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Learn by Extending a Helping Hand

I’ve been listening to a friend talk about a deal he was considering. It was a big real estate deal, something I’m not experienced in. I didn’t have a stake in it, but I decided to help in a way that leveraged my strengths. I’m a numbers guy, so I built a crude financial model to help clarify the worst-case scenario. We talked it over and he shared his insights on what the model was saying and things it didn’t account for.

Today, I learned that the deal fell apart. Not the outcome we were hoping for, but I realized that supporting my friend had been a great experience. First, it always feels good to contribute to someone else’s success. My assistance wasn’t material (in my opinion), but every little bit helps when you’re trying to do the impossible. Second, helping my friend, who’s experienced in a space that I consider a future area of interest, was a terrific opportunity for me. I learned a lot, fast, from the combination of his wisdom and my own research.

If you’d like to learn about an area or gain some experience in it, try to find a way to offer your skills, free of charge, to someone knowledgeable. Give back by helping a friend or colleague . . . learn about something that interests you . . . it’s a win–win!

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2021: The Year of . . . ?

I had a good conversation with a buddy about 2020 and 2021. He said that 2021 will be a year of experimentation for him. He plans to try several different things, knowing that many will not work out. His goal is to learn and have a few successful experiments that pay dividends.

My friend isn’t an entrepreneur, but I love his perspective. Though we’re living in uncertain times, he understands that doing nothing isn’t an option. He has to take action toward reaching the goals he’s set for himself and his family. His action will be risk adjusted. He’s not going to bet the farm on his experiments . . . but he will make some bets. Worst-case scenario, all his experiments fail and he learns a lot. To him that knowledge will be valuable even if the monetary value of his bets shrinks to zero.

Perspective is important, and I think the beginning of the year is a great time to think about it.

What will 2021 be about for you?

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Good Partnerships Have Balance, Not Perpetual Agreement

I had a conversation the other day with an entrepreneur (let’s call him “Ed”) who was frustrated with his business partner (“Phil”). Ed is extroverted and focused on the big ideas. Phil is introverted and detail oriented. Ed’s frustration is rooted in feeling like Phil hasn’t been supportive of some of his ideas.

I came to the conclusion that these two are the perfect match. They balance each other’s weaknesses and together are a well-rounded team. The difficulty is Ed’s perspective on the situation. He can’t forget times when Phil has disagreed with ideas he felt strongly about.

Ed and I went through some of their most successful initiatives of 2020 and the role each person played. I pointed out how each of them contributed and how unlikely each success would have been without both of them. Sure, some ideas didn’t pan out, but the ones that did were successful because of the partnership.

In my opinion, in this partnership, Ed has more to be happy about than unhappy about. He just needs to adjust his thinking. Does he want to play team ball or beef up his own stat line? Partnerships are difficult. Sometimes you get your way and sometimes you don’t. In the end, it doesn’t matter as long as you end up wearing the championship ring.

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A Different Way to Keep the Spirit of Christmas Alive

Yesterday was a unique Christmas, to say the least. Many people couldn’t get together with friends and family the way they usually do. There was a silver lining, though. I assume because they couldn’t do “Christmas as usual,” lots more people reached out to me than normally do at Christmas. I had some great phone conversations and FaceTime calls that I really enjoyed.

Christmas may be over, but we’re still in the holiday season. If you think about someone, reach out. I’m sure they’ll appreciate the gesture. Who doesn’t like being reminded that someone cares about them and is thinking of them? You never know: you might just make their day!

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Christmas: the Bright Spot of 2020

Tomorrow is Christmas, my favorite holiday. The one I most associate with spending quality time with family and friends. It’s also a reminder that the year is coming to a close. Over the past few years it’s become more significant to me, and I completely unplug and stop working from Christmas Eve through New Year’s Day. This allows me to be present with family and friends.

It’s been an eventful year. Many people have experienced unimaginable pain and suffering. I hope that tomorrow can be the bright spot of 2020 and everyone is able to enjoy the holiday.

Merry Christmas and enjoy your downtime with the people you care about!

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Partnerships Aren’t Perfect

I’ve noticed a pattern in the lives of people I admire most in life. They tend to be members of great partnerships that contributed to their success. Co-founders . . . business partners . . . spouses. Being part of a team has allowed them to accomplish things they otherwise wouldn’t have. Because their strengths offset their partner’s weaknesses, and vice versa, they form a well-rounded team.

Almost universally, great partnerships go through rough patches. It happened to Bill Gates and Paul Allen. Such a time is a defining moment for the partnership, and how the partners work through it will determine whether their partnership becomes stronger or dies. The partners don’t see eye to eye, but if they make the effort to understand each other and resolve points of conflict in a respectful way, it will demonstrate commitment to the partnership and go a long way toward moving past the period of conflict.

I’m a huge fan of co-founders. I think startups increase their chances of success by having more than one founder. But it’s almost inevitable that the co-founders won’t always get along. If this happens to you, consider taking a step back to think carefully about how you want to resolve the rift. In fact, you might even consider planning for it in advance. Your approach will have a lasting impact on your partnership—not to mention your business and your life.

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Close the Loop

Over the years, I’ve been humbled. I used to think I was superhuman—capable of doing anything. Now I recognize that I’m not good at everything, nor do I have the experience to navigate certain situations. I’ve learned to ask for help. Learning from the experiences of others has been invaluable in challenging times. If I’d done it more in those early years, it would’ve saved me tons of time and energy. I encourage early founders to learn from my experience.

Learning from others isn’t a one-time thing. It requires investing in and maintaining relationships. I’m a big believer in healthy relationships being bidirectional. As an early startup founder, it doesn’t feel like you have much to offer people who are sharing their wisdom with you. That may be true, but you can do one important that they’ll appreciate: close the loop. When you ask people for help or advice, follow back up with them to let them know the outcome. Good, bad, or ugly. They’ll appreciate the effort.

I sometimes fall short, but I do my best to close the loop. I appreciate and respect other people’s time, and I make sure to thank them when I close the loop. Simple to say, simple to do—but powerful. It will strengthen your relationships.

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What I Least Expected to Gain

I was talking with an early entrepreneur, who asked a great question. “What’s the most meaningful thing you gained from your journey that you least expected?” Now, I admit . . . I was totally stumped. I needed time to answer. I wanted to think about it so I could give an authentic response. Toward the end of our conversation, it came to me: friends who understand me and experienced the struggle too.

Being an entrepreneur is hard. You’re trying to do the impossible with limited resources. You’re pushing yourself and your team to the limit. It’s not something that most people understand or can relate to. I had a great support system of friends and family before I founded my company. I was able to talk with them about most things in my life. But when I became a founder, that changed. I was experiencing things they hadn’t and that they couldn’t relate to. After a while, I steered conversations with them away from work. My company was an outsized part of my life, so I found myself on an island without anyone to talk to who could relate.

I eventually connected with other entrepreneurs at a similar stage and this changed. All of a sudden, I could talk to people who got it. They were problem solvers facing the same challenges I was, and they had crazy visions that others in their life couldn’t understand. Over the years, those peers became wonderful friends. The friendship dynamics are hard to explain, but because we supported each other during some of our toughest times, the bonds are tight.

When I decided to start my company, I wanted it to be a success and I wanted to enjoy everything that came with it. I achieved success, but the thing that stands out more than that are the friendships I formed with other entrepreneurs. We come from different backgrounds, but we bonded over our shared desire to solve tough problems by building amazing companies. Companies can be bought and sold, but true friendships like these are invaluable.

If you’re looking to do something great (even if it’s not entrepreneurship), consider connecting with others who are traveling a similar road. No matter how great your accomplishments, the friendships you’ll build along the way will be priceless.

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Vesting Schedules Protect Company Equity

I’ve written about how important finding a co-founder is for entrepreneurs. But equity (company ownership) is a big concern. Specifically, what happens if things don’t work out? If one founder isn’t pulling their weight, do they own as much of the company as they would if they were contributing mightily?

It’s a valid concern. But there’s a simple tool to mitigate it: a vesting schedule. A vesting schedule outlines when each person’s equity is theirs, free and clear. Keep in mind that equity should be earned, not granted, for early employees and founders. The vesting schedule is a great tool to set expectations about equity.

The most common vesting schedule is time-based. You typically see a four-year schedule with a one-year cliff. What does this mean? No equity vests until after a year of employment. If someone leaves in month eleven, they receive zero equity. On their one-year anniversary, 25% of their equity will vest (they stayed for one of four years, or 25% of the four-year schedule). After that, their equity vests in equal monthly increments until the forty-eighth month.  Carta has a good article with details and examples.

At CCAW, we used a milestone-based vesting schedule with revenue as our milestone. As we reached certain revenue targets (while maintaining profitability), equity for leaders would vest. We had a minimum revenue threshold (i.e., cliff) the company had to hit before any equity vested. This schedule was very helpful because everyone was aligned. Our approach was specific to what we were trying to accomplish at the time and may not work for everyone.

Many investors will want to see that founders are on some sort of vesting schedule, which ensures that they’re committed to building the company. There are lots of details that I won’t get into, but the takeaway is that founders should have a vesting schedule (in some form or fashion) if they’re raising investor capital.

A vesting schedule is a great way to protect against someone who isn’t contributing having equity in a company. Finding a co-founder is hard, but vesting schedules overcome one hurdle.

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Idea Compounding

Today I participated in an idea session with my Outlander Labs teammates. No agenda, just a topic and a conversation about ideas. It was a topic that I’m not knowledgeable about, so my goal was to listen and learn. And boy, did I! The team’s collective knowledge was vast and we ended up with great ideas. Today was an opportunity for me to fill a knowledge gap, and it highlighted something else for me too.

As I listened, I noticed a pattern. Idea compounding. Sounds weird, so let me explain. Our team is composed of highly intelligent people who, individually, have great ideas and unique perspectives. As one person shared a thought, you could see the wheels turning in everyone else’s head. Then someone else shared an idea inspired by the previous one. This went on for an hour and resulted in more great ideas than we can possibly execute. A high-class problem for sure.

Our idea-generating exercise was highly effective because we approached the topic as a team. Had we assigned it to one person, I have no doubt that their ideas would have been really good. But approaching it as a team resulted in ideas that are great (or so we think).

I wish I had had the benefit of idea compounding in my early days at CCAW. I chose the solo founder path, and it was difficult. I was forced to come up with all the ideas, which were far from great. Years later I hired high-level thinkers and our idea compounding led to some of CCAW’s greatest breakthroughs. We overcame enormous hurdles and made tons of traction in a relatively short time.

Idea compounding is one of the many benefits of working with a team. And great ideas can be the difference between success and failure for early-stage companies. For any founder wondering why you should consider recruiting a co-founder: idea compounding is one of the many reasons you shouldn’t go it alone!

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