Connor Pera

In the recovery community we have a saying that goes “you get sober with your feet, not your head.” This lesson applies to so many other areas of life. Stop thinking and planning - take action.

Earlier this week was talking to someone about the rarity of the SMB acquisition entrepreneur “hat trick”: 1. Business that comfortably services its debt 2. Business is growing significantly and consistently 3. Owner pays themselves a market salary They’re out there, but don’t let X convince you it’s common. The hat trick is the exception not the rule.

Part of why I left corporate was the bureaucracy. At big companies, getting anything done usually means alignment meetings, signoffs and decks about the deck. I wanted to move fast and own the decision. What I didn’t appreciate at the time is that no bureaucracy doesn’t mean freedom. Once you start growing, it means chaos. We’ve doubled TPA, and a lot of what I’m fixing now is the cost of moving fast: decisions made on the fly, processes that live in someone’s head, and work that piles up because nobody slowed down to design how it should flow. (We get the business we deserve, and I built a lot of this one.) I’ve come to see it as a trade-off, not a good-versus-bad. When you’re small, fast decisions are an advantage, and breaking things is how you learn. At scale, slow decisions start to make sense, because a bad call ripples across hundreds of people and millions of dollars. Too slow, and you get boredom and bureaucracy. Too fast, and you get chaos and disorder. The skill is knowing where you are on that curve and moving the dial on purpose as you grow. I’m learning to turn it a few clicks toward the side I once ran away from.

Huge pet peeve of mine: people “confirming” a meeting with text in an email and not sending a calendar invite. “Sounds great, see you Tuesday at 2!” Great. Where’s the invite? Now I have to email you back and ask for one, like I’m your assistant. Honestly, I don’t get how people run their days without a calendar. My calendar is my day. If it’s not on there, it isn’t happening. It’s one of the only reasons I still like Outlook – the calendar product is great, and I’m very used to it. So when you confirm by email and stop there, you haven’t scheduled a meeting. Cranky old man vibes, I know, but felt compelled to share. Please send an invite.

So many things in life follow the midwit meme. The simple answer is right, but you only earn it by going through the complicated middle. For me right now, it’s “hire a GM and build a holdco.” It sounds like something an SMB course seller would say, and for the last several years I’d have argued against it. You don’t know the business yet. You haven’t built the systems. Hiring a GM too early just hands someone else a mess you don’t understand. All of that was true when I bought TPA. It ran on hero effort, and I needed to be in the seat to change that. Three and a half years later, I’ve landed back on the simple answer. The difference is that now I know why. I’m better at seeing the bold move and allocating capital than at running the daily machine, and the business deserves someone who loves the daily machine. To be clear, I’m not there yet. There’s still a lot of building to do before a GM can own TPA, and I’m figuring out the holdco piece in real time. (Ask me in a few years how it went.) But I know which direction I’m walking now, and it’s a lot easier to do the work when you know why you’re doing it, and have more realistic expectations for how hard it will be and how long it will take.

Next year’s goal is $1MM in EBITDA. We’re currently very, very, very far off, but I’m not backing down from the goal. I’m going to do everything in my power to hit it. But the long-term goal matters more which is getting truly excellent at building and leading companies. If I do that, the enterprise value takes care of itself, and I believe that’s a $100MM+ company someday. My BJJ instructor recommended Mastery by George Leonard, and it’s reframing how I hold both of those goals. Leonard’s argument is that real progress in anything happens on the plateau – long, flat stretches of practice where it feels like nothing is happening. Our culture hates the plateau. We’re trained to want the result now, the quarter, the bottom line. (Jiu-jitsu cures you of this fast, by the way. You can go months feeling like you’re getting worse.) Business has its own version of this. If next year’s number becomes the only thing that matters, you’ll eventually buy the wrong company at the wrong price because the calendar told you to. You’ll stretch the debt coverage, skip the diligence and convince yourself it fits. A forced deal can set the long game back years. Missing a goal costs you a year. So I’ll push hard for the number. If it comes down to the number or the long game, the long game wins every time, and I’d rather be on the plateau getting better than chasing a shortcut that costs me down the road.

I caught up with an old friend recently and gave him the quick update on how business ownership is going: revenue has doubled since I bought the business, the team runs the day-to-day without me, and profitability still isn’t anywhere near where I want it. I spend most of my time on that last part. It matters, but honestly, I’m also never satisfied and I lose perspective easily. His reaction was basically “that’s great dude... isn’t this the first business you’ve run?” (Technically no, I had a side hustle before, but basically yes.) What hit me wasn’t that he was impressed. It was where he started from. His default assumption was that running a business is insanely hard and mostly problems. So doubling revenue and building a team that runs without me sounded like a lot of progress. My default was that it should already be working. So all I could see was thin margins. Same facts, different starting point. I’m trying to measure from where we began instead of from where I wish we were.

The bar for standing out is so low that a tiny bit of extra effort puts you ahead of almost everyone. Thank-you notes are my favorite example (if you’ve followed me for any length of time, you’ve read one of my rants on this). Someone gives you 30 minutes of their time or an intro, and maybe 1 in 10 people follow up with even a two-sentence email. Two minutes. Completely unforced error. Same with staying in touch. Three years ago, I traded a few messages with someone and never heard from him again. This week he came back asking me to help with diligence on his deal. (I’m not doing free diligence for anyone, for the record.) A two-line note every 6-12 months, and I’d have happily hopped on a call. And job searches. “I’ve applied to 100 jobs and nobody’s called me back.” How many were Easy Apply? From the hiring side, those get skimmed and usually skipped. The person who took five extra seconds to upload an actual PDF gets ten times the attention. Add a short note to the hiring manager, and you’re in a category of maybe a handful of people. None of this takes talent. It takes caring a little more than the default, consistently.

A heuristic I keep coming back to on AI and job displacement: get closer to the person making the decision to buy. The further your work sits from that moment, the easier it is to replace you with a process a model can learn. I’m watching this happen with back-office work across a lot of small businesses right now. What’s hard to replace is sitting with a customer, hearing the problem they didn’t put in the RFQ, deeply understanding why they’re considering buying (and what moves the needle on that decision), and being the person they trust to solve it. It’s not a perfect rule. But if I were early in my career today, it’s the one I’d steer by.

Sometimes the hardest part of running a business isn’t picking the bets. It’s picking the order you make them in. Hire the GM before the next acquisition, or after? Fix production before the building move, or let the move force the fix? Clean up finance first, or grow into a finance team that can handle it? Each one makes sense on its own. Done in the wrong sequence, they stack on top of each other and the team pays for it. I spend more and more time thinking about the sequence than on the decisions themselves, and I still don’t feel like I’ve got a reliable way to get it right.

My business mostly runs without me in the day-to-day. I’m proud of that, and I’ve paid dearly for it. I built a leadership team ahead of where the revenue said I should. That was an explicit trade-off, and our margins are tighter than they’d be if I were running the floor myself. The bet is that as we scale, the business keeps paying me enough to cover my bills while it runs without me, and I go buy the next one and run the same playbook. On paper, the path really is as simple as the internet makes it look. It’s just much harder, longer and more grueling than anyone posting about it lets on. Most days it feels nearly impossible. And I’m not certain it’s the right bet. I believe it is, but there’s real doubt in it, and the downside if I’m wrong isn’t small. Living with that uncertainty is a bigger part of the job than I expected.

We’ve started down the lean path in production. 5S first, now looking hard at flow. The biggest opportunity I see for us is moving toward single piece flow: a job moving from prepress to press to finishing to shipping without sitting in a queue between each step. Right now most of our lead time is waiting, not work. Print is built around batching, though. Gang runs, makeready efficiency, finishing in big lots. I’m sure some of what we batch should stay batched. I’d love to talk with anyone in print or print-adjacent work who’s actually made this shift: what worked, what didn’t translate, and what you’d do differently. DMs open.

I spent part of this week writing our part-time employee policy. Hours, scheduling, how unpaid time off works. In a $2M print shop, you don’t need that written down. Everyone knows everyone, the owner makes the call, and it mostly works out. We’re at a $4M+ annual run rate now, and this had quietly stopped working. Every unwritten rule became a one-off decision by whoever got asked, and those decisions weren’t consistent. Nobody did anything wrong. The business just outgrew the way it had always been run. We’ve been running into versions of this everywhere lately: how we cost jobs, how we close the books, how work moves across the floor. What got us to $4M won’t get us to $10M either. More and more, my job is to see where the next thing is going to break and get a system in place before it does.

Question for operators who’ve solved this: Once a job ships, what does your path look like from delivery to finished monthly financials? We’re mapping ours step by step right now. Ship confirmation, invoicing, collections, bills, payables, close, reporting. It touches the shop, the CSRs, a bookkeeper, and a fractional CFO, and nobody owns the whole thing end to end. I’m wrestling with whether to in-house all of it or just tighten the handoffs. Would love to compare notes with anyone who’s been through it.

For a long time, I thought being a good leader meant staying close to the details. \ It turns out my team doesn’t want that from me, and I'm not great at it anyway. What they want from me is a few things: what we're doing, why it matters, and what success looks like. Then they want me out of the way while they figure out the how. It was another Strategic Coach tool that made this click for me: the Impact Filter. It's one page – purpose, importance, the ideal outcome, and the specific criteria for success. Writing it forces me to do my job properly. Handing it off forces me to stop doing theirs. Now my involvement after kickoff is two things: updates and asking what's blocking them. Everything in between belongs to the people actually doing the work – and they're better at it than I'd be anyway. AND they don’t want to come up with the new ideas either, which is all I want to do. Win-win!

The other day I posted about how a lot of the value our company creates is in the coordination and distribution layer, and the logical response is usually “why can't a 3PL just handle this?” For storing and shipping finished goods at scale, they should. They'll beat a printer every time. But campaign print breaks their model in a few ways: · Every store's kit is versioned at production (this one gets the 36" header for its older fixtures, that one gets double door decals) · The materials have a shelf life of weeks, not months · A misprint found at the warehouse goes back to the printer, the timeline slips, and two vendors point at each other · Shipping from printer to warehouse to store adds a step, time, and damage risk When the same team prints, kits, and ships, there's one place to fix problems and one party accountable. (And for the big storage-and-shipping volume? We'd happily use a 3PL as a subcontractor. They're a partner here, not the competition.)

I keep a short list of people I'm intentionally investing in. Not prospects or a pipeline, just people I want to add value to over years. The framework is Strategic Coach's Top 20 Club and Farm Club, and it's the first relationship management system that has actually stuck for me. Most tools give you half of it. A CRM gives you cadence (remind me every 60 days) but treats every contact as equally important. The 80/20 advice tells you a few relationships drive most of the value, but gives you no system for actually keeping up with them. This does both. The Top 20 are the vital few relationships, each with a reason they're on the list, a touch cadence, and a next action with a date. The Farm Club is the next ring out, people I'm investing in early, each with a clear thesis for what would move them up. Most of the work is simple: an intro, an article, a check-in when something big happens in their life. Almost none of it pays off in a straight line. Over enough time, it ends up being where most of our best opportunities come from (and some of my most rewarding relationships).

Everyone says print is dying. Print as a product is. Flyers, business cards, anything a buyer can price-shop online is a race to the bottom, and that part of the story is true. But a brand with 200 stores doesn't just need flyers. It needs every location to get the right materials, kitted to its own fixtures, delivered by the same date, with a record of what went where. The ink is the smallest part of that job. The coordination is most of the value, and it gets harder every year as brands add locations, SKUs, versions, and campaigns. That's the part of print I'm building around.

Most of the travel I do for work is exhibiting a booth at a conference for a customer or for business development, and it’s almost always something in the franchising space. Obviously, I’m there as a print vendor and I’m happy to answer questions and pitch our services, but what actually resonates much more with franchisees is asking how their business is going, what they were doing before, and sharing a little bit of my ETA journey with them. There’s a camaraderie between entrepreneurs that exists almost nowhere else in the world and I love it so much.