Remind yourself even if you fail at this one thing, you are a kind, honest, high integrity person that does everything in your control to do the right thing. This matters a lot more to meaning, purpose, and happiness than professional ups and downs, and should help reduce any guilt that you may let someone else down. I found it helpful to ask myself: is ruminating on this guilt helping me succeed, or will letting it go help me succeed?

The Fear of Failure is one of the most common restraints that holds people back from pursuing great ideas. Imagine if we could become totally free from the fear of failure. Imagine what we could then manifest and create. In this interview series, we are talking to leaders who can share stories and insights from their experience about “Becoming Free From the Fear of Failure.” As a part of this series, I had the distinct pleasure of interviewing Ryan Renteria.

Ryan is a chief executive coach who helps CEOs/founders maximize professional & personal growth and performance through his firm Dominate Your Fate. Previously he spent 9 seasons using data science to advise Indiana Pacers front office executives on trades, draft picks, and free agents, and the coaching staff on opponents and game strategies. Prior to this Ryan spent 9 years in finance at Goldman Sachs and two hedge funds, Balyasny and Karsch, where he was a partner and managing director of consumer investments. Ryan earned a BA in economics from Stanford University with awards of highest honors for academic excellence from Stanford’s Latino community.

Thank you so much for joining us! Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’?

I’m excited to kick this off, thanks! I was raised in a lower-middle class household in Sacramento by a single mom who worked as a Kindergarten teacher. I went to a public high school with awful test scores, a 50%+ dropout rate, and metal detectors from all the violence on campus. Thankfully I landed a Hail Mary as the first person from my high school in 20+ years to get into Stanford.

I was woefully unprepared for the rigors of Stanford and nearly dropped out after getting some C’s & D’s early on. Having turning things around, I graduated in 2001 as the dotcom bubble was bursting and headed to Wall Street to work at Goldman Sachs. Then I worked at 2 hedge funds and was a partner and managing director of consumer investments. After about a decade-long good run, I walked into my boss’ office and told him I had decided to leave Wall Street to focus on volunteering with kids.

Spending 2 years volunteering most days at 5 children’s charities focused on cancer, abuse, and disabilities was very spiritually and emotionally fulfilling, but I was ready for the next big professional challenge. I wanted to pursue a dream to work for an NBA team and felt that analytics was my best shot. I learned how to code at a basic level, built my own algorithms for evaluating basketball players in different leagues, and presented to several NBA owners/GMs in meetings I landed through contacts or cold cover letters. I agreed to become a Moneyball data science advisor to the Indiana Pacers where I worked with Presidents/GMs on personnel and the coaches on game strategies for 9 seasons.

Over those 18 years on Wall Street and with the Pacers, I studied a lot of executives and literature on what makes great leaders and coaches. It’s vital to understand the traits of a great CEO when you’re in the investing business and must choose which CEOs to back. I also saw a wide range of styles for how to lead and motivate a team of high achievers in my work with different fund managers, and with NBA Presidents/GMs, coaches, and players. I took all that experience and research and developed a proprietary process for high-performance coaching. I help CEOs/founders maximize growth and create tremendously rewarding cultures for their talented employees.

Can you share with us the most interesting story from your career? Can you tell us what lessons or ‘take aways’ you learned from that?

In my first year of advising the Pacers, we faced the Knicks in the second round of the playoffs. Their star Carmelo Anthony was such a versatile scorer. He could beat you off the dribble, nail the pull-up jumper or take you down low in the post. We’re at the morning shootaround at Madison Square Garden & head coach Frank Vogel calls me over to ask questions about my scouting report on Carmelo. Then he calls over Paul George, who will be guarding Melo that night, and says “Renteria has some fascinating analysis of Melo’s post-up tendencies to share. You may want to take them into consideration when you’re guarding him in the post tonight.” That night in the stands I see Paul guarding Melo in the post and I get this huge burst of meaning & purpose in seeing my contributions matter. We went on to win the game and series, and even though I was just a tiny part of it, Frank made me feel so incredibly valued.

I learned a lot of lessons in leadership from Frank that influence what I teach CEOs. First, he had the humility to ask me open-ended questions, truly listen to what one tool in the toolbox (analytics) was saying and incorporate that information. Frank has vastly superior basketball knowledge so he could have interrupted me or ignored me, but he didn’t. Second, he showed me the power of giving your teammate a highly specific compliment, especially in front of others, which made me feel purpose and loyal to the team. Lastly, he showed his increasing trust in me. Next preseason we’re in Asia playing the Rockets, some of the players ask me if they can get analysis directly from me on who they’re guarding & Frank says, “absolutely that’s OK, I trust you.” I learned when a leader says he trusts you and shows it by giving you even more responsibility and autonomy to take ownership, it creates a tremendous feeling of loyalty.

You are a successful leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

I have an acronym for the 3 most important character traits to success, and that is RED. This stands for Research, Execution and Differentiation.

Research: over 18 years I voraciously consumed the best books, academic papers & podcasts on important leadership topics (communication, culture, hiring/developing/retaining talent, and decision-making). This research helped me develop evidenced-based practices to successfully coach CEOs.

Execution: leaders must execute swiftly with conviction by developing an excellent decision-making process. Three examples that helped me the most: 1) becoming a student of the cognitive biases that wreck our decisions, 2) reviewing checklists of top lessons from past mistakes before committing to decisions, and 3) conducting pre-mortems to lower the odds of failure. Through painful lessons from my own mistakes, I learned to dispassionately determine whether a roadblock is a mistake in the process/plan (so we must quickly adapt!), or an unlucky outcome to persevere through with conviction.

Differentiation: I always try to emphasize what is unique about me. Most leaders understand the importance of doing this with their product. Fewer realize how vital it is to differentiate your leadership style to attract and retain A-players. Many leaders run a micro-managing, pressure-cooker culture high in yelling and low in retention. Those who differentiate their leadership styles to emphasize trust, empowerment, and great communication create loyalty among A-players.

Ok, thank you for all that. Now let’s shift to the main focus of this interview. We would like to explore and flesh out the concept of becoming free from failure. Let’s zoom in a bit. From your experience, why exactly are people so afraid of failure? Why is failure so frightening to us?

Failure is frightening to us for several reasons. First, we mistakenly tie our professional outcomes to our feelings of self-worth. So, if we have a failed professional outcome, we may feel worthless. This undervalues our valiant effort, and our process that may have suffered bad luck. It also discounts what matters much more, that we are honest, kind, high-integrity people trying our best to do the right thing. Second, our ego can take a painful hit if others find out that we failed, especially in a very public way. Lastly, we may feel guilty that we disappointed our parents’ expectations of us or let down our partners and kids by not providing them with an even better life.

What are the downsides of being afraid of failure? How can it limit people?

Fear of failure paralyzes our decision-making process and hinders our creativity. We won’t pursue potentially great ideas and amazing opportunities. We’ll fail to take calculated risks and default to the safest and least innovative choices. We’ll fail even more by not maximizing our professional and personal growth and therefore not achieving purpose, meaning, and our higher-level needs per Maslow. This ultimately leads to agonizing regrets throughout life.

In contrast, can you help articulate a few ways how becoming free from the free of failure can help improve our lives?

Our overall well-being and mental health skyrockets because we aren’t constantly in fear. Removing these mental roadblocks allows our productivity to soar, decision-making to improve, and creativity to flourish. We raise the ceilings of what we and our teams can achieve because we’ve opened our opportunity set to more innovative ideas and higher upside opportunities. We achieve peace knowing, no matter the outcome, we’ve given it our all and left nothing on the field.

We would love to hear your story about your experience dealing with failure. Would you be able to share a story about that with us?

My first trimester at Stanford was a complete failure. I entered Stanford with far inferior academic skills to my peers who had gone to better high schools. I started working on my first history paper 3 weeks before the deadline, revised a lot of drafts, and had my stepdad and high school English teacher review it before I turned it in. My TA read it and wrote at the top, in dark red ink and all caps, “did you slop this out the night before?” That same week I got a D on my first calculus exam.

Despite all the hard work I was putting in, I felt completely worthless because of the results. It was a downward snowball because the constant ruminating made it even harder to focus on my studies and steps to improve my grades. I considered dropping out before Stanford would force me out, because I might feel less embarrassed publicly if I made up some reason why I chose to leave on my own terms (yeah right!). If I stayed, I thought about taking easier classes to lower the odds they’d force me out. The most overwhelming emotion was tremendous guilt that my mom had sacrificed so much to get me here and I was letting her down.

How did you rebound and recover after that? What did you learn from this whole episode? What advice would you give to others based on that story?

I finally got so fed up with the situation I just said forget this! What’s the worst that can happen if I give it my all and fail? If I don’t give it my all, I imagine the lifelong regrets of “what could have been” will be worse. This mindset set the stage for things to turn around because I freed up a lot of mental space taken up by fear. I started to think creatively about how I could work with TA’s & conduct my own research to improve my fundamental skills. I made smarter decisions about how to allocate my study time, which became a lot more productive. I trusted that my process of hard work & research would eventually pay off in the results.

The ultimate test would come during the third trimester of my freshman year. I had poured my heart and soul into improving my skills and preparing for my final calculus exam. I walked in feeling quite confident. When I walked out, I felt shattered. It was so hard, I felt like I bombed it, and this would be the final nail in the coffin. A few days later when I went to pick up the exam from my TA he said, “you got a 32 out of 100.” I was about to implode when he said, “We made the test so hard that 32 was a great score compared to the others. On the grading curve you got a B+.”

This was one of the most pivotal moments of my life. I learned not to care so much about what others may think, that powering through fear leads to clearer thinking and higher odds of success, and to trust that a strong process will eventually lead to good outcomes. Those are the 3 things I would advise folks to consider.

Fantastic. Here is the main question of our interview. In your opinion, what are 5 steps that everyone can take to become free from the fear of failure”? Please share a story or an example for each.

First, find a piece of paper and write down these questions and your answers to them. What’s the worst that can happen? Will you survive if it happens? In the end, you will probably be OK! So what if some people think less of you? They’ll think about it for a few moments and then move on to their own challenges. Once you’ve accepted that the worst-case scenario won’t destroy you, then you can start asking things like, “am I catastrophizing? What evidence do I have that this bad scenario will occur? Is there a middle ground outcome that has higher odds of playing out?” Re-read your answers to those questions every day because it takes a lot of repetition to become engrained in your subconscious, mental muscle memory, and actions. This process helped me continue to make investments a lot longer than I imagined.

Second, I’d consider conducting a pre-mortem, also known as a negative visualization. Picture yourself in the future having failed at this. What are the most likely reasons you failed? What adjustments can you plan to make if those risk factors begin to emerge? What other steps can you take now to lower the odds that those risk factors come to fruition? Completing this negative visualization process should reduce your fear and aid your confidence because you’re more prepared for various risk factors. It certainly helped me feel in triple threat position and able to quickly adapt as new information emerged on my investments.

Third, conduct an extensive research process to master the challenge causing you this fear. Then remind yourself you have done everything in your control to maximize the odds of success. That should help reduce your fear of failure knowing if you have a bad outcome, it will be largely out of your control, you’ll have no regrets, and you will have left nothing on the field. For example, I had a 20-step research process for evaluating potential investments. Let’s say I thought if the bullish scenario came true, I would make 30% and if the bearish scenario came true, I would lose 10%. That’s a good reward-to-risk (3-to-1). Assume I was intellectually honest in laying out all the upside factors & risk factors. If one of the risks I identified came true, the stock went down 10% & I sold it as a failed investment, of course the outcome would be painful. However, I’d have no regrets or fears making similar investments in the future knowing I handled what was in my control (my process) and that process will allow me to succeed more than fail over time.

Fourth, remind yourself even if you fail at this one thing, you are a kind, honest, high integrity person that does everything in your control to do the right thing. This matters a lot more to meaning, purpose, and happiness than professional ups and downs, and should help reduce any guilt that you may let someone else down. I found it helpful to ask myself: is ruminating on this guilt helping me succeed, or will letting it go help me succeed?

Fifth, review lessons from your past mistakes before making any future decisions. Then remind yourself of this great quote from Thomas Jefferson: “How much pain they have cost us, the evils which have never happened.” Several times after investment mistakes I’d extrapolate this trend into the future, fearing I would repeat those mistakes and ultimately fail as an investor. Having a systematic process such as a lessons checklist to avoid repeating those mistakes, and this quote to remind oneself not to make catastrophe extrapolations, can help you quite a lot.

See my 5 Things video here.

The famous Greek philosopher Aristotle once said, “It is possible to fail in many ways…while to succeed is possible only in one way.” Based on your experience, have you found this quote to be true? What do you think Aristotle really meant?

I believe Aristotle meant that you’ll make a lot of mistakes and face many roadblocks along the way, but you should continue to adapt and persevere until you succeed. I have absolutely found this to be true. Some may argue he’s also implying that there is only one way to truly succeed. If that means powering through fear, executing a strong research process, and doing everything in your control to maximize the odds of success and growth, then I would agree that’s the way!

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. 🙂

Assume positive intent. Do referees purposefully try to rig calls against your team, or are they trying their best and simply make some honest mistakes? Are people who cut you off in traffic intending to be a jerk to gain a 2-second advantage in driving time, or did they accidentally not see you because they’re distracted thinking about an important family issue? The answers should be obvious, and you should consider assuming more positive intent, particularly in more important areas of life than watching a game or driving. Once you internalize that most people are kind folks who try to do the right thing, your behavior will change for the better. You’ll show more kindness and empathy. You’re more likely to help others in need. You will act with even higher integrity. If we could assume more positive intent, the world would have more love and peace, and less conflict and gridlock.

We are blessed that some very prominent leaders read this column. Is there a person in the world, or in the US, with whom you would love to have a private breakfast or lunch, and why? He or she might just see this, especially if we tag them 🙂

I’d choose Tim Ferriss because he’s such a kindred spirit. His philosophies on productivity, personal growth, and creating professional flexibility to leave room for personal interests have shaped my own life and views. I admire his courage to power through fear of failure when conducting all these experiments on himself. He’s also conversed with world-class experts on virtually every topic, so he knows the 80/20 best practices to succeed in so many different areas of life.

How can our readers further follow your work online?

Readers can follow me on LinkedIn (

This was very inspiring. Thank you so much for the time you spent on this. We wish you only continued success.

Thank you for everything, and to everyone’s success!


  • Savio P. Clemente

    TEDx Speaker, Media Journalist, Board Certified Wellness Coach, Best-Selling Author & Cancer Survivor

    Savio P. Clemente, TEDx speaker and Stage 3 cancer survivor, infuses transformative insights into every article. His journey battling cancer fuels a mission to empower survivors and industry leaders towards living a truly healthy, wealthy, and wise lifestyle. As a Board-Certified Wellness Coach (NBC-HWC, ACC), Savio guides readers to embrace self-discovery and rewrite narratives by loving their inner stranger, as outlined in his acclaimed TEDx talk: "7 Minutes to Wellness: How to Love Your Inner Stranger." Through his best-selling book and impactful work as a media journalist — covering inspirational stories of resilience and exploring wellness trends — Savio has collaborated with notable celebrities and TV personalities, bringing his insights to diverse audiences and touching countless lives. His philosophy, "to know thyself is to heal thyself," resonates in every piece.