Many startup CEOs spend all their time on product roadmaps and investor decks. Henry Shapiro of Reclaim.ai makes sure he also has time for LinkedIn. This isn’t a distraction from his “real work” — it’s a key part of his growth strategy, one that’s proving as valuable as feature releases and VC pitches.
In this interview, Henry explains his content creation process, revealing how he turns everyday business experiences into authentic, value-packed posts that resonate with his audience and drive growth for Reclaim.ai. His approach offers a playbook in founder-led content strategy, balancing personal insights with company messaging.
Editor’s note: We’ve lightly edited this interview for clarity and readability.
Tim: How do you approach the content you put out as a founder? Is there a strategic approach, and how did you decide to start talking about the product and company on your own account?
Henry: I’ve seen other founders focus on three main flavors of content, and I tend to do the same depending on our focus that week.
One flavor is founder-led content, which is a luxury smaller companies tend to have more of. It’s casual, almost intentionally unedited, like Loom videos or walkthroughs of stuff we built or are working on in the product. There’s an element of tying the vision of where you’re going with the product to what you just released.
The second is about startups and what I call “founder wisdom.” I don’t love doing posts like that, and sometimes I question who that content is really for. I get tired of reading about investor metrics, VC benchmarks, and ambiguous messages around running a startup.
What I’ve been really interested in writing about recently is internal processes — the pragmatic elements of how you do something at a company. Startups tend to do things that don’t scale, and there’s some unintuitive logic in the processes we use internally for things like customer support.
How did you discover that topic — was it your own itch or feedback and engagement you were getting?
There was a huge surge in popularity around the idea that your SaaS product likely doesn’t need a free plan. The conversation inevitably shifted to the support burden and expense of supporting free users.
So, I wrote what I viewed as my manifesto or thesis on why founder-led support is really important and why you can’t underrate the value of the feedback and connection you get with users when you do that job directly.
It got a lot of engagement from people with interesting perspectives and founders who feel similarly. One person I really admire who does a great job talking about this is Susana de Sousa, a support leader at Loom. She had been banging this drum for a while.
I felt this was something we were really interested in, so I started thinking more about writing about it since people seemed interested in learning more. I started talking about our process and how we close the loop with users. That led to some engagement from Des Traynor, the founder of Intercom, because I mentioned we use Intercom and Linear in our process.
Then, I wrote a blog post about our process and how we go through it. With a lot of things, sometimes you throw ideas out and if something sticks, you pull the thread further to see what comes of it.
One thing we learned from taking the support example is that there’s probably a whole fleet of content we could write just about how we do certain types of customer support interactions at Reclaim. There are probably five other blog posts I could write about all the subtopics that leak out of the posts I wrote originally.
Do you find that social posts can be a test or inspiration for larger blog posts since blogs are a much bigger investment? Are you seeing that happen more often, or was the support topic a coincidence?
Definitely. Another example, which is a mix of both social engagement and answering questions in support, is a glossary we just put on our website. It’s a compendium of productivity and calendar management terms, meant to be a mostly unopinionated glossary you would find in the world of productivity or time management.
There were obviously SEO motivations for doing that, and a lot of good stuff will come from it organically. But the way it emerged was through conversations where I felt there was a real vacuum of knowledge around this set of topics. There are highly opinionated thought-leadership articles and literal technical how-to guides from Google or Outlook, but there isn’t a glossary of terms defining them without sifting through paragraphs of information.
It’s helped me have stronger opinions on what kinds of content will be valuable. I’m not the person who spots keyword opportunities — we have people on the team much smarter about that than I am. But I can at least spot or see opportunities where no one’s really talking about something or writing about it in a particular way and bring that back into content marketing, brand marketing, or product marketing.
Are you mainly focusing on LinkedIn, or are you using other channels as well, like video? How do you view that?
Mostly LinkedIn and YouTube are the two channels I’ve spent the most time being active in. I prefer the LinkedIn format — I like writing longer posts and having room to develop thoughts and think through things out loud.
Twitter is a space I’ve never fully figured out how to be successful in. I feel like there’s an ancient lore or set of unspoken rules decided decades ago by the earliest Twitter users.
Is there anything on your radar that you or your team are considering trying in the future, like TikTok, Substack, or other platforms?
Podcasting has definitely been on our radar for a while, but we haven’t gone down that road yet, primarily due to resources and time.
We’ve done a little experimentation on TikTok and Instagram and could probably do more, but mostly LinkedIn and YouTube have been our main focus.
What I really like about LinkedIn, LinkedIn podcasts, YouTube, and even Substack to some extent, is that you get an audience more aligned with our product. TikTok and Instagram are great places for pithy, stamped-out videos about prosumer productivity topics.
At its core, our product is really about busy professionals — people slammed with meetings, trying to carve out time to make their work week more aligned with their priorities. I think more of those people hang out on those channels, at least when they’re looking for information about things like Reclaim or interested in learning about those types of topics.
You clearly have other people on your team working on content. How do you balance between what you write and what they do, both in terms of logistics and approval processes? How do those things interplay?
We try to do what we call a “ship it” at our marketing standup every day. The goal is that we, as a marketing team, should be saying something to the market every day. There’s always something for us to talk about — features that have been out for two years that lots of people haven’t used, things we can post around best practices, blog content, product videos, and walkthroughs we’ve done.
It’s usually one of the most fun parts of the morning. We’ll have our standup and then spend the remaining 20 or 30 minutes doing a “ship it” where we’ll throw some ideas around and come up with something to post. We have a designer on the team who will spin up an asset really quickly, or we’ve got folks who can pull together something.
We have “ship it” weeks on the product front too, and we’ve done “ship it” days for product as well. But those are a little different — they require a bit more prep because it’s engineering work. With marketing, there’s only so much damage we can do.
There’s not a ton of coordination around it. Sometimes, I will propose things where I say, “Hey, I really want to do X, Y, Z, and the way that the team can support me is by helping with [it].” Sometimes, it’s an idea that I come up with, and sometimes, it’s an idea that we talk through as a group. We conclude that it would make more sense if it were tweeted by someone specific — not even necessarily me. Sometimes, it’s like, “We think one of the engineers who built this thing should do a demo,” or “We think Patrick should talk about it because he’s the most familiar with it.”
Sometimes what will come out of those discussions is “Hey, this is something that Henry should write,” or “I feel like it should come from his personal account,” or “It’d be really cool if he could take five minutes after this to record a video about it.”
There’s this funny, fuzzy border, especially with marketing, where there are things that really don’t make sense to post from a corporate account, not because they’re legally risky or make your brand look bad, but they’re just so much less impactful when tweeted from a corporate account.
For example, when people mention our product on social or give us love on the internet, I usually go from my own personal account and respond to it. I think it’s more impactful for me to show that there’s a person who’s listening and not a social media manager using a corporate account.
No matter which way you take it, creating posts takes time. Do you have any tricks or time management tips for other founders who struggle to find the time?
The first element is having a habit, routine, and benchmark for yourself of “I will do X, Y, Z.” I go through ebbs and flows on this, but I try to have something provocative or interesting to say at least once or twice a week. I use Reclaim to make it a habit, and that’s great.
But the other problem people run into is they’re afraid of posting something that gets zero traction. You have to be okay with that being an outcome. You have to look at your winners and losers and try to figure out what about the winner worked.
Sometimes, it’s really small things like tone — a little bit of tone that snuck in there that made it come off as snarky or too cynical, or maybe it was too upbeat to the point of being saccharine.
There’s this balance, and finding your own authentic voice is hard, especially when there’s this style, particularly with Twitter, where everyone talks the same and uses the same jargon. You want to imitate that, but I’ve had a lot more success just trying to find my own voice, even if sometimes it’s different than the voice I maybe aspire to have.
With blog post writing, I’ve always employed a strategy I learned in high school called focused free writing or just free writing. It’s where you basically don’t stop typing or writing. Don’t judge what you just wrote and don’t editorialize as you write — just get all the ideas out. The goal is to have a full draft very quickly, and then you can go and editorialize and reread it.
Sometimes, you’re not in the right headspace to do that, so there’s also a time of day element. People need to find the time of day when they feel they’re most able to do this. For me, it’s usually in the evenings when I feel my brain’s freest to think about this stuff.
How do you justify the time you spend on content, even reading other people’s stuff on LinkedIn? Is it worth your time, and what benefits do you see from your own LinkedIn content — connections, conversations, or other things?
I think a big part of how you justify the investment is that it’s experimentation. For us, it’s not so much marketing strategy as it is about learning and figuring out what works.
I’m always curious to see how other founders are doing that job — how they talk about their brand and company, what topics they focus on, how much they pull their own product into it versus general startup advice, and where they find their swim lane.
Having direct experience talking about your company, what your users care about, things that are important to the business, or the processes your team uses — giving yourself reps on doing that kind of work is almost the reward in and of itself.
Connect with Henry on LinkedIn and explore his company at Reclaim.ai.
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