Open Coffee For Fractionals with David Raistrick

This is an Open Coffee for Fractionals session — part of my coaching practice. In this 20th and final Open Coffee session, we had a strong mix of new and familiar voices: Chris Hilton, Jim Grey, Michael Berris, Noel Putaansuu, and me. We dug into what it really means to build a fractional practice, how to structure offers, and where the pitfalls show up when you drift into agency models. We got in...

This is an Open Coffee for Fractionals session — part of my coaching practice. Chris Hilton brought in a live dilemma: when a founder friend wants you full-time but you’re only willing to engage fractionally, how do you make it work? We compared notes on retainers, boundaries, and the risks of equity-heavy compensation, while also detouring into business acquisitions, old cars, and the politics of...

This is an Open Coffee for Fractionals session — part of my coaching practice. Noel Putaansuu joined this session just before heading into a job interview. We compared buying a business versus getting a job, and dug into what it means to keep the lights on while still trying to build something bigger. We talked about the lag on publishing Open Coffee episodes, batching content, and why LinkedIn Li...

This is an Open Coffee for Fractionals session — part of my coaching practice. Michael Payne joined me for a Monday catch-up, where we compared notes on buying businesses, bidding on local chamber RFPs, and how AI is reshaping the work of fractionals. We dug into how AI can empower rather than replace us — from drafting proposals and building lightweight SDLCs to quickly ramping up on new industri...

This is an Open Coffee for Fractionals session — part of my coaching practice. Michael Payne shared where he’s been focusing lately — getting more intentional about local networking, Rotary, and building visibility as he gets ready to launch his book, Beyond the Commit: The Human Side of Software Development. Preorder: https://www.amazon.com/Beyond-Commit-Software-Development-English-ebook/dp/B0FP...

This is an Open Coffee for Fractionals session — part of my coaching practice. Chris Hilton joined this session as he considered stepping into the fractional CTO path. Kevin Knoepp and Diego Woitasen brought in their own perspectives from private equity portfolio work and consulting. The conversation moved from DevOps history into the real challenges of building a fractional business: positioning,...

This is an Open Coffee for Fractionals session — part of my coaching practice. We started with Thomas Smith joining from his truck — peaceful, quiet, and ready to talk shop. That led straight into a deep dive on why shell scripts break developers’ brains, the difference between command languages and programming languages, and why determinism in infrastructure is mostly a myth. From there, Michael...

This is an Open Coffee for Fractionals session — part of my coaching practice. Livio Zanardo jumped in mid-gaming break to share how his fractional practice has gone from quiet to bursting — enough that a waiting list might be next. We talked through picking the high-value work, parking the low-value stuff, and how calling yourself “fractional” makes strategic sales easier. Stephen Lauck drew a ha...

This is an Open Coffee for Fractionals session — part of my coaching practice. Ying Wang joined after a two-week grind chasing a timeout bug in DigitalOcean. The fix turned into a Michelin-star dinner for the engineer who stuck it out. She’s interim CTO for a mortgage tech startup, deep in B2B SaaS, and thinking about when to niche further — and when to shift from a single full-time client to a tr...

This is an Open Coffee for Fractionals session — part of my coaching practice. Noel Putaansuu is a fire investigator, engineer, and inventor — building smart, wireless systems to help wood stoves burn cleaner than new. He’s got patents, prototypes, working sensors, and field testers — but he’s still solo. This call turned into a go-to-market jam session: how to find the right partner, what a fract...

This is an Open Coffee for Fractionals session — part of my coaching practice. Ben Mills talked through building his fractional CFO practice — from early referrals to cold outreach and content experiments. He shared how a single lucky LinkedIn Navigator DM turned into a client, and how he tracks everything to learn what works. Diego Woitasen reflected on shifting from agency owner to solo consulta...

This is an Open Coffee for Fractionals session — part of my coaching practice. Michael Payne joined for the first time and shared what it’s like going from consulting architect to fractional CTO — mostly solo, mostly govtech, mostly East Texas. Adam White came in hot with a new positioning experiment: Technical Waste Management . His pitch? Let your best engineers build — I’ll clean up everything...

This is an Open Coffee for Fractionals session — part of my coaching practice. This one went deep on delivery models, retainers, and how different Fractionals think about packaging value — from finance to DevOps and everything in between. Jim Grey just landed his first fractional gig and walked us through the process — from outreach to proposal to finally realizing: “I like building things and fix...

This is an Open Coffee for Fractionals session — part of my coaching practice. Noel Putaansuu joined us to talk about measuring smoke opacity, fine particulates, and what it’s like running a fractional business where you’re the engineer, the scientist, the marketer — and the only one who understands the chart. Stephen Lauck cut straight to it: fractional work isn’t about technical hurdles — it’s a...

This is an Open Coffee for Fractionals session — part of my coaching practice. This one got deep into the business of being Fractional: Stephen Lauck and Sam Taggart swapped war stories about Zoom chaos, Teams pain, and what tool sprawl does to delivery flow. Adam White shared his path from full-time to fractional to full-time again — and back — plus the existential dread of pitching live to other...

This is an Open Coffee for Fractionals session — part of my coaching practice. This session went long and deep — and hit a lot of notes on what it actually means to run a fractional business. Karl Schmidt, Lukas Czerwinski, Sam Taggart, Travis Russi, and Russ Waddell all joined. We talked about: client acquisition when your network runs out why founders say “CTO” when they mean “coder for equity”...

This is an Open Coffee for Fractionals session — part of my coaching practice. In this session, I talked with Daniel Afonso about what it’s like to be a fractional ops person trapped in a broken full-time environment — and what it takes to build a business around automating infrastructure. We dug into: how CI/CD can be used to hide bad decisions behind fake security why hourly billing often leads...

This is an Open Coffee for Fractionals session — part of my coaching practice. Livio Zanardo kicked this one off with a classic: “None of this happened until I started calling myself a fractional CTO.” The positioning shift that launched a bunch of new work. We followed that thread all the way through pricing, nonprofits, fixed-fee framing, and how hard it is to back out of hourly once it’s in the...

This is an Open Coffee for Fractionals session — part of my coaching practice. Brian Ng, Karl Schmidt, and Jan Nala Thundi joined me for this one. Karl was heading into Web Summit and dreading the small talk. We flipped it: what if it’s just a listening tour? Brian shared how his post-Meta reconnection work has hinged on low-pressure follow-ups and long-tail relationships. Jan dropped signal from...

This is an Open Coffee for Fractionals session — part of my coaching practice. Brian Ng was the very first guest at Open Coffee for Fractionals. We talked about what it’s like to go from Director at Meta to solo fractional — and how weird it feels to sell yourself for the first time. Brian's building his practice now: mentoring founders, advising startups, and figuring out what he doesn’t want to...