Jim Watson

“IT should just work” is a fair expectation. When ownership is split across vendors, tools, and roles, issues linger and repeat. IT works best when accountability is clear - someone owns the outcome, not just the ticket.

@SecretCFO #4 is key!

It’s hard to find balanced takes on what AI means for finance teams in the short term. Over on LinkedIn, people are fully losing their minds. My feed is filled with fantasies of CFOs firing their whole team after a heavy weekend of vibe coding. Let’s be clear: AI is going to transform the CFO's office. But not in the ways you’re reading about. Not yet. Like every tech wave before it, Amara’s Law will apply. We overestimate the short-term productivity impact and underestimate the long-term one. AI is right on cue. And this time, the curve may well be steeper. But that doesn’t make today’s hype any more helpful. You’re being told to fire half your team. Rebuild your stack from scratch. Learn to code like an engineer. For CFOs that is nonsense. Very little AI tech for CFOs is truly enterprise-ready yet. If the world’s best engineers - backed by billions in funding and full-stack AI teams - are still building, what makes you think you can crack it with two mugs of coffee and a 45-minute YouTube Replit tutorial? The idea that a CFO or their finance team should be building proprietary AI software isn’t just unrealistic... today it’s borderline reckless. You’re not a product org. You’re not a startup. You’re the steward of your company’s finances. Your job is to protect the business’s assets and grow shareholder value. To be clear, this advice is for established CFOs and senior finance leaders. If you’re early in your career, or you’re a current or aspiring CFOTech founder? You should absolutely be experimenting more aggressively. That’s a different playbook (and not one I should write.) But if you’re already in the seat. Running a finance team, managing cost pressure, tariff chaos, audit reform, and a volatile boardroom... your job is not to vibe-code your way through it. Now let’s talk about the “95% myth.” There’s this idea floating around that AI can do 95% of a finance task in five minutes - board packs, forecast models, strategy decks, you name it. But in finance, precision beats direction. Just because something looks 95% done doesn’t mean it is. Worse, it gives a false sense of confidence. You think you’re nearly there. You’re not. The final 5% is where all the risk lives. All the value. All the judgment. That’s the bit that matters most. CFOs aren’t paid for the first 95%. That’s the commodity layer. They’re paid for the last 5%, the sharp end of the decision. The edge. And the best-paid CFOs, are paid seven or even eight-figures ones for the final 0.1%. The part that only experience and real-world judgment can deliver. So if you shouldn’t be hacking your team to death with AI experiments, what should you be doing? Here’s the practical AI playbook for CFOs today as I see it: 1. Reframe where AI can actually help. It can’t write your board paper. But it can help you tighten it. It won’t build your model. But it can sanity check it. It won’t find your narrative. But it can pressure test it. 2. Don’t trust the “95%” myth. People say AI gets you 95% of the way there. But that’s an illusion. Just because something looks 95% done doesn’t mean it is. And in finance, that last 5% - the nuance, the judgment, the risk - is everything. It’s not the final touch. It’s the whole game. 3. Let the builders build. Take the demos. Work with tech vendors who live and breathe finance problems. Your job isn’t to build an AI-powered P2P system from scratch. It’s to pick the best one on the market and implement it well. We are a generation of CFOs scarred by horrendous tech implementations. But AI will make implementation and customization infinitely easier than we've seen before. 4. Get your data organized. AI loves structured data. The more your data is clean, consistent, and well-structured, in a proper data warehouse layer, the more AI-ready you actually are. Think integrity, granularity, metadata. That's what will unlock what comes next. 5. Experiment in low-stakes environments. Play where failure doesn't hurt. In my case, I built custom AI bots to help my kids with homework, tailored to their curriculum, learning preference, instructed to guide to the answer not give them the answer, etc. That’s stretched my thinking and showed me the art of the possible, more than any finance workflow. It’s where I’ve learned the most. You want cheap feedback loops, fast iterations, low risk. And for what it’s worth, here’s where I’ve seen AI be genuinely useful so far: - Editing comms: emails, specs, board packs - Sorting and prioritizing inboxes - Stress-testing story outlines and presentations - Surfacing directional insights from messy data - Scoring candidates against hiring criteria - Acting as a thinking partner when I need to challenge my own assumptions. So no, don’t fire your FP&A team and vibe-code a workflow replacement. Experiment, yes. But pick simple workflows. Low stakes. Clear feedback loops. Don’t eat the hyperbole. Keep one eye on AI, not both eyes and both hands. Your job is to run the business, not chase the unproven LinkedIn fever dreams. Keep your hands on the wheel. Stay curious. Stay skeptical. But most of all ... stay very f*cking crispy.

@RegZeller Hey Reg - Interested in learning more about what you have planned for the group. Acting CFO for our SMB

Just kicked off an exec-level finance peer group. Currently 15 SMB companies (probably add a handful more). Goal is to bring AI/ML/RPA into their functions. We’re looking for a few presenters to come in and chat through the basics of where to start, what can be done/tools, examples, etc initially, then more advanced topics as they progress Can’t promise anything from presenting beyond a captive audience. DM’s open

@sweatystartup A nice shoutout to @bankwithrelay, @ycwest!

There is a proven playbook to grow companies. What tools to use, agencies to hire, strategies to employ. Well here is my exact 12 step plan and my exact strategy for supercharging a business: #1 - New logo with 99 designs. It costs $299 and is good enough for me. #2 - New website by webrun.com. They've built 5 of my websites. Whoever you chose, make sure it is SEO optimized and has landing pages for each of your services and each location. KEEP IT SIMPLE. A person who knows nothing about your business should be able to become your customer in 5 minutes or less. #3 - Link building plan to increase domain authority and Google ranking with boldseo.com. The website structured correctly, content and these links are what will work for you. Make sure to do "citations" as well with your name, address, phone number that list your company on all the directory sites like Yelp, Angies list, Yellow pages and more. #4 - A LATAM or filipino hire through supportshepherd.com. $5 an hour can get you an excellent back office employee. Game changer. 80% of my employees at a SELF STORAGE company are overseas. You would be surprised how much can be managed and done from afar. #5 - A Google Business profile you check and post on every single day. And you get all of your customers to write you a review. This is a game changer as well and low hanging fruit. #6 - Google ads running with adrhino.com. Make sure you hire a company that can setup Google Analytics 4 and track how the ads convert to customers. You should get an ad spend amount per customer acquired so you can track profitability. #7 - Make sure to get a premium .com domain for a few thousand bucks with less than 13 characters. English words. Not .co. Not .net. Not .io. People invest thousands into their business but make due with a $19 domain wit hyphens. Makes no sense. #8 - Online banking with relayFi. It is easy to send money and get cards for all your employees. Don't accept cash or check. It is a waste of time and money. And people will steal it. #9 - An online software to run your business. Jobber or another one like it. A customer should be able to log in and pay an invoice in 2 minutes. And you should be able to send them a professional invoice and take auto-payment for services. #10 - Payroll tools like Deel (international) and Gusto make it super easy to run payroll. #11 - Bookkeeping and tax returns through BetterBookkeeping.com. I use them and they are awesome. Send monthly reports and prep tax returns. #12 - Slack for communication. Loom for sharing training videos. Avoma for recording meetings. It’s a cheat code to have these vendors to amplify my companies. (I’m a partner in several of these companies) What do you have in your tech stack that I’m missing? What tools do you love that I didn't share?

Take the lead and don’t pass the buck. Help make things right

@guessworkinvest Agree on your line of thinking, but would want to be sure to prioritize which problems you solve. Excel works great for us from a team sharing perspective and I used to be on Google Sheets. Understanding the true problem is key so you don’t move systems and have the same problem.

How do we compete as small business owners with no "real" skills or experience (actual know-how in the trades, 30 years of blood/sweat/tears, etc.)? I have been so reticent to move off Excel and start building dashboards in Google Sheets. It's clearly worse from a spreadsheet-building standpoint, but clearly easier in a team-sharing context, which is more relevant to me now than my PE days. But another former searcher turned operator reminded me -- if I'm not able to learn new tools, I'm no different than the older owners we buy businesses from, who refuse to switch from paper invoices to digital. That worked fine for them, because they were top notch service providers or had other skillsets that built great businesses without moving to more efficient systems. I don't have those skills, so I can't afford to also be bad at learning & implementing new tools/processes. Guess who's building in Google Sheets now...

@Fischbooks And vice versa…you may have a favorite but don’t necessarily focus on it nor have a specialty in it.

@Fischbooks To me, “having a niche” means having a focus in a particular industry/function/area. But…you may not be good at it and you may not love it. But you like it enough for it to be where you want to spend your time and to try and have expertise.

This got me thinking. Is having a favourite industry to work with the same as having a niche? 🤔

@extremesb Well, it was the Feed, buuuuutttt….

Belly Check time today…✅ road tour looking for the best chicken sandwich in the GTA….independent #QSR or off the map little chain preferred…any suggestions…..? #chicken #QSR $HBFG $QSR $SHAK $PTLO $SG $CMG $MTY.TO

@EAHelp Hello! Trying to get my son going on NHL 22 HUT (Xbox Series S) but getting an insufficient permissions error. What permissions are needed to enable the game?

@Fischbooks All good answers from others. Have implemented EOS and happy to chat about it if/when you have questions.

For those of you who have read Traction and/or Rocket Fuel or been through an #EOS implementation, what are the top 3-5 terms you think are critical to understand for a newbie?

@WealthandBiz @floAngel0 @jayvasdigital Not if it’s in Canada…

@floAngel0 @jayvasdigital correct. because you can debt finance 80% of this

$1.3M ARR software biz: $850k SDE, 100% net retention, 0% growth, largest customer is less than 0.5% of ARR, 2 contractor employees. I can’t mention the niche without people finding it. But it’s a mature non-growth industry. What would you pay for this?

@guessworkinvest Nice! Any benchmarks or framework you’re using to budget #3 or all gut intuition?

3 weeks to push through to end of year. Excited to finish strong by: 1) getting virtual CSR trained on rest of admin processes (started her with just 2 simple things). 2) launch new service line, including onboarding of tech who will lead it. 3) end of year bonuses & party!

@girdley Don’t for get the fifth one that wonders if you’re trapped under a bus or asks to pick if it’s because if A, B, or C

One cold email: fine First just trying again: fine Fourth cold email in a month: I click the “report spam” button

@guessworkinvest If you haven’t already, be sure to look at unique numbers. A lot of times, the same number is falling back multiple times. While it doesn’t really change if all you need is 1 to convert, but may help see other trends.

The bet on a virtual CSR: - Last 30 days, we missed 267 calls - 86 of those were at times we didn’t have call coverage and now will - Of that 86, 33 didn’t leave voicemails If just 1 of those 33-86 convert, the GM on that 1 should be ~45% higher than the monthly cost of the CSR.

@telsky Sounds like a juicy story

@jj_watson Have I ever told you about the “Haribo Layover”? forbes.com/sites/samlemon…

Twitter must’ve known I was in YQB and staying next to the Museum. I did catch many poop books in their windows and forgot to look into why until I saw this article. mcq.org/en/exposition?…

@sweatystartup You’re welcome: amazon.com/Go-F-Sleep-Ada…

My son is 5. What is a good book I should read to him aloud?

@divitkos Three key areas so far: business system foundations (EOS), clearer financials, and focus.

I’d love to hear from #CEOs from #SMBtwitter as well: What seemingly small changes have yielded the largest financial, operational, or even personal benefits? I’d love to feature some of your answers on the pod.

Working on a new pod episode featuring 4 mini case studies on 4 CEOs at different stages (from <1 year in the seat to fully exited), where I ask each only 1 question: What are the smallest changes you’ve made that have had the most outsized financial/operational impacts?

@AndrewDumont Congrats! So happy for you! Hope all is well!

Breaking my Twitter hiatus for some personal news… ✨