Building The Billion Dollar Business

Latest Episodes:

Special Edition with Michael Kitces, Part 1 Oct 13, 2026

Show notes

Every growing firm reaches a point where getting bigger requires changing how the business works. In part one of this two-part special edition of Building The Billion Dollar Business, Ray Sclafani, Founder and CEO of ClientWise, flips the script with Michael Kitces. Instead of discussing the industry, they talk entrepreneur to entrepreneur about what it takes to build and lead a growing organization.

Michael has led multiple businesses from a handful of people to teams of 30, 50, and 100+, and he outlines the four stages every growing firm moves through, starting with the founder-centered “starfish org chart.” He shares the hiring roadmap that is guiding his next three key hires, explains why word of mouth eventually needs support from a deliberate growth engine, and opens up his EOS quarterly rocks, from data automation and management training to written culture statements and a careful approach to AI.

Firm leaders will come away with a clear lens for identifying their own stage of growth and the structure their next stage requires. As Michael puts it, every day you wake up, you are running the largest company you have ever run, and that is where the opportunity lives.

WHAT YOU’LL LEARN IN THIS EPISODE

The four stages of business growth and how leadership changes at each one
When formal career tracks become essential for attracting and retaining talent
How a hiring roadmap helps leadership rank priorities across every department
Why a 15 to 25 percent annual growth target balances opportunity and sustainability
Where AI can add value in a firm, and where precision requires human control

Michael Kitces, MSFS, MTAX, CFP®, CLU, ChFC, RHU, REBC, CASL, is the Chief Financial Planning Nerd at Kitces.com and Head of Planning Strategy at Focus Partners Wealth, an independent RIA with more than $50 billion in assets under management. He is a co-founder of XY Planning Network, AdvicePay, New Planner Recruiting, fpPathfinder, FA BeanCounters, and NexGen, and hosts the Financial Advisor Success podcast. A recipient of the Financial Planning Association’s Heart of Financial Planning award, Michael is dedicated to helping financial advisors become better and more successful.

Building the Billion Dollar Business is hosted by Ray Sclafani, Founder and CEO of ClientWise, the financial services industry's leading executive coaching and team development firm for elite advisors and wealth management teams. Ray Sclafani is also a Wealthies CEO of the Year Finalist (2026) and Luminaries Thought Leader of the Year Finalist (2026).

Find Ray and the ClientWise Team on the ClientWise website or LinkedIn | Twitter | Instagram | Facebook | YouTube

Do You Know Your People? Oct 06, 2026

Show notes

Before you evaluate anyone else this review season, take a moment to evaluate yourself. In this episode of Building the Billion Dollar Business, Ray Sclafani, Founder and CEO of ClientWise, explores followership: whether the people you lead believe in your vision, believe you are committed to their development, and believe you have their best interests in mind. Your title gives you authority. Followership is earned one conversation at a time.

Drawing on research from Robert Kelley, Korn Ferry, SHRM, Steven Rogelberg, and McKinsey, Ray shows why one-on-ones are the clearest window into whether you have earned it. He shares a six-question self-check that reveals how well you truly know each person on your team, along with a personal story about what happens when a leader shuts down a team member's ambition instead of supporting it.

Firm leaders will leave with a practical next step: run the self-check for every person who reports to you, turn any gaps into the agenda for your next one-on-one, and ask the hardest question of all about what you might be making harder than it needs to be.

WHAT YOU'LL LEARN IN THIS EPISODE

What followership is and the three beliefs that define it
Why one-on-ones are the best place to see whether you have earned your team's followership
What the research reveals about engagement, meeting quality, and why people leave
Six questions every leader should be able to answer about each team member
How to support a team member who tells you who they want to become

THE SIX-QUESTION ONE-ON-ONE SELF-CHECK

When their week goes really well, what happens? When a week wears them down, what's usually behind it?
Do they know what kind of support they need from you right now, and have they asked for it?
How do they want to be recognized when they excel, and how do they want to hear about it when something misses the mark?
Where do they want to be in two to three years, and what skills, competencies, and experiences stand in the way?
What matters to them outside of work right now?
Have they completed their own professional development plan, and have you read and discussed it?

REFLECTION QUESTIONS FOR YOUR LEADERSHIP TEAM

What do you need to know about your team that would help you support them more effectively in achieving their career goals?
What is one thing you, or your organization, do that makes your team's job harder than it needs to be?

RESOURCES MENTIONED

Find Ray and the ClientWise Team on the ClientWise website or LinkedIn | Twitter | Instagram | Facebook | YouTube

Capacity Is The Place Where Strategy Gets Honest Sep 29, 2026

Show notes

Every growth plan reaches the moment where strategy meets the team that will carry it. In this episode of Building the Billion Dollar Business, Ray Sclafani, Founder and CEO of ClientWise, explores team structure and capacity planning, one of the ten interlocking areas of the ClientWise Talent Strategy Operating System. Ray shows why capacity is a strategic lever for advisory firms of every size, from multi-office regional firms to advisors concentrated in a single hub.

Drawing on Michael Kitces' 2025 research on delegating to associate advisors, Ray explains how the right support structure frees lead advisors for business development and deeper client relationships. He then walks through a practical 12-month capacity forecast that helps leaders map future work to the right roles, track measurable capacity signals, and prepare for the service models that tomorrow's more complex, multigenerational clients will require.

Firm leaders will leave with a simple next step: build a one-page capacity forecast for one advisory team and ask what will break first. It is a focused way to hire ahead of demand, protect top talent, and build a firm ready to absorb its next stage of growth.

WHAT YOU'LL LEARN IN THIS EPISODE

Why capacity planning is a strategy issue as well as a staffing issue
What Michael Kitces' research reveals about the time savings of delegating to associate advisors
How to build a 12-month capacity forecast that works as an operating tool
How mapping work to roles frees senior advisors and leaders for higher-value work
Why the future firm builds growth on capacity, role clarity, delegation, and leadership discipline

THE ONE-PAGE CAPACITY FORECAST

Client segments
Households
Revenue
Meeting volume
Planning work
Service load
Advisor ratios
Workload distribution
Manager span of control
Expected growth over the next twelve months

CAPACITY SIGNALS

Number of households per advisor
Number of meetings per month
Planning cases per team member
Open service requests
Turnaround time
Overtime
Missed follow-up
CRM backlog
Manager span of control
Number of exceptions

REFLECTION QUESTIONS FOR YOUR LEADERSHIP TEAM

What part of your growth plan does your current capacity model not support?
Where is work being carried by the wrong person because the team design is outdated?
Which client segments require a different service model?

RESOURCES MENTIONED

Find Ray and the ClientWise Team on the ClientWise website or LinkedIn | Twitter | Instagram | Facebook | YouTube

Where Real Learning Happens Sep 22, 2026

Show notes

Most advisory firm leaders think the cost of isolation is paid in loneliness. It's not. It's paid in months of problem-solving you'd solve in nine minutes with one peer conversation. The most expensive sentence in business is "I'll figure it out myself"—it sounds like strength but costs like a mortgage. While you're quietly working through a decision, someone else already solved it, already paid the tuition, and would have handed you the answer if you'd asked. Ray Sclafani reveals why peer networks and community aren't nice-to-have luxuries for advisory leaders—they're the fastest ROI you can get on your time and attention.

WHAT YOU'LL LEARN IN THIS EPISODE

Why the "lone founder in a garage" narrative is misleading and what actually builds remarkable advisory businesses
How to build real community as a practice (not a membership) with one honest conversation at a time
Why strategic planning must start with gathering, not deciding, and how to gather the three things that matter most

THE COMMUNITY PRACTICE FRAMEWORK

Start with one honest conversation. Not a conference, not a mastermind application. One conversation with someone who's done the thing—a former colleague, a supplier who serves firms like yours, a non-competing peer two markets over. The community builders Ray admires didn't find their room; they started it usually with two people and a standing phone call.
Ask real questions, not polished ones. The mistake is protecting your image. Instead, ask the slightly embarrassing question: "How do you actually handle that? What did it cost you? What would you do differently?" Then do the harder part—be the one who shares your real number, your failed launch, your wrong hire. Vulnerability builds permission for everyone else to be honest.
Tap the scar tissue you cannot buy. Five years of somebody else's hard-earned experience cannot be purchased. It can only be given to you by someone willing to share. Every successful leader Ray has studied had someone three steps ahead willing to tell them the uncomfortable true thing over lunch and save them two years of hard knocks.
Gather before you decide. Most bad decisions aren't bad thinking—they're good thinking on bad inputs. Before your next planning cycle, collect three things: your actual numbers (not the ones you feel), the exact words your clients use to describe their problems (sitting in your inbox right now, free), and what someone slightly ahead of you did when they were standing exactly where you are. Two of these three you can start in the next hour alone.

REFLECTION QUESTIONS FOR YOUR LEADERSHIP TEAM

Who in your network is three steps ahead of you and willing to share? If that list is short, what's one honest conversation you could start this week?
What decision are you currently "figuring out yourself" that a peer could solve in nine minutes?
Where is your team protecting image instead of asking real questions? What permission do you need to give them to be vulnerable?
When you plan next year, will you gather actual data from your network and clients, or will you invent the future from a blank document?
If building a peer advisory circle became a business practice (not a nice-to-have), how would that change your firm's decision-making speed and confidence?

Find Ray and the ClientWise Team on the ClientWise website or LinkedIn | Twitter | Instagram | Facebook | YouTube

Career Paths are Becoming Design Work Sep 15, 2026

Show notes

Your employees do not experience your growth plan directly. They experience whether their own future at the firm feels clear or vague. That clarity, or the lack of it, shapes retention long before compensation ever does. Many advisory firms avoid career path conversations because they fear making promises they cannot keep, so employees are left guessing at what growth actually requires. Schwab's 2025 Advisor Services research found that 77% of firms now offer career pathing and 67% offer coaching and mentorship, meaning this has moved from a nice to have to a market expectation. Ray Sclafani reveals why career pathing is really a design exercise built on skills, experience, and contribution, and why AI is quietly rewriting what every role in your firm requires next.

WHAT YOU'LL LEARN IN THIS EPISODE

Why career paths should be built on skills, experience, and contribution rather than tenure or personality
How AI is shifting the value of roles like associate advisor toward judgment, interpretation, and client insight
How to build a credible one page career path for a single role using six simple sections

THE CAREER PATH DESIGN FRAMEWORK

Skills- Every role needs technical skills, relational skills, judgment skills, and communication skills defined clearly. For an associate advisor that might mean planning software and tax awareness alongside listening, follow through, and knowing when to escalate.
Experience- People grow by doing harder things with support, not by reading role descriptions. A future lead advisor needs to lead parts of a client meeting. A future manager needs to coach someone. Experience is the bridge between potential and readiness.
Contribution- A larger role should require a larger contribution, measured through client impact, team leadership, business development, mentoring, or culture. Promotion should be based on evidence, not tenure.
AI Fluency- As AI takes over meeting notes, drafting, and data organization, the human value in each role shifts toward better questions, judgment, tone, and interpretation. Career paths need to train toward that shift, not ignore it.

REFLECTION QUESTIONS FOR YOUR LEADERSHIP TEAM

Where do employees have a job description but no visible growth map?
What experiences should become required before someone moves into a larger role?
How will AI change the skills required for each career path in your firm?
Which roles in your firm are being held together by personality and memory instead of clear structure?
If a high performer asked you tomorrow what their next two years could look like, could you answer with specifics?

Find Ray and the ClientWise Team on the ClientWise website or LinkedIn | Twitter | Instagram | Facebook | YouTube

Managers Are the System Sep 08, 2026

Show notes

Your people do not experience your strategy directly. They experience their manager. That manager sets the tone for clarity, feedback, accountability, and growth, yet most advisory firms treat management as an honorary title rather than a craft. Only 44% of managers globally have received formal training, and advisory firms routinely promote strong individual contributors into leadership roles without building management skills. The result: retention risk, performance risk, culture risk, and ultimately client experience risk. Ray Sclafani reveals why management is the delivery system for everything that matters and introduces the four-part operating rhythm that scales culture and prevents leadership fracture as your firm grows.

WHAT YOU'LL LEARN IN THIS EPISODE

Why managers are the delivery system for strategy, culture, and employee experience, and why founders often overestimate how much strategy reaches employees directly
How only 44% of managers have formal training, yet advisory firms promote their best individual contributors without teaching them management skills
Why strong producers often make weak managers, and what happens when you assume management talent transfers from client work
The four-part manager operating rhythm: monthly one-on-ones focused on development, quarterly performance calibration, documented development plans, and team health dashboards
Why a 90-minute calibration meeting with four key questions reveals more about firm culture than most annual retreats

THE MANAGER OPERATING RHYTHM FRAMEWORK

1. Monthly One-on-Ones
Move beyond status updates. Cover priorities, obstacles, decisions, feedback, learning, capacity, and development. Manager leaves knowing what the person needs. Employee leaves knowing what matters next.

2. Quarterly Performance Calibration
Bring managers together to discuss performance consistency across roles. Define what meeting, exceeding, and far exceeding expectations look like. Reduce favoritism, vague feedback, and compensation surprises. Identify high-potential talent early.

3. Documented Development Plans
Every employee gets one or two development focuses: client presence, planning skill, follow-through, leadership behavior, delegation, communication, AI fluency, business development. Plans connect to role and firm future.

4. Team Health Dashboard
Managers track engagement, workload, retention risk, development progress, client pressure, meeting rhythm, and open issues. Dashboard makes invisible problems visible.

THE 90-MINUTE CALIBRATION MEETING QUESTIONS

Ask your leadership team these four questions together:

Who is performing well and ready for more?
Who is underperforming and needs direct feedback?
Who is overloaded?
Who might leave if nothing changes?

REFLECTION QUESTIONS FOR YOUR LEADERSHIP TEAM

What do employees experience consistently because of your managers right now, and does it align with your stated strategy?
Which of your managers are carrying titles without enough training, support, or clarity about their role in culture and retention?
Where do your managers need a clearer operating rhythm, and what is the cost of that gap?
How would performance and retention improve if feedback became normal instead of occasional or avoided?
What should your managers be held accountable for beyond personal production, and how will you measure it?

Find Ray and the ClientWise Team on the ClientWise website or LinkedIn | Twitter | Instagram | Facebook | YouTube

The Next Generation Is Asking A Better Question Sep 01, 2026

Show notes

Next generation talent isn't rejecting ambition, they're rejecting vague ambition. They want to know what they're becoming, not just what the job is. By 2030, Gen Z and millennials will comprise 74% of the global workforce, and they're clear about what they need: purpose-driven work, real development, and a visible career path. Yet most advisory firms still operate from an old bargain: work hard, wait patiently, opportunities will come. That no longer retains talent.

Ray Sclafani reveals the five-question framework that turns retention into strategy. Learn how to make the future visible, treat development as intentional leadership practice, and connect work to real meaning. The practical next step is immediate: schedule one conversation with each direct report within 60-90 days and document the next experience they need, not just the next title.

WHAT YOU'LL LEARN IN THIS EPISODE

Why next generation talent rejects vague ambition, not ambition itself, and what question they're really asking about their future
How to use the five-question conversation framework to clarify career paths, development plans, and professional identity
Why making the future visible requires outlining growth, development ownership, possible career tracks, meaning, and AI impact
How to document the next experience rather than the next title so growth happens through structured opportunities
Why connecting younger professionals to client impact and meaningful outcomes is essential for retention in advisory firms

THE FUTURE CONVERSATION FRAMEWORK

What are you learning here?
Who do you see as developing you?
Where do you believe you can go in this firm?
How do you believe your work matters?
How will AI change your role and how will we help you grow with it?

REFLECTION QUESTIONS FOR YOUR LEADERSHIP TEAM

How will your next generation talent see a future in your firm that is clear enough they want to be a part of it?
Where are you assigning them to work but not developing them?
What leadership opportunities can your next generation leaders gain before they receive the leadership title?
How will AI make their future role more valuable, not less?
What visible career path can you outline this week that clarifies identity, not just compensation?

Find Ray and the ClientWise Team on the ClientWise website or LinkedIn | Twitter | Instagram | Facebook | YouTube

The Budget Reveals the Strategy Aug 25, 2026

Show notes

Your budget tells the truth about your strategy. A firm can say it wants to develop next generation leaders, strengthen succession readiness, improve management capability, prepare its people for AI, and increase enterprise value. But if those priorities do not appear in the talent budget, the strategy may be more aspirational than operational. Ray Sclafani explores why the talent budget is one of the clearest ways for an advisory firm's leadership team to determine whether its stated priorities are actually being funded.

In this episode, you'll learn how to build a simple talent budget scorecard that reveals where your firm is investing in its people and what those investments are expected to produce. You'll also discover how Association for Talent Development benchmarks can provide a useful reference point, why talent development should be treated as infrastructure rather than a discretionary expense, and how to connect investments in leadership, coaching, onboarding, and AI fluency to measurable business outcomes. By the end, you'll have a practical framework to evaluate your current talent budget and identify where your spending needs to align more closely with your firm's growth priorities.

This framework is designed for advisory firm leaders who are thinking beyond today's staffing needs and building the capabilities required for future growth, succession, leadership depth, and AI readiness. The central question is simple: Does your budget reveal the firm you're building, or the firm you once were?

WHAT YOU'LL LEARN IN THIS EPISODE

Why your talent budget may reveal more about your actual strategy than your strategic plan
How to connect talent investments to measurable outcomes such as retention, succession readiness, manager capability, and AI adoption
Why talent development should be treated as infrastructure in a growth-oriented advisory firm
How to align talent spending with your firm's top three strategic priorities
Why the goal is not simply to spend more, but to build the capabilities your firm will need in the future

THE TALENT BUDGET SCORECARD

Total annual talent development spend
Talent development spend as a percentage of gross revenue
Leadership development spend
Coaching and professional development spend
New employee onboarding spend
AI fluency and tool adoption training spend
Measurable business outcomes tied to talent investment

REFLECTION QUESTIONS FOR YOUR LEADERSHIP TEAM

What does your current talent budget reveal about what your firm actually believes?
Where are you expecting future growth from the people you're underinvesting in today?
What measurable business outcome should your talent investment deliver over the next 12 months?
How would your budget change if talent development were treated as firm infrastructure?
What capability must your firm build now so it is not constrained three years from now?

Find Ray and the ClientWise Team on the ClientWise website or LinkedIn | Twitter | Instagram | Facebook | YouTube

Stop Hiring Into Confusion Aug 18, 2026

Show notes

Bad hires cost advisory firms upwards of three times salary in direct and indirect costs. But the real issue isn't always the person, it's the system. When firms grow fast and operate under pressure, they hire quickly without clear role definition, leading new hires to navigate confusion, tribal knowledge, and conflicting expectations. Ray Sclafani explores why onboarding cannot be a first-day checklist in advisory firms where work is technical, judgment-dependent, and outcomes matter. The solution is building a better receiving system before the candidate arrives, starting with role clarity.

In this episode, you'll learn the eight-question framework, the 100-Day Role Clarity Map, that separates successful hires from failed ones. You'll also discover why structuring the first 100 days into three distinct phases dramatically improves outcomes, how to assign decision rights without confusion, and why your employee value proposition is as critical as your client value proposition. By the end, you'll have a practical template to use before your next hire and coaching questions to lead your leadership team through the design process.

This framework applies to advisory firms of all sizes and maturity levels, and it's grounded in research from Korn Ferry and SHRM that shows structured onboarding directly correlates with retention, performance, and firm growth.

WHAT YOU'LL LEARN IN THIS EPISODE

The true cost of a bad hire and why good hires in confused systems fail faster than bad hires in clear ones
The eight critical questions every role must answer to ensure success
Why decision rights are non-negotiable and how to assign them
How to structure the first 30, 60, and 100 days into measurable milestones
The connection between employee value proposition and retention

THE 100-DAY ROLE CLARITY MAP

Why does this role exist? (Purpose and problem it solves)
What outcomes define success? (Not activities, outcomes)
What decisions can this person make? (Independent, approval, escalation)
Who are the key relationships? (Manager, mentor, buddy, stakeholders)
What should happen in the first 30 days? (Context-building phase)
What should happen by day 60? (Ownership and feedback phase)
What should happen by day 100? (Readiness and coaching phase)
What AI tools and guardrails apply to the role? (Approved tools, data rules, review requirements)

REFLECTION QUESTIONS FOR YOUR LEADERSHIP TEAM

What would each new hire need to understand in their first hundred days to maximize their impact?
How are you measuring the quality of hire after the employee starts?
Which parts of your onboarding process today still rely too heavily on informal tribal knowledge?
What changes or improvements can you make to your employee value proposition, including a presentation deck that you share with prospective and current employees?
How will AI expectations be communicated to every new hire before habits form?

Find Ray and the ClientWise Team on the ClientWise website or LinkedIn | Twitter | Instagram | Facebook | YouTube

Culture is What the Firm Allows Aug 11, 2026

Show notes

In this episode, Ray explores the uncomfortable truth: firm culture is revealed through what leaders reward, tolerate, and ignore on a typical Monday morning. For advisory firm owners, understanding your actual culture, not your aspirational values, has direct business impact.

Ray makes the connection concrete: research from SHRM shows that employee experience and engagement account for 42% of turnover intent. Regrettable attrition is expensive. More importantly, in relational advisory businesses, internal culture becomes external client experience. Clients feel when teams are aligned, communication is clear, and people are supported. They also feel when turnover disrupts continuity and people are burned out.

This episode is built around an immediately actionable framework: the culture evidence review. Rather than running another employee survey, Ray walks you through five practical questions that move culture from sentiment to evidence. You'll learn what to examine, what it means when certain behaviors are tolerated, and how to use stay interviews to listen early before exit interviews teach expensive lessons.

WHAT YOU'LL LEARN IN THIS EPISODE

Why culture is revealed through behavior, not proclamation, and how to examine evidence instead of language
How employee experience and engagement directly correlate with turnover intent (and the research that proves it)
The five-question culture evidence review framework that translates culture into measurable leadership decisions
Why tolerated behaviors become permission and what behaviors are costing your firm stability and client continuity
How to use stay interviews to listen early and understand what your best people need to stay engaged

THE FIVE-QUESTION CULTURE EVIDENCE REVIEW

What behaviors are rewarded around here? Look past the value statement. Who gets promoted, praised, paid, invited to important conversations? Do you reward people who develop others or only those who generate revenue? Do you reward collaboration or information control? Do you reward system improvement or crisis heroics?
What behaviors are tolerated? Every firm tolerates something. Poor follow-through, weak meetings, avoided feedback, disrespectful communication, hoarded clients, undermining peers, not using the CRM, treating staff as support instead of colleagues. When leaders tolerate these behaviors, tolerance becomes permission.
What do employees fear saying out loud? Your team may know where the firm is stuck before leaders admit it. They know which processes are broken, which client segments drain the team, which advisors are difficult. A healthy culture gives truth a place to go.
What are stay interviews telling us? Ask why people stay, what might cause them to leave, where they feel underutilized or unsupported, and what would help them grow. Listen early.
What is AI anxiety doing to the culture? Employees may not directly name AI fear. They hesitate to use tools, fear being replaced, or assume productivity gains mean more work. Leaders need to surface this conversation.

COACHING QUESTIONS FOR YOUR LEADERSHIP TEAM

What behaviors are shaping your culture more than your stated values do?
Where is the firm tolerating behavior that undermines trust or performance?
What would your employees say the culture rewards most in your firm?
What are stay interviews telling you before exit interviews make the lesson costly?
How is AI anxiety manifesting in the culture, even if people are not naming it directly?

Find Ray and the ClientWise Team on the ClientWise website or LinkedIn | Twitter | Instagram | Facebook | YouTube

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