For Holden Page, director of FinLedger, business writing is changing tech for the better

It all started with WordPress. When Holden Page was growing up in a small Minnesota town, the blogging app was a place where he could connect to an audience and build community. “Looking back, it was just a bunch of people who were being really nice to me, and entertaining the fact that I was writing,” he told Free Radicals. 

Page started building WordPress sites, and landed a series of product-oriented jobs that led to more writing, and then to editorial work. “I probably have set up over 100 WordPress websites—paid, unpaid, multi-sites—and that made me interesting to a lot of folks running media publications on WordPress,” he explained. He spent two-and-a-half years as the managing editor of Crunchbase, and then led research operations at Golden, an SF-based startup that focuses on structured data and natural language processing. 

Page is now the director of FinLedger, a fintech news site that focuses on demystifying the intersection of technology and finance in a way that is easily legible without insider jargon. That theme of accessibility extends out from his editorial approach, into the culture he is building for his team. 

As a veteran of several startups, Page is intimately familiar with both the rewards of grind culture, and the very real toll it takes on people and the businesses that encourage 80-hour work weeks and demand hockey-stick shaped growth. At FinLedger he is thinking deeply about how to support employees at work, making sure his team feels listened to and acknowledged, and that writers feel secure enough to take risks. Each story is an experiment, and there are no failures, just new data. 

Though he’s clear that hustling, working, and learning on the job has been a rewarding path (he went to college for two years, but has largely taken it upon himself to upskill a la carte), even before the pandemic Page had come to realize that job security, a manageable pace for work, and real appreciation for mental health had to be central to any team he would lead going forward. Burnout, he acknowledged, is real, and high churn rates caused by stress and overwork can weaken companies over time. Cultivating a more sustainable work culture and supporting the structures that make it possible are a sign of maturity—of an organization as well as its leaders. 

Sherrell Dorsey spoke with Page about the importance of company culture, his optimistic vision for the future of journalism, and how product and editorial are learning to work together. 

You’ve been at FinLedger since March 2021, less than a year. Tell me about how you ended up there.

I predominantly worked in environments where my multiple, generalist skill sets, from product, from writing, from editing, have come together to where I can do all those things at once. But I can't do all those things forever. I am getting older, and I do want to see some things get more stabilized, I want to have a family. With a startup environment, the expectation is you do all those things. I feel like I've gotten what I've wanted out of those experiences. 

When I was looking for a new opportunity, I actually had a list written down. I wanted at minimum a Series C startup. In my experience, that’s about the time where HR departments get real, teams are built out, some culture things are solidifying—for good or bad. I wanted 50 to 250 employees, and I wanted pretty seasoned, non-traditional tech executives. Tech, especially the SF scene, wants to keep reinventing the wheel, at least culturally. It’s where we see the problems that we do, with these younger founders who are like, Yeah, we're gonna make this brand new culture. And I'm like, Well, there are some things that are done this way, for good reasons. 

HW Media, which is the parent company of Housingwire, RealTrends, and FinLedger, has those support systems, that maturity, and, at the same time, a pretty bold vision of where they want to go. That is an intersection of company attributes that's really difficult to find. 

I've also always wanted to build a publication. It’s one of my dreams. I can't do what journalists do. I can write, but I've never found my way to getting the story as good as they can. What I do know is that I love seeing those stories, I like supporting those stories. I like finding a way to make journalism profitable. And I definitely have that internal, against the man vibe, and I love being a part of funding it. 

The director of FinLedger role allows me to build this publication from that angle, and build a team that can look at the financial space in a way that I think is critical, which is demystifying it a bit. Fintech sounds very innovative and big. And it is, but it tends to not get translated, it's not made accessible, and it relies on buzzwords. I think FinLedger gives me an opportunity to break down those barriers. Because I do think anyone can go into fintech. However, they also need the language to get there.You shouldn't have to be able to speak the buzzwords to get into the meetings that you need to. But that's the reality. And we can explain those. 

While I get to build FinLedger from the ground up, I'm not doing it without help. There is a SVP there who has worked at, I believe The Wall Street Journal, and her experience I'm going to defer to a lot. I don't have that in my wheelhouse. We have a marketing team, a client success team. And there's not this expectation for me to carry it all, as there was in a startup environment. 

However, HW Media still has that mindset of wanting to be big. I still get to maintain that crazy vibe, where I'm like, I want this to be as big as Bloomberg, which is insane. But HW Media doesn't balk at wanting to own a market. 

It’s so interesting to hear that balance you’re describing between gaining skills at a startup, but then the development and training and resources in a more established company. Can you elaborate?

I'm going to answer this through a personal lens. Every startup environment that I have been through has been invaluable in teaching me a number of things. Startups taught me what limits I can hit. Operating in an environment where you have to just go—from a personal perspective, that is something that leads to burnout. That is something that is not sustainable over the long haul. And that is something that is not going to be acknowledged in a startup environment, because there is a board, and that board wants 10x returns, and that CEO is pressured to get those returns. 

I have seen some of my former bosses at startups be able to manage that kind of pressure in a way that is more sustainable, but it's always hanging over your head. The burn rate is always there. There's always that low-key pressure to exist. 

The other thing is resource allocation. It's hard. When a funding raise gets announced, people want their budgets, they want their positions, and all that acts as a very big accelerant to anxiety. That's a lot to manage. That's a lot to deal with. 

When you move to an environment—to be clear, not all more established environments are like this—there’s a sense of, Okay, this is how we run things. We have steps, we have procedures. Over time there's just more frameworks for how to adapt to employee concerns regarding how to manage employee disputes. You're entering a place of psychological safety. In startup environments that maybe simmers a bit more. 

That is not only good for my own mental well being, I think it's good for the longevity of a business. That's going to reduce that turnover. It's going to keep that institutional knowledge in play. There seems to be more incentive for people to want to make each other successful over a long period of time. 

The average startup employee turnover is 18 months [The data on this varies depending on how you slice it, but it is clear that tech has a higher turnover rate than other industries. —Ed.] That's a lot of new faces. That can quickly dehumanize things when you're staring at the numbers, which we do at startups. I think that having a little bit more of that stability is a really good thing. 

There's more experience. A lot of people get promoted within a startup environment. They may be in their late twenties. They got promoted based on all this work that they did, which is totally valid, they grinded that 80 hours a week. They deserve something more. Does that mean that they deserve management? Yes. Will they get the executive coaching alongside that? Probably not. That can create a startup culture that is difficult to keep healthy and sustainable. 

As you're approaching this new role, and as you're thinking about team building, culture building, what are the principles for you?

There are two parts. The newsroom in general and how I manage my life to stay sane. 

We know we're focusing on fintech. I view every piece that goes out not so much as a piece of journalism—it is to that writer and it should be—but for me, it's also an experiment. I view it through that product lens. I'm like, We wrote about that startup in Africa that's redefining micro payments through cell phones. Does it flop, does it succeed? Do we see it go above the average? Okay, let's do three more of those. 

This is why I think journalists are so awesome—I'm not a very dictatorial editor, I've never really assigned things. I'm like, Here's generally what we want, but I hired you for a reason. And so come at it. One of the things that I think is true for all editors, and all leaders, is the instinct to say no, based on frameworks that you've already built through hard-won experience. The experience exists for a reason. But what I like to do when I feel that twinge of anxiety toward an unorthodox pitch is to remind myself that this is an experiment. You're starting something new, give this person an opportunity to try that thing that falls outside of your realm. 

On the personal side, I really do try to work a maximum of 50 hours a week. I need sleep. I do CrossFit. I have rules that I don't do more than four hours of networking a week. I have a therapist, I go to her weekly. And we really do talk about the challenges of trying to lead something.

I think being a leader also means you're not a robot, but you do need to maintain composure. It's making sure substance use is in check. I know a lot of people in tech, especially if they're ramping up quickly, where self-medication starts to become a thing. I'm not saying that I'm above those things. I've struggled with those issues as I've gotten stressed out as well. And that's why I'm going to therapy and making sure that I stay on this path. 

To do that, I have an actual list on my desk of triggers. So if I haven't been sleeping, if I haven’t been eating three times a day, I look at that. My view is if you're fucking up on these basic needs, you're not going to be a good leader, you're not going to be a good husband, or a good co-worker—get your shit together.

How has the pandemic changed those strategies?

Focusing on the relationships with my wife and my friends. Before this, I traveled to San Francisco every six weeks—that's been the standard for our relationship over seven years. Now all of a sudden, I'm home all the time.  

I’m really working on communication. I'm a product of a startup environment. I charge forward, make decisions quickly, think about things in a managerial sense—here's the levers we can pull. I think that was something that was tolerated by my wife before, but it wasn't sustainable over the long haul. 

I also recognized that at home, I talked about work a lot. Eventually, my wife was like, Hey, we need to talk about things other than your job. Now we've very purposefully worked on carving out individual time. I've had to learn how to be quieter, and also just being a bit more respectful. 

I do the typical man thing of talking over and not realizing it. We talked about how if I'm doing that, she has the right to say, Hey, I'm just speaking. Internally, I get irritated, but it's actually really useful for her to be able to be candid about my communication style. The pandemic has led to a lot of new discoveries about how to communicate and how to give each other permission to say, Hey, this isn't sustainable, in a way that isn't going to lead to imminent divorce.

Have these practices at home translated into your work and your plan to really set up the culture for this new endeavor?

The number one thing is just listening more, taking more time to absorb the facts. One of the things that I do—this is a result of me having ADHD—I will sit down with my notebook and I'm actively trying to sit there and write what is being said. That helps me in two ways: One, it makes sure that I am engaged since I am writing, and two, it tends to make me shut up more. 

In terms of culture, I do have ADHD. So that's real. I have anxiety. These things are real. So I tried to be very cognizant of that. 

I don't Slack messages that say, Hey, I want to talk and just leave it at that. I'm very deliberate about saying, Hey, I would like to discuss this. What does your schedule look like? Yes, I am a director. Yes, I approve editorial. No, I don't do their job. I need to respect their time. And I try to do my best to do that and make sure that I'm at least giving people some maneuverability to tell me no, because I don't think people get that, often. That is something that I want to bring into the culture at FinLedger. 

I want to take bets on people. I did not graduate from college. I grew up in Hutchinson, Minnesota, a town of 10,000 people. My dad worked at Seagate [a data storage company]. My mom worked at Family Video—this isn't a poor background story thing. This is saying I didn't really innately deserve the opportunities I have had. I know other people have had to work a lot harder to get to where I'm at.

You’re naming white privilege, and some of the biggest undercurrents in our supposed meritocracy right now. Where does that sense of self-awareness come from for you? 

It's a couple things. I grew up in a conservative family, that family is still very conservative. The saying “pain hurts as long as you let it” drove me for about 10 years. It's not healthy.  It was expected that I did things. I was told, You know, when you're 18, you can make your own decisions when you leave the house. I also wanted to leave. I saw Y Combinator spend $100,000 on these cool apps. I was already kind of a nerd with WordPress. So there was that motivation there. The high school years were built on that. 

I wasn't bullied or anything in school, to be clear. I also didn't exactly fit in. I'm bi. I didn't really know that in high school, but I knew that I wanted to pursue opportunities outside of the social group that I had. I think you are the people you are around, and I knew I wanted to change who I was around very rapidly. 

I only went to college for two years. That broke a lot of my internal values that had existed before, and I adapted to new values that I like way better. I also kept the idea of, Hey, you gotta grind, you have to take chances. I really do believe the worst thing you can be told is “No.” I encourage people to take chances all the time. Rejection sucks. But eventually, something will happen, if you're willing to put in the work.

The cool thing about writing is you can learn it. You can learn a beat. So my judgment of a writer is: Do they show up? Are they personable? And are they willing to sit there and grind through those edits? And take care to show up the next day?

One thing I'll add is that I have really good people around me. For a long time, I didn't handle rejection well. I had a lot of anxiety. I dropped out of tech for a while after a failed startup and one of my friends sat me down one day and was like, Hey, you need to go back into this because you're actually good at it. I've relied on those people for a super long time, they've balanced me out. Without them I'm not sure I would be handling the pressures of the things that I've tried to do. 

I feel like we don't hear enough of those kinds of stories. 

Between every job I give myself a six-month grace period. And I ask, Where did you mess up? What do you do well? I tend to go really hard and then hit a wall, and I've learned to avoid hitting that wall. But it took me time to do that.

I’d like to hear your thoughts on how business news is shaping the conversation.

I think journalism, especially in business news, sets a foundation. It says these are the facts, these are the things that are happening right now, and this is what you need to know. That facts-based foundational knowledge can be built on by the founders, operators, and investors. Those facts can then be used by these parties to support their arguments, whether it’s a founder looking to justify their market opportunity to an investor or just giving an operator ammo to get through their next coffee meeting with something interesting and relevant to say about their industry. They can pick and choose the things that they need—to go to their investor, to go to that coffee meeting, to go to that board meeting—to make something relatable to somebody who doesn't have the context or the background to see the innovative idea that they're bringing to the table. 

Journalism gets to say, Here's how your market works. We know that in your McKinsey consultant report you're doing for a client, they probably prefer things to look rosy. But we can give you that accurate view of the market, and then you can use that to push your thoughts and your ideas forward.

This also demands that business publications go deeper than they maybe did before, focusing on demystifying corporate strategies, for instance. And I think that business publications that are going to succeed will be able to provide their readership with useful information that helps them push their agendas forward, that will allow them to innovate, that allows them to go to venture capitalists and sound intelligent, and makes new ideas accessible to larger audiences within their own network. 

You seem to have a lot of optimism about journalism, but it also feels like in the industry there’a a lot of fear right now about the future. What is your big picture view?

I have to remain optimistic to work in this industry, 100 percent. I think that's probably one of my most valuable assets. Aside from blind faith, there are actually things that I do believe in. I look at publications getting more intelligent and thinking of their offerings in a more SaaS, product-focused context.

Product roles test the boundaries between business and editorial. When you are a product manager—and probably when you’re an engineer—you're straddling business needs with a newsroom’s editorial independence. It takes time to figure out that balance, especially at large, institutional publications. Now, they did hire product people, but it required a culture change to make those folks feel successful. It also takes time to build up trust. Journalists tend to work with other journalists well, but tend to get real tight around anyone who operates outside of the newsroom. But as we see publications like The New York Times continue to succeed at creating a culture that balances product goals alongside editorial independence, other publications will have a model to follow. The culture is going to trickle down. 

Do you have advice for journalists trying to survive in a tough industry?

What I tell journalists is to actively build your own audience from the brand that you're writing for. One thing that I've taught a lot of journalists who work under me is concepts like conversion funnels. X number of people are coming to your Twitter account, you can pin a tweet promoting your newsletter, and X number of those people will convert to subscribers you own. 

I don't think that's something that editors sit down and actually explain to writers. I think part of that is because established journalists don't really think about marketing concepts. I think newer journalists are more inclined to think about that. The way I describe it to junior reporters  is that you're building your insurance plan, even for jobs outside of journalism. 

This was a conversation between Sherrell Dorsey and  Holden Page, edited for length and clarity by Annaliese Griffin and Rachel Jepsen. Reply to this email if there's someone you'd like to see us interview in the future.