Rachel Chalmers:

Today, I'm so thrilled to welcome to the podcast, Brad Henriksen. Brad's a leadership coach and the co-organizer of the San Francisco CTO Club. He's the former CTO of Scoop Technologies and VP of Engineering at Earnest, which was acquired by Navient and Keen IO, which was acquired by Scale Works. Brad co-founded two start ups of his own, Shotwell products and Zoosk, which was acquired by Spark Networks. He has a computer science degree from the University of Washington and spent six years at Microsoft. Brad, thank you so much for coming on the show. It's great to have you.

Brad Henrickson:

It's great to be here, Rachel. Thanks for having me.

Rachel Chalmers:

Tell us about the San Francisco CTO club.

Brad Henrickson:

I really love the San Francisco CTO club. We've built this fantastic community of technical leaders in the Bay Area, a really open group. We have a lot of discussions around a variety of different topics. We've been going for about five years. We'll cover topics like founding companies, mental health, and organizational maturation. It's a place for all of us to help really develop our thinking in startups and how we think about our practice as leaders within those organizations. For me, it's been a fantastic space to help develop my practice and also build a community that's really passionate about bringing technology and driving change in industry. 

Rachel Chalmers:

What would you say are the top three issues on CTO’s minds these days?

Brad Henrickson:

‍Well, this last year is - I think a lot of us have been really aware of the challenges in our personal lives and also in our professional lives. There've been a lot of challenges that we've been looking at, whether it be balancing our work and personal lives and how we think about our mental health. That's been a very active forefront one because we've been very driven by our stories and these organizations that have been trying to build throughout this period of time. It's been hard to figure out how to do that, especially as an executive. How do we navigate those things? How do we think which works for us, what works for our larger community? That's been one of the really big ones that's been recurrent.

A second one that's really come up a lot has been people trying to figure out remote work. How we think about hiring, how we attract talent. This is a perennial topic. This topic has been around as long as I've been involved in industry, as you try to figure out the way to navigate this, but it's really shifted a lot. It used to be a lot more about how to bring people into my Bay Area company. How do I attract people to that opportunity? How do we hire people in a variety of different locales and onboard them in a way that really makes sense to integrate and have them be additive to our company cultures? That's been an important second one. That's, I think, a little bit more unique to this last year.

And a third one has been organizational maturation. How do you deal with organizational growth and contraction with some of the different changes we've seen this last year? There's been a lot more of that than you would typically see, a lot more fluctuation in terms of the company's rate of growth or contractions as well. 

Rachel Chalmers:

All three issues make me think about precarity. Even the least ego driven technical leaders are invested in our narrative because we want to make sure that we get the gig after next and the gig after that. We want to still be able to provide for our families. The challenges with hiring and with hiring remotely are how do we guarantee people's wellbeing? How do we give them some kind of job security in a market that is so volatile?

Brad Henrickson:

I think that's very much true. There has been this precariousness through this last period, and I think it's asked a lot more from people to step up to that and understand how we're going to navigate that. That's just been one of these pieces I don't think any of us really saw coming for this last year. Creating new companies and new offerings into the market has always been kind of a precarious thing, but not coming even closer to home in terms of how do we actually navigate that. It's really important this last year to have invested in community and finding support to be able to be successful in that for yourself, for your career and for those in your community.

Rachel Chalmers:

I've got to say what a delightful and refreshing thing it is to hear a man talk about the importance of mental health in the workplace and that how you manage your mental health is a qualifier, a key component of how you model leadership. I think women in the industry, as the embattled gender, have long had back channels in ways to band together and share resources. I love to see men stepping up and doing some of that work for themselves as well. Is it difficult to overcome the taboos about talking about these kinds of things

Brad Henrickson:

I'd say that, yes, for me. When I first started an industry, I very much had this attitude of I'm just going to soldier through this or I'm going to tough it out. There was a lot of attitude around ideas of grit and like this very masculine way of talking about being a leader in technology. It took a lot of work, internal work, finding support to be able to change some of that lens and really come around to thinking about self care and community in a way that was outside of just myself, for myself, but also for people around me. So it wasn't intuitive for me. I don't think it's intuitive for a lot of people, particularly in the engineering field, as people are starting to come up. So it definitely took a lot of work for me to get there. It wasn't necessarily the first thing that would come to mind as challenges would appear when I was starting.

Rachel Chalmers:

I really hear that because I spent the first 20 years of my career soldiering through the hard times as well and I don't think women are naturally more nurturing. I think we're forced into it by circumstance. You eventually realize that you're reacting from a place of damage and all of the hits that you've taken, and you have to deconstruct all of that to be present for people in a real way. But I think there is a growing awareness that we need to dismantle those because when you find yourself treating younger people coming into the industry the way you were treated that you hated at the time, if you have a shred of self-awareness, you've got to try and push back against those implanted impulses to do harm.

Brad Henrickson:

I very much agree. I think a lot of the responsibility for making sure that we create a workplace that really supports people, however they show up or whatever their biases are, is that we end up helping support people along that way. It's really incumbent on those of us who've been around for a while to make sure that that holds true. I don't want to pass down some of those experiences, some of them which are really positive, frankly, but some of the more negative ones to people who are now coming to the industry.

Rachel Chalmers:

More generally, what has holding CTO and VP engineering positions taught you about innovation, about how to bring new products to market?

Brad Henrickson:

It's a great question. First thing that I would say is that I come to this from a technologist perspective. I've been involved in technology for a very long time. For the longest while for me, it very much started with technology and I kind of moved around to what's the innovation and what's the thing that we're trying to realize in the world. What I've really learned is if you really want to think about innovation and technology, you have to start with, what's the thing that we want to bring into the world? What is this audacious idea that I believe is possible, maybe not even possible, but that I dream that I wish was actually realized, something that would delight and exceed customers expectations.

You have to start there. If you start with this, it is the well-contained problem that we're at. It's a problem that we have today. I'm going to make it 10 percent better. You're really not going to be driving that innovative idea that truly creates that step function change, which creates impact for customers and for people and really changes the world around us. One of the quotes I find really interesting here is from William Gibson, which is “the future is already here, just not evenly distributed.” Looking at the environment around you and dreaming of what's possible, there's more that's possible than I think most of us realize on a daily basis.  Starting there and then moving to, “How do we want to realize what's possible?”. “What's there for us to learn?” It’s a really key way to do it. If you start with where you are today, you're going to see all the barriers and everything that gets in the way for you to realize your dream. You've got to start with the dream and then work backwards. I think you'll really surprise yourselves. I certainly surprised myself in some ways and what's possible for teams to accomplish if you do that. Technology is not an end in itself. It's just something which helps you orient on creating that impact.

Rachel Chalmers:

I love when people pull in science fiction references because I think what gets lost in implementing technology is precisely that imagination, that vision, that boldness to bring into being, things that don't exist yet. More of us in technology than we necessarily admit are inspired by folks like Gibson and Kim Stanley Robinson and Bruce Stirling, who have audacious versions of the future that sound really good and that we want to build towards.

Brad Henrickson:

It's been very influential for me in a lot of ways in terms of dreaming of what's possible, but it's also very somewhat at odds with the engineering mindset where there's this very, very grounded creating something tangible in the world that must work, which is very separate from this big dream audacity that's present with a lot of that science fiction writing. Another really fascinating piece of science fiction which leads into innovation is that there's a lot of thinking about how societies function in science fiction. At the end of the day, if you're a business trying to create something that creates changes, that change doesn't lie in the technology, it lies in society, and it changes some of the framing in terms of where are you thinking about things, what are the ideas that you're playing with and then you can route back at the technology.

Rachel Chalmers:

So I've got to both agree and disagree. You're completely right that when you're coding just to implement a function, you're pretty narrowly focused on your OKRs and your KPIs, and it's just an algorithm in algorithm out type function. But when you look back to the great early thinkers of computer science people like Dijkstra and the creators of Unix, they were systems thinkers by definition. They thought about networks and they thought about network effects and the social impacts of technology in a way that we kind of lost. I do wonder if it's because as tech became more and more profitable, we had the cynical finance bros come in and make everything about money. We lost respect for those soft skills, those social skills, and respect for the visions that could grow out of them.

Brad Henrickson:

I certainly think there's been a lot of large shifts in how we've oriented around our technology. I was watching Something Ventured the other day for a discussion, and it was really fascinating to go back to some of those parts on how capital is introduced. There's something very true to what you're talking about. This idea of earlier on there was a little bit more of a pure ideation and playing with ideas of what was possible. These ideas around what we could do with artificial intelligence in the summer. There are a lot of just really fascinating pieces of the creation of Unix, as you're talking about. There were these great ideas that people were bringing to bear about what was possible to be done, and a lot of that did change.

Nowadays, a lot of people in the computer science field and in the software development field are trying to think about great ideas, but they're also the hull container in the landscape. A lot of that gets framed by returns. Like what is the thing that we're building? What's the revenue that's attached for it? I don't think when they're saying we're going to create artificial intelligence in a summer, there'll be this big monetary return on the other side of it. It was more pure research idea or with creating some of these great systems like Unix, it was what is a vision for an operating system that we think would be really incredible. I think the landscape has shifted quite a lot from where it once was.

Rachel Chalmers:

Another science fiction book I like to quote is Vernor Vinge's A Deepness in the Sky, in which one of the characters Pham, his title is he's a software archeologist, and he's digging through the software systems on his starship, and he finds that the system clock started when humans first walked on the Moon, and you realize that within a degree of margin of error, he's talking about Unix. It's the Unix clock that started in 1970 and has been going into this far future. It's completely plausible because we already have Unix systems running on other planets. You think about the vision with which those men put together a system so open and flexible and adaptable that was still running at 50 years later. It will probably be running thousands of years in the future. That's the kind of ambition in a very practical sense that drew me into the tech industry in the first place and that I'm always drawn to when I find it in other people.

Brad Henrickson:

That makes a lot of sense to me. I believe we've lost some of that in the current day and age. There's such a rapidity to how we create things today that the long term mindset to envision where you're going to be down the line requires space, requires not being in this point of threat of, “How do I get this thing across the line?” You need to back up from the time pressure and say, “What's possible for us to realize?” That's always been my perspective about it. I spent a lot of time in the, “What’s next in the immediate?” mindset and it's taken a while to shift to this longer perspective of, where do we really want to be? What's the larger vision of it? I think I largely agree with you in terms of that lens.

Rachel Chalmers:

I really wanted to ask about your coaching practice. I'm doing a lot of coaching for our accelerator teams at the moment. What are your coaching clients struggling with the most these days?

Brad Henrickson:

Some of this overlaps with some of the things people are seeing within the San Francisco CTO Club. There's definitely the overcoming burnout piece, which has become very prevalent. There's been a lot of people who are working round the clock, particularly if they have offices in a variety of different time zones. I know some companies have some people working in Pacific Time and people in India, and it's just all around the clock and the barriers to work have all completely dropped. There've been a lot of people who are just going through this cycle and not figuring out how to rejuvenate for themselves, how to carve out their space. That's been one of these recurrent themes in the people I've been working with is, “How do you actually deal with that? How do you actually create that space? How do you make sure that you're feeling reached?” So that's a significant one.

Another one, because a lot of the companies I'm talking about are in this growth phase. There's a lot of questions about how we deal with the next stage. “How do we deal with my organization doubling in size? What do I think about organizational structures? How do I think about my role as a leader?” Interestingly, I find a lot of these two. These two topics that I've mentioned really overlap. What I'm seeing from people is that they have these narratives and stories about what they should be doing and as more fuel gets put on the fire, they just keep bringing on more and more to help them, to help grow with the company. “I need to do X, Y and Z, and I should be doing all of these things and I can't drop any of them”.  This contributes to the burnout.

I've seen a lot of people who are struggling with this growth. No good boundaries with time and so theyr are not finding ways to restore themselves. And they're in a position where they can make a great impact and they're paying the price on every single side and people are having a hard time finding the support that they need to navigate that for themselves. That's been a very consistent theme with people I've been working with is navigating that piece of it, particularly with executives, in which case they feel so closely aligned to what their company is doing and what their team is doing.

Rachel Chalmers:

That's the thing we're socialized so strongly to peg our sense of self-worth, to whether or not we meet the expectations we place on ourselves. At the same time, there's all of this societal pressure to place completely unreasonable expectations on ourselves, and you just can't square that circle. You end up in a place of, I am not worth anything because I am not doing all of the work in the world, and that's not a useful place to be.

Brad Henrickson:

Exactly. We pay a very high cost for this, but also those around us and the things that we care about pay a high cost. There's a lot of elements here to me around identity and self-worth that tie in a lot of this, which gets very intertwined when we're building something. We have this audacity to dream about something that we want to bring into the world and we want to do it, and we believe we can create an incredible change, and we believe that we're the tip of the spear to create that, to realize that in the world. There's also this odd piece where we say we have to pay this massive personal cost on the way. Let's see what's really true here. Let's see what's important for people to stand for. What are the stories I'm bringing to the table that I have to do this thing, that I'm a failure if this doesn't succeed, that the only way to solve this problem is X. These are all stories we bring to the table that might not be serving us for the things that we're really trying to accomplish. So it's important in my coaching practice to help people to start examining some of these things and figure out a way to orient themselves forward into the future in a way that helps serve them, their mission and their community.

Rachel Chalmers:

That narrative, we don't hear it. It's certainly the story of my career. I tried to do too much. I failed horribly. I burned out really hard. I had to take a year off and I'm so grateful that it happened because everything that's happened since has been informed by it and has been better because of it. A more compassionate leader, I have more precedence. I can see problems coming further in advance. I lean on that experience every day.

Brad Henrickson:

I can very much relate to that. I had this experience when we were building Zoosk. I was there for around five years. I put myself completely on the line there every moment of my day, except for the moments where I go rock climbing to recharge. It was basically a six month detox where  I just put the computers away, just went outdoors, traveled the world, and I just needed to reboot. It was a clear sign to me that the way I was operating was not sustainable for myself, thus paying this incredible cost. It’s a lesson that I've carried with me ever since then. In a similar way, it sounds like you have.

I'm so proud and so excited about the things that I accomplished there, and at the same time, there are much better ways I could have approached a lot of what was going on. And unfortunately, it took me putting myself right on the line and paying the personal cost to start gaining some insight and say, “I'm not going to go there again.” There's a different way to operate, and part of my coaching practice really orients around how I help people to build that awareness and set themselves up for success so they don't get there.

Rachel Chalmers:

If tech teaches us anything, it's that humans aren't machines and that humans are really good at stuff machines aren't good at like processing nuance and having intuition and being able to follow hunches. So it doesn't make any sense that we would treat humans as fungible machine parts that we can burn up and throw away. It's just economically irrational apart from everything else.

Brad Henrickson:

Oh, agreed. Absolutely. I like to say that the most important aspect of creating a company are the people that are involved in it. That is it at the end of the day. The experiences that you craft together, and so this notion of fungible human capital is just a very disturbing notion to me personally because it reduces people in a way that I find to be lacking respect for everyone who shows up.

Rachel Chalmers:

It's a delusion of the bankers. Brad, when you look back on your work, what are you proudest of?

Brad Henrickson:

Well, for the things I talked about at Zoosk and for all the times I put myself through, I will say that the thing I'm absolutely most proudest of is the team that we built there. It always comes back to people for me. It doesn't matter how much was raised or what access looked like. Of course, I love the impact that we create with the products and the companies that we're building. But the piece that really resonates for me of being most proudest of is the communities that I've been a part of and helped to create. It's something which to me lasts on, well, past whatever engagement that I'm in. Without that, I'm just not interested in creating something. I feel like there's this incredible opportunity or this incredible thing we're going to go do, and I go talk to the people and I'm like, Yeah, this is not what I'm going to be a part of. It almost always comes down to whether it matches in terms of who is involved and who are the people that are there?

Rachel Chalmers:

It really feels like community is our best countermeasure against the precarity we were talking about earlier. You can't rely on distant bankers for your next gig, but you can work with people and want to work with them again and have them want to work with you again. That's longevity in our industry.

Brad Henrickson:

I think that's very true, and we learn from the people that are around us. We have so much to give each other and support each other as we're doing these adventures on a daily basis. Whether it be companies that were advising or companies that were building or peer groups that we’re a part of. Without that, you're just a mercenary out in the market in some sense, trying to force something into the world. But the only way that you're going to be able to create that impact or grow again inside or become better at your practice, is to be able to invest in that community. It really does create this longevity, and it's really incredible when you look back and you say, “Hey, I wonder what so-and-so is doing today or you catch up on old stories and it's always to me just really heartwarming to go back and see some of those things and also watch how our paths together intertwine into the future.

Rachel Chalmers:

It's the best science fiction plot. Ragtag band of misfits becomes a found family. If you had one do over, what would you do differently? You’ve got a time travel device, go back and fix something. 

Brad Henrickson:

For me, it's finding more structured mentorship and coaching early on. I grew up in a family where I was very much of an independent figure in our mindset. We had a tribe of three brothers, and that mindset was very helpful for me, for sure. But it took me longer to turn that corner from Brad solving the problem and moving it to how can we, as a group, solve the problem and create more space for others. There was a lot of solo grinding things out, taking a lot of responsibility and overloading myself. Being harder on myself than I needed to be, and I think I paid a big cost for that. It also, at the same time, served me in a lot of different ways, but I think it would have been much better off and grown a lot faster with more structured, supported mentoring and coaching. For example, I used to be a lot more conflict avoidant and that really didn't serve me because there's places where conflict was a really important part of the role, especially as a leader. If you shy away from it, the community is going to pay a big cost.

I usually get feedback, for example, once I started getting more coaching and support. I wasn't particularly approachable, and it would have really been helpful for me to gain more of that insight earlier on, as opposed to putting on my hard hat and just trying to move through things. There's a number of pieces where I think getting more structured coaching and mentorship would have really helped me to have a better experience and also helped with my career and accelerated pieces of my career. I also think when there's this mental model I have in terms of time to get any signal back.

So when you start a software development, you write some code, you compile it or nowadays you have it interpreted and then you can see if it worked or not. The feedback cycle is really fast, which means that you can get this feedback and learn little nuggets of wisdom or nuggets of knowledge pretty quickly and test your hypotheses in the world. With executive leadership, the lead time to getting signals back is way longer. So it might be six months a year, maybe longer before, you know if the thing that you did really worked and there's a lot of different variables that are also entwined with it. So the rate of learning slows significantly, and I think you can help address some of that by getting some of this support as well.

Rachel Chalmers:

That just sounds like a superhero origin story now, putting forward into the world the coaching and mentorship that you wish you'd had when you were younger.

Brad Henrickson:

I think that's partially true. It's something which I've seen for myself to provide a lot of value. When I talk to people, I see people who are struggling with their own challenges and could get that support that I couldn't find for myself. When I was younger I didn't have the foresight to say this is something that would really serve me, and I feel really grateful for the people that I work with in this space because I think it is something which is really crucial for us as we continue to develop. As we develop as an industry and as we develop as individuals.

Rachel Chalmers:

What do you think makes innovation so difficult?

Brad Henrickson:

We touched a bit on changes in terms of how startups and how some innovations have been brought to market. I think that some of the innovation that happens creates this marketplace in some sense that allows capital that's being applied to it and allows people to be able to take some bets that they couldn't take beforehand. But at the same time, it can also create states of threat for people where people feel, “Hey, I need to just do this one thing and you get this one deal across the line and you get very caught up in the day to day. You feel like you're in this threat state. When you're in a threat state, it's much harder to think out of the box.

You get a lot more into what is the immediate thing that I need to deliver, which is great from an operational perspective, but isn't as great from this notion of, “How do we think about the problems that we truly need to solve as a business. That requires headroom. That requires being in an environment where you don't have to constantly justify or rationalize your thinking? And if you're in an operational role, you end up spending a lot of your day probably thinking about how we are actually going to deal with execution. What are the realities on the ground? Innovation pays a cost as it gets paired with capital and the desire for us to get returns. I think a lot of us in the schooling that we are brought up in was very much to what tests we needed to pass. And so you learn how to solve whatever the domain is, as opposed to actually, there's a different answer to the test, and I'm going to come up with my own answers.

I think there's a two piece part here. One is I think we've gone to this world where we don't create enough headroom to think about what we really need to do to create that innovation because of the operational realities of running businesses. Then the second one, that the educational side, at least that I was raised and I think a lot of people are raised in there was a let's try to get good grades and let's try to pass this test as opposed to let's really explore and innovate and explore these ideas, which is a very different mindset, which is very crucial for successful innovation. 

Rachel Chalmers:

As somebody with investor burnout, I'm going to say both of those aspects can be traced to impatient investors. People not investing for the long term, not investing with enough ambition to give people that headroom and to let people explore the problem domain rather than answer the next immediate problem.

Brad Henrickson:

I think that's very true, and you see companies that sort of play this pattern. If you think about the sort of cycle of a lot of these companies, it’s seed an angel and at that stage, you better get your product market fit right. Because then we're going to pull on the gas and then we're going to run, run, run as fast as we can and grow this thing. Well, if you're in the run, run, run and grow this thing and you say “Over here, there's actually an opportunity that's even bigger, it's like, well, how are we going to rationalize that with this growth that we're after? And it's like, well, the answer is, you're probably going to still go after the growth and then as a secondary or tertiary concern, maybe you'll spend some time and resources on that other piece. If we're sort of satisfied with that main premise of this company. It's a very tricky thing. You're allowed to innovate at the very top of that funding cycle. But as you're going down the line, let's focus on execution.

Rachel Chalmers:

Our degrees of freedom are pretty significantly narrowed. I look back to places like Bell Labs and Xerox Parc and SRI back in the day, and sure, they were bureaucratic and inefficient, and sometimes they were disappointing. But sometimes they produced innovations that were still teasing out the implications of all of this time later.

Brad Henrickson:

They did some incredible things in terms of organizational design, where they would set up research departments that had a lot of autonomy and they would go to the mat to preserve those things, which enabled a lot of that innovation to really come out and come through. And so some of the most important innovations from technology came from some of those investments that they made. Today you don't typically fund pure research in that way. It's a very different way of approaching it then that sort of a structure.

Rachel Chalmers:

How would you distill your experience into, say, two or three lessons for our listeners?

Brad Henrickson:

There's a couple things here. They're going to be kind of zoomed in towards me because of my experience in the world. I always think when we're talking about experiences, my experience probably doesn't match a lot of other people's experiences as we all have our own unique ones in this world. One that's been really important for me has been really challenging your “shoulds”. When I sit down and say, “Oh, I really ‘should’ do this thing”, that's a little flag for me. It's a little flag for me to say, “Why ‘should’ I do this? What's the should that's really present here? What am I actually trying to accomplish? Because I'm very quick to load on a lot of “shoulds” like I should do this, I should talk to that person. I should X, Y and Z. And then all of a sudden, I'm just loaded up with my full day and my full calendar is just a bunch of “shoulds” for the day.

What do I actually want to do? What's the really important thing to do? And is that actually captured there? Because if they’re “shoulds”, they're probably some sort of obligation or some other piece that's present for me, that's helping, that's driving my behavior. And so it's a little notice for me when the “shoulds” show up to question, why am I doing this thing? What am I really trying to do? I created that, and it's important for me to unpack it, to make sure that how I'm choosing to spend my time and energy really is in service of myself and for my community.

That's really key because if you have a “should”, you have a choice there. Do you actually do it or not? That's up to you. You don't have to do it. No one's going to force you to do it. That's a really important one for me, noticing those shoulds as they show up and find your preference. I think that's a really key one. The second one, and again, this is a little bit towards me. One of the things that tends to happen for me is that my wants are a little suppressed, and so I end up saying yes to a lot of things as opposed to saying, “What is that I really, truly want?” So for example, this week every morning, I go through my morning ritual of getting ready for my day and figuring out what else I want to realize in my day.

And so in the morning, I now write down what are my wants for the day? What are my “yes’s” for the day? What are the things I'm really going to orient around? So that way, I know at the end of the day, I went and did the thing that I really want to do for the day. Otherwise you wake up and have all these obligations. I have all these other pieces that are going on. I'm not fully in touch with what I want, but I sure can see all the other things that the world wants from me. One of the really important lessons there is to be really clear with yourself, what it is that you want, whether it be with work and your personal life, with whatever it is, you're going to be spending your energy on. Be really clear with that because you're going to be the expert in that. And if you're not clear about it, someone else or something else is going to inform that for you.

Rachel Chalmers:

Super interesting. How do you think the pandemic might affect corporations in the longer term?

Brad Henrickson:

So I think we're already seeing some of this based on a number of the coaching conversations I've been having with people. Obviously, the remote workforce thing is going to stick around for a while. People that I've been speaking with, they're not looking forward to commuting again. There's been a very, very public, from the Bay Area perspective, people moving to Tahoe, people moving out of the state. I like to talk about this as where we were 10 years ago in terms of technology supporting remote work. All that stuff has just compressed and gone out to everyone at the same time. And so there's this really fascinating piece where usually they talk about two or three weeks being the sort of timeline for a new habit to be ingrained for people. Well, we're what, 14 months into it at this point?

So there's new habits, there's new behaviors that we've learned and it's going to stick around in one flavor or another. I think this idea, particularly within knowledge work, of people working in a variety of different places is here to stay. We did it on the margin before and there were cases where people would try to prioritize that as a company priority. But this is just the way of the world now, and I think that isn't going to change.

Rachel Chalmers:

I'm definitely in the camp, I will work from home as long as I possibly can, because it has enabled a different pace of workday for me. I might still work into the evenings, but I'll run errands in the afternoon. In between meetings, I'll go out and sit in the garden and check in with my partner, and it's just very different to me, at least more human arc of the hours of the workday.

Brad Henrickson:

I totally relate to that. I do think it also requires people to orient themselves on how they really want to spend their time during their day. It gives you a lot of flexibility and if you're able to structure in a way that serves you and what you're doing that works really, really well. There's a flip side of this which is, “Well, now I'm working from home, I’m going to work all the time. Or, hey, I don't naturally reach out to connect to people, and I relied on work to do that and being in the workplace, if I'm remote, that's a very painful place to be.” So I very much hear that. I'm excited for the flexibility that remote work has had for me and the ability to run my practice from my house and a variety of other things. That's been really, really empowering in a lot of ways that I really appreciate.

A second thing which is going to be affecting corporations long term is that there's been this exuberance that has been present within startups, I think, for about 10 or 11 years post, financial crisis of 2008, that has just been building and building and building. I remember coming back in 2013 or 2014 after traveling for a year and just looking around in the street and just seeing all of this energy that had grown and there was, this very “sky's the limit” attitude and a very free attitude around capital.

I believe over this last year, we've seen a lot more return to fundamentals for businesses thinking about how they are actually exercising that capital, how are they going to operate. What do they think about their financial plans? A lot more diligence around how people think about expenses. There's almost this contraction that's happening, which I think is going to create a really healthy set of companies that are coming out of this set of changes. There's this muscle that hasn't been exercised as much in a while, which is “How do we deal with really strong headwinds? That is going to be a strengthening of the next crop of innovative businesses that really come out. I'm really excited for that.

I know there's challenges, of course, that comes with that. But I've personally been excited for this return to fundamentals and this return to really building businesses for the long term as opposed to, “Hey, we'll just build something, get some cheap capital and see if it works.

Rachel Chalmers:

It's a rule of thumb for investors that great companies are built in the downturns. I would also say, as a loyal San Franciscan, that San Francisco is actually pretty great during the downturns because the people who don't particularly care, all go and the people who are really in it to build something are still here.

Brad Henrickson:

Yes, I think that's very, very true. You get to decide how you want to orient and deal with it. Are you in this for the long haul or are you in it for the boom times?

Rachel Chalmers:

We've talked a lot about burnout. What are some strategies that you personally use to manage or avoid it?

Brad Henrickson:

This has been very important for me throughout my career. I'll talk a little bit about some high level things and I'll talk about one very sort of tactical thing that people can do to help themselves in terms of avoiding burnout. There's an important piece of setting clear boundaries and expectations. You've got the anxiety of the unknown, particularly whether it be with your co-founder or other executives that you're working with or a board. Be really clear about what those boundaries and expectations, and acknowledge how you’re feeling along the way. It’s very important. I can't just keep my feelings all crammed down. I need to be very open about them. I will talk about it . Make time for activities that help invigorate yourself and reveal yourself.

In terms of something very tactical that you can do, this is a great practice that I do on a pretty regular basis, which is, an energy review. What I mean by that is take your calendar for the week, print out your whole calendar. Look at all the entire calendar, every single meeting that's in there and then color code your calendar. If something gives you energy. I'm excited for that. Make it green. If there's something in your calendar you look at and you're saying, “Oh, wow, yeah, I really am not excited about that”, mark it red. Then just keep track of the percentage of time that's green and red for your week and for the green ones. Great. Cool. Keep those things going. For the red ones, you can make two decisions about it. One, “Do I stop doing it?” This could be delegating it. Maybe you find out that you're actually not needed there, or if you do need to keep going to it, figure out how you want to change it. Maybe there's something you can bring to that meeting or that discussion. Maybe there's some way for you to be able to inject some fun into it. Maybe it's shortening the links, changing the structure of it, but find a way to make sure that your days aren't just big walls of red. Because what you really have when you wake up to when you go to sleep is just your time. And if all of your time is being sunk into things that make you feel drained, you are going to burn out. I guarantee it. And so by going down and doing this calendar and energy review, it'll allow you to sit down and restructure your day and take responsibility for your day and figure out how you can actually shift it into a way that really serves you better. 

Rachel Chalmers:

I love that. That's super cool.  

Brad Henrickson:

Yeah, pretty much. You want to wake up in the morning and be excited for my day, not wake up and say, “How long can I stay in my bed and stay warm and cozy before I have to grind through my day?” It's that mindset of “How do you spark joy in your day?”

Rachel Chalmers:

It also reminds me of conversations with my two favorite bosses, Ravi, who I'm working for now, and Sam Ramji, who's now at Data Stacks, both of whom, when I went to work for them, asked me, “What is it that feeds you? What is it that nurtures your soul?” And in both cases it was mentoring and coaching young entrepreneurs. So building my career around that has made it much more sustainable and much more fun for me.

Brad, what is the best way for our listeners to connect or follow your work?

Brad Henrickson:

I'm not super active on social media, part of managing my attention, but you can find me on LinkedIn, and you can also find me at my leadership practice, which is Henricksonleadership.com. Both of those, I post some content on and off, and there's also links to a number of resources that I find to be really helpful for people as they're thinking about navigating their careers and their companies.

Rachel Chalmers:

What does the future look like for you personally? Any plans?

Brad Henrickson:

For sure. It's to continue to develop my leadership practice. It's one of the ways which I love to help stay connected and help to support people in their growth for their careers. I'll probably either eventually start another startup or found another startup. This is actually one of these areas that I work with my executive coach on. I've been on this four or five month journey right now of just discovering and exploring what I want to do next. I'm sure I'm going to go back or I'm going to either found another startup. It's just a very interesting time. It's a period of giving back to others and figuring out how I can support people in their journey. Those are the really big threads for me.

Rachel Chalmers:

You get to wave a magic wand and the next five years of our industry pan out exactly as you would like them to. What do things look like in 2026?

Brad Henrickson:

2026 feels like a long way away right now. I see a lot of these tech regulations that are showing up, and I really want to see companies move out of this SAS model that we've gotten into where there's a lot of companies that are just, “Hey, how can you build software that builds revenue?” I would really love to see this move to a space where it's like, “Hey, there are all these different types of spaces that we can really be in that's outside of just pure software technology.” Whether it be biotech or thinking about energy or thinking about health care. I think there's so many opportunities that are out there for us to do good in this world and also to really account for the overall costs of the companies that we're building. That there's this notion of taking full responsibility and moving into spaces that I haven't seen as much investment in. I would just absolutely love to see the technology industry shift to a little bit more.

Rachel Chalmers:

So things like product carbon lifecycle and cradle to grave sustainability?

Brad Henrickson:

Yes, like those sorts of things. Obviously, I care a lot about mindfulness and mental health. I think there's a lot in that space that could be done. When we talk about secondary effects, I think there's been a lot of negative impacts and positive impacts to mental health as a result of some of the things that's happened in technology. I would love to see some of these things invested in and see really stronger support for people in their journeys. I think it's one of the areas that we've somehow missed a bit over the last 10 years. 

Rachel Chalmers:

What else should I have asked you?

Brad Henrickson:

I think that covers most of it. I'm really excited by a lot of the talent that I've seen coming into the industry. There's been this entrepreneurial spirit and this deep desire to create impact that is really refreshing to me. I think for some of the downsides of the boom times, one of the really big upsides has been when people get an idea, they want to bring it out and realize it. This is a really beautiful aspect of innovation and something to be really, really celebrated. I hope that continues and I hope that people continue to diversify the ideas and really continue to deliver on those. I think it's a very exciting time in terms of the talent that's in industry.

Rachel Chalmers:

Yeah, I agree that the kids are all right. They're bringing amazing ideas to the table and it's so exciting to see.

Brad, it's been an absolute delight to have you on the show. Thank you so much.

Brad Henrickson:

Thank you so much, Rachel. It's been really fantastic chatting with you, and I really enjoyed our time together.