LinkedIn — 30 Day
Jack Yen — LinkedIn 30-Day Content Calendar
"Receipts from the Back Office"
Window: Days 1–30 | Primary Lane: Donuts (Golden Glaze) | Voice: Operator, reflective, real numbers
1. Positioning
Channel intent on LinkedIn (vs IG / TikTok):
- IG / TikTok = short-form proof-of-life, behind-the-scenes texture, audience growth.
- LinkedIn = the receipts channel. Longer cadence, fewer posts, more reflection, more numbers. The audience here is ex-tech peers, SMB operators, PE / ETA / search fund people, vertical SaaS founders, and the occasional LP. They will scroll past anything that smells like a motivational deck. They will read 400 words if there is one real number in the first line.
Differentiator from the rest of the "ex-tech buys an SMB" feed:
Most of that content is either (a) acquisition-stage romance ("here's how I found the deal") or (b) cosplay — Loom tours of a business someone is about to run for the first time. Jack's lane is operator year 2: actually running 7 donut shops with 20+ deskless employees while building the software himself in the back office. Different shape. Less glamorous. More credible.
Format mix (target over 30 days):
- 60% native long-text posts
- 25% document carousels (uploaded as PDFs — heavier dwell-time weight than image carousels)
- 10% native video (under 90 seconds, captioned, vertical-friendly but trimmed for desktop)
- 5% polls (used surgically — once, around a real operator question)
Cadence:
- 4–5 posts per week, primary publish window Tuesday–Thursday, 7:00–9:00 AM CT
- Friday used for lighter reflection / week-in-review type content
- No weekend posting in Month 1 (saved for repurposing later if a post needs a second life)
- ~20 posts across the 30-day window
Hashtags: 3–5 niche per post, never generic. #smbtwitter over #business. #searchfund over #entrepreneurship. Often zero hashtags is correct on LinkedIn — used only when the niche is precise enough to matter.
2. Content Pillars
Five pillars carry the calendar. Month 1 leans 80% into Pillar 1 (Donut Operations) with Pillar 4 (Tech-to-Operator) as the through-line. STR/MTR (Pillar 2) is briefly introduced in the Day 1 origin post only — its dedicated lane opens in Month 2.
Pillar 1 — Donut Operations (Golden Glaze)
7 shops, GP/LP fund structure (Reg D 506(b)), 20+ deskless employees, 4am production floors. Unit economics, hiring, turnover, equipment failures, the actual decisions. The unglamorous middle.
Pillar 2 — STR / MTR Portfolio
11 units across Hawaii, DFW, Tampa. Insurance housing, displaced families, traveling employees. Different lane than the Airbnb-bro content. Introduced in Day 1 origin only during Month 1. Full lane opens Month 2.
Pillar 3 — Custom Software (Built Solo with AI)
Discord ops layer, daily reporting, automated investor reports, scheduling. Now building inventory management and guest messaging. $60K/yr of third-party SaaS replaced so far. The "vertical SaaS for myself" angle that resonates with the technical half of the audience.
Pillar 4 — Tech-to-Operator Tradeoffs
13 years in tech, 6 companies, six-figure salary, planned layoff, six-figure severance. The honest math on what changes when you swap the W-2 for the portfolio. Variance, identity, decision speed, deskless management. This is the highest-engagement lane.
Pillar 5 — Fund / Capital Structure
GP/LP mechanics, investor reporting cadence, why automated reports matter when you're a sub-scale GP. Lighter touch — used to attract LP and search-fund attention without sounding like a pitch.
3. Day-by-Day Calendar
Day 1 — Tuesday, May 19 | Format: Long text | Pillar 4 (origin)
October 2024. 13 years in tech, six different companies, six-figure salary, full golden handcuffs. Every Sunday night I dreaded Monday and told myself it was just a season. I told myself that for five years.
Then I planned my way to a layoff.
Read the room — tech was deep in layoff cycles in 2024 — and let the timing work for me. Walked out with a six-figure severance. By that point I already had 5 short-term rentals cashflowing across Hawaii and DFW, and 12 months of savings stacked. Not a leap. A runway.
18 months in now.
11 STR/MTR units across Hawaii, DFW, and Tampa — more than doubled. Displaced families, traveling employees, insurance housing. Different lane than the Airbnb-bro content.
7 donut shops in DFW. GP/LP fund structure. 20+ employees on a kitchen floor at 4am. Running on custom software I built solo in three weeks with AI — Discord ops layer, daily reporting, automated investor reports, scheduling. Now building inventory management and guest messaging too. Roughly $60K/yr of third-party software replaced so far. Still growing.
Two physical-asset businesses. One operator. One laptop in the back office.
The hardest part wasn't the math. I managed engineers on Slack and Teams for 13 years. I'd never managed a deskless workforce — 20 people on a kitchen floor at 4am who don't read messages between shifts. Different problem. Different tooling. None of the SMB SaaS in this category was built for it.
So I'm building it.
I'm not here to tell you to buy a small business. Most of the "ex-tech buys an SMB" content online is cosplay. The work is unglamorous. Margins are thin. You will spend a Saturday driving between locations because a POS won't sync or a turnover crew is late.
But if you spent a decade building software that someone else owned, and you're wondering whether the operator side is more interesting than the IC side — I'll tell you what I'm learning. With real numbers. As I go.
Following along here. No motivational stuff. Just receipts.
Hashtags: #smbtwitter #searchfund #etaforum
Day 2 — Wednesday, May 20 | Format: Long text | Pillar 1
4:12 AM, three weeks into owning Golden Glaze.
I drove to one of the shops because the opener didn't clock in. Walked in expecting an empty kitchen and instead found three of my employees already mid-production. No one had texted me. They just started.
That was the first time I understood the gap between managing engineers on Slack and running a deskless workforce.
Engineers self-report. They write status updates. They DM when blocked. The whole culture is built around making work visible because the work is invisible.
In a donut kitchen at 4am, the work is the visible part. The status update is the tray of glazed old-fashioneds on the rack. If you want to know what's happening, you go look. Nobody is going to type it for you.
That single shift broke 13 years of mental model.
It's also why almost none of the SMB software I evaluated felt right. It was all designed around the assumption that the operator wants more reporting surface. What I actually wanted was less. I wanted the floor to push exceptions to me, not status. Tell me when something is off. Otherwise, assume the trays are getting made.
Building toward that now.
If you're moving from managing knowledge workers to managing deskless ones, the biggest unlearning is this: don't replace the floor's visibility with a dashboard. Replace it with an exception channel.
Hashtags: #operations #smb #deskless
Day 3 — Friday, May 22 | Format: Document carousel (PDF, 8 slides) | Pillar 3
Title slide:
"I replaced $60K/yr of third-party software with 3 weeks of AI-assisted code. Here's the stack."
Slide 2: What I was paying for before (line items, no logos — scheduling platform, ops chat tool, reporting suite, investor portal, SMS broadcast).
Slide 3: The unlock — I'm the only user that matters. Vertical SaaS is built for the median customer. I'm not the median. I can ship for an audience of one.
Slide 4: Layer 1 — Discord as the ops surface. Why a free chat tool beat purpose-built ops software for a deskless team.
Slide 5: Layer 2 — Daily reporting. One job, one Slack-style summary, exception-first.
Slide 6: Layer 3 — Automated investor reports. GP/LP fund structure means quarterly reporting isn't optional. So it's a job that runs itself.
Slide 7: Layer 4 — Scheduling. The piece I expected to be hardest. Was the easiest.
Slide 8: What I'm building next — inventory management + guest messaging. Different problems, same pattern: replace the SaaS bill with the smallest possible internal tool.
Post copy accompanying the carousel:
Most "I replaced my SaaS stack with AI" posts on this site are theoretical. Here is what I actually did.
Three weeks. Solo. ~$60K/yr of contract value replaced.
The full stack in the carousel. I'll do a follow-up on what I would NOT recommend building yourself — the line moves faster than people think.
Hashtags: #verticalsaas #aiengineering #smbtech
Day 4 — Tuesday, May 26 | Format: Long text | Pillar 1
Hiring for a donut shop is a different skill than hiring for a tech team.
In tech, the cost of a bad hire is months. You see it slowly — slipped commits, weak reviews, fading ownership. There's time to course-correct.
On a kitchen floor, the cost of a bad hire is one shift. You see it the next morning at 4am when the fryer wasn't preheated.
That compression has changed how I interview.
I stopped asking about experience. I started asking what someone does between 4 and 6am at their current job. If the answer is detailed and specific, they're a worker. If it's vague, they're a story. The job is too physical and too early for stories.
I also stopped optimizing for the best candidate in the room. I optimize for the candidate who is going to be on the floor in 90 days. Tech taught me to hire for ceiling. Donuts taught me to hire for retention. Different math.
The retention math:
- A great hire who stays 8 months costs me less than a "perfect" hire who quits in week 6.
- A 6-month tenure across 20 employees at $14/hr beats a 3-month tenure at any number you can dream up.
- Training cost is the entire game.
If you've only ever hired knowledge workers, the deskless playbook is genuinely different. Not harder. Different.
Hashtags: #hiring #operations #smb
Day 5 — Wednesday, May 27 | Format: Long text | Pillar 4
The day I signed the donut deal, three different people told me the same thing.
"You're going to miss the salary."
They were half right. I miss the predictability. I don't miss the salary.
Six-figure W-2 sounds like a lot until you actually sit with what it costs. It costs the option to say no on a Sunday night. It costs the right to choose what problem you work on Monday morning. It costs the calendar you don't own.
The portfolio doesn't pay better on a monthly basis. Some months it pays worse. But the swap I made — I traded a fixed price for an option.
The option to walk a shop at 5am and watch how the team works.
The option to ship a feature on a Tuesday because I noticed a gap on a Monday.
The option to take a Wednesday off and not ask anyone.
The salary was the easy part to replace. The identity around the salary was the hard part. I'd been "Jack at $TechCo" for 13 years. Now I'm just Jack, and the only person grading the work is the P&L.
That's a harder grader. But it's a more honest one.
Hashtags: #careerpivot #operatorlife
Day 6 — Thursday, May 28 | Format: Long text | Pillar 3
The piece of software I was most embarrassed to build is the one that's saved me the most time.
It's a Discord bot.
Not a SaaS app. Not a fancy dashboard. A Discord bot that lives in a server with my managers and runs the entire daily ops loop.
When I tell technical friends this, they wince. "Why Discord?" The answer is unsexy: because my managers were already on their phones, Discord is free, the notification model works for shift workers, and the bot I needed didn't exist as a product.
Here's what it actually does:
- Receives end-of-shift summaries from each shop manager via a structured prompt.
- Flags exceptions automatically (variance on waste, no-shows, equipment notes).
- Pushes me a single morning digest at 6:45 AM with the previous day rolled up by shop.
- Routes the photos managers send to a Drive folder named by date and shop, so I can audit visually without re-asking.
Cost: free chat tool + my own time.
Replaced: ~$1,400/mo of "team ops" SaaS I was demoing.
Time to build: a long weekend.
The lesson isn't "build everything yourself." The lesson is: when your team is already living in a free tool, the highest-leverage software is often the bot that meets them where they are. Not the platform that asks them to migrate.
Hashtags: #buildinpublic #opstech
Day 7 — Tuesday, June 2 | Format: Long text | Pillar 1
Week 2 of June, GP-LP quarterly reporting season starts ramping.
I want to talk about something I underestimated when I set up the fund: how much trust is built or lost in the cadence of reports, not the content of them.
GP/LP, Reg D 506(b), seven donut shops in DFW. My LPs are people I know — friends, ex-colleagues, a couple of family members who came in as accredited investors. The amount is meaningful to them. The relationship is meaningful to me.
What I learned in the first cycle: nobody actually reads the report cover to cover. What they remember is whether it showed up on time.
If the report is on time and clear, the assumption is the operation is on time and clear.
If the report is late, every line item gets re-read with suspicion.
So I built the automated investor report flow first, before I built anything sexier. Pulls from the books, runs the variance, formats the PDF, queues the email. I press one button on the same day every quarter.
That's the unglamorous truth about being a sub-scale GP. The reporting discipline is the reputation. The reputation is the next raise.
If you're thinking about syndicating into SMB, do this part first. Not last.
Hashtags: #searchfund #smbpe #gpilp
Day 8 — Wednesday, June 3 | Format: Native video (~75s) | Pillar 1
Video setup: Shot inside one of the shops, early morning, ambient prep noise. Vertical 9:16 framed loose enough to use horizontally on LinkedIn. Captions burned in.
Script:
(0:00) "It's 4:47 AM at Shop 3."
(0:05) "There are four people on this floor right now. None of them have read a Slack message today. None of them are going to."
(0:13) "I spent 13 years managing engineers who lived in their inbox. This is a completely different management problem."
(0:22) "The tools you reach for first don't work. Group chats get ignored. Dashboards get ignored. Even text messages get ignored because phones are in lockers during the shift."
(0:35) "What works is a board on the wall. A whiteboard schedule. A printed prep sheet. And one person — the lead — who absorbs everything and reports it after."
(0:48) "I built a Discord bot to capture that one report, structured, every morning. That's the entire ops layer. It cost me nothing and it replaced four pieces of software."
(1:00) "If you're moving from a desk-job team to a deskless one, the unlearning is this: meet your team where their hands are. Not where your laptop is."
(1:12) End card: "More receipts at jackyen.com — link in profile."
Post copy accompanying the video:
A 75-second walkthrough of why the deskless workforce broke my entire management playbook in week one.
Watch with sound — there's prep noise in the background, which is the whole point.
Hashtags: #deskless #operations
Day 9 — Friday, June 5 | Format: Long text | Pillar 4
I had three job offers on the table when I left tech in October 2024. I turned all of them down.
I want to be honest about something I almost never see in the "ex-tech" content: I was not running from a bad job. I was running from a great job that was making me bad at my own life.
The offers were generous. One was a Director title at a name-brand company. One was a startup with real equity. One was a quieter L6 role at a place I respected. On paper, any of them was the right move.
And every Sunday, I'd think about taking one of them, and feel the exact same dread I'd felt for five years.
Here's the test I eventually used. I asked myself: if I take this job, what does my Tuesday at 2pm look like in 18 months?
For every offer, the answer was the same. Standups. Quarterly planning. A roadmap I'd inherit. A review cycle I'd manage. None of it bad. None of it mine.
Then I asked the same question about the donut deal that was on the table. Tuesday at 2pm: probably at the bakery, probably looking at the previous day's waste numbers, probably annoyed at something a vendor did, probably ten feet from the actual product.
The first picture was clean. The second was messy.
I picked the messy one.
18 months later, the Tuesday is messier than I imagined and more interesting than I hoped. I'm not telling you to do this. I'm telling you the Tuesday test is a more honest filter than the comp test.
Hashtags: #careerdecisions #operator
Day 10 — Tuesday, June 9 | Format: Long text | Pillar 1
A vendor tried to upsell me a $48,000/yr inventory system last month.
It would, allegedly, automate counts, integrate with my POS, predict waste, and "unlock data-driven decisions."
I asked the rep three questions:
- How many of your customers have under 10 locations?
- Of those, how many actively use the predictive features?
- What's the median monthly active user count per account?
The answers were, in order: "a few," "honestly, most don't get there," and "usually one or two."
So I'm paying $48K/yr for a tool that one of my managers might open twice a week. No.
I went home and started building the smallest possible internal tool that solves the actual problem. Mobile-first count entry. One screen per shop. Variance flag if today's count doesn't reconcile with yesterday + receiving - sales. That's it.
Three weekends of work. Maybe four.
This is the recurring pattern I keep running into: vertical SaaS in the SMB tier is priced for what it could do, not what the customer actually uses. The 80/20 of most of these tools is genuinely small.
If you're technical and you're running an SMB, you have a structural advantage the median operator doesn't. Use it. Build the 20%.
Hashtags: #verticalsaas #buildvsbuy
Day 11 — Wednesday, June 10 | Format: Document carousel (PDF, 7 slides) | Pillar 1
Title slide:
"7 donut shops. One operator. Here's the morning routine."
Slide 2: 5:00 AM — Discord digest is already in my inbox from the overnight bot. Skim the exception flags. Three usually. Today, none.
Slide 3: 5:30 AM — Drive folder check. Yesterday's end-of-shift photos auto-routed by shop. 20 seconds per shop to skim. Visual audit. No questions for managers unless something's off.
Slide 4: 6:00 AM — Inbox. Ten minutes max. Vendor stuff, lease stuff, one LP question.
Slide 5: 6:30 AM — One shop visit, rotating. I'm physically in a different shop each weekday morning. Two shops per week never see me. By design. They run themselves or they don't.
Slide 6: 8:00 AM — Back at the desk. This is the only block where I write code or build. Two hours, uninterrupted. Phone face down.
Slide 7: Closing card: "The whole operation runs because I built the systems that let the morning end at 10am, not 2pm. Following along for more."
Post copy accompanying the carousel:
The version of this post that exists in 95% of LinkedIn "founder routine" content is fake. Here is the real one. With timestamps.
If you're considering operator-life, look at the timestamps and ask yourself if that's the shape of day you actually want. It is not for everyone. It is for me.
Hashtags: #operator #dailyroutine #smb
Day 12 — Thursday, June 11 | Format: Poll | Pillar 4
Poll question:
If you left a six-figure tech salary to run a small business, what's the single hardest part of the transition?
Options (LinkedIn allows 4):
- The variance in income shape
- Managing a deskless team
- Losing the "what do you do" identity
- The lack of a peer cohort
Post copy:
I'll tell you which one I underestimated the most. But I'm curious what the room says first.
For context: I left tech in October 2024 to operate 7 donut shops and 11 STR/MTR units. 18 months in. All four of these have been real. One of them surprised me.
Voting closes Friday. I'll do a follow-up post on the one I picked.
Hashtags: none (polls don't need them).
Day 13 — Friday, June 12 | Format: Long text | Pillar 4 (poll follow-up)
Poll closed yesterday. The vote was close — "deskless management" and "variance in income shape" basically tied. The third was "identity." Almost nobody picked "peer cohort."
The one I personally underestimated the most was the peer cohort.
I want to talk about that one because it's the least discussed in the ex-tech operator pipeline.
In tech, I had a cohort by default. Standups. All-hands. Engineering Slack. Conferences. I'd walk into a coffee shop in any major city and recognize three people. The cohort was the air I breathed and I didn't notice.
In operator-land, the default is silence. My managers are not my peers — they work for me. My LPs are not my peers — they trust me with capital. My vendors are not my peers. My family is supportive but not in this fight.
The first six months, I genuinely didn't notice. I was too busy. By month nine, I noticed.
Here's what I've done about it, in case it's useful:
- One real recurring call with another GP/operator I trust. Every other Friday. Both sides bring numbers.
- Two looser group chats with ex-tech-now-operator folks. Lower frequency, higher signal than I expected.
- LinkedIn, used like this — receipts, not theater — has started to do some of the work too.
If you're considering this jump, the question to ask yourself isn't whether you can handle the work. It's whether you can build the cohort from scratch. That part doesn't come with the deal.
Hashtags: #operator #smbtwitter
Day 14 — Tuesday, June 16 | Format: Long text | Pillar 3
The piece of advice that saved me the most software-build time this year:
Don't build features. Build the absence of meetings.
Every internal tool I've shipped has had the same test: does this remove a recurring conversation?
The Discord ops bot — removed the 7am call with managers.
The daily digest job — removed the "how did yesterday go" check-in.
The automated investor report — removed the "any update on the quarter?" emails.
The scheduling layer — removed the back-and-forth on shift swaps.
I never set out to build software. I set out to delete meetings. Software just turned out to be the cheapest way.
This is also why I don't try to build a real product out of any of it. The moment I'd ship it externally, I'd have to add the features that justify the price tag — admin panels, RBAC, multi-tenancy, support docs. That's a different game. That's the game I just spent 13 years inside of.
The 80/20 of internal tooling is genuinely beautiful. Build for one. Ship in days. Delete the meeting. Move on.
Hashtags: #engineeringleadership #opstech
Day 15 — Wednesday, June 17 | Format: Long-form essay (long text) | Pillar 4
Essay: "The W-2 sells you stability. The portfolio sells you control. You don't get both."
The hardest adjustment after leaving corporate wasn't the money. It was the variance.
For 13 years, tech salary was the same direct deposit every other Friday. The number was big, but more importantly, the number was flat. Same date. Same amount. Same buffer it built into my checking account on a predictable curve. I could plan a year around it without thinking about it.
Now my income is 7 donut shops, plus distributions from the STR/MTR portfolio, plus the occasional GP-side draw from the fund. Same average over a 12-month window. Very different shape.
What I underestimated was how much mental overhead the variance costs until you build the discipline for it.
The first six months, I'd find myself doing math in my head at strange times. Standing in line for coffee, I'd suddenly think about whether a vendor invoice cleared. Mid-conversation at dinner, I'd remember that the LP distribution went out yesterday and the operating account was lower than I liked. The math wasn't hard. The math was unbidden. That's the cost. Not the dollars — the cycles.
The W-2 charges you a premium for stability. People talk about it like the premium is opportunity cost, the spread between your salary and what you could earn running your own thing. That's part of it, but it's not the load-bearing part. The load-bearing part is cognitive. The W-2 outsources your cash forecasting to your employer. The day you leave, you take that job back. Most people are not prepared for how much mental real estate it consumes.
So I built the observability for it. Same way I would have built it for a service at any tech job. A 13-week rolling cash forecast that updates from the books nightly. Anomaly alerts when a category swings beyond its rolling stddev. A buffer rule — operating account never drops below a defined floor, and if it gets within 20% of that floor, the system pings me before I notice. The same software discipline I used to deploy for someone else's product. Now deployed for the only customer that matters.
Once that existed, the cognitive load dropped to almost nothing. Not because the variance went away. Because the variance became someone else's job, and that someone else was a script that didn't need to think about it in line at coffee.
This is the part of the operator transition I wish I'd heard from someone before I made it: the goal isn't to eliminate the variance. The variance is the price of admission for the control. The goal is to build the discipline so the variance stops costing you cycles.
The W-2 sells you stability. The portfolio sells you control. You don't get both. But if you set up the observability right, you don't have to pay for the variance with your attention. You pay for it once, by building the system. Then the system pays for itself, every single day, by giving you back the cycles you used to spend worrying.
If you're considering the jump and the salary number is what's holding you up — the salary is rarely the right thing to optimize against. Optimize against the cognitive load. That's the real number.
Hashtags: #operator #careerpivot #smbfinance
Day 16 — Thursday, June 18 | Format: Long text | Pillar 1
A donut machine broke at 3:42 AM on a Tuesday last month.
The opener texted my GM. The GM texted me. I was awake by 3:55. By 4:10 I'd called the service vendor who's on our list. By 4:30 the vendor had a tech routed. By 5:15 the tech was on-site. By 6:00 we were producing again.
We lost roughly 90 minutes of production at one shop. Maybe $400 of contribution margin.
Now — for any of my software peers reading this — sit with that response time. That is the entire incident response loop. Page → triage → vendor dispatch → fix → resume → post-mortem. In 2 hours and 18 minutes. With one operator on a phone in pajamas.
I tell this story not to brag about the response. I tell it because it is the exact same pattern I ran for 13 years on web infrastructure. Page. Triage. Mitigate. Resolve. Post-mortem. The shape is identical.
What's different is the post-mortem.
In tech, the post-mortem is a doc. People read it. Engineers nod. Action items get filed in Jira. Maybe two of them ship.
In donuts, the post-mortem was me sitting with the GM at 7am, asking why the vendor on the top of our list wasn't the one we called first. Answer: she'd never actually had to call them, and the old GM had a different vendor in his head. So we updated the laminated card next to the manager's office. Done. Closed.
Two hours. One change. No Jira.
There is a version of incident response in SMB that is so much faster than tech precisely because there are fewer people in the loop. That is the whole job.
Hashtags: #incidentresponse #operations
Day 17 — Tuesday, June 23 | Format: Long text | Pillar 1
The single biggest unlock at Golden Glaze in the first 12 months wasn't software. It was a laminated card.
I'm serious.
When I took over the shops, every manager had a different mental model of what to do when something went wrong. Different escalation paths. Different vendors. Different "I'll just handle it myself" reflexes that quietly cost me money.
So I made a card. Single page. Front and back. Plastic-coated.
Front: every common failure mode, ranked by likelihood. Fryer down. POS offline. No-show opener. Refrigeration alarm. Walk-in temp drift. Each with three lines — who to call, what to do in the meantime, when to escalate to me.
Back: the daily close checklist, the deposit drop process, and the cash variance threshold above which the GM gets called.
Cost to produce: ~$60 at the print shop for 14 cards (two per shop).
Cost saved in the first six months: I genuinely can't add it up. It's in the hundreds of monthly hours of decision overhead that just stopped happening.
The funny part is, this is the same thing I'd been building as a Confluence doc in tech for a decade. Runbooks. The only difference is plastic instead of HTML, and a wall instead of a wiki.
The runbook itself is the leverage. The format follows the workforce.
Hashtags: #operations #runbooks
Day 18 — Wednesday, June 24 | Format: Document carousel (PDF, 6 slides) | Pillar 5
Title slide:
"What a sub-scale GP actually does. 5 honest slides on running a small fund."
Slide 2: The structure — Reg D 506(b), GP/LP, accredited investors only, real-asset SMB (donuts). Why this structure made sense for the size.
Slide 3: What "sub-scale" really means — under the threshold where institutional capital pays attention, over the threshold where you take this seriously. It's a real tier and most content ignores it.
Slide 4: Reporting cadence is the relationship. Quarterly report, automated, on the same day every cycle. The discipline of the date matters more than the prose.
Slide 5: The boring math no one posts — fees, alignment, the carry conversation, why I structured my own GP draw the way I did.
Slide 6: What I would do differently if I started today. Spoiler: build the reporting automation before the first close, not after.
Post copy accompanying the carousel:
The "I run a fund" content on LinkedIn skews to two extremes: institutional PE people, and people pretending to be them. There's a real middle tier — sub-scale GPs running real businesses with friends-and-family-and-accredited capital. That's where I sit.
Here is what that tier actually looks like, with no varnish.
Hashtags: #searchfund #smbpe #regd
Day 19 — Thursday, June 25 | Format: Long text | Pillar 4
A thing I notice about ex-tech operators that I want to name out loud:
Most of us are quietly homesick for the codebase.
It comes out in weird ways. We over-build internal tools. We refactor the chart of accounts. We spend a Saturday "automating" something that could be done with a sticky note. We call this "leverage" but sometimes it's just nostalgia in a hoodie.
I caught myself doing this around month seven. I'd spent a weekend re-architecting the Discord bot to support "future expansion." There was no future expansion. There was one bot, one user, one workflow. I was just lonely for the part of my brain that ran for 13 years.
I cut the refactor. Shipped the bot at the original quality level. Went and walked a shop.
The walk-the-shop muscle is the one that atrophies in ex-tech operators. The build-the-thing muscle is the one we'll over-train on, given the slightest excuse.
If you're early in this transition, here's the test: when you find yourself opening the editor on a Saturday for an "improvement," ask whether a manager would notice the change. If the answer is no, close the editor. Go to a location instead.
The codebase isn't where the leverage is anymore. The floor is.
Hashtags: #operator #engineerleader
Day 20 — Tuesday, June 30 | Format: Long text | Pillar 1
Month-end at Golden Glaze.
Some numbers from the last 30 days, because LinkedIn rewards specificity and because I said this would be a receipts feed:
- 7 shops, all producing daily, zero closures.
- One overnight equipment failure, mitigated in under 3 hours.
- 2 hires, 1 resignation, current floor headcount sitting where I want it.
- Software: shipped two updates to the daily digest bot, started the inventory module.
- Investor side: prepared the Q2 report, on track to send the day it's due.
- STR / MTR side: portfolio held steady at 11 units, occupancy where it should be for this season. (Lane I'll write more about next month.)
What I'm watching going into July:
- A vendor contract that's coming up for renewal where I think I can negotiate $9K/yr out of the line.
- A second tier of inventory build, where the variance flag goes from "tells me" to "tells the manager and tells me."
- A shop where the lead's tenure is now over a year. Promotion conversation is teed up.
The shape of the month is unglamorous. That is the point. The wins are in the variance staying flat and the systems staying boring.
If you're considering this lane, this is what a "good month" looks like from the inside. No fireworks. Just the dials staying where I put them.
Hashtags: #smb #operations #monthlyrecap
4. Newsletter — "Receipts from the Back Office"
Cadence: Bi-weekly, published natively on LinkedIn as a Newsletter (own the subscriber list, decoupled from the feed algorithm).
Length: 800–1,200 words per issue. Longer than a post, shorter than an essay.
Promise: Real numbers from an operator who builds his own software. No motivational content.
Issue 1 — "How I planned my way to a layoff"
The full timeline of the October 2024 exit. The financial setup that made it possible (5 STRs cashflowing, 12 months savings). The honest cost-benefit. What I would not recommend doing the same way. The piece of advice I keep giving ex-tech friends who ask.
Issue 2 — "$60K/yr of SaaS, replaced in three weeks"
The full stack breakdown of the internal tools — Discord bot, daily digest, investor reports, scheduling. What each one replaced. What I would NOT recommend building yourself (calendar, payroll, accounting — leave alone). The pattern for deciding build vs buy when you're an audience of one.
Issue 3 — "Managing 20 people on a kitchen floor at 4am"
The deskless workforce playbook. Why Slack/Teams instincts fail. The laminated card. The whiteboard culture. The single Discord report that replaced four standups. The hiring filter changes. The retention math.
Issue 4 — "Variance is the price of admission"
The expanded essay from the Day 15 post. The cash forecasting system. The buffer rules. The cognitive cost of unbidden math. How to set up the observability so you stop paying for variance with your attention.
Issue 5 — "What a sub-scale GP actually does"
The Reg D 506(b) structure, plainly. Quarterly reporting as relationship infrastructure. The honest mechanics — fees, alignment, the carry conversation, the GP draw decision. What I'd structure differently if I started today. (Note: structured carefully — informational, not a solicitation.)
5. Engagement Plan
Daily target: 5 substantive comments on 5 different accounts. Not "great post." Genuine extensions of the original idea, ideally adding one specific number or counterexample from operator life. This is the warm-up before the post-publish window.
Profile types to engage with daily:
- Ex-tech operators / SMB acquirers — people 6–24 months into their own buy-out. Mutual signal. Build the peer cohort the Day 13 post named.
- Search fund / ETA voices — the established names (operators with 3+ year track records) and the rising voices (people sharing real LOI / diligence content). Comment for visibility-in-the-niche, not for follows.
- Vertical SaaS founders in SMB-adjacent categories — restaurant tech, deskless workforce tools, ops platforms. Jack's "I built it myself" lane is interesting to them because it's the customer voice they rarely hear.
- LP / family-office voices who post publicly — light-touch engagement on substance, never pitch. Plays a long game for future fund growth.
- Ex-tech career-pivot voices — broader resonance audience. People considering the jump are the strongest future newsletter subscribers.
Post-publish engagement protocol:
- First 60 minutes: respond to every comment, substantively. Reward the early commenters with a real reply, not a thank-you.
- Hours 1–4: keep checking, keep replying. The algorithm reads continued conversation as quality signal.
- Day 2 morning: one last sweep of any overnight comments.
- Never thank generic compliments with another generic thank-you. Either extend the idea or pass.
6. Lead Magnet (LinkedIn-Specific)
Title: "The Ex-Tech Operator's Internal Tools Stack — what I built, what I bought, what I'd skip"
Format: A 12-page PDF, gated by email signup to the Newsletter. Distinct from any IG/TikTok lead magnet, which leans more lifestyle/transition-narrative. The LinkedIn magnet is technical and operator-facing.
Contents:
- The 4 internal tools I built in 3 weeks (Discord ops, daily digest, investor reports, scheduling) — what each replaced and what it cost.
- The 3 categories I refuse to build myself (accounting, payroll, calendar) and why.
- The build-vs-buy decision matrix I actually use.
- A copy-pasteable Discord bot starter skeleton for end-of-shift reporting.
- The "audience of one" principle — why most SMB SaaS pricing makes building yourself rational.
Why it converts on LinkedIn specifically: the audience here is technical enough to want the artifact, busy enough to value the shortcut, and senior enough that the email-signup friction is non-blocking.
Distribution mechanic: Pinned to the Featured section on the profile. Referenced in the Newsletter welcome flow. Mentioned in carousel CTAs (Day 3, Day 11, Day 18), never in long-text posts (where pitching breaks the voice).
7. Connection Request Strategy
Default rule: Never use the default LinkedIn copy. Every request is personalized, references a specific piece of content, and ends with no ask.
Three templates Jack will rotate:
Template A — Commenter-to-connection (highest conversion):
Saw your comment on the [topic] post — your point about [specific detail] was the part I was hoping someone would push back on. Connecting because I'd like more of your voice in my feed. No ask.
Template B — Operator peer:
18 months into running 7 donut shops and 11 STRs after leaving tech. Saw you're [specific stage / specific business]. Always trying to build the cohort. No pitch, just want to follow your stuff.
Template C — Vertical SaaS founder:
Building internal tools for my own SMB after replacing ~$60K/yr of vertical SaaS. Saw your post on [their product / category]. Curious to follow — I think the "audience of one" operator is a customer profile your category underweights.
Volume: 10–15 personalized requests per week. Quality over throughput. 30%+ acceptance is the floor — anything lower means the personalization is sloppy and needs to be tightened.
Who NOT to send to in Month 1:
- LPs or potential LPs (no capital conversations during brand-build phase — protect the line)
- Recruiters (different lane, different signal, dilutes the operator positioning)
- Generic "founder" accounts with no specific intersection
8. Month 1 Success Criteria
By Day 30, the calendar is considered on-track if:
- 4+ posts cross 10K impressions (LinkedIn's natural ceiling for a small but quality follower base in this niche).
- 1+ post crosses 50K impressions. Likely candidates: Day 1 origin, Day 15 essay, Day 18 GP carousel.
- 30%+ of comments are substantive (more than emoji or "great post").
- At least 5 inbound DMs from the target profile types (ex-tech operators, vertical SaaS founders, search-fund voices). Recruiter spam doesn't count.
- Newsletter live by Day 14, Issue 1 published by Day 21, 100+ subscribers by Day 30.
- Featured section optimized with lead magnet by Day 7.
- Profile headline rewritten by Day 3 (working draft: "Operating 7 donut shops + 11 STR/MTR units after 13 years in tech. Building the software in the back office. Receipts, not theater.")
If the post that underperforms is Day 1, the voice is too soft — re-cut. If the post that overperforms is Day 15, the calendar is correctly weighted toward the tech-to-operator lane and Month 2 should keep that ratio.
End of 30-day plan. Month 2 opens the STR/MTR lane (Pillar 2), introduces the second carousel cadence, and triggers the first newsletter cross-promotion to IG/TikTok audiences.