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.

Dan Povitsky

Co-Founder @ Vine Ventures

I have had the pleasure and benefit of working with Josh for several years. His coaching has meaningfully accelerated my growth as a leader. Josh is phenomenal at helping me better understand critical situations, deconstruct them to first principle truths, and arrive at solutions. Most importantly, his approach scales beyond our 1x1 sessions. He leaves me with valuable frameworks that I am able to reapply and align to current and future situations. I have recommended Josh to founders inside and out of our portfolio at Vine and folks always come back with high praise for his work. If you are interested in leveling up as a leader, problem solver, decision maker, and whatever else your organization requires, you should definitely work with Josh.

Heather Hartnett

Co-Founder & CEO @ Human Ventures

Josh and I worked together as I wound down Human’s first fund and prepared to raise its second. In that time, Josh supported me through what we affectionately called a “revolution of selfhood.” Our sessions were a place that I could process big questions about who I really am, what I want to stand for, and how to stay true to myself as a woman in VC. He helped me discover how to “attract” results instead of just push, to rest in ways that actually restore 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. 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.

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.

Dan Teran

Co-Founder & Managing Partner @ Gutter Capital

I first met Josh several years ago, and in that time he has grown into a close personal friend and trusted advisor.  I have worked with many professional development coaches in my career as an entrepreneur, and I highly recommend Josh for anyone looking to take their own growth to the next level. 

Josh is unique in his ability to meet people where they are, and while I don't think he would bill himself as a performance coach, in my experience my professional performance improved through better understanding myself and others.  To this day I think about my work with Josh at least on a weekly basis as various interactions come up inside and outside of work, and I'm quick to share what I've learned about the enneagram with others.  Again, if you have a chance to work with Josh you should do it!  It just might change your life :)

Kelsey Bishop

Founder & CEO @ Candor

Josh’s method of asking the right questions and really listening is what sets him apart. I could be mulling over the same questions for days, but after a session with Josh, I feel like I’m able to dissect the problem with new eyes. I think it’s a mix of thoughtfulness and perceptiveness that allows him to see things clearly. Most of the time, he’ll start with questions and maybe share anecdotes from authors or poets. It feels like he’s with you on the journey and open to exploring, without ever rushing your process or giving up the answer.

That’s one of the coolest things about working with Josh - just when you’re at the end of your string, or you feel like you’ve pushed hard enough, he can ask the right question or reframe your perspective in a really profound way.

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. Having Josh in this moment, I knew I couldn’t back down even though I was scared shitless of failing. I think part of me needed the accountability, but part of me also knew what he saw in me and through all the doubts, I started to see it too.

Josh has this incredible way of being able to articulate his perception of you. He does it in a subtle way, but I feel like my self awareness has increased a lot because of how Josh can perceive my blind spots and share them in a way that’s not scary.

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.

If you are thinking about working with Josh, I’m not really sure why you’re still thinking about it. As a founder, you will face some of the most difficult situations in your life and that’s very fucking cool, IF you have a partner in that. Josh fills a role that a co-founder, investor, or even my boyfriend would never fit - he’s a supporter that sees all of me, holds me accountable, and will ride the wave of every journey I’m on.

Praveen Chekuri

Co-Founder & Co-CEO @ Ascend

As a second-time founder & manager of a cross-functional team, I've had to navigate a myriad of challenges, both internal & external. Josh's insights, guidance, and ability to ask very fundamental questions have helped me approach complex business & people problems with confidence. Josh's approach of combining practical strategies & frameworks with a deep understanding of people dynamics has transformed me as a leader, and beyond. 

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 person of inherent startup chaos. This created my largest period of personal growth because it allowed me to take a step back and organized 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.

Andrew Wynn

Co-Founder & Co-CEO @ Ascend

I was introduced to Josh by a friend despite having just finished working with a professional coach provided by my company. Josh, however, is far more than a professional coach. His holistic style goes much deeper than any "normal" coaching, not "just" working through specific, tactical issues, but getting at the root of your personhood and how it informs your relationship with the world. Josh is a kind, caring, and good-hearted person who is truly motivated and driven by helping and watching you succeed and grow into yourself. I recommend Josh without reservation and hope that you can have a similarly positive experience as I did. 

Meredith & Laura, Co-Founders @ WATS

Josh has helped us as co-founders to identify our individual values and how we can more productively use them to maximize our working relationship. 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. It’s still early for us in this journey, but we’re beginning to focus on the source of the challenges that arise, so we can work to keep conflicts from bubbling up in the first place.

Working with Josh is helping us to make sense of our personal triggers and conflict resolution preferences, which delivers impacts and benefits even outside of our founder relationship.

Aaron & Jeremy

Co-Founders @ Delta Lima

We started the session calling each other assholes, and we ended up virtually hugging each other. Highly recommend.

Dean Furbush

Serial CEO: FreshDirect, Ingage, Kitchen to Kitchen

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.

Josh facilitated a team-building workshop to help us clarify our organization’s purpose and values. He first taught us the Enneagram — it was fascinating to watch team members come alive as they recognized themselves in Josh's almost theatrical re-enactments. His presentation sparked meaningful sharing, which included everyone, and which set the stage for an exploration towards the values we came to see were precisely at the core of where we want to work. I   watched our team members invent and start using the Purpose and Values right in front of me — in many cases eschewing my preconceptions of where we should go. The depth and heart that I watched my teammates exhibit during the exploration were a privilege to be part of; and I blame Josh. He‘s an articulate facilitator, who values silence, pauses in between viewpoint expressions, and listening above gabbing. His listening, and our listening, means that the room (where it happens) becomes a creative engine inside of which each of us feels comfortable and valued. Can you tell? I recommend Josh.

Nicola Fleischer

Co-Founder & Executive Director @ edwell

I joined this retreat to learn more about myself, my actions and reactions, and how I relate to my partner and family. I also came seeking authentic connection and community with others as we begin to emerge from our sheltered pandemic lifestyle, and I found just that. The weekend gave me a richer understanding of my enneagram type— or types, really— and I left more deeply at peace with both the strengths and the challenges of my unique nature. I’m clearer on who I am and how I can shift my attention towards the inner wisdom I have been spending so much time trying to find outside of myself instead.

Malte Kramer

Founder of Luxury Presence and author of Play for Something 

Josh is an incredible teacher, and it is clear that he has spent years acquiring deep knowledge. Every teaching moment came with stories from his own life that really brought the Enneagram to life. Josh managed to create a safe space in which I felt encouraged to dive beyond the surface and reflect and share who I am and who I might want to become. I highly recommend Josh as a teacher and the Enneagram as a framework to anyone looking to explore on a deep level who they are.

Carolyn Farley

Partner @ Arborview Capital

Josh is a gentle, yet firm teacher. He fosters mutual respect and rigorous honesty, which enables deeper learning. Within our group, individuals had varying degrees of experience with introspection. Josh seamlessly brought the group together and met each member at his/her level. I highly recommend the Enneagram and Josh as a facilitator.

Alexander Bisignano

Founder & CEO @ Phosphorus

Josh presented the Enneagram to our team at a team-building happy hour. It was engaging and had an immediate impact on our ability to work together smoothly — a few of our teammates had profound "aha" moments that softened how they relate to others on the team, and it gave each of us a fresh lens to see our teammates with empathy. In the days following Josh's presentation, the office was abuzz with new interpersonal insights, and the few people that couldn't make it wished that he could come back and do the whole thing again! As a CEO, I definitely recommend the Enneagram as a team building framework and Josh as a teacher and facilitator.

Heather Hartnett

Co-Founder & General Partner @ Human Ventures

In addition to working with Josh as my coach, I also attended his Enneagram retreat, which was remarkable. I think about the Enneagram all the time now, and I feel it’s an incredible tool for founders, or really anyone. 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.

Brian Rook

Director of Information Technology @ Quanta 

I have studied and applied the Enneagram for over ten years. During this time I have attended several extended, in-depth classes on understanding and applying the Enneagram. After attending Josh’s three day retreat I gained a deeper understanding in this timeframe than all my previous training combined. The material was clearly presented, the content was rich, but overwhelmingly the value of the class – and what stood apart from all my other training – was Josh’s thorough ability to clearly and concisely distill complex information into easily digestible pieces. It was remarkable. The class was extremely well structured and facilitated deep, meaningful dialogue amongst everyone.

Amit Mukherjee

Operating Partner @ Village Global
Founder & Managing Partner @ ChainForest

Josh I just want to express my appreciation for this workshop. It was just amazing. Your presence and centeredness... we can see how you check in with yourself before you communicate, and  the level of calmness that it caused in me as I was observing and following you. Having studied the Enneagram, I’ve never heard anyone talk about it with so much clarity and eloquence, like how you could dive into the history, pull it back up in the space of a minute or two, the language you put together around scaffolding, it seems like it’s unique to you and it’s beautifully, beautifully done.

Dan Teran

Co-Founder & General Partner @ Gutter Capital

Josh’s Enneagram class blew my mind. I want everyone I work with to know this tool. If you are a start up founder, a leader of any organization, or a human in any other context, you should know this tool. And you should learn it from Josh.