Coaching

Meredith & Laura, Co-Founders @ WATS

Being a co-founder of a startup is hard, time is precious, and sometimes conflicts arise and things get messy. Since we have started working with Josh, we are able to more clearly see and fix challenges that arise, so we can focus on the good stuff. 

Lotti Siniscalco

Partner, Emergence Capital

Over the last six years, I have worked with many coaches, on both personal and professional development. After trying multiple styles of coaching, I knew I needed someone who could lead with profound empathy, while also engaging with me in deep intellectual explorations. Importantly, I was also looking for someone who would openly share their thoughts and opinions. Said in other words, I wanted to work with an opinionated, very smart, empath, and I'm incredibly fortunate to have found Josh.

Kelsey Bishop

Founder & CEO, Candor

I can’t really begin to explain what it feels like to have Josh in these moments of life where things can go in such different directions. And it’s not like having a friend or partner in your corner. Josh knows your inner being - what you’re capable of, what your greatest life desires are, and your deepest fears.

There are few people that actually change the trajectory of your life. And trust me, I don’t say this lightly. Josh has absolutely changed the trajectory of my life. Not just in the obvious sense of starting a business, but in a deeply personal sense. I can live my life as ME today. I’m the most me I ever have been and I don’t know what my life would have looked like if I didn’t start leaning into my deepest desires and facing my biggest fears.

Dan Teran

Co-Founder & Managing Partner, Gutter Capital
Former Founder/CEO, Managed By Q

It is not an exaggeration to say that the weekend program and Josh's coaching through the lens of the enneagram changed my life in a very real way.  Through Josh's teaching of the enneagram I came to understand myself better as well as how I show up in the world to others, and I revisited some of the most critical relationships in my life.  I found myself reaching new levels of understanding of not only important professional relationships, but also my most sacred and longstanding personal relationships.

Heather Hartnett

CEO & General Partner, Human Ventures

20 minutes into my first call with Josh, I asked him to be my coach. I’m very grateful that I followed my gut.

Josh and I worked together as I prepared to raise my second venture capital fund. It's a big junction point given each fund is a 10-year commitment. In that time, Josh supported me through what we affectionately called a “Heather Revolution.” In our sessions, Josh helped me process big questions about who I really am, what I really stand for, and how I can stay true to myself as a woman in an industry predominantly run by men. He helped me discover how to “attract” results instead of just “push hard,” to rest in ways that actually restored me, and to weave my personal and professional life together more seamlessly. He even encouraged me to explore my femininity and find a place for it at work — a wonderful surprise. (I do want to say: Josh coached me on the practical stuff too — workflow management, comms, etc — but all of that fell under the umbrella of a more holistic and personal focus.)

I also attended Josh’s Enneagram retreat, which was game changing. He teaches beautifully, and honestly I think about the Enneagram all the time now. It’s been incredibly useful for understanding my own patterns and in helping me interact more effectively with everyone in my life — my partner, my colleagues, and the founders I support.

In short, Josh was the probably most influential person that I met in 2021 for my personal growth, and I owe him a great deal. I feel ready for the next and most important decade of my professional life, and I feel like I can truly do it as “me.”

Devin Bostick

Founder & CEO, LuckyTruck

As a solo founder running a VC backed company, it’s been difficult to find the right flow between professional life and the rest of my endeavors. Josh really helped me document parts of my identity through his approach via the Enneagram, work through regular journaling, content recommendations to find a better grounding during a period of inherent startup chaos. This created my largest period of personal growth because it allowed me to take a step back and organize who I am and how I want to lead.

I definitely recommend working with Josh as long as you’re willing to be vulnerable about your strengths, weaknesses and where you want to go. Additionally, if you do work with Josh, read some of the content, take notes during each session, read through his content as well and come prepared analytically to get to a deeper part of yourself. Because we’re all difficult, a lot of the sessions are focused around what feels intuitive to one’s personality and how to be the best one can based on one’s tendencies. In a world that likes to pattern match and promote different ideal types - I really like how Josh helped me address the core of my being within the context of my personal and professional journey.

Dean Furbush

Serial CEO

A million years ago I was Chief Economist and Director of Strategic Planning at the Nasdaq Stock Market, and have gone from there to several leadership roles, all of which involved offsites seeking strategic direction, valuable culture, and team-building. Yeah, I've attended a lot of offsites. So it’s with some experience that I can report that Josh is an excellent facilitator.

If you want a ropes course and trust falls, don't use Josh; if you want a formal, corporate strategy session, don’t use Josh; in fact, if you’re a manager who thinks you know ahead of time, any predetermined outcome from the offsite, still not Josh. But if you want a caring and authentic environment in which your leaders are respected and listened to, and thus feel comfortable to learn about and appreciate their different strengths and opportunity areas, and to see in realtime how their differences add value to your organization, Josh is your guy.