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⚖️ Legal Disclaimer

All opinions expressed by the guests are their own. 9×90™ and its affiliates do not endorse or guarantee any specific outcomes discussed in this episode. This podcast is for informational and entertainment purposes only and does not constitute financial, legal, or investment advice. Listeners should conduct their own due diligence and consult with professional advisors before making any investment or business decisions. Nothing discussed in this episode constitutes an offer to sell, or a solicitation of an offer to buy, any securities. Any such offer or solicitation will be made only through official offering documents and to qualified, accredited investors, in accordance with applicable securities laws. The views expressed by guests are their own and do not necessarily reflect those of the host or 9×90™.

About this episode

What happens when a 20-year Apple veteran applies Silicon Valley’s obsession with user experience to the broken world of job hunting?

In this episode of 9×90™, Adi Soozin sits down with Garrett Rice, founder of Callings.ai, an AI-powered platform transforming how candidates navigate the modern job market. Drawing on two decades at Apple, Garrett shares how he infused design thinking and relentless iteration into a platform built for job seekers—not hiring companies.

Together, they dive into:
✅ How AI is reshaping resume reviews, interviews, and global competition.
✅ Why networking—not applications—is the most undervalued career skill.
✅ The hidden pitfalls of the modern job hunt and how Callings.ai helps users overcome them with tools like AI-powered job ratings, customized resumes, and “My Insights” for career clarity.

Garrett’s insights are a masterclass in balancing cutting-edge technology with deeply human challenges. Whether you’re a founder, an executive, or navigating your next career move, this episode is packed with revelations about the future of work—and how to position yourself ahead of it.

About this guest

Garrett Rice is a visionary technologist and entrepreneur redefining the future of careers. After an extraordinary 20-year tenure at Apple, where he honed his expertise in product development and mastered the art of blending technology with seamless user experiences, Garrett is now pioneering his own venture: Callings.ai.

As the founder of Callings.ai, Garrett is tackling one of the most pressing challenges of the modern era—the job search. His AI-powered platform is designed to revolutionize how candidates navigate their career journeys, offering intelligent tools for job discovery, resume optimization, networking, and interview preparation.

A recognized authority in the tech and career space, Garrett’s insights have been featured on prominent shows including The Job Interview Experience Podcast and The Job Hunt Podcast. He brings a unique perspective shaped by decades at the cutting edge of innovation, paired with a deep understanding of the challenges today’s professionals face in an increasingly AI-driven job market.

In this episode, Garrett shares how his Apple experience shaped Callings.ai’s user-centric design philosophy, the groundbreaking features empowering job seekers to thrive, and his perspective on the future of work in a globalized, technology-fueled economy.

Connect with this guest

1. https://www.linkedin.com/in/garrettrice
2. callings.ai

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Show Notes Generated by Gemini

These show notes were generated by AI

• Introduction of Garrett Rice and Callings.ai – Adi Soozin introduced Garrett Rice, a former Apple visionary with 20 years of experience, now the founder of Callings.ai. Adi highlighted Callings.ai as an AI-powered platform designed to revolutionize the job hunt for candidates. Garrett stated that Callings aims to balance the playing field for job seekers (00:01:04).
• Influence of Apple Experience on Callings.ai – Adi Soozin asked about the influence of Garrett Rice’s Apple background on Callings.ai’s user experience and innovation. Garrett explained that Apple’s culture, which focused on user experience, shaped his approach—emphasizing the job seeker as the primary user, unlike many platforms focused on hiring companies (00:02:15). He added that continuous iteration and improvement are key to his product innovation ethos (00:03:35).
• Challenges in the Modern Job Hunt – Garrett Rice detailed the difficulties faced by the average job seeker, including a longer search time (6 months to a year), hundreds of applications, and global competition due to remote work (00:03:35). He noted that AI is now heavily involved in resume evaluation and interviewing, often bypassing human involvement in the early stages (00:04:27).
• Solutions Offered by Callings.ai – Adi Soozin inquired about how Callings.ai addresses these challenges. Garrett outlined several features, including AI-powered job rating, resume analysis against job posts, help with research, customized resumes and cover letters, and an AI networking tool to connect with hiring managers and recruiters (00:05:24). The platform also assists with interview preparation and provides coaching (00:06:23).
• Callings.ai Platform Details and Pricing – Adi Soozin asked about the launch and cost of Callings.ai. Garrett confirmed that they had a soft launch and are now available, with a monthly subscription of $29.99 and discounted rates for longer-term agreements (00:07:15). He mentioned that users can search and save jobs for free, with payment required for the advanced AI tools, and a two-week free trial is available (00:08:14).
• Early Feedback and Job Market Shifts – Adi Soozin inquired about placement records, but Garrett Rice stated it was too early for definitive data (00:08:14). However, he shared anecdotal feedback from beta users indicating a 65% acceleration in their job hunts (00:09:09). When asked about significant job market shifts beyond AI, Garrett emphasized increased automation in application processes and the reality of a global job market. He stressed the need for job seekers to market themselves effectively and leverage networking (00:11:11).
• Networking Strategy and Callings.ai’s Role – Garrett Rice underscored the importance of networking, suggesting that having around 500 people aware of a job search could lead to a few helpful connections. He explained that Callings.ai helps users find the right networking contacts and drafts outreach messages to make the process easier and less stressful (00:14:01).
• Inspiration for Callings.ai and Addressing AI Intimidation – Adi Soozin asked about the origin of the idea for Callings.ai (00:19:56). Garrett Rice explained that the concept arose from discussions with co-founders Philippe Caillou and Horse Goven, recognizing the pain points in the modern job hunt and the potential of AI (00:21:02). Regarding intimidation around AI, he advised users to engage with and demystify AI tools like ChatGPT to understand their capabilities (00:22:16). He clarified that AI is a powerful tool that augments human wisdom but cannot replace it (00:23:17).
• Callings.ai’s “My Insights” Feature and Knowing Oneself – Garrett Rice highlighted the “My Insights” feature on Callings.ai, which uses AI to ask users questions about their preferences and goals to help them understand their ideal job and career path (00:25:15) (00:30:03). He emphasized the importance of self-awareness as the first step in a successful job hunt, a point emphasized by their career coach co-founder Horse Goen (00:29:11).
• Addressing Career Services and International Reach – Adi Soozin inquired if career services at universities could coordinate with Callings.ai. Garrett Rice welcomed the idea and provided his contact information (garrett@callings.ai and LinkedIn: Garrett Rice) (00:34:09). In response to a question about international functionality, Garrett stated that while currently focused on the U.S., Callings.ai would significantly expand its global job pool within the next month to a month and a half. He also mentioned their strategy to aggregate jobs directly from hiring company sites (00:36:16).

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Transcript

This transcription was generated by Gemini & edited by ChatGPT

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Adi Soozin: Welcome to another episode of 9×90. Today’s guest comes highly recommended—at the enthusiastic insistence of Brandon Lane Larson—who told me I absolutely had to bring one of his brilliant, genius friends onto the show. And I have to say, you’re all in for a real treat. Joining us is Garrett Rice, a true visionary in the tech and career space.

Now before you assume this intro was written by ChatGPT, let me assure you—it wasn’t. Garrett has earned every word of this praise. He spent an extraordinary 20-year career at Apple, honing his expertise in product development and mastering the intricate dance between technology and user experience.

Garrett Rice: So much better in action than ChatGPT could have done for me, I assure you.

Adi Soozin: Exactly. Garrett is now channeling his innovation and wisdom into his own entrepreneurial venture, Callings.ai—an AI-powered platform uniquely designed to revolutionize the job hunt for candidates. As a recognized authority in the field, Garrett’s insights have also been featured on prominent shows like The Job Interview Experience Podcast and The Job Hunt Podcast.

For those of you wondering how you can compete in today’s AI-driven job market and get your resume in front of the right people, Garrett is here to share answers and strategies.

Garrett Rice: Callings is here to level the playing field for you. If you’re looking for your next opportunity, we’d love to help.

Adi Soozin: I know a lot of people are going to be very excited to check out your software. Given your two decades of experience building products at Apple, how has that background influenced your approach to creating Callings.ai, particularly when it comes to user experience and product innovation for job seekers?

Garrett Rice: Thank you, Adi. I’m excited to be here. Working at Apple was truly a crucible. The culture there is laser-focused on what the experience is like for the user. That ethos shaped my perspective profoundly: it’s about understanding who the end user is and designing for them relentlessly.

At Callings.ai, we’ve carried forward that philosophy. The modern job hunt has become incredibly challenging for candidates, and unlike many platforms that focus primarily on hiring companies or recruiters—because that’s where the money is—we’ve made it our mission to focus on the job seeker. For us, the candidate is the end user, and everything we do is built around their experience.

When it comes to product innovation, we believe in continuous iteration. The goal is to never stop improving—to add features, simplify processes, and continually solve the real-world problems of today’s job seekers.

Adi Soozin: That’s such an Apple mindset—iterate until it’s extraordinary. What are some of the biggest challenges job seekers face in this new environment?

Garrett Rice: The challenges are significant. Today, the average job seeker spends between six months and a year finding their next role. For more senior, white-collar positions, it trends toward a year. People are applying to hundreds of jobs because competition is now global.

Thanks to remote work and tools like Zoom, companies realized they’re no longer restricted to hiring locally. That creates arbitrage situations where candidates are competing against applicants from around the world—often on cost as well as qualifications.

On top of that, AI is now heavily involved in resume screening and interviews. In many cases, a human being never even sees your application in the early phases.

Adi Soozin: That’s daunting. How does Callings.ai help candidates navigate all of this?

Garrett Rice: We’ve designed Callings.ai to address these pain points directly. First, we help users identify which jobs they have a strong chance of landing by using AI to rate positions. We break down job descriptions against a candidate’s resume, highlight strengths and weaknesses, and suggest improvements.

We also assist with customized resumes and cover letters to ensure alignment with the company’s language and culture—because even highly qualified candidates are often rejected when their materials don’t “speak the same language” as the hiring team.

Beyond that, networking is critical. About 70–80% of successful hires involve some kind of human connection. That’s why we built a powerful AI networking tool that helps users identify hiring managers, recruiters, and team members. We even draft outreach messages to make connecting easier and less intimidating.

We also prep users for interviews and offer coaching—bringing it all together in one seamless platform.

Adi Soozin: That’s phenomenal. It really sounds like you’re equipping job seekers with everything they need to succeed. Did you already launch Callings.ai?

Garrett Rice: Yes, we’ve had a soft launch and are now live. Anyone can sign up and start using the platform today. We’re talking to users constantly, gathering feedback, and iterating rapidly to make it even better.

Adi Soozin: And how much does it cost?

Garrett Rice: If you’re paying month-to-month, it’s $29.99. But if you know you’re serious about your job search, we offer six-month and one-year subscriptions at a 33% and 50% discount respectively.

We’ve also made the platform accessible—users can search and save jobs for free forever, and they only pay for advanced AI tools. Plus, we offer a two-week free trial so people can experience the value before committing.

Adi Soozin: That’s incredibly reasonable, especially considering the potential impact. Do you have any placement data yet?

Garrett Rice: It’s still early to report definitive numbers, but the anecdotal feedback from our beta users is promising. On average, they’ve seen their job searches accelerate by about 65%. We’ve already heard success stories of people landing roles using Callings.ai tools for applications and interviews.

Adi Soozin: That’s fantastic. You’ve mentioned there are dramatic shifts happening in the job market. Beyond AI, what other trends should job seekers be paying attention to?

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Adi Soozin: And it’s remarkable how your platform is helping people adapt in real time.

Garrett Rice: Exactly. And let’s be honest—if you’re in the job market today, especially if you’re over 30, there’s a reality you need to face.

Adi Soozin: I am over 30, thank you very much.

Garrett Rice: But you also have a job, so this is more for your audience, not you. For many of us in that “over 30” category, the job market feels completely different from the one we entered years ago. When I started out, I could make a few phone calls, hand-deliver a resume, and expect to at least get an interview.

Adi Soozin: Yes.

Garrett Rice: That approach no longer works. In just the past five to seven years, everything has become highly automated. Today, companies receive hundreds—even thousands—of applications for a single position. They’re using keyword searches and AI to filter candidates. Often, no human ever sees your resume during the initial stages.

Adi Soozin: Right.

Garrett Rice: And on top of that, we’re in a global job market now. You’re not just competing with people in your city or country—you’re competing with the entire world for roles like product manager or designer. It’s become a game of musical chairs, and the challenge is getting noticed and making it to the final round.

Adi Soozin: That’s intense.

Garrett Rice: It is. And it’s only going to get more competitive as AI and other technologies continue transforming talent acquisition. To succeed, candidates need to think of themselves as marketers—marketing their own story. Every job application is a new audience, and you need to tailor your narrative for each one.

Adi Soozin: That’s so true.

Garrett Rice: Networking is another critical piece of this puzzle. It’s the single most powerful way to bypass bottlenecks in the hiring process. For every job you apply to, you should be reaching out to multiple people—three, five, even seven contacts per opportunity—to ensure your application stands out.

Adi Soozin: So you’re saying job seekers really need to think like salespeople?

Garrett Rice: Exactly. Early in my career, I worked in sales and learned this lesson the hard way: if there’s nothing at the top of the funnel, nothing comes out the bottom. To land a role, you probably need 500 people to know you’re looking for a job so that two or three will actually help you get it.

Adi Soozin: Wow.

Garrett Rice: That sounds daunting, but it doesn’t have to be. With the right tools, networking becomes second nature. Most people panic because networking feels like walking into a room of strangers and introducing yourself. It’s uncomfortable—psychologically, it ranks right up there with public speaking and standing on a high cliff.

That’s why Callings.ai is designed to make the process effortless. Our platform identifies the right people to contact, drafts outreach messages for you, and integrates seamlessly with LinkedIn. You wake up every day knowing exactly who to reach out to, what to say, and how to say it—with no stress.

Adi Soozin: So you’ve basically taken overwhelmed, stressed-out job seekers and helped them project calm, emotional intelligence, and confidence—qualities every hiring manager wants to see.

Garrett Rice: That’s the goal. The job search is one of life’s most psychologically challenging experiences. It’s right up there with divorce, serious illness, or loss. You can’t escape that reality, but you can take small, consistent actions every day.

You may not be able to force someone to offer you a job, but you can put yourself in motion—have conversations, make connections, and let people know you’re looking. The confidence boost when someone calls you back is incredible. Suddenly, you’re prepared and focused, and you’re no longer alone in the process.

Adi Soozin: That’s brilliant. And Garrett, I’m not sure if Brandon mentioned this, but my book recently hit the bestseller list—number two in the US.

Garrett Rice: Congratulations! That’s fantastic.

Adi Soozin: Thank you. I was hired to write this 444-page guide teaching marketers how to use AI effectively—so they become indispensable to their companies instead of being replaced by AI. It’s a topic so many people are anxious about right now.

Garrett Rice: That’s incredibly timely.

Adi Soozin: Some people even think I’m under 30, which cracks me up.

Garrett Rice: My mother used to say every birthday was her “29th again” until she turned 60.

Adi Soozin: I love that. In commercial real estate, there’s a saying that you should “pretend you’re 40” until you finally turn 40. It’s all about projecting the right mix of youth and maturity.

Garrett Rice: Exactly—you want to seem both young and seasoned.

Adi Soozin: But coming back to the book, my goal was to help junior marketers level up quickly—to make them irreplaceable in a world where roles are being outsourced or automated. For example, my social media, customer success, and design teams are in the Philippines. I get exceptional talent there for $800 a month, pay them double what they’d make elsewhere to ensure loyalty, and invest heavily in their training.

Garrett Rice: That illustrates the challenge U.S. job seekers face. Ten years ago, this kind of global outsourcing wasn’t feasible. Companies didn’t have the tools or infrastructure to manage overseas talent effectively. But with platforms like Zoom and Slack, the barriers are gone. Now, U.S.-based candidates are competing against a global workforce.

Adi Soozin: It’s a totally different world.

Garrett Rice: It is. But there’s still opportunity—especially for people with deep experience and strong skills. The key is finding the right companies and positioning yourself as the ideal candidate for their needs.

Adi Soozin: That’s such a powerful perspective.

Garrett Rice: Thank you.

Adi Soozin: So let’s go back to Callings.ai. You’ve essentially built a platform that functions like a 300-person HR team for a single job seeker. That’s incredible. Where did the idea come from?

Garrett Rice: It started with my co-founders, Philippe Caillou and Horst Goven. Horst is a professional career coach, and after many years at Apple, I decided to search for a role outside that ecosystem for the first time. I hired Horst to help me navigate the modern job market, and together we realized just how broken and overwhelming the process had become.

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Garrett Rice: At the time, I wasn’t entirely certain what I wanted to do next. That’s when I met Philippe through HRT’s career coaching group, and we instantly connected. Even back then—years before AI truly exploded—we were both convinced it would become the next major revolution in tech. We’re both product people, with a shared passion for building elegant, impactful solutions.

We started talking about how painful and broken the modern job search process had become. It’s a nightmare for most job seekers—and as we’ve both been trained to see it, a pain point that significant signals an opportunity for a product. Philippe began building tools for job seekers, and soon after, we formalized the company. Horst joined us as a co-founder, bringing his expertise as a professional career coach. Fast forward 18 months to two years later, and we now have a comprehensive, fully developed job search platform that’s helping people around the world. It’s been incredibly exciting to see it take off.

Adi Soozin: That makes so much sense now. I was wondering how someone with two decades at Apple transitioned to building a platform for job seekers.

Garrett Rice: (laughs) Yes, it’s been quite the journey.

Adi Soozin: With the rapid advancement of AI, what’s one major misconception about its role in the job market you’d like to clear up for our audience? And what advice would you give job seekers who feel intimidated by all these changes?

Garrett Rice: Let me take the second question first. You’re absolutely right—there are big changes happening, and it’s natural to feel intimidated. But the best way to build confidence in an environment of rapid change is to understand it.

I encourage everyone—no matter what field you’re in—to get hands-on with AI. Demystify it. Once you start using it, AI stops feeling like a wolf at the door and starts feeling more like a helpful companion. Philippe says it best: AI is just a tool. Like fire or the wheel, those who learn how to use it will thrive, while those who don’t risk getting left behind.

Adi Soozin: I love that analogy.

Garrett Rice: The biggest misconception I see is this idea that AI alone can replace expertise. If you don’t understand marketing and you ask AI to do marketing for you, it won’t turn you into a great marketer. But if you do understand marketing and you pair that expertise with AI, you’ll be dramatically more effective than someone who doesn’t use it at all.

Adi Soozin: Exactly.

Garrett Rice: So, think of AI as an accelerant. It’s not replacing the core wisdom and judgment that comes from human experience—it’s amplifying it. Those who embrace AI as a partner in their workflow will be in high demand. At our company, we use AI across every department, from operations to product development. But the critical decisions still rest with human beings.

For job seekers, the takeaway is clear: you have to level the playing field. It’s an AI-driven world now, and to compete effectively, you need to embrace these tools.

Adi Soozin: That’s so true.

Garrett Rice: Start small. Try ChatGPT. Upload your resume and ask for feedback. Explore platforms like ours to streamline your workflow. On Callings.ai, for example, we have a feature called My Insights. It starts by analyzing your resume and then asks you a series of thoughtful questions—like what you truly want in your next role.

Adi Soozin: That’s brilliant.

Garrett Rice: It helps surface your needs and preferences, which many people haven’t fully articulated. As Horst, our career coach co-founder, often says: “The first step in any successful job search is to know yourself.” If you’re pursuing roles you’re not excited about, you’re unlikely to succeed. And even if you do succeed, why invest your energy in a role you don’t want?

Adi Soozin: That’s so important.

Garrett Rice: Exactly. Many people assume they know what they want, but often they haven’t taken the time to really discover it. That’s where a structured, Socratic approach can help.

Once you complete the My Insights process, we provide three key deliverables:

• An Ideal Job Report, which reflects back to you what you’ve defined as your perfect role.
• A Goals Report, summarizing your objectives for the job search.
• And a detailed Personal Branding Document, which includes your 30-second elevator pitch, your two-minute pitch, and the core bullet points about who you are and what makes you stand out.

These are powerful tools that leverage AI to help job seekers clarify their vision and present themselves with confidence.

Adi Soozin: That’s incredible. You’ve essentially combined the insights of a top-tier career coach with the power of AI—and made it scalable for the individual job seeker.

Garrett Rice: That’s exactly what we set out to do.

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Garrett Rice: Sometimes it’s difficult to reach clarity about yourself just by typing prompts into ChatGPT—unless you specifically ask it to start interrogating you with thoughtful, layered questions. What we’ve done with our platform is take that process to the next level. We’ve designed it to draw out those insights in a structured way. That feature alone has quickly become one of the most popular elements on our platform.

Adi Soozin: I love that. This morning, I had a friend in Australia reach out asking if I could help him land a tech job. Then he discovered I’m hiring a Chief Investment Officer for my real estate fund and asked if he could apply for that role instead. I had to explain to him that these two jobs are not synonymous. One involves determining the value of $15–100 million assets and being absolutely accurate because we’ve promised our investors a return.

Garrett Rice: (chuckles) Maybe he has a passion for both?

Adi Soozin: Possibly, but there’s a key difference—I could be sued if I put him in the wrong role on the fund, whereas I won’t be sued if he writes the wrong line of code. After this, I’m sending him this podcast episode.

Garrett Rice: (laughs) That’s a perfect example of why “know thyself” is such a critical first step in any career journey.

Adi Soozin: Yes. And yet, in the United States, we have entire industries of marketing and entertainment that seem designed to keep people from ever truly knowing themselves.

Garrett Rice: That’s true, though I also believe it’s a lifelong journey. The encouraging thing I’ve discovered after speaking with thousands of job seekers is how earnestly people want to understand themselves. They’re not just chasing roles out of desperation; they’re seeking careers that genuinely matter to them.

Adi Soozin: I agree. That desire to make an impact is deeply ingrained in American culture—perhaps even more so than in many other countries. It’s something I see in every guest who comes on 9×90. They’re all transforming the economy in some way, whether at a micro or macro scale.

Garrett Rice: Hopefully we’re doing our part by helping to reduce unemployment rates as well.

Adi Soozin: Significantly, I’d say. I have friends working in career services at top-tier universities. I imagine they’d be very eager to bring your platform to their alumni networks. As you know, schools are often measured by their graduates’ employment rates. Is there a way they could reach out to coordinate an arrangement?

Garrett Rice: Absolutely. They can reach me directly at garrett@callings.ai.

Adi Soozin: And on social media?

Garrett Rice: I’m most active on LinkedIn—Garrett Rice. I’d love to connect with them there. Interestingly, we haven’t yet focused on the education space, but we’ve already seen success stories. One Yale student used our platform and immediately landed two interviews—despite struggling with his school’s placement tools.

Adi Soozin: That’s fantastic. Does your platform work internationally? Say, if a business school in Madrid wanted to offer it to alumni seeking opportunities in Europe, the Middle East, or Latin America?

Garrett Rice: Yes, we’re built for a global audience. At the moment, most of our focus is on the U.S. market, but within the next month or so, we’re scaling our job pool 40-fold. That will give us one of the most robust global job inventories in the industry.

Adi Soozin: Impressive. How do you source the jobs in your database?

Garrett Rice: We aggregate directly from company career sites. This approach ensures candidates aren’t bounced between multiple job boards or forced to register across several platforms just to apply. Our goal is to bring users directly to the source, simplifying the process and increasing their chances of success. With hundreds of applicants for each posting, getting in early—without unnecessary handoffs—is absolutely critical.

Adi Soozin: That makes sense. Well, Garrett, thank you for answering all my questions—and for surviving this episode. I appreciate you staying alive throughout the conversation.

Garrett Rice: (laughs) The pleasure was all mine, and yes, I managed to make it through in one piece.

Adi Soozin: It was very selfless of you. I look forward to having you back on the show—and now we have our first inside joke, so clearly, we’re friends for life.

Garrett Rice: I couldn’t agree more.

Adi Soozin: And to everyone listening, thank you for joining us for another episode of 9×90.

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Listen to this episode using your favorite app

⚖️ Legal Disclaimer

All opinions expressed by the guests are their own. 9×90™ and its affiliates do not endorse or guarantee any specific outcomes discussed in this episode. This podcast is for informational and entertainment purposes only and does not constitute financial, legal, or investment advice. Listeners should conduct their own due diligence and consult with professional advisors before making any investment or business decisions. Nothing discussed in this episode constitutes an offer to sell, or a solicitation of an offer to buy, any securities. Any such offer or solicitation will be made only through official offering documents and to qualified, accredited investors, in accordance with applicable securities laws. The views expressed by guests are their own and do not necessarily reflect those of the host or 9×90™.

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