Today I'm joined by Sam Vander Wielen, a former lawyer who built an eight-figure creator business while recovering from brain surgery.

In this episode, we explore how Sam went from burnt-out lawyer to building a $1.6M/year digital product business with just one full-time employee.

She shares the strategy behind her evergreen funnel, the mindset shifts that helped her grow, and the systems that kept the business running after losing both of her parents.

Timestamps:
00:00 Introduction
01:16 Discovering Her True Calling in Business
03:00 Frustrations with the Legal Industry
06:15 Early Signs of Entrepreneurial Spirit
08:55 Food Blog to Legal Templates Pivot
10:24 Starting with SEO and Organic Content
13:01 First Month Revenue & Early Wins
15:47 Scaling to 1.6M with One Product
17:19 “All Roads Lead to the Email List”
18:42 Evergreen Webinar Funnel that Converts
21:04 Ad Strategy & Scaling Mistakes
23:29 Voice of Customer Research System
26:30 The Power of a Simple Product Suite
28:04 Navigating Brain Surgery & Caregiving
33:45 Building a Business While Grieving
38:50 Dropping Social Media & Saying No
41:27 Systems for Automation & Scrubbing
43:30 The Power of Writing a Weekly Newsletter
44:52 Book Launch: When I Start My Business I’ll Be Happy
47:10 Why “Community Over Competition” is BS
49:18 Preparing for Craft & Commerce
51:17 What’s Next for Sam

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

Follow Nathan:
Instagram: https://www.instagram.com/nathanbarry
LinkedIn: https://www.linkedin.com/in/nathanbarry
X: https://twitter.com/nathanbarry
YouTube: https://www.youtube.com/@thenathanbarryshow
Website: https://nathanbarry.com

Follow Sam:
Newsletter: https://www.samvanderwielen.com/samsidebar
Instagram: https://www.instagram.com/samvanderwielen
Website: https://www.samvanderwielen.com
Book: When I Start My Business I’ll Be Happy – available wherever books are sold

Featured in this episode:
Ultimate Bundle: https://www.samvanderwielen.com/ultimate-bundle
Kit: https://kit.com
Melissa Griffin: https://melissagriffin.com
Craft + Commerce: https://convertkit.com/craft-commerce

Today I'm joined by Jay Singh, AI expert and founder of Casper Studios, to explore how AI is transforming both product creation and internal workflows for creators and businesses alike.

We dive deep into the future of personalized software, unlocking AI use cases for creators, and building tools with platforms like Cursor, MindStudio, and Replit.

Jay shares how creators can implement fast, practical automations to save time, boost output, and stay ahead in a rapidly changing AI landscape.

You'll learn how to identify your best automation opportunities, spin up AI-driven products from transcripts and meeting notes, and use AI to turn raw data into insight, revenue, and leverage.

Timestamps:
00:00 – Introduction
02:17 – Why AI Helps 95% of Tasks—but Gets Used for 50%
06:12 – Creators, Voice, and the Future of AI
08:33 – Jay’s Background at Microsoft & LinkedIn
10:09 – The 3-Step Framework for AI Product Thinking
13:26 – Automating Finance, Accounting & Accuracy
18:02 – How Jay’s Agency Designs AI Workflows
20:19 – Zapier, MindStudio & Real AI Implementations
24:36 – Going From Transcript to Product Requirements in Minutes
27:11 – V0, Cursor & AI Product Design Workflows
33:07 – Kit's App Store Vision & The Future of Personalized Software
38:15 – Building AI Tools Without Knowing the Future
42:24 – AI Tools Every Creator Should Be Using
45:42 – Meeting Transcripts → LinkedIn Content
48:19 – AI-Powered Weekly Metrics Reports for Creators
51:06 – How to Spot Your Own Automation Opportunities
55:09 – Why Everyone Thinks Their Job is “Safe” From AI

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

Follow Nathan:
Instagram: https://www.instagram.com/nathanbarry
LinkedIn: https://www.linkedin.com/in/nathanbarry
X: https://twitter.com/nathanbarry
YouTube: https://www.youtube.com/@thenathanbarryshow
Website: https://nathanbarry.com

Follow Jay:
LinkedIn: https://www.linkedin.com/in/jaysingh
X: https://x.com/JSingh_08
Website: https://casperstudios.xyz

Featured in this episode:
MindStudio: https://mindstudio.com
Cursor: https://cursor.sh
V0: https://v0.dev
Fireflies: https://fireflies.ai
Replit: https://replit.com
Kit: https://kit.com

Today I’m joined by Lars Tiger, a Norwegian music producer who makes $500,000 a year—almost entirely profit—working just two hours a week from his home in the south of France.

We dive deep into the experiment that made it possible: releasing thousands of piano tracks with no marketing, using pure volume to generate income and data. Lars shares how he redefined quality, stopped chasing perfectionism, and built a flywheel that creators in any industry can apply.

You’ll learn how volume creates financial stability, how to think like a fisherman (not a perfectionist), and why quantity—not quality—is the fastest path to mastery.

Timestamps:
00:00 Introduction
01:26 Lars’ $500K/yr, 2-hour workweek model
04:12 Creating 1,000 tracks with zero marketing
08:10 Why 80% quality is enough (and often better)
14:05 The Pottery Class Experiment
17:52 From hits to stability: the math behind his model
20:21 Why Spotify only brings in 15–20% of revenue
22:30 What actually drives plays (hint: not TikTok)
25:42 Helping traditional artists embrace volume
30:38 Can this model scale to $1M+?
34:50 YouTube, repurposing, and platform expansion
39:00 Balancing freedom vs scale
46:04 Faceless creators, pen names, and creative freedom
52:02 What are you optimizing for?

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

Follow Nathan:
Instagram: https://www.instagram.com/nathanbarry
LinkedIn: https://www.linkedin.com/in/nathanbarry
X: https://twitter.com/nathanbarry
YouTube: https://www.youtube.com/@thenathanbarryshow
Website: https://nathanbarry.com

Follow Lars:
Website: https://www.larstiger.com
Instagram: https://www.instagram.com/larstiger/
LinkedIn: https://www.linkedin.com/in/larstiger

Featured in this episode:
Lars’ Free Music Catalog Course: https://www.larstiger.com
ConvertKit: https://convertkit.com
Flywheels Course: https://nathanbarry.com/flywheels
The Personal MBA: https://personalmba.com

#musicproducer #entrepreneur #songwriter

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

If you enjoyed this episode, please like, subscribe, share, and leave a comment with your thoughts or questions for a future episode – we read every single one!

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

Follow Tiffany Uman:
Website: https://tiffanyuman.com
LinkedIn: https://www.linkedin.com/in/tiffany-uman-career-strategy-coach
Instagram: https://www.instagram.com/tiffany.uman
TikTok: https://www.tiktok.com/@tiffany.uman
X: https://x.com/tiffanyuman
YouTube: https://www.youtube.com/@UCQqfl93s1XEyc5pbMYoyF_g

Follow Nathan:
Instagram: https://www.instagram.com/nathanbarry
LinkedIn: https://www.linkedin.com/in/nathanbarry
X: https://twitter.com/nathanbarry
YouTube: https://www.youtube.com/@thenathanbarryshow
Website: https://nathanbarry.com

Featured in this episode:
Tiffany Uman Coaching - https://tiffanyuman.com
Andrew Huberman - https://www.youtube.com/@UC2D2CMWXMOVWx7giW1n3LIg
Ryan Holiday - The Obstacle In The Way (book) - https://ryanholiday.net/books-courses/
Deliverability Defined Podcast - https://deliverability.transistor.fm/
Lil Jon's Wellness Wednesdays - https://liljon.kit.com/newsletter
Microsoft – https://www.microsoft.com
L’Oréal – https://www.loreal.com
LinkedIn Learning – https://www.linkedin.com/learning

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

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

Follow Nathan:
Instagram: https://www.instagram.com/nathanbarry/
LinkedIn: https://www.linkedin.com/in/nathanbarry/
X: https://x.com/nathanbarry
YouTube: https://www.youtube.com/@thenathanbarryshow
Website: https://nathanbarry.com

Follow Matthew:
Instagram: https://www.instagram.com/nomadicmatt/
Website: https://www.nomadicmatt.com
X: https://x.com/nomadicmatt
LinkedIn: https://www.linkedin.com/in/nomadicmatt/

Featured in this episode:
How to Travel the World on $75 a Day: https://www.nomadicmatt.com/how-to-travel-the-world
Kit: https://kit.com
Home Exchange: https://www.homeexchange.com
Southwest Airlines: https://www.southwest.com
Japan Rail Pass: https://www.japanrailpass.net

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

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

Follow Nathan:
Instagram: https://www.instagram.com/nathanbarry
LinkedIn: https://www.linkedin.com/in/nathanbarry
X: https://twitter.com/nathanbarry
YouTube: https://www.youtube.com/@thenathanbarryshow
Website: https://nathanbarry.com

Follow Ali:
LinkedIn: https://www.linkedin.com/in/alischwanke
Website: https://www.alischwanke.com
Instagram: https://www.instagram.com/alischwanke/
X: https://x.com/alischwanke
YouTube: https://youtube.com/@HubSpotHacks

Featured in this episode:
Simple Strat: https://www.simplestrat.com
Marketing Deconstructed: https://marketingdeconstructed.com
HubSpot Hacks: https://youtube.com/@HubSpotHacks
Tubebuddy: https://www.tubebuddy.com
Kit: https://kit.com

Highlights:
00:09 – We need to retrain how we think about marketing
01:13 – “Marketing is simple when strategy is sound”
03:07 – Start with what already works
08:20 – From YouTube tutorials to a $2M agency
16:00 – Potential offers and decoy pricing
45:40 – Becoming the “Oprah of marketing”

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

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

Follow Nathan:
Instagram: https://www.instagram.com/nathanbarry
LinkedIn: https://www.linkedin.com/in/nathanbarry
X: https://twitter.com/nathanbarry
YouTube: https://www.youtube.com/@thenathanbarryshow
Website: https://nathanbarry.com

Follow Charli:
Instagram: https://www.instagram.com/charliprangley
LinkedIn: https://www.linkedin.com/in/charliprangley
Twitter: https://twitter.com/charliprangley
YouTube: https://www.youtube.com/user/charlimarietv
Website: https://charlimarie.com

Featured in this episode:
Kit: https://kit.com
Koto (Brand Strategy Partner): https://www.kotoagency.com
Square Black (Development Agency): https://squareblack.com
Tom Brady’s Newsletter: https://www.tombrady.com/newsletter
Morgan Freeman: https://themorganfreeman.com

Highlights:
06:03 – Churn: The Leaky Bucket Challenge
15:05 – Unpacking the 6-Step Direct Sales Flywheel
22:05 – Overcoming Migration Objections with Concierge Setups
29:21 – The Zero-to-One of Personal Branding
36:08 – Scheduling & Measurement: Locking In Daily Priorities
49:20 – Innovating Pricing Strategies for Expansion Revenue

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

Follow Nathan:
Instagram: https://www.instagram.com/nathanbarry/
LinkedIn: https://www.linkedin.com/in/nathanbarry/
X: https://x.com/nathanbarry
YouTube: https://www.youtube.com/@thenathanbarryshow
Website: https://nathanbarry.com

Follow Laura:
Website - https://laurasprinkle.com/
Rootabl (10% discount) - https://rootabl.com/special-offer/
Instagram - https://www.instagram.com/imlaurasprinkle/
Linkedin - https://www.linkedin.com/in/imlaurasprinkle/

Featured in this episode:
- Rootabl: https://rootabl.com
- Kit: https://kit.com
- Mighty Networks: https://www.mightynetworks.com