Jon Cowley | Decision Tech + AI Founder
2.4K posts

Jon Cowley | Decision Tech + AI Founder
@whatifi_io
I help teams make better decisions with scenario planning + AI. Ex-VFX studio head (150 artists, $27M revenue). Building a visual alternative to spreadsheets.
Vancouver, British Columbia Katılım Ocak 2017
823 Takip Edilen529 Takipçiler
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I'm going to be documenting the AI agentification of my tech startup. We've gone deep on product, and we've absolutely sucked at distribution. We have a ton of awareness, but have done a lousy job of maintaining those relationships and keeping communication going. As we start getting busy with individual pilots, it becomes even harder to maintain that bigger communication loop. So here's what's happened so far: the Mac Mini arrived about a month ago. I've been watching a ton of videos. Here's my current "agent" tech stack plan:
Notion
Slack
Gmail
Moving off of HubSpot into a new CRM that's less expensive
N8N
OpenAI
OpenClaw
Progress so far: cracked a bottle of wine last night and installed open claw. Created a stand-alone account on the iMac.
Connected OpenClaw to Slack and my Gmail.
Created my first automation, which is a cron job that runs through the last 24 hours of my email and bubbles up all the priority emails and posts them to a stand-alone Slack channel.
Took about two hours to set it up, and a lot of it was asking ChatGPT questions as I progressed.
Checked Slack this morning, and there was our first automation message. Nothing important came in over Saturday, so the summary was pretty underwhelming, but at least it triggered.
So here's the big goal. I have a piece of very complex and novel scenario planning technology that we've created over the last couple of years, bootstrapped, and I've been full-time on it for about two years.
At our largest, our team was seven, and now we're down to two and a half. Core product is built but being maintained as we onboard new customers.
I've also been doing a lot of service work to pay the bills. I've gone so deep on Lovable that people are now asking me to build custom software for them to run their businesses.
I've also spun up a few little mini projects on lovable as part of my learning curve. My plan is to use AI agents to market and distribute those mini products as a learning exercise for me. Once those systems are in place, I intend to migrate those learnings over to my core product.
One of the first things I want to do is monitor some social media posts to see if I can find opportunities to discuss one of my many products. It's a B2C property management set up for off-grid and hard-to-access properties.
At the same time, I'm going into my years' worth of Notion data for my core product and starting to clean that up to make it more agent-friendly. Right now, it is a dog's breakfast of outdated pages and duplicated databases, so I'm trying to bring structure to that.
More to follow.

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I don't think @TELUS @TELUSsupport realizes how much their constant sales/slop support phone calls are destroying their business brand. I just got a call from one of their reps overseas asking me for feedback, even after I filled out a monstrous feedback form yesterday online. After I had previously told multiple TELUS reps that I was only a customer because I am trying to shut down my father's accounts after his passing and to stop calling me and trying to sell me new services, given my situation.
When I tried to explain this to the person who just called, they made a bunch of inappropriate and juvenile sounds and then hung up on me.
There is zero chance that I would move any of my services to TELUS at this stage.
This is the hidden cost of outsourcing sales and support and making every phone call into a pseudo sales call.
I still have several services to wind down with Telus on my parents behalf - home security, internet, home phone - an I cringe thinking about how much time I will spend on the phone and the quality of those upcoming experiences.
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I can't even begin to express my extreme frustration with @telus as a company and their customer service workflow. My father passed away 3 weeks ago. I've been trying to settle his account, close accounts, pay bills, etc. I've spent 5 hours on the phone to date... 6 calls.
And just received another $500+ "overdue" bill that I settled weeks ago.
And you try to call their support number on their website. And instead you get a sales pitch... no opt out. So I "press #" and it kicks you out saying this number doesn't work in my calling area (I'm in Canada). So I write down the number they suggest... only to have it come right back to the same voice workflow... and the same death loop.
I was able to reroute my Father's hydro bill in less than 10 minutes.
I don't think Telus realizes how much potential revenue they are losing as a result of their clunky, poor quality controlled customer experience.
Try to book a call back? Only to be told they will call back in three days... and when they do... the automated voice system is entirely in French....
And EVERY single rep I talk to ends up just trying to upsell me on a new service... when all I am trying to do is shut down my father's accounts, settle his bills, and move on.
Every step of my experience with Telus has been unnecessarily painful.

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@jasonlk - you've built all your agents from an already established company with established SOPs, and then refining down. So you knew what you needed, and then you just had to systematize it.
What advice would you have going the other direction for a super small team looking to expand in the other direction and bring on AI SDRs and social media agents w/o systems in place?
What are the first three stair-steps you would take on this journey?
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In my opinion, there are three layers here there is the “database” layer, the calculation layer, and the view layer and currently Excel is all three of these. That’s why it works. That’s also why it has the potential to be disrupted.
I think we all agree that Excel really shouldn’t be used as a database, but often it is. Once that migrates to being a true database, and AI is really forcing that to happen in all sorts of business functions, then that layer goes away.
So now you’re left with calculations and view. Most folks are already exploring other tools to view their data. They’re just locked into the Excel world because of the first three layers. But now you can build these few layers in half an hour with vibe coding.
So all that’s left now is the calculation layer and yes, that is excels biggest strength but I had to argue that there are ways that AI can overtake that as well. I know that firsthand because I’m in the space. It’s not a solved problem yet, but I can see how it can be solved. So now, if all of these things become interchangeable, then the technical moat is gone. Now it is back to your point, a comfort zone most.
English

There’s a growing idea that AI is going to replace tools like Excel with a world of one-off, AI-generated apps.
To be fair, there will be real disruption here. The tools will change and the interface may look very different. It may not be “Excel” in the way we recognize it today.
But inside organizations, work still depends on shared structure. Teams need a common place where data lives, where definitions stay consistent, and where someone else can open a model and understand what’s going on.
That’s what tools like Excel have done extremely well. They create network effects. The more people who can work in the same system, the more useful that system becomes as a shared workspace.
If everyone starts building their own AI-generated tools, that shared layer starts to break down. Things might work individually, but they become harder to audit, connect, and scale across a team.
So yes, disruption is coming. But you can’t ignore the importance of shared standards and network effects. Whatever replaces or evolves from Excel will still need to solve for that.
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“There are now real, well-funded AI-native CRM platforms that didn’t exist two years ago. And for the right company, they might be the better answer.
•@lightfld started over with a CRM built around “complete customer memory.” You never enter data. Connect your inbox, and five minutes later you have a populated pipeline. 2,500 companies in three months. 100+ YC startups. $81M raised at a $300M valuation. Hundreds already migrating from HubSpot. If you poll current YC startups, the vast majority are using neither Salesforce nor HubSpot. Lightfield is eating that cohort. Best for founder-led sales through ~50 employees at $36/user/month.
•@MonacoGTM is Sam Blond’s play (ex-CRO Brex, ex-Founders Fund). $35M raised from top angels and Founders Fund. The differentiation: AI-native CRM + prospect database + AI agents, all supervised by experienced human salespeople Monaco employs. You’re not just getting software. You’re getting a sales team. And unlikely other AI GTM vendors, it literally gets you appointments set in your calendar with opt-in prospects. We use Monaco ourselves and it was booking meetings with top AI companies from Day 1. Best for outbound-first seed and Series A startups.
•@aurasellai goes after mid-market tool sprawl. Ex-Harness CRO and CTO, $30M seed from Menlo and Unusual. Replaces 15+ GTM tools with one AI-native platform. The smart move: they also offer a GTM OS layer that runs on top of your existing Salesforce or HubSpot, so you don’t have to rip and replace on day one.
•@reevo_ai has raised $80M from Khosla Ventures and Kleiner Perkins. Founded by David Zhu (ex-Head of Engineering at DoorDash, scaled from $700M to $75B market cap) and three other DoorDash/Square/Stripe operators. Similar to Aurasell in ambition (replace the whole fragmented GTM stack) but broader in scope, spanning marketing, sales, and customer success in one platform. 90 employees already, engineering-heavy team. They generate their own first-party activity data instead of relying on integrations.
•@attio has become the CRM of choice for many AI-native companies (Lovable, Granola, Modal, Replicate). $141M raised, $52M Series B from Google Ventures, 5,000 customers, 4x ARR growth. Flexible, programmable data model for technical teams that want to shape CRM to exactly match their GTM motion.”
Jason ✨👾SaaStr.Ai✨ Lemkin@jasonlk
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@jasonlk But will they use an AI to drag their heels and extend out their payment terms?
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@whatifi_io i think we can do collections though
let's see
English

An experiment we want to run after SaaStr AI Annual in May ...
Can a custom "AI VP Finance" manage and run eight figures of collections?
Maybe
We already have 10K, our AI VP of Finance integration all Salesforce and other revenue data, contacts, etc.
And QBee our VP of Customer Success already follows up with all sponsors better than any human did
Can an AI Agent do collections, for real? Collections is always a top headache.
We're curious to see. Watch this space.
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@rexsalisbury @Apple I use Wispr on my Mac and iPhone. Game changer. Even works well when, ironically, I’m whispering.
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@apple pls fix voice transcription. Your built in stuff sucks. Do better.
I spend all day talking to my computer.
Then I pick up my phone and I am immediately frustrated.
The iPhone does not feel magical. It’s this frustrating barrier between me and everything I wanna do.
most frustrating part of my stack.
I am starting to hate my iPhone. I want to throw it away. Go back to my laptop.
Or buy a pixel.
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Ask an LLM what 24X3 is.
Chances are it will respond 72.
But then ask it how it calculated that.
This is the problem we’ve solved with whatifi.
The ability for LLMs to reliably, accurately, and repeatably run complex (and simple) timeline based financial and operational calculations without code.
We’ll be at WebSummit Vancouver next month if you want to see our AI powered financial scenario modelling on action.


English

Ask an LLM what 24X3 is.
Chances are it will respond 72.
But then ask it how it calculated that.
This is the problem we’ve solved with whatifi.
The ability for LLMs to reliably, accurately, and repeatably run complex (and simple) timeline based financial and operational calculations without code.
We’ll be at WebSummit Vancouver next month if you want to see our AI powered financial scenario modelling on action.


English

@connoredwards I’ll be around. Built a framework and API that turns large language models into large finance models. Ability to reliably run financial calculations and hundreds of scenarios embedded into every day LLMs.
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Yep, they are large LANGUAGE models, not large FINANCE models. Inherently LLMs don’t have a sense of time or timelines.
Been awhile since we caught up but what needs to happen is a whole separate framework that large language models can use to run financial calculations. Basically it’s tool calling where the LLM can reach out to a third-party service and repeatedly and reliably run the exact same calculations every single time and then use those values in their downstream actions.
Been building tech to do this. I’ll reach out if you’re interested.
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Okay, so I am tech founder and I think AI is an absolute game changer.
But… my father died this week and I have been trying to pay his @TELUS bill for the past three days and my interaction with their poorly implemented AI and callback system has been nearly as stressful as our time in the hospital.
And something about having an AI say “we’re sorry about your loss” and then putting me on hold for twenty-plus minutes and counting missed the mark.
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