Search & Replace Episode S01E04: Daniel Tobon

Daniel Tobon has held a few different roles in his career. As a self-described corporate lawyer turned serial entrepreneur, he’s been a startup founder, a general counsel, a COO and a CEO. He also served in the US Army Infantry, and it’s a group of his fellow combat veterans that noticed that things weren’t quite right with Daniel’s work/life balance. 

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Announcer: [00:00:00] Support for the following podcast is provided by the user experience specialist at Johns and Taylor, more information follows this episode. 

Joe Taylor: [00:00:10] If the biggest battle you were fighting is over your calendar, there's an army veteran who's got a simple plan to help. I'm Joe Taylor, Jr. This is Search and Replace

Daniel Tobon has held a few different roles in his career. As a self-described corporate lawyer turned serial entrepreneur. He's been a startup founder, a general counsel, a COO and the CEO. He also served in the U S Army Infantry and it's a group of his fellow combat veterans that noticed that things weren't quite right with Daniel's work life balance.

Daniel Tobon: [00:00:46] We do this kind of small reunion for all the guys that were in combat in Iraq together. And I was very much looking forward to this weekend. We were going out to Colorado in a small mountain town, just kind of hanging out and getting some skiing in. And I spent a lot of time away from those guys working. To the point where even they were like, Hey, what's going on, man?  You know, you're supposed to be relaxing or hanging out with us. Like, Hey man, are you okay? You seem stressed. And in on me while we were supposed to be in this like relaxing, fun environment. And that's when I realized maybe I wasn't ok. I was miserable. I don't get to see these guys very often- some of my closest friends. I should have been completely focused on enjoying that time and being in that moment.

And then when those guys started making sure that my mental health was okay, it wasn't directly connected to something we saw in Iraq and it was connected to my job. That's when I realized that, like, what the hell am I doing. 

Joe Taylor: [00:01:44] One Daniel was doing was fully immersing himself in startup culture.

But the practice of throwing yourself completely into your work isn't just a Silicon Valley trend. Here in the United States, company leaders find themselves trading lots of time now for the promise of a future payoff. 

Daniel Tobon: [00:02:02] Time is probably your most valuable commodity. So when you get into the rhythm of an early stage startup, it's one of the cheapest commodities that you have to spend.

So you train yourself to just be available for everybody at all times. And once you get in that rhythm, it's really hard to step back from that and change the way you work. One of the biggest things that gets founders and executives at these early stage companies is the fatigue. And I believe a lot of that fatigue comes from the way that we trade ourselves as early stage entrepreneurs, to be so giving with the time. 

Joe Taylor: [00:02:38] Fatigue came up in conversations between Daniel and his wife, who pointed out that her high- profile career didn't come with the same kinds of all-consuming expectations. 

Daniel Tobon: [00:02:48] My wife is also a person with a very demanding career. She's a liver transplant doctor at the children's hospital. And she knows when her vacations are going to be, she's going to know which weekend she's on call, she's going to know when she's on service. So it's far less traumatizing for her to submit to this really demanding lifestyle then it was for me where the grind culture and the hustle culture, that's permeated American work life- and probably started with a startup culture. So the first thing I did, when I was trying to solve this problem, was I sat down and thought about it.

That's how I came up with those solutions that worked for me. I had more time to think about my mental health and how happy I was and the things that I could do in order to change that. And then I get to use that extra time that I had. My wife and I started planning vacations with a lot more certainty and we weren't buying refundable tickets just in case I had to bail.

So, it really helped and improved the happiness in my relationship with my partner. 

Joe Taylor: [00:03:51] Daniel discovered that setting boundaries around his time and getting to clear conversations about those boundaries made all the difference in reclaiming his calendar. That said those conversations, they sound different depending on who you're talking to. 

Daniel Tobon: [00:04:06] Some boundaries are very easy to set and some were very difficult to set.

Just by nature of the relationship and types of interactions that I would have with these different people that were competing for my time. Obviously with subordinates, where you control the structure and you control the ground rules, it's much easier to do that. With people that are your peers or people that you report to, those are where I find that most people get in trouble. Those are the people that justify expectation of their position, you have to defer to even when it would be not socially acceptable in any other kind of interaction. I found that when I started to think about how I would set up these boundaries, I literally just tracked the people that were making requests for my time. And then I started basically figuring out how often they made these requests and my scale of how inappropriate these requests were. One board member who repeatedly wanted Saturday evening meetings, beyond what was already normally acceptable for a board member request.

And with that, I have to make a concerted effort to address that person directly and be like, Hey this is what you're doing to me and my team. This is why I don't think it's a good idea to do this. And this is where I suggest as a change that works for everybody. And it turned out to the guy who was just, like, retired and sitting on his balcony looking at the ocean and he was wanting to have something to do on a Saturday afternoon. I'm like, okay great. Let's do that Thursday evenings. And then we can be your Thursday evening hang out. 

Joe Taylor: [00:05:37] So Daniel's got some thoughts for you if you're considering how to take better control over the boundaries in your professional relationships. 

Daniel Tobon: [00:05:44] No one else will make it a priority except you.

So that's number one- the number one thing to keep in mind. Companies don't have social workers or mental health care specialists on staff who are going to come in and say, Hey Dan, you need to slow it down. That's not how our institutions work. So, most people will completely understand. One because they realize that you're human as well and you need these things in order to live your life. And two, because a lot of times it actually starts conversations with other people about how they should do that more. And then it leads to a conversation like this where they're like, we would like to do this. And the one negative response that I did receive was from somebody who was one of these serial offenders that just demanded time all the time, no matter when.

And I actually ended that professional relationships specifically because when I told that person not only did they respond negatively, they refused to listen or abide by that. That's a decision as the priorities that you have to make if you you're actually going to set these boundaries and be consistent. 

Joe Taylor: [00:06:49] That's entrepreneur Daniel Tobon. You can learn more about Daniel and find links to a few of his projects on our website at

Announcer: [00:07:04] This has been a Podcast Taxi radio production. Support for Search and Replace is provided by Johns and Taylor user, experience specialists serving media and technology companies that want their websites to work. Learn more about how top performing businesses eliminate barriers between customers and their goals at

Joe Taylor Jr. has produced stories about media, technology, entertainment, and personal finance for over 25 years. His work has been featured on NPR, CNBC, Financial Times Television, and ABC News. After launching one of public radio's first successful digital platforms, Joe helped dozens of client companies launch or migrate their online content libraries. Today, Joe serves as a user experience consultant for a variety of Fortune 500 and Inc. 5000 businesses. Twitter | Facebook | Instagram

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