How to Pick a Business You ACTUALLY Enjoy (In 64 Mins) | 065 - The Nathan Barry Show

The Nathan Barry Show, Episode 065
How to Pick a Business You ACTUALLY Enjoy (In 64 Mins)
Date: February 20, 2025
Guest: Isaac French

Episode Overview

In this episode, Nathan Barry sits down with Isaac French, a creator and entrepreneur who has rapidly built over $5 million in enterprise value within two years, primarily through his innovative approach to experiential hospitality and creator business flywheels. The discussion centers on how to choose your next business move when faced with multiple enticing options, balancing personal fulfillment, financial ambition, and lifestyle design. The session doubles as live coaching, diving into strategy, audience-building, digital products, content flywheels, and optimizing for quality of life.

Key Discussion Points & Insights

Isaac's Journey & Current Business Structure ([01:16]–[10:09])

Origin Story & Success Stats:
- Found property in Waco, TX, designed & built Live Oak Lake: seven modern cabins, $2.3M invested.
- Achieved 95% occupancy, 80% direct bookings, built 140k Instagram followers in 15 months.
- Sold for $7M in less than two years, then began sharing the journey online.
- Grew audience on Twitter (now X), transitioned to a newsletter and launched a subscription-based masterclass & membership for hospitality operators.
Digital Product Funnel:
- Free 7-day email course leading to paid masterclass.
- Automated FOMO sales sequence with early-bird discounts.
- Recently added calls with a sales team to close higher-priced deals.
- Community membership at $250/month or $2,000/year.
Key Numbers:
- Masterclass revenue: $600,000 ([06:58])
- Community recurring revenue: $200,000 ARR ([07:26])
- Combined digital revenue: ~$800,000
- Facebook lead acquisition: ~$3/lead ([05:05])
Flywheel Effect:
- Automated onboarding, community feeds course, Isaac tells community members' stories as X threads, which drive more leads and create a virtuous loop.
“The members in my community, the recurring revenue community, which are super high value - I get to coach them, learn from them... pick the best stories, share those as threads which generate a ton because I'm the expert now” – Isaac French ([09:03])

Mapping Future Paths: Four Business Options ([10:09]–[19:18])

Nathan and Isaac brainstorm and dissect four main opportunities:

Content Agency:
- Replicating the social/content results Isaac achieved for Live Oak Lake for other property owners, potentially with a 50/50 split with agency partners.
- Direct application of flywheels: teach owners, consult, then offer a done-for-you service as they realize the workload.
SaaS Product:
- Creating a “Shopify for experiential hospitality” (direct booking engine software).
- High long-term enterprise value route, but requires focus, domain mastery, and willingness to play the long game (5–10 years).
“If you came to me and said, hey, the thing that I am optimizing for most is enterprise value...it's for me it would be the next property or it'd be software.” — Nathan Barry ([23:46])
New Property Development:
- Building another Live Oak Lake (but perhaps smaller, in the 1–3 unit range for manageability and story appeal).
- Access to capital is strong, but Isaac prioritizes intentional scaling and maintaining quality.
Scaling Content:
- Going all-in on YouTube, potentially starting a podcast, and focusing on storytelling to expand the audience and amplify personal brand equity.
“That’s kind of my dream, is to grow a really nice YouTube audience...” – Isaac French ([19:18])

Decision-Making Criteria & Optimizing for Quality of Life ([19:50]–[26:21])

What To Optimize For?
- Not just money: “I want both [cashflow and equity]. I really want, like, I want 50/50. I want a nice lifestyle… and I want a nice nest egg that I can pass on.” — Isaac French ([22:01])
- Core values: quality of life, small team, engaging work, travel, faith, family.
- Avoiding overexpansion and burnout; preferring a hands-on, high-integrity approach.
Two Buckets: Cashflow vs. Enterprise Value
- Nathan emphasizes distinguishing between short-term profits and long-term value.
  
  “One mistake that I see a lot of creators make is they don’t think about the difference. They don’t think of those two buckets.” — Nathan Barry ([21:01])
Small Team Preference:
- Isaac resists the idea of building a large staff, preferring either solo or a tiny, high-performance team.
“Do not want a big team...the thought of managing a team or dealing with HR...I'm allergic to that.” – Isaac French ([30:10])

Analyzing Each Option in Depth ([26:21]–[43:16])

SaaS Off the Table (For Now):
- Software only makes sense if you go “all-in” and have a world-class operator as a partner; not a half-hearted or side project.
- Nathan’s advice: Be realistic about the learning curve and commitment.
  
  “Software is going to have this very, very slow ramp up...but you should go in with it being that difficult, long game.” — Nathan Barry ([31:39])
Agency Option:
- Valid, but must find the ideal partner/operator; explore the space, take calls, don’t commit hastily.
- Passive strategy: collect ideas, interview prospects, prepare, but don’t rush.
  
  “You can say, hey, over the next year I'm going to meet 10 to 20 people who might be this operator and...I'll start to know what it takes to build a world class agency.” – Nathan Barry ([35:34])
Next Property:
- Doing a small, high-quality, story-driven project (1–3 units) maximizes audience and community impact while controlling risk.
- Encourages inspiring newcomers and creating approachable, replicable models.
  
  “Three units is like micro resort...some exponential difference where you create, like, a communal setting...a lot more approachable in terms of finances and just overall work than seven.” — Isaac French ([40:26])
Content Scaling:
- Primary goal: Mastering storytelling via YouTube and possibly podcasting.
- Audience as the real form of “equity.”
- Success means greater impact, invitations, cashflow potential, and audience leverage.
  
  “I want to create films that move people.” — Isaac French ([49:09])

Isaac's Personal Philosophy and Guardrails ([51:18]–[62:06])

Money as a Means, Not the End:
- Financial security is desirable, but the main focus is impact, joy, and enrichment.
  
  "I've found so much value in...connecting with an audience, telling stories, living a life that I'm privileged to live. And I just don't want to mess that up." — Isaac French ([51:19])
Personal Brand as Long-Term Asset:
- Audience value can be “locked” but has compounding utility: launches, investments, influence.
  
  “The most valuable thing you have is your reputation...your ability to raise millions of capital if you want it...to sell a digital product, to create any of these things in the future.” — Isaac French ([41:37])
Being Recognizable, But Not Celebrity:
- Sweet spot: Respected and recognized by the community that matters, but not mainstream “celebrity”.
- Draws inspiration from his grandfather—master craftsman, private integrity.
  
  “I want to be famous enough where I can talk to anyone I want, but people don't really know me.” — Isaac French ([58:14])
  
  “He never spent a dime on marketing, but just basically put his all into it. Cared for each project, each customer like they were his own family...” — Isaac French ([61:12])

Actionable Plan & Roadmap ([53:59]–[64:06])

What Nathan Recommends:

Agency: Put on passive mode; start collecting data, have exploratory conversations, but don't commit yet.
SaaS: Off the table for 3–5 years; table until there’s time, capital, and ideal cofounder.
Next Property: Go all-in on a small (1–3 unit) project, with a focus on storytelling; quality > scale.
Scaling Content: Invest significant time & money into mastering visual storytelling for YouTube (and possibly podcasting), focusing on skill development over audience size or immediate ROI.
Newsletter: Continue building the email list as a central asset.
Maintain optionality and low overhead: All choices maintain flexibility for larger moves down the line.

“If I were in your position...the next property, you go all in on a small three unit. The storytelling is perfect, and you're really optimizing for the story and the equity value through the audience...And then I would set aside a certain amount of money from the masterclass...and invest 100, $200,000 a year into...mastering storytelling and growing the YouTube audience.” — Nathan Barry ([53:59])

Memorable Quotes & Moments

On making business choices:

“The difference between successful people and really successful people is that really successful people say no to almost everything.” — Nathan Barry quoting Warren Buffett ([00:32], [10:54])
On the value of community:

“It's the best feeling in the world that I have a small but valuable audience that can make a meaningful difference in these people's lives.” — Isaac French ([20:16])
On long-term planning and personal happiness:

"I love connecting with people. That's why I love this community so much. Like minded people that care about design. And I love traveling and seeing new places, meeting new people..." — Isaac French ([19:50])

Key Timestamps

[01:16] Isaac’s journey from real estate to digital business
[03:21] Masterclass sales funnel & automation
[06:58] Digital product revenue numbers
[09:03–10:09] Community-content flywheel effect
[11:21] Exploring business options: Content agency, SaaS, more properties, content scaling
[19:50] Isaac’s core decision criteria: optimizing for quality of life, community, and fulfillment
[23:46] Nathan breaks down value: cashflow vs. equity
[31:39] SaaS as a path—how hard is it really?
[36:05] Agency partnerships and choosing the right operator
[41:14–41:37] Micro-resort idea: impact and approachability over sheer scale
[49:09] Mastering storytelling as self-realization and business multiplier
[58:14] Finding the right level of visibility and fame
[61:12] Isaac’s grandfather: legacy and values

Final Takeaways

Choose business opportunities that align with your values, desired lifestyle, and skills you’re eager to master—not just with financial upside.
Maximize leverage with flywheels: community, content, and personal brand feed each other for compounding results.
Be intentional with scaling: Small teams can create outsized results when backed by the right frameworks and clear decision filters.
Prioritize learning, storytelling, and community-building, as these build lasting enterprise value and preserve optionality.
Actively say “no” to maintain focus, bandwidth, and quality in both work and life.

Where to Find Isaac French

Instagram & Twitter: @isaacfrench_
Newsletter: isaacjfrench.com

The Nathan Barry Show, Episode 065
How to Pick a Business You ACTUALLY Enjoy (In 64 Mins)
Date: February 20, 2025
Guest: Isaac French

Episode Overview

Key Discussion Points & Insights

Isaac's Journey & Current Business Structure ([01:16]–[10:09])

Origin Story & Success Stats:
- Found property in Waco, TX, designed & built Live Oak Lake: seven modern cabins, $2.3M invested.
- Achieved 95% occupancy, 80% direct bookings, built 140k Instagram followers in 15 months.
- Sold for $7M in less than two years, then began sharing the journey online.
- Grew audience on Twitter (now X), transitioned to a newsletter and launched a subscription-based masterclass & membership for hospitality operators.
Digital Product Funnel:
- Free 7-day email course leading to paid masterclass.
- Automated FOMO sales sequence with early-bird discounts.
- Recently added calls with a sales team to close higher-priced deals.
- Community membership at $250/month or $2,000/year.
Key Numbers:
- Masterclass revenue: $600,000 ([06:58])
- Community recurring revenue: $200,000 ARR ([07:26])
- Combined digital revenue: ~$800,000
- Facebook lead acquisition: ~$3/lead ([05:05])
Flywheel Effect:
- Automated onboarding, community feeds course, Isaac tells community members' stories as X threads, which drive more leads and create a virtuous loop.
“The members in my community, the recurring revenue community, which are super high value - I get to coach them, learn from them... pick the best stories, share those as threads which generate a ton because I'm the expert now” – Isaac French ([09:03])

Mapping Future Paths: Four Business Options ([10:09]–[19:18])

Nathan and Isaac brainstorm and dissect four main opportunities:

Content Agency:
- Replicating the social/content results Isaac achieved for Live Oak Lake for other property owners, potentially with a 50/50 split with agency partners.
- Direct application of flywheels: teach owners, consult, then offer a done-for-you service as they realize the workload.
SaaS Product:
- Creating a “Shopify for experiential hospitality” (direct booking engine software).
- High long-term enterprise value route, but requires focus, domain mastery, and willingness to play the long game (5–10 years).
“If you came to me and said, hey, the thing that I am optimizing for most is enterprise value...it's for me it would be the next property or it'd be software.” — Nathan Barry ([23:46])
New Property Development:
- Building another Live Oak Lake (but perhaps smaller, in the 1–3 unit range for manageability and story appeal).
- Access to capital is strong, but Isaac prioritizes intentional scaling and maintaining quality.
Scaling Content:
- Going all-in on YouTube, potentially starting a podcast, and focusing on storytelling to expand the audience and amplify personal brand equity.
“That’s kind of my dream, is to grow a really nice YouTube audience...” – Isaac French ([19:18])

Decision-Making Criteria & Optimizing for Quality of Life ([19:50]–[26:21])

What To Optimize For?
- Not just money: “I want both [cashflow and equity]. I really want, like, I want 50/50. I want a nice lifestyle… and I want a nice nest egg that I can pass on.” — Isaac French ([22:01])
- Core values: quality of life, small team, engaging work, travel, faith, family.
- Avoiding overexpansion and burnout; preferring a hands-on, high-integrity approach.
Two Buckets: Cashflow vs. Enterprise Value
- Nathan emphasizes distinguishing between short-term profits and long-term value.
  
  “One mistake that I see a lot of creators make is they don’t think about the difference. They don’t think of those two buckets.” — Nathan Barry ([21:01])
Small Team Preference:
- Isaac resists the idea of building a large staff, preferring either solo or a tiny, high-performance team.
“Do not want a big team...the thought of managing a team or dealing with HR...I'm allergic to that.” – Isaac French ([30:10])

Analyzing Each Option in Depth ([26:21]–[43:16])

SaaS Off the Table (For Now):
- Software only makes sense if you go “all-in” and have a world-class operator as a partner; not a half-hearted or side project.
- Nathan’s advice: Be realistic about the learning curve and commitment.
  
  “Software is going to have this very, very slow ramp up...but you should go in with it being that difficult, long game.” — Nathan Barry ([31:39])
Agency Option:
- Valid, but must find the ideal partner/operator; explore the space, take calls, don’t commit hastily.
- Passive strategy: collect ideas, interview prospects, prepare, but don’t rush.
  
  “You can say, hey, over the next year I'm going to meet 10 to 20 people who might be this operator and...I'll start to know what it takes to build a world class agency.” – Nathan Barry ([35:34])
Next Property:
- Doing a small, high-quality, story-driven project (1–3 units) maximizes audience and community impact while controlling risk.
- Encourages inspiring newcomers and creating approachable, replicable models.
  
  “Three units is like micro resort...some exponential difference where you create, like, a communal setting...a lot more approachable in terms of finances and just overall work than seven.” — Isaac French ([40:26])
Content Scaling:
- Primary goal: Mastering storytelling via YouTube and possibly podcasting.
- Audience as the real form of “equity.”
- Success means greater impact, invitations, cashflow potential, and audience leverage.
  
  “I want to create films that move people.” — Isaac French ([49:09])

Isaac's Personal Philosophy and Guardrails ([51:18]–[62:06])

Money as a Means, Not the End:
- Financial security is desirable, but the main focus is impact, joy, and enrichment.
  
  "I've found so much value in...connecting with an audience, telling stories, living a life that I'm privileged to live. And I just don't want to mess that up." — Isaac French ([51:19])
Personal Brand as Long-Term Asset:
- Audience value can be “locked” but has compounding utility: launches, investments, influence.
  
  “The most valuable thing you have is your reputation...your ability to raise millions of capital if you want it...to sell a digital product, to create any of these things in the future.” — Isaac French ([41:37])
Being Recognizable, But Not Celebrity:
- Sweet spot: Respected and recognized by the community that matters, but not mainstream “celebrity”.
- Draws inspiration from his grandfather—master craftsman, private integrity.
  
  “I want to be famous enough where I can talk to anyone I want, but people don't really know me.” — Isaac French ([58:14])
  
  “He never spent a dime on marketing, but just basically put his all into it. Cared for each project, each customer like they were his own family...” — Isaac French ([61:12])

Actionable Plan & Roadmap ([53:59]–[64:06])

What Nathan Recommends:

Agency: Put on passive mode; start collecting data, have exploratory conversations, but don't commit yet.
SaaS: Off the table for 3–5 years; table until there’s time, capital, and ideal cofounder.
Next Property: Go all-in on a small (1–3 unit) project, with a focus on storytelling; quality > scale.
Scaling Content: Invest significant time & money into mastering visual storytelling for YouTube (and possibly podcasting), focusing on skill development over audience size or immediate ROI.
Newsletter: Continue building the email list as a central asset.
Maintain optionality and low overhead: All choices maintain flexibility for larger moves down the line.

“If I were in your position...the next property, you go all in on a small three unit. The storytelling is perfect, and you're really optimizing for the story and the equity value through the audience...And then I would set aside a certain amount of money from the masterclass...and invest 100, $200,000 a year into...mastering storytelling and growing the YouTube audience.” — Nathan Barry ([53:59])

Memorable Quotes & Moments

On making business choices:

“The difference between successful people and really successful people is that really successful people say no to almost everything.” — Nathan Barry quoting Warren Buffett ([00:32], [10:54])
On the value of community:

“It's the best feeling in the world that I have a small but valuable audience that can make a meaningful difference in these people's lives.” — Isaac French ([20:16])
On long-term planning and personal happiness:

"I love connecting with people. That's why I love this community so much. Like minded people that care about design. And I love traveling and seeing new places, meeting new people..." — Isaac French ([19:50])

Key Timestamps

[01:16] Isaac’s journey from real estate to digital business
[03:21] Masterclass sales funnel & automation
[06:58] Digital product revenue numbers
[09:03–10:09] Community-content flywheel effect
[11:21] Exploring business options: Content agency, SaaS, more properties, content scaling
[19:50] Isaac’s core decision criteria: optimizing for quality of life, community, and fulfillment
[23:46] Nathan breaks down value: cashflow vs. equity
[31:39] SaaS as a path—how hard is it really?
[36:05] Agency partnerships and choosing the right operator
[41:14–41:37] Micro-resort idea: impact and approachability over sheer scale
[49:09] Mastering storytelling as self-realization and business multiplier
[58:14] Finding the right level of visibility and fame
[61:12] Isaac’s grandfather: legacy and values

Final Takeaways

Choose business opportunities that align with your values, desired lifestyle, and skills you’re eager to master—not just with financial upside.
Maximize leverage with flywheels: community, content, and personal brand feed each other for compounding results.
Be intentional with scaling: Small teams can create outsized results when backed by the right frameworks and clear decision filters.
Prioritize learning, storytelling, and community-building, as these build lasting enterprise value and preserve optionality.
Actively say “no” to maintain focus, bandwidth, and quality in both work and life.

Where to Find Isaac French

Instagram & Twitter: @isaacfrench_
Newsletter: isaacjfrench.com

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How to Pick a Business You ACTUALLY Enjoy (In 64 Mins) | 065

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Summary

Episode Overview

Key Discussion Points & Insights

Isaac's Journey & Current Business Structure ([01:16]–[10:09])

Mapping Future Paths: Four Business Options ([10:09]–[19:18])

Decision-Making Criteria & Optimizing for Quality of Life ([19:50]–[26:21])

Analyzing Each Option in Depth ([26:21]–[43:16])

Isaac's Personal Philosophy and Guardrails ([51:18]–[62:06])

Actionable Plan & Roadmap ([53:59]–[64:06])

Memorable Quotes & Moments

Key Timestamps

Final Takeaways

Where to Find Isaac French

Summary

Episode Overview

Key Discussion Points & Insights

Isaac's Journey & Current Business Structure ([01:16]–[10:09])

Mapping Future Paths: Four Business Options ([10:09]–[19:18])

Decision-Making Criteria & Optimizing for Quality of Life ([19:50]–[26:21])

Analyzing Each Option in Depth ([26:21]–[43:16])

Isaac's Personal Philosophy and Guardrails ([51:18]–[62:06])

Actionable Plan & Roadmap ([53:59]–[64:06])

Memorable Quotes & Moments

Key Timestamps

Final Takeaways

Where to Find Isaac French