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Money clarity, human first.®

Money clarity, human first.®Money clarity, human first.®Money clarity, human first.®

Keep Asking How™

Keep Asking How™Keep Asking How™

FINANCIAL COACHING THAT MEETS YOU WHERE YOU ARE.

One conversation to get clarity. Then choose the path that fits your season.

One conversation to get clarity. Then choose the path that fits your season.

One conversation to get clarity. Then choose the path that fits your season.

Book a Fit Call 

Book A Fit Call

Momentum 120 - CUT THE NOISE. CHOOSE YOUR NEXT MOVE.

One conversation to get clarity. Then choose the path that fits your season.

One conversation to get clarity. Then choose the path that fits your season.

 A two-hour financial coaching session that simplifies your month and points you to the right program—credit included. 

Start your breakthrough

Services and Programs

Money Map Sprint

Four weeks to cash‑flow calm. 

Reset your month and cut 2–3 “silent fees.” 

Start the Sprint

Financial Foundations 90

Ninety days to durable habits and a safety buffer. 

Begin Foundations

Momentum 90

Expat Launch: Living Abroad 101

Expat Launch: Living Abroad 101

Turn wins into ROI stories and follow‑through—for a raise, transition, or leadership clarity. 

Start Momentum

Expat Launch: Living Abroad 101

Expat Launch: Living Abroad 101

Expat Launch: Living Abroad 101

Living Abroad 101 — education‑first planning: visa path types, tax residency vs. residency, healthcare abroad, and re‑entry/long‑term care considerations. 

Start Expat Plan

Deep Dive Into Our Services And Programs

man invested in money breakthrough 120 and feels happy with keep asking how and financial coaching

Money Breakthrough 120 — 2 hours

Best for: quick clarity, immediate wins, new budgeters, or jumping back in after a hectic season. Also great if you want a low-risk start before choosing a longer program.

You’ll leave with: a one-page Money Map, 2–3 expenses trimmed (or renegotiations started), a simple weekly caps plan, and one 7-day action you can take right away.

 You get (in 2 hours):

  • Money Map QuickStart (one page) completed live. 
  • Unnecessary Expense Audit: identify and trim 2–3 recurring expenses; add a reusable renegotiation script. 
  • Weekly Caps plan (paper or bank-app notes) for 2–3 spending categories. 
  • 7-Day Action Plan (1–2 specific tasks with date/time). 
  • Recap email within 2 business days with: copies of your Money Map, scripts/templates, and your next check-in option. 
  • Credit note: $250 credits to any program within 14 days.

Cadence:

  • 1 × 120-minute working session (live, collaborative)
  • Recap email within 2 business days with links, scripts, and next-step options

Fit if: you want traction this week without a long program, or you’re deciding whether to do Sprint/Foundations/Momentum/Expat Launch and want proof first.
Not a fit if: you need career or transition coaching (see Momentum 90), multi-week habit installation (Foundations 90), or expat feasibility planning (Expat Money Launch).

Flat fee: $250 — credits to any program within 14 days.

Start your breakthrough

How do I see more immediate financial results?

woman invested in money map sprint financial coaching with brad biren at keep asking how

Money Map Sprint — 4 weeks

Best for: quick reset, immediate wins, new budgeters, or coming back after a hectic season. 

You’ll leave with:  a one-page monthly snapshot, 2–3 fee cuts, and a simple weekly loop you can keep running. 

 

You get (over 4 weeks):

  • Kickoff: build your Purpose Budget (one page) and set auto-transfers for buffers. 
  • Unnecessary Expense Audit: complete 2–3 cancellations/renegotiations (or start them) with email/phone scripts. 
  • Weekly Caps installed (paper tracker or bank-app notes) + quick check method. 
  • One-page Monthly Snapshot (printable) cash-flow, buffer, expenses trimmed.
  • Bills & Benefits Organizer (lite): prompts for renewals, beneficiaries, and “who to call” list. 
  • After each session: short email notes with what changed and what’s next. 
  • End-of-Sprint Proof: one-page summary of results (expenses trimmed $, buffer progress, habit streak) + your suggested next step.

 Cadence: 

  • 1 × 60‑min kickoff 
  • 3 × 45‑min check‑ins 
  • lightweight email touchpoints
     

Fit if: you want traction this month without a long program.
Not a fit if: you need career/transition coaching—see Momentum 90.


Flat fee option (save up to 10%): $789 (covers up to 5 hours over 4 weeks; additional time $175/hr). 

Breakthrough $250 credit applies within 14 days. 

Start the Sprint

How do I learn about personal money management?

man coaching mentee on achieving success

Financial Foundations 90 — 90 days

Best for: habit build + safety; you want a durable system, not a one‑off reset.
You’ll leave with: debt/asset rules, a funded buffer plan, and a weekly tracker you actually use.

You get (over 90 days):

  • Rules of the Road (one page): plain-English guidelines for debt, assets, benefits, and when to ask a pro. 
  • Buffer Build Plan: target amount, auto-transfers, and “when life happens” rules. 
  • Weekly Tracker (paper or simple sheet): 12-week habit log for caps, transfers, and check-ins. 
  • Quarter-Ahead Preview: calendar of known expenses (insurance, taxes, travel, gifts) with month-by-month impact. 
  • Bills & Beneficiaries prompts (lite): checklist to review payees, beneficiaries, and renewal dates. 
  • Resilience Toolkit: emergency request script, bill-relief negotiation script, and income-dip playbook. 
  • Progress reviews at weeks 4, 8, and 12 with simple metrics (buffer growth, expenses trimmed $, habit streaks). 
  • Quarter Close-Out: 1-page “what’s working/what to keep” and a light plan for the next 90 days.

 Cadence: 

  • 1 × 75‑min start line 
  • Bi‑weekly 45‑min sessions (5 total) 
  • async check‑ins

Fit if: you want consistency and less money noise day‑to‑day.
Not a fit if: you’re planning a cross‑border move soon—see Expat Money Launch. 

Flat fee option (save up to 10%): $1,575 (covers up to 10 hours over 90 days; additional time $175/hr). 

Breakthrough $250 credit applies within 14 days.  

Begin Foundations

How do I learn more about finances as a leader?

african american leader who invested in momentum 90 with keep asking how and brad biren

Momentum 90 — 90 DAYS

Best for: raises/offer prep, job change, or leadership clarity.
You’ll leave with: a story bank (wins → numbers), negotiation prep, and follow‑through that sticks.
You get (over 90 days):

  • Purpose Projects Plan: pick 1–2 money-aligned projects (giving plan, part-time pivot, board/leadership role) with checkpoints. 
  • ROI Story Bank: capture wins and metrics; turn them into short stories you can use in reviews, offers, or board bios. 
  • Offer/Raise Prep: a Value Case one-pager, compensation/benefits micro-scripts, and a mock conversation. 
  • Household Money Quieting: a 30-minute agenda for calm money talks + “friction audit” actions. 
  • Execution Rhythm: bi-weekly follow-through checklist and a simple “done/not done” review. 
  • Finish Line Packet: 3 proof stories, a next-quarter cadence, and optional referrals (neutral; no compensation).

Cadence:  

  • 1 × 75‑min start line 
  • Bi‑weekly 45‑min sessions (5 total) 
  • Short email reviews

Fit if: you want your money decisions to support a move you’re making at work.
Not a fit if: you only need a one‑time tune‑up—start with Breakthrough 120. 

Flat fee option (save up to 10%): $1,890 (covers up to 12 hours over 90 days; additional time $175/hr). 

Breakthrough $250 credit applies within 14 days. 

Start Momentum

How hard is it to move abroad?

woman living abroad as a US expat happy she used expat money launch with keep asking how Brad Biren

Expat Launch: Living Abroad 101 — 6–8 sessions (~90 days)

Best for: exploring a move abroad or testing feasibility within a clear time window.
You’ll leave with: a one‑page Living Abroad 101 Roadmap (visa path types snapshot, U.S. tax‑tie overview, healthcare notes) plus a Country Comparison Scorecard and Re‑entry/Long‑Term Care checklist. Deliverables:

  • Living Abroad 101 Roadmap (one page) — visa path types (education only), tax‑tie overview, healthcare & insurance questions, and re‑entry/LTC checklist.
  • Country Comparison Scorecard (quality of life, protections, climate, language, proximity, at‑a‑glance costs).
  • Healthcare & Insurance Questions Pack (for planners/insurers abroad and at home).
  • Referral‑Prep Sheet + Neutral Resource List (what to ask a cross‑border CPA/immigration attorney; government portals/directories).

Cadence: 

  • 1 × 75‑min start line 
  • Weekly 45‑min sessions (6–8) 
  • Document reviews

Fit if: you want education‑first clarity before you move.
Not a fit if: you need ongoing household habit work—see Foundations 90.

Flat fee option (save up to 10%): $1,890 (covers up to 12 hours over 6–12 weeks; additional time $175/hr). Breakthrough $250 credit applies within 14 days.

Start Expat Plan

Starter Session

A low‑friction start. Map your money, set one 7‑day action, and feel the needle move.

• Money Map QuickStart • 2 micro‑scripts • recap email within 2 business days.
Credit: $250 credits to any program within 14 days. 

Begin Foundations

What are my options?

Which Program Is For Me?

 Fast chooser:


  • “We need quick traction this month.” → Money Map Sprint
  • “We want a durable system and safety.” → Foundations 90
  • “I’m moving roles/negotiating and need ROI.” → Momentum 90
  • “We’re planning to live abroad.” → Expat Money Launch


  • “Not sure yet.” → Money Breakthrough 120 — $250
     

Schedule Your fit call

Frequently Asked Questions (FAQs)

Please reach us at brad@keepaskinghow.com if you cannot find an answer to your question.

No—I’m a financial coach and attorney. This is educational coaching, not legal, tax, or investment advice. When specialized advice is needed, we help you prepare questions and can provide neutral referrals (no compensation received). 


No—we focus on clarity, cash‑flow, fees, benefits, and decisions you control.  


Yes—Money Map QuickStart, trackers, scripts, and recap notes are included. 


Book a Fit Call or try Breakthrough 120—it’s $250 and fully credits to any program within 14 days.  


Flexible—just ask in your Fit Call.  


“Why work with me vs. a counselor or planner?”

Clear money moves, not theory: fees cut, decisions made, habits set. I coach action; I don’t diagnos

Clear money moves, not theory: fees cut, decisions made, habits set. I coach action; I don’t diagnos

Clear money moves, not theory: fees cut, decisions made, habits set. I coach action; I don’t diagnos

Therapy heals the “why.” Planning optimizes the “what.” Coaching gets the “how” done. We turn confusion into two small moves you’ll take this week, then we track proof you can see—cash-flow, buffer growth, and fewer fees. When a topic needs clinical, legal, tax, or investment expertise, we loop in the right pro and keep you moving. 

Book a fit call

Credentials & lane statement

Clear money moves, not theory: fees cut, decisions made, habits set. I coach action; I don’t diagnos

Clear money moves, not theory: fees cut, decisions made, habits set. I coach action; I don’t diagnos

I’m an attorney with a background in international/retirement matters who now works as a financial coach. In coaching, I operate outside the practice of law and do not provide legal, tax, or investment advice. If legal work is appropriate, I’ll say so and offer to handle it under a separate written engagement or refer you to another qualified professional. Staying in my lane is part of doing this work responsibly. 

How I help (and how I don’t)

I’m a financial coach.

How we handle the edges

How we handle the edges

  I help you get clear on cash-flow, cut “silent fees,” use your benefits well, and make decisions you’ll keep. This is educational coaching—not legal, tax, or investment advice. When specialized advice is needed, I’ll help you prepare questions and connect you with neutral referrals (I don’t take referral fees). 

How we handle the edges

How we handle the edges

How we handle the edges

If a question crosses into a regulated area, I’ll flag it, pause, and help you talk to the right professional—often with a one-page brief so your time (and money) is used well. 

Read More

What I do

What I don’t do

What I don’t do

  • Build a simple monthly system you can run 
  • Find and cut 2–3 recurring “silent fees” 
  • Set weekly caps and auto-transfers 
  • Prep for negotiations and money conversations 
  • Map first-month budgets for expat moves 
  • Create checklists, scripts, and a small dashboard

What I don’t do

What I don’t do

What I don’t do

  • No investment selection or portfolio management 
  • No tax return preparation or individualized tax advice 
  • No legal advice within coaching (separate engagement required) 
  • No mental-health treatment or diagnosis

General Disclaimer

 Educational coaching only—no legal, tax, or investment advice. No attorney‑client relationship is formed through this site or coaching. When specialized advice is needed, we help you prepare questions and can provide neutral referral options (no compensation received). 

Find out more

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