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Open Coffee For Fractionals with David Raistrick
David Raistrick
20 episodes
2 days ago
Weekly open office hours for fractional professionals, hosted by David Raistrick. These are real, unscripted conversations about what’s working, what’s not, and how to build a business that fits your life. It’s part of David’s coaching practice and the For Fractionals community. No slides. No pitches. No agenda. Just honest conversation.
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Entrepreneurship
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All content for Open Coffee For Fractionals with David Raistrick is the property of David Raistrick and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
Weekly open office hours for fractional professionals, hosted by David Raistrick. These are real, unscripted conversations about what’s working, what’s not, and how to build a business that fits your life. It’s part of David’s coaching practice and the For Fractionals community. No slides. No pitches. No agenda. Just honest conversation.
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Entrepreneurship
Business
Episodes (20/20)
Open Coffee For Fractionals with David Raistrick
Open Coffee For Fractitionals #20

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 into:

  • Why proposals work better as structured menus than open-ended negotiations
  • Starting a fractional practice when you’ve only worked in corporate
  • How to handle pricing, retainers, and avoiding hourly traps
  • Growing vs. staying solo — and why many regret moving into agency models
  • Using testimonials, recordings, and tools to reinforce value
  • Noel’s work measuring smoke for wood stoves and wildfire prevention
  • My own pivot from fractional coaching toward buying a business

No slides. No pitches. No agenda. Just honest conversation.

📅 Recorded September 15, 2025
🎙️ Hosted by David Raistrick

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1 week ago
1 hour 14 minutes 38 seconds

Open Coffee For Fractionals with David Raistrick
Open Coffee For Fractionals #19

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 refrigerants.

We got into:

  • Structuring retainers to balance client comfort and fractional freedom
  • Why equity in exchange for comp is often a scam at the engineer level
  • The realities of SBA loans and specialty financing in auto-related acquisitions
  • Stories of Model Ts, VW buses, and EV charging frustrations
  • Refrigerants, regulation, and the absurdity of industry transitions
  • Insurance adjusters, home repairs, and the value of documentation

No slides. No pitches. No agenda. Just honest conversation.

📅 Recorded September 8, 2025
🎙️ Hosted by David Raistrick

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2 weeks ago
1 hour 16 seconds

Open Coffee For Fractionals with David Raistrick
Open Coffee For Fractionals #18

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 Live isn’t worth the headache. Noel walked through his clean energy project, SAFE notes, and the search for a lead investor. We ended up in DevOps land: on-call culture, cowboy fixes, hero syndrome, and the strange red flags that show up in interviews.

We got into:

  • Buying a job vs getting a job
  • Batching Open Coffee episodes four weeks behind
  • SAFE notes, lead investors, and startup fundraising
  • Emissions monitoring, stoves, and Beer–Lambert law
  • DevOps on-call fatigue and hero culture
  • Interview red flags and trust in ops roles
  • Florida vs Pacific Northwest weather stories

No slides. No pitches. No agenda. Just honest conversation.

📅 Recorded September 1, 2025
🎙️ Hosted by David Raistrick

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3 weeks ago
44 minutes 25 seconds

Open Coffee For Fractionals with David Raistrick
Open Coffee For Fractionals #17

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 industries. Along the way, we also talked scams, old tech still hanging around, and the economics of big-tech hiring and layoffs.

We got into:

  • Exploring a car-industry acquisition with management already in place
  • Chamber of commerce RFPs and why web vs IT is still a fuzzy line
  • Using ChatGPT and Claude for proposals, docs, and SDLC prompt packs
  • Study/learn modes for certifications and domain ramp-up
  • Phishing scams, PDFs, and the ghost of Microsoft Access
  • Big tech layoffs, over-hiring, and the brain drain that follows

No slides. No pitches. No agenda. Just honest conversation.

📅 Recorded August 25, 2025
🎙️ Hosted by David Raistrick

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1 month ago
48 minutes 52 seconds

Open Coffee For Fractionals with David Raistrick
Open Coffee For Fractionals #16

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/B0FP4239CD (available October 6, 2025)

From there we went wide. Fractional roles, DevOps tools, wood stove smoke sensors, HVAC systems, and how every business is now both a tech and a data business. It was one of those conversations where the connections kept surprising us.

We got into:

  • Increasing your “surface area” for luck through Rotary, Chamber, and community connections
  • Publishing books as credibility builders for Fractionals (Michael’s preorder: https://www.amazon.com/Beyond-Commit-Software-Development-English-ebook/dp/B0FP4239CD)
  • Fractional CTO and DevOps work in venture/PE-backed companies
  • Startups around combustion air controllers and smoke sensors
  • The intersection of HVAC, IoT, and service models
  • Why all businesses today are tech businesses (and data businesses)

No slides. No pitches. No agenda. Just honest conversation.

📅 Recorded August 18, 2025
🎙️ Hosted by David Raistrick

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1 month ago
1 hour 6 minutes 30 seconds

Open Coffee For Fractionals with David Raistrick
Open Coffee For Fractionals #15

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, pricing, politics, and people.

We got into:

  • Early stage startups expecting a fractional CTO to act like a founder
  • Navigating equity offers and why they’re really investment decisions
  • Deciding when to take loss-leader projects for credibility
  • How much politics you can (and can’t) avoid in leadership roles
  • Building trust through content and positioning
  • Using contractors and agencies to keep momentum post-acquisition
  • The limits of job interviews vs. building a client pipeline

No slides. No pitches. No agenda. Just honest conversation.

📅 Recorded August 11, 2025
🎙️ Hosted by David Raistrick

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1 month ago
1 hour 1 minute 48 seconds

Open Coffee For Fractionals with David Raistrick
Open Coffee For Fractionals #14

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 Payne walked through turning a dev contract into a local fractional CTO role, and the pros and cons of offering small-town IT services as a lead-in to higher-value fractional work.

We got into:

  • compliance by checkbox (and why nobody cares until a big client forces it)
  • brittle automation and why error handling in Bash matters
  • command language vs programming language in DevOps and infra
  • deterministic builds, golden images, and why reality always drifts
  • local business IT as lead-gen vs distraction
  • Rotary Club networking as a fractional growth tactic
  • AI as context engine and trust gap filler for non-technical clients

No slides. No pitches. No agenda. Just honest conversation.

📅 Recorded August 4, 2025
🎙️ Hosted by David Raistrick

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1 month ago
1 hour 12 minutes 14 seconds

Open Coffee For Fractionals with David Raistrick
Open Coffee For Fractionals #13

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 hard line between strategy and delivery — why mixing them can bury the real work — and made the case that most companies don’t need a DevOps army, just a couple of great people to build and run the pipelines.

Michael Payne told a cautionary tale about a 30-person infrastructure team that couldn’t ship in over a year, and how that inability to deliver sank the project.

We got into:

  • Agile’s leaky abstractions and why it rarely works as advertised
  • Tool-building rabbit holes that never reach the outcome
  • Giving teams “air” so technical debt disappears
  • Risk, compliance, and the hot-rod-to-Costco problem

No slides. No pitches. No agenda. Just honest conversation.

📅 Recorded July 28, 2025
🎙️ Hosted by David Raistrick.

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2 months ago
1 hour 8 minutes 21 seconds

Open Coffee For Fractionals with David Raistrick
Open Coffee For Fractionals #12

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 true fractional portfolio.

Matt DiBerardino came in mid-career transition, looking to figure out what “fractional” really means and how it overlaps with consulting. We dug into definitions, positioning, and why the label matters when you’re trying to be found.

We got into:

  • why all strategies start as hypotheses
  • how niche focus makes marketing easier
  • interim roles vs multi-client portfolios
  • why equity-only “fractionals” are really co-founders
  • and why narrowing your ICP is hard (even when you know better)

Noel Putaansuu brought live data from his smoke-measurement system — graphs for opacity and color shift — and the question of whether extra measurements matter when scientists only care about one. We talked about signal vs noise, what data actually gets used, and how you translate technical readings into customer-level value.

No slides. No pitches. No agenda. Just honest conversation.

📅 Recorded July 21, 2025
🎙️ Hosted by David Raistrick.

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2 months ago
47 minutes 17 seconds

Open Coffee For Fractionals with David Raistrick
Open Coffee For Fractionals #11

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 fractional CEO actually does, and why talking to chimney sweeps might matter more than raising VC.

Livio Zanardo helped frame the real ask — and connected the dots between regulated markets, retrofit demand, and business partnerships that actually work.

We got into:

  • why fractional CEOs often aren’t looking for equity-only roles
  • how local regulations shape hardware markets
  • selling to mom-and-pop shops vs manufacturers
  • the role of “hero customers” in early traction
  • the physics of burning wood (and why your dog shouldn’t nap by the stove)

No slides. No pitches. No agenda. Just honest conversation.

📅 Recorded July 14, 2025
🎙️ Hosted by David Raistrick

Join a future session | Explore the For Fractionals community

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2 months ago
44 minutes 29 seconds

Open Coffee For Fractionals with David Raistrick
Open Coffee For Fractionals #10

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 consultant — and how a Kubernetes post from five years ago closed his biggest deal. We dug into long-tail content, building writing habits, and how fractional credibility shows up over time.

We got into:

  • reframing what “100% capacity” means
  • why early referrals create a false sense of stability
  • how long sales cycles test your patience
  • why hybrid delivery still matters — especially for CFOs
  • how AI can help draft content (as long as you still edit)
  • remote meetings, camera setup, and the social side of consulting

No slides. No pitches. No agenda. Just honest conversation.

📅 Recorded July 7, 2025
🎙️ Hosted by David Raistrick

Join a future session | Explore the For Fractionals community

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2 months ago
54 minutes 21 seconds

Open Coffee For Fractionals with David Raistrick
Open Coffee For Fractionals #9

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 else.

Stephen Lauck mapped the CTO spectrum into three types: the fixer, the tech lead, and the customer-facing business mind.

We got into:

  • who fixes your AI MVP when it breaks?
  • why positioning around risk (not hours) helps sell retainers
  • how isolation makes nontechnical founders seek fractional partners
  • why companies don’t hire juniors (and how that breaks the pipeline)
  • how trades and tech both cling to the hourly myth — and what to do instead
  • retainers as risk transfer: you’re not paying for time, you’re paying to not hold the bag when stuff breaks

No slides. No pitches. No agenda. Just honest conversation.

📅 Recorded June 30, 2025
🎙️ Hosted by David Raistrick

Join a future session | Explore the For Fractionals community

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3 months ago
1 hour 21 minutes 7 seconds

Open Coffee For Fractionals with David Raistrick
Open Coffee For Fractionals #8

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 fixing things — but not running them forever.”

Ben Mills shared his shift from 25 years in public accounting to fractional CFO work — and how he now avoids time tracking entirely. His engagements focus on oversight, cash flow, and being the person the CEO actually talks to.

Stephen Lauck described a delivery-led DevOps model that blends software, team upskilling, and delivery artifacts — with pricing in the $15–20K/month range. His big win: skip the full-time hire and let us train your team with safety rails.

We got into pricing structures: onboarding fees, flat monthly retainers, and what happens when you remove hours from the conversation entirely.

Daniel Afonso talked about the gap between the content we want to make — and the content buyers actually connect with.

And we kept circling back to a core thread: The business outcome is usually money. Everything else is just flipping bits until you get there.

Also featuring:

  • J Z on public speaking as a lead source
  • Diego Woitasen building product with AI tools and letting a non-technical family member keep it moving
  • Everyone dunking on jargon (including our own)

📅 Recorded June 23, 2025
🎙️ Hosted by David Raistrick

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3 months ago
1 hour 5 minutes 3 seconds

Open Coffee For Fractionals with David Raistrick
Open Coffee For Fractionals #7

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 about human ones. Internal politics. Indecision. Fear of making the wrong move. His advice? Flip a coin, pick a path, and iterate.

Adam White took that advice and used Claude to generate a lead gen playbook — then actually started messaging people he’d been putting off. AI as fractional accountability buddy? Maybe.

We ended on a core truth: authenticity sells. Don’t water yourself down. Don’t over-edit. Clients buy you — not your AI-polished LinkedIn twin.

No slides. No pitches. No agenda. Just honest conversation.

📅 Recorded June 16, 2025
🎙️ Hosted by David Raistrick

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3 months ago
1 hour 4 minutes 22 seconds

Open Coffee For Fractionals with David Raistrick
Open Coffee For Fractionals #5

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 CTOs.

Meena Narsinghani broke down the challenge of straddling product and engineering — and how AI agents are already reshaping backlog grooming and user story generation.

Karl Schmidt brought back a report from Vancouver's Web Summit: AI is the question everyone’s asking — even if no one has answers yet.

We talked about selling advisory vs delivery, and how most clients still don’t understand what fractional is — or how to engage us. The line between contractor and peer is blurry, and structuring these relationships takes real work.

Also covered:

  • the ego traps in CTO sales
  • fractional DevOps as both emergency patch and long-term solution
  • why advisory work is about being the outside voice — not the fixer
  • the invisible buyer: why HR, COO, and CFOs might be better entry points than CTOs

📅 Recorded June 2, 2025
🎙️ Hosted by David Raistrick

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3 months ago
1 hour 16 seconds

Open Coffee For Fractionals with David Raistrick
Open Coffee For Fractionals #3

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”
  • how to pitch retainers without selling hours
  • pricing advisory work by value, not time
  • targeting Crunchbase-funded startups who still don’t have technical leads
  • nontraditional fractional work — from roofing businesses to shadow CTO roles
  • how chance meetings and birthday parties lead to 5-year clients

No slides. No pitches. No agenda. Just honest conversation.

📅 Recorded May 19, 2025
🎙️ Hosted by David Raistrick

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3 months ago
1 hour 17 minutes 26 seconds

Open Coffee For Fractionals with David Raistrick
Open Coffee For Fractionals #2

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 to work that never needs to finish
  • what real infra automation looks like — and why so few people can do it well
  • how to target buyers instead of fans
  • the moment when founders say the thing that means they need you

Daniel’s trying to shift from payroll into a new vertical — and we talked through what it takes to pick a niche, build a POV, and actually get attention from the right people.

📅 Recorded May 12, 2025
🎙️ Hosted by David Raistrick
🎧 Guest: Daniel Afonso

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3 months ago
27 minutes 28 seconds

Open Coffee For Fractionals with David Raistrick
Open Coffee For Fractionals #6

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 room.

Then Adam White dropped a live demo of using Claude Code to generate a full production-ready website in a couple hours — SonarCloud checks, test coverage, design system and all. Not hypothetical. Not a toy. Real code, shipping soon.

Stephen Lauck and I pushed on that edge — if anyone can build anything now, where does the actual value live? (Spoiler: it’s not in scaffolding.)

The real job might be moving toward the producer seat: orchestrating meaning, outcomes, and connections. Especially when tools can generate endless sugar with no nutrition.

Other things we hit:

  • Replit, Bolt, Lovable, and the growing pile of “almost usable” LLM scaffolding tools
  • fractional roles as AI translators — connecting business needs to buildable prompts
  • using LLMs for architectural decisions, not just code generation
  • prompt verbosity, writing voice, and why longer isn’t always better
  • layering and remixing your own transcripts to create content — yes, including this very episode

Participants: David Raistrick, Stephen Lauck, Adam White, Livio Zanardo, Diego Woitasen, Karan Krishnani

📅 Recorded June 9, 2025
🎙️ Hosted by David Raistrick

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3 months ago
1 hour 4 minutes 38 seconds

Open Coffee For Fractionals with David Raistrick
Open Coffee For Fractionals #4

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 the UK finance market — fractional roles are underpaid, misunderstood, and rarely packaged well.

We got into:

  • how to turn casual intros into paid audits
  • why follow-up coffee is where the actual trust gets built
  • Facebook games, internal tools, and ex-corporate re-entry
  • rethinking day rates and how finance directors package themselves

No slides. No pitches. No agenda. Just honest conversation.

📅 Recorded May 26, 2025
🎙️ Hosted by David Raistrick

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3 months ago
57 minutes 24 seconds

Open Coffee For Fractionals with David Raistrick
Open Coffee For Fractionals #1

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 do — all while reconnecting with his network and exploring what kind of fractional CTO work actually fits.

We got into:

  • why so many of us leave full-time to work across more than one product at a time
  • the difference between helping and building — and where the leverage is
  • why fractional work is just another startup (except the product is you)
  • how listening tours help you find your market
  • what not to do with Calendly

No script. No slides. Just honest conversation.

📅 Recorded May 5, 2025
🎙️ Hosted by David Raistrick

Join a future session | Explore the For Fractionals community

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3 months ago
30 minutes 15 seconds

Open Coffee For Fractionals with David Raistrick
Weekly open office hours for fractional professionals, hosted by David Raistrick. These are real, unscripted conversations about what’s working, what’s not, and how to build a business that fits your life. It’s part of David’s coaching practice and the For Fractionals community. No slides. No pitches. No agenda. Just honest conversation.