Made it in Thailand

Scott Pressimone
  • 4.0 (1)
  • Entrepreneurship
  • Updated Weekly

Interviews with entrepreneurs and business leaders who’ve “made it” in Thailand. Real stories of ambition, setbacks, and strategic wins on the path to success. Built for founders and operators who want to win in Thailand. Guests from the US, UK, Australia, and Thailand. Honest journeys and cross-cultural lessons. Inspiration for anyone building in the Thai market. Apply to be a guest: https://madeitinthailand.com/apply Hosted by Scott Pressimone, a US expat based in Thailand for 13+ years and owner of Fractiond, a Thailand-based strategy consultancy. #ThailandBusiness #ExpatSuccess #ThaiExpat

  1. Jun 2

    Corporate to Business Owner: What It Really Takes to Make the Jump | Steven McGinnes

    Event Details & Registrationhttps://www.scottpressimone.com/freedom-bkk/ Steven McGinnes lives in Phuket, works from a sailboat, and has built the kind of life that looks effortless on LinkedIn. He's also one of the most honest people I've spoken with about what it actually costs to get there. That gap between the 4pm on the water and the 4am worrying about whether the invoice lands is exactly what this conversation is about. Steven spent his career in the creative agency world before going out on his own. He's watched enough people make the same avoidable mistakes to know which ones to flag early. We covered a lot of ground, but it kept returning to the same core tension: freedom and accountability scale together. The more of one you want, the more of the other you're signing up for. What most people making the jump from corporate underestimate is not the hustle. It's the invisible infrastructure they never had to think about. The vendor setup. The payment terms. The cash flow gap. The fact that 65% of business failures come not from a lack of clients, but from the timing of when money arrives versus when it goes out. We also got into the T-shaped skill set. You don't need to become an expert in finance or new business development or legal setup. You need to be competent enough that none of them kill you. And you need to start building your network before you desperately need it, because the people who wait until they're hungry are already too late. ABOUT THE GUESTSteven McGinnes is a Bangkok and Phuket-based independent operator and keynote speaker with a background in creative agency leadership across Asia. After building a career running client teams and regional creative operations, he went out on his own and has been working from Thailand ever since, with clients across Asia, the US, and beyond. He's co-organizing our upcoming June 26th event on making the jump from corporate to independent.https://www.linkedin.com/in/stevenmcginnes/ ABOUT THE HOSTI'm Scott Pressimone, a Fractional Commercial Leader and Interim Country Director with over a decade of executive experience on the ground in Bangkok. I help foreign companies and founders bridge the gap between Western expectations and Thai operational realities.https://www.linkedin.com/in/scottalanpress/ CHAPTERS00:00 Introduction00:47 Meet Steven03:23 Event in Bangkok05:04 Three Reasons to Go Solo07:27 Identity and Disappearing Roles09:50 T Shaped Skills for Founders15:14 Sales Discomfort and Accountability19:57 Passion vs Paid Market26:05 Unknown Unknowns and Admin27:07 Vendor Setup Headaches27:32 Cash Flow Payment Delays28:35 Founder Mindset Shift30:24 Is It Worth It32:10 Freedom Versus Accountability33:57 Job Security Illusion37:24 Working From Thailand39:31 Doing It Above Board43:09 Hidden Costs Unknowns46:44 Build Network Early48:04 Choosing Clients Saying No49:39 Workshop Format Follow Up53:02 Final Takeaways Closing #CorporateToEntrepreneur #GoingFractional #BangkokBusiness #WorkingInThailand #IndependentOperator #ThailandEntrepreneur #FractionalLeadership #BusinessInAsia

    54 min

  2. May 5

    The School Question Parents in Thailand Get Wrong | Donnah Ciempka

    The most common question in every family-focused Thailand expat group is "what's the best school?" and it's the wrong place to start. I sat down with Donnah Ciempka, who spent five years as Head of School at Ascot International Bangkok, to work through what parents actually need to be thinking about, partly because I'm raising my own children here and I wanted the honest version. We covered a lot of ground, but most of it kept coming back to the same thing: families committing to a 10 to 20 million baht education investment without running the numbers all the way through. School fees in Thailand increase two to six percent every year, employer-covered packages have largely left the picture, and what looks manageable at age four looks very different at age 14. We talked about bilingual education, why it requires a longer commitment than most families plan for, and why the timing window is narrower than people realize. Technology came up too, both as a parenting challenge and as something specific to Thailand, where what's accessible on social media operates under different conditions than what parents from Australia or the UK are used to. The point that stayed with me was simpler: kids who have never heard no or had to push through something hard are not being set up for what's ahead, and it falls on parents to hold that line. If you are raising children in Bangkok, or about to relocate here with a family, these questions come around eventually. Better to have them early. ABOUT THE GUEST Donnah Ciempka served five years as Head of School at Ascot International School, a leading K-12 IB World School in Bangkok. She has spent over 17 years as an IB consultant and visiting team leader across Asia Pacific, and completed three years as President of the Australian-Thai Chamber of Commerce (AustCham Thailand). Few people working in Bangkok's education space have her combination of in-school leadership and regional consulting experience. https://www.linkedin.com/in/donnah-ciempka-4a4b31b3/ ABOUT THE HOST I am Scott Pressimone, a Fractional Commercial Leader and Interim Country Director with over a decade of executive experience on the ground in Bangkok. I help foreign capital, founders, and CEOs bridge the gap between Western expectations and Thai operational realities. https://www.scottpressimone.com/ CHAPTERS 00:00 Introduction 02:15 Leaving Ascot 04:21 Expat Life With Kids 08:38 Choosing Your School Path 12:34 University Pathways Planning 14:47 Real Cost of Education 25:05 Bilingual Schools 27:41 Culture and Community 29:26 Language Proficiency Stakes 31:11 Tech in Education 35:57 Device Rules at Home 38:18 Online Safety in Thailand 40:45 Attention and Addiction 44:08 Preparing for Change 46:50 Thai Values to Learn 48:19 Find Your Tribe 49:54 Closing #InternationalSchoolsBangkok #BilingualEducation #ExpatsInThailand #RaisingKidsAbroad #BusinessInThailand

    51 min

  3. Apr 21

    The Tax Mistakes That Are Costing Expats in Thailand More Than They Know | Bobby Casey

    What started as a conversation about Thailand's shifting tax environment with Bobby Casey turned into a full operational teardown of the most expensive structural mistakes location-independent entrepreneurs make. We cover the collapse of Hong Kong and Singapore as go-to nomad jurisdictions, why a Wyoming LLC is the correct default structure for non-US founders doing business in Thailand (and why most Americans set it up in a way that destroys their own privacy), the HoldCo structure that saves a $300K earner roughly $25,000 a year in self-employment tax, the bonafide residency test that most Americans living abroad have never heard of, and why California has a specific tax trap that follows you across borders even if you haven't set foot in the state in five years. If you are building a business while living or traveling in Southeast Asia, this is the conversation I wish existed when I first arrived in Bangkok in 2012. This video was NOT sponsored. About the Guest:Bobby Casey is the founder of Business Anywhere, an online platform serving location-independent entrepreneurs who need company registration, registered agent services, virtual mailboxes, banking solutions, bookkeeping, and tax consulting all in one place. He has built one of the most recognized compliance and tax optimization platforms in the digital nomad space, with a client base spanning dozens of countries and a content library of over 2,000 specialist articles. His practice focuses almost exclusively on the tax and structural realities of operating across multiple jurisdictions, and he has personally guided clients through some of the most complex cross-border compliance situations in the industry.https://businessanywhere.io About the Host:I'm Scott Pressimone, a Fractional Country Director and strategist with over a decade of executive experience on the ground in Bangkok. I help foreign capital, founders, and CEOs bridge the gap between Western expectations and Thai operational realities.https://www.scottpressimone.com/ Chapters:00:00 Introduction03:00 Thailand's Tax Crackdown06:14 Residency vs. Tax Residency08:06 Scott's Permanent Residency Story09:30 Stop Taking Advice From Facebook13:01 The Compliance Gray Scale14:44 Portugal, US LLCs and Tax Treaties17:03 Why Hong Kong and Singapore Are Dead22:05 The Seven-Figure Bank Account Trap24:02 Why a Wyoming LLC Wins26:19 When Simple Is Better27:48 The $300K American in Thailand31:49 The DIY LLC Privacy Mistake35:53 The HoldCo That Saves $25K a Year38:23 The German Nomad Simple Setup42:19 Why Paying Thai Tax Matters43:25 The California Tax Trap44:48 The Bona Fide Residency Test51:13 Final Mistakes and Oh Shit Moments57:37 How to Find Bobby Casey

    59 min

  4. Apr 7

    High Performers Burn Out Faster. Thailand's Wim Hof Advanced Instructor Explains Why.

    High-level operators are burning out because they have lost the ability to switch off their nervous systems, and most of them do not even know it is happening. I wanted to understand the mechanics behind this, so I invited Stuart Wilson to break it down. Stuart left a high-stress financial career in Dubai, went through an ayahuasca reset in the Amazon, and eventually became Bangkok's leading certified breath work and cold exposure instructor. Our conversation goes far beyond wellness. We get into the real intersection of executive performance, lifestyle design, and entrepreneurship in Bangkok. Stuart walks through the neuroscience of chronic stress and why a holiday will not fix a default mode network that never shuts down. From there we move into the operational realities of building Breath Inspired from the ground up, including candid insights on navigating intellectual property theft in Thailand, why Stuart actively prefers hiring local Thai talent over foreign staff, and what it actually looks like to scale a cross-cultural business with a Thai co-founder. ABOUT THE GUEST Stuart Wilson is the co-founder of Breath Inspired, an Advanced Wim Hof Method Instructor, and the only Oxygen Advantage Master Instructor in Asia. After experiencing burnout in Dubai's financial sector, he relocated to Bangkok to build the region's premier science-backed breath work and cold exposure community alongside his wife and co-founder, Kam. https://www.breathinspired.com/ ABOUT THE HOST I'm Scott Pressimone, a Fractional & Interim Country Director and strategist with over a decade of executive experience on the ground in Bangkok. I help foreign capital, founders, and CEOs bridge the gap between Western expectations and Thai operational realities. https://www.scottpressimone.com/ CHAPTERS 00:00 - The Ice Bath Illusion05:01 - Burnout in Dubai09:36 - The Wim Hof Discovery13:20 - Default Mode Network23:20 - Building Breath Inspired35:12 - Copycats and True Fans48:13 - IP Theft in Thailand59:39 - Running a Cross-Cultural Business1:13:55 - Visas and Company Setup1:23:04 - The Hiring Mistake Expats Make #ExecutiveBurnout #DoingBusinessInThailand #WimHofMethod #BangkokBusiness #FractionalDirector

    1h 31m

  5. Mar 24

    Scaling Operations in Thailand: The Systems The Biggest Brands Use | Chokdee Wisansing

    As foreign founders and corporate operators, we often assume that our successful global playbooks will seamlessly translate to the Thai market. The reality is that scaling operations here requires a deep, structural localization of our systems, our products, and our leadership style. In this episode, I sit down with Khun Chokdee Wisansing, former Chief Operating Officer and Chief People Officer for major conglomerates like KFC, AWC, and Central Group. We discuss the mechanics of bridging generational gaps, adapting global systems, and building high-trust, lean teams in Thailand. Core executive takeaways:• The global to local playbook: Why international giants like KFC succeed in Thailand by rigidly maintaining their world-class systems while completely adapting their product to the local palate and consumer behavior.• The 3 S framework of scaling: How to architect your strategy, system, and structure so that no single employee is bigger than the organization.• The talent retention trap: A Chief People Officer perspective on why job hopping for incremental salary bumps destroys long term executive influence, and how to successfully integrate new tech skills with senior leadership wisdom.• Demystifying Thai time: How to establish a high performance culture of punctuality, accountability, and mutual respect without aggressively clashing with local operational norms. Timestamps:00:00 Introduction03:49 Climbing the Ladder05:34 Why Job Hopping Fails08:01 Long Game Networking09:51 Systems People Mindset10:59 Strategy System Structure14:00 Clear Roles No Gray Areas17:43 Winning in Thailand17:57 Localizing Global Brands22:33 Thai Time and Respect27:19 Bridging Generations32:17 Respect And Learning33:18 Mentorship Through Coaching34:33 Stability In Uncertainty36:11 Lean Team Strategy39:20 Small Business Confidence43:01 Delivering And Trust44:06 Why Candy Crush47:34 Lead By Example49:34 Degrees Versus Skills53:11 Control Your Future55:57 Reach Out For Help58:03 Conclusion Expanding your business in Thailand? Connect with me for a diagnostic consultation: https://www.expatden.com/thailand-business-growth-strategy-session/ Guest contact details:Khun Chokdee WisansingWebsite: http://www.candycrushthailand.comLinkedIn: Search "Chokdee Wisansing"

    59 min

  6. Mar 10

    The Visa & Work Permit Truth for Founders in Thailand with Benjamin Hart

    As foreign founders and corporate operators, we often underestimate the administrative friction of entering and scaling a team in the Thai market. The reality is that a competitive salary is just the baseline. The true cost of talent is hidden in the compliance. In this episode of Made it in Thailand, I sit down with Benjamin Hart, Managing Director at Integrity Legal, to discuss the operational realities of corporate structuring, foreign talent acquisition, and long-term residency in Thailand. We move past the surface-level advice and look at the actual mechanics of building a sustainable, compliant business in Thailand. Core Executive Takeaways:• The Hidden Sunk Costs of Talent: Why work permits, mandatory Thai staff ratios, and early burnout drastically shrink our operational runway.• The US Treaty of Amity Advantage: How American founders can leverage this agreement to secure 100% corporate ownership and bypass standard BOI oversight.• The DTV & LTR Corporate Trap: Why these highly publicized new visas carry hidden long-term compliance and residency risks for our executive teams.• The Thinking Backwards Framework: How to structure your local entities today to effortlessly survive the regulatory audits and PR applications of tomorrow. Structure your Thai operations for the long game: To de-risk your market entry and explore fractional executive support, connect with me for a diagnostic consultation at scottpressimone.com. Timestamps:00:00 Introduction03:20 PR & Citizenship08:03 DTV & LTR Visa Risks15:58 Working From vs. In Thailand34:16 Currency Flows & Strategy44:52 US Treaty of Amity49:13 BOI vs. US Treaty of Amity51:19 Market Outlook55:09 The Suez Canal Shift59:43 Market Entry Advice01:02:49 Hidden Sunk Costs01:07:27 Conclusion Guest Contact Details:Benjamin Hart, Integrity Legalinfo@legal.co.thThailand: +66 2-266-3698 USA Toll Free 1-877-231-7533http://www.integrity-legal.com/www.youtube.com/@UCO6aDpt9xRwgueZvwIsBpWg Guest Contact Details:Benjamin Hart, Integrity Legalinfo@legal.co.thThailand: +66 2-266-3698 USA Toll Free 1-877-231-7533http://www.integrity-legal.com/www.youtube.com/@UCO6aDpt9xRwgueZvwIsBpWg

    1h 9m

  7. Feb 24

    From PhD to 150k Followers: Scaling a Digital Education Business in Thailand

    Most business owners underestimate the operational complexity of scaling a digital brand. This interview with Thai entrepreneur Wasinee "New" Phonsri, founder of Thai Lessons by New, breaks down exactly how she grew her following to 150K and built an education platform with multiple revenue streams. She transitioned from a solo creator to a highly leveraged, lean business. 👉 If you are a founder or executive looking to build out your operational systems and team in Thailand, book a strategic diagnostic session here:https://www.scottpressimone.com/ Key Business Takeaways:• Scaling a Creator-Led Brand: Despite managing 150K followers across YouTube, Facebook, and TikTok, New remains the sole content creator. She breaks down her Eisenhower Matrix time-blocking system, content batching strategy, and how she leverages AI and a lean team (a business partner and PR support) to increase output without bloating payroll.• The Partnership Inflection Point: After operating entirely alone for two years, New realized she was the bottleneck. Hear the decision framework she used to evaluate bringing on a business partner, and how this team expansion filled specific operational gaps (cold ads, evergreen funnels, payment infrastructure) so she could focus purely on product and content.• Revenue Architecture & Passive Income Design: How New structured her business across four distinct revenue streams to create predictable monthly recurring revenue while maintaining ultimate operational flexibility.• Decoding Thai Talent (The Education System): As a Thai native who spent 12 years in Australia, New provides critical context for foreign executives managing Thai teams. She explains how local education impacts workplace communication, decision-making autonomy, and why Western-style management often requires cultural adjustments.• Market Positioning & Customer Segmentation: New's customer base skews heavily toward early-retired executives and former CEOs. Learn how she uses their feedback to iterate on scalable course offerings. Why This Matters for Foreign Executives in Thailand:If you are building or managing a team in Thailand, understanding cultural differences is critical. New's unique background (Thai academic foundation + over a decade in Western work cultures) gives her the perfect vantage point to explain how Thai professionals learn, adapt, and work. Furthermore, her transition from a solo hustle to a structured, lean operation is a masterclass for any founder looking to prioritize systems and leverage over raw headcount. Timestamps:00:00 - Introduction01:55 - YouTube vs Facebook02:25 - The Secret PhD04:40 - Why YouTube & Passive Income06:11 - Overcoming Camera Fear09:00 - Using Comments to Improve10:11 - Thai Education System14:56 - Learning Independence Early18:36 - Advice for Learning Thai21:41 - AI in Language Learning24:06 - Staying Adaptable with AI25:20 - Building a Scalable Business26:06 - Designing for Freedom28:00 - Why Keep 1-on-1 Lessons29:59 - Launching Patreon31:29 - Free Content Mission32:28 - Finding a Business Partner & Expanding the Team33:56 - Thinking Like a Company37:05 - Value-First Business41:59 - Time Management & Balance46:11 - Where to Find New 👉 Ready to untangle your operations in Thailand? Book a strategic diagnostic session here: https://www.scottpressimone.com/ About the Guest:New holds a PhD in Chemistry and spent a decade in academic research before pivoting to digital education. She now runs Thai Lessons by New, an education business with nearly 150,000 followers. Her lean, creator-led business model combines free decentralized educational content with premium offerings, generating revenue through Patreon, self-paced courses, and 1-on-1 tutoring. About Made it in Thailand:Hosted by Fractional Country Director Scott Pressimone, the Made it in Thailand podcast sits down with the country's top entrepreneurs, executives, and operators. We decode the operational, cultural, and strategic challenges of building businesses in Southeast Asia, bringing a practitioner's perspective to market entry, cross-cultural leadership, and scaling in the ASEAN market. #ThailandBusiness #CreatorEconomy #SEAsia #StartupThailand #BusinessScaling #MadeItInThailand

    47 min

  8. Feb 10

    Selling Trust in a Low Trust Market: How Butler Garage Beats the "Cheapest" Shops

    In this episode of Made It In Thailand, we sit down with a young founder who built a premium service business in Thailand during COVID. He shares what it really takes to build trust, deliver accountability, and grow a business in the Thai market as an entrepreneur. Kei Sekiguchi, founder of Butler Garage, explains how he went from struggling to pay staff to running one of Thailand’s most trusted service businesses. We talk about customer service, leadership, hiring, and the realities of doing business in Thailand as a young business owner. In this conversation, we cover: – Building a business in Thailand as a foreigner – Why accountability matters more than price – Customer service mistakes most businesses make – Hiring and managing staff in Thailand – Founder mindset during hard years of growth This podcast is for entrepreneurs, founders, and professionals interested in business, startups, and careers in Thailand. Subscribe for founder stories and real business conversations from Thailand. Guest Details:Kei Sekiguchi, Butler Garagehttps://www.butlergarage.com/https://www.instagram.com/butler.garagehttps://www.facebook.com/ButlerGarage/https://www.tiktok.com/@butlergarage

    56 min
See All (42)

About

Interviews with entrepreneurs and business leaders who’ve “made it” in Thailand. Real stories of ambition, setbacks, and strategic wins on the path to success. Built for founders and operators who want to win in Thailand. Guests from the US, UK, Australia, and Thailand. Honest journeys and cross-cultural lessons. Inspiration for anyone building in the Thai market. Apply to be a guest: https://madeitinthailand.com/apply Hosted by Scott Pressimone, a US expat based in Thailand for 13+ years and owner of Fractiond, a Thailand-based strategy consultancy. #ThailandBusiness #ExpatSuccess #ThaiExpat

Information

  • Creator
    Scott Pressimone
  • Years Active
    2024 - 2026
  • Episodes
    42
  • Rating
    Explicit
  • Copyright
    © 2026 Fractiond
  • Show Website
    Made it in Thailand