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In this Office Hours episode, we sit down with Irving Betesh, the Co-Founder & CEO of SION, who defied the odds to build a successful business in the travel and tech industries. Known for his passion, straightforward approach, and ability to thrive under pressure, Irving shares his journey from humble beginnings to becoming a respected name in his field. From attending a life-changing Tony Robbins seminar in his 20s to selling a watch to pay rent in his early days, Irving has consistently demonstrated that hard work and resilience can open doors.
Key Moments:
2:30: The Early Influence of a Tony Robbins Seminar: How a powerful seminar in his 20s shifted Irving’s perspective and set him on a new path.8:15: Selling a Watch to Pay Rent: Irving’s decision to sell his watch to make ends meet and why he believes nothing is ever “handed to you.”14:00: From Common Sense to Company Founder: Irving discusses launching companies in travel and tech with little formal training and relying on his intuition.23:45: Passion and Bluntness in Business: How Irving’s approach to life and work—being direct and passionate—has shaped his journey.31:20: Lessons Learned and Advice for Aspiring Entrepreneurs: Irving offers his top takeaways on resilience, taking the first step, and maintaining faith in your vision.Key Takeaways:
Success often stems from resilience and the courage to make difficult choices, especially in challenging times.The power of intuition in business is sometimes as valuable as formal training, and common sense can often lead the way.Finding mentors or events that shift your perspective, like Irving’s Tony Robbins seminar experience, can provide lasting motivation.Irving’s advice for aspiring entrepreneurs: nothing will be handed to you, but by making that first step and committing to your plan, you’ll create your own momentum for success. -
Episode Summary:
In this episode of Office Hours, Grace hosts an engaging conversation with David Chait, CEO and Founder of Travefy, the go-to platform for travel advisors who need a powerful way to streamline trip planning, communication, and client engagement. David walks us through his journey from corporate strategy consulting at McKinsey to a pivotal role at the U.S. Small Business Administration, where he was immersed in the challenges of small businesses during the Great Recession. Inspired by these experiences, David caught the entrepreneurial bug and set out to create Travefy, a platform initially aimed at consumers that found its true mission in supporting travel advisors.
David shares the critical moments and hard-won insights behind Travefy’s growth, from navigating product-market fit to self-funding for long-term sustainability. He reveals how Travefy balanced listening to user feedback with strategic foresight to build a suite of tools tailored specifically for travel advisors, ultimately helping them succeed on their own terms. In this episode, you’ll hear how Travefy tackled the unprecedented challenges of COVID-19, built trust in the advisor community, and why staying mission-driven has been key to their success. Plus, David dives into the qualities he values in his team and his strategic approach to innovation and offers sage advice for aspiring entrepreneurs on setting both success and “off-track” metrics.
Chapters:
00:00 Introduction and David’s Career Journey 01:12 From Strategy Consulting to Small Business Advocacy 06:32 Transitioning Travefy from Consumer to B2B 08:26 Finding Product-Market Fit for Travel Advisors 10:04 Capital Decisions: Self-Funding and Sustainable Growth 14:54 Building with a Mission: Supporting Travel Advisors 17:19 Travefy’s Methodical Approach to Product Development 21:33 Expanding Tools for Travel Advisors: Education & Integration 28:48 Navigating COVID-19: Adapting with Empathy and Innovation 32:01 New Tools for Branding and Workflows 35:43 Advice for Aspiring Entrepreneurs: Setting Success and Failure Metrics 38:01 Early Strategies for Connecting with Advisors 40:45 Hiring for Empathy and User-Centric Values 43:00 Rapid Fire with David: Technology Trends, Industry Misconceptions, and Key Traits for EntrepreneursTakeaways:
Travefy’s journey from a consumer to a B2B tool underscores the importance of identifying a core audience and iterating based on user feedback.David’s experience with small business challenges at the U.S. Small Business Administration influenced Travefy’s mission to empower solopreneurs.Customer-focused product development and clear values have driven Travefy’s growth and resilience.Aspiring entrepreneurs can benefit from setting both success and off-track metrics early in their journey to make quicker, more informed adjustments. -
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In this episode, Grace interviews Caroline Casson, Partner at VITALIZE Venture Capital, a seed-stage fund investing in the future of work. Caroline shares her unconventional path into venture capital, starting from a corporate finance role at GE to helping incubate a startup in the drone industry with GE Ventures. She discusses her transition to VITALIZE, the evolution of the fund’s thesis, and the importance of having a focus when sourcing deals. Caroline dives into the qualities she looks for in founders, from attention to detail to passion for solving specific problems. She reflects on navigating the VC landscape while staying grounded amidst hype cycles. She also shares practical advice for founders on evaluating their company's potential for venture funding and the benefits of capital efficiency.
Chapters:
00:00 Introduction and Caroline’s Venture Journey 01:22 Getting Into Venture Capital 04:36 The Transition to VITALIZE 07:35 From Corporate to Startup: Challenges and Lessons 09:43 Understanding Risk and Timing 11:30 Evaluating Startups: Key Tools and Insights 16:13 Identifying Successful Founder Traits 17:53 The Focus on the Future of Work at VITALIZE 21:20 Differentiating Trends from Real Opportunities 23:14 The Midwest Advantage in VC 25:38 Providing Value Beyond Capital: VITALIZE’s Network Approach 28:11 Should You Raise Venture Capital or Not? 31:26 Final Advice for FoundersTakeaways:
Caroline’s journey shows that unconventional paths can lead to successful venture careers.Attention to detail and a genuine passion for solving problems are vital founder traits.VITALIZE focuses on redefining workflows across industries, not just trendy markets.Founders should align their funding strategy with their business model and lifestyle goals. -
In this episode, Grace interviews Matthew Upchurch, CEO of Virtuoso, a global luxury travel network with over 1,000 agency locations and 20,000 advisors across more than 50 countries. Matthew shares his journey, beginning with his family's travel legacy, to leading Virtuoso and growing it into a network that recorded more than $26 billion in annual sales. He discusses the company’s founding principles, its evolution through technological changes, and his insights into building a human-centric business. Matthew delves into how Virtuoso has embraced technology to amplify human connections, maintained its focus on personalized travel experiences, and navigated market changes. He also offers valuable advice on leadership, business strategy, and staying curious in an ever-changing industry.
Chapters:
00:00 Introduction and Matthew's Travel Legacy01:28 The Founding of Virtuoso04:15 Empathy and Understanding in Business11:37 Evolution of Virtuoso: Keeping Up with Industry Changes13:13 Balancing Technology and Human Connection18:24 Future of Travel Advisors and Industry Insights22:36 Personal Values and Guiding Principles32:38 Embracing Frameworks and Learning from Coaches45:14 Building Team Culture and StructureTakeaways:
Matthew's experience underscores the importance of empathy in business and understanding multiple perspectives.He highlights the power of collaboration and partnership in building Virtuoso.The discussion emphasizes using technology as a tool to enhance human connections rather than replace them.Matthew’s focus on culture and continual learning has been a key driver in Virtuoso’s growth. -
In this episode, Ashwin Kamlani shares his dynamic journey from an e-commerce pioneer at Melia Hotels to becoming a serial entrepreneur and the CEO of Juicer. Ashwin dives deep into the critical moments that shaped his career, including how he transformed Melia’s e-commerce strategy from the ground up, his leap into entrepreneurship after a bold offer from a Danish entrepreneur, and his decision to bootstrap his first company.
Ashwin highlights the lessons he learned from bootstrapping versus raising capital and shares his unique perspective on transparency, leadership, and balancing the personal with the professional. From walking into meetings with the chairman of Melia as a young leader to driving across the U.S. in a pink polka-dot RV with his daughter—meeting clients along the way—Ashwin offers powerful insights into the entrepreneurial mindset. He also reflects on the importance of staying true to yourself in business and how bringing his personal life into his professional world has helped him build trust and lasting relationships.
Throughout the episode, Ashwin candidly discusses the challenges of scaling a business, the tough calls he's had to make, and why intuition and authenticity remain his guiding principles.
Chapters
00:00 Introduction and Ashwin's Early Career at Melia02:17 Rising through the Ranks: From Intern to Global VP 06:55 Pioneering E-Commerce at Melia Hotels 10:58 The Leap into Entrepreneurship: Regatta Travel Solutions 14:53 Bootstrapping vs. Raising Capital: Lessons from Both Worlds 21:12 Navigating Acquisition and the Next Chapter 24:48 Juicer’s Origin and Navigating Dynamic Pricing 32:09 On the Road: Ashwin’s RV Journey with His Daughter 39:24 Personal Insights: The Role of Family in EntrepreneurshipTakeaways
Ashwin’s journey underscores the importance of bold risk-taking, from relentlessly pursuing an unpaid internship to launching his first startup after a life-changing opportunity.Authenticity and transparency in business foster trust, leading to deeper client relationships and stronger connections, even in highly competitive industries like hospitality and restaurants.Successful entrepreneurs must balance instinct with adaptability, knowing when to pivot and when to stick to their vision.Bootstrapping taught Ashwin independence and ownership, while raising capital with Juicer gave him the resources to scale quickly—each path offers valuable lessons.Dynamic pricing in restaurants offers a vast opportunity, but fear of consumer backlash is a hurdle many companies are hesitant to tackle.Ashwin’s journey across the U.S. in a pink polka-dot RV with his 12-year-old daughter offers a unique blend of personal and professional life, illustrating how family and business can intersect in meaningful ways.Having institutional investors who trust your judgment and support your vision can be a game-changer for scaling a business. -
In this episode, Dmitry Koltunov shares his inspiring journey from a software engineer in Ukraine to becoming a successful entrepreneur, founding two companies, ALICE and Arbor. He emphasizes the power of storytelling in both the hospitality and nonprofit sectors, explaining how emotional connections can drive impact and engagement. Dmitry explores the qualities that define successful founders, including resilience, curiosity, and self-awareness, and he stresses the significance of customer feedback in driving business growth. Reflecting on his experiences in the Startup Leadership Program, Dmitry offers valuable insights on entrepreneurship, creativity, and collaboration.
Dmitry also draws parallels between the world of theater and startups, underscoring how creativity and teamwork play essential roles in building successful ventures. He highlights the potential for impact in the nonprofit sector, sharing how emotional storytelling can lead to higher donations and stronger engagement. Throughout the conversation, Dmitry emphasizes the importance of passion for the problem at hand and the ongoing need for sales and customer connection in sustaining a startup's success.
Chapters
00:00 Introduction and Background13:02 Lessons from the Startup Leadership Program 16:08 Insights from Theater and Art 22:55 Building and Leading Effective Teams 29:26 Personal Life Stories and Key LearningsTakeaways
Dmitry’s entrepreneurial journey reflects a transformation from fear to leadership, driven by a passion for solving problems.Storytelling plays a critical role in both hospitality and nonprofit sectors, creating emotional connections that lead to greater impact.Successful founders are resilient, curious, and self-aware, with a focus on continuous learning.Customer feedback is essential for refining and scaling a business.The nonprofit sector offers unique opportunities to create meaningful impact, especially through emotional storytelling.Sales is not a one-time activity but a continuous focus that helps businesses stay connected with their audience.A strong, collaborative team environment fosters innovation and creativity.Passion and a deep understanding of the problem being solved are key to sustaining long-term entrepreneurial success.This episode offers a wealth of knowledge for aspiring entrepreneurs, nonprofit leaders, and anyone interested in the intersection of storytelling, AI, and business growth.
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In this episode, Ted Teng, a renowned leader in the hospitality industry, shares his remarkable journey from an unexpected entry into Cornell’s hotel school to becoming the CEO of Leading Hotels of the World. Ted recounts his early career, highlighting his rapid rise at Sheraton and his influential roles at Disney, Westin, and Wyndham. He underscores the importance of hard work, embracing new challenges, and the power of building meaningful relationships. Ted also discusses the value of networking and selflessly helping others, which has been a cornerstone of his success.
As CEO of Leading Hotels of the World during the 2008 financial crisis, Ted faced significant challenges, including poor revenue performance and a negative company culture. He shares his strategic approach to revitalizing the organization, focusing on preserving its core strengths, shifting from a B2B to a B2C model, and investing in marketing. Beyond his executive roles, Ted talks about his contributions as President of Cornell's Hotel Society and his involvement in creating the Cornell Hotel School Hall of Fame. He also shares his concerns about the industry's reliance on cheap labor, the disruptive potential of generative AI, and the need for greater innovation and collaboration within the sector. This episode is a masterclass in leadership, resilience, and forward-thinking in the ever-evolving world of hospitality.
Chapters
00:00 Accidental Entry into the Hospitality Industry03:30 Fast-Track Progression and Building Relationships09:48 The Power of Hard Work and Networking24:31 Leading Hotels of the World: Applying Business Skills27:04 Joining Leading Hotels of the World during the 2008 financial crisis28:29 Turning around a wounded organization29:03 The need for quality improvement at Leading Hotels31:29 Improving revenue performance32:29 Cultivating a positive culture at Leading Hotels36:26 Building a community of recognition and respect42:41 Ownership and distribution as key industry changes50:28 Concerns about the industry's reliance on cheap labor52:25 The potential and challenges of generative AI53:32 The need for greater innovation and collaboration with third partiesTakeaways
Accidental entry into the hotel school at Cornell led to a successful career in the hospitality industryHard work, taking on new challenges, and building strong relationships contributed to Teng's fast-track progressionNetworking and helping others without expecting anything in return can lead to opportunitiesTeng's entrepreneurial project focused on creating small, dedicated hotels in office buildingsTeng's role as CEO of Leading Hotels of the World allowed him to apply his business skills and market knowledge Joining Leading Hotels of the World during the 2008 financial crisis presented challenges and opportunities.Teng focused on improving the company's quality, revenue performance, and culture.He shifted the company's focus from B2B to B2C and invested in marketing.Teng is currently the President of Cornell's Hotel Society and has created the Cornell Hotel School Hall of Fame.He expresses concerns about the industry's reliance on cheap labor, the impact of generative AI, and the need for greater innovation and collaboration with third parties. -
In this episode, Melissa Krueger, CEO of Classic Vacations, shares her inspiring journey from a small town in the Northwest to leading a significant luxury travel company. She reflects on her early experiences at Club Med and Travel Impressions, providing valuable insights into the role of wholesale companies in the travel industry. Melissa emphasizes the significance of embracing new challenges, particularly the importance of managing a P&L, as a key to career growth. With a focus on leadership, she discusses the value of resourcefulness, curiosity, and making meaningful contributions to her team. Melissa also touches on the importance of work-life integration, the power of relationships in business, and the need for young professionals to lead with a work ethic, seek feedback, and take risks in pursuit of their dreams. This episode is packed with practical advice and personal stories highlighting the essentials of leadership and success in the luxury travel industry.
Chapters:
00:00 Introduction and Excitement to Learn00:49 Early Life and Upbringing05:26 Deciding on College and Career Path08:10 Embracing Hard Work and Challenging Expectations11:14 Entering the Travel Industry13:17 Wholesale Companies and Their Success21:13 Transition to Classic Vacations25:33 Career Growth and Opportunities30:21 Taking on New Responsibilities and Running a P&L32:35 The Power of Resourcefulness and Curiosity in Leadership34:11 Work-Life Integration: Balancing Career and Personal Life35:03 Leading with Work Ethic and Seeking Feedback for Growth36:26 Articulating Dreams and Taking Risks for SuccessTakeaways
Melissa Krueger grew up in a small town in the Northwest and had a simple and easy childhood.She developed a passion for learning and observing other families while attending school.Melissa started her career in the travel industry at Club Med and later joined Travel Impressions, a wholesale company that packages and markets hotels to travel advisors.She transitioned to Classic Vacations and experienced career growth within the company.Melissa emphasizes the importance of being nimble, curious, and creating a demand internally to support the success of others.She values loyalty and believes in asking for opportunities to grow and contribute.Melissa's career path demonstrates that there is not one linear path to success and that unconventional experiences can lead to valuable skills and insights. Taking on new responsibilities and running a P&L can provide valuable experience and open doors for career advancement.Resourcefulness, curiosity, and making things meaningful for others are important traits in leadership.Work-life integration allows for a more fulfilling and balanced life.Showing up, leading with work ethic, and asking for feedback are key to personal and professional growth.Articulating one's dreams and taking risks can lead to success and opportunities.
