I caught up with a buddy today to discuss an opportunity he’s evaluating. He said he knows he says yes to too many things, often too quickly, and that he’s looking for another perspective before deciding. I’ve known him for years, and I agreed with him. His self-awareness impressed me and made our conversation about his opportunity more substantive. I realized that he and I are opposites, which is likely why he called me. I quickly say no to most things and am slow to say yes to things I’m interested in as I evaluate them.

Being self-aware is difficult but valuable. It helps you understand the areas you can improve upon (your weaknesses) and those you should lean into (your strengths). My conversation today was a timely reminder that in 2021, I want to do a better job jumping on good opportunities that interest me. My habits won’t change overnight, so my plan is to recruit the perspectives of people who recognize good opportunities and are good at saying yes quickly.

I’m glad I connected with my buddy today. Our opposite styles are complementary, which is valuable to both of us. In the end, we agreed to balance each other in 2021. I’m looking forward to that!

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.

Yesterday, I shared what I learned from Inside Bill’s Brain: Decoding Bill Gates. I don’t watch much TV, but this was an insightful series. Today I’ve been thinking about Bill’s “think weeks.” He regularly spends a week alone in a cabin reading and thinking. The quietude and stillness give him an optimal environment for his best thinking, allowing him to distill things and solve complex problems.

Bill’s intelligence and ability to rapidly comprehend things have been remarkable all his life. (His siblings, coworkers, and wife all confirmed this.) And they’re at their highest level when he reduces his activity level and just thinks.

I started to wonder what environment allows me to do my best thinking. I usually need to get in the zone to think about complex things. Big blocks of time let me do that, and then I can concentrate and make significant progress on a problem. Once I see progress, I get excited and want to keep going. Interruptions or lots of activity around me are disruptive, so I try to be somewhere quiet and still when I need to get in the zone. I’ve also learned that writing helps me make connections and solve complex problems. It forces me to organize and communicate my scattered thoughts in a way others can understand.

This year has been challenging, to say the least. Like everyone, I’m ready for it to be over. In tough situations, I try to look for the silver lining. I believe life is about perspective and there’s always something positive; you just have to look for it. This year is no exception. Less activity and a slower-paced life because of the pandemic have given me more time to think than I’ve ever had. I’ve accomplished things I’ve been putting off for years (like blogging) and worked through some tough problems. Bill Gates does think weeks. I’ve sort of done a think year.

Bill Gates is a brilliant person who made an impact on society through entrepreneurship and is doing it again through philanthropy. I love learning from the experiences of people smarter than me, like Bill. There’s a lot to be said for his practice of taking week-long blocks of time to think. (If someone of his stature continues to prioritize this, there must be something to it!) I don’t have the luxury of doing think weeks, but I’ll work toward being more intentional about taking time to read and think in the right environment.  

Tomorrow is Thanksgiving, a holiday that’s special to me. When I decided to quit corporate America and start a company, I broke the news to my parents over a Thanksgiving holiday. In the early years, the holiday was an opportunity for me to make progress on big projects. Eventually, though, it dawned on me what a terrible way of doing things that was, and I began enjoying the day with people I loved.

Unplugging was something I struggled with for a long time. I was worried about failing, so work issues were always racing through my mind. I eventually realized there weren’t many weekdays when I could mentally disconnect and learned to set work aside when they came around. Thanksgiving was definitely one of those days. I also found it to be a great time to reflect and give thanks for everything that had gone right that year.

Have a great Thanksgiving and enjoy your downtime with people you care about!

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.

I recently chatted with a startup team. I wanted to know how they resolve disagreements. They all said they first listen to each other’s points to understand the different perspectives. Then they discuss what’s in the best interests of the customer. They’ve disagreed over the years on some pivotal issues that changed the company’s trajectory, but it never hurt the team. If anything, it helped build trust because each person felt heard and understood even if the ultimate decision wasn’t what they wanted.

Listening with the intent of understanding different perspectives is effective. I’ve consistently seen that teams who handle disagreements this way resolve them more effectively and make better decisions.

The next time you don’t see eye to eye with someone, consider taking the time to listen to them. Don’t interrupt. Keep listening until you understand their perspective. This simple but powerful approach can lead to a compromise that everyone can live with.

An elder once told me, “You can have whatever you want, but you can’t have it all at once.” I didn’t appreciate the wisdom in that statement back then, but I do now. I learned how right he was from some painful experiences. People have a finite amount of time and energy, so accomplishing an infinite list of things at any given time isn’t realistic. Prioritization is the key.

Here are a few things I’ve learned about prioritizing over the years:

• Start with the end in mind – I first try to determine where I want to end up or at least the direction to head in. This compass helps me when I’m struggling to prioritize.
• Time sensitivity – If something is time sensitive or its window of opportunity is closing, I try to assign it a higher priority. Everything isn’t time sensitive.
• Things will drop off – Some stuff won’t make the cut and that’s OK. If I know something won’t get done because it isn’t one of my priorities, I try to communicate that to anyone else who’s involved.
• Small number of priorities – I do best when I have a list of three to five priorities. More than that and I’m less effective.
• Impact on others – I’ve caused and been on the receiving end of collateral damage when too many things are forced at once. When you don’t prioritize, others can be affected as much as or more than you are.

I’m still a work in progress. I haven’t mastered prioritization yet, but it’s become a little easier now than I’ve learned these things. I hope you’ll find them helpful too.

Today I had a great conversation with a founder friend that reminded me of something. The journey of a founder is an evolution. The needs and priorities of a founder will change.

Founders who build successful companies often end up selling them. What then? Many struggle to decide what they want the answer to that question to be. Do they start over with another company? Do they retire to a tropical island? Do they use their experience and skills to re-focus their efforts on giving back?

And it’s not just their professional lives—all aspects of a founder’s life evolve. I was 100% focused on CCAW as an early founder. I worked all-nighters and prioritized CCAW’s success above most other things. I don’t recommend that approach, but it’s what I did. As I’ve gained more experience, a lot has changed. I don’t do all-nighters anymore. My brain and body don’t respond to them like they used to. My priorities have also changed. Family and friends rank higher than professional success. And how I define success has even changed. I now think of success as helping others reach their full potential as opposed to building my own successful company. As I continue to live, I’m sure more changes will come.

Evolution is part of life. From my experience, it’s important for founders to recognize this evolution, embrace what comes from it, and adjust accordingly. I didn’t recognize that my needs and priorities were changing—I carried on with the same approach, the same habits. It took life slapping me in the face to change and make a ton of adjustments quickly. I wish that I’d taken time to regularly reflect on this and make gradual adjustments periodically. Now, I plan to reflect annually during the Christmas holidays. It’s a perfect time to think about the past year and the one coming next.

Founders should begin their journey with the understanding that who they are now probably isn’t who they will always be. This will make it easier to recognize their evolution, process it emotionally over time, make practical decisions, and implement changes gradually. Life never stands still!

I caught up with a good friend yesterday. He’s an entrepreneur who has attained what I consider to be an elite level of success. He said something that stuck with me. Business conquests are great, but they haven’t brought him joy. Celebrating life’s moments and sharing experiences with people who matter most are what truly makes him happy.

Entrepreneurs have a vision that they’re trying to make a reality. Often, they think about little else—and sometimes that’s not a good thing. For example, one of my closest friends once invited me to join him and another college friend on a trip to South Africa. It was an opportunity to see a special part of the world with people I’m close to. But I was so focused on making CCAW a success that I thought I couldn’t afford to take the time off. To this day I regret that decision.

I agree with what my friend said. For all the success I had with CCAW, it’s the moments with friends and family that I cherish most. If you know what brings you joy, don’t routinely sacrifice it to your work. Faced with a decision like mine, make it carefully. The opportunity to go to South Africa with friends—or whatever version of such an opportunity turns up in your life—may never come again. Even ordinary chances to enjoy a meal, a concert—whatever floats your boat—with your family or friends are gold. Yes, if you’re an entrepreneur, you must work super hard. But don’t sacrifice your relationships. Make time for what matters most.

Yesterday I caught up with a good friend who’s also an entrepreneur. He said he was recently asked, “What would you change or do differently?” We’ve both been asked this question for various reasons, so we had a great chat about it.

Things will inevitably get challenging during the entrepreneurial journey. Entrepreneurs will find themselves making important decisions based on imperfect information. Having lived this scenario many times, we agreed about what matters most:

• Everything happens for a reason. The reason may not be clear at the time, but there is one. Take time to reflect on what happened, and why, so you can apply what you learn in the future. What seems like a failure today could be a steppingstone to a decision that leads to massive success. Reflection and the understanding it engenders are key to improving your decision-making.
• Neither of us would change any of our decisions. We don’t second-guess them. We didn’t know then what we know now, and we stand by our decisions because we did the best we could with the knowledge and other resources available to us. Don’t continually relive the past. Focus on the future.
• It isn’t over until the clock reads double zero. Stay focused on getting the win. Sometimes you’ll make decisions that don’t pan out. That’s OK. Dust yourself off and get back in the game. Remember that it isn’t over yet and you can still make a comeback. If you win in the end, all your turnovers and air balls don’t matter anymore.

My conversation with my buddy was a great reminder for both of us that we wouldn’t change a single thing. As he so eloquently put it, “All windshield, no rearview mirror over here!”