#43 The start-up phase. Chronicles of a Founder Dad.
One year of indi, a Whoop that doesn't lie, and a secret I can only tell you
🤖 AI - What a month of really leaning in has taught me
Over the last month I’ve gone from dabbling with AI tools to properly leaning in and trying to unlock what’s possible when you build a company around them. I don’t have all the answers, especially not the technical ones, but I’ve got some thinking that I reckon is worth sharing for anyone else trying to figure this out.
Pick a tech stack that’s AI connected - strong connections increase what you can do and save time. Loose ones don’t.
Don’t lock yourself in. Every month AI is demolishing another B2B SaaS tool, so pay month to month and iterate as you go.
Treat it as an investment, not a cost. Because most people still file it under “nice to have” and they’re going to get left behind.
Build for where it’ll be in six months, not where it is today. We’re putting things in place now that we can already assume will be table stakes in six months. Keeps us ahead of the pack.
Rip your old plan to pieces. Your headcount modelling is done, so how you think about a lot of things can change too. This is an opportunity.
Be aware of who and what is about to wipe you out and make sure you’re building your moat. We use an 8 Moats Framework (proprietary data, regulatory, workflow, proprietary distribution, ecosystem, network effect, physical infrastructure, scale) internally - you need to be hitting at least four for it to matter.
Figure out where AI still sucks and humans win - that’s relevant to your build. Put people there. But make sure they’ve got an AI appetite, because otherwise soon they’ll be dead headcount too.
This is the era of the multitasker and the generalist. Context switching while Claude thinks is a genuine superpower. The leverage is there for sure, but it’s intense.
It’s exciting and scary. Hold space for both. And take it seriously. Whilst this has the potential to drive a lot of positive change, I think we’d be naive to assume there won’t be mental health implications up ahead.
Use AI to create less screen time, not more. Supercharge what you stand for with it - don’t deviate from it.
To give you a sense of what this looks like in practice - I’ve basically built an interconnected brain across the company. Notion, Slack, Gmail, Calendar, Fireflies, HubSpot, PostHog, Stripe, Sentry, Supabase - all wired together through Claude, talking to each other, learning from each other. It does my morning briefing by pulling context from across all of those systems. It processes every call transcript and feeds learnings back into our strategy docs. It preps my 1:1s with the team by cross-referencing actions, Slack conversations, and pipeline data. It monitors competition in real time. It’s working when I’m resting. And it’s context is feeding every other part of the build too.
It’s like having a team of five that never sleeps. But you still need to know what to ask for - that’s the bit most people underestimate.
💤 My Whoop doesn’t lie
When Indi isn’t regulated, none of us are. We’re running on fumes and shot to pieces - the cortisol, the weight, the brain fog at 2pm when you’ve been up until 4am and you’re supposed to be leading a company. Your body keeps score even when you pretend it doesn’t.
So a tweak to Indi’s sleep meds, her regulation improving in the daytime, and boom - I’m physically playing at another level. You can literally see it in the Whoop data. The green recovery scores started appearing and it’s almost the new baseline.
Let’s be clear, we aren’t in the problem solved stage. On Sunday night i was up with indi from midnight to 5am, then 1 hour sleep, alarm goes off and i’m up and to work. But doing that only a couple of times a week is a MASSIVE improvement. And most importantly - a regulated indi is a happy indi!
🌏 Two great weekends
We’ve had a great couple of weekends as a family. I haven’t been able to say that for over two years. It feels really good. No words, just pics.
📱 Birthdays for Beckham & the indi app
It was Beckham’s birthday party on Saturday at a bike park and lo and behold, Indi jumped off a bouncy castle, 6 feet, solid floor, hurt legs. So Saturday night we got to head to Monash Children’s Hospital Emergency Room... again.
But this time, we had everything we needed. On route in the car, I said to Allie “we’ll see the triage nurse when we get there - tell the app what’s happened and tell it to get prepped” …. and it did. We had everything we needed - in triage, seeing the doctors, on discharge, at home after and communicating with everyone that needed to know. Easily.
Was it the app, was it the sunflower lanyard, the headphones, the fact Indi is older now so the disability is less hidden … all of the above? Something was different about this visit. We weren’t gaslit, we were offered a sensory room and given icey poles. Yeah it wasn’t the dream Saturday night, but it was pretty good! After 3 of us pinned indi down to have x-rays and she fell asleep, it was almost like Allie and I were on a date night!! Carls Jr on the way home - dreamy.
And this Saturday, as a company we are officially 1 year old! And so Indi presented us with the perfect test, to see where we are at, 12 months in.
As a business, in one year we’ve moved fast and learned a lot … and it’s pretty much time to put our foot down on bringing parents and clinics on, hard. Almost. One more sprint of iterations and then we go into proper acquisition mode. And maybe we can attack one of the bat shit crazy ideas we have in the idea bank.
Andddd we may have just closed a fresh investment 😉 🤫 There won’t be any PR for this one and I’ve retired from LinkedIn, so my secret is safe with you.
If you’ve been reading since Episode 1, you know what this means. More runway, more confidence from people who’ve looked under the hood, and more fuel for what’s about to come.
Hope you are having an epic week. We are. Orrin xoxo
🔗 Links
Gotta catch up. I've been leaning in a lot, too!
Every single time. I love reading your words. I love hearing about how you are tackling all the things. You're amazing. Hope Indi is having one of her good weeks xoxo