Podcast Summary: Success Story with Scott D. Clary

Episode: Lessons - The Ex-Con Who Built an Empire | Ryan Stewman - Sales Coaching Mogul
Date: December 29, 2025
Host: Scott D. Clary
Guest: Ryan Stewman

Overview

This episode of the Success Story podcast explores the remarkable journey of Ryan Stewman, a former convict who transformed his life by building a multi-million dollar sales coaching and business empire. Stewman and Clary dissect the foundational steps of creating a scalable coaching business, emphasizing the power of leveraging personal expertise, validating demand before building products, and evolving from a solo operator to the founder of a thriving entrepreneurial network.

Key Discussion Points & Insights

1. From Prison to Entrepreneur: The First Hustle

• Authentic Beginnings: After being released from federal prison, Stewman started a social media marketing agency, directly leveraging the skills and hustle he knew.
  • "People that know me well say I'm one of the greatest writers alive. And back then I would write for you—for a hundred dollars a month, I would write five Facebook posts a day for you." — Ryan Stewman (00:38)
• Capacity & Learning: He landed 70 clients solo, learning firsthand about different industries and social media responses.
  • "I built this thing to 70 people. Again, no partners, no helpers, no investors, no bank, no advisors. I don't know what the fuck I was doing. I just knew I was onto something..." — Ryan Stewman (00:52)

2. Pivoting to Coaching: Scaling Smarter

• Why Coaching? Stewman realized teaching what he knew was more scalable than done-for-you services.
  • "I can just teach people how to do [...] that's obviously a more scalable route. At least when you're one person, group coaching is more scalable than individual social media." — Ryan Stewman (01:43)
• Standing Out in Crowded Markets: Both social media marketing (2011) and coaching became crowded spaces; Stewman’s edge was real experience and clear outcomes.

3. “Sell on the Level That You’re At”: Positioning and Offers

• Credibility Through Results: Stewman only sold what he’d mastered himself, delivering programs to help loan officers increase their monthly production based on his own track record.
  • "Sell on the level that you're at... I knew I could teach people that were making five or $10,000 a month how I got to 30." — Ryan Stewman (03:47)
• Niche Marketing: He stuck to industries he knew—primarily mortgages and title companies—and crafted offers directly to their pain points.

4. Validating Demand and Pre-Selling

• Minimum Viable Offer: Instead of building a full course first, he presold a six-week bootcamp via a simple funnel (YouTube video + Wufu survey form), enrolling students before recording the training content.
  • "Most people [...] spend time creating this digital product, and then they go to sell it—nobody buys. [...] I made sure everybody wanted, so I pre-sold it." — Ryan Stewman (06:58)
• Results-Based Pricing: The price ($2,000) aligned with the customer’s tangible ROI (closing just one more loan covered the cost).

5. Funnel Evolution and Scaling Tactics

• Iterating Offers: By initially targeting anyone under $2 million/month in mortgage production, Stewman faced high objection rates due to affordability. Adjusting to target those already producing $2 million+ improved conversion dramatically.
  • "I changed the offer from if you're a loan officer doing 2 million or less to if you're a loan officer who's closing at least $2 million a month [...] at that point, it takes all the people who... at least you're making about 20 grand a month." — Ryan Stewman (09:55)
• Operational Lessons: Early on, Stewman did everything—sales, marketing, content. Over time, he learned to hire and delegate as the business scaled.

6. Product and Program Expansion: Building an Ecosystem

• From Individual Products to a Movement: The business evolved into “Apex,” a tiered network for top professionals across industries—surpassing Stewman as the central draw, and offering a community for high-performers to connect, learn, and grow.
  • "It's evolved into something now that's got 2,000 active members. We are doing well—well into eight figures a year... with only two sales guys." — Ryan Stewman (12:24)
• Providing Platforms for Others: Apex gives a stage to talented but lesser-known leaders, fostering a strong, value-driven community.
  • "I get to put unknown names that are brilliant with huge companies on stages to speak that wouldn’t normally get the FaceTime..." — Ryan Stewman (12:19)

Notable Quotes & Memorable Moments

• On scrappiness and early struggles:
  "I didn't have no damn money. You know what I'm saying? Like, I didn't have the money to waste time. [...] I had to hustle." — Ryan Stewman (07:51)

• On the psychology of pricing:
  "My whole pitch on the phone call was, like...for sure we can get at least one more loan over the course of six weeks from what I’m going to teach you..." — Ryan Stewman (08:25)

• On overcoming the solo founder bottleneck:
  "I'm the only sales guy, I'm the only marketer, I'm making the funnel, making the video, editing the video... I didn't have mentors." — Ryan Stewman (08:48)

• On accelerating through niche focus:
  "Eventually, there's only 300,000 loan officers in America—and I sold products to 20-something thousand of them. So eventually, I kind of ran through that marketplace pretty good, right? And I got bored." — Ryan Stewman (11:18)

Timestamps for Key Segments

• 00:38 – Ryan describes his first post-prison business as a copywriter and social media manager.
• 01:49 – Pivoting from services to scalable coaching due to operational constraints.
• 03:47 – “Sell at the level you’re at” and the origin of targeting fellow loan officers.
• 06:58 – Building and iterating his first sales funnel; the value of pre-selling.
• 08:25 – Crafting a no-brainer coaching offer ($2,000/6 weeks) for loan officers.
• 09:55 – Narrowing the target market to high-performing clients for better close rates.
• 12:19 – The birth and evolution of the “Apex” network—beyond Ryan and into a movement.
• 12:24 – Reaching eight figures with only two sales staff, focusing on community and quality.

Conclusion

Ryan Stewman's journey showcases the transformational power of leveraging lived experience, starting lean, validating market demand, and consistently refining both offer and audience. His candid recounting of operational mistakes, pricing psychology, and ultimate shift from solopreneurship to building a sustainable, scalable ecosystem offers real, actionable insight for anyone interested in the coaching or expert business space.

If you want more in-depth strategies or to hear the full conversation, check out the episode on the Success Story Podcast.