In this episode of The Next Next, host Jason Jacobs interviews Steve Schlafman, founder of Downshift, a professional transition coaching company. Steve, who has extensive experience as a venture capitalist and now an executive coach, helps founders and high performers through significant life transitions and recovery from burnout. The discussion covers Steve's personal journey and the kind of clients who benefit most from his services. They delve into the common challenges these clients face, including feeling lost and transitioning too quickly to new pursuits. Jason and Steve also explore how modern tools like AI are reshaping the way ambitious professionals can balance work and personal fulfillment. Steve emphasizes the importance of intentionality and values in navigating transitions, while offering insights from his coaching programs and personal practices.
Navigating Transitions with Steve Schlafman
Hosted by Jason Jacobs, this episode of The Next Next features Steve Schlafman, founder of Downshift, a professional transition coach. The discussion delves into Steve's shift from venture capital to coaching, the philosophy behind Downshift which aids executives and founders transitioning out of demanding careers, and recovering from burnout. Steve discusses the common struggles of highly ambitious professionals, the process of reconnecting with personal values, and the importance of intentional transitions. The conversation also covers the evolving nature of work, the potential of AI, and achieving a balanced life while maintaining professional excellence.
00:00 Introduction to Steve Schlafman
00:26 Steve's Journey from VC to Coach
00:43 The Concept of Downshift
01:15 Discussion on Life Transitions
01:46 Jason's Introduction and Show Purpose
03:43 Steve's Work and Personal Evolution
05:03 The Birth of Downshift
07:13 Navigating Transitions and Coaching
14:27 The Importance of Slowing Down
15:00 Client Experiences and Success Stories
18:17 Changing Work Dynamics and AI
27:46 Balancing Ambition and Happiness
31:21 Balancing Ambition and Family Life
33:20 Navigating Resentment and Creative Juices
34:25 Exploring Ambition in Personal and Professional Life
36:48 Advice for Those in Transition
40:33 Downshift Program Overview
45:36 Future Plans and Personal Values
48:49 Innovative Ideas and Closing Thoughts
Jason Jacobs: On today's episode of The Next Next, I'm pleased to bring on Steve Schlafman. Steve is the founder of Downshift, a professional transition coach who's based in New York and guides executives and founders through intentional transitions and recovery from burnout.
Steve also writes Where the Road Bends, which is a newsletter exploring personal evolutions and life transitions. Now, I've known Steve a long time, back even before the days that he was a venture capitalist. He went on to be a VC at several top firms in New York and then he went on a journey of his own where he learned how to be an executive coach.
He thought about combining coaching and investing and raising a fund that offered coaching as a key differentiator. And now he's focused on downshift where he's specifically working with founders and other high performers who have been running hard for a long time, who are in the process of transitioning out.
And rather than just blindly running hard straight into the next thing. They're longing to take a step back, to take stock, to ask themselves, what are the key criteria that's going to make me happiest personally and professionally in this next chapter? Because we don't have that many chapters in life, and especially as you get older, you want to make them count.
We have a great discussion in this episode about Steve's journey to doing the work that he does, about what types of clients tend to get the most value from his services. We also talk about what types of transitions they're going through, what some of their challenges are, and what some tips are for people that are going through these kinds of transitions to do so effectively.
We have a great discussion in this episode, and a timely one for me, and I hope you enjoy it. But before we get started
I'm Jason Jacobs, and this is the next, next, it's not really a show. It's more of a learning journey to explore how founders can build ambitious companies while being present for family and not compromising flexibility and control, and also how emerging AI tools can assist with that. Each week, we bring on guests who are at the tip of the spear on redefining how ambitious companies get built.
And selfishly, the goal is for this to help me better understand how to do that myself. While bringing all of you along for the ride. Not sure where this is going to go, but it's going to be fun.
Okay. Steve Schlafman. Welcome to the show.
Steve Schlafman: Thanks, Jason. So stoked to be on.
Jason Jacobs: Yeah. It's kind of interesting because I think. Well, one, I've known you a long time. Two, we're, you know, of a similar age and demographic midlife, you know, entrepreneurs slash investors and so some commonality there three, I think some of the work you're doing now with Downshift in terms of helping ambitious people you know, unwind from intense periods and figure out. What's left and where to go and how to proceed and I don't want to put words in your mouth, but that's certainly relevant to some of the stuff I'm sorting through and then I think the last piece is just that I was actually a client of yours from a coaching standpoint when I was you know, kind of unwinding from You know, from how I've been spending my time operationally over the last six years.
And so you've kind of had a front row seat to some of the transition that I've been going through as well. So just psyched to have you on and to catch up in public, I guess.
Steve Schlafman: Yeah. It's a real honor. It's rare for me to want to jump onto a podcast and get going, but this one, the next, next I really feel the energy and the spirit coming through you. And yeah, I'm just, I'm thrilled to see what unfolds in this next journey for you.
Jason Jacobs: Well, to kick things off, Steve, maybe for those that don't know you as well as I do, talk, about the work you're doing now and what led you to the work that you're doing now.
Steve Schlafman: Yeah. And I want to put a pin on that for a second. And if you had asked me that question a decade ago. I would have said, I'm a VC and this is what I do, and this is who I am in that context. And 10 years later, I think it's really important to note that I see myself as much more than just a professional.
Certainly I'm the founder of a company called Downshift. Yes, I'm a coach and a guide that helps ambitious professionals navigate transition. with, a lot of intentionality and at the same time, I'm appreciating that I am so much more than that. I'm a father, I'm a son I'm a meditator.
There's just so much more to me now
Jason Jacobs: Comedian? Are you a comedian as well?
Steve Schlafman: Unfortunately, I'm not a comedian. I like to think that I have some humor. My wife doesn't agree with me. But really the heart of it now is like I'm embracing, as I like to say, like I contain multitudes, potentials, and contradictions, and I'm embracing all of that.
But practically speaking, as I said, I'm the founder of a company called Downshift, and it was really born out of a desire and a need that I had. Back in 2017, exactly eight years ago, when I made partner at RRE Ventures in New York, and I was basically one of the rising stars and I went in and I resigned and my partners thought I was going to a competitor and they said, what are you doing?
And I was like, I have no clue. And I went on a six month sabbatical. Paid sabbatical and I was completely fucking lost. I had no idea what I was doing and I'm basically building the executive coaching firm and Practice that I wish I had access to in that point in time.
Jason Jacobs: And was it with the benefit of hindsight that was leading you to feel lost? And how much of it was internal versus external, do you think?
Steve Schlafman: It was all internal I have a big belief that our internal state dramatically shapes how we perceive the world and the problems and opportunities that are in front of us. And again, with the benefit of hindsight, what I've come to realize is a lot of the.
Things that were in my way in those times this confusion, this disorientation, this lostness were largely based on my inner state. And what I've also come to appreciate having studied transformation and transition is that it's very common. It's very common when we go through these periods of significant change when we're unmoored, untethered to something and high performers, high achievers, ambitious professionals, whatever you want to call us can feel that lack of safety when there's no more structure, when there's nothing to cling onto and hang our identity on.
And so it, in the benefit of hindsight, what I realized is that it's a very familiar occurrence for those navigating transition.
Jason Jacobs: And you said that you're building Downshift as the coach that you wish you had at the time. What were you seeking at the time? And I know some of this is With the benefit of hindsight, which is fine, but yeah, what do you wish you had?
Steve Schlafman: Yeah what I really wish I had was a sparring partner, was a thought partner that was really grounded in both the world that I came from. Which was entrepreneurship and investing venture capital while also being deeply grounded in transformational and transitional coaching. And when I looked out into the world, when I thought about getting a coach at that period of time, like I got support from some great people, but most of them were my colleagues in the venture business, which basically were giving me advice that they would heed themselves.
Most of the executive coaches that I knew at the time were focused predominantly on leadership development and working with founders and executives in the seat versus these really transitionary periods. That to me was what I ultimately saw as the opportunity. As it unfolded, it's not like I saw the opportunity in my shoes. There was a long period of time where I thought I was actually going to go become an executive coach and I was going to pair together venture capital and coaching and build a unique firm that kind of marries these two worlds together.
I looked out at all these venture firms and was like why aren't there any firms that really work with the founder at a holistic level? And that was the path that I thought I was going to go down. I started training to become a coach. I still had one foot in the investing world and there was this oscillation that took place between these identities over almost two years.
And eventually what happened was, is I went through in some ways or in a lot of ways, an identity crisis where I was like, am I a coach or am I an investor? And at that point, this was about five and a half years ago. I was like, you know what? I'm ready to step fully into coaching. And the first two years of my practice was working with executives and.
General partners and managing directors at venture capital funds. And what started to happen because I was so public about my transition and I wrote about it, I started having founders and investors and executives coming to me in confidence saying, Hey, I saw the transition that you went through and it was like really brave and I'm in the same.
The same spot. I think I'm thinking of three people right now. Three, three founders in particular. One, actually two backed by YC and another one backed by Sequoia. And we started working together. And I loved it. And I supported these three entrepreneurs through a variety of one in particular over a year and these other two for about six months.
And I started to say Oh, leaders in transition, this is a really interesting part. And I was really passionate. And then I was writing online on my newsletter. Everything I was writing about wasn't about leadership. It was about change and transition. And this journey that I went through and that I'm observing in the world and a lot of these professionals and ambitious performers that are in midlife.
And then eventually I was like, actually, I think this is what I want to do full time. And so about three years ago, I pivoted my practice and emailed. All of my clients, I had a full roster of CEOs and investors and I basically said, we're going to pause. I'm transitioning and literally within three months I had a full practice.
And so I knew I was on to something instinctive. I didn't do any business planning. There was no like market research. It was just based on my own experience and everything I was hearing from these clients and knowing that there were so many more people out there like us that wanted something like this.
Jason Jacobs: So, when I was in between when I had left ASICS after Runkeeper was acquired and before I had gotten into MCJ, I was in this WhatsApp group with a bunch of founders in transition and what was really jarring to me at the time. So, I think. I mean, this, this was before downshift and there were some fancy people in there, like well known entrepreneurs who have these public personas of being confident and visionary and futurists and leaders and setting the tone for where the world's going to go and stuff like that.
And like, these people were like fucking lost, you know? And. The contrast between the public persona and what's going on under the hood, particularly in times of transition is so jarring. And then there's really no outlet because if you're just kind of like, there's, I think very few people that understand, but also it's like, wah, wah, cry me a river, you know, shut up rich boy.
Right. And it's just kind of a lonely place to be. So I think the fact that you've kind of tapped into that, at least from my little data points shows that, and what I've experienced personally, that it's a real problem. And it's not one that has had a lot of outlets to address it historically.
Steve Schlafman: Yeah, really well said two things that come to mind as I was listening to Jason, the first one I couldn't help but think about the CTO of loom who recently posted very publicly a blog post about how he's made all this money and yet he feels incredibly lost in life. It was incredibly moving and brave expression that he shared with the world.
And it was met with both I think a lot of skepticism from people being like, poor you, while also scores of other people basically saying, yeah, this is, I've experienced this too. This is really something that is more common than most people would think. And so that was the first point I wanted to make.
And then the second is, and this kind of ties into the work that we're doing at Downshift, is that There is this idea of lostness and putting on this public persona and yet deeply inside being disoriented and not knowing what to do in this confusion that you experienced in this group. The other thing as it relates to downshift is that oftentimes sled dogs need a sled to pull as my partner, Andy Johns likes to say.
And inevitably they just go searching for the next thing as quickly as possible because sitting with that feeling of not having something to tie themselves to and pull forward. And so what happens is they just rush what we see a lot as they, and I've seen it with several of my clients, they rush into the next thing because they can't bear being with it.
And then they realize that's actually not the thing that they really want at this point in their lives, especially Those that have families and have aging parents, you know what they call the sandwich generation. And so for us, a downshift, we're not saying you have to downshift your life forever, but it's how do you slow down just a little bit, just enough in these really important moments of change so that you can start to connect to what actually really matters and what's the kind of company that or what's the kind of pursuit that feels most aligned in the next chapter.
Jason Jacobs: So is it mostly founders that you work with?
Steve Schlafman: Variety. Founders, C level executives, investors. So it's pretty wide range. I've worked with, founders that have taken their companies, public founders that have exited like yourself venture capitalists that are exiting the business. I've worked with a senior advisor of Obama.
I've worked with a multi star Michelin chef who wanted to express himself more creatively in other pursuits, but not really sure how to do that in the context of his restaurants. And so it's a pretty amazing group of people. I think the common thread across all of them is that they've had a fair amount of success, and there's a lot of optionality, meaning that it's not like they're a chief product officer and they know they want to just go find another chief product officer job.
It's almost like the possibilities are endless and they don't know how to sort through it. And not all are post economic, though I would say a fair amount of them are, meaning that they have the means to retire. But they're hungry. They still want to find something that they can pour themselves into but hopefully do it in a way that's different than the last time.
Jason Jacobs: Huh. And how, in your mind, by calling it downshift, should I think about downshift more like slow down to speed up again? Or is it more like step off the train with intention?
Steve Schlafman: I think it's, our philosophy is really, it's up to the person. And what it is that they discover about themselves, as the metaphor, we, at Downshift, we love using metaphor and, the idea of a downshift is that you're a race car, and you're going around the turn, and to be able to accelerate through the turn, you actually have to switch gears, and for us, it's not up to us to say, you have to slow down, it's how do you just slow down enough while you're going through these turns to ultimately determine what actually really matters, what really matters and also to look at some of these behavior patterns that might be getting in the way or creating more suffering and wanting to basically develop a new relationship with work.
Okay. Or with life and add more dimensionality, like to give you a sense, like I'm just wrapping up with a CEO client who's actually still in the seat of being a CEO. And he just is saying my whole life's work, my whole, my entire life is work. And I want. More multidimensionality. I'm working with a C level executive at a major airline company right now.
Fortune 500 airline. Same thing. He is I'm gonna kill myself. I'm I want to continue to maintain my edge at work, but I need to start to create healthier boundaries and I want to take care of myself and spend time with my husband and so on and so forth. So I think the point is we're not here to dictate ultimately.
How much someone slows down is more like helping them really connect to what it is that they want.
Jason Jacobs: Huh. Well, here's a question I've been curious about. I know how I've been feeling as a founder in terms of needing to work different. Part of that is a life stage that I, I'm, you know, older, I'm feeling more mortal, you know, how many cycles do I have left, my family's at an age where my kids need a lot of attention, I want to be present.
But what I'm wondering is, how much of it is life stage specific versus an actual shift across the labor force in terms of desiring to work? different. What do you think? Is it just because we're middle aged? It seems like, you know, this is what everyone wants, but it's critical. Of course, our peer group is all middle aged like us, right?
Or is it actually changing across the board?
Steve Schlafman: I think it's changing across the board. That's my sense. Certainly in mid, those in midlife are bumping up against this. Especially those that were told that achievement. And success and accumulating wealth and resources and material objects would make us feel whole.
And when we're like, Oh, actually that's not entirely true. It creates a cognitive dissonance. And so I've seen a fair amount of that. I've also seen, if you look at like Gen Z, which, they're they come at the criticism of the older generations for their work ethic. But I think that COVID really showed people that that there can be a different way to work while also maintaining edge.
And that's what I'm at least, what I'm trying to figure out. In this chapter of life, like you I'm in my mid to late forties. I'm knocking on the door 46. I have two kids. I have one parent remaining and she, my mom's 78. There's a lot on my plate right now.
And so it's, how do I build a company that hopefully I can work on for the next five to 10 years while also not killing myself because, I want to take care of my body. I want to have time with my family and I want to express myself creatively and I want to build a business. And so it's how do I do all of those things in a way that is effective and, is at a good pace, as I like to say to our team at downshift.
We're not running through walls we're walking through doors at a very brisk pace. And so it's up to me to set the tone, but I think it really comes down to pace and how do we take a longer term mindset such that we're not trying to burn ourselves out. And I have a whole bunch of different philosophies around seeing companies, not as companies that need to scale as quickly as possible, but as more containers for emergence that basically it's just a series of experiments and then being open to what emerges.
And then in these periods sort of picking our heads up and then feeling into what's emerging and then making the next set of decisions. So it's a very different orientation than going to try to like. Build the next unicorn and scale to, millions of users.
Jason Jacobs: So I'll take a slightly different angle here, which is a related thing that I've been wrestling with, which is that it seems that innovation cycles keep compressing and getting faster and faster. And things like moats and defensibility are harder to come by and it seems like in many cases, certainly not all cases, but in many cases, the competitive edge comes from moving fast and contrast that with the desire of a growing group of people to work different.
How do those go together where innovation requires that you need to keep working faster and harder to win at the same time that so many people need to get off the train or they're going to fry themselves.
Steve Schlafman: Yeah I would say that there's the way I think about it is twofold. I think on one side is like a traditional venture scale company that is really pushing the boundaries of innovation. And trying to create something that is truly groundbreaking. And in that case, I do believe that speed and scale matter.
I also think that there's, and you're aware of this, I believe is this idea of a calm company. Where the goal isn't necessarily to build the biggest, fastest company, but to build a high quality company that serves a problem and serves it really well. And that's the kind of company that we want to build a downshift and the stance that we're taking is that we're going to innovate and we're going to use the tools that are at our disposal, meaning software and AI.
To give us leverage and to us, that's what we see is the beauty in this is that we can get leverage and get some of our time back, while also taking a really long term view on this,
Jason Jacobs: And when you think about company creation, I mean, obviously, you and I both come from the venture backed startup world. Historically, do you see that that world will actually evolve and change, or is it more like that world's just going to do what that world does, but there's a new, essentially a new asset class or a new risk profile or a new type of company emerging that will be separate and distinct?
Steve Schlafman: I think so. Yeah, that's what I'm seeing and I hear it and I've spent a lot of time with Bryce at Indie, friends with of Tyler at formerly calm fund, and I just think that for a certain class of entrepreneurs, those that have been through the boom bust cycle of the last 15 years, there's a lot of people, especially with the emergence of AI is I just want to do it differently. Like I'm working with a founder right now who is like, my next company, I don't want to raise venture capital. I don't want the pressure. I want to be able to have a lot more creative latitude and also I'm going to use AI. And I have a lot of confidence that between, my ability as an entrepreneur and leveraging these tools that I'm going to be able to get a lot more leverage and I don't have to be saddled and I can build a company exactly the way that I want to build it.
Jason Jacobs: Huh. And speaking of AI I mean, there's all over the spectrum right now, there's kind of one extreme that's like, oh, it's overblown and it's hype and it's a toy and why are we still talking about this? It's a distraction. It'll blow over like other fads blow over.
It's the pet rock of the, of the, you know of 2025. And the other extreme is like none of us are going to work anymore because AI is going to do everything. And like, we've got to derive purpose another way because we're all going to be here. And our nine to fives aren't going to be nine to five anymore.
I know, neither of us is like. Steeped in the technological underpinnings of AI, but from your seat, how are you thinking about the implications for the future and how it might affect people like your clients when it comes to finding purpose?
Steve Schlafman: Yeah. Think it's important to share where I land and by no means am I'm no longer a venture capitalist I'm not in the belly of the beast. I'm not actively evaluating companies. I don't know what's on the bleeding edge But I believe that AI is The most profound technology that we've seen in our lives.
I think the productivity gains relative to the cost that it's unlocking is unlike anything I've ever seen before. And I really do believe that it is a paradigm shift and I'm incredibly bullish on it. Even the tool set that we have now is so powerful. It blows the mind what it can do now.
And I feel like we're still in the very early innings. Am I in the camp of it's going to destroy all of our jobs? I don't know. I can't say. I do think there is the argument of every major technological wave that has come previously. Everyone has said it would wipe out all the jobs.
And for the most part, the jobs have largely Some have obviously died off but new jobs were created. I haven't thought enough about to see what are the new jobs? Like the way I think about how I use AI, which is. How does it unlock my existing creativity and get and give me the leverage.
And so the way I see myself as more of a producer and an editor and a manager of sorts. And I think that's where it gets really interesting is where it basically takes. A lot of these tasks. And that's where I'm like, huh, like there are times where I get nervous as a coach where I use chat GPT with very carefully written prompts for integration after therapy sessions.
And coaching sessions where I get feedback. It gives me things. And so for me, I think that there are going to be certain markets of human labor, especially on the low end. And the mid tier that I think are a threat potentially. Because I think sort of that long tail.
And then I think in certain industries like the human aspect is really going to matter
Jason Jacobs: I mean, I'm switching gears a bit, but relatedly, in terms of purpose, do you think it's possible to achieve greatness and be happy? Do those go together?
Steve Schlafman: Let's take the word greatness to you. What does greatness mean
Jason Jacobs: so I mean, I guess what I'm asking is if I look at people that have achieved truly outsized accomplishments and that might be founders like Bezos or the like, but it could be composers, musicians who tour all the time professional athletes.
I mean, anyone who's kind of at the tippy top of their game to achieve that level, to perform at that level. It requires immense sacrifice. And I guess what I'm just curious is are any of those people happier? Do you need to be tortured at some level to be able to make the level of sacrifice that cuts so much into bone of your daily joy?
Steve Schlafman: Yeah. I don't know if the highest of the most talented performers in the world are tortured, so to speak. I do believe that achieving a certain level of greatness requires sacrifice and it requires constraints and it requires commitment and focus. I fundamentally believe it.
And to me, I think that in order to really push things forward in an industry require continuously going outside of our comfort zones. in order to continue to expand the range of tolerance, the range of competency. And I think to get to the heart of your question, I think that there are periods where sacrifice is required, and whether that creates suffering, I think is largely dependent upon the individual.
I could imagine like Tom Brady, right? I'm a huge Pat's fan and a fan of Brady. Like my guess, I've never asked him this question, but my guess is he deeply loves football, loved it. And that's where he got a tremendous amount of meaning. To me, I don't know if happiness is the ultimate goal.
I think our society has made happiness like that goal. But to me, it's connection in meaning. And I think it's possible to be a high performer and have that connection and meaning as long as it, it is deeply authentic to who they are and they're not trying to just do it out of desire to accumulate money and all these other things it's the act.
That they love. It's, it's whether it's a pianist or Tom or Picasso or any of these greats, it brings them alive. There's a love to it.
Jason Jacobs: I could see the critics from a distance of what you're doing one critique might be Hey, downshift is great for anyone that's decided they're ready to water down their ambition to experience more daily joy. But that's not for me because like, you know, I, I've got all the things you just said, the love of creation and the, you know, achieving mastery and like, and, and, and that's my meaning.
And so I want nothing to do with downshift.
Steve Schlafman: Yeah.
Jason Jacobs: What would you say to those people?
Steve Schlafman: I would say, look at me where I am. I don't think I've ever been as ambitious in my life and, I want to build a great company. I have a lot of ambition and just to give you a sense right now, I'm enrolled in two different coaching programs. Intensives. I'm reading two other books.
I'm meditating an hour a day every morning and I have a full practice. I'm writing, at least one essay a month and like I'm building a team of really incredible people who are as ambitious as I am, but are also very interested in doing it in a slightly different way. I want to be excellent at what I do.
I want to be at the top of my game. It's, if you look at the way I spend my time it's moving in that direction. And yet, I'm unwilling to work around the clock. I, frankly, I just like my sleep too much. I want seven, eight hours of sleep a night.
Jason Jacobs: Do you feel guilty when you're with your family that you're not pushing the ball forward with downshift? And do you feel guilty when you're pushing the ball forward with downshift that you're not with your family?
Steve Schlafman: Great question. I would say to tackle the latter. When I'm working on downshift, I'm working on downshift. That's my focus. I love it. I'm immersed in it. It honestly, I, it, when I'm in it, there's nothing more than I want to be doing. If as much as I love my family and my girls for a long time, I have two daughters, six and two. I would say that with one child, I was able to be very ambitious and didn't feel like family was really pulling me much from my pursuits. Once we had our second, it blew everything up. And for almost the first year and a half, I had a lot of resentment. If I'm just being honest, I had a lot of resentment towards my family because I could feel a lot of creative juices and ambition online, but also feeling like this was a time in my life where I had to be there for my family, for my daughters, for my wife to support her.
And so what I ultimately had to do was a process. That resentment and process that those feelings of angst that I had when I was with my family, but unable to really drive my creative projects forward. And now I have a very different relationship to it because I recognize the preciousness of life and where just where they are like.
They're young once. And so for me, when I'm with them I'm with them, but when I'm working on downshift I'm really in it.
Jason Jacobs: Yeah, and I ask selfishly because it's one of the things that I wrestle with. Because on the one hand, it's like, oh, I figured it out, this next venture, I'm going to build different and I'm going to explore how to be ambitious, like what you were saying, but also be ambitious on the personal front.
Matt Slye, who we both know, corrected me because I was saying ambitious and still be, you know, without compromising essentially family time. And he's like, well, I think about it a little different. It's actually like investing in family with the same ambition that you invest in your professional pursuits.
And that really resonates. So it's like, okay, on the one hand, I'm going to explore how to build different where I can be ambitious in both of those lanes and they can coexist. But then the other is how some of these emerging tools can enable it. And it's like, Oh, perfect.
This is timely and I'm figuring out a lot of other people are going to be figuring out and it's now becoming possible. What wasn't possible before because of these tools. So it's like, Oh, so Zen, like in flow state. But then the practical realities are like my kids need so much and no matter how much I give them, I feel like there's more I could be giving them that would be better for them and better for family.
And, you know, hatching a new company from zero needs so much that no matter how much I give it, it could use more. And so on the one hand, it's like zen like, and on the other, like, I'm frickin tortured. Because every, it's just so confusing to me because normally I get manic about one thing and I just go all in and I just, I can't and I don't want to do it this time, but that doesn't mean that every day I'm not, like, banging my head against a wall trying to figure out the how.
Steve Schlafman: Yeah. Me too. It's something I'm still figuring out. And my job as a leader of this company is to find ways. to drive it forward. At the end of the day, I have to set the pace. And if I'm hanging out and not focused on it, like I have to set the pace.
And so I do it in the confines of my role as a father and I try my best. I'm not perfect. There are times where I'll say to my wife, I need 10 minutes and I sneak away and drop a voice note in the chat GPT to basically get a first draft of something that I'm battling around in my head.
And then I go back to being with the family and just that getting it off my chest. I'm like, Oh, now I can be present again and fully be with them because I know that this thing is waiting for me tonight or in the morning or on Monday.
Jason Jacobs: Steve, given that you have worked with lots of people who are sorting through some of these challenges themselves, for anyone listening who is in the midst of or sorting through them, or maybe will find themselves in three months and will remember this discussion, what advice do you have for them in terms of where to start, how to go about it, What to think about, tools, resources, anything that might be helpful for people that are trying to undo these knots for themselves.
Steve Schlafman: Yeah. I think it, again, this is really dependent on the person. What I would say in. We're recording this in January, so we're on the heels of the new year. Every year I release an annual review process a template, and we did it this year under the downshift banner. And in that review this year, it was not taking a goals oriented approach.
Instead, it was helping People connect to their values and the domains of life that really matter. And then to be able to articulate and express what those values actually mean, not like pie in the sky, but actually what does it mean on a day to day basis? And to me, what I would say is anyone that's either in transition or contemplating it is like really.
How do you connect with your values and articulate like what is really important to you at this phase? What is that? And, so that's the first thing. The other thing I would say is for those of you that are either on the verge of a transition or just on the other side of it, meaning the ending has happened, is what is any unfinished business that needs to be cleared up?
What needs to be grieved? What needs to be let go of? What conversations need to be had? So that you can add to the best of what emotions need to be expressed so that you can wipe the slate clean and be able to step into this new period without any of that sort of that emotional residue.
Weighing you down. Like for me, I would say and this was several of the firms that I worked with I didn't realize how much resentment I had built up towards my partners until many years later and things that I wish I had really processed in that time, such that I was like, wow, like, why is this stuff still coming up?
Like these guys are living rent free in my head all these years later. And it was because I didn't. Process those endings and fully give them the space that they needed to step into what's next. So those are just two, but there's, there's a whole range of resources that we have. But to me, the other thing I would say is and this goes back to Sly's comment.
And I wrote a piece on this maybe three years ago called Rethinking Ambition, which is, we in our society have a definition that ambition is solely tied to outcomes and work. And to me, I would just ask what is it that you want to be ambitious about? If it's fully work, great. Own it, fully own it.
But if it's other things like, look at that. And what are those things that you really want to be ambitious about? For me, I think the three things that I'm ambitious about is my health first. Cause I, if I can't be of service to anybody, if I don't feel well and I'm not operating at a high level, the second is a family.
And then the third is downshift. That's it. That's what's in my bucket right now. That's what I'm really ambitious about.
Jason Jacobs: And maybe just since we didn't really get into much of the guts of, of Downshift, just talk a bit about what your portfolio of activities and services looks like today, and then where things are heading if you look two, three, five years out in the future with Downshift.
Steve Schlafman: Yeah right now we have our core Decelerators program it's a seven week experience, so kicks off with a four day retreat in upstate New York. We've had 24 participants from literally all over the world in our two cohorts Kenya, London, Mississippi, Denver, San Francisco, Boston, New York, Los Angeles.
So very diverse group of people, largely in, in the tech and tech founders, investors, executives, creators. We take them on, we kick off with a retreat and then we take them on the seven week journey where we explore The idea behind this, that the program is to help someone an ambitious professional kind of fine tune their inner compass and to be able to redefine their relationship to work and basically carve a next chapter that is intentional, authentic and energizing.
And we're not the ones that define how that is. That they get to determine what that means and what that looks like. So that's the program. In the program, we talk everything from. Relationship to ambition and achievement, money and security, core values, zone of genius, experimentation, and a bunch of other things.
And it's a great, I'm biased, if you look at the NPS scores, it's been eight, nines and tens across the board, and predominantly tens across the board. So people have recovered from illness, navigated divorce. Recovered from addiction, moved abroad, extended their sabbaticals, found their callings and stepped in, started new companies.
So like we're starting to see the results, which is really exciting. Our next program actually launches in March of this year. I don't know when this podcast will go live applications open up.
Jason Jacobs: Soon, like, yeah, I'm editing myself using Descript and I'm finding the turnaround can be pretty quick. It's not, I wouldn't call it high production value, but it's cheap and fast and good enough, which for where I'm at is perfect.
Steve Schlafman: Yeah. Applications open next week, February 3rd and applications are due Feb 27th and the program kicks off on March 18th. And yeah, so we're really excited about that. So that's one offering. It's a mix. We call it, it's a blended experience with in person and then virtual. There aren't many of these programs that exist today.
Most are either retreats or cohort based courses online. We believe that a blended experience is best for a range of reasons. The second offering is. core personalized, individualized coaching one on one that's very personalized, where we take a lot of the foundations of our philosophy and the way we engage and weave that in.
But it's a lot more personalized and specific to the individual. And then what I'm really excited about. We had Andy Johns. I don't know if you've ever come across Andy. He's brilliant. And he's, he was previously he was the president of wealth front early Facebook
Jason Jacobs: Yeah, well, he was an early growth hacker, right?
Steve Schlafman: Yeah, exactly. And it was an EIR at Greylock and a VC and just like an amazing human being and went through his own crazy transformational journey. And Andy joined our team in the fall and he's basically had a product and what we call knowledge. And so he's in the process of building a new website that then, and I don't think I've ever.
shared this publicly. That's basically we're going to build the Web's largest repository of information for people navigating transition and change for these ambitious professionals. And so that's going to come starting in probably a few months and we're going to build out this whole knowledge library.
And then we're going to start to layer on online courses. I'm starting to work on what the next one is going to be. That's going to be pure virtual experience. And then we're going to see what unfolds. But I'd imagine similar to the annual review, we're going to launch a range of guides.
To support people depending on where they are in their journey. And yeah we're gonna go after this. We think there's a really special opportunity to build a great company and also do it in aligned with our values.
Jason Jacobs: Uh-huh, and this might be too personal, I've never asked this in a public forum like a podcast before, so if it is You don't have to answer it and we
Steve Schlafman: No, no
Jason Jacobs: take it out.
Steve Schlafman: off limits.
Jason Jacobs: but given your answer how we talked about ambition and for you how it's kind of three vectors company and family and health I want to ask you the same question about kind of where you're at and where you hope things will, or where things are heading over the next two, three, five years as it relates to family and health.
Steve Schlafman: Yeah. This year when I went through my annual review process, there were five values that I identified. The first is spacious presence. Which basically begins with me being awake, as I navigate life, unconscious. That's the first one. Second one is holistic health. The third is devotional service.
And I just think about those three things. The first two are related. Holistic health. And to me, it's, I gotta move my body a little bit every day. I have my meditation practice. And I need to get time in nature. And I have to Eliminate as much time on my mobile device as possible because it creates a lot of stress and anxiety.
And to me I want to be fit, I want to live a long life. And so that means. Regular body scans, blood work. It means movement. It's just, it's like treating my body as an expression and a vessel of life and honoring it, eating really clean and limiting sugar. Obviously I've been sober coming up on 10 years, so no alcohol.
No, no cannabis. I see an incredible therapist that's trained in a method that I'm actually learning called Takomi. That's been really life changing. So to me, that's the health bucket. And so it's just continuing to double down on what I'm already doing. I'm 46 years old. People think I'm in my early forties.
I take really good care of myself and that's not going to change. I can't be in going to back to that word devotional service. I can't be of service to my family and to my company. If I don't have a healthy body in mind. That's where it starts.
Jason Jacobs: What about family, Steve?
Steve Schlafman: And family I do drop off and pick up.
I do bedtime. I cook it's I, again, I don't think it's really doing anything outlandish beyond what I'm already doing. Like I'm a great partner to my wife. I'm in the trenches. I'm very much in the trenches and so I feel really good about it. Like I love reading with them.
I love being active and involved. Like it would break my heart. Like I have a few business trips coming up this year that are already planned and I have to go to Boulder for four days in April. And I'm like, Oh, like when I'm not near them, I can't sleep. I don't do as well without them.
And for me, I think. It's continuing just to double down on what I'm doing and really just continuing to lean into it and also not shy away from those feelings of like, when I am with them and I want to be working, like acknowledging them and expressing them and balancing it.
And it's a dialogue with my wife too. She's an entrepreneur, and she knows I'm building something new. And we're in constant communication, but family comes first and then the company comes second and that's just how it is right now
Jason Jacobs: So I have a couple ideas that I want to pitch to you and then maybe we can close out if that's okay. So,
Steve Schlafman: I want to hear
Jason Jacobs: yeah. So one is it's just something I've been thinking about, but you know, that's what I mean. Reid Hoffman wrote that book, blitzscaling kind of lionizing and walking through the process of one way to build technology companies, which happened to be a pervasive way in this last.
era of company building and some of the things we've been talking about, about this new way to build where it tends to be more appealing to people with middle age that have more going on, but it's not exclusively for those people. It's just people that want to be more balanced and more intentional and not necessarily have work consume their whole lives and things like that.
So what I'm wondering is for founders that are building this new way, if there's a new term for how to build those companies, then if someone should write that book, that's one idea.
Steve Schlafman: Yeah, I love that I love the idea a book that we love internally that everyone on the team has read is it doesn't have to be crazy at work by Jason Freed of 30 of I think they, I think now the company is called base camp or maybe they rebranded back to 37 signals. I don't know, but I think that's what we look to.
And I think he was. Among the first to use the term calm company. I don't know what it's called. But like w we're taking that and we're doing it in our own way as well. Like we're infusing our own way into it. But yeah we take a lot of inspiration from those guys.
Jason Jacobs: And the other one that I wanted to run by you is in my travels as I, you know, I'm catching up with old friends and meeting new friends and sorting through how I'm going to build different and finding other people that are building different or have built different or interested in figuring out how to build different.
What I'm finding is that they have just as many problems, insecurities tensions, things they're wrestling with, they're just as dysfunctional, if you will, as young founders but they just have different problems, right? It's not less problems, it's just different problems, and Silicon Val
Steve Schlafman: different contexts, different problems.
Jason Jacobs: Yeah!
And so there's this show, Silicon Valley, that was you know, that I feel like the prototype characters were these like, you know, YC hacker types, right? And it was all kind of built like, like the satirical version of, of that and bringing their stresses and insecurities and problems and tensions and, and all that to life.
And it was, it was funny as hell. I, I used to tune into that. Religiously. And so what I'm wondering, if there could be a new one focused on this demographic called Foggy Founders and it could be an ongoing series, but it doesn't need to start there. Like, and I know you're anti phone and, and stuff, so maybe this isn't going to resonate with you,
Steve Schlafman: I'm not anti phone. I'm pro responsible phone usage.
Jason Jacobs: But you could start just by fleshing out characters on someplace like TikTok or Instagram, and then if you kind of bring the characters to life and build followings around specific characters, you can start weaving them together into stories that could graduate into a show. So that's another idea that I've been kicking around that I wanted to run by you.
Steve Schlafman: I I love it. It's creative. What I would say is initially, as I heard the words fogey founders, I felt a little bit of constriction because I don't consider us fogies. I feel like we're really at our prime. Like we've been building to this moment for several decades, and this is a real opportunity for us to be able to show the world what we're capable of, but doing it in an entirely new way.
So I love the show concept. I can already imagine scenes in my head, though I don't like the term fogey cause I think
Jason Jacobs: Give me an alternative.
Steve Schlafman: I don't
Jason Jacobs: an alternative.
Steve Schlafman: I don't know, but I'd imagine something good will pop into my mind and I'll text you about it.
Jason Jacobs: Awesome. Well, Steve, this has been an awesome discussion. Is there anything I didn't ask that I should have or any parting words for listeners?
Steve Schlafman: I here's what I would say is like for us. At downshift we believe that, especially in this time in life that particularly mid age that it's that you can be a great parent. You can have some semblance of balance. If that's what you really want.
And if you want to go build, my wife is part of YPO. If you want to go try to like, there's a lot of founders that she knows that are in transition and they just go find the next big opportunity. If that's what you want to do. Great, go do it if you want to do it slightly differently this time around and you want to be more intentional and holistic about it, then I think downshift is a great option and the way we view it is we're working on this for the next five to 10 years, hopefully, God willing, right?
And we can take a really long term view and I just think with the set of tools that are coming out, it allows us to get a lot of leverage and we can build it exactly in the way that we want to build it. And I think for us, we want to do it in as a humanely possible way that's aligned with our values and maintain a brisk pace, but not sprinting and burn ourselves out.
We want to have fun doing it.
Jason Jacobs: And then last question, just who do you want to hear from and how might they get in touch with you?
Steve Schlafman: Yeah, if anything, what I said resonates and speaks to you feel free to reach out. You can find me downshift. me is our website. So you can check it out. Our next cohort kicks off in March and applications are due towards the end of February. We had over a hundred people on our wait list, which is pretty amazing already.
And then you can find me on my personal site, schlaf. co, which is just, you can learn a lot about the path that I've been on. And then you can find me on Twitter at schlaf, S C H L A F at schlaff. And I write a sub stack called where the road bends. And that also has a lot of my longer form essays and musings about walking the path and going through transition and supporting others through that process.
Jason Jacobs: All right, Steve. Well, thanks again for coming on. Always a pleasure.
Steve Schlafman: Thanks.
Jason Jacobs: Thank you for tuning into the next, next, if you enjoyed it, you can subscribe from your favorite podcast player. In addition to the podcast, which typically publishes weekly, there's also a weekly newsletter on sub stack at the next, next dot sub stack. com. That's essentially for weekly accountability of the ground.
I'm covering areas I'm tackling next and where I could use some help as well. And it's a great area to foster discussion and dialogue around the topics that we cover on the show. Thanks for tuning in. See you next week!