest monthly at a minimum) and stick to it. Sporadic updates with constantly changing formats and KPIs give the impression that the company or founder is unfocused.

Updates shouldn’t be all about everything that’s going well. Running a startup is hard, and things are constantly going wrong. Share those things, too. When you’re open about where you need help, it’s easier for people to help you. And people will tend to trust you if they feel they’re getting the complete story. If you say your startup never struggles, people won’t believe you.

If you’re an early-stage founder, consider asking people you meet with (at the end of the meeting) if you can add them to your update email list. And send regular updates to everyone on it.

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3 Questions to Ask Before You Start Pitching

I recently listened to a founder’s pitch to an investor that went off the rails as soon as the founder opened his mouth. The investor struggled to understand what the founder was trying to communicate. The entire meeting was painful to watch. A few hours later, the same founder pitched another investor, and the meeting went great. What was the difference? At the beginning of the second meeting, the founder sought to understand his audience by asking a few simple questions. This allowed him to deliver his pitch in the way the audience preferred. The change was small but powerful. Here are a few questions founders can ask to help understand their audience:

  • Have you had a chance to review any of our materials? Founders often assume investors have reviewed their pitch deck, one-pager, product demo video, etc. But sometimes investors haven’t received the materials or haven’t had an opportunity to review them. They’re human; they miss things. Some are just busy and run out of time. Understanding what they know about your company (if anything) is important. Filling in gaps is different from starting with a blank canvas.
  • Where would it be most beneficial for me to start? Some investors want to dive straight into the solution you’ve built and the business. Others want to understand the founder and their journey that led to founding a company. Beginning the conversation with what matters most to the audience greatly increases the likelihood that they’ll clearly understand what you’re trying to do.
  • Would it be more helpful to stay high level or to explain the details? For technical founders who live in the weeds of their technology, this is an especially important question to ask. Some investors love the technical details, while others love the big picture. It’s important to understand this and deliver your pitch at a level that interests them. Miss the mark and the conversation could spiral downhill fast.

Understanding the audience goes a long way toward helping founders communicate effectively and gain support. The questions above will help accomplish that, but it’s by no means an exhaustive list. Plenty of other questions would also work. Regardless of what you ask, I’d limit it to two or three questions.

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To Be a Great Leader, You Need a High EQ

One of the toughest situations I had to navigate as a founder was a key team member threatening to leave my team. During a strategy session about an important topic, Bob and I saw things differently. Neither of us backed away from our position, and it turned into a heated debate. We were respectful of each other, but later that day I received an email from Bob saying he would like to leave the team because we didn’t see eye to eye. Bob was extremely smart and talented. He owned all the details of a critical part of the business. Translation: it would be hard to replace Bob, and a critical part of the business would come to a standstill if he left.

I didn’t realize the seriousness of the situation until I read Bob’s email. I immediately realized that it could spiral out of control unless I handled it correctly. I got Bob on the phone, and we listened to each other’s viewpoints (instead of pushing our own). I told him I valued him as a team member, and we agreed to sleep on things.

I felt there was more there, so over the next few days we talked it over and got to the root of his frustrations. I learned that it had nothing to do with what we were originally debating. The company was growing, and Bob’s role was becoming more demanding. He didn’t understand why he was being asked to take on many new responsibilities. This was news to me, but once I understood the problem I came up with a solution.

I realized I hadn’t articulated my vision for where the company was going, so the extra work didn’t make sense to Bob. He didn’t understand how he fit in. He just felt overworked. I started communicating my high-level vision more clearly and frequently to the entire team so that everyone would understand their importance to making the vision reality. I transitioned certain responsibilities away from Bob and hired someone to work closely with Bob and take them on. We put the plan in writing and agreed to it. Everything was back on track. Bob and the rest of the team understood the vision and were satisfied.

That situation was a great lesson. I learned that being a leader is not just about being hard-charging and executing. It’s about people, too (other people—not just you). Leaders need to have emotional intelligence and awareness to understand what your team needs (even if they can’t—or don’t—articulate it) and provide it.

Cultivate this ability in yourself. Your team will run through walls for you.

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