My mission is to help high-growth startup CEOs, founders, and executives navigate the practical and emotional challenges of building companies and lives they're proud of.
I coach CEOs, founders, and C-Level executives at high-growth startups. Most of my clients are founder-CEOs, but I work with several non-CEO founders, and seveal non-founder C-level executives.
I prefer clients to have at least 10 employees at their company before we begin working together, and I do best once the company has at least what First Round Capital calls “nascent” product-market fit. Almost all of my clients are B2B software companies and are usually venture-backed.
The practical challenges of building a startup have to do with solving problems and learning specific skills, often that you have no experience with (e.g., designing a hiring process that works, managing performance, running great meetings, etc.). Many practical challenges have tried and true best practices that I like to think about a New York Times Cooking recipe—start with the recipe and made adjustments as you please.
The emotional challenges of company building is often overlooked, dismissed as touchy feely, or put in the purgatory of "important, but not urgent." It's the loneliness of being a the top, the dread and anxiety over whether this thing you've poured your soul into will survive, the anger and frustration when things go wrong, and the fights and arguments with co-founders, executives, and employees (and your spouse!). Learning to notice and regulate your emotions is a key part of becoming an effective leader.
I believe it's critical we address both so you can perform at the highest level.
A consultant might offer to come in and build a great hiring process for you. I won't do that. I will help you create one that works. At every step, my goal is to enable you to be a more effective leader, and that means teaching you to fish.
It's dreadfully tempting to think one can publish a manual, curriculum, guidebook, or “one-size fits all” approach to becoming a successful founder or CEO. But since every founder responds to, copes with, manages, and experiences these challenges in such different ways, that’s impossible.
Instead of giving you a book to read on how to ski, I’d rather we strap the skis on, get on the chairlift, and we’ll use any challenge on the way down the mountain as an opportunity to learn and improve. That said, for the readers out there, I periodically update Andy's Coaching Curriculum for Founders with resources under specific headings that may be helpful with certain tasks or functions.
Another way flexibility plays into my approach to coaching is that I can switch between a few different “hats.”
I find that clients love it when I put on “The Founder Hat,” because I’ve curated an extensive library of very specific and useful resources for different scenarios, but I also try to be cautious not to offer advice or problem-solve too soon, as that’s an easy way to end up solving the wrong thing or rob you from the opportunity to learn to self-coach without me—the last thing I want is to foster a dependent relationship.
Peter Drucker was wise when he wrote:
“Executives who do not manage themselves for effectiveness cannot possibly expect to manage their associates and subordinates. Management is largely by example. Executives who do not know how to make themselves effective in their own job and work set the wrong example.”
While it is your responsibility to drive the agenda of our work, I will encourage you over and over to focus on what you can control first instead of trying to control other people. This will mean understanding your thoughts, feelings, and gut instincts (and how they lead to behaviors that work for or against you).
If you aren't managing your own time well, appropriately allocating time between important and non-urgent work and "urgent" sirens like answering every single email, it's unlikely the best use of our time is to try and fix someone else's behavior before first addressing yours.
Startup founders often treat symptoms and overlook root causes. How does this relate to you, the CEO, and your relationship with me? An underperforming employee may “feel better” when you, the CEO, change your 1:1 approach, but if you leave underlying causes untreated, underperformance will become a recurring topic over years of coaching.
Good coaching is care, whether by a professional, CEO, or manager. And care is a four-step process that boosts confidence, agency, and independence. The four steps are:
Apply this process to a patient with a headache: identify symptom (headache) → relieve symptom (take Advil) → diagnose root cause (dehydration) → treatment & prevention plan (drink enough water daily).
Too often in my work as a coach, I notice that care stops at (2) for “Issue A” because CEOs tend to skip (3) and (4) to work on relieving symptoms for “Issue B” once we resolve symptoms of “Issue A.” I may slow things down to fully resolve Issue A before moving to Issue B.
You may not love this at first. To continue with the headache example, many prefer to take a pill and ignore the root cause. Diagnosing and treating the root cause is harder in the short term. It requires effort, while symptom relief feels easy at first but can have costlier long-term consequences. Establishing a habit of drinking enough water daily is harder in the short term than simply taking an Advil for each headache, but stomach bleeding from the pills will be harder in the long term.
To return to business, let’s address an underperforming employee. CEOs often view underperformance as an isolated issue. They might reprimand someone on Slack, vent to a friend, loved one, or coach, fire somebody, give feedback, or help the friendly neighborhood bartender grow their nest egg after work.
Symptom relief isn't "wrong"; it's necessary but not sufficient [4]. Avoiding long-term underperformance demands a deep analysis and treatment of root causes and often requires a multi-part solution. Here’s an example of how a CEO treating the root causes of underperformance:
If we practice this together, and you with your team when in the coach seat, I'm confident you will outperform teams that don’t.