Peer Effect

The Power of Slowing Down to Scale Up, with Sam Rosen

James Johnson Season 3 Episode 20

What if the secret to scaling your business successfully lies not in speeding up but in slowing down?

In this episode, I explore this unconventional yet powerful strategy with Sam Rosen, co-founder and CEO of DeskPass. From the inception of DeskPass to its current state post-Series A, Sam shares his transformative journey of stepping back to make thoughtful, less emotionally charged decisions.

Listen to the full episode as we unpack:
• The critical role patience and empathy play in leadership
• How creating space for reflection can lead to improved outcomes and stronger team relationships.
• Practical tips for managing the chaos of entrepreneurial life.

For more insights, follow Sam Rosen on LinkedIn!

More from James:

Connect with James on LinkedIn or at peer-effect.com


Speaker 1:

One lesson that most founders learn in their first three years of their business is the idea of it's all about speed, and that definitely works in the survival stage of zero to one, but is often a lesson that needs to be unlearned as you start scaling later on. That's why I'm delighted today to be joined by Sam Rosen. He's the co-founder and CEO of DeskPask, a platform that's changing the way businesses and individuals think about flexible workspaces by connecting them with over 2,200 unique locations in 220 cities. But, like most founders, sam's journey hasn't been without its challenges, and today he's here to share the wisdom he's picked up along the way. If it's your first time listening, I'm James Johnson and I coach Series A Plus founders to take back control so they can take their business further and live a great life. Before we kick things off, be sure to follow the show or add it to your favorites to avoid missing out on new insightful founder stories.

Speaker 2:

So it's called DeskPass and what we do is we connect companies and individuals with co-working and flexible workspaces all over the world. We do it through a platform that means like JJ can, hey, I'm looking for a meeting space in the West End tomorrow for three people at 2 pm, and you could find that through our platform. But we also predominantly work with companies small and large large that are offering these types of spaces to their employees so that they can give employees places to work and connect and collaborate outside of just their home or a kind of a more traditional office and what sort of stage are you just to set the scene for the listeners?

Speaker 1:

Sort of size braids, anything like that?

Speaker 2:

Yeah, so we did our Series A. In October of last year we did an interesting deal with a company called Industrious, which is one of the largest co-working operators in the world, and we merged. They owned a company called Breather I think Series C or D company that raised 150 million dollars. We merged that company with our company. So we've been at it for like five, six years and have thousands and thousands of customers all over the world that use our platform and have about 2200 unique locations in 220 cities all over the world sounds like you're well into the one to two stage in terms of some days some days we're way back at one I've started to feel like minus one some days.

Speaker 1:

It's kind of like yeah, yeah on.

Speaker 2:

Yeah, I think that any any good entrepreneur that in common, unless something's uncanny.

Speaker 1:

So now you're at this stage and you've been doing this for a while what is one thing you'd share with other late-stage founders?

Speaker 2:

You know, I'm curious if other people have offered this advice, and it's something that I've gotten a little slack about sometimes.

Speaker 2:

But it's this notion of slowing down, I think, like in this game that we play and the sort of rat race of it all.

Speaker 2:

It's so often it's go fast, make decisions quickly and fail and learn from that, and I'm all for all of those things, but to me, what's been like, I think, a really important tool in my toolbox is the ability to slow down and take a beat, and especially when it comes to like decision making important decision making often there's like this imminent demand, like we have to make this decision right now, we have to move forward right now, we have to take action now, and there's a this imminent demand like we have to make this decision right now, we have to move forward right now, we have to take action now, and there's a lot of like, I think, pressure around that, and those are the moments that I found are really helpful for me to actually do the opposite, which is to stop, is to take a beat, take a breath, take a night step away from the problem, and I find that I really tend to find a lot of clarity and focus and a lot of like. The emotion of the decision making goes away in that process.

Speaker 1:

Was there a particular instance that really sort of caused this change of approach?

Speaker 2:

You know, it's been something in my career that I think has happened over and over again. So I think often when it comes to decisions around funding, like around hiring or firing, like, there's people that I've often acted like very emotionally to, and I'm kind of an emotional person, so there are folks that I think maybe a younger me or a less disciplined person of myself would have been like rash in either kind of acting emotionally in a decision to let somebody to go or to say something that would be like a net negative and by kind of taking the beat, having the patience. The other thing that I think is kind of interesting about this tactic is, in the heat of it, it's two ways. So especially in like a discussion or in a fight, in that space I tend to find that it gives room for the other person, like the person you're counterparty, to do the same. So when you come back to the table you're not quite at the same odds.

Speaker 2:

You might have been before where both have had some time to empathize with the other person's position, to empathize with the other person's position and though it might not be, hey, I've changed my mind completely, but I've like taken the time to think about your point of view, your perspective and let's. I could kind of come to the table again and I don't know. To me that's kind of like that vulnerability and and and that is where the magic happens. So I know that's not the most specific examples, but for me it often has to do with gut emotional stuff, with people where I feel triggered and that triggering makes me want to act very responsibly and that beat allows me to take a break. What I find is it works two ways. It works for me, but it often works for that. Your counterparty.

Speaker 1:

So how would that work in practice? So you're kind of you're in it, you're in a meeting, it's of. It becomes a bit of a bit of a sort of a computational emotionally charged. What would you, what would you, what would you say or do?

Speaker 2:

you know, often it's like, hey man, hey woman, I hear you, I don't think we have to decide this right now, like no one's gonna die, like we're not gonna lose a customer like this can wait 24 hours. I'm going to take a beat, let's take a break and let's connect again tomorrow or the next day. It's really just the process of stopping and shutting it down. I think sometimes there's resistance to that, like no, we have to figure this out now. And it's like I don't know. In my experience in running a business, there are very few decisions that have to be made on the spot, so it's it's kind of pushing against that, that instinct and reaction that like no, this has to figure, be figured out now so does the resistance come to a person where they're like?

Speaker 1:

no, no, this needs to be. This needs to be resolved now yeah, absolutely.

Speaker 2:

I mean, have you experienced this before?

Speaker 1:

yeah, yeah, it's interesting. When you talked about this idea of taking a, taking a beat, I thought this might go in direction of, let's say, not making decisions rashly or creating space to examine things, but it's people haven't. People haven't flagged this like this one-on-one situation as a, as a space to take the time, because I do agree, like I think, particularly as the leader, you can control that time frame, and you can if you're conscious about it, if you make a conscious choice to go no, okay, we can slow down, because everyone often thinks that speed is the way to impress. It's like it's a very let's take it off let's get it done.

Speaker 1:

Let's move forward, let's move, but are you moving in the right direction?

Speaker 2:

I. That, I think, is the heart of it, is like I also think is like an early stage entrepreneur, if you have backing. Like it's like go, go, go. We don't have time to waste make a decision. But it's like go, go, go, we don't have time to waste. Make a decision. But it's like make the right. Making the right decision tomorrow is going to be a better outcome than making a shitty sort of emotionally driven decision now, or even just like the like, when things sort of rise to the level of like oh, this is, this, is not war, this is this is not war, this is business. You know what I mean.

Speaker 2:

When I think things like there's value in emotional conversations, there's value in tension, there's value in some aggressiveness, but like there's a lot of value in stopping and taking a beat and sort of what comes with that. I know like for me, over the last couple years I've like through therapy, I've learned a lot about your nervous system, right, and it's this notion of, like your sympathetic and parasympathetic nervous system and it's basically that when you are triggered in that sympathetic nervous system, your body changes, like your tools that you have available to you change and you make different types of decisions than if you are in sort of this other mode. The only way to fix that, the only way to solve that, is to calm down. It works with your partner too. It's like if your partner is triggered and angry and like in this mode, the only thing you can do as a good partner is help calm them down and help them switch modes.

Speaker 2:

And unlocking that mode like that's where, like I think constructive, uh work can be done. So when you're it, when you, when you, when you recognize you're in that mode, that's, I think, a really good tactic and tool is like, alright, let's get out of that mode. And to me it's just easiest to say hey, let's take a break, we'll talk about this later, and that alone solves a lot. And then you can look at it and evaluate it and hopefully now you've measured it with whoever you're working with perspective a little bit better and can empathize.

Speaker 1:

Have you heard of a book called Chimp Paradox by Professor Steve Peters?

Speaker 2:

No, I think I've seen Steve Peters talk about nervous system stuff.

Speaker 1:

It's to do with the brain. It's basically there's a model he was the sports psychologist for, like, the british olympic team and england football team, and he came up with this model which is simplified like transaction analysis and brings in this idea of, like you have this you have your chimps, your human and your computer in your brain and basically when your chimp is taking control, like like you visibly look different, like it's kind of you respond in a different way, your motivations change and actually that's taking, it's very responsive, whereas actually a human is who you'd like to be and like when you take a breath and it's kind of.

Speaker 1:

But once you're in chimp communication and certainly when you go chimp to chimp with someone else, it's a very different thing and actually the tactics to like move away from that, how to get people back into human and how to then have that humor. It's. It's all the stuff that you're you're talking about, so I I think that's obviously, I think that's right on.

Speaker 1:

You can like, I think, in debate, in a conversation, you can always, you can feel it when you do it and you can feel it when someone else does it I increasingly feel that efficiency is actually a dangerous word, because it's really saying how can we do something quicker, and it doesn't really feel like are we even doing the right thing in the first place and I and I think particularly for founders we it does start with us, like how we like our culture does start with us.

Speaker 1:

Our control of our business, of our lives, starts with us. But I really think, looking at effectiveness rather than efficiency, because actually take a step back. Do we need to do everything we're doing? Probably not, like we can do a lot less. It's all about, like, achieving more rather than doing more.

Speaker 2:

Totally.

Speaker 1:

At Betrayers. We're so brainwashed by the early stage of our career where it's like here's a task list, get it done. Okay, well done get promoted yeah, okay, you've got bigger task list. Now make your team do that task this quicker. Well done, and so, by the time you were found the number of times I'm going to be oh, how do I make my time management more better? How do I get more efficient? Do I make more? It's like you're trying to solve the wrong problem, like efficiency is like almost like fourth down the list.

Speaker 2:

Yeah, I think that's so wise. Actually, the guy who originally founded Breather, this company that we merged with, is a guy named Julian Shapiro, and he had a post the other day that really hit me and I'm so guilty of this and I think it's a really hard, hard thing to do. You have to be really disciplined and really smart. But it's like if you've got 30 things on your to-do list and I do you're doing it wrong. You know what I mean. Like there's no way there are 30 things that are going to. You know, there are, at best, five things you could be working on right now that deserve your time will move the needle.

Speaker 2:

And whenever I hear that, it hits really hard because I think, especially at, like, the founder level, you get a lot on your plate and there's a lot you can be doing, and it's not you know, it's not how much you get done, it's getting the right things done in the right order, and that takes a lot of discipline and a lot of effort and a lot of practice. But it's true of effort and a lot of practice, but it's true. I mean I, so many times I'm like you you cross off these small things because they're easy wins and it gets your list down. But it's like, man, if I just did this one thing today, it would have been a much better use of my time than the 10 things that I did. Do.

Speaker 1:

I think the other thing is it's like who controls the urgence? There's a prioritization on your list. I think it can become quite easy, particularly into the second phase of scaling. Suddenly it's like maybe it's your customers controlling your to-do lists, like where it goes where. Maybe it's your VC if they're putting money in, but often it kind of your team, your team can hijack your in. But often it's kind of your team, your team can hijack your.

Speaker 1:

Totally, I think it's really hard to create the space. Okay, no, no. What are my priorities? I'm the founder. How do I control this?

Speaker 2:

How do I?

Speaker 1:

create the space to really make sure I'm working on things that I believe are going to really move the needle.

Speaker 2:

Yeah, I mean in that Call Calm Company book. One of the things they talk about is this idea that anyone can put a time on your calendar whenever. It's such a crazy idea that somebody can interject a meeting and a time in your day, sometimes without your consent, consent or knowledge. Right, it's such a wild premise and it's like how do you create the rules and space to protect that, not just for yourself but for your company and for your culture?

Speaker 1:

how do you set that space calmness for your team?

Speaker 2:

I mean, I think a lot of it is leading by example in practice. I think part of it is. And then cultural, like how you respect and appreciate other people's time. There are like more practical tools, right, like time blocking. You know, I will block off large parts of my calendar that are a do not disturb or I'm working like don't bug me here, and you know, and I think everyone in our company knows, like you know, if it's an emergency, like that's fine, right. But I think that practice of other people seeing that, hey, this is blog, that's okay to do, that's okay to say, I think in tools like slack, like communication channels, this notion of like what is the right communication method for a particular problem, oftentimes laying out a problem and creating a thread, that's like async, that I can like take the time to lay out the problem, the question, and give people the ability to think about it, respond to it on their own time frame and kind of in their own way Versus, like hey, we're going to all hop on a call, we all have to be present in this call at this time, irrespective of what's going on in people's professional or personal life.

Speaker 2:

Some of it, I think, is just like modeling what works for you and sharing those insights. And then I think there's some rules like a like, and I've seen something like with slack. It's like try to keep things in channels and not in like one-off messages. If things are not urgent, don't make them a phone call or a text message or a Slack message. Make them an email or make them a whatever kind of pick-of-your-poison project management tool.

Speaker 2:

Put them there. But it's also like then, as a leader, you have to make sure the priorities are clear and everybody is aligned on what is the most important thing and how we should be focusing our time and energy I think it's actually quite hard, isn't it?

Speaker 1:

it's a lot of work to create a calm company because it requires, like, clear goals. It requires good role modeling by you, requires thinking ahead, it requires hiring the right people, like there are so many elements that you need to know. It's much easier to create a hectic, just get stuff done quickly culture, even if, and then you might feel good about it for three years before your business crashes, but it's much, much harder to do that the deep work to create a calm company yeah, and I think it's you're gonna mess up most of the time.

Speaker 2:

It's not about getting it right the first time and sticking with it. It's about like evolving. Every company is different. Tactics work for individually, as a company, differently, so it's like learning, screwing it up, trying it again, reminding people. You're letting people have a voice in it. I always think about this with workspace, because this is our business, right? It's like where you get your best work done might be very different than where I get my best work done because of your job, because of what project you're working on, because of how your week's going. It's not a static thing. It's a set of processes and tools that hopefully are always evolving and hopefully you create a culture within your organization that you can talk about it.

Speaker 1:

Big thanks to Sam Rosen for joining us on today's show. If you've listened to the show before, you'll know that I'm a huge advocate for going slow to get there faster and, reflecting on my conversation with Sam, it's clear that taking a moment to pause and reflect really is essential for resolving conflict or making decisions that push your businesses forward. Rushing might feel like it's getting you there quickly, but slowing down will get you there right. Join me next week as we continue to learn from top founders who've been exactly where you are, because the truth is, you don't need to navigate founder life alone and you can avoid making mistakes by learning from those who've paved the way. See you next time.

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