Office Hours

In this Office Hours episode, Grace Van Hollebeke sits down with Karen Magee, President of Valerie Wilson Travel, to discuss leading a legacy luxury travel brand into the future. Karen shares her journey from finance to travel, the values that define exceptional hospitality, and how travel advisors can stand out in an increasingly competitive landscape.

They explore what it takes to scale a high-touch luxury brand while staying true to its roots, the power of strong client relationships, and how evolving technology is shaping the industry. Plus, Karen shares candid insights on leadership, balancing career and family, and the lessons she’s learned stepping into this role during a pivotal time for Valerie Wilson Travel.

If you're looking to build a lasting brand in travel, this episode is full of insights on growth, differentiation, and high-impact leadership.

Key Moments:

• (02:06) From Finance to Luxury Travel – How Karen made the leap from the financial industry to leading a major travel brand.
• (04:38) Learning from Legacy Advisors – Why experience is invaluable and how to blend it with fresh perspectives.
• (10:50) The Future of Travel Advisors – How the industry is evolving and where travel advisors should focus their energy.
• (14:12) Building a Hospitality-Driven Brand – The values at the core of Valerie Wilson Travel and why they matter now more than ever.
• (16:56) Standing Out in a Crowded Market – How advisors can differentiate themselves in a world of increasing competition and digital noise.
• (20:48) The Role of Social Media & Marketing – Does social media really bring in business, or is it just brand hygiene?
• (27:29) Leadership Lessons & Navigating Change – The key skills Karen has sharpened as she leads Valerie Wilson Travel into its next chapter.
• (32:48) Balancing Career, Family & Travel – Karen’s honest take on juggling leadership, motherhood, and a demanding industry.
• (36:36) Taking Risks & Trusting the Process – The mindset shifts that helped Karen embrace leadership and change with confidence.

Key Takeaways:

• Luxury travel is built on relationships. The best advisors don’t just book trips—they anticipate needs and elevate experiences.
• Experience matters. Travel advisors get better with time, and learning from those with decades of knowledge is a competitive advantage.
• Social media is a resume, not a sales tool. While important for credibility, real business still comes from referrals and direct outreach.
• Leadership requires patience and vision. Trust, communication, and a clear mission are essential for leading a company through change.
• Balancing work and life isn’t perfect. Success comes from being intentional, setting priorities, and knowing when to say no.

Follow Along:

Karen Magee: LinkedIn | Valerie Wilson Travel

Grace Van Hollebeke: LinkedIn

Lucia: Website

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In this Office Hours episode, Grace sits down with Nikita Leca, a branding and content strategist specializing in travel and hospitality. Nikita shares her journey from working a 9-to-5 to launching her own business, overcoming the fear of putting herself out there, and building a personal brand that attracts ideal clients.

They discuss the importance of branding, storytelling, and content strategy—plus, practical ways to engage your audience, leverage UGC, and optimize your online presence. If you've ever struggled with what to post or how to stand out, this episode is packed with actionable insights.

Key Moments:

• (02:01) The Leap from 9-to-5 to Entrepreneurship – Nikita shares how she transitioned from working in design to running her own branding business.
• (04:15) Why Personal Branding Is Non-Negotiable – The psychology behind why people buy from people, not faceless businesses.
• (07:30) Storytelling That Sells – How to craft content that connects by linking personal experiences with business insights.
• (13:20) The Most Common Mistakes in Branding & Content Strategy – What NOT to do when trying to grow an audience online.
• (18:50) Why Going Viral Doesn't Matter – The difference between vanity metrics and engagement that actually leads to business growth.
• (27:10) Leveraging UGC to Build Trust & Visibility – How to encourage clients to create content that markets your business for you.
• (36:40) How to Actually Get Engagement on Social Media – Strategies for interacting with your audience to boost visibility and conversions.
• (39:50) The Power of a Controversial Hook – Why starting with an unexpected or bold statement can transform your content.
• (41:10) Final Takeaway: Optimize Your Profile – The simple but essential tweaks that will instantly improve your online presence.

Key Takeaways:

• People buy from people. A personal brand builds trust and connection faster than a faceless business.
• Your content should show, not tell. Instead of saying what you do, demonstrate it through behind-the-scenes storytelling.
• Stop chasing vanity metrics. Focus on engagement and conversions over followers and likes.
• User-generated content is a game-changer. Make it easy for clients to share their experiences with your brand.
• Be consistent. Posting frequency matters more than perfection.

Follow Along:

• Nikita Leca: Lucia Profile | LinkedIn | Instagram
• Grace Van Hollebeke: LinkedIn
• Office Hours Podcast: Website
• Lucia: Website

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In this episode of Office Hours, Grace Van Hollebeke talks about overcoming the fear of posting on social media and how personal branding can help grow your business. Drawing from her own experiences, she shares thoughtful tips and practical strategies to help you show up authentically, create content that resonates, and build trust with your audience. Whether you're just starting out or looking for fresh ideas, this episode offers a supportive and approachable guide to feeling more confident online.

Key Moments:

(00:01) Welcome & Why This Matters: Why your personal brand is your business brand — and how leaning into it builds trust and opens doors.

(02:00) Overcoming the Fear of Posting: How to stop stressing about what people think and start showing up online with confidence.

(05:00) Consistency Beats Perfection: Why being top of mind matters way more than crafting perfect posts.

(08:00) Content Ideas That Work: Behind-the-scenes stories, personal milestones, and lessons from your business journey that people actually want to see.

(12:00) Content Pillars for Consistency: How to create 4-5 content pillars that simplify your content strategy and keep you showing up consistently.

(18:00) Progress Over Perfection: Why starting messy is better than not starting at all — and how practice builds confidence.

Key Takeaways:

• Nobody Cares as Much as You Think: People are busy — they’ll scroll past or engage without overanalyzing your posts.
• Your Personal Brand = Your Business Brand: Show who you are, not just what you sell.
• Start Small: Post one piece of content this week — share a win, a lesson, or something you’re excited about.
• Content Pillars Keep You Focused: Choose 4-5 core themes that matter most to you and your business.
• Be Authentic, Not Perfect: Consistency beats perfection every time.

Follow Along:

• Grace Van Hollebeke: LinkedIn | Instagram
• Office Hours Podcast: Official Site
• Lucia: Learn More

Grace sits down for a spontaneous Friday afternoon chat about how to actually market a small business. Drawing from her experiences working with entrepreneurs in travel, tech, and hospitality, Grace shares creative, no-nonsense strategies that go beyond the usual “post on social media” advice. This solo session is packed with practical tips on email marketing, content creation, partnerships, and more—all focused on getting results without breaking the bank.

Key Moments:

• (02:15) Social Media Isn't the Fix-All: Why social media shouldn’t be your first marketing move—and how to use it as a credibility tool instead.
• (05:48) Email Marketing Done Right: Why collecting email addresses is the most serious marketing move you can make—and how to start now.
• (15:20) Creating Valuable Content: How to use case studies, customer reviews, and real-life stories to build trust and engage your audience.
• (23:40) Partnerships That Pay Off: How to co-host webinars, events, and cross-promotions to expand your reach and tap into new markets.
• (31:12) Asking for What You Want: Why business owners should ask for referrals, feedback, and partnerships regularly—and how it leads to surprising opportunities.
• (37:50) Mastering One Thing at a Time: Why it’s better to be great at one marketing channel before expanding to others.

Key Takeaways:

• Own Your Audience: Collect email addresses and build your list—you own that audience, unlike social media followers.
• Show, Don’t Tell: Use customer stories, reviews, and user-generated content to demonstrate what your business can deliver.
• Be Present and Valuable: Share content that educates, entertains, or inspires—without constantly selling your services.
• Partnerships Matter: Cross-promote with aligned businesses for mutual growth and greater visibility.
• Start Now, Improve Later: You won’t be perfect at first, but taking action is better than waiting.

Follow Along:

• Grace Van Hollebeke: LinkedIn | Instagram
• Office Hours Podcast: Official Site
• Lucia: Learn More

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.