The Nathan Barry Show

Today I’m joined by Tiffany Uman, a transformational coach and marketing strategist who built her multi‑million dollar coaching business from scratch.

In this episode, Tiffany shares the four pillars behind her success, reveals how she transitioned from corporate L’Oréal to launching her business during maternity leave, and outlines her proven strategies for scaling revenue and driving client transformation.

Timestamps:
00:00 – Introduction
01:27 – Tiffany’s Four Pillars of Business Growth
03:28 – From Corporate Executive at L’Oréal to Entrepreneur
06:39 – Starting a Coaching Business While on Maternity Leave
11:24 – Balancing Family & Business Growth
16:28 – Identifying and Overcoming Key Man Risk
20:19 – The Turning Point: Scaling Beyond $500K
24:14 – How to Break Past Growth Plateaus
32:00 – Diversifying Revenue Streams & Leveraging B2B
37:14 – Tiffany’s Approach to Building a Team
41:12 – Elevating Team Members to Reduce Dependency on You
45:18 – Identifying & Overcoming Limiting Beliefs
49:02 – Using Flywheels to Create Sustainable Growth
53:17 – Leveraging AI to Streamline Operations
1:00:03 – Where to Follow Tiffany & Closing Thoughts

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Today I’m joined by Matthew Kepnes (Nomadic Matt) to break down how to turn travel into a profitable business in 2025.

Matt has spent over 15 years traveling full-time, building one of the world’s most recognized travel brands. We discuss how travel creators can monetize effectively—through email, events, and brand deals—while staying authentic.

Matt shares his five-step system for making money while traveling, from why every creator needs a website to how to sell experiences and build a loyal community.

Timestamps:
00:00 - Introduction
01:22 – From Budget Traveler to Travel Entrepreneur
03:06 – The Turning Point: How Matt Built His Blog
05:04 – The $75 a Day Strategy: Traveling Affordably
07:17 – Why Travel Content is Still Profitable in 2025
09:30 – The 5 Essential Steps to Making Money While Traveling
12:57 – Why Every Creator Needs a Website in 2025
15:25 – The Power of Email Lists & Webinars for Monetization
19:48 – Building Community Through Events & Tours
22:55 – The Truth About Travel Brand Deals
27:21 – Scaling a Travel Business Without Burnout
30:57 – Lessons from Attending 15 Taylor Swift Concerts
35:10 – How to Monetize a Travel Blog Without Relying on Ads
40:16 – The Best Ways to Land High-Paying Brand Deals
45:45 – What’s Changed in the Travel Industry Post-COVID
50:26 – The Updated Edition of How to Travel the World on $75 a Day
52:30 – Closing Thoughts: The Future of Travel Content Creation

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Learn more about The Nathan Barry Show: https://nathanbarry.com/show

Today I'm joined by Ali Schwanke for a coaching session to map out how she can add $100K in creator income to her thriving services business.

We dive deep into pricing, bundling digital products, and leveraging Ali’s existing audience—showing exactly how to build profitable, scalable offers without cannibalizing core services.

You'll learn our approach to identifying your best passive income opportunities, packaging your expertise into clear products, and quickly validating your idea before launching.

Timestamps:
00:00 Introduction
01:13 Marketing Is Simple When Your Strategy Is Sound
03:07 Escaping Marketing Chaos
06:18 Why Most LinkedIn Outreach Fails
08:02 How Ali Built Simple Strat
10:08 Growing Her HubSpot YouTube Channel
15:59 Mapping Revenue & Audience Assets
21:11 Finding Ali’s Best Passive Income Opportunities
25:48 How to Price & Package Digital Products
38:51 Using Decoy Pricing To Boost Sales
46:39 Designing the Perfect Pilot Program
55:18 Recap & Next Steps

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Today I’m joined by Charli Prangley as we revisit our bold rebrand from ConvertKit to Kit - a journey of rapid change, decisive leadership, and preserving what truly matters.

In this episode, we explore how we built a new identity without starting from scratch, the lessons learned along the way, and how our internal culture has evolved as a result.

Timestamps:
00:00 Introduction to Branding
00:49 The Kit Rebrand Journey
01:55 Lessons Learned from Rebranding
05:11 Maintaining Brand Equity
06:39 Challenges and Successes
08:25 The Importance of Brand Strategy
12:42 Messaging and Positioning
15:33 Internal Shifts and Bold Actions
18:56 Kit's Self-Belief and Leadership
22:45 Creating Tutorials and Overcoming Roadblocks
24:51 Celebrity Endorsements and Success Stories
25:28 The Impact of a Strong Brand
31:24 Executing a Successful Rebrand
36:27 Dreaming Big and Making It Happen
39:27 Reflecting on Leadership and Growth
43:13 Final Thoughts and Encouragement

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Today I’m joined by Laura Sprinkle for a live coaching session on scaling her new affiliate-tracking SaaS, Rootabl, from $5,000 MRR to $25,000 MRR while maintaining the flexibility and freedom she values.

Laura has deep expertise in affiliate launches and is now shifting into the software world - facing new challenges like churn, onboarding friction, and deciding which features to build first.

We map out her next steps - from clarifying her ideal target customer and harnessing personal branding for trust, to using direct outreach as a repeatable engine for sustainable growth. You’ll learn why concierge migrations can be a secret weapon, how to choose the right community integrations, and why narrowing your audience often leads to better results.

Timestamps:
00:00 Introduction
01:14 Why Creator-Led SaaS Is Harder (Yet More Rewarding)
02:39 How Laura Reached $5K MRR
07:36 Tackling Churn and Onboarding Friction
11:29 Using Personal Branding to Increase Conversions
14:55 The Direct Sales Flywheel Explained
19:48 Turning “Concierge Migrations” into a Competitive Advantage
30:57 Choosing Your Integrations Wisely
31:24 New Features vs. Doubling Down on Existing Ones
37:17 Reducing Churn
40:16 Narrowing Your Customer Profile for Faster Growth
45:45 Using Outreach to Drive Predictable Revenue
47:11 Introducing Tiered Pricing for Expansion
50:26 Tracking Progress & Staying Focused
51:52 The Power of Iteration in SaaS Growth
01:02:54 Closing Thoughts

If you enjoyed this episode, please like and subscribe, share it with your friends, and leave us a review. We read every single one.

Learn more about The Nathan Barry Show: https://nathanbarry.com/show