Field Notes: What's going on inside HG and MO

HG MCP, Harry's joined, MO S26 wrapped

Jun 11, 2026

👋 Hey, it’s Shaina, and I’m back for another issue of On Work, the weekly letter on independent entrepreneurship, fractional work, portfolio careers, and more

If you’re new, hi! Welcome. Help me spread the word by sharing with your friends, and please say hello in the comments.

Making some editorial changes

Before we get into today’s issue, I want to share some changes I’m making to this Substack.

I’ve been writing this for a few years now, mostly when I had something built up worth saying. A how-to here, a portfolio breakdown there, a few months of quiet in between as work got busy. And I love those posts.

But I’ve been sitting on an itch of sorts. Despite my longtime reticence to fully join the “build in public” movement, I want to share more with you of what’s going on behind the scenes. The messy in between bits inside the businesses I run, and a bit more of what’s happening in my life.

So I’m changing up this Substack for a few months to try on a new format and see how it feels.

We’re going weekly, on a four-week rhythm. Same reader, you, building (or seriously considering) something independent, but more to share with you along the way.

Here’s the shape of what you can expect:

Week 1: Field Notes. Sharing the inner goings on of HG and MO out loud, with some added context on my life as a fellow independent. What we tried and are trying, what we’ve changed, what we’re learning, and more from me personally on the circus of early motherhood, living abroad, and working independently. (You’re reading the first one now.)
Week 2: Open Tabs. What I’m seeing across the independent-work space right now. Pulled from the many phone calls I take with you each week, research we do to stay current, cool and helpful things crossing my desk. I hope to write this in the same vein as the many link-packs I love around the internet.
Week 3: Community Cuts. HG and MO sourced Q&A work like this and this. I’ll get one out a month, building on the format you’ve already been loving.
Week 4: Playbooks. Independent work how-tos like this and this. I suspect this was the reason a lot of you first subscribed. Still here, just sharper, and more consistent.

That’s the vision: four angles on our independent work world, one a week. I’m feeling inspired, and hope you continue to read.

Which brings me to today. We’re in the middle of rebuilding HG from the ground up to be AI native — and I decided the honest thing to do was show you that while it’s happening, not after it’s pretty. So that’s today’s first Field Notes: what it looks like to rebuild your company’s entire tech stack, mid-migration, with a lot still undecided.

Field Notes, June 2026

3 big things are happening in the Hello Generalist and Manual Override world right now. I’ll unpack each one below.

We are rebuilding HG’s app and infrastructure to be AI native (neither Harry nor I are engineers).
Harry officially joined the HG team, now working with me across both HG and MO.
Manual Override’s second cohort, S26, wrapped in May, and we’re planning what comes next.

1. Rebuilding HG to be AI native.

Back in ye olden days of 2022, Elyse used a state-of-the-art-at-the-time low code tool to build Hello Generalist’s current app, and we hacked together Airtable, Stripe, Gusto, Google Sheets, Tally, Docusign, and Notion to enable the app experience. Then, she and a contract engineer wrote the code by hand for our current marketing site.

We cobbled this all together in 4 weeks, which, at the time, was total and complete wizardry.

Now, of course, this is wildly outdated. HG grew up on tools and workflows that assume a human clicks every button — but much of HG’s work is incredibly well suited to agentic workflows instead.

The phrase “AI native” is thrown around a lot right now, but here’s what I’ve come to appreciate it actually meaning: AI native refers to AI used not as a feature bolted onto the side, but as the thing the whole system is built around. The old way: build the workflow for a human, then add an AI helper in the corner. AI native: assume an AI is doing the work, and design everything backward from that. HG’s marketplace works today because I know, or infer, an operator’s skills from their background, and can match them to a company’s job accordingly. AI will be better at most parts of that than me, and will do it at scale.

The goal now is nothing short of a rebuild: taking down the current infrastructure and replacing it with an AI native foundation.

And the payoff is exciting to think about: companies and operators will have an easier time finding each other, interacting, and ultimately doing more work together. Beyond finally building our table-stakes product that replaces the hacked together app-stack, I have a litany of ideas that I’m so excited to bring to the marketplace.

I've been slowly building internal AI tooling that makes my life easier (job scope writers, payment and payout automations, application screeners), but this move is customer-facing. My comfort zone as an operator is those internal tools (longtime Google Sheets hacker here), but I'm not an engineer, and I never thought I'd be contributing to customer-facing features the way I can now. I'm really enjoying it.

The scariest and biggest part — the part that enables everything else — happens next week: we’re migrating our current database in Xano into Supabase. New logins for everyone, a real cutover, a real window where things could break. By the next Field Notes I'll either be telling you it went clean or telling you what broke. Wish us luck!

2. Harry’s fully joined the team.

Maybe you picked up on this above? Harry has officially joined HG, building on his existing role as MO’s Co-founder.

To our great delight, we end up in matching shirts several times a week.

I feel lucky to have seen Harry’s independent journey from the jump: He and I connected the day he left his full-time job, and I had a Fractional Operations contract for him through HG the next week. Since then, his portfolio has exploded (portfolio-maxing anyone?): he’s built a full-blown AI enablement firm for startups and SMBs, does coaching work with operators, and as of last summer, is building MO with me.

Working with Harry is easy. Our skills are complementary. We laugh a lot. He’s patient. He’s incredibly smart. It was a no brainer to get him working on HG when he expressed interest. His work with HG will be initially focused on building AI into our product, and I expect will extend into product-lead growth work soon.

As a non-technical solopreneur since 2022, I’ve spent a long time believing the technical build was the part I had to outsource forever — that a trade-off in building the business the way that I am would be a wall between “operator who understands the business” and “person who can build the thing.” Bringing Harry feels like both a sigh of relief, and an energetic boost for the next chapter of this business.

3. MO S26 wrapped, and we’re planning for what’s next.

Blink and you missed it: Manual Override’s second ever cohort wrapped last month.

We started MO because there's a hole in the market. Getting started working for yourself is the easy part — talk to the people you know, and they'll hire you. Keeping it going is where it gets hard: making the leap from employee to entrepreneur on your own, funding it with personal savings, with no one to hand the hard parts to. There are plenty of courses and individual coaches in this space, but we wanted an accelerator in the vein of YC and Techstars. Now it exists!

Coming out of S26, I think we’re on the right track:

100% of participants shared they would do MO again.
9.9 / 10 average score on if they’d recommend us to a friend.
4.9 / 5 rating (from a group of almost all non-technical operators) on their ability to now work with AI.
Half the cohort running a self-built AI Operating System daily within six weeks.
Many booked first ever customers inside the 6 weeks, and more have active pipelines they’re working on closing.

Hell yeah.

We’ll run the next cohort, Fall 2026, in October/November this year, and in the meantime, are working on a brand refresh and marketing site update to showcase all the cool work our alumni have done. I’ll share more with you here on that next time.

Would love to hear from you on this new format. Is this interesting? Navel gazing? Boring? Excited for the next one? Please do let me know.

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