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The CTOx Podcast
CTOx
30 episodes
1 week ago
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Entrepreneurship
Business
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Entrepreneurship
Business
Episodes (20/30)
The CTOx Podcast
More Than a Retainer: How to Confidently Negotiate Upside Into Your Fractional Deals
In this episode, Marissa and Lior break down how top Fractional CTOs move beyond retainers to build wealth through equity, revenue share, and performance-based upside. Leor shares how reframing your value around business outcomes—rather than hours or deliverables—changes everything about how clients perceive and reward your impact. You’ll learn how to structure deals that feel like win-wins, turn risk into trust, and align your compensation with measurable growth. Whether you’re new to fractional work or looking to elevate your deal strategy, this episode gives you a practical playbook for negotiating upside without sounding defensive or discounting your worth.   You’ll learn: Why retainers are a starting point—not the ceiling—for your fractional income. How to position yourself as a growth partner, not a cost center. Three proven models for upside: revenue share, performance bonuses, and enterprise value. How to protect yourself while maintaining trust and flexibility. Conversation tactics that create instant win-win energy with CEOs. If you’re a Fractional CTO—or any kind of visionary leader—this conversation is a must-listen.   🔔 Subscribe for more insights on tech leadership   #FractionalCTO #Leadership #Hiring #TechLeadership #StartupGrowth
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1 week ago
20 minutes

The CTOx Podcast
Between You and What You Want: A Pile of No’s
Fractional CTOs don’t stall because they fail—they stall because they freeze. In this episode, Marissa and Lior reframe “no” as useful signal, not a verdict, and show how high-performing CTOs build momentum by stacking rejections, extracting feedback, and iterating fast. You’ll learn why ten consistent “nos” beat silence, how to track them objectively, and how to swap campaign thinking for true experiments with clear hypotheses, stop conditions, and next steps. Leor shares a client story where pushing past an initial “no” flipped a major contract, plus practical ways to protect your mindset, reduce scope on tough days, and keep your growth system moving. Actionable, candid, and immediately applicable for deal flow and resilience.   You’ll learn: How to turn a “no” into data you can act on—message, timing, avatar, or channel—and what to change next. The “no stack” method: why collecting consistent rejections proves traction and prevents vacuum guessing. How to replace fixed campaigns with experiments that define hypothesis, sample size, and stop rules. A simple anti-burnout loop: track outcomes, standardize inputs, and keep scope small (do five reach-outs, not zero). Pipeline discipline: read signals at each funnel stage and persist—sometimes the 12th touch turns a contract.   If you’re a Fractional CTO—or any kind of visionary leader—this conversation is a must-listen.   🔔 Subscribe for more insights on tech leadership   #FractionalCTO #Leadership #Hiring #TechLeadership #StartupGrowth
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1 week ago
24 minutes

The CTOx Podcast
Good Enough to Start: The Truth About Confidence, Credentials, and Client Impact
In this episode, Marissa and Lior go deeper than “impostor syndrome” to unpack what it really takes to start serving at a high level—before you feel ready. They reframe confidence as a byproduct of action, emphasizing minimum viable expertise, outcome ownership, and the core CTO skill: figure-out-ability. You’ll hear how to shift attention from people to problems, protect your confidence with evidence folders, and use humility as a strategic advantage. Lior contrasts mastery with expertise, champions delegation and the “who, not how” muscle, and explains why most SMB clients buy results, not résumés. If you’re building a fractional practice, this is a practical, mindset-first blueprint for showing up, activating teams, and delivering measurable impact. You’ll learn: Shift attention from “who’s watching” to the problem—map outcomes, steps A→B→C, and watch impostor feelings drop. Aim for minimum viable expertise, not mastery—know the next “rock,” name the gaps, and call domain specialists when needed. Lead humans, not code—clients buy outcomes over résumés; build people leadership and the ability to activate teams. Protect confidence—keep an evidence folder (“cookie jar”) of wins, quotes, and artifacts to review and reuse in marketing. Scale with “who, not how”—delegate, cultivate figure-out-ability, and treat hesitation as curiosity to fuel innovation. If you’re a Fractional CTO—or any kind of visionary leader—this conversation is a must-listen. 🔔 Subscribe for more insights on tech leadership.#FractionalCTO #Leadership #Hiring #TechLeadership #StartupGrowth
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3 weeks ago
24 minutes

The CTOx Podcast
Policy, Preference, or Regulation? Why Fractional CTOs Must Ask Better Questions
In this episode, Marissa and Lior dig into a deceptively simple leadership filter: before you act, ask whether a rule is policy, preference, or regulation—and why it exists. From the “new leader grace period” to cutting through acronym soup, they show how fractional CTOs earn trust by questioning assumptions, depersonalizing debates, and reframing requests in business terms. You’ll hear practical ways to set decision criteria, protect engineers from whiplash, educate stakeholders on product process, and handle compliance with calm, cost-aware judgment—sometimes even choosing to pay a small fine instead of adding costly overhead. If you help companies ship, scale, and stay sane, this conversation gives you language, frameworks, and confidence to lead change in real, complex environments today. You’ll learn: How to use the “policy vs preference vs regulation” question to unblock decisions and avoid blind rule-following. Tactics for the first 60–90 days: earn grace, decode acronyms, map “untouchables,” and build buy-in with levity. A simple decision lens: revenue, savings, or risk—plus criteria for true urgency and sequencing. Practical compliance mindset: treat it like a guard dog, assess cost versus risk, and when paying the fine makes sense. Coaching the business: translate ideas into requirements, flows, estimates, and cadence; protect engineers from whiplash by inserting process. If you’re a Fractional CTO—or any kind of visionary leader—this conversation is a must-listen. 🔔 Subscribe for more insights on tech leadership#FractionalCTO#Leadership #Hiring #TechLeadership #StartupGrowth
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4 weeks ago
35 minutes

The CTOx Podcast
Can't AI Eat My Vegetables for Me?
This episode challenges the myth that AI can “eat the vegetables” of a fractional CTO practice. Marissa and Lior break down the non-delegable work—discernment in prospecting, trust-building in sales, and real-time leadership—while showing where AI truly accelerates: prep, polish, and follow-up. Listeners get a clear, practical lens for balancing automation with human judgment, focusing efforts for signal and learning, and protecting credibility in high-stakes decisions.   You’ll learn: A simple lens to separate “automate this” vs. “requires my judgment” in your funnel. Why contracts follow contact—and how discernment drives prospecting, messaging, and closes. How to avoid “AI outsourcing” traps, including a real example of LLM hallucination costing an opportunity. The focus-over-frameworks play: niche, volume, iteration, and learning loops that compound. The hard no’s: never let AI pitch your proposal or lead in key moments—use it to prep and follow up instead.   If you’re a Fractional CTO—or any kind of visionary leader—this conversation is a must-listen.   🔔 Subscribe for more insights on tech leadership   #FractionalCTO #Leadership #Hiring #TechLeadership #StartupGrowth
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1 month ago
30 minutes

The CTOx Podcast
The Hard Way vs. The Easy Way: Why Going Solo Isn’t a Badge of Honor
Going solo as a Fractional CTO may feel bold, but in reality, it’s often the slow and costly route. In this episode, Marissa and Lior explore why doing everything yourself isn’t a badge of honor—and how community, proven frameworks, and mentorship can accelerate growth. They break down the hidden opportunity costs of trial-and-error, the common traps solo founders fall into, and why accountability and structure are essential for scaling without burnout. Real success stories show how tech leaders have replaced salaries in weeks, unlocked freedom in their schedules, and built thriving practices with less stress. If you’ve been white-knuckling your way through, this episode will reframe what’s possible when you stop going it alone.   You’ll learn: Why “figure-it-out” mentality slows your growth without a framework How to avoid common traps like equity-only deals and underestimating sales effort The true cost of going solo: wasted years, lost income, and decision fatigue How community, mentorship, and shared playbooks accelerate traction Practical examples of reframing proposals to increase income and reduce delivery time If you’re a Fractional CTO—or any kind of visionary leader—this conversation is a must-listen.   🔔 Subscribe for more insights on tech leadership   #FractionalCTO #Leadership #Hiring #TechLeadership #StartupGrowth
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1 month ago
30 minutes

The CTOx Podcast
Mindset Matters Part 1: The Fear of Selling (And How to Make It Disappear)
Sales can feel intimidating—especially for technical founders and Fractional CTOs who don’t see themselves as “salespeople.” In this episode, Marissa and Lior reframe selling from something uncomfortable into a powerful act of service. They break down the psychology behind why sales often feels icky, and offer practical mindset shifts to help you move from fear to confidence. From building trust through curiosity and storytelling to anchoring pricing in real business outcomes, this conversation shows you how to embrace selling as part of your identity as a leader. If you’ve ever struggled with the discomfort of pitching your value, this episode will give you the clarity, tools, and confidence to transform sales into one of your biggest strengths. You'll learn: Why many Fractional CTOs fear selling—and how to reframe it as service Practical ways to build trust through curiosity, listening, and giving value early How to use storytelling and “yes, and” thinking to connect and build rapport Why clarity in messaging and discovery drives stronger pricing confidence How to position your services authentically without sounding salesy Sales doesn’t have to feel like a battle—it can be the most meaningful way you serve clients and help them realize their vision. If you’re ready to shift your mindset and lead with confidence, keep following the CTOx Podcast. 🔔 Subscribe today and join the conversation shaping the future of Fractional CTO leadership #FractionalCTO #MindsetMatters #SalesMindset #CTOLeadership #StartupGrowth 
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1 month ago
45 minutes

The CTOx Podcast
Mindset Matters Part 2: Why Imposter Syndrome Is the Enemy of Impact (And How to Beat It)
This episode tackles impostor syndrome for fractional CTOs, with Marissa and Lior breaking down why even seasoned leaders feel it—and how to move through it. They reframe confidence around proven activities, not titles or encyclopedic knowledge, and highlight leadership as creating new capabilities, not doing all the hands‑on work. Expect practical tools like an “evidence folder,” the “experience & impact inventory,” an Uber-inspired “in charge, not in control” model, and a strong bias to action that turns outreach into contracts.   You’ll learn: Why impostor syndrome shows up even for experienced leaders—and why niche context matters more than titles. How to build confidence assets: an evidence folder plus an experience & impact inventory that documents wins and outcomes. The leader’s real job: create new capabilities, orchestrate “who not how,” and allocate the best people instead of being hands‑on. A practical mindset shift: be “in charge, not in control,” using the Uber back‑seat analogy to scale impact across clients. Why action beats analysis: outreach → conversations → contracts; optimize for more at‑bats, not perfect swings.   For Fractional CTOs and tech leaders ready to trade analysis paralysis for decisive leadership, this conversation offers clear next steps—build evidence, lead from the back seat, and take action now. 🔔Subscribe for more playbooks tailored to Fractional CTO leaders.   #FractionalCTO #Leadership #Mindset #ImposterSyndrome #TechStrategy
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1 month ago
37 minutes

The CTOx Podcast
Breaking the Tech Corporate Mold: A Day in the Life of a Fractional CTO
In this episode of the CTOx Podcast, host Marissa sits down with Lior to unpack what it really means to leave corporate tech and step into the life of a Fractional CTO. Far from abstract theory, this conversation dives into daily rhythms, mindset shifts, and the systems that create both freedom and sustainability. From structuring client relationships with intention to balancing delivery with pipeline building, Lior shares a transparent look at what it takes to thrive in this entrepreneurial career path. Listeners will come away with clarity on how to design a fulfilling workweek, avoid burnout, and build a practice that supports not just business growth but also personal wellbeing.   You’ll learn: How to reframe your identity from “corporate leader” to entrepreneur in control of your day Why the right client mix creates stability, scalability, and resilience in your practice Practical routines for structuring your week to balance work, health, and family time A delegation framework that helps CTOs avoid burnout and focus on outcomes over firefighting Why consistent pipeline building is essential—even when you’re fully booked If you’re a Fractional CTO—or any kind of visionary leader—this conversation is a must-listen.   🔔 Subscribe for more insights on tech leadership.   #FractionalCTO #Leadership #Hiring #TechLeadership #StartupGrowth
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1 month ago
20 minutes

The CTOx Podcast
From Employee to Fractional: Making the Leap with Intention
Making the leap from a W2 job to a fractional CTO role isn’t just about swapping paychecks—it’s about redefining value, outcomes, and freedom. In this episode, Marissa Brassfield and Lior Weinstein unpack the realities of leaving traditional employment and stepping into the autonomy of fractional work. They explore the mindset shifts needed to thrive, how to build trust and relevancy in your network, and why your first 30 days can make or break your trajectory. Whether you’re weighing the leap or already navigating early contracts, this conversation delivers the clarity, tools, and frameworks to approach the transition with intention and confidence. You’ll learn: Why outcome—not effort—is the foundation of fractional success How to convert your current employer into your first client The role of trust, relevancy, and content in building your pipeline How to frame compensation and scope to avoid hourly traps The critical moves to prioritize in your first 30 days as a fractional If you’re a Fractional CTO—or any kind of visionary leader—this conversation is a must-listen. 🔔 Subscribe for more insights on tech leadership   #FractionalCTO #Leadership #Hiring #TechLeadership #StartupGrowth
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1 month ago
39 minutes

The CTOx Podcast
AI Agents Are Drivers, Not Robots Designing Tech That Thinks for Itself
In this episode, Lior Weinstein reframes how we think about AI—not as robots blindly following scripts, but as drivers navigating toward a mission. Using the powerful metaphor of AI agents as drivers, Leor explains why discernment, alignment, and judgment matter more than speed. From redefining automation to avoiding the trap of “artificial intimacy,” this conversation explores how fractional CTOs can integrate AI in ways that elevate human strengths instead of replacing them. You’ll hear examples of how agentic workflows are transforming business processes, what risks to avoid when automating high-stakes interactions, and why the future of tech leadership lies in designing capabilities that adapt and grow alongside human decision-making.   You’ll learn: Why AI agents differ fundamentally from traditional automation and RPA How judgment, alignment, and discernment shape responsible AI adoption Practical ways to identify workflows where agents create the most value The risks of over-automating communication-heavy or high-stakes interactions How leaders can grow organizations without over-hiring by leveraging AI agents   If you’re a Fractional CTO—or any kind of visionary leader—this conversation is a must-listen.   🔔 Subscribe for more insights on tech leadership   #FractionalCTO #Leadership #Hiring #TechLeadership #StartupGrowth
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2 months ago
35 minutes

The CTOx Podcast
Core Functions of a Business That Are Fractional by Nature (But Not by Name)
This episode of the CTOx Podcast explores how fractional leadership extends beyond technology into the very core functions of business. Marissa and Lior unpack why roles in legal, finance, and marketing have long operated fractionally, even if not called that, and how this perspective helps founders and CEOs better understand the value of a Fractional CTO. With clarity and candor, the discussion reframes fractional work as efficient leadership, not part-time labor, offering practical ways to rethink organizational design. You’ll learn:• Why “fractional” refers to financial structure, not leadership quality• How legal and finance functions set the precedent for fractional leadership• The role of identity and industry history in shaping perceptions of fractional executives• Practical frameworks for deciding which roles should be fractional versus in-house• Signals that indicate a business is misaligning full-time and part-time talent This conversation challenges traditional assumptions about full-time leadership and highlights how fractional executives drive efficiency across core business functions. Fractional CTOs and tech leaders looking to reimagine their value in the modern economy won’t want to miss these insights.  🔔 Subscribe to the CTOx Podcast for more strategies to thrive as a FractionalCTO. #FractionalCTO #TechLeadership #BusinessStrategy #StartupGrowth #OrganizationalDesign
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2 months ago
35 minutes

The CTOx Podcast
Consultant vs. Fractional CTO: Sit-Ups, Six-Packs, and True Ownership
In this episode of the CTOx Podcast, Marissa and Lior tackle the critical difference between consultants and Fractional CTOs—and why true leadership is about ownership, not just deliverables. Using memorable metaphors like sit-ups versus six-packs and firefighters versus sprinkler systems, they illustrate how consultants provide advice while Fractional CTOs embed within the business, lead teams, and stay accountable for outcomes. The discussion dives into how shifting from deliverables to responsibilities transforms trust, efficiency, and long-term impact. Whether you’re positioning yourself in the market or navigating client expectations, this conversation offers clarity on what it really means to lead as a tech executive.You’ll learn:• Why consultants focus on solving problems while Fractional CTOs define and own them.• How shifting from deliverables to responsibilities builds deeper client trust.• The role of accountability in creating long-term leadership impact.• Practical ways to position yourself beyond “consultant” language.• How to design efficient systems that prevent firefighting and protect your time. If you’re a Fractional CTO—or any kind of visionary leader—this conversation is a must-listen.   🔔 Subscribe for more insights on tech leadership   #FractionalCTO #Leadership #Hiring #TechLeadership #StartupGrowth
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2 months ago
30 minutes 3 seconds

The CTOx Podcast
Building Your Olympic Gold Medalist Leadership Team as a Fractional CTO
Building Your Olympic Gold Medalist Leadership Team as a Fractional CTO | w/ Chris Johnson   In this episode, we sit down with leadership strategist and hiring expert Chris Johnson to explore how Fractional CTOs can build what he calls an “Olympic gold medalist leadership team.” Whether you’re scaling a startup or leading a tech transformation in a legacy company, assembling a world-class team is the difference between burnout and breakthrough.   Chris shares: •What elite hiring actually looks like •How to spot A-players before your competition does •Why most tech leaders hire too fast and regret it •The mindset shift needed to lead at the highest level •Tactical frameworks to assess leadership fit and cultural alignment   If you’re a Fractional CTO—or any kind of visionary leader—this conversation is a must-listen.   🔔 Subscribe for more insights on tech leadership   #FractionalCTO #Leadership #Hiring #TechLeadership #StartupGrowth
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3 months ago
37 minutes 35 seconds

The CTOx Podcast
Money Matters | Managing Finances, Taxes, and Cash Flow as a Fractional CTO
Today we dive into how you manage your cash flow as a Fractional CTO
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3 months ago
32 minutes 37 seconds

The CTOx Podcast
Build A Magnetic Personal Brand As A Fractional CTO
In this episode of the CTOx Podcast, we explore how fractional CTOs can position themselves as high-value leaders by building a magnetic personal brand. Learn how to differentiate yourself in a crowded market, communicate your unique value, and attract ideal clients without chasing them. Whether you’re just starting out or looking to scale your consulting business, this conversation will give you the tools and mindset to elevate your visibility, credibility, and demand as a technology leader.
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3 months ago
43 minutes 52 seconds

The CTOx Podcast
Scaling Yourself: Managing Multiple Clients Without Losing Your Freedom
Today we dive into how to scale your business and not lose your freedom.
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4 months ago
24 minutes 43 seconds

The CTOx Podcast
Functional Technology Framework, Unclogging, De-risking, and Scaling Tech Teams
Today we discuss functional technology framework, unclogging, de-risking, and scaling tech teams.
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4 months ago
39 minutes 10 seconds

The CTOx Podcast
From Pitch to Close Practical Sales Tactics for Fractional CTOs
Today we discuss sales tactics that Fractional CTOs can use to grow their business
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4 months ago
45 minutes 3 seconds

The CTOx Podcast
Why Most Fractional CTOs Don’t Make Real Money
In this brutally honest episode, Lior and Marissa break down why so many talented fractional CTOs stay broke—or worse, burn out. If you’ve ever felt stuck trading time for dollars, this one’s for you. From mindset to messaging to model, learn what actually drives revenue in a successful fCTO business (and what keeps most people spinning their wheels). No fluff. Just facts, frameworks, and a roadmap to making your tech skills pay off.
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4 months ago
13 minutes 48 seconds

The CTOx Podcast