Tales From The Sky Lounge-A Business Podcast

Todd Merrill

Welcome to Tales from the Sky Lounge, a podcast where host Todd Merrill—a veteran software engineer and founder—takes you on an intimate journey through the world of business, consulting, and venture investing. From our virtual perch high above the daily grind, we dive into candid conversations with entrepreneurs, consultants, and investors who share their battle-tested insights and untold stories from the startup trenches, offering fresh perspectives on what it takes to thrive in today's dynamic business landscape.

  1. Sep 23

    Ep53 Jim Hasty—The Crawl-Walk-Run Playbook for Adopting AI

    Jim Hasty joins us in the Sky Lounge today to talk about the transformative power of AI in business consulting and software development. With his extensive experience across various sectors, Jim reveals how companies can revolutionize their operations by embracing AI technologies. If you're a leader struggling to keep pace with rapid technological changes, this episode is a must-listen. In this insightful conversation, Jim shares his journey from finance to founding the Cogle Group, a technology services company that helps organizations harness the potential of AI. He discusses the common pitfalls businesses face when integrating AI and the importance of fostering a culture open to innovation. You'll discover how to identify mundane tasks ripe for automation, the significance of leadership buy-in, and strategies for measuring the success of AI initiatives. We break down the challenges organizations encounter, from cultural resistance to the slow adoption of new technologies. Jim emphasizes the need for a balanced approach – taking the time to understand AI's capabilities while avoiding the trap of overwhelming complexity. He shares compelling examples of companies successfully leveraging AI to enhance productivity and streamline operations, highlighting the opportunities available for those willing to experiment. The stakes are high: failing to adapt could leave your business behind in a rapidly evolving landscape. This episode underscores the potential for AI to not just improve efficiency but also to free up valuable time for teams to focus on what truly matters. ABOUT OUR GUEST: Accomplished technology business development leader focused on helping clients achieve success and competitive advantage by Adopting AI and embracing rapid development and delivery of next-generation software combining Cloud Computing, Big and Fast Data, Analytics, and Mobile to help better Serve (and understand) their customers and businesses. As a regional sales leader, Jim has increased sales bookings and new client acquisition year after year. Jim leverages a consultative sales approach and values building relationships with clients and partners which has enabled him to grow existing accounts while continuing to drive new business. Jim has developed and implemented mentoring programs in each of his roles and continues to serve as a mentor in business and in the local community to help young men realize their potential. Jim believes in giving back to the community and serves on the board of a local non profit with a focus on helping homeless families get back on their feet. CONTACT: https://www.linkedin.com/in/jwhasty/ 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 a fractional/interim CTO and CISO and former C-level SaaS executive. An entrepreneur, turnaround expert, and mentor, he has held full P&L and product responsibility and led international engineering, DevOps, QA, and customer success teams. 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 Follow Tales From The SkyLounge on Social Media 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

    Ep53 Jim Hasty—The Crawl-Walk-Run Playbook for Adopting AI

  2. Sep 9

    Ep52 Steve Walsh — Founders: These Are the Mistakes You Don't Know You're Going to Make

    Today in the Sky Lounge, we are joined by Steve Walsh, founder of Hands On Angel. Steve spent 25 years in US broadband doing the same job twice: building a B2B division out of nothing. At Cox Communications it went from no customers and no revenue to a billion dollars. At Comcast, he walked into a room with two other people, a mandate to launch 25 markets in two years, and unlimited capital. He asked what the plan was. His boss stood up, told him that was why they hired him, and left the room. Ten years later it was a $10 billion business.Nine years ago he started over. Roughly 6,000 founder conversations have produced the 69 companies he actually works with — about $1 billion raised in aggregate and 11 exits. He explains why he won't touch anything that isn't a Delaware C corp, why a founder who hires a VP of sales at three customers is already finished, why onboarding is the last real differentiator, and why he thinks 90% of people shouldn't start companies at all. Plus a rented Slovenian castle, a dungeon wine cellar, and a 2 a.m. question with an answer that made the work worth it. ABOUT OUR GUEST: Steve Walsh is the Founder of Hands On Angel, a media platform helping early-stage technology founders navigate the startup journey. Every day, Steve creates content focused on fundraising, founder decision-making, investor perspectives, and company building—all grounded in real conversations with founders. As an active angel investor in 69 startups and a Mentor in Residence at Techstars, he combines decades of operating experience with practical advice that's helping the next generation of entrepreneurs raise capital and build enduring companies. Companies in his portfolio have gone on to raise more than $1.4 billion. CONTACT: www.handsonangel.com steve@handsonangel.com linkedin.com/in/handsonangel 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 Follow Tales From The SkyLounge on Social Media 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

    Ep52 Steve Walsh — Founders: These Are the Mistakes You Don't Know You're Going to Make

  3. Aug 12

    Ep 51 -Gregg Ficery— If You're Not Making Money, You're Not Worth Money — Tips from 1,000 Valuations

    Today in the Sky Lounge, we are joined by Gregg Ficery, founder of Integgra Valuation & Advisory Services and one of the people founders call when a number has to hold up — in a funding round, in a divorce, or on a witness stand. Gregg left MCI Telecom for an Atlanta internet consultancy called IXL right after WorldCom took MCI over, collected his first stock options, and watched them go to zero when youdecide.com's business model never worked. He landed in valuation because the IRS created 409A and somebody had to do the work. Three firms later — including Silicon Valley Bank's group, the largest in the country — he had watched all three fail to make money at a business he found conspicuously simple. So in 2011 he started charging less and keeping more. He explains why revenue multiples are the number he trusts least, what happened when a departing agency partner demanded $10 million for her third of the business, and why SPACs were the no-doc mortgage of going public. Then there's the fifteen-year project: a box of photographs in his grandmother’s Pittsburgh basement that started a journey through his family’s legacy in football and the game’s backstory in his book “Gridiron Legacy: Pro Football’s Missing Origin Story.” And an experience in Florence that took some travel in a rough direction! ABOUT OUR GUEST: Gregg Ficery is the founder and president of Integgra Valuation & Advisory Services, which he launched in 2011 after more than 20 years in the field and nearly 1,000 private company valuations. He came to it by way of a decade in finance, accounting, and corporate development across technology, telecom, and financial services, then a Director role at SVB Analytics — Silicon Valley Bank's valuation arm — where he led over 150 engagements pricing stock options for 409A and SFAS 123R compliance, and before that a Senior Director post at Atlanta boutique Taylor Consulting Group handling M&A, financial reporting, tax, and litigation work, including expert witness testimony. He is also the #1 Amazon best-selling author of Gridiron Legacy: Pro Football's Missing Origin Story, and a speaker. CONTACT: https://integgra.com/ https://www.gridironlegacy.com/ 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 Follow Tales From The SkyLounge on Social Media 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

    Ep 51 -Gregg Ficery— If You're Not Making Money, You're Not Worth Money — Tips from 1,000 Valuations

  4. Jul 22

    Ep 50 - Kirby Winters —Parallel Entrepreneurism: Shipping Startups Side by Side

    Today in the Sky Lounge, we are joined by Kirby Winters — a returning guest and a self-described multipreneur running several companies at the same time. Most founders build one thing and give it everything. Kirby's bet is different: when AI compresses the build cycle from years to months, you can run companies in parallel. He and Todd get into why that's suddenly viable — and what it actually takes to hold three (and more) ventures in your head at once. The anchor is Cyber Savi, the compliance firm he built after walking away from consulting six months ago, now up to seven tools. But the same velocity that let him ship those tools also powers the others: Literally Vodka, a celiac-friendly brand born from his wife's search for something sippable and gluten-free, now expanding across the Southeast; and Unshucked, an app for tracking and rating oysters by origin and salinity. Along the way: why knowledge stopped being worth selling, the """"AI DR"""" problem nobody's planning for, and a bucket-list parachute landing at a beach bar. ABOUT OUR GUEST: Kirby Winters has been a lifelong student of technology, immersing himself in the field for decades. His career began in the wireless industry with GTE Wireless, where he gained diverse experience in roles ranging from marketing manager to database administrator. He then transitioned to the internet sector, launching Winter Media, a consultancy for new internet ventures and software development. In 1999, he co-founded Solar Velocity, a full-service interactive marketing firm he led for over a decade before selling the company in 2011. Kirby joined TechCXO at the end of 2015, where he contributed to their team of C-level professionals providing fractional services to organizations nationwide. Beyond his primary work, he has been an active investor and advisor in the startup ecosystem, serving on the Board of Advisors for the legal video advice platform LawTake and acting as a founding member and head of technology for the live-streaming event company CrowdCams. He maintains a strong interest in supporting dynamic, early-stage companies with significant potential. CONTACT: https://www.linkedin.com/in/kirbywinters Learn more: https://cybersavi.com/ https://literallydrink.com/about-us/ https://unshucked.co/ 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 Follow Tales From The SkyLounge on Social Media 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

    Ep 50 - Kirby Winters —Parallel Entrepreneurism: Shipping Startups Side by Side

  5. Jun 24

    Ep 49—Jen Bonnett - The CEO Is The Salesperson: Why Founders Can't Just Hand Off the Pitch

    Today in the Sky Lounge, we are joined by Jennifer Bonnett — a longtime Atlanta tech entrepreneur who coded a search engine called eTour.com in 1997, five years before Google existed, and rode it to one of the most-trafficked websites in the world. After years building Georgia's startup ecosystem at ATDC, the Savannah Economic Development Authority, and Invest Atlanta's Women's Entrepreneurship Initiative, she's done something deliberate: walked away to spend the summer ""playing with AI."" This conversation moves fast across what's actually changing. Jen explains how she sold a no-AI city government on its first pilots, why she runs a Hermes agent that drafts her email every morning but never hits send, and the moment her voice-controlled recipe app jumped ahead because someone across the kitchen said ""next."" She and Todd map out a $30K model for starting companies in an era where software is cheap — and why the CEO still has to be the one selling. Plus: the real case for co-founders, why fewer than 2% of venture capital reaches women, and the three cities Jen has called home. ABOUT OUR GUEST: Jennifer Bonnett transforms ideas into impact. A Technology Executive and Startup Ecosystem Developer with over two decades in software development and IT management, she's built a career on empowering entrepreneurs and fostering disruptive innovation — because in every founder's dream, she sees a milestone for the industry. Her track record spans turning a struggling non-profit into a thriving hub, relocating tech firms, and pioneering programs like the Savannah Logistics Innovation Center, alongside championing women's entrepreneurship through StartupChicks. Today she's most intrigued by AI, Fintech, and Sustainable Tech — always watching for trends that serve a broader societal benefit. CONTACT: Linkedin: https://www.linkedin.com/in/jenniferbonnett/ 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 Follow Tales From The SkyLounge on Social Media 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

    Ep 49—Jen Bonnett - The CEO Is The Salesperson: Why Founders Can't Just Hand Off the Pitch

  6. May 13

    Ep 48 Kumar Ampapathini: What Builders Get Wrong About Capital—From Someone Who's Lived Both Sides

    Today in the Sky Lounge, we are joined by Kumar Amapathini, fractional CFO and Tech CXO partner with over 25 years spanning Cisco engineering, Merrill Lynch investment banking, JP Morgan, and Guggenheim Partners. Kumar started as a software developer watching Cisco make billion-dollar acquisitions he couldn't fully decode — not because the technology was over his head, but because the business logic was. That gap sent him to the University of Chicago for an MBA and into a finance career that eventually took him back to the startup world he'd left behind. Today he serves growth-stage companies as a fractional CFO, bringing Wall Street-level deal experience to founders who need it most before they can afford it full-time. He walks through what institutional investors actually want to see — and why it's usually not what founders think — unpacks the M&A process behind the Schedule City acquisition by Vagaro in October 2024, and makes the case that the highest bidder almost never wins a deal. He also shares the """"corporate athlete"""" approach that keeps him sharp across a full client travel schedule — including the food poisoning lesson that permanently ended his airport culinary experiments. ABOUT OUR GUEST: Kumar Ampapathini is a TechCXO Partner and experienced finance executive who serves clients as C-Suite / Board advisor and an interim and fractional CFO. Kumar manages all financial aspects of his clients’ businesses, including Capital / Revenue Planning, Fundraising, Cap Table Management, Contract Negotiation, FP&A, Strategy, M&A, Audit, Dashboards / Scorecards, Investor Reporting, Payroll, and Taxes. Kumar’s select current and past clients include Wabbi (Cyber Security, SaaS), Security Journey (SaaS), Schedulicity (fintech, SaaS), MobileWalla (DaaS, SaaS), Delve (Software, Advertising), Pison Technology (Software / Hardware), Pippin Title (fintech, SaaS), GoodUnited (tech, SaaS), Nav.it (fintech, SaaS), Ness (Credit Card), Families in Transition (non-profit), Our Village United (non-profit), genrae (crypto), GeoXEnergy (Geothermal), etc. CONTACT: LinkedIn: https://www.linkedin.com/in/kumar-ampapathini-cpa-mba-063375/ 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 Follow Tales From The SkyLounge on Social Media 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

    Ep 48 Kumar Ampapathini: What Builders Get Wrong About Capital—From Someone Who's Lived Both Sides

  7. May 1

    Ep 47 Karen Rands—The Compassionate Capitalist: Inside Secrets to Angel and Crowdfund Investing

    Today in the Sky Lounge, we are joined by Karen Rands, founder of the Compassionate Capitalist Movement and author of Inside Secrets to Angel Investing and Inside Secrets to Crowdfund Investing. Karen spent years at IBM navigating the transition from mainframe dominance to distributed computing — watching Dell, Compaq, and Apple take market share from a company that assumed loyalty was permanent. That front-row seat to corporate stagnation shaped everything that came after: a pivot into intrapreneurship, a failed dot-com-era fundraising run that introduced her to angel investing, and a moment in a parking deck outside an Atlanta investor meeting where she found her calling with goosebumps. She took over a nearly-defunct angel group — discovered the membership was largely fictitious and the revenue model nonexistent — rebuilt it into one of the top 50 most active angel networks in the U.S., and has spent the years since solving the one problem nobody else is tackling: most people who have the means to be angel investors have never heard the term. Karen and Todd dig into why the angel investing model hasn't been innovated since the 1980s, what revenue share financing unlocks for Main Street businesses that VCs will never touch, and why AI is finally making Karen's long-held vision of a digital investor education platform actually executable. Plus: the snowstorm, the last flight out of LaGuardia, and what happens when IBM opens the bar mid-circle over Hartsfield. ABOUT OUR GUEST: Karen Rands, founder of the Compassionate Capitalist™ Movement, is a nationally recognized thought leader on angel and crowdfund investing. A former IBM innovator and past Managing Director of a leading angel group, she has spent 20+ years advising entrepreneurs and guiding investors. As the author of two books as part of the 'Inside Secrets' Series about Angel and Crowdfund Investing, host of the top rated podcast The Compassionate Capitalist Show, and creator of The Compassionalist Academy™; a digital on demand training platform for learning how to be angel / crowdfund investors, Karen inspires and equips people to build wealth by investing in private businesses, fund innovation and share in the success of those founders' businesses. All of her links to books, podcast, academy, free resources and social links are available at http://bit.ly/linkCCS. CONTACT: http://bit.ly/linkCCS 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. 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 Follow Tales From The SkyLounge on Social Media 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

    Ep 47 Karen Rands—The Compassionate Capitalist: Inside Secrets to Angel and Crowdfund Investing

  8. Apr 15

    Ep 46 Rachel Zeller of Kitces.com—Hiring Humans in an AI World

    Today in the Sky Lounge, we are joined by Rachel Zeller, Managing Director and Integrator at Kitces.com, the leading education and resource platform for financial advisors. Rachel started as a virtual bookkeeper doing five hours a month for founder Michael Kitces in 2006 — before remote work was a thing anyone took seriously. Nine years later, he asked her to drop every other client and come run the operation full-time. The job description was essentially: "I have no idea what it's going to look like, but it's going to be so much fun." In this conversation, Rachel walks through what happened when Kitces doubled its staff in 2021, how she built systems while the plane was already in the air, and why she now requires candidates to submit their AI transcript alongside their work sample. She talks through the candidate whose eyes kept going up and to the right mid-interview, why she turned off LinkedIn Easy Apply, and what """"culture fit every time, flat out"""" actually means in practice. Plus: what she's coaching her college-age son to develop that no AI can replicate."" ABOUT OUR GUEST: With a background in counseling and a love of spreadsheets and project management, I have found a role that allows me to lean into those skills simultaneously. My time as Managing Director is split between executing company strategy and overseeing the projects that roadmap towards those goals and ensuring my Team has everything they need to be their best selves at work. CONTACT: LinkedIn: https://www.linkedin.com/in/rachel-zeller-51013656 Email: rachel@kitces.com 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 Follow Tales From The SkyLounge on Social Media 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

    Ep 46 Rachel Zeller of Kitces.com—Hiring Humans in an AI World
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About

Welcome to Tales from the Sky Lounge, a podcast where host Todd Merrill—a veteran software engineer and founder—takes you on an intimate journey through the world of business, consulting, and venture investing. From our virtual perch high above the daily grind, we dive into candid conversations with entrepreneurs, consultants, and investors who share their battle-tested insights and untold stories from the startup trenches, offering fresh perspectives on what it takes to thrive in today's dynamic business landscape.

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