Meet the Founders: The Origin Story of Retirement Analyzer & the What If That Started It All
- E1
- 44:02
- March 16th 2026
In this debut episode of The What If Show, host Mike Langford sits down with Thomas Gold Solutions founders Brooke Thomas and Steve Goldstein to pull back the curtain on the origin story behind one of the most trusted retirement planning platforms in the financial services industry — Retirement Analyzer.
You'll hear how a solo producer in Idaho named Chuck Cravens built the foundation of RA on Excel spreadsheets over 30 years ago because he was obsessed with answering client "what if" questions at the click of a button. How a 23-year-old Brooke Thomas, fresh out of college with zero sales experience, used that software to generate $150,000 in commissions in her very first year. And how a Wall Street trader named Steve Goldstein made a career leap into financial advising, fell in love with Retirement Analyzer, introduced Brooke at a webinar by reading nervously off a piece of paper — and ended up building a company with her a decade later.
But this episode isn't just a great origin story. Brooke and Steve go deep on the concepts that define their approach to retirement planning, including:
- Why financial plans have so many moving parts — and why that's actually an opportunity for advisors
- The budget conversation most advisors avoid (and why the ones who require it close the biggest cases)
- What the famous "red line" in RA really means and why showing it to clients is a confidence-building superpower
- Why Thomas Gold picks up the phone when you call — even on weekends
The episode wraps with the debut of Retirement BS with Brooke and Steve — the show's recurring segment that tackles common retirement planning myths and misconceptions. First up: the age-old client question, "Should I just pay off my mortgage?"
Whether you're a seasoned financial planner, a newer advisor looking for an edge, or just curious about what makes Retirement Analyzer different, this is the episode that sets the stage for everything that follows on The What If Show.
Chapters:
00:00 Welcome to The What If Show
01:32 Why It's Called "The What If Show"
03:15 Brooke's Story: From Zero Sales Experience to $150K Year One
05:43 Steve's Story: From Wall Street Trader to FinTech Founder
06:48 How Brooke and Steve Actually Met
09:33 Why Financial Plans Have So Many Moving Parts
11:37 The Budget Conversation Most Advisors Avoid
15:21 Why Thomas Gold Actually Answers the Phone
19:14 Getting Over the "New Software" Hump
23:12 Continuous Continuing Education
27:08 Small Changes, Big Outcomes (The Tour de France Analogy)
28:58 The Red Line Explained
32:34 Tab by Tab: How RA Builds Advisor Confidence
34:42 Let the Math Tell the Story
38:27 Introducing "Retirement BS" with Brooke & Steve
39:13 Retirement BS #1: Should You Pay Off Your Mortgage?
41:42 What Do YOU Want Us to Cover Next?
The What If Show
What if your next client appointment was your best one yet?
The What If Show is the podcast for financial advisors and financial planners who want to show up to every client meeting with confidence, clarity, and a plan that actually answers the hard questions. Hosted by Brooke Thomas and Steve Goldstein and powered by the team at Thomas Gold Solutions the company behind Retirement Analyzer... each episode explores the strategies, tools, and mindset shifts that help advisors deliver better retirement planning outcomes for their clients.
Because in retirement planning, every client walks in with the same unspoken question: Am I going to be okay? The best advisors don't just answer that question — they answer every "what if" that comes with it.
From debunking retirement planning myths in the Retirement BS segment to deep dives with industry experts, practitioners, and the people behind one of the most advisor-trusted planning platforms in the country, The What If Show gives you the insights and inspiration to become the advisor your clients can't stop referring.
New episodes drop regularly. Subscribe now and start answering the what ifs with confidence.
Brooke Thomas is the co-founder of Thomas Gold Solutions and one of the most experienced voices in retirement planning software in the financial services industry. Her story with Retirement Analyzer starts at the very beginning — she was the first person recruited by RA's original creator, Chuck Cravens, to test whether the platform could work for someone brand new to the business. At 23 years old, fresh out of college, with zero sales experience, Brooke went out and proved it could, turning over $150,000 in commissions in her first year.
That experience — knowing firsthand what it feels like to sit across from a client and need the right answer right now — shapes everything about how Thomas Gold operates today. Brooke oversees training, customer support, and product development with one guiding principle: advisors deserve a partner who actually picks up the phone.
Steve Goldstein spent 22 years as a trader on Wall Street before the market changed and he decided it was time to change with it. He became a financial advisor in the early 2000s — and quickly discovered that what he loved most about the work wasn't the products. It was the teaching. The moment a client actually understood their financial picture. The aha.
That obsession with clarity led him to Retirement Analyzer, and eventually to co-founding Thomas Gold Solutions with Brooke Thomas in 2010. Today the company serves more than 6,000 financial advisors and Steve is still the one who answers the phone on a Saturday morning from the aisle at Costco if that's what it takes. He travels the country leading bootcamps and training sessions with one mission: helping advisors become the most confident, capable version of themselves in every client appointment.