The field of coaching has a ton of variability. Some folks woke up one day and decided to be a coach, others have a Ph.D. in psychology, others are academics, and so on. So when I meet someone interested in working together, they inevitably have a lot of questions. Below, you’ll find a bit of context on me and how I got here followed by a set of the most frequently asked questions and my answers.
I’ll start with a bit on my career before I became an executive coach to startup founders and follow that with a bit on how I went from entrepreneur to coach.
Since 2009, I’ve started four companies. The first one makes me laugh because it was an elaborate homebrewing operation I started at 19 that has evolved to become known as “the brewery” amongst friends and family. The second was a sort of proto-ProductHunt. The third was Mattermark, a business analytics and database company where we grew from $0 - $5M in ARR in 3.5 years. And the fourth was Holloway, a digital book publishing company. I’ve been the CEO and the COO. Across my companies, we raised more than $20M in VC money (not necessarily a good thing). And finally, I wrote a book, The Holloway Guide to Raising Venture Capital.
In 2020, I left Holloway to become a coach. Whenever I asked colleagues what my “superpower” was, they’d say, “listening.” I never thought that could be a career, but as I contemplated what to do in the next chapter of my career, friends and colleagues suggested I explore becoming a coach. Since then, I have studied to become a coach at The Hudson Institute of Coaching through a 9-month training program.
Together, my experience as an entrepreneur and a coach allows me to both coach and advise. My goal as a coach is to help you become more self-aware and use your agency to contribute to the world in a way that aligns with your values. I believe that if you do that, you have a pretty damn good shot at being a successful entrepreneur.
If this and my answers below leave you feeling interested in working together, you can contact me here.
I love working with early-stage founders whose companies are growing quickly. This doesn’t necessarily mean they’ve taken venture funding, but in many cases, the founders I coach have raised a seed or series A round of funding. I prefer to work with founders once they’ve found at least some product-market fit. Almost all of my clients are CEOs. If you’re a non-CEO founder, I will not work with you unless your CEO co-founder is either working with a coach now or has worked with a coach for a significant period of time. I also do not work with co-CEOs or CEO/President or any other co-founder arrangement where there is not a clear CEO.
My maximum is 20 clients at a time, and most of the time I have about ~15 clients.
I don’t coach with a fixed timeline in mind. I have some clients I’ve worked with for more than a year and others who I’ve only worked with for three months. Most clients, however, work with me for 6 months or more.
I also don’t coach with a fixed structure. I recommend thinking of our coaching engagement in three-month sprints where we will meet every other week (~6 sessions). In the first 1-2 sessions, we’ll set some goals for what you’d like to get out of our work together and then spend the following 4-5 sessions working on those goals. In a 7th session, we’ll do a retrospective, look back on the goals, and see if there’s anything you’d like to change about your goals or how we work together—at this point you should be able to unquestionably see progress.
I do not have a fixed system. Each founder brings unique challenges, relationships, and history and I adapt how I work to each client. In my work, I draw upon research and frameworks on how people change, transitions, interpersonal relationships, conflict management, recruiting, management, and much much more.
One good metaphor for how to think about our work together is that coaching is a bit like Google Maps. Huh? Like in Google Maps, you have to understand where you are—where your blue dot is—how you got there, what you like about it and what you don’t. Then, you have to pick a destination. Once we’re clear on the here and the there, we can begin to work on picking a route. This metaphor applies to three-month sprints and inside of individual sessions.