18 Principles on Leadership and Culture

Over the last 15 years, I have served in the non-profit world and co-founded several for-profit businesses.

I have led hundreds of people in the process, and I’ve learned a lot along the way.

Here are 18 leadership principles that have transformed how I lead teams:

  1. No One Is Above the Culture

You cannot build a strong culture unless everyone submits to its values and norms. No one gets a free pass because of their position, productivity, or tenure.

People will not respect or follow hypocritical leaders.

2. Leadership is About Serving

Selfish leaders believe that leadership is all about others working hard to help the leader win.

Servant leaders know that leadership is about sacrificing for those you lead to help everyone succeed.

3. Keep short accounts

One simple rule for conflict and frustration: don’t let it fester.

Take the initiative to address conflict openly and directly. Be quick to apologize and forgive.

4. Team Building

Hire for character, aptitude, and drive in that order.

No matter how much drive or talent a person possesses, lack of character is a fatal flaw.

5. Cast Compelling Vision

Antoine de Saint-Exupéry once said:

“If you want to build a ship, don’t drum up the men to gather wood, divide the work, and give orders. Instead, teach them to yearn for the vast and endless sea.”

6. View Mistakes as Tuition

Create a culture that views mistakes and failures as the required cost of pursuing excellence. When an initiative goes poorly, use it to stimulate learning and growth instead of finger-pointing and regret.
7. Dispense Grace

People will make mistakes. Often mistakes are going to be frustrating and expensive.

When possible, make every effort to respond with grace. It will strengthen your relationship with that person and positively impact how they lead others in the future.

8. Accelerators and Brake Pads

Every organization needs people who help push it forward (accelerators) to capture opportunities.

It also needs people who slow it down when trying to do too much (brake pads).

Effective teams have a balance of both types of people.

9. One Helpful Question

At the end of every one on one meeting, ask the question, “What can I do to help you?”

This question will help surface areas where the team needs support or resources, and it can also help surface feedback they have for you as a leader.

10. Gather Missionaries, Not Mercenaries

Mercenaries are primarily motivated by the potential for personal gain.

Missionaries strive to make meaning, and they long to be part of a cause bigger than themselves.

Teams built around a shared mission consistently outperform mercenaries.

11. Don’t Strive To Be The Smartest

Leading is not about having the best ideas but discerning who does and empowering them to act.

Steve Jobs said it best:

“It doesn’t make sense to hire smart people and tell them what to do. We hire smart people so they can tell us what to do.”

12. Be Strategic with Challenging Feedback

Take time to crystalize what they need to hear and provide concrete examples.

Never share feedback while you are angry.

Intentionally wait for an opportunity when the other person can receive constructive criticism.

13. Encourage Frequently

Affirming others doesn’t cost anything more than our time and intentionality, but its impact is profound.

Intentionally track your ratio of encouragement to constructive criticism. It should be at least 2 to 1.

14. Give Freedom to Fail

We stunt the growth of others when there is a fear of making mistakes.

Mark Twain once observed:

“Good judgment is the result of experience, and experience the result of bad judgment.”

Leaders help others learn how to convert failures into judgment.

15. Culture is Like a Garden

A garden only thrives if everyone pulls the weeds, waters the plants, and fertilizes the soil.

Challenge every team member to be a part of the cultivation process. A healthy culture is the result of an intentional collective effort.

16. Same Song, Different Verse

The best leaders consistently communicate the same core ideas and strategies, but they creatively find new and fresh ways to express those concepts.

People need repetition, but they hate redundancy.

17. Great Leaders Help Create More Leaders

Leadership isn’t being the strongest and most competent person in the organization.

It is taking responsibility to foster an environment where everyone thrives and grows.

18. Lead Yourself First

You cannot impart what you do not possess.

You cannot help lead others to deeper maturity and competence if you haven’t attained it yourself.

Which of these points resonated the most deeply with you? How can you apply one of these principles this week?


3 Stages of Leadership

Being CEO of a quickly growing company is hard, and each growth stage requires a different type of leadership.

To succeed, you will have to excel in the roles of:




Here’s what I have learned about high-growth organizational leadership.

Stage 1: Player

In the earliest days of any company, the founders are doing all of the work. There is no extra money to hire others, and you have to be ready to grind. Being a player means late nights, tactical tasks, often feeling overwhelmed, and lots of learning.

During this stage, you build high competency in execution and develop expertise in several core areas of the business. This period is exhausting because there is so much to do, and the pressure is 100% on your shoulders. It can feel like your work is all-consuming.

To use a football analogy:

During the “player” stage, you are like a running back. If you aren’t carrying the ball and scoring touchdowns, your team isn’t winning.

As the company succeeds, you have the resources to hire & the inability to get everything done.

Stage 2: Player/Coach

You won’t have the resources to hire someone for every aspect of execution in the company, but you start to fill significant positions of need. These new team members you are hiring need direction and coaching.

Ironically, adding people to the company only increases your workload short term. There is always a period (ranging from several weeks to months) where you devote significant time to coaching these new teammates. Still, they are only able to contribute a little execution-wise. As a result, you still have heavy execution and tactical responsibilities, but you are also responsible for coaching others.

You will commonly hear people in this phase say things like “I feel buried” or “I wish I could just get some time to think and prioritize.”

This stage is uniquely dangerous for leaders. Up until now, the company has succeeded because of your execution, and the new team members can’t execute at your level + require lots of coaching. The temptation is to give up trying to develop others and double down on your execution. Another danger during this stage is that you are so busy with coaching and executing that there is not much free time to focus on strategy.

During this stage, you learn to teach others and balance the disparate demands of the job.

Success at the player/coach stage requires a commitment to truly building a team.

During the “player/coach” phase, you are a quarterback. You are calling plays, organizing the team, correcting mistakes on the field, AND throwing touchdowns.

Stage 3: Coach

The company no longer relies on your ability to execute at this stage. The teammates you have been coaching can now perform at a high level and teach these skills to new hires. Your role is now focused on strategy, recruiting, and leading.

You’ve been looking forward to this stage for a long time, but something unexpected can happen. You suddenly feel unproductive.

For years, success was getting stuff done. Now your job isn’t a to-do list of things to knock out. Now your job is leading and developing others.

Success during the coach stage starts with understanding the enormous leverage you now possess. By coaching and leading others well, you can now accomplish 50x, 100x, or 1000x more than you could ever do alone. You can now multiply the time you invest in the company.

Each stage is fun and challenging in its unique way. The common thread is that healthy organizations are full of challenge, learning, growth, and mentorship.


Text and Subtext

One simple truth that redefined my understanding of leadership:

Values aren’t defined by what a leader says or the words in a mission statement.

Values are expressed by the reality of what a team rewards, celebrates, and sacrifices.

Some thoughts on the concept of the principle of “text” and “subtext”.

On December 2nd, 2011 Enron Energy Company went bankrupt. In the following days, pervasive accounting fraud and manipulation at the company were revealed. Arthur Anderson was their lead accounting firm. Anderson had annualized revenues of around 10 billion before the scandal. The evidence in the Enron bankruptcy was so damning that Arthur Anderson went out of business. Ironically, Enron had proudly proclaimed these four core company values for many years: Integrity Respect Communication Excellence But that’s not how values actually work.

To understand why it’s important to understand the concept of text and subtext. Text is what we say and write. It’s the things that we explicitly communicate. The subtext is all of the things we communicate inexplicitly with our actions, behaviors, nonverbals, and attitudes. It is easy to assume that leadership is about the things that we explicitly communicate, but research consistently confirms the opposite. People hear the inexplicit messages of an organization far louder than what it explicitly communicates. A couple of examples:

First, a classic scene from the movie Office Space. The audio on this clip isn’t great but it is definitely worth watching:

The boss, Bill Lumbergh, is introducing a consultant who is obviously there to fire some of the team members. it doesn’t matter what is said, everyone knows the subtext is bad for them. Then hilariously Lumbergh introduces the forced corporate fun of “Hawaiian Shirt Day” at the end.

Second, an actual Enron example. Ironically, I was in college in 2001 and part of a group of students who toured Enron and Arthur Anderson on the same weekend just weeks before the house of cards fell apart. During the office tour, we asked one employee if he liked working at Enron. His response was, “I do on paydays.” No matter what Enron explicitly communicated about its mission or values, everyone in the building had viewed the culture to be about making as much money as possible. The fraud and greed are easy to explain in that context.

What are the clues about an organization’s true values?

Who gets hired?

Who gets promoted?

Who gets rewarded?

What motivates sacrifice?

A great quote that has stuck with me is, “A team should be able to point to examples of how they have made sacrifices for their core values.”

It’s important to be clear about one thing. Leadership absolutely requires explicitly sharing values and vision. All great leaders repeatedly and explicitly talk about values. The danger is when what we say and what people experience don’t align.

There are few insults more stinging than to call someone a hypocrite. If you ask most people what that word means they will answer, “To say one thing and then do another.” That’s an example of hypocrisy, but the historical definition is even more helpful. Merriam Webster says this: ‘Hypocrite’ comes from the Greek word ‘hypokrites’, which means “an actor.” … The Greek word took on an extended meaning to refer to any person who was wearing a figurative mask and pretending to be someone or something they were not.


Simon Sinek has famously said, “People don’t buy what you do, they buy why you do it.” Leadership is similar. As a leader, your “why” matters as much or more than your competence to others.

Leadership is ultimately about trust. People will follow imperfect leaders who they can trust, but they will rebel against those in positions of authority that they do not trust. They view them as hypocrites. Healthy culture starts with the text and subtext of team matching.

This concept can be powerfully applied to almost any context. Here are a few:

Are you a part of an organization where there is a chasm between the stated values and the real values? How can you help to create change? If change is impossible, is it the right time to exit?

We all have gaps between what we say we value and what we value with our actions. What areas can you see this gap in your life? Ask a couple of trusted friends to share what they see. Self-Awareness is hard, but it leads to growth and transformation.

Are you actively leading a team? How are you monitoring the subtext and health of that team? Are you fostering an environment where others can tell you when your words and their experience don’t align? Are you receptive or defensive to feedback?

If you have children: What are the values you hope to be impressing on your kids? Ask them to tell you what values they are learning. How are those lists different?

Leadership isn’t about being a perfect person. Those don’t exist. It’s about fostering an environment where everyone knows what is valued and rallies towards a common goal. A culture where the text and subtext are the same.

entrepreneurship, mindset

The Art of Quitting

Over the past 12 years, I have been a part of starting several companies. I’ve been fortunate to be a part of some incredible successes, but I’ve also seen my share of flameouts. I am constantly seeking to understand how to be a better leader and entrepreneur. In this blog, I hope to share some of the things that I have learned along the way.

What personality traits are the biggest predictors of success? Historically experts have identified things like intelligence, raw talent, and charisma. Newer research shows that our mindset might be the most important predictor of future achievement. Specifically, a mindset of persistence may be a more powerful leading indicator than raw talent. In Angela Duckworth’s acclaimed book Grit, she says this about the necessity of persistence in pursuing excellence:

“…there are no shortcuts to excellence. Developing real expertise, figuring out really hard problems, it all takes time―longer than most people imagine….Grit is about working on something you care about so much that you’re willing to stay loyal to it…it’s doing what you love, but not just falling in love―staying in love.”

That aligns with my experience. It’s impossible to build a business, a relationship, or any expertise without staying the course. But I’ve learned another paradoxical truth. Successful entrepreneurs are simultaneously skilled at persistence and at the art of quitting.

2nd Time is Not the Charm

In October 2009, I was a part of a team that launched an online auction business. Against all odds, it was an incredible success that surpassed our wildest expectations. We were young and naive; at 30, I was the oldest person in the company. Emboldened by our success, we began planning a 2nd e-commerce startup in 2011. Abundant time, money, and passion were poured into the 2-year buildup to launch. Confidence was high that this new venture would be another huge success. The concept was an online store where customers could shop for any product in mainstream categories. During the checkout process, they would play a short flash game to win a discount on their order. We believed our creation would add excitement and entertainment to the shopping process. We finally launched the website in 2013 with high hopes. We were exhausted but excited.

By the time the first customers saw the website, I had personally invested thousands of hours and a large amount of personal savings into funding the project. I eagerly watched to see how customers would respond. The early results were…terrible. The average customer was not responding at all. Potential customers were bouncing off the landing page like it was a trampoline. It would be hard to overstate our discouragement at the initial results. Internally, company morale sank as the reality began to set in.

In retrospect, we made several missteps in the process of launching:

-We didn’t spend enough time talking to potential customers
-We did not create a minimum viable product (MVP) and tried to launch a polished product
-We were overconfident because of the success of our first company
-We underestimated how quickly Amazon was consolidating market share in e-commerce
-We picked a technology that would soon be extinct (Flash)
-We designed around desktop instead of mobile

It’s quite a list of missteps now that I type it all out. And yet, I don’t have many regrets about the mistakes we made in launching. Hindsight is always 20/20, and anytime you try to do something new, there is a decent chance that people won’t get it. The question before us was “What do we do now?”

“Don’t Give Up”

Back to the research on the mindset of successful entrepreneurs. Conventional startup wisdom affirms the value of the statement “Don’t give up.”  There are epic stories of people who refused to give up and were rewarded for their persistence.  One great example Business Insider recounts here is Pandora: 

Pandora was not able to pay its employees for an astounding two years between 2002 to 2004 while it worked on producing a viable commercial product. Not paying full-time employees is very, very illegal in California, where Pandora is based.

“We had no idea we were breaking the law,” Westergren said.

Over that period, Pandora accumulated $2 million in back wages owed. Westergren himself ran up a $500,000 debt on “maxed-out cards” while he paid bills and as many salaries as he could afford. 

He paid a little at a time in the order they were due, an experience he describes as like “playing Tetris” with his finances, which he “[doesn’t] recommend.” 

Two employees sued for back wages. And Pandora’s original model of licensing out its Internet music recommendation engine to retailers and labels was not working out. 

But Westergren, a musician by training who had little to fall back on if he defaulted on the debts, managed to keep most of the team together. To keep employees motivated, he gave speeches upon speeches, encouraging them that the potential market was huge, and so was Pandora’s potential impact on music and culture. 

Somehow — Westergren says he is not sure how — the company was able to close a $9 million round of funding in 2004, when money was much harder to come by than it is today. 

Westergren called an all-hands meeting for everybody in Pandora that same day. Everybody was expecting another stirring speech, he says. Instead, he pulled a stack of envelopes from his back pocket and paid out the $2 million among the 50 employees right then and there. 

“Everybody thought it was a bad joke, like it would bounce or something,” Westergren says.

What an epic story! The scene of Westergren handing out envelopes full of back pay is incredible.

This story can serve as a reinforcement to my natural disposition to be persistent. I don’t like giving up on things.  I am the kind of person that will keep working on a brainteaser longer than other people just because it drives me nuts if I can’t figure it out.  Hearing the Pandora story only strengthens my resolve. “No matter what – don’t ever give up.  Sometimes success comes from sheer force of will.”

The problem with lionizing stories like the one above is that it lacks two important pieces of context.

1. Why was Westergren so convinced that he should bet everything he had to keep going? Was there clear evidence that they were on the cusp of a breakthrough? Was it obvious they had product/market fit? Was their main challenge a temporary disruption to fundraising due to the tech bubble bursting?

2. How many stories exist where things didn’t turn out so cheerfully? Survivorship bias tells us that using anecdotes and stories of successful entrepreneurs is dangerous. How many times has the founder of a company “played Tetris” with their finances only to see it end in bankruptcy? We never hear that multitude of stories because they don’t get articles in Business Insider.

The point I am driving at is this: What if persistence isn’t always the answer? What if sometimes persistence prevents success?

Toxic Persistence

The last 20 years have seen an explosion of reality TV talent shows. One of the most notable is American Idol, which has led to stars like Kelly Clarkson and Carrie Underwood. Several years ago, American Idol was must-see TV for my wife and me each week. Without a doubt, the most cringe-worthy part of each season was the compilation of failed auditions. The clip below is a fan’s “top” 10 worst auditions of all time.

The hardest part of watching these auditions was not the off-key singing. It is how contestants responded to negative feedback from the judges. Instead of introspection, contestants would often reply with something like, “I’m not giving up on my dream!” or “I’ll prove you wrong!” These contestants are exercising persistence, but it is the darker side of persistence. I call this type of persistence “toxic persistence” because it harms us.

At its core, persistence is continuing on the same course despite difficulty or adversity. Belief is what fuels persistence. A belief that if we keep going, better days are ahead. But when we are heading in the wrong direction, the last thing we want to do is persist! Unfortunately, our psychological software has a bug called “belief perseverance.” When we sincerely hold a belief, we don’t process new evidence properly. Several studies have shown that being presented evidence contrary to a deeply held belief can strengthen the incorrect view. When evidence contradicts our beliefs, we tend to choose our beliefs. Ironically, aspiring entrepreneurs can be the most susceptible to toxic persistence precisely because they are so committed. Author C.S. Lewis once observed:

“Progress means getting nearer to the place you want to be. And if you have taken a wrong turn, then to go forward does not get you any nearer.

If you are on the wrong road, progress means doing an about-turn and walking back to the right road; and in that case, the man who turns back soonest is the most progressive man.”

Quit isn’t a Four Letter Word.

As I told you earlier, the second launch I led as an entrepreneur could not have gone worse. We made countless strategic errors leading up to the launch. However, when I reflect on this period, I don’t think it was the mistakes I made before launch that I regret. I regret the decisions I made after launching far more.

I regret not giving up sooner. It was clear that our business hypothesis was wrong. Not just that we were in the wrong zip code, more like we were on the wrong planet. In the face of plentiful evidence that we were not on the right path, we continued to push ahead. Over the next year and a half, we would waste even more time, resources, and morale trying to redeem a project more supported by belief than market evidence.

Why? I think the primary reason is identity. When you pour a lot of yourself into something, the lines can begin to blur. The project can transition from something you are working on to something that defines you. Once your heart makes that jump, it is excruciatingly difficult to allow it to fail. The project becomes a referendum on your worth as an individual. You become willing to prioritize belief over evidence because a failed project means laying off friends and painful conversations.

Another reason that we resist quitting is the sunk-cost fallacy. When we have invested significant time or money into something, we develop an irrational attachment to it. Imagine you buy a used car. A month later, you discover that it will require repairs that exceed the value of the car. Studies have shown that we are likely to pay for the repairs even though it isn’t rational. 

I kept going because I was too afraid to quit. That’s not helpful. In fact, it will actively prevent you from accomplishing your goals. It is a bottomless pit that can devour all of your devotion, time, passion, and money. The more you indulge it, the more dangerous it becomes.

My point is that persistence must be paired with another skill to be valuable. Knowing when to quit. Our culture celebrates starting things and mourns ending things. Our emotional and societal incentives all discourage quitting. I call it the art of quitting because it requires judgment, maturity, and humility. In Seth Godin’s book “The Dip”, he examines the importance of strategic quitting and makes the observation:

“Winners quit fast, quit often, and quit without guilt.”

W.C. Fields surely agreed with this sentiment when he famously said:

“If at first, you don’t succeed, try, try – and then quit! No use being a fool about it.”

Toxic persistence is pressing on when quitting would be wiser. Quitting saves us from devoting our resources to efforts that are destined to fail. It stimulates growth and learning while bolstering our humility. It is the foundation that future success is built upon. As Mulla Nasrudin observes:

“Wisdom comes from experience, and experience comes from failure.”

Redemptive Persistence

Redemptive persistence is flexible and adaptive. To use an example from above, imagine someone who deeply loves music and wants a career as a singer. For a variety of reasons, including talent and circumstances, this might not be possible. Toxic persistence leads to a mindset that the only path to success is by becoming a professional singer. It would lead someone to continue to pursue a career in singing even when all the evidence from the market is that they don’t have a future as a performance artist. Redemptive persistence would lead someone to incorporate feedback and explore other areas to find a career in music. How many successful producers, songwriters, and agents only unlocked their full potential when they quit trying to be a singer? Redemptive persistence is about pursuing a career that engages your love of music while being open-handed with the specific context.

I recently read the biography of a man who dreamed of becoming an officer in the British military. He gained his first significant military assignment at the age of 20 and commanded troops by 21. He distinguished himself for courage and bravery in several battles, but after a few years, it became apparent that he would never be able to advance to a higher rank because of where he was born. After several years of service in the British military, he quit and pursued a new career in farming and politics in Virginia. Years later, he would unexpectedly realize his dreams of leading in a military context when he was appointed General of the Continental Army. As you have probably guessed, that man was George Washington. Washington’s willingness to resign from the British military instead of pressing forward created the context and opportunities that culminated in serving as the first U.S. president. How would the world be different if he had pressed on instead?

Conversely, it was Washington’s redemptive persistence that made him such an exceptional leader during historic times. He had not attended college and was woefully underprepared to serve as General of the Continental Army. He made repeated mistakes during the Revolutionary War and won very few significant battles until receiving substantial French aid. He was always low on resources and troops. But America won the war, in large part, because of Washington’s persistence. He correctly observed the enormous financial cost of the war for the British. Even though the battles weren’t going particularly well, America could win the war with endurance. He successfully held the ragtag army together until the British bills mounted and the French joined the war as allies of America.

Final Thoughts

How can we identify when our persistence is toxic or redemptive? I’m going to tackle this more in future posts, but I would offer two thoughts.

  1. Redemptive persistence is almost always predicated on evidence that objectively points towards possible future success. It is flexible and adjusts to feedback. Toxic persistence is often a defiant “doubling down” in the face of the evidence. It is characterized by a rigid definition of success that we become unwilling to change.
  2. This highlights the important role of judgment. We don’t know what would have happened if Washington had continued in the British military. Maybe it would have led to his promotion to leadership despite being born in the colonies. Conversely, many contemporaries of Washington believed the Revolutionary War was a lost cause at points. This mental model does not remove the need for judgment; rather, it highlights the necessity to carefully and strategically choose when to quit and when to press on.

In 2012 I started working on what would be the most significant professional failure of my life. It took me almost a year and a half to break free from a mindset of toxic persistence. That failure was one of the best things to ever happen to me. It helped me learn the art of quitting, and I am a better leader and entrepreneur. It would turn out that my most significant professional failure would set the stage for the highlight of my business career so far: Co-founding Simple Modern.


Behind the Curtain

Last year I did a 1 on 1 meeting with every member of the Simple Modern team. One of the questions I asked each person was,

“What is the best part of Simple Modern’s culture?”

I intentionally left it open-ended so that I could see what patterns emerged. One word surfaced repeatedly:


We live in a world with unprecedented access to information. Social media and smartphones have given us more insight into the lives of others than ever before. And yet, our hunger for authenticity and transparency continues to run deep. Why is that?

We share more with the world than ever before with the internet, but what we share is still highly curated. We present the image that we want others to see. Yet we all long for a world in which we are fully known and still fully accepted.

If you want to help others develop and grow it runs deeper than leading by example and doing the right things. It means inviting others into the motivations, heart attitudes, thought processes, doubts, and fears behind your decisions and actions. It requires vulnerability and allowing others to see your imperfections.

A few questions that help me to apply this principle:

  1. Am I sharing the “Why” behind my actions and decisions with my teammates?
  2. How do I respond when someone is transparent about something negative happening within themselves or the team? Am I receptive or dismissive?
  3. Am I more concerned with projecting a good image or sharing the reality to those around me?


35 Reflections on Life and Business

Recently I celebrated my 42nd birthday. I took some time to reflect on life and business. Here are some of the top things I have learned:

1. Relationships with depth, trust, and intimacy are the primary way to achieve lasting contentment in life.

2. Have a clearly defined personal mission. The reasons behind your actions have a profound impact on how others experience you—having a clear why serves as a north star during trying times and inspires others to join in the journey with you.

3. Who you are is more important than what you do. A wise mentor has emphasized this to me over time. Ultimately your character is far more important than your resume or accomplishments. The Bible says it best: “What does it profit a man to gain the whole world but lose his soul?”

4. Don’t be too proud to ask for forgiveness. Forgiveness doesn’t change the past, but it does enlarge the future

5. Generosity is the antidote for greed. Be generous with everyone. Give to people and situations where you don’t stand to gain anything in return.

6. Affirmation and encouragement are among the most encouraging and life-giving things we can offer to others. The best part of all is that they don’t cost us anything. Be generous with your words of praise.

7. The best parts of life are a result of compounding. At 42, I can trace out how my favorite things have resulted from repeatedly prioritizing and working on the same essential things.

8. Be transparent and honest. It is tempting to try to manage how others perceive us, but it always backfires in the end. When there is integrity between the perception of others and our reality is much less stressful.

9. Ask others for feedback and be willing to change. We cannot grow unless we understand how others experience us. Instead of being defensive when we receive hard feedback, assume it is accurate and look for applications.

10. Think backward when making major life decisions. How will you feel about this decision when you are 80 or on your deathbed? It is incredible how much this helps me at forks in the road points in life.

11. Cultivate thankfulness in your heart. Find ways to deliberately identify and give thanks for the things that bring joy and happiness to your life. Thankfulness is the vaccine against bitterness as we age.

12. Investigating what the Bible says about Jesus was life-changing for me.

13. Fulfillment comes from a life that is devoted to something larger than self. Reject the idea that fulfillment comes from chasing all your internal desires.

14. Reading biographies is one of the easiest ways to learn from the experiences of others. It also makes people from different eras more relatable and accessible. The great people that came before us dealt with all the same challenges and desires that we experience.

15. Having discernment about when to forge ahead or strategically quit is a superpower. My tendency to persist has been my biggest strength and biggest weakness at different points in my life.

16. View mistakes as tuition. The lost resources (time, money, etc.) offer the potential to learn a valuable lesson for the future.

17. Develop a growth mindset. Intentionally challenge yourself to grow in areas that are uncomfortable or where you lack natural talent. The process of getting better through effort and determination is empowering.

18. The culture you immerse in will shape the person that you become. A steak gradually takes on the flavor of a marinade it sits in, and similarly, we become a reflection of the cultures we are a part of every day. Choose the friends, spouse, and jobs that promote a healthy culture.

19. Learn through doing. The internet has made it easier than ever to gain knowledge about any subject you desire, but we learn best through doing. Don’t settle for acquiring knowledge. Find ways to start applying that knowledge in your life immediately.

20. The world is more complex than ever before. Our natural response is to simplify, but complicated things aren’t simple or black and white. The answer to complexity isn’t simplicity; it’s focus. Reject simplistic narratives and embrace nuance.

21. Compete with yourself instead of others. Instead of fixating on being “the best,” spend time focusing on reaching “your best.”

22. Achieving excellence comes through iterative improvement. The paradox of excellence is that it can only be achieved by practicing at a less than excellent level for a long time.

23. Life is full of trade-offs and opportunity costs. Saying “yes” to one thing means saying “no” to countless other things simultaneously. Learn to say “no” frequently so you have the margin to say “yes” to the right things.

24. Help others to believe in themselves. Everyone needs an encourager that helps them to see their full potential.

25. Make asymmetric bets. Find places where you can invest time and resources with a fixed downside, but the upside could be 10x or 100x. Some examples are mentoring, investing, and going on a first date.

26. When planning a business, identify how you can create moats (sustainable competitive advantages). Building a company is hard work and will take years of your life. Build something defensible from the beginning so that you don’t have to watch the market erode what you have built.

27. Don’t settle when hiring. Be slow to hire and prioritize character, competency, curiosity, and hunger.

28. Entitlement is like emotional cancer. Pat Riley once described it as “the disease of me,” and in my experience, it is the number one risk to successful teams. Focus on treating other people better than they deserve instead of focusing on how you should be treated.

29.  Constantly cast vision to those that you are leading. “If you want to build a ship, don’t drum up the men to gather wood, divide the work, and give orders. Instead, teach them to yearn for the vast and endless sea.”

30. The best entrepreneurs I know are like scientists. They are constantly forming theories and designing experiments to test those theories and learn more about the world.

31. The most successful individuals have plenty of failures in their careers. What makes them successful is that they keep taking swings. Be more afraid of never hitting a home run than of striking out.

32. If you start a business, bootstrap for as long as you can before raising money. One of the most freeing aspects of Simple Modern is that we don’t answer to outside investors. We are a stronger, more generous company as a result.

33. The very best way to learn about business is to join a high-growth startup. There is no better place to grow your skill set, advance your career, and learn how to build a company.

34. Focus on process over results. I have found that results and the process are often less correlated than I would expect. I cannot control outcomes, but I can dictate how I approach the process. Over time, this is a winning strategy.

35. Life requires a bias to action. There will be countless times when it is unclear what is the right next step; making an imperfect choice and iterating is almost always better than doing nothing.

Which of these resonate with you?

entrepreneurship, mindset

Past Shapes Present

William Wordsworth, a well-known 18th century English poet, wrote:

“Life is divided into three terms – that which was, which is, and which will be. Let us learn from the past to profit by the present, and from the present, to live better in the future.”

Wordsworth was making a salient point: Our past experiences shape our present reality, and how we steward today impacts our future. Before founding Simple Modern in 2015, I worked for a non-profit ministry for nine years, and that experience powerfully shaped my approach to business and culture.

Three lessons, in particular, stuck with me as I began my journey as an entrepreneur.  Each of them directly impacts how I lead Simple Modern—both now and into the future.

Lesson 1: Creating A Culture Of Humility

Humility is one of Simple Modern’s core values, and it profoundly impacts our company’s culture and day-to-day operations. I would define humility as having a sober-minded view of self. It is not pretending that we aren’t any good in an area that we are truly gifted. Conversely, humility also is not having a puffed-up or overly elevated view of our importance or abilities. As a former leader of a ministry team, I experienced how critical it is to a team’s culture.

As with most non-profit organizations, our team was small but dedicated, usually consisting of 6-8 people at any given time. Everyone had to be willing to do the unglamorous day-to-day work needed to keep the ministry operating. No team member was above any task. Another area where humility was critical was in our self-awareness. Ministry is about helping other people to experience internal breakthroughs in how they view themselves and the world around them. Howard Hendricks once said, “You cannot impart what you do not possess.” It is impossible to help others have a higher level of self-awareness unless you have personally done the hard work of personal excavation.

Each of us has areas of our character that we consistently struggle with throughout life. For me, my pride has been the most consistent thorn in my side. I have learned that, when left unchecked, it leads to me having an inflated view of self. Humility is the antidote to pride. It neutralizes the poisonous effects that pride can have on our relationships and career. When we check our ego at the door, we become better teammates and better leaders.

One of the most impactful decisions I have made in my life happened about halfway through my college career. It started when I realized that I was far more flawed than I had ever been willing to admit. Up until that point, when I received negative or even constructive feedback, I would immediately respond with defensiveness. In my mind, it was up to the person offering the feedback to prove that their observations were correct. This epiphany led to a small but significant change in mindset. From that point forward, when I received unflattering feedback, I assumed that it was true instead of having the default assumption that it was false. This simple decision has transformed my self-awareness and led to countless growth opportunities as I have learned more about how others experience me. The key was my willingness to lay down my pride in search of a more accurate view of myself.

Giannis Antetokounmpo is one of the 2-3 best basketball players in the world. He is a two-time MVP and is now the reigning Finals MVP and leader of the world champion Milwaukee Bucks. Recently, a reporter asked how he dealt with his ego as he grew as a person and player. I thought his response was remarkable:

When we founded Simple Modern in 2015, we knew that humility needed to be a part of the foundation. Over the past six years, we have been fortunate to experience a lot of success. Our collective desire to prioritize humility has helped prevent competition, ego, entitlement, and pride from eroding our culture. Not only that, it has spurred tremendous internal growth for our team.

Lesson 2: It’s Not About The Profits.

The word non-profit means precisely what you would think. No profit. During my years in ministry, my team and I raised support to pay our salaries. All additional funds and resources went towards the organization’s administrative costs. In the non-profit world, the point of the money is to enable serving others. For this reason, in the ministry world, profit can seem like a four-letter word.

You can imagine the tension I felt when I first transitioned from ministry into the business world. In the business world, especially e-commerce, there is a bias toward numbers and profit. An organization’s success criteria usually revolve around what drives the most profit. I wrestled with this for several years before seeing how these seemingly contradictory ideas could work together.

Simple Modern’s culture is founded on the idea that generating profits makes generosity possible. As someone with non-profit and business experience, I now understand that profit is not necessarily bad. Profits can be redemptive and beneficial when used to care for and serve employees, partners and customers. For our company, this looks like giving generously to worthy non-profit causes, investing in our team members and their families, and offering premium quality at generous prices to our customers. In other words, in a healthy business, the profits make it possible to impact more lives positively.

Lesson 3: Explain The “Why”

In the non-profit world, you come to understand the need and importance of mission and vision. Mission and vision motivate people. In my non-profit leadership role, I wasn’t paying my team. We were all raising our salaries. To keep them invested in the ministry, I had to repeatedly articulate “why” we were doing what we were doing and coach and lead them using motivation.

Author Simon Sinek wrote a book called Start With Why. In his book, he explains the significance of starting with the question, “why,” as opposed to “what” or “who.” According to Sinek, explaining “why” we are doing what we are doing is critical. It unifies the team and creates a common reason for everyone to work together, leading to increased engagement and success.

This lesson translates to the business world. Whether it is sales or recruiting, leaders must get people to buy into the overarching mission and vision. When employees feel connected to the mission and vision of the company, they more deeply bond with their teammates, have greater job satisfaction and are ultimately more empowered to do their best work.

Antoine de Saint-Exupéry, a French writer and poet, captured the essence of this when he wrote:

“If you want to build a ship, don’t drum up the men to gather wood, divide the work, and give orders. Instead, teach them to yearn for the vast and endless sea.”

Rather than telling people what to do, communicate mission and vision, and tell people why they are doing what they are doing. Teach them to yearn.

Closing Thoughts

My perspective was irrevocably shaped by my years working in a non-profit context. That experience had a profound impact on how I view my life’s mission and the purpose of my career. Not surprisingly, the Simple Modern mission statement is straightforward:

We exist to give generously.

It is possible to fuse the most potent aspects of the non-profit and for-profit worlds to create thriving organizations. We all want our lives to be a part of impacting the world in a positive and redemptive way. When we lead with humility, generosity, and vision, it enlarges all our futures.


Creative Collaboration

Team Collaboration: How to Maximize Productivity (& the Tools to Help) -  Lifesize

Collaboration is one of the five core values of Simple Modern. We believe that teams produce better results than individuals, so collaboration plays a significant role in the day-to-day structure of our company. We view every interaction with our teammates, manufacturers, partners, and customers as an opportunity to work together. This environment of collaboration plays a critical role in our process of creating world-class products.

We define collaboration as solving problems by incorporating the strengths and ideas of the entire team. Collaboration is almost always helpful, but this is especially true in creative endeavors. Research has shown that in procedural jobs, the best performers are usually 2x as effective as an average performer. In creative endeavors, the best performers are a shocking 10x more effective than average. When talented and collaborative teams focus their effort on creative work, extraordinary things are possible. As Steve Jobs once observed:

“The total [is] greater than the sum of the parts. That’s how I see business: great things in business are never done by one person; they’re done by a team of people.”

Working in an environment where everyone’s perspective is valued and encouraged has several benefits

  • Leverages the gifts and talents of the whole team to achieve a common goal.
  • Allows leaders diverse feedback sources to incorporate into the decision-making process.
  • Amplifies everyone’s voice to be heard and helps develop junior team members into leaders.
  • Creates awareness of different points of view
  • Encourages bonding and communication among team members

In this setting, everyone contributes to the team’s effectiveness by bringing their individual experiences, perspectives, skills, and strengths to the table. It also results in better decisions and products.

Collaboration Strikes Back

Creating a movie is an excellent example of the collaborative process. For starters, the story can be about literally anything real or imagined. This wide range of possibilities creates an expansive creative canvas to collaborate. What is impressive to me is the sheer number of people that are involved in helping to make the movies that we love. If you look at the top 20 grossing films from 1994-2014, you have a subset of 1,000 different movie projects. These films averaged 3.5 writers, 7 producers, 55 people in the art department, 32 in sound, 55 in camera/electrical, and 156 in visual effects. That’s over 300 people before you even start counting actors and the countless other people involved in the production. These numbers can swell into the thousands. Iron Man 3 sported an enormous cast of 3,310 people!

When a movie is released, we see one cohesive story, but that comes from countless collaborative conversations and brainstorming sessions throughout the production process. When Toy Story premiered in 1995, Critics universally praised its humor, graphics, and creativity. Its path to glory was far from a foregone conclusion, however. In 1993, Disney canceled the film because of how cynical and unlikeable Woody was in the original screening versions of the film. Steve Jobs and Pixar were able to convince Disney to allow them to work on redoing the film. The ultimate result of the creative process was a timeless classic.

One more example of how the collaborative process often produces a better result is in the dialogue of a film. Below is a famous scene from The Empire Strikes Back:

This iconic moment is even more remarkable because Harrison Ford’s line in the script was “I love you too.” Ford intuitively understood that Han Solo would never have responded to Leah quite so conventionally. He insisted that the line should be “I know.” Ford’s suggestion was such a collaborative improvement that the crew never filmed the scene with the original line.

Collaboration and Leadership

My natural bend is to have a big tent mentality towards leadership. I like to incorporate the thoughts and voices of others. But over the years, as I have held various leadership positions, I have struggled with the balance of knowing when to make decisions and when to encourage collaboration and dialogue.

I have learned that enabling collaboration requires humility. It starts with creating an environment where the conversation is not guided by title and role but by the merit of ideas. Leaders may have the authority, but collaboration involves a conscious choice to bring others into the decision-making process. As others share their perspectives, leaders must then ask, “How do I turn these voices into a decision?” Leaders have the authority to make the final decision; they also have the responsibility to make sure other people’s voices help inform the decision-making process.

It is important to note that there will be instances when collaboration does not result in a consensus opinion. Input from more people can lead to better decisions, yet more voices can also result in conflicting thoughts and ideas. Though challenging at times, the lack of consensus may produce additional clarity for the leader. Ultimately, a leader’s responsibility is to create a collaborative environment and then chart a course weighing all the feedback if the group cannot reach a consensus.

Collaboration benefits leaders in several key ways:

  • The collaborative process can “stress test” proposed decisions to see if they hold up while also sparking creativity and new ideas.
  • It gives the leader credibility when they value the entire team’s perspective. Because they have shaped a decision, teammates will have more buy-in to the path forward.
  • Even when a leader enters a discussion with a strong opinion, it can be helpful to bring the idea or proposed decision in front of a group for feedback and peer review.

Steve Jobs: Champion of Collaboration

In many cases, the best collaborations are serendipitous and unplanned.  No one understood this better than the late Apple founder and CEO Steve Jobs, and he placed a high value on collaboration.

Jobs serve as CEO of Pixar through its early years of growth and becoming a public company. Though Jobs wasn’t involved in making Pixar films, he took responsibility for designing the Pixar Headquarters building. Jobs intentionally designed the building to mirror the left and right sides of the brain: creative offices on the right side and technical offices on the left.  Jobs insisted on a central atrium in the middle of the 218,000 sq. ft. building.

Traveling anywhere in the headquarters required that individuals pass through the central atrium, thus encouraging chance interactions and collaborations with others throughout the day. Jobs believed that in-person interactions spark innovation, so he purposefully designed the building to bring 700+ employees together and encourage as much collaboration as possible. This atrium was the home to countless collaborative conversations that produced classics like Finding Nemo, The Incredibles, Wall-E, and Monsters Inc.

Pixar's critically-acclaimed Emeryville campus - San Francisco Business  Times
The central atrium in Pixar Headquarters

How To Be An Effective Collaborator

Everyone is a collaborator to some degree. Whether collaborating with a co-worker at work or a spouse in marriage, collaboration is a vital part of our life. It begs the question, “How do I become a more effective collaborator?”

One way to be an effective, healthy collaborator is to understand the difference between opinion, persuasion, and conviction level beliefs. We each have a hierarchy of beliefs that we hold with varying degrees of strength. These different belief levels—opinion, persuasion, and conviction—must be kept in check for the collaboration to be as successful as possible. Imagine a pyramid divided into three sections.

  • The pyramid’s base represents a person’s opinions: assumptions, desires, wishes, and preferences.  Some examples would be “Mint Chocolate Chip Ice Cream is the best” or “The Oklahoma City Thunder are my favorite basketball team.” These opinions matter to me, but they don’t influence my treatment of others, and I can still get some ice cream with someone who mistakenly claims that Rocky Road is the best flavor.
  • The second level of the pyramid represents persuasion-level beliefs. Compared to opinion-level beliefs, persuasion beliefs are held more tightly and influence how we interact and work with others. These beliefs usually center around more consequential topics, influence our behavior, and shape our interaction with others. They are usually more tightly held because we believe that there is significant evidence for holding these beliefs. We can continue to collaborate and work with others with different persuasion level beliefs but will often try to influence those around us on these issues. An example of a persuasion level belief is how to educate your kids between public, private, or home school.
  • The top of the pyramid represents a person’s convictions: those few central beliefs that a person feels strongly and is unwilling to compromise. Collaboration on an issue where there are different conviction level beliefs is by definition almost impossible. One example would be the inability for Pro-Life and Pro-Choice activists to collaborate on legislation toge

Effective collaborators have a healthy balance of opinion, persuasion, and conviction beliefs. Just like most of the volume of a pyramid is in its base and only a tiny amount is in its tip, we should strive for a balance where our conviction level beliefs are far fewer than our opinion level beliefs. An unbalanced distribution of these beliefs can harm the collaborative process and affect the group dynamic. Having very few convictions and persuassions communicates that you don’t stand for anything and makes it impossible effectively contribute a strong point of view. On the other hand, having an excessive amount of conviction level beliefs makes us more closed off to different perspectives. Collaborating with people who believe their perspective on every issue is a hill to die on is often exhausting and unproductive.

Your Ideas are Not Your Identity

The challenging thing about collaboration is that it requires emotional maturity. Growing up, I realized something about myself. When I proposed an idea to a group that was well-received, I felt great.  Conversely, when others disregarded or disliked an idea that I suggested, it was devastating. In those situations, I found that I would get defensive, shut down, and stop contributing to the collaborative process.

Over time, I have learned that ideas are objective things, not my value or identity as a human being. I have ideas, but they don’t define who I am. This allows me to evaluate ideas on their merits and not simply based on their origin. Effective collaborators don’t find their identities in their ideas. They can lead productive conversations and won’t be discouraged or hurt if people don’t like their ideas because that’s not where they find their identity. The best leaders and collaborators can advocate an idea and then drop it to support a stronger idea from someone else a few minutes later. Leading others in collaboration starts with leading ourselves.

Collaboration at Simple Modern

We believe that we are smarter than me. As a result, we’ve built our company to promote collaboration in everything we do. Our hiring process is a multi-person endeavor as we work together to find the best possible candidate. It’s not uncommon to find clusters of people gathered together at our office, troubleshooting a problem or brainstorming our next great idea. As founder and CEO, I meet with all of our employees a few times a year to ensure that they have the opportunity to offer feedback and have their voices heard.

I believe Simple Modern’s exponential growth and continued success are due to the high value we place on collaboration. We encourage our team members to collaborate, contribute to conversations, propose ideas, and defend what they think—in a low-stress, helpful and friendly environment. Once we make decisions, we move forward together as one team. I believe this attitude is a driving force of how we have grown to almost 100,000,000 in annual revenue in just five short years.

Here are a few questions I ask myself to continue to grow in this area:

Do I have a balanced belief pyramid? What is my distribution of beliefs between opinion, persuasion, and conviction?

Where am I finding identity in my ideas? How can I refocus where I am finding my identity?

How can I create an environment around me where people know their input and ideas are welcomed and encouraged?



The early days of a startup are a singularly unique experience. You are bringing something new into the world, no one knows who you are, and no one cares. It is obvious quickly how difficult it is to gain traction and become relevant. When we started Simple Modern in 2015, the hydration market was full of established, well-run, strong brands. During the first couple of years, I was repeatedly asked questions like, “Aren’t you just selling a knockoff?” and “Why would anyone want to buy your product over the other options that already exist?”

Also, money is always scarce. Every startup that I have been a part of has been bootstrapped. While I am partial to this funding method, it all but guarantees that money will be tight for at least the first few years. Our foundering team did not draw any salary until the company was almost a year old. Our office in the early days was an upstairs room in my house or the local Panera Bread. We scrounged for ways to do things less expensively and conserved the limited resources we did have for inventory purchases. In contrast, during our first year of operation, two of our hydration competitors were bought by large corporations for sums approaching half a billion dollars each. After a couple of years, we swallowed hard and invested the money to attend the International Home and Housewares trade show. The day before the show was used by exhibitors for booth setup. While we admired the 6 figure displays that other competing brands had created for the show, we sheepishly set up shelving that we had purchased at IKEA. At one point, we watched employees from a competitor walk by our booth, literally pointing and laughing at us.

Ironically, the difficulty of building a startup is also an important part of why the experience is so rewarding. Without the advantages our competitors enjoyed, we had to think creatively. We compensated for our relative lack of resources with sweat equity. There were long days and nights, but in the process, our early team bonded deeply. We developed a tenacious underdog mentality and a correspondingly big chip on our shoulders. I saw growth in my personal character and humility as my role called me to help lead us through challenging situations. As the business grew, it filled us with immense gratitude because we knew how difficult it had been to accomplish. When we talked about the future, it felt like a big place full of possibility and promise. The early days were an incubator of relational, personal, and professional growth for all of us.

My experience had taught me about the emotions behind running a startup. Before I co-founded Simple Modern, I had been a part of starting and scaling several e-commerce businesses. As a company grows, it is easy to focus on the future not yet obtained instead of enjoying the present. I would often spend my time thinking about acquiring the next group of customers, improving our processes to reduce chaos, implementing the latest technology, and achieving greater stability. As a result, I consistently had a feeling of wanting to graduate to the next phase. But when I looked back on those years, I realized that it was truly the process and not the destination that I had enjoyed. The clip below from The Office sums it up perfectly:

Because Simple Modern was not my first rodeo, I made a conscious effort to live in the present. Those early days were some of the best days of my life.


I vividly remember taking my son to Disney World for the first time in the spring of 2016. Simple Modern had just started selling water bottles the week before we left for our vacation. During our trip, I was struck by the number of water bottles and tumblers in the park. I began to take mental notes about the brands and types of water bottled I spotted the most frequently. When I returned, I set up a Slack channel called #inthewild where our team could post pictures when we spotted others using our products. Early on, I was surprised at how infrequently we posted on the channel. It turns out that you need to sell a LOT of products before you start to see them organically.

We were fortunate that Simple Modern quickly experienced product/market fit. As we released products, we saw our sales and brand presence continue to increase. A little after the company’s 2nd birthday, Target offered Simple Modern nationwide distribution. When my family revisited Disney World in the summer of 2019, I usually spotted several of our products each day. Not only were we successfully selling more units, but our brand was beginning to really resonate with customers. People loved our combination of premium quality, affordable prices, and dedication to generosity.

As our sales and customer base grew, everything else followed suit. We moved into our first office in May 2017, and by mid-2018, we had already begun looking at options for a larger office. The team also continued to grow. From our initial core team of 10, we slowly grew to 15. We had a strongly ingrained “slow to hire” mentality, but by the time we made our next batch of hires, it was obvious we had waited too long. After months of not hiring, we hired 5 people during one particularly hectic week in Fall 2019. The new reality was also impacting the company’s bank account. For the first time, it felt like we had a little financial breathing room. Although our circumstances had changed, things still felt very much like a startup. There were very few established processes, and most core leaders still wore several different hats out of necessity. At times, chaos reigned as we sprinted to keep up with our growth. I reminded my teammates to soak in the experience. I would say things like, “Even though things feel stressful and crazy right now, don’t be in a hurry to get to the next phase. In the future, you will remember these days and wish you could experience them again.”

The End of the Beginning

As we have been building Simple Modern, I have been squarely in the season of raising young children. When we founded the company, my son was four, and my daughter was not quite one. The experience of being a father has been one of the most enjoyable highlights of my life. Recently my wife and I cleaned out some old toys, and I was struck with a pang of sadness and nostalgia. I looked at toys that my children had once adored and thought about playtimes gone by. It was a poignant reminder that my kids are growing up. Someday soon, they will no longer be children. I have always been aware that is happening, but that moment underscored a gradual transition happening every day.

My work life has been filled with signs of transition as well. Last year our team moved into an incredible office that could serve as the company headquarters for years to come. We have grown from 3 co-founders to 45 amazing full-time teammates in just a little over 5 years. We now serve millions of customers worldwide and have the privilege to partner with some of the world’s leading retailers.

Last week our company experienced another significant milestone. The fifth person to join our team transitioned to his next adventure. He was a great teammate and friend. He had accomplished everything that he wanted to achieve with Simple Modern, and he is leaving on great terms with everyone. I am excited for his entire family as they will now live close to both sets of grandparents. Personally, it was a sobering experience for me. His transition was a concrete reminder that Simple Modern is no longer in its infancy. I realized that it was just like watching my kids grow up, it has been happening gradually all along, but this moment highlighted that we are at the end of a season. As I reflected on this reality, I was reminded of Winston Churchill’s words:

“Now, this is not the end. It is not even the beginning of the end. But it is, perhaps, the end of the beginning.”

I think our company has a tremendous future. I’m encouraged by the products we are developing, the customers we get to serve, and the opportunities to give generously that the business provides. We have the most talented team that I have ever had the opportunity to work with, and it seems obvious to me that there are decades of growth and expansion in front of Simple Modern. At the same time, it feels right to reflect at the close of a chapter in our story. The main question I am asking myself is, “As our company continues to grow, what should never change?”

A picture from our first annual company retreat in 2017

Always Day 1

Over the last 25+ years, Amazon has grown from a garage startup to perhaps the most significant company in the world. As it grew, one of the attitudes that Jeff Bezos consistently championed was a “Day One” mindset. “Day One” thinking acknowledges that although the internet has made a tremendous impact on our lives and our society over the last 30 years, we are still at the very beginning of its story. As Amazon grew, Bezos wanted the focus to lie on the vast possibility ahead instead of how much Amazon had accomplished and grown. When asked what “Day 2” is at Amazon Bezos said this:

“Day 2 is stasis. Followed by irrelevance. Followed by excruciating, painful decline. Followed by death. And that is why it is always Day 1.

I’m interested in the question, how do you fend off Day 2? What are the techniques and tactics? How do you keep the vitality of Day 1, even inside a large organization?”

This way of thinking has helped Amazon stay innovative, agile, and creative even as they have scaled to a behemoth company with almost a million workers.

It is still Day One at Simple Modern. We have come a long way from the plucky startup that we founded 6 years ago, but we have just begun to scratch the surface of the impact that I believe we are destined to make. We started Simple Modern based on the belief that there is a better form of capitalism. We believe that so strongly that our company mission statement is “We Exist to Give Generously.” As we experience a growing company’s changing seasons, my goal is to keep a startup spirit and commitment to generosity central in everything we do.

When I am 80 (if I get that long), what will I remember about the last few years? More than anything else, I will remember the relationships. The singular best part about Simple Modern is being surrounded by people that I deeply respect and enjoy. Being a startup CEO has helped me to grow immensly as a person. I have learned that career success pales compared to relational connection, and I have seen just how many weaknesses I have. I need to be challenged and loved by others who are for me. When I was younger, I thought the goal of leadership was to build organizations. Over time I realized a simple fact – in life, we are all passing through. Every person who works at Simple Modern will someday exit, even me. Organizations are simply containers that we pass through over the course of our life. I believe that what defines great organizations is that they help the people who pass through them flourish. As the chapter turns, I am thankful to have been a part of creating an organization that puts people first.

Here are some questions for refelection on this subject:

“What is an area of my life where I am in a hurry to graduate to the next phase? How is that impacting my ability to learn from and enjoy the experience today?”

“What will I remember about this season of life when I am 80? What are the areas that I am investing my time, money, or effort that will not matter to me when I look back on my life?”

“Where am I experiencing grief from a difficult transition? Who can I process these feelings with?”

“Am I taking regular time to reflect and express gratitude, or am I overly focused on the future?”

“Where am I scared to transition to the next season even though it is time?”

entrepreneurship, mindset

Mistakes are Tuition

Over the course of his 84 year life, Thomas Edison acquired a record 1,093 patents and helped create the movie camera, microphone, the stock ticker, and even an early version of the tattoo gun. Edison famously only slept around 3 hours per night and could exist on such a small amount of sleep because of his frequent catnaps. He was also an exceptional promoter and businessman. His company, General Electric, is one of the oldest and most successful companies in US history.

His crowning achievement was the development of the incandescent light bulb. Over a several-year period, he worked to find an affordable and reliable solution to gas-powered lighting. The primary challenge centered around developing a filament that would be durable but cheap. In total, his team tested more than 6,000 possible materials before finding a solution made from carbonized bamboo. The process was expensive and full of prototypes that did not produce the desire results. However, when asked to reflect on these trials, Edison said:

“I have not failed 10,000 times. I have successfully found 10,000 ways that will not work.”

Edison’s mindset is worth examining. He did not view the thousands of unsuccessful experiments as failures. Instead, he saw them as the stepping stones that eventually led to the successful prototype.

How We Learn

There is a growing body of evidence that we learn most effectively by experimenting and analyzing the results. When we are young, we learn about the world around us by touching and tasting everything. No matter how many times we hear that a stove is hot, we ultimately have to experience the discomfort of being burned to understand. As a parent of two children under 10, I have concluded that good parenting includes allowing your children to fail in non-fatal ways.

In one recent study, researchers in Singapore examined how seventh-grade math students learned. Researchers divided students into a “direct instruction” group and a “productive failure” group. The direct instruction group learned how to work problems through a step by step tutorial from an instructor. In contrast, the productive failure group was allowed to struggle and fail at solving the problem. After allowing the students to attempt several unsuccessful methods of solving the problem, an instructor would help them analyze the failed attempts and find the correct answer. The study culminated with a final exam. The productive failure group significantly outscored the direct instruction group on all problem types. The most successful students were productive failure group participants who now could solve problems through several different approaches. The unsuccessful attempts had laid the mental framework for successful mathematical thinking.

The Cost of Wisdom

What are the implications? It means we don’t retain spoonfed wisdom very well. Instead, our learning correlates to its cost. Several psychological terms describe this tendency, like the sunk-cost fallacyendowment effect, and the Veblen good. One recent US Bureau of Labor Statistics study found that college students who worked a part-time job had an average GPA of 3.13, while nonworking students had an average GPA of 3.04. When you are washing dishes to pay for your classes, you are more motivated to absorb the information. We use the word tuition to describe the cost we pay to acquire wisdom and knowledge. Sometimes tuition is financial, but it can also be time, effort, reputation, or physical health. The more tuition we pay, the more deeply the experience impacts our future thoughts and actions.

At Simple Modern, we are deliberate about empowering teammates to make decisions and learn from the results. Sometimes this doesn’t go well. It could take the form of a new product that fizzles out before launch or a marketing campaign that fails to connect with our customers. Over the years, I have made two different leadership mistakes in these situations:

Mistake 1: Responding with frustration, anger, and disappointment. When I react this way, it expresses disapproval. If done repeatedly over time, this creates an environment of fear. It discourages innovative thinking and experimentation. I have learned a simple lesson about leadership – it’s never helpful to get angry.

Mistake 2: Minimizing the situation. It is equally unhelpful to sweep a disappointment under the rug. This behavior can be motivated by a misguided desire to protect ourselves or others. Unfortunately, it discourages honest assessment and introspection. It can also invalidate the disappointment others are feeling.

I am learning to respond differently to these situations. First, no one enjoys the feeling of disappointment. Give yourself and others empathy and grace. That will create a safe environment where real analysis can happen. After providing some time for introspection and reflection do a postmortem. What went wrong? Why didn’t things go as planned? If we could do this project over again, what decisions would we make differently? What unknown weaknesses did this situation expose? Just as Edison’s thousands of unsuccessful lightbulb filaments made his ultimate triumph possible, these clear-eyed evaluations are the foundation of personal development and growth.

A Million Dollar Mistake

Around the beginning of 2016, Simple Modern was about to launch its first insulated water bottle. We observed that the larger drinkware market lacked premium quality but affordably priced licensed drinkware options. Internally, we believed we could create the ideal solution, so we began the lengthy process of pursuing NCAA licenses while simultaneously launching our branded products. After building several samples, the University of Oklahoma agreed to be our first licensing partner. Shortly after, we had one of the most significant breaks in our company’s history when the retailer Sam’s Club agreed to consider our products. We were incredibly fortunate to show our product to a buyer that shared our vision and excitement. That meeting would set in motion a purchase of several hundred thousand units for retail programs in 2017. As you can imagine, we were ecstatic. Every consumer brand’s goal is to gain customer awareness. This program would be a massive shot in the arm for our new company.

There was a small but gnawing question in the back of my head. “Who is going to buy all of these tumblers?” Throughout the sales process we had been so focused on the product that we had not spent much time evaluating the order size. Everyone agreed that there would be a lot of demand for the product, but we would be launching something brand new. I pushed those thoughts to the back of my mind because there was plenty of other work to be done. We were simultaneously managing rapid growth in our branded business while executing on a complex order for Sam’s Club. In May 2017, our team spent almost two solid weeks unloading containers and loading trucks with over 500,000 NCAA licensed tumblers. In addition, we had discovered a packaging issue that required us to unpack scores of pallets, individually sticker the units, and then re-palletize the products. You can check out a time lapse of that process below.

One of my favorite memories from those days was a night where we loaded trucks until 10 pm and then went to watch a late-night showing of Guardians of the Galaxy 2. The picture below is a panoramic of all the product before we began to ship it out.

The initial sales data looked promising. A few clubs had sold through entire pallets in the first weekend. The program had launched right before Father’s Day, and our item had been a big hit as a gift purchase. It was a real mountain top moment for the company. In the weeks that followed, we realized something less encouraging. Father’s Day weekend was the peak of demand for the entire summer, and it was starting to look like we would not sell through all the two packs during the allotted program time. As the summer drifted towards August, it became evident that we had a problem. The product was great, and it had sold well, but we had shipped Sam’s Club way too many. When a retail program doesn’t perform to the sales plan, the brand leadership and buyer devise a strategy to fix things. In this case, there were tens of thousands of extra two packs that needed a home. During one of the conference calls during this period our buyer said something that has stuck with me when she observed, “Everyone talks about wanting to be a great partner but during situations like this you learn who really values partnership.” We were fortunate to be working with a buyer that was a true partner. Working together we devised a plan, but for it to work we had to make the painful decision to buy back almost $1,000,000 of product. It was the right decision, but company finances would be very tight for most of the next year and a half.

It was disappointing not to sell through all of our products, but the experience was not a failure. It was tuition. We had initially believed growing our brand required us to sell as many units as possible, but we learned that selling an appropriate amount of product is even more critical. Over the last few years, I have seen how learning from that tuition helped us grow into a more effective company. In 2020, we were preparing to ship another licensed order to Sam’s Club when the COVID stay-at-home orders went into effect. We worked quickly with our partners at Sam’s Club to modify the order’s size before it shipped. The result was a great program where everyone won.

When things don’t go well, it creates the perfect environment to grow and learn. We can convert our mistakes into the fuel for our growth. As Henry Ford once said:

The only real mistake is the one from which we learn nothing.

Reflection Questions

What is your most recent disappointing outcome? Did you view it as a failure or tuition?

When have you empowered someone else by reframing a disappointing outcome as an opportunity for growth?

What is an example of failing to use a setback or mistake as tuition in your own life?

Who are the people looking to you for leadership (at home, work, personal life)? How can you apply this principle to responding to their misstakes or missteps?