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BONUS EPISODE: The CEO Whisperer In Action (w/ Executive Coach Jason Gore)

BONUS EPISODE: The CEO Whisperer In Action (w/ Executive Coach Jason Gore)
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At the end of his interview, as the conversation was coming to a close, executive coach Jason Gore tossed out one final question for Louis:

“What’s it like being coached?”

His answer, and a full-blown guest-host reversal, on this week’s bonus episode.

(And if you haven’t, check out Jason’s full episode of The Startup Stack here.)

This Week’s Guest

Jason Gore headshot

Jason Gore

Managing Partner & Executive Coach @ Neuberg Gore

Jason Gore is half of the founding team of Neuberg, Gore & Associates, an executive coaching firm that supports startup CEOs in Boulder, SF, NYC and LA.


The Startup Stack’s Host
This image has an empty alt attribute; its file name is louis-1024x1002.png

Louis Beryl

CEO, Co-Founder of Rocketplace

Rocketplace is a curated marketplace of high quality professional service providers. A 3x founder, investor, and board member, Louis began his tech career as a partner at Andreessen Horowitz. When he’s not working or podcasting, Louis enjoys cooking for his family. His pizza, he’d like you to know, is incredible. 


Full Episode Transcript

Louis Beryl: Hi! It’s Louis Beryl, again. Welcome to a special bonus episode of “The Startup Stack”. A quick refresh this week we had on Jason Gore, executive coach and entrepreneur and founder of Neuberg Gore. I was wrapping up after an amazing full 30 minute conversation about coaching and business when seconds from finishing the session, Jason asked. 

Jason Gore: Wait wait Louis, You can’t leave this without talking about your experience with coaching.

Louis Beryl: So here’s my answer. Plus, more insights from Jason. Enjoy!

Louis Beryl: In my experience with coaching, it’s so funny because you were talking earlier about what makes a good client. And I said, to quickly summarize, was like, you know, maybe what makes a good client is someone who wants coaching, you know? But I think if I’m very honest with myself, I think when I first met you and Brian, I’m not sure I wanted coaching. And, you know, I say that with the giant caveat of I do want to be a great CEO. And I also recognize that in order to be great at anything, you have to constantly work at it. And so, I think I did bring that mindset of obviously I’m failing at something and how do I keep up leveling my game and becoming a better leader, a better a better co-founder, a better executive. But, you know, I think I was probably reluctant to do the idea of coaching at first. And I think what I found, it’s a combination of listening and challenging that I found so valuable.  I found that for me, having a coach, that’s a really good listener that is able to build a relationship. The fabric of that relationship starts understanding the full context of the company, the product, the challenges, the investors, the other team members. It’s not just one meeting; this relationship has been built over time. So they have good listeners and they understand what’s going on. As you bring up challenges that you’re having, things that you’re failing at, things that are frustrating you. They are good at challenging you directly to think about how to solve those and maybe the things that you’re doing wrong or blind spots that you have. I found that incredibly valuable. And I think the perspective that a coach can bring is really different from almost all of the relationships, because that’s hard. It’s hard for another executive in your company to bring that. It’s hard for an investor to bring that perspective. Yeah. So ultimately, I think it was great for me.

Jason Gore: I think that a CEO can find other thought partners, other CEOs, other people outside of the system. Right. And they could find people that can walk them through some decisions and whatnot. But, you know, I think where a coach provides very unique value is they could call your blindspots with 100 percent having your back at the same time. And so let me ask you to be vulnerable here. What was a blind spot that you got called out on and how did you grow through it?

Louis Beryl: One of the ways that I think I’ve really evolved and I and I talked about this a little bit before in my relationship with my co-founder, Ben. A blind spot I had, even though I think I understood this lesson, was that I had a certain expectation of what a role or a person should be. And I think that as I’ve grown, what I have come into a little bit more comfortably is, you know, this idea of what people are great at and really encouraging them to do more of what they’re great at and what they love. If they’re not great at something, instead of trying to fit a square peg into a round hole, actually just being a better leader to recognize what isn’t working and figuring out a different way to solve that problem. Yeah, and sometimes that can be a critical problem. Like, you know, as you pointed out, you know, maybe a CTO that needs a VP complement. The blindspot that I had maybe initially was as good a friend and a trusted relationship as I had with my co-founder. I think maybe there were things that I just thought a co-founder should do right or like I thought a CEO should do. And I think it took some time for me to and for us to have lots of honest conversations about, like, OK, well, you’re not good at that either. And like…and just being OK with neither of us are good at this thing. Why don’t we find support in a different way?

Jason Gore: Totally. I saw that each of you became more yourselves. You kind of relaxed into your strengths and you delegated those other pieces and you not only accepted each other more, but you also carved out the roles, knowing who you were and, you know, when you guys got acquired, you fought tooth and nail for each other to, like, contract it as such. And it was really beautiful to watch that.

Louis Beryl: Yeah. I mean, when you go through the full life cycle with somebody and come out on the other side, that it really helps solidify the relationship. I think it’s actually nice because I think there’s such a deep sense of trust, you know, almost almost like a marriage that despite any fight we have, we know everything’s fine.

Jason Gore: Do you fight or do you just disagree?

Louis Beryl: Both. You’re right though, you’re right. We don’t fight that much. We disagree a lot and we don’t fight that much.

Jason Gore: Yeah, I mean, I think that’s where you really know. I say you don’t know who your friends are until you really learn how to resolve problems where you get into something that’s really hard and you resolve it well together. Yeah.

Jason Gore: What was one of your biggest lessons learned from running Ernest?

Louis Beryl: People ask me that all the time, and I think about it all the time. And I probably spent a year just thinking about all the lessons. I could really talk about a lot of topics. I think one topic in particular that I maybe would break up into two things is about team building and hiring and about culture. About team building. When I look back at how I first built a team at Ernest, I think although we had raised plenty of money, I think that I had a mentality as a CEO of really pinching pennies. And I think that extended into how I thought about building the team, whether it was the level of seniority we would hire or even in negotiating people’s compensation packages. We were really pinching pennies. And although I think it is obviously good for founders to be scrappy and make sure they have the correct amount of runway.

Jason Gore: For sure.

Louis Beryl: I think that it had some pretty significant negative effects. I think we hired overall, if I looked at the whole team, even as we scaled up to like one hundred people, the ratios of leaders and more senior people, more experienced people, was really off. And that ultimately creates a lot of what I would like to describe as management debt on the more senior people right there. There’s more people for them to train and more people for them to manage and totally. And those junior people aren’t getting the proper level of mentorship and to grow in their career. And so it can have a lot of knock on effects on people’s happiness and productivity at the company. And so, as I thought about building Rocketplace, we were definitely much more thoughtful about how we think about the level of seniority. What do we think about spending money in a way that’s healthy? The other thing I brought up was culture. Obviously, everyone thinks that culture is important. No, I doubt I mean, maybe you’ve met a few CEOs that don’t believe that. But I think that what my more naΓ―ve view on it was that, you know, you do things like you put into place good values and try to institute certain practices and policies to create a culture. And I think as I’ve matured, my view, my current view on culture is that it’s kind of like diet and exercise. You have to have a plan and that could be your values. You also have to be constantly reassessing, reinforcing actually like asking yourself what’s not working, changing things up, like culture is like this constant practice. And really, if you’re going to create a great culture, what you’re going to do is you’re going to work on it every day. Right. Almost like physical fitness. What then happens is like it’s like the sum total of all of that thoughtfulness and all of those changes and all of the all of the different ways you conduct meetings and people interact with each other and emails that get sent to the company, all of those little things that add up over time. That’s actually the culture.

Jason Gore: Beautiful. You know, thank you so much for sharing that. It’s a good segway into sharing one of the free tools that’s on our sister company’s website, saturn leadership.org. And if you look at what we call the leadership micro practices right. They’re, micro they’re practices. There’s these little things that if you don’t do that are going to come to bite you sooner or later. And they’re going to show up negatively in our culture. And so in the leadership tab instead of Saturn Leadership are the micro practices that Neuberg Gore basically holds all of our clients accountable to and looking at what are their blind spots and which ones are going to have the highest impact if they change and the biggest negative impact if they don’t change. Someone who can’t afford right now, I would just encourage you to go to that list and identify two things that you could do to improve yourself. Tell someone else whether it’s another CEO, a co-founder, a friend, this is what I’m working on and have an accountability partner to hold you accountable to that, to check in. How are you doing there? What are you doing? What are your experiments? What are you trying out? What’s not working and starting to grow now as a leader? Because I think a lot of what a coach does for our clients.

Louis Beryl: That is actually the end of the Jason Gore “Startup Stack” conversation, at least for now. Sending one big final thanks to Jason for joining us and for giving us so much amazing material that we had to create a second spillover episode. That’s it for “The Startup Stack until next week. See you then.

Announcer: The Startup Stack. Written and edited by Hannah Levy, produced by Leah Jackson. 

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