#93 20 Minute Playbook: Edward Sullivan – CEO and Managing Partner of Velocity Coaching

Edward Sullivan is CEO and Managing Partner of Velocity Coaching, an executive coaching firm that helps founders scale their businesses. In this episode, Edward and Daniel discuss routines, successes, and failures.
Last updated
August 13, 2023
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Edward Sullivan has coached and advised start-up founders, Fortune 500 executives, and political leaders for over 20 years.
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#93 20 Minute Playbook: Edward Sullivan – CEO and Managing Partner of Velocity Coaching

“Anyone who thinks they're perfect is actually hiding a very deep sense of insecurity.” – Edward Sullivan

Velocity Coaching works with hyper-growth companies, helping founders who have found product-market fit scale their businesses 10-100x. Their clients include DoorDash, MasterClass, Airtable, Google, and Apple, and they’ve worked with some of the biggest names in tech, including Tony Hseih of Zappos. Edward Sullivan has coached and advised start-up founders, Fortune 500 executives, and political leaders for over 20 years. At Velocity Coaching, Edward Sullivan serves as the CEO and Managing Partner for a team of over 25 coaches located around the world.

Topics discussed with Edward Sullivan

  • 00:01:18 – Edward’s latest deep dive into surfing
  • 00:02:26 – Superpowers and struggles 
  • 00:04:41 – Habits, routines, diet, and exercise
  • 00:07:53 – Recommended books
  • 00:10:02 – On failure and success

Books Recommended by Edward Sullivan


Daniel Scrivner (00:06):

Hello, and welcome to another episode of Outlier Academy's Playbook Series, where each week we sit down with an elite performer from iconic founders to world renowned investors and bestselling authors, to dive into the tactics, routines, and habits that got them to the top of their game and keep them there, all in less than 30 minutes. I'm Daniel Scrivner and on the show today, I sit down with Edward Sullivan, who is the CEO and Managing Partner of Velocity Coaching. Velocity has a team of over 25 coaches located around the world and they work with the world's best hyper growth founders to help them scale their companies and their leadership skills through that crucial 10 to 100 X growth phase.

Daniel Scrivner (00:44):

Velocity has worked with almost all of the biggest names in tech, including DoorDash, Masterclass, Airtable, Google, and even Apple. You can find the notes and transcript for this episode at outlieracademy.com/93. And you can learn more about Velocity Coaching at velocitycoaching.com. And you can also follow Edward Sullivan in on Twitter @edwardlsullivan. With that, please enjoy my conversation with Edward Sullivan, Managing Partner and CEO of Velocity Coaching. Edward Sullivan, thank you so much for joining me again on Outlier Academy.

Edward Sullivan (01:15):

So happy to be here.

Daniel Scrivner (01:18):

So this should be fun. This is a little bit shorter, a little bit fast paced. Let's go ahead and get started. The first question is always about a recent fascination. And so looking for something that you can't stop thinking about, you can't get out of your head. What is that these days?

Edward Sullivan (01:32):

I would say it has to be surfing, over pandemic.

Daniel Scrivner (01:36):

Surfing, in New York?

Edward Sullivan (01:38):

Here's the story. Over pandemic, in 2020, I got essentially trapped in California. It's a fancy, great place to be trapped actually. I was there on a ski trip with some friends on March 11th. On March 13th, flights were canceled and New York basically shut down. I ended up staying in California for nine months with nothing more than the clothes I had packed on a ski trip. I rented a place in Santa Barbara for six months, bought myself a surfboard and relearned to surf. I surfed a lot as a kid and in my twenties, but not so much in the last probably 20 years. So now, I don't know if you can see over my shoulder, I've got three surfboards in the corner here in my apartment in New York, and another two surfboards back in California. I've just become completely obsessed.

Daniel Scrivner (02:26):

That's a great thing to become obsessed with. When you think about your superpowers, what are those and how do those show up day to day?

Edward Sullivan (02:35):

I would say my superpowers are first and foremost empathy. I think that I have an almost weird ability sometimes of understanding what people are feeling, sometimes before they understand what they're feeling. It can be a little bit confronting for people if I give myself the permission to name it, but it can also establish really great connections really quickly. And I also have a special gift for having small barbecues on my roof here in the West Village and my friends are-

Daniel Scrivner (03:09):

Well, that sounds great.

Edward Sullivan (03:11):

Are just waiting for spring and summer to come.

Daniel Scrivner (03:14):

We're close. We're getting close-ish. On the flip side of that, what do you feel like you struggle with personally? And I think what we're trying to get at here is, one, get people to be open about not just about what they're good at, but also what they struggle with. But also to share with others how they've struggled, how they've improved, how they've worked around it. What comes to mind when you think of that?

Edward Sullivan (03:37):

Yeah. The first thing that comes to mind when you say struggle, and it is I think a struggle for many is, throughout my life I've had episodes of depression, to be very honest. And that is sometimes related to incidents or events. After a breakup, or I got a little depressed after the death of my father. But it's something I think that actually unifies us as a species, right? I think we're all inherently emotional people, and to not talk about the fact that it makes it harder for others. We don't have to go through the sad times alone. I also thought a little bit about isolation is one of those things I struggle with. It's been hard during the pandemic to feel isolated from friends and family. I'm a very social person. I mentioned on our, last time we recorded, I have 500 friends in New York, only because I just love people. So to feel that isolation over the last couple years has been hard. And I have found, I think, a lot of solace in the outdoors. I found a lot of solace surfing, and just taking really long walks.

Daniel Scrivner (04:41):

On the habit and routine side, what habits have you played around with? And/or, do you have a daily routine? And if you do, how dialed in is that? And that can be everything from, here's the things I do every single day, which may be who you are, I'm guessing it's probably not. Or may be here's the things I try sometimes. Here's the things that often work for me. What do you do with habits and routines that help you show up at your best each day?

Edward Sullivan (05:05):

I mean, I will admit, and it might sound sacrilegious, given the current way things are going with habits and atomic habits and everything else. I'm really bad with habits. I'm really bad with morning routines. I used to have a religious mindfulness habit. I've got a little bit off of it recently. One habit that is completely unshakable is my morning coffee. I go to the coffee shop across the street and I walk in and they're already making it, they can see me through the window. My eight ounce cappuccino at Partners at Charles and Seventh Avenue. I'm learning, actually, as the company grows that I need to be better about certain habits. I'm developing much better hygiene around following up, better hygiene around using our CRM and doing all those nitty gritty things that are simply the cost of running a growing business. I coach around all these habits and coach people who are running much bigger businesses than I run at this point, but I still have to work on it.

Daniel Scrivner (06:04):

On the fitness side, what's your approach to diet, exercise and sleep? And how have those evolved over time?

Edward Sullivan (06:10):

How have they evolved over time? I didn't have any habits around exercise, diet or sleep until my mid thirties. And I was actually working as the Executive Vice President of Communications and Government Affairs at a solar company at that point. I was wearing a suit to work every day. It was a very formal office. And I was having three cups of coffee a day and three cookies, and didn't have any time to work out. And I took my suit pants down to the tailor on the corner, and I handed them to him to make these bigger. I was giving up. I'm officially giving up to middle age.

Edward Sullivan (06:50):

As he walked into the back with my pants, I said, "Wait, bring them back. I'm going to change my habits around this." So I started, every time I wanted coffee, every time I wanted a cookie, I would do 10 pushups behind my desk. And then 10 turned into 20, then 20 turned into 50. And pretty soon, the head of HR was like, "Edward, have you been working out?" It was like that one bit of positive feedback completely changed my attitude towards fitness the rest of my life. So since then, maybe I am decent at some habits. Since then, I've been fairly good at eating less carbs. I'm not keto, I just eat less. I work out three to five times a week. And I try to get as much sleep as I can. But it's hard running a company. It's hard traveling. And it's hard in New York.

Daniel Scrivner (07:37):

Yeah. I imagine it was really difficult that first time you tried to do 10 pushups instead of eating that cookie.

Edward Sullivan (07:43):

I couldn't do 10 pushups. I felt so pathetic. It was amazing. I hadn't exercised in literally years.

Daniel Scrivner (07:49):


Edward Sullivan (07:50):

Aside from doing a couple marathons, which doesn't do much for your upper body strength.

Daniel Scrivner (07:53):

No, no, no, no, that does not. Okay. Favorite books. What books have had the biggest impact on the ways you work or think? And if you can't think of any, I think the way I would reframe that is, books that often come up in conversations with clients.

Edward Sullivan (08:09):

Yeah. Obviously writing our book had an incredible impact on how I think. I hope eventually someone mentions it in one of these interviews as having an impact on them. I've really enjoyed in the last couple of years, is it Permission to be Disliked?

Daniel Scrivner (08:23):

Yes. The Courage to be Disliked.

Edward Sullivan (08:25):

Courage to be Disliked. Really enjoyed that. I go back to Flow a lot. And I also go back to just about anything by Alan Watts. I have most of his books, some of them within an arm's grasp at any moment. So I do a lot of just short reading of Alan Watts just to keep myself connected.

Daniel Scrivner (08:49):

I typically wouldn't do this, but no one on the podcast has brought up the Courage to be Disliked, and it's a book that I know, I don't know a lot of people that have read it, but the people that have read it, love it, and refer it. It has a very high net promoter score for people that have gotten all the way through the book. Which is a good thing. Can you just try to do even just, in a short bit of justice, what you found profound about the book and why you thought it was so important?

Edward Sullivan (09:15):

As a lifelong people pleaser, as someone who was the class clown growing up and student body president in high school and blah, blah, blah, someone who always was looking for accolades, to read a volume that gave me permission to say no, gave me permission to be contrarian, that gives me a way of thinking about the world in which my values should come first, as opposed to my interest in going with the flow or being liked. Just profound.

Daniel Scrivner (09:53):

That's a great job, and it's a good reminder that I need to actually finish that book. Because I started it, but I've never finished it.

Edward Sullivan (09:59):

I need to remember the title.

Daniel Scrivner (10:02):

On the personal growth side, one of the questions that we always ask is for a favorite failure. And I think what we're trying to get at there is, in life we attempt a lot and there's a lot of things that don't work out as intended. But that doesn't necessarily mean it wasn't a great thing to do and we don't find ourselves in a better place for having tried or having tried and failed. Do you have any favorite failures? Do any stories come to mind?

Edward Sullivan (10:26):

The one story that comes to mind when I talk about failures, just because it was so spectacular. Coming out of my work in solar, I organized a conference in California to bring scientists in from all over the world to talk about climate change, and to talk specifically about carbon sequestration. As a result of that, there was talk of investing in potentially risky, but potentially ultimately needed more now today than it was 10 years ago when we did this conference, of geoengineering and carbon sequestration technology. Who was going to fund that? Someone from Richard Branson's Carbon War Room was at this conference, and I had developed a relationship with him.

Edward Sullivan (11:09):

And I developed this entire pitch deck for putting together basically the world's first venture fund to support very high risk carbon sequestration technology. I did all the research, put together the model, put together the deck, did a preliminary pitch to this guy. And he said, okay, Sir Richard is ready to hear your presentation. It's going to be ... what time was it? Let's say 11 in the afternoon, London time, which was five in the morning or four in the morning when I lived in San Francisco. And I was all prepared. I was ready to do it, went to bed that night, woke up at 9:00 AM that day, and slept right through my presentation with Richard Branson. Because at the time, in the iPhone, it was very simple to flip from AM to PM. And I learned a very valuable lesson, which is to set multiple alarms when you're going to talk to Richard Branson in the morning.

Daniel Scrivner (12:04):

Wow. All because of an iPhone alarm.

Edward Sullivan (12:08):

Fabulous, that failure. And I did not get a second chance, unfortunately.

Daniel Scrivner (12:13):

And when you woke up, did you immediately realize what day it was and what time it was? Like how disorienting was it?

Edward Sullivan (12:18):

Oh yeah. I woke up and I burst into tears. I did.

Daniel Scrivner (12:22):

Well. That is an amazing story. That's probably the best story that anyone's said. So thank you for sharing. Okay, more fun question, and then we'll wrap with the last question. It's all about success. And I think, I have two questions for you. Number one, what does success mean to you now and how has that definition changed over time?

Edward Sullivan (12:43):

I think success at one point meant that I was, frankly, just living up to someone else's idea of success. I had a title, I was on a career track, I had access to certain powerful people, did a lot of work in politics. I really let some incredible mentors shape my idea of success and ultimately shape my career path up until probably 10 years ago. Since that time, success to me means being able to do what I love. And not only in my personal life, but also at work.

Edward Sullivan (13:22):

I mean, there's nothing I can imagine doing aside from working with founders of companies and CEOs and executives who are trying to build the great companies of tomorrow. I feel very lucky to be able to do this work. And I also feel very lucky that the work, now at least, is fully digital. So I can do it from just about anywhere. I try to spend every January now in some beautiful place surfing. Try to spend part of February in some beautiful place skiing. And I feel very privileged and very lucky to be able to do that. But to me, that is success.

Daniel Scrivner (13:56):

Doing what you love. And it sounds like moving into a much more personal definition of what you love as well, too. Yeah,

Edward Sullivan (14:04):

Yeah, absolutely. Absolutely.

Daniel Scrivner (14:05):

Some of the Courage to be Disliked in that answer. Last question. What are you most grateful for in this phase of your life?

Edward Sullivan (14:16):

I would say I'm grateful for giving fewer fucks. I think, the twenties, thirties, teenage years, there's a lot of giving of fucks. There's a lot of caring what everyone thinks. There's a lot of living up to certain standards, trying to make your father happy, trying to make friends happy. And I think some people get to this very early in life. I got to this somewhere around my 40th birthday, where I really stopped caring what other people thought and I started doing what I loved doing and living life the way I wanted to live my life. And I'm a much happier person and I think I'm much easier to be around.

Daniel Scrivner (14:54):

I would imagine. Well, that's a perfect note to end on. Thank you so much for the time, Edward.

Edward Sullivan (15:00):

Thank you.

Daniel Scrivner (15:01):

It's been incredible to have you on twice, so I really appreciate it.

Edward Sullivan (15:03):

Thank you, Dan.

Daniel Scrivner (15:05):

Thank you so much for listening to this episode. You can find links to everything that we discussed as well as the notes and transcript for this episode at outlieracademy.com/93, it's 93. For more from Edward, listen to episode 90, where he joins me on our spotlight series to go deep on coaching the world's best hyper growth founders, from DoorDash and MasterClass to Google and Apple, including how Velocity Coaching helps companies transition from product market fit to hyper growth, scaling their companies 10 to 100 X while scaling their leadership skills in parallel. You can find more incredible interviews with the founders of Superhuman, Levels, Rally, Commonstock and Primal Kitchen, as well as bestselling authors and the world's smartest investors at outlieracademy.com. You can now also find us on YouTube at youtube.com/outlieracademy. On our channel, you'll find all of our full length interviews as well as our favorite clips from every episode, including this one. For more from our entire team, we hope you enjoy the show and we hope to see you right here next week on Outlier Academy's Playbook Series.

On Outlier Academy, Daniel Scrivner explores the tactics, routines, and habits of world-class performers working at the edge—in business, investing, entertainment, and more. In each episode, he decodes what they've mastered and what they've learned along the way. Start learning from the world’s best today. 

Explore all episodes of Outlier Academy, be the first to hear about new episodes, and subscribe on your favorite podcast platform.

Daniel Scrivner and Mighty Publishing LLC own the copyright in and to all content in and transcripts of the Outlier Academy podcast, with all rights reserved, including Daniel’s right of publicity.

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