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Diehard Entrepreneur Stories

Diehard Entrepreneur Stories

Di: Devin Ramos
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Hi, I’m Devin Ramos, and welcome to Diehard Entrepreneur Stories—a podcast built for entrepreneurs who won’t settle, who fight through the tough times, and know there’s something extraordinary inside, waiting to be unleashed. 💪 On this podcast, I have the privilege of interviewing countless entrepreneurs, and witnessing the relentless grit it takes to succeed. I sit down with those who’ve been in the trenches, faced setbacks, and came out the other side. Together we extract the lessons that can help you do the same. I started this podcast to share the raw, unfiltered stories and lessons learned of entrepreneurs who faced challenges and still came out on top.


You’ll hear from incredible entrepreneurs 👩🏻‍💼👨🏻‍💼 like a blind and deaf entrepreneur who survived a devastating explosion in the military then went on to build a successful confectionary business 💼. You’ll hear stories from six-figure earners who quit their corporate jobs to chase their passion in real estate 🏡 and then gained time freedom. These are just a couple inspiring stories you’ll hear of entrepreneurs breaking boundaries and overcoming life-altering events. I created this podcast to share the raw, unfiltered stories of these entrepreneurs who faced challenges and still came out on top.


I believe every one of us carries a purpose deep inside, even if we're not sure how to pursue it or what it looks like. Together, we’ll awaken that purpose inside you, learn how to cultivate it 🌱, and share stories and lessons learned of those that’ve proved anything is possible when you refuse to quit.


Success isn’t handed to anyone. It’s earned through work.

⚡️Tune in to Diehard Entrepreneur Stories and discover how others have turned hard work into legacy.


I’m on a MISSION to help entrepreneurs create IMPACT.

Get on board at: 🤝 www.devinramos.com


⚡ Let's stay in touch:

Instagram | Facebook | Youtube | LinkedIn


#diehardentrepreneur #businessstrategy #entrepreneurjourney #resilienceinbusiness #growthmindset #realentrepreneurstories #scalingbusiness #expertinterviews #actionableadvice #entrepreneurshiptruths #successmindset #highperformancehabits #entrepreneurlifestyle #buildingwealth #veteranentrepreneurs #businessleaders #entrepreneurpodcast #forwardfactor #devinramos

Hosted on Acast. See acast.com/privacy for more information.

Devin Ramos
Economia Finanza personale Gestione e leadership Leadership
  • The End of Diehard Entrepreneur Stories: Why I'm Choosing Focus over Everything | EP52
    Oct 15 2025

    This is the most important message I've ever recorded.


    In this final episode of Diehard Entrepreneur Stories, I share a decision I've been wrestling with and the powerful lesson behind it: Exponential growth is only possible through ruthless focus and deliberate elimination.


    This isn't about quitting—it’s about pruning. Just like in business, when you cut back, you create the space for deeper roots and stronger growth.

    I walk you through my personal journey, explaining why I'm winding down this beloved podcast to concentrate fully on scaling my businesses, Forward Factor and Made in America. This choice wasn't easy, but it's a necessary step in practicing what I preach.


    If this show has meant anything to you, let it remind you: Diehard Entrepreneurs aren't the ones who do everything. They're the ones who stay relentless about what matters most.


    Listen now for the challenge that will help you identify the one thing you need to prune to unlock your next level of growth.

    I’m on a MISSION to help entrepreneurs build strong, successful businesses. Get on board at: 🤝

    https://www.devinramos.com

    TIMESTAMPS

    00:00 – The Most Important Episode I’ve Recorded

    00:12 – Exponential Growth Comes from Focus and Elimination

    01:04 – The Mission of Diehard Entrepreneur Stories

    01:46 – Why My Focus Became Diluted

    02:11 – Focus Comes From Within

    02:31 – The Tough Choice: Winding Down the Podcast

    02:43 – This Isn't Quitting: It's Pruning

    02:54 – Where My Content and Impact are Moving Next

    03:17 – The Simple Challenge to Unlock Your Growth

    03:40 – Recap: Relentless on What Matters Most

    03:59 – Thank You for This Chapter

    🎬Watch this on Youtube:

    https://youtu.be/bPPhJ-GTKB8


    ⚡ Let's stay in touch:

    Instagram:

    https://www.instagram.com/devinramos/

    Facebook:

    https://www.facebook.com/devinjramos035/

    LinkedIn:

    https://www.linkedin.com/in/devin-ramos-602a811ab


    🎬 Produced by:

    https://daretopodcast.com/

    #FocusAndClarity #PruningForGrowth #Entrepreneurship #BusinessFocus #RuthlessElimination #ExponentialGrowth #BusinessStrategy #MakingToughDecisions #FinalEpisode #DiehardEntrepreneurStories #ScaleUp #ProductivityHacks #BusinessPodcast #DevinRamos #EntrepreneurStories #Motivation #MindsetMatters #Leadership #BusinessTips #forwardfactor

    Hosted on Acast. See acast.com/privacy for more information.

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    4 min
  • Flips Out, Funds In: Mike Simmons’ Pivot to Lending Millions | Ep 51
    Oct 8 2025

    What does it take to build a thriving 7-figure real estate business and successfully pivot into hard money lending?


    In this episode of Diehard Entrepreneur Stories, Devin Ramos talks with Mike Simmons, who grew a successful house flipping and wholesaling business over a decade before co-founding Express Hard Money. Mike shares his journey from corporate jobs to real estate entrepreneurship, the challenges of building scalable systems, and winning a 7-figure flipping contest in 10 months.


    We discuss the shift from hands-on flipping to wholesaling for faster growth, managing sales teams, and navigating the ups and downs of marketing strategies—including overcoming the COVID-19 direct mail collapse.


    Mike also dives deep into starting his lending company, how real estate experience shapes his approach, and the nuances of raising capital from family offices versus high net worth individuals. He reveals the importance of smooth customer experience over low interest rates, and lessons learned about fund administration and institutional investor expectations.


    Entrepreneurs, real estate investors, and leaders will gain insights on resilience, scaling businesses, and pivoting to new growth opportunities.


    Connect with Mike Simmons:

    Website: mikesimmons.com

    Express Hard Money: expresshardmoney.com

    TIMESTAMPS

    00:00 Introduction

    06:00 From UPS and corporate to real estate entrepreneurship

    14:00 Early flipping struggles and pivot to wholesaling

    25:20 Losing contractor and realtor, discovering wholesaling potential

    30:00 Marketing scale-up and hiring sales team

    32:50 Joining Seven Figure Flipping and rapid growth to $1M

    36:00 Challenges managing sales team and business systems

    38:30 COVID-19 impact on direct mail marketing and recovery with PPC

    42:00 Maintaining $1M revenue as a lifestyle business, scaling again in 2023-24

    44:00 Managing partner dynamics and eventual amicable buyout

    56:30 Launching Express Hard Money lending company

    58:30 Lending niche insights: real estate experience benefits

    1:01:00 Raising capital from family offices vs. high net worth individuals

    1:14:30 Building proper fund administration and data room setup

    1:18:00 Importance of professionalism and patience with institutional investors

    1:22:00 Closing thoughts and where to find Mike Simmons online

    🎬Watch this on Youtube:

    https://youtu.be/I-2RIR5WRQ4

    ⚡ Let's stay in touch:

    Instagram: https://www.instagram.com/devinramos/

    Facebook: https://www.facebook.com/devinjramos035/

    LinkedIn: https://www.linkedin.com/in/devin-ramos-602a811ab

    🎬 Produced by: https://daretopodcast.com/

    #RealEstate #HardMoneyLending #Entrepreneurship #RealEstateInvesting #HouseFlipping #Wholesaling #BusinessGrowth #InvestorTips #PassiveIncome #StartupLife #SmallBusiness #Leadership #DevInRamos #ForwardFactor #DiehardEntrepreneur

    Hosted on Acast. See acast.com/privacy for more information.

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    1 ora e 23 min
  • The Real Cost of Marketing in 2025 and How We're Cutting It | EP50
    Oct 1 2025

    Feeling like your marketing costs are rising but sales are dropping in 2025?


    In this video, I share real stories from my real estate and cleaning businesses about how we handle higher marketing expenses, fewer quality leads, and lower sales conversions.


    Learn simple ways to save money on marketing like using cheaper direct mail options, improving online ads, and focusing only on what works best.

    I also explain how to find better customers faster and why cutting your marketing budget can actually hurt your business.


    If you want easy-to-follow marketing tips to grow your small business, get more leads, and improve profits, this video is for you.


    Subscribe and join me on the journey to smarter marketing and business success!


    Website: 🤝

    https://www.devinramos.com

    TIMESTAMPS:

    00:00 - Introduction

    00:45 - Host Introduction and Topic Setup

    01:09 - Overview of Business Models (Real Estate & Cleaning)

    02:12 - Marketing Cost Increase and Impact

    03:54 - Lead Quality and Conversion Decline Effects

    06:41 - Strategies to Reduce Marketing Costs

    10:03 - Exploring Alternative Direct Mail Methods

    11:56 - Agency Outsourcing and SEO Efforts for Cost Efficiency

    13:28 - Focusing on Effective Marketing Channels and Cutting Ineffective Ones

    16:40 - Addressing Lower Conversion Rates and Lead Screening Improvements

    20:03 - Targeting the Right Audience and Refining Messaging

    🎬Watch this on Youtube:

    https://youtu.be/ponpFA6UPUQ

    ⚡ Let's stay in touch:

    Instagram:

    https://www.instagram.com/devinramos/

    Facebook:

    https://www.facebook.com/devinjramos035/

    LinkedIn:

    https://www.linkedin.com/in/devin-ramos-602a811ab

    🎬Produced by:

    https://daretopodcast.com/

    #marketingtips #smallbusinessmarketing #digitalmarketing #directmailmarketing #realestatemarketing #cleaningbusiness #leadgeneration #marketingstrategy #smallbusinessgrowth #businesssuccess #marketingcosts #businessowner #entrepreneurtips #marketingroi #onlineadvertising #ppl #seo #salesconversion #businessgrowth #marketinghelp #leadquality #marketingbudget #marketingideas #marketinghacks #businesstips #marketing2025 #entrepreneurship #marketingchallenges #smallbusinessowner #localbusiness #devinramos #forwardfactor

    Hosted on Acast. See acast.com/privacy for more information.

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    22 min
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