March 2026: Florida Man, Big AI, and the Value of a Business

Work in Progress: March 2026

Florida is growing on me. For most of my adult life, I struggled to enjoy vacationing in Florida.

Too many strip malls. Too artificial. Too much plastic waste. It felt as if a tank top and a casino had a baby and grew it up to be a personal injury lawyer. And yet, on my trip to Southwest Florida last week, something shifted.

Maybe it was the need to be warm after the never-ending winter we had (are still having) in Toronto this year or perhaps after enough years of living in a highly organized, rule-based society like Canada, there is something refreshing about taking a break in a place that feels like it was built on a double dare.

In a world of increasing surveillance, signalling, and trying very hard to appear correct at all times, there is something nice about being somewhere that feels a little less concerned.

I wouldn’t say I’m becoming a Florida man…But I’m no longer ruling it out.

All that + more from March:

1. What good team offsites actually deliver

2. Are we all just going to work for Anthropic?

3. Be prepared for "Big AI", but believe in humans

4. Betting on "one to many" over traditional direct sales

5. Selling your B2B distribution business

1. What good team offsites actually deliver

We took some of the team down to Orlando, Florida last week to spend time with @Tom Moore and the CounterpartOS team.

Offsites are easy to get wrong. Too structured and they feel corporate. Too mystical and they feel too self-indulgent. This one was neither.

Tom is exceptional at this. He has a lot of gifts, but one of the biggest is that he distributes courage in bulk. And courage is not exactly flooding the market right now.

There’s a lot of fear out there. In the market, in teams, in founders. So being around someone who helps you think bigger, be braver, and move with purpose is pure gold right now.

Good offsites are rare, and this one made me realize the specific quality of good ones: you leave with more clarity and better questions than you arrived with. 

Not a polished deck. Not a list of action items that will be forgotten next week. Actual clarity about what you're building, why it matters, and what's been getting in the way.

There's a reason most teams don't get there on their own. Day-to-day work is a terrible environment for honest thinking. The noise is too loud. A good offsite gives you the space to zoom out, say the uncomfortable things, and think at a level a calendar doesn’t allow.

The most valuable takeaway isn't a better plan. It's the courage to commit to one.

And honestly, maybe that's Florida's whole thing too. Less second-guessing. More committing.

2. Are we all just going to work for Anthropic?

My wife rhetorically asked this question the other day.

What does that really mean? To me, it points to two underlying questions.

First, are we heading toward a future where people lose jobs to AI agents in the name of efficiency, while weakening tax bases, communities, and the social systems built around broad human participation in the economy?

Second, will a small number of frontier model companies end up with outsized control over the workforce itself, able to charge what they want, behave how they want, and make business and financial independence harder to maintain?

That is a pretty dark version of the future. However,  I don’t think this future is the most probable one.

I am not convinced it will be commercially or technically worthwhile to build models and agents for every job, even many lower-skilled ones. Replacing humans is not only emotionally difficult, it also has to make economic sense, and in many cases the ROI may simply not be there.

On top of that, much of the developed world is facing a population contraction and problem and an impending labor shortage. AI may prove more valuable as a supplement to human capacity and a multiplier of human ingenuity more than as a replacement for it.

Humans have always adapted to major technological change, and we tend to become stronger through that process. Across history, technical evolution has created disruption, fear, and real dislocation but it has also expanded what people are capable of building and becoming.

The bet I’m making: AI will not be the thing that replaces us. It will be one more chapter in the long history of tools that make us stronger.

With that framing in mind, I had a great conversation with @Leo Lu from @Foundation Capital. He and @Joanne Chen put together a beauty of a thought piece on how work eventually gets reorganized. Some work moves to software. Human value shifts upward into judgment, accountability, trust, design, validation, and relationships. You can read the full article here. 

I found the org chart particularly useful as a visual for thinking through where that shift is already happening.

3. Be prepared for "Big AI", but believe in humans

If you, like us, are building AI workflows that will augment jobs and in some cases replace them, you have some responsibility to help level people up. Full stop.

I’ve been feeling this pull lately toward leaving the world a little better than I found it. So alongside the AI workflows we’re building, we’re going to set up a training program for our customers to help people build basic to intermediate AI skills. 

This is helpful not just from a social cause point of view but from an onboarding one too.  Broadly, we have a culture gap in the work force as it pertains to “AI readiness”.

You can have the best AI tools in the world, but if the people expected to use them are intimidated, threatened, or resistant, you are not getting that idea, you are not making progress. Your buyer may be excited. Your core user may not be.. And if that gap doesn’t close, you’re dead on arrival.

A stubborn user group will outlast a great product every time. The technology is rarely the problem. The people are the project.

If you’re going to do some clear cutting, you need a tree-planting program in place too.

4. We're betting on "one to many" over traditional direct sales

The venture community right now expects every company to be faster, leaner, smarter, more scalable, and somehow more durable… while hiring fewer people and making fewer mistakes. 

At first you laugh. Then you get a bit depressed. Then you stop looking for a playbook and start getting creative.

That part I’m enjoying.

The old school go-to-market formulas feel tired to me. In 2020, in B2B SaaS, everyone was basically running the same motion and the main difference was who executed it best.

I’m less sure that works now. 

So I keep coming back to a much simpler question: What is actually true for us?

For me, I’ve been feeling more bullish on channels, partnerships, and community. One-to-one sales still matter. But I’m not convinced it scales on its own at the speed the market now expects. We know how to sell our product. We know the ecosystem. We have relationships. We can teach the motion. We can build trust through people who already have it.  

“One to many” is the bet we’re making.

On the performance side, we ended the quarter right on plan. I wanted a bit more, because I always want a bit more, but April is shaping up well and we’ve made a few decisions that I think should improve sales velocity.

One honest miss: the impending energy crisis as a result of the”Iran situation” has made one part of my freight-as-a-percentage-of-PO-value thinking look pretty naive in the near term. So I’m learning. Which is good. I like learning. I just prefer the version where tuition isn’t paid in actual money.  That said I am still very bullish on getting to an “under writing freight” pricing model at scale bc it just makes the most sense and our customers really want it.

5. Selling your B2B distribution business

Here's a stat worth sitting with: Over 70% of mid-market businesses are expected to change hands over the next decade. That means a lot of our customers are heading toward an exit… whether they're thinking about it yet or not.

I’m thinking about an interesting question beyond “how do we save our customers a few bucks?” 

The question I'm now focused on is: how do we help double the value of their businesses before they sell?

I spent some time this month with business valuation experts looking at the gap between a business-as-usual distributor and a much more systemized, scalable, and digital operation. which I’ve been loosely calling “Amazon good.” 

I used GPT research to do an initial comparison, then had a business evaluator react to it. His feedback was basically: “directionally right and good start, but context matters”. So now we’re working on building something more grounded and more useful.  I share the breakdown here. 

If we can help a company become more systemized, more visible, more measurable, less dependent on heroics, and less reliant on tribal knowledge, we are not just helping them run better. We are helping them become a fundamentally better asset.

That’s super interesting to me.

And it feels a lot more value added than the usual software pitch.  Not to mention, it's very exciting mission to work on.

In summary:

Florida is growing on me.

Beware of "Big AI", but believe in humans. We win every time.

And I'm increasingly interested in helping build businesses that are not just more efficient, but more valuable.

We can have it all.

Justin