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.
My clients are mostly founding CEOs of high-growth startups. I’m also comfortable with non-CEO founders and C-Level executives.
I prefer clients to have at least ten employees and 3+ direct reports before we start working together. Client companies usually have $1M+ in revenue (up to $100M+), are mostly B2B software companies, and are usually venture-backed. Most are in San Francisco or New York City, but I coach over Zoom or phone, so as long as clients can work reasonable hours in EST, location isn’t an issue.
I’m interested in building a long-term relationship with my clients, as I’ve worked with many for 3+ years.
While I don’t assign homework or required reading, I invest time and effort into curating specific helpful resources. Clients willing to read get more out of our work than those who don’t.
Clients must be willing to pay my rates. There are more affordable coaches, but I’m confident my clients feel the money is well spent.
I spend 100+ hours a year studying a range of disciplines—couples therapy, philosophy, management theory, history, psychotherapy, and more to be the best coach and advisor to my clients. Many people are experts in one domain or “literature” (e.g. “couples therapy literature” or “leadership literature”), but few management experts draw on couples therapists’ wisdom. Relationships between co-founders and executives have similar failure modes as marriages.
I maintain a Notion database of 1,500+ excerpts, articles, books, podcasts, mental models, and more that I’ve collected and tagged over time to (1) develop as a coach and (2) recommend items to my clients at the right moments. I’ve compiled some of these resources into reading lists here.
While the categories of skills or challenges founders and executives face seem endless, I find they fit into two buckets: practical and emotional.
Building a startup involves solving problems and learning specific skills often unfamiliar to you (e.g., designing a hiring process, managing performance, running meetings). Many challenges have best practices I think of as a New York Times Cooking recipe—start with the recipe and adjust (more or less salt? more or less founder mode?).
The emotional challenges of company building are often overlooked, dismissed as touchy-feely, or put in the purgatory of "important, but not urgent." It's the loneliness of being at 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, employees, and your spouse. Learning to notice and regulate your emotions is key to becoming an effective leader.
It's critical we address both so you can perform at your best.
While addressing these challenges is crucial, my role is not to solve your problems, but to guide you in finding your own solutions.
As a coach, my job is to help you identify the root causes of problems so you can address them. I’m not here to solve your problems. At some point in our work together, you’ll identify a problem you’d like someone to solve or help solve. I won’t be that person. I can show you what a great hiring or sales process looks like, but you have to build it (or work with a consultant) yourself.
My goal is to enable you to be a more effective leader, and that means teaching you to fish. I won't consult for you, and Idon't believe in a one-size-fits-all approach to coaching.
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 differently, that’s impossible.
Instead of giving you a book on skiing, I’d rather we strap on the skis, get on the chairlift, and use any challenges on the way down as learning opportunities. For readers, I periodically update Andy’s Coaching Curriculum for Founders with resources under specific headings that may help with certain tasks or functions.
Flexibility in my coaching approach allows me to switch between different “hats.”
Clients love when I put on “The Founder Hat” because I’ve curated an extensive library of specific resources for different scenarios, but I try to avoid offering advice or problem-solve too soon, as that’s an easy way to end up solving the wrong thing or rob you of the opportunity to learn to self-coach without me—the last thing I want is to foster a dependent relationship.
This flexible approach allows me to adapt to your needs, but it's important to note that there's one consistent emphasis in my coaching.
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’s your responsibility to drive our agenda, I’ll encourage you to focus on what you can control first instead of trying to control others. This means understanding your thoughts, feelings, and gut instincts (and how they lead to behaviors that work for or against you).
If you're not managing your time well, balancing important and non-urgent work with "urgent" sirens like answering every email, it's unlikely the best use of your time is to fix someone else's behavior before 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” with a changed 1:1 approach, but if underlying causes are untreated, underperformance will recur over years of coaching.
Good coaching is care, whether by a professional, CEO, or manager. Care is a four-step process that boosts confidence, agency, and independence. The four steps are:
Apply this process to a headache patient: identify symptom (headache) → relieve symptom (take Advil) → diagnose root cause (dehydration) → treatment & prevention plan (drink enough water daily).
In my coaching work, I notice that care stops at (2) for “Issue A” because CEOs skip (3) and (4) to relieve 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. Many prefer to take a pill and ignore the root cause of a headache. Diagnosing and treating the root cause is harder short-term. It requires effort, while symptom relief feels easy but can have costlier long-termconsequences. Establishing a habit of drinking enough water daily is harder short-term than taking an Advil for each headache, but stomach bleeding from the pills will be harder long-term.
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, often requiring a multi-part solution. Here's an example of a CEO addressing the root causes of underperformance:
If we practice together and you with your team in the coach seat, I’m confident you’ll outperform teams that don’t.
My coaching approach helps you become a more effective leader by addressing the practical and emotional challenges of building a high-growth startup. By focusing on root causes, preventing re-injury, and emphasizing self-management, we'll develop sustainable solutions beyond quick fixes.
There's no one-size-fits-all approach to becoming a successful founder or CEO. Our work will be tailored to your unique situation, drawing from a wealth of resources and experiences while focusing on your growth and independence.
As we navigate your role, my goal is to help you build a successful company and a life you're proud of. By combining practical skills with emotional intelligence, you'll be better equipped to lead your team, make tough decisions, and overcome the challenges of a high-growth startup.
Cheers,
Andy