Tom O'Neill

Customization Is Cheaper Than Confusion Confused crews waste time. Generic tools kill buy-in. Every missed step costs you money. Custom workflows aren’t bells and whistles—they’re how teams align, move faster, and stop asking “how does this thing work?” Because clarity isn’t nice to have. It’s operational fuel.

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Everyone hates building their board decks... It's the worst. "Can't I do this in claude?" NOPE Every other BYOAI caps you at 15-20 slides. But, Steerco agents have the ability to create 150-Slide Presentations at the push of a button. Perfect if you're a Chief-of-Staff tasked with creating the board deck. No more chasing functional leaders for decks that all look different, using last year's template, or last decade's logo... You've already got the board book done! You should be able to just generate the presentation too.

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Nine months into what felt like the most important project of my career at Airtable... I had to tell my team it was getting "deprioritized." In hindsight, the warning signs were there. I just didn't know how to read them. If you work in tech, the story is probably all too relatable. Company changes direction, leadership shifts priorities, key stakeholders quietly withdraw support, dependencies fall through, and the project you've poured your heart into just... disappears. The latest post on the Curious Blog is a framework that can help you prevent these moments. https://lnkd.in/gZRe3dPH

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Weather delays. Compliance gaps. Lost days and lost dollars. Every contractor knows the pain. Pavewise, based in North Dakota and built by operators who’ve lived it, has just raised a $2.5M seed round led by C2 Ventures Fund II, alongside Connetic Ventures, Service Provider Capital, M25, gener8tor 1889, and Broadwater Capital. Their platform brings real-time compliance, weather, and production tracking to road construction, helping crews make better calls, cut rework, and keep projects on time. This is exactly what we mean when we talk about our thesis, Dirty, Dull, and Dangerous innovation: solving real operational problems in essential industries with durable tech. https://lnkd.in/eecPMHdN

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I’ve been talking with founders about how painful enterprise customization still is — even in 2025. David Dworsky and Gordon Ritter just put words to what we’ve been seeing: the age of point-and-click configuration is ending, and the next category winners will make customization conversational. For early-stage founders, this is the wedge: - Own one painful workflow - Capture the data - Build toward becoming a system of record If you’re building in this space, I’d love to hear how you’re approaching it. Link to the full article on this in the comments. 

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Leading product teams in regulated environments requires a different kind of discipline. In this episode of the HTD Agile Leaders Podcast, I sat down with Melissa Douros, CPO at Green Dot Corporation, to talk about how product leaders can move faster without sacrificing trust, governance, or customer safety. I enjoyed this conversation on product delivery, AI done responsibly, and what it really takes to lead transformation at scale.

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ARR was built for products. But what happens when your product starts acting like a person? In our latest [Un]Churned episode, Brett Queener dropped a spicy take: | “It's the end of ARR — and I feel fine.” If software behaves like a hire — an agent that actually does the work — then the old 12-month license model doesn’t make sense anymore. You wouldn’t sign a new employee to a two-year, prepaid, non-cancelable contract. You’d hire them at will and expect them to perform. That’s where AI agents take us. Software you don’t just buy — you employ. You pay for the work it performs and the capacity it creates, not the number of seats or licenses you own. For founders and operators, that means re-thinking: ✔️ Pricing → value delivered > seats sold ✔️ Renewals → prove impact every day, not once a year ✔️ Success metrics → how fast it delivers value > how long it retains revenue AI is pushing SaaS toward product purity — either it does the job, or it doesn’t. Would you feel fine if ARR ended tomorrow? How would you rebuild your model around outcomes, not contracts? Full episode with Brett Queener (Bonfire Ventures) and Chuck Ganapathi (Gainsight): https://lnkd.in/eaTaRbKH

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Most contractors don’t fully understand how much revenue is being left on the table by not optimizing their referral channel. I joined Lance Bachmann on Build It To Sell It and we talked about how businesses are 25x’ing referrals by making them automatic, not optional with ReferPro. Check it out: https://lnkd.in/gMsvdQrG

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Seth Levine nailed it! The concentration problem isn't just a GP pain point... it's choking innovation. When capital pools around the same 20 funds, emerging managers and founders get shut out. Love that he's using his platform to call this out. Foundry has backed 50+ emerging managers. That's the diversification the ecosystem needs. This is exactly why Carta exists — making capital allocation visible and accessible. Capital Evolution hits at exactly the right moment. Thanks for having us Daniel Dart. Team Carta loves the community of FUTURE TITANS you have built 🚀

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