Claim OwnershipThe Way In
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© 2025 Shijia Mao
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The Way In dives into the choices, risks, and lessons behind building a business. Each week, founders and small business owners share how they carved their own path - one choice, one risk, one step at a time.
20 Episodes
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In this episode of The Way In, I speak with Trevor, CTO of Olive Legal, about stepping into leadership at a company he didn’t start.Trevor joined Olive Legal as the first engineering hire, drawn by the chance to learn from experienced founders. When those founders later moved on to a new venture, Trevor was faced with an unexpected opportunity: take over a revenue-generating business while untangling an inherited codebase and finding the right partner to build alongside.In this episode, we cover:Taking over a company you didn’t foundBuilding vs. operating an existing businessLessons carried forward from Trevor's first startupHow lawyers worked before Olive Legal and what changes afterDesigning tools that support, not replace, legal professionalsHiring a CEO as a technical founderMeasuring success through retention and real usage
In this episode of The Way In, I speak with Eric and Dev, the founder duo behind Marmalaide, a company using generative AI to create high-quality marketing content.Eric shares his background as an independent filmmaker and how the writers’ and actors’ strikes pushed him to experiment with AI, leading to a viral parody video that helped catalyze Marmalaide’s early momentum. Dev breaks down the business model, from defining the ideal customer profile to balancing one-off projects with long-term collaborations, and shares their view on the future of AI in marketing.
In this episode of The Way In, I speak with Sid Sridharan, co-founder and CEO of Spendflo, about the evolution of the company from SaaS spend management to an AI-native platform.Sid shares lessons from founding and scaling Spendflo, the role of venture capital, the difficult decision to exit a market, and why he’s now focused on building AI teammates to reshape how procurement work gets done.
In this episode, Sol shares her personal journey with prenups and how Neptune is changing the narrative around these conversations. We discuss the lessons she learned from her first startup, the challenges couples face when talking about money and prenups, and how Neptune aims to simplify the process through education and access to trusted experts. Sol also reflects on the role of AI in legal matters and shares her long-term vision for Neptune as the company expands its services.
Brian, founder of Verteel, didn’t start out in tech — he started in the cockpit. In this episode, Brian shares his journey from being a professional pilot to building a drone company focusing on transforming medical logistics. He discusses the challenges of navigating regulatory environments, the importance of customer discovery, and the innovative approaches Vertel is taking to improve healthcare delivery through drone technology. The conversation also touches on the future of drone delivery, the competitive landscape, and Brian's personal growth as an entrepreneur.
In this episode, Maggi shares the journey behind Sumly, from its early prototype to its official launch after a year of development. During pilot testing, users saw an average savings of $2,350, a clear signal that the product was solving a real and painful problem. From meeting her co-founder at Columbia to building a product focused on putting money back in users’ pockets, Maggi offers an honest look at what it takes to build a financial tool for solopreneurs - and shares practical tips on home office deductions.
Kartik’s journey checks all the classic tech-founder boxes -MIT dropout, YC alum - but the real story begins when he walks away from his first product. After realizing their hedge-fund modeling tool wasn’t sticking, he made a sharp pivot into a far more chaotic world: medical billing.With insights from his physician father and dozens of billers, Kartik quickly saw how broken and costly the system really is. Instead of trying to replace billers, he’s building AI tools that amplify them - helping practices capture more revenue while reducing the administrative drag that burns out doctors.In this episode, we dive into his early drive, the YC experience, what convinced him to pivot, how Quill Bills’ modular products actually work in the field, and his vision for a billing platform designed to fix one of healthcare’s messiest workflows.
Dana’s path to founding Selformer Pilates is far from traditional. After nearly 20 years as a music photographer - constantly traveling and carrying heavy gear - she turned to Pilates to repair her body, eventually discovering a new calling. With no business background, she built Selformer by embracing her “misfit” identity and trusting her creative instincts.Based in the fitness-saturated neighborhoods of Greenpoint and Williamsburg, Selformer stands out not by competing, but by being intentionally different.This episode is full of unconventional reflections, raw honesty, and a refreshingly nontraditional take on entrepreneurship in the wellness world.
Launching a startup is often about timing - and Gu’s journey with Adzviser is a perfect example. As he was building the first version of the product, ChatGPT launched, creating a sudden surge of interest in AI tools. The timing was serendipitous: Adzviser quickly became one of the first tools recommended by OpenAI, giving it an early edge in the market.But timing alone doesn’t build a business. Gu has stayed obsessively focused on delivering real value, talking to users, and iterating fast. In this episode, he reflects on the role of a growth mindset, the discipline required to bootstrap a SaaS business, and what it takes to scale in an ever-changing AI landscape.
Alvina, founder of SHUMINGYU, didn’t come from a traditional fashion background. A humanities student who later worked at Christie’s, she draws inspiration from a wide range of artistic genres and notices the subtle nuances in Chinese culture. From classical poetry to watercolor paintings, Alvina shares how Chinese art informs her clean, contemporary silhouettes, and how she creates clothing that quietly weaves culture into everyday life.
In this episode, Kiki, co-founder of Sourmilk, breaks down how she built a sold-out yogurt brand in record time. In just 10 months, Sourmilk landed on shelves at two NYC grocery stores, sitting right next to industry giants like Chobani. Was it luck, relentless hustle, or the right partnership at the right time?Kiki shares how social media became her most powerful growth engine, what she’s learned from building a company with her best friend, and the strategic steps (from corporate catering to neighborhood drop-offs) that shaped Sourmilk’s go-to-market playbook.
Chef Cipollone knows what it takes to earn a Michelin star -and more importantly, to keep one. In this episode, he shares how years in top kitchens shaped his approach to leadership, creativity, and building a team that lasts. We talk about the mentors who pushed him, the lessons behind Francie’s success, and how his new project, Allegretto, brings together design, energy, and heart in a whole new way.
Logan started out as a Paulie Gee’s fan - now he’s behind the counter running his own location in Gowanus. In this episode, he shares how a love for great pizza turned into a full-time pursuit, what he learned opening a restaurant in New York City, and why consistency, community, and craft matter more than ever in the food business.Chapters01:05 The Journey into Pizza Making04:39 Training and Learning the Craft07:23 Experimentation and Creativity in Pizza08:07 Expanding to Gowanus: The decision Process10:44 Working with Family: The Brother Dynamic11:21 Challenges in Opening a New Location14:26 Navigating Competition in the Pizza Industry18:21 Understanding Cost Structures in Restaurants20:21 Trends in the Pizza Industry22:07 Rapid Fire Questions and Personal Favorites
This episode is full of energy, grit, and heart — just like Kiah herself.After years in the Bay Area restaurant scene and co-founding Far Out Catering, Chef Kiah Fuller took a leap to start Plated by Chef Kiah — a private dining brand that brings high-end experiences to people’s homes and communities.In this episode, Kiah shares what she learned from her time in fine dining, the scrappy early days of entrepreneurship, and how she’s building a business rooted in artistry, inclusivity, and joy.Chapters01:17 The Impact of Studying Abroad in Florence02:24 Navigating Culinary School and Fine Dining 06:23 The Birth of Far Out Catering09:08 Adapting to the Pandemic: Flexibility and Resilience12:02 Lessins Learned and Future Aspirations14:49 Introducing Plated by Chef Kiah17:10 Building Online Prescence as a Private Chef18:52 Creating sustainable Menus23:36 Advice for Culinary Graduates
In this episode of The Way In, I sit down with Daniel, the new owner of three PingPod franchise locations in Williamsburg, Downtown Brooklyn, and the Lower East Side.Daniel shares what inspired him to move from investor and advisor to franchise owner, his transition from analyzing businesses to operating them, how he's applying his analytical toolkit to optimize pricing models and community building, and his vision for using ping pong as more than just a sport. Daniel’s vision centers on accessibility, wellness, and human connection.We also discuss his partnerships with organizations like the Parkinson's Association and where he sees these three locations heading in the years to come.Chapters00:00 Daniel's Background in Business Transformation02:19 Connection to Table Tennis Community05:05 The Evolution of PingPod and Daniel's Role07:02 Two reasons for Becoming an Owner Operator09:48 Pricing Strategy and Community Engagement11:49 Figuring out the Yield Per Fixed Table14:07 Marketing and Attracting Local Communities17:23 Building a Vibrant Table Tennis Community20:05 Surprises of Franchise Operations24:23 Concluding Thoughts and Personal Goals for Being a Franchisee
When it comes to protein bars, 99% of the market is dominated by chocolate or peanut butter flavors. Frustrated by the lack of variety, Gene set out to create something different - savory protein bars inspired by international flavors. After hundreds of recipe iterations, he and his mom hand-made 40,000 bars at a commercial kitchen.Four years later, Afar Foods’ savory bars can now be found in airports across the NYC area. In this episode, Gene shares how he tackled early operational challenges, what it’s like to build a company with family, and his vision for where Afar Foods is headed next.Chapters00:57 Gene's Journey from Finance to Food Entrepreneurship02:49 The Creative Process Behind Flavor Development06:08 Marketing a New Snack Category: Challenges and Strategies08:47 Quality Control in Early Production Stages11:41 Navigating Co-Manufacturing Challenges14:57 Go-to-Market Strategy: E-commerce vs. Retail17:59 Building Brand Recognition Through Diverse Channels21:00 Future Plans: Balancing E-commerce and Retail Growth22:50 The Role of Family in Business Operations25:58 Adjusting to the Entrepreneurial Lifestyle29:01 Funding and Maintaining Control in Business29:52 Rapid Fire Questions: Insights and Aspirations
From her early days as a hostess at COTE Korean Steakhouse to partnering with wine bars across New York City, Jennifer has carved her own path with Club Soda — a proof of concept that Chinese dishes and natural wine can be a perfect match. In this episode, Jennifer shares what motivated her to pursue a career in food, how she pushed herself to create original dishes, and the lessons she’s learned running pop-ups. We talk about the balance between intimate 10-person dinners and high-energy events for 100+ guests, and what it takes to prioritize as both a chef and a business owner.Chapters00:54 Early Influences and Career Path in Food02:22 Experiences at Notable Restaurants04:39 Transitioning to Pop-Ups and Business Maturity06:24 Inventory Management Challenges07:52 Cooking for Different Group Sizes10:11 Planning and Execution of Pop-Ups12:31 Sustainability and Competition in the Pop-Up Scene14:55 Cultural Representation through Food17:12 Mooncake Project and Seasonal Offerings18:24 Lessons Learned in the Pop-Up Industry19:57 Personal Reflections on Dining and Appreciation21:39 Self-Care and Staying Inspired22:52 Rapid Fire Questions and Closing Thoughts
If you visit Puerto Rico, chances are you'll find yourself exploring the breathtaking El Yunque rainforest. And if you're there, you'll likely go on one of the waterfall hikes that have become a must-do experience. But these adventure tours didn't exist until just 5-6 years ago, when a few local companies began offering immersive outdoor experiences to travelers.Among the pioneers is Spotin, founded by Bryan. In this episode, Bryan shares his journey of navigating the volatile travel industry - from pivoting after the devastating Hurricane Maria and surviving the COVID-19 pandemic, to ultimately becoming the top-rated El Yunque rainforest tour on Viator with over 10,000 five-star reviews...Chapters02:51 The Impact of Hurricane Maria on Business05:46 Navigating COVID-19 and Business Growth08:30 The Art of Delegation and Leadership11:30 Challenges in the Tourism Industry14:29 Marketing Strategies and Trends in Tourism17:10 Operational Challenges and Customer Experience20:13 Volume Game: Keeping Prices Low22:58 Future Growth and New Opportunities26:02 Advice for Aspiring Travel Entrepreneurs28:42 Learning from Mistakes and Innovations31:39 Rapid Fire Questions and Conclusion
From in-house designer to cofounder of Koi Studios, Anyi has never shied away from taking risks - including sponsoring herself as a foreigner working in the U.S. What started as juggling client needs, design work, and even accounting has evolved into her leading business development at the company. In this episode, Anyi opens up about the realities of entrepreneurship, her hot take on AI in design, her approach to work–life balance, and more.https://www.koistudios.io/
As a firm believer in the power of compounding, Ryan began managing money for his family and friends at the age of 25. But in the early days, his fund lost more than 30% in just two quarters. In this episode, Ryan shares how he pushed through those tough times and stayed laser-focused on research. Three years later, his strategy has paid off - he’s outperformed the market by more than 70%. He also reveals a hidden gem stock that has rallied 7x since his initial investment...Chapters02:21 The Genesis of Infuse Asset Management05:15 Landing Initial LPs and Early Challenges08:48 Navigating Market Volatility and Lessons Learned10:53 Adapting to Market Changes as an Active Investor13:06 Identifying Unique Investment Opportunities17:36 Daily Operations and Research Focus22:04 Building Trust with LPs and Fund Structure24:05 The One-Man Show: Future Plans25:34 Self-Reflection and Accountability in Investing26:02 Tools and Resources for Research27:10 Qualities for Success in Investing28:23 Future Investment Strategies29:40 Rapid Fire Round: Insights and Recommendationshttps://www.infuse-am.com/lettershttps://www.koyfin.com/
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