The Funded 2024: OVF’s CEO Summit

Matt Compton

October 2024

Each year OVF convenes the venture-backed CEO founders in our region for an afternoon to work on our collective craft as leaders. This year, we met in September at the beautiful Stoller Family Estates.

At 2023’s event, Scott Roth, CEO of LegitScript and former CEO of Jama, highlighted the importance of personal development for growth company CEOs with the following maxim: If a company is growing at 100% per year, the leader of that company needs to be getting 100% better every year. That got everyone’s attention and inspired our theme for this year: Peak Performance for Leaders. We explored two areas of peak performance: 1) activating the high-performance state of flow for yourself and your teams and 2) traits, habits, and abilities of great leaders.

Flow state is defined as a mental state in which a person is fully immersed in a feeling of energized focus, performing at their absolute top level, and enjoying the process of the activity. Time speeds up and the rest of the world melts away. It is a state of high performance. Many of us have experienced this in sports, music, writing, art or design. It is an incredibly effective and productive state and one of the happiest states a person can experience. The challenge is it often feels haphazard and can be hard to replicate on demand.

We were fortunate to have Dan Quiggle from the Flow Research Collective join us this year. The FRC was founded by Steve Kotler and has developed methodologies for activating flow in individuals and teams in a repeatable and predictable way.

We explored the four pillars of flow: Blockers, Proneness, Triggers, and Cycle.

Blockers include distractions such as phone alerts, lack of clear goals or priorities, and insufficient sleep. Perceived lack of time can be a factor as well. One needs to prioritize chunks of time for flow and come in with the mindset that the activity, task, or challenge may be hard but is achievable.

Most people are most “prone” to flow in the morning when they first wake up. Dan shared a practical approach for best initiating flow first thing in the AM.  Make all logistical decisions the night before and set aside a block of 1-3 hours in the morning to do your very most important work for the day, turn off phones and eliminate all distractions.

There are also several triggers for flow. It may not be possible for all to be present but the more triggers you activate, the easier it will be to enter flow state. These include:

  • A clear goal for the task or activity

  • A mechanism for immediate feedback on the quality of the work

  • The activity should be challenging but not feel impossible

  • Full concentration on the activity

  • High consequence for failure

  • Activity includes aspects of novelty for you

  • Complexity - the task should not be routine or monotonous

  • Some unpredictability in the outcome - success is not a sure thing

In reading this, one can see how flow is often associated with action sports or gaming. With some imagination, you can create many of these triggers each day around your most important work.

With elimination of blockers, setting up an environment that is prone to flow, and enabling as many triggers as possible, you can predictably enter a flow cycle. The cycle is comprised of four parts: Struggle, Release, Flow, Recovery. 

The initial struggle with the task, activity or project is critical to activating flow. So instead of avoiding the struggle, sprint towards it. Grapple with the task for 15 minutes or so and then Release. Step away for a couple minutes with a break. This break should be boring – eg, simple stretching, standing up and staring at the wall, deep breathing, etc. You are not trying to engage in a new activity. Just a quick release to activate your brain into flow state.

After a few minutes, re-engage in the activity and enjoy the Flow! Your inner voice and time disappear, you are absorbed by the activity and your performance and productivity go through the roof.

To consistently create flow state weekly or daily, you must follow flow with a recovery phase. Recovery should be active: exercise, meditation, breath work, nature immersion, cold or heat therapy, etc. Top performing execs often schedule their recovery time just like their flow blocks.  Finally, we need to commit to high quality sleep. 99% of us cannot perform at a high level without 8 hours of high-quality sleep. Accept it and embrace it.  Work first. Recover later, but never skip recovery.

Flow can often be most easily accessed when you first wake up.  One of the more radical ideas we discussed is if you are truly optimizing for flow state, try starting your most important, demanding work within 90 seconds of waking up. This is an extreme idea and is most applicable to individual work, but it prompted us to think about how much we would need to change to construct our morning routines around optimizing for Flow. [I tried experimenting with this in writing this blog, starting immediately after waking up. It felt significantly easier and more enjoyable than staring at a blank page in the late afternoon. See what you think.]

The flow cycle pattern is about being intentional with your time and energy. The goal is to either be flowing at optimum performance levels or actively recovering. Don’t get caught in the gray zone like many people do, grinding out endless hours of medium to low quality work with no time for recovery or the activities and people you love. We also explore three traits, abilities and habits of great leaders including Gratitude, EQ (Emotional Intelligence), and the Kitchen Cabinet.

How lucky are we to pursue our visions and goals with support from incredibly talented peers and employees. We thought about identifying two people in our personal life and two in our professional life who have been kind, generous, or helpful to us. Our facilitator Dan Quiggle challenged us to go out and express our gratitude that same day. How about you? Is there someone you would like to thank today?

EQ may be the most important trait of a great leader, especially with respect to recruiting and retaining talent and leading through challenging events such as RIFs or bad quarters. Talent tends to follow leaders who have high self-awareness and the ability to think about a situation from another person’s perspective. EQ is a great trust builder. People will follow leaders through tough times when there is a strong sense of trust.

Finally, we worked on the concept of the Kitchen Cabinet. Leaders who prioritize their development actively surround themselves with a diverse set of peers and mentors who are engaged in their life - i.e., their kitchen cabinet. Try this out: make a list of five or so people whom you admire and who are not in your immediate family, nor work in the same organization as you. Reach out to them for a 30 min meeting. You might be surprised how many people would love to work with you on this.  Also, consider how you might contribute to someone else’s kitchen cabinet.

It was a very thought-provoking and informative day as we also discussed the fallacy of Work-Life balance.  CEO founders have very demanding jobs and their companies and employees are a huge part of their lives.  A more achievable and perhaps more rewarding idea is Work-Life Presence. When you are working, be fully engaged and effective as possible. When recovering, commit fully to the rest and recovery. When with friends and family, set aside the work and be fully present.

We finished on the concept of a leadership legacy statement. We wrote down what we hoped loved ones would say about us once we were gone. This was a powerful concept and quickly brought the most important things in one’s life front and center.

Founders have incredibly unique, demanding, and rewarding jobs. We at OVF thank you for all you do and hope you take the time to learn, invest in yourself, and build the career and life you want to live.

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