In this Office Hours episode, Grace sits down with Ellen Yui, founder of Yui+Company, a trailblazing communications consultancy celebrating 33 years of success. Ellen shares her journey from a young leader in a big Irish family to launching her own company while pregnant and navigating the challenges of entrepreneurship. Ellen discusses the importance of values, joy, and authenticity in business and life with candor and humor.

Key Moments:

• (03:54) The Pregnancy That Sparked a Business: Ellen shares how starting her company while pregnant catalyzed her entrepreneurial success.
• (09:01) Client Loyalty That Built a Legacy: How Ellen’s early clients followed her and helped her establish Yui+Company.
• (18:43) The Role of Values in Leadership: Ellen discusses why knowing and embodying your values is foundational to personal and professional success.
• (29:20) Using Joy as a Tool in Business: Why Ellen believes joy is the “divine spark” that fuels creativity and connection.
• (35:02) Simplifying Communication for Impact: Practical tips for tailoring messages to your audience and avoiding unnecessary noise.
• (52:52) Advice for Aspiring Entrepreneurs: Ellen offers wisdom for those starting out, emphasizing the importance of knowing yourself and thinking beyond the present.

Key Takeaways:

• Authenticity and values are the cornerstones of lasting success.
• Communication isn’t about making noise—it’s about making connections.
• Joy is a powerful driver in business, both as a motivator and as a tool to inspire others.
• Risk tolerance and resilience are essential traits for entrepreneurs.
• Always think ahead and believe that the world will catch up to your vision.

Follow along:

• Grace Van Hollebeke: https://www.linkedin.com/in/gracevanholl/
• Office Hours: https://www.officehourspod.com/
• Lucia: https://letslucia.com/

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 Entrepreneurs

Takeaways:

• 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.

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 Founders

Takeaways:

• 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 Legacy
• 01:28 The Founding of Virtuoso
• 04:15 Empathy and Understanding in Business
• 11:37 Evolution of Virtuoso: Keeping Up with Industry Changes
• 13:13 Balancing Technology and Human Connection
• 18:24 Future of Travel Advisors and Industry Insights
• 22:36 Personal Values and Guiding Principles
• 32:38 Embracing Frameworks and Learning from Coaches
• 45:14 Building Team Culture and Structure

Takeaways:

• 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 Melia

• 02:17 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 Entrepreneurship

Takeaways

• 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 Background
• 13:02 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 Learnings

Takeaways

• 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.

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 Industry
• 03:30 Fast-Track Progression and Building Relationships
• 09:48 The Power of Hard Work and Networking
• 24:31 Leading Hotels of the World: Applying Business Skills
• 27:04 Joining Leading Hotels of the World during the 2008 financial crisis
• 28:29 Turning around a wounded organization
• 29:03 The need for quality improvement at Leading Hotels
• 31:29 Improving revenue performance
• 32:29 Cultivating a positive culture at Leading Hotels
• 36:26 Building a community of recognition and respect
• 42:41 Ownership and distribution as key industry changes
• 50:28 Concerns about the industry's reliance on cheap labor
• 52:25 The potential and challenges of generative AI
• 53:32 The need for greater innovation and collaboration with third parties

Takeaways

• Accidental entry into the hotel school at Cornell led to a successful career in the hospitality industry
• Hard work, taking on new challenges, and building strong relationships contributed to Teng's fast-track progression
• Networking and helping others without expecting anything in return can lead to opportunities
• Teng's entrepreneurial project focused on creating small, dedicated hotels in office buildings
• Teng'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.