Tales From The Sky Lounge-A Business Podcast

Joining us in the Sky Lounge today is Lisa Calhoun, founding managing partner of Valor Ventures! Lisa shares her journey as a fourth-generation entrepreneur, the importance of relationships in venture capital, and her investment philosophy. She and Todd discuss the current state of the venture landscape, the impact of AI on startups, and advice for young entrepreneurs. Lisa shares her insights on navigating challenges in the industry and the transformative power of travel and personal growth.

Growing up, working for her family's commercial print shop, cold-calling clients as a teenager, and witnessing the rise of the microcomputer revolution firsthand, Lisa's got a lot of experience with making things happen in the tech industry. She explains how those experiences shaped her investing philosophy at Valor, where she leads seed-stage AI and SaaS deals across the South.

ABOUT OUR GUEST:

Lisa Calhoun is an experienced leader in venture capital. Lisa was recently named Atlanta Investor of the Year by Startup Atlanta and highlighted among Business Insider’s Top 30 Women Early-stage Investors in the U.S. She is the founder and managing partner of Valor Ventures, the South’s first woman-led, institutional venture capital firm, now investing its third fund. Valor’s portfolio employs just over 1,000 people and has a footprint across 25 countries.

Under her leadership, Valor leverages a high performance portfolio of AI and SaaS software companies based in the South. Valor’s first checks into AI startups change the real world. Valor portfolio firms are helping guide major law firms (Visalaw); major city industrial cores around vehicle automation (Autonoma); US hospitals (AI genomics and mental health monitors); as well is on the front in Ukraine (AI drone intelligence).

Valor is also known for developing Vic, a visionary AI-powered investment management platform integrated with industry leaders like Salesforce, Carta, and PitchBook. Valor funds are backed by notable institutional investors as well as thoughtful private capital.

CONTACT:

https://www.linkedin.com/in/lisacalhoun/

https://valor.vc/

What is THE SKY LOUNGE?

Tales from the Sky Lounge takes you on a journey through business, consulting, and venture investing, hearing stories from the entrepreneurs, consultants, and investors shaping these industries.

ABOUT OUR HOST:

Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CiSO as a partner at TechCXO.

He has served in a series of companies as a C-Level executive focused on leveraging the Cloud to bring SaaS offerings to market. As an entrepreneur, turn-around expert, technology and product leader, and mentor, Todd has held full corporate P&L and product development responsibilities and directed diverse international teams of Engineering Managers, Mobile Architects, Developers, Dev Ops, QA, and Customer Success professionals.

Subscribe and turn on notifications to listen to new episodes as they launch!

YouTube: https://www.youtube.com/playlist?list=PLfeCS-Varb4gu2uCwyRTXWWEdP676Huh6

Spotify: https://open.spotify.com/show/6jz6ubcaUZ20Xh8TXhwzEN

Apple: https://podcasts.apple.com/us/podcast/tales-from-the-sky-lounge/id1730134658

Amazon: https://music.amazon.com/podcasts/4ba289a5-0d33-4589-95c7-83416731a864/tales-from-the-sky-lounge

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Learn more about TechCXO: https://www.techcxo.com/

Production/Design: James Liebman

Music: Soundstripe/Cody Martin-Sunrise

Joining us today in the Sky Lounge is Alan Gold, a marketing and sales strategist with decades of experience in M&A, startups, and growth strategy. Alan has been on both sides of the table—helping companies scale, navigating acquisitions, and leading turnarounds. From being part of the launch team for Wi-Fi technology to working on speech recognition and AI-powered business tools, he’s seen how markets evolve and what it really takes to stay ahead.

We dive into:

Plus, Alan shares hilarious and wild travel stories, including a baboon with an attitude and getting detained in Colombia.

If you’re in startups, consulting, M&A, or just trying to grow a business, this one’s for you.

Alan’s a veteran of the B2B marketing world, having been an executive in startups, international public companies, high-growth technology and services companies, leading marketing and sometimes both marketing and sales efforts.

Over my career, I have launched new technologies that are integral to our daily lives, repositioned companies to take advantage of new markets, and been involved in M&A activities on both sides of the process. I’ve worked in many different industries, including software, supply chain, medical and pharma, healthcare applications and services, as well as telecom and AI-driven planning software.

Email: [email protected]

Tales from the SkyLounge is a podcast where we take you on a journey through the world of business, consulting, and venture investing. In each episode, we gather in our virtual sky lounge, high above the hustle and bustle of the everyday world, to hear stories from the people who are shaping the future of these industries. From entrepreneurs who are disrupting the status quo, consultants who are helping companies solve their biggest challenges, and investors who are making bets on the next big thing.

Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CISO as a partner at TechCXO. He has served in a series of companies as a C-Level executive focused on leveraging the Cloud to bring SaaS offerings to market.

Learn more about TechCXO

Joining us today in the Sky Lounge is Antonio Pagano, founder of Wawandco and co-founder of Symbol Security. Todd and Antonio discuss cybersecurity’s human element, compliance, evolving phishing attacks, and AI’s role in scams. Antonio shares insights on real-world incidents, cyber insurance trends, and the dynamics of running a business with a remote co-founder. He also delves into the challenges and successes of entrepreneurship, emphasizing the balance between ambition and well-being, and how staying grounded fuels creativity and success.

Antonio Pagano is a visionary entrepreneur from Barranquilla, Colombia, dedicated to making technology accessible. In 2013, he founded Wawandco, a software development company delivering efficient, high-quality solutions for US and European clients. His expertise spans web applications, mobile solutions, APIs, and UX.

Antonio co-founded Symbol Security, a SaaS company focused on cybersecurity awareness. By addressing human risk factors, Symbol Security helps organizations protect their assets. His innovation extends to tools like Releaso, leveraging AI for product communication, and Retabler, optimizing data workflows. Beyond business, Antonio is a devoted family man who enjoys sports, outdoor activities, and quality time with loved ones.

Email: [email protected] | [email protected]

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Tales from the Sky Lounge is a podcast that takes you through business, consulting, and venture investing, featuring stories from entrepreneurs, consultants, and investors shaping these industries.

Todd Merrill is an experienced software executive assisting clients as a fractional or interim CTO and CISO at TechCXO. A SaaS leader, Todd blends technical expertise with mentoring.

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Learn more about TechCXO

Production/Design: James Liebman

Today in the Sky Lounge, Bryan Dennstedt joins Todd Merrill as they bring their unique perspectives from years in business, technology, and investing for a deep dive into the trends that will shape 2025. From venture capital’s cautious return to the AI-driven reshaping of industries, this episode is a candid discussion about what’s next for tech, work, and investing. Everything from whether AI is going to hit speed bumps or keep climbing, blockchain’s role in authenticity in AI and the future of collaboration tools is on the table!

Bryan Dennstedt is an accomplished Fractional CTO or Fractional CIO with TechCXO in Charlotte, North Carolina, where he has focused his efforts as a hands-on Fractional CTO and Interim CIO with numerous clients. He is an expert in mobile application development, healthcare integrations, and all aspects of telemedicine and has worked on over 40 engagements in a fractional capacity for the firm. His experience includes managing all information technology operations, from fractional CTO product development to Interim CIO large-scale technology migrations. Bryan works to ensure that his clients’ high-level Information Technology roadmaps are well-defined and then digs into the details to ensure that established metrics, accountability, and results are being delivered by the team he leads. Once a client is up and running with his methodologies, the Fractional CIO capacity can be leveraged in an ongoing model, and it can be ramped up to Part-Time CIO as needed throughout a project.

Tales from the Sky Lounge is a podcast where we take you on a journey through the world of business, consulting, and venture investing. In each episode, we gather in our virtual sky lounge, high above the hustle and bustle of the everyday world, to hear stories from the people who are shaping the future of these industries. From entrepreneurs who are disrupting the status quo, consultants who are helping companies solve their biggest challenges, and investors who are making bets on the next big thing.

Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CISO as a partner at TechCXO. With a history of leadership and innovation in SaaS product development, Todd combines technical expertise with a knack for mentoring.

Learn more about TechCXO

Production/Design: James Liebman

This year has been a whirlwind of adventure, and as we gear up for an incredible 2025, we’re hitting pause to share something special—our favorite travel stories! From mind-boggling mishaps to inspiring lessons learned on the road, these tales are all about the joy, challenges, and magic of exploring the world while living in the world of business.

We’re so grateful to our amazing guests and YOU, our listeners, for making this journey unforgettable. Sit back, relax, and let these stories take you places. Here’s to another year of growth, adventure, and connection. See you in 2025!

Tales from the Sky Lounge takes you on a journey through business, consulting, and venture investing, hearing stories from the entrepreneurs, consultants, and investors shaping these industries.

Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CiSO as a partner at TechCXO.

He has served in a series of companies as a C-Level executive focused on leveraging the Cloud to bring SaaS offerings to market. As an entrepreneur, turn-around expert, technology and product leader, and mentor, Todd has held full corporate P&L and product development responsibilities and directed diverse international teams of Engineering Managers, Mobile Architects, Developers, Dev Ops, QA, and Customer Success professionals.

Learn more about TechCXO

Production/Design: James Liebman

Joining us today in the Sky Lounge is Jim Rozich, founder of Wheels Up Sales and Marketing. Jim specializes in helping early-stage startups overcome the unglamorous yet essential challenges of building solid sales and marketing processes. From CRM implementation to crafting value-driven email campaigns, Jim shares practical insights that founders need to create traction and scale effectively.

In this episode, we explore the realities of early-stage startup sales, common pitfalls, and the art of developing scalable processes that work. Jim also shares his thoughts on the evolving venture investing landscape and why startups are becoming the “new bricks and mortar.” Plus, we dive into the tools and tactics that can help founders thrive, including the strategic use of CRMs, leveraging AI for marketing, and the critical importance of personalization in sales.

ABOUT OUR GUEST

With a dynamic career spanning two decades in sales and marketing, I’m Jim Rozich. As an industry veteran, I have consistently navigated the intricacies of bringing products and services to market - honing my expertise in crafting tailored strategies for CRM implementation, devising lead generation tactics, and refining messages that resonate with target audiences.

My genuine passion for business development and startups is what sets me apart. Embark on your journey with confidence, knowing that you have a trusted ally with a 20-year history of propelling businesses to new heights.

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Contact info

Email: [email protected]

What is THE SKYLOUNGE?

Tales from the SkyLounge is a podcast where we take you on a journey through the world of business, consulting, and venture investing. In each episode, we gather in our virtual sky lounge, high above the hustle and bustle of the everyday world, to hear stories from the people shaping these industries' future. From entrepreneurs who are disrupting the status quo, consultants who are helping companies solve their biggest challenges, and investors who are making bets on the next big thing.

ABOUT OUR HOST

Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CiSO as a partner at TechCXO.

He has served in a series of companies as a C-Level executive focused on leveraging the Cloud to bring SaaS offerings to market. As an entrepreneur, turn-around expert, technology and product leader, and mentor, Todd has held full corporate P&L and product development responsibilities and directed diverse international teams of Engineering Managers, Mobile Architects, Developers, Dev Ops, QA, and Customer Success professionals.

Subscribe and turn on notifications to listen to new episodes as they launch!

Follow Tales From The SkyLounge on Social Media

Learn more about TechCXO

Production/Design: James Liebman
Music: Soundstripe/Cody Martin-Sunrise

Today in the Sky Lounge, we’re joined by Adam Lehde, co-founder of Happen Technologies, to explore the art of building businesses across borders. Adam shares how he turned his initial doubts about outsourcing into a thriving hybrid business model that bridges Midwest strategy with Ukrainian tech talent.

We dive into Adam’s journey from a rocky internship to mastering mobile development, the resilience of Ukrainian developers amidst wartime, and why culture always matters in tech. Adam also reveals how personal priorities and work-life balance shaped his company’s values and offers insights into the ever-evolving remote work landscape.

And yes, you’ll want to hear why Ukraine’s tech scene is full of PhDs and rocket scientists—and what makes it an underestimated hub for startups and innovation.

Prior to founding Happen Technologies, Adam spent his career building mobile apps and managing software projects for national brands, including Mazda, Hyundai, Anheuser-Busch, National Car Rental, and more.

He has a passion (maybe an obsession) for improving everything he encounters and looks for EVERY opportunity to make it better.

Email: [email protected]

Tales from the SkyLounge is a podcast where we take you on a journey through the world of business, consulting, and venture investing. In each episode, we gather in our virtual sky lounge, high above the hustle and bustle of the everyday world, to hear stories from the people shaping these industries' future. From entrepreneurs who are disrupting the status quo, consultants who are helping companies solve their biggest challenges, and investors who are making bets on the next big thing.

Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CiSO as a partner at TechCXO.

He has served in a series of companies as a C-Level executive focused on leveraging the Cloud to bring SaaS offerings to market. As an entrepreneur, turn-around expert, technology and product leader, and mentor, Todd has held full corporate P&L and product development responsibilities and directed diverse international teams of Engineering Managers, Mobile Architects, Developers, Dev Ops, QA, and Customer Success professionals.

Learn more about TechCXO

Production/Design: James Liebman

Joining us today in the Sky Lounge is Kathryn O'Day, entrepreneur and partner at Atlanta Ventures. Kathryn shares her journey of building multiple successful startups and being a major part of massive acquisitions. We dive deep into the parallels between endurance sports and entrepreneurship, uncovering how triathlon training taught her key lessons in consistency, grit, and pushing through difficult times.

Kathryn also reveals key insights into startup culture, highlights how Atlanta Ventures finds and molds startups to be their best selves and shares the value of being “positive, supportive, and self-starting”—qualities that shaped her experience at Pardot and beyond. We explore the importance of confidence, especially for women in tech, and discuss why being nice can be a superpower in business.

Kathryn is a partner at Atlanta Ventures, where she empowers entrepreneurs to learn, build, and grow. She has been scaling Atlanta tech companies for over a decade as employee #9 at Pardot (acquired by Salesforce) and COO at Rigor (acquired by Splunk).

Kathryn lives in Atlanta with her husband and two sons. She is a 7x Ironman Triathlon Finisher, including two World Championships.

LinkedIn: https://www.linkedin.com/in/kathrynoday/

Join us for Office Hours (Open Q&A w/Atlanta Ventures Partners): https://www.atlantaventures.com/events

Tales from the Sky Lounge takes you on a journey through business, consulting, and venture investing, hearing stories from the entrepreneurs, consultants, and investors shaping these industries.

Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CiSO as a partner at TechCXO.

He has served in a series of companies as a C-Level executive focused on leveraging the Cloud to bring SaaS offerings to market. As an entrepreneur, turn-around expert, technology and product leader, and mentor, Todd has held full corporate P&L and product development responsibilities and directed diverse international teams of Engineering Managers, Mobile Architects, Developers, Dev Ops, QA, and Customer Success professionals.

Subscribe and turn on notifications to listen to new episodes as they launch!

Follow Tales From The SkyLounge on Social Media

Learn more about TechCXO

Production/Design: James Liebman

In this episode, Ghazenfer Mansoor shares his journey from engineer to global entrepreneur. He dives into the entrepreneurial mindset needed to grow startups, develop smart products, and manage teams across multiple countries. Ghazenfer explains the challenges of building a multi-continent business and offers insights on product development blueprints, adapting post-COVID, and the importance of flexibility in business operations.

Ghazenfer Mansoor, originally from Pakistan, relocated to the United States in 1999 and has since made his home in Virginia, near the Washington DC area. He lives there with his wife and three children.

Technology Rivers, a bespoke software development firm, excels in aiding businesses to craft innovative software products. Initially launched as a mobile app development company in 2015, it has progressively shifted its focus towards custom healthcare and AI solutions. Keeping pace with the latest technological advances, the company has recently concentrated its efforts on developing cutting-edge applications powered by Artificial Intelligence, Machine Learning, and Generative AI.

https://linkedin.com/in/gmansoor
https://x.com/gmansoor
https://x.com/techrivers
https://www.instagram.com/gmansoorus
https://www.instagram.com/techrivers

Ghazenfer Mansoor
[email protected]

The Top 8 Ways App Development Goes Wrong & How to Get Back on Track

Tales from the Sky Lounge takes you on a journey through business, consulting, and venture investing, hearing stories from the entrepreneurs, consultants, and investors shaping these industries.

Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CiSO as a partner at TechCXO.

Learn more about and Contact Todd

YouTube: https://www.youtube.com/playlist?list=PLfeCS-Varb4gu2uCwyRTXWWEdP676Huh6
Spotify: https://open.spotify.com/show/6jz6ubcaUZ20Xh8TXhwzEN
Apple: https://podcasts.apple.com/us/podcast/tales-from-the-sky-lounge/id1730134658
Amazon: https://music.amazon.com/podcasts/4ba289a5-0d33-4589-95c7-83416731a864/tales-from-the-sky-lounge

X/Twitter: https://x.com/TFTSkyLounge
Instagram: https://www.instagram.com/tftskylounge/

Learn more about TechCXO: https://www.techcxo.com/

Production/Design: James Liebman
Music: Soundstripe/Cody Martin-Sunrise

Joining us in the Sky Lounge today is Kirby Winters—tech entrepreneur, cybersecurity expert, and partner at TechCXO. Kirby takes us through his journey from telecom to launching (and selling) his own business before diving back into consulting. He also shares some serious Eagle Scout leadership insights, breaks down the world of cybersecurity, and how AI is changing the game.

Kirby J. Winters is a leader in the cybersecurity and technology-based communications industry with extensive experience across multiple sectors. Since 2016, he has led the Information Security Practice at TechCXO, working with healthcare, banking, and Department of Defense clients. His leadership has delivered innovative solutions, including advanced Electronic Medical Record systems, AI-driven practice management, and wireless health monitoring tools.

Kirby has held executive positions across numerous industries. Kirby founded Winter Media in 2011, offering custom application development and information security services to clients like the US Navy, Department of Defense, and various healthcare organizations.

TechCXO Profile

Tales from the SkyLounge is a podcast where we take you on a journey through the world of business, consulting, and venture investing.

Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CiSO as a partner at TechCXO.

Learn more about TechCXO