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The Founder's Journey Podcast
Greg Moran
103 episodes
4 months ago
Telling the stories of startup founders and creators and their unique journey. Each episode features actionable tips, practical advice and inspirational insight.
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Entrepreneurship
Personal Journals,
Business,
Society & Culture
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All content for The Founder's Journey Podcast is the property of Greg Moran and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
Telling the stories of startup founders and creators and their unique journey. Each episode features actionable tips, practical advice and inspirational insight.
Show more...
Entrepreneurship
Personal Journals,
Business,
Society & Culture
Episodes (20/103)
The Founder's Journey Podcast
How 8 Coaches Made Me a Better Founder, Partner & Leader

Welcome to Founders Collective, where we bring you the most inspiring stories from trailblazing Founders. Most founders struggle with loneliness and decision-making. But what if you had a personal board of advisors just like a company? In this episode, we dive deep into how top entrepreneurs structure their lives using coaches, mentors, and consultants to make smarter, faster decisions.
00:00 - The Reality of Founder Loneliness
00:31 - How I Built a Personal Board of 8+ Advisors
01:07 - Why This Approach is Rare in Business
01:33 - Adding a 9th Coach for Relationships & Marriage
01:48 - How My Life Organization Works Like a Company
02:30 - Balancing Business, Health, and Relationships
02:49 - Decision-Making with Multiple Experts
03:26 - The Power of Combining Different Perspectives
04:12 - Founders Struggle to Ask for Help
05:10 - Shifting from a Solo Mindset to a Team Mindset
06:14 - Early Struggles and the Importance of Guidance
07:09 - Lessons from Scaling a Multi-Million Dollar Business
07:47 - Building a Support System for Life & Business
08:04 - Final Thoughts: Why Every Founder Needs a Team

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8 months ago
8 minutes

The Founder's Journey Podcast
I Lost $750K And Learned A VALUABLE Lesson

Welcome to Founders Collective, where we bring you the most inspiring stories from trailblazing Founders. Imagine signing a $750K investment deal, celebrating with your team… only for the money to never arrive. This is the true story of how we almost lost everything during the holiday season when an investor completely vanished.

00:00 – The Scariest Day as a Founder
00:21 – How I Perform Under Pressure
01:00 – Our Startup’s Near-Death Experience
02:21 – The Investor That Vanished
03:40 – The Financial Crisis Hits
04:53 – How We Handled It & Lessons Learned

 Subscribe to The Founder’s Journey Newsletter and never miss an episode!  Our subscribers receive exclusive content, too! – https://www.thefounderscollective.com/

📌 Connect with us:
Website: https://www.thefounderscollective.com/
LinkedIn: https://www.linkedin.com/in/gregmoran/ 
Instagram: https://www.instagram.com/t.h.e._founders_collective/ 


#startup #entrepreneur #businessfailures #founderstory #startuplife #VALUABLELesson #ILost$750K

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9 months ago
6 minutes

The Founder's Journey Podcast
The Biggest Hiring Mistakes That Can Destroy Your Startup!

Welcome to Founders Collective, where we bring you the most inspiring stories from trailblazing Founders. Hiring the right people is one of the toughest challenges founders face. But what happens when you make the wrong hire?

In this episode, we dive deep into the biggest hiring mistakes founders make and the emotional and business consequences of keeping the wrong person on board for too long.

We share real-world lessons from founders who’ve been there, covering: 
✅ Why recruiting is one of the hardest parts of running a business
✅ How hiring mistakes impact company culture & performance
✅ The cost of keeping the wrong person for too long
✅ Why employees don’t speak up about bad hires
✅ How to hire slow & fire fast (without regret)

00:00 – The biggest hiring mistake founders make
00:36 – Why recruiting is emotionally difficult
01:16 – A real founder’s hiring regret
02:37 – The impact of hiring the wrong person
05:01 – Why teams don’t speak up about bad hires
06:21 – The problem with desperation hires
07:32 – Best advice: Hire slow, fire fast

📌 Subscribe to The Founder’s Journey Newsletter and never miss an episode!  Our subscribers receive exclusive content, too! – https://www.thefounderscollective.com/

📌 Connect with us:
Website: https://www.thefounderscollective.com/
LinkedIn: https://www.linkedin.com/in/gregmoran/ 
Instagram: https://www.instagram.com/t.h.e._founders_collective/ 

#StartupLessons #HiringMistakes #Entrepreneurship #Leadership #BusinessGrowth #TheBiggestHiringMistakes #HiringMistakes #Startup

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9 months ago
8 minutes

The Founder's Journey Podcast
Unlock the Secret to Demand Generation Success

Welcome to Founders Collective, where we bring you the most inspiring stories from trailblazing Founders. Unlock the Secret to Demand Generation Success. Are you launching a business and unsure whether to focus on branding or demand generation? In this episode, we break down why demand generation should come first, how to test market responses, and why early-stage businesses need a strong foundation before investing in big-brand strategies. Learn from real startup stories including a costly NASCAR sponsorship mistake!

00:00 - Where Should Startups Begin? (Branding vs. Demand Generation)
00:20 - Why Demand Generation Comes First (Testing market response)
00:43 - How Demand Gen Becomes Part of Your Brand
01:07 - The Risk of Branding Without a Call-to-Action
01:28 - What to Prioritize in Demand Generation
01:52 - A Costly Startup Mistake: NASCAR Sponsorship Gone Wrong
02:39 - Big vs. Small Marketing Budgets: What Works?
03:24 - How Market Changes Impact Startup Growth Strategies
04:02 - Finding the Right People for Demand Generation
04:19 - What Makes a Great Demand Gen Marketer? (Key skills)
05:02 - The Importance of SEO, Analytics & CRM in Marketing
05:22 - Why Startups Need Data-Driven Decision Making


#MarketingStrategy #StartupGrowth #DemandGeneration #B2BMarketing #SEO #BrandingTips #Entrepreneurship #SmallBusiness #DemandGeneration #UnlocktheSecret #GenerationSuccess

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9 months ago
5 minutes

The Founder's Journey Podcast
Discover the GOLDMINE Hidden in Your Customer Data!
9 months ago
8 minutes

The Founder's Journey Podcast
The Hard Truth About Doing It Alone as a Founder

Welcome to Founders Collective, where we bring you the most inspiring stories from trailblazing Founders. In this episode of Founders Collective, we explore The Hard Truth About Doing It Alone as a Founder and the essential qualities that make great leaders stand out: empathy, self-awareness, and resilience. Join us for an honest discussion about overcoming imposter syndrome, navigating the challenges of the music industry, and creating a support system for success. Learn three key lessons from a 21-year entrepreneurial journey: the importance of teamwork, financial literacy, and showing grace. This episode is packed with insights for founders and creatives alike.


00:00 - Intro: Empathy and self-awareness in leadership
00:20 - Understanding your unique journey and making choices
01:02 - Battling imposter syndrome as a founder
02:22 - Working with some of the most famous people in the world
03:42 - The importance of creating a support system
04:06 - Three biggest lessons: teamwork, financial literacy, and grace

📌 Subscribe to The Founder’s Journey Newsletter and never miss an episode!  Our subscribers receive exclusive content, too! – https://www.thefounderscollective.com/

📌 Connect with us:
Website: https://www.thefounderscollective.com/
LinkedIn: https://www.linkedin.com/in/gregmoran/ 
Instagram: https://www.instagram.com/t.h.e._founders_collective/ 

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9 months ago
5 minutes

The Founder's Journey Podcast
My Journey from Homelessness to Hosting Justin Bieber and Mariah Carey

Don't make these studio building mistakes! Learn from the Founder’s Journey, avoid challenges, and persevere to reach your vision.
Welcome to Founders Collective, where we bring you the most inspiring stories from trailblazing Founders. In this episode, we dive deep into the journey of the founder of Lounge Studios—a story of unmatched perseverance, sacrifice, and vision. Starting in New York City with just $50, this founder faced countless challenges, including homelessness, to pursue a dream of building a creative haven for some of the biggest names in the music industry.

From carrying drywall on a train to constructing the studio by hand, every step of the process was marked by determination and resourcefulness. Today, Lounge Studios stands as a testament to resilience, hosting legends like Justin Bieber, Mariah Carey, and Ed Sheeran.

If you've ever wondered what it takes to transform a vision into reality or to overcome extraordinary obstacles, this is a story you don't want to miss. Join us as we celebrate the power of dreaming big and staying true to your goals, no matter how difficult the road.

Timestamps:
00:00 - Intro: Building Lounge Studios from nothing
00:21 - Moving to New York City with $50
00:44 - Early struggles and Bronx living conditions
01:18 - Working with at-risk youth and saving for a studio
01:41 - Building the studio by hand with limited resources
02:17 - Hosting music industry legends like Justin Bieber and Mariah Carey
03:08 - Choosing sacrifice to pursue long-term success
03:47 - The personal decision to embrace homelessness for a dream
04:11 - Creative ways to survive and build on a tight budget
05:11 - Reflecting on the 12-year journey and the lessons learned

📌 Subscribe to The Founder’s Journey Newsletter and never miss an episode!  Our subscribers receive exclusive content, too! – https://www.thefounderscollective.com/

📌 Connect with us:
Website: www.TheFoundersJourneyPodcast.com 
LinkedIn: https://www.linkedin.com/in/gregmoran/ 
Instagram: https://www.instagram.com/t.h.e._founders_collective/ 

#EntrepreneurialSuccessStories, #BuildingLoungeStudios, #MusicIndustryLegends, #FromHomeless, #InspirationalEntrepreneurialJourney, #StartupSacrifices, #HostingJustinBieber, #CreativeBusinessSuccess, #MyJourney # MariahCarey

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9 months ago
5 minutes

The Founder's Journey Podcast
How the FBI Became My First Major Client

Discover how a young entrepreneur’s technical expertise and perseverance landed the FBI as his very first major client. From writing software articles in niche magazines to presenting at conferences, this founder shares the pivotal moment that shaped his company’s future.

Learn how navigating early challenges, including disorganization and tight deadlines, led to a successful project and ultimately, a thriving business. This story is packed with lessons on resilience, taking risks, and recognizing opportunities in unexpected places.

💡 What You’ll Learn:
How to turn conference opportunities into business deals
Lessons from working with high-pressure government projects
Overcoming early-stage challenges as a founder
Building a successful business through perseverance

Timestamps
0:00 – 0:34 | Early struggles in pre-internet marketing
0:35 – 0:59 | First big break with a government client
1:00 – 1:35 | Delivering a successful project and lessons learned
1:36 – 2:16 | Near payroll disaster and risky financial decisions
2:17 – 3:18 | Using unconventional methods to stay afloat
3:19 – 4:16 | Struggles with micromanagement and burnout
4:17 – 5:18 | Transitioning leadership and delegating responsibilities
5:19 – 6:00 | Key lessons on growth, delegation, and leadership

What’s the toughest decision you’ve made as a leader? Share your story in the comments below, and don’t forget to like, subscribe, and hit the bell for more inspiring founder journeys.

Free Resource: Download our white paper on scaling sustainable businesses: Understanding the Behavioral DNA of Successful Founders

Connect with Enduring Ventures for more insights on scaling and long-term business success: https://emep.io/

#startupsuccess #entrepreneurship #foundersjourney #FBIClientStory
#businessgrowth #governmentcontracts #LandingMajorClients
#networkingtips #startuplessons  
#buildingabusiness #successstories #entrepreneurmotivation #businessjourney  #overcomingchallenges #resilienceinbusiness 

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9 months ago
5 minutes

The Founder's Journey Podcast
Hard Times, Big Lessons: Overcoming Financial Disaster

What happens when a single mistake costs you $4 million? This is the story of Overcoming Financial Disasters, and the power of a supportive partnership.
In this emotional episode of The Founders Journey Podcast, a founder shares how a $4 million mistake nearly derailed his life and career, and how his wife’s unwavering support helped him rebuild. Learn how resilience, sacrifice, and alignment in values can make or break a partnership, whether in business or marriage.

Key Topics Covered:
- Learning from a $4 million mistake
- The importance of alignment in marriage and business
- Overcoming financial disasters as a team
- Valuing experiences over material possessions
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Timestamps
0:00 – 0:33 | The $4 million mistake and Lyla’s reaction
0:34 – 1:12 | Sacrifices and struggles in the early days
1:13 – 2:00 | Valuing experiences over material possessions
2:01 – 2:56 | The importance of alignment in marriage and business
2:57 – 3:48 | Raising a family while building a company
3:49 – 5:12 | Balancing temperaments in a partnership
5:13 – 6:00 | Lessons learned: resilience, trust, and support
---------------------------------------------------------------------------------------------------------------------------
Free Resource: Download our white paper on scaling sustainable businesses: Understanding the Behavioral DNA of Successful Founders

Connect with Enduring Ventures for more insights on scaling and long-term business success: https://emep.io/
---------------------------------------------------------------------------------------------------------------------------
What’s the biggest challenge you’ve faced in your entrepreneurial journey? Share your story in the comments, and don’t forget to like, subscribe, and turn on notifications for more inspiring stories.

#resilienceinbusiness   #EntrepreneurshipLessons #foundersjourney   #SacrificeAndSuccess #supportivepartnership   #financialdisaster

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10 months ago
5 minutes

The Founder's Journey Podcast
The Day My Life Changed Forever: The Power of Second Chances! | TFJP 95

What happens when life gives you the gift of second chances? Chris Kaplan shares his powerful story of resilience, transformation, and the power of real connections.
In this moving episode of The Founders Journey Podcast, Chris Kaplan opens up about his journey from addiction and incarceration to sobriety and success. Through mentorship, Ironman training, and the power of connection, Chris shares how he turned his life around and embraced a life of purpose, real relationships, and growth.

Key Takeaways:
How addiction led to transformation and connection
The role of real relationships in recovery
Building a meaningful life after second chances
Lessons in resilience, gratitude, and purpose
---------------------------------------------------------------------------------------------------------------------------
Timestamps
0:00 – 0:22 | Chris Kaplan introduces his story
0:23 – 0:46 | Childhood struggles and early challenges
0:47 – 1:29 | Sobriety at 17 and challenges in high school
1:30 – 2:25 | Facing incarceration and turning to faith
2:26 – 3:15 | The moment of transformation in jail
3:16 – 4:02 | Building a new life: Treatment, education, and career
4:03 – 5:16 | Gratitude for mentors and second chances
5:17 – 6:08 | The power of connection in sobriety and life
6:09 – 6:38 | Final thoughts: Real relationships and purpose
---------------------------------------------------------------------------------------------------------------------------
Free Resource: Download our white paper on scaling sustainable businesses: Understanding the Behavioral DNA of Successful Founders

Connect with Enduring Ventures for more insights on scaling and long-term business success: https://emep.io/
---------------------------------------------------------------------------------------------------------------------------#transformationstory  #sobrietyjourney  #foundersjourney  #resilience  
#powerofconnections  #secondchances  #redemption  #resiliance

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10 months ago
6 minutes

The Founder's Journey Podcast
Hyperfocus for Founders: Lessons from 90 Days of Commitment | TFJP 94

Discover the lessons Kris learned through hyperfocus for founders, resilience, and committing to 90 days of challenge.

In this episode of The Founders Journey Podcast, Kris shares his story of building Criston Cole, balancing family, sobriety, and entrepreneurship. Learn how 90-day commitments, prioritization, and resilience can transform your life and business. From Ironman training to AA meetings, Chris shows how founders can overcome challenges and scale their companies sustainably.

Key Takeaways:
- How hyperfocus and prioritization help founders thrive
- Lessons from Ironman training applied to entrepreneurship
- The value of sticking to a goal for 90 days before reassessing
- Overcoming founder challenges with resilience and discipline
---------------------------------------------------------------------------------------------------------------------------
Timestamps
0:00 – 0:26 | Introduction: Chris’ journey balancing life and business
0:27 – 0:48 | Ironman training and the value of prioritization
0:49 – 1:17 | The importance of self-care for entrepreneurs
1:18 – 2:04 | Learning hyperfocus through trial and error
2:05 – 2:24 | How 90-day commitments lead to better results
2:25 – 3:06 | Sticking to goals versus giving up too early
3:07 – 3:48 | Overcoming the curse of overthinking as a founder
3:49 – 4:58 | Testing, failing, and learning through action
---------------------------------------------------------------------------------------------------------------------------
Free Resource: Download our white paper on scaling sustainable businesses: Understanding the Behavioral DNA of Successful Founders

Connect with Enduring Ventures for more insights on scaling and long-term business success: https://emep.io/
---------------------------------------------------------------------------------------------------------------------------

#Entrepreneurship #StartupSuccess #FounderResilience #PrioritizationTips
#90DayCommitment #Hyperfocus #Founders

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10 months ago
5 minutes

The Founder's Journey Podcast
The Role Of An Angel Investor: How To Add Value Beyond Capital | TFJP 93

Angel investing is so much more than writing a check. The best investors mentor, connect, and empower startups to thrive. Learn how you can add real value beyond capital.
Greg Moran from Evergreen Mountain Equity Partners shares the top ways angel investors can make a lasting impact on early-stage startups. From providing mentorship and opening key connections to talent acquisition and strategic guidance, Greg highlights how investors can help founders scale successfully and increase their investment ROI. Whether you're a new angel investor or a seasoned pro, these tips will help you become a truly valuable partner to startups.
How do you add value to the startups you invest in? Share your thoughts in the comments below! And don’t forget to like, subscribe, and hit the bell for more startup investing insights.
---------------------------------------------------------------------------------------------------------------------------
Key Takeaways:
- Why capital alone isn’t enough to support startups
- The power of mentorship, connections, and talent acquisition
- How strategic guidance and resilience help startups succeed
---------------------------------------------------------------------------------------------------------------------------
Timestamps
0:00 – 0:13 | Introduction: Adding Value as an Angel Investor
0:14 – 0:36 | Beyond the check: Why angel investors need to do more
0:37 – 1:21 | The impact of mentorship on startup success
1:22 – 2:25 | How engaged investors improve startup performance
2:26 – 3:54 | Mentorship tips: Regular check-ins and actionable advice
3:55 – 4:43 | Avoiding micromanagement as an investor
4:44 – 6:23 | Leveraging your network to open doors and drive growth
6:24 – 7:48 | Assisting with talent acquisition and building a team
7:49 – 9:23 | Providing strategic guidance for growth and scaling
9:24 – 12:02 | Encouraging resilience: Supporting founders through challenges
12:03 – 13:11 | Final thoughts: Why adding value matters for ROI and success
---------------------------------------------------------------------------------------------------------------------------
What do you think is the most impactful way angel investors can help startups succeed? Share your thoughts below!

Free Resource: Download our white paper on scaling sustainable businesses: Understanding the Behavioral DNA of Successful Founders

Connect with Enduring Ventures for more insights on scaling and long-term business success: https://emep.io/
---------------------------------------------------------------------------------------------------------------------------
#angelinvesting  #startupsuccess  #EarlyStageInvesting #foundersjourney 
#entrepreneurship #investorinsights   #businessgrowth 
#startupadvice

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10 months ago
13 minutes

The Founder's Journey Podcast
Understanding Startup Valuations: How to Determine a Fair Price Before Investing | TFJP 92

How do you value a startup?
Valuing startups is both an art and a science, especially for early-stage companies. In this episode of The Founders Journey Podcast, Greg Moran from Evergreen Mountain Equity Partners breaks down the most effective methods for assessing startup value. From Comparable Company Analysis (CCA) to the Berkus Method, Discounted Cash Flow (DCF), and Venture Capital Method, Greg explains how to evaluate potential investments and align with founders for sustainable growth.

💡 What You’ll Learn:
Why startup valuation is more about predicting future potential than current performance
The strengths and weaknesses of different valuation methods
How founder quality impacts valuation and long-term success
Tips for negotiating fair terms and avoiding common pitfalls
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📌 Timestamps:
0:00 – 0:28 | Introduction to Startup Valuation
Greg Moran introduces the topic of startup valuation and its challenges, especially for early-stage companies.
0:29 – 1:34 | Why Valuing Startups Is Difficult
Discussion of the subjective nature of early-stage valuations due to lack of revenue and stable cash flow.
1:35 – 2:28 | Aligning Founders and Investors
The importance of valuation in setting mutual expectations and enabling long-term growth.
2:29 – 3:37 | Comparable Company Analysis (CCA)
Explanation of the CCA method, its pros and cons, and tips for using it effectively.
3:38 – 5:01 | Berkus Method for Pre-Revenue Startups
How the Berkus Method assigns monetary value to factors like team quality, product rollout, and strategic relationships.
5:02 – 7:02 | Discounted Cash Flow (DCF) Method
Overview of DCF for later-stage startups, including its reliance on revenue projections and risk adjustment.
7:03 – 9:35 | Venture Capital (VC) Method
How the VC method calculates startup valuation based on potential exit value and target returns.
9:36 – 12:31 | The Role of Founder Quality in Valuation
Why founder traits like resilience, adaptability, and accountability significantly influence early-stage valuations.
12:32 – 14:18 | Tips for Negotiating Fair Valuations
Strategies for transparency, risk adjustments, and structuring deals with milestones or equity-based compensation.
14:19 – 15:53 |
Recap of valuation methods, importance of founder assessment, and invitation to connect with Evergreen Mountain Equity Partners.
---------------------------------------------------------------------------------------------------------------------------
Free Resource: Download our white paper on scaling sustainable businesses: Understanding the Behavioral DNA of Successful Founders

Connect with Enduring Ventures for more insights on scaling and long-term business success: https://emep.io/
---------------------------------------------------------------------------------------------------------------------------------------------------------------
#StartupValuation #AngelInvesting #BusinessGrowth #Entrepreneurship #StartupTips

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11 months ago
16 minutes

The Founder's Journey Podcast
Red Flags in Startup Due Diligence: What Angel Investors Should Watch Out For | TFJP 91

Welcome to the Founders Journey podcast! In this episode, Greg Moran of Evergreen Mountain Equity Partners breaks down the essentials of startup due diligence. Whether you're an angel investor or exploring the world of venture capital, this guide will help you identify red flags and make informed investment decisions.
------------------------------------------------------------------------------------------------------------------------------------------------------------------
Key Topics Covered:
:key: Importance of due diligence in startup investing
:female-technologist: Evaluating founders' qualities and potential
:chart_with_upwards_trend: Understanding product-market fit and customer retention
:moneybag: Financial projections and CAC-to-LTV ratio analysis
:earth_africa: Assessing market size and competition
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Timestamp Chapters:
0:00 - Welcome to the Founders Journey
Introduction to the podcast and its purpose.
0:10 - The Importance of Due Diligence
Overview of why due diligence is critical in angel investing.
0:30 - How to Conduct Due Diligence
Steps and strategies to identify red flags during the process.
0:53 - The Startup Investment Landscape
Statistics on success rates and the potential for high returns.
1:18 - Evaluating Startup Founders
Key traits of resilient, humble, and accountable founders.
2:20 - Product-Market Fit
Why it matters and metrics to assess it effectively.
3:55 - Financial Projections and Assumptions
Analyzing the realism behind financial forecasts.
5:03 - Customer Acquisition Cost vs. Lifetime Value
Understanding critical metrics for sustainable growth.
6:27 - Market and Competition Analysis
Assessing market size, competition, and differentiation.
10:18 - Recap: Key Areas of Due Diligence
Summary of the five essential areas and the disciplined approach needed.
10:40 - Call to Action
Encouragement to engage with the content, subscribe, and connect for more insights.------------------------------------------------------------------------------------------------------------------------------------------------------
Free Resource: Download our white paper on scaling sustainable businesses: Understanding the Behavioral DNA of Successful Founders

Connect with Enduring Ventures for more insights on scaling and long-term business success: https://emep.io/
------------------------------------------------------------------------------------------------------------------------------------------------------------------
:loudspeaker: Don’t forget to subscribe for more tips and strategies for successful startup investing! Hit the :bell: to get notified of our latest content.
Have questions or insights? Drop them in the comments below, and let’s chat!
#StartupInvesting #AngelInvesting #DueDiligence #VentureCapital #FoundersJourney

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11 months ago
11 minutes

The Founder's Journey Podcast
The Worst Startup Advice Ever with Scot Chisholm | TFJP 90

Is ‘Fail Fast’ the worst advice for startups?
In this episode of The Founders Journey Podcast, Greg Moran, Peter Dean, and Scot Chisholm (founder of Classy) dive deep into the myths surrounding popular startup advice like “fail fast” and “find a bigger market.” Scott shares hard-earned lessons from Classy’s journey, including the importance of aligning with the right investors, avoiding premature scaling, and building a sustainable business.

:bulb: What You’ll Learn:
- Why “fail fast” often leads to bad pivots
- How to align with investors who share your values
- The dangers of scaling too quickly
- Lessons from Classy’s path to becoming a unicorn
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:alarm_clock: Timestamps:0:00 - Introduction: Failing Fast Misunderstood
0:23 - What Pivoting Really Means
0:43 - Welcome to Founders Journey Podcast
0:57 - Reunion with Peter Dean
1:12 - Introducing Scott Chisholm, Founder of Classy
2:28 - Scott’s Journey: Classy’s Origins and Growth
4:00 - Challenges in Nonprofit Technology Adoption
6:00 - Private Equity Challenges and Lessons Learned
8:00 - Culture Shift and Boardroom Conflicts
10:33 - Rescuing the Company from Investor Issues
14:13 - Importance of Value Alignment with Investors
15:10 - Building Relationships with the Right Partners
17:00 - Worst Advice in Startups: Failing Fast Critiqued
20:48 - Why Founders Should Avoid Constant Pivoting
23:07 - Business with Friends: A Debate
26:15 - Focus on Core Markets First
29:00 - Shiny Object Syndrome in Hiring Experienced Executives
34:00 - Raising Capital: The Right Approach
38:10 - Transitioning from Bootstrapping to Spending Methodically
42:50 - Balancing Frugality with Scaling
46:00 - How to Reach and Work with Scott Chisholm
47:25 - Closing Remarks and Future Advice
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Free Resource: Download our white paper on scaling sustainable businesses: Understanding the Behavioral DNA of Successful Founders

Connect with Enduring Ventures for more insights on scaling and long-term business success: https://emep.io/

website link of the guest -  scotchisholm.com
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:movie_camera: Don’t miss these unfiltered startup insights and real-world advice from leaders who’ve been there.
:+1: Like this video? Share it with fellow founders and subscribe for more episodes of The Founders Journey Podcast!
#StartupAdvice #Entrepreneurship #FailFastMyths #BusinessGrowth #FoundersJourney

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11 months ago
49 minutes

The Founder's Journey Podcast
Diversifying Your Portfolio: Why Angels Should Invest Across Sectors And Stages | TFJP 89

Welcome to The Founders Journey Podcast, where we deliver inspiration and education for Founders by Founders.
In this episode, Greg Moran from Evergreen Mountain Equity Partners dives deep into one of the most effective strategies for managing risk in startup investing: diversification. Whether you're a seasoned angel investor or new to this asset class, you'll learn:

-  Why over 75% of venture-backed startups fail and how to protect your investments.
- How to diversify across sectors, stages, and geographies to balance risk and maximize returns.
- The importance of founder selection and the unique traits successful founders share.
- Insights into the Adaptive Innovator Founder Assessment Model developed by Evergreen Mountain.
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0:00 - Introduction
Welcome to The Founders Journey Podcast: Inspiration and education for Founders by Founders.
0:10 - Overview of Startup Investing Risks
Greg Moran introduces the topic of diversification as a key strategy for managing risks in startup investing.
0:29 - Importance of Diversification
Explanation of why startup investments carry unique risks and the role of diversification in mitigating them.
1:12 - How Angel Investors Should Diversify
Discussion on diversification across sectors, stages, and geographies to balance risks and maximize returns.
2:10 - High Failure Rates in Startups
Insights into research showing that over 75% of venture-backed startups fail and how diversification helps manage this.
2:34 - Sector Diversification
Examples of how investing in industries with unique growth cycles, like SaaS and healthcare tech, can create a safety net.
3:48 - Stage Diversification
Exploring the risk-return profiles of early, mid, and late-stage investments to stabilize portfolio returns.
4:32 - Geographic Diversification
The importance of investing globally, including regions like Southeast Asia, Latin America, and Europe, for better risk distribution.
6:01 - Founder Selection for Risk Management
Introduction to Evergreen Mountain’s proprietary founder assessment model and the four key traits of successful founders.
7:40 - Conclusion & Call to Action
Summarizing the benefits of diversification and founder selection. Encouraging viewers to like, subscribe, and download the free whitepaper for more insights.
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Free Resource: Download our white paper on scaling sustainable businesses: Understanding the Behavioral DNA of Successful Founders

Connect with Enduring Ventures for more insights on scaling and long-term business success: https://emep.io/
------------------------------------------------------------------------------------------------------------------------------------------------------------------
💡 Don't forget to like, subscribe, and hit the bell for updates on new content!
#StartupInvesting #AngelInvesting #Diversification #FoundersJourney #InvestSmart #WealthBuilding #VentureCapital

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11 months ago
8 minutes

The Founder's Journey Podcast
Breaking Free From The Founder's Fallacy: Practical Steps For Founders | TFJP 88

Breaking Free from Founder Burnout | Practical Strategies for Success
Struggling to balance your life as a founder? You're not alone.  In this episode of the Founders Journey Podcast, Greg Moran from Evergreen Mountain Equity Partners shares his personal story and actionable steps to overcome the Founder’s Fallacy, reduce anxiety, and build a sustainable, fulfilling life.

✨ What You’ll Learn:
- How to separate meta decisions from micro decisions to delegate effectively.
- Proven routines to manage anxiety and prevent burnout.
- The importance of creating an identity outside of your business.
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⏰ Timestamps: 0:00 - Welcome to the Founders Journey Podcast
0:10 - Breaking the Founder’s Fallacy
0:33 - Meta Decisions vs. Micro Decisions
1:24 - Managing Anxiety
2:15 - Building Daily Routines
3:04 - Finding Identity Beyond Work
4:12 - Final Thoughts
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Free Resource: Download our white paper on scaling sustainable businesses: Understanding the Behavioral DNA of Successful Founders

Connect with Enduring Ventures for more insights on scaling and long-term business success: https://emep.io/
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💬 Share Your Thoughts: What strategies have helped you as a founder? Comment below!
📢 Help Others: Share this video with someone who could benefit from it.

🌟 Join a community of founders learning to thrive beyond their business. Let’s grow together! 🚀

#FoundersJourney #FounderBurnout #DecisionMaking #FoundersFallacy #StartupAdvice #PersonalGrowthJourney #ProductivityHacks

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11 months ago
4 minutes

The Founder's Journey Podcast
The Key to Smooth Founder to CEO Transitions Done Right | TFJP 87

What does it take to transition from founder-led leadership to a second CEO?
In this episode of the Founders Journey Podcast, Peter Dean speaks with Matt Sharrers, author of The Second CEO, about the challenges and strategies for navigating leadership transitions. From cultural evolution to rebuilding leadership teams, Matt shares actionable insights for founders, investors, and second CEOs looking to ensure a smooth and successful transition.

:bulb: Key Topics Covered:
Why "bringing the band back together" doesn’t work
The emotional journey of stepping down as a founder
The “Transition Trifecta” for second CEOs
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0:00 - Intro: Starting a new journey with a second CEO
0:22 - Challenges in Leadership Transitions: Why bringing "the old team" might not work
1:15 - Founder Cultures: Balancing respect and evolution in leadership
2:10 - Guest Introduction: Peter Dean welcomes Matt, author of The Second CEO
4:09 - The Emotional Transition: Moving from CEO to Chairman
6:18 - Defining Success for Founders: Preparing for a seamless CEO transition
8:43 - Culture Shift Strategies: From startup mentality to scalable operations
11:56 - Maintaining Company Ethos: Avoiding conflict during leadership transitions
15:06 - Scaling Challenges: The importance of new leadership styles
18:22 - Measuring Success: How the first year sets the tone for a second CEO
22:26 - Common Pitfalls: Avoiding mismatched leadership approaches
27:46 - Case Studies: A success story and a failure example from leadership changes
30:00 - Key Takeaways: Humility, self-awareness, and asking for help
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Free Resource: Download our white paper on scaling sustainable businesses: Understanding the Behavioral DNA of Successful Founders

Connect with Enduring Ventures for more insights on scaling and long-term business success: https://emep.io/
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:movie_camera: Don’t miss these insights from Matt Sharrers and learn how to set up your business for growth beyond its founder.
:+1: Like this video? Share it with fellow entrepreneurs and subscribe for more episodes of the Founders Journey Podcast!

#SecondCEO #LeadershipTransition #FoundersJourney #BusinessLeadership #Entrepreneurship

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11 months ago
33 minutes

The Founder's Journey Podcast
How to Assess a Startup’s Potential: Key Metrics Every Angel Investor Should Know | TFJP 86

Want to succeed in angel investing?
In this episode of the Founders Journey podcast, Greg Moran from Evergreen Mountain Equity Partners shares the essential metrics and strategies every angel investor needs to know. Learn how to evaluate startups through key indicators like traction, customer acquisition cost (CAC), lifetime value (LTV), and runway.
But it’s not just about the numbers—Greg explains why founder selection is a crucial factor that can make or break a startup’s success. With insights from Evergreen Mountain’s proprietary founder assessment model, this video is a must-watch for anyone looking to navigate the high-risk, high-reward world of startup investing.

💡 What You’ll Learn:
The top metrics for evaluating startup potential
How to assess founder resilience and adaptability
Why traction and efficient growth matter in early-stage startups
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📌 Timestamps:
0:00 – Welcome to the Founders Journey podcast
0:25 – Why evaluating startups is critical for angel investing
1:21 – Key metric #1: Traction
3:17 – Key metric #2: CAC and LTV
6:11 – Key metric #3: Runway and burn rate
8:51 – The importance of founder selection
10:11 – Evergreen Mountain’s founder assessment model
11:12 – Summary: Metrics, founder qualities, and successful investing
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🎥 Don’t forget to:
👍 Like this video if it was helpful!
💬 Drop your questions about angel investing in the comments below.
🔔 Subscribe to stay updated with more insights from the Founders Journey series.

#AngelInvesting #StartupSuccess #FounderSelection #Entrepreneurship #StartupMetrics

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11 months ago
12 minutes

The Founder's Journey Podcast
Losing Control and Losing Identity: The Emotional Toll Post Exit | TFJP 85

What happens when your identity as a founder becomes your entire life?
In part two of our three-part series on The Founders Fallacy, Greg Moran explores the deep connection between a founder’s identity and their need for control. After exiting his business, Greg shares how he faced emptiness, anxiety, and challenges in personal relationships—all tied to losing his "founder" identity.

This candid discussion offers valuable insights for entrepreneurs at any stage, whether you're just starting or considering an exit. Discover practical tips to build balance, find purpose beyond work, and avoid the emotional toll of tying your identity solely to your business.
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Timestamps:
0:00 – Introduction: The Founders Fallacy Part 2
0:21 – How founder identity ties into control
0:42 – The emptiness after exiting a business
1:26 – Struggles with personal relationships and mental health
2:26 – Finding purpose beyond your business
3:08 – Practical tips to start balancing life and work
3:55 – Preview of Part 3 and closing thoughts
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Free Resource: Download our white paper on scaling sustainable businesses: Understanding the Behavioral DNA of Successful Founders

Connect with Enduring Ventures for more insights on scaling and long-term business success: https://emep.io/
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Key Takeaways:
Why founders struggle to let go of control and identity after an exit
The impact on mental health, relationships, and personal growth
How to start building a balanced life beyond business

:speech_balloon: Does this resonate with you? Share your thoughts in the comments—we’d love to hear your story!
:bell: Subscribe to catch the next episode, where Greg shares actionable strategies for managing anxiety and breaking free from The Founders Fallacy.

#FoundersFallacy #Entrepreneurship #WorkLifeBalance #MentalHealthForFounders #LifeBeyondBusiness

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11 months ago
4 minutes

The Founder's Journey Podcast
Telling the stories of startup founders and creators and their unique journey. Each episode features actionable tips, practical advice and inspirational insight.