Ryan Caldbeck’s User Manual

Introduction:

My name is Ryan Caldbeck. I grew up in Vermont and moved to California for graduate school at Stanford in 2003. I’m married to Kim and I have three kids. Prior to starting the technology company CircleUp in 2011, I worked as a growth equity investor in San Francisco. 

This is a living document. I plan on updating this User Manual as I learn more about myself over time. 

My relationships:

I thrive when working with people that have high integrity and intelligence, who work hard and take pride in their work, and who try to be great teammates. I greatly appreciate those that have a sense of humor, particularly during stressful times. 

I struggle in relationships with those that don’t demonstrate respect for themselves or others. I have little patience for those that lean negative. I like confidence and I am really turned off by arrogance. I am drawn to those who are intellectually curious and like to challenge their own and others’ assumptions.  

I love to work with people who strive to take ownership of their projects and embrace accountability. As CEO I really enjoy letting others own their projects. I tend to give a lot of rope up front and it stays that way unless my trust has been broken. I like to define trust using the following equation: Trust = [Reliability x Credibility x Authenticity]/(Self-Interest). Credibility is “can the person do what they say?” Reliability is “will the person do what they say?” 

My communication style:

I believe strongly in the importance of open, clear and frequent communication. I am very responsive and struggle to be an effective partner to those that aren’t during working hours. I really appreciate the “let me think about it” or “I’m on it” email as opposed to several days of silence. For short questions or semi-synchronous communication I prefer Slack, for longer and asynchronous communication I prefer email. Text is my least preferred medium. If email chains include more than two responses, I tend to want to just talk about the topic live. Sometimes my emails are very short and some perceive them as curt. Please trust that if I have an issue I’ll tell you directly—a brief email is not an indication of anything more than efficiency. I’m comfortable with Zoom, phone calls or in-person meetings, though I find Zoom to be the most mentally taxing of the live communication options. 

I don’t need responses or presentations to be polished. If my input is needed, I generally prefer seeing the output mid-flight and unfinished instead of waiting for a final draft to give comments. 

I believe in addressing problems head on. If Person A comes to me about Person B, I will always push to have Person A & B talk about the issues directly (perhaps with mediation).

Meetings:

I think 1:1s every week, or every other week, are very helpful with direct reports. I also believe in skip levels every quarter. I like to provide direct and clear feedback, and strive to do so in the moment and with examples. When providing immediate feedback is difficult, I aim to not wait until a regularly scheduled meeting. Similarly, I like to receive feedback in the moment and not on delay. More than anything, I just want it to be direct. 

Meetings should have clear agendas and goals. I rarely think recurring meetings are a good idea and will push for clear takeaways and reasons for their continuation. I struggle to believe that meetings larger than 10-12 people are an efficient use of time (I believe in Jeff Bezos’s two pizzas rule). 

If I don’t think it’s productive for me to be in a meeting (i.e. if I’m not adding value or receiving value from being there), I will leave. I encourage others to do the same. If I’m taking a backseat in a meeting, it’s usually because I’m trying to create space for others to step up. 

My frameworks:

I often refer to frameworks I have found useful, including:

Bugs (according to 360s):

• Not celebrating wins as much as I should

• I hate surprises—I’m ok with bad news, but if a goal is going to be missed I want to know as soon as we are aware it will happen, not at a regularly scheduled OKR meeting

• Difficulty saying no to people, particularly teammates

• Possibly too responsive over email and Slack which some find disruptive to their workflow

• Differentiating between the urgent and the important

• Sometimes my questioning comes across as interrogation when I’m trying to learn more about a topic

Features (according to 360s):

• The ability to be transparent, vulnerable and authentic

• Creativity, adaptability, passion and resourcefulness

• Inspiring leadership and empowering teammates 

• Grit and persistence, particularly in the face of great adversity

• Galvanizing stakeholders and attracting terrific talent 

• Not letting perfect be the enemy of good

My support system:

I have worked to build a support system for myself that includes a CEO support group (today that is in part my YPO forum), a management coach and a therapist. I like providing my unedited previous 360 reviews to those that I work with so they can get a sense of what I’m like professionally. I’m also happy to provide references from anyone I’ve ever worked with, including those who didn’t enjoy the experience. I would always prefer people to know my faults up front before electing to work with me. I am most effective when my teammates believe in me or my competition doubts me. 

My lifestyle:

I have tried to create harmony in my life but it is a never-ending quest. I exercise five times a week and always before work. I like to play basketball. I bring my kids to school or pick them up most days. I make it home for dinner at 5pm with my family and am online after they are in bed. I love animals, particularly cows and dogs. I have struggled to unplug during vacations in the past but I’m trying to do much better going forward. I tend to avoid traveling for work apart from when necessary. I am extremely protective of my time and tend to not go to “coffee catch-ups” or networking events. I like doing science experiments with my kids (if you have suggestions I love hearing them). I want my teammates to have a work-life harmony that works for them and I tend to encourage them to unplug on weekends and on vacations. 

I love to read and have a list of my favorite books (and podcasts) here. I occasionally make angel investments (here).